Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615015223/wq3094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015223/wq3094Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015223/wq3094IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015223/wq3094IIIsup4.hkl |
CCDC references: 1418861; 1418860; 1418859
In the chemical, biological and material sciences, isomers exhibit a variety of properties (Zhang et al., 2009). For instance, although positional isomers display similar functionalities (Park et al., 2005), stereoisomers of pharmaceutical compounds can exhibit profoundly different biological activities (Wermuth et al., 1997; Rebek, 2005), while for molecule-based functional materials, the bulk properties are not only related to a single molecular property but are also influenced to a large extent by intermolecular interactions. Changes in the position of substituent groups can significantly alter the molecular configurations and crystal structures of the isomers (Fan & Yan, 2014). A slight difference in molecular structure can lead to a profound impact on crystal packing.
Various substituted N-phenyl phthalimide derivatives have shown potential anticonvulsant activity (Yadav et al., 2012). Taurine is known to have anti-epileptic activity, but as yet this has not been applied in the clinical setting (Gupta et al., 2005). 2-Phthalimido-N-substituted-phenylethanesulfonamides have been designed as potent anticonvulsant compounds and evaluated for anticonvulsant activity in animal experiments. Anticonvulsant activity has been shown to be sensitive to the position of the chlorine substituents. Thus, the ortho-chloro substituted isomer (I) is more active than (II) and (III) (Akgul et al., 2007). The para-substituted isomer (II) can be used as a disposable electrochemical biosensor and redox indicator; it reduces guanine base oxidation and can cause mutation (Ozkan-Ariksoysal et al., 2010).
We now report the structures of these three positional isomers of N-chlorophenyl-2-phthalimidoethanesulfonamide derivatives, namely N-(2-chlorophenyl)-2-phthalimidoethanesulfonamide, (I), N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), and N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide, (III) (see scheme). The purpose of this study is to determine the impact of the chlorine position on the intermolecular interactions and ultimately on the crystal packing.
Synthesis and crystallization processes were reported in a previous study (Akgul et al., 2007).
Crystal data, data collection and structure refinement details are summarized in Table 1. For all three structures, H atoms were refined freely, giving C—H = 0.90 (4)–0.98 (3) Å and N—H = 0.83 (3) Å. [Please check added details and correct as necessary]
In the molecule of (I) (Fig. 1) there are two C—H···O and N—H···O type intramolecular interactions (Table 2), which generate S(6) and S(8) motifs (Bernstein et al., 1995), respectively. There are also two types of intermolecular interaction. A polymeric chain along the b axis is generated by C7—H7A···O4i_I intermolecular interactions with graph set C(6), while C7—H7B···O2ii_I intermolecular interactions form a second polymeric chain, with graph set C(4), extending along the a axis [symmetry codes: (i_I) 1 - x, -1/2 + y, 1/2 - z; (ii_I) -1 + x, y, z]. Considering these two interactions together, they form a two-dimensional polymeric sheet parallel to the ab plane. In this plane, two graph sets, R44(18) and R54(18), can be defined, as shown in Fig 2.
In the molecule of (II) (Fig. 3), although there no significant intramolecular interactions are observed, there do exist N—H···O, C—H···O and π–π type intermolecular interactions (Table 3). The N1–H1···O2i_II interaction forms a centrosymmetric dimer between the molecules with fractional coordinates (x, y, z) and (-x, 1 - y, -z), forming an R22(8) motif [symmetry code: (i_II) -x, 1 - y, -z]. In addition to this hydrogen bond, the dimer is stabilised by π–π interactions between the C1–C6 benzene ring and the C10–C15 ring, with a centroid-to-centroid distance of 3.8723 (18) Å. Finally, there is a C4—H4···O4ii_II interaction, which results in the formation of a one-dimensional polymeric chain extending along the b axis with a C(11) motif [symmetry code: (ii_II) x, -1 + y, z]. Considering this chain and the dimeric interaction generated by the N1—H1···O2i_II and π–π interactions, a one-dimensional bi-chain is formed along the b axis (Fig. 4).
In the molecule of (III) (Fig. 5) there is an intramolecular C5—H5···O1 hydrogen bond which gives rise to an S(6) motif (Table 4). In addition, the C11—H11···O3i_III interaction forms a dimeric structure, which can be described as an R22(12) motif, with the inversion-related molecule [symmetry code: (i_III) 1 - x, -y, -z]. The N1—H1···O4ii_III intermolecular interaction gives rise to a one-dimensional polymeric chain, described as a C(8) motif, extending along the a axis (Fig. 6) [symmetry code: (ii_III) 1 + x, y, z]. Considering this C(8) chain and the dimeric interaction together, they generate a two-dimensional sheet parallel to the (031) plane. Providing further stabilisation to the C(8) chain is a C2—H2···Cl1iii_III interaction, which generates a one-dimensional polymeric chain described as a C(5) motif extending along the a axis (Fig. 7) [symmetry code: (iii_III) 1 + x, 1/2 - y, 1/2 + z]. Considering this C(5) chain and the dimeric interaction together, they form a two-dimensional sheet perpendicular to the b axis. Finally, considering these three interactions together, all molecules in the structure of (III) are connected to each other via C—H···O, N—H···O and C—H···Cl type intermolecular interactions.
Intra- and intermolecular hydrogen bonds play an important role in molecular and crystal structural conformations. To investigate the conformational differences of the three title compounds, the torsion angles around the C7—C8 and S1—C7 bonds were compared (Tables 5–7). The conformations about the S1—C7 bond for (I), (II) and (III) are -sc (-synclinal), +ap (+antiperiplanar) and -sc, respectively. The conformations about the C7—C8 bond for (I), (II) and (III) are -sc, -sc and +sc, respectively. Considering the intramolecular interactions, (I) has an N—H···O type interaction which folds the molecule into an -sc, -sc conformation.
The conformational differences between the three isomers is highlighted by comparison of the T1 (N1—S1—C7—C8) and T2 (S1—C7—C8—N2) torsion angles. Comparing the conformations of (I) and (II), the T2 angles are similar (-62.7 and -70.9°, respectively), but the T1 angles give rise to the difference, with values of -52.0 and -176.8°, respectively. Comparing (I) and (III), the T1 angles are similar (-52.0 and -70.2°, respectively) but the T2 angles lead to the difference, with values of -62.7 and +64.7°, respectively. In summary, the T1 dihedral angle is responsible for the difference between (I) and (II) and between (II) and (III), while the T2 angle is responsible for the difference between (I) and (III) and between (II) and (III). The bond distances and angles of the flexible linkage between the aromatic systems do not differ significantly between (I), (II) and (III), despite the differing conformations of these linkers.
The molecular structures of the three title compounds consist of two planar/aromatic rings, which are benzene and isoindole rings. The dihedral angles between the mean planes of these rings for (I), (II) and (III) are 62.7 (1), 12.50 (9) and 8.25 (7)°, respectively.
Positional isomerization not only affects topology and packing differences, but also affects the physicochemical (Liao et al., 2010), kinetic and thermodynamic (Dhalluin et al., 2005) properties and the pharmaceutical activities of compounds (Banba et al., 2013). Considering the drug activity of the title compounds (Akgul et al., 2007), (I) was found to be more active than the others, while (II) and (III) show equal and weak activity compared with (I). In addition, the toxicity of aromatic compounds is higher than that of non-aromatics (Pramanik & Roy, 2014). Although (I) does not show any neurotoxic effect, (II) and (III) do show neurotoxicity.
To compare the efficiency of the title compounds as potential anticonvulsant drugs, their aromaticities were calculated and compared. Hypotetically, because of electron delocalization, the ortho- and para-positions of nitro-substituted benzene are partially negative charged. When an electron-withdrawing group (chlorine) is attached in the para- or ortho-postion, the aromticity of benzene decreases. To compare the aromaticities of these benzene rings, highest occupied molecular orbital (HOMA; Krygowski, 1993) aromaticity indices were calculated. Comparing the HOMA values of these compounds, the obtained values are 0.919, 0.930 and 0.948 for (I), (II) and (III), respectively. Thus, (I) is slightly less aromatic than (II) and (III), and so is a more suitable candidate for anticonvulsant drugs.
