Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015011342/su5144sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989015011342/su5144Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015011342/su5144Isup3.cml |
CCDC reference: 1406065
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.010 Å
- R factor = 0.056
- wR factor = 0.129
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.973 Note PLAT234_ALERT_4_C Large Hirshfeld Difference C6A -- C7A .. 0.17 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0099 Ang. PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.167 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.597 76 Report PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 86 %
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 36.87 Why ? PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 22 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The reactions of substrates with one or two sulfanyl chloride, acid chloride, and/or (alkoxydichloromethyl)sulfanyl moieties have been of interest to our laboratory for some time (Barany et al., 1983; Barany & Mott, 1984; Schroll & Barany, 1986; Schroll et al., 1990, 2012). In some of these experiments, bis[methyl(phenyl)amino]trisulfane was a component of more complicated mixtures of polysulfanes with varying numbers of S atoms. One such mixture was separated by preparative HPLC at 298 K, eluting with methanol–water (17:3). The fraction containing the title compound (dissolved in the eluting solvent) was cooled to 277 K, after which the trisulfane was obtained directly in crystalline form.
The title compound, (1), was obtained in crystalline form after preparative HPLC, as described by Schroll & Barany (1986). The proposed molecular structure of (1) was confirmed by single-crystal X-ray analysis at 173 K. The molecules do not take advantage of the twofold axis provided as an available symmetry option by the Fdd2 space group. Instead, there are two molecules, (1a) and (1b), in the asymmetric unit, and both of them display a pseudo-trans conformation. All bond distances and angles in both molecules are within expected ranges. Selected geometric parameters for compound (1) are given in Table 1. The two consecutive S—S bond lengths (comprising the trisulfane) of molecule (1a) are 2.064 (3) and 2.078 (3) Å, and for molecule (1b) are 2.076 (3) and 2.067 (2) Å. These values are similar to the value of 2.07 Å reported for the S—S bond length in elemental sulfur (S8). Torsion angles about each of the two S—S bonds (comprising the trisulfane) are, respectively, 86.6 (2) and 87.0 (2)° for (1a), and -84.6 (2) and -85.9 (2)° for (1b). The core atoms, viz. the N—S—S—S—N moiety, of the two units superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enantiomers. Moreover, with respect to the four measured torsion angles, which range in absolute value from 84.6 (2) to 87.0 (2)°, these are slightly smaller than the theoretical optimum of 90.0° (Pauling, 1949; Torrico-Vallejos et al., 2010). Finally, given the presence of three consecutive linearly connected sulfur atoms, representing two dihedral angles close to 90°, it is noteworthy that both of the molecules in the asymmetric unit display a pseudo-trans conformation (torsion angles +,+ or -,- across the two S—S bonds). The theoretically possible pseudo-cis (torsion angles +,- or -,+) conformation (Meyer, 1976) was not observed for these structures.
In the crystal of (1), molecules are linked via C—H···π interactions, forming sheets lying parallel to (010) (see Table 2 and Fig. 2).
A search of the Cambridge Structural Database (CSD, Version 5.36, May 2015; Groom & Allen, 2014) revealed the presence of two compounds (see Fig. 3) that also have an N—S—S—S—N moiety, viz. bis(oxamido)trisulfane, (2) (CSD refcode GEHPUE; Brunn et al., 1988), and bis[tert-butyl(di-tert-butylfluorosilyl)amino]trisulfane, (3) (SOTLAO; Klingebiel et al., 1991). Unlike the title compound, (1), compounds (2) and (3) each have a unique conformation in the unit cell (Z' = 1). Selected geometric parameters of (1) and the comparison compounds, (2) and (3), are given in Table 1. While the average S—S bond length of the title compound is ca 2.07 Å, the corresponding value is longer (2.09 Å) in (3) and shorter (2.04 Å) in (2). The absolute value of the average torsion angle of the title compound (1) is ca 86.0°, while the corresponding value is larger (93.2 and -89.5°) and closer to the theoretical optimum in (2), and significantly larger (109.7 and 95.9°) in (3).
Note regarding nomenclature: In the discussion above, a consistent nomenclature scheme has been used that differs from the names used in the original publications, viz. bis(oxamido)trisulfan, (2) (Brunn et al., 1988) and 1,3-bis[tert-butyl(di-tert-butylfluorsilyl)amino]trisulfan, (3) (Klingebiel et al., 1991).
