Evaluation of the Bruker SMART X2S: crystallography for the nonspecialist?

An evaluation of the Bruker SMART X2S for the collection of crystallographic diffraction data, structure solution and refinement is carried out with a variety of materials with different electron densities, presenting some of the successes and challenges of automation in chemical crystallography.

1. Introduction

Chemical crystallography is a mature science in which structural analysis of well formed single crystals is routine for many samples (Ooi, 2010), with the largest amount of time spent on problematic cases, such as twinning, disorder etc. (Herbst-Irmer & Sheldrick, 1998; Müller, 2007, 2009). Automation is developing for both chemical and biological crystallography (Adams et al., 2010; Dolomanov et al., 2009; Fuller et al., 2010). Automation can increase awareness of a technique, but can also lead to reduced understanding and knowledge of the scientific theory involved and reduced appreciation of its difficulties or limitations. A criticism is that it leads to a `black box' philosophy, characterized by noncritical appraisal of, and over-reliance on, the results obtained.

The Bruker SMART X2S is a benchtop crystallography instrument designed to enable more widespread use of crystallography in the wider chemical community, in the same way that NMR and mass spectrometry have become commonplace. The design has centred not only on automatic data collection, structure solution and refinement, but also on some critical analysis of the structural results obtained. The main features are the air-cooled Breeze CCD detector and an Mo microfocus source. The use of CCD detectors for X-ray diffraction is a mature technology (Gruner et al., 2002), with an air-cooled detector available since 2006. [See supplementary information¹ for further details of the instrument; see also Kirschbaum et al. (1997) and Schulz et al. (2009).] Herein, we discuss our experiences with the Bruker SMART X2S, presenting data for a representative range of chemical samples, highlighting its successes and challenges.

2. Sample preparation – alignment

Correct sample alignment remains critical for good quality diffraction data (Müller, 2009) and is a major consideration for any automated process. The effect of sample misalignment on the overall data quality and success of the instrument has been investigated with a crystal (0.24 × 0.28 × 0.29 mm) of dibenzyl sulfone, (1), for which a crystal structure had been previously reported by Rudolph et al. (2010). Three experiments were run with the crystal intentionally placed in the following positions: (i) correctly in the middle of the mount, (ii) incorrectly below the centre of the mount and (iii) incorrectly to the side of the centre of the mount. Table 1 in the supplementary information summarizes the data.

The first two experiments have similar data, both of which are perfectly acceptable for publication: a slight increase in R1, wR2 and goodness of fit (GooF) for the second experiment suggests the overall data quality is slightly worse, and the experiment took longer. For the third experiment, the crystal is sufficiently far from the centre of the mount that it is precessing in and out of the beam. Thus, the symmetry-equivalent reflections do not match, the Laue check fails and the larger centred unit cell is not identified. The checkCIF output highlights the missed symmetry, as well as the high R_int and final R values, and should alert the nonspecialist to the fact that there is a problem.

In summary, the large beam size means that alignment is not as critically important as on other instruments, particularly in the horizontal direction, although for short data collection times and good quality data, it is still important.

3. Sample preparation – sample size

Crystal size is of paramount importance for successful experiments (Müller, 2009). Different sized crystals of N-cyano-S-benzyl-S-(2-fluorophenyl)sulfilimine, (2), synthesized (Barry et al., 2009) and obtained from the same batch, were used to investigate the effects of crystal size on the capabilities of the SMART X2S. The effective minimum crystal size limit was of particular interest. Table 2 in the supplementary information summarizes the results, which show that the minimum practical crystal dimensions for a moderate scatterer, in this case S, are 0.20 mm in two directions and 0.1 mm in the third. For smaller dimensions, the system aborted data collection owing to insufficient diffraction from this compound.

Of course, one cannot completely generalize from these results to all samples since the diffracting power of each compound depends upon a number of different factors, e.g. the scattering power of the atoms, the degree of disorder, the crystal mosaicity etc.

4. Correct structure assignment

The reliability of the software for a range of compounds to which we have ready access was tested, viz. transition metal complexes, organic compounds, cocrystals and hydrates. Compounds (3), (4) and (11) are novel (see the supplementary information for their synthesis). Literature methods were used for the synthesis of (5) (Feng et al., 2009), (6) (Singh et al., 2002), (7) (Barbosa et al., 2009), (8) (Takada et al., 1997) and (9) (Brondel et al., 2010). Compound (10) was obtained from Sigma–Aldrich. The crystal structures of (9) and (10) (Himes et al., 1981) are known. For all compounds the correct structure was obtained, with satisfactory results in terms of R factor, GooF, C—C bond precision etc. (see supplementary information , Scheme 1 and Table 3). The polarity of compound (9), as evidenced by the Flack (1983) parameter, was also correctly assigned. Thus, for these compounds, the hardware and software work well to produce crystallographic and structural data of publishable quality, suitable for deposition in the Cambridge Structural Database (Allen, 2002).

5. Incorrect structure assignment – one-electron differences

Scheme 2 and Table 4 in the supplementary information show that for compounds (12)–(14) an incorrect structure was obtained. The data quality seems fine, with no evidence of twinning or disorder, so what types of issues have occurred? The errors involve differentiation between atoms that differ by one electron, e.g. N and O atoms are reversed in (12) (Wardell et al., 2005), and C and N in (13) (Kiran et al., 2008; Kelly et al., 2010). For (14) (synthesis previously described; Barry et al., 2009), an extra H atom has been placed on the N atom attached to the S atom, which is part of the unusual functional group S=N—C≡N. This group was also found in (2), for which there were no problems. Interestingly, the crystal is a racemic twin, although whether this has caused the incorrect assignment is unclear. The software did detect that there was a problem, which it attributed to twinning, and finished at this point.

Scientists have always scrutinized crystallographic results to verify that the structure makes chemical sense. This is still important, no matter what combination of hardware and software is producing the crystallographic result. As with all crystallographic experiments, evidence from other techniques is always required.

6. Crystals with multiple moieties

Compounds (2)–(14) are anhydrous samples, without any solvent present. The effectiveness of the system for crystals containing more than one compound was investigated: a hydrate, a solvate and a cocrystal, (15)–(17) (see the supplementary information for their synthesis; see also Scheme 3 and Table 5).

The structures of both (15) and (17) were assigned correctly. For (16), a C and an N atom were misassigned, as discussed in §5. The H atoms of the water molecule were not assigned, probably because of the low scattering ability of hydrogen and the fact that the experiment was not performed at low temperature. Interestingly, this is a new polymorph of (16), which has been prepared by a different method to the known polymorph (Alléaume et al., 1976) and has been confirmed by powder X-ray diffraction analysis of bulk samples of both polymorphs, as well as a comparative data collection on a Bruker APEX DUO (see §8).

7. Inputting the incorrect formula

The effect of inputting the incorrect molecular formula was investigated, since it is necessary to input a formula at the start of the experiment, and in some cases the identity of the crystal may not be known. For example, (5), C₁₃H₁₀OS, was incorrectly input as the sulfoxide, C₁₃H₁₀O₂S, and (10), C₁₅H₁₂N₂O, was input as C₂₇H₂₂N₂O₂S. The hydrate (16) and solvate (15) were input as the pure material. The software is robust and coped with an incorrect molecular formula in the majority of cases, with 80% of samples obtaining the correct structure.

There is one issue that causes inconvenience. The system does not update the CIF and report files with the molecular formula based on the structure obtained, but instead uses the formula input by the user. This requires manual refinement for cases where the submitted formula is different from the structure obtained.

8. Comparison with a Bruker APEX DUO

A comparative study with a Bruker APEX DUO was undertaken at room temperature using a sealed-tube Mo Kα source for (2), (8), (11), (12), (16) and (18), which include samples of both good and poor crystal quality. The synthesis of (18), 4-methyl-N-phenylbenzenesulfonamide, has been described by Massah et al. (2006). The results, summarized in Tables 6 and 7 in the supplementary information , are comparable for the two instruments. The biggest difference is the higher intensity of the incident beam of the APEX DUO, leading to shorter experiments for poor quality crystals.

9. Concluding remarks

The SMART X2S is a benchtop instrument designed for routine chemical crystallography and powered from a normal mains supply. The combination of the Breeze detector and the Mo microfocus source means that good quality data from crystals of large to moderate size can be collected, solved and refined without external help within a few hours. For all our samples the overall success rate is approximately >90% for correct structure assignment, rising to >99% when off-line refinement has been undertaken. (There have been two samples from over 200 experiments for which data collection has taken place and we have been unable to solve the structure.)

The checkCIF output allows fast diagnosis of any issues in the experiment. Inputting an incorrect formula at the start of the experiment, for example, will immediately become obvious from the checkCIF output because of differences in formula, density etc. In our experience, those users who are familiar with the checkCIF output after an experienced crystallographer has finalized a crystal structure are asking more questions about the checkCIF output they obtain from the SMART X2S. Novice users are also asking similar questions and some of these questions are about the technique itself. This is a major advantage of the output from the instrument, in that it does seem to be increasing awareness of crystallography among the synthetic chemists.

Instrumentation at an early stage of evolution will inevitably present minor issues that are not optimal, or at least not to an end-user's liking; for example, re-numbering of atoms has to be done off-line, using the APEX2 software suite (Bruker, 2007) which is supplied with the SMART X2S. In addition, some extra cycles of refinement would be beneficial since the software does terminate too early in some cases, as evidenced by the Δ/σ values.

In some experiments, F_obs for the very low angle reflections are much smaller than F_calc, with ΔF²/σ values significantly higher (>10) than the rest of the data set (<5), owing to the beam stop blocking or partially blocking the correct measurement of these reflections in some orientations. This is not unusual for chemical crystallography and omitting these from the latter cycles of refinement would be useful, although it may be better not to do this in a routine manner.

In summary, the SMART X2S as an instrument has allowed chemists with no crystallography experience to obtain crystallographic data for novel compounds. The instrument has greatly increased the use of crystallography in the department, with little training required to operate a user-friendly and easy-to-use instrument.

The CIF data (Hall & McMahon, 2006) for all experiments are provided as supplementary information and have been deposited with the Cambridge Crystallographic Data Centre (CCDC) for the novel crystals (2)–(8), (11) and (14)–(18). [The following computer programs were used in the refinement: APEX2, GIS, SADABS and SAINT (Bruker (2009), SHELXS97 and SHELXL97 (Sheldrick, 2008), and PLATON (Spek, 2009).]

Supporting information

Computing details

Data collection: Bruker GIS for Compound_1_Below, Compound_1_Centre, Compound_1_Side, Compound_2_Run_1, Compound_2_Run_2, Compound_2_Run_3, Compound_2_Run_4, Compound_3_CCDC, Compound_3_X2S, Compound_4_CCDC, Compound_4_X2S, Compound_5_CCDC, Compound_5_X2S, Compound_6_CCDC, Compound_6_X2S, Compound_7_CCDC, Compound_7_X2S, Compound_8_CCDC, Compound_8_X2S, Compound_9_X2S, Compound_10_X2S, Compound_11_CCDC, Compound_11_X2S, Compound_12_Manual, Compound_12_X2S, Compound_13_Manual, Compound_13_X2S, Compound_14_CCDC, Compound_14_Manual, Compound_14_X2S, Compound_15_CCDC, Compound_15_Manual, Compound_15_X2S, Compound_16_Manual, Compound_16_X2S, Compound_17_CCDC, Compound_17_X2S, Compound_18_CCDC, Compound_18_Manual, Compound_18_X2S; Bruker Instrument Service v2008, 7, 0, 0 for Compound_2_APEX, Compound_2_CCDC; Bruker Instrument Service v2009, 7, 0, 0 for Compound_8_APEX, Compound_11_APEX, Compound_12_APEX, Compound_16_APEX, Compound_16_CCDC. Cell refinement: Bruker SAINT for Compound_1_Below, Compound_1_Centre, Compound_1_Side, Compound_2_Run_1, Compound_2_Run_2, Compound_2_Run_3, Compound_2_Run_4, Compound_3_CCDC, Compound_3_X2S, Compound_4_CCDC, Compound_4_X2S, Compound_5_CCDC, Compound_5_X2S, Compound_6_CCDC, Compound_6_X2S, Compound_7_CCDC, Compound_7_X2S, Compound_8_CCDC, Compound_8_X2S, Compound_9_X2S, Compound_10_X2S, Compound_11_CCDC, Compound_11_X2S, Compound_12_Manual, Compound_12_X2S, Compound_13_Manual, Compound_13_X2S, Compound_14_CCDC, Compound_14_Manual, Compound_14_X2S, Compound_15_CCDC, Compound_15_Manual, Compound_15_X2S, Compound_16_Manual, Compound_16_X2S, Compound_17_CCDC, Compound_17_X2S, Compound_18_CCDC, Compound_18_Manual, Compound_18_X2S; SAINT V7.66A (Bruker AXS, 2009) for Compound_2_APEX, Compound_2_CCDC, Compound_8_APEX, Compound_11_APEX, Compound_12_APEX; APEX2 v2010.1-2 (Bruker AXS) for Compound_16_APEX, Compound_16_CCDC. Data reduction: Bruker SAINT for Compound_1_Below, Compound_1_Centre, Compound_1_Side, Compound_2_Run_1, Compound_2_Run_2, Compound_2_Run_3, Compound_2_Run_4, Compound_3_CCDC, Compound_3_X2S, Compound_4_CCDC, Compound_4_X2S, Compound_5_CCDC, Compound_5_X2S, Compound_6_CCDC, Compound_6_X2S, Compound_7_CCDC, Compound_7_X2S, Compound_8_CCDC, Compound_8_X2S, Compound_9_X2S, Compound_10_X2S, Compound_11_CCDC, Compound_11_X2S, Compound_12_Manual, Compound_12_X2S, Compound_13_Manual, Compound_13_X2S, Compound_14_CCDC, Compound_14_Manual, Compound_14_X2S, Compound_15_CCDC, Compound_15_Manual, Compound_15_X2S, Compound_16_Manual, Compound_16_X2S, Compound_17_CCDC, Compound_17_X2S, Compound_18_CCDC, Compound_18_Manual, Compound_18_X2S; SAINT V7.66A (Bruker AXS, 2009) for Compound_2_APEX, Compound_2_CCDC, Compound_8_APEX, Compound_11_APEX, Compound_12_APEX, Compound_16_APEX, Compound_16_CCDC. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: Bruker APEX2 for Compound_1_Below, Compound_1_Centre, Compound_1_Side, Compound_2_Run_1, Compound_2_Run_2, Compound_2_Run_3, Compound_2_Run_4, Compound_3_X2S, Compound_4_CCDC, Compound_4_X2S, Compound_5_CCDC, Compound_5_X2S, Compound_6_CCDC, Compound_6_X2S, Compound_7_CCDC, Compound_7_X2S, Compound_8_CCDC, Compound_8_X2S, Compound_9_X2S, Compound_10_X2S, Compound_11_CCDC, Compound_11_X2S, Compound_12_Manual, Compound_12_X2S, Compound_13_Manual, Compound_13_X2S, Compound_14_CCDC, Compound_14_Manual, Compound_14_X2S, Compound_15_CCDC, Compound_15_Manual, Compound_15_X2S, Compound_16_Manual, Compound_16_X2S, Compound_17_CCDC, Compound_17_X2S, Compound_18_CCDC, Compound_18_Manual, Compound_18_X2S.

(Compound_1_Below)

Crystal data

C14H14O2S	Z = 2
Mr = 246.31	F(000) = 260
Triclinic, P1	Dx = 1.333 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.736 (3) Å	Cell parameters from 317 reflections
b = 10.819 (5) Å	θ = 3.8–21.8°
c = 12.206 (6) Å	µ = 0.25 mm^−1
α = 89.727 (15)°	T = 300 K
β = 78.904 (14)°	Block, colorless
γ = 89.977 (18)°	0.29 × 0.28 × 0.24 mm
V = 613.6 (5) Å^3

Data collection

Bruker SMART X2S diffractometer	1596 independent reflections
Radiation source: micro-focus sealed tube	628 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.200
ω scans	θmax = 22.8°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −5→5
Tmin = 0.471, Tmax = 0.885	k = −11→11
4509 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.321	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1406P)^2] where P = (Fo^2 + 2Fc^2)/3
1596 reflections	(Δ/σ)max = 0.032
154 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.3529 (6)	0.2502 (3)	0.5002 (3)	0.0371 (11)
O1	0.2212 (15)	0.3500 (8)	0.4474 (7)	0.052 (3)
O2	0.1687 (15)	0.1538 (8)	0.5500 (8)	0.055 (3)
C1	0.275 (3)	0.0704 (16)	0.1172 (14)	0.063 (4)
H1	0.1958	0.0463	0.0565	0.076*
C2	0.224 (3)	0.0055 (16)	0.2125 (16)	0.072 (5)
H2	0.1094	−0.0650	0.2178	0.087*
C3	0.338 (3)	0.0417 (12)	0.3031 (13)	0.053 (4)
H3	0.2988	−0.0038	0.3692	0.064*
C4	0.511 (2)	0.1444 (11)	0.2961 (12)	0.039 (3)
C5	0.633 (2)	0.1823 (11)	0.3966 (10)	0.038 (3)
H5A	0.7873	0.2417	0.3741	0.046*
H5B	0.7125	0.1106	0.4280	0.046*
C6	0.529 (2)	0.3159 (11)	0.6027 (10)	0.044 (3)
H6A	0.6584	0.2557	0.6254	0.052*
H6B	0.6415	0.3870	0.5715	0.052*
C7	0.309 (2)	0.3546 (11)	0.7020 (11)	0.036 (3)
C8	0.262 (2)	0.2880 (13)	0.7984 (12)	0.053 (4)
H8	0.3674	0.2162	0.8027	0.063*
C9	0.058 (3)	0.3257 (15)	0.8921 (12)	0.066 (4)
H9	0.0337	0.2821	0.9591	0.079*
C10	−0.106 (3)	0.4286 (16)	0.8818 (15)	0.067 (4)
H10	−0.2474	0.4533	0.9414	0.081*
C11	0.448 (3)	0.1747 (16)	0.1108 (13)	0.070 (5)
H11	0.4868	0.2196	0.0445	0.085*
C12	0.564 (2)	0.2136 (13)	0.1999 (11)	0.051 (4)
H12	0.6760	0.2848	0.1950	0.062*
C13	0.146 (2)	0.4600 (11)	0.6943 (13)	0.054 (4)
H13	0.1754	0.5071	0.6292	0.065*
C14	−0.061 (3)	0.4936 (14)	0.7865 (14)	0.061 (4)
H14	−0.1726	0.5635	0.7815	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0237 (15)	0.045 (2)	0.043 (2)	−0.0031 (13)	−0.0062 (14)	0.0026 (16)
O1	0.044 (5)	0.056 (6)	0.059 (6)	0.016 (4)	−0.020 (5)	−0.010 (5)
O2	0.040 (5)	0.061 (6)	0.063 (7)	−0.013 (4)	−0.010 (5)	−0.003 (5)
C1	0.046 (8)	0.099 (13)	0.049 (11)	0.015 (8)	−0.020 (8)	−0.037 (10)
C2	0.048 (9)	0.094 (13)	0.074 (14)	−0.003 (8)	−0.010 (9)	−0.029 (11)
C3	0.054 (8)	0.044 (10)	0.060 (10)	0.001 (7)	−0.006 (8)	0.011 (8)
C4	0.020 (5)	0.031 (8)	0.062 (10)	0.008 (5)	0.001 (6)	−0.008 (7)
C5	0.030 (6)	0.042 (8)	0.041 (8)	0.002 (5)	−0.004 (6)	0.011 (6)
C6	0.041 (7)	0.044 (8)	0.047 (9)	−0.008 (6)	−0.012 (7)	0.009 (7)
C7	0.032 (6)	0.031 (7)	0.050 (9)	−0.013 (5)	−0.016 (6)	0.010 (7)
C8	0.039 (7)	0.068 (10)	0.051 (10)	0.007 (6)	−0.010 (7)	0.008 (8)
C9	0.064 (9)	0.099 (13)	0.034 (9)	0.003 (9)	−0.008 (8)	0.005 (8)
C10	0.038 (8)	0.093 (13)	0.067 (13)	−0.009 (8)	0.001 (8)	−0.021 (10)
C11	0.069 (9)	0.108 (14)	0.038 (10)	−0.002 (9)	−0.019 (8)	0.001 (9)
C12	0.042 (7)	0.067 (10)	0.043 (9)	−0.014 (6)	−0.003 (7)	0.017 (8)
C13	0.048 (7)	0.039 (9)	0.070 (11)	−0.014 (6)	−0.001 (8)	−0.001 (8)
C14	0.047 (8)	0.062 (11)	0.073 (13)	0.008 (7)	−0.011 (8)	−0.008 (9)

Geometric parameters (Å, º)

S1—O2	1.418 (9)	C6—H6A	0.9700
S1—O1	1.455 (8)	C6—H6B	0.9700
S1—C6	1.782 (12)	C7—C8	1.357 (16)
S1—C5	1.807 (12)	C7—C13	1.389 (16)
C1—C2	1.34 (2)	C8—C9	1.412 (17)
C1—C11	1.389 (19)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.37 (2)
C2—C3	1.38 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—C14	1.34 (2)
C3—C4	1.371 (16)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.377 (18)
C4—C12	1.371 (17)	C11—H11	0.9300
C4—C5	1.514 (17)	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.393 (18)
C5—H5B	0.9700	C13—H13	0.9300
C6—C7	1.499 (16)	C14—H14	0.9300
O2—S1—O1	116.9 (5)	C7—C6—H6B	109.8
O2—S1—C6	109.0 (5)	S1—C6—H6B	109.8
O1—S1—C6	108.2 (5)	H6A—C6—H6B	108.2
O2—S1—C5	107.9 (5)	C8—C7—C13	119.4 (13)
O1—S1—C5	108.2 (5)	C8—C7—C6	121.6 (11)
C6—S1—C5	106.0 (5)	C13—C7—C6	119.0 (12)
C2—C1—C11	118.6 (13)	C7—C8—C9	121.4 (12)
C2—C1—H1	120.7	C7—C8—H8	119.3
C11—C1—H1	120.7	C9—C8—H8	119.3
C1—C2—C3	120.9 (15)	C10—C9—C8	118.2 (14)
C1—C2—H2	119.6	C10—C9—H9	120.9
C3—C2—H2	119.6	C8—C9—H9	120.9
C4—C3—C2	120.2 (14)	C14—C10—C9	120.3 (14)
C4—C3—H3	119.9	C14—C10—H10	119.8
C2—C3—H3	119.9	C9—C10—H10	119.8
C3—C4—C12	120.2 (13)	C12—C11—C1	121.9 (14)
C3—C4—C5	119.3 (12)	C12—C11—H11	119.0
C12—C4—C5	120.5 (11)	C1—C11—H11	119.0
C4—C5—S1	109.6 (7)	C4—C12—C11	118.2 (13)
C4—C5—H5A	109.8	C4—C12—H12	120.9
S1—C5—H5A	109.8	C11—C12—H12	120.9
C4—C5—H5B	109.8	C7—C13—C14	118.5 (14)
S1—C5—H5B	109.8	C7—C13—H13	120.8
H5A—C5—H5B	108.2	C14—C13—H13	120.8
C7—C6—S1	109.6 (7)	C10—C14—C13	122.2 (13)
C7—C6—H6A	109.8	C10—C14—H14	118.9
S1—C6—H6A	109.8	C13—C14—H14	118.9

(Compound_1_Centre)

Crystal data

C14H14O2S	F(000) = 520
Mr = 246.31	Dx = 1.327 Mg m^−3
Monoclinic, C12/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2014 reflections
a = 24.003 (3) Å	θ = 3.4–25.0°
b = 4.7435 (6) Å	µ = 0.25 mm^−1
c = 10.8255 (12) Å	T = 300 K
β = 90.185 (4)°	Block, colorless
V = 1232.6 (3) Å^3	0.29 × 0.28 × 0.24 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1094 independent reflections
Radiation source: micro-focus sealed tube	894 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.031
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −28→28
Tmin = 0.769, Tmax = 0.886	k = −5→5
3757 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0805P)^2 + 0.0091P] where P = (Fo^2 + 2Fc^2)/3
1094 reflections	(Δ/σ)max = 0.003
78 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.5000	0.14712 (15)	0.2500	0.0388 (3)
O1	0.47410 (6)	0.3057 (3)	0.15153 (14)	0.0516 (5)
C1	0.69124 (12)	0.4134 (6)	0.0722 (3)	0.0700 (9)
H1	0.7216	0.5214	0.0479	0.084*
C2	0.69521 (11)	0.2466 (7)	0.1749 (3)	0.0708 (8)
H2	0.7282	0.2405	0.2200	0.085*
C3	0.64978 (10)	0.0866 (5)	0.2114 (2)	0.0559 (7)
H3	0.6522	−0.0243	0.2820	0.067*
C4	0.60086 (9)	0.0907 (4)	0.1436 (2)	0.0407 (6)
C5	0.55117 (9)	−0.0820 (4)	0.1842 (2)	0.0440 (6)
H5A	0.5628	−0.2209	0.2448	0.053*
H5B	0.5354	−0.1807	0.1138	0.053*
C6	0.59791 (10)	0.2614 (5)	0.0397 (2)	0.0513 (6)
H6	0.5652	0.2664	−0.0067	0.062*
C7	0.64250 (12)	0.4227 (6)	0.0043 (3)	0.0645 (8)
H7	0.6399	0.5377	−0.0651	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0421 (5)	0.0264 (4)	0.0479 (5)	0.000	0.0034 (3)	0.000
O1	0.0529 (10)	0.0442 (10)	0.0575 (11)	0.0059 (8)	0.0023 (8)	0.0128 (8)
C1	0.0606 (19)	0.0567 (18)	0.093 (2)	−0.0104 (13)	0.0298 (16)	−0.0048 (15)
C2	0.0445 (15)	0.0691 (18)	0.099 (2)	−0.0050 (14)	0.0004 (15)	−0.0002 (19)
C3	0.0514 (16)	0.0526 (15)	0.0636 (16)	0.0058 (12)	0.0002 (13)	0.0053 (12)
C4	0.0442 (13)	0.0322 (12)	0.0458 (13)	0.0038 (9)	0.0090 (10)	−0.0081 (9)
C5	0.0482 (14)	0.0297 (11)	0.0543 (13)	0.0007 (9)	0.0059 (11)	−0.0044 (9)
C6	0.0575 (15)	0.0524 (14)	0.0441 (13)	−0.0014 (12)	0.0044 (11)	−0.0009 (12)
C7	0.080 (2)	0.0565 (16)	0.0576 (16)	−0.0010 (14)	0.0226 (15)	0.0061 (13)

Geometric parameters (Å, º)

S1—O1	1.4437 (15)	C3—C4	1.383 (3)
S1—O1^i	1.4437 (15)	C3—H3	0.9300
S1—C5	1.790 (2)	C4—C6	1.388 (3)
S1—C5^i	1.790 (2)	C4—C5	1.513 (3)
C1—C2	1.368 (4)	C5—H5A	0.9700
C1—C7	1.380 (4)	C5—H5B	0.9700
C1—H1	0.9300	C6—C7	1.371 (3)
C2—C3	1.387 (4)	C6—H6	0.9300
C2—H2	0.9300	C7—H7	0.9300
O1—S1—O1^i	117.21 (14)	C3—C4—C6	118.6 (2)
O1—S1—C5	108.47 (10)	C3—C4—C5	120.5 (2)
O1^i—S1—C5	108.41 (10)	C6—C4—C5	120.9 (2)
O1—S1—C5^i	108.41 (10)	C4—C5—S1	109.24 (14)
O1^i—S1—C5^i	108.48 (10)	C4—C5—H5A	109.8
C5—S1—C5^i	105.22 (14)	S1—C5—H5A	109.8
C2—C1—C7	120.5 (3)	C4—C5—H5B	109.8
C2—C1—H1	119.7	S1—C5—H5B	109.8
C7—C1—H1	119.7	H5A—C5—H5B	108.3
C1—C2—C3	119.7 (3)	C7—C6—C4	121.0 (2)
C1—C2—H2	120.1	C7—C6—H6	119.5
C3—C2—H2	120.1	C4—C6—H6	119.5
C4—C3—C2	120.5 (2)	C6—C7—C1	119.6 (3)
C4—C3—H3	119.7	C6—C7—H7	120.2
C2—C3—H3	119.7	C1—C7—H7	120.2

Symmetry code: (i) −x+1, y, −z+1/2.

(Compound_1_Side)

Crystal data

C14H14O2S	F(000) = 520
Mr = 246.31	Dx = 1.326 Mg m^−3
Monoclinic, C12/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2014 reflections
a = 24.012 (3) Å	θ = 3.4–25.0°
b = 4.7429 (5) Å	µ = 0.25 mm^−1
c = 10.8321 (13) Å	T = 300 K
β = 90.197 (4)°	Block, colorless
V = 1233.6 (3) Å^3	0.29 × 0.28 × 0.24 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1097 independent reflections
Radiation source: micro-focus sealed tube	960 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.024
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −28→28
Tmin = 0.783, Tmax = 0.886	k = −5→5
3662 measured reflections	l = −12→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0759P)^2 + 0.2443P] where P = (Fo^2 + 2Fc^2)/3
1097 reflections	(Δ/σ)max = 0.008
78 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.5000	0.14726 (12)	0.2500	0.0365 (3)
O1	0.47421 (6)	0.3056 (3)	0.15149 (13)	0.0499 (4)
C1	0.69130 (10)	0.4145 (6)	0.0721 (3)	0.0678 (7)
H1	0.7217	0.5222	0.0479	0.081*
C2	0.64257 (11)	0.4232 (5)	0.0043 (2)	0.0625 (7)
H2	0.6400	0.5378	−0.0651	0.075*
C3	0.59767 (9)	0.2611 (5)	0.03988 (19)	0.0501 (6)
H3	0.5649	0.2660	−0.0062	0.060*
C4	0.60095 (7)	0.0913 (4)	0.14369 (18)	0.0384 (5)
C5	0.55121 (7)	−0.0823 (4)	0.18398 (19)	0.0422 (5)
H5A	0.5628	−0.2216	0.2444	0.051*
H5B	0.5355	−0.1806	0.1135	0.051*
C6	0.69499 (9)	0.2478 (6)	0.1750 (3)	0.0691 (7)
H6	0.7279	0.2425	0.2203	0.083*
C7	0.64984 (8)	0.0870 (5)	0.2119 (2)	0.0535 (6)
H7	0.6524	−0.0238	0.2825	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0389 (4)	0.0240 (4)	0.0466 (4)	0.000	0.0039 (3)	0.000
O1	0.0504 (8)	0.0425 (8)	0.0567 (9)	0.0056 (6)	0.0027 (7)	0.0133 (7)
C1	0.0555 (14)	0.0548 (14)	0.0931 (19)	−0.0110 (11)	0.0280 (13)	−0.0038 (14)
C2	0.0778 (17)	0.0537 (13)	0.0563 (14)	−0.0018 (12)	0.0239 (12)	0.0068 (11)
C3	0.0548 (12)	0.0520 (12)	0.0435 (12)	−0.0012 (10)	0.0034 (10)	−0.0013 (10)
C4	0.0416 (10)	0.0299 (9)	0.0438 (11)	0.0034 (7)	0.0080 (8)	−0.0068 (7)
C5	0.0446 (11)	0.0282 (9)	0.0539 (12)	0.0021 (8)	0.0063 (9)	−0.0038 (8)
C6	0.0426 (12)	0.0689 (16)	0.096 (2)	−0.0035 (12)	−0.0001 (13)	−0.0014 (16)
C7	0.0493 (12)	0.0489 (12)	0.0622 (14)	0.0061 (9)	0.0010 (10)	0.0066 (10)

Geometric parameters (Å, º)

S1—O1^i	1.4429 (14)	C3—C4	1.385 (3)
S1—O1	1.4429 (14)	C3—H3	0.9300
S1—C5^i	1.7930 (18)	C4—C7	1.385 (3)
S1—C5	1.7930 (18)	C4—C5	1.516 (2)
C1—C6	1.369 (4)	C5—H5A	0.9700
C1—C2	1.380 (4)	C5—H5B	0.9700
C1—H1	0.9300	C6—C7	1.386 (3)
C2—C3	1.380 (3)	C6—H6	0.9300
C2—H2	0.9300	C7—H7	0.9300
O1^i—S1—O1	117.25 (12)	C3—C4—C7	119.17 (19)
O1^i—S1—C5^i	108.32 (9)	C3—C4—C5	120.46 (18)
O1—S1—C5^i	108.54 (8)	C7—C4—C5	120.36 (18)
O1^i—S1—C5	108.54 (8)	C4—C5—S1	109.09 (13)
O1—S1—C5	108.32 (9)	C4—C5—H5A	109.9
C5^i—S1—C5	105.22 (12)	S1—C5—H5A	109.9
C6—C1—C2	120.2 (2)	C4—C5—H5B	109.9
C6—C1—H1	119.9	S1—C5—H5B	109.9
C2—C1—H1	119.9	H5A—C5—H5B	108.3
C3—C2—C1	119.8 (2)	C1—C6—C7	120.3 (2)
C3—C2—H2	120.1	C1—C6—H6	119.9
C1—C2—H2	120.1	C7—C6—H6	119.9
C2—C3—C4	120.6 (2)	C4—C7—C6	120.0 (2)
C2—C3—H3	119.7	C4—C7—H7	120.0
C4—C3—H3	119.7	C6—C7—H7	120.0

Symmetry code: (i) −x+1, y, −z+1/2.

(Compound_2_APEX)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.31	Dx = 1.334 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.100 (2) Å	Cell parameters from 2568 reflections
b = 11.365 (2) Å	θ = 2.6–22.5°
c = 11.300 (2) Å	µ = 0.25 mm^−1
β = 97.464 (5)°	T = 291 K
V = 1286.1 (4) Å^3	Plate, clear colourless
Z = 4	0.27 × 0.21 × 0.14 mm

Data collection

Bruker APEX II DUO diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3333 pixels mm^-1	θmax = 24.7°, θmin = 2.0°
φ & ω scans	h = −11→11
Absorption correction: multi-scan SADABS Version 2008/1	k = −13→13
Tmin = 0.83, Tmax = 0.95	l = −13→13
13491 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.278P] where P = (Fo^2 + 2Fc^2)/3
2180 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34284 (5)	0.47322 (4)	0.12743 (4)	0.05047 (17)
F18	0.12948 (13)	0.63513 (11)	0.16614 (12)	0.0783 (4)
N2	0.40076 (18)	0.36620 (15)	0.05260 (15)	0.0669 (5)
N4	0.36314 (19)	0.37798 (18)	−0.16644 (17)	0.0754 (5)
C15	−0.0887 (3)	0.3848 (3)	0.1554 (2)	0.0872 (8)
H15	−0.1777	0.367	0.1603	0.105*
C14	−0.0465 (2)	0.5001 (2)	0.16551 (18)	0.0736 (7)
H14	−0.1054	0.5605	0.1776	0.088*
C13	0.0851 (2)	0.52274 (19)	0.15715 (16)	0.0551 (5)
C12	0.17434 (18)	0.43502 (17)	0.14101 (15)	0.0488 (5)
C5	0.42218 (19)	0.43316 (18)	0.27464 (16)	0.0569 (5)
H5A	0.4127	0.3492	0.2862	0.068*
H5B	0.5168	0.451	0.2812	0.068*
C6	0.36170 (18)	0.49808 (17)	0.36994 (16)	0.0505 (5)
C11	0.3991 (2)	0.61265 (19)	0.39841 (18)	0.0607 (5)
H11	0.4621	0.6499	0.3583	0.073*
C10	0.3432 (2)	0.6717 (2)	0.4860 (2)	0.0713 (6)
H10	0.3684	0.7489	0.5045	0.086*
C9	0.2509 (3)	0.6177 (2)	0.5457 (2)	0.0757 (7)
H9	0.2137	0.658	0.6049	0.091*
C16	−0.0016 (3)	0.2960 (2)	0.1382 (2)	0.0843 (7)
H16	−0.0321	0.2188	0.1311	0.101*
C17	0.1307 (2)	0.31998 (19)	0.13135 (18)	0.0671 (6)
H17	0.1899	0.2595	0.1204	0.081*
C3	0.37844 (18)	0.37816 (17)	−0.0639 (2)	0.0552 (5)
C7	0.2681 (2)	0.44387 (18)	0.43051 (18)	0.0611 (5)
H7	0.2421	0.3669	0.412	0.073*
C8	0.2133 (2)	0.5038 (2)	0.5185 (2)	0.0754 (7)
H8	0.1506	0.4671	0.5594	0.09*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0522 (3)	0.0485 (3)	0.0524 (3)	0.0051 (2)	0.0130 (2)	0.0035 (2)
F18	0.0779 (9)	0.0585 (8)	0.0993 (10)	0.0139 (6)	0.0145 (7)	−0.0098 (7)
N2	0.0810 (13)	0.0642 (11)	0.0592 (11)	0.0219 (9)	0.0225 (9)	0.0011 (8)
N4	0.0753 (13)	0.0887 (14)	0.0646 (12)	0.0039 (10)	0.0187 (10)	−0.0080 (10)
C15	0.0562 (15)	0.143 (3)	0.0619 (15)	−0.0258 (17)	0.0066 (11)	0.0082 (16)
C14	0.0519 (13)	0.111 (2)	0.0575 (13)	0.0096 (13)	0.0067 (10)	−0.0021 (13)
C13	0.0553 (12)	0.0621 (13)	0.0474 (11)	0.0019 (10)	0.0050 (9)	−0.0018 (9)
C12	0.0518 (11)	0.0522 (11)	0.0419 (10)	−0.0007 (9)	0.0048 (8)	0.0022 (8)
C5	0.0516 (12)	0.0613 (12)	0.0571 (12)	0.0090 (9)	0.0048 (9)	0.0075 (10)
C6	0.0470 (11)	0.0565 (12)	0.0459 (10)	0.0050 (9)	−0.0018 (8)	0.0053 (9)
C11	0.0539 (12)	0.0631 (14)	0.0625 (13)	−0.0030 (10)	−0.0023 (10)	0.0030 (10)
C10	0.0789 (16)	0.0589 (14)	0.0713 (15)	0.0047 (12)	−0.0078 (13)	−0.0075 (11)
C9	0.0874 (18)	0.0785 (18)	0.0610 (14)	0.0226 (13)	0.0094 (12)	−0.0050 (12)
C16	0.0851 (19)	0.0875 (19)	0.0789 (17)	−0.0320 (16)	0.0053 (14)	0.0079 (14)
C17	0.0730 (15)	0.0595 (14)	0.0688 (14)	−0.0085 (11)	0.0095 (11)	0.0035 (10)
C3	0.0442 (11)	0.0575 (12)	0.0668 (14)	−0.0003 (9)	0.0187 (10)	−0.0046 (10)
C7	0.0690 (14)	0.0549 (12)	0.0602 (12)	0.0002 (10)	0.0114 (11)	0.0076 (10)
C8	0.0827 (17)	0.0808 (18)	0.0669 (14)	0.0066 (13)	0.0258 (12)	0.0146 (12)

Geometric parameters (Å, º)

S1—N2	1.6325 (16)	C5—H5B	0.97
S1—C12	1.7822 (19)	C6—C7	1.382 (3)
S1—C5	1.8084 (19)	C6—C11	1.382 (3)
F18—C13	1.353 (2)	C11—C10	1.376 (3)
N2—C3	1.313 (3)	C11—H11	0.93
N4—C3	1.149 (3)	C10—C9	1.365 (3)
C15—C16	1.369 (4)	C10—H10	0.93
C15—C14	1.378 (4)	C9—C8	1.372 (3)
C15—H15	0.93	C9—H9	0.93
C14—C13	1.369 (3)	C16—C17	1.375 (3)
C14—H14	0.93	C16—H16	0.93
C13—C12	1.372 (3)	C17—H17	0.93
C12—C17	1.380 (3)	C7—C8	1.380 (3)
C5—C6	1.499 (3)	C7—H7	0.93
C5—H5A	0.97	C8—H8	0.93
N2—S1—C12	105.87 (9)	C11—C6—C5	120.42 (18)
N2—S1—C5	98.23 (9)	C10—C11—C6	120.1 (2)
C12—S1—C5	99.99 (9)	C10—C11—H11	119.9
C3—N2—S1	114.56 (14)	C6—C11—H11	119.9
C16—C15—C14	121.0 (2)	C9—C10—C11	120.4 (2)
C16—C15—H15	119.5	C9—C10—H10	119.8
C14—C15—H15	119.5	C11—C10—H10	119.8
C13—C14—C15	117.8 (2)	C10—C9—C8	120.0 (2)
C13—C14—H14	121.1	C10—C9—H9	120.0
C15—C14—H14	121.1	C8—C9—H9	120.0
F18—C13—C14	119.2 (2)	C15—C16—C17	120.6 (2)
F18—C13—C12	118.60 (18)	C15—C16—H16	119.7
C14—C13—C12	122.2 (2)	C17—C16—H16	119.7
C13—C12—C17	119.37 (19)	C16—C17—C12	119.1 (2)
C13—C12—S1	119.06 (15)	C16—C17—H17	120.5
C17—C12—S1	121.53 (16)	C12—C17—H17	120.5
C6—C5—S1	111.33 (13)	N4—C3—N2	173.6 (2)
C6—C5—H5A	109.4	C8—C7—C6	120.1 (2)
S1—C5—H5A	109.4	C8—C7—H7	120.0
C6—C5—H5B	109.4	C6—C7—H7	120.0
S1—C5—H5B	109.4	C9—C8—C7	120.1 (2)
H5A—C5—H5B	108.0	C9—C8—H8	119.9
C7—C6—C11	119.25 (19)	C7—C8—H8	119.9
C7—C6—C5	120.33 (18)

(Compound_2_CCDC)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.31	Dx = 1.334 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.100 (2) Å	Cell parameters from 2568 reflections
b = 11.365 (2) Å	θ = 2.6–22.5°
c = 11.300 (2) Å	µ = 0.25 mm^−1
β = 97.464 (5)°	T = 291 K
V = 1286.1 (4) Å^3	Plate, clear colourless
Z = 4	0.27 × 0.21 × 0.14 mm

Data collection

Bruker APEX II DUO diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3333 pixels mm^-1	θmax = 24.7°, θmin = 2.0°
φ & ω scans	h = −11→11
Absorption correction: multi-scan SADABS Version 2008/1	k = −13→13
Tmin = 0.83, Tmax = 0.95	l = −13→13
13491 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.278P] where P = (Fo^2 + 2Fc^2)/3
2180 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34284 (5)	0.47322 (4)	0.12743 (4)	0.05047 (17)
F18	0.12948 (13)	0.63513 (11)	0.16614 (12)	0.0783 (4)
N2	0.40076 (18)	0.36620 (15)	0.05260 (15)	0.0669 (5)
N4	0.36314 (19)	0.37798 (18)	−0.16644 (17)	0.0754 (5)
C15	−0.0887 (3)	0.3848 (3)	0.1554 (2)	0.0872 (8)
H15	−0.1777	0.367	0.1603	0.105*
C14	−0.0465 (2)	0.5001 (2)	0.16551 (18)	0.0736 (7)
H14	−0.1054	0.5605	0.1776	0.088*
C13	0.0851 (2)	0.52274 (19)	0.15715 (16)	0.0551 (5)
C12	0.17434 (18)	0.43502 (17)	0.14101 (15)	0.0488 (5)
C5	0.42218 (19)	0.43316 (18)	0.27464 (16)	0.0569 (5)
H5A	0.4127	0.3492	0.2862	0.068*
H5B	0.5168	0.451	0.2812	0.068*
C6	0.36170 (18)	0.49808 (17)	0.36994 (16)	0.0505 (5)
C11	0.3991 (2)	0.61265 (19)	0.39841 (18)	0.0607 (5)
H11	0.4621	0.6499	0.3583	0.073*
C10	0.3432 (2)	0.6717 (2)	0.4860 (2)	0.0713 (6)
H10	0.3684	0.7489	0.5045	0.086*
C9	0.2509 (3)	0.6177 (2)	0.5457 (2)	0.0757 (7)
H9	0.2137	0.658	0.6049	0.091*
C16	−0.0016 (3)	0.2960 (2)	0.1382 (2)	0.0843 (7)
H16	−0.0321	0.2188	0.1311	0.101*
C17	0.1307 (2)	0.31998 (19)	0.13135 (18)	0.0671 (6)
H17	0.1899	0.2595	0.1204	0.081*
C3	0.37844 (18)	0.37816 (17)	−0.0639 (2)	0.0552 (5)
C7	0.2681 (2)	0.44387 (18)	0.43051 (18)	0.0611 (5)
H7	0.2421	0.3669	0.412	0.073*
C8	0.2133 (2)	0.5038 (2)	0.5185 (2)	0.0754 (7)
H8	0.1506	0.4671	0.5594	0.09*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0522 (3)	0.0485 (3)	0.0524 (3)	0.0051 (2)	0.0130 (2)	0.0035 (2)
F18	0.0779 (9)	0.0585 (8)	0.0993 (10)	0.0139 (6)	0.0145 (7)	−0.0098 (7)
N2	0.0810 (13)	0.0642 (11)	0.0592 (11)	0.0219 (9)	0.0225 (9)	0.0011 (8)
N4	0.0753 (13)	0.0887 (14)	0.0646 (12)	0.0039 (10)	0.0187 (10)	−0.0080 (10)
C15	0.0562 (15)	0.143 (3)	0.0619 (15)	−0.0258 (17)	0.0066 (11)	0.0082 (16)
C14	0.0519 (13)	0.111 (2)	0.0575 (13)	0.0096 (13)	0.0067 (10)	−0.0021 (13)
C13	0.0553 (12)	0.0621 (13)	0.0474 (11)	0.0019 (10)	0.0050 (9)	−0.0018 (9)
C12	0.0518 (11)	0.0522 (11)	0.0419 (10)	−0.0007 (9)	0.0048 (8)	0.0022 (8)
C5	0.0516 (12)	0.0613 (12)	0.0571 (12)	0.0090 (9)	0.0048 (9)	0.0075 (10)
C6	0.0470 (11)	0.0565 (12)	0.0459 (10)	0.0050 (9)	−0.0018 (8)	0.0053 (9)
C11	0.0539 (12)	0.0631 (14)	0.0625 (13)	−0.0030 (10)	−0.0023 (10)	0.0030 (10)
C10	0.0789 (16)	0.0589 (14)	0.0713 (15)	0.0047 (12)	−0.0078 (13)	−0.0075 (11)
C9	0.0874 (18)	0.0785 (18)	0.0610 (14)	0.0226 (13)	0.0094 (12)	−0.0050 (12)
C16	0.0851 (19)	0.0875 (19)	0.0789 (17)	−0.0320 (16)	0.0053 (14)	0.0079 (14)
C17	0.0730 (15)	0.0595 (14)	0.0688 (14)	−0.0085 (11)	0.0095 (11)	0.0035 (10)
C3	0.0442 (11)	0.0575 (12)	0.0668 (14)	−0.0003 (9)	0.0187 (10)	−0.0046 (10)
C7	0.0690 (14)	0.0549 (12)	0.0602 (12)	0.0002 (10)	0.0114 (11)	0.0076 (10)
C8	0.0827 (17)	0.0808 (18)	0.0669 (14)	0.0066 (13)	0.0258 (12)	0.0146 (12)

Geometric parameters (Å, º)

S1—N2	1.6325 (16)	C5—H5B	0.97
S1—C12	1.7822 (19)	C6—C7	1.382 (3)
S1—C5	1.8084 (19)	C6—C11	1.382 (3)
F18—C13	1.353 (2)	C11—C10	1.376 (3)
N2—C3	1.313 (3)	C11—H11	0.93
N4—C3	1.149 (3)	C10—C9	1.365 (3)
C15—C16	1.369 (4)	C10—H10	0.93
C15—C14	1.378 (4)	C9—C8	1.372 (3)
C15—H15	0.93	C9—H9	0.93
C14—C13	1.369 (3)	C16—C17	1.375 (3)
C14—H14	0.93	C16—H16	0.93
C13—C12	1.372 (3)	C17—H17	0.93
C12—C17	1.380 (3)	C7—C8	1.380 (3)
C5—C6	1.499 (3)	C7—H7	0.93
C5—H5A	0.97	C8—H8	0.93
N2—S1—C12	105.87 (9)	C11—C6—C5	120.42 (18)
N2—S1—C5	98.23 (9)	C10—C11—C6	120.1 (2)
C12—S1—C5	99.99 (9)	C10—C11—H11	119.9
C3—N2—S1	114.56 (14)	C6—C11—H11	119.9
C16—C15—C14	121.0 (2)	C9—C10—C11	120.4 (2)
C16—C15—H15	119.5	C9—C10—H10	119.8
C14—C15—H15	119.5	C11—C10—H10	119.8
C13—C14—C15	117.8 (2)	C10—C9—C8	120.0 (2)
C13—C14—H14	121.1	C10—C9—H9	120.0
C15—C14—H14	121.1	C8—C9—H9	120.0
F18—C13—C14	119.2 (2)	C15—C16—C17	120.6 (2)
F18—C13—C12	118.60 (18)	C15—C16—H16	119.7
C14—C13—C12	122.2 (2)	C17—C16—H16	119.7
C13—C12—C17	119.37 (19)	C16—C17—C12	119.1 (2)
C13—C12—S1	119.06 (15)	C16—C17—H17	120.5
C17—C12—S1	121.53 (16)	C12—C17—H17	120.5
C6—C5—S1	111.33 (13)	N4—C3—N2	173.6 (2)
C6—C5—H5A	109.4	C8—C7—C6	120.1 (2)
S1—C5—H5A	109.4	C8—C7—H7	120.0
C6—C5—H5B	109.4	C6—C7—H7	120.0
S1—C5—H5B	109.4	C9—C8—C7	120.1 (2)
H5A—C5—H5B	108.0	C9—C8—H8	119.9
C7—C6—C11	119.25 (19)	C7—C8—H8	119.9
C7—C6—C5	120.33 (18)

(Compound_2_Run_1)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.31	Dx = 1.323 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2425 reflections
a = 10.1414 (9) Å	θ = 2.6–22.4°
b = 11.3865 (9) Å	µ = 0.24 mm^−1
c = 11.3289 (9) Å	T = 300 K
β = 97.400 (3)°	Block, colorless
V = 1297.31 (19) Å^3	0.50 × 0.35 × 0.21 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2277 independent reflections
Radiation source: micro-focus sealed tube	1729 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.029
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.888, Tmax = 0.931	k = −13→13
8247 measured reflections	l = −9→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0954P)^2] where P = (Fo^2 + 2Fc^2)/3
2277 reflections	(Δ/σ)max = 0.012
163 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.84242 (6)	0.47328 (5)	0.12753 (5)	0.0501 (3)
F1	0.62909 (17)	0.63504 (13)	0.16615 (16)	0.0791 (5)
N1	0.9003 (2)	0.36623 (18)	0.05259 (19)	0.0672 (6)
N2	0.8633 (2)	0.3788 (2)	−0.1664 (2)	0.0768 (7)
C1	0.4123 (3)	0.3846 (4)	0.1554 (3)	0.0890 (11)
H1	0.3236	0.3667	0.1603	0.107*
C2	0.4537 (3)	0.5002 (3)	0.1658 (3)	0.0734 (8)
H2	0.3948	0.5602	0.1780	0.088*
C3	0.5851 (2)	0.5228 (2)	0.1575 (2)	0.0552 (6)
C4	0.6739 (2)	0.4351 (2)	0.14091 (19)	0.0472 (6)
C5	0.9219 (2)	0.4334 (2)	0.2749 (2)	0.0574 (6)
H5A	0.9126	0.3496	0.2865	0.069*
H5B	1.0160	0.4513	0.2812	0.069*
C6	0.8616 (2)	0.4984 (2)	0.3702 (2)	0.0503 (6)
C7	0.7683 (3)	0.4444 (2)	0.4306 (2)	0.0612 (7)
H7	0.7426	0.3674	0.4122	0.073*
C8	0.7129 (3)	0.5044 (3)	0.5183 (3)	0.0761 (8)
H8	0.6500	0.4680	0.5588	0.091*
C9	0.7513 (3)	0.6181 (3)	0.5455 (3)	0.0756 (9)
H9	0.7144	0.6584	0.6047	0.091*
C10	0.4990 (3)	0.2956 (3)	0.1381 (3)	0.0848 (9)
H10	0.4687	0.2185	0.1308	0.102*
C11	0.6298 (3)	0.3199 (2)	0.1317 (2)	0.0654 (7)
H11	0.6889	0.2595	0.1211	0.078*
C12	0.8778 (2)	0.3785 (2)	−0.0636 (3)	0.0554 (6)
C13	0.8433 (3)	0.6722 (3)	0.4860 (3)	0.0721 (8)
H13	0.8683	0.7492	0.5047	0.086*
C14	0.8993 (3)	0.6133 (2)	0.3986 (2)	0.0602 (7)
H14	0.9621	0.6504	0.3586	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0537 (4)	0.0479 (4)	0.0505 (4)	0.0051 (2)	0.0134 (3)	0.0037 (2)
F1	0.0796 (11)	0.0578 (9)	0.1008 (13)	0.0147 (8)	0.0155 (9)	−0.0114 (8)
N1	0.0849 (16)	0.0641 (14)	0.0557 (14)	0.0254 (11)	0.0215 (12)	0.0013 (10)
N2	0.0775 (17)	0.0924 (18)	0.0631 (16)	0.0049 (12)	0.0193 (13)	−0.0066 (13)
C1	0.0594 (18)	0.150 (4)	0.0571 (19)	−0.027 (2)	0.0064 (14)	0.0102 (19)
C2	0.0566 (16)	0.107 (2)	0.0565 (18)	0.0070 (16)	0.0083 (13)	−0.0036 (16)
C3	0.0555 (14)	0.0651 (16)	0.0446 (14)	0.0034 (12)	0.0049 (11)	−0.0010 (11)
C4	0.0505 (13)	0.0510 (13)	0.0398 (12)	−0.0004 (10)	0.0045 (10)	0.0013 (10)
C5	0.0529 (14)	0.0642 (15)	0.0546 (15)	0.0103 (12)	0.0052 (11)	0.0077 (12)
C6	0.0476 (13)	0.0587 (14)	0.0431 (13)	0.0058 (10)	−0.0001 (10)	0.0064 (10)
C7	0.0713 (17)	0.0555 (14)	0.0580 (16)	−0.0001 (12)	0.0129 (13)	0.0063 (12)
C8	0.086 (2)	0.080 (2)	0.0659 (19)	0.0063 (15)	0.0259 (16)	0.0125 (15)
C9	0.091 (2)	0.079 (2)	0.0560 (17)	0.0222 (16)	0.0099 (15)	−0.0044 (14)
C10	0.088 (2)	0.088 (2)	0.076 (2)	−0.0312 (18)	0.0032 (17)	0.0083 (17)
C11	0.0752 (18)	0.0571 (16)	0.0633 (16)	−0.0092 (13)	0.0067 (14)	0.0032 (13)
C12	0.0473 (14)	0.0576 (15)	0.0647 (18)	0.0002 (10)	0.0200 (12)	−0.0056 (12)
C13	0.0835 (19)	0.0591 (16)	0.0691 (18)	0.0042 (14)	−0.0070 (15)	−0.0094 (14)
C14	0.0546 (14)	0.0605 (16)	0.0625 (17)	−0.0048 (11)	−0.0036 (12)	0.0024 (12)

Geometric parameters (Å, º)

S1—N1	1.637 (2)	C5—H5B	0.9700
S1—C4	1.788 (2)	C6—C7	1.381 (3)
S1—C5	1.816 (2)	C6—C14	1.389 (3)
F1—C3	1.353 (3)	C7—C8	1.383 (4)
N1—C12	1.315 (4)	C7—H7	0.9300
N2—C12	1.155 (3)	C8—C9	1.375 (4)
C1—C10	1.373 (5)	C8—H8	0.9300
C1—C2	1.381 (4)	C9—C13	1.366 (4)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.373 (4)	C10—C11	1.366 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.374 (3)	C11—H11	0.9300
C4—C11	1.386 (3)	C13—C14	1.377 (4)
C5—C6	1.502 (3)	C13—H13	0.9300
C5—H5A	0.9700	C14—H14	0.9300
N1—S1—C4	105.87 (12)	C14—C6—C5	120.3 (2)
N1—S1—C5	98.30 (11)	C6—C7—C8	120.2 (3)
C4—S1—C5	100.20 (11)	C6—C7—H7	119.9
C12—N1—S1	114.37 (17)	C8—C7—H7	119.9
C10—C1—C2	121.4 (3)	C9—C8—C7	119.8 (3)
C10—C1—H1	119.3	C9—C8—H8	120.1
C2—C1—H1	119.3	C7—C8—H8	120.1
C3—C2—C1	117.4 (3)	C13—C9—C8	120.4 (3)
C3—C2—H2	121.3	C13—C9—H9	119.8
C1—C2—H2	121.3	C8—C9—H9	119.8
F1—C3—C2	119.1 (2)	C11—C10—C1	120.2 (3)
F1—C3—C4	118.7 (2)	C11—C10—H10	119.9
C2—C3—C4	122.1 (3)	C1—C10—H10	119.9
C3—C4—C11	119.2 (2)	C10—C11—C4	119.6 (3)
C3—C4—S1	119.03 (18)	C10—C11—H11	120.2
C11—C4—S1	121.76 (19)	C4—C11—H11	120.2
C6—C5—S1	111.38 (16)	N2—C12—N1	173.4 (3)
C6—C5—H5A	109.4	C9—C13—C14	120.4 (3)
S1—C5—H5A	109.4	C9—C13—H13	119.8
C6—C5—H5B	109.4	C14—C13—H13	119.8
S1—C5—H5B	109.4	C13—C14—C6	119.9 (3)
H5A—C5—H5B	108.0	C13—C14—H14	120.0
C7—C6—C14	119.3 (2)	C6—C14—H14	120.0
C7—C6—C5	120.3 (2)

(Compound_2_Run_2)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.32	Dx = 1.327 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4016 reflections
a = 10.1385 (11) Å	θ = 2.6–24.7°
b = 11.3898 (11) Å	µ = 0.24 mm^−1
c = 11.3325 (12) Å	T = 300 K
β = 97.467 (4)°	Block, colorless
V = 1297.5 (2) Å^3	0.39 × 0.34 × 0.15 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2291 independent reflections
Radiation source: micro-focus sealed tube	1818 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.041
ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.911, Tmax = 0.967	k = −13→13
12421 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0589P)^2 + 0.270P] where P = (Fo^2 + 2Fc^2)/3
2291 reflections	(Δ/σ)max = 0.015
163 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.84219 (5)	0.52676 (5)	0.12735 (5)	0.0491 (2)
F1	0.62902 (15)	0.36501 (12)	0.16636 (14)	0.0786 (4)
N1	0.8998 (2)	0.63377 (17)	0.05248 (17)	0.0666 (6)
N2	0.8630 (2)	0.6212 (2)	−0.1664 (2)	0.0765 (6)
C1	0.7513 (3)	0.3823 (3)	0.5455 (2)	0.0763 (8)
H1	0.7143	0.3420	0.6046	0.092*
C2	0.7133 (3)	0.4959 (3)	0.5183 (2)	0.0755 (8)
H2	0.6508	0.5325	0.5590	0.091*
C3	0.7682 (2)	0.5557 (2)	0.4305 (2)	0.0621 (6)
H3	0.7423	0.6326	0.4120	0.075*
C4	0.8617 (2)	0.50161 (19)	0.36974 (18)	0.0507 (5)
C5	0.9215 (2)	0.5668 (2)	0.27466 (19)	0.0562 (6)
H5A	1.0158	0.5493	0.2810	0.067*
H5B	0.9117	0.6506	0.2863	0.067*
C6	0.6735 (2)	0.56475 (19)	0.14085 (17)	0.0473 (5)
C7	0.6298 (3)	0.6799 (2)	0.1313 (2)	0.0662 (6)
H7	0.6889	0.7401	0.1204	0.079*
C8	0.4987 (3)	0.7043 (3)	0.1381 (2)	0.0848 (9)
H8	0.4685	0.7814	0.1311	0.102*
C9	0.4118 (3)	0.6152 (4)	0.1554 (2)	0.0883 (10)
H9	0.3231	0.6329	0.1602	0.106*
C10	0.8438 (3)	0.3280 (2)	0.4859 (2)	0.0715 (7)
H10	0.8691	0.2511	0.5047	0.086*
C11	0.8995 (2)	0.3871 (2)	0.3980 (2)	0.0595 (6)
H11	0.9622	0.3500	0.3578	0.071*
C12	0.5850 (2)	0.4772 (2)	0.15752 (19)	0.0553 (6)
C13	0.4537 (3)	0.5002 (3)	0.1656 (2)	0.0736 (8)
H13	0.3948	0.4400	0.1776	0.088*
C14	0.8776 (2)	0.62124 (19)	−0.0639 (2)	0.0548 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0526 (3)	0.0471 (3)	0.0493 (3)	−0.0051 (2)	0.0130 (2)	−0.0039 (2)
F1	0.0790 (10)	0.0574 (9)	0.1005 (11)	−0.0140 (7)	0.0152 (8)	0.0105 (7)
N1	0.0836 (14)	0.0618 (13)	0.0579 (12)	−0.0228 (10)	0.0226 (10)	−0.0010 (9)
N2	0.0774 (15)	0.0917 (17)	0.0629 (14)	−0.0045 (12)	0.0181 (11)	0.0077 (11)
C1	0.091 (2)	0.083 (2)	0.0555 (15)	−0.0254 (16)	0.0095 (14)	0.0051 (13)
C2	0.0847 (19)	0.082 (2)	0.0645 (16)	−0.0080 (15)	0.0269 (14)	−0.0127 (14)
C3	0.0718 (15)	0.0562 (14)	0.0593 (14)	−0.0007 (11)	0.0124 (12)	−0.0085 (11)
C4	0.0486 (12)	0.0569 (13)	0.0445 (11)	−0.0055 (10)	−0.0016 (9)	−0.0061 (9)
C5	0.0518 (12)	0.0617 (14)	0.0543 (13)	−0.0103 (10)	0.0039 (10)	−0.0079 (10)
C6	0.0513 (12)	0.0513 (12)	0.0389 (10)	0.0008 (10)	0.0041 (9)	−0.0035 (9)
C7	0.0742 (16)	0.0594 (15)	0.0647 (15)	0.0086 (12)	0.0078 (12)	−0.0039 (12)
C8	0.087 (2)	0.089 (2)	0.0768 (19)	0.0331 (18)	0.0026 (15)	−0.0088 (15)
C9	0.0580 (16)	0.146 (3)	0.0599 (16)	0.0269 (19)	0.0051 (13)	−0.0107 (17)
C10	0.0814 (18)	0.0603 (15)	0.0682 (16)	−0.0036 (13)	−0.0080 (14)	0.0090 (13)
C11	0.0535 (13)	0.0615 (15)	0.0606 (14)	0.0041 (11)	−0.0036 (11)	−0.0029 (11)
C12	0.0547 (13)	0.0659 (15)	0.0447 (11)	−0.0038 (11)	0.0040 (10)	0.0010 (10)
C13	0.0542 (14)	0.111 (2)	0.0557 (15)	−0.0087 (15)	0.0060 (11)	0.0014 (14)
C14	0.0465 (12)	0.0570 (14)	0.0643 (15)	0.0003 (10)	0.0203 (11)	0.0058 (11)