Although the main difference between the three title compounds is simply the position of the chlorine substituent, the resulting crystal systems and space groups are different from each other. Compound (I) crystallizes in a noncentrosymmetric chiral orthorhombic space group, while (II) and (III) crystallize in centrosymmetric triclinic and monoclinic space groups. In brief, positional isomerization plays an important role in the packing and structural conformation of the studied compounds.
For related literature, see: Ozkan-Ariksoysal et al. (2010); Bernstein et al. (1995); Fan & Yan (2014); Gupta et al. (2005); Park et al. (2005); Rebek (2005); Wermuth et al. (1997); Yadav et al. (2012); Zhang et al. (2009).
For all compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C16H13ClN2O4S | Dx = 1.546 Mg m−3 |
Mr = 364.79 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1162 reflections |
a = 5.4126 (2) Å | θ = 3.9–24.3° |
b = 12.7656 (5) Å | µ = 0.40 mm−1 |
c = 22.6827 (8) Å | T = 293 K |
V = 1567.26 (11) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.07 × 0.05 mm |
F(000) = 752 |
Agilent Xcalibur Eos diffractometer | 2894 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2484 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 16.1333 pixels mm-1 | θmax = 26.4°, θmin = 3.2° |
ω scans | h = −5→6 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | k = −9→15 |
Tmin = 0.989, Tmax = 0.998 | l = −28→28 |
4676 measured reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0353P)2 + 0.1242P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.22 e Å−3 |
2894 reflections | Δρmin = −0.29 e Å−3 |
269 parameters | Absolute structure: Flack x parameter determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.02 (4) |
C16H13ClN2O4S | V = 1567.26 (11) Å3 |
Mr = 364.79 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.4126 (2) Å | µ = 0.40 mm−1 |
b = 12.7656 (5) Å | T = 293 K |
c = 22.6827 (8) Å | 0.35 × 0.07 × 0.05 mm |
Agilent Xcalibur Eos diffractometer | 2894 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | 2484 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 0.998 | Rint = 0.018 |
4676 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.082 | Δρmax = 0.22 e Å−3 |
S = 1.06 | Δρmin = −0.29 e Å−3 |
2894 reflections | Absolute structure: Flack x parameter determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
269 parameters | Absolute structure parameter: 0.02 (4) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.1528 (2) | 0.56965 (9) | 0.18287 (5) | 0.0680 (4) | |
S1 | 0.55647 (15) | 0.26803 (7) | 0.19537 (4) | 0.0370 (2) | |
O1 | 0.5602 (5) | 0.1892 (2) | 0.15096 (11) | 0.0553 (7) | |
O2 | 0.7807 (4) | 0.2950 (2) | 0.22485 (11) | 0.0506 (7) | |
O3 | 0.4455 (5) | 0.2256 (2) | 0.40447 (10) | 0.0553 (7) | |
O4 | 0.5984 (6) | 0.49229 (19) | 0.27603 (11) | 0.0546 (8) | |
N1 | 0.4553 (6) | 0.3769 (2) | 0.16682 (13) | 0.0393 (7) | |
N2 | 0.4780 (5) | 0.3494 (2) | 0.33100 (11) | 0.0339 (6) | |
C1 | 0.1054 (7) | 0.4755 (3) | 0.12845 (15) | 0.0407 (8) | |
C2 | −0.0807 (8) | 0.4903 (4) | 0.0879 (2) | 0.0573 (11) | |
C3 | −0.1259 (9) | 0.4152 (4) | 0.0464 (2) | 0.0661 (14) | |
C4 | 0.0144 (9) | 0.3270 (4) | 0.04528 (19) | 0.0670 (14) | |
C5 | 0.2043 (8) | 0.3126 (4) | 0.08425 (17) | 0.0541 (11) | |
C6 | 0.2538 (6) | 0.3869 (3) | 0.12702 (14) | 0.0372 (8) | |
C7 | 0.3380 (7) | 0.2312 (3) | 0.24945 (15) | 0.0338 (7) | |
C8 | 0.2735 (6) | 0.3148 (3) | 0.29420 (15) | 0.0360 (8) | |
C9 | 0.5444 (7) | 0.3021 (3) | 0.38401 (14) | 0.0374 (8) | |
C10 | 0.7535 (6) | 0.3651 (3) | 0.40753 (14) | 0.0354 (8) | |
C11 | 0.8922 (8) | 0.3531 (3) | 0.45783 (16) | 0.0490 (10) | |
C12 | 1.0798 (8) | 0.4249 (4) | 0.46783 (17) | 0.0527 (11) | |
C13 | 1.1236 (8) | 0.5051 (4) | 0.42894 (19) | 0.0522 (11) | |
C14 | 0.9833 (7) | 0.5175 (3) | 0.37819 (17) | 0.0466 (10) | |
C15 | 0.7968 (6) | 0.4469 (3) | 0.36876 (14) | 0.0354 (8) | |
C16 | 0.6205 (6) | 0.4376 (3) | 0.31878 (14) | 0.0350 (8) | |
H8A | 0.142 (5) | 0.290 (2) | 0.3206 (12) | 0.024 (8)* | |
H7A | 0.397 (6) | 0.172 (3) | 0.2652 (14) | 0.039 (10)* | |
H14 | 1.007 (7) | 0.574 (3) | 0.3536 (16) | 0.054 (12)* | |
H5 | 0.301 (7) | 0.250 (3) | 0.0823 (16) | 0.047 (11)* | |
H1 | 0.480 (6) | 0.429 (3) | 0.1884 (14) | 0.035 (10)* | |
H8B | 0.206 (6) | 0.379 (3) | 0.2774 (14) | 0.033 (9)* | |
H3 | −0.238 (7) | 0.428 (3) | 0.0187 (18) | 0.062 (13)* | |
H7B | 0.202 (6) | 0.211 (2) | 0.2276 (14) | 0.038 (10)* | |
H11 | 0.862 (7) | 0.295 (3) | 0.4814 (15) | 0.046 (11)* | |
H13 | 1.238 (8) | 0.554 (3) | 0.4382 (17) | 0.057 (12)* | |
H2 | −0.165 (7) | 0.546 (3) | 0.0902 (16) | 0.044 (12)* | |
H12 | 1.174 (7) | 0.417 (3) | 0.5054 (17) | 0.062 (12)* | |
H4 | −0.017 (8) | 0.275 (4) | 0.0182 (19) | 0.074 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0714 (7) | 0.0491 (6) | 0.0834 (8) | 0.0162 (6) | −0.0174 (6) | −0.0138 (6) |
S1 | 0.0316 (4) | 0.0414 (5) | 0.0380 (4) | 0.0095 (4) | −0.0001 (4) | −0.0008 (4) |