The title compound, (1), was synthesized and obtained in crystalline form after preparative HPLC, as described by Schroll & Barany (1986): compound (37) in that publication.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C14H16N2S3 | Dx = 1.348 Mg m−3 |
Mr = 308.47 | Melting point: 353 K |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 1945 reflections |
a = 19.284 (3) Å | θ = 2.4–24.9° |
b = 56.440 (8) Å | µ = 0.48 mm−1 |
c = 11.1695 (15) Å | T = 173 K |
V = 12157 (3) Å3 | Plate, colorless |
Z = 32 | 0.25 × 0.22 × 0.04 mm |
F(000) = 5184 |
Bruker SMART CCD area-detector diffractometer | 4978 independent reflections |
Radiation source: sealed tube | 3097 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = 0→22 |
Tmin = 0.890, Tmax = 0.981 | k = 0→67 |
15884 measured reflections | l = −13→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0357P)2 + 36.8709P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4978 reflections | Δρmax = 0.43 e Å−3 |
347 parameters | Δρmin = −0.31 e Å−3 |
1 restraint | Absolute structure: 2194 Friedel pairs (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.08 (12) |
C14H16N2S3 | V = 12157 (3) Å3 |
Mr = 308.47 | Z = 32 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 19.284 (3) Å | µ = 0.48 mm−1 |
b = 56.440 (8) Å | T = 173 K |
c = 11.1695 (15) Å | 0.25 × 0.22 × 0.04 mm |
Bruker SMART CCD area-detector diffractometer | 4978 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3097 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.981 | Rint = 0.075 |
15884 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0357P)2 + 36.8709P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | Δρmax = 0.43 e Å−3 |
4978 reflections | Δρmin = −0.31 e Å−3 |
347 parameters | Absolute structure: 2194 Friedel pairs (Flack, 1983) |
1 restraint | Absolute structure parameter: 0.08 (12) |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.16203 (9) | 0.35562 (3) | 0.42989 (17) | 0.0509 (5) | |
S2A | 0.13888 (9) | 0.37674 (3) | 0.28446 (18) | 0.0512 (5) | |
S3A | 0.05789 (9) | 0.39854 (3) | 0.33839 (17) | 0.0529 (5) | |
N1A | 0.1096 (2) | 0.33225 (10) | 0.4230 (5) | 0.0430 (14) | |
N2A | 0.0925 (3) | 0.42227 (10) | 0.4033 (5) | 0.0460 (14) | |
C1A | 0.0371 (3) | 0.33682 (13) | 0.4515 (6) | 0.0555 (19) | |
H1AA | 0.0155 | 0.3222 | 0.4809 | 0.083* | |
H1AB | 0.0129 | 0.3422 | 0.3794 | 0.083* | |
H1AC | 0.0343 | 0.3491 | 0.5133 | 0.083* | |
C2A | 0.1179 (4) | 0.41859 (13) | 0.5256 (6) | 0.063 (2) | |