Geometric parameters (Å, º)

S1—N1	1.6356 (19)	C5—H5A	0.9700
S1—C6	1.789 (2)	C5—H5B	0.9700
S1—C5	1.815 (2)	C6—C12	1.372 (3)
F1—C12	1.353 (3)	C6—C7	1.384 (3)
N1—C14	1.316 (3)	C7—C8	1.370 (4)
N2—C14	1.152 (3)	C7—H7	0.9300
C1—C10	1.372 (4)	C8—C9	1.375 (4)
C1—C2	1.374 (4)	C8—H8	0.9300
C1—H1	0.9300	C9—C13	1.378 (4)
C2—C3	1.381 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.382 (3)
C3—C4	1.387 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C11	1.385 (3)	C12—C13	1.371 (4)
C4—C5	1.500 (3)	C13—H13	0.9300
N1—S1—C6	105.89 (11)	C7—C6—S1	121.50 (18)
N1—S1—C5	98.31 (10)	C8—C7—C6	119.4 (3)
C6—S1—C5	100.06 (10)	C8—C7—H7	120.3
C14—N1—S1	114.38 (16)	C6—C7—H7	120.3
C10—C1—C2	120.2 (2)	C7—C8—C9	120.2 (3)
C10—C1—H1	119.9	C7—C8—H8	119.9
C2—C1—H1	119.9	C9—C8—H8	119.9
C1—C2—C3	119.9 (3)	C8—C9—C13	121.2 (3)
C1—C2—H2	120.0	C8—C9—H9	119.4
C3—C2—H2	120.0	C13—C9—H9	119.4
C2—C3—C4	120.3 (2)	C1—C10—C11	120.3 (2)
C2—C3—H3	119.9	C1—C10—H10	119.8
C4—C3—H3	119.9	C11—C10—H10	119.8
C11—C4—C3	119.4 (2)	C10—C11—C4	119.9 (2)
C11—C4—C5	120.4 (2)	C10—C11—H11	120.1
C3—C4—C5	120.2 (2)	C4—C11—H11	120.0
C4—C5—S1	111.37 (15)	F1—C12—C13	119.3 (2)
C4—C5—H5A	109.4	F1—C12—C6	118.8 (2)
S1—C5—H5A	109.4	C13—C12—C6	121.9 (2)
C4—C5—H5B	109.4	C12—C13—C9	117.9 (3)
S1—C5—H5B	109.4	C12—C13—H13	121.1
H5A—C5—H5B	108.0	C9—C13—H13	121.1
C12—C6—C7	119.4 (2)	N2—C14—N1	173.3 (3)
C12—C6—S1	119.06 (17)

(Compound_2_Run_3)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.31	Dx = 1.322 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2278 reflections
a = 10.1375 (11) Å	θ = 2.6–22.7°
b = 11.3871 (14) Å	µ = 0.24 mm^−1
c = 11.3412 (14) Å	T = 300 K
β = 97.482 (4)°	Block, colorless
V = 1298.0 (3) Å^3	0.27 × 0.21 × 0.14 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2275 independent reflections
Radiation source: micro-focus sealed tube	1692 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.043
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −11→12
Tmin = 0.888, Tmax = 0.988	k = −13→13
8248 measured reflections	l = −13→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.1168P] where P = (Fo^2 + 2Fc^2)/3
2275 reflections	(Δ/σ)max = 0.008
163 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34243 (6)	0.02671 (5)	0.12747 (5)	0.0493 (2)
F1	0.12900 (15)	−0.13483 (13)	0.16612 (15)	0.0781 (5)
N1	0.4002 (2)	0.13378 (19)	0.05241 (19)	0.0665 (6)
N2	0.3629 (2)	0.1214 (2)	−0.1664 (2)	0.0760 (7)
C1	0.2510 (3)	−0.1177 (3)	0.5455 (2)	0.0748 (8)
H1	0.2138	−0.1579	0.6044	0.090*
C2	0.3433 (3)	−0.1720 (3)	0.4858 (3)	0.0711 (8)
H2	0.3685	−0.2491	0.5044	0.085*
C3	0.3991 (2)	−0.1129 (2)	0.3983 (2)	0.0606 (7)
H3	0.4618	−0.1501	0.3584	0.073*
C4	0.3618 (2)	0.0016 (2)	0.3699 (2)	0.0501 (6)
C5	0.4216 (2)	0.0667 (2)	0.2746 (2)	0.0557 (6)
H5A	0.5159	0.0491	0.2810	0.067*
H5B	0.4120	0.1505	0.2861	0.067*
C6	0.1739 (2)	0.0651 (2)	0.14121 (19)	0.0466 (5)
C7	0.1303 (3)	0.1801 (2)	0.1314 (2)	0.0657 (7)
H7	0.1893	0.2404	0.1201	0.079*
C8	−0.0010 (3)	0.2043 (3)	0.1384 (3)	0.0836 (9)
H8	−0.0313	0.2814	0.1316	0.100*
C9	−0.0877 (3)	0.1156 (4)	0.1554 (3)	0.0874 (11)
H9	−0.1764	0.1336	0.1602	0.105*
C10	0.2683 (3)	0.0559 (2)	0.4306 (2)	0.0613 (7)
H10	0.2424	0.1328	0.4121	0.074*
C11	0.2135 (3)	−0.0039 (3)	0.5182 (3)	0.0746 (8)
H11	0.1510	0.0329	0.5588	0.089*
C12	0.0848 (2)	−0.0227 (2)	0.1578 (2)	0.0537 (6)
C13	−0.0462 (3)	−0.0002 (3)	0.1656 (2)	0.0737 (8)
H13	−0.1052	−0.0603	0.1773	0.088*
C14	0.3779 (2)	0.1213 (2)	−0.0639 (3)	0.0545 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0526 (4)	0.0466 (4)	0.0501 (4)	−0.0050 (2)	0.0125 (3)	−0.0040 (3)
F1	0.0777 (10)	0.0580 (10)	0.0994 (13)	−0.0148 (8)	0.0152 (9)	0.0102 (8)
N1	0.0840 (16)	0.0634 (14)	0.0554 (14)	−0.0225 (11)	0.0210 (12)	0.0001 (10)
N2	0.0764 (16)	0.0905 (19)	0.0628 (16)	−0.0038 (12)	0.0161 (13)	0.0082 (13)
C1	0.088 (2)	0.080 (2)	0.0567 (17)	−0.0242 (16)	0.0098 (15)	0.0050 (15)
C2	0.0806 (19)	0.0599 (17)	0.0676 (18)	−0.0027 (14)	−0.0096 (15)	0.0092 (14)
C3	0.0546 (14)	0.0630 (17)	0.0612 (16)	0.0049 (11)	−0.0036 (12)	−0.0018 (13)
C4	0.0461 (13)	0.0571 (15)	0.0449 (13)	−0.0052 (10)	−0.0019 (10)	−0.0061 (11)
C5	0.0512 (13)	0.0590 (15)	0.0561 (15)	−0.0084 (11)	0.0042 (11)	−0.0075 (12)
C6	0.0511 (13)	0.0502 (14)	0.0382 (12)	0.0003 (10)	0.0046 (10)	−0.0033 (10)
C7	0.0738 (18)	0.0575 (17)	0.0657 (17)	0.0090 (13)	0.0080 (14)	−0.0033 (13)
C8	0.086 (2)	0.085 (2)	0.078 (2)	0.0321 (18)	0.0053 (17)	−0.0072 (17)
C9	0.0578 (17)	0.146 (4)	0.0578 (18)	0.027 (2)	0.0055 (14)	−0.009 (2)
C10	0.0707 (17)	0.0549 (16)	0.0588 (16)	−0.0010 (12)	0.0103 (13)	−0.0067 (12)
C11	0.083 (2)	0.080 (2)	0.0642 (18)	−0.0082 (15)	0.0242 (16)	−0.0124 (15)
C12	0.0545 (14)	0.0613 (16)	0.0444 (13)	−0.0026 (12)	0.0030 (11)	0.0013 (11)
C13	0.0539 (16)	0.110 (3)	0.0570 (17)	−0.0101 (16)	0.0053 (13)	0.0026 (16)
C14	0.0445 (13)	0.0574 (16)	0.0640 (18)	0.0000 (10)	0.0165 (12)	0.0074 (13)

Geometric parameters (Å, º)

S1—N1	1.638 (2)	C5—H5A	0.9700
S1—C6	1.790 (2)	C5—H5B	0.9700
S1—C5	1.813 (2)	C6—C12	1.376 (3)
F1—C12	1.353 (3)	C6—C7	1.382 (3)
N1—C14	1.317 (3)	C7—C8	1.371 (4)
N2—C14	1.152 (3)	C7—H7	0.9300
C1—C2	1.371 (4)	C8—C9	1.369 (5)
C1—C11	1.375 (4)	C8—H8	0.9300
C1—H1	0.9300	C9—C13	1.384 (4)
C2—C3	1.379 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.379 (4)
C3—C4	1.384 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C10	1.387 (3)	C12—C13	1.367 (4)
C4—C5	1.502 (3)	C13—H13	0.9300
N1—S1—C6	105.85 (12)	C7—C6—S1	121.57 (19)
N1—S1—C5	98.39 (11)	C8—C7—C6	119.2 (3)
C6—S1—C5	99.90 (11)	C8—C7—H7	120.4
C14—N1—S1	114.45 (17)	C6—C7—H7	120.4
C2—C1—C11	120.0 (3)	C9—C8—C7	120.4 (3)
C2—C1—H1	120.0	C9—C8—H8	119.8
C11—C1—H1	120.0	C7—C8—H8	119.8
C1—C2—C3	120.3 (3)	C8—C9—C13	121.4 (3)
C1—C2—H2	119.9	C8—C9—H9	119.3
C3—C2—H2	119.9	C13—C9—H9	119.3
C2—C3—C4	120.2 (3)	C11—C10—C4	120.2 (3)
C2—C3—H3	119.9	C11—C10—H10	119.9
C4—C3—H3	119.9	C4—C10—H10	119.9
C3—C4—C10	119.2 (2)	C1—C11—C10	120.1 (3)
C3—C4—C5	120.6 (2)	C1—C11—H11	119.9
C10—C4—C5	120.2 (2)	C10—C11—H11	119.9
C4—C5—S1	111.51 (16)	F1—C12—C13	119.2 (2)
C4—C5—H5A	109.3	F1—C12—C6	118.6 (2)
S1—C5—H5A	109.3	C13—C12—C6	122.2 (3)
C4—C5—H5B	109.3	C12—C13—C9	117.4 (3)
S1—C5—H5B	109.3	C12—C13—H13	121.3
H5A—C5—H5B	108.0	C9—C13—H13	121.3
C12—C6—C7	119.4 (2)	N2—C14—N1	173.3 (3)
C12—C6—S1	119.00 (18)

(Compound_2_Run_4)

Crystal data

C14H11FN2S	F(000) = 536
Mr = 258.31	Dx = 1.318 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2021 reflections
a = 10.137 (3) Å	θ = 2.5–22.4°
b = 11.413 (4) Å	µ = 0.24 mm^−1
c = 11.345 (3) Å	T = 300 K
β = 97.465 (11)°	Block, colorless
V = 1301.5 (7) Å^3	0.23 × 0.20 × 0.13 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2277 independent reflections
Radiation source: micro-focus sealed tube	1626 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.043
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→11
Tmin = 0.793, Tmax = 0.888	k = −11→13
8133 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.1803P] where P = (Fo^2 + 2Fc^2)/3
2277 reflections	(Δ/σ)max = 0.016
163 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.84217 (6)	0.47329 (6)	0.12755 (6)	0.0501 (2)
F1	0.62881 (17)	0.63496 (16)	0.16605 (16)	0.0786 (5)
N1	0.8999 (2)	0.3662 (2)	0.0527 (2)	0.0667 (7)
N2	0.8629 (3)	0.3789 (3)	−0.1664 (2)	0.0767 (8)
C1	0.4122 (4)	0.3848 (5)	0.1552 (3)	0.0890 (12)
H1	0.3233	0.3673	0.1596	0.107*
C2	0.4545 (3)	0.5003 (3)	0.1657 (3)	0.0741 (9)
H2	0.3958	0.5604	0.1779	0.089*
C3	0.5852 (3)	0.5227 (3)	0.1576 (2)	0.0548 (7)
C4	0.6739 (2)	0.4349 (2)	0.1410 (2)	0.0471 (6)
C5	0.9213 (3)	0.4330 (3)	0.2747 (2)	0.0570 (7)
H5A	0.9113	0.3494	0.2863	0.068*
H5B	1.0157	0.4503	0.2811	0.068*
C6	0.8615 (2)	0.4983 (2)	0.3700 (2)	0.0506 (7)
C7	0.7679 (3)	0.4444 (3)	0.4306 (2)	0.0612 (8)
H7	0.7418	0.3677	0.4121	0.073*
C8	0.7131 (3)	0.5043 (3)	0.5184 (3)	0.0757 (9)
H8	0.6508	0.4677	0.5593	0.091*
C9	0.7508 (3)	0.6176 (3)	0.5452 (3)	0.0739 (9)
H9	0.7133	0.6578	0.6040	0.089*
C10	0.4986 (4)	0.2960 (4)	0.1385 (3)	0.0851 (11)
H10	0.4681	0.2192	0.1317	0.102*
C11	0.6294 (3)	0.3198 (3)	0.1316 (2)	0.0671 (8)
H11	0.6882	0.2593	0.1208	0.081*
C12	0.8775 (2)	0.3789 (2)	−0.0639 (3)	0.0546 (7)
C13	0.8433 (3)	0.6721 (3)	0.4860 (3)	0.0717 (9)
H13	0.8686	0.7488	0.5048	0.086*
C14	0.8988 (3)	0.6127 (3)	0.3982 (2)	0.0614 (8)
H14	0.9614	0.6498	0.3581	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0528 (4)	0.0488 (4)	0.0505 (4)	0.0047 (3)	0.0137 (3)	0.0033 (3)
F1	0.0767 (12)	0.0601 (12)	0.0998 (13)	0.0142 (9)	0.0143 (10)	−0.0101 (9)
N1	0.0828 (17)	0.0627 (17)	0.0583 (15)	0.0237 (13)	0.0232 (13)	0.0014 (12)
N2	0.0778 (18)	0.092 (2)	0.0632 (17)	0.0038 (14)	0.0192 (14)	−0.0083 (14)
C1	0.057 (2)	0.150 (4)	0.059 (2)	−0.029 (2)	0.0065 (15)	0.009 (2)
C2	0.0543 (18)	0.112 (3)	0.0557 (18)	0.0111 (18)	0.0065 (14)	−0.0029 (18)
C3	0.0532 (16)	0.065 (2)	0.0451 (15)	0.0012 (14)	0.0038 (12)	−0.0002 (13)
C4	0.0512 (15)	0.0522 (17)	0.0376 (13)	0.0006 (12)	0.0047 (11)	0.0014 (11)
C5	0.0519 (16)	0.0625 (18)	0.0558 (16)	0.0101 (13)	0.0044 (13)	0.0069 (13)
C6	0.0479 (14)	0.0587 (19)	0.0434 (14)	0.0060 (12)	−0.0006 (11)	0.0075 (12)
C7	0.0689 (18)	0.0573 (19)	0.0579 (17)	−0.0011 (14)	0.0108 (15)	0.0083 (14)
C8	0.088 (2)	0.081 (3)	0.064 (2)	0.0081 (18)	0.0294 (17)	0.0126 (17)
C9	0.087 (2)	0.080 (3)	0.0556 (18)	0.0230 (19)	0.0099 (16)	−0.0034 (16)
C10	0.081 (2)	0.094 (3)	0.078 (2)	−0.034 (2)	0.0038 (19)	0.007 (2)
C11	0.077 (2)	0.059 (2)	0.0656 (19)	−0.0083 (15)	0.0077 (15)	0.0035 (15)
C12	0.0453 (15)	0.0572 (18)	0.0652 (19)	−0.0004 (12)	0.0218 (14)	−0.0057 (14)
C13	0.081 (2)	0.061 (2)	0.068 (2)	0.0034 (16)	−0.0088 (17)	−0.0099 (16)
C14	0.0550 (16)	0.066 (2)	0.0607 (18)	−0.0048 (14)	−0.0022 (14)	0.0030 (15)

Geometric parameters (Å, º)

S1—N1	1.639 (2)	C5—H5B	0.9700
S1—C4	1.787 (3)	C6—C14	1.385 (4)
S1—C5	1.815 (3)	C6—C7	1.386 (4)
F1—C3	1.355 (3)	C7—C8	1.383 (4)
N1—C12	1.320 (4)	C7—H7	0.9300
N2—C12	1.153 (3)	C8—C9	1.372 (5)
C1—C10	1.369 (5)	C8—H8	0.9300
C1—C2	1.387 (5)	C9—C13	1.371 (4)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.364 (4)	C10—C11	1.365 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.376 (4)	C11—H11	0.9300
C4—C11	1.389 (4)	C13—C14	1.383 (4)
C5—C6	1.504 (4)	C13—H13	0.9300
C5—H5A	0.9700	C14—H14	0.9300
N1—S1—C4	105.67 (13)	C7—C6—C5	120.1 (3)
N1—S1—C5	98.21 (13)	C8—C7—C6	120.2 (3)
C4—S1—C5	99.92 (12)	C8—C7—H7	119.9
C12—N1—S1	114.27 (19)	C6—C7—H7	119.9
C10—C1—C2	121.3 (3)	C9—C8—C7	120.0 (3)
C10—C1—H1	119.4	C9—C8—H8	120.0
C2—C1—H1	119.4	C7—C8—H8	120.0
C3—C2—C1	117.7 (3)	C13—C9—C8	120.5 (3)
C3—C2—H2	121.2	C13—C9—H9	119.8
C1—C2—H2	121.2	C8—C9—H9	119.8
F1—C3—C2	118.9 (3)	C11—C10—C1	120.3 (3)
F1—C3—C4	119.1 (2)	C11—C10—H10	119.8
C2—C3—C4	122.0 (3)	C1—C10—H10	119.8
C3—C4—C11	119.2 (3)	C10—C11—C4	119.5 (3)
C3—C4—S1	118.7 (2)	C10—C11—H11	120.3
C11—C4—S1	122.0 (2)	C4—C11—H11	120.3
C6—C5—S1	111.34 (18)	N2—C12—N1	173.3 (3)
C6—C5—H5A	109.4	C9—C13—C14	119.9 (3)
S1—C5—H5A	109.4	C9—C13—H13	120.0
C6—C5—H5B	109.4	C14—C13—H13	120.0
S1—C5—H5B	109.4	C13—C14—C6	120.2 (3)
H5A—C5—H5B	108.0	C13—C14—H14	119.9
C14—C6—C7	119.2 (3)	C6—C14—H14	119.9
C14—C6—C5	120.7 (2)

(Compound_3_CCDC)

Crystal data

C17H20Cl2N2Pd	F(000) = 864
Mr = 429.65	Dx = 1.587 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8388 reflections
a = 9.356 (2) Å	θ = 2.9–25.2°
b = 9.9295 (19) Å	µ = 1.33 mm^−1
c = 19.357 (4) Å	T = 300 K
β = 90.470 (7)°	Plate, orange
V = 1798.2 (7) Å^3	0.35 × 0.31 × 0.29 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	3229 independent reflections
Radiation source: micro-focus sealed tube	2821 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.066
ω scans	θmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −11→11
Tmin = 0.654, Tmax = 0.700	k = −11→11
16537 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0717P)^2] where P = (Fo^2 + 2Fc^2)/3
3229 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −1.67 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.34165 (3)	0.36794 (3)	0.474015 (13)	0.03696 (15)
Cl2	0.33207 (12)	0.48746 (11)	0.37305 (5)	0.0569 (3)
Cl3	0.39048 (14)	0.17596 (12)	0.41288 (6)	0.0700 (3)
N17	0.2901 (3)	0.5254 (3)	0.53575 (14)	0.0362 (6)
N4	0.3513 (3)	0.2777 (3)	0.56776 (16)	0.0421 (7)
C18	0.2724 (4)	0.6643 (4)	0.5106 (2)	0.0445 (8)
H18A	0.3438	0.6818	0.4757	0.053*
H18B	0.2899	0.7259	0.5487	0.053*
C19	0.1262 (4)	0.6928 (4)	0.4804 (2)	0.0547 (10)
H19A	0.0552	0.6929	0.5166	0.066*
H19B	0.1006	0.6238	0.4470	0.066*
C20	0.1306 (5)	0.8321 (5)	0.4448 (3)	0.0648 (12)
H20A	0.1659	0.8983	0.4776	0.078*
H20B	0.1973	0.8284	0.4067	0.078*
C21	−0.0122 (6)	0.8767 (5)	0.4179 (3)	0.0791 (16)
H21A	−0.0780	0.8855	0.4561	0.095*
H21B	−0.0499	0.8090	0.3865	0.095*
C22	−0.0016 (8)	1.0109 (6)	0.3802 (4)	0.108 (2)
H22A	0.0232	1.0805	0.4125	0.162*
H22B	−0.0919	1.0316	0.3588	0.162*
H22C	0.0707	1.0051	0.3454	0.162*
C10	0.2750 (3)	0.4970 (3)	0.59983 (18)	0.0370 (7)
C11	0.2242 (4)	0.5924 (4)	0.65287 (18)	0.0410 (8)
C12	0.0778 (5)	0.6088 (4)	0.6635 (2)	0.0566 (10)
H12	0.0124	0.5602	0.6370	0.068*
C13	0.0306 (6)	0.6968 (5)	0.7130 (3)	0.0755 (14)
H13	−0.0670	0.7070	0.7199	0.091*
C14	0.1242 (6)	0.7695 (5)	0.7521 (3)	0.0753 (14)
H14	0.0903	0.8286	0.7854	0.090*
C15	0.2709 (6)	0.7557 (5)	0.7423 (2)	0.0743 (14)
H15	0.3350	0.8053	0.7690	0.089*
C16	0.3202 (5)	0.6677 (5)	0.6927 (2)	0.0594 (11)
H16	0.4180	0.6586	0.6858	0.071*
C9	0.3110 (4)	0.3580 (3)	0.6206 (2)	0.0383 (8)
C5	0.3924 (5)	0.1505 (4)	0.5816 (3)	0.0610 (12)
H5	0.4218	0.0951	0.5457	0.073*
C6	0.3918 (5)	0.1009 (5)	0.6483 (3)	0.0715 (14)
H6	0.4198	0.0125	0.6567	0.086*
C7	0.3506 (5)	0.1803 (5)	0.7016 (2)	0.0628 (12)
H7	0.3498	0.1470	0.7465	0.075*
C8	0.3093 (4)	0.3130 (5)	0.6877 (2)	0.0502 (9)
H8	0.2811	0.3698	0.7233	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0400 (2)	0.0360 (2)	0.0348 (2)	0.00346 (10)	−0.00390 (13)	−0.00320 (10)
Cl2	0.0755 (7)	0.0628 (7)	0.0324 (5)	0.0177 (5)	−0.0037 (4)	0.0013 (4)
Cl3	0.0954 (9)	0.0484 (6)	0.0663 (7)	0.0069 (6)	0.0090 (6)	−0.0190 (6)
N17	0.0376 (14)	0.0362 (16)	0.0345 (15)	0.0036 (12)	−0.0098 (11)	0.0013 (12)
N4	0.0440 (16)	0.0375 (17)	0.0448 (17)	0.0043 (13)	−0.0014 (13)	0.0046 (14)
C18	0.060 (2)	0.0362 (19)	0.038 (2)	0.0050 (17)	−0.0083 (16)	−0.0022 (16)
C19	0.056 (2)	0.050 (2)	0.058 (2)	0.0135 (19)	−0.0080 (18)	0.003 (2)
C20	0.068 (3)	0.057 (3)	0.069 (3)	0.009 (2)	−0.018 (2)	0.001 (2)
C21	0.080 (4)	0.068 (4)	0.088 (4)	0.013 (2)	−0.027 (3)	0.000 (3)
C22	0.137 (5)	0.067 (4)	0.120 (6)	0.013 (3)	−0.052 (4)	0.020 (4)
C10	0.0349 (16)	0.0371 (19)	0.0390 (18)	0.0013 (14)	−0.0088 (13)	−0.0024 (15)
C11	0.048 (2)	0.0408 (19)	0.0343 (18)	0.0037 (16)	−0.0036 (15)	−0.0007 (16)
C12	0.051 (2)	0.059 (3)	0.060 (3)	−0.0023 (19)	0.0044 (19)	−0.007 (2)
C13	0.073 (3)	0.072 (3)	0.081 (3)	0.015 (3)	0.028 (3)	−0.011 (3)
C14	0.108 (4)	0.064 (3)	0.054 (3)	0.023 (3)	0.018 (3)	−0.014 (2)
C15	0.099 (4)	0.070 (3)	0.054 (3)	0.002 (3)	−0.008 (3)	−0.022 (2)
C16	0.055 (2)	0.073 (3)	0.050 (2)	0.004 (2)	−0.0096 (18)	−0.018 (2)
C9	0.0337 (17)	0.041 (2)	0.040 (2)	0.0000 (13)	−0.0046 (14)	0.0039 (14)
C5	0.069 (3)	0.046 (2)	0.069 (3)	0.020 (2)	0.012 (2)	0.013 (2)
C6	0.075 (3)	0.058 (3)	0.081 (4)	0.023 (2)	0.009 (3)	0.031 (3)
C7	0.062 (3)	0.071 (3)	0.055 (3)	0.008 (2)	−0.001 (2)	0.030 (3)
C8	0.045 (2)	0.064 (3)	0.042 (2)	0.0034 (19)	−0.0027 (15)	0.011 (2)

Geometric parameters (Å, º)

Pd1—N4	2.025 (3)	C22—H22C	0.9600
Pd1—N17	2.028 (3)	C10—C9	1.476 (5)
Pd1—Cl2	2.2875 (10)	C10—C11	1.478 (5)
Pd1—Cl3	2.2917 (11)	C11—C12	1.396 (5)
N17—C10	1.281 (5)	C11—C16	1.397 (6)
N17—C18	1.471 (5)	C12—C13	1.372 (6)
N4—C5	1.347 (5)	C12—H12	0.9300
N4—C9	1.353 (5)	C13—C14	1.360 (8)
C18—C19	1.511 (5)	C13—H13	0.9300
C18—H18A	0.9700	C14—C15	1.393 (7)
C18—H18B	0.9700	C14—H14	0.9300
C19—C20	1.546 (6)	C15—C16	1.380 (6)
C19—H19A	0.9700	C15—H15	0.9300
C19—H19B	0.9700	C16—H16	0.9300
C20—C21	1.498 (7)	C9—C8	1.373 (5)
C20—H20A	0.9700	C5—C6	1.381 (7)
C20—H20B	0.9700	C5—H5	0.9300
C21—C22	1.523 (8)	C6—C7	1.357 (7)
C21—H21A	0.9700	C6—H6	0.9300
C21—H21B	0.9700	C7—C8	1.399 (6)
C22—H22A	0.9600	C7—H7	0.9300
C22—H22B	0.9600	C8—H8	0.9300
N4—Pd1—N17	79.75 (11)	C21—C22—H22C	109.5
N4—Pd1—Cl2	175.01 (9)	H22A—C22—H22C	109.5
N17—Pd1—Cl2	95.49 (8)	H22B—C22—H22C	109.5
N4—Pd1—Cl3	94.99 (9)	N17—C10—C9	116.3 (3)
N17—Pd1—Cl3	174.12 (8)	N17—C10—C11	124.8 (3)
Cl2—Pd1—Cl3	89.83 (4)	C9—C10—C11	118.9 (3)
C10—N17—C18	120.9 (3)	C12—C11—C16	118.9 (4)
C10—N17—Pd1	115.4 (2)	C12—C11—C10	119.9 (3)
C18—N17—Pd1	123.7 (2)	C16—C11—C10	121.2 (3)
C5—N4—C9	118.9 (3)	C13—C12—C11	119.9 (4)
C5—N4—Pd1	127.1 (3)	C13—C12—H12	120.0
C9—N4—Pd1	114.0 (2)	C11—C12—H12	120.0
N17—C18—C19	113.8 (3)	C14—C13—C12	121.2 (5)
N17—C18—H18A	108.8	C14—C13—H13	119.4
C19—C18—H18A	108.8	C12—C13—H13	119.4
N17—C18—H18B	108.8	C13—C14—C15	120.1 (4)
C19—C18—H18B	108.8	C13—C14—H14	119.9
H18A—C18—H18B	107.7	C15—C14—H14	119.9
C18—C19—C20	108.2 (3)	C16—C15—C14	119.5 (4)
C18—C19—H19A	110.1	C16—C15—H15	120.3
C20—C19—H19A	110.1	C14—C15—H15	120.3
C18—C19—H19B	110.1	C15—C16—C11	120.4 (4)
C20—C19—H19B	110.1	C15—C16—H16	119.8
H19A—C19—H19B	108.4	C11—C16—H16	119.8
C21—C20—C19	113.1 (4)	N4—C9—C8	121.9 (3)
C21—C20—H20A	109.0	N4—C9—C10	114.1 (3)
C19—C20—H20A	109.0	C8—C9—C10	123.9 (3)
C21—C20—H20B	109.0	N4—C5—C6	121.1 (4)
C19—C20—H20B	109.0	N4—C5—H5	119.4
H20A—C20—H20B	107.8	C6—C5—H5	119.4
C20—C21—C22	111.4 (5)	C7—C6—C5	120.5 (4)
C20—C21—H21A	109.4	C7—C6—H6	119.8
C22—C21—H21A	109.4	C5—C6—H6	119.8
C20—C21—H21B	109.4	C6—C7—C8	118.7 (4)
C22—C21—H21B	109.4	C6—C7—H7	120.6
H21A—C21—H21B	108.0	C8—C7—H7	120.6
C21—C22—H22A	109.5	C9—C8—C7	118.9 (4)
C21—C22—H22B	109.5	C9—C8—H8	120.6
H22A—C22—H22B	109.5	C7—C8—H8	120.6

(Compound_3_X2S)

Crystal data

C17H20Cl2N2Pd	F(000) = 864
Mr = 429.65	Dx = 1.587 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8388 reflections
a = 9.356 (2) Å	θ = 2.9–25.2°
b = 9.9295 (19) Å	µ = 1.33 mm^−1
c = 19.357 (4) Å	T = 300 K
β = 90.470 (7)°	Plate, orange
V = 1798.2 (7) Å^3	0.35 × 0.31 × 0.29 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	3229 independent reflections
Radiation source: micro-focus sealed tube	2821 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.066
ω scans	θmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −11→11
Tmin = 0.220, Tmax = 0.700	k = −11→11
16537 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0723P)^2 + 0.1997P] where P = (Fo^2 + 2Fc^2)/3
3229 reflections	(Δ/σ)max = 0.011
200 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −1.66 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.34165 (3)	0.36794 (3)	0.474015 (13)	0.03692 (15)
Cl1	0.33208 (12)	0.48747 (11)	0.37305 (5)	0.0569 (3)
Cl2	0.39048 (14)	0.17595 (12)	0.41289 (7)	0.0699 (3)
N1	0.3512 (3)	0.2777 (3)	0.56775 (16)	0.0421 (7)
N2	0.2902 (3)	0.5254 (3)	0.53575 (14)	0.0362 (6)
C1	0.3923 (5)	0.1504 (4)	0.5816 (3)	0.0610 (12)
H1	0.4214	0.0950	0.5456	0.073*
C2	0.3918 (6)	0.1009 (5)	0.6483 (3)	0.0713 (14)
H2	0.4200	0.0126	0.6567	0.086*
C3	0.3506 (5)	0.1803 (5)	0.7016 (2)	0.0627 (12)
H3	0.3499	0.1471	0.7465	0.075*
C4	0.3092 (4)	0.3129 (5)	0.6877 (2)	0.0502 (9)
H4	0.2809	0.3697	0.7233	0.060*
C5	0.3110 (4)	0.3580 (3)	0.6206 (2)	0.0384 (8)
C6	0.2750 (3)	0.4970 (3)	0.59986 (18)	0.0371 (7)
C7	0.2723 (4)	0.6643 (4)	0.5106 (2)	0.0444 (8)
H7A	0.3437	0.6819	0.4757	0.053*
H7B	0.2897	0.7259	0.5487	0.053*
C8	0.1262 (4)	0.6928 (4)	0.4804 (2)	0.0546 (10)
H8A	0.0552	0.6929	0.5166	0.066*
H8B	0.1007	0.6238	0.4470	0.066*
C9	0.1307 (5)	0.8321 (5)	0.4448 (3)	0.0647 (12)
H9A	0.1660	0.8983	0.4775	0.078*
H9B	0.1973	0.8284	0.4067	0.078*
C10	−0.0122 (7)	0.8767 (5)	0.4179 (4)	0.0789 (16)
H10A	−0.0779	0.8855	0.4561	0.095*
H10B	−0.0500	0.8090	0.3866	0.095*
C11	−0.0016 (8)	1.0109 (6)	0.3802 (4)	0.108 (2)
H11A	0.0236	1.0804	0.4125	0.162*
H11B	−0.0921	1.0318	0.3590	0.162*
H11C	0.0703	1.0050	0.3452	0.162*
C12	0.2242 (4)	0.5925 (4)	0.65285 (18)	0.0410 (8)
C13	0.0778 (5)	0.6087 (4)	0.6635 (3)	0.0566 (11)
H13	0.0124	0.5600	0.6371	0.068*
C14	0.0307 (6)	0.6968 (6)	0.7130 (3)	0.0757 (15)
H14	−0.0670	0.7071	0.7199	0.091*
C15	0.1245 (6)	0.7695 (5)	0.7522 (3)	0.0753 (15)
H15	0.0906	0.8284	0.7856	0.090*
C16	0.2708 (6)	0.7556 (5)	0.7423 (3)	0.0741 (14)
H16	0.3349	0.8053	0.7690	0.089*
C17	0.3202 (5)	0.6678 (5)	0.6928 (2)	0.0594 (11)
H17	0.4180	0.6586	0.6859	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0399 (2)	0.0360 (2)	0.0348 (2)	0.00347 (10)	−0.00391 (13)	−0.00320 (10)
Cl1	0.0754 (7)	0.0628 (7)	0.0324 (5)	0.0177 (5)	−0.0037 (4)	0.0013 (4)
Cl2	0.0953 (9)	0.0484 (6)	0.0663 (7)	0.0068 (6)	0.0090 (6)	−0.0190 (6)
N1	0.0440 (16)	0.0373 (17)	0.0449 (17)	0.0043 (13)	−0.0014 (13)	0.0046 (14)
N2	0.0374 (14)	0.0363 (16)	0.0346 (15)	0.0036 (12)	−0.0098 (11)	0.0014 (12)
C1	0.069 (3)	0.045 (2)	0.069 (3)	0.020 (2)	0.012 (2)	0.013 (2)
C2	0.076 (3)	0.058 (3)	0.081 (4)	0.023 (2)	0.009 (3)	0.031 (3)
C3	0.062 (3)	0.071 (3)	0.055 (3)	0.007 (2)	−0.001 (2)	0.030 (3)
C4	0.045 (2)	0.064 (3)	0.042 (2)	0.0034 (19)	−0.0027 (16)	0.011 (2)
C5	0.0338 (18)	0.041 (2)	0.040 (2)	0.0002 (13)	−0.0046 (14)	0.0037 (14)
C6	0.0349 (17)	0.0372 (19)	0.0389 (19)	0.0013 (14)	−0.0088 (13)	−0.0023 (15)
C7	0.059 (2)	0.0361 (19)	0.038 (2)	0.0048 (17)	−0.0084 (16)	−0.0021 (16)
C8	0.056 (2)	0.050 (2)	0.058 (2)	0.014 (2)	−0.0080 (18)	0.003 (2)
C9	0.068 (3)	0.057 (3)	0.069 (3)	0.008 (2)	−0.018 (2)	0.000 (2)
C10	0.080 (4)	0.068 (4)	0.088 (4)	0.013 (2)	−0.027 (3)	0.000 (3)
C11	0.136 (6)	0.067 (4)	0.120 (6)	0.013 (4)	−0.052 (5)	0.021 (4)
C12	0.048 (2)	0.0407 (19)	0.0342 (18)	0.0035 (16)	−0.0037 (15)	−0.0009 (16)
C13	0.051 (2)	0.059 (3)	0.059 (3)	−0.0021 (19)	0.004 (2)	−0.007 (2)
C14	0.074 (3)	0.073 (3)	0.081 (4)	0.015 (3)	0.028 (3)	−0.011 (3)
C15	0.107 (4)	0.065 (3)	0.054 (3)	0.022 (3)	0.018 (3)	−0.014 (2)
C16	0.099 (4)	0.070 (3)	0.054 (3)	0.002 (3)	−0.008 (3)	−0.022 (2)
C17	0.055 (2)	0.073 (3)	0.050 (3)	0.003 (2)	−0.0095 (19)	−0.019 (2)

Geometric parameters (Å, º)

Pd1—N1	2.025 (3)	C8—H8A	0.9700
Pd1—N2	2.028 (3)	C8—H8B	0.9700
Pd1—Cl1	2.2876 (11)	C9—C10	1.497 (7)
Pd1—Cl2	2.2917 (12)	C9—H9A	0.9700
N1—C1	1.347 (5)	C9—H9B	0.9700
N1—C5	1.353 (5)	C10—C11	1.523 (8)
N2—C6	1.282 (5)	C10—H10A	0.9700
N2—C7	1.472 (5)	C10—H10B	0.9700
C1—C2	1.382 (7)	C11—H11A	0.9600
C1—H1	0.9300	C11—H11B	0.9600
C2—C3	1.358 (8)	C11—H11C	0.9600
C2—H2	0.9300	C12—C13	1.395 (6)
C3—C4	1.398 (7)	C12—C17	1.397 (6)
C3—H3	0.9300	C13—C14	1.373 (7)
C4—C5	1.374 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.362 (8)
C5—C6	1.475 (5)	C14—H14	0.9300
C6—C12	1.479 (5)	C15—C16	1.390 (7)
C7—C8	1.510 (5)	C15—H15	0.9300
C7—H7A	0.9700	C16—C17	1.380 (6)
C7—H7B	0.9700	C16—H16	0.9300
C8—C9	1.546 (6)	C17—H17	0.9300
N1—Pd1—N2	79.76 (12)	C7—C8—H8B	110.1
N1—Pd1—Cl1	175.01 (9)	C9—C8—H8B	110.1
N2—Pd1—Cl1	95.49 (8)	H8A—C8—H8B	108.4
N1—Pd1—Cl2	94.99 (9)	C10—C9—C8	113.1 (4)
N2—Pd1—Cl2	174.12 (9)	C10—C9—H9A	109.0
Cl1—Pd1—Cl2	89.83 (4)	C8—C9—H9A	109.0
C1—N1—C5	118.9 (4)	C10—C9—H9B	109.0
C1—N1—Pd1	127.1 (3)	C8—C9—H9B	109.0
C5—N1—Pd1	114.0 (2)	H9A—C9—H9B	107.8
C6—N2—C7	120.9 (3)	C9—C10—C11	111.3 (5)
C6—N2—Pd1	115.4 (2)	C9—C10—H10A	109.4
C7—N2—Pd1	123.7 (2)	C11—C10—H10A	109.4
N1—C1—C2	121.1 (4)	C9—C10—H10B	109.4
N1—C1—H1	119.4	C11—C10—H10B	109.4
C2—C1—H1	119.4	H10A—C10—H10B	108.0
C3—C2—C1	120.5 (4)	C10—C11—H11A	109.5
C3—C2—H2	119.8	C10—C11—H11B	109.5
C1—C2—H2	119.8	H11A—C11—H11B	109.5
C2—C3—C4	118.7 (4)	C10—C11—H11C	109.5
C2—C3—H3	120.6	H11A—C11—H11C	109.5
C4—C3—H3	120.6	H11B—C11—H11C	109.5
C5—C4—C3	118.9 (4)	C13—C12—C17	119.0 (4)
C5—C4—H4	120.6	C13—C12—C6	119.9 (3)
C3—C4—H4	120.6	C17—C12—C6	121.2 (3)
N1—C5—C4	121.9 (3)	C14—C13—C12	119.8 (4)
N1—C5—C6	114.2 (3)	C14—C13—H13	120.1
C4—C5—C6	123.9 (4)	C12—C13—H13	120.1
N2—C6—C5	116.3 (3)	C15—C14—C13	121.1 (5)
N2—C6—C12	124.7 (3)	C15—C14—H14	119.4
C5—C6—C12	119.0 (3)	C13—C14—H14	119.5
N2—C7—C8	113.8 (3)	C14—C15—C16	120.1 (4)
N2—C7—H7A	108.8	C14—C15—H15	119.9
C8—C7—H7A	108.8	C16—C15—H15	119.9
N2—C7—H7B	108.8	C17—C16—C15	119.6 (5)
C8—C7—H7B	108.8	C17—C16—H16	120.2
H7A—C7—H7B	107.7	C15—C16—H16	120.2
C7—C8—C9	108.2 (4)	C16—C17—C12	120.3 (4)
C7—C8—H8A	110.1	C16—C17—H17	119.8
C9—C8—H8A	110.1	C12—C17—H17	119.8

(Compound_4_CCDC)

Crystal data

C16H18Cl2N2Pd	Z = 2
Mr = 415.62	F(000) = 416
Triclinic, P1	Dx = 1.639 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5305 (11) Å	Cell parameters from 4927 reflections
b = 9.6211 (14) Å	θ = 2.5–25.2°
c = 10.9880 (16) Å	µ = 1.41 mm^−1
α = 72.593 (4)°	T = 300 K
β = 78.780 (5)°	Block, orange
γ = 83.039 (4)°	0.51 × 0.31 × 0.19 mm
V = 842.2 (2) Å^3

Data collection

Bruker SMART X2S diffractometer	3017 independent reflections
Radiation source: micro-focus sealed tube	2740 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.025
ω scans	θmax = 25.3°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→9
Tmin = 0.533, Tmax = 0.775	k = −11→11
8425 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.45	w = 1/[σ^2(Fo^2) + (0.0494P)^2] where P = (Fo^2 + 2Fc^2)/3
3017 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.78 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.24607 (3)	1.03943 (2)	0.48489 (2)	0.03525 (13)
Cl3	0.16891 (13)	1.21022 (11)	0.30576 (11)	0.0561 (3)
Cl2	0.32131 (13)	1.22359 (10)	0.54955 (10)	0.0539 (3)
N17	0.3073 (3)	0.8747 (3)	0.6379 (3)	0.0321 (6)
N4	0.1933 (3)	0.8650 (3)	0.4348 (3)	0.0360 (6)
C18	0.3699 (4)	0.9003 (4)	0.7444 (3)	0.0376 (8)
H18A	0.4520	0.9697	0.7083	0.045*
H18B	0.4199	0.8094	0.7918	0.045*
C19	0.2416 (4)	0.9583 (4)	0.8387 (3)	0.0387 (8)
H19	0.1847	1.0454	0.7898	0.046*
C20	0.1206 (4)	0.8458 (4)	0.9148 (4)	0.0498 (9)
H20A	0.0613	0.8261	0.8567	0.075*
H20B	0.0483	0.8833	0.9780	0.075*
H20C	0.1762	0.7572	0.9577	0.075*
C21	0.3272 (5)	1.0017 (5)	0.9319 (5)	0.0676 (13)
H21A	0.2492	1.0393	0.9919	0.101*
H21B	0.3999	1.0752	0.8834	0.101*
H21C	0.3857	0.9175	0.9786	0.101*
C10	0.2878 (4)	0.7450 (4)	0.6329 (3)	0.0342 (7)
C11	0.3177 (4)	0.6086 (4)	0.7384 (3)	0.0355 (7)
C12	0.1848 (4)	0.5353 (4)	0.8153 (4)	0.0454 (9)
H12	0.0822	0.5666	0.7970	0.054*
C13	0.2090 (5)	0.4146 (4)	0.9198 (4)	0.0574 (11)
H13	0.1213	0.3666	0.9728	0.069*
C14	0.3621 (6)	0.3649 (4)	0.9459 (4)	0.0586 (11)
H14	0.3769	0.2849	1.0164	0.070*
C15	0.4912 (5)	0.4346 (4)	0.8671 (4)	0.0562 (10)
H15	0.5938	0.3997	0.8833	0.067*
C16	0.4719 (4)	0.5557 (4)	0.7640 (4)	0.0449 (9)
H16	0.5610	0.6021	0.7117	0.054*
C9	0.2284 (4)	0.7344 (4)	0.5188 (3)	0.0362 (8)
C5	0.1371 (5)	0.8662 (4)	0.3301 (4)	0.0483 (9)
H5	0.1125	0.9553	0.2723	0.058*
C6	0.1145 (5)	0.7388 (5)	0.3050 (4)	0.0563 (11)
H6	0.0724	0.7432	0.2319	0.068*
C7	0.1532 (5)	0.6060 (5)	0.3863 (4)	0.0520 (10)
H7	0.1414	0.5196	0.3685	0.062*
C8	0.2104 (4)	0.6050 (4)	0.4956 (4)	0.0436 (9)
H8	0.2369	0.5167	0.5537	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03283 (19)	0.02384 (18)	0.0393 (2)	0.00006 (12)	−0.00018 (12)	0.00119 (12)
Cl3	0.0553 (6)	0.0398 (5)	0.0575 (6)	−0.0016 (4)	−0.0153 (5)	0.0128 (4)
Cl2	0.0674 (7)	0.0262 (4)	0.0606 (6)	−0.0091 (4)	0.0001 (5)	−0.0056 (4)
N17	0.0280 (14)	0.0252 (14)	0.0384 (15)	−0.0019 (11)	−0.0002 (11)	−0.0051 (12)
N4	0.0332 (15)	0.0305 (15)	0.0356 (16)	0.0016 (12)	−0.0013 (12)	−0.0005 (12)
C18	0.0330 (17)	0.0293 (17)	0.050 (2)	−0.0022 (14)	−0.0102 (15)	−0.0085 (15)
C19	0.0396 (18)	0.0304 (17)	0.048 (2)	−0.0004 (15)	−0.0120 (16)	−0.0125 (15)
C20	0.053 (2)	0.048 (2)	0.047 (2)	−0.0089 (19)	0.0008 (18)	−0.0153 (18)
C21	0.063 (3)	0.070 (3)	0.087 (3)	−0.003 (2)	−0.024 (3)	−0.042 (3)
C10	0.0315 (17)	0.0277 (17)	0.0368 (18)	−0.0016 (14)	0.0019 (14)	−0.0041 (14)
C11	0.0430 (19)	0.0239 (16)	0.0359 (18)	−0.0031 (14)	−0.0043 (14)	−0.0043 (14)
C12	0.047 (2)	0.0317 (18)	0.051 (2)	−0.0071 (16)	−0.0054 (17)	−0.0027 (16)
C13	0.063 (3)	0.037 (2)	0.059 (3)	−0.016 (2)	0.004 (2)	0.0033 (19)
C14	0.088 (3)	0.032 (2)	0.047 (2)	0.000 (2)	−0.016 (2)	0.0043 (17)
C15	0.059 (3)	0.041 (2)	0.059 (3)	0.0086 (19)	−0.019 (2)	0.0002 (19)
C16	0.043 (2)	0.0356 (19)	0.047 (2)	0.0017 (16)	−0.0035 (16)	−0.0026 (16)
C9	0.0308 (17)	0.0328 (18)	0.0372 (19)	0.0011 (14)	0.0010 (14)	−0.0039 (15)
C5	0.054 (2)	0.048 (2)	0.039 (2)	0.0043 (19)	−0.0164 (18)	−0.0038 (17)
C6	0.062 (3)	0.068 (3)	0.043 (2)	−0.002 (2)	−0.0181 (19)	−0.018 (2)
C7	0.054 (2)	0.050 (2)	0.055 (2)	−0.0022 (19)	−0.0059 (19)	−0.022 (2)
C8	0.051 (2)	0.0325 (19)	0.046 (2)	−0.0021 (17)	−0.0040 (17)	−0.0119 (16)

Geometric parameters (Å, º)

Pd1—N4	2.037 (3)	C10—C11	1.502 (5)
Pd1—N17	2.039 (3)	C11—C16	1.402 (5)
Pd1—Cl2	2.2940 (11)	C11—C12	1.401 (5)
Pd1—Cl3	2.3052 (10)	C12—C13	1.396 (6)
N17—C10	1.297 (4)	C12—H12	0.9300
N17—C18	1.471 (4)	C13—C14	1.389 (6)
N4—C5	1.326 (5)	C13—H13	0.9300
N4—C9	1.358 (5)	C14—C15	1.369 (6)
C18—C19	1.529 (5)	C14—H14	0.9300
C18—H18A	0.9700	C15—C16	1.380 (5)
C18—H18B	0.9700	C15—H15	0.9300
C19—C20	1.527 (5)	C16—H16	0.9300
C19—C21	1.542 (5)	C9—C8	1.374 (5)
C19—H19	0.9800	C5—C6	1.377 (6)
C20—H20A	0.9600	C5—H5	0.9300
C20—H20B	0.9600	C6—C7	1.367 (6)
C20—H20C	0.9600	C6—H6	0.9300
C21—H21A	0.9600	C7—C8	1.379 (5)
C21—H21B	0.9600	C7—H7	0.9300
C21—H21C	0.9600	C8—H8	0.9300
C10—C9	1.475 (5)
N4—Pd1—N17	80.38 (11)	N17—C10—C9	117.2 (3)
N4—Pd1—Cl2	175.33 (8)	N17—C10—C11	123.2 (3)
N17—Pd1—Cl2	95.56 (8)	C9—C10—C11	119.5 (3)
N4—Pd1—Cl3	94.57 (9)	C16—C11—C12	119.7 (3)
N17—Pd1—Cl3	174.93 (8)	C16—C11—C10	122.4 (3)
Cl2—Pd1—Cl3	89.50 (4)	C12—C11—C10	117.9 (3)
C10—N17—C18	122.7 (3)	C13—C12—C11	118.8 (4)
C10—N17—Pd1	114.3 (2)	C13—C12—H12	120.6
C18—N17—Pd1	123.0 (2)	C11—C12—H12	120.6
C5—N4—C9	118.6 (3)	C14—C13—C12	121.0 (4)
C5—N4—Pd1	127.7 (3)	C14—C13—H13	119.5
C9—N4—Pd1	113.6 (2)	C12—C13—H13	119.5
N17—C18—C19	113.6 (3)	C15—C14—C13	119.4 (4)
N17—C18—H18A	108.9	C15—C14—H14	120.3
C19—C18—H18A	108.9	C13—C14—H14	120.3
N17—C18—H18B	108.9	C14—C15—C16	121.3 (4)
C19—C18—H18B	108.9	C14—C15—H15	119.4
H18A—C18—H18B	107.7	C16—C15—H15	119.4
C20—C19—C18	112.2 (3)	C15—C16—C11	119.7 (4)
C20—C19—C21	110.1 (3)	C15—C16—H16	120.1
C18—C19—C21	107.8 (3)	C11—C16—H16	120.1
C20—C19—H19	108.9	N4—C9—C8	121.4 (3)
C18—C19—H19	108.9	N4—C9—C10	114.4 (3)
C21—C19—H19	108.9	C8—C9—C10	124.2 (3)
C19—C20—H20A	109.5	N4—C5—C6	121.6 (4)
C19—C20—H20B	109.5	N4—C5—H5	119.2
H20A—C20—H20B	109.5	C6—C5—H5	119.2
C19—C20—H20C	109.5	C7—C6—C5	120.7 (4)
H20A—C20—H20C	109.5	C7—C6—H6	119.6
H20B—C20—H20C	109.5	C5—C6—H6	119.6
C19—C21—H21A	109.5	C6—C7—C8	117.5 (4)
C19—C21—H21B	109.5	C6—C7—H7	121.2
H21A—C21—H21B	109.5	C8—C7—H7	121.2
C19—C21—H21C	109.5	C9—C8—C7	120.0 (4)
H21A—C21—H21C	109.5	C9—C8—H8	120.0
H21B—C21—H21C	109.5	C7—C8—H8	120.0

(Compound_4_X2S)

Crystal data

C16H18Cl2N2Pd	Z = 2
Mr = 415.62	F(000) = 416
Triclinic, P1	Dx = 1.639 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5305 (11) Å	Cell parameters from 4927 reflections
b = 9.6211 (14) Å	θ = 2.5–25.2°
c = 10.9880 (16) Å	µ = 1.41 mm^−1
α = 72.593 (4)°	T = 300 K
β = 78.780 (5)°	Block, orange
γ = 83.039 (4)°	0.51 × 0.31 × 0.19 mm
V = 842.2 (2) Å^3

Data collection

Bruker SMART X2S diffractometer	3017 independent reflections
Radiation source: micro-focus sealed tube	2740 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.025
ω scans	θmax = 25.3°, θmin = 2.0°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→9
Tmin = 0.533, Tmax = 0.775	k = −11→11
8425 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.23	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.1355P] where P = (Fo^2 + 2Fc^2)/3
3017 reflections	(Δ/σ)max = 0.011
192 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.78 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.24612 (3)	1.03943 (2)	0.48490 (2)	0.03536 (12)
Cl1	0.32147 (13)	1.22355 (9)	0.54961 (10)	0.0541 (3)
Cl2	0.16898 (12)	1.21023 (10)	0.30576 (10)	0.0561 (3)
N1	0.3076 (3)	0.8746 (3)	0.6379 (3)	0.0322 (6)
N2	0.1938 (3)	0.8650 (3)	0.4349 (3)	0.0363 (6)
C1	0.3700 (4)	0.9005 (3)	0.7440 (3)	0.0375 (7)
H1A	0.4518	0.9702	0.7077	0.045*
H1B	0.4203	0.8098	0.7913	0.045*
C2	0.2419 (4)	0.9582 (4)	0.8385 (3)	0.0388 (7)
H2	0.1848	1.0452	0.7895	0.047*
C3	0.3271 (5)	1.0024 (5)	0.9309 (5)	0.0674 (12)
H3A	0.2490	1.0389	0.9915	0.101*
H3B	0.3984	1.0770	0.8821	0.101*
H3C	0.3872	0.9188	0.9768	0.101*
C4	0.1210 (4)	0.8459 (4)	0.9145 (4)	0.0495 (9)
H4A	0.0625	0.8255	0.8562	0.074*
H4B	0.0480	0.8838	0.9771	0.074*
H4C	0.1765	0.7577	0.9581	0.074*
C5	0.2885 (4)	0.7449 (3)	0.6331 (3)	0.0339 (7)
C6	0.2293 (4)	0.7342 (4)	0.5192 (3)	0.0365 (7)
C7	0.1374 (4)	0.8661 (4)	0.3301 (3)	0.0491 (9)
H7	0.1128	0.9552	0.2723	0.059*
C8	0.1145 (5)	0.7389 (5)	0.3047 (4)	0.0570 (10)
H8	0.0720	0.7431	0.2318	0.068*
C9	0.1541 (5)	0.6058 (4)	0.3866 (4)	0.0522 (9)
H9	0.1425	0.5193	0.3689	0.063*
C10	0.2115 (4)	0.6045 (4)	0.4961 (3)	0.0435 (8)
H10	0.2382	0.5162	0.5541	0.052*
C11	0.3179 (4)	0.6085 (3)	0.7383 (3)	0.0354 (7)
C12	0.1856 (4)	0.5352 (4)	0.8152 (4)	0.0456 (8)
H12	0.0830	0.5666	0.7970	0.055*
C13	0.2091 (5)	0.4148 (4)	0.9195 (4)	0.0573 (10)
H13	0.1212	0.3671	0.9723	0.069*
C14	0.3615 (5)	0.3650 (4)	0.9456 (4)	0.0581 (10)
H14	0.3761	0.2850	1.0160	0.070*
C15	0.4907 (5)	0.4347 (4)	0.8668 (4)	0.0562 (10)
H15	0.5933	0.3998	0.8830	0.067*
C16	0.4713 (4)	0.5558 (4)	0.7635 (3)	0.0451 (8)
H16	0.5603	0.6020	0.7110	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03294 (17)	0.02393 (16)	0.03945 (18)	0.00005 (11)	−0.00020 (11)	0.00114 (11)
Cl1	0.0677 (6)	0.0262 (4)	0.0608 (6)	−0.0091 (4)	0.0001 (5)	−0.0057 (4)
Cl2	0.0551 (6)	0.0400 (5)	0.0576 (6)	−0.0016 (4)	−0.0152 (4)	0.0127 (4)
N1	0.0285 (13)	0.0254 (13)	0.0381 (14)	−0.0016 (10)	−0.0011 (11)	−0.0049 (11)
N2	0.0338 (14)	0.0305 (14)	0.0359 (15)	0.0016 (11)	−0.0013 (11)	−0.0007 (11)
C1	0.0328 (16)	0.0295 (16)	0.0499 (19)	−0.0017 (13)	−0.0106 (14)	−0.0084 (14)
C2	0.0399 (17)	0.0305 (16)	0.0482 (19)	−0.0004 (14)	−0.0125 (15)	−0.0124 (14)
C3	0.063 (3)	0.070 (3)	0.087 (3)	−0.002 (2)	−0.024 (2)	−0.043 (3)
C4	0.053 (2)	0.048 (2)	0.046 (2)	−0.0086 (17)	−0.0001 (16)	−0.0150 (17)
C5	0.0311 (15)	0.0279 (15)	0.0364 (17)	−0.0015 (13)	0.0005 (13)	−0.0037 (13)
C6	0.0318 (16)	0.0329 (17)	0.0375 (17)	0.0010 (13)	0.0008 (13)	−0.0042 (14)
C7	0.056 (2)	0.048 (2)	0.039 (2)	0.0043 (18)	−0.0158 (17)	−0.0039 (16)
C8	0.063 (2)	0.068 (3)	0.044 (2)	−0.003 (2)	−0.0174 (18)	−0.018 (2)
C9	0.055 (2)	0.050 (2)	0.055 (2)	−0.0029 (18)	−0.0053 (18)	−0.0221 (18)
C10	0.051 (2)	0.0329 (17)	0.045 (2)	−0.0022 (15)	−0.0042 (16)	−0.0119 (15)
C11	0.0423 (18)	0.0241 (15)	0.0364 (17)	−0.0027 (13)	−0.0047 (14)	−0.0043 (13)
C12	0.0462 (19)	0.0321 (17)	0.052 (2)	−0.0065 (15)	−0.0060 (16)	−0.0028 (15)
C13	0.064 (2)	0.037 (2)	0.058 (2)	−0.0154 (19)	0.0031 (19)	0.0032 (17)
C14	0.087 (3)	0.0318 (18)	0.046 (2)	−0.001 (2)	−0.016 (2)	0.0045 (16)
C15	0.060 (2)	0.042 (2)	0.059 (2)	0.0085 (18)	−0.0198 (19)	−0.0005 (18)
C16	0.0433 (19)	0.0354 (18)	0.048 (2)	0.0017 (15)	−0.0036 (15)	−0.0022 (15)

Geometric parameters (Å, º)

Pd1—N2	2.036 (3)	C5—C11	1.499 (4)
Pd1—N1	2.040 (3)	C6—C10	1.377 (5)
Pd1—Cl1	2.2944 (10)	C7—C8	1.378 (6)
Pd1—Cl2	2.3054 (10)	C7—H7	0.9300
N1—C5	1.296 (4)	C8—C9	1.374 (6)
N1—C1	1.466 (4)	C8—H8	0.9300
N2—C7	1.328 (4)	C9—C10	1.381 (5)
N2—C6	1.361 (4)	C9—H9	0.9300
C1—C2	1.529 (4)	C10—H10	0.9300
C1—H1A	0.9700	C11—C12	1.397 (4)
C1—H1B	0.9700	C11—C16	1.394 (5)
C2—C4	1.524 (5)	C12—C13	1.391 (5)
C2—C3	1.536 (5)	C12—H12	0.9300
C2—H2	0.9800	C13—C14	1.384 (6)
C3—H3A	0.9600	C13—H13	0.9300
C3—H3B	0.9600	C14—C15	1.369 (6)
C3—H3C	0.9600	C14—H14	0.9300
C4—H4A	0.9600	C15—C16	1.381 (5)
C4—H4B	0.9600	C15—H15	0.9300
C4—H4C	0.9600	C16—H16	0.9300
C5—C6	1.472 (5)
N2—Pd1—N1	80.34 (11)	N1—C5—C6	117.1 (3)
N2—Pd1—Cl1	175.21 (8)	N1—C5—C11	123.5 (3)
N1—Pd1—Cl1	95.52 (8)	C6—C5—C11	119.3 (3)
N2—Pd1—Cl2	94.63 (8)	N2—C6—C10	121.3 (3)
N1—Pd1—Cl2	174.96 (7)	N2—C6—C5	114.5 (3)
Cl1—Pd1—Cl2	89.52 (4)	C10—C6—C5	124.2 (3)
C5—N1—C1	122.7 (3)	N2—C7—C8	121.8 (3)
C5—N1—Pd1	114.5 (2)	N2—C7—H7	119.1
C1—N1—Pd1	122.9 (2)	C8—C7—H7	119.1
C7—N2—C6	118.8 (3)	C9—C8—C7	120.3 (4)
C7—N2—Pd1	127.7 (2)	C9—C8—H8	119.9
C6—N2—Pd1	113.4 (2)	C7—C8—H8	119.9
N1—C1—C2	113.7 (3)	C8—C9—C10	117.9 (4)
N1—C1—H1A	108.8	C8—C9—H9	121.0
C2—C1—H1A	108.8	C10—C9—H9	121.0
N1—C1—H1B	108.8	C6—C10—C9	119.9 (3)
C2—C1—H1B	108.8	C6—C10—H10	120.1
H1A—C1—H1B	107.7	C9—C10—H10	120.1
C4—C2—C1	112.3 (3)	C12—C11—C16	119.5 (3)
C4—C2—C3	110.4 (3)	C12—C11—C5	118.2 (3)
C1—C2—C3	107.9 (3)	C16—C11—C5	122.3 (3)
C4—C2—H2	108.7	C13—C12—C11	119.2 (3)
C1—C2—H2	108.7	C13—C12—H12	120.4
C3—C2—H2	108.7	C11—C12—H12	120.4
C2—C3—H3A	109.5	C14—C13—C12	120.9 (3)
C2—C3—H3B	109.5	C14—C13—H13	119.6
H3A—C3—H3B	109.5	C12—C13—H13	119.6
C2—C3—H3C	109.5	C15—C14—C13	119.4 (3)
H3A—C3—H3C	109.5	C15—C14—H14	120.3
H3B—C3—H3C	109.5	C13—C14—H14	120.3
C2—C4—H4A	109.5	C14—C15—C16	121.2 (4)
C2—C4—H4B	109.5	C14—C15—H15	119.4
H4A—C4—H4B	109.5	C16—C15—H15	119.4
C2—C4—H4C	109.5	C15—C16—C11	119.8 (3)
H4A—C4—H4C	109.5	C15—C16—H16	120.1
H4B—C4—H4C	109.5	C11—C16—H16	120.1