O1 | 0.0665 (17) | 0.0525 (17) | 0.0468 (14) | 0.0235 (15) | 0.0072 (14) | −0.0098 (12) |
O2 | 0.0267 (13) | 0.067 (2) | 0.0581 (16) | 0.0053 (12) | −0.0039 (11) | 0.0075 (14) |
O3 | 0.0695 (18) | 0.0529 (16) | 0.0436 (14) | −0.0213 (16) | 0.0029 (13) | 0.0108 (13) |
O4 | 0.083 (2) | 0.0342 (15) | 0.0469 (15) | −0.0101 (14) | −0.0184 (14) | 0.0089 (12) |
N1 | 0.0435 (17) | 0.0360 (18) | 0.0383 (15) | 0.0020 (15) | −0.0063 (14) | 0.0005 (14) |
N2 | 0.0383 (16) | 0.0328 (15) | 0.0306 (13) | −0.0038 (13) | −0.0022 (12) | −0.0003 (12) |
C1 | 0.037 (2) | 0.044 (2) | 0.0415 (19) | 0.0017 (17) | 0.0005 (16) | 0.0076 (17) |
C2 | 0.048 (3) | 0.060 (3) | 0.064 (3) | 0.008 (3) | −0.006 (2) | 0.016 (2) |
C3 | 0.054 (3) | 0.093 (4) | 0.052 (3) | 0.005 (3) | −0.019 (2) | 0.010 (3) |
C4 | 0.073 (3) | 0.081 (4) | 0.047 (2) | 0.005 (3) | −0.019 (2) | −0.011 (2) |
C5 | 0.059 (3) | 0.061 (3) | 0.042 (2) | 0.016 (2) | −0.010 (2) | −0.008 (2) |
C6 | 0.0316 (18) | 0.049 (2) | 0.0309 (16) | 0.0009 (17) | 0.0039 (14) | 0.0048 (16) |
C7 | 0.0302 (17) | 0.0317 (19) | 0.0396 (18) | 0.0004 (17) | −0.0050 (15) | −0.0012 (17) |
C8 | 0.0323 (18) | 0.035 (2) | 0.0412 (19) | 0.0002 (16) | 0.0013 (16) | −0.0032 (16) |
C9 | 0.045 (2) | 0.0363 (19) | 0.0306 (16) | 0.0012 (17) | 0.0067 (16) | −0.0005 (15) |
C10 | 0.0393 (19) | 0.0348 (19) | 0.0323 (16) | 0.0024 (16) | 0.0041 (15) | −0.0043 (15) |
C11 | 0.059 (3) | 0.052 (3) | 0.0358 (19) | 0.002 (2) | −0.0061 (18) | 0.0011 (19) |
C12 | 0.054 (3) | 0.062 (3) | 0.042 (2) | 0.006 (2) | −0.014 (2) | −0.009 (2) |
C13 | 0.046 (2) | 0.056 (3) | 0.055 (2) | −0.004 (2) | −0.0061 (19) | −0.019 (2) |
C14 | 0.053 (2) | 0.039 (2) | 0.048 (2) | −0.0068 (19) | 0.0028 (18) | −0.0052 (19) |
C15 | 0.0373 (18) | 0.0337 (19) | 0.0353 (17) | −0.0010 (16) | 0.0021 (15) | −0.0064 (15) |
C16 | 0.042 (2) | 0.0279 (17) | 0.0350 (17) | −0.0016 (16) | −0.0004 (14) | −0.0011 (15) |
Cl1—C1 | 1.742 (4) | C5—C6 | 1.383 (5) |
S1—O1 | 1.424 (3) | C5—H5 | 0.96 (4) |
S1—O2 | 1.428 (3) | C7—C8 | 1.514 (5) |
S1—N1 | 1.629 (3) | C7—H7A | 0.90 (4) |
S1—C7 | 1.768 (4) | C7—H7B | 0.92 (3) |
O3—C9 | 1.207 (4) | C8—H8A | 0.98 (3) |
O4—C16 | 1.201 (4) | C8—H8B | 0.97 (3) |
N1—C6 | 1.421 (4) | C9—C10 | 1.487 (5) |
N1—H1 | 0.83 (3) | C10—C11 | 1.374 (5) |
N2—C8 | 1.455 (4) | C10—C15 | 1.385 (5) |
N2—C9 | 1.392 (4) | C11—C12 | 1.386 (6) |
N2—C16 | 1.393 (4) | C11—H11 | 0.93 (3) |
C1—C2 | 1.378 (5) | C12—C13 | 1.372 (6) |
C1—C6 | 1.388 (5) | C12—H12 | 1.00 (4) |
C2—C3 | 1.365 (7) | C13—C14 | 1.388 (5) |
C2—H2 | 0.85 (4) | C13—H13 | 0.90 (4) |
C3—C4 | 1.359 (7) | C14—C15 | 1.370 (5) |
C3—H3 | 0.89 (4) | C14—H14 | 0.93 (4) |
C4—C5 | 1.368 (6) | C15—C16 | 1.487 (4) |
C4—H4 | 0.92 (4) | ||
O1—S1—O2 | 119.32 (15) | C8—C7—H7A | 114 (2) |
O1—S1—N1 | 109.09 (16) | C8—C7—H7B | 112 (2) |
O1—S1—C7 | 108.21 (17) | H7A—C7—H7B | 105 (3) |
O2—S1—N1 | 105.43 (16) | N2—C8—C7 | 115.0 (3) |
O2—S1—C7 | 107.94 (16) | N2—C8—H8A | 107.5 (16) |
N1—S1—C7 | 106.13 (17) | N2—C8—H8B | 105.0 (19) |
S1—N1—H1 | 113 (2) | C7—C8—H8A | 110.2 (17) |
C6—N1—S1 | 125.9 (3) | C7—C8—H8B | 114.5 (19) |
C6—N1—H1 | 115 (2) | H8A—C8—H8B | 104 (3) |
C9—N2—C8 | 124.1 (3) | O3—C9—N2 | 124.6 (3) |
C9—N2—C16 | 112.3 (3) | O3—C9—C10 | 129.6 (3) |
C16—N2—C8 | 123.5 (3) | N2—C9—C10 | 105.8 (3) |
C2—C1—Cl1 | 119.1 (3) | C11—C10—C9 | 130.8 (3) |
C2—C1—C6 | 121.3 (4) | C11—C10—C15 | 121.2 (3) |
C6—C1—Cl1 | 119.6 (3) | C15—C10—C9 | 108.0 (3) |
C1—C2—H2 | 118 (3) | C10—C11—C12 | 117.5 (4) |
C3—C2—C1 | 119.7 (4) | C10—C11—H11 | 118 (2) |
C3—C2—H2 | 123 (3) | C12—C11—H11 | 124 (2) |
C2—C3—H3 | 119 (3) | C11—C12—H12 | 117 (2) |
C4—C3—C2 | 119.7 (4) | C13—C12—C11 | 120.9 (4) |
C4—C3—H3 | 121 (3) | C13—C12—H12 | 122 (2) |
C3—C4—C5 | 121.3 (5) | C12—C13—C14 | 121.6 (4) |
C3—C4—H4 | 120 (3) | C12—C13—H13 | 119 (3) |
C5—C4—H4 | 118 (3) | C14—C13—H13 | 119 (3) |
C4—C5—C6 | 120.4 (4) | C13—C14—H14 | 121 (2) |
C4—C5—H5 | 119 (2) | C15—C14—C13 | 117.2 (4) |
C6—C5—H5 | 120 (2) | C15—C14—H14 | 122 (2) |
C1—C6—N1 | 120.1 (3) | C10—C15—C16 | 108.4 (3) |
C5—C6—N1 | 122.2 (3) | C14—C15—C10 | 121.4 (3) |
C5—C6—C1 | 117.6 (3) | C14—C15—C16 | 130.1 (3) |
S1—C7—H7A | 105 (2) | O4—C16—N2 | 125.2 (3) |
S1—C7—H7B | 104 (2) | O4—C16—C15 | 129.3 (3) |
C8—C7—S1 | 115.6 (3) | N2—C16—C15 | 105.5 (3) |
Cl1—C1—C2—C3 | −177.5 (4) | C8—N2—C9—C10 | −177.6 (3) |
Cl1—C1—C6—N1 | −4.8 (4) | C8—N2—C16—O4 | −3.1 (5) |
Cl1—C1—C6—C5 | 177.9 (3) | C8—N2—C16—C15 | 177.0 (3) |
S1—N1—C6—C1 | 146.9 (3) | C9—N2—C8—C7 | −88.2 (4) |
S1—N1—C6—C5 | −36.0 (5) | C9—N2—C16—O4 | −179.5 (3) |
S1—C7—C8—N2 | −62.7 (4) | C9—N2—C16—C15 | 0.6 (4) |
O1—S1—N1—C6 | 42.2 (3) | C9—C10—C11—C12 | 179.3 (3) |
O1—S1—C7—C8 | −169.0 (3) | C9—C10—C15—C14 | −178.7 (3) |
O2—S1—N1—C6 | 171.4 (3) | C9—C10—C15—C16 | −1.1 (4) |
O2—S1—C7—C8 | 60.6 (3) | C10—C11—C12—C13 | 0.4 (6) |
O3—C9—C10—C11 | 1.0 (6) | C10—C15—C16—O4 | −179.6 (4) |
O3—C9—C10—C15 | −178.6 (4) | C10—C15—C16—N2 | 0.3 (4) |
N1—S1—C7—C8 | −52.0 (3) | C11—C10—C15—C14 | 1.6 (5) |