H2AA | 0.1143 | 0.4334 | 0.5706 | 0.095* | |
H2AB | 0.1665 | 0.4135 | 0.5230 | 0.095* | |
H2AC | 0.0899 | 0.4064 | 0.5649 | 0.095* | |
C3A | 0.1249 (3) | 0.31310 (11) | 0.3459 (6) | 0.0428 (18) | |
C4A | 0.1941 (3) | 0.30690 (11) | 0.3200 (6) | 0.0501 (19) | |
H4AA | 0.2307 | 0.3164 | 0.3502 | 0.060* | |
C5A | 0.2096 (4) | 0.28734 (13) | 0.2520 (7) | 0.059 (2) | |
H5AA | 0.2567 | 0.2832 | 0.2383 | 0.071* | |
C6A | 0.1577 (4) | 0.27368 (13) | 0.2037 (7) | 0.056 (2) | |
H6AA | 0.1684 | 0.2605 | 0.1544 | 0.067* | |
C7A | 0.0894 (5) | 0.27962 (12) | 0.2284 (7) | 0.063 (2) | |
H7AA | 0.0531 | 0.2699 | 0.1980 | 0.076* | |
C8A | 0.0733 (3) | 0.29903 (12) | 0.2953 (7) | 0.0514 (19) | |
H8AA | 0.0260 | 0.3030 | 0.3076 | 0.062* | |
C9A | 0.1215 (3) | 0.44089 (11) | 0.3334 (7) | 0.0408 (17) | |
C10A | 0.1734 (3) | 0.45591 (12) | 0.3798 (6) | 0.0458 (19) | |
H10A | 0.1906 | 0.4533 | 0.4584 | 0.055* | |
C11A | 0.1992 (3) | 0.47418 (11) | 0.3132 (7) | 0.052 (2) | |
H11A | 0.2340 | 0.4841 | 0.3462 | 0.062* | |
C12A | 0.1756 (4) | 0.47837 (12) | 0.2001 (8) | 0.055 (2) | |
H12A | 0.1935 | 0.4912 | 0.1542 | 0.066* | |
C13A | 0.1253 (4) | 0.46368 (12) | 0.1536 (7) | 0.055 (2) | |
H13A | 0.1086 | 0.4665 | 0.0749 | 0.066* | |
C14A | 0.0987 (4) | 0.44514 (12) | 0.2171 (7) | 0.0514 (19) | |
H14A | 0.0646 | 0.4352 | 0.1821 | 0.062* | |
S1B | 0.34517 (9) | 0.60013 (3) | 0.43382 (17) | 0.0503 (5) | |
S2B | 0.35517 (9) | 0.62207 (3) | 0.28572 (18) | 0.0504 (5) | |
S3B | 0.44058 (9) | 0.64310 (3) | 0.32075 (16) | 0.0473 (5) | |
N1B | 0.3972 (2) | 0.57722 (9) | 0.4127 (5) | 0.0406 (13) | |
N2B | 0.4133 (3) | 0.66599 (9) | 0.3995 (5) | 0.0410 (14) | |
C1B | 0.4706 (3) | 0.58075 (12) | 0.4394 (7) | 0.056 (2) | |
H1BA | 0.4893 | 0.5665 | 0.4775 | 0.084* | |
H1BB | 0.4758 | 0.5943 | 0.4936 | 0.084* | |
H1BC | 0.4958 | 0.5839 | 0.3649 | 0.084* | |
C2B | 0.3957 (4) | 0.66091 (11) | 0.5245 (6) | 0.0502 (18) | |
H2BA | 0.4010 | 0.6754 | 0.5724 | 0.075* | |
H2BB | 0.4269 | 0.6486 | 0.5554 | 0.075* | |
H2BC | 0.3477 | 0.6554 | 0.5293 | 0.075* | |
C3B | 0.3785 (3) | 0.55805 (10) | 0.3387 (6) | 0.0360 (15) | |
C4B | 0.4264 (3) | 0.54146 (11) | 0.2998 (6) | 0.0470 (18) | |
H4BA | 0.4739 | 0.5435 | 0.3201 | 0.056* | |
C5B | 0.4072 (4) | 0.52205 (12) | 0.2322 (6) | 0.0528 (19) | |
H5BA | 0.4413 | 0.5108 | 0.2098 | 0.063* | |
C6B | 0.3392 (4) | 0.51874 (12) | 0.1965 (7) | 0.052 (2) | |
H6BA | 0.3259 | 0.5056 | 0.1486 | 0.062* | |
C7B | 0.2916 (3) | 0.53537 (11) | 0.2336 (6) | 0.0467 (18) | |