(Compound_5_CCDC)

Crystal data

C13H10OS	F(000) = 448
Mr = 214.27	Dx = 1.310 Mg m^−3
Monoclinic, P121/n1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2019 reflections
a = 8.007 (2) Å	θ = 2.8–25.1°
b = 16.958 (5) Å	µ = 0.27 mm^−1
c = 8.031 (2) Å	T = 300 K
β = 95.097 (10)°	Block, colorless
V = 1086.1 (5) Å^3	0.31 × 0.31 × 0.27 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1910 independent reflections
Radiation source: micro-focus sealed tube	1366 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.049
ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.922, Tmax = 0.932	k = −20→20
6685 measured reflections	l = −9→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0875P)^2] where P = (Fo^2 + 2Fc^2)/3
1910 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.95308 (8)	0.89514 (5)	0.33211 (9)	0.0507 (3)
O9	1.1091 (3)	0.78594 (14)	0.5555 (3)	0.0697 (7)
C13	0.7126 (4)	1.0597 (2)	−0.0634 (4)	0.0657 (9)
H13	0.6673	1.0936	−0.1463	0.079*
C12	0.7805 (4)	1.0894 (2)	0.0841 (4)	0.0681 (9)
H12	0.7802	1.1435	0.1026	0.082*
C11	0.8499 (4)	1.03928 (19)	0.2066 (4)	0.0580 (8)
H11	0.8970	1.0599	0.3074	0.070*
C10	0.8500 (3)	0.95873 (17)	0.1806 (3)	0.0440 (6)
C2	0.7876 (3)	0.86483 (16)	0.4498 (3)	0.0406 (6)
C3	0.8173 (3)	0.80788 (15)	0.5752 (3)	0.0452 (7)
C4	0.6855 (4)	0.78208 (19)	0.6636 (4)	0.0604 (8)
H4	0.7058	0.7439	0.7460	0.073*
C5	0.5271 (4)	0.8115 (2)	0.6320 (4)	0.0660 (9)
H5	0.4401	0.7929	0.6906	0.079*
C14	0.7104 (4)	0.9800 (3)	−0.0911 (4)	0.0735 (10)
H14	0.6627	0.9602	−0.1924	0.088*
C15	0.7787 (4)	0.9287 (2)	0.0311 (4)	0.0624 (8)
H15	0.7766	0.8746	0.0125	0.075*
C7	0.6253 (3)	0.89590 (18)	0.4229 (4)	0.0505 (7)
H7	0.6029	0.9353	0.3435	0.061*
C6	0.4983 (4)	0.8686 (2)	0.5132 (4)	0.0608 (8)
H6	0.3911	0.8895	0.4926	0.073*
C8	0.9816 (4)	0.77186 (18)	0.6176 (4)	0.0604 (8)
H8	0.9879	0.7340	0.7016	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0457 (4)	0.0526 (5)	0.0545 (5)	0.0039 (3)	0.0086 (3)	0.0098 (3)
O9	0.0586 (13)	0.0641 (15)	0.0862 (16)	0.0103 (11)	0.0048 (12)	0.0112 (12)
C13	0.0630 (19)	0.073 (3)	0.060 (2)	0.0035 (17)	−0.0011 (16)	0.0179 (17)
C12	0.079 (2)	0.052 (2)	0.071 (2)	0.0047 (16)	−0.0055 (18)	0.0105 (16)
C11	0.0697 (18)	0.049 (2)	0.0536 (17)	−0.0013 (15)	−0.0049 (15)	−0.0019 (14)
C10	0.0422 (14)	0.0471 (18)	0.0435 (14)	−0.0019 (12)	0.0077 (11)	0.0019 (12)
C2	0.0440 (14)	0.0361 (15)	0.0416 (14)	−0.0028 (11)	0.0023 (11)	−0.0082 (11)
C3	0.0556 (16)	0.0326 (15)	0.0472 (15)	−0.0039 (12)	0.0041 (13)	−0.0021 (12)
C4	0.070 (2)	0.0509 (19)	0.0616 (19)	−0.0069 (15)	0.0128 (16)	0.0056 (15)
C5	0.065 (2)	0.069 (2)	0.067 (2)	−0.0158 (17)	0.0248 (16)	0.0006 (17)
C14	0.082 (2)	0.091 (3)	0.0454 (17)	−0.003 (2)	−0.0073 (16)	0.0006 (18)
C15	0.078 (2)	0.057 (2)	0.0519 (18)	−0.0019 (16)	0.0047 (16)	−0.0039 (15)
C7	0.0486 (15)	0.0544 (19)	0.0481 (16)	0.0008 (13)	0.0017 (13)	−0.0016 (13)
C6	0.0449 (16)	0.075 (2)	0.0637 (19)	−0.0020 (15)	0.0085 (14)	−0.0059 (17)
C8	0.069 (2)	0.0398 (18)	0.072 (2)	0.0017 (15)	0.0011 (17)	0.0125 (15)

Geometric parameters (Å, º)

S1—C2	1.771 (3)	C3—C4	1.394 (4)
S1—C10	1.773 (3)	C3—C8	1.463 (4)
O9—C8	1.199 (4)	C4—C5	1.365 (5)
C13—C12	1.355 (4)	C4—H4	0.9300
C13—C14	1.369 (5)	C5—C6	1.365 (5)
C13—H13	0.9300	C5—H5	0.9300
C12—C11	1.379 (4)	C14—C15	1.387 (5)
C12—H12	0.9300	C14—H14	0.9300
C11—C10	1.382 (4)	C15—H15	0.9300
C11—H11	0.9300	C7—C6	1.380 (4)
C10—C15	1.380 (4)	C7—H7	0.9300
C2—C3	1.400 (4)	C6—H6	0.9300
C2—C7	1.401 (4)	C8—H8	0.9300
C2—S1—C10	102.59 (12)	C5—C4—H4	119.2
C12—C13—C14	120.5 (3)	C3—C4—H4	119.2
C12—C13—H13	119.7	C6—C5—C4	119.1 (3)
C14—C13—H13	119.7	C6—C5—H5	120.5
C13—C12—C11	119.9 (3)	C4—C5—H5	120.5
C13—C12—H12	120.0	C13—C14—C15	120.3 (3)
C11—C12—H12	120.0	C13—C14—H14	119.8
C12—C11—C10	120.5 (3)	C15—C14—H14	119.8
C12—C11—H11	119.8	C10—C15—C14	119.4 (3)
C10—C11—H11	119.8	C10—C15—H15	120.3
C15—C10—C11	119.3 (3)	C14—C15—H15	120.3
C15—C10—S1	120.3 (2)	C6—C7—C2	120.6 (3)
C11—C10—S1	120.3 (2)	C6—C7—H7	119.7
C3—C2—C7	117.8 (3)	C2—C7—H7	119.7
C3—C2—S1	119.8 (2)	C5—C6—C7	121.2 (3)
C7—C2—S1	122.4 (2)	C5—C6—H6	119.4
C4—C3—C2	119.6 (3)	C7—C6—H6	119.4
C4—C3—C8	117.2 (3)	O9—C8—C3	127.0 (3)
C2—C3—C8	123.2 (3)	O9—C8—H8	116.5
C5—C4—C3	121.6 (3)	C3—C8—H8	116.5

(Compound_5_X2S)

Crystal data

C13H10OS	F(000) = 448
Mr = 214.27	Dx = 1.310 Mg m^−3
Monoclinic, P121/n1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2019 reflections
a = 8.007 (2) Å	θ = 2.8–25.1°
b = 16.958 (5) Å	µ = 0.27 mm^−1
c = 8.031 (2) Å	T = 300 K
β = 95.097 (10)°	Block, colorless
V = 1086.1 (5) Å^3	0.31 × 0.31 × 0.27 mm
Z = 4

Data collection

Radiation source: fine-focus sealed tube	1366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	θmax = 25.1°, θmin = 2.4°
Tmin = 0.922, Tmax = 0.932	h = −9→9
6685 measured reflections	k = −20→20
1910 independent reflections	l = −9→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0904P)^2] where P = (Fo^2 + 2Fc^2)/3
1910 reflections	(Δ/σ)max = 0.013
136 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.04691 (8)	0.10486 (5)	0.66790 (9)	0.0507 (3)
O1	−0.1091 (3)	0.21406 (14)	0.4445 (3)	0.0697 (7)
C1	0.2874 (4)	−0.0596 (2)	1.0634 (4)	0.0657 (9)
H1	0.3327	−0.0936	1.1464	0.079*
C2	0.2195 (4)	−0.0894 (2)	0.9159 (4)	0.0681 (9)
H2	0.2198	−0.1435	0.8974	0.082*
C3	0.1501 (4)	−0.03928 (19)	0.7934 (4)	0.0580 (8)
H3	0.1030	−0.0598	0.6926	0.070*
C4	0.1500 (3)	0.04127 (17)	0.8194 (3)	0.0441 (6)
C5	0.2124 (3)	0.13516 (16)	0.5502 (3)	0.0407 (6)
C6	0.1827 (3)	0.19211 (15)	0.4248 (3)	0.0452 (7)
C7	0.0184 (4)	0.22814 (18)	0.3825 (4)	0.0604 (8)
H7	0.0121	0.2660	0.2984	0.072*
C8	0.2213 (4)	0.0713 (2)	0.9689 (4)	0.0624 (8)
H8	0.2234	0.1254	0.9875	0.075*
C9	0.2897 (4)	0.0200 (3)	1.0912 (4)	0.0734 (10)
H9	0.3373	0.0398	1.1924	0.088*
C10	0.3145 (4)	0.21791 (19)	0.3364 (4)	0.0604 (8)
H10	0.2942	0.2561	0.2540	0.073*
C11	0.4729 (4)	0.1885 (2)	0.3680 (4)	0.0660 (9)
H11	0.5599	0.2071	0.3094	0.079*
C12	0.5017 (4)	0.1314 (2)	0.4868 (4)	0.0609 (8)
H12	0.6089	0.1104	0.5074	0.073*
C13	0.3747 (3)	0.10408 (18)	0.5771 (4)	0.0505 (7)
H13	0.3971	0.0647	0.6565	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0457 (4)	0.0526 (5)	0.0545 (5)	0.0039 (3)	0.0086 (3)	0.0098 (3)
O1	0.0586 (13)	0.0641 (15)	0.0862 (16)	0.0104 (11)	0.0049 (12)	0.0112 (12)
C1	0.0630 (19)	0.073 (3)	0.060 (2)	0.0035 (17)	−0.0011 (16)	0.0179 (17)
C2	0.079 (2)	0.052 (2)	0.071 (2)	0.0046 (16)	−0.0055 (18)	0.0105 (16)
C3	0.0697 (18)	0.049 (2)	0.0536 (17)	−0.0012 (15)	−0.0049 (15)	−0.0019 (14)
C4	0.0423 (14)	0.0471 (18)	0.0435 (14)	−0.0019 (12)	0.0077 (11)	0.0019 (12)
C5	0.0440 (14)	0.0361 (15)	0.0416 (14)	−0.0028 (11)	0.0023 (11)	−0.0082 (11)
C6	0.0556 (16)	0.0326 (15)	0.0472 (15)	−0.0039 (12)	0.0041 (13)	−0.0021 (12)
C7	0.069 (2)	0.0398 (18)	0.072 (2)	0.0017 (15)	0.0011 (17)	0.0125 (15)
C8	0.078 (2)	0.057 (2)	0.0519 (18)	−0.0019 (16)	0.0047 (16)	−0.0039 (15)
C9	0.082 (2)	0.091 (3)	0.0455 (17)	−0.003 (2)	−0.0073 (16)	0.0005 (18)
C10	0.070 (2)	0.0510 (19)	0.0616 (19)	−0.0070 (15)	0.0129 (16)	0.0056 (15)
C11	0.065 (2)	0.069 (2)	0.067 (2)	−0.0159 (17)	0.0248 (16)	0.0006 (17)
C12	0.0449 (16)	0.075 (2)	0.0637 (19)	−0.0020 (15)	0.0085 (14)	−0.0059 (17)
C13	0.0486 (15)	0.0544 (19)	0.0481 (16)	0.0008 (13)	0.0018 (13)	−0.0016 (13)

Geometric parameters (Å, º)

S1—C5	1.771 (3)	C6—C10	1.394 (4)
S1—C4	1.773 (3)	C6—C7	1.463 (4)
O1—C7	1.199 (4)	C7—H7	0.9300
C1—C2	1.355 (4)	C8—C9	1.387 (5)
C1—C9	1.368 (5)	C8—H8	0.9300
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.379 (4)	C10—C11	1.365 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.382 (4)	C11—C12	1.365 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C8	1.380 (4)	C12—C13	1.380 (4)
C5—C6	1.400 (4)	C12—H12	0.9300
C5—C13	1.401 (4)	C13—H13	0.9300
C5—S1—C4	102.59 (12)	O1—C7—H7	116.5
C2—C1—C9	120.5 (3)	C6—C7—H7	116.5
C2—C1—H1	119.7	C4—C8—C9	119.4 (3)
C9—C1—H1	119.7	C4—C8—H8	120.3
C1—C2—C3	119.9 (3)	C9—C8—H8	120.3
C1—C2—H2	120.0	C1—C9—C8	120.3 (3)
C3—C2—H2	120.0	C1—C9—H9	119.9
C2—C3—C4	120.4 (3)	C8—C9—H9	119.9
C2—C3—H3	119.8	C11—C10—C6	121.6 (3)
C4—C3—H3	119.8	C11—C10—H10	119.2
C8—C4—C3	119.3 (3)	C6—C10—H10	119.2
C8—C4—S1	120.3 (2)	C12—C11—C10	119.1 (3)
C3—C4—S1	120.3 (2)	C12—C11—H11	120.5
C6—C5—C13	117.8 (3)	C10—C11—H11	120.5
C6—C5—S1	119.8 (2)	C11—C12—C13	121.2 (3)
C13—C5—S1	122.4 (2)	C11—C12—H12	119.4
C10—C6—C5	119.6 (3)	C13—C12—H12	119.4
C10—C6—C7	117.2 (3)	C12—C13—C5	120.6 (3)
C5—C6—C7	123.2 (3)	C12—C13—H13	119.7
O1—C7—C6	127.0 (3)	C5—C13—H13	119.7

(Compound_6_CCDC)

Crystal data

C12H16O3	F(000) = 448
Mr = 208.25	Dx = 1.238 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1463 reflections
a = 8.894 (4) Å	θ = 2.5–21.9°
b = 16.220 (8) Å	µ = 0.09 mm^−1
c = 7.742 (3) Å	T = 300 K
β = 90.214 (14)°	Block, colorless
V = 1116.9 (9) Å^3	0.44 × 0.38 × 0.27 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1944 independent reflections
Radiation source: micro-focus sealed tube	1285 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.043
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→9
Tmin = 0.962, Tmax = 0.977	k = −19→19
7217 measured reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0956P)^2] where P = (Fo^2 + 2Fc^2)/3
1944 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O10	0.27549 (17)	0.40331 (10)	0.09433 (17)	0.0413 (5)
O9	0.1882 (2)	0.50089 (10)	−0.39245 (19)	0.0577 (6)
H9	0.1755	0.4652	−0.4661	0.087*
O14	0.18947 (17)	0.36544 (10)	0.36779 (17)	0.0432 (5)
C13	0.3372 (3)	0.26728 (15)	0.2005 (3)	0.0506 (7)
H13A	0.3497	0.2352	0.3037	0.076*
H13C	0.4266	0.2635	0.1317	0.076*
H13B	0.2531	0.2466	0.1356	0.076*
C11	0.3092 (2)	0.35671 (14)	0.2484 (3)	0.0396 (6)
C4	0.1317 (2)	0.39187 (13)	0.0277 (3)	0.0351 (6)
C3	0.1055 (2)	0.42109 (13)	−0.1399 (3)	0.0369 (6)
C2	−0.0379 (3)	0.41084 (15)	−0.2091 (3)	0.0451 (6)
H2	−0.0572	0.4301	−0.3201	0.054*
C1	−0.1536 (3)	0.37279 (15)	−0.1182 (3)	0.0478 (6)
C7	−0.3093 (3)	0.3633 (2)	−0.1979 (4)	0.0766 (9)
H7A	−0.3491	0.3100	−0.1694	0.115*
H7B	−0.3025	0.3686	−0.3211	0.115*
H7C	−0.3745	0.4054	−0.1534	0.115*
C12	0.4460 (3)	0.39724 (18)	0.3284 (3)	0.0576 (7)
H12C	0.4229	0.4535	0.3563	0.086*
H12A	0.5278	0.3957	0.2480	0.086*
H12B	0.4739	0.3682	0.4317	0.086*
C5	0.0182 (2)	0.35579 (14)	0.1236 (3)	0.0369 (6)
C6	−0.1231 (2)	0.34571 (15)	0.0476 (3)	0.0448 (6)
H6	−0.1989	0.3201	0.1102	0.054*
C8	0.2320 (3)	0.46348 (15)	−0.2347 (3)	0.0442 (6)
H8A	0.2748	0.5054	−0.1600	0.053*
H8B	0.3100	0.4233	−0.2583	0.053*
C15	0.0497 (3)	0.33104 (16)	0.3084 (3)	0.0467 (6)
H15B	−0.0314	0.3501	0.3816	0.056*
H15A	0.0539	0.2714	0.3164	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O10	0.0397 (9)	0.0478 (10)	0.0365 (9)	−0.0064 (7)	−0.0044 (7)	0.0084 (7)
O9	0.0938 (15)	0.0440 (11)	0.0353 (9)	0.0017 (10)	0.0003 (9)	0.0077 (7)
O14	0.0495 (10)	0.0484 (10)	0.0316 (8)	−0.0030 (8)	−0.0003 (7)	−0.0042 (7)
C13	0.0579 (16)	0.0507 (15)	0.0430 (14)	0.0106 (12)	−0.0036 (12)	0.0000 (11)
C11	0.0427 (13)	0.0462 (14)	0.0300 (12)	−0.0007 (11)	−0.0036 (10)	0.0033 (10)
C4	0.0365 (13)	0.0353 (12)	0.0336 (12)	0.0022 (10)	−0.0030 (10)	−0.0018 (9)
C3	0.0452 (14)	0.0325 (12)	0.0328 (12)	0.0023 (10)	−0.0015 (10)	−0.0007 (9)
C2	0.0541 (16)	0.0434 (14)	0.0376 (13)	0.0106 (11)	−0.0090 (12)	−0.0018 (10)
C1	0.0420 (15)	0.0510 (15)	0.0504 (15)	0.0045 (12)	−0.0101 (12)	−0.0101 (12)
C7	0.0491 (17)	0.098 (3)	0.082 (2)	0.0007 (17)	−0.0237 (15)	−0.0046 (18)
C12	0.0544 (16)	0.0677 (18)	0.0508 (15)	−0.0096 (14)	−0.0127 (12)	0.0023 (13)
C5	0.0405 (13)	0.0377 (13)	0.0323 (12)	0.0021 (10)	0.0023 (10)	−0.0039 (9)
C6	0.0378 (13)	0.0481 (14)	0.0485 (15)	−0.0028 (11)	0.0034 (11)	−0.0044 (11)
C8	0.0571 (16)	0.0404 (14)	0.0351 (13)	−0.0025 (11)	0.0009 (11)	0.0043 (10)
C15	0.0471 (15)	0.0531 (15)	0.0399 (14)	−0.0070 (12)	0.0051 (11)	0.0036 (11)

Geometric parameters (Å, º)

O10—C4	1.390 (3)	C2—H2	0.9300
O10—C11	1.443 (3)	C1—C6	1.383 (3)
O9—C8	1.417 (3)	C1—C7	1.522 (3)
O9—H9	0.8200	C7—H7A	0.9600
O14—C11	1.420 (3)	C7—H7B	0.9600
O14—C15	1.437 (3)	C7—H7C	0.9600
C13—C11	1.518 (3)	C12—H12C	0.9600
C13—H13A	0.9600	C12—H12A	0.9600
C13—H13C	0.9600	C12—H12B	0.9600
C13—H13B	0.9600	C5—C6	1.395 (3)
C11—C12	1.513 (3)	C5—C15	1.511 (3)
C4—C5	1.385 (3)	C6—H6	0.9300
C4—C3	1.400 (3)	C8—H8A	0.9700
C3—C2	1.392 (3)	C8—H8B	0.9700
C3—C8	1.511 (3)	C15—H15B	0.9700
C2—C1	1.393 (3)	C15—H15A	0.9700
C4—O10—C11	115.15 (16)	H7A—C7—H7B	109.5
C8—O9—H9	109.5	C1—C7—H7C	109.5
C11—O14—C15	113.77 (16)	H7A—C7—H7C	109.5
C11—C13—H13A	109.5	H7B—C7—H7C	109.5
C11—C13—H13C	109.5	C11—C12—H12C	109.5
H13A—C13—H13C	109.5	C11—C12—H12A	109.5
C11—C13—H13B	109.5	H12C—C12—H12A	109.5
H13A—C13—H13B	109.5	C11—C12—H12B	109.5
H13C—C13—H13B	109.5	H12C—C12—H12B	109.5
O14—C11—O10	109.39 (17)	H12A—C12—H12B	109.5
O14—C11—C12	107.08 (18)	C4—C5—C6	118.7 (2)
O10—C11—C12	105.97 (18)	C4—C5—C15	119.1 (2)
O14—C11—C13	112.25 (19)	C6—C5—C15	122.1 (2)
O10—C11—C13	109.41 (17)	C1—C6—C5	121.8 (2)
C12—C11—C13	112.5 (2)	C1—C6—H6	119.1
C5—C4—O10	121.95 (19)	C5—C6—H6	119.1
C5—C4—C3	121.4 (2)	O9—C8—C3	114.3 (2)
O10—C4—C3	116.65 (19)	O9—C8—H8A	108.7
C2—C3—C4	117.7 (2)	C3—C8—H8A	108.7
C2—C3—C8	123.4 (2)	O9—C8—H8B	108.7
C4—C3—C8	118.88 (19)	C3—C8—H8B	108.7
C3—C2—C1	122.4 (2)	H8A—C8—H8B	107.6
C3—C2—H2	118.8	O14—C15—C5	110.92 (18)
C1—C2—H2	118.8	O14—C15—H15B	109.5
C6—C1—C2	117.8 (2)	C5—C15—H15B	109.5
C6—C1—C7	121.3 (2)	O14—C15—H15A	109.5
C2—C1—C7	120.8 (2)	C5—C15—H15A	109.5
C1—C7—H7A	109.5	H15B—C15—H15A	108.0
C1—C7—H7B	109.5

(Compound_6_X2S)

Crystal data

C12H16O3	F(000) = 448
Mr = 208.25	Dx = 1.238 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1463 reflections
a = 8.894 (4) Å	θ = 2.5–21.9°
b = 16.220 (8) Å	µ = 0.09 mm^−1
c = 7.742 (3) Å	T = 300 K
β = 90.214 (14)°	Block, colorless
V = 1116.9 (9) Å^3	0.44 × 0.38 × 0.27 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1944 independent reflections
Radiation source: micro-focus sealed tube	1285 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.043
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→9
Tmin = 0.848, Tmax = 0.977	k = −19→19
7217 measured reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1061P)^2] where P = (Fo^2 + 2Fc^2)/3
1944 reflections	(Δ/σ)max = 6.481
140 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.27547 (18)	0.40331 (10)	0.09437 (18)	0.0415 (5)
O2	0.1881 (2)	0.50078 (10)	−0.3929 (2)	0.0578 (6)
H2	0.1770	0.4651	−0.4668	0.087*
O3	0.18947 (18)	0.36545 (10)	0.36778 (19)	0.0433 (5)
C1	0.3372 (3)	0.26728 (16)	0.2005 (3)	0.0507 (7)
H1A	0.3499	0.2352	0.3037	0.076*
H1B	0.4265	0.2635	0.1316	0.076*
H1C	0.2531	0.2465	0.1358	0.076*
C2	0.3092 (3)	0.35675 (15)	0.2484 (3)	0.0397 (6)
C3	0.1317 (3)	0.39191 (14)	0.0278 (3)	0.0353 (6)
C4	0.1054 (3)	0.42110 (14)	−0.1399 (3)	0.0370 (6)
C5	−0.0379 (3)	0.41084 (16)	−0.2091 (3)	0.0453 (7)
H5	−0.0572	0.4301	−0.3201	0.054*
C6	−0.1537 (3)	0.37284 (17)	−0.1182 (3)	0.0480 (7)
C7	−0.3094 (3)	0.3634 (2)	−0.1979 (4)	0.0767 (10)
H7A	−0.3482	0.3096	−0.1716	0.115*
H7B	−0.3029	0.3700	−0.3208	0.115*
H7C	−0.3752	0.4047	−0.1514	0.115*
C8	0.4459 (3)	0.39727 (19)	0.3285 (3)	0.0577 (8)
H8A	0.4230	0.4536	0.3560	0.087*
H8B	0.5279	0.3955	0.2484	0.087*
H8C	0.4735	0.3684	0.4321	0.087*
C9	0.0181 (3)	0.35583 (15)	0.1236 (3)	0.0371 (6)
C10	−0.1232 (3)	0.34571 (16)	0.0478 (3)	0.0449 (7)
H10	−0.1990	0.3200	0.1104	0.054*
C11	0.2320 (3)	0.46342 (16)	−0.2348 (3)	0.0445 (7)
H11A	0.2748	0.5054	−0.1601	0.053*
H11B	0.3101	0.4232	−0.2581	0.053*
C12	0.0497 (3)	0.33103 (17)	0.3084 (3)	0.0468 (7)
H12A	−0.0314	0.3501	0.3817	0.056*
H12B	0.0540	0.2714	0.3164	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0399 (10)	0.0479 (10)	0.0366 (10)	−0.0064 (8)	−0.0045 (7)	0.0085 (7)
O2	0.0929 (15)	0.0445 (11)	0.0358 (10)	0.0019 (10)	0.0006 (10)	0.0089 (8)
O3	0.0498 (10)	0.0486 (10)	0.0317 (9)	−0.0029 (8)	−0.0003 (8)	−0.0042 (7)
C1	0.0583 (17)	0.0507 (16)	0.0433 (15)	0.0108 (13)	−0.0039 (12)	0.0000 (12)
C2	0.0427 (14)	0.0463 (14)	0.0301 (13)	−0.0008 (11)	−0.0035 (11)	0.0031 (10)
C3	0.0367 (14)	0.0353 (13)	0.0339 (13)	0.0020 (10)	−0.0028 (10)	−0.0018 (10)
C4	0.0452 (14)	0.0328 (12)	0.0329 (13)	0.0021 (10)	−0.0016 (10)	−0.0006 (10)
C5	0.0544 (17)	0.0437 (15)	0.0376 (14)	0.0108 (12)	−0.0088 (12)	−0.0018 (11)
C6	0.0419 (15)	0.0512 (16)	0.0508 (16)	0.0045 (12)	−0.0101 (13)	−0.0103 (13)
C7	0.0492 (18)	0.099 (3)	0.082 (2)	0.0008 (18)	−0.0236 (16)	−0.0046 (19)
C8	0.0545 (17)	0.0678 (19)	0.0507 (16)	−0.0097 (14)	−0.0125 (13)	0.0024 (14)
C9	0.0411 (14)	0.0378 (13)	0.0325 (13)	0.0020 (11)	0.0024 (10)	−0.0040 (10)
C10	0.0377 (14)	0.0484 (15)	0.0486 (16)	−0.0027 (11)	0.0033 (12)	−0.0042 (12)
C11	0.0574 (17)	0.0403 (15)	0.0359 (14)	−0.0024 (12)	0.0011 (12)	0.0043 (11)
C12	0.0473 (15)	0.0534 (16)	0.0398 (15)	−0.0071 (12)	0.0052 (12)	0.0036 (12)

Geometric parameters (Å, º)

O1—C3	1.389 (3)	C5—H5	0.9300
O1—C2	1.442 (3)	C6—C10	1.384 (4)
O2—C11	1.419 (3)	C6—C7	1.522 (3)
O2—H2	0.8201	C7—H7A	0.9600
O3—C2	1.420 (3)	C7—H7B	0.9600
O3—C12	1.437 (3)	C7—H7C	0.9600
C1—C2	1.519 (4)	C8—H8A	0.9600
C1—H1A	0.9600	C8—H8B	0.9600
C1—H1B	0.9600	C8—H8C	0.9600
C1—H1C	0.9600	C9—C10	1.395 (3)
C2—C8	1.513 (3)	C9—C12	1.511 (3)
C3—C9	1.386 (3)	C10—H10	0.9300
C3—C4	1.400 (3)	C11—H11A	0.9700
C4—C5	1.391 (3)	C11—H11B	0.9700
C4—C11	1.511 (3)	C12—H12A	0.9700
C5—C6	1.393 (4)	C12—H12B	0.9700
C3—O1—C2	115.18 (17)	H7A—C7—H7B	109.5
C11—O2—H2	109.1	C6—C7—H7C	109.4
C2—O3—C12	113.76 (17)	H7A—C7—H7C	109.5
C2—C1—H1A	109.5	H7B—C7—H7C	109.5
C2—C1—H1B	109.4	C2—C8—H8A	109.5
H1A—C1—H1B	109.5	C2—C8—H8B	109.5
C2—C1—H1C	109.6	H8A—C8—H8B	109.5
H1A—C1—H1C	109.5	C2—C8—H8C	109.4
H1B—C1—H1C	109.5	H8A—C8—H8C	109.5
O3—C2—O1	109.42 (18)	H8B—C8—H8C	109.5
O3—C2—C8	107.05 (19)	C3—C9—C10	118.8 (2)
O1—C2—C8	106.0 (2)	C3—C9—C12	119.1 (2)
O3—C2—C1	112.2 (2)	C10—C9—C12	122.1 (2)
O1—C2—C1	109.41 (18)	C6—C10—C9	121.8 (2)
C8—C2—C1	112.5 (2)	C6—C10—H10	119.1
C9—C3—O1	122.0 (2)	C9—C10—H10	119.1
C9—C3—C4	121.3 (2)	O2—C11—C4	114.2 (2)
O1—C3—C4	116.7 (2)	O2—C11—H11A	108.4
C5—C4—C3	117.8 (2)	C4—C11—H11A	108.8
C5—C4—C11	123.4 (2)	O2—C11—H11B	109.0
C3—C4—C11	118.8 (2)	C4—C11—H11B	108.6
C4—C5—C6	122.4 (2)	H11A—C11—H11B	107.6
C4—C5—H5	118.8	O3—C12—C9	110.93 (19)
C6—C5—H5	118.8	O3—C12—H12A	109.5
C10—C6—C5	117.8 (2)	C9—C12—H12A	109.6
C10—C6—C7	121.3 (3)	O3—C12—H12B	109.4
C5—C6—C7	120.9 (2)	C9—C12—H12B	109.4
C6—C7—H7A	109.5	H12A—C12—H12B	108.0
C6—C7—H7B	109.5

(Compound_7_CCDC)

Crystal data

C13H18N2O3S	F(000) = 600
Mr = 282.35	Dx = 1.334 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3155 reflections
a = 12.8651 (14) Å	θ = 2.7–24.5°
b = 15.3291 (14) Å	µ = 0.24 mm^−1
c = 7.1435 (8) Å	T = 300 K
β = 93.379 (4)°	Plate, colorless
V = 1406.3 (3) Å^3	0.31 × 0.27 × 0.26 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2482 independent reflections
Radiation source: micro-focus sealed tube	1862 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.049
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −15→15
Tmin = 0.665, Tmax = 0.745	k = −18→18
13591 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0759P)^2 + 0.1981P] where P = (Fo^2 + 2Fc^2)/3
2482 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.33421 (5)	0.08148 (4)	0.13084 (9)	0.0460 (2)
O3	0.37111 (16)	−0.00654 (12)	0.1230 (3)	0.0638 (6)
O2	0.28767 (17)	0.11992 (14)	−0.0362 (2)	0.0686 (6)
O18	0.82865 (16)	0.21154 (14)	0.4203 (4)	0.0801 (7)
N16	0.69547 (16)	0.30608 (14)	0.3613 (3)	0.0412 (5)
N4	0.24633 (16)	0.08330 (12)	0.2859 (3)	0.0410 (5)
C19	0.8656 (2)	0.36289 (19)	0.4482 (5)	0.0682 (8)
H19A	0.8841	0.3659	0.5803	0.102*
H19B	0.8296	0.4152	0.4092	0.102*
H19C	0.9275	0.3570	0.3807	0.102*
C17	0.7967 (2)	0.28616 (18)	0.4089 (4)	0.0494 (6)
C13	0.61163 (18)	0.25016 (14)	0.3147 (3)	0.0352 (5)
C12	0.51548 (18)	0.28784 (14)	0.2663 (3)	0.0381 (5)
H12	0.5084	0.3482	0.2691	0.046*
C11	0.43124 (18)	0.23701 (14)	0.2145 (3)	0.0400 (6)
H11	0.3673	0.2630	0.1824	0.048*
C10	0.44080 (19)	0.14621 (14)	0.2096 (3)	0.0388 (6)
C5	0.1775 (2)	0.15986 (18)	0.2942 (4)	0.0581 (7)
H5A	0.1592	0.1809	0.1685	0.070*
H5B	0.2131	0.2064	0.3641	0.070*
C6	0.0804 (2)	0.1340 (2)	0.3889 (6)	0.0772 (10)
H6A	0.0419	0.0914	0.3120	0.093*
H6B	0.0364	0.1849	0.4007	0.093*
C7	0.1067 (2)	0.0956 (2)	0.5822 (5)	0.0711 (9)
H7A	0.1369	0.1405	0.6641	0.085*
H7B	0.0434	0.0752	0.6352	0.085*
C14	0.6206 (2)	0.15967 (15)	0.3121 (4)	0.0464 (6)
H14	0.6843	0.1336	0.3457	0.056*
C15	0.5362 (2)	0.10891 (16)	0.2602 (4)	0.0469 (6)
H15	0.5431	0.0485	0.2590	0.056*
C9	0.2776 (2)	0.04738 (16)	0.4722 (3)	0.0469 (6)
H9A	0.3165	0.0909	0.5459	0.056*
H9B	0.3222	−0.0030	0.4585	0.056*
C8	0.1820 (2)	0.02099 (18)	0.5717 (4)	0.0565 (7)
H8A	0.1480	−0.0273	0.5054	0.068*
H8B	0.2028	0.0015	0.6975	0.068*
H16	0.6805 (19)	0.3588 (17)	0.358 (3)	0.040 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0590 (4)	0.0342 (4)	0.0449 (4)	−0.0094 (3)	0.0046 (3)	−0.0039 (3)
O3	0.0740 (13)	0.0337 (10)	0.0858 (14)	−0.0087 (9)	0.0225 (11)	−0.0175 (9)
O2	0.0882 (15)	0.0745 (14)	0.0413 (10)	−0.0276 (12)	−0.0119 (10)	0.0064 (9)
O18	0.0498 (12)	0.0545 (13)	0.135 (2)	0.0142 (10)	−0.0071 (13)	−0.0031 (12)
N16	0.0417 (12)	0.0302 (12)	0.0521 (13)	0.0024 (9)	0.0081 (9)	0.0026 (9)
N4	0.0423 (11)	0.0321 (11)	0.0482 (12)	0.0015 (8)	−0.0002 (9)	0.0052 (8)
C19	0.0481 (17)	0.063 (2)	0.093 (2)	−0.0049 (14)	−0.0014 (16)	0.0025 (16)
C17	0.0430 (15)	0.0488 (16)	0.0566 (16)	0.0044 (12)	0.0054 (12)	0.0009 (12)
C13	0.0411 (13)	0.0314 (12)	0.0342 (12)	0.0021 (10)	0.0109 (10)	0.0014 (9)
C12	0.0454 (14)	0.0240 (12)	0.0454 (13)	0.0022 (10)	0.0077 (11)	0.0004 (9)
C11	0.0447 (14)	0.0316 (13)	0.0438 (13)	0.0038 (10)	0.0030 (11)	0.0030 (10)
C10	0.0487 (14)	0.0315 (12)	0.0368 (12)	−0.0014 (10)	0.0084 (11)	0.0003 (9)
C5	0.0531 (17)	0.0443 (15)	0.0761 (19)	0.0094 (13)	−0.0035 (15)	0.0105 (13)
C6	0.0448 (17)	0.072 (2)	0.114 (3)	0.0142 (15)	0.0030 (17)	−0.0042 (19)
C7	0.0583 (19)	0.073 (2)	0.084 (2)	−0.0074 (16)	0.0245 (17)	−0.0135 (17)
C14	0.0448 (14)	0.0319 (13)	0.0629 (16)	0.0085 (11)	0.0074 (12)	0.0045 (11)
C15	0.0562 (16)	0.0253 (12)	0.0601 (16)	0.0047 (11)	0.0112 (13)	0.0020 (11)
C9	0.0513 (15)	0.0423 (14)	0.0465 (14)	−0.0001 (12)	−0.0015 (12)	0.0062 (11)
C8	0.0656 (19)	0.0530 (17)	0.0518 (16)	−0.0101 (14)	0.0104 (14)	0.0018 (12)

Geometric parameters (Å, º)

S1—O2	1.430 (2)	C11—H11	0.9300
S1—O3	1.432 (2)	C10—C15	1.382 (3)
S1—N4	1.629 (2)	C5—C6	1.508 (4)
S1—C10	1.758 (2)	C5—H5A	0.9700
O18—C17	1.217 (3)	C5—H5B	0.9700
N16—C17	1.361 (3)	C6—C7	1.521 (5)
N16—C13	1.402 (3)	C6—H6A	0.9700
N16—H16	0.83 (3)	C6—H6B	0.9700
N4—C5	1.473 (3)	C7—C8	1.504 (4)
N4—C9	1.475 (3)	C7—H7A	0.9700
C19—C17	1.490 (4)	C7—H7B	0.9700
C19—H19A	0.9600	C14—C15	1.370 (3)
C19—H19B	0.9600	C14—H14	0.9300
C19—H19C	0.9600	C15—H15	0.9300
C13—C12	1.390 (3)	C9—C8	1.510 (4)
C13—C14	1.392 (3)	C9—H9A	0.9700
C12—C11	1.368 (3)	C9—H9B	0.9700
C12—H12	0.9300	C8—H8A	0.9700
C11—C10	1.398 (3)	C8—H8B	0.9700
O2—S1—O3	118.62 (13)	C6—C5—H5A	109.9
O2—S1—N4	106.67 (12)	N4—C5—H5B	109.9
O3—S1—N4	106.71 (11)	C6—C5—H5B	109.9
O2—S1—C10	108.35 (11)	H5A—C5—H5B	108.3
O3—S1—C10	106.86 (12)	C5—C6—C7	111.3 (3)
N4—S1—C10	109.40 (10)	C5—C6—H6A	109.4
C17—N16—C13	129.3 (2)	C7—C6—H6A	109.4
C17—N16—H16	116.2 (17)	C5—C6—H6B	109.4
C13—N16—H16	114.5 (17)	C7—C6—H6B	109.4
C5—N4—C9	113.2 (2)	H6A—C6—H6B	108.0
C5—N4—S1	118.96 (17)	C8—C7—C6	111.0 (3)
C9—N4—S1	116.38 (16)	C8—C7—H7A	109.4
C17—C19—H19A	109.5	C6—C7—H7A	109.4
C17—C19—H19B	109.5	C8—C7—H7B	109.4
H19A—C19—H19B	109.5	C6—C7—H7B	109.4
C17—C19—H19C	109.5	H7A—C7—H7B	108.0
H19A—C19—H19C	109.5	C15—C14—C13	120.3 (2)
H19B—C19—H19C	109.5	C15—C14—H14	119.9
O18—C17—N16	122.9 (3)	C13—C14—H14	119.9
O18—C17—C19	122.3 (3)	C14—C15—C10	120.9 (2)
N16—C17—C19	114.8 (2)	C14—C15—H15	119.5
C12—C13—C14	118.9 (2)	C10—C15—H15	119.5
C12—C13—N16	117.8 (2)	N4—C9—C8	109.8 (2)
C14—C13—N16	123.3 (2)	N4—C9—H9A	109.7
C11—C12—C13	120.6 (2)	C8—C9—H9A	109.7
C11—C12—H12	119.7	N4—C9—H9B	109.7
C13—C12—H12	119.7	C8—C9—H9B	109.7
C12—C11—C10	120.3 (2)	H9A—C9—H9B	108.2
C12—C11—H11	119.9	C7—C8—C9	111.4 (2)
C10—C11—H11	119.9	C7—C8—H8A	109.4
C15—C10—C11	118.9 (2)	C9—C8—H8A	109.4
C15—C10—S1	120.92 (18)	C7—C8—H8B	109.4
C11—C10—S1	120.12 (19)	C9—C8—H8B	109.4
N4—C5—C6	109.0 (2)	H8A—C8—H8B	108.0
N4—C5—H5A	109.9

(Compound_7_X2S)

Crystal data

C13H18N2O3S	F(000) = 600
Mr = 282.35	Dx = 1.334 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3155 reflections
a = 12.8651 (14) Å	θ = 2.7–24.5°
b = 15.3291 (14) Å	µ = 0.24 mm^−1
c = 7.1435 (8) Å	T = 300 K
β = 93.379 (4)°	Plate, colorless
V = 1406.3 (3) Å^3	0.31 × 0.27 × 0.26 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2482 independent reflections
Radiation source: micro-focus sealed tube	1862 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.049
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −15→15
Tmin = 0.665, Tmax = 0.745	k = −18→18
13591 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0911P)^2 + 0.2744P] where P = (Fo^2 + 2Fc^2)/3
2482 reflections	(Δ/σ)max = 0.178
173 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.33423 (5)	0.08148 (4)	0.13084 (9)	0.0460 (2)
O1	0.37112 (17)	−0.00653 (12)	0.1231 (3)	0.0639 (6)
O2	0.28768 (17)	0.11992 (14)	−0.0363 (2)	0.0686 (6)
O3	0.82867 (16)	0.21154 (14)	0.4203 (4)	0.0803 (7)
N1	0.69540 (15)	0.30618 (12)	0.3612 (3)	0.0411 (5)
H1	0.6807	0.3609	0.3594	0.049*
N2	0.24632 (16)	0.08331 (12)	0.2859 (3)	0.0411 (5)
C1	0.8656 (2)	0.3629 (2)	0.4483 (5)	0.0684 (8)
H1A	0.8820	0.3672	0.5809	0.103*
H1B	0.8306	0.4151	0.4050	0.103*
H1C	0.9287	0.3560	0.3845	0.103*
C2	0.7967 (2)	0.28618 (18)	0.4089 (4)	0.0495 (6)
C3	0.61164 (18)	0.25016 (14)	0.3148 (3)	0.0353 (5)
C4	0.51545 (18)	0.28786 (14)	0.2662 (3)	0.0382 (5)
H4	0.5083	0.3482	0.2690	0.046*
C5	0.43120 (18)	0.23700 (15)	0.2145 (3)	0.0401 (6)
H5	0.3673	0.2630	0.1825	0.048*
C6	0.44078 (19)	0.14622 (14)	0.2096 (3)	0.0390 (6)
C7	0.2776 (2)	0.04740 (16)	0.4723 (3)	0.0470 (6)
H7A	0.3165	0.0909	0.5459	0.056*
H7B	0.3222	−0.0029	0.4585	0.056*
C8	0.1821 (2)	0.02102 (18)	0.5718 (4)	0.0566 (7)
H8A	0.1481	−0.0274	0.5056	0.068*
H8B	0.2029	0.0016	0.6977	0.068*
C9	0.1067 (2)	0.0956 (2)	0.5822 (5)	0.0712 (9)
H9A	0.1369	0.1405	0.6641	0.085*
H9B	0.0434	0.0752	0.6352	0.085*
C10	0.6206 (2)	0.15966 (15)	0.3122 (4)	0.0465 (6)
H10	0.6842	0.1336	0.3459	0.056*
C11	0.5362 (2)	0.10888 (16)	0.2602 (4)	0.0470 (6)
H11	0.5431	0.0485	0.2589	0.056*
C12	0.1775 (2)	0.15985 (18)	0.2943 (4)	0.0583 (7)
H12A	0.1593	0.1809	0.1686	0.070*
H12B	0.2131	0.2064	0.3643	0.070*
C13	0.0804 (2)	0.1340 (2)	0.3889 (6)	0.0774 (10)
H13A	0.0419	0.0914	0.3120	0.093*
H13B	0.0364	0.1849	0.4007	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0590 (4)	0.0342 (4)	0.0449 (4)	−0.0094 (3)	0.0046 (3)	−0.0038 (2)
O1	0.0742 (13)	0.0338 (10)	0.0857 (14)	−0.0088 (9)	0.0225 (11)	−0.0174 (9)
O2	0.0881 (15)	0.0747 (14)	0.0414 (10)	−0.0279 (12)	−0.0117 (10)	0.0064 (9)
O3	0.0499 (12)	0.0545 (13)	0.135 (2)	0.0141 (10)	−0.0071 (13)	−0.0030 (12)
N1	0.0415 (11)	0.0311 (11)	0.0514 (12)	0.0021 (8)	0.0080 (9)	0.0026 (8)
N2	0.0424 (11)	0.0320 (11)	0.0485 (12)	0.0014 (8)	−0.0004 (9)	0.0051 (8)
C1	0.0485 (17)	0.063 (2)	0.093 (2)	−0.0048 (14)	−0.0014 (16)	0.0026 (16)
C2	0.0433 (15)	0.0488 (16)	0.0568 (16)	0.0044 (12)	0.0054 (12)	0.0009 (12)
C3	0.0412 (13)	0.0314 (12)	0.0343 (11)	0.0021 (10)	0.0109 (10)	0.0014 (9)
C4	0.0454 (14)	0.0241 (12)	0.0457 (13)	0.0023 (10)	0.0077 (11)	0.0003 (9)
C5	0.0447 (14)	0.0316 (12)	0.0440 (13)	0.0038 (10)	0.0029 (11)	0.0030 (10)
C6	0.0488 (14)	0.0316 (12)	0.0372 (12)	−0.0013 (10)	0.0082 (10)	0.0003 (9)
C7	0.0516 (15)	0.0421 (14)	0.0467 (14)	−0.0002 (12)	−0.0014 (12)	0.0062 (11)
C8	0.0655 (18)	0.0532 (17)	0.0519 (16)	−0.0102 (14)	0.0103 (14)	0.0019 (12)
C9	0.0586 (19)	0.073 (2)	0.084 (2)	−0.0072 (16)	0.0246 (17)	−0.0136 (17)
C10	0.0449 (14)	0.0319 (13)	0.0630 (16)	0.0086 (11)	0.0073 (12)	0.0047 (11)
C11	0.0560 (16)	0.0256 (12)	0.0603 (16)	0.0047 (11)	0.0112 (13)	0.0020 (11)
C12	0.0531 (17)	0.0442 (15)	0.0766 (19)	0.0094 (12)	−0.0031 (14)	0.0105 (13)
C13	0.0449 (17)	0.072 (2)	0.115 (3)	0.0142 (15)	0.0030 (17)	−0.0042 (19)

Geometric parameters (Å, º)

S1—O2	1.431 (2)	C5—H5	0.9300
S1—O1	1.432 (2)	C6—C11	1.383 (3)
S1—N2	1.629 (2)	C7—C8	1.510 (4)
S1—C6	1.758 (2)	C7—H7A	0.9700
O3—C2	1.217 (3)	C7—H7B	0.9700
N1—C2	1.362 (3)	C8—C9	1.504 (4)
N1—C3	1.402 (3)	C8—H8A	0.9700
N1—H1	0.8600	C8—H8B	0.9700
N2—C12	1.473 (3)	C9—C13	1.521 (5)
N2—C7	1.474 (3)	C9—H9A	0.9700
C1—C2	1.491 (4)	C9—H9B	0.9700
C1—H1A	0.9600	C10—C11	1.369 (4)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—H11	0.9300
C3—C4	1.391 (3)	C12—C13	1.508 (4)
C3—C10	1.392 (3)	C12—H12A	0.9700
C4—C5	1.368 (3)	C12—H12B	0.9700
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.398 (3)	C13—H13B	0.9700
O2—S1—O1	118.62 (13)	C8—C7—H7A	109.7
O2—S1—N2	106.68 (12)	N2—C7—H7B	109.7
O1—S1—N2	106.71 (11)	C8—C7—H7B	109.7
O2—S1—C6	108.34 (11)	H7A—C7—H7B	108.2
O1—S1—C6	106.87 (12)	C9—C8—C7	111.4 (2)
N2—S1—C6	109.39 (10)	C9—C8—H8A	109.4
C2—N1—C3	129.2 (2)	C7—C8—H8A	109.4
C2—N1—H1	115.4	C9—C8—H8B	109.4
C3—N1—H1	115.4	C7—C8—H8B	109.4
C12—N2—C7	113.2 (2)	H8A—C8—H8B	108.0
C12—N2—S1	118.96 (17)	C8—C9—C13	111.0 (3)
C7—N2—S1	116.37 (16)	C8—C9—H9A	109.4
C2—C1—H1A	109.5	C13—C9—H9A	109.4
C2—C1—H1B	109.5	C8—C9—H9B	109.4
H1A—C1—H1B	109.5	C13—C9—H9B	109.4
C2—C1—H1C	109.5	H9A—C9—H9B	108.0
H1A—C1—H1C	109.5	C11—C10—C3	120.3 (2)
H1B—C1—H1C	109.5	C11—C10—H10	119.8
O3—C2—N1	122.9 (3)	C3—C10—H10	119.8
O3—C2—C1	122.3 (3)	C10—C11—C6	120.9 (2)
N1—C2—C1	114.8 (2)	C10—C11—H11	119.6
C4—C3—C10	118.9 (2)	C6—C11—H11	119.6
C4—C3—N1	117.68 (19)	N2—C12—C13	109.0 (2)
C10—C3—N1	123.4 (2)	N2—C12—H12A	109.9
C5—C4—C3	120.6 (2)	C13—C12—H12A	109.9
C5—C4—H4	119.7	N2—C12—H12B	109.9
C3—C4—H4	119.7	C13—C12—H12B	109.9
C4—C5—C6	120.3 (2)	H12A—C12—H12B	108.3
C4—C5—H5	119.8	C12—C13—C9	111.3 (3)
C6—C5—H5	119.8	C12—C13—H13A	109.4
C11—C6—C5	118.9 (2)	C9—C13—H13A	109.4
C11—C6—S1	120.89 (18)	C12—C13—H13B	109.4
C5—C6—S1	120.13 (19)	C9—C13—H13B	109.4
N2—C7—C8	109.8 (2)	H13A—C13—H13B	108.0
N2—C7—H7A	109.7

(Compound_8_APEX)

Crystal data

C21H21NO3S2	F(000) = 840
Mr = 399.51	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7771 (7) Å	Cell parameters from 9992 reflections
b = 11.4544 (6) Å	θ = 2.8–25.0°
c = 14.9031 (9) Å	µ = 0.29 mm^−1
β = 95.945 (1)°	T = 291 K
V = 1999.6 (2) Å^3	Block, clear colourless
Z = 4	0.43 × 0.41 × 0.27 mm

Data collection

Bruker APEX II DUO diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	3109 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.3333 pixels mm^-1	θmax = 25.1°, θmin = 1.7°
φ & ω scans	h = −14→14
Absorption correction: multi-scan SADABS Version 2008/1	k = −13→13
Tmin = 0.84, Tmax = 0.93	l = −17→17
26025 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 0.999P] where P = (Fo^2 + 2Fc^2)/3
3551 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.91971 (4)	0.21669 (4)	0.81440 (3)	0.03634 (13)
S2	0.78404 (4)	0.40992 (4)	0.79051 (3)	0.03870 (13)
O1	1.24609 (11)	0.17686 (12)	1.14080 (8)	0.0502 (3)
O2	0.71155 (13)	0.47433 (13)	0.84429 (8)	0.0571 (4)
O3	0.88781 (11)	0.46575 (12)	0.76918 (9)	0.0536 (4)
N1	0.80920 (12)	0.28740 (13)	0.84166 (9)	0.0394 (3)
C1	1.2362 (2)	0.2417 (2)	1.22155 (13)	0.0635 (6)
H1A	1.2431	0.3236	1.2094	0.095*
H1B	1.2956	0.2185	1.267	0.095*
H1C	1.1631	0.2267	1.2424	0.095*
C2	1.16706 (14)	0.19384 (16)	1.06907 (11)	0.0386 (4)
C3	1.18363 (15)	0.12763 (17)	0.99314 (12)	0.0450 (4)
H3A	1.2461	0.0778	0.9944	0.054*
C4	1.10890 (15)	0.13527 (17)	0.91682 (12)	0.0435 (4)
H4	1.121	0.0919	0.8659	0.052*
C5	1.01436 (14)	0.20857 (15)	0.91591 (11)	0.0353 (4)
C6	0.70321 (14)	0.37950 (15)	0.68654 (10)	0.0354 (4)
C7	0.75666 (15)	0.34315 (17)	0.61306 (11)	0.0423 (4)
H7	0.8358	0.3372	0.6174	0.051*
C8	0.69235 (17)	0.31579 (18)	0.53356 (12)	0.0479 (4)
H8	0.7288	0.2908	0.4846	0.058*
C9	0.57456 (17)	0.32469 (19)	0.52483 (12)	0.0502 (5)
C10	0.5053 (2)	0.2921 (3)	0.43719 (15)	0.0783 (7)
H10A	0.4393	0.2483	0.4499	0.117*
H10B	0.5511	0.2456	0.4013	0.117*
H10C	0.4814	0.3618	0.4048	0.117*
C11	0.99757 (15)	0.27512 (16)	0.99015 (11)	0.0399 (4)
H11	0.9349	0.3247	0.9887	0.048*
C12	1.07427 (15)	0.26834 (16)	1.06728 (12)	0.0423 (4)
H12	1.0634	0.3136	1.1175	0.051*
C13	0.86641 (17)	0.06721 (16)	0.80931 (12)	0.0456 (4)
H13A	0.9301	0.0132	0.8122	0.055*
H13B	0.824	0.0523	0.8605	0.055*
C14	0.79035 (15)	0.04823 (15)	0.72325 (11)	0.0400 (4)
C15	0.67372 (16)	0.06473 (18)	0.72001 (13)	0.0505 (5)
H15	0.6415	0.0884	0.7714	0.061*
C16	0.60467 (17)	0.0460 (2)	0.64022 (15)	0.0598 (6)
H16	0.5261	0.0564	0.6383	0.072*
C17	0.65223 (18)	0.0120 (2)	0.56390 (14)	0.0586 (5)
H17	0.6059	0.0001	0.5102	0.07*
C18	0.76801 (18)	−0.00444 (19)	0.56687 (13)	0.0542 (5)
H18	0.7999	−0.0279	0.5153	0.065*
C19	0.83695 (16)	0.01362 (17)	0.64584 (12)	0.0461 (4)
H19	0.9153	0.0025	0.6473	0.055*
C20	0.52325 (17)	0.3614 (2)	0.59898 (15)	0.0644 (6)
H20	0.4442	0.368	0.5946	0.077*
C21	0.58601 (16)	0.3883 (2)	0.67931 (13)	0.0547 (5)
H21	0.5495	0.4123	0.7285	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0402 (2)	0.0387 (2)	0.0296 (2)	−0.00158 (17)	0.00101 (16)	0.00320 (16)
S2	0.0453 (3)	0.0368 (2)	0.0330 (2)	−0.00009 (18)	−0.00091 (17)	0.00377 (17)
O1	0.0514 (8)	0.0547 (8)	0.0412 (7)	0.0070 (6)	−0.0108 (6)	−0.0028 (6)
O2	0.0751 (9)	0.0553 (9)	0.0406 (7)	0.0175 (7)	0.0039 (6)	−0.0070 (6)
O3	0.0537 (8)	0.0515 (8)	0.0531 (8)	−0.0158 (6)	−0.0063 (6)	0.0136 (6)
N1	0.0407 (8)	0.0431 (9)	0.0345 (7)	0.0018 (6)	0.0039 (6)	0.0097 (6)
C1	0.0896 (16)	0.0490 (12)	0.0461 (11)	0.0056 (11)	−0.0205 (11)	−0.0084 (9)
C2	0.0400 (9)	0.0389 (10)	0.0357 (9)	−0.0032 (7)	−0.0016 (7)	0.0023 (7)
C3	0.0411 (10)	0.0477 (11)	0.0455 (10)	0.0115 (8)	0.0012 (8)	−0.0031 (8)
C4	0.0453 (10)	0.0486 (11)	0.0366 (9)	0.0062 (8)	0.0046 (7)	−0.0067 (8)
C5	0.0367 (9)	0.0373 (9)	0.0314 (8)	−0.0015 (7)	0.0012 (6)	0.0021 (7)
C6	0.0372 (9)	0.0372 (9)	0.0313 (8)	0.0023 (7)	0.0017 (6)	0.0056 (7)
C7	0.0371 (9)	0.0509 (11)	0.0397 (9)	0.0012 (8)	0.0075 (7)	0.0026 (8)
C8	0.0573 (11)	0.0526 (12)	0.0351 (9)	−0.0015 (9)	0.0104 (8)	−0.0020 (8)
C9	0.0546 (11)	0.0541 (12)	0.0397 (10)	−0.0040 (9)	−0.0055 (8)	0.0034 (8)
C10	0.0830 (17)	0.092 (2)	0.0544 (13)	−0.0111 (14)	−0.0195 (12)	−0.0032 (12)
C11	0.0399 (9)	0.0401 (10)	0.0395 (9)	0.0062 (7)	0.0031 (7)	−0.0013 (7)
C12	0.0482 (10)	0.0423 (10)	0.0359 (9)	0.0037 (8)	0.0026 (7)	−0.0057 (7)
C13	0.0577 (11)	0.0366 (10)	0.0403 (10)	−0.0034 (8)	−0.0058 (8)	0.0037 (7)
C14	0.0476 (10)	0.0322 (9)	0.0387 (9)	−0.0043 (7)	−0.0027 (7)	0.0023 (7)
C15	0.0496 (11)	0.0522 (12)	0.0501 (11)	−0.0048 (9)	0.0072 (9)	−0.0012 (9)
C16	0.0393 (10)	0.0684 (15)	0.0696 (14)	−0.0070 (10)	−0.0044 (9)	0.0019 (11)
C17	0.0577 (12)	0.0639 (14)	0.0499 (11)	−0.0110 (10)	−0.0147 (9)	−0.0016 (10)
C18	0.0626 (13)	0.0567 (13)	0.0422 (10)	−0.0025 (10)	0.0002 (9)	−0.0064 (9)
C19	0.0442 (10)	0.0465 (11)	0.0463 (10)	0.0013 (8)	−0.0012 (8)	−0.0019 (8)
C20	0.0368 (10)	0.0946 (18)	0.0599 (13)	0.0107 (11)	−0.0040 (9)	−0.0027 (12)
C21	0.0412 (10)	0.0804 (15)	0.0427 (10)	0.0141 (10)	0.0060 (8)	−0.0045 (10)

Geometric parameters (Å, º)

S1—N1	1.6200 (15)	C9—C20	1.379 (3)
S1—C5	1.7861 (16)	C9—C10	1.513 (3)
S1—C13	1.8226 (19)	C10—H10A	0.96
S2—O2	1.4343 (14)	C10—H10B	0.96
S2—O3	1.4435 (13)	C10—H10C	0.96
S2—N1	1.6099 (14)	C11—C12	1.389 (2)
S2—C6	1.7673 (16)	C11—H11	0.93
O1—C2	1.357 (2)	C12—H12	0.93
O1—C1	1.430 (2)	C13—C14	1.502 (2)
C1—H1A	0.96	C13—H13A	0.97
C1—H1B	0.96	C13—H13B	0.97
C1—H1C	0.96	C14—C15	1.382 (3)
C2—C12	1.385 (2)	C14—C19	1.386 (3)
C2—C3	1.393 (2)	C15—C16	1.386 (3)
C3—C4	1.367 (2)	C15—H15	0.93
C3—H3A	0.93	C16—C17	1.375 (3)
C4—C5	1.393 (2)	C16—H16	0.93
C4—H4	0.93	C17—C18	1.373 (3)
C5—C11	1.375 (2)	C17—H17	0.93
C6—C21	1.377 (2)	C18—C19	1.375 (3)
C6—C7	1.383 (2)	C18—H18	0.93
C7—C8	1.375 (2)	C19—H19	0.93
C7—H7	0.93	C20—C21	1.375 (3)
C8—C9	1.384 (3)	C20—H20	0.93
C8—H8	0.93	C21—H21	0.93
N1—S1—C5	105.11 (8)	C9—C10—H10B	109.5
N1—S1—C13	101.42 (9)	H10A—C10—H10B	109.5
C5—S1—C13	99.69 (8)	C9—C10—H10C	109.5
O2—S2—O3	117.49 (9)	H10A—C10—H10C	109.5
O2—S2—N1	105.95 (8)	H10B—C10—H10C	109.5
O3—S2—N1	111.84 (8)	C5—C11—C12	119.99 (16)
O2—S2—C6	107.08 (8)	C5—C11—H11	120.0
O3—S2—C6	106.60 (8)	C12—C11—H11	120.0
N1—S2—C6	107.41 (8)	C2—C12—C11	119.66 (16)
C2—O1—C1	118.66 (15)	C2—C12—H12	120.2
S2—N1—S1	115.49 (8)	C11—C12—H12	120.2
O1—C1—H1A	109.5	C14—C13—S1	110.11 (12)
O1—C1—H1B	109.5	C14—C13—H13A	109.6
H1A—C1—H1B	109.5	S1—C13—H13A	109.6
O1—C1—H1C	109.5	C14—C13—H13B	109.6
H1A—C1—H1C	109.5	S1—C13—H13B	109.6
H1B—C1—H1C	109.5	H13A—C13—H13B	108.2
O1—C2—C12	125.39 (16)	C15—C14—C19	119.20 (16)
O1—C2—C3	114.82 (15)	C15—C14—C13	120.83 (17)
C12—C2—C3	119.78 (16)	C19—C14—C13	119.97 (17)
C4—C3—C2	120.59 (16)	C14—C15—C16	120.09 (18)
C4—C3—H3A	119.7	C14—C15—H15	120.0
C2—C3—H3A	119.7	C16—C15—H15	120.0
C3—C4—C5	119.44 (16)	C17—C16—C15	120.03 (19)
C3—C4—H4	120.3	C17—C16—H16	120.0
C5—C4—H4	120.3	C15—C16—H16	120.0
C11—C5—C4	120.51 (15)	C18—C17—C16	120.04 (19)
C11—C5—S1	121.58 (13)	C18—C17—H17	120.0
C4—C5—S1	117.87 (12)	C16—C17—H17	120.0
C21—C6—C7	119.67 (16)	C17—C18—C19	120.24 (19)
C21—C6—S2	119.92 (13)	C17—C18—H18	119.9
C7—C6—S2	120.38 (13)	C19—C18—H18	119.9
C8—C7—C6	119.72 (16)	C18—C19—C14	120.41 (18)
C8—C7—H7	120.1	C18—C19—H19	119.8
C6—C7—H7	120.1	C14—C19—H19	119.8
C7—C8—C9	121.46 (17)	C21—C20—C9	121.69 (18)
C7—C8—H8	119.3	C21—C20—H20	119.2
C9—C8—H8	119.3	C9—C20—H20	119.2
C20—C9—C8	117.74 (17)	C20—C21—C6	119.72 (17)
C20—C9—C10	121.7 (2)	C20—C21—H21	120.1
C8—C9—C10	120.59 (19)	C6—C21—H21	120.1
C9—C10—H10A	109.5