N2—C9—C10—C11 | −179.0 (4) | C11—C10—C15—C16 | 179.3 (3) |
N2—C9—C10—C15 | 1.4 (3) | C11—C12—C13—C14 | −0.2 (6) |
C1—C2—C3—C4 | −0.6 (7) | C12—C13—C14—C15 | 0.7 (6) |
C2—C1—C6—N1 | 175.6 (3) | C13—C14—C15—C10 | −1.4 (6) |
C2—C1—C6—C5 | −1.6 (5) | C13—C14—C15—C16 | −178.4 (3) |
C2—C3—C4—C5 | −1.3 (7) | C14—C15—C16—O4 | −2.2 (6) |
C3—C4—C5—C6 | 1.8 (7) | C14—C15—C16—N2 | 177.7 (4) |
C4—C5—C6—N1 | −177.5 (4) | C15—C10—C11—C12 | −1.1 (5) |
C4—C5—C6—C1 | −0.3 (6) | C16—N2—C8—C7 | 95.7 (4) |
C6—C1—C2—C3 | 2.1 (6) | C16—N2—C9—O3 | 178.8 (3) |
C7—S1—N1—C6 | −74.2 (3) | C16—N2—C9—C10 | −1.2 (4) |
C8—N2—C9—O3 | 2.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.84 (4) | 2.24 (3) | 2.984 (4) | 148 (3) |
C5—H5···O1 | 0.96 (4) | 2.24 (4) | 2.912 (5) | 127 (3) |
C7—H7A···O4i | 0.90 (4) | 2.48 (4) | 3.123 (5) | 129 (3) |
C7—H7B···O2ii | 0.92 (3) | 2.52 (3) | 3.174 (4) | 128 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z. |
C16H13ClN2O4S | Z = 2 |
Mr = 364.79 | F(000) = 376 |
Triclinic, P1 | Dx = 1.487 Mg m−3 |
a = 7.5484 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9887 (10) Å | Cell parameters from 2152 reflections |
c = 11.2112 (10) Å | θ = 3.6–27.6° |
α = 100.624 (8)° | µ = 0.39 mm−1 |
β = 98.405 (7)° | T = 293 K |
γ = 95.661 (8)° | Needle, colourless |
V = 815.01 (13) Å3 | 0.18 × 0.12 × 0.06 mm |
Agilent Xcalibur Eos diffractometer | 3287 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2245 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 16.1333 pixels mm-1 | θmax = 26.4°, θmin = 3.1° |
ω scans | h = −8→9 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | k = −12→11 |
Tmin = 0.974, Tmax = 0.991 | l = −13→13 |
5967 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | All H-atom parameters refined |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.1892P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3287 reflections | Δρmax = 0.36 e Å−3 |
269 parameters | Δρmin = −0.37 e Å−3 |
C16H13ClN2O4S | γ = 95.661 (8)° |
Mr = 364.79 | V = 815.01 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5484 (7) Å | Mo Kα radiation |
b = 9.9887 (10) Å | µ = 0.39 mm−1 |
c = 11.2112 (10) Å | T = 293 K |
α = 100.624 (8)° | 0.18 × 0.12 × 0.06 mm |
β = 98.405 (7)° |
Agilent Xcalibur Eos diffractometer | 3287 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | 2245 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.991 | Rint = 0.023 |
5967 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.36 e Å−3 |
3287 reflections | Δρmin = −0.37 e Å−3 |
269 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.12262 (9) | 0.64365 (6) | 0.17046 (6) | 0.0474 (2) | |
Cl1 | 0.40898 (13) | 0.21113 (9) | 0.55665 (7) | 0.0877 (3) | |
O1 | 0.1404 (3) | 0.74094 (19) | 0.28272 (16) | 0.0617 (5) | |
O2 | 0.0077 (2) | 0.66582 (19) | 0.06416 (16) | 0.0613 (5) | |
N2 | 0.3718 (3) | 0.8007 (2) | 0.00577 (19) | 0.0526 (6) | |
O3 | 0.4483 (3) | 0.6276 (2) | −0.13529 (19) | 0.0730 (6) | |
O4 | 0.2650 (3) | 0.9967 (2) | 0.09429 (19) | 0.0753 (6) | |
N1 | 0.0440 (3) | 0.4938 (3) | 0.1914 (2) | 0.0567 (6) | |
C15 | 0.2363 (3) | 0.9237 (2) | −0.1272 (2) | 0.0449 (6) | |
C10 | 0.2968 (3) | 0.8135 (2) | −0.1968 (2) | 0.0443 (6) | |
C11 | 0.2729 (4) | 0.7948 (3) | −0.3226 (3) | 0.0568 (7) | |
C5 | 0.1819 (3) | 0.2998 (3) | 0.2443 (2) | 0.0475 (6) | |
C1 | 0.1694 (5) | 0.4902 (3) | 0.4040 (3) | 0.0661 (8) | |
C6 | 0.1349 (3) | 0.4282 (3) | 0.2810 (2) | 0.0471 (6) | |
C4 | 0.2632 (4) | 0.2323 (3) | 0.3294 (2) | 0.0515 (7) | |
C3 | 0.3013 (4) | 0.2958 (3) | 0.4514 (2) | 0.0543 (7) | |
C9 | 0.3824 (3) | 0.7322 (3) | −0.1123 (2) | 0.0503 (6) | |
C16 | 0.2867 (4) | 0.9181 (3) | 0.0042 (3) | 0.0522 (7) | |
C13 | 0.1220 (4) | 0.9958 (3) | −0.3088 (3) | 0.0649 (8) | |
C7 | 0.3389 (4) | 0.6241 (3) | 0.1331 (3) | 0.0518 (7) | |
C14 | 0.1475 (4) | 1.0161 (3) | −0.1820 (3) | 0.0555 (7) | |
C8 | 0.4433 (4) | 0.7558 (4) | 0.1163 (3) | 0.0616 (8) | |
C2 | 0.2545 (5) | 0.4229 (3) | 0.4887 (3) | 0.0696 (9) | |
C12 | 0.1851 (4) | 0.8875 (4) | −0.3776 (3) | 0.0664 (8) | |
H5 | 0.160 (3) | 0.256 (2) | 0.159 (2) | 0.051 (7)* | |
H7A | 0.401 (3) | 0.595 (2) | 0.199 (2) | 0.046 (7)* | |
H4 | 0.298 (3) | 0.151 (3) | 0.304 (2) | 0.058 (8)* | |
H2 | 0.282 (4) | 0.466 (3) | 0.567 (3) | 0.069 (9)* | |
H8A | 0.444 (4) | 0.833 (3) | 0.185 (3) | 0.069 (9)* | |
H14 | 0.112 (4) | 1.085 (3) | −0.133 (3) | 0.066 (9)* | |
H7B | 0.325 (3) | 0.553 (3) | 0.063 (2) | 0.056 (7)* | |
H11 | 0.315 (4) | 0.720 (3) | −0.370 (3) | 0.077 (9)* | |
H12 | 0.170 (5) | 0.881 (4) | −0.463 (3) | 0.102 (12)* | |
H13 | 0.060 (4) | 1.059 (3) | −0.343 (3) | 0.063 (8)* | |
H8B | 0.564 (5) | 0.739 (4) | 0.111 (3) | 0.093 (11)* | |
H1 | 0.010 (3) | 0.448 (3) | 0.130 (2) | 0.047 (8)* | |
H1A | 0.132 (3) | 0.575 (3) | 0.428 (2) | 0.063 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0565 (4) | 0.0443 (4) | 0.0406 (3) | 0.0169 (3) | −0.0005 (3) | 0.0080 (3) |
Cl1 | 0.1223 (7) | 0.0831 (6) | 0.0596 (5) | 0.0158 (5) | −0.0063 (5) | 0.0348 (4) |