H7BA | 0.2444 | 0.5335 | 0.2110 | 0.056* | |
C8B | 0.3098 (3) | 0.55452 (10) | 0.3020 (6) | 0.0418 (16) | |
H8BA | 0.2753 | 0.5656 | 0.3249 | 0.050* | |
C9B | 0.3837 (3) | 0.68621 (10) | 0.3444 (7) | 0.0369 (16) | |
C10B | 0.3412 (3) | 0.70186 (10) | 0.4077 (6) | 0.0446 (18) | |
H10B | 0.3288 | 0.6984 | 0.4881 | 0.054* | |
C11B | 0.3175 (4) | 0.72197 (13) | 0.3558 (8) | 0.060 (2) | |
H11B | 0.2898 | 0.7326 | 0.4015 | 0.072* | |
C12B | 0.3328 (4) | 0.72757 (12) | 0.2363 (8) | 0.054 (2) | |
H12B | 0.3158 | 0.7417 | 0.2003 | 0.065* | |
C13B | 0.3730 (3) | 0.71203 (11) | 0.1735 (7) | 0.0481 (17) | |
H13B | 0.3840 | 0.7153 | 0.0922 | 0.058* | |
C14B | 0.3981 (3) | 0.69158 (11) | 0.2259 (7) | 0.0436 (17) | |
H14B | 0.4257 | 0.6810 | 0.1800 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0414 (11) | 0.0603 (11) | 0.0510 (14) | 0.0036 (8) | −0.0136 (9) | −0.0069 (10) |
S2A | 0.0612 (11) | 0.0511 (10) | 0.0414 (12) | −0.0137 (8) | 0.0091 (10) | −0.0026 (10) |
S3A | 0.0373 (10) | 0.0635 (11) | 0.0577 (14) | −0.0058 (8) | −0.0102 (9) | 0.0142 (10) |
N1A | 0.032 (3) | 0.054 (3) | 0.043 (4) | 0.006 (2) | −0.002 (3) | 0.008 (3) |
N2A | 0.049 (3) | 0.054 (4) | 0.035 (4) | 0.005 (3) | 0.000 (3) | 0.001 (3) |
C1A | 0.029 (4) | 0.085 (5) | 0.053 (5) | 0.000 (3) | 0.002 (3) | 0.019 (4) |
C2A | 0.070 (5) | 0.090 (5) | 0.029 (5) | 0.029 (4) | −0.007 (4) | −0.003 (4) |
C3A | 0.033 (4) | 0.050 (4) | 0.046 (5) | −0.006 (3) | −0.005 (3) | 0.017 (4) |
C4A | 0.038 (4) | 0.055 (4) | 0.057 (6) | −0.003 (3) | −0.008 (4) | −0.005 (4) |
C5A | 0.058 (5) | 0.057 (5) | 0.062 (6) | −0.004 (4) | 0.001 (4) | 0.000 (4) |
C6A | 0.072 (6) | 0.055 (5) | 0.041 (5) | −0.008 (4) | −0.002 (4) | 0.006 (3) |
C7A | 0.084 (6) | 0.049 (5) | 0.056 (6) | −0.024 (4) | −0.029 (4) | 0.018 (4) |
C8A | 0.042 (4) | 0.053 (4) | 0.060 (6) | −0.010 (3) | −0.015 (4) | 0.014 (4) |
C9A | 0.030 (4) | 0.049 (4) | 0.043 (5) | 0.014 (3) | −0.001 (3) | −0.005 (3) |
C10A | 0.042 (4) | 0.059 (4) | 0.037 (5) | 0.011 (3) | −0.013 (3) | −0.018 (3) |
C11A | 0.047 (4) | 0.035 (4) | 0.074 (7) | 0.001 (3) | −0.012 (4) | −0.018 (4) |
C12A | 0.061 (5) | 0.035 (4) | 0.069 (6) | 0.005 (3) | 0.007 (4) | −0.002 (4) |
C13A | 0.067 (5) | 0.050 (4) | 0.050 (6) | 0.002 (4) | −0.012 (4) | 0.000 (4) |
C14A | 0.052 (4) | 0.050 (4) | 0.052 (6) | −0.005 (3) | −0.019 (4) | −0.004 (4) |
S1B | 0.0489 (11) | 0.0517 (10) | 0.0502 (14) | −0.0096 (8) | 0.0123 (10) | −0.0097 (9) |