(Compound_8_CCDC)

Crystal data

C21H21NO3S2	F(000) = 840
Mr = 399.51	Dx = 1.319 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3129 reflections
a = 11.7937 (9) Å	θ = 2.5–23.1°
b = 11.4816 (7) Å	µ = 0.29 mm^−1
c = 14.9358 (12) Å	T = 300 K
β = 95.972 (3)°	Block, colorles
V = 2011.5 (3) Å^3	0.43 × 0.41 × 0.27 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	3546 independent reflections
Radiation source: micro-focus sealed tube	2664 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −14→14
Tmin = 0.870, Tmax = 0.870	k = −13→12
12920 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0813P)^2] where P = (Fo^2 + 2Fc^2)/3
3546 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.91969 (5)	0.21665 (5)	0.81432 (4)	0.0375 (2)
S3	0.78419 (6)	0.40976 (5)	0.79044 (4)	0.0402 (2)
O26	1.24615 (15)	0.17768 (16)	1.14026 (12)	0.0512 (5)
O4	0.88809 (16)	0.46532 (16)	0.76935 (13)	0.0556 (5)
O5	0.71164 (17)	0.47438 (17)	0.84434 (12)	0.0589 (6)
N2	0.80930 (17)	0.28747 (17)	0.84147 (14)	0.0400 (5)
C27	1.2366 (3)	0.2421 (3)	1.22105 (19)	0.0652 (9)
H27A	1.2449	0.3237	1.2094	0.098*
H27B	1.2952	0.2178	1.2666	0.098*
H27C	1.1632	0.2281	1.2414	0.098*
C23	1.1673 (2)	0.1941 (2)	1.06897 (17)	0.0399 (6)
C24	1.1835 (2)	0.1282 (2)	0.99287 (17)	0.0464 (7)
H24	1.2460	0.0786	0.9939	0.056*
C25	1.1088 (2)	0.1358 (2)	0.91676 (17)	0.0453 (7)
H25	1.1210	0.0924	0.8661	0.054*
C20	1.0144 (2)	0.2087 (2)	0.91535 (16)	0.0349 (6)
C6	0.7033 (2)	0.3795 (2)	0.68668 (15)	0.0361 (6)
C7	0.5863 (2)	0.3880 (3)	0.67936 (19)	0.0566 (8)
H7	0.5498	0.4125	0.7283	0.068*
C8	0.5234 (2)	0.3601 (3)	0.5991 (2)	0.0682 (9)
H8	0.4444	0.3658	0.5950	0.082*
C9	0.5746 (2)	0.3239 (2)	0.52474 (18)	0.0507 (7)
C12	0.5053 (3)	0.2913 (3)	0.4369 (2)	0.0809 (11)
H12A	0.4373	0.2513	0.4496	0.121*
H12B	0.5497	0.2413	0.4026	0.121*
H12C	0.4851	0.3606	0.4030	0.121*
C10	0.6923 (2)	0.3151 (2)	0.53404 (18)	0.0494 (7)
H10	0.7289	0.2899	0.4853	0.059*
C11	0.7563 (2)	0.3426 (2)	0.61328 (17)	0.0432 (6)
H11	0.8353	0.3365	0.6176	0.052*
C13	0.8663 (2)	0.0672 (2)	0.80893 (17)	0.0467 (7)
H13A	0.9299	0.0133	0.8120	0.056*
H13B	0.8237	0.0523	0.8599	0.056*
C14	0.7905 (2)	0.0481 (2)	0.72290 (17)	0.0403 (6)
C19	0.8364 (2)	0.0135 (2)	0.64557 (18)	0.0474 (7)
H19	0.9147	0.0020	0.6470	0.057*
C18	0.7677 (3)	−0.0041 (2)	0.5667 (2)	0.0564 (8)
H18	0.7996	−0.0271	0.5151	0.068*
C17	0.6520 (3)	0.0120 (3)	0.5640 (2)	0.0597 (8)
H17	0.6057	0.0004	0.5104	0.072*
C16	0.6047 (2)	0.0453 (3)	0.6398 (2)	0.0613 (8)
H16	0.5263	0.0550	0.6380	0.074*
C15	0.6738 (2)	0.0645 (2)	0.71944 (19)	0.0515 (7)
H15	0.6416	0.0884	0.7706	0.062*
C21	0.9981 (2)	0.2752 (2)	0.99003 (17)	0.0418 (6)
H21	0.9354	0.3246	0.9887	0.050*
C22	1.0742 (2)	0.2690 (2)	1.06678 (17)	0.0429 (6)
H22	1.0634	0.3146	1.1166	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0423 (4)	0.0394 (4)	0.0301 (4)	−0.0018 (3)	0.0008 (3)	0.0032 (3)
S3	0.0473 (4)	0.0380 (4)	0.0341 (4)	−0.0003 (3)	−0.0014 (3)	0.0044 (3)
O26	0.0520 (11)	0.0568 (11)	0.0415 (11)	0.0091 (9)	−0.0111 (9)	−0.0030 (9)
O4	0.0546 (12)	0.0531 (11)	0.0564 (12)	−0.0178 (10)	−0.0069 (10)	0.0154 (10)
O5	0.0762 (14)	0.0570 (12)	0.0433 (12)	0.0202 (11)	0.0048 (10)	−0.0078 (9)
N2	0.0426 (12)	0.0423 (12)	0.0351 (12)	0.0036 (10)	0.0041 (9)	0.0109 (9)
C27	0.094 (2)	0.0495 (17)	0.0460 (18)	0.0055 (17)	−0.0224 (17)	−0.0085 (14)
C23	0.0414 (15)	0.0395 (14)	0.0378 (15)	−0.0018 (12)	−0.0002 (12)	0.0019 (11)
C24	0.0426 (15)	0.0499 (15)	0.0455 (16)	0.0128 (13)	−0.0004 (12)	−0.0041 (13)
C25	0.0487 (16)	0.0507 (16)	0.0370 (15)	0.0058 (13)	0.0070 (12)	−0.0066 (12)
C20	0.0359 (13)	0.0374 (13)	0.0311 (13)	−0.0002 (11)	0.0022 (10)	0.0027 (11)
C6	0.0382 (13)	0.0362 (13)	0.0334 (14)	0.0016 (11)	0.0017 (11)	0.0064 (11)
C7	0.0429 (16)	0.084 (2)	0.0429 (17)	0.0156 (15)	0.0062 (13)	−0.0062 (15)
C8	0.0376 (15)	0.102 (3)	0.063 (2)	0.0153 (17)	−0.0078 (15)	−0.0009 (19)
C9	0.0546 (17)	0.0554 (17)	0.0401 (16)	−0.0033 (14)	−0.0047 (14)	0.0005 (13)
C12	0.088 (3)	0.094 (3)	0.054 (2)	−0.010 (2)	−0.0242 (19)	−0.0017 (18)
C10	0.0574 (18)	0.0549 (16)	0.0372 (16)	−0.0012 (14)	0.0114 (13)	−0.0013 (13)
C11	0.0381 (14)	0.0513 (16)	0.0409 (15)	0.0001 (12)	0.0065 (12)	0.0031 (13)
C13	0.0575 (17)	0.0392 (14)	0.0416 (16)	−0.0026 (13)	−0.0036 (13)	0.0047 (12)
C14	0.0472 (15)	0.0332 (13)	0.0389 (15)	−0.0053 (12)	−0.0024 (12)	0.0016 (11)
C19	0.0442 (15)	0.0487 (16)	0.0480 (17)	0.0023 (13)	−0.0016 (13)	−0.0033 (13)
C18	0.0638 (19)	0.0607 (18)	0.0438 (17)	−0.0005 (16)	0.0018 (14)	−0.0073 (14)
C17	0.0572 (19)	0.068 (2)	0.0500 (19)	−0.0094 (16)	−0.0159 (15)	−0.0032 (16)
C16	0.0389 (16)	0.069 (2)	0.074 (2)	−0.0087 (15)	−0.0059 (16)	−0.0001 (17)
C15	0.0506 (17)	0.0539 (17)	0.0504 (18)	−0.0024 (14)	0.0077 (14)	−0.0012 (14)
C21	0.0418 (14)	0.0417 (14)	0.0418 (15)	0.0088 (12)	0.0036 (12)	−0.0014 (12)
C22	0.0489 (15)	0.0441 (15)	0.0352 (14)	0.0040 (12)	0.0018 (12)	−0.0063 (12)

Geometric parameters (Å, º)

S1—N2	1.622 (2)	C9—C10	1.383 (4)
S1—C20	1.784 (2)	C9—C12	1.519 (4)
S1—C13	1.826 (3)	C12—H12A	0.9600
S3—O5	1.4401 (19)	C12—H12B	0.9600
S3—O4	1.4450 (19)	C12—H12C	0.9600
S3—N2	1.610 (2)	C10—C11	1.373 (3)
S3—C6	1.768 (2)	C10—H10	0.9300
O26—C23	1.352 (3)	C11—H11	0.9300
O26—C27	1.430 (3)	C13—C14	1.503 (3)
C27—H27A	0.9600	C13—H13A	0.9700
C27—H27B	0.9600	C13—H13B	0.9700
C27—H27C	0.9600	C14—C19	1.384 (4)
C23—C22	1.392 (3)	C14—C15	1.385 (4)
C23—C24	1.395 (4)	C19—C18	1.374 (4)
C24—C25	1.367 (3)	C19—H19	0.9300
C24—H24	0.9300	C18—C17	1.374 (4)
C25—C20	1.391 (3)	C18—H18	0.9300
C25—H25	0.9300	C17—C16	1.367 (4)
C20—C21	1.382 (3)	C17—H17	0.9300
C6—C7	1.376 (3)	C16—C15	1.387 (4)
C6—C11	1.384 (3)	C16—H16	0.9300
C7—C8	1.380 (4)	C15—H15	0.9300
C7—H7	0.9300	C21—C22	1.383 (3)
C8—C9	1.383 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—H22	0.9300
N2—S1—C20	105.21 (11)	C9—C12—H12B	109.5
N2—S1—C13	101.52 (12)	H12A—C12—H12B	109.5
C20—S1—C13	99.90 (11)	C9—C12—H12C	109.5
O5—S3—O4	117.46 (13)	H12A—C12—H12C	109.5
O5—S3—N2	105.99 (11)	H12B—C12—H12C	109.5
O4—S3—N2	111.70 (11)	C11—C10—C9	121.7 (3)
O5—S3—C6	107.08 (12)	C11—C10—H10	119.1
O4—S3—C6	106.75 (11)	C9—C10—H10	119.1
N2—S3—C6	107.41 (11)	C10—C11—C6	120.0 (2)
C23—O26—C27	119.0 (2)	C10—C11—H11	120.0
S3—N2—S1	115.58 (12)	C6—C11—H11	120.0
O26—C27—H27A	109.5	C14—C13—S1	110.29 (17)
O26—C27—H27B	109.5	C14—C13—H13A	109.6
H27A—C27—H27B	109.5	S1—C13—H13A	109.6
O26—C27—H27C	109.5	C14—C13—H13B	109.6
H27A—C27—H27C	109.5	S1—C13—H13B	109.6
H27B—C27—H27C	109.5	H13A—C13—H13B	108.1
O26—C23—C22	125.5 (2)	C19—C14—C15	118.8 (2)
O26—C23—C24	115.1 (2)	C19—C14—C13	120.4 (2)
C22—C23—C24	119.4 (2)	C15—C14—C13	120.8 (2)
C25—C24—C23	120.8 (2)	C18—C19—C14	120.7 (3)
C25—C24—H24	119.6	C18—C19—H19	119.6
C23—C24—H24	119.6	C14—C19—H19	119.6
C24—C25—C20	119.8 (2)	C19—C18—C17	120.1 (3)
C24—C25—H25	120.1	C19—C18—H18	119.9
C20—C25—H25	120.1	C17—C18—H18	119.9
C21—C20—C25	119.9 (2)	C16—C17—C18	120.1 (3)
C21—C20—S1	121.81 (19)	C16—C17—H17	119.9
C25—C20—S1	118.25 (19)	C18—C17—H17	119.9
C7—C6—C11	119.4 (2)	C17—C16—C15	120.1 (3)
C7—C6—S3	120.0 (2)	C17—C16—H16	120.0
C11—C6—S3	120.51 (19)	C15—C16—H16	120.0
C6—C7—C8	119.8 (3)	C14—C15—C16	120.2 (3)
C6—C7—H7	120.1	C14—C15—H15	119.9
C8—C7—H7	120.1	C16—C15—H15	119.9
C7—C8—C9	121.8 (3)	C20—C21—C22	120.5 (2)
C7—C8—H8	119.1	C20—C21—H21	119.7
C9—C8—H8	119.1	C22—C21—H21	119.7
C8—C9—C10	117.3 (3)	C21—C22—C23	119.6 (2)
C8—C9—C12	121.8 (3)	C21—C22—H22	120.2
C10—C9—C12	120.9 (3)	C23—C22—H22	120.2
C9—C12—H12A	109.5

(Compound_8_X2S)

Crystal data

C21H21NO3S2	F(000) = 840
Mr = 399.51	Dx = 1.319 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3129 reflections
a = 11.7937 (9) Å	θ = 2.5–23.1°
b = 11.4816 (7) Å	µ = 0.29 mm^−1
c = 14.9358 (12) Å	T = 300 K
β = 95.972 (3)°	Block, colorless
V = 2011.5 (3) Å^3	0.43 × 0.41 × 0.27 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	3546 independent reflections
Radiation source: micro-focus sealed tube	2664 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −14→14
Tmin = 0.870, Tmax = 0.870	k = −13→12
12920 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0849P)^2 + 0.0076P] where P = (Fo^2 + 2Fc^2)/3
3546 reflections	(Δ/σ)max = 0.161
246 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.78419 (6)	0.40976 (5)	0.79044 (4)	0.0402 (2)
S2	0.91969 (5)	0.21664 (5)	0.81432 (4)	0.0374 (2)
O1	1.24615 (15)	0.17766 (16)	1.14025 (12)	0.0512 (5)
O2	0.88808 (16)	0.46531 (16)	0.76934 (13)	0.0556 (5)
O3	0.71164 (17)	0.47438 (17)	0.84433 (12)	0.0589 (6)
N1	0.80930 (17)	0.28746 (17)	0.84147 (14)	0.0400 (5)
C1	0.5053 (3)	0.2914 (3)	0.4369 (2)	0.0809 (11)
H1A	0.4371	0.2517	0.4495	0.121*
H1B	0.5496	0.2412	0.4027	0.121*
H1C	0.4853	0.3607	0.4029	0.121*
C2	0.5746 (2)	0.3240 (2)	0.52474 (18)	0.0507 (7)
C3	0.5234 (2)	0.3601 (3)	0.5991 (2)	0.0682 (9)
H3	0.4444	0.3658	0.5950	0.082*
C4	0.5863 (2)	0.3880 (3)	0.67935 (19)	0.0566 (8)
H4	0.5498	0.4125	0.7283	0.068*
C5	0.7033 (2)	0.3795 (2)	0.68666 (15)	0.0361 (6)
C6	1.0144 (2)	0.2087 (2)	0.91536 (16)	0.0349 (6)
C7	0.9981 (2)	0.2752 (2)	0.99003 (17)	0.0418 (6)
H7	0.9354	0.3245	0.9887	0.050*
C8	1.0742 (2)	0.2690 (2)	1.06679 (17)	0.0429 (6)
H8	1.0634	0.3146	1.1167	0.052*
C9	1.1673 (2)	0.1941 (2)	1.06896 (17)	0.0399 (6)
C10	1.2366 (3)	0.2421 (3)	1.22106 (19)	0.0652 (9)
H10A	1.2449	0.3237	1.2094	0.098*
H10B	1.2952	0.2177	1.2666	0.098*
H10C	1.1632	0.2281	1.2414	0.098*
C11	0.8663 (2)	0.0672 (2)	0.80896 (17)	0.0467 (7)
H11A	0.9299	0.0133	0.8120	0.056*
H11B	0.8237	0.0523	0.8600	0.056*
C12	0.7905 (2)	0.0481 (2)	0.72291 (17)	0.0403 (6)
C13	0.6738 (2)	0.0645 (2)	0.71947 (19)	0.0515 (7)
H13	0.6416	0.0884	0.7707	0.062*
C14	0.6047 (2)	0.0453 (3)	0.6398 (2)	0.0613 (8)
H14	0.5263	0.0551	0.6380	0.074*
C15	0.6520 (3)	0.0121 (3)	0.5640 (2)	0.0598 (8)
H15	0.6056	0.0004	0.5104	0.072*
C16	0.7677 (3)	−0.0041 (2)	0.5667 (2)	0.0564 (8)
H16	0.7996	−0.0271	0.5151	0.068*
C17	0.8365 (2)	0.0135 (2)	0.64559 (18)	0.0474 (7)
H17	0.9147	0.0020	0.6470	0.057*
C18	1.1088 (2)	0.1358 (2)	0.91676 (17)	0.0453 (7)
H18	1.1209	0.0924	0.8661	0.054*
C19	1.1835 (2)	0.1282 (2)	0.99286 (17)	0.0464 (7)
H19	1.2460	0.0786	0.9939	0.056*
C20	0.7563 (2)	0.3427 (2)	0.61328 (17)	0.0432 (6)
H20	0.8354	0.3365	0.6176	0.052*
C21	0.6923 (2)	0.3152 (2)	0.53404 (18)	0.0494 (7)
H21	0.7289	0.2900	0.4853	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0473 (4)	0.0380 (4)	0.0341 (4)	−0.0003 (3)	−0.0014 (3)	0.0043 (3)
S2	0.0423 (4)	0.0394 (4)	0.0301 (4)	−0.0018 (3)	0.0008 (3)	0.0032 (3)
O1	0.0520 (11)	0.0568 (11)	0.0415 (11)	0.0090 (9)	−0.0111 (9)	−0.0030 (9)
O2	0.0548 (12)	0.0531 (11)	0.0564 (12)	−0.0178 (10)	−0.0069 (10)	0.0154 (10)
O3	0.0762 (14)	0.0570 (12)	0.0433 (12)	0.0201 (11)	0.0048 (10)	−0.0077 (9)
N1	0.0427 (12)	0.0423 (12)	0.0351 (12)	0.0036 (10)	0.0041 (9)	0.0109 (9)
C1	0.088 (3)	0.094 (3)	0.054 (2)	−0.010 (2)	−0.0242 (19)	−0.0016 (18)
C2	0.0546 (17)	0.0554 (17)	0.0400 (16)	−0.0033 (14)	−0.0048 (13)	0.0005 (13)
C3	0.0376 (15)	0.102 (3)	0.063 (2)	0.0153 (17)	−0.0078 (14)	−0.0010 (19)
C4	0.0429 (16)	0.084 (2)	0.0430 (17)	0.0156 (15)	0.0062 (13)	−0.0063 (15)
C5	0.0382 (13)	0.0362 (13)	0.0334 (14)	0.0016 (11)	0.0016 (11)	0.0064 (11)
C6	0.0359 (13)	0.0375 (13)	0.0311 (13)	−0.0003 (11)	0.0022 (10)	0.0027 (11)
C7	0.0418 (14)	0.0417 (14)	0.0419 (15)	0.0087 (12)	0.0036 (12)	−0.0014 (12)
C8	0.0489 (15)	0.0441 (15)	0.0353 (14)	0.0040 (12)	0.0018 (12)	−0.0063 (12)
C9	0.0414 (14)	0.0395 (14)	0.0378 (15)	−0.0018 (12)	−0.0002 (12)	0.0020 (11)
C10	0.094 (2)	0.0495 (17)	0.0460 (18)	0.0055 (17)	−0.0224 (17)	−0.0084 (14)
C11	0.0575 (17)	0.0392 (14)	0.0415 (16)	−0.0026 (13)	−0.0037 (13)	0.0047 (12)
C12	0.0473 (15)	0.0332 (13)	0.0389 (15)	−0.0053 (12)	−0.0024 (12)	0.0016 (11)
C13	0.0505 (17)	0.0540 (17)	0.0504 (17)	−0.0023 (14)	0.0076 (14)	−0.0013 (14)
C14	0.0390 (15)	0.069 (2)	0.074 (2)	−0.0086 (15)	−0.0058 (15)	−0.0001 (17)
C15	0.0572 (19)	0.068 (2)	0.0501 (19)	−0.0094 (16)	−0.0158 (15)	−0.0032 (15)
C16	0.0639 (19)	0.0608 (18)	0.0439 (17)	−0.0005 (16)	0.0018 (14)	−0.0072 (14)
C17	0.0442 (15)	0.0486 (16)	0.0481 (17)	0.0023 (13)	−0.0016 (13)	−0.0033 (13)
C18	0.0488 (15)	0.0508 (16)	0.0370 (15)	0.0059 (13)	0.0070 (12)	−0.0066 (12)
C19	0.0427 (15)	0.0499 (15)	0.0454 (16)	0.0128 (13)	−0.0005 (12)	−0.0041 (13)
C20	0.0381 (14)	0.0513 (16)	0.0408 (15)	0.0002 (12)	0.0066 (11)	0.0032 (13)
C21	0.0574 (17)	0.0549 (16)	0.0372 (15)	−0.0013 (14)	0.0114 (13)	−0.0013 (13)

Geometric parameters (Å, º)

S1—O3	1.4400 (19)	C8—H8	0.9300
S1—O2	1.4450 (19)	C9—C19	1.395 (4)
S1—N1	1.610 (2)	C10—H10A	0.9600
S1—C5	1.768 (2)	C10—H10B	0.9600
S2—N1	1.622 (2)	C10—H10C	0.9600
S2—C6	1.784 (2)	C11—C12	1.503 (3)
S2—C11	1.826 (3)	C11—H11A	0.9700
O1—C9	1.352 (3)	C11—H11B	0.9700
O1—C10	1.430 (3)	C12—C17	1.384 (4)
C1—C2	1.519 (4)	C12—C13	1.385 (4)
C1—H1A	0.9600	C13—C14	1.387 (4)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.367 (4)
C2—C3	1.382 (4)	C14—H14	0.9300
C2—C21	1.383 (4)	C15—C16	1.374 (4)
C3—C4	1.380 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.374 (4)
C4—C5	1.376 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C20	1.383 (3)	C18—C19	1.367 (3)
C6—C7	1.382 (3)	C18—H18	0.9300
C6—C18	1.391 (3)	C19—H19	0.9300
C7—C8	1.383 (3)	C20—C21	1.373 (3)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.392 (3)	C21—H21	0.9300
O3—S1—O2	117.46 (13)	O1—C10—H10B	109.5
O3—S1—N1	105.99 (11)	H10A—C10—H10B	109.5
O2—S1—N1	111.70 (11)	O1—C10—H10C	109.5
O3—S1—C5	107.07 (12)	H10A—C10—H10C	109.5
O2—S1—C5	106.74 (11)	H10B—C10—H10C	109.5
N1—S1—C5	107.41 (11)	C12—C11—S2	110.27 (17)
N1—S2—C6	105.22 (11)	C12—C11—H11A	109.6
N1—S2—C11	101.52 (12)	S2—C11—H11A	109.6
C6—S2—C11	99.88 (11)	C12—C11—H11B	109.6
C9—O1—C10	119.0 (2)	S2—C11—H11B	109.6
S1—N1—S2	115.58 (12)	H11A—C11—H11B	108.1
C2—C1—H1A	109.5	C17—C12—C13	118.8 (2)
C2—C1—H1B	109.5	C17—C12—C11	120.4 (2)
H1A—C1—H1B	109.5	C13—C12—C11	120.8 (2)
C2—C1—H1C	109.5	C12—C13—C14	120.2 (3)
H1A—C1—H1C	109.5	C12—C13—H13	119.9
H1B—C1—H1C	109.5	C14—C13—H13	119.9
C3—C2—C21	117.3 (3)	C15—C14—C13	120.1 (3)
C3—C2—C1	121.8 (3)	C15—C14—H14	120.0
C21—C2—C1	120.8 (3)	C13—C14—H14	120.0
C4—C3—C2	121.8 (3)	C14—C15—C16	120.1 (3)
C4—C3—H3	119.1	C14—C15—H15	119.9
C2—C3—H3	119.1	C16—C15—H15	119.9
C5—C4—C3	119.8 (3)	C17—C16—C15	120.1 (3)
C5—C4—H4	120.1	C17—C16—H16	120.0
C3—C4—H4	120.1	C15—C16—H16	120.0
C4—C5—C20	119.4 (2)	C16—C17—C12	120.7 (3)
C4—C5—S1	120.0 (2)	C16—C17—H17	119.7
C20—C5—S1	120.49 (19)	C12—C17—H17	119.7
C7—C6—C18	119.9 (2)	C19—C18—C6	119.8 (2)
C7—C6—S2	121.82 (19)	C19—C18—H18	120.1
C18—C6—S2	118.24 (19)	C6—C18—H18	120.1
C6—C7—C8	120.5 (2)	C18—C19—C9	120.8 (2)
C6—C7—H7	119.7	C18—C19—H19	119.6
C8—C7—H7	119.7	C9—C19—H19	119.6
C7—C8—C9	119.6 (2)	C21—C20—C5	120.0 (2)
C7—C8—H8	120.2	C21—C20—H20	120.0
C9—C8—H8	120.2	C5—C20—H20	120.0
O1—C9—C8	125.5 (2)	C20—C21—C2	121.7 (3)
O1—C9—C19	115.1 (2)	C20—C21—H21	119.1
C8—C9—C19	119.4 (2)	C2—C21—H21	119.1
O1—C10—H10A	109.5

(Compound_9_X2S)

Crystal data

C13H10F2OS	F(000) = 520
Mr = 252.27	Dx = 1.448 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2280 reflections
a = 8.3649 (16) Å	θ = 3.7–24.7°
b = 5.5063 (10) Å	µ = 0.29 mm^−1
c = 25.129 (4) Å	T = 300 K
V = 1157.4 (4) Å^3	Block, colorless
Z = 4	0.31 × 0.27 × 0.24 mm

Data collection

Bruker SMART X2S diffractometer	2013 independent reflections
Radiation source: micro-focus sealed tube	1760 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.037
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.749, Tmax = 0.871	k = −6→5
6646 measured reflections	l = −29→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0681P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max = 0.020
2013 reflections	Δρmax = 0.18 e Å^−3
154 parameters	Δρmin = −0.19 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (10)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.29434 (9)	0.17051 (14)	0.00059 (3)	0.0413 (2)
F1	0.5368 (4)	0.3431 (4)	−0.21543 (9)	0.0785 (8)
F2	0.2986 (4)	0.1816 (5)	0.25419 (9)	0.0833 (10)
O1	0.3161 (3)	−0.0944 (4)	0.01086 (11)	0.0571 (7)
C1	0.4817 (5)	0.3033 (8)	−0.16523 (14)	0.0539 (10)
C2	0.5299 (5)	0.0960 (8)	−0.13933 (16)	0.0543 (10)
H2	0.5982	−0.0150	−0.1555	0.065*
C3	0.4728 (4)	0.0590 (7)	−0.08826 (14)	0.0449 (8)
H3	0.5015	−0.0808	−0.0698	0.054*
C4	0.3734 (4)	0.2274 (6)	−0.06441 (12)	0.0376 (7)
C5	0.4491 (4)	0.3284 (6)	0.03887 (13)	0.0389 (8)
H5A	0.5535	0.2622	0.0305	0.047*
H5B	0.4491	0.5000	0.0301	0.047*
C6	0.4130 (4)	0.2934 (6)	0.09713 (13)	0.0355 (8)
C7	0.3139 (4)	0.4548 (6)	0.12431 (16)	0.0447 (8)
H7	0.2734	0.5894	0.1065	0.054*
C8	0.2746 (5)	0.4194 (8)	0.17711 (15)	0.0534 (9)
H8	0.2073	0.5264	0.1950	0.064*
C9	0.3383 (5)	0.2213 (8)	0.20225 (15)	0.0501 (9)
C10	0.3817 (5)	0.4729 (8)	−0.14335 (15)	0.0557 (10)
H10	0.3514	0.6102	−0.1624	0.067*
C11	0.3270 (5)	0.4339 (7)	−0.09210 (16)	0.0495 (9)
H11	0.2590	0.5461	−0.0762	0.059*
C12	0.4383 (4)	0.0590 (8)	0.17791 (15)	0.0521 (10)
H12	0.4804	−0.0725	0.1964	0.063*
C13	0.4747 (4)	0.0967 (7)	0.12502 (16)	0.0468 (9)
H13	0.5419	−0.0119	0.1076	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0374 (4)	0.0481 (5)	0.0383 (4)	−0.0047 (3)	0.0004 (4)	−0.0003 (5)
F1	0.102 (2)	0.095 (2)	0.0385 (13)	−0.0210 (15)	0.0127 (13)	0.0005 (14)
F2	0.108 (3)	0.106 (2)	0.0354 (13)	0.0111 (16)	0.0135 (14)	0.0080 (14)
O1	0.0728 (17)	0.0439 (14)	0.0547 (19)	−0.0159 (12)	0.0016 (13)	0.0059 (13)
C1	0.064 (2)	0.066 (3)	0.0309 (18)	−0.016 (2)	0.0007 (17)	−0.0048 (18)
C2	0.056 (2)	0.056 (3)	0.051 (2)	0.0008 (19)	0.0058 (18)	−0.0130 (19)
C3	0.049 (2)	0.0390 (18)	0.046 (2)	0.0013 (16)	−0.0057 (16)	−0.0006 (17)
C4	0.0372 (17)	0.0408 (19)	0.0348 (17)	−0.0036 (14)	−0.0052 (14)	−0.0015 (15)
C5	0.0365 (17)	0.0358 (19)	0.044 (2)	−0.0057 (14)	0.0007 (14)	−0.0021 (14)
C6	0.0307 (16)	0.0359 (18)	0.0399 (19)	−0.0039 (13)	−0.0016 (12)	−0.0019 (14)
C7	0.047 (2)	0.044 (2)	0.043 (2)	0.0070 (15)	−0.0016 (17)	−0.0015 (19)
C8	0.054 (2)	0.063 (2)	0.043 (2)	0.0097 (19)	0.0076 (17)	−0.0108 (18)
C9	0.054 (2)	0.065 (3)	0.0320 (18)	−0.0019 (19)	0.0019 (16)	0.0001 (18)
C10	0.069 (3)	0.055 (2)	0.043 (2)	−0.005 (2)	−0.0079 (19)	0.0074 (19)
C11	0.055 (2)	0.044 (2)	0.050 (2)	0.0074 (17)	−0.0038 (17)	0.0014 (18)
C12	0.056 (2)	0.058 (2)	0.042 (2)	0.0077 (19)	0.0001 (17)	0.0115 (17)
C13	0.0467 (19)	0.048 (2)	0.045 (2)	0.0098 (15)	0.0018 (18)	−0.0029 (19)

Geometric parameters (Å, º)

S1—O1	1.493 (3)	C5—H5B	0.9700
S1—C4	1.790 (3)	C6—C13	1.390 (5)
S1—C5	1.832 (3)	C6—C7	1.393 (5)
F1—C1	1.361 (4)	C7—C8	1.381 (5)
F2—C9	1.364 (5)	C7—H7	0.9300
C1—C10	1.369 (6)	C8—C9	1.368 (6)
C1—C2	1.375 (6)	C8—H8	0.9300
C2—C3	1.384 (5)	C9—C12	1.369 (6)
C2—H2	0.9300	C10—C11	1.384 (6)
C3—C4	1.382 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C11	1.388 (5)	C12—C13	1.379 (5)
C5—C6	1.507 (5)	C12—H12	0.9300
C5—H5A	0.9700	C13—H13	0.9300
O1—S1—C4	106.50 (16)	C7—C6—C5	120.9 (3)
O1—S1—C5	106.67 (15)	C8—C7—C6	121.5 (3)
C4—S1—C5	97.76 (15)	C8—C7—H7	119.3
F1—C1—C10	118.0 (4)	C6—C7—H7	119.3
F1—C1—C2	118.2 (4)	C9—C8—C7	117.6 (3)
C10—C1—C2	123.7 (4)	C9—C8—H8	121.2
C1—C2—C3	117.4 (4)	C7—C8—H8	121.2
C1—C2—H2	121.3	F2—C9—C12	118.1 (4)
C3—C2—H2	121.3	F2—C9—C8	118.3 (3)
C4—C3—C2	120.7 (3)	C12—C9—C8	123.5 (3)
C4—C3—H3	119.6	C1—C10—C11	118.1 (4)
C2—C3—H3	119.6	C1—C10—H10	121.0
C3—C4—C11	120.0 (3)	C11—C10—H10	121.0
C3—C4—S1	120.0 (3)	C10—C11—C4	120.1 (4)
C11—C4—S1	119.8 (3)	C10—C11—H11	120.0
C6—C5—S1	107.9 (2)	C4—C11—H11	120.0
C6—C5—H5A	110.1	C9—C12—C13	117.9 (4)
S1—C5—H5A	110.1	C9—C12—H12	121.1
C6—C5—H5B	110.1	C13—C12—H12	121.1
S1—C5—H5B	110.1	C12—C13—C6	121.4 (3)
H5A—C5—H5B	108.4	C12—C13—H13	119.3
C13—C6—C7	118.1 (3)	C6—C13—H13	119.3
C13—C6—C5	121.0 (3)

(Compound_10_X2S)

Crystal data

C15H12N2O	F(000) = 496
Mr = 236.27	Dx = 1.333 Mg m^−3
Monoclinic, P121/n1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1875 reflections
a = 7.5500 (16) Å	θ = 2.9–22.8°
b = 11.186 (3) Å	µ = 0.09 mm^−1
c = 13.954 (3) Å	T = 300 K
β = 92.938 (8)°	Block, colorless
V = 1176.9 (5) Å^3	0.31 × 0.27 × 0.23 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	2066 independent reflections
Radiation source: micro-focus sealed tube	1550 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.033
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −8→8
Tmin = 0.974, Tmax = 0.981	k = −13→9
7461 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ^2(Fo^2) + (0.0626P)^2] where P = (Fo^2 + 2Fc^2)/3
2066 reflections	(Δ/σ)max = 0.012
169 parameters	Δρmax = 0.14 e Å^−3
3 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.50554 (16)	0.37794 (11)	0.09342 (9)	0.0443 (4)
N1	0.29539 (19)	0.23506 (13)	0.06062 (10)	0.0369 (4)
N2	0.3205 (2)	0.39934 (16)	−0.03842 (12)	0.0502 (5)
H2B	0.229 (2)	0.379 (2)	−0.0735 (14)	0.075*
H2A	0.368 (3)	0.4663 (13)	−0.0538 (15)	0.075*
C1	0.5228 (3)	0.05566 (18)	0.25480 (14)	0.0502 (5)
H1	0.6304	0.0165	0.2667	0.060*
C2	0.4892 (2)	0.11456 (17)	0.16873 (13)	0.0434 (5)
H2	0.5742	0.1145	0.1228	0.052*
C3	0.3300 (2)	0.17365 (16)	0.15044 (11)	0.0342 (4)
C4	0.1537 (2)	0.18899 (16)	−0.00154 (12)	0.0368 (4)
C5	−0.0219 (2)	0.19900 (16)	0.02550 (13)	0.0401 (5)
C6	−0.1551 (3)	0.16093 (18)	−0.04081 (14)	0.0495 (5)
H6	−0.2730	0.1675	−0.0252	0.059*
C7	−0.1165 (3)	0.11392 (18)	−0.12869 (15)	0.0550 (6)
H7	−0.2079	0.0897	−0.1716	0.066*
C8	0.3971 (3)	0.05490 (18)	0.32303 (13)	0.0507 (5)
H8	0.4193	0.0151	0.3809	0.061*
C9	0.2388 (3)	0.11326 (17)	0.30511 (12)	0.0454 (5)
H9	0.1552	0.1129	0.3518	0.054*
C10	0.1998 (2)	0.17331 (16)	0.21848 (11)	0.0361 (4)
C11	0.3809 (2)	0.34055 (16)	0.04112 (12)	0.0342 (4)
C12	0.1924 (3)	0.13928 (18)	−0.08928 (13)	0.0474 (5)
H12	0.3099	0.1305	−0.1052	0.057*
C13	0.0569 (3)	0.10278 (18)	−0.15299 (14)	0.0539 (6)
H13	0.0830	0.0708	−0.2121	0.065*
C14	−0.0683 (3)	0.24309 (17)	0.11938 (14)	0.0461 (5)
H14	−0.1752	0.2840	0.1218	0.055*
C15	0.0269 (3)	0.23079 (17)	0.20214 (14)	0.0464 (5)
H15	−0.0230	0.2627	0.2561	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0404 (8)	0.0412 (8)	0.0505 (8)	−0.0133 (6)	−0.0054 (6)	0.0087 (6)
N1	0.0394 (9)	0.0351 (9)	0.0360 (8)	−0.0117 (7)	0.0003 (6)	0.0059 (6)
N2	0.0529 (11)	0.0451 (11)	0.0514 (10)	−0.0160 (8)	−0.0097 (8)	0.0173 (8)
C1	0.0516 (13)	0.0452 (13)	0.0529 (12)	−0.0007 (10)	−0.0051 (10)	0.0071 (10)
C2	0.0413 (11)	0.0443 (12)	0.0449 (11)	−0.0076 (9)	0.0036 (9)	0.0029 (9)
C3	0.0395 (11)	0.0285 (10)	0.0347 (9)	−0.0088 (8)	0.0013 (8)	0.0014 (7)
C4	0.0428 (11)	0.0309 (10)	0.0366 (10)	−0.0093 (8)	0.0004 (8)	0.0046 (8)
C5	0.0427 (11)	0.0307 (10)	0.0467 (11)	−0.0072 (8)	−0.0007 (8)	0.0075 (8)
C6	0.0440 (12)	0.0429 (13)	0.0606 (13)	−0.0090 (9)	−0.0059 (10)	0.0088 (10)
C7	0.0668 (16)	0.0397 (13)	0.0562 (13)	−0.0138 (11)	−0.0195 (11)	0.0056 (10)
C8	0.0684 (15)	0.0426 (12)	0.0402 (11)	−0.0083 (11)	−0.0046 (10)	0.0072 (9)
C9	0.0592 (13)	0.0425 (12)	0.0351 (10)	−0.0120 (10)	0.0090 (9)	−0.0019 (9)
C10	0.0446 (11)	0.0298 (10)	0.0342 (9)	−0.0064 (8)	0.0043 (8)	−0.0052 (7)
C11	0.0335 (10)	0.0312 (10)	0.0384 (10)	−0.0033 (8)	0.0076 (8)	0.0026 (8)
C12	0.0555 (12)	0.0453 (12)	0.0417 (11)	−0.0074 (10)	0.0054 (9)	0.0013 (9)
C13	0.0761 (17)	0.0428 (13)	0.0422 (11)	−0.0079 (11)	−0.0041 (11)	−0.0041 (9)
C14	0.0401 (11)	0.0390 (12)	0.0597 (13)	0.0010 (9)	0.0078 (9)	−0.0030 (10)
C15	0.0507 (12)	0.0417 (12)	0.0478 (12)	−0.0037 (9)	0.0136 (9)	−0.0083 (9)

Geometric parameters (Å, º)

O1—C11	1.234 (2)	C5—C14	1.459 (3)
N1—C11	1.379 (2)	C6—C7	1.379 (3)
N1—C4	1.438 (2)	C6—H6	0.9300
N1—C3	1.441 (2)	C7—C13	1.375 (3)
N2—C11	1.349 (2)	C7—H7	0.9300
N2—H2B	0.858 (9)	C8—C9	1.373 (3)
N2—H2A	0.862 (9)	C8—H8	0.9300
C1—C8	1.379 (3)	C9—C10	1.401 (2)
C1—C2	1.382 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C15	1.462 (3)
C2—C3	1.384 (2)	C12—C13	1.382 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C10	1.401 (2)	C13—H13	0.9300
C4—C12	1.389 (3)	C14—C15	1.336 (2)
C4—C5	1.401 (3)	C14—H14	0.9300
C5—C6	1.398 (3)	C15—H15	0.9300
C11—N1—C4	121.95 (14)	C6—C7—H7	120.0
C11—N1—C3	120.90 (13)	C9—C8—C1	119.67 (18)
C4—N1—C3	116.74 (13)	C9—C8—H8	120.2
C11—N2—H2B	124.5 (15)	C1—C8—H8	120.2
C11—N2—H2A	120.1 (14)	C8—C9—C10	121.84 (18)
H2B—N2—H2A	115.1 (18)	C8—C9—H9	119.1
C8—C1—C2	120.06 (19)	C10—C9—H9	119.1
C8—C1—H1	120.0	C9—C10—C3	117.51 (17)
C2—C1—H1	120.0	C9—C10—C15	119.47 (16)
C1—C2—C3	120.46 (18)	C3—C10—C15	123.02 (16)
C1—C2—H2	119.8	O1—C11—N2	122.46 (16)
C3—C2—H2	119.8	O1—C11—N1	121.61 (15)
C2—C3—C10	120.46 (16)	N2—C11—N1	115.93 (16)
C2—C3—N1	120.33 (15)	C13—C12—C4	120.2 (2)
C10—C3—N1	119.21 (15)	C13—C12—H12	119.9
C12—C4—C5	120.95 (17)	C4—C12—H12	119.9
C12—C4—N1	119.41 (17)	C7—C13—C12	119.84 (19)
C5—C4—N1	119.60 (16)	C7—C13—H13	120.1
C6—C5—C4	117.12 (18)	C12—C13—H13	120.1
C6—C5—C14	119.97 (18)	C15—C14—C5	126.73 (18)
C4—C5—C14	122.88 (16)	C15—C14—H14	116.6
C7—C6—C5	121.8 (2)	C5—C14—H14	116.6
C7—C6—H6	119.1	C14—C15—C10	128.06 (18)
C5—C6—H6	119.1	C14—C15—H15	116.0
C13—C7—C6	120.05 (19)	C10—C15—H15	116.0
C13—C7—H7	120.0

(Compound_11_APEX)

Crystal data

C13H10INO2S	Z = 2
Mr = 371.18	F(000) = 360
Triclinic, P1	Dx = 1.936 Mg m^−3
a = 7.4946 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7421 (11) Å	Cell parameters from 4101 reflections
c = 11.4816 (16) Å	θ = 2.7–27.1°
α = 95.418 (3)°	µ = 2.67 mm^−1
β = 103.879 (3)°	T = 291 K
γ = 96.985 (3)°	Block, colourless
V = 636.65 (16) Å^3	0.38 × 0.31 × 0.28 mm

Data collection

Bruker APEX II DUO diffractometer	2786 independent reflections
Radiation source: fine-focus sealed tube	2492 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.3333 pixels mm^-1	θmax = 27.3°, θmin = 1.8°
φ & ω scans	h = −4→9
Absorption correction: multi-scan SADABS Version 2008/1	k = −9→9
Tmin = 0.56, Tmax = 0.76	l = −14→14
7653 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 0.3359P] where P = (Fo^2 + 2Fc^2)/3
2786 reflections	(Δ/σ)max = 0.004
163 parameters	Δρmax = 1.41 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	1.32050 (2)	1.17267 (3)	1.412333 (19)	0.04289 (9)
S1	0.54670 (9)	0.71959 (11)	0.91681 (7)	0.0413 (2)
O1	−0.3387 (3)	0.3512 (4)	0.7134 (3)	0.0599 (7)
O2	−0.2470 (3)	0.3193 (4)	0.5501 (2)	0.0598 (7)
N1	−0.2198 (3)	0.3702 (3)	0.6568 (3)	0.0395 (6)
C1	1.0642 (4)	1.0503 (4)	1.2973 (3)	0.0328 (6)
C2	0.9027 (4)	1.0497 (4)	1.3363 (3)	0.0395 (7)
H2	0.9061	1.1044	1.4126	0.047*
C3	0.7356 (4)	0.9660 (4)	1.2595 (3)	0.0395 (7)
H3	0.6271	0.9657	1.2853	0.047*
C4	0.7265 (4)	0.8831 (4)	1.1456 (3)	0.0312 (6)
C5	0.5358 (4)	0.7918 (4)	1.0649 (3)	0.0378 (7)
H5A	0.4464	0.873	1.0613	0.045*
H5B	0.4926	0.692	1.1012	0.045*
C6	0.3162 (4)	0.6227 (4)	0.8469 (3)	0.0332 (6)
C7	0.1686 (4)	0.6265 (4)	0.9014 (3)	0.0386 (7)
H7	0.1882	0.6834	0.9794	0.046*
C8	−0.0077 (4)	0.5444 (4)	0.8379 (3)	0.0357 (7)
H8	−0.1072	0.5464	0.8729	0.043*
C9	−0.0341 (4)	0.4602 (4)	0.7227 (3)	0.0328 (6)
C10	0.8916 (4)	0.8863 (4)	1.1080 (3)	0.0388 (7)
H10	0.8891	0.8328	1.0315	0.047*
C11	1.0595 (4)	0.9698 (4)	1.1851 (3)	0.0403 (7)
H11	1.1688	0.9706	1.1602	0.048*
C12	0.2851 (4)	0.5383 (4)	0.7294 (3)	0.0379 (7)
H12	0.3835	0.5371	0.6932	0.046*
C13	0.1094 (4)	0.4566 (4)	0.6663 (3)	0.0370 (7)
H13	0.0882	0.4005	0.5879	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03388 (11)	0.04810 (15)	0.03853 (15)	−0.00226 (8)	0.00008 (8)	−0.00079 (10)
S1	0.0279 (3)	0.0544 (5)	0.0359 (4)	−0.0025 (3)	0.0055 (3)	−0.0048 (4)
O1	0.0352 (11)	0.0776 (19)	0.0622 (18)	−0.0071 (11)	0.0170 (11)	−0.0061 (14)
O2	0.0434 (12)	0.0770 (19)	0.0448 (16)	−0.0103 (12)	0.0002 (11)	−0.0098 (14)
N1	0.0305 (11)	0.0382 (15)	0.0439 (17)	−0.0002 (10)	0.0026 (11)	0.0013 (13)
C1	0.0299 (12)	0.0326 (15)	0.0327 (16)	0.0020 (10)	0.0037 (11)	0.0023 (12)
C2	0.0368 (14)	0.0465 (19)	0.0317 (17)	0.0036 (12)	0.0071 (12)	−0.0053 (14)
C3	0.0332 (13)	0.0507 (19)	0.0341 (18)	0.0046 (12)	0.0106 (12)	0.0000 (15)
C4	0.0301 (12)	0.0292 (15)	0.0329 (16)	0.0035 (10)	0.0060 (11)	0.0032 (12)
C5	0.0335 (13)	0.0321 (16)	0.055 (2)	0.0085 (11)	0.0198 (13)	0.0152 (15)
C6	0.0265 (11)	0.0343 (16)	0.0364 (17)	0.0032 (10)	0.0041 (11)	0.0042 (13)
C7	0.0369 (14)	0.0458 (18)	0.0305 (17)	0.0042 (12)	0.0089 (12)	−0.0061 (14)
C8	0.0305 (12)	0.0414 (17)	0.0338 (17)	0.0027 (11)	0.0092 (11)	−0.0019 (14)
C9	0.0288 (12)	0.0307 (15)	0.0348 (17)	0.0015 (10)	0.0023 (11)	0.0021 (13)
C10	0.0363 (14)	0.0483 (19)	0.0293 (17)	0.0027 (13)	0.0093 (12)	−0.0054 (14)
C11	0.0320 (13)	0.0504 (19)	0.0376 (19)	0.0042 (12)	0.0099 (12)	0.0010 (15)
C12	0.0328 (13)	0.0477 (18)	0.0326 (17)	0.0031 (12)	0.0103 (12)	0.0005 (14)
C13	0.0370 (13)	0.0421 (17)	0.0286 (17)	0.0035 (12)	0.0057 (12)	−0.0024 (14)

Geometric parameters (Å, º)

I1—C1	2.106 (3)	C5—H5B	0.97
S1—C6	1.760 (3)	C6—C12	1.395 (4)
S1—C5	1.763 (3)	C6—C7	1.397 (4)
O1—N1	1.225 (3)	C7—C8	1.388 (4)
O2—N1	1.211 (4)	C7—H7	0.93
N1—C9	1.468 (3)	C8—C9	1.376 (4)
C1—C11	1.368 (5)	C8—H8	0.93
C1—C2	1.388 (4)	C9—C13	1.384 (4)
C2—C3	1.389 (4)	C10—C11	1.394 (4)
C2—H2	0.93	C10—H10	0.93
C3—C4	1.384 (4)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.383 (4)
C4—C10	1.404 (4)	C12—H12	0.93
C4—C5	1.548 (4)	C13—H13	0.93
C5—H5A	0.97
C6—S1—C5	102.67 (14)	C12—C6—S1	115.8 (2)
O2—N1—O1	123.8 (3)	C7—C6—S1	124.3 (2)
O2—N1—C9	118.4 (3)	C8—C7—C6	119.4 (3)
O1—N1—C9	117.8 (3)	C8—C7—H7	120.3
C11—C1—C2	120.6 (3)	C6—C7—H7	120.3
C11—C1—I1	119.4 (2)	C9—C8—C7	119.6 (3)
C2—C1—I1	120.0 (2)	C9—C8—H8	120.2
C1—C2—C3	119.0 (3)	C7—C8—H8	120.2
C1—C2—H2	120.5	C8—C9—C13	122.1 (3)
C3—C2—H2	120.5	C8—C9—N1	119.4 (3)
C4—C3—C2	121.7 (3)	C13—C9—N1	118.4 (3)
C4—C3—H3	119.1	C11—C10—C4	120.1 (3)
C2—C3—H3	119.1	C11—C10—H10	120.0
C3—C4—C10	118.2 (3)	C4—C10—H10	120.0
C3—C4—C5	119.0 (2)	C1—C11—C10	120.3 (3)
C10—C4—C5	122.7 (3)	C1—C11—H11	119.8
C4—C5—S1	112.32 (18)	C10—C11—H11	119.8
C4—C5—H5A	109.1	C13—C12—C6	120.6 (3)
S1—C5—H5A	109.1	C13—C12—H12	119.7
C4—C5—H5B	109.1	C6—C12—H12	119.7
S1—C5—H5B	109.1	C12—C13—C9	118.4 (3)
H5A—C5—H5B	107.9	C12—C13—H13	120.8
C12—C6—C7	119.9 (3)	C9—C13—H13	120.8

(Compound_11_CCDC)

Crystal data

C13H10INO2S	Z = 2
Mr = 371.18	F(000) = 360
Triclinic, P1	Dx = 1.925 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5076 (15) Å	Cell parameters from 1954 reflections
b = 7.760 (2) Å	θ = 2.7–22.5°
c = 11.507 (3) Å	µ = 2.66 mm^−1
α = 95.317 (8)°	T = 300 K
β = 103.999 (7)°	Plate, colorless
γ = 97.013 (7)°	0.31 × 0.27 × 0.11 mm
V = 640.4 (3) Å^3

Data collection

Bruker SMART X2S diffractometer	2224 independent reflections
Radiation source: micro-focus sealed tube	1836 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.038
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −8→8
Tmin = 0.350, Tmax = 0.879	k = −9→9
6315 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0532P)^2] where P = (Fo^2 + 2Fc^2)/3
2224 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 1.07 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I9	1.32038 (5)	1.17269 (5)	1.41230 (3)	0.04524 (18)
S1	0.54650 (19)	0.71990 (19)	0.91683 (13)	0.0426 (4)
N16	−0.2196 (6)	0.3702 (6)	0.6576 (4)	0.0414 (11)
C6	1.0642 (7)	1.0497 (7)	1.2974 (5)	0.0347 (12)
C7	1.0591 (7)	0.9687 (7)	1.1848 (5)	0.0414 (13)
H7	1.1679	0.9692	1.1597	0.050*
C8	0.8917 (7)	0.8862 (7)	1.1091 (5)	0.0394 (13)
H8	0.8890	0.8317	1.0330	0.047*
C3	0.7270 (7)	0.8839 (6)	1.1454 (5)	0.0312 (11)
C2	0.5347 (7)	0.7908 (7)	1.0641 (5)	0.0370 (12)
H2A	0.4447	0.8711	1.0602	0.044*
H2B	0.4923	0.6908	1.1003	0.044*
C10	0.3168 (7)	0.6231 (6)	0.8477 (5)	0.0320 (11)
C11	0.1686 (7)	0.6268 (7)	0.9017 (5)	0.0390 (13)
H11	0.1878	0.6845	0.9792	0.047*
C12	−0.0060 (7)	0.5443 (7)	0.8390 (5)	0.0376 (12)
H12	−0.1050	0.5453	0.8744	0.045*
C13	−0.0336 (7)	0.4603 (6)	0.7237 (5)	0.0335 (12)
C14	0.1094 (7)	0.4575 (7)	0.6674 (5)	0.0392 (12)
H14	0.0876	0.4024	0.5890	0.047*
C15	0.2851 (7)	0.5381 (7)	0.7299 (5)	0.0404 (13)
H15	0.3831	0.5360	0.6937	0.048*
C4	0.7373 (8)	0.9647 (7)	1.2590 (5)	0.0419 (13)
H4	0.6296	0.9619	1.2856	0.050*
C5	0.9016 (7)	1.0490 (7)	1.3341 (5)	0.0417 (13)
H5	0.9039	1.1055	1.4095	0.050*
O17	−0.3386 (6)	0.3506 (6)	0.7142 (4)	0.0602 (12)
O18	−0.2465 (6)	0.3196 (6)	0.5506 (4)	0.0627 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I9	0.0337 (2)	0.0521 (3)	0.0409 (3)	−0.00336 (16)	−0.00011 (17)	−0.00113 (17)
S1	0.0282 (7)	0.0567 (9)	0.0359 (8)	−0.0038 (6)	0.0042 (6)	−0.0048 (6)
N16	0.029 (3)	0.044 (3)	0.045 (3)	0.001 (2)	0.003 (2)	−0.001 (2)
C6	0.032 (3)	0.037 (3)	0.029 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C7	0.026 (3)	0.057 (3)	0.038 (3)	0.001 (2)	0.009 (2)	−0.003 (3)
C8	0.037 (3)	0.051 (3)	0.027 (3)	0.001 (3)	0.009 (2)	−0.009 (2)
C3	0.026 (3)	0.034 (3)	0.030 (3)	0.000 (2)	0.004 (2)	0.001 (2)
C2	0.026 (3)	0.037 (3)	0.055 (4)	0.008 (2)	0.020 (3)	0.015 (3)
C10	0.025 (3)	0.037 (3)	0.032 (3)	0.004 (2)	0.005 (2)	0.002 (2)
C11	0.039 (3)	0.043 (3)	0.030 (3)	0.001 (2)	0.006 (2)	−0.006 (2)
C12	0.028 (3)	0.049 (3)	0.036 (3)	0.003 (2)	0.014 (2)	−0.006 (2)
C13	0.030 (3)	0.030 (3)	0.041 (3)	0.003 (2)	0.010 (2)	0.006 (2)
C14	0.037 (3)	0.048 (3)	0.029 (3)	0.001 (2)	0.007 (2)	−0.003 (2)
C15	0.030 (3)	0.055 (3)	0.035 (3)	0.003 (2)	0.010 (2)	0.000 (3)
C4	0.032 (3)	0.055 (3)	0.036 (3)	−0.002 (2)	0.011 (2)	−0.001 (3)
C5	0.038 (3)	0.050 (3)	0.035 (3)	0.005 (3)	0.009 (3)	−0.003 (3)
O17	0.034 (2)	0.078 (3)	0.062 (3)	−0.007 (2)	0.015 (2)	−0.007 (2)
O18	0.041 (2)	0.082 (3)	0.050 (3)	−0.010 (2)	−0.001 (2)	−0.011 (2)

Geometric parameters (Å, º)

I9—C6	2.109 (5)	C2—H2B	0.9700
S1—C2	1.759 (6)	C10—C15	1.403 (7)
S1—C10	1.755 (5)	C10—C11	1.401 (7)
N16—O18	1.217 (6)	C11—C12	1.378 (7)
N16—O17	1.230 (6)	C11—H11	0.9300
N16—C13	1.472 (7)	C12—C13	1.379 (7)
C6—C7	1.376 (7)	C12—H12	0.9300
C6—C5	1.384 (8)	C13—C14	1.383 (7)
C7—C8	1.385 (7)	C14—C15	1.380 (7)
C7—H7	0.9300	C14—H14	0.9300
C8—C3	1.396 (7)	C15—H15	0.9300
C8—H8	0.9300	C4—C5	1.371 (8)
C3—C4	1.377 (7)	C4—H4	0.9300
C3—C2	1.565 (7)	C5—H5	0.9300
C2—H2A	0.9700
C2—S1—C10	102.2 (2)	C15—C10—S1	115.7 (4)
O18—N16—O17	124.0 (5)	C11—C10—S1	124.7 (4)
O18—N16—C13	118.3 (5)	C12—C11—C10	119.5 (5)
O17—N16—C13	117.8 (5)	C12—C11—H11	120.2
C7—C6—C5	119.8 (5)	C10—C11—H11	120.2
C7—C6—I9	119.5 (4)	C11—C12—C13	119.8 (5)
C5—C6—I9	120.7 (4)	C11—C12—H12	120.1
C8—C7—C6	119.9 (5)	C13—C12—H12	120.1
C8—C7—H7	120.0	C12—C13—C14	121.8 (5)
C6—C7—H7	120.0	C12—C13—N16	119.7 (5)
C7—C8—C3	120.8 (5)	C14—C13—N16	118.4 (5)
C7—C8—H8	119.6	C15—C14—C13	118.7 (5)
C3—C8—H8	119.6	C15—C14—H14	120.6
C4—C3—C8	117.8 (5)	C13—C14—H14	120.6
C4—C3—C2	119.3 (4)	C14—C15—C10	120.4 (5)
C8—C3—C2	122.9 (4)	C14—C15—H15	119.8
C3—C2—S1	112.0 (3)	C10—C15—H15	119.8
C3—C2—H2A	109.2	C5—C4—C3	122.0 (5)
S1—C2—H2A	109.2	C5—C4—H4	119.0
C3—C2—H2B	109.2	C3—C4—H4	119.0
S1—C2—H2B	109.2	C4—C5—C6	119.7 (5)
H2A—C2—H2B	107.9	C4—C5—H5	120.1
C15—C10—C11	119.6 (5)	C6—C5—H5	120.1

(Compound_11_X2S)

Crystal data

C13H10INO2S	Z = 2
Mr = 371.18	F(000) = 360
Triclinic, P1	Dx = 1.925 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5076 (15) Å	Cell parameters from 1954 reflections
b = 7.760 (2) Å	θ = 2.7–22.5°
c = 11.507 (3) Å	µ = 2.66 mm^−1
α = 95.317 (8)°	T = 300 K
β = 103.999 (7)°	Plate, colorless
γ = 97.013 (7)°	0.31 × 0.27 × 0.11 mm
V = 640.4 (3) Å^3

Data collection

Bruker SMART X2S diffractometer	2224 independent reflections
Radiation source: micro-focus sealed tube	1836 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.038
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −8→8
Tmin = 0.691, Tmax = 0.879	k = −9→9
6315 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0536P)^2] where P = (Fo^2 + 2Fc^2)/3
2224 reflections	(Δ/σ)max = 0.025
163 parameters	Δρmax = 1.07 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	1.32038 (5)	1.17269 (5)	1.41230 (3)	0.04524 (18)
S1	0.54650 (19)	0.71990 (19)	0.91682 (13)	0.0426 (4)
O1	−0.2465 (6)	0.3196 (6)	0.5506 (4)	0.0627 (12)
O2	−0.3386 (6)	0.3506 (6)	0.7142 (4)	0.0602 (12)
N1	−0.2196 (6)	0.3702 (6)	0.6576 (4)	0.0414 (11)
C1	1.0642 (7)	1.0497 (7)	1.2974 (5)	0.0347 (12)
C2	1.0591 (7)	0.9687 (7)	1.1848 (5)	0.0414 (13)
H2	1.1679	0.9693	1.1597	0.050*
C3	0.8917 (7)	0.8862 (7)	1.1091 (5)	0.0394 (13)
H3	0.8890	0.8317	1.0331	0.047*
C4	0.7270 (7)	0.8839 (6)	1.1454 (5)	0.0312 (11)
C5	0.5347 (7)	0.7908 (7)	1.0641 (5)	0.0370 (12)
H5A	0.4447	0.8711	1.0603	0.044*
H5B	0.4923	0.6908	1.1003	0.044*
C6	0.3168 (7)	0.6231 (6)	0.8477 (5)	0.0320 (11)
C7	0.1686 (7)	0.6268 (7)	0.9017 (5)	0.0390 (13)
H7	0.1878	0.6845	0.9792	0.047*
C8	−0.0060 (7)	0.5443 (7)	0.8390 (5)	0.0376 (12)
H8	−0.1050	0.5453	0.8743	0.045*
C9	−0.0336 (7)	0.4603 (6)	0.7237 (5)	0.0336 (12)
C10	0.1094 (7)	0.4575 (7)	0.6674 (5)	0.0393 (12)
H10	0.0876	0.4024	0.5890	0.047*
C11	0.2851 (7)	0.5381 (7)	0.7299 (5)	0.0404 (13)
H11	0.3831	0.5360	0.6937	0.048*
C12	0.7373 (8)	0.9647 (7)	1.2590 (5)	0.0419 (13)
H12	0.6296	0.9619	1.2856	0.050*
C13	0.9016 (7)	1.0490 (7)	1.3341 (5)	0.0417 (13)
H13	0.9039	1.1055	1.4095	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0337 (2)	0.0521 (3)	0.0409 (3)	−0.00336 (16)	−0.00011 (17)	−0.00113 (17)
S1	0.0282 (7)	0.0567 (9)	0.0359 (8)	−0.0039 (6)	0.0042 (6)	−0.0048 (6)
O1	0.041 (2)	0.082 (3)	0.050 (3)	−0.010 (2)	−0.001 (2)	−0.011 (2)
O2	0.034 (2)	0.078 (3)	0.062 (3)	−0.007 (2)	0.015 (2)	−0.007 (2)
N1	0.029 (3)	0.044 (3)	0.045 (3)	0.001 (2)	0.003 (2)	−0.001 (2)
C1	0.032 (3)	0.037 (3)	0.029 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C2	0.026 (3)	0.057 (3)	0.038 (3)	0.001 (2)	0.009 (2)	−0.003 (3)
C3	0.037 (3)	0.051 (3)	0.027 (3)	0.001 (2)	0.009 (2)	−0.009 (2)
C4	0.026 (3)	0.034 (3)	0.030 (3)	0.000 (2)	0.004 (2)	0.001 (2)
C5	0.026 (3)	0.037 (3)	0.055 (4)	0.008 (2)	0.020 (3)	0.015 (3)
C6	0.025 (3)	0.037 (3)	0.033 (3)	0.004 (2)	0.005 (2)	0.002 (2)
C7	0.039 (3)	0.043 (3)	0.030 (3)	0.001 (2)	0.006 (2)	−0.006 (2)
C8	0.028 (3)	0.049 (3)	0.036 (3)	0.003 (2)	0.014 (2)	−0.006 (2)
C9	0.030 (3)	0.030 (3)	0.041 (3)	0.003 (2)	0.010 (2)	0.006 (2)
C10	0.037 (3)	0.048 (3)	0.029 (3)	0.001 (2)	0.007 (2)	−0.003 (2)
C11	0.030 (3)	0.055 (3)	0.035 (3)	0.003 (2)	0.010 (2)	0.000 (3)
C12	0.032 (3)	0.055 (3)	0.036 (3)	−0.002 (2)	0.011 (2)	−0.001 (3)
C13	0.038 (3)	0.050 (3)	0.035 (3)	0.005 (3)	0.009 (3)	−0.003 (3)