O1 | 0.0830 (13) | 0.0531 (11) | 0.0479 (11) | 0.0239 (10) | 0.0074 (9) | 0.0020 (9) |
O2 | 0.0680 (12) | 0.0588 (12) | 0.0541 (11) | 0.0206 (10) | −0.0117 (9) | 0.0142 (9) |
N2 | 0.0622 (14) | 0.0519 (13) | 0.0482 (13) | 0.0144 (11) | 0.0111 (10) | 0.0163 (10) |
O3 | 0.0917 (15) | 0.0619 (13) | 0.0829 (15) | 0.0417 (12) | 0.0363 (12) | 0.0258 (11) |
O4 | 0.1066 (16) | 0.0588 (13) | 0.0559 (12) | 0.0174 (11) | 0.0175 (11) | −0.0068 (10) |
N1 | 0.0596 (15) | 0.0568 (15) | 0.0479 (14) | 0.0016 (12) | −0.0068 (12) | 0.0116 (12) |
C15 | 0.0470 (14) | 0.0355 (13) | 0.0542 (15) | 0.0059 (11) | 0.0141 (11) | 0.0098 (11) |
C10 | 0.0427 (13) | 0.0407 (13) | 0.0499 (15) | 0.0053 (11) | 0.0105 (11) | 0.0084 (11) |
C11 | 0.0640 (18) | 0.0544 (17) | 0.0523 (17) | 0.0109 (14) | 0.0148 (13) | 0.0060 (14) |
C5 | 0.0486 (15) | 0.0531 (16) | 0.0369 (14) | 0.0018 (12) | 0.0029 (11) | 0.0048 (12) |
C1 | 0.101 (2) | 0.0536 (18) | 0.0443 (16) | 0.0170 (17) | 0.0117 (15) | 0.0075 (14) |
C6 | 0.0484 (14) | 0.0503 (15) | 0.0424 (14) | 0.0023 (12) | 0.0057 (11) | 0.0125 (12) |
C4 | 0.0583 (17) | 0.0480 (16) | 0.0488 (15) | 0.0087 (13) | 0.0087 (12) | 0.0104 (13) |
C3 | 0.0639 (17) | 0.0545 (17) | 0.0456 (15) | −0.0005 (13) | 0.0051 (12) | 0.0204 (13) |
C9 | 0.0522 (15) | 0.0468 (15) | 0.0596 (17) | 0.0147 (13) | 0.0190 (12) | 0.0183 (13) |
C16 | 0.0571 (16) | 0.0426 (15) | 0.0577 (17) | 0.0066 (13) | 0.0143 (13) | 0.0085 (13) |
C13 | 0.0613 (18) | 0.066 (2) | 0.073 (2) | 0.0147 (16) | 0.0043 (15) | 0.0308 (17) |
C7 | 0.0614 (17) | 0.0526 (17) | 0.0454 (15) | 0.0205 (14) | 0.0046 (13) | 0.0168 (14) |
C14 | 0.0542 (16) | 0.0443 (15) | 0.070 (2) | 0.0129 (13) | 0.0132 (14) | 0.0115 (14) |
C8 | 0.062 (2) | 0.069 (2) | 0.0535 (18) | 0.0055 (16) | −0.0020 (14) | 0.0211 (16) |
C2 | 0.109 (3) | 0.0590 (19) | 0.0333 (15) | 0.0028 (17) | −0.0019 (15) | 0.0049 (14) |
C12 | 0.070 (2) | 0.074 (2) | 0.0571 (19) | 0.0095 (16) | 0.0050 (15) | 0.0219 (17) |
S1—O1 | 1.4214 (18) | C5—C4 | 1.374 (4) |
S1—O2 | 1.4333 (17) | C5—H5 | 0.96 (2) |
S1—N1 | 1.626 (3) | C1—C6 | 1.379 (4) |
S1—C7 | 1.764 (3) | C1—C2 | 1.381 (4) |
Cl1—C3 | 1.729 (3) | C1—H1A | 0.93 (3) |
N2—C9 | 1.391 (3) | C4—C3 | 1.373 (4) |
N2—C16 | 1.393 (3) | C4—H4 | 0.88 (3) |
N2—C8 | 1.445 (3) | C3—C2 | 1.360 (4) |
O3—C9 | 1.203 (3) | C13—C14 | 1.379 (4) |
O4—C16 | 1.202 (3) | C13—C12 | 1.377 (5) |
N1—C6 | 1.428 (3) | C13—H13 | 0.93 (3) |
N1—H1 | 0.75 (2) | C7—C8 | 1.522 (4) |
C15—C10 | 1.384 (3) | C7—H7A | 0.92 (3) |
C15—C16 | 1.480 (4) | C7—H7B | 0.94 (3) |
C15—C14 | 1.375 (4) | C14—H14 | 0.89 (3) |
C10—C11 | 1.372 (4) | C8—H8A | 0.98 (3) |
C10—C9 | 1.477 (4) | C8—H8B | 0.95 (3) |
C11—C12 | 1.374 (4) | C2—H2 | 0.89 (3) |
C11—H11 | 0.95 (3) | C12—H12 | 0.93 (4) |
C5—C6 | 1.371 (4) | ||
O1—S1—O2 | 118.61 (11) | C4—C3—Cl1 | 118.9 (2) |
O1—S1—N1 | 108.99 (13) | C2—C3—Cl1 | 120.7 (2) |
O1—S1—C7 | 109.18 (13) | C2—C3—C4 | 120.5 (3) |
O2—S1—N1 | 105.52 (12) | N2—C9—C10 | 105.8 (2) |
O2—S1—C7 | 108.63 (13) | O3—C9—N2 | 124.6 (3) |
N1—S1—C7 | 105.05 (13) | O3—C9—C10 | 129.6 (3) |
C9—N2—C16 | 111.9 (2) | N2—C16—C15 | 105.9 (2) |
C9—N2—C8 | 123.7 (2) | O4—C16—N2 | 124.8 (3) |
C16—N2—C8 | 124.4 (2) | O4—C16—C15 | 129.3 (3) |
S1—N1—H1 | 109 (2) | C14—C13—H13 | 115.8 (18) |
C6—N1—S1 | 122.31 (18) | C12—C13—C14 | 121.0 (3) |
C6—N1—H1 | 114 (2) | C12—C13—H13 | 123.1 (18) |
C10—C15—C16 | 108.0 (2) | S1—C7—H7A | 105.0 (15) |
C14—C15—C10 | 121.2 (3) | S1—C7—H7B | 107.9 (16) |
C14—C15—C16 | 130.8 (2) | C8—C7—S1 | 114.2 (2) |
C15—C10—C9 | 108.4 (2) | C8—C7—H7A | 108.6 (15) |
C11—C10—C15 | 120.8 (3) | C8—C7—H7B | 112.4 (17) |
C11—C10—C9 | 130.8 (2) | H7A—C7—H7B | 108 (2) |
C10—C11—C12 | 118.1 (3) | C15—C14—C13 | 117.7 (3) |
C10—C11—H11 | 120.9 (19) | C15—C14—H14 | 117.4 (19) |
C12—C11—H11 | 121.0 (19) | C13—C14—H14 | 124.9 (19) |
C6—C5—C4 | 120.4 (2) | N2—C8—C7 | 113.5 (2) |
C6—C5—H5 | 120.4 (15) | N2—C8—H8A | 105.8 (17) |
C4—C5—H5 | 119.2 (15) | N2—C8—H8B | 107 (2) |
C6—C1—C2 | 119.4 (3) | C7—C8—H8A | 112.4 (18) |
C6—C1—H1A | 119.1 (17) | C7—C8—H8B | 108 (2) |
C2—C1—H1A | 121.4 (17) | H8A—C8—H8B | 110 (3) |
C5—C6—N1 | 119.3 (2) | C1—C2—H2 | 119 (2) |
C5—C6—C1 | 119.8 (3) | C3—C2—C1 | 120.3 (3) |
C1—C6—N1 | 120.8 (3) | C3—C2—H2 | 121.0 (19) |
C5—C4—H4 | 119.7 (18) | C11—C12—C13 | 121.1 (3) |
C3—C4—C5 | 119.5 (3) | C11—C12—H12 | 121 (2) |
C3—C4—H4 | 120.7 (18) | C13—C12—H12 | 118 (2) |
S1—N1—C6—C5 | −123.3 (2) | C4—C3—C2—C1 | −0.6 (5) |
S1—N1—C6—C1 | 59.3 (3) | C9—N2—C16—O4 | −178.0 (3) |
S1—C7—C8—N2 | −70.9 (3) | C9—N2—C16—C15 | 0.8 (3) |
Cl1—C3—C2—C1 | 179.7 (3) | C9—N2—C8—C7 | −69.7 (4) |
O1—S1—N1—C6 | −58.7 (2) | C9—C10—C11—C12 | 179.2 (3) |
O1—S1—C7—C8 | −60.0 (2) | C16—N2—C9—O3 | −179.3 (3) |
O2—S1—N1—C6 | 172.9 (2) | C16—N2—C9—C10 | 0.2 (3) |
O2—S1—C7—C8 | 70.7 (2) | C16—N2—C8—C7 | 111.3 (3) |
N1—S1—C7—C8 | −176.8 (2) | C16—C15—C10—C11 | −178.2 (2) |
C15—C10—C11—C12 | −0.8 (4) | C16—C15—C10—C9 | 1.7 (3) |