S2B | 0.0595 (11) | 0.0440 (10) | 0.0476 (12) | 0.0073 (8) | −0.0123 (10) | −0.0093 (9) |
S3B | 0.0400 (10) | 0.0478 (10) | 0.0540 (14) | 0.0062 (7) | 0.0123 (9) | 0.0058 (8) |
N1B | 0.039 (3) | 0.041 (3) | 0.041 (4) | −0.011 (2) | −0.004 (3) | 0.005 (3) |
N2B | 0.039 (3) | 0.045 (3) | 0.039 (4) | −0.004 (2) | −0.002 (3) | −0.002 (3) |
C1B | 0.045 (4) | 0.061 (4) | 0.062 (6) | −0.011 (3) | −0.016 (4) | 0.009 (4) |
C2B | 0.057 (4) | 0.061 (4) | 0.033 (5) | −0.014 (3) | −0.003 (4) | 0.002 (4) |
C3B | 0.039 (4) | 0.040 (4) | 0.028 (4) | −0.007 (3) | 0.004 (3) | 0.007 (3) |
C4B | 0.037 (4) | 0.057 (4) | 0.047 (5) | 0.013 (3) | 0.000 (4) | 0.009 (4) |
C5B | 0.050 (5) | 0.056 (4) | 0.052 (5) | 0.016 (3) | 0.002 (4) | −0.008 (4) |
C6B | 0.060 (5) | 0.047 (4) | 0.049 (6) | 0.001 (3) | 0.006 (4) | −0.001 (3) |
C7B | 0.041 (4) | 0.050 (4) | 0.049 (5) | −0.012 (3) | −0.001 (3) | −0.005 (3) |
C8B | 0.034 (4) | 0.045 (4) | 0.047 (5) | 0.004 (3) | 0.001 (3) | −0.002 (3) |
C9B | 0.029 (3) | 0.037 (4) | 0.045 (5) | −0.007 (3) | 0.002 (3) | −0.014 (3) |
C10B | 0.051 (4) | 0.045 (4) | 0.037 (5) | −0.004 (3) | 0.001 (3) | −0.005 (3) |
C11B | 0.061 (5) | 0.048 (5) | 0.071 (7) | 0.003 (4) | 0.000 (5) | −0.015 (4) |
C12B | 0.051 (4) | 0.041 (4) | 0.071 (6) | 0.004 (3) | −0.013 (4) | −0.007 (4) |
C13B | 0.042 (4) | 0.057 (4) | 0.045 (5) | −0.002 (3) | 0.005 (4) | 0.005 (4) |
C14B | 0.044 (4) | 0.042 (4) | 0.044 (5) | 0.004 (3) | 0.017 (3) | −0.006 (3) |
S1A—N1A | 1.664 (5) | S1B—N1B | 1.653 (5) |
S1A—S2A | 2.064 (3) | S1B—S2B | 2.076 (3) |
S2A—S3A | 2.078 (3) | S2B—S3B | 2.067 (2) |
S3A—N2A | 1.663 (6) | S3B—N2B | 1.649 (5) |
N1A—C3A | 1.413 (8) | N1B—C3B | 1.408 (8) |
N1A—C1A | 1.457 (7) | N1B—C1B | 1.460 (7) |
N2A—C9A | 1.424 (8) | N2B—C9B | 1.416 (8) |
N2A—C2A | 1.465 (8) | N2B—C2B | 1.465 (8) |
C1A—H1AA | 0.9800 | C1B—H1BA | 0.9800 |
C1A—H1AB | 0.9800 | C1B—H1BB | 0.9800 |
C1A—H1AC | 0.9800 | C1B—H1BC | 0.9800 |
C2A—H2AA | 0.9800 | C2B—H2BA | 0.9800 |
C2A—H2AB | 0.9800 | C2B—H2BB | 0.9800 |
C2A—H2AC | 0.9800 | C2B—H2BC | 0.9800 |
C3A—C8A | 1.393 (8) | C3B—C4B | 1.386 (8) |
C3A—C4A | 1.410 (9) | C3B—C8B | 1.401 (8) |
C4A—C5A | 1.373 (9) | C4B—C5B | 1.381 (9) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.373 (9) | C5B—C6B | 1.383 (9) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.388 (10) | C6B—C7B | 1.377 (9) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C8A | 1.362 (10) | C7B—C8B | 1.369 (8) |
C7A—H7AA | 0.9500 | C7B—H7BA | 0.9500 |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—C14A | 1.392 (9) | C9B—C14B | 1.386 (9) |