Geometric parameters (Å, º)

I1—C1	2.109 (5)	C5—H5B	0.9700
S1—C6	1.755 (5)	C6—C7	1.401 (7)
S1—C5	1.759 (6)	C6—C11	1.403 (7)
O1—N1	1.217 (6)	C7—C8	1.378 (7)
O2—N1	1.230 (6)	C7—H7	0.9300
N1—C9	1.472 (7)	C8—C9	1.379 (7)
C1—C2	1.376 (7)	C8—H8	0.9300
C1—C13	1.384 (8)	C9—C10	1.382 (7)
C2—C3	1.385 (7)	C10—C11	1.380 (7)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.396 (7)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.371 (8)
C4—C12	1.377 (7)	C12—H12	0.9300
C4—C5	1.565 (7)	C13—H13	0.9300
C5—H5A	0.9700
C6—S1—C5	102.2 (2)	C7—C6—S1	124.6 (4)
O1—N1—O2	124.0 (5)	C11—C6—S1	115.7 (4)
O1—N1—C9	118.3 (5)	C8—C7—C6	119.5 (5)
O2—N1—C9	117.8 (5)	C8—C7—H7	120.2
C2—C1—C13	119.8 (5)	C6—C7—H7	120.2
C2—C1—I1	119.5 (4)	C7—C8—C9	119.8 (5)
C13—C1—I1	120.8 (4)	C7—C8—H8	120.1
C1—C2—C3	119.9 (5)	C9—C8—H8	120.1
C1—C2—H2	120.0	C10—C9—C8	121.8 (5)
C3—C2—H2	120.0	C10—C9—N1	118.4 (5)
C2—C3—C4	120.8 (5)	C8—C9—N1	119.7 (5)
C2—C3—H3	119.6	C9—C10—C11	118.8 (5)
C4—C3—H3	119.6	C9—C10—H10	120.6
C12—C4—C3	117.8 (5)	C11—C10—H10	120.6
C12—C4—C5	119.3 (4)	C10—C11—C6	120.4 (5)
C3—C4—C5	122.9 (4)	C10—C11—H11	119.8
C4—C5—S1	112.0 (3)	C6—C11—H11	119.8
C4—C5—H5A	109.2	C13—C12—C4	122.0 (5)
S1—C5—H5A	109.2	C13—C12—H12	119.0
C4—C5—H5B	109.2	C4—C12—H12	119.0
S1—C5—H5B	109.2	C12—C13—C1	119.7 (5)
H5A—C5—H5B	107.9	C12—C13—H13	120.1
C7—C6—C11	119.6 (5)	C1—C13—H13	120.1

(Compound_12_APEX)

Crystal data

C7H5NO3S	F(000) = 376
Mr = 183.18	Dx = 1.593 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5830 (12) Å	Cell parameters from 2150 reflections
b = 6.9252 (8) Å	θ = 3.4–25.7°
c = 11.8518 (15) Å	µ = 0.38 mm^−1
β = 103.815 (3)°	T = 291 K
V = 763.78 (16) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.21 mm

Data collection

Bruker APEX II DUO diffractometer	1473 independent reflections
Radiation source: fine-focus sealed tube	1283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.3333 pixels mm^-1	θmax = 25.8°, θmin = 2.2°
φ & ω scans	h = −11→11
Absorption correction: multi-scan SADABS Version 2008/1	k = −8→8
Tmin = 0.664, Tmax = 0.745	l = −14→14
5166 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0346P)^2 + 0.3571P] where P = (Fo^2 + 2Fc^2)/3
1473 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.71048 (5)	0.77117 (7)	0.34633 (4)	0.03726 (16)
O1	0.58436 (15)	0.6573 (2)	0.33741 (13)	0.0569 (4)
O2	0.74426 (16)	0.8307 (2)	0.24099 (11)	0.0533 (4)
O3	1.01830 (14)	0.69119 (19)	0.60358 (10)	0.0418 (3)
N1	0.85064 (16)	0.6592 (2)	0.43101 (13)	0.0393 (4)
H1	0.8815	0.5501	0.4121	0.047*
C1	0.7808 (2)	1.2299 (3)	0.62054 (18)	0.0486 (5)
H1A	0.7988	1.3211	0.6799	0.058*
C2	0.8669 (2)	1.0675 (3)	0.62928 (15)	0.0404 (4)
H2	0.9433	1.0489	0.6934	0.049*
C3	0.83630 (18)	0.9339 (2)	0.54028 (14)	0.0320 (4)
C4	0.72226 (19)	0.9636 (3)	0.44499 (15)	0.0339 (4)
C5	0.91367 (19)	0.7512 (2)	0.53243 (15)	0.0327 (4)
C6	0.6680 (2)	1.2579 (3)	0.52409 (19)	0.0512 (5)
H6	0.612	1.3686	0.5198	0.061*
C7	0.6362 (2)	1.1259 (3)	0.43402 (18)	0.0464 (5)
H7	0.5608	1.1454	0.3693	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0382 (3)	0.0362 (3)	0.0332 (3)	0.00348 (19)	0.00034 (18)	−0.00066 (18)
O1	0.0429 (8)	0.0574 (9)	0.0628 (9)	−0.0100 (7)	−0.0022 (7)	−0.0059 (7)
O2	0.0720 (10)	0.0534 (9)	0.0338 (7)	0.0087 (8)	0.0113 (7)	0.0023 (6)
O3	0.0451 (7)	0.0412 (7)	0.0341 (7)	0.0121 (6)	−0.0003 (5)	0.0015 (5)
N1	0.0436 (9)	0.0310 (8)	0.0384 (8)	0.0098 (7)	0.0000 (7)	−0.0037 (6)
C1	0.0632 (14)	0.0379 (10)	0.0483 (11)	0.0048 (9)	0.0204 (10)	−0.0072 (9)
C2	0.0491 (11)	0.0391 (10)	0.0326 (9)	0.0023 (8)	0.0088 (8)	−0.0005 (8)
C3	0.0354 (9)	0.0304 (8)	0.0310 (8)	0.0034 (7)	0.0094 (7)	0.0031 (7)
C4	0.0357 (9)	0.0330 (9)	0.0327 (9)	0.0033 (7)	0.0074 (7)	0.0017 (7)
C5	0.0355 (9)	0.0315 (9)	0.0310 (8)	0.0022 (7)	0.0078 (7)	0.0032 (7)
C6	0.0561 (13)	0.0368 (10)	0.0649 (14)	0.0167 (9)	0.0227 (11)	0.0036 (9)
C7	0.0437 (11)	0.0457 (11)	0.0478 (11)	0.0141 (9)	0.0070 (9)	0.0079 (9)

Geometric parameters (Å, º)

S1—O2	1.4236 (14)	C1—H1A	0.93
S1—O1	1.4258 (15)	C2—C3	1.381 (2)
S1—N1	1.6640 (15)	C2—H2	0.93
S1—C4	1.7585 (18)	C3—C4	1.387 (2)
O3—C5	1.219 (2)	C3—C5	1.480 (2)
N1—C5	1.367 (2)	C4—C7	1.381 (3)
N1—H1	0.86	C6—C7	1.383 (3)
C1—C2	1.384 (3)	C6—H6	0.93
C1—C6	1.387 (3)	C7—H7	0.93
O2—S1—O1	117.48 (9)	C2—C3—C4	120.34 (16)
O2—S1—N1	110.13 (9)	C2—C3—C5	127.05 (16)
O1—S1—N1	109.56 (9)	C4—C3—C5	112.61 (15)
O2—S1—C4	111.82 (9)	C7—C4—C3	122.25 (17)
O1—S1—C4	112.78 (9)	C7—C4—S1	127.72 (14)
N1—S1—C4	92.16 (8)	C3—C4—S1	110.02 (13)
C5—N1—S1	115.88 (12)	O3—C5—N1	124.53 (16)
C5—N1—H1	122.1	O3—C5—C3	126.13 (16)
S1—N1—H1	122.1	N1—C5—C3	109.33 (14)
C2—C1—C6	120.58 (19)	C7—C6—C1	121.89 (18)
C2—C1—H1A	119.7	C7—C6—H6	119.1
C6—C1—H1A	119.7	C1—C6—H6	119.1
C3—C2—C1	118.25 (18)	C4—C7—C6	116.68 (18)
C3—C2—H2	120.9	C4—C7—H7	121.7
C1—C2—H2	120.9	C6—C7—H7	121.7

(Compound_12_Manual)

Crystal data

C7H5NO3S	F(000) = 376
Mr = 183.18	Dx = 1.583 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1234 reflections
a = 9.6083 (16) Å	θ = 3.4–21.5°
b = 6.9347 (10) Å	µ = 0.38 mm^−1
c = 11.882 (2) Å	T = 300 K
β = 103.834 (6)°	Plate, colorless
V = 768.7 (2) Å^3	0.32 × 0.25 × 0.11 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1346 independent reflections
Radiation source: micro-focus sealed tube	1025 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→11
Tmin = 0.832, Tmax = 0.981	k = −8→8
4799 measured reflections	l = −14→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0766P)^2] where P = (Fo^2 + 2Fc^2)/3
1346 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.21039 (8)	0.22889 (11)	0.84628 (7)	0.0398 (3)
O1	0.2438 (2)	0.1694 (3)	0.74080 (18)	0.0563 (7)
O2	0.0848 (2)	0.3425 (3)	0.8371 (2)	0.0600 (7)
N1	0.3503 (3)	0.3404 (4)	0.9311 (2)	0.0425 (7)
O3	0.5180 (2)	0.3087 (3)	1.10339 (17)	0.0441 (6)
C1	0.2220 (3)	0.0374 (4)	0.9451 (2)	0.0361 (7)
C2	0.1361 (3)	−0.1255 (4)	0.9339 (3)	0.0486 (8)
H2	0.0612	−0.1454	0.8691	0.058*
C3	0.1674 (4)	−0.2569 (5)	1.0240 (3)	0.0544 (10)
H3	0.1113	−0.3672	1.0197	0.065*
C4	0.2804 (4)	−0.2292 (5)	1.1211 (3)	0.0499 (9)
H4	0.2978	−0.3200	1.1804	0.060*
C5	0.4128 (3)	0.2489 (4)	1.0322 (2)	0.0333 (7)
C6	0.3354 (3)	0.0660 (4)	1.0399 (2)	0.0330 (7)
C7	0.3663 (3)	−0.0680 (4)	1.1294 (3)	0.0435 (8)
H7	0.4429	−0.0495	1.1932	0.052*
H1	0.376 (3)	0.446 (4)	0.913 (3)	0.047 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0416 (5)	0.0388 (5)	0.0344 (5)	−0.0035 (3)	−0.0001 (3)	0.0002 (3)
O1	0.0787 (18)	0.0566 (14)	0.0335 (12)	−0.0095 (13)	0.0131 (11)	−0.0021 (10)
O2	0.0464 (14)	0.0584 (15)	0.0670 (17)	0.0113 (11)	−0.0029 (12)	0.0054 (12)
N1	0.0483 (16)	0.0321 (14)	0.0401 (15)	−0.0117 (12)	−0.0030 (12)	0.0027 (12)
O3	0.0491 (13)	0.0445 (12)	0.0335 (12)	−0.0134 (10)	−0.0005 (10)	−0.0029 (9)
C1	0.0387 (15)	0.0349 (15)	0.0345 (15)	−0.0030 (13)	0.0082 (12)	−0.0031 (12)
C2	0.0479 (19)	0.0491 (19)	0.0480 (19)	−0.0160 (15)	0.0100 (15)	−0.0083 (16)
C3	0.060 (2)	0.0386 (18)	0.070 (3)	−0.0177 (16)	0.0243 (19)	−0.0050 (16)
C4	0.067 (2)	0.0383 (18)	0.048 (2)	−0.0054 (15)	0.0207 (18)	0.0052 (14)
C5	0.0377 (16)	0.0298 (14)	0.0323 (16)	−0.0024 (12)	0.0081 (13)	−0.0014 (12)
C6	0.0380 (15)	0.0294 (14)	0.0323 (15)	−0.0032 (12)	0.0098 (12)	−0.0039 (12)
C7	0.0556 (19)	0.0403 (17)	0.0328 (16)	−0.0020 (15)	0.0072 (14)	0.0003 (13)

Geometric parameters (Å, º)

S1—O2	1.423 (2)	C2—C3	1.383 (4)
S1—O1	1.427 (2)	C2—H2	0.9300
S1—N1	1.665 (2)	C3—C4	1.395 (5)
S1—C1	1.758 (3)	C3—H3	0.9300
N1—C5	1.364 (4)	C4—C7	1.379 (4)
N1—H1	0.82 (3)	C4—H4	0.9300
O3—C5	1.224 (3)	C5—C6	1.484 (4)
C1—C6	1.382 (4)	C6—C7	1.390 (4)
C1—C2	1.386 (4)	C7—H7	0.9300
O2—S1—O1	117.24 (14)	C2—C3—C4	122.1 (3)
O2—S1—N1	109.65 (15)	C2—C3—H3	119.0
O1—S1—N1	110.33 (15)	C4—C3—H3	119.0
O2—S1—C1	112.72 (15)	C7—C4—C3	120.3 (3)
O1—S1—C1	112.09 (13)	C7—C4—H4	119.8
N1—S1—C1	91.92 (13)	C3—C4—H4	119.8
C5—N1—S1	116.0 (2)	O3—C5—N1	124.6 (2)
C5—N1—H1	124 (2)	O3—C5—C6	126.1 (3)
S1—N1—H1	120 (2)	N1—C5—C6	109.3 (2)
C6—C1—C2	122.0 (3)	C1—C6—C7	120.7 (3)
C6—C1—S1	110.3 (2)	C1—C6—C5	112.4 (2)
C2—C1—S1	127.6 (2)	C7—C6—C5	126.9 (3)
C3—C2—C1	116.7 (3)	C4—C7—C6	118.2 (3)
C3—C2—H2	121.7	C4—C7—H7	120.9
C1—C2—H2	121.7	C6—C7—H7	120.9

(Compound_12_X2S)

Crystal data

C7H5NO3S	F(000) = 356
Mr = 178.14	Dx = 1.539 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1234 reflections
a = 9.6083 (16) Å	θ = 3.4–21.5°
b = 6.9347 (10) Å	µ = 0.38 mm^−1
c = 11.882 (2) Å	T = 300 K
β = 103.834 (6)°	Plate, colorless
V = 768.7 (2) Å^3	0.32 × 0.25 × 0.11 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	1346 independent reflections
Radiation source: micro-focus sealed tube	1025 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −10→11
Tmin = 0.860, Tmax = 0.981	k = −8→8
4799 measured reflections	l = −14→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.115P)^2 + 0.9183P] where P = (Fo^2 + 2Fc^2)/3
1346 reflections	(Δ/σ)max = 0.025
109 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.21050 (11)	0.22887 (16)	0.84648 (9)	0.0402 (4)
O1	0.2443 (4)	0.1688 (5)	0.7411 (3)	0.0571 (10)
O2	0.0844 (3)	0.3423 (5)	0.8376 (3)	0.0613 (10)
O3	0.3507 (4)	0.3425 (5)	0.9303 (3)	0.0625 (10)
N1	0.5181 (3)	0.3091 (4)	1.1032 (2)	0.0289 (7)
C1	0.2217 (4)	0.0375 (6)	0.9452 (3)	0.0370 (10)
C2	0.1361 (5)	−0.1235 (7)	0.9337 (4)	0.0496 (12)
H2	0.0610	−0.1428	0.8690	0.060*
C3	0.1681 (6)	−0.2572 (7)	1.0247 (5)	0.0555 (14)
H3	0.1125	−0.3680	1.0203	0.067*
C4	0.2805 (5)	−0.2290 (7)	1.1214 (4)	0.0501 (12)
H4	0.2979	−0.3194	1.1809	0.060*
C5	0.4136 (5)	0.2491 (5)	1.0326 (3)	0.0355 (10)
C6	0.3351 (4)	0.0658 (5)	1.0399 (3)	0.0337 (9)
C7	0.3660 (5)	−0.0686 (6)	1.1297 (4)	0.0448 (11)
H7	0.4425	−0.0501	1.1935	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0424 (7)	0.0387 (7)	0.0351 (7)	−0.0034 (4)	0.0004 (5)	0.0003 (4)
O1	0.079 (2)	0.058 (2)	0.0350 (17)	−0.0078 (18)	0.0146 (16)	−0.0016 (15)
O2	0.0475 (19)	0.057 (2)	0.071 (2)	0.0115 (16)	−0.0027 (16)	0.0066 (18)
O3	0.067 (2)	0.056 (2)	0.056 (2)	−0.0094 (18)	−0.0039 (17)	0.0016 (17)
N1	0.0325 (16)	0.0295 (16)	0.0196 (15)	−0.0128 (13)	−0.0037 (12)	−0.0028 (12)
C1	0.039 (2)	0.038 (2)	0.033 (2)	−0.0032 (18)	0.0074 (17)	−0.0030 (17)
C2	0.050 (3)	0.050 (3)	0.049 (3)	−0.018 (2)	0.011 (2)	−0.008 (2)
C3	0.060 (3)	0.041 (3)	0.070 (4)	−0.017 (2)	0.024 (3)	−0.003 (2)
C4	0.065 (3)	0.041 (3)	0.048 (3)	−0.006 (2)	0.021 (2)	0.005 (2)
C5	0.046 (2)	0.030 (2)	0.033 (2)	0.0003 (17)	0.0131 (19)	0.0024 (16)
C6	0.040 (2)	0.030 (2)	0.033 (2)	−0.0041 (17)	0.0107 (17)	−0.0024 (16)
C7	0.058 (3)	0.043 (2)	0.031 (2)	0.000 (2)	0.0065 (19)	0.0002 (18)

Geometric parameters (Å, º)

S1—O2	1.428 (3)	C2—H2	0.9300
S1—O1	1.428 (3)	C3—C4	1.389 (7)
S1—O3	1.669 (3)	C3—H3	0.9300
S1—C1	1.758 (4)	C4—C7	1.372 (6)
O3—C5	1.383 (5)	C4—H4	0.9300
N1—C5	1.217 (5)	C5—C6	1.491 (5)
C1—C2	1.374 (6)	C6—C7	1.394 (6)
C1—C6	1.381 (6)	C7—H7	0.9300
C2—C3	1.402 (7)
O2—S1—O1	117.6 (2)	C4—C3—H3	119.1
O2—S1—O3	109.5 (2)	C2—C3—H3	119.1
O1—S1—O3	109.9 (2)	C7—C4—C3	120.5 (4)
O2—S1—C1	112.4 (2)	C7—C4—H4	119.8
O1—S1—C1	111.98 (19)	C3—C4—H4	119.8
O3—S1—C1	92.66 (18)	N1—C5—O3	124.1 (4)
C5—O3—S1	115.1 (3)	N1—C5—C6	126.6 (4)
C2—C1—C6	122.3 (4)	O3—C5—C6	109.3 (3)
C2—C1—S1	127.4 (3)	C1—C6—C7	120.7 (4)
C6—C1—S1	110.3 (3)	C1—C6—C5	112.7 (4)
C1—C2—C3	116.4 (4)	C7—C6—C5	126.6 (4)
C1—C2—H2	121.8	C4—C7—C6	118.2 (4)
C3—C2—H2	121.8	C4—C7—H7	120.9
C4—C3—C2	121.9 (4)	C6—C7—H7	120.9

(Compound_13_Manual)

Crystal data

C6H5IN2O2	F(000) = 992
Mr = 264.02	Dx = 2.243 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3493 reflections
a = 7.7617 (15) Å	θ = 2.6–26.0°
b = 12.912 (3) Å	µ = 4.05 mm^−1
c = 15.663 (3) Å	T = 296 K
β = 95.141 (6)°	Block, yellow
V = 1563.5 (6) Å^3	0.45 × 0.45 × 0.40 mm
Z = 8

Data collection

Bruker SMART X2S diffractometer	2796 independent reflections
Radiation source: micro-focus sealed tube	2258 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.030
ω scans	θmax = 25.2°, θmin = 3.1°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→8
Tmin = 0.263, Tmax = 0.295	k = −15→14
9846 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0212P)^2 + 1.3049P] where P = (Fo^2 + 2Fc^2)/3
2796 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.83 e Å^−3
4 restraints	Δρmin = −0.65 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.39584 (4)	0.67281 (2)	0.153677 (16)	0.05022 (11)
I2	0.82449 (4)	0.87837 (2)	0.219736 (16)	0.05021 (11)
N1	0.3357 (5)	0.8471 (3)	0.2986 (2)	0.0481 (9)
H1A	0.301 (5)	0.850 (4)	0.2450 (8)	0.063 (15)*
H1B	0.301 (6)	0.893 (3)	0.333 (3)	0.079 (18)*
O1	0.7446 (4)	0.5151 (3)	0.52627 (18)	0.0624 (9)
O2	0.7598 (5)	0.4463 (3)	0.4020 (2)	0.0767 (11)
N4	1.0047 (6)	0.6712 (3)	0.3079 (3)	0.0582 (11)
H4A	0.964 (7)	0.678 (5)	0.2553 (12)	0.10 (2)*
H4B	1.062 (5)	0.618 (2)	0.328 (3)	0.068 (17)*
C10	0.4198 (5)	0.7641 (3)	0.3335 (2)	0.0342 (9)
N2	0.7104 (4)	0.5151 (3)	0.4481 (2)	0.0477 (9)
O3	0.7340 (5)	1.0189 (3)	0.5397 (2)	0.0691 (10)
O4	0.8666 (4)	0.9236 (3)	0.63678 (18)	0.0688 (10)
C1	0.4690 (5)	0.6788 (3)	0.2852 (2)	0.0339 (9)
C2	0.5637 (5)	0.5972 (3)	0.3222 (2)	0.0371 (9)
H2A	0.5976	0.5426	0.2889	0.044*
C3	0.6070 (5)	0.5984 (3)	0.4097 (2)	0.0358 (9)
C4	0.5562 (5)	0.6793 (3)	0.4600 (2)	0.0406 (10)
H4D	0.5840	0.6786	0.5190	0.049*
C5	0.4657 (5)	0.7593 (3)	0.4225 (2)	0.0398 (10)
H5	0.4325	0.8132	0.4568	0.048*
C6	0.9654 (5)	0.7407 (3)	0.3682 (2)	0.0391 (10)
C7	0.8817 (5)	0.8341 (3)	0.3476 (2)	0.0345 (9)
C8	0.8343 (5)	0.8999 (3)	0.4107 (2)	0.0352 (9)
H8	0.7751	0.9609	0.3962	0.042*
C9	0.8755 (5)	0.8745 (3)	0.4961 (2)	0.0364 (9)
N3	0.8213 (5)	0.9431 (3)	0.5614 (2)	0.0478 (9)
C11	0.9651 (5)	0.7839 (3)	0.5185 (2)	0.0422 (10)
H11	0.9949	0.7680	0.5758	0.051*
C12	1.0087 (5)	0.7185 (3)	0.4556 (3)	0.0455 (10)
H12	1.0685	0.6579	0.4706	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0660 (2)	0.0550 (2)	0.02816 (14)	−0.00721 (15)	−0.00371 (12)	−0.00356 (12)
I2	0.0681 (2)	0.0520 (2)	0.03015 (14)	−0.00639 (15)	0.00247 (12)	0.00068 (13)
N1	0.060 (2)	0.045 (3)	0.040 (2)	0.0112 (19)	0.0049 (19)	0.0021 (19)
O1	0.087 (2)	0.058 (2)	0.0393 (17)	0.0076 (18)	−0.0081 (16)	0.0072 (15)
O2	0.111 (3)	0.057 (3)	0.060 (2)	0.038 (2)	−0.0021 (19)	−0.0045 (18)
N4	0.067 (3)	0.040 (3)	0.070 (3)	0.008 (2)	0.017 (2)	−0.014 (2)
C10	0.032 (2)	0.035 (3)	0.0360 (19)	−0.0050 (18)	0.0046 (16)	−0.0008 (18)
N2	0.057 (2)	0.044 (2)	0.042 (2)	0.0002 (18)	−0.0021 (17)	0.0034 (18)
O3	0.099 (3)	0.055 (2)	0.0537 (19)	0.026 (2)	0.0106 (18)	−0.0101 (17)
O4	0.102 (3)	0.073 (3)	0.0315 (16)	−0.009 (2)	0.0055 (16)	−0.0037 (16)
C1	0.038 (2)	0.037 (2)	0.0267 (18)	−0.0073 (18)	0.0029 (16)	−0.0008 (17)
C2	0.045 (2)	0.031 (3)	0.036 (2)	−0.0032 (18)	0.0087 (17)	−0.0068 (17)
C3	0.037 (2)	0.036 (3)	0.0335 (19)	−0.0031 (18)	0.0013 (16)	0.0029 (18)
C4	0.046 (2)	0.047 (3)	0.0292 (19)	−0.003 (2)	0.0063 (17)	−0.0008 (19)
C5	0.050 (2)	0.037 (3)	0.0325 (19)	0.006 (2)	0.0093 (17)	−0.0045 (18)
C6	0.038 (2)	0.034 (3)	0.047 (2)	−0.0018 (18)	0.0103 (18)	0.0001 (19)
C7	0.038 (2)	0.035 (2)	0.0297 (18)	−0.0031 (18)	0.0029 (16)	0.0028 (17)
C8	0.041 (2)	0.030 (2)	0.0346 (19)	0.0000 (17)	0.0013 (16)	0.0029 (17)
C9	0.043 (2)	0.034 (2)	0.0324 (19)	−0.0046 (19)	0.0029 (17)	−0.0033 (17)
N3	0.061 (2)	0.048 (3)	0.0342 (19)	−0.011 (2)	0.0080 (16)	−0.0045 (17)
C11	0.041 (2)	0.045 (3)	0.039 (2)	−0.004 (2)	−0.0047 (18)	0.011 (2)
C12	0.041 (2)	0.034 (3)	0.061 (3)	0.0083 (19)	0.003 (2)	0.009 (2)

Geometric parameters (Å, º)

I1—C1	2.089 (3)	C2—C3	1.382 (5)
I2—C7	2.092 (4)	C2—H2A	0.9300
N1—C10	1.345 (5)	C3—C4	1.387 (6)
N1—H1A	0.858 (5)	C4—C5	1.353 (5)
N1—H1B	0.859 (5)	C4—H4D	0.9300
O1—N2	1.229 (4)	C5—H5	0.9300
O2—N2	1.229 (4)	C6—C7	1.393 (5)
N4—C6	1.358 (5)	C6—C12	1.408 (5)
N4—H4A	0.860 (5)	C7—C8	1.379 (5)
N4—H4B	0.859 (5)	C8—C9	1.385 (5)
C10—C5	1.408 (5)	C8—H8	0.9300
C10—C1	1.409 (5)	C9—C11	1.390 (6)
N2—C3	1.441 (5)	C9—N3	1.444 (5)
O3—N3	1.221 (5)	C11—C12	1.363 (6)
O4—N3	1.228 (4)	C11—H11	0.9300
C1—C2	1.382 (5)	C12—H12	0.9300
C10—N1—H1A	122 (3)	C4—C5—C10	122.6 (4)
C10—N1—H1B	118 (4)	C4—C5—H5	118.7
H1A—N1—H1B	119 (5)	C10—C5—H5	118.7
C6—N4—H4A	121 (4)	N4—C6—C7	122.7 (4)
C6—N4—H4B	115 (3)	N4—C6—C12	119.5 (4)
H4A—N4—H4B	124 (5)	C7—C6—C12	117.9 (4)
N1—C10—C5	120.6 (4)	C8—C7—C6	121.0 (3)
N1—C10—C1	123.3 (3)	C8—C7—I2	118.1 (3)
C5—C10—C1	116.1 (4)	C6—C7—I2	120.9 (3)
O2—N2—O1	122.3 (4)	C7—C8—C9	119.5 (4)
O2—N2—C3	119.1 (3)	C7—C8—H8	120.2
O1—N2—C3	118.6 (4)	C9—C8—H8	120.2
C2—C1—C10	122.1 (3)	C8—C9—C11	120.7 (4)
C2—C1—I1	118.2 (3)	C8—C9—N3	118.8 (4)
C10—C1—I1	119.7 (3)	C11—C9—N3	120.6 (3)
C1—C2—C3	118.7 (3)	O3—N3—O4	122.4 (4)
C1—C2—H2A	120.6	O3—N3—C9	119.0 (3)
C3—C2—H2A	120.6	O4—N3—C9	118.6 (4)
C2—C3—C4	121.1 (4)	C12—C11—C9	119.3 (4)
C2—C3—N2	118.8 (3)	C12—C11—H11	120.4
C4—C3—N2	120.1 (3)	C9—C11—H11	120.4
C5—C4—C3	119.4 (4)	C11—C12—C6	121.6 (4)
C5—C4—H4D	120.3	C11—C12—H12	119.2
C3—C4—H4D	120.3	C6—C12—H12	119.2

(Compound_13_X2S)

Crystal data

(C5H3IN2O3)·(C7H3IN2O)	F(000) = 952
Mr = 258.98	Dx = 2.200 Mg m^−3
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3493 reflections
a = 7.7617 (15) Å	θ = 2.6–26.0°
b = 12.912 (3) Å	µ = 4.04 mm^−1
c = 15.663 (3) Å	T = 296 K
β = 95.141 (6)°	Block, yellow
V = 1563.5 (6) Å^3	0.45 × 0.45 × 0.40 mm
Z = 8

Data collection

Bruker SMART X2S diffractometer	2799 independent reflections
Radiation source: micro-focus sealed tube	2259 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.030
ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→8
Tmin = 0.263, Tmax = 0.295	k = −15→14
9857 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 3.6546P] where P = (Fo^2 + 2Fc^2)/3
2799 reflections	(Δ/σ)max = 0.014
199 parameters	Δρmax = 0.97 e Å^−3
0 restraints	Δρmin = −0.76 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.39577 (6)	0.67279 (4)	0.15371 (2)	0.04982 (17)
I2	−0.17547 (6)	0.87836 (4)	0.21971 (2)	0.04987 (17)
O1	0.3317 (7)	0.8477 (4)	0.2977 (3)	0.0669 (14)
O2	0.7466 (7)	0.5151 (4)	0.5263 (3)	0.0623 (13)
O3	0.7616 (8)	0.4462 (4)	0.4021 (3)	0.0768 (17)
O4	0.0061 (8)	0.6701 (5)	0.3072 (4)	0.0798 (18)
N1	0.4183 (7)	0.7641 (5)	0.3335 (4)	0.0506 (14)
N2	0.7117 (7)	0.5153 (5)	0.4482 (3)	0.0468 (13)
N3	−0.2632 (8)	1.0182 (5)	0.5402 (3)	0.0504 (14)
N4	−0.1327 (7)	0.9236 (5)	0.6364 (3)	0.0505 (14)
C1	0.4682 (7)	0.6783 (5)	0.2854 (3)	0.0340 (13)
C2	0.5646 (8)	0.5967 (5)	0.3228 (4)	0.0378 (14)
H2	0.5990	0.5422	0.2895	0.045*
C3	0.6079 (7)	0.5979 (5)	0.4095 (4)	0.0361 (13)
C4	0.5570 (8)	0.6785 (5)	0.4605 (4)	0.0416 (15)
H4	0.5854	0.6777	0.5195	0.050*
C5	0.4639 (8)	0.7595 (5)	0.4224 (4)	0.0393 (14)
H5	0.4299	0.8131	0.4568	0.047*
C6	−0.0336 (7)	0.7401 (5)	0.3681 (4)	0.0389 (14)
C7	−0.1180 (7)	0.8340 (5)	0.3476 (4)	0.0350 (13)
C8	−0.1647 (7)	0.8999 (5)	0.4107 (3)	0.0353 (13)
H8	−0.2230	0.9612	0.3961	0.042*
C9	−0.1246 (7)	0.8743 (5)	0.4961 (4)	0.0374 (13)
C10	−0.1781 (8)	0.9428 (5)	0.5614 (3)	0.0328 (13)
C11	−0.0337 (8)	0.7833 (5)	0.5183 (4)	0.0428 (15)
H11	−0.0030	0.7675	0.5756	0.051*
C12	0.0092 (8)	0.7185 (5)	0.4559 (4)	0.0454 (15)
H12	0.0686	0.6577	0.4711	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0654 (3)	0.0547 (3)	0.0279 (2)	−0.0070 (2)	−0.00393 (18)	−0.00348 (18)
I2	0.0676 (3)	0.0519 (3)	0.0299 (2)	−0.0062 (2)	0.00246 (19)	0.00085 (18)
O1	0.073 (3)	0.062 (4)	0.066 (3)	0.011 (3)	0.007 (3)	0.011 (3)
O2	0.087 (4)	0.057 (3)	0.041 (3)	0.006 (3)	−0.007 (2)	0.007 (2)
O3	0.109 (4)	0.058 (4)	0.061 (3)	0.036 (3)	−0.003 (3)	−0.004 (3)
O4	0.085 (4)	0.058 (4)	0.100 (5)	0.001 (3)	0.029 (4)	−0.022 (3)
N1	0.048 (3)	0.053 (4)	0.050 (3)	−0.006 (3)	0.005 (2)	0.000 (3)
N2	0.057 (3)	0.043 (3)	0.039 (3)	0.001 (3)	−0.002 (2)	0.001 (3)
N3	0.074 (4)	0.042 (3)	0.036 (3)	0.014 (3)	0.011 (3)	−0.013 (3)
N4	0.075 (4)	0.051 (4)	0.025 (2)	−0.009 (3)	0.005 (2)	−0.005 (2)
C1	0.042 (3)	0.034 (3)	0.026 (3)	−0.006 (3)	0.003 (2)	−0.003 (2)
C2	0.047 (3)	0.031 (3)	0.036 (3)	−0.004 (3)	0.008 (3)	−0.007 (3)
C3	0.039 (3)	0.035 (4)	0.034 (3)	−0.004 (3)	0.002 (2)	0.004 (3)
C4	0.047 (3)	0.049 (4)	0.030 (3)	−0.003 (3)	0.007 (3)	0.000 (3)
C5	0.053 (4)	0.036 (4)	0.030 (3)	0.007 (3)	0.011 (3)	−0.005 (3)
C6	0.041 (3)	0.031 (3)	0.047 (3)	−0.001 (3)	0.013 (3)	0.001 (3)
C7	0.038 (3)	0.037 (4)	0.030 (3)	−0.004 (3)	0.003 (2)	0.002 (2)
C8	0.041 (3)	0.033 (3)	0.032 (3)	−0.003 (3)	0.002 (2)	0.001 (2)
C9	0.041 (3)	0.035 (4)	0.035 (3)	−0.005 (3)	0.002 (2)	0.000 (3)
C10	0.042 (3)	0.031 (3)	0.025 (3)	−0.010 (3)	0.006 (2)	−0.005 (2)
C11	0.041 (3)	0.045 (4)	0.040 (3)	−0.005 (3)	−0.005 (3)	0.013 (3)
C12	0.041 (3)	0.034 (4)	0.062 (4)	0.009 (3)	0.003 (3)	0.006 (3)

Geometric parameters (Å, º)

I1—C1	2.089 (5)	C3—C4	1.391 (9)
I2—C7	2.093 (6)	C4—C5	1.376 (9)
O1—N1	1.364 (8)	C4—H4	0.9300
O2—N2	1.230 (7)	C5—H5	0.9300
O3—N2	1.232 (7)	C6—C7	1.401 (8)
O4—C6	1.369 (8)	C6—C12	1.414 (9)
N1—C1	1.413 (8)	C7—C8	1.378 (8)
N1—C5	1.408 (8)	C8—C9	1.385 (8)
N2—C3	1.438 (8)	C8—H8	0.9300
N3—C10	1.206 (8)	C9—C11	1.399 (9)
N4—C10	1.221 (7)	C9—C10	1.441 (8)
C1—C2	1.391 (8)	C11—C12	1.351 (9)
C2—C3	1.368 (8)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
O1—N1—C1	123.3 (5)	O4—C6—C7	122.8 (6)
O1—N1—C5	120.7 (6)	O4—C6—C12	119.9 (6)
C1—N1—C5	116.0 (5)	C7—C6—C12	117.3 (5)
O2—N2—O3	121.9 (6)	C8—C7—C6	121.2 (5)
O2—N2—C3	119.1 (5)	C8—C7—I2	118.1 (4)
O3—N2—C3	119.0 (5)	C6—C7—I2	120.7 (4)
C2—C1—N1	122.1 (5)	C7—C8—C9	119.7 (6)
C2—C1—I1	118.5 (4)	C7—C8—H8	120.2
N1—C1—I1	119.4 (4)	C9—C8—H8	120.2
C3—C2—C1	119.0 (5)	C8—C9—C11	120.3 (6)
C3—C2—H2	120.5	C8—C9—C10	119.0 (6)
C1—C2—H2	120.5	C11—C9—C10	120.7 (5)
C2—C3—C4	121.4 (6)	N3—C10—N4	122.2 (6)
C2—C3—N2	119.2 (5)	N3—C10—C9	119.0 (5)
C4—C3—N2	119.3 (5)	N4—C10—C9	118.8 (6)
C3—C4—C5	119.0 (6)	C12—C11—C9	119.5 (6)
C3—C4—H4	120.5	C12—C11—H11	120.3
C5—C4—H4	120.5	C9—C11—H11	120.3
C4—C5—N1	122.5 (6)	C11—C12—C6	122.0 (6)
C4—C5—H5	118.8	C11—C12—H12	119.0
N1—C5—H5	118.8	C6—C12—H12	119.0

(Compound_14_CCDC)

Crystal data

C15H14N2O2S	F(000) = 600
Mr = 286.34	Dx = 1.349 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3129 reflections
a = 7.7598 (10) Å	θ = 2.5–23.1°
b = 9.9684 (13) Å	µ = 0.23 mm^−1
c = 18.231 (2) Å	T = 300 K
V = 1410.2 (3) Å^3	Block, colourless
Z = 4	0.33 × 0.31 × 0.21 mm

Data collection

Bruker SMART X2S diffractometer	2472 independent reflections
Radiation source: micro-focus sealed tube	1992 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.041
ω scans	θmax = 25.1°, θmin = 3.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.776, Tmax = 0.893	k = −11→11
8867 measured reflections	l = −19→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0396P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2472 reflections	Δρmax = 0.19 e Å^−3
182 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.14933 (8)	0.31893 (7)	0.72679 (3)	0.03844 (18)
O19	0.1780 (3)	0.40556 (19)	1.04551 (9)	0.0553 (5)
O2	0.1842 (3)	0.44623 (19)	0.69310 (10)	0.0546 (6)
N3	−0.0175 (3)	0.2413 (2)	0.70470 (11)	0.0482 (6)
N5	−0.2980 (3)	0.3529 (3)	0.72921 (16)	0.0817 (9)
C20	0.0861 (4)	0.3247 (3)	1.09773 (14)	0.0612 (8)
H20A	−0.0350	0.3282	1.0872	0.092*
H20B	0.1066	0.3584	1.1463	0.092*
H20C	0.1254	0.2336	1.0946	0.092*
C16	0.1661 (3)	0.3757 (3)	0.97230 (13)	0.0393 (6)
C17	0.0742 (3)	0.2686 (3)	0.94382 (13)	0.0379 (6)
H17	0.0165	0.2097	0.9748	0.046*
C18	0.0695 (3)	0.2503 (2)	0.86843 (13)	0.0372 (6)
H18	0.0085	0.1786	0.8486	0.045*
C13	0.1551 (3)	0.3383 (2)	0.82300 (12)	0.0345 (6)
C6	0.3144 (3)	0.2015 (3)	0.70575 (13)	0.0420 (7)
H6A	0.4244	0.2377	0.7214	0.050*
H6B	0.2940	0.1196	0.7331	0.050*
C7	0.3238 (3)	0.1686 (2)	0.62547 (12)	0.0354 (6)
C8	0.2464 (3)	0.0549 (3)	0.59824 (14)	0.0434 (6)
H8	0.1858	−0.0014	0.6296	0.052*
C9	0.2582 (4)	0.0238 (3)	0.52452 (15)	0.0466 (7)
H9	0.2067	−0.0539	0.5068	0.056*
C10	0.3457 (4)	0.1070 (3)	0.47724 (14)	0.0484 (7)
H10	0.3530	0.0857	0.4277	0.058*
C15	0.2529 (4)	0.4642 (3)	0.92658 (14)	0.0449 (7)
H15	0.3146	0.5355	0.9464	0.054*
C14	0.2473 (3)	0.4459 (3)	0.85180 (15)	0.0440 (6)
H14	0.3046	0.5049	0.8207	0.053*
C12	0.4112 (3)	0.2525 (3)	0.57734 (14)	0.0444 (7)
H12	0.4630	0.3303	0.5949	0.053*
C11	0.4218 (4)	0.2212 (3)	0.50332 (15)	0.0487 (8)
H11	0.4807	0.2778	0.4715	0.058*
C4	−0.1661 (4)	0.3047 (3)	0.71876 (14)	0.0524 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0397 (3)	0.0478 (4)	0.0278 (3)	−0.0003 (3)	0.0008 (3)	0.0000 (3)
O19	0.0695 (14)	0.0665 (13)	0.0299 (10)	−0.0079 (11)	−0.0053 (10)	−0.0103 (9)
O2	0.0728 (15)	0.0502 (11)	0.0408 (10)	−0.0001 (11)	0.0061 (9)	0.0073 (9)
N3	0.0421 (13)	0.0678 (15)	0.0346 (11)	−0.0036 (12)	−0.0016 (10)	−0.0110 (11)
N5	0.0405 (16)	0.131 (3)	0.0737 (19)	0.0055 (15)	−0.0044 (14)	−0.027 (2)
C20	0.078 (2)	0.078 (2)	0.0275 (14)	0.0001 (19)	0.0007 (13)	0.0026 (16)
C16	0.0407 (15)	0.0472 (14)	0.0302 (14)	0.0051 (14)	−0.0054 (12)	−0.0071 (12)
C17	0.0431 (15)	0.0421 (15)	0.0287 (13)	0.0008 (13)	0.0042 (11)	0.0028 (12)
C18	0.0405 (13)	0.0364 (14)	0.0348 (14)	−0.0043 (12)	−0.0056 (11)	−0.0031 (13)
C13	0.0339 (12)	0.0415 (14)	0.0280 (12)	0.0006 (14)	0.0035 (11)	−0.0017 (11)
C6	0.0393 (16)	0.0504 (16)	0.0364 (14)	0.0010 (13)	−0.0019 (11)	−0.0036 (12)
C7	0.0339 (13)	0.0398 (13)	0.0327 (13)	0.0022 (13)	0.0016 (10)	0.0011 (12)
C8	0.0451 (15)	0.0409 (15)	0.0442 (16)	0.0000 (14)	0.0105 (13)	0.0014 (13)
C9	0.0497 (16)	0.0478 (17)	0.0424 (16)	−0.0020 (14)	0.0014 (13)	−0.0109 (14)
C10	0.0514 (16)	0.0619 (17)	0.0318 (14)	0.0073 (17)	0.0044 (14)	−0.0058 (14)
C15	0.0493 (16)	0.0443 (15)	0.0413 (16)	−0.0118 (14)	−0.0056 (13)	−0.0100 (13)
C14	0.0461 (15)	0.0460 (15)	0.0398 (16)	−0.0088 (14)	0.0035 (13)	0.0007 (14)
C12	0.0458 (16)	0.0431 (15)	0.0443 (16)	−0.0040 (13)	0.0034 (12)	−0.0072 (14)
C11	0.0537 (17)	0.0501 (19)	0.0423 (16)	−0.0007 (14)	0.0106 (13)	0.0121 (15)
C4	0.0433 (16)	0.084 (2)	0.0303 (14)	−0.0023 (17)	−0.0033 (14)	−0.0100 (16)

Geometric parameters (Å, º)

S1—O2	1.436 (2)	C6—C7	1.502 (3)
S1—N3	1.561 (2)	C6—H6A	0.9700
S1—C13	1.765 (2)	C6—H6B	0.9700
S1—C6	1.777 (2)	C7—C8	1.375 (3)
O19—C16	1.370 (3)	C7—C12	1.389 (3)
O19—C20	1.437 (3)	C8—C9	1.382 (4)
N3—C4	1.340 (4)	C8—H8	0.9300
N5—C4	1.146 (3)	C9—C10	1.375 (4)
C20—H20A	0.9600	C9—H9	0.9300
C20—H20B	0.9600	C10—C11	1.368 (4)
C20—H20C	0.9600	C10—H10	0.9300
C16—C17	1.385 (3)	C15—C14	1.376 (3)
C16—C15	1.388 (4)	C15—H15	0.9300
C17—C18	1.387 (3)	C14—H14	0.9300
C17—H17	0.9300	C12—C11	1.387 (4)
C18—C13	1.378 (3)	C12—H12	0.9300
C18—H18	0.9300	C11—H11	0.9300
C13—C14	1.391 (3)
O2—S1—N3	118.95 (12)	C7—C6—H6B	109.0
O2—S1—C13	108.88 (11)	S1—C6—H6B	109.0
N3—S1—C13	109.38 (12)	H6A—C6—H6B	107.8
O2—S1—C6	110.73 (12)	C8—C7—C12	118.8 (2)
N3—S1—C6	102.46 (12)	C8—C7—C6	120.7 (2)
C13—S1—C6	105.55 (12)	C12—C7—C6	120.5 (2)
C16—O19—C20	119.4 (2)	C9—C8—C7	120.5 (2)
C4—N3—S1	115.52 (19)	C9—C8—H8	119.8
O19—C20—H20A	109.5	C7—C8—H8	119.8
O19—C20—H20B	109.5	C10—C9—C8	120.4 (3)
H20A—C20—H20B	109.5	C10—C9—H9	119.8
O19—C20—H20C	109.5	C8—C9—H9	119.8
H20A—C20—H20C	109.5	C9—C10—C11	119.8 (2)
H20B—C20—H20C	109.5	C9—C10—H10	120.1
O19—C16—C17	124.5 (2)	C11—C10—H10	120.1
O19—C16—C15	114.5 (2)	C14—C15—C16	119.7 (2)
C17—C16—C15	121.0 (2)	C14—C15—H15	120.2
C18—C17—C16	119.1 (2)	C16—C15—H15	120.2
C18—C17—H17	120.4	C15—C14—C13	119.5 (2)
C16—C17—H17	120.4	C15—C14—H14	120.2
C17—C18—C13	119.9 (2)	C13—C14—H14	120.2
C17—C18—H18	120.0	C11—C12—C7	120.5 (2)
C13—C18—H18	120.0	C11—C12—H12	119.7
C18—C13—C14	120.8 (2)	C7—C12—H12	119.7
C18—C13—S1	121.01 (19)	C10—C11—C12	120.0 (2)
C14—C13—S1	118.19 (18)	C10—C11—H11	120.0
C7—C6—S1	112.91 (17)	C12—C11—H11	120.0
C7—C6—H6A	109.0	N5—C4—N3	176.2 (3)
S1—C6—H6A	109.0

(Compound_14_Manual)

Crystal data

C15H14N2O2S	F(000) = 600
Mr = 286.34	Dx = 1.349 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3129 reflections
a = 7.7598 (10) Å	θ = 2.5–23.1°
b = 9.9684 (13) Å	µ = 0.23 mm^−1
c = 18.231 (2) Å	T = 300 K
V = 1410.2 (3) Å^3	Block, colourless
Z = 4	0.33 × 0.31 × 0.21 mm

Data collection

Bruker SMART X2S diffractometer	2472 independent reflections
Radiation source: micro-focus sealed tube	1992 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.041
ω scans	θmax = 25.1°, θmin = 3.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.776, Tmax = 0.893	k = −11→11
8867 measured reflections	l = −19→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0396P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2472 reflections	Δρmax = 0.19 e Å^−3
182 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.14933 (8)	0.31893 (7)	0.72679 (3)	0.03844 (18)
O19	0.1780 (3)	0.40556 (19)	1.04551 (9)	0.0553 (5)
O2	0.1842 (3)	0.44623 (19)	0.69310 (10)	0.0546 (6)
N3	−0.0175 (3)	0.2413 (2)	0.70470 (11)	0.0482 (6)
N5	−0.2980 (3)	0.3529 (3)	0.72921 (16)	0.0817 (9)
C20	0.0861 (4)	0.3247 (3)	1.09773 (14)	0.0612 (8)
H20A	−0.0350	0.3282	1.0872	0.092*
H20B	0.1066	0.3584	1.1463	0.092*
H20C	0.1254	0.2336	1.0946	0.092*
C16	0.1661 (3)	0.3757 (3)	0.97230 (13)	0.0393 (6)
C17	0.0742 (3)	0.2686 (3)	0.94382 (13)	0.0379 (6)
H17	0.0165	0.2097	0.9748	0.046*
C18	0.0695 (3)	0.2503 (2)	0.86843 (13)	0.0372 (6)
H18	0.0085	0.1786	0.8486	0.045*
C13	0.1551 (3)	0.3383 (2)	0.82300 (12)	0.0345 (6)
C6	0.3144 (3)	0.2015 (3)	0.70575 (13)	0.0420 (7)
H6A	0.4244	0.2377	0.7214	0.050*
H6B	0.2940	0.1196	0.7331	0.050*
C7	0.3238 (3)	0.1686 (2)	0.62547 (12)	0.0354 (6)
C8	0.2464 (3)	0.0549 (3)	0.59824 (14)	0.0434 (6)
H8	0.1858	−0.0014	0.6296	0.052*
C9	0.2582 (4)	0.0238 (3)	0.52452 (15)	0.0466 (7)
H9	0.2067	−0.0539	0.5068	0.056*
C10	0.3457 (4)	0.1070 (3)	0.47724 (14)	0.0484 (7)
H10	0.3530	0.0857	0.4277	0.058*
C15	0.2529 (4)	0.4642 (3)	0.92658 (14)	0.0449 (7)
H15	0.3146	0.5355	0.9464	0.054*
C14	0.2473 (3)	0.4459 (3)	0.85180 (15)	0.0440 (6)
H14	0.3046	0.5049	0.8207	0.053*
C12	0.4112 (3)	0.2525 (3)	0.57734 (14)	0.0444 (7)
H12	0.4630	0.3303	0.5949	0.053*
C11	0.4218 (4)	0.2212 (3)	0.50332 (15)	0.0487 (8)
H11	0.4807	0.2778	0.4715	0.058*
C4	−0.1661 (4)	0.3047 (3)	0.71876 (14)	0.0524 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0397 (3)	0.0478 (4)	0.0278 (3)	−0.0003 (3)	0.0008 (3)	0.0000 (3)
O19	0.0695 (14)	0.0665 (13)	0.0299 (10)	−0.0079 (11)	−0.0053 (10)	−0.0103 (9)
O2	0.0728 (15)	0.0502 (11)	0.0408 (10)	−0.0001 (11)	0.0061 (9)	0.0073 (9)
N3	0.0421 (13)	0.0678 (15)	0.0346 (11)	−0.0036 (12)	−0.0016 (10)	−0.0110 (11)
N5	0.0405 (16)	0.131 (3)	0.0737 (19)	0.0055 (15)	−0.0044 (14)	−0.027 (2)
C20	0.078 (2)	0.078 (2)	0.0275 (14)	0.0001 (19)	0.0007 (13)	0.0026 (16)
C16	0.0407 (15)	0.0472 (14)	0.0302 (14)	0.0051 (14)	−0.0054 (12)	−0.0071 (12)
C17	0.0431 (15)	0.0421 (15)	0.0287 (13)	0.0008 (13)	0.0042 (11)	0.0028 (12)
C18	0.0405 (13)	0.0364 (14)	0.0348 (14)	−0.0043 (12)	−0.0056 (11)	−0.0031 (13)
C13	0.0339 (12)	0.0415 (14)	0.0280 (12)	0.0006 (14)	0.0035 (11)	−0.0017 (11)
C6	0.0393 (16)	0.0504 (16)	0.0364 (14)	0.0010 (13)	−0.0019 (11)	−0.0036 (12)
C7	0.0339 (13)	0.0398 (13)	0.0327 (13)	0.0022 (13)	0.0016 (10)	0.0011 (12)
C8	0.0451 (15)	0.0409 (15)	0.0442 (16)	0.0000 (14)	0.0105 (13)	0.0014 (13)
C9	0.0497 (16)	0.0478 (17)	0.0424 (16)	−0.0020 (14)	0.0014 (13)	−0.0109 (14)
C10	0.0514 (16)	0.0619 (17)	0.0318 (14)	0.0073 (17)	0.0044 (14)	−0.0058 (14)
C15	0.0493 (16)	0.0443 (15)	0.0413 (16)	−0.0118 (14)	−0.0056 (13)	−0.0100 (13)
C14	0.0461 (15)	0.0460 (15)	0.0398 (16)	−0.0088 (14)	0.0035 (13)	0.0007 (14)
C12	0.0458 (16)	0.0431 (15)	0.0443 (16)	−0.0040 (13)	0.0034 (12)	−0.0072 (14)
C11	0.0537 (17)	0.0501 (19)	0.0423 (16)	−0.0007 (14)	0.0106 (13)	0.0121 (15)
C4	0.0433 (16)	0.084 (2)	0.0303 (14)	−0.0023 (17)	−0.0033 (14)	−0.0100 (16)

Geometric parameters (Å, º)

S1—O2	1.436 (2)	C6—C7	1.502 (3)
S1—N3	1.561 (2)	C6—H6A	0.9700
S1—C13	1.765 (2)	C6—H6B	0.9700
S1—C6	1.777 (2)	C7—C8	1.375 (3)
O19—C16	1.370 (3)	C7—C12	1.389 (3)
O19—C20	1.437 (3)	C8—C9	1.382 (4)
N3—C4	1.340 (4)	C8—H8	0.9300
N5—C4	1.146 (3)	C9—C10	1.375 (4)
C20—H20A	0.9600	C9—H9	0.9300
C20—H20B	0.9600	C10—C11	1.368 (4)
C20—H20C	0.9600	C10—H10	0.9300
C16—C17	1.385 (3)	C15—C14	1.376 (3)
C16—C15	1.388 (4)	C15—H15	0.9300
C17—C18	1.387 (3)	C14—H14	0.9300
C17—H17	0.9300	C12—C11	1.387 (4)
C18—C13	1.378 (3)	C12—H12	0.9300
C18—H18	0.9300	C11—H11	0.9300
C13—C14	1.391 (3)
O2—S1—N3	118.95 (12)	C7—C6—H6B	109.0
O2—S1—C13	108.88 (11)	S1—C6—H6B	109.0
N3—S1—C13	109.38 (12)	H6A—C6—H6B	107.8
O2—S1—C6	110.73 (12)	C8—C7—C12	118.8 (2)
N3—S1—C6	102.46 (12)	C8—C7—C6	120.7 (2)
C13—S1—C6	105.55 (12)	C12—C7—C6	120.5 (2)
C16—O19—C20	119.4 (2)	C9—C8—C7	120.5 (2)
C4—N3—S1	115.52 (19)	C9—C8—H8	119.8
O19—C20—H20A	109.5	C7—C8—H8	119.8
O19—C20—H20B	109.5	C10—C9—C8	120.4 (3)
H20A—C20—H20B	109.5	C10—C9—H9	119.8
O19—C20—H20C	109.5	C8—C9—H9	119.8
H20A—C20—H20C	109.5	C9—C10—C11	119.8 (2)
H20B—C20—H20C	109.5	C9—C10—H10	120.1
O19—C16—C17	124.5 (2)	C11—C10—H10	120.1
O19—C16—C15	114.5 (2)	C14—C15—C16	119.7 (2)
C17—C16—C15	121.0 (2)	C14—C15—H15	120.2
C18—C17—C16	119.1 (2)	C16—C15—H15	120.2
C18—C17—H17	120.4	C15—C14—C13	119.5 (2)
C16—C17—H17	120.4	C15—C14—H14	120.2
C17—C18—C13	119.9 (2)	C13—C14—H14	120.2
C17—C18—H18	120.0	C11—C12—C7	120.5 (2)
C13—C18—H18	120.0	C11—C12—H12	119.7
C18—C13—C14	120.8 (2)	C7—C12—H12	119.7
C18—C13—S1	121.01 (19)	C10—C11—C12	120.0 (2)
C14—C13—S1	118.19 (18)	C10—C11—H11	120.0
C7—C6—S1	112.91 (17)	C12—C11—H11	120.0
C7—C6—H6A	109.0	N5—C4—N3	176.2 (3)
S1—C6—H6A	109.0

(Compound_14_X2S)

Crystal data

C15H14N2O2S	F(000) = 608
Mr = 288.36	Dx = 1.358 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3129 reflections
a = 7.7592 (10) Å	θ = 2.5–23.1°
b = 9.9677 (13) Å	µ = 0.23 mm^−1
c = 18.230 (2) Å	T = 300 K
V = 1409.9 (3) Å^3	Block, colorless
Z = 4	0.33 × 0.31 × 0.21 mm

Data collection

Bruker SMART X2S diffractometer	2458 independent reflections
Radiation source: micro-focus sealed tube	1984 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.041
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.776, Tmax = 0.893	k = −11→11
8816 measured reflections	l = −21→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 0.2488P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.070
2458 reflections	Δρmax = 0.15 e Å^−3
183 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (12)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.14932 (11)	0.31891 (9)	0.72682 (4)	0.0374 (2)
O1	0.1782 (4)	0.4052 (3)	1.04528 (12)	0.0546 (7)
O2	0.1822 (4)	0.4455 (3)	0.69252 (14)	0.0544 (7)
H2	0.2623	0.4830	0.7135	0.082*
N1	−0.0176 (4)	0.2436 (3)	0.70515 (15)	0.0487 (8)
H1	−0.0143	0.1655	0.6852	0.058*
N2	−0.2979 (4)	0.3532 (5)	0.7290 (2)	0.0800 (12)
C1	0.3451 (5)	0.1060 (4)	0.47732 (19)	0.0477 (9)
H1A	0.3527	0.0845	0.4278	0.057*
C2	0.2579 (5)	0.0229 (4)	0.5241 (2)	0.0458 (9)
H2A	0.2065	−0.0548	0.5063	0.055*
C3	0.2461 (5)	0.0540 (3)	0.59781 (19)	0.0431 (8)
H3	0.1855	−0.0023	0.6293	0.052*
C4	0.3240 (4)	0.1687 (3)	0.62498 (17)	0.0355 (7)
C5	0.3147 (4)	0.2019 (4)	0.70568 (17)	0.0412 (9)
H5A	0.4247	0.2384	0.7212	0.049*
H5B	0.2948	0.1199	0.7331	0.049*
C6	0.1549 (4)	0.3382 (3)	0.82328 (16)	0.0341 (7)
C7	0.0698 (4)	0.2497 (3)	0.86932 (17)	0.0369 (8)
H7	0.0097	0.1774	0.8497	0.044*
C8	0.0738 (4)	0.2685 (3)	0.94418 (17)	0.0370 (8)
H8	0.0155	0.2099	0.9752	0.044*
C9	0.1653 (5)	0.3753 (3)	0.97274 (17)	0.0382 (8)
C10	0.0868 (5)	0.3244 (5)	1.09696 (18)	0.0589 (10)
H10A	−0.0341	0.3261	1.0857	0.088*
H10B	0.1047	0.3590	1.1455	0.088*
H10C	0.1281	0.2337	1.0945	0.088*
C11	0.4215 (5)	0.2213 (4)	0.5032 (2)	0.0491 (10)
H11	0.4797	0.2779	0.4711	0.059*
C12	0.4115 (4)	0.2529 (4)	0.57708 (19)	0.0438 (9)
H12	0.4636	0.3305	0.5946	0.053*
C13	−0.1663 (5)	0.3050 (4)	0.71875 (18)	0.0512 (9)
C14	0.2524 (5)	0.4634 (4)	0.92723 (19)	0.0450 (9)
H14	0.3142	0.5345	0.9472	0.054*
C15	0.2474 (4)	0.4457 (4)	0.85222 (19)	0.0423 (8)
H15	0.3050	0.5049	0.8213	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0385 (4)	0.0468 (5)	0.0270 (4)	−0.0002 (4)	0.0007 (4)	−0.0001 (4)
O1	0.0695 (18)	0.0653 (17)	0.0291 (13)	−0.0096 (15)	−0.0053 (13)	−0.0106 (12)
O2	0.068 (2)	0.0523 (15)	0.0426 (15)	−0.0042 (14)	0.0028 (12)	0.0049 (13)
N1	0.0462 (18)	0.0628 (19)	0.0370 (16)	−0.0045 (16)	−0.0026 (14)	−0.0184 (15)
N2	0.041 (2)	0.125 (4)	0.073 (3)	0.005 (2)	−0.0043 (19)	−0.027 (3)
C1	0.052 (2)	0.061 (2)	0.0307 (18)	0.010 (2)	0.0032 (18)	−0.0072 (17)
C2	0.048 (2)	0.048 (2)	0.041 (2)	−0.0008 (19)	0.0017 (17)	−0.0105 (18)
C3	0.044 (2)	0.0412 (19)	0.044 (2)	0.0013 (18)	0.0096 (17)	0.0020 (17)
C4	0.0337 (17)	0.0401 (17)	0.0327 (17)	0.0023 (17)	0.0030 (14)	0.0012 (16)
C5	0.040 (2)	0.046 (2)	0.0370 (19)	0.0014 (16)	−0.0016 (14)	−0.0036 (16)
C6	0.0334 (16)	0.0407 (18)	0.0284 (16)	0.0006 (18)	0.0013 (15)	−0.0020 (14)
C7	0.0404 (17)	0.0373 (18)	0.0329 (18)	−0.0050 (16)	−0.0058 (14)	−0.0015 (16)
C8	0.0422 (19)	0.0404 (19)	0.0283 (17)	0.0010 (16)	0.0048 (15)	0.0031 (15)
C9	0.0395 (19)	0.0448 (18)	0.0303 (18)	0.0025 (18)	−0.0032 (16)	−0.0057 (15)
C10	0.075 (3)	0.076 (3)	0.0258 (18)	0.000 (2)	0.0000 (17)	0.004 (2)
C11	0.054 (2)	0.053 (3)	0.040 (2)	0.0000 (19)	0.0111 (17)	0.0126 (19)
C12	0.045 (2)	0.0426 (19)	0.044 (2)	−0.0035 (17)	0.0038 (16)	−0.0067 (18)
C13	0.040 (2)	0.082 (3)	0.0313 (18)	−0.002 (2)	−0.0031 (18)	−0.012 (2)
C14	0.050 (2)	0.043 (2)	0.041 (2)	−0.0108 (18)	−0.0081 (17)	−0.0106 (17)
C15	0.045 (2)	0.0443 (19)	0.038 (2)	−0.0099 (18)	0.0043 (17)	−0.0005 (17)