C15—C10—C9—N2 | −1.2 (3) | C16—C15—C14—C13 | 178.8 (3) |
C15—C10—C9—O3 | 178.2 (3) | C7—S1—N1—C6 | 58.2 (3) |
C10—C15—C16—N2 | −1.6 (3) | C14—C15—C10—C11 | 1.3 (4) |
C10—C15—C16—O4 | 177.2 (3) | C14—C15—C10—C9 | −178.8 (2) |
C10—C15—C14—C13 | −0.5 (4) | C14—C15—C16—N2 | 179.0 (3) |
C10—C11—C12—C13 | −0.3 (5) | C14—C15—C16—O4 | −2.2 (5) |
C11—C10—C9—N2 | 178.7 (3) | C14—C13—C12—C11 | 1.1 (5) |
C11—C10—C9—O3 | −1.8 (5) | C8—N2—C9—O3 | 1.6 (4) |
C5—C4—C3—Cl1 | −178.3 (2) | C8—N2—C9—C10 | −179.0 (2) |
C5—C4—C3—C2 | 2.0 (4) | C8—N2—C16—O4 | 1.1 (4) |
C6—C5—C4—C3 | −1.7 (4) | C8—N2—C16—C15 | 180.0 (2) |
C6—C1—C2—C3 | −1.0 (5) | C2—C1—C6—N1 | 178.7 (3) |
C4—C5—C6—N1 | −177.4 (2) | C2—C1—C6—C5 | 1.3 (5) |
C4—C5—C6—C1 | 0.0 (4) | C12—C13—C14—C15 | −0.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.75 (2) | 2.24 (2) | 2.961 (3) | 162 (2) |
C4—H4···O4ii | 0.89 (3) | 2.53 (2) | 3.196 (3) | 133 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
C16H13ClN2O4S | F(000) = 752 |
Mr = 364.79 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5652 (2) Å | Cell parameters from 2243 reflections |
b = 25.5022 (12) Å | θ = 3.7–28.6° |
c = 11.5536 (5) Å | µ = 0.39 mm−1 |
β = 97.800 (4)° | T = 293 K |
V = 1624.58 (12) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.15 × 0.09 mm |
Agilent Xcalibur Eos diffractometer | 3298 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2582 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.1333 pixels mm-1 | θmax = 26.4°, θmin = 3.2° |
ω scans | h = −5→6 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | k = −31→22 |
Tmin = 0.982, Tmax = 0.996 | l = −12→14 |
7040 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | All H-atom parameters refined |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3678P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3298 reflections | Δρmax = 0.19 e Å−3 |
269 parameters | Δρmin = −0.40 e Å−3 |
0 restraints |
C16H13ClN2O4S | V = 1624.58 (12) Å3 |
Mr = 364.79 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.5652 (2) Å | µ = 0.39 mm−1 |
b = 25.5022 (12) Å | T = 293 K |
c = 11.5536 (5) Å | 0.50 × 0.15 × 0.09 mm |
β = 97.800 (4)° |
Agilent Xcalibur Eos diffractometer | 3298 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | 2582 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.996 | Rint = 0.022 |
7040 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.101 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.19 e Å−3 |
3298 reflections | Δρmin = −0.40 e Å−3 |
269 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.57180 (11) | 0.26538 (2) | 0.08458 (7) | 0.0707 (2) | |
S1 | 0.03092 (9) | 0.09436 (2) | 0.03822 (4) | 0.04136 (16) | |
O1 | −0.0363 (3) | 0.12447 (7) | −0.06525 (12) | 0.0621 (5) | |
O2 | 0.2110 (3) | 0.05457 (6) | 0.03952 (14) | 0.0571 (4) | |
O3 | 0.2310 (3) | 0.00238 (6) | 0.31988 (13) | 0.0531 (4) | |
O4 | −0.4443 (2) | 0.10432 (6) | 0.31218 (12) | 0.0473 (4) | |
N1 | 0.1327 (3) | 0.13385 (7) | 0.14414 (15) | 0.0408 (4) | |
N2 | −0.1244 (3) | 0.05004 (6) | 0.28675 (13) | 0.0367 (4) | |
C1 | 0.0852 (4) | 0.19565 (9) | 0.29543 (19) | 0.0489 (5) | |
C2 | −0.0380 (5) | 0.23626 (11) | 0.3393 (2) | 0.0686 (8) | |
C3 | −0.2418 (5) | 0.25774 (11) | 0.2757 (2) | 0.0647 (7) | |
C4 | −0.3173 (4) | 0.23846 (8) | 0.1670 (2) | 0.0472 (5) | |
C5 | −0.1972 (4) | 0.19835 (8) | 0.11952 (19) | 0.0411 (5) | |
C6 | 0.0044 (3) | 0.17622 (7) | 0.18532 (16) | 0.0360 (4) | |
C7 | −0.2415 (3) | 0.06659 (8) | 0.07370 (17) | 0.0375 (4) | |
C8 | −0.2175 (4) | 0.02790 (8) | 0.17376 (18) | 0.0412 (5) | |
C9 | 0.0935 (3) | 0.03358 (7) | 0.35299 (17) | 0.0380 (4) | |
C10 | 0.1084 (3) | 0.06212 (7) | 0.46552 (16) | 0.0375 (4) | |
C11 | 0.2853 (4) | 0.06133 (9) | 0.56105 (19) | 0.0487 (5) | |
C12 | 0.2481 (5) | 0.09233 (10) | 0.6556 (2) | 0.0558 (6) | |
C13 | 0.0431 (5) | 0.12297 (10) | 0.6528 (2) | 0.0567 (6) | |
C14 | −0.1332 (4) | 0.12401 (9) | 0.55640 (19) | 0.0484 (5) | |
C15 | −0.0968 (3) | 0.09288 (7) | 0.46262 (16) | 0.0366 (4) | |
C16 | −0.2489 (3) | 0.08511 (7) | 0.34885 (16) | 0.0360 (4) | |
H7A | −0.350 (4) | 0.0969 (7) | 0.0854 (17) | 0.036 (5)* | |
H14 | −0.271 (4) | 0.1439 (8) | 0.5533 (17) | 0.042 (6)* | |
H7B | −0.301 (4) | 0.0496 (8) | 0.0047 (19) | 0.051 (6)* | |
H8A | −0.381 (4) | 0.0139 (8) | 0.1790 (18) | 0.048 (6)* | |
H8B | −0.107 (4) | −0.0013 (8) | 0.1612 (17) | 0.045 (6)* | |
H1A | 0.223 (4) | 0.1804 (8) | 0.3377 (18) | 0.046 (6)* | |
H11 | 0.425 (4) | 0.0413 (9) | 0.562 (2) | 0.059 (7)* | |
H5 | −0.246 (4) | 0.1862 (8) | 0.050 (2) | 0.049 (6)* | |
H1 | 0.246 (4) | 0.1223 (9) | 0.1910 (19) | 0.045 (6)* | |
H12 | 0.366 (5) | 0.0923 (10) | 0.721 (2) | 0.071 (8)* | |
H3 | −0.316 (5) | 0.2865 (11) | 0.306 (2) | 0.078 (8)* | |
H13 | 0.022 (4) | 0.1425 (9) | 0.715 (2) | 0.066 (7)* | |
H2 | 0.020 (5) | 0.2491 (11) | 0.413 (3) | 0.091 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0515 (3) | 0.0599 (4) | 0.0954 (5) | 0.0073 (3) | −0.0096 (3) | 0.0214 (3) |