C9A—C10A | 1.410 (9) | C9B—C10B | 1.396 (8) |
C10A—C11A | 1.365 (9) | C10B—C11B | 1.354 (9) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.363 (10) | C11B—C12B | 1.403 (10) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.378 (9) | C12B—C13B | 1.365 (9) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.365 (9) | C13B—C14B | 1.382 (9) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
N1A—S1A—S2A | 106.9 (2) | N1B—S1B—S2B | 107.3 (2) |
S1A—S2A—S3A | 106.05 (11) | S3B—S2B—S1B | 105.41 (11) |
N2A—S3A—S2A | 107.6 (2) | N2B—S3B—S2B | 107.2 (2) |
C3A—N1A—C1A | 118.0 (5) | C3B—N1B—C1B | 118.2 (5) |
C3A—N1A—S1A | 120.5 (4) | C3B—N1B—S1B | 122.0 (4) |
C1A—N1A—S1A | 115.6 (4) | C1B—N1B—S1B | 116.9 (4) |
C9A—N2A—C2A | 119.0 (6) | C9B—N2B—C2B | 118.6 (5) |
C9A—N2A—S3A | 120.9 (5) | C9B—N2B—S3B | 121.9 (5) |
C2A—N2A—S3A | 115.3 (5) | C2B—N2B—S3B | 115.4 (4) |
N1A—C1A—H1AA | 109.5 | N1B—C1B—H1BA | 109.5 |
N1A—C1A—H1AB | 109.5 | N1B—C1B—H1BB | 109.5 |
H1AA—C1A—H1AB | 109.5 | H1BA—C1B—H1BB | 109.5 |
N1A—C1A—H1AC | 109.5 | N1B—C1B—H1BC | 109.5 |
H1AA—C1A—H1AC | 109.5 | H1BA—C1B—H1BC | 109.5 |
H1AB—C1A—H1AC | 109.5 | H1BB—C1B—H1BC | 109.5 |
N2A—C2A—H2AA | 109.5 | N2B—C2B—H2BA | 109.5 |
N2A—C2A—H2AB | 109.5 | N2B—C2B—H2BB | 109.5 |
H2AA—C2A—H2AB | 109.5 | H2BA—C2B—H2BB | 109.5 |
N2A—C2A—H2AC | 109.5 | N2B—C2B—H2BC | 109.5 |
H2AA—C2A—H2AC | 109.5 | H2BA—C2B—H2BC | 109.5 |
H2AB—C2A—H2AC | 109.5 | H2BB—C2B—H2BC | 109.5 |
C8A—C3A—C4A | 116.9 (7) | C4B—C3B—C8B | 116.3 (6) |
C8A—C3A—N1A | 122.3 (6) | C4B—C3B—N1B | 122.2 (6) |
C4A—C3A—N1A | 120.8 (6) | C8B—C3B—N1B | 121.5 (6) |
C5A—C4A—C3A | 121.2 (6) | C5B—C4B—C3B | 121.8 (6) |
C5A—C4A—H4AA | 119.4 | C5B—C4B—H4BA | 119.1 |
C3A—C4A—H4AA | 119.4 | C3B—C4B—H4BA | 119.1 |
C4A—C5A—C6A | 120.7 (7) | C4B—C5B—C6B | 121.3 (6) |
C4A—C5A—H5AA | 119.6 | C4B—C5B—H5BA | 119.3 |
C6A—C5A—H5AA | 119.6 | C6B—C5B—H5BA | 119.3 |
C5A—C6A—C7A | 118.6 (8) | C7B—C6B—C5B | 116.9 (7) |
C5A—C6A—H6AA | 120.7 | C7B—C6B—H6BA | 121.5 |
C7A—C6A—H6AA | 120.7 | C5B—C6B—H6BA | 121.5 |
C8A—C7A—C6A | 121.3 (7) | C8B—C7B—C6B | 122.3 (6) |
C8A—C7A—H7AA | 119.3 | C8B—C7B—H7BA | 118.8 |
C6A—C7A—H7AA | 119.3 | C6B—C7B—H7BA | 118.8 |
C7A—C8A—C3A | 121.2 (7) | C7B—C8B—C3B | 121.2 (6) |
C7A—C8A—H8AA | 119.4 | C7B—C8B—H8BA | 119.4 |
C3A—C8A—H8AA | 119.4 | C3B—C8B—H8BA | 119.4 |
C14A—C9A—C10A | 117.7 (6) | C14B—C9B—C10B | 117.5 (6) |
C14A—C9A—N2A | 121.0 (6) | C14B—C9B—N2B | 120.7 (6) |