Geometric parameters (Å, º)

S1—O2	1.431 (3)	C5—H5A	0.9700
S1—N1	1.548 (3)	C5—H5B	0.9700
S1—C6	1.769 (3)	C6—C7	1.385 (4)
S1—C5	1.777 (3)	C6—C15	1.394 (4)
O1—C9	1.359 (4)	C7—C8	1.378 (4)
O1—C10	1.428 (4)	C7—H7	0.9300
O2—H2	0.8200	C8—C9	1.381 (5)
N1—C13	1.330 (5)	C8—H8	0.9300
N1—H1	0.8600	C9—C14	1.384 (5)
N2—C13	1.144 (5)	C10—H10A	0.9600
C1—C11	1.376 (5)	C10—H10B	0.9600
C1—C2	1.368 (5)	C10—H10C	0.9600
C1—H1A	0.9300	C11—C12	1.386 (5)
C2—C3	1.382 (5)	C11—H11	0.9300
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.385 (5)	C14—C15	1.379 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C12	1.388 (5)	C15—H15	0.9300
C4—C5	1.509 (4)
O2—S1—N1	117.71 (17)	C7—C6—S1	121.4 (2)
O2—S1—C6	109.52 (16)	C15—C6—S1	118.2 (2)
N1—S1—C6	109.07 (16)	C8—C7—C6	120.2 (3)
O2—S1—C5	110.81 (17)	C8—C7—H7	119.9
N1—S1—C5	103.34 (17)	C6—C7—H7	119.9
C6—S1—C5	105.60 (16)	C7—C8—C9	119.3 (3)
C9—O1—C10	118.8 (3)	C7—C8—H8	120.3
S1—O2—H2	109.5	C9—C8—H8	120.3
C13—N1—S1	117.1 (3)	O1—C9—C14	114.1 (3)
C13—N1—H1	121.4	O1—C9—C8	125.0 (3)
S1—N1—H1	121.4	C14—C9—C8	120.9 (3)
C11—C1—C2	120.3 (3)	O1—C10—H10A	109.5
C11—C1—H1A	119.8	O1—C10—H10B	109.5
C2—C1—H1A	119.8	H10A—C10—H10B	109.5
C3—C2—C1	120.2 (3)	O1—C10—H10C	109.5
C3—C2—H2A	119.9	H10A—C10—H10C	109.5
C1—C2—H2A	119.9	H10B—C10—H10C	109.5
C2—C3—C4	120.3 (3)	C1—C11—C12	119.9 (3)
C2—C3—H3	119.9	C1—C11—H11	120.1
C4—C3—H3	119.9	C12—C11—H11	120.1
C3—C4—C12	119.2 (3)	C11—C12—C4	120.1 (3)
C3—C4—C5	120.6 (3)	C11—C12—H12	119.9
C12—C4—C5	120.3 (3)	C4—C12—H12	119.9
C4—C5—S1	112.9 (2)	N2—C13—N1	177.0 (4)
C4—C5—H5A	109.0	C15—C14—C9	120.0 (3)
S1—C5—H5A	109.0	C15—C14—H14	120.0
C4—C5—H5B	109.0	C9—C14—H14	120.0
S1—C5—H5B	109.0	C14—C15—C6	119.2 (3)
H5A—C5—H5B	107.8	C14—C15—H15	120.4
C7—C6—C15	120.4 (3)	C6—C15—H15	120.4

(Compound_15_CCDC)

Crystal data

C14H17N3O4S2·C3H6O	F(000) = 872
Mr = 413.50	Dx = 1.299 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.811 (4) Å	Cell parameters from 137 reflections
b = 17.503 (10) Å	θ = 3.5–22.5°
c = 15.892 (9) Å	µ = 0.28 mm^−1
β = 103.305 (17)°	T = 300 K
V = 2114 (2) Å^3	Block, colorless
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer	3694 independent reflections
Radiation source: micro-focus sealed tube	2806 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.044
ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.665, Tmax = 0.745	k = −20→20
19952 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0858P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
3694 reflections	Δρmax = 0.37 e Å^−3
250 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.28837 (8)	0.63439 (3)	0.46309 (4)	0.0404 (2)
S6	−0.04773 (9)	0.64674 (4)	0.31660 (4)	0.0556 (3)
O18	0.0932 (2)	1.00041 (8)	0.75637 (10)	0.0517 (5)
N4	−0.1225 (3)	0.58031 (10)	0.46378 (12)	0.0435 (5)
O3	−0.3655 (2)	0.66530 (9)	0.37768 (10)	0.0490 (5)
O17	−0.0133 (3)	0.99439 (11)	0.60986 (12)	0.0919 (8)
O2	−0.4001 (2)	0.59171 (10)	0.50589 (11)	0.0551 (5)
C22	−0.0274 (7)	1.1278 (2)	0.7235 (3)	0.145 (2)
H22A	−0.0660	1.1191	0.6625	0.217*
H22B	−0.0033	1.1811	0.7340	0.217*
H22C	−0.1180	1.1121	0.7517	0.217*
O24	0.4299 (4)	0.79797 (16)	0.62932 (17)	0.1176 (10)
C19	0.2825 (7)	1.0937 (2)	0.7105 (2)	0.1193 (17)
H20B	0.3843	1.0646	0.7377	0.179*
H19C	0.3126	1.1469	0.7114	0.179*
H19A	0.2416	1.0771	0.6517	0.179*
C20	0.1385 (4)	1.08189 (13)	0.75896 (17)	0.0620 (8)
C16	0.0248 (4)	0.96523 (14)	0.68011 (15)	0.0504 (6)
N15	0.0047 (3)	0.89072 (10)	0.69721 (11)	0.0424 (5)
H15	0.0381	0.8772	0.7505	0.051*
C12	−0.0642 (3)	0.83270 (12)	0.63812 (13)	0.0368 (5)
C13	−0.0826 (3)	0.76149 (13)	0.67259 (14)	0.0469 (6)
H13	−0.0486	0.7540	0.7320	0.056*
C14	−0.1507 (3)	0.70191 (13)	0.61948 (14)	0.0478 (6)
H14	−0.1628	0.6542	0.6433	0.057*
C9	−0.2019 (3)	0.71180 (12)	0.53041 (13)	0.0368 (5)
C5	−0.0217 (3)	0.58938 (12)	0.40788 (15)	0.0406 (6)
N9	0.1271 (3)	0.54800 (11)	0.41620 (13)	0.0480 (5)
H9	0.1607	0.5158	0.4576	0.058*
C8	0.2219 (3)	0.56063 (16)	0.35420 (17)	0.0571 (7)
H8	0.3268	0.5359	0.3532	0.069*
C7	0.1465 (4)	0.61199 (18)	0.2962 (2)	0.0675 (8)
H7	0.1924	0.6276	0.2499	0.081*
C11	−0.1154 (3)	0.84304 (13)	0.54868 (15)	0.0488 (6)
H11	−0.1033	0.8907	0.5248	0.059*
C10	−0.1838 (3)	0.78245 (13)	0.49567 (15)	0.0484 (6)
H10	−0.2178	0.7895	0.4362	0.058*
C21	0.2082 (4)	1.09676 (15)	0.85507 (17)	0.0667 (8)
H21B	0.1190	1.0844	0.8855	0.100*
H21C	0.2396	1.1497	0.8640	0.100*
H21A	0.3101	1.0656	0.8764	0.100*
C23	0.3811 (4)	0.8226 (2)	0.5564 (2)	0.0817 (10)
C25	0.3123 (5)	0.7697 (2)	0.4830 (2)	0.0972 (12)
H25B	0.3283	0.7178	0.5029	0.146*
H25C	0.3749	0.7778	0.4384	0.146*
H25A	0.1893	0.7794	0.4604	0.146*
C26	0.3885 (7)	0.9041 (3)	0.5367 (4)	0.149 (2)
H26C	0.2712	0.9239	0.5188	0.223*
H26A	0.4490	0.9109	0.4910	0.223*
H26B	0.4503	0.9309	0.5873	0.223*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0483 (4)	0.0345 (3)	0.0351 (4)	−0.0001 (3)	0.0028 (3)	−0.0039 (2)
S6	0.0527 (5)	0.0572 (4)	0.0558 (4)	0.0029 (3)	0.0100 (3)	0.0228 (3)
O18	0.0812 (12)	0.0318 (9)	0.0372 (9)	−0.0067 (8)	0.0034 (8)	−0.0030 (7)
N4	0.0611 (13)	0.0327 (10)	0.0368 (10)	0.0069 (9)	0.0118 (9)	0.0001 (8)
O3	0.0577 (10)	0.0457 (10)	0.0356 (9)	0.0055 (8)	−0.0061 (7)	−0.0048 (7)
O17	0.171 (2)	0.0448 (11)	0.0417 (11)	−0.0210 (13)	−0.0129 (13)	0.0058 (9)
O2	0.0604 (11)	0.0469 (10)	0.0590 (11)	−0.0133 (9)	0.0159 (9)	−0.0050 (8)
C22	0.190 (5)	0.050 (2)	0.138 (4)	0.039 (3)	−0.076 (3)	−0.023 (2)
O24	0.163 (3)	0.105 (2)	0.0744 (18)	0.0005 (19)	0.0062 (17)	−0.0149 (16)
C19	0.192 (4)	0.105 (3)	0.065 (2)	−0.084 (3)	0.039 (3)	−0.015 (2)
C20	0.100 (2)	0.0296 (13)	0.0475 (15)	−0.0092 (13)	−0.0023 (15)	−0.0003 (11)
C16	0.0752 (18)	0.0358 (13)	0.0342 (13)	−0.0033 (12)	0.0001 (12)	−0.0012 (10)
N15	0.0579 (12)	0.0360 (10)	0.0277 (10)	−0.0001 (9)	−0.0014 (9)	−0.0003 (8)
C12	0.0403 (13)	0.0348 (12)	0.0331 (12)	0.0025 (10)	0.0039 (10)	−0.0022 (9)
C13	0.0687 (17)	0.0389 (13)	0.0288 (12)	0.0024 (12)	0.0027 (11)	0.0024 (10)
C14	0.0688 (16)	0.0319 (12)	0.0379 (13)	−0.0004 (11)	0.0023 (11)	0.0032 (10)
C9	0.0414 (12)	0.0337 (12)	0.0329 (12)	0.0027 (10)	0.0033 (10)	−0.0014 (9)
C5	0.0482 (14)	0.0286 (11)	0.0395 (13)	−0.0015 (10)	−0.0015 (11)	−0.0010 (10)
N9	0.0530 (12)	0.0430 (11)	0.0449 (11)	0.0079 (10)	0.0051 (10)	0.0035 (9)
C8	0.0452 (15)	0.0640 (18)	0.0626 (17)	−0.0002 (13)	0.0133 (13)	0.0018 (14)
C7	0.0543 (17)	0.083 (2)	0.0680 (19)	0.0012 (16)	0.0205 (14)	0.0252 (17)
C11	0.0728 (18)	0.0352 (13)	0.0342 (13)	−0.0070 (12)	0.0038 (12)	0.0030 (10)
C10	0.0693 (17)	0.0404 (13)	0.0311 (12)	−0.0042 (12)	0.0024 (11)	0.0004 (10)
C21	0.102 (2)	0.0395 (15)	0.0504 (16)	−0.0064 (15)	0.0021 (15)	−0.0090 (12)
C23	0.074 (2)	0.084 (2)	0.083 (3)	0.0108 (19)	0.0084 (19)	−0.004 (2)
C25	0.103 (3)	0.101 (3)	0.078 (2)	0.023 (2)	0.001 (2)	−0.007 (2)
C26	0.141 (4)	0.083 (3)	0.204 (6)	0.002 (3)	0.002 (4)	0.024 (3)

Geometric parameters (Å, º)

S1—O2	1.4337 (18)	C13—C14	1.370 (3)
S1—O3	1.4566 (17)	C13—H13	0.9300
S1—N4	1.602 (2)	C14—C9	1.390 (3)
S1—C9	1.762 (2)	C14—H14	0.9300
S6—C7	1.733 (3)	C9—C10	1.375 (3)
S6—C5	1.737 (2)	C5—N9	1.350 (3)
O18—C16	1.355 (3)	N9—C8	1.380 (3)
O18—C20	1.468 (3)	N9—H9	0.8600
N4—C5	1.325 (3)	C8—C7	1.325 (4)
O17—C16	1.201 (3)	C8—H8	0.9300
C22—C20	1.518 (5)	C7—H7	0.9300
C22—H22A	0.9600	C11—C10	1.383 (3)
C22—H22B	0.9600	C11—H11	0.9300
C22—H22C	0.9600	C10—H10	0.9300
O24—C23	1.213 (4)	C21—H21B	0.9600
C19—C20	1.516 (5)	C21—H21C	0.9600
C19—H20B	0.9600	C21—H21A	0.9600
C19—H19C	0.9600	C23—C26	1.465 (5)
C19—H19A	0.9600	C23—C25	1.489 (5)
C20—C21	1.521 (4)	C25—H25B	0.9600
C16—N15	1.349 (3)	C25—H25C	0.9600
N15—C12	1.404 (3)	C25—H25A	0.9600
N15—H15	0.8600	C26—H26C	0.9600
C12—C13	1.382 (3)	C26—H26A	0.9600
C12—C11	1.397 (3)	C26—H26B	0.9600
O2—S1—O3	118.00 (11)	C10—C9—C14	119.2 (2)
O2—S1—N4	105.56 (11)	C10—C9—S1	120.56 (17)
O3—S1—N4	112.71 (10)	C14—C9—S1	120.19 (17)
O2—S1—C9	107.61 (11)	N4—C5—N9	120.1 (2)
O3—S1—C9	107.38 (10)	N4—C5—S6	130.96 (18)
N4—S1—C9	104.71 (10)	N9—C5—S6	108.93 (18)
C7—S6—C5	90.82 (13)	C5—N9—C8	115.8 (2)
C16—O18—C20	120.64 (19)	C5—N9—H9	122.1
C5—N4—S1	121.92 (16)	C8—N9—H9	122.1
C20—C22—H22A	109.5	C7—C8—N9	112.3 (2)
C20—C22—H22B	109.5	C7—C8—H8	123.8
H22A—C22—H22B	109.5	N9—C8—H8	123.8
C20—C22—H22C	109.5	C8—C7—S6	112.1 (2)
H22A—C22—H22C	109.5	C8—C7—H7	124.0
H22B—C22—H22C	109.5	S6—C7—H7	124.0
C20—C19—H20B	109.5	C10—C11—C12	120.0 (2)
C20—C19—H19C	109.5	C10—C11—H11	120.0
H20B—C19—H19C	109.5	C12—C11—H11	120.0
C20—C19—H19A	109.5	C9—C10—C11	120.4 (2)
H20B—C19—H19A	109.5	C9—C10—H10	119.8
H19C—C19—H19A	109.5	C11—C10—H10	119.8
O18—C20—C19	108.7 (2)	C20—C21—H21B	109.5
O18—C20—C22	108.9 (3)	C20—C21—H21C	109.5
C19—C20—C22	114.1 (3)	H21B—C21—H21C	109.5
O18—C20—C21	102.9 (2)	C20—C21—H21A	109.5
C19—C20—C21	110.5 (3)	H21B—C21—H21A	109.5
C22—C20—C21	111.1 (3)	H21C—C21—H21A	109.5
O17—C16—N15	125.6 (2)	O24—C23—C26	122.1 (4)
O17—C16—O18	126.9 (2)	O24—C23—C25	120.4 (4)
N15—C16—O18	107.43 (19)	C26—C23—C25	117.6 (4)
C16—N15—C12	127.54 (19)	C23—C25—H25B	109.5
C16—N15—H15	116.2	C23—C25—H25C	109.5
C12—N15—H15	116.2	H25B—C25—H25C	109.5
C13—C12—C11	119.3 (2)	C23—C25—H25A	109.5
C13—C12—N15	116.49 (19)	H25B—C25—H25A	109.5
C11—C12—N15	124.3 (2)	H25C—C25—H25A	109.5
C14—C13—C12	120.2 (2)	C23—C26—H26C	109.5
C14—C13—H13	119.9	C23—C26—H26A	109.5
C12—C13—H13	119.9	H26C—C26—H26A	109.5
C13—C14—C9	120.8 (2)	C23—C26—H26B	109.5
C13—C14—H14	119.6	H26C—C26—H26B	109.5
C9—C14—H14	119.6	H26A—C26—H26B	109.5

(Compound_15_Manual)

Crystal data

C14H17N3O4S2·C3H6O	F(000) = 872
Mr = 413.50	Dx = 1.299 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.811 (4) Å	Cell parameters from 137 reflections
b = 17.503 (10) Å	θ = 3.5–22.5°
c = 15.892 (9) Å	µ = 0.28 mm^−1
β = 103.305 (17)°	T = 300 K
V = 2114 (2) Å^3	Block, colorless
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer	3694 independent reflections
Radiation source: micro-focus sealed tube	2806 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.044
ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.665, Tmax = 0.745	k = −20→20
19952 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0858P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
3694 reflections	Δρmax = 0.37 e Å^−3
250 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.28837 (8)	0.63439 (3)	0.46309 (4)	0.0404 (2)
S6	−0.04773 (9)	0.64674 (4)	0.31660 (4)	0.0556 (3)
O18	0.0932 (2)	1.00041 (8)	0.75637 (10)	0.0517 (5)
N4	−0.1225 (3)	0.58031 (10)	0.46378 (12)	0.0435 (5)
O3	−0.3655 (2)	0.66530 (9)	0.37768 (10)	0.0490 (5)
O17	−0.0133 (3)	0.99439 (11)	0.60986 (12)	0.0919 (8)
O2	−0.4001 (2)	0.59171 (10)	0.50589 (11)	0.0551 (5)
C22	−0.0274 (7)	1.1278 (2)	0.7235 (3)	0.145 (2)
H22A	−0.0660	1.1191	0.6625	0.217*
H22B	−0.0033	1.1811	0.7340	0.217*
H22C	−0.1180	1.1121	0.7517	0.217*
O24	0.4299 (4)	0.79797 (16)	0.62932 (17)	0.1176 (10)
C19	0.2825 (7)	1.0937 (2)	0.7105 (2)	0.1193 (17)
H20B	0.3843	1.0646	0.7377	0.179*
H19C	0.3126	1.1469	0.7114	0.179*
H19A	0.2416	1.0771	0.6517	0.179*
C20	0.1385 (4)	1.08189 (13)	0.75896 (17)	0.0620 (8)
C16	0.0248 (4)	0.96523 (14)	0.68011 (15)	0.0504 (6)
N15	0.0047 (3)	0.89072 (10)	0.69721 (11)	0.0424 (5)
H15	0.0381	0.8772	0.7505	0.051*
C12	−0.0642 (3)	0.83270 (12)	0.63812 (13)	0.0368 (5)
C13	−0.0826 (3)	0.76149 (13)	0.67259 (14)	0.0469 (6)
H13	−0.0486	0.7540	0.7320	0.056*
C14	−0.1507 (3)	0.70191 (13)	0.61948 (14)	0.0478 (6)
H14	−0.1628	0.6542	0.6433	0.057*
C9	−0.2019 (3)	0.71180 (12)	0.53041 (13)	0.0368 (5)
C5	−0.0217 (3)	0.58938 (12)	0.40788 (15)	0.0406 (6)
N9	0.1271 (3)	0.54800 (11)	0.41620 (13)	0.0480 (5)
H9	0.1607	0.5158	0.4576	0.058*
C8	0.2219 (3)	0.56063 (16)	0.35420 (17)	0.0571 (7)
H8	0.3268	0.5359	0.3532	0.069*
C7	0.1465 (4)	0.61199 (18)	0.2962 (2)	0.0675 (8)
H7	0.1924	0.6276	0.2499	0.081*
C11	−0.1154 (3)	0.84304 (13)	0.54868 (15)	0.0488 (6)
H11	−0.1033	0.8907	0.5248	0.059*
C10	−0.1838 (3)	0.78245 (13)	0.49567 (15)	0.0484 (6)
H10	−0.2178	0.7895	0.4362	0.058*
C21	0.2082 (4)	1.09676 (15)	0.85507 (17)	0.0667 (8)
H21B	0.1190	1.0844	0.8855	0.100*
H21C	0.2396	1.1497	0.8640	0.100*
H21A	0.3101	1.0656	0.8764	0.100*
C23	0.3811 (4)	0.8226 (2)	0.5564 (2)	0.0817 (10)
C25	0.3123 (5)	0.7697 (2)	0.4830 (2)	0.0972 (12)
H25B	0.3283	0.7178	0.5029	0.146*
H25C	0.3749	0.7778	0.4384	0.146*
H25A	0.1893	0.7794	0.4604	0.146*
C26	0.3885 (7)	0.9041 (3)	0.5367 (4)	0.149 (2)
H26C	0.2712	0.9239	0.5188	0.223*
H26A	0.4490	0.9109	0.4910	0.223*
H26B	0.4503	0.9309	0.5873	0.223*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0483 (4)	0.0345 (3)	0.0351 (4)	−0.0001 (3)	0.0028 (3)	−0.0039 (2)
S6	0.0527 (5)	0.0572 (4)	0.0558 (4)	0.0029 (3)	0.0100 (3)	0.0228 (3)
O18	0.0812 (12)	0.0318 (9)	0.0372 (9)	−0.0067 (8)	0.0034 (8)	−0.0030 (7)
N4	0.0611 (13)	0.0327 (10)	0.0368 (10)	0.0069 (9)	0.0118 (9)	0.0001 (8)
O3	0.0577 (10)	0.0457 (10)	0.0356 (9)	0.0055 (8)	−0.0061 (7)	−0.0048 (7)
O17	0.171 (2)	0.0448 (11)	0.0417 (11)	−0.0210 (13)	−0.0129 (13)	0.0058 (9)
O2	0.0604 (11)	0.0469 (10)	0.0590 (11)	−0.0133 (9)	0.0159 (9)	−0.0050 (8)
C22	0.190 (5)	0.050 (2)	0.138 (4)	0.039 (3)	−0.076 (3)	−0.023 (2)
O24	0.163 (3)	0.105 (2)	0.0744 (18)	0.0005 (19)	0.0062 (17)	−0.0149 (16)
C19	0.192 (4)	0.105 (3)	0.065 (2)	−0.084 (3)	0.039 (3)	−0.015 (2)
C20	0.100 (2)	0.0296 (13)	0.0475 (15)	−0.0092 (13)	−0.0023 (15)	−0.0003 (11)
C16	0.0752 (18)	0.0358 (13)	0.0342 (13)	−0.0033 (12)	0.0001 (12)	−0.0012 (10)
N15	0.0579 (12)	0.0360 (10)	0.0277 (10)	−0.0001 (9)	−0.0014 (9)	−0.0003 (8)
C12	0.0403 (13)	0.0348 (12)	0.0331 (12)	0.0025 (10)	0.0039 (10)	−0.0022 (9)
C13	0.0687 (17)	0.0389 (13)	0.0288 (12)	0.0024 (12)	0.0027 (11)	0.0024 (10)
C14	0.0688 (16)	0.0319 (12)	0.0379 (13)	−0.0004 (11)	0.0023 (11)	0.0032 (10)
C9	0.0414 (12)	0.0337 (12)	0.0329 (12)	0.0027 (10)	0.0033 (10)	−0.0014 (9)
C5	0.0482 (14)	0.0286 (11)	0.0395 (13)	−0.0015 (10)	−0.0015 (11)	−0.0010 (10)
N9	0.0530 (12)	0.0430 (11)	0.0449 (11)	0.0079 (10)	0.0051 (10)	0.0035 (9)
C8	0.0452 (15)	0.0640 (18)	0.0626 (17)	−0.0002 (13)	0.0133 (13)	0.0018 (14)
C7	0.0543 (17)	0.083 (2)	0.0680 (19)	0.0012 (16)	0.0205 (14)	0.0252 (17)
C11	0.0728 (18)	0.0352 (13)	0.0342 (13)	−0.0070 (12)	0.0038 (12)	0.0030 (10)
C10	0.0693 (17)	0.0404 (13)	0.0311 (12)	−0.0042 (12)	0.0024 (11)	0.0004 (10)
C21	0.102 (2)	0.0395 (15)	0.0504 (16)	−0.0064 (15)	0.0021 (15)	−0.0090 (12)
C23	0.074 (2)	0.084 (2)	0.083 (3)	0.0108 (19)	0.0084 (19)	−0.004 (2)
C25	0.103 (3)	0.101 (3)	0.078 (2)	0.023 (2)	0.001 (2)	−0.007 (2)
C26	0.141 (4)	0.083 (3)	0.204 (6)	0.002 (3)	0.002 (4)	0.024 (3)

Geometric parameters (Å, º)

S1—O2	1.4337 (18)	C13—C14	1.370 (3)
S1—O3	1.4566 (17)	C13—H13	0.9300
S1—N4	1.602 (2)	C14—C9	1.390 (3)
S1—C9	1.762 (2)	C14—H14	0.9300
S6—C7	1.733 (3)	C9—C10	1.375 (3)
S6—C5	1.737 (2)	C5—N9	1.350 (3)
O18—C16	1.355 (3)	N9—C8	1.380 (3)
O18—C20	1.468 (3)	N9—H9	0.8600
N4—C5	1.325 (3)	C8—C7	1.325 (4)
O17—C16	1.201 (3)	C8—H8	0.9300
C22—C20	1.518 (5)	C7—H7	0.9300
C22—H22A	0.9600	C11—C10	1.383 (3)
C22—H22B	0.9600	C11—H11	0.9300
C22—H22C	0.9600	C10—H10	0.9300
O24—C23	1.213 (4)	C21—H21B	0.9600
C19—C20	1.516 (5)	C21—H21C	0.9600
C19—H20B	0.9600	C21—H21A	0.9600
C19—H19C	0.9600	C23—C26	1.465 (5)
C19—H19A	0.9600	C23—C25	1.489 (5)
C20—C21	1.521 (4)	C25—H25B	0.9600
C16—N15	1.349 (3)	C25—H25C	0.9600
N15—C12	1.404 (3)	C25—H25A	0.9600
N15—H15	0.8600	C26—H26C	0.9600
C12—C13	1.382 (3)	C26—H26A	0.9600
C12—C11	1.397 (3)	C26—H26B	0.9600
O2—S1—O3	118.00 (11)	C10—C9—C14	119.2 (2)
O2—S1—N4	105.56 (11)	C10—C9—S1	120.56 (17)
O3—S1—N4	112.71 (10)	C14—C9—S1	120.19 (17)
O2—S1—C9	107.61 (11)	N4—C5—N9	120.1 (2)
O3—S1—C9	107.38 (10)	N4—C5—S6	130.96 (18)
N4—S1—C9	104.71 (10)	N9—C5—S6	108.93 (18)
C7—S6—C5	90.82 (13)	C5—N9—C8	115.8 (2)
C16—O18—C20	120.64 (19)	C5—N9—H9	122.1
C5—N4—S1	121.92 (16)	C8—N9—H9	122.1
C20—C22—H22A	109.5	C7—C8—N9	112.3 (2)
C20—C22—H22B	109.5	C7—C8—H8	123.8
H22A—C22—H22B	109.5	N9—C8—H8	123.8
C20—C22—H22C	109.5	C8—C7—S6	112.1 (2)
H22A—C22—H22C	109.5	C8—C7—H7	124.0
H22B—C22—H22C	109.5	S6—C7—H7	124.0
C20—C19—H20B	109.5	C10—C11—C12	120.0 (2)
C20—C19—H19C	109.5	C10—C11—H11	120.0
H20B—C19—H19C	109.5	C12—C11—H11	120.0
C20—C19—H19A	109.5	C9—C10—C11	120.4 (2)
H20B—C19—H19A	109.5	C9—C10—H10	119.8
H19C—C19—H19A	109.5	C11—C10—H10	119.8
O18—C20—C19	108.7 (2)	C20—C21—H21B	109.5
O18—C20—C22	108.9 (3)	C20—C21—H21C	109.5
C19—C20—C22	114.1 (3)	H21B—C21—H21C	109.5
O18—C20—C21	102.9 (2)	C20—C21—H21A	109.5
C19—C20—C21	110.5 (3)	H21B—C21—H21A	109.5
C22—C20—C21	111.1 (3)	H21C—C21—H21A	109.5
O17—C16—N15	125.6 (2)	O24—C23—C26	122.1 (4)
O17—C16—O18	126.9 (2)	O24—C23—C25	120.4 (4)
N15—C16—O18	107.43 (19)	C26—C23—C25	117.6 (4)
C16—N15—C12	127.54 (19)	C23—C25—H25B	109.5
C16—N15—H15	116.2	C23—C25—H25C	109.5
C12—N15—H15	116.2	H25B—C25—H25C	109.5
C13—C12—C11	119.3 (2)	C23—C25—H25A	109.5
C13—C12—N15	116.49 (19)	H25B—C25—H25A	109.5
C11—C12—N15	124.3 (2)	H25C—C25—H25A	109.5
C14—C13—C12	120.2 (2)	C23—C26—H26C	109.5
C14—C13—H13	119.9	C23—C26—H26A	109.5
C12—C13—H13	119.9	H26C—C26—H26A	109.5
C13—C14—C9	120.8 (2)	C23—C26—H26B	109.5
C13—C14—H14	119.6	H26C—C26—H26B	109.5
C9—C14—H14	119.6	H26A—C26—H26B	109.5

(Compound_15_X2S)

Crystal data

C17H23N3O5S2	F(000) = 784
Mr = 413.50	Dx = 1.229 Mg m^−3
Monoclinic, P121/n1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 654 reflections
a = 7.811 (4) Å	θ = 2.7–19.4°
b = 17.503 (10) Å	µ = 0.28 mm^−1
c = 15.892 (9) Å	T = 300 K
β = 103.305 (17)°	Block, colorless
V = 2114 (2) Å^3	0.50 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer	3694 independent reflections
Radiation source: micro-focus sealed tube	2806 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.044
ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −9→9
Tmin = 0.908, Tmax = 0.964	k = −20→20
19952 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.200	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max = 10.903
3694 reflections	Δρmax = 0.47 e Å^−3
250 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.28837 (11)	0.63441 (5)	0.46312 (5)	0.0401 (4)
S2	−0.04779 (13)	0.64676 (6)	0.31651 (7)	0.0553 (4)
O4	0.0930 (4)	1.00042 (13)	0.75657 (14)	0.0519 (7)
N1	−0.1221 (4)	0.58038 (16)	0.46378 (19)	0.0455 (8)
O2	−0.3657 (3)	0.66520 (14)	0.37762 (15)	0.0494 (7)
O3	−0.0125 (6)	0.99437 (17)	0.60986 (19)	0.0925 (13)
O1	−0.4001 (3)	0.59177 (14)	0.50607 (16)	0.0557 (7)
C21	−0.0298 (12)	1.1273 (3)	0.7249 (5)	0.145 (4)
H21A	−0.0577	1.1263	0.6628	0.218*
H21B	−0.0128	1.1792	0.7445	0.218*
H21C	−0.1247	1.1050	0.7455	0.218*
O5	0.4307 (7)	0.7978 (2)	0.6291 (2)	0.1149 (14)
C1	0.2845 (10)	1.0934 (3)	0.7102 (3)	0.117 (3)
H1A	0.3854	1.0635	0.7369	0.176*
H1B	0.3166	1.1464	0.7118	0.176*
H1C	0.2428	1.0775	0.6512	0.176*
C2	0.1381 (7)	1.0819 (2)	0.7594 (3)	0.0622 (12)
C3	0.0246 (5)	0.9654 (2)	0.6801 (2)	0.0502 (9)
N3	0.0045 (4)	0.89061 (15)	0.69727 (16)	0.0411 (7)
H4	0.0375	0.8770	0.7506	0.049*
C5	−0.0640 (4)	0.83285 (18)	0.6381 (2)	0.0374 (8)
C6	−0.0830 (5)	0.76141 (19)	0.6731 (2)	0.0472 (9)
H6	−0.0497	0.7540	0.7326	0.057*
C7	−0.1510 (5)	0.7017 (2)	0.6196 (2)	0.0483 (9)
H7	−0.1633	0.6540	0.6432	0.058*
C8	−0.2019 (4)	0.71193 (19)	0.53025 (19)	0.0370 (8)
C9	−0.0216 (5)	0.58954 (17)	0.4079 (2)	0.0401 (8)
N2	0.1269 (4)	0.54796 (16)	0.41667 (17)	0.0461 (7)
H10	0.1607	0.5161	0.4584	0.055*
C11	0.2223 (5)	0.5601 (2)	0.3534 (3)	0.0575 (10)
H11	0.3267	0.5351	0.3521	0.069*
C12	0.1463 (6)	0.6116 (3)	0.2956 (3)	0.0667 (12)
H12	0.1917	0.6272	0.2492	0.080*
C13	−0.1153 (5)	0.8431 (2)	0.5488 (2)	0.0481 (9)
H13	−0.1032	0.8907	0.5247	0.058*
C14	−0.1844 (5)	0.7823 (2)	0.4958 (2)	0.0483 (9)
H14	−0.2191	0.7894	0.4363	0.058*
C15	0.2085 (7)	1.0968 (2)	0.8541 (2)	0.0674 (12)
H15A	0.1197	1.0849	0.8849	0.101*
H15B	0.2409	1.1496	0.8627	0.101*
H15C	0.3100	1.0653	0.8752	0.101*
C16	0.3815 (7)	0.8227 (3)	0.5563 (4)	0.0819 (14)
C17	0.3128 (8)	0.7700 (4)	0.4832 (3)	0.0964 (17)
H17A	0.3212	0.7183	0.5039	0.145*
H17B	0.3809	0.7756	0.4404	0.145*
H17C	0.1920	0.7821	0.4580	0.145*
C19	0.3884 (7)	0.9044 (3)	0.5353 (3)	0.1110 (15)
H19A	0.2710	0.9245	0.5193	0.167*
H19B	0.4446	0.9105	0.4880	0.167*
H19C	0.4540	0.9315	0.5848	0.167*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0480 (6)	0.0344 (5)	0.0348 (5)	−0.0003 (3)	0.0030 (4)	−0.0038 (3)
S2	0.0521 (7)	0.0568 (7)	0.0559 (7)	0.0030 (4)	0.0100 (5)	0.0229 (4)
O4	0.0802 (18)	0.0324 (13)	0.0382 (13)	−0.0066 (12)	0.0039 (12)	−0.0030 (10)
N1	0.064 (2)	0.0334 (16)	0.0388 (16)	0.0074 (15)	0.0112 (15)	0.0001 (13)
O2	0.0583 (16)	0.0455 (14)	0.0364 (13)	0.0058 (12)	−0.0059 (11)	−0.0057 (10)
O3	0.169 (4)	0.0469 (17)	0.0438 (16)	−0.022 (2)	−0.0126 (19)	0.0058 (13)
O1	0.0606 (16)	0.0481 (15)	0.0596 (16)	−0.0129 (12)	0.0162 (13)	−0.0060 (12)
C21	0.193 (8)	0.052 (3)	0.137 (6)	0.041 (4)	−0.074 (5)	−0.022 (4)
O5	0.161 (4)	0.101 (3)	0.072 (2)	0.000 (3)	0.006 (2)	−0.013 (2)
C1	0.185 (7)	0.106 (5)	0.064 (3)	−0.081 (5)	0.036 (4)	−0.016 (3)
C2	0.100 (3)	0.0293 (18)	0.048 (2)	−0.0086 (19)	−0.002 (2)	0.0002 (16)
C3	0.076 (2)	0.0354 (19)	0.0330 (18)	−0.0019 (17)	−0.0006 (16)	−0.0015 (14)
N3	0.0544 (16)	0.0359 (14)	0.0277 (13)	−0.0005 (12)	−0.0015 (11)	−0.0006 (11)
C5	0.0412 (18)	0.0353 (17)	0.0334 (17)	0.0028 (14)	0.0038 (14)	−0.0012 (13)
C6	0.068 (2)	0.0387 (18)	0.0310 (16)	0.0034 (16)	0.0032 (15)	0.0033 (14)
C7	0.069 (2)	0.0328 (18)	0.0375 (17)	−0.0001 (16)	0.0016 (16)	0.0021 (14)
C8	0.0417 (18)	0.0348 (17)	0.0322 (16)	0.0020 (13)	0.0036 (13)	−0.0022 (13)
C9	0.0482 (19)	0.0309 (17)	0.0363 (17)	−0.0024 (14)	−0.0005 (14)	−0.0006 (13)
N2	0.0502 (16)	0.0420 (15)	0.0436 (15)	0.0078 (13)	0.0059 (12)	0.0038 (12)
C11	0.046 (2)	0.064 (2)	0.063 (2)	−0.0014 (18)	0.0136 (19)	0.001 (2)
C12	0.055 (2)	0.086 (3)	0.063 (3)	0.002 (2)	0.023 (2)	0.027 (2)
C13	0.072 (3)	0.0365 (18)	0.0327 (17)	−0.0065 (17)	0.0057 (17)	0.0030 (14)
C14	0.069 (2)	0.0402 (18)	0.0319 (17)	−0.0034 (17)	0.0036 (16)	−0.0006 (14)
C15	0.104 (3)	0.039 (2)	0.052 (2)	−0.008 (2)	0.002 (2)	−0.0070 (17)
C16	0.076 (3)	0.083 (3)	0.082 (4)	0.011 (3)	0.008 (3)	−0.006 (3)
C17	0.099 (4)	0.103 (4)	0.079 (3)	0.022 (3)	0.004 (3)	−0.006 (3)
C19	0.114 (3)	0.095 (4)	0.122 (3)	0.002 (3)	0.021 (3)	0.004 (3)

Geometric parameters (Å, º)

S1—O1	1.435 (3)	C6—C7	1.375 (5)
S1—O2	1.457 (3)	C6—H6	0.9300
S1—N1	1.605 (3)	C7—C8	1.395 (5)
S1—C8	1.762 (3)	C7—H7	0.9300
S2—C9	1.737 (3)	C8—C14	1.368 (5)
S2—C12	1.737 (4)	C9—N2	1.349 (4)
O4—C3	1.356 (4)	N2—C11	1.398 (5)
O4—C2	1.467 (4)	N2—H10	0.8600
N1—C9	1.324 (5)	C11—C12	1.327 (6)
O3—C3	1.200 (4)	C11—H11	0.9300
C21—C2	1.524 (8)	C12—H12	0.9300
C21—H21A	0.9603	C13—C14	1.387 (5)
C21—H21B	0.9603	C13—H13	0.9300
C21—H21C	0.9603	C14—H14	0.9300
O5—C16	1.212 (6)	C15—H15A	0.9602
C1—C2	1.540 (8)	C15—H15B	0.9602
C1—H1A	0.9600	C15—H15C	0.9602
C1—H1B	0.9600	C16—C17	1.484 (7)
C1—H1C	0.9600	C16—C19	1.472 (7)
C2—C15	1.501 (5)	C17—H17A	0.9600
C3—N3	1.353 (4)	C17—H17B	0.9600
N3—C5	1.400 (4)	C17—H17C	0.9600
N3—H4	0.8600	C19—H19A	0.9601
C5—C6	1.390 (5)	C19—H19B	0.9601
C5—C13	1.396 (4)	C19—H19C	0.9601
O1—S1—O2	117.96 (16)	C14—C8—C7	119.5 (3)
O1—S1—N1	105.68 (17)	C14—C8—S1	120.7 (2)
O2—S1—N1	112.66 (16)	C7—C8—S1	119.8 (3)
O1—S1—C8	107.63 (15)	N1—C9—N2	119.6 (3)
O2—S1—C8	107.37 (15)	N1—C9—S2	131.1 (3)
N1—S1—C8	104.66 (16)	N2—C9—S2	109.3 (3)
C9—S2—C12	90.89 (18)	C9—N2—C11	115.5 (3)
C3—O4—C2	120.6 (3)	C9—N2—H10	122.2
C9—N1—S1	121.9 (2)	C11—N2—H10	122.3
C2—C21—H21A	109.9	C12—C11—N2	111.9 (4)
C2—C21—H21B	109.8	C12—C11—H11	124.2
H21A—C21—H21B	109.4	N2—C11—H11	123.9
C2—C21—H21C	108.8	C11—C12—S2	112.3 (3)
H21A—C21—H21C	109.5	C11—C12—H12	123.7
H21B—C21—H21C	109.4	S2—C12—H12	123.9
C2—C1—H1A	108.8	C14—C13—C5	120.0 (3)
C2—C1—H1B	110.0	C14—C13—H13	120.0
H1A—C1—H1B	109.5	C5—C13—H13	120.0
C2—C1—H1C	109.6	C8—C14—C13	120.6 (3)
H1A—C1—H1C	109.5	C8—C14—H14	119.7
H1B—C1—H1C	109.5	C13—C14—H14	119.8
O4—C2—C15	103.3 (3)	C2—C15—H15A	109.4
O4—C2—C21	108.4 (4)	C2—C15—H15B	109.4
C15—C2—C21	110.9 (5)	H15A—C15—H15B	109.5
O4—C2—C1	108.2 (4)	C2—C15—H15C	109.6
C15—C2—C1	110.0 (4)	H15A—C15—H15C	109.5
C21—C2—C1	115.3 (6)	H15B—C15—H15C	109.4
O3—C3—N3	125.6 (3)	O5—C16—C17	120.1 (5)
O3—C3—O4	127.1 (3)	O5—C16—C19	123.1 (5)
N3—C3—O4	107.3 (3)	C17—C16—C19	116.8 (5)
C3—N3—C5	127.4 (3)	C16—C17—H17A	109.6
C3—N3—H4	116.3	C16—C17—H17B	109.2
C5—N3—H4	116.3	H17A—C17—H17B	109.5
C6—C5—C13	119.4 (3)	C16—C17—H17C	109.6
C6—C5—N3	116.1 (3)	H17A—C17—H17C	109.5
C13—C5—N3	124.5 (3)	H17B—C17—H17C	109.5
C7—C6—C5	119.9 (3)	C16—C19—H19A	109.5
C7—C6—H6	120.1	C16—C19—H19B	109.1
C5—C6—H6	120.0	H19A—C19—H19B	109.5
C6—C7—C8	120.7 (3)	C16—C19—H19C	109.9
C6—C7—H7	119.6	H19A—C19—H19C	109.5
C8—C7—H7	119.7	H19B—C19—H19C	109.5

(Compound_16_APEX)

Crystal data

C7H10N4O2S·H2O	F(000) = 244
Mr = 232.27	Dx = 1.504 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.6095 (10) Å	Cell parameters from 58 reflections
b = 7.3299 (15) Å	θ = 4.8–20.3°
c = 12.491 (2) Å	µ = 0.31 mm^−1
β = 93.297 (5)°	T = 291 K
V = 512.74 (17) Å^3	Plate, colourless
Z = 2	0.32 × 0.12 × 0.12 mm

Data collection

Bruker APEX II DUO diffractometer	1940 independent reflections
Radiation source: fine-focus sealed tube	1825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.3333 pixels mm^-1	θmax = 25.8°, θmin = 1.6°
φ & ω scans	h = −6→6
Absorption correction: multi-scan SADABS Version 2008/1	k = −8→8
Tmin = 0.85, Tmax = 0.96	l = −15→15
3017 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0366P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1940 reflections	Δρmax = 0.21 e Å^−3
168 parameters	Δρmin = −0.22 e Å^−3
9 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.25231 (9)	0.67472 (7)	0.29318 (4)	0.02799 (14)
O2	0.4569 (3)	0.7875 (2)	0.32229 (13)	0.0390 (4)
O3	0.0204 (3)	0.7536 (2)	0.31138 (13)	0.0383 (4)
C4	0.2552 (4)	0.6311 (3)	0.15512 (18)	0.0288 (5)
C5	0.4389 (4)	0.6951 (4)	0.09561 (17)	0.0328 (5)
H5	0.5701	0.7519	0.1302	0.039*
C6	0.4292 (4)	0.6755 (4)	−0.01354 (17)	0.0365 (5)
H6	0.5534	0.7197	−0.0524	0.044*
C7	0.2341 (4)	0.5897 (3)	−0.06721 (19)	0.0328 (5)
C8	0.0541 (4)	0.5205 (3)	−0.00646 (19)	0.0353 (6)
H8	−0.0739	0.4591	−0.0407	0.042*
C9	0.0620 (4)	0.5410 (3)	0.10280 (19)	0.0348 (5)
H9	−0.0607	0.4952	0.142	0.042*
N10	0.2172 (5)	0.5763 (4)	−0.17744 (19)	0.0485 (6)
H10A	0.114 (4)	0.498 (3)	−0.206 (2)	0.049 (9)*
H10B	0.345 (3)	0.599 (5)	−0.212 (2)	0.065 (11)*
N11	0.2506 (3)	0.4835 (3)	0.35355 (14)	0.0315 (4)
C12	0.4486 (4)	0.3789 (3)	0.36231 (17)	0.0312 (5)
N13	0.6673 (4)	0.4356 (3)	0.34474 (19)	0.0442 (5)
H13A	0.693 (4)	0.5519 (11)	0.338 (2)	0.039 (7)*
H13B	0.785 (4)	0.359 (3)	0.355 (2)	0.064 (10)*
N14	0.4182 (4)	0.2065 (3)	0.38980 (19)	0.0451 (6)
H14A	0.275 (2)	0.168 (4)	0.401 (2)	0.048 (8)*
H14B	0.541 (3)	0.141 (3)	0.410 (2)	0.056 (9)*
O15	0.9224 (4)	0.0654 (3)	0.43379 (15)	0.0429 (4)
H15A	0.906 (5)	0.036 (4)	0.4964 (9)	0.058 (10)*
H15B	0.949 (6)	−0.033 (2)	0.406 (2)	0.067 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0299 (3)	0.0243 (2)	0.0301 (3)	0.0016 (3)	0.00459 (19)	−0.0018 (3)
O2	0.0430 (11)	0.0349 (10)	0.0386 (9)	−0.0053 (8)	−0.0016 (7)	−0.0065 (8)
O3	0.0382 (9)	0.0336 (9)	0.0441 (9)	0.0093 (7)	0.0121 (7)	0.0002 (8)
C4	0.0280 (11)	0.0268 (14)	0.0316 (11)	0.0020 (8)	0.0028 (9)	0.0004 (9)
C5	0.0286 (11)	0.0331 (13)	0.0368 (11)	−0.0048 (11)	0.0019 (9)	−0.0011 (12)
C6	0.0354 (11)	0.0369 (11)	0.0382 (11)	−0.0016 (14)	0.0107 (9)	0.0011 (14)
C7	0.0440 (14)	0.0232 (11)	0.0312 (11)	0.0056 (10)	0.0020 (11)	−0.0006 (9)
C8	0.0327 (13)	0.0322 (13)	0.0405 (13)	−0.0045 (10)	−0.0035 (10)	−0.0032 (10)
C9	0.0296 (12)	0.0344 (13)	0.0410 (14)	−0.0054 (10)	0.0073 (10)	−0.0017 (11)
N10	0.0660 (17)	0.0468 (14)	0.0327 (11)	−0.0047 (13)	0.0033 (12)	−0.0006 (10)
N11	0.0313 (10)	0.0313 (10)	0.0326 (10)	0.0025 (8)	0.0071 (8)	0.0030 (8)
C12	0.0339 (13)	0.0324 (13)	0.0274 (11)	0.0050 (10)	0.0030 (9)	−0.0025 (9)
N13	0.0315 (12)	0.0383 (13)	0.0629 (14)	0.0070 (10)	0.0037 (10)	−0.0008 (11)
N14	0.0427 (13)	0.0342 (15)	0.0585 (14)	0.0087 (11)	0.0039 (11)	0.0117 (10)
O15	0.0553 (12)	0.0392 (11)	0.0347 (11)	0.0075 (9)	0.0085 (9)	−0.0005 (8)

Geometric parameters (Å, º)

S1—O2	1.4443 (18)	C8—H8	0.93
S1—O3	1.4535 (17)	C9—H9	0.93
S1—N11	1.592 (2)	N10—H10A	0.873 (5)
S1—C4	1.755 (2)	N10—H10B	0.870 (5)
C4—C5	1.386 (3)	N11—C12	1.349 (3)
C4—C9	1.399 (3)	C12—N14	1.323 (3)
C5—C6	1.369 (3)	C12—N13	1.326 (3)
C5—H5	0.93	N13—H13A	0.869 (5)
C6—C7	1.400 (3)	N13—H13B	0.871 (5)
C6—H6	0.93	N14—H14A	0.870 (5)
C7—N10	1.378 (3)	N14—H14B	0.867 (5)
C7—C8	1.393 (3)	O15—H15A	0.821 (5)
C8—C9	1.371 (3)	O15—H15B	0.822 (5)
O2—S1—O3	116.00 (10)	C9—C8—H8	119.4
O2—S1—N11	114.29 (10)	C7—C8—H8	119.4
O3—S1—N11	104.25 (10)	C8—C9—C4	119.8 (2)
O2—S1—C4	107.43 (10)	C8—C9—H9	120.1
O3—S1—C4	106.57 (10)	C4—C9—H9	120.1
N11—S1—C4	107.82 (10)	C7—N10—H10A	117.4 (19)
C5—C4—C9	119.3 (2)	C7—N10—H10B	118 (2)
C5—C4—S1	120.97 (16)	H10A—N10—H10B	118 (3)
C9—C4—S1	119.62 (17)	C12—N11—S1	120.75 (16)
C6—C5—C4	120.7 (2)	N14—C12—N13	118.5 (2)
C6—C5—H5	119.7	N14—C12—N11	116.5 (2)
C4—C5—H5	119.7	N13—C12—N11	125.0 (2)
C5—C6—C7	120.6 (2)	C12—N13—H13A	119.0 (18)
C5—C6—H6	119.7	C12—N13—H13B	119 (2)
C7—C6—H6	119.7	H13A—N13—H13B	121 (3)
N10—C7—C8	120.5 (2)	C12—N14—H14A	119 (2)
N10—C7—C6	121.2 (2)	C12—N14—H14B	120 (2)
C8—C7—C6	118.3 (2)	H14A—N14—H14B	120 (3)
C9—C8—C7	121.3 (2)	H15A—O15—H15B	102 (3)

(Compound_16_CCDC)

Crystal data

C7H10N4O2S·H2O	F(000) = 244
Mr = 232.27	Dx = 1.504 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.6095 (10) Å	Cell parameters from 58 reflections
b = 7.3299 (15) Å	θ = 4.8–20.3°
c = 12.491 (2) Å	µ = 0.31 mm^−1
β = 93.297 (5)°	T = 291 K
V = 512.74 (17) Å^3	Plate, colourless
Z = 2	0.32 × 0.12 × 0.12 mm

Data collection

Bruker APEX II DUO diffractometer	1940 independent reflections
Radiation source: fine-focus sealed tube	1825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.3333 pixels mm^-1	θmax = 25.8°, θmin = 1.6°
φ & ω scans	h = −6→6
Absorption correction: multi-scan SADABS Version 2008/1	k = −8→8
Tmin = 0.85, Tmax = 0.96	l = −15→15
3017 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0366P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1940 reflections	Δρmax = 0.21 e Å^−3
168 parameters	Δρmin = −0.22 e Å^−3
9 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.25231 (9)	0.67472 (7)	0.29318 (4)	0.02799 (14)
O2	0.4569 (3)	0.7875 (2)	0.32229 (13)	0.0390 (4)
O3	0.0204 (3)	0.7536 (2)	0.31138 (13)	0.0383 (4)
C4	0.2552 (4)	0.6311 (3)	0.15512 (18)	0.0288 (5)
C5	0.4389 (4)	0.6951 (4)	0.09561 (17)	0.0328 (5)
H5	0.5701	0.7519	0.1302	0.039*
C6	0.4292 (4)	0.6755 (4)	−0.01354 (17)	0.0365 (5)
H6	0.5534	0.7197	−0.0524	0.044*
C7	0.2341 (4)	0.5897 (3)	−0.06721 (19)	0.0328 (5)
C8	0.0541 (4)	0.5205 (3)	−0.00646 (19)	0.0353 (6)
H8	−0.0739	0.4591	−0.0407	0.042*
C9	0.0620 (4)	0.5410 (3)	0.10280 (19)	0.0348 (5)
H9	−0.0607	0.4952	0.142	0.042*
N10	0.2172 (5)	0.5763 (4)	−0.17744 (19)	0.0485 (6)
H10A	0.114 (4)	0.498 (3)	−0.206 (2)	0.049 (9)*
H10B	0.345 (3)	0.599 (5)	−0.212 (2)	0.065 (11)*
N11	0.2506 (3)	0.4835 (3)	0.35355 (14)	0.0315 (4)
C12	0.4486 (4)	0.3789 (3)	0.36231 (17)	0.0312 (5)
N13	0.6673 (4)	0.4356 (3)	0.34474 (19)	0.0442 (5)
H13A	0.693 (4)	0.5519 (11)	0.338 (2)	0.039 (7)*
H13B	0.785 (4)	0.359 (3)	0.355 (2)	0.064 (10)*
N14	0.4182 (4)	0.2065 (3)	0.38980 (19)	0.0451 (6)
H14A	0.275 (2)	0.168 (4)	0.401 (2)	0.048 (8)*
H14B	0.541 (3)	0.141 (3)	0.410 (2)	0.056 (9)*
O15	0.9224 (4)	0.0654 (3)	0.43379 (15)	0.0429 (4)
H15A	0.906 (5)	0.036 (4)	0.4964 (9)	0.058 (10)*
H15B	0.949 (6)	−0.033 (2)	0.406 (2)	0.067 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0299 (3)	0.0243 (2)	0.0301 (3)	0.0016 (3)	0.00459 (19)	−0.0018 (3)
O2	0.0430 (11)	0.0349 (10)	0.0386 (9)	−0.0053 (8)	−0.0016 (7)	−0.0065 (8)
O3	0.0382 (9)	0.0336 (9)	0.0441 (9)	0.0093 (7)	0.0121 (7)	0.0002 (8)
C4	0.0280 (11)	0.0268 (14)	0.0316 (11)	0.0020 (8)	0.0028 (9)	0.0004 (9)
C5	0.0286 (11)	0.0331 (13)	0.0368 (11)	−0.0048 (11)	0.0019 (9)	−0.0011 (12)
C6	0.0354 (11)	0.0369 (11)	0.0382 (11)	−0.0016 (14)	0.0107 (9)	0.0011 (14)
C7	0.0440 (14)	0.0232 (11)	0.0312 (11)	0.0056 (10)	0.0020 (11)	−0.0006 (9)
C8	0.0327 (13)	0.0322 (13)	0.0405 (13)	−0.0045 (10)	−0.0035 (10)	−0.0032 (10)
C9	0.0296 (12)	0.0344 (13)	0.0410 (14)	−0.0054 (10)	0.0073 (10)	−0.0017 (11)
N10	0.0660 (17)	0.0468 (14)	0.0327 (11)	−0.0047 (13)	0.0033 (12)	−0.0006 (10)
N11	0.0313 (10)	0.0313 (10)	0.0326 (10)	0.0025 (8)	0.0071 (8)	0.0030 (8)
C12	0.0339 (13)	0.0324 (13)	0.0274 (11)	0.0050 (10)	0.0030 (9)	−0.0025 (9)
N13	0.0315 (12)	0.0383 (13)	0.0629 (14)	0.0070 (10)	0.0037 (10)	−0.0008 (11)
N14	0.0427 (13)	0.0342 (15)	0.0585 (14)	0.0087 (11)	0.0039 (11)	0.0117 (10)
O15	0.0553 (12)	0.0392 (11)	0.0347 (11)	0.0075 (9)	0.0085 (9)	−0.0005 (8)

Geometric parameters (Å, º)

S1—O2	1.4443 (18)	C8—H8	0.93
S1—O3	1.4535 (17)	C9—H9	0.93
S1—N11	1.592 (2)	N10—H10A	0.873 (5)
S1—C4	1.755 (2)	N10—H10B	0.870 (5)
C4—C5	1.386 (3)	N11—C12	1.349 (3)
C4—C9	1.399 (3)	C12—N14	1.323 (3)
C5—C6	1.369 (3)	C12—N13	1.326 (3)
C5—H5	0.93	N13—H13A	0.869 (5)
C6—C7	1.400 (3)	N13—H13B	0.871 (5)
C6—H6	0.93	N14—H14A	0.870 (5)
C7—N10	1.378 (3)	N14—H14B	0.867 (5)
C7—C8	1.393 (3)	O15—H15A	0.821 (5)
C8—C9	1.371 (3)	O15—H15B	0.822 (5)
O2—S1—O3	116.00 (10)	C9—C8—H8	119.4
O2—S1—N11	114.29 (10)	C7—C8—H8	119.4
O3—S1—N11	104.25 (10)	C8—C9—C4	119.8 (2)
O2—S1—C4	107.43 (10)	C8—C9—H9	120.1
O3—S1—C4	106.57 (10)	C4—C9—H9	120.1
N11—S1—C4	107.82 (10)	C7—N10—H10A	117.4 (19)
C5—C4—C9	119.3 (2)	C7—N10—H10B	118 (2)
C5—C4—S1	120.97 (16)	H10A—N10—H10B	118 (3)
C9—C4—S1	119.62 (17)	C12—N11—S1	120.75 (16)
C6—C5—C4	120.7 (2)	N14—C12—N13	118.5 (2)
C6—C5—H5	119.7	N14—C12—N11	116.5 (2)
C4—C5—H5	119.7	N13—C12—N11	125.0 (2)
C5—C6—C7	120.6 (2)	C12—N13—H13A	119.0 (18)
C5—C6—H6	119.7	C12—N13—H13B	119 (2)
C7—C6—H6	119.7	H13A—N13—H13B	121 (3)
N10—C7—C8	120.5 (2)	C12—N14—H14A	119 (2)
N10—C7—C6	121.2 (2)	C12—N14—H14B	120 (2)
C8—C7—C6	118.3 (2)	H14A—N14—H14B	120 (3)
C9—C8—C7	121.3 (2)	H15A—O15—H15B	102 (3)

(Compound_16_Manual)

Crystal data

(C7H10N4O2S)·(H2O)	F(000) = 244
Mr = 232.27	Dx = 1.492 Mg m^−3
Monoclinic, P1211	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 654 reflections
a = 5.6245 (17) Å	θ = 2.7–19.4°
b = 7.354 (3) Å	µ = 0.31 mm^−1
c = 12.521 (5) Å	T = 300 K
β = 93.445 (13)°	Plate, colorless
V = 517.0 (3) Å^3	0.32 × 0.12 × 0.12 mm
Z = 2

Data collection

Bruker SMART X2S diffractometer	1776 independent reflections
Radiation source: micro-focus sealed tube	1427 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.039
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −6→6
Tmin = 0.908, Tmax = 0.964	k = −8→8
3381 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.039P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1776 reflections	Δρmax = 0.24 e Å^−3
161 parameters	Δρmin = −0.28 e Å^−3
2 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.25 (12)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.25269 (16)	0.67473 (12)	0.29322 (7)	0.0311 (3)
O2	0.4567 (5)	0.7871 (4)	0.3221 (2)	0.0404 (7)
O3	0.0207 (4)	0.7534 (4)	0.3117 (2)	0.0393 (7)
C4	0.2550 (6)	0.6314 (4)	0.1553 (3)	0.0277 (9)
C5	0.4377 (6)	0.6955 (6)	0.0954 (3)	0.0334 (9)
H5	0.5683	0.7530	0.1297	0.040*
C6	0.4281 (6)	0.6752 (7)	−0.0132 (3)	0.0372 (9)
H6	0.5522	0.7190	−0.0518	0.045*
C7	0.2344 (7)	0.5896 (5)	−0.0670 (3)	0.0347 (10)
C8	0.0542 (7)	0.5210 (5)	−0.0057 (3)	0.0377 (10)
H8	−0.0747	0.4608	−0.0397	0.045*
C9	0.0641 (6)	0.5406 (5)	0.1026 (3)	0.0354 (10)
H9	−0.0571	0.4934	0.1417	0.042*
N10	0.2171 (7)	0.5772 (6)	−0.1769 (3)	0.0503 (10)
H10A	0.125 (6)	0.493 (4)	−0.206 (3)	0.060*
H10B	0.345 (7)	0.596 (7)	−0.214 (4)	0.060*
N11	0.2500 (5)	0.4831 (4)	0.3533 (2)	0.0325 (8)
C12	0.4486 (7)	0.3796 (5)	0.3620 (3)	0.0321 (10)
N13	0.6678 (7)	0.4350 (6)	0.3451 (3)	0.0462 (10)
H13A	0.693 (8)	0.540 (7)	0.336 (4)	0.055*
H13B	0.794 (8)	0.354 (6)	0.351 (3)	0.055*
N14	0.4174 (7)	0.2067 (5)	0.3900 (3)	0.0484 (11)
H14A	0.280 (7)	0.156 (7)	0.396 (3)	0.058*
H14B	0.537 (7)	0.135 (6)	0.401 (3)	0.058*
O15	0.9215 (6)	0.0652 (4)	0.4337 (3)	0.0474 (9)
H15A	0.945 (8)	−0.021 (7)	0.403 (4)	0.057*
H15B	0.905 (7)	0.038 (6)	0.498 (4)	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0326 (5)	0.0272 (5)	0.0338 (5)	0.0022 (5)	0.0047 (4)	−0.0012 (5)
O2	0.0443 (18)	0.0355 (17)	0.0411 (17)	−0.0081 (14)	−0.0004 (13)	−0.0085 (13)
O3	0.0351 (15)	0.0378 (16)	0.0461 (17)	0.0108 (12)	0.0114 (13)	−0.0020 (13)
C4	0.0262 (18)	0.026 (3)	0.032 (2)	0.0033 (16)	0.0031 (16)	0.0006 (16)
C5	0.0284 (19)	0.032 (2)	0.040 (2)	−0.003 (2)	0.0045 (16)	−0.004 (2)
C6	0.037 (2)	0.038 (2)	0.038 (2)	−0.003 (3)	0.0133 (17)	−0.002 (2)
C7	0.044 (2)	0.026 (2)	0.034 (2)	0.007 (2)	0.005 (2)	−0.0007 (17)
C8	0.032 (2)	0.037 (3)	0.044 (3)	−0.0034 (19)	−0.003 (2)	−0.005 (2)
C9	0.030 (2)	0.036 (2)	0.041 (3)	−0.0065 (19)	0.0093 (18)	0.0017 (19)
N10	0.066 (3)	0.050 (2)	0.035 (2)	−0.005 (2)	0.0055 (19)	−0.0018 (17)
N11	0.0334 (19)	0.0310 (18)	0.0337 (19)	0.0037 (16)	0.0069 (14)	0.0058 (15)
C12	0.033 (3)	0.036 (3)	0.028 (2)	0.003 (2)	0.0041 (17)	−0.0020 (17)
N13	0.032 (2)	0.040 (2)	0.068 (3)	0.004 (2)	0.0070 (18)	0.000 (2)
N14	0.047 (2)	0.036 (3)	0.062 (2)	0.0070 (19)	0.003 (2)	0.0122 (18)
O15	0.060 (2)	0.045 (2)	0.039 (2)	0.0074 (17)	0.0100 (18)	−0.0032 (15)