S1 | 0.0345 (3) | 0.0566 (3) | 0.0341 (3) | −0.0054 (2) | 0.0089 (2) | −0.0095 (2) |
O1 | 0.0704 (11) | 0.0859 (12) | 0.0308 (8) | −0.0143 (9) | 0.0103 (7) | 0.0030 (8) |
O2 | 0.0370 (8) | 0.0699 (10) | 0.0664 (10) | 0.0019 (8) | 0.0141 (7) | −0.0268 (8) |
O3 | 0.0456 (8) | 0.0532 (9) | 0.0607 (10) | 0.0172 (7) | 0.0076 (7) | −0.0016 (7) |
O4 | 0.0358 (8) | 0.0567 (9) | 0.0484 (8) | 0.0123 (7) | 0.0021 (6) | −0.0009 (7) |
N1 | 0.0325 (8) | 0.0476 (10) | 0.0400 (10) | −0.0006 (8) | −0.0035 (8) | −0.0073 (8) |
N2 | 0.0366 (8) | 0.0395 (8) | 0.0340 (8) | 0.0051 (7) | 0.0049 (7) | 0.0000 (7) |
C1 | 0.0487 (12) | 0.0544 (13) | 0.0404 (12) | 0.0072 (11) | −0.0054 (10) | −0.0044 (10) |
C2 | 0.0779 (18) | 0.0743 (18) | 0.0486 (14) | 0.0214 (15) | −0.0094 (13) | −0.0201 (13) |
C3 | 0.0697 (16) | 0.0584 (15) | 0.0642 (16) | 0.0189 (14) | 0.0033 (13) | −0.0112 (13) |
C4 | 0.0420 (11) | 0.0422 (12) | 0.0557 (13) | 0.0009 (10) | 0.0010 (10) | 0.0108 (10) |
C5 | 0.0423 (11) | 0.0429 (11) | 0.0361 (11) | −0.0071 (10) | −0.0020 (9) | 0.0047 (9) |
C6 | 0.0344 (10) | 0.0376 (10) | 0.0360 (10) | −0.0044 (9) | 0.0048 (8) | 0.0018 (8) |
C7 | 0.0286 (9) | 0.0482 (12) | 0.0348 (10) | −0.0031 (9) | 0.0010 (8) | −0.0074 (9) |
C8 | 0.0401 (11) | 0.0407 (11) | 0.0426 (11) | −0.0017 (10) | 0.0048 (9) | −0.0057 (9) |
C9 | 0.0338 (10) | 0.0368 (10) | 0.0440 (11) | 0.0030 (9) | 0.0070 (8) | 0.0065 (9) |
C10 | 0.0381 (10) | 0.0368 (10) | 0.0373 (10) | −0.0005 (9) | 0.0044 (8) | 0.0085 (8) |
C11 | 0.0450 (12) | 0.0521 (13) | 0.0470 (13) | −0.0003 (11) | −0.0009 (10) | 0.0119 (10) |
C12 | 0.0612 (15) | 0.0617 (15) | 0.0404 (13) | −0.0097 (13) | −0.0080 (11) | 0.0089 (11) |
C13 | 0.0752 (17) | 0.0573 (14) | 0.0382 (12) | −0.0103 (14) | 0.0098 (12) | −0.0061 (11) |
C14 | 0.0530 (13) | 0.0497 (13) | 0.0439 (12) | 0.0029 (11) | 0.0117 (10) | −0.0018 (10) |
C15 | 0.0374 (10) | 0.0381 (10) | 0.0351 (10) | −0.0002 (9) | 0.0076 (8) | 0.0063 (8) |
C16 | 0.0337 (10) | 0.0375 (10) | 0.0377 (10) | 0.0009 (9) | 0.0086 (8) | 0.0043 (8) |
Cl1—C4 | 1.738 (2) | C5—C6 | 1.387 (3) |
S1—O1 | 1.4274 (16) | C5—H5 | 0.87 (2) |
S1—O2 | 1.4248 (16) | C7—C8 | 1.512 (3) |
S1—N1 | 1.6262 (17) | C7—H7A | 1.000 (19) |
S1—C7 | 1.7711 (19) | C7—H7B | 0.93 (2) |
O3—C9 | 1.202 (2) | C8—H8A | 0.99 (2) |
O4—C16 | 1.215 (2) | C8—H8B | 0.99 (2) |
N1—C6 | 1.413 (3) | C9—C10 | 1.482 (3) |
N1—H1 | 0.83 (2) | C10—C11 | 1.376 (3) |
N2—C8 | 1.452 (2) | C10—C15 | 1.382 (3) |
N2—C9 | 1.407 (2) | C11—C12 | 1.386 (3) |
N2—C16 | 1.389 (2) | C11—H11 | 0.93 (2) |
C1—C2 | 1.376 (3) | C12—C13 | 1.380 (4) |
C1—C6 | 1.382 (3) | C12—H12 | 0.93 (3) |
C1—H1A | 0.94 (2) | C13—C14 | 1.381 (3) |
C2—C3 | 1.378 (4) | C13—H13 | 0.90 (2) |
C2—H2 | 0.93 (3) | C14—C15 | 1.380 (3) |
C3—C4 | 1.360 (3) | C14—H14 | 0.92 (2) |
C3—H3 | 0.93 (3) | C15—C16 | 1.477 (3) |
C4—C5 | 1.376 (3) | ||
O1—S1—N1 | 108.78 (10) | C8—C7—H7A | 113.1 (11) |
O1—S1—C7 | 105.89 (10) | C8—C7—H7B | 109.7 (13) |
O2—S1—O1 | 119.73 (10) | H7A—C7—H7B | 108.9 (17) |
O2—S1—N1 | 105.09 (9) | N2—C8—C7 | 114.67 (16) |
O2—S1—C7 | 109.62 (10) | N2—C8—H8A | 107.8 (12) |
N1—S1—C7 | 107.17 (9) | N2—C8—H8B | 105.7 (12) |
S1—N1—H1 | 115.4 (16) | C7—C8—H8A | 107.2 (12) |
C6—N1—S1 | 125.93 (14) | C7—C8—H8B | 111.8 (11) |
C6—N1—H1 | 115.2 (15) | H8A—C8—H8B | 109.5 (16) |
C9—N2—C8 | 123.32 (16) | O3—C9—N2 | 124.27 (19) |
C16—N2—C8 | 124.91 (17) | O3—C9—C10 | 129.93 (19) |
C16—N2—C9 | 111.38 (16) | N2—C9—C10 | 105.80 (15) |
C2—C1—C6 | 119.5 (2) | C11—C10—C9 | 130.20 (19) |
C2—C1—H1A | 122.4 (13) | C11—C10—C15 | 121.77 (19) |
C6—C1—H1A | 118.1 (13) | C15—C10—C9 | 108.03 (17) |
C1—C2—C3 | 121.2 (2) | C10—C11—C12 | 117.2 (2) |
C1—C2—H2 | 118.2 (18) | C10—C11—H11 | 121.8 (14) |
C3—C2—H2 | 120.6 (18) | C12—C11—H11 | 121.0 (14) |
C2—C3—H3 | 119.2 (17) | C11—C12—H12 | 118.4 (16) |
C4—C3—C2 | 118.5 (2) | C13—C12—C11 | 121.1 (2) |
C4—C3—H3 | 122.1 (17) | C13—C12—H12 | 120.6 (16) |
C3—C4—Cl1 | 119.33 (18) | C12—C13—C14 | 121.6 (2) |
C3—C4—C5 | 122.1 (2) | C12—C13—H13 | 119.5 (16) |
C5—C4—Cl1 | 118.60 (18) | C14—C13—H13 | 118.9 (16) |
C4—C5—C6 | 119.0 (2) | C13—C14—H14 | 122.7 (13) |
C4—C5—H5 | 121.7 (14) | C15—C14—C13 | 117.3 (2) |
C6—C5—H5 | 119.3 (14) | C15—C14—H14 | 120.0 (13) |
C1—C6—N1 | 117.91 (18) | C10—C15—C16 | 108.50 (16) |
C1—C6—C5 | 119.76 (19) | C14—C15—C10 | 121.07 (19) |
C5—C6—N1 | 122.33 (18) | C14—C15—C16 | 130.43 (19) |
S1—C7—H7A | 105.8 (11) | O4—C16—N2 | 124.41 (18) |
S1—C7—H7B | 101.9 (13) | O4—C16—C15 | 129.33 (18) |
C8—C7—S1 | 116.65 (14) | N2—C16—C15 | 106.27 (16) |
Cl1—C4—C5—C6 | −179.24 (15) | C8—N2—C9—C10 | −174.67 (16) |
S1—N1—C6—C1 | 160.96 (16) | C8—N2—C16—O4 | −5.5 (3) |
S1—N1—C6—C5 | −18.8 (3) | C8—N2—C16—C15 | 174.53 (16) |
S1—C7—C8—N2 | 64.7 (2) | C9—N2—C8—C7 | −118.4 (2) |
O1—S1—N1—C6 | 58.08 (18) | C9—N2—C16—O4 | −178.48 (18) |
O1—S1—C7—C8 | 173.80 (15) | C9—N2—C16—C15 | 1.5 (2) |
O2—S1—N1—C6 | −172.55 (16) | C9—C10—C11—C12 | −179.51 (19) |
O2—S1—C7—C8 | 43.34 (18) | C9—C10—C15—C14 | 179.86 (17) |