C10A—C9A—N2A | 121.4 (6) | C10B—C9B—N2B | 121.8 (7) |
C11A—C10A—C9A | 120.8 (7) | C11B—C10B—C9B | 120.8 (7) |
C11A—C10A—H10A | 119.6 | C11B—C10B—H10B | 119.6 |
C9A—C10A—H10A | 119.6 | C9B—C10B—H10B | 119.6 |
C12A—C11A—C10A | 121.0 (7) | C10B—C11B—C12B | 121.6 (7) |
C12A—C11A—H11A | 119.5 | C10B—C11B—H11B | 119.2 |
C10A—C11A—H11A | 119.5 | C12B—C11B—H11B | 119.2 |
C11A—C12A—C13A | 118.6 (7) | C13B—C12B—C11B | 117.6 (7) |
C11A—C12A—H12A | 120.7 | C13B—C12B—H12B | 121.2 |
C13A—C12A—H12A | 120.7 | C11B—C12B—H12B | 121.2 |
C14A—C13A—C12A | 122.1 (7) | C12B—C13B—C14B | 121.2 (7) |
C14A—C13A—H13A | 119.0 | C12B—C13B—H13B | 119.4 |
C12A—C13A—H13A | 119.0 | C14B—C13B—H13B | 119.4 |
C13A—C14A—C9A | 119.8 (7) | C13B—C14B—C9B | 121.2 (6) |
C13A—C14A—H14A | 120.1 | C13B—C14B—H14B | 119.4 |
C9A—C14A—H14A | 120.1 | C9B—C14B—H14B | 119.4 |
N1A—S1A—S2A—S3A | 86.6 (2) | N1B—S1B—S2B—S3B | −84.6 (2) |
S1A—S2A—S3A—N2A | 87.0 (2) | S1B—S2B—S3B—N2B | −85.9 (2) |
S2A—S1A—N1A—C3A | 80.2 (5) | S2B—S1B—N1B—C3B | −79.9 (5) |
S2A—S1A—N1A—C1A | −72.2 (5) | S2B—S1B—N1B—C1B | 80.3 (5) |
S2A—S3A—N2A—C9A | 77.9 (5) | S2B—S3B—N2B—C9B | −83.1 (5) |
S2A—S3A—N2A—C2A | −77.0 (5) | S2B—S3B—N2B—C2B | 73.7 (5) |
C1A—N1A—C3A—C8A | 1.3 (9) | C1B—N1B—C3B—C4B | 5.8 (9) |
S1A—N1A—C3A—C8A | −150.5 (5) | S1B—N1B—C3B—C4B | 165.7 (5) |
C1A—N1A—C3A—C4A | −176.4 (6) | C1B—N1B—C3B—C8B | −175.2 (6) |
S1A—N1A—C3A—C4A | 31.7 (8) | S1B—N1B—C3B—C8B | −15.3 (8) |
C8A—C3A—C4A—C5A | −2.5 (10) | C8B—C3B—C4B—C5B | −2.3 (10) |
N1A—C3A—C4A—C5A | 175.4 (6) | N1B—C3B—C4B—C5B | 176.7 (6) |
C3A—C4A—C5A—C6A | 2.3 (12) | C3B—C4B—C5B—C6B | 2.4 (11) |
C4A—C5A—C6A—C7A | −2.2 (11) | C4B—C5B—C6B—C7B | −1.4 (11) |
C5A—C6A—C7A—C8A | 2.5 (11) | C5B—C6B—C7B—C8B | 0.5 (11) |
C6A—C7A—C8A—C3A | −2.8 (11) | C6B—C7B—C8B—C3B | −0.6 (11) |
C4A—C3A—C8A—C7A | 2.8 (10) | C4B—C3B—C8B—C7B | 1.4 (10) |
N1A—C3A—C8A—C7A | −175.1 (6) | N1B—C3B—C8B—C7B | −177.6 (6) |
C2A—N2A—C9A—C14A | −179.5 (6) | C2B—N2B—C9B—C14B | −179.3 (5) |
S3A—N2A—C9A—C14A | 26.5 (8) | S3B—N2B—C9B—C14B | −23.2 (8) |
C2A—N2A—C9A—C10A | −0.7 (8) | C2B—N2B—C9B—C10B | 3.1 (9) |
S3A—N2A—C9A—C10A | −154.7 (5) | S3B—N2B—C9B—C10B | 159.1 (5) |
C14A—C9A—C10A—C11A | 1.1 (9) | C14B—C9B—C10B—C11B | −2.5 (10) |
N2A—C9A—C10A—C11A | −177.8 (6) | N2B—C9B—C10B—C11B | 175.2 (6) |
C9A—C10A—C11A—C12A | −0.1 (10) | C9B—C10B—C11B—C12B | 1.8 (11) |
C10A—C11A—C12A—C13A | −0.3 (10) | C10B—C11B—C12B—C13B | −0.3 (10) |
C11A—C12A—C13A—C14A | −0.2 (11) | C11B—C12B—C13B—C14B | −0.4 (10) |