Geometric parameters (Å, º)

S1—O2	1.443 (3)	C8—H8	0.9300
S1—O3	1.458 (3)	C9—H9	0.9300
S1—N11	1.598 (3)	N10—H10A	0.872 (5)
S1—C4	1.757 (4)	N10—H10B	0.89 (4)
C4—C5	1.391 (5)	N11—C12	1.351 (5)
C4—C9	1.396 (5)	C12—N13	1.328 (5)
C5—C6	1.365 (5)	C12—N14	1.334 (5)
C5—H5	0.9300	N13—H13A	0.80 (5)
C6—C7	1.397 (5)	N13—H13B	0.93 (4)
C6—H6	0.9300	N14—H14A	0.86 (4)
C7—N10	1.377 (5)	N14—H14B	0.86 (4)
C7—C8	1.402 (5)	O15—H15A	0.76 (5)
C8—C9	1.361 (5)	O15—H15B	0.84 (5)
O2—S1—O3	116.02 (16)	C9—C8—H8	119.3
O2—S1—N11	114.66 (17)	C7—C8—H8	119.3
O3—S1—N11	103.96 (16)	C8—C9—C4	120.4 (3)
O2—S1—C4	107.32 (16)	C8—C9—H9	119.8
O3—S1—C4	106.72 (16)	C4—C9—H9	119.8
N11—S1—C4	107.66 (16)	C7—N10—H10A	118 (3)
C5—C4—C9	118.7 (3)	C7—N10—H10B	120 (3)
C5—C4—S1	121.2 (3)	H10A—N10—H10B	112 (4)
C9—C4—S1	120.0 (3)	C12—N11—S1	120.3 (3)
C6—C5—C4	120.9 (3)	N13—C12—N14	118.2 (4)
C6—C5—H5	119.6	N13—C12—N11	125.8 (4)
C4—C5—H5	119.6	N14—C12—N11	115.9 (4)
C5—C6—C7	120.9 (3)	C12—N13—H13A	120 (3)
C5—C6—H6	119.6	C12—N13—H13B	120 (3)
C7—C6—H6	119.6	H13A—N13—H13B	120 (4)
N10—C7—C6	121.2 (4)	C12—N14—H14A	125 (3)
N10—C7—C8	120.9 (4)	C12—N14—H14B	121 (3)
C6—C7—C8	117.8 (4)	H14A—N14—H14B	115 (5)
C9—C8—C7	121.3 (3)	H15A—O15—H15B	109 (5)

(Compound_16_X2S)

Crystal data

(C7H6N3O3S)·(O)	F(000) = 204
Mr = 196.23	Dx = 1.261 Mg m^−3
Monoclinic, P1211	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 654 reflections
a = 5.6245 (17) Å	θ = 2.7–19.4°
b = 7.354 (3) Å	µ = 0.28 mm^−1
c = 12.521 (5) Å	T = 300 K
β = 93.445 (13)°	Plate, colorless
V = 517.0 (3) Å^3	0.32 × 0.12 × 0.12 mm
Z = 2

Data collection

Bruker SMART X2S diffractometer	1777 independent reflections
Radiation source: micro-focus sealed tube	1247 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.145
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −6→6
Tmin = 0.908, Tmax = 0.964	k = −8→8
3392 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.087	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.228	w = 1/[σ^2(Fo^2) + (0.130P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.048
1777 reflections	Δρmax = 0.47 e Å^−3
136 parameters	Δρmin = −0.63 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.9 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.2528 (3)	0.1633 (2)	0.29341 (14)	0.0305 (5)
O1S	0.9229 (10)	−0.2237 (8)	0.4347 (5)	0.0463 (16)
O1	0.2494 (11)	0.3545 (9)	0.3539 (5)	0.0543 (17)
O2	0.0217 (10)	0.0856 (7)	0.3121 (4)	0.0401 (15)
O3	0.4579 (9)	0.0512 (7)	0.3228 (4)	0.0384 (14)
N1	0.2179 (14)	0.2629 (12)	−0.1792 (6)	0.052 (2)
N2	0.4151 (14)	0.6325 (10)	0.3908 (6)	0.0477 (19)
N3	0.4273 (14)	0.1626 (14)	−0.0142 (6)	0.058 (2)
H3	0.5423	0.1227	−0.0499	0.070*
C1	0.2329 (14)	0.2485 (11)	−0.0676 (6)	0.0337 (19)
C2	0.0544 (15)	0.3172 (11)	−0.0060 (7)	0.041 (2)
H2	−0.0731	0.3792	−0.0399	0.049*
C3	0.0619 (14)	0.2959 (12)	0.1032 (7)	0.038 (2)
H3A	−0.0607	0.3410	0.1423	0.046*
C4	0.2542 (13)	0.2064 (9)	0.1551 (6)	0.0284 (18)
C5	0.4503 (14)	0.4594 (10)	0.3620 (6)	0.0309 (19)
C6	0.6662 (11)	0.4018 (11)	0.3456 (6)	0.0286 (17)
H6A	0.7947	0.4811	0.3540	0.034*
H6B	0.6905	0.2817	0.3256	0.034*
C7	0.4359 (13)	0.1413 (11)	0.0960 (6)	0.0338 (18)
H7	0.5653	0.0826	0.1305	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0313 (10)	0.0250 (9)	0.0354 (10)	−0.0025 (10)	0.0036 (7)	0.0018 (9)
O1S	0.052 (4)	0.039 (4)	0.049 (4)	−0.005 (3)	0.007 (3)	0.000 (3)
O1	0.055 (4)	0.046 (4)	0.062 (4)	0.009 (3)	0.003 (3)	−0.011 (3)
O2	0.040 (3)	0.036 (3)	0.046 (3)	−0.007 (3)	0.014 (3)	0.005 (3)
O3	0.039 (3)	0.026 (3)	0.049 (3)	0.007 (3)	−0.004 (3)	0.008 (3)
N1	0.071 (5)	0.047 (4)	0.039 (4)	−0.006 (4)	0.002 (4)	−0.003 (3)
N2	0.059 (4)	0.035 (5)	0.049 (4)	−0.007 (4)	−0.001 (3)	−0.014 (3)
N3	0.060 (5)	0.053 (4)	0.062 (5)	0.005 (6)	0.013 (4)	−0.004 (5)
C1	0.038 (5)	0.024 (4)	0.039 (5)	−0.007 (4)	−0.002 (4)	0.006 (3)
C2	0.037 (5)	0.032 (5)	0.052 (5)	0.005 (4)	−0.006 (4)	0.003 (4)
C3	0.030 (4)	0.041 (5)	0.043 (5)	0.003 (4)	0.003 (4)	−0.001 (4)
C4	0.028 (4)	0.025 (5)	0.032 (4)	−0.001 (3)	0.003 (3)	0.003 (3)
C5	0.031 (5)	0.030 (4)	0.032 (4)	−0.013 (4)	0.002 (3)	0.007 (3)
C6	0.012 (4)	0.026 (4)	0.048 (4)	−0.004 (3)	0.006 (3)	0.002 (3)
C7	0.034 (4)	0.027 (4)	0.040 (4)	0.011 (4)	0.004 (3)	0.002 (4)

Geometric parameters (Å, º)

S1—O3	1.447 (6)	C1—C2	1.397 (11)
S1—O2	1.452 (6)	C2—C3	1.375 (11)
S1—O1	1.598 (6)	C2—H2	0.9300
S1—C4	1.760 (7)	C3—C4	1.394 (11)
O1—C5	1.367 (9)	C3—H3A	0.9300
N1—C1	1.398 (11)	C4—C7	1.383 (10)
N2—C5	1.341 (10)	C5—C6	1.314 (10)
N3—C7	1.386 (10)	C6—H6A	0.9300
N3—C1	1.398 (11)	C6—H6B	0.9300
N3—H3	0.8600	C7—H7	0.9300
O3—S1—O2	116.3 (3)	C2—C3—C4	119.6 (7)
O3—S1—O1	114.4 (3)	C2—C3—H3A	120.2
O2—S1—O1	103.5 (3)	C4—C3—H3A	120.2
O3—S1—C4	107.6 (3)	C7—C4—C3	119.5 (7)
O2—S1—C4	106.6 (3)	C7—C4—S1	120.8 (6)
O1—S1—C4	108.0 (3)	C3—C4—S1	119.6 (6)
C5—O1—S1	119.9 (5)	C6—C5—N2	120.0 (7)
C7—N3—C1	120.5 (7)	C6—C5—O1	125.1 (7)
C7—N3—H3	119.8	N2—C5—O1	114.9 (7)
C1—N3—H3	119.8	C5—C6—H6A	120.0
C2—C1—N1	121.5 (7)	C5—C6—H6B	120.0
C2—C1—N3	117.8 (7)	H6A—C6—H6B	120.0
N1—C1—N3	120.7 (7)	C4—C7—N3	120.7 (7)
C3—C2—C1	121.9 (7)	C4—C7—H7	119.6
C3—C2—H2	119.1	N3—C7—H7	119.6
C1—C2—H2	119.1

(Compound_17_CCDC)

Crystal data

C18H15OP·C7H7NS·	Z = 2
Mr = 415.47	F(000) = 436
Triclinic, P1	Dx = 1.234 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2699 (10) Å	Cell parameters from 3717 reflections
b = 11.1605 (10) Å	θ = 2.4–25.0°
c = 11.1911 (12) Å	µ = 0.23 mm^−1
α = 85.945 (3)°	T = 300 K
β = 67.750 (3)°	Plate, yellow
γ = 70.671 (3)°	0.45 × 0.21 × 0.10 mm
V = 1118.07 (19) Å^3

Data collection

Bruker SMART X2S diffractometer	3900 independent reflections
Radiation source: micro-focus sealed tube	3000 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.903, Tmax = 0.977	k = −13→13
11052 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.3084P] where P = (Fo^2 + 2Fc^2)/3
3900 reflections	(Δ/σ)max < 0.001
268 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S28	0.00829 (8)	0.95834 (6)	0.80459 (7)	0.0636 (2)
P1	0.36152 (6)	0.31286 (5)	0.14058 (5)	0.03709 (16)
O2	0.52104 (15)	0.30422 (14)	0.07712 (14)	0.0476 (4)
N29	0.2043 (3)	0.8500 (2)	0.9086 (2)	0.0619 (6)
H29A	0.278 (4)	0.799 (3)	0.910 (3)	0.093*
H29B	0.164 (4)	0.917 (3)	0.957 (3)	0.093*
C12	0.2106 (3)	0.1851 (3)	−0.1505 (3)	0.0656 (7)
H12	0.1820	0.1574	−0.2102	0.079*
C11	0.1127 (3)	0.2848 (3)	−0.0629 (2)	0.0613 (7)
H11	0.0179	0.3248	−0.0636	0.074*
C10	0.1537 (2)	0.3266 (2)	0.0264 (2)	0.0508 (6)
H10	0.0864	0.3944	0.0854	0.061*
C9	0.2952 (2)	0.2675 (2)	0.02846 (19)	0.0403 (5)
C15	0.3317 (2)	0.21045 (19)	0.27353 (19)	0.0389 (5)
C20	0.3980 (3)	0.2117 (2)	0.3615 (2)	0.0465 (5)
H20	0.4567	0.2630	0.3494	0.056*
C19	0.3770 (3)	0.1368 (2)	0.4665 (2)	0.0580 (7)
H19	0.4205	0.1387	0.5254	0.070*
C18	0.2920 (3)	0.0598 (2)	0.4840 (2)	0.0627 (7)
H18	0.2787	0.0089	0.5542	0.075*
C3	0.2430 (2)	0.47108 (19)	0.21007 (18)	0.0384 (5)
C4	0.1000 (2)	0.4958 (2)	0.3044 (2)	0.0501 (6)
H4	0.0618	0.4296	0.3331	0.060*
C5	0.0151 (3)	0.6191 (2)	0.3551 (2)	0.0604 (7)
H5	−0.0803	0.6359	0.4179	0.072*
C6	0.0719 (3)	0.7170 (2)	0.3124 (2)	0.0642 (7)
H6	0.0148	0.7996	0.3469	0.077*
C7	0.2115 (3)	0.6933 (2)	0.2196 (3)	0.0656 (7)
H7	0.2488	0.7599	0.1908	0.079*
C8	0.2976 (3)	0.5706 (2)	0.1685 (2)	0.0522 (6)
H8	0.3928	0.5550	0.1056	0.063*
C13	0.3503 (3)	0.1263 (3)	−0.1501 (3)	0.0722 (8)
H13	0.4165	0.0585	−0.2095	0.087*
C14	0.3935 (3)	0.1671 (2)	−0.0619 (2)	0.0591 (6)
H14	0.4891	0.1272	−0.0630	0.071*
C16	0.2453 (3)	0.1333 (2)	0.2928 (2)	0.0544 (6)
H16	0.1997	0.1320	0.2355	0.065*
C17	0.2267 (3)	0.0577 (3)	0.3981 (3)	0.0678 (7)
H17	0.1694	0.0052	0.4104	0.081*
C24	0.3296 (4)	0.4823 (3)	0.6075 (3)	0.0861 (9)
H24	0.3681	0.4044	0.5609	0.103*
C25	0.3361 (3)	0.4885 (3)	0.7265 (3)	0.0746 (8)
H25	0.3786	0.4146	0.7611	0.089*
C26	0.2798 (3)	0.6039 (2)	0.7955 (2)	0.0561 (6)
H26	0.2855	0.6072	0.8761	0.067*
C21	0.2148 (2)	0.7154 (2)	0.7463 (2)	0.0455 (5)
C27	0.1491 (2)	0.8390 (2)	0.8232 (2)	0.0469 (5)
C23	0.2667 (4)	0.5904 (4)	0.5575 (3)	0.0883 (10)
H23	0.2632	0.5859	0.4761	0.106*
C22	0.2074 (3)	0.7076 (3)	0.6262 (3)	0.0670 (7)
H22	0.1630	0.7805	0.5916	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S28	0.0588 (4)	0.0497 (4)	0.0905 (5)	−0.0093 (3)	−0.0452 (4)	0.0086 (3)
P1	0.0308 (3)	0.0392 (3)	0.0373 (3)	−0.0069 (2)	−0.0128 (2)	0.0033 (2)
O2	0.0317 (8)	0.0522 (9)	0.0511 (9)	−0.0097 (7)	−0.0112 (7)	0.0047 (7)
N29	0.0526 (13)	0.0526 (13)	0.0825 (16)	0.0012 (10)	−0.0404 (12)	−0.0147 (11)
C12	0.084 (2)	0.0725 (18)	0.0579 (15)	−0.0341 (16)	−0.0373 (15)	0.0024 (14)
C11	0.0546 (15)	0.0806 (19)	0.0594 (15)	−0.0233 (14)	−0.0328 (13)	0.0099 (14)
C10	0.0424 (13)	0.0584 (14)	0.0469 (13)	−0.0081 (11)	−0.0184 (10)	−0.0011 (11)
C9	0.0412 (12)	0.0425 (12)	0.0357 (10)	−0.0116 (10)	−0.0154 (9)	0.0067 (9)
C15	0.0331 (11)	0.0386 (11)	0.0385 (11)	−0.0039 (9)	−0.0135 (9)	0.0025 (9)
C20	0.0489 (13)	0.0443 (12)	0.0451 (12)	−0.0090 (10)	−0.0214 (10)	0.0000 (10)
C19	0.0635 (16)	0.0566 (15)	0.0446 (13)	−0.0010 (13)	−0.0267 (12)	0.0047 (11)
C18	0.0632 (17)	0.0560 (15)	0.0476 (14)	−0.0048 (13)	−0.0134 (12)	0.0175 (12)
C3	0.0357 (11)	0.0414 (11)	0.0351 (10)	−0.0080 (9)	−0.0143 (9)	0.0039 (9)
C4	0.0420 (13)	0.0480 (13)	0.0496 (13)	−0.0088 (11)	−0.0114 (10)	0.0049 (10)
C5	0.0438 (14)	0.0615 (16)	0.0498 (14)	0.0016 (12)	−0.0053 (11)	−0.0023 (12)
C6	0.0699 (18)	0.0429 (14)	0.0584 (15)	0.0046 (13)	−0.0206 (13)	−0.0012 (12)
C7	0.0744 (19)	0.0407 (14)	0.0670 (16)	−0.0146 (13)	−0.0155 (14)	0.0069 (12)
C8	0.0472 (13)	0.0480 (14)	0.0477 (13)	−0.0119 (11)	−0.0069 (10)	0.0054 (11)
C13	0.082 (2)	0.0617 (17)	0.0658 (17)	−0.0052 (15)	−0.0331 (15)	−0.0176 (14)
C14	0.0541 (15)	0.0564 (15)	0.0606 (15)	−0.0027 (12)	−0.0266 (12)	−0.0072 (12)
C16	0.0536 (14)	0.0612 (15)	0.0576 (14)	−0.0248 (12)	−0.0276 (12)	0.0157 (12)
C17	0.0678 (18)	0.0658 (17)	0.0713 (17)	−0.0336 (15)	−0.0216 (14)	0.0244 (14)
C24	0.084 (2)	0.076 (2)	0.093 (2)	−0.0198 (18)	−0.0291 (19)	−0.0275 (19)
C25	0.082 (2)	0.0508 (16)	0.087 (2)	−0.0185 (15)	−0.0293 (17)	−0.0029 (15)
C26	0.0612 (16)	0.0512 (14)	0.0567 (14)	−0.0179 (12)	−0.0228 (12)	−0.0001 (12)
C21	0.0392 (12)	0.0500 (13)	0.0506 (13)	−0.0191 (10)	−0.0168 (10)	0.0035 (11)
C27	0.0424 (13)	0.0461 (13)	0.0581 (14)	−0.0171 (10)	−0.0236 (11)	0.0064 (11)
C23	0.090 (2)	0.111 (3)	0.0656 (18)	−0.024 (2)	−0.0343 (17)	−0.0232 (19)
C22	0.0668 (18)	0.0778 (19)	0.0593 (16)	−0.0188 (15)	−0.0303 (14)	0.0007 (14)

Geometric parameters (Å, º)

S28—C27	1.680 (2)	C4—H4	0.9300
P1—O2	1.4905 (15)	C5—C6	1.378 (4)
P1—C9	1.805 (2)	C5—H5	0.9300
P1—C3	1.805 (2)	C6—C7	1.366 (4)
P1—C15	1.806 (2)	C6—H6	0.9300
N29—C27	1.312 (3)	C7—C8	1.382 (3)
N29—H29A	0.78 (3)	C7—H7	0.9300
N29—H29B	0.84 (3)	C8—H8	0.9300
C12—C13	1.367 (4)	C13—C14	1.382 (3)
C12—C11	1.371 (4)	C13—H13	0.9300
C12—H12	0.9300	C14—H14	0.9300
C11—C10	1.381 (3)	C16—C17	1.391 (3)
C11—H11	0.9300	C16—H16	0.9300
C10—C9	1.392 (3)	C17—H17	0.9300
C10—H10	0.9300	C24—C23	1.360 (5)
C9—C14	1.392 (3)	C24—C25	1.367 (4)
C15—C16	1.381 (3)	C24—H24	0.9300
C15—C20	1.396 (3)	C25—C26	1.378 (3)
C20—C19	1.384 (3)	C25—H25	0.9300
C20—H20	0.9300	C26—C21	1.388 (3)
C19—C18	1.373 (4)	C26—H26	0.9300
C19—H19	0.9300	C21—C22	1.385 (3)
C18—C17	1.369 (4)	C21—C27	1.488 (3)
C18—H18	0.9300	C23—C22	1.390 (4)
C3—C8	1.381 (3)	C23—H23	0.9300
C3—C4	1.395 (3)	C22—H22	0.9300
C4—C5	1.385 (3)
O2—P1—C9	111.58 (9)	C7—C6—C5	120.4 (2)
O2—P1—C3	111.93 (9)	C7—C6—H6	119.8
C9—P1—C3	108.62 (9)	C5—C6—H6	119.8
O2—P1—C15	111.96 (9)	C6—C7—C8	120.2 (2)
C9—P1—C15	107.14 (10)	C6—C7—H7	119.9
C3—P1—C15	105.29 (9)	C8—C7—H7	119.9
C27—N29—H29A	121 (2)	C3—C8—C7	120.4 (2)
C27—N29—H29B	118 (2)	C3—C8—H8	119.8
H29A—N29—H29B	120 (3)	C7—C8—H8	119.8
C13—C12—C11	120.0 (2)	C12—C13—C14	120.3 (2)
C13—C12—H12	120.0	C12—C13—H13	119.8
C11—C12—H12	120.0	C14—C13—H13	119.8
C12—C11—C10	120.6 (2)	C13—C14—C9	120.5 (2)
C12—C11—H11	119.7	C13—C14—H14	119.7
C10—C11—H11	119.7	C9—C14—H14	119.7
C11—C10—C9	120.2 (2)	C15—C16—C17	119.8 (2)
C11—C10—H10	119.9	C15—C16—H16	120.1
C9—C10—H10	119.9	C17—C16—H16	120.1
C10—C9—C14	118.4 (2)	C18—C17—C16	120.7 (2)
C10—C9—P1	124.38 (17)	C18—C17—H17	119.7
C14—C9—P1	117.21 (17)	C16—C17—H17	119.7
C16—C15—C20	119.06 (19)	C23—C24—C25	119.8 (3)
C16—C15—P1	123.23 (16)	C23—C24—H24	120.1
C20—C15—P1	117.70 (16)	C25—C24—H24	120.1
C19—C20—C15	120.3 (2)	C24—C25—C26	120.2 (3)
C19—C20—H20	119.8	C24—C25—H25	119.9
C15—C20—H20	119.8	C26—C25—H25	119.9
C18—C19—C20	120.0 (2)	C25—C26—C21	120.9 (2)
C18—C19—H19	120.0	C25—C26—H26	119.5
C20—C19—H19	120.0	C21—C26—H26	119.5
C17—C18—C19	120.1 (2)	C22—C21—C26	118.3 (2)
C17—C18—H18	120.0	C22—C21—C27	120.9 (2)
C19—C18—H18	120.0	C26—C21—C27	120.7 (2)
C8—C3—C4	119.2 (2)	N29—C27—C21	116.8 (2)
C8—C3—P1	118.24 (16)	N29—C27—S28	121.30 (18)
C4—C3—P1	122.51 (17)	C21—C27—S28	121.86 (17)
C5—C4—C3	119.8 (2)	C24—C23—C22	121.0 (3)
C5—C4—H4	120.1	C24—C23—H23	119.5
C3—C4—H4	120.1	C22—C23—H23	119.5
C6—C5—C4	120.0 (2)	C21—C22—C23	119.8 (3)
C6—C5—H5	120.0	C21—C22—H22	120.1
C4—C5—H5	120.0	C23—C22—H22	120.1

(Compound_17_X2S)

Crystal data

(C7H7NS)·(C18H15OP)	Z = 2
Mr = 415.47	F(000) = 436
Triclinic, P1	Dx = 1.234 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2699 (10) Å	Cell parameters from 3717 reflections
b = 11.1605 (10) Å	θ = 2.4–25.0°
c = 11.1911 (12) Å	µ = 0.23 mm^−1
α = 85.945 (3)°	T = 300 K
β = 67.750 (3)°	Plate, yellow
γ = 70.671 (3)°	0.45 × 0.21 × 0.10 mm
V = 1118.07 (19) Å^3

Data collection

Bruker SMART X2S diffractometer	3902 independent reflections
Radiation source: micro-focus sealed tube	3000 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.035
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.903, Tmax = 0.977	k = −13→13
11064 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0955P)^2 + 0.143P] where P = (Fo^2 + 2Fc^2)/3
3902 reflections	(Δ/σ)max = 0.044
268 parameters	Δρmax = 0.27 e Å^−3
3 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.00828 (8)	0.95842 (7)	−0.19544 (8)	0.0627 (3)
P1	0.36154 (6)	0.31287 (5)	0.14058 (5)	0.0362 (2)
O1	0.52110 (17)	0.30414 (16)	0.07717 (15)	0.0467 (4)
N1	0.2045 (3)	0.8498 (2)	−0.0915 (3)	0.0606 (6)
H@2	0.285 (2)	0.798 (2)	−0.090 (3)	0.091*
H@1	0.168 (3)	0.9166 (19)	−0.043 (3)	0.091*
C1	0.2110 (4)	0.1848 (3)	−0.1506 (3)	0.0648 (8)
H1	0.1825	0.1570	−0.2102	0.078*
C2	0.1128 (3)	0.2845 (3)	−0.0630 (3)	0.0609 (7)
H2	0.0180	0.3242	−0.0638	0.073*
C3	0.1537 (3)	0.3264 (3)	0.0264 (2)	0.0503 (6)
H3	0.0864	0.3943	0.0853	0.060*
C4	0.2954 (3)	0.2674 (2)	0.0285 (2)	0.0396 (5)
C5	0.3317 (2)	0.2103 (2)	0.2735 (2)	0.0384 (5)
C6	0.3982 (3)	0.2117 (2)	0.3614 (2)	0.0460 (6)
H6	0.4568	0.2631	0.3492	0.055*
C7	0.3771 (3)	0.1366 (3)	0.4667 (2)	0.0573 (7)
H7	0.4204	0.1384	0.5257	0.069*
C8	0.2922 (3)	0.0596 (3)	0.4838 (3)	0.0615 (8)
H8	0.2790	0.0087	0.5539	0.074*
C9	0.2431 (2)	0.4710 (2)	0.2101 (2)	0.0378 (5)
C10	0.1001 (3)	0.4957 (2)	0.3045 (2)	0.0493 (6)
H10	0.0619	0.4295	0.3332	0.059*
C11	0.0151 (3)	0.6191 (3)	0.3553 (3)	0.0597 (7)
H11	−0.0802	0.6358	0.4182	0.072*
C12	0.0718 (3)	0.7172 (3)	0.3125 (3)	0.0628 (8)
H12	0.0146	0.7999	0.3468	0.075*
C13	0.2118 (3)	0.6934 (3)	0.2198 (3)	0.0647 (8)
H13	0.2494	0.7599	0.1913	0.078*
C14	0.2975 (3)	0.5707 (2)	0.1684 (2)	0.0514 (6)
H14	0.3926	0.5552	0.1053	0.062*
C15	0.3506 (4)	0.1261 (3)	−0.1503 (3)	0.0711 (9)
H15	0.4169	0.0583	−0.2097	0.085*
C16	0.3938 (3)	0.1671 (3)	−0.0621 (3)	0.0583 (7)
H16	0.4894	0.1273	−0.0633	0.070*
C17	0.2454 (3)	0.1332 (3)	0.2927 (3)	0.0534 (7)
H17	0.1997	0.1318	0.2354	0.064*
C18	0.2270 (4)	0.0574 (3)	0.3981 (3)	0.0669 (8)
H18	0.1698	0.0048	0.4104	0.080*
C19	0.3295 (4)	0.4824 (4)	−0.3927 (4)	0.0855 (11)
H19	0.3675	0.4045	−0.4394	0.103*
C20	0.3365 (4)	0.4882 (3)	−0.2736 (3)	0.0743 (9)
H20	0.3793	0.4143	−0.2392	0.089*
C21	0.2801 (3)	0.6039 (2)	−0.2046 (3)	0.0557 (7)
H21	0.2858	0.6072	−0.1240	0.067*
C22	0.2148 (3)	0.7154 (2)	−0.2536 (2)	0.0451 (6)
C23	0.1491 (3)	0.8393 (2)	−0.1768 (2)	0.0463 (6)
C24	0.2667 (4)	0.5905 (4)	−0.4427 (3)	0.0868 (11)
H24	0.2634	0.5860	−0.5241	0.104*
C25	0.2075 (3)	0.7078 (3)	−0.3741 (3)	0.0661 (8)
H25	0.1631	0.7808	−0.4087	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0580 (5)	0.0489 (4)	0.0895 (6)	−0.0091 (3)	−0.0448 (4)	0.0086 (4)
P1	0.0300 (3)	0.0383 (3)	0.0365 (3)	−0.0068 (2)	−0.0124 (2)	0.0032 (2)
O1	0.0305 (9)	0.0515 (10)	0.0501 (9)	−0.0093 (7)	−0.0106 (7)	0.0045 (8)
N1	0.0515 (14)	0.0525 (14)	0.0810 (17)	0.0000 (11)	−0.0398 (13)	−0.0144 (12)
C1	0.083 (2)	0.0715 (19)	0.0565 (16)	−0.0348 (18)	−0.0361 (16)	0.0016 (15)
C2	0.0541 (16)	0.080 (2)	0.0592 (16)	−0.0241 (15)	−0.0328 (14)	0.0109 (15)
C3	0.0418 (14)	0.0585 (16)	0.0459 (13)	−0.0084 (12)	−0.0176 (11)	−0.0012 (12)
C4	0.0405 (13)	0.0417 (12)	0.0355 (11)	−0.0113 (10)	−0.0158 (10)	0.0066 (10)
C5	0.0328 (12)	0.0387 (12)	0.0377 (11)	−0.0041 (10)	−0.0134 (9)	0.0028 (9)
C6	0.0487 (14)	0.0439 (13)	0.0445 (13)	−0.0091 (11)	−0.0214 (11)	0.0004 (11)
C7	0.0630 (18)	0.0558 (16)	0.0436 (14)	−0.0003 (14)	−0.0267 (13)	0.0047 (12)
C8	0.0624 (18)	0.0546 (16)	0.0467 (15)	−0.0048 (14)	−0.0132 (13)	0.0169 (13)
C9	0.0343 (12)	0.0412 (12)	0.0346 (11)	−0.0078 (10)	−0.0138 (9)	0.0034 (9)
C10	0.0413 (14)	0.0473 (14)	0.0486 (14)	−0.0086 (11)	−0.0110 (11)	0.0048 (11)
C11	0.0433 (15)	0.0614 (18)	0.0488 (15)	0.0015 (13)	−0.0049 (12)	−0.0033 (13)
C12	0.0691 (19)	0.0416 (15)	0.0569 (16)	0.0043 (14)	−0.0200 (14)	−0.0015 (13)
C13	0.073 (2)	0.0397 (15)	0.0668 (18)	−0.0142 (14)	−0.0152 (15)	0.0061 (13)
C14	0.0470 (15)	0.0470 (15)	0.0471 (14)	−0.0121 (12)	−0.0070 (11)	0.0051 (11)
C15	0.082 (2)	0.0608 (19)	0.0645 (18)	−0.0055 (16)	−0.0328 (17)	−0.0164 (15)
C16	0.0537 (16)	0.0557 (16)	0.0596 (16)	−0.0032 (13)	−0.0261 (13)	−0.0067 (13)
C17	0.0535 (16)	0.0601 (16)	0.0564 (15)	−0.0252 (13)	−0.0277 (13)	0.0153 (13)
C18	0.0672 (19)	0.0644 (19)	0.0704 (19)	−0.0328 (16)	−0.0212 (16)	0.0249 (15)
C19	0.084 (2)	0.078 (2)	0.090 (3)	−0.021 (2)	−0.028 (2)	−0.028 (2)
C20	0.081 (2)	0.0503 (17)	0.087 (2)	−0.0189 (16)	−0.0281 (18)	−0.0034 (16)
C21	0.0613 (17)	0.0503 (16)	0.0559 (15)	−0.0175 (13)	−0.0227 (13)	−0.0001 (13)
C22	0.0385 (13)	0.0491 (14)	0.0506 (14)	−0.0184 (11)	−0.0165 (11)	0.0030 (11)
C23	0.0422 (14)	0.0447 (14)	0.0580 (15)	−0.0170 (11)	−0.0235 (12)	0.0066 (11)
C24	0.089 (3)	0.108 (3)	0.065 (2)	−0.023 (2)	−0.0338 (19)	−0.022 (2)
C25	0.0663 (19)	0.077 (2)	0.0578 (17)	−0.0189 (16)	−0.0300 (15)	0.0003 (15)

Geometric parameters (Å, º)

S1—C23	1.679 (2)	C10—H10	0.9300
P1—O1	1.4906 (16)	C11—C12	1.380 (4)
P1—C9	1.804 (2)	C11—H11	0.9300
P1—C4	1.805 (2)	C12—C13	1.367 (4)
P1—C5	1.806 (2)	C12—H12	0.9300
N1—C23	1.312 (3)	C13—C14	1.382 (4)
N1—H@2	0.843 (10)	C13—H13	0.9300
N1—H@1	0.844 (10)	C14—H14	0.9300
C1—C15	1.366 (4)	C15—C16	1.381 (4)
C1—C2	1.370 (4)	C15—H15	0.9300
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.383 (4)	C17—C18	1.391 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.393 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C24	1.359 (5)
C4—C16	1.392 (3)	C19—C20	1.370 (5)
C5—C17	1.381 (3)	C19—H19	0.9300
C5—C6	1.397 (3)	C20—C21	1.380 (4)
C6—C7	1.388 (4)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.389 (4)
C7—C8	1.371 (4)	C21—H21	0.9300
C7—H7	0.9300	C22—C25	1.388 (4)
C8—C18	1.367 (4)	C22—C23	1.489 (4)
C8—H8	0.9300	C24—C25	1.392 (5)
C9—C14	1.382 (3)	C24—H24	0.9300
C9—C10	1.396 (3)	C25—H25	0.9300
C10—C11	1.386 (4)
O1—P1—C9	111.94 (10)	C13—C12—C11	120.3 (3)
O1—P1—C4	111.57 (10)	C13—C12—H12	119.8
C9—P1—C4	108.71 (10)	C11—C12—H12	119.8
O1—P1—C5	111.91 (10)	C12—C13—C14	120.2 (3)
C9—P1—C5	105.33 (10)	C12—C13—H13	119.9
C4—P1—C5	107.06 (11)	C14—C13—H13	119.9
C23—N1—H@2	123 (2)	C13—C14—C9	120.5 (2)
C23—N1—H@1	120 (2)	C13—C14—H14	119.7
H@2—N1—H@1	116 (3)	C9—C14—H14	119.7
C15—C1—C2	120.1 (3)	C1—C15—C16	120.2 (3)
C15—C1—H1	120.0	C1—C15—H15	119.9
C2—C1—H1	120.0	C16—C15—H15	119.9
C1—C2—C3	120.5 (3)	C15—C16—C4	120.6 (3)
C1—C2—H2	119.7	C15—C16—H16	119.7
C3—C2—H2	119.8	C4—C16—H16	119.7
C2—C3—C4	120.2 (2)	C5—C17—C18	119.8 (2)
C2—C3—H3	119.9	C5—C17—H17	120.1
C4—C3—H3	119.9	C18—C17—H17	120.1
C3—C4—C16	118.3 (2)	C8—C18—C17	120.7 (3)
C3—C4—P1	124.37 (18)	C8—C18—H18	119.7
C16—C4—P1	117.32 (18)	C17—C18—H18	119.7
C17—C5—C6	119.1 (2)	C24—C19—C20	119.9 (3)
C17—C5—P1	123.27 (18)	C24—C19—H19	120.1
C6—C5—P1	117.58 (18)	C20—C19—H19	120.1
C7—C6—C5	120.2 (2)	C19—C20—C21	120.0 (3)
C7—C6—H6	119.9	C19—C20—H20	120.0
C5—C6—H6	119.9	C21—C20—H20	120.0
C8—C7—C6	120.0 (3)	C20—C21—C22	121.0 (3)
C8—C7—H7	120.0	C20—C21—H21	119.5
C6—C7—H7	120.0	C22—C21—H21	119.5
C18—C8—C7	120.3 (2)	C25—C22—C21	118.3 (3)
C18—C8—H8	119.9	C25—C22—C23	120.8 (2)
C7—C8—H8	119.9	C21—C22—C23	120.9 (2)
C14—C9—C10	119.2 (2)	N1—C23—C22	116.6 (2)
C14—C9—P1	118.32 (17)	N1—C23—S1	121.5 (2)
C10—C9—P1	122.51 (19)	C22—C23—S1	121.87 (18)
C11—C10—C9	119.8 (2)	C19—C24—C25	121.1 (3)
C11—C10—H10	120.1	C19—C24—H24	119.5
C9—C10—H10	120.1	C25—C24—H24	119.5
C12—C11—C10	120.1 (2)	C22—C25—C24	119.7 (3)
C12—C11—H11	120.0	C22—C25—H25	120.2
C10—C11—H11	120.0	C24—C25—H25	120.2

(Compound_18_APEX)

Crystal data

C13H13NO2S	Z = 4
Mr = 247.30	F(000) = 520
Triclinic, P1	Dx = 1.275 Mg m^−3
a = 10.259 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.050 (4) Å	Cell parameters from 6965 reflections
c = 13.380 (5) Å	θ = 2.4–24.4°
α = 67.808 (8)°	µ = 0.24 mm^−1
β = 87.291 (8)°	T = 291 K
γ = 67.435 (7)°	Block, colorless
V = 1288.4 (7) Å^3	0.32 × 0.30 × 0.18 mm

Data collection

Bruker APEX II DUO diffractometer	4600 independent reflections
Radiation source: fine-focus sealed tube	3117 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3333 pixels mm^-1	θmax = 25.7°, θmin = 2.2°
φ & ω scans	h = −12→12
Absorption correction: multi-scan SADABS Version 2008/1	k = −13→13
Tmin = 0.78, Tmax = 0.94	l = −15→16
23008 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.266	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.1686P)^2 + 0.2365P] where P = (Fo^2 + 2Fc^2)/3
4600 reflections	(Δ/σ)max = 0.008
333 parameters	Δρmax = 0.37 e Å^−3
30 restraints	Δρmin = −0.44 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.20036 (14)	0.42400 (11)	0.11580 (12)	0.0794 (5)	0.85
O2A	0.1773 (4)	0.3848 (4)	0.0299 (4)	0.1042 (12)	0.85
O3A	0.2814 (4)	0.3131 (3)	0.2164 (3)	0.0877 (10)	0.85
N4A	0.0420 (4)	0.5094 (4)	0.1407 (4)	0.0852 (11)	0.85
H4A	0.0081	0.5482	0.0731	0.128*	0.85
S1B	0.2538 (10)	0.3996 (10)	0.1608 (8)	0.0751 (19)*	0.15
O2B	0.142 (2)	0.395 (3)	0.101 (2)	0.103 (7)*	0.15
O3B	0.384 (2)	0.281 (2)	0.2015 (19)	0.113 (7)*	0.15
N4B	0.191 (2)	0.443 (2)	0.2605 (14)	0.080 (5)*	0.15
H4B	0.2683	0.3816	0.3048	0.121*	0.15
C5	0.0092 (5)	0.5767 (4)	0.2165 (4)	0.0944 (13)
C6	−0.1227 (7)	0.6922 (6)	0.1955 (5)	0.1273 (19)
H6	−0.1812	0.7294	0.1311	0.153*
C7	−0.1628 (7)	0.7496 (6)	0.2749 (6)	0.139 (2)
H7	−0.2512	0.8231	0.2651	0.167*
C8	−0.0728 (8)	0.6978 (7)	0.3660 (5)	0.138 (2)
H8	−0.0983	0.7355	0.4189	0.165*
C9	0.0527 (7)	0.5918 (6)	0.3782 (5)	0.1205 (17)
H9	0.1151	0.5594	0.4396	0.145*
C10	0.0940 (5)	0.5295 (6)	0.3078 (5)	0.1074 (15)
H10	0.1809	0.4527	0.3216	0.129*
C11A	0.2825 (6)	0.5444 (5)	0.0630 (4)	0.0744 (19)	0.85
C12A	0.3931 (6)	0.5318 (4)	0.1276 (3)	0.085 (2)	0.85
H12A	0.4264	0.4565	0.1950	0.102*	0.85
C13A	0.4537 (4)	0.6316 (5)	0.0916 (4)	0.0887 (15)	0.85
H13A	0.5277	0.6231	0.1349	0.106*	0.85
C14A	0.4038 (5)	0.7440 (4)	−0.0090 (5)	0.0920 (16)	0.85
C15A	0.2933 (6)	0.7567 (5)	−0.0736 (3)	0.104 (2)	0.85
H15A	0.2600	0.8320	−0.1409	0.125*	0.85
C16A	0.2327 (5)	0.6569 (6)	−0.0376 (4)	0.0897 (19)	0.85
H16A	0.1587	0.6654	−0.0808	0.108*	0.85
C17A	0.4636 (8)	0.8606 (8)	−0.0505 (8)	0.140 (3)	0.85
H17A	0.4937	0.8738	0.0101	0.210*	0.85
H17B	0.3911	0.9483	−0.0980	0.210*	0.85
H17C	0.5431	0.8324	−0.0894	0.210*	0.85
C11B	0.284 (3)	0.548 (3)	0.0854 (18)	0.031 (5)*	0.15
C12B	0.408 (3)	0.555 (3)	0.1164 (15)	0.060 (8)*	0.15
H12B	0.4585	0.4925	0.1841	0.072*	0.15
C13B	0.456 (3)	0.655 (3)	0.0463 (18)	0.074 (9)*	0.15
H13B	0.5383	0.6594	0.0671	0.089*	0.15
C14B	0.380 (3)	0.748 (3)	−0.0550 (16)	0.087 (11)*	0.15
C15B	0.256 (3)	0.742 (3)	−0.0860 (17)	0.105 (14)*	0.15
H15B	0.2053	0.8042	−0.1537	0.126*	0.15
C16B	0.208 (3)	0.642 (3)	−0.016 (2)	0.085 (12)*	0.15
H16B	0.1254	0.6373	−0.0366	0.102*	0.15
C17B	0.429 (3)	0.867 (3)	−0.129 (2)	0.097 (9)*	0.15
H17D	0.3863	0.9496	−0.1125	0.146*	0.15
H17E	0.4015	0.8906	−0.2041	0.146*	0.15
H17F	0.5309	0.8325	−0.1170	0.146*	0.15
S18	0.47506 (9)	0.21890 (9)	0.50060 (8)	0.0703 (4)
O19	0.4133 (3)	0.3707 (3)	0.4496 (3)	0.0923 (9)
O20	0.3851 (3)	0.1422 (3)	0.5255 (3)	0.0873 (8)
N21	0.5778 (3)	0.1580 (4)	0.4202 (3)	0.0746 (9)
H21	0.588 (5)	0.075 (4)	0.438 (4)	0.089*
C22	0.7029 (4)	0.1844 (4)	0.3923 (3)	0.0693 (9)
C23	0.8226 (4)	0.0736 (5)	0.3889 (3)	0.0872 (12)
H23	0.8206	−0.0154	0.4061	0.105*
C24	0.9449 (5)	0.0940 (6)	0.3602 (4)	0.1098 (16)
H24	1.0249	0.0184	0.3577	0.132*
C25	0.9518 (6)	0.2230 (7)	0.3353 (5)	0.1157 (17)
H25	1.0354	0.2355	0.3157	0.139*
C26	0.8355 (7)	0.3323 (7)	0.3394 (4)	0.1127 (16)
H26	0.8404	0.4195	0.3250	0.135*
C27	0.7089 (5)	0.3164 (5)	0.3649 (4)	0.0944 (12)
H27	0.6282	0.3939	0.3636	0.113*
C28	0.5841 (3)	0.1697 (3)	0.6181 (3)	0.0567 (7)
C29	0.6398 (4)	0.0303 (4)	0.6901 (3)	0.0692 (9)
H29	0.6152	−0.0369	0.6792	0.083*
C30	0.7324 (4)	−0.0089 (4)	0.7785 (3)	0.0785 (10)
H30	0.7685	−0.1030	0.8281	0.094*
C31	0.7728 (4)	0.0881 (4)	0.7953 (3)	0.0745 (10)
C32	0.7152 (5)	0.2273 (4)	0.7233 (3)	0.0873 (12)
H32	0.7391	0.2943	0.7350	0.105*
C33	0.6219 (4)	0.2700 (4)	0.6332 (3)	0.0784 (11)
H33	0.5853	0.3642	0.5839	0.094*
C34	0.8804 (5)	0.0425 (7)	0.8902 (4)	0.1181 (18)
H34A	0.8837	0.1253	0.8960	0.177*
H34B	0.9725	−0.0150	0.8785	0.177*
H34C	0.8529	−0.0116	0.9561	0.177*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0729 (7)	0.0549 (6)	0.1040 (10)	−0.0135 (5)	−0.0189 (7)	−0.0328 (6)
O2A	0.097 (2)	0.084 (2)	0.133 (3)	−0.0147 (18)	−0.027 (2)	−0.060 (2)
O3A	0.098 (3)	0.0488 (16)	0.094 (2)	−0.0202 (16)	−0.0181 (19)	−0.0099 (16)
N4A	0.069 (2)	0.078 (2)	0.108 (3)	−0.0302 (19)	−0.005 (2)	−0.033 (2)
C5	0.093 (3)	0.071 (2)	0.131 (4)	−0.046 (2)	0.040 (3)	−0.041 (3)
C6	0.141 (5)	0.101 (4)	0.118 (4)	−0.043 (4)	0.011 (4)	−0.025 (3)
C7	0.136 (5)	0.097 (4)	0.136 (5)	−0.002 (3)	0.024 (4)	−0.042 (4)
C8	0.154 (5)	0.114 (4)	0.112 (4)	−0.015 (4)	0.024 (4)	−0.048 (4)
C9	0.124 (4)	0.117 (4)	0.127 (4)	−0.052 (4)	0.041 (4)	−0.055 (4)
C10	0.082 (3)	0.107 (4)	0.151 (5)	−0.042 (3)	0.026 (3)	−0.066 (4)
C11A	0.078 (3)	0.067 (3)	0.073 (4)	−0.012 (2)	0.004 (3)	−0.039 (3)
C12A	0.081 (4)	0.067 (3)	0.093 (4)	−0.019 (3)	−0.006 (3)	−0.027 (3)
C13A	0.075 (3)	0.094 (4)	0.094 (4)	−0.037 (3)	0.018 (3)	−0.031 (3)
C14A	0.080 (3)	0.071 (3)	0.110 (4)	−0.022 (3)	0.031 (3)	−0.031 (3)
C15A	0.107 (5)	0.078 (4)	0.084 (4)	−0.013 (3)	0.014 (3)	−0.009 (3)
C16A	0.092 (4)	0.074 (3)	0.073 (3)	−0.015 (3)	0.001 (3)	−0.015 (3)
C17A	0.118 (5)	0.116 (5)	0.177 (6)	−0.052 (4)	0.046 (5)	−0.045 (4)
S18	0.0561 (5)	0.0679 (6)	0.0923 (7)	−0.0261 (4)	0.0076 (4)	−0.0352 (5)
O19	0.0717 (16)	0.0669 (16)	0.116 (2)	−0.0160 (13)	−0.0073 (15)	−0.0218 (15)
O20	0.0577 (13)	0.0974 (19)	0.129 (2)	−0.0388 (13)	0.0175 (14)	−0.0593 (18)
N21	0.0699 (18)	0.085 (2)	0.085 (2)	−0.0397 (17)	0.0102 (15)	−0.0407 (18)
C22	0.072 (2)	0.093 (2)	0.0527 (17)	−0.046 (2)	0.0098 (16)	−0.0258 (17)
C23	0.081 (3)	0.096 (3)	0.091 (3)	−0.041 (2)	0.023 (2)	−0.038 (2)
C24	0.085 (3)	0.120 (4)	0.116 (4)	−0.044 (3)	0.030 (3)	−0.035 (3)
C25	0.096 (3)	0.142 (5)	0.116 (4)	−0.071 (4)	0.030 (3)	−0.036 (4)
C26	0.127 (4)	0.124 (4)	0.112 (4)	−0.089 (4)	0.033 (3)	−0.033 (3)
C27	0.101 (3)	0.090 (3)	0.097 (3)	−0.051 (3)	0.021 (2)	−0.029 (2)
C28	0.0579 (16)	0.0484 (15)	0.0716 (18)	−0.0247 (13)	0.0168 (15)	−0.0289 (14)
C29	0.070 (2)	0.0559 (18)	0.091 (2)	−0.0344 (16)	0.0127 (18)	−0.0289 (17)
C30	0.079 (2)	0.064 (2)	0.086 (2)	−0.0264 (18)	0.005 (2)	−0.0239 (18)
C31	0.072 (2)	0.095 (3)	0.072 (2)	−0.038 (2)	0.0208 (18)	−0.045 (2)
C32	0.114 (3)	0.084 (3)	0.097 (3)	−0.056 (2)	0.015 (2)	−0.053 (2)
C33	0.105 (3)	0.0532 (18)	0.086 (2)	−0.0375 (19)	0.008 (2)	−0.0307 (17)
C34	0.100 (3)	0.164 (5)	0.103 (3)	−0.046 (3)	0.004 (3)	−0.070 (4)

Geometric parameters (Å, º)

S1A—O2A	1.431 (4)	C13B—C14B	1.3900
S1A—O3A	1.444 (3)	C13B—H13B	0.9300
S1A—N4A	1.628 (4)	C14B—C15B	1.3900
S1A—C11A	1.754 (4)	C14B—C17B	1.562 (17)
N4A—C5	1.429 (6)	C15B—C16B	1.3900
N4A—H4A	0.8631	C15B—H15B	0.9300
S1B—O3B	1.412 (16)	C16B—H16B	0.9300
S1B—O2B	1.450 (16)	C17B—H17D	0.9600
S1B—N4B	1.608 (15)	C17B—H17E	0.9600
S1B—C11B	1.71 (2)	C17B—H17F	0.9600
N4B—C10	1.405 (16)	S18—O20	1.428 (3)
N4B—H4B	0.8753	S18—O19	1.429 (3)
N4B—H10	0.8606	S18—N21	1.617 (3)
C5—C10	1.338 (6)	S18—C28	1.753 (3)
C5—C6	1.407 (8)	N21—C22	1.425 (5)
C6—C7	1.402 (8)	N21—H21	0.82 (4)
C6—H6	0.9300	C22—C23	1.375 (5)
C7—C8	1.356 (8)	C22—C27	1.389 (6)
C7—H7	0.9300	C23—C24	1.370 (6)
C8—C9	1.332 (8)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.366 (8)
C9—C10	1.330 (7)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.350 (8)
C10—H10	0.9300	C25—H25	0.9300
C11A—C12A	1.3900	C26—C27	1.386 (7)
C11A—C16A	1.3900	C26—H26	0.9300
C12A—C13A	1.3900	C27—H27	0.9300
C12A—H12A	0.9300	C28—C29	1.372 (5)
C13A—C14A	1.3900	C28—C33	1.388 (4)
C13A—H13A	0.9300	C29—C30	1.376 (5)
C14A—C15A	1.3900	C29—H29	0.9300
C14A—C17A	1.542 (7)	C30—C31	1.380 (5)
C15A—C16A	1.3900	C30—H30	0.9300
C15A—H15A	0.9300	C31—C32	1.371 (5)
C16A—H16A	0.9300	C31—C34	1.518 (6)
C17A—H17A	0.9600	C32—C33	1.387 (5)
C17A—H17B	0.9600	C32—H32	0.9300
C17A—H17C	0.9600	C33—H33	0.9300
C11B—C12B	1.3900	C34—H34A	0.9600
C11B—C16B	1.3900	C34—H34B	0.9600
C12B—C13B	1.3900	C34—H34C	0.9600
C12B—H12B	0.9300
O2A—S1A—O3A	118.6 (2)	C13B—C12B—H12B	120.0
O2A—S1A—N4A	105.0 (2)	C14B—C13B—C12B	120.0
O3A—S1A—N4A	108.8 (2)	C14B—C13B—H13B	120.0
O2A—S1A—C11A	106.8 (3)	C12B—C13B—H13B	120.0
O3A—S1A—C11A	109.0 (2)	C15B—C14B—C13B	120.0
N4A—S1A—C11A	108.2 (2)	C15B—C14B—C17B	120.7 (17)
C5—N4A—S1A	126.2 (3)	C13B—C14B—C17B	119.2 (17)
C5—N4A—H4A	126.2	C14B—C15B—C16B	120.0
S1A—N4A—H4A	92.9	C14B—C15B—H15B	120.0
O3B—S1B—O2B	120.5 (15)	C16B—C15B—H15B	120.0
O3B—S1B—N4B	107.7 (13)	C15B—C16B—C11B	120.0
O2B—S1B—N4B	109.2 (14)	C15B—C16B—H16B	120.0
O3B—S1B—C11B	110.0 (15)	C11B—C16B—H16B	120.0
O2B—S1B—C11B	108.6 (14)	C14B—C17B—H17D	109.5
N4B—S1B—C11B	98.6 (13)	C14B—C17B—H17E	109.5
C10—N4B—S1B	154.4 (16)	H17D—C17B—H17E	109.5
C10—N4B—H4B	112.1	C14B—C17B—H17F	109.5
S1B—N4B—H4B	92.8	H17D—C17B—H17F	109.5
C10—N4B—H10	40.1	H17E—C17B—H17F	109.5
S1B—N4B—H10	164.6	O20—S18—O19	119.48 (17)
H4B—N4B—H10	72.1	O20—S18—N21	103.58 (17)
C10—C5—C6	119.8 (5)	O19—S18—N21	108.41 (19)
C10—C5—N4A	122.9 (4)	O20—S18—C28	109.63 (17)
C6—C5—N4A	117.2 (5)	O19—S18—C28	108.35 (16)
C7—C6—C5	117.8 (6)	N21—S18—C28	106.64 (15)
C7—C6—H6	121.1	C22—N21—S18	122.5 (2)
C5—C6—H6	121.1	C22—N21—H21	115 (3)
C8—C7—C6	120.0 (5)	S18—N21—H21	107 (3)
C8—C7—H7	120.0	C23—C22—C27	118.5 (4)
C6—C7—H7	120.0	C23—C22—N21	117.8 (4)
C9—C8—C7	118.7 (6)	C27—C22—N21	123.7 (4)
C9—C8—H8	120.7	C24—C23—C22	120.2 (5)
C7—C8—H8	120.7	C24—C23—H23	119.9
C10—C9—C8	123.9 (6)	C22—C23—H23	119.9
C10—C9—H9	118.1	C25—C24—C23	121.4 (5)
C8—C9—H9	118.1	C25—C24—H24	119.3
C9—C10—C5	119.8 (5)	C23—C24—H24	119.3
C9—C10—N4B	155.9 (10)	C26—C25—C24	119.1 (5)
C5—C10—N4B	83.6 (9)	C26—C25—H25	120.5
C9—C10—H10	120.7	C24—C25—H25	120.5
C5—C10—H10	119.5	C25—C26—C27	121.0 (5)
N4B—C10—H10	36.6	C25—C26—H26	119.5
C12A—C11A—C16A	120.0	C27—C26—H26	119.5
C12A—C11A—S1A	118.5 (3)	C26—C27—C22	119.8 (5)
C16A—C11A—S1A	121.4 (3)	C26—C27—H27	120.1
C13A—C12A—C11A	120.0	C22—C27—H27	120.1
C13A—C12A—H12A	120.0	C29—C28—C33	120.6 (3)
C11A—C12A—H12A	120.0	C29—C28—S18	119.7 (2)
C14A—C13A—C12A	120.0	C33—C28—S18	119.6 (3)
C14A—C13A—H13A	120.0	C28—C29—C30	119.3 (3)
C12A—C13A—H13A	120.0	C28—C29—H29	120.4
C13A—C14A—C15A	120.0	C30—C29—H29	120.4
C13A—C14A—C17A	121.9 (5)	C29—C30—C31	121.5 (4)
C15A—C14A—C17A	118.0 (5)	C29—C30—H30	119.2
C16A—C15A—C14A	120.0	C31—C30—H30	119.2
C16A—C15A—H15A	120.0	C32—C31—C30	118.5 (3)
C14A—C15A—H15A	120.0	C32—C31—C34	120.3 (4)
C15A—C16A—C11A	120.0	C30—C31—C34	121.2 (4)
C15A—C16A—H16A	120.0	C31—C32—C33	121.3 (3)
C11A—C16A—H16A	120.0	C31—C32—H32	119.4
C14A—C17A—H17A	109.5	C33—C32—H32	119.4
C14A—C17A—H17B	109.5	C32—C33—C28	118.8 (3)
H17A—C17A—H17B	109.5	C32—C33—H33	120.6
C14A—C17A—H17C	109.5	C28—C33—H33	120.6
H17A—C17A—H17C	109.5	C31—C34—H34A	109.5
H17B—C17A—H17C	109.5	C31—C34—H34B	109.5
C12B—C11B—C16B	120.0	H34A—C34—H34B	109.5
C12B—C11B—S1B	117.0 (15)	C31—C34—H34C	109.5
C16B—C11B—S1B	121.4 (15)	H34A—C34—H34C	109.5
C11B—C12B—C13B	120.0	H34B—C34—H34C	109.5
C11B—C12B—H12B	120.0
O2A—S1A—N4A—C5	−176.5 (4)	O2B—S1B—C11B—C16B	0 (2)
O3A—S1A—N4A—C5	55.6 (4)	N4B—S1B—C11B—C16B	−114.0 (17)
C11A—S1A—N4A—C5	−62.7 (4)	C16B—C11B—C12B—C13B	0.0
O3B—S1B—N4B—C10	174 (4)	S1B—C11B—C12B—C13B	165.5 (19)
O2B—S1B—N4B—C10	−53 (4)	C11B—C12B—C13B—C14B	0.0
C11B—S1B—N4B—C10	60 (4)	C12B—C13B—C14B—C15B	0.0
S1A—N4A—C5—C10	−30.7 (7)	C12B—C13B—C14B—C17B	176 (3)
S1A—N4A—C5—C6	153.1 (4)	C13B—C14B—C15B—C16B	0.0
C10—C5—C6—C7	−3.0 (8)	C17B—C14B—C15B—C16B	−176 (3)
N4A—C5—C6—C7	173.3 (5)	C14B—C15B—C16B—C11B	0.0
C5—C6—C7—C8	3.0 (10)	C12B—C11B—C16B—C15B	0.0
C6—C7—C8—C9	−0.4 (11)	S1B—C11B—C16B—C15B	−165 (2)
C7—C8—C9—C10	−2.4 (11)	O20—S18—N21—C22	−167.2 (3)
C8—C9—C10—C5	2.4 (10)	O19—S18—N21—C22	65.0 (3)
C8—C9—C10—N4B	166 (2)	C28—S18—N21—C22	−51.5 (3)
C6—C5—C10—C9	0.4 (8)	S18—N21—C22—C23	138.4 (3)
N4A—C5—C10—C9	−175.7 (5)	S18—N21—C22—C27	−43.9 (5)
C6—C5—C10—N4B	−173.1 (10)	C27—C22—C23—C24	0.8 (6)
N4A—C5—C10—N4B	10.8 (10)	N21—C22—C23—C24	178.6 (4)
S1B—N4B—C10—C9	−146 (2)	C22—C23—C24—C25	0.5 (7)
S1B—N4B—C10—C5	20 (4)	C23—C24—C25—C26	0.2 (9)
O2A—S1A—C11A—C12A	−138.6 (3)	C24—C25—C26—C27	−2.2 (9)
O3A—S1A—C11A—C12A	−9.3 (4)	C25—C26—C27—C22	3.5 (8)
N4A—S1A—C11A—C12A	108.8 (3)	C23—C22—C27—C26	−2.7 (6)
O2A—S1A—C11A—C16A	46.2 (4)	N21—C22—C27—C26	179.6 (4)
O3A—S1A—C11A—C16A	175.4 (3)	O20—S18—C28—C29	38.7 (3)
N4A—S1A—C11A—C16A	−66.4 (3)	O19—S18—C28—C29	170.7 (3)
C16A—C11A—C12A—C13A	0.0	N21—S18—C28—C29	−72.8 (3)
S1A—C11A—C12A—C13A	−175.3 (4)	O20—S18—C28—C33	−146.1 (3)
C11A—C12A—C13A—C14A	0.0	O19—S18—C28—C33	−14.1 (4)
C12A—C13A—C14A—C15A	0.0	N21—S18—C28—C33	102.4 (3)
C12A—C13A—C14A—C17A	177.5 (5)	C33—C28—C29—C30	0.8 (6)
C13A—C14A—C15A—C16A	0.0	S18—C28—C29—C30	175.9 (3)
C17A—C14A—C15A—C16A	−177.6 (5)	C28—C29—C30—C31	−1.3 (6)
C14A—C15A—C16A—C11A	0.0	C29—C30—C31—C32	2.0 (6)
C12A—C11A—C16A—C15A	0.0	C29—C30—C31—C34	−177.1 (4)
S1A—C11A—C16A—C15A	175.2 (4)	C30—C31—C32—C33	−2.1 (6)
O3B—S1B—C11B—C12B	−32 (2)	C34—C31—C32—C33	176.9 (4)
O2B—S1B—C11B—C12B	−165.7 (17)	C31—C32—C33—C28	1.7 (6)
N4B—S1B—C11B—C12B	80.6 (17)	C29—C28—C33—C32	−1.0 (6)
O3B—S1B—C11B—C16B	133.5 (18)	S18—C28—C33—C32	−176.1 (3)

(Compound_18_CCDC)

Crystal data

C13H13NO2S	Z = 4
Mr = 247.30	F(000) = 520
Triclinic, P1	Dx = 1.264 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2890 (11) Å	Cell parameters from 5366 reflections
b = 11.0563 (12) Å	θ = 2.5–24.7°
c = 13.4402 (15) Å	µ = 0.24 mm^−1
α = 67.823 (3)°	T = 300 K
β = 87.573 (4)°	Plate, colorless
γ = 67.616 (3)°	0.32 × 0.30 × 0.18 mm
V = 1299.9 (2) Å^3