O3—C9—C10—C11 | 1.4 (3) | C9—C10—C15—C16 | 0.0 (2) |
O3—C9—C10—C15 | −178.81 (19) | C10—C11—C12—C13 | −0.6 (3) |
N1—S1—C7—C8 | −70.20 (18) | C10—C15—C16—O4 | 179.11 (19) |
N2—C9—C10—C11 | −178.86 (19) | C10—C15—C16—N2 | −0.9 (2) |
N2—C9—C10—C15 | 0.9 (2) | C11—C10—C15—C14 | −0.3 (3) |
C1—C2—C3—C4 | −1.1 (4) | C11—C10—C15—C16 | 179.78 (17) |
C2—C1—C6—N1 | −178.8 (2) | C11—C12—C13—C14 | 0.1 (4) |
C2—C1—C6—C5 | 1.0 (3) | C12—C13—C14—C15 | 0.3 (3) |
C2—C3—C4—Cl1 | −179.3 (2) | C13—C14—C15—C10 | −0.2 (3) |
C2—C3—C4—C5 | 0.2 (4) | C13—C14—C15—C16 | 179.7 (2) |
C3—C4—C5—C6 | 1.2 (3) | C14—C15—C16—O4 | −0.8 (3) |
C4—C5—C6—N1 | 177.96 (17) | C14—C15—C16—N2 | 179.24 (19) |
C4—C5—C6—C1 | −1.8 (3) | C15—C10—C11—C12 | 0.7 (3) |
C6—C1—C2—C3 | 0.5 (4) | C16—N2—C8—C7 | 69.4 (2) |
C7—S1—N1—C6 | −55.98 (19) | C16—N2—C9—O3 | 178.21 (18) |
C8—N2—C9—O3 | 5.1 (3) | C16—N2—C9—C10 | −1.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.87 (2) | 2.46 (2) | 3.071 (3) | 128 (2) |
N1—H1···O4i | 0.83 (2) | 2.12 (2) | 2.939 (2) | 172 (2) |
C11—H11···O3ii | 0.93 (2) | 2.46 (2) | 3.282 (3) | 147 (2) |
C2—H2···Cl1iii | 0.93 (3) | 2.83 (3) | 3.573 (3) | 138 (2) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x+1, −y+1/2, z+1/2. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C16H13ClN2O4S | C16H13ClN2O4S | C16H13ClN2O4S |
Mr | 364.79 | 364.79 | 364.79 |
Crystal system, space group | Orthorhombic, P212121 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 5.4126 (2), 12.7656 (5), 22.6827 (8) | 7.5484 (7), 9.9887 (10), 11.2112 (10) | 5.5652 (2), 25.5022 (12), 11.5536 (5) |
α, β, γ (°) | 90, 90, 90 | 100.624 (8), 98.405 (7), 95.661 (8) | 90, 97.800 (4), 90 |
V (Å3) | 1567.26 (11) | 815.01 (13) | 1624.58 (12) |
Z | 4 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.40 | 0.39 | 0.39 |
Crystal size (mm) | 0.35 × 0.07 × 0.05 | 0.18 × 0.12 × 0.06 | 0.50 × 0.15 × 0.09 |
Data collection | |||
Diffractometer | Agilent Xcalibur Eos diffractometer | Agilent Xcalibur Eos diffractometer | Agilent Xcalibur Eos diffractometer |
Absorption correction | Analytical (CrysAlis PRO; Agilent, 2014) | Analytical (CrysAlis PRO; Agilent, 2014) | Analytical (CrysAlis PRO; Agilent, 2014) |
Tmin, Tmax | 0.989, 0.998 | 0.974, 0.991 | 0.982, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4676, 2894, 2484 | 5967, 3287, 2245 | 7040, 3298, 2582 |
Rint | 0.018 | 0.023 | 0.022 |
(sin θ/λ)max (Å−1) | 0.625 | 0.625 | 0.625 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.082, 1.06 | 0.044, 0.117, 1.02 | 0.040, 0.101, 1.04 |
No. of reflections | 2894 | 3287 | 3298 |
No. of parameters | 269 | 269 | 269 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.22, −0.29 | 0.36, −0.37 | 0.19, −0.40 |
Absolute structure | Flack x parameter determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) | ? | ? |
Absolute structure parameter | 0.02 (4) | ? | ? |
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS (Sheldrick, 2008), SHELXL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.84 (4) | 2.24 (3) | 2.984 (4) | 148 (3) |
C5—H5···O1 | 0.96 (4) | 2.24 (4) | 2.912 (5) | 127 (3) |
C7—H7A···O4i | 0.90 (4) | 2.48 (4) | 3.123 (5) | 129 (3) |
C7—H7B···O2ii | 0.92 (3) | 2.52 (3) | 3.174 (4) | 128 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.75 (2) | 2.24 (2) | 2.961 (3) | 162 (2) |
C4—H4···O4ii | 0.89 (3) | 2.53 (2) | 3.196 (3) | 133 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.87 (2) | 2.46 (2) | 3.071 (3) | 128 (2) |
N1—H1···O4i | 0.83 (2) | 2.12 (2) | 2.939 (2) | 172 (2) |
C11—H11···O3ii | 0.93 (2) | 2.46 (2) | 3.282 (3) | 147 (2) |
C2—H2···Cl1iii | 0.93 (3) | 2.83 (3) | 3.573 (3) | 138 (2) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x+1, −y+1/2, z+1/2. |
Cl1—C1 | 1.742 (4) | S1—C7 | 1.768 (4) |
S1—O1 | 1.424 (3) | N2—C8 | 1.455 (4) |
S1—O2 | 1.428 (3) | C7—C8 | 1.514 (5) |
S1—N1 | 1.629 (3) | ||
O1—S1—O2 | 119.32 (15) | O2—S1—C7 | 107.94 (16) |
O1—S1—N1 | 109.09 (16) | N1—S1—C7 | 106.13 (17) |
O1—S1—C7 | 108.21 (17) | C8—C7—S1 | 115.6 (3) |
O2—S1—N1 | 105.43 (16) | N2—C8—C7 | 115.0 (3) |
S1—C7—C8—N2 | −62.7 (4) | N1—S1—C7—C8 | −52.0 (3) |
S1—O1 | 1.4214 (18) | Cl1—C3 | 1.729 (3) |
S1—O2 | 1.4333 (17) | N2—C8 | 1.445 (3) |
S1—N1 | 1.626 (3) | C7—C8 | 1.522 (4) |
S1—C7 | 1.764 (3) | ||
O1—S1—O2 | 118.61 (11) | O2—S1—C7 | 108.63 (13) |
O1—S1—N1 | 108.99 (13) | N1—S1—C7 | 105.05 (13) |
O1—S1—C7 | 109.18 (13) | C8—C7—S1 | 114.2 (2) |
O2—S1—N1 | 105.52 (12) | N2—C8—C7 | 113.5 (2) |
S1—C7—C8—N2 | −70.9 (3) | N1—S1—C7—C8 | −176.8 (2) |
Cl1—C4 | 1.738 (2) | S1—C7 | 1.7711 (19) |
S1—O1 | 1.4274 (16) | N2—C8 | 1.452 (2) |
S1—O2 | 1.4248 (16) | C7—C8 | 1.512 (3) |
S1—N1 | 1.6262 (17) | ||
O1—S1—N1 | 108.78 (10) | O2—S1—C7 | 109.62 (10) |
O1—S1—C7 | 105.89 (10) | N1—S1—C7 | 107.17 (9) |
O2—S1—O1 | 119.73 (10) | C8—C7—S1 | 116.65 (14) |
O2—S1—N1 | 105.09 (9) | N2—C8—C7 | 114.67 (16) |
S1—C7—C8—N2 | 64.7 (2) | N1—S1—C7—C8 | −70.20 (18) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register