C12A—C13A—C14A—C9A | 1.1 (11) | C12B—C13B—C14B—C9B | −0.4 (10) |
C10A—C9A—C14A—C13A | −1.5 (10) | C10B—C9B—C14B—C13B | 1.8 (9) |
N2A—C9A—C14A—C13A | 177.4 (6) | N2B—C9B—C14B—C13B | −175.9 (6) |
Cg1, Cg2, Cg3, and Cg4 are the centroids of rings C3A–C8A, C9A–C14A, C3B–C8B, and C9B–C14B, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1AA···Cg2i | 0.98 | 2.91 | 3.810 (7) | 153 |
C2A—H2AA···Cg3ii | 0.98 | 2.76 | 3.658 (8) | 153 |
C1B—H1BA···Cg4iii | 0.98 | 2.73 | 3.575 (7) | 145 |
C2B—H2BA···Cg1ii | 0.98 | 2.98 | 3.870 (7) | 151 |
Symmetry codes: (i) x−1/4, −y+3/4, z+1/4; (ii) −x+1/2, −y+1, z+1/2; (iii) x+1/4, −y+5/4, z+1/4. |
(1a) | (1b) | (2) | (3) | |
S1—N1 | 1.664 (5) | 1.653 (5) | 1.693 (2) | 1.668 (2) |
S1—S2 | 2.064 (3) | 2.076 (3) | 2.040 (1) | 2.102 (1) |
S2—S3 | 2.078 (3) | 2.067 (2) | 2.045 (1) | 2.082 (1) |
S3—N2 | 1.663 (6) | 1.649 (5) | 1.687 (2) | 1.680 (2) |
N1—S1—S2 | 106.9 (2) | 107.3 (2) | 105.0 (1) | 110.0 (1) |
S1—S2—S3 | 106.05 (11) | 105.41 (11) | 105.2 (2) | 104.7 (1) |
N2—S3—S2 | 107.6 (2) | 107.2 (2) | 103.8 (1) | 110.3 (1) |
N1—S1—S2—S3 | 86.6 (2) | -84.6 (2) | 93.2 (7) | 109.7 (2) |
S1—S2—S3—N2 | 87.0 (2) | -85.9 (2) | -89.5 (2) | 95.9 (1) |
Cg1, Cg2, Cg3, and Cg4 are the centroids of rings C3A–C8A, C9A–C14A, C3B–C8B, and C9B–C14B, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1A—H1AA···Cg2i | 0.98 | 2.91 | 3.810 (7) | 153 |
C2A—H2AA···Cg3ii | 0.98 | 2.76 | 3.658 (8) | 153 |
C1B—H1BA···Cg4iii | 0.98 | 2.73 | 3.575 (7) | 145 |
C2B—H2BA···Cg1ii | 0.98 | 2.98 | 3.870 (7) | 151 |
Symmetry codes: (i) x−1/4, −y+3/4, z+1/4; (ii) −x+1/2, −y+1, z+1/2; (iii) x+1/4, −y+5/4, z+1/4. |
Experimental details
Crystal data | |
Chemical formula | C14H16N2S3 |
Mr | 308.47 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 173 |
a, b, c (Å) | 19.284 (3), 56.440 (8), 11.1695 (15) |
V (Å3) | 12157 (3) |
Z | 32 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.25 × 0.22 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.890, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15884, 4978, 3097 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.129, 1.06 |
No. of reflections | 4978 |
No. of parameters | 347 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0357P)2 + 36.8709P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.43, −0.31 |
Absolute structure | 2194 Friedel pairs (Flack, 1983) |
Absolute structure parameter | 0.08 (12) |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).