Data collection

Bruker SMART X2S diffractometer	4544 independent reflections
Radiation source: micro-focus sealed tube	3364 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.036
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.890, Tmax = 0.890	k = −13→13
12851 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1035P)^2 + 0.2796P] where P = (Fo^2 + 2Fc^2)/3
4544 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 0.25 e Å^−3
30 restraints	Δρmin = −0.40 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.20015 (11)	0.42407 (8)	0.11615 (9)	0.0804 (3)	0.85
O2A	0.1771 (3)	0.3842 (3)	0.0303 (3)	0.1086 (9)	0.85
O3A	0.2814 (3)	0.3134 (3)	0.2163 (2)	0.0912 (8)	0.85
N4A	0.0413 (3)	0.5097 (3)	0.1408 (3)	0.0875 (8)	0.85
H4A	0.0075	0.5485	0.0732	0.131*	0.85
S1B	0.2538 (7)	0.3989 (8)	0.1617 (6)	0.0738 (13)*	0.15
O2B	0.1418 (18)	0.403 (2)	0.0960 (15)	0.108 (5)*	0.15
O3B	0.3793 (16)	0.2769 (15)	0.2076 (12)	0.101 (5)*	0.15
N4B	0.1907 (16)	0.4415 (16)	0.2611 (11)	0.084 (4)*	0.15
H4B	0.2677	0.3802	0.3054	0.126*	0.15
C5	0.0088 (4)	0.5769 (3)	0.2161 (3)	0.0946 (10)
C6	−0.1234 (5)	0.6920 (5)	0.1949 (4)	0.1306 (13)
H6	−0.1820	0.7284	0.1308	0.157*
C7	−0.1638 (5)	0.7499 (5)	0.2741 (4)	0.1409 (16)
H7	−0.2519	0.8231	0.2641	0.169*
C8	−0.0732 (6)	0.6984 (5)	0.3653 (4)	0.1407 (16)
H8	−0.0981	0.7369	0.4174	0.169*
C9	0.0519 (5)	0.5918 (5)	0.3785 (4)	0.1245 (13)
H9	0.1132	0.5580	0.4406	0.149*
C10	0.0941 (4)	0.5305 (4)	0.3062 (4)	0.1085 (11)
H10	0.1809	0.4537	0.3200	0.130*
C11A	0.2814 (4)	0.5458 (4)	0.0635 (3)	0.0717 (15)	0.85
C12A	0.3936 (4)	0.5321 (3)	0.1267 (2)	0.0774 (12)	0.85
H12A	0.4279	0.4566	0.1936	0.093*	0.85
C13A	0.4547 (3)	0.6314 (4)	0.0901 (3)	0.0926 (11)	0.85
H13A	0.5298	0.6222	0.1324	0.111*	0.85
C14A	0.4036 (3)	0.7443 (3)	−0.0098 (4)	0.0930 (11)	0.85
C15A	0.2913 (4)	0.7579 (3)	−0.0731 (2)	0.1015 (13)	0.85
H15A	0.2571	0.8335	−0.1399	0.122*	0.85
C16A	0.2303 (4)	0.6587 (4)	−0.0364 (3)	0.0955 (15)	0.85
H16A	0.1552	0.6678	−0.0788	0.115*	0.85
C17A	0.4640 (6)	0.8593 (5)	−0.0516 (5)	0.143 (2)	0.85
H17A	0.4943	0.8731	0.0084	0.215*	0.85
H17B	0.3923	0.9468	−0.0996	0.215*	0.85
H17C	0.5432	0.8300	−0.0898	0.215*	0.85
C11B	0.293 (3)	0.543 (2)	0.0859 (16)	0.044 (5)*	0.15
C12B	0.408 (3)	0.562 (2)	0.1180 (12)	0.094 (10)*	0.15
H12B	0.4566	0.5048	0.1869	0.113*	0.15
C13B	0.450 (2)	0.665 (3)	0.0470 (14)	0.084 (8)*	0.15
H13B	0.5270	0.6781	0.0685	0.101*	0.15
C14B	0.377 (2)	0.750 (2)	−0.0560 (12)	0.079 (7)*	0.15
C15B	0.262 (2)	0.732 (2)	−0.0880 (12)	0.079 (7)*	0.15
H15B	0.2129	0.7884	−0.1569	0.095*	0.15
C16B	0.220 (2)	0.628 (3)	−0.0171 (18)	0.063 (6)*	0.15
H16B	0.1425	0.6152	−0.0385	0.076*	0.15
C17B	0.424 (3)	0.867 (2)	−0.1305 (18)	0.108 (8)*	0.15
H17D	0.3813	0.9504	−0.1142	0.162*	0.15
H17E	0.3946	0.8905	−0.2046	0.162*	0.15
H17F	0.5251	0.8339	−0.1192	0.162*	0.15
S18	0.47516 (6)	0.21883 (7)	0.50060 (6)	0.0710 (2)
O19	0.4129 (2)	0.3703 (2)	0.45041 (18)	0.0956 (6)
O20	0.38487 (18)	0.1421 (2)	0.52602 (18)	0.0875 (6)
N21	0.5786 (2)	0.1583 (3)	0.41986 (19)	0.0748 (6)
H21	0.583 (3)	0.078 (3)	0.435 (2)	0.090*
C22	0.7038 (3)	0.1843 (3)	0.39199 (18)	0.0702 (7)
C23	0.8225 (3)	0.0741 (3)	0.3889 (2)	0.0882 (8)
H23	0.8203	−0.0149	0.4068	0.106*
C24	0.9449 (4)	0.0939 (5)	0.3598 (3)	0.1137 (12)
H24	1.0243	0.0189	0.3566	0.136*
C25	0.9503 (4)	0.2241 (5)	0.3353 (3)	0.1194 (13)
H25	1.0332	0.2376	0.3160	0.143*
C26	0.8345 (5)	0.3319 (5)	0.3397 (3)	0.1155 (12)
H26	0.8389	0.4194	0.3247	0.139*
C27	0.7077 (4)	0.3158 (4)	0.3662 (3)	0.0957 (9)
H27	0.6276	0.3922	0.3664	0.115*
C28	0.5846 (2)	0.1698 (2)	0.61768 (19)	0.0588 (5)
C29	0.6400 (3)	0.0302 (3)	0.6903 (2)	0.0710 (6)
H29	0.6151	−0.0370	0.6797	0.085*
C30	0.7321 (3)	−0.0090 (3)	0.7783 (2)	0.0788 (7)
H30	0.7685	−0.1032	0.8273	0.095*
C31	0.7725 (3)	0.0881 (3)	0.7960 (2)	0.0777 (7)
C32	0.7150 (3)	0.2275 (3)	0.7228 (3)	0.0888 (9)
H32	0.7396	0.2946	0.7337	0.107*
C33	0.6219 (3)	0.2695 (3)	0.6339 (2)	0.0781 (7)
H33	0.5846	0.3638	0.5852	0.094*
C34	0.8796 (4)	0.0418 (5)	0.8906 (3)	0.1205 (13)
H34A	0.8801	0.1241	0.8990	0.181*
H34B	0.9720	−0.0118	0.8775	0.181*
H34C	0.8546	−0.0162	0.9554	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0732 (5)	0.0573 (5)	0.1042 (7)	−0.0142 (4)	−0.0176 (5)	−0.0336 (5)
O2A	0.0998 (18)	0.0889 (17)	0.139 (2)	−0.0140 (14)	−0.0282 (16)	−0.0658 (17)
O3A	0.0983 (19)	0.0493 (13)	0.1012 (17)	−0.0179 (12)	−0.0221 (14)	−0.0115 (13)
N4A	0.0702 (16)	0.0789 (18)	0.112 (2)	−0.0297 (14)	−0.0040 (15)	−0.0342 (16)
C5	0.091 (2)	0.0746 (19)	0.132 (3)	−0.0475 (17)	0.043 (2)	−0.0422 (19)
C6	0.140 (3)	0.107 (3)	0.118 (3)	−0.042 (3)	0.009 (3)	−0.023 (2)
C7	0.138 (4)	0.103 (3)	0.137 (4)	−0.006 (3)	0.032 (3)	−0.044 (3)
C8	0.159 (4)	0.117 (3)	0.121 (3)	−0.023 (3)	0.033 (3)	−0.053 (3)
C9	0.124 (3)	0.122 (3)	0.135 (3)	−0.048 (3)	0.041 (3)	−0.060 (3)
C10	0.086 (2)	0.111 (3)	0.149 (3)	−0.049 (2)	0.030 (2)	−0.064 (3)
C11A	0.071 (2)	0.067 (2)	0.069 (3)	−0.0099 (16)	0.001 (2)	−0.034 (2)
C12A	0.076 (2)	0.065 (2)	0.083 (2)	−0.0221 (18)	0.0026 (17)	−0.0255 (16)
C13A	0.074 (2)	0.092 (3)	0.106 (3)	−0.034 (2)	0.013 (2)	−0.032 (3)
C14A	0.078 (2)	0.078 (3)	0.107 (3)	−0.022 (2)	0.032 (2)	−0.030 (3)
C15A	0.105 (4)	0.078 (3)	0.087 (3)	−0.019 (2)	0.021 (2)	−0.015 (2)
C16A	0.102 (3)	0.073 (3)	0.079 (3)	−0.017 (2)	−0.004 (2)	−0.013 (2)
C17A	0.117 (3)	0.116 (3)	0.186 (5)	−0.060 (3)	0.058 (3)	−0.039 (3)
S18	0.0555 (4)	0.0707 (4)	0.0935 (5)	−0.0277 (3)	0.0104 (3)	−0.0363 (4)
O19	0.0731 (12)	0.0685 (12)	0.1222 (16)	−0.0136 (9)	−0.0070 (11)	−0.0259 (11)
O20	0.0596 (10)	0.1004 (14)	0.1271 (16)	−0.0433 (10)	0.0236 (10)	−0.0595 (12)
N21	0.0703 (13)	0.0884 (16)	0.0856 (15)	−0.0432 (12)	0.0144 (11)	−0.0431 (13)
C22	0.0731 (16)	0.0928 (19)	0.0541 (13)	−0.0455 (14)	0.0095 (11)	−0.0258 (12)
C23	0.0813 (18)	0.097 (2)	0.094 (2)	−0.0448 (17)	0.0275 (15)	−0.0361 (17)
C24	0.086 (2)	0.130 (3)	0.121 (3)	−0.050 (2)	0.037 (2)	−0.041 (2)
C25	0.103 (3)	0.156 (4)	0.114 (3)	−0.081 (3)	0.038 (2)	−0.039 (3)
C26	0.128 (3)	0.127 (3)	0.118 (3)	−0.090 (3)	0.038 (2)	−0.038 (2)
C27	0.104 (2)	0.095 (2)	0.095 (2)	−0.0550 (19)	0.0237 (17)	−0.0288 (17)
C28	0.0584 (12)	0.0515 (12)	0.0772 (14)	−0.0271 (10)	0.0205 (11)	−0.0319 (11)
C29	0.0732 (15)	0.0569 (14)	0.0936 (18)	−0.0358 (12)	0.0137 (13)	−0.0307 (13)
C30	0.0799 (17)	0.0657 (15)	0.0849 (18)	−0.0301 (13)	0.0103 (14)	−0.0219 (13)
C31	0.0737 (16)	0.099 (2)	0.0777 (16)	−0.0377 (15)	0.0207 (13)	−0.0498 (16)
C32	0.115 (2)	0.088 (2)	0.099 (2)	−0.0581 (18)	0.0183 (18)	−0.0549 (18)
C33	0.103 (2)	0.0588 (14)	0.0873 (18)	−0.0411 (14)	0.0128 (15)	−0.0343 (13)
C34	0.105 (3)	0.166 (4)	0.105 (2)	−0.048 (3)	0.005 (2)	−0.072 (3)

Geometric parameters (Å, º)

S1A—O2A	1.438 (3)	C13B—C14B	1.3900
S1A—O3A	1.443 (3)	C13B—H13B	0.9300
S1A—N4A	1.640 (3)	C14B—C15B	1.3900
S1A—C11A	1.761 (2)	C14B—C17B	1.537 (15)
N4A—C5	1.428 (4)	C15B—C16B	1.3900
N4A—H4A	0.8657	C15B—H15B	0.9300
S1B—O3B	1.407 (13)	C16B—H16B	0.9300
S1B—O2B	1.460 (15)	C17B—H17D	0.9600
S1B—N4B	1.611 (12)	C17B—H17E	0.9600
S1B—C11B	1.719 (14)	C17B—H17F	0.9600
N4B—C10	1.406 (13)	S18—O19	1.427 (2)
N4B—H4B	0.8773	S18—O20	1.4332 (19)
N4B—H10	0.8481	S18—N21	1.633 (2)
C5—C10	1.333 (4)	S18—C28	1.754 (2)
C5—C6	1.411 (5)	N21—C22	1.429 (3)
C6—C7	1.411 (6)	N21—H21	0.81 (3)
C6—H6	0.9300	C22—C23	1.370 (4)
C7—C8	1.364 (6)	C22—C27	1.378 (4)
C7—H7	0.9300	C23—C24	1.376 (4)
C8—C9	1.335 (6)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.372 (5)
C9—C10	1.352 (5)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.345 (6)
C10—H10	0.9333	C25—H25	0.9300
C11A—C12A	1.3900	C26—C27	1.396 (5)
C11A—C16A	1.3900	C26—H26	0.9300
C12A—C13A	1.3900	C27—H27	0.9300
C12A—H12A	0.9300	C28—C29	1.379 (3)
C13A—C14A	1.3900	C28—C33	1.386 (3)
C13A—H13A	0.9300	C29—C30	1.370 (4)
C14A—C15A	1.3900	C29—H29	0.9300
C14A—C17A	1.534 (5)	C30—C31	1.388 (4)
C15A—C16A	1.3900	C30—H30	0.9300
C15A—H15A	0.9300	C31—C32	1.379 (4)
C16A—H16A	0.9300	C31—C34	1.514 (4)
C17A—H17A	0.9600	C32—C33	1.379 (4)
C17A—H17B	0.9600	C32—H32	0.9300
C17A—H17C	0.9600	C33—H33	0.9300
C11B—C12B	1.3900	C34—H34A	0.9600
C11B—C16B	1.3900	C34—H34B	0.9600
C12B—C13B	1.3900	C34—H34C	0.9600
C12B—H12B	0.9300
O2A—S1A—O3A	118.41 (15)	C13B—C12B—H12B	120.0
O2A—S1A—N4A	105.11 (17)	C12B—C13B—C14B	120.0
O3A—S1A—N4A	108.96 (17)	C12B—C13B—H13B	120.0
O2A—S1A—C11A	107.0 (2)	C14B—C13B—H13B	120.0
O3A—S1A—C11A	109.04 (17)	C13B—C14B—C15B	120.0
N4A—S1A—C11A	107.90 (18)	C13B—C14B—C17B	118.3 (15)
C5—N4A—S1A	126.2 (2)	C15B—C14B—C17B	121.7 (15)
C5—N4A—H4A	126.2	C16B—C15B—C14B	120.0
S1A—N4A—H4A	92.8	C16B—C15B—H15B	120.0
O3B—S1B—O2B	122.3 (11)	C14B—C15B—H15B	120.0
O3B—S1B—N4B	105.4 (9)	C15B—C16B—C11B	120.0
O2B—S1B—N4B	110.0 (10)	C15B—C16B—H16B	120.0
O3B—S1B—C11B	110.2 (12)	C11B—C16B—H16B	120.0
O2B—S1B—C11B	106.1 (12)	C14B—C17B—H17D	109.5
N4B—S1B—C11B	100.8 (10)	C14B—C17B—H17E	109.5
C10—N4B—S1B	153.6 (12)	H17D—C17B—H17E	109.5
C10—N4B—H4B	112.8	C14B—C17B—H17F	109.5
S1B—N4B—H4B	92.6	H17D—C17B—H17F	109.5
C10—N4B—H10	40.1	H17E—C17B—H17F	109.5
S1B—N4B—H10	164.4	O19—S18—O20	119.00 (12)
H4B—N4B—H10	72.8	O19—S18—N21	108.65 (13)
C10—C5—C6	120.2 (4)	O20—S18—N21	104.34 (12)
C10—C5—N4A	122.7 (3)	O19—S18—C28	108.23 (12)
C6—C5—N4A	117.0 (4)	O20—S18—C28	109.50 (12)
C7—C6—C5	117.8 (4)	N21—S18—C28	106.42 (11)
C7—C6—H6	121.1	C22—N21—S18	123.11 (18)
C5—C6—H6	121.1	C22—N21—H21	118 (2)
C8—C7—C6	119.9 (4)	S18—N21—H21	106 (2)
C8—C7—H7	120.1	C23—C22—C27	119.5 (3)
C6—C7—H7	120.1	C23—C22—N21	118.1 (3)
C9—C8—C7	118.9 (4)	C27—C22—N21	122.4 (3)
C9—C8—H8	120.5	C22—C23—C24	120.6 (3)
C7—C8—H8	120.5	C22—C23—H23	119.7
C8—C9—C10	123.5 (5)	C24—C23—H23	119.7
C8—C9—H9	118.3	C25—C24—C23	120.2 (4)
C10—C9—H9	118.3	C25—C24—H24	119.9
C5—C10—C9	119.7 (4)	C23—C24—H24	119.9
C5—C10—N4B	84.4 (7)	C26—C25—C24	119.3 (3)
C9—C10—N4B	155.6 (7)	C26—C25—H25	120.4
C5—C10—H10	119.6	C24—C25—H25	120.4
C9—C10—H10	120.6	C25—C26—C27	121.7 (4)
N4B—C10—H10	35.8	C25—C26—H26	119.1
C12A—C11A—C16A	120.0	C27—C26—H26	119.1
C12A—C11A—S1A	118.6 (2)	C22—C27—C26	118.6 (4)
C16A—C11A—S1A	121.3 (2)	C22—C27—H27	120.7
C13A—C12A—C11A	120.0	C26—C27—H27	120.7
C13A—C12A—H12A	120.0	C29—C28—C33	120.0 (2)
C11A—C12A—H12A	120.0	C29—C28—S18	119.86 (17)
C12A—C13A—C14A	120.0	C33—C28—S18	120.02 (19)
C12A—C13A—H13A	120.0	C30—C29—C28	119.6 (2)
C14A—C13A—H13A	120.0	C30—C29—H29	120.2
C13A—C14A—C15A	120.0	C28—C29—H29	120.2
C13A—C14A—C17A	121.8 (4)	C29—C30—C31	121.7 (3)
C15A—C14A—C17A	118.2 (4)	C29—C30—H30	119.1
C16A—C15A—C14A	120.0	C31—C30—H30	119.1
C16A—C15A—H15A	120.0	C32—C31—C30	117.8 (3)
C14A—C15A—H15A	120.0	C32—C31—C34	121.1 (3)
C15A—C16A—C11A	120.0	C30—C31—C34	121.1 (3)
C15A—C16A—H16A	120.0	C33—C32—C31	121.5 (2)
C11A—C16A—H16A	120.0	C33—C32—H32	119.3
C14A—C17A—H17A	109.5	C31—C32—H32	119.3
C14A—C17A—H17B	109.5	C32—C33—C28	119.4 (3)
H17A—C17A—H17B	109.5	C32—C33—H33	120.3
C14A—C17A—H17C	109.5	C28—C33—H33	120.3
H17A—C17A—H17C	109.5	C31—C34—H34A	109.5
H17B—C17A—H17C	109.5	C31—C34—H34B	109.5
C12B—C11B—C16B	120.0	H34A—C34—H34B	109.5
C12B—C11B—S1B	121.6 (15)	C31—C34—H34C	109.5
C16B—C11B—S1B	117.6 (15)	H34A—C34—H34C	109.5
C11B—C12B—C13B	120.0	H34B—C34—H34C	109.5
C11B—C12B—H12B	120.0
O2A—S1A—N4A—C5	−176.5 (3)	O2B—S1B—C11B—C16B	−1.7 (17)
O3A—S1A—N4A—C5	55.6 (3)	N4B—S1B—C11B—C16B	−116.4 (13)
C11A—S1A—N4A—C5	−62.7 (3)	C16B—C11B—C12B—C13B	0.0
O3B—S1B—N4B—C10	174 (2)	S1B—C11B—C12B—C13B	169.5 (18)
O2B—S1B—N4B—C10	−53 (3)	C11B—C12B—C13B—C14B	0.0
C11B—S1B—N4B—C10	59 (3)	C12B—C13B—C14B—C15B	0.0
S1A—N4A—C5—C10	−30.2 (4)	C12B—C13B—C14B—C17B	178 (2)
S1A—N4A—C5—C6	153.4 (3)	C13B—C14B—C15B—C16B	0.0
C10—C5—C6—C7	−3.1 (6)	C17B—C14B—C15B—C16B	−178 (2)
N4A—C5—C6—C7	173.4 (4)	C14B—C15B—C16B—C11B	0.0
C5—C6—C7—C8	2.8 (7)	C12B—C11B—C16B—C15B	0.0
C6—C7—C8—C9	−1.0 (8)	S1B—C11B—C16B—C15B	−169.9 (18)
C7—C8—C9—C10	−0.6 (8)	O19—S18—N21—C22	65.2 (2)
C6—C5—C10—C9	1.6 (5)	O20—S18—N21—C22	−166.9 (2)
N4A—C5—C10—C9	−174.7 (3)	C28—S18—N21—C22	−51.1 (2)
C6—C5—C10—N4B	−174.3 (7)	S18—N21—C22—C23	138.1 (2)
N4A—C5—C10—N4B	9.4 (7)	S18—N21—C22—C27	−43.3 (3)
C8—C9—C10—C5	0.3 (7)	C27—C22—C23—C24	−0.4 (4)
C8—C9—C10—N4B	170.4 (17)	N21—C22—C23—C24	178.2 (3)
S1B—N4B—C10—C5	23 (3)	C22—C23—C24—C25	1.3 (5)
S1B—N4B—C10—C9	−147.9 (17)	C23—C24—C25—C26	−0.4 (6)
O2A—S1A—C11A—C12A	−137.1 (2)	C24—C25—C26—C27	−1.4 (6)
O3A—S1A—C11A—C12A	−7.9 (3)	C23—C22—C27—C26	−1.3 (4)
N4A—S1A—C11A—C12A	110.3 (2)	N21—C22—C27—C26	−179.9 (3)
O2A—S1A—C11A—C16A	46.7 (3)	C25—C26—C27—C22	2.2 (6)
O3A—S1A—C11A—C16A	175.8 (2)	O19—S18—C28—C29	169.83 (19)
N4A—S1A—C11A—C16A	−66.0 (3)	O20—S18—C28—C29	38.7 (2)
C16A—C11A—C12A—C13A	0.0	N21—S18—C28—C29	−73.6 (2)
S1A—C11A—C12A—C13A	−176.3 (3)	O19—S18—C28—C33	−14.0 (2)
C11A—C12A—C13A—C14A	0.0	O20—S18—C28—C33	−145.2 (2)
C12A—C13A—C14A—C15A	0.0	N21—S18—C28—C33	102.6 (2)
C12A—C13A—C14A—C17A	177.7 (4)	C33—C28—C29—C30	0.0 (4)
C13A—C14A—C15A—C16A	0.0	S18—C28—C29—C30	176.11 (19)
C17A—C14A—C15A—C16A	−177.8 (4)	C28—C29—C30—C31	−0.6 (4)
C14A—C15A—C16A—C11A	0.0	C29—C30—C31—C32	1.0 (4)
C12A—C11A—C16A—C15A	0.0	C29—C30—C31—C34	−177.1 (3)
S1A—C11A—C16A—C15A	176.2 (3)	C30—C31—C32—C33	−0.9 (4)
O3B—S1B—C11B—C12B	−37.1 (15)	C34—C31—C32—C33	177.2 (3)
O2B—S1B—C11B—C12B	−171.4 (14)	C31—C32—C33—C28	0.3 (4)
N4B—S1B—C11B—C12B	73.8 (14)	C29—C28—C33—C32	0.2 (4)
O3B—S1B—C11B—C16B	132.6 (14)	S18—C28—C33—C32	−176.0 (2)

(Compound_18_Manual)

Crystal data

C13H13NO2S	Z = 4
Mr = 247.30	F(000) = 520
Triclinic, P1	Dx = 1.264 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2890 (11) Å	Cell parameters from 5366 reflections
b = 11.0563 (12) Å	θ = 2.5–24.7°
c = 13.4402 (15) Å	µ = 0.24 mm^−1
α = 67.823 (3)°	T = 300 K
β = 87.573 (4)°	Plate, colorless
γ = 67.616 (3)°	0.32 × 0.30 × 0.18 mm
V = 1299.9 (2) Å^3

Data collection

Bruker SMART X2S diffractometer	4544 independent reflections
Radiation source: micro-focus sealed tube	3364 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.036
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.890, Tmax = 0.890	k = −13→13
12851 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1035P)^2 + 0.2796P] where P = (Fo^2 + 2Fc^2)/3
4544 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 0.25 e Å^−3
30 restraints	Δρmin = −0.40 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.20015 (11)	0.42407 (8)	0.11615 (9)	0.0804 (3)	0.85
O2A	0.1771 (3)	0.3842 (3)	0.0303 (3)	0.1086 (9)	0.85
O3A	0.2814 (3)	0.3134 (3)	0.2163 (2)	0.0912 (8)	0.85
N4A	0.0413 (3)	0.5097 (3)	0.1408 (3)	0.0875 (8)	0.85
H4A	0.0075	0.5485	0.0732	0.131*	0.85
S1B	0.2538 (7)	0.3989 (8)	0.1617 (6)	0.0738 (13)*	0.15
O2B	0.1418 (18)	0.403 (2)	0.0960 (15)	0.108 (5)*	0.15
O3B	0.3793 (16)	0.2769 (15)	0.2076 (12)	0.101 (5)*	0.15
N4B	0.1907 (16)	0.4415 (16)	0.2611 (11)	0.084 (4)*	0.15
H4B	0.2677	0.3802	0.3054	0.126*	0.15
C5	0.0088 (4)	0.5769 (3)	0.2161 (3)	0.0946 (10)
C6	−0.1234 (5)	0.6920 (5)	0.1949 (4)	0.1306 (13)
H6	−0.1820	0.7284	0.1308	0.157*
C7	−0.1638 (5)	0.7499 (5)	0.2741 (4)	0.1409 (16)
H7	−0.2519	0.8231	0.2641	0.169*
C8	−0.0732 (6)	0.6984 (5)	0.3653 (4)	0.1407 (16)
H8	−0.0981	0.7369	0.4174	0.169*
C9	0.0519 (5)	0.5918 (5)	0.3785 (4)	0.1245 (13)
H9	0.1132	0.5580	0.4406	0.149*
C10	0.0941 (4)	0.5305 (4)	0.3062 (4)	0.1085 (11)
H10	0.1809	0.4537	0.3200	0.130*
C11A	0.2814 (4)	0.5458 (4)	0.0635 (3)	0.0717 (15)	0.85
C12A	0.3936 (4)	0.5321 (3)	0.1267 (2)	0.0774 (12)	0.85
H12A	0.4279	0.4566	0.1936	0.093*	0.85
C13A	0.4547 (3)	0.6314 (4)	0.0901 (3)	0.0926 (11)	0.85
H13A	0.5298	0.6222	0.1324	0.111*	0.85
C14A	0.4036 (3)	0.7443 (3)	−0.0098 (4)	0.0930 (11)	0.85
C15A	0.2913 (4)	0.7579 (3)	−0.0731 (2)	0.1015 (13)	0.85
H15A	0.2571	0.8335	−0.1399	0.122*	0.85
C16A	0.2303 (4)	0.6587 (4)	−0.0364 (3)	0.0955 (15)	0.85
H16A	0.1552	0.6678	−0.0788	0.115*	0.85
C17A	0.4640 (6)	0.8593 (5)	−0.0516 (5)	0.143 (2)	0.85
H17A	0.4943	0.8731	0.0084	0.215*	0.85
H17B	0.3923	0.9468	−0.0996	0.215*	0.85
H17C	0.5432	0.8300	−0.0898	0.215*	0.85
C11B	0.293 (3)	0.543 (2)	0.0859 (16)	0.044 (5)*	0.15
C12B	0.408 (3)	0.562 (2)	0.1180 (12)	0.094 (10)*	0.15
H12B	0.4566	0.5048	0.1869	0.113*	0.15
C13B	0.450 (2)	0.665 (3)	0.0470 (14)	0.084 (8)*	0.15
H13B	0.5270	0.6781	0.0685	0.101*	0.15
C14B	0.377 (2)	0.750 (2)	−0.0560 (12)	0.079 (7)*	0.15
C15B	0.262 (2)	0.732 (2)	−0.0880 (12)	0.079 (7)*	0.15
H15B	0.2129	0.7884	−0.1569	0.095*	0.15
C16B	0.220 (2)	0.628 (3)	−0.0171 (18)	0.063 (6)*	0.15
H16B	0.1425	0.6152	−0.0385	0.076*	0.15
C17B	0.424 (3)	0.867 (2)	−0.1305 (18)	0.108 (8)*	0.15
H17D	0.3813	0.9504	−0.1142	0.162*	0.15
H17E	0.3946	0.8905	−0.2046	0.162*	0.15
H17F	0.5251	0.8339	−0.1192	0.162*	0.15
S18	0.47516 (6)	0.21883 (7)	0.50060 (6)	0.0710 (2)
O19	0.4129 (2)	0.3703 (2)	0.45041 (18)	0.0956 (6)
O20	0.38487 (18)	0.1421 (2)	0.52602 (18)	0.0875 (6)
N21	0.5786 (2)	0.1583 (3)	0.41986 (19)	0.0748 (6)
H21	0.583 (3)	0.078 (3)	0.435 (2)	0.090*
C22	0.7038 (3)	0.1843 (3)	0.39199 (18)	0.0702 (7)
C23	0.8225 (3)	0.0741 (3)	0.3889 (2)	0.0882 (8)
H23	0.8203	−0.0149	0.4068	0.106*
C24	0.9449 (4)	0.0939 (5)	0.3598 (3)	0.1137 (12)
H24	1.0243	0.0189	0.3566	0.136*
C25	0.9503 (4)	0.2241 (5)	0.3353 (3)	0.1194 (13)
H25	1.0332	0.2376	0.3160	0.143*
C26	0.8345 (5)	0.3319 (5)	0.3397 (3)	0.1155 (12)
H26	0.8389	0.4194	0.3247	0.139*
C27	0.7077 (4)	0.3158 (4)	0.3662 (3)	0.0957 (9)
H27	0.6276	0.3922	0.3664	0.115*
C28	0.5846 (2)	0.1698 (2)	0.61768 (19)	0.0588 (5)
C29	0.6400 (3)	0.0302 (3)	0.6903 (2)	0.0710 (6)
H29	0.6151	−0.0370	0.6797	0.085*
C30	0.7321 (3)	−0.0090 (3)	0.7783 (2)	0.0788 (7)
H30	0.7685	−0.1032	0.8273	0.095*
C31	0.7725 (3)	0.0881 (3)	0.7960 (2)	0.0777 (7)
C32	0.7150 (3)	0.2275 (3)	0.7228 (3)	0.0888 (9)
H32	0.7396	0.2946	0.7337	0.107*
C33	0.6219 (3)	0.2695 (3)	0.6339 (2)	0.0781 (7)
H33	0.5846	0.3638	0.5852	0.094*
C34	0.8796 (4)	0.0418 (5)	0.8906 (3)	0.1205 (13)
H34A	0.8801	0.1241	0.8990	0.181*
H34B	0.9720	−0.0118	0.8775	0.181*
H34C	0.8546	−0.0162	0.9554	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0732 (5)	0.0573 (5)	0.1042 (7)	−0.0142 (4)	−0.0176 (5)	−0.0336 (5)
O2A	0.0998 (18)	0.0889 (17)	0.139 (2)	−0.0140 (14)	−0.0282 (16)	−0.0658 (17)
O3A	0.0983 (19)	0.0493 (13)	0.1012 (17)	−0.0179 (12)	−0.0221 (14)	−0.0115 (13)
N4A	0.0702 (16)	0.0789 (18)	0.112 (2)	−0.0297 (14)	−0.0040 (15)	−0.0342 (16)
C5	0.091 (2)	0.0746 (19)	0.132 (3)	−0.0475 (17)	0.043 (2)	−0.0422 (19)
C6	0.140 (3)	0.107 (3)	0.118 (3)	−0.042 (3)	0.009 (3)	−0.023 (2)
C7	0.138 (4)	0.103 (3)	0.137 (4)	−0.006 (3)	0.032 (3)	−0.044 (3)
C8	0.159 (4)	0.117 (3)	0.121 (3)	−0.023 (3)	0.033 (3)	−0.053 (3)
C9	0.124 (3)	0.122 (3)	0.135 (3)	−0.048 (3)	0.041 (3)	−0.060 (3)
C10	0.086 (2)	0.111 (3)	0.149 (3)	−0.049 (2)	0.030 (2)	−0.064 (3)
C11A	0.071 (2)	0.067 (2)	0.069 (3)	−0.0099 (16)	0.001 (2)	−0.034 (2)
C12A	0.076 (2)	0.065 (2)	0.083 (2)	−0.0221 (18)	0.0026 (17)	−0.0255 (16)
C13A	0.074 (2)	0.092 (3)	0.106 (3)	−0.034 (2)	0.013 (2)	−0.032 (3)
C14A	0.078 (2)	0.078 (3)	0.107 (3)	−0.022 (2)	0.032 (2)	−0.030 (3)
C15A	0.105 (4)	0.078 (3)	0.087 (3)	−0.019 (2)	0.021 (2)	−0.015 (2)
C16A	0.102 (3)	0.073 (3)	0.079 (3)	−0.017 (2)	−0.004 (2)	−0.013 (2)
C17A	0.117 (3)	0.116 (3)	0.186 (5)	−0.060 (3)	0.058 (3)	−0.039 (3)
S18	0.0555 (4)	0.0707 (4)	0.0935 (5)	−0.0277 (3)	0.0104 (3)	−0.0363 (4)
O19	0.0731 (12)	0.0685 (12)	0.1222 (16)	−0.0136 (9)	−0.0070 (11)	−0.0259 (11)
O20	0.0596 (10)	0.1004 (14)	0.1271 (16)	−0.0433 (10)	0.0236 (10)	−0.0595 (12)
N21	0.0703 (13)	0.0884 (16)	0.0856 (15)	−0.0432 (12)	0.0144 (11)	−0.0431 (13)
C22	0.0731 (16)	0.0928 (19)	0.0541 (13)	−0.0455 (14)	0.0095 (11)	−0.0258 (12)
C23	0.0813 (18)	0.097 (2)	0.094 (2)	−0.0448 (17)	0.0275 (15)	−0.0361 (17)
C24	0.086 (2)	0.130 (3)	0.121 (3)	−0.050 (2)	0.037 (2)	−0.041 (2)
C25	0.103 (3)	0.156 (4)	0.114 (3)	−0.081 (3)	0.038 (2)	−0.039 (3)
C26	0.128 (3)	0.127 (3)	0.118 (3)	−0.090 (3)	0.038 (2)	−0.038 (2)
C27	0.104 (2)	0.095 (2)	0.095 (2)	−0.0550 (19)	0.0237 (17)	−0.0288 (17)
C28	0.0584 (12)	0.0515 (12)	0.0772 (14)	−0.0271 (10)	0.0205 (11)	−0.0319 (11)
C29	0.0732 (15)	0.0569 (14)	0.0936 (18)	−0.0358 (12)	0.0137 (13)	−0.0307 (13)
C30	0.0799 (17)	0.0657 (15)	0.0849 (18)	−0.0301 (13)	0.0103 (14)	−0.0219 (13)
C31	0.0737 (16)	0.099 (2)	0.0777 (16)	−0.0377 (15)	0.0207 (13)	−0.0498 (16)
C32	0.115 (2)	0.088 (2)	0.099 (2)	−0.0581 (18)	0.0183 (18)	−0.0549 (18)
C33	0.103 (2)	0.0588 (14)	0.0873 (18)	−0.0411 (14)	0.0128 (15)	−0.0343 (13)
C34	0.105 (3)	0.166 (4)	0.105 (2)	−0.048 (3)	0.005 (2)	−0.072 (3)

Geometric parameters (Å, º)

S1A—O2A	1.438 (3)	C13B—C14B	1.3900
S1A—O3A	1.443 (3)	C13B—H13B	0.9300
S1A—N4A	1.640 (3)	C14B—C15B	1.3900
S1A—C11A	1.761 (2)	C14B—C17B	1.537 (15)
N4A—C5	1.428 (4)	C15B—C16B	1.3900
N4A—H4A	0.8657	C15B—H15B	0.9300
S1B—O3B	1.407 (13)	C16B—H16B	0.9300
S1B—O2B	1.460 (15)	C17B—H17D	0.9600
S1B—N4B	1.611 (12)	C17B—H17E	0.9600
S1B—C11B	1.719 (14)	C17B—H17F	0.9600
N4B—C10	1.406 (13)	S18—O19	1.427 (2)
N4B—H4B	0.8773	S18—O20	1.4332 (19)
N4B—H10	0.8481	S18—N21	1.633 (2)
C5—C10	1.333 (4)	S18—C28	1.754 (2)
C5—C6	1.411 (5)	N21—C22	1.429 (3)
C6—C7	1.411 (6)	N21—H21	0.81 (3)
C6—H6	0.9300	C22—C23	1.370 (4)
C7—C8	1.364 (6)	C22—C27	1.378 (4)
C7—H7	0.9300	C23—C24	1.376 (4)
C8—C9	1.335 (6)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.372 (5)
C9—C10	1.352 (5)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.345 (6)
C10—H10	0.9333	C25—H25	0.9300
C11A—C12A	1.3900	C26—C27	1.396 (5)
C11A—C16A	1.3900	C26—H26	0.9300
C12A—C13A	1.3900	C27—H27	0.9300
C12A—H12A	0.9300	C28—C29	1.379 (3)
C13A—C14A	1.3900	C28—C33	1.386 (3)
C13A—H13A	0.9300	C29—C30	1.370 (4)
C14A—C15A	1.3900	C29—H29	0.9300
C14A—C17A	1.534 (5)	C30—C31	1.388 (4)
C15A—C16A	1.3900	C30—H30	0.9300
C15A—H15A	0.9300	C31—C32	1.379 (4)
C16A—H16A	0.9300	C31—C34	1.514 (4)
C17A—H17A	0.9600	C32—C33	1.379 (4)
C17A—H17B	0.9600	C32—H32	0.9300
C17A—H17C	0.9600	C33—H33	0.9300
C11B—C12B	1.3900	C34—H34A	0.9600
C11B—C16B	1.3900	C34—H34B	0.9600
C12B—C13B	1.3900	C34—H34C	0.9600
C12B—H12B	0.9300
O2A—S1A—O3A	118.41 (15)	C13B—C12B—H12B	120.0
O2A—S1A—N4A	105.11 (17)	C12B—C13B—C14B	120.0
O3A—S1A—N4A	108.96 (17)	C12B—C13B—H13B	120.0
O2A—S1A—C11A	107.0 (2)	C14B—C13B—H13B	120.0
O3A—S1A—C11A	109.04 (17)	C13B—C14B—C15B	120.0
N4A—S1A—C11A	107.90 (18)	C13B—C14B—C17B	118.3 (15)
C5—N4A—S1A	126.2 (2)	C15B—C14B—C17B	121.7 (15)
C5—N4A—H4A	126.2	C16B—C15B—C14B	120.0
S1A—N4A—H4A	92.8	C16B—C15B—H15B	120.0
O3B—S1B—O2B	122.3 (11)	C14B—C15B—H15B	120.0
O3B—S1B—N4B	105.4 (9)	C15B—C16B—C11B	120.0
O2B—S1B—N4B	110.0 (10)	C15B—C16B—H16B	120.0
O3B—S1B—C11B	110.2 (12)	C11B—C16B—H16B	120.0
O2B—S1B—C11B	106.1 (12)	C14B—C17B—H17D	109.5
N4B—S1B—C11B	100.8 (10)	C14B—C17B—H17E	109.5
C10—N4B—S1B	153.6 (12)	H17D—C17B—H17E	109.5
C10—N4B—H4B	112.8	C14B—C17B—H17F	109.5
S1B—N4B—H4B	92.6	H17D—C17B—H17F	109.5
C10—N4B—H10	40.1	H17E—C17B—H17F	109.5
S1B—N4B—H10	164.4	O19—S18—O20	119.00 (12)
H4B—N4B—H10	72.8	O19—S18—N21	108.65 (13)
C10—C5—C6	120.2 (4)	O20—S18—N21	104.34 (12)
C10—C5—N4A	122.7 (3)	O19—S18—C28	108.23 (12)
C6—C5—N4A	117.0 (4)	O20—S18—C28	109.50 (12)
C7—C6—C5	117.8 (4)	N21—S18—C28	106.42 (11)
C7—C6—H6	121.1	C22—N21—S18	123.11 (18)
C5—C6—H6	121.1	C22—N21—H21	118 (2)
C8—C7—C6	119.9 (4)	S18—N21—H21	106 (2)
C8—C7—H7	120.1	C23—C22—C27	119.5 (3)
C6—C7—H7	120.1	C23—C22—N21	118.1 (3)
C9—C8—C7	118.9 (4)	C27—C22—N21	122.4 (3)
C9—C8—H8	120.5	C22—C23—C24	120.6 (3)
C7—C8—H8	120.5	C22—C23—H23	119.7
C8—C9—C10	123.5 (5)	C24—C23—H23	119.7
C8—C9—H9	118.3	C25—C24—C23	120.2 (4)
C10—C9—H9	118.3	C25—C24—H24	119.9
C5—C10—C9	119.7 (4)	C23—C24—H24	119.9
C5—C10—N4B	84.4 (7)	C26—C25—C24	119.3 (3)
C9—C10—N4B	155.6 (7)	C26—C25—H25	120.4
C5—C10—H10	119.6	C24—C25—H25	120.4
C9—C10—H10	120.6	C25—C26—C27	121.7 (4)
N4B—C10—H10	35.8	C25—C26—H26	119.1
C12A—C11A—C16A	120.0	C27—C26—H26	119.1
C12A—C11A—S1A	118.6 (2)	C22—C27—C26	118.6 (4)
C16A—C11A—S1A	121.3 (2)	C22—C27—H27	120.7
C13A—C12A—C11A	120.0	C26—C27—H27	120.7
C13A—C12A—H12A	120.0	C29—C28—C33	120.0 (2)
C11A—C12A—H12A	120.0	C29—C28—S18	119.86 (17)
C12A—C13A—C14A	120.0	C33—C28—S18	120.02 (19)
C12A—C13A—H13A	120.0	C30—C29—C28	119.6 (2)
C14A—C13A—H13A	120.0	C30—C29—H29	120.2
C13A—C14A—C15A	120.0	C28—C29—H29	120.2
C13A—C14A—C17A	121.8 (4)	C29—C30—C31	121.7 (3)
C15A—C14A—C17A	118.2 (4)	C29—C30—H30	119.1
C16A—C15A—C14A	120.0	C31—C30—H30	119.1
C16A—C15A—H15A	120.0	C32—C31—C30	117.8 (3)
C14A—C15A—H15A	120.0	C32—C31—C34	121.1 (3)
C15A—C16A—C11A	120.0	C30—C31—C34	121.1 (3)
C15A—C16A—H16A	120.0	C33—C32—C31	121.5 (2)
C11A—C16A—H16A	120.0	C33—C32—H32	119.3
C14A—C17A—H17A	109.5	C31—C32—H32	119.3
C14A—C17A—H17B	109.5	C32—C33—C28	119.4 (3)
H17A—C17A—H17B	109.5	C32—C33—H33	120.3
C14A—C17A—H17C	109.5	C28—C33—H33	120.3
H17A—C17A—H17C	109.5	C31—C34—H34A	109.5
H17B—C17A—H17C	109.5	C31—C34—H34B	109.5
C12B—C11B—C16B	120.0	H34A—C34—H34B	109.5
C12B—C11B—S1B	121.6 (15)	C31—C34—H34C	109.5
C16B—C11B—S1B	117.6 (15)	H34A—C34—H34C	109.5
C11B—C12B—C13B	120.0	H34B—C34—H34C	109.5
C11B—C12B—H12B	120.0
O2A—S1A—N4A—C5	−176.5 (3)	O2B—S1B—C11B—C16B	−1.7 (17)
O3A—S1A—N4A—C5	55.6 (3)	N4B—S1B—C11B—C16B	−116.4 (13)
C11A—S1A—N4A—C5	−62.7 (3)	C16B—C11B—C12B—C13B	0.0
O3B—S1B—N4B—C10	174 (2)	S1B—C11B—C12B—C13B	169.5 (18)
O2B—S1B—N4B—C10	−53 (3)	C11B—C12B—C13B—C14B	0.0
C11B—S1B—N4B—C10	59 (3)	C12B—C13B—C14B—C15B	0.0
S1A—N4A—C5—C10	−30.2 (4)	C12B—C13B—C14B—C17B	178 (2)
S1A—N4A—C5—C6	153.4 (3)	C13B—C14B—C15B—C16B	0.0
C10—C5—C6—C7	−3.1 (6)	C17B—C14B—C15B—C16B	−178 (2)
N4A—C5—C6—C7	173.4 (4)	C14B—C15B—C16B—C11B	0.0
C5—C6—C7—C8	2.8 (7)	C12B—C11B—C16B—C15B	0.0
C6—C7—C8—C9	−1.0 (8)	S1B—C11B—C16B—C15B	−169.9 (18)
C7—C8—C9—C10	−0.6 (8)	O19—S18—N21—C22	65.2 (2)
C6—C5—C10—C9	1.6 (5)	O20—S18—N21—C22	−166.9 (2)
N4A—C5—C10—C9	−174.7 (3)	C28—S18—N21—C22	−51.1 (2)
C6—C5—C10—N4B	−174.3 (7)	S18—N21—C22—C23	138.1 (2)
N4A—C5—C10—N4B	9.4 (7)	S18—N21—C22—C27	−43.3 (3)
C8—C9—C10—C5	0.3 (7)	C27—C22—C23—C24	−0.4 (4)
C8—C9—C10—N4B	170.4 (17)	N21—C22—C23—C24	178.2 (3)
S1B—N4B—C10—C5	23 (3)	C22—C23—C24—C25	1.3 (5)
S1B—N4B—C10—C9	−147.9 (17)	C23—C24—C25—C26	−0.4 (6)
O2A—S1A—C11A—C12A	−137.1 (2)	C24—C25—C26—C27	−1.4 (6)
O3A—S1A—C11A—C12A	−7.9 (3)	C23—C22—C27—C26	−1.3 (4)
N4A—S1A—C11A—C12A	110.3 (2)	N21—C22—C27—C26	−179.9 (3)
O2A—S1A—C11A—C16A	46.7 (3)	C25—C26—C27—C22	2.2 (6)
O3A—S1A—C11A—C16A	175.8 (2)	O19—S18—C28—C29	169.83 (19)
N4A—S1A—C11A—C16A	−66.0 (3)	O20—S18—C28—C29	38.7 (2)
C16A—C11A—C12A—C13A	0.0	N21—S18—C28—C29	−73.6 (2)
S1A—C11A—C12A—C13A	−176.3 (3)	O19—S18—C28—C33	−14.0 (2)
C11A—C12A—C13A—C14A	0.0	O20—S18—C28—C33	−145.2 (2)
C12A—C13A—C14A—C15A	0.0	N21—S18—C28—C33	102.6 (2)
C12A—C13A—C14A—C17A	177.7 (4)	C33—C28—C29—C30	0.0 (4)
C13A—C14A—C15A—C16A	0.0	S18—C28—C29—C30	176.11 (19)
C17A—C14A—C15A—C16A	−177.8 (4)	C28—C29—C30—C31	−0.6 (4)
C14A—C15A—C16A—C11A	0.0	C29—C30—C31—C32	1.0 (4)
C12A—C11A—C16A—C15A	0.0	C29—C30—C31—C34	−177.1 (3)
S1A—C11A—C16A—C15A	176.2 (3)	C30—C31—C32—C33	−0.9 (4)
O3B—S1B—C11B—C12B	−37.1 (15)	C34—C31—C32—C33	177.2 (3)
O2B—S1B—C11B—C12B	−171.4 (14)	C31—C32—C33—C28	0.3 (4)
N4B—S1B—C11B—C12B	73.8 (14)	C29—C28—C33—C32	0.2 (4)
O3B—S1B—C11B—C16B	132.6 (14)	S18—C28—C33—C32	−176.0 (2)

(Compound_18_X2S)

Crystal data

C13H12NO2S·'C13H12NO2S'	Z = 4
Mr = 246.30	F(000) = 516
Triclinic, P1	Dx = 1.258 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2890 (11) Å	Cell parameters from 5366 reflections
b = 11.0563 (12) Å	θ = 2.5–24.7°
c = 13.4402 (15) Å	µ = 0.24 mm^−1
α = 67.823 (3)°	T = 300 K
β = 87.573 (4)°	Plate, colorless
γ = 67.616 (3)°	0.32 × 0.30 × 0.18 mm
V = 1299.9 (2) Å^3

Data collection

Bruker SMART X2S diffractometer	4545 independent reflections
Radiation source: micro-focus sealed tube	3364 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.036
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS)	h = −12→12
Tmin = 0.890, Tmax = 0.890	k = −13→13
12857 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.227	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1107P)^2 + 1.0378P] where P = (Fo^2 + 2Fc^2)/3
4545 reflections	(Δ/σ)max = 0.143
317 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.79831 (13)	0.57698 (11)	0.88214 (11)	0.0918 (4)
S2	0.52478 (9)	0.78104 (10)	0.49944 (8)	0.0697 (3)
O1	0.7163 (4)	0.6829 (3)	0.7873 (3)	0.1073 (11)
O2	0.8242 (4)	0.6160 (4)	0.9678 (4)	0.1296 (15)
O3	0.6151 (3)	0.8583 (3)	0.4736 (3)	0.0858 (8)
O4	0.5872 (3)	0.6296 (3)	0.5500 (3)	0.0935 (9)
C13	0.5389 (8)	0.1403 (7)	1.0562 (8)	0.186 (4)
H13A	0.4397	0.1812	1.0314	0.279*
H13B	0.5525	0.1004	1.1339	0.279*
H13C	0.5873	0.0670	1.0301	0.279*
C2	0.7088 (7)	0.2478 (6)	1.0726 (4)	0.1151 (19)
H2	0.7434	0.1748	1.1406	0.138*
C1	0.5981 (6)	0.2550 (5)	1.0137 (5)	0.1072 (17)
C26	0.7708 (5)	0.3463 (5)	1.0336 (4)	0.0965 (14)
H26	0.8462	0.3396	1.0741	0.116*
C3	0.7170 (4)	0.4541 (4)	0.9329 (3)	0.0707 (9)
N1	0.9588 (4)	0.4898 (5)	0.8599 (4)	0.1038 (13)
C4	0.9911 (5)	0.4226 (5)	0.7834 (5)	0.0920 (14)
C5	0.9062 (6)	0.4700 (6)	0.6953 (5)	0.1073 (16)
H5	0.8186	0.5448	0.6829	0.129*
C6	0.9472 (7)	0.4084 (7)	0.6212 (5)	0.1229 (18)
H6	0.8856	0.4415	0.5594	0.147*
C7	1.0751 (9)	0.3005 (7)	0.6359 (6)	0.140 (2)
H7	1.1015	0.2618	0.5840	0.168*
C8	1.1231 (7)	0.3085 (7)	0.8056 (5)	0.130 (2)
H8	1.1814	0.2728	0.8697	0.156*
C9	1.1638 (8)	0.2501 (7)	0.7268 (6)	0.140 (2)
H9	1.2519	0.1766	0.7374	0.168*
C10	0.6054 (4)	0.4643 (4)	0.8753 (4)	0.0830 (11)
H10	0.5685	0.5389	0.8083	0.100*
C11	0.5463 (5)	0.3654 (6)	0.9149 (5)	0.1037 (15)
H11	0.4704	0.3734	0.8741	0.124*
C12	0.1212 (6)	0.9585 (7)	0.1090 (4)	0.1196 (19)
H12A	0.1239	0.8764	0.0984	0.179*
H12B	0.1436	1.0203	0.0448	0.179*
H12C	0.0282	1.0081	0.1236	0.179*
C14	0.2283 (4)	0.9120 (5)	0.2037 (3)	0.0752 (10)
C15	0.2857 (5)	0.7728 (5)	0.2767 (4)	0.0869 (12)
H15	0.2615	0.7057	0.2653	0.104*
C16	0.3777 (5)	0.7304 (4)	0.3658 (3)	0.0781 (11)
H16	0.4145	0.6361	0.4145	0.094*
C17	0.4155 (3)	0.8304 (3)	0.3824 (3)	0.0573 (8)
N2	0.4216 (4)	0.8407 (5)	0.5805 (3)	0.0737 (9)
C18	0.2963 (4)	0.8157 (4)	0.6082 (3)	0.0693 (9)
C19	0.1779 (5)	0.9257 (5)	0.6117 (4)	0.0874 (12)
H19	0.1804	1.0145	0.5942	0.105*
C20	0.0554 (5)	0.9062 (7)	0.6407 (4)	0.1120 (17)
H20	−0.0235	0.9812	0.6444	0.134*
C21	0.0489 (7)	0.7766 (8)	0.6643 (5)	0.1175 (19)
H21	−0.0344	0.7637	0.6827	0.141*
C22	0.2679 (4)	1.0088 (4)	0.2214 (3)	0.0778 (10)
H22	0.2314	1.1029	0.1723	0.093*
C23	0.3601 (4)	0.9697 (4)	0.3098 (3)	0.0693 (9)
H23	0.3849	1.0369	0.3204	0.083*
C24	0.1651 (7)	0.6686 (7)	0.6603 (5)	0.1138 (17)
H24	0.1608	0.5809	0.6756	0.137*
C25	0.2919 (5)	0.6846 (5)	0.6337 (4)	0.0942 (13)
H25	0.3719	0.6081	0.6334	0.113*
H2A	0.408 (5)	0.915 (4)	0.564 (3)	0.074 (15)*
H1A	1.031 (6)	0.452 (6)	0.921 (5)	0.14 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0889 (8)	0.0610 (6)	0.1194 (10)	−0.0190 (5)	−0.0020 (7)	−0.0382 (6)
S2	0.0541 (5)	0.0695 (6)	0.0928 (7)	−0.0273 (4)	0.0101 (4)	−0.0363 (5)
O1	0.112 (2)	0.087 (2)	0.119 (3)	−0.0316 (18)	−0.020 (2)	−0.0415 (19)
O2	0.115 (3)	0.101 (2)	0.177 (4)	−0.017 (2)	−0.042 (2)	−0.078 (3)
O3	0.0575 (14)	0.098 (2)	0.126 (2)	−0.0422 (14)	0.0233 (14)	−0.0584 (18)
O4	0.0711 (17)	0.0682 (17)	0.119 (2)	−0.0140 (13)	−0.0078 (16)	−0.0252 (16)
C13	0.130 (5)	0.115 (5)	0.287 (10)	−0.060 (4)	0.100 (6)	−0.047 (6)
C2	0.121 (4)	0.081 (3)	0.086 (3)	−0.007 (3)	0.030 (3)	−0.007 (3)
C1	0.083 (3)	0.082 (3)	0.139 (5)	−0.026 (3)	0.045 (3)	−0.035 (3)
C26	0.095 (3)	0.081 (3)	0.085 (3)	−0.012 (2)	−0.005 (2)	−0.023 (2)
C3	0.066 (2)	0.061 (2)	0.076 (2)	−0.0111 (17)	0.0049 (18)	−0.0314 (18)
N1	0.080 (2)	0.095 (3)	0.134 (4)	−0.036 (2)	−0.007 (2)	−0.039 (3)
C4	0.092 (3)	0.075 (3)	0.127 (4)	−0.049 (3)	0.044 (3)	−0.044 (3)
C5	0.086 (3)	0.112 (4)	0.141 (5)	−0.050 (3)	0.028 (3)	−0.058 (4)
C6	0.124 (5)	0.120 (5)	0.128 (5)	−0.048 (4)	0.039 (4)	−0.054 (4)
C7	0.161 (6)	0.111 (5)	0.125 (5)	−0.028 (4)	0.038 (5)	−0.052 (4)
C8	0.139 (5)	0.106 (4)	0.115 (4)	−0.038 (4)	0.008 (4)	−0.021 (4)
C9	0.136 (5)	0.105 (4)	0.129 (5)	−0.002 (4)	0.028 (4)	−0.042 (4)
C10	0.080 (3)	0.073 (2)	0.084 (3)	−0.022 (2)	0.003 (2)	−0.026 (2)
C11	0.074 (3)	0.101 (4)	0.138 (4)	−0.033 (3)	0.013 (3)	−0.051 (3)
C12	0.107 (4)	0.158 (5)	0.102 (4)	−0.044 (4)	−0.001 (3)	−0.066 (4)
C14	0.071 (2)	0.096 (3)	0.075 (2)	−0.037 (2)	0.0194 (19)	−0.048 (2)
C15	0.112 (3)	0.087 (3)	0.097 (3)	−0.057 (3)	0.016 (3)	−0.055 (3)
C16	0.104 (3)	0.057 (2)	0.089 (3)	−0.041 (2)	0.015 (2)	−0.0351 (19)
C17	0.0562 (17)	0.0511 (17)	0.075 (2)	−0.0265 (14)	0.0185 (15)	−0.0312 (16)
N2	0.070 (2)	0.085 (3)	0.084 (2)	−0.0419 (19)	0.0133 (16)	−0.041 (2)
C18	0.072 (2)	0.093 (3)	0.0539 (19)	−0.046 (2)	0.0106 (16)	−0.0270 (18)
C19	0.081 (3)	0.097 (3)	0.092 (3)	−0.046 (2)	0.027 (2)	−0.037 (2)
C20	0.084 (3)	0.129 (5)	0.118 (4)	−0.047 (3)	0.037 (3)	−0.042 (3)
C21	0.106 (4)	0.152 (5)	0.110 (4)	−0.083 (4)	0.039 (3)	−0.037 (4)
C22	0.078 (2)	0.065 (2)	0.084 (3)	−0.0286 (19)	0.013 (2)	−0.0221 (19)
C23	0.072 (2)	0.055 (2)	0.091 (3)	−0.0358 (17)	0.0144 (19)	−0.0297 (18)
C24	0.126 (5)	0.119 (4)	0.118 (4)	−0.084 (4)	0.037 (3)	−0.035 (3)
C25	0.101 (3)	0.094 (3)	0.097 (3)	−0.055 (3)	0.026 (3)	−0.031 (3)

Geometric parameters (Å, º)

S1—O1	1.385 (3)	C9—H9	0.9300
S1—O2	1.439 (4)	C10—C11	1.373 (7)
S1—N1	1.646 (5)	C10—H10	0.9300
S1—C3	1.769 (4)	C11—H11	0.9300
S2—O4	1.428 (3)	C12—C14	1.515 (6)
S2—O3	1.438 (3)	C12—H12A	0.9600
S2—N2	1.631 (4)	C12—H12B	0.9600
S2—C17	1.753 (4)	C12—H12C	0.9600
C13—C1	1.522 (8)	C14—C15	1.378 (6)
C13—H13A	0.9600	C14—C22	1.378 (6)
C13—H13B	0.9600	C15—C16	1.372 (6)
C13—H13C	0.9600	C15—H15	0.9300
C2—C1	1.375 (8)	C16—C17	1.393 (5)
C2—C26	1.392 (8)	C16—H16	0.9300
C2—H2	0.9300	C17—C23	1.376 (5)
C1—C11	1.371 (8)	N2—C18	1.425 (5)
C26—C3	1.379 (6)	N2—H2A	0.72 (4)
C26—H26	0.9300	C18—C19	1.369 (6)
C3—C10	1.357 (6)	C18—C25	1.377 (6)
N1—C4	1.442 (6)	C19—C20	1.375 (6)
N1—H1A	0.98 (6)	C19—H19	0.9300
C4—C5	1.308 (7)	C20—C21	1.373 (8)
C4—C8	1.404 (8)	C20—H20	0.9300
C5—C6	1.375 (8)	C21—C24	1.347 (8)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.357 (8)	C22—C23	1.376 (5)
C6—H6	0.9300	C22—H22	0.9300
C7—C9	1.353 (9)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.396 (7)
C8—C9	1.409 (9)	C24—H24	0.9300
C8—H8	0.9300	C25—H25	0.9300
O1—S1—O2	118.8 (2)	C3—C10—C11	120.7 (4)
O1—S1—N1	111.7 (3)	C3—C10—H10	119.7
O2—S1—N1	103.1 (2)	C11—C10—H10	119.7
O1—S1—C3	107.0 (2)	C1—C11—C10	120.7 (5)
O2—S1—C3	108.6 (2)	C1—C11—H11	119.6
N1—S1—C3	107.18 (19)	C10—C11—H11	119.6
O4—S2—O3	119.07 (18)	C14—C12—H12A	109.5
O4—S2—N2	108.3 (2)	C14—C12—H12B	109.5
O3—S2—N2	104.57 (18)	H12A—C12—H12B	109.5
O4—S2—C17	108.50 (17)	C14—C12—H12C	109.5
O3—S2—C17	109.26 (17)	H12A—C12—H12C	109.5
N2—S2—C17	106.48 (17)	H12B—C12—H12C	109.5
C1—C13—H13A	109.5	C15—C14—C22	118.0 (4)
C1—C13—H13B	109.5	C15—C14—C12	121.1 (4)
H13A—C13—H13B	109.5	C22—C14—C12	120.9 (4)
C1—C13—H13C	109.5	C16—C15—C14	121.7 (4)
H13A—C13—H13C	109.5	C16—C15—H15	119.1
H13B—C13—H13C	109.5	C14—C15—H15	119.1
C1—C2—C26	122.0 (5)	C15—C16—C17	119.3 (4)
C1—C2—H2	119.0	C15—C16—H16	120.4
C26—C2—H2	119.0	C17—C16—H16	120.4
C11—C1—C2	118.1 (5)	C23—C17—C16	119.8 (4)
C11—C1—C13	121.4 (7)	C23—C17—S2	120.0 (3)
C2—C1—C13	120.5 (6)	C16—C17—S2	120.1 (3)
C3—C26—C2	117.9 (5)	C18—N2—S2	123.5 (3)
C3—C26—H26	121.1	C18—N2—H2A	111 (4)
C2—C26—H26	121.1	S2—N2—H2A	108 (4)
C10—C3—C26	120.5 (4)	C19—C18—C25	119.4 (4)
C10—C3—S1	121.6 (3)	C19—C18—N2	118.4 (4)
C26—C3—S1	117.8 (3)	C25—C18—N2	122.2 (4)
C4—N1—S1	125.1 (4)	C18—C19—C20	120.7 (5)
C4—N1—H1A	117 (3)	C18—C19—H19	119.7
S1—N1—H1A	113 (4)	C20—C19—H19	119.7
C5—C4—C8	121.8 (5)	C21—C20—C19	120.4 (5)
C5—C4—N1	122.1 (5)	C21—C20—H20	119.8
C8—C4—N1	116.1 (6)	C19—C20—H20	119.8
C4—C5—C6	119.6 (6)	C24—C21—C20	118.9 (5)
C4—C5—H5	120.2	C24—C21—H21	120.5
C6—C5—H5	120.2	C20—C21—H21	120.5
C7—C6—C5	121.8 (7)	C23—C22—C14	121.7 (4)
C7—C6—H6	119.1	C23—C22—H22	119.1
C5—C6—H6	119.1	C14—C22—H22	119.1
C9—C7—C6	119.3 (6)	C22—C23—C17	119.5 (3)
C9—C7—H7	120.4	C22—C23—H23	120.2
C6—C7—H7	120.4	C17—C23—H23	120.2
C4—C8—C9	117.3 (6)	C21—C24—C25	121.8 (5)
C4—C8—H8	121.3	C21—C24—H24	119.1
C9—C8—H8	121.3	C25—C24—H24	119.1
C7—C9—C8	120.2 (6)	C18—C25—C24	118.7 (5)
C7—C9—H9	119.9	C18—C25—H25	120.6
C8—C9—H9	119.9	C24—C25—H25	120.6

 

Footnotes

¹Supplementary material for this paper is available from the IUCr electronic archives (Reference: KK5074 ). Services for accessing this material are described at the back of the journal.