2-Methyl-5-[(3-methyl-4-nitro-benz-yl)sulfan-yl]-1,3,4-thia-diazole.

The mol-ecule of the title thia-diazole derivative, C(11)H(11)N(3)O(2)S(2), has a butterfly-like structure and the whole mol-ecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The mol-ecule is disordered in such a way that the 3-methyl-4-nitro-phenyl units of the major and minor components are approximately related by 180° rotation around the C-N bond axis. The dihedral angle between the 1,3,4-thia-diazole and benzene rings is 70.8 (4)° in the major component and 74.9 (6)° in the minor component. In the crystal, mol-ecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak inter-molecular C-H⋯O and C-H⋯π inter-actions and a short C⋯O contact [3.005 (7) Å] are present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Wang et al. (2010 ▶). For background to and applications of thia­diazole derivatives, see: Bernard et al. (1985 ▶); Chandrakantha et al. (2010 ▶); Isloor et al. (2010 ▶); Kalluraya et al. (2004 ▶); Oruç et al. (2004 ▶); Salimon et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H11N3O2S2

M = 281.37

Orthorhombic,

a = 13.8210 (14) Å

b = 4.5720 (5) Å

c = 19.7929 (19) Å

V = 1250.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 100 K

0.46 × 0.30 × 0.10 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.831, T max = 0.959

10019 measured reflections

3754 independent reflections

3250 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.091

S = 1.10

3754 reflections

330 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 1234 Friedel pairs

Flack parameter: 0.04 (6)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052505/is2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052505/is2643Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H11N3O2S2	Dx = 1.494 Mg m−3
Mr = 281.37	Melting point = 443–445 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3.12 reflections
a = 13.8210 (14) Å	θ = 30.0–2899°
b = 4.5720 (5) Å	µ = 0.42 mm−1
c = 19.7929 (19) Å	T = 100 K
V = 1250.7 (2) Å3	Plate, yellow
Z = 4	0.46 × 0.30 × 0.10 mm
F(000) = 584

Bruker APEX DUO CCD area-detector diffractometer	3754 independent reflections
Radiation source: sealed tube	3250 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 33.7°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.831, Tmax = 0.959	k = −7→6
10019 measured reflections	l = −30→21

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3754 reflections	Δρmax = 0.45 e Å−3
330 parameters	Δρmin = −0.42 e Å−3
1 restraint	Absolute structure: Flack (1983), 1234 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (6)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.03130 (17)	0.3490 (8)	0.96362 (19)	0.0300 (3)	0.629 (4)
S2	0.1578 (2)	−0.0159 (8)	0.8790 (3)	0.0328 (6)	0.629 (4)
O2	−0.0136 (2)	−0.4228 (6)	1.29413 (14)	0.0518 (8)	0.629 (4)
O3	−0.1559 (3)	−0.4789 (7)	1.25002 (19)	0.0478 (9)	0.629 (4)
N1	0.2757 (4)	−0.0884 (15)	0.9791 (3)	0.0420 (11)	0.629 (4)
N2	0.2002 (4)	0.0921 (19)	1.0023 (4)	0.0346 (12)	0.629 (4)
N3	−0.0749 (2)	−0.3679 (6)	1.25069 (13)	0.0349 (6)	0.629 (4)
C1	0.0766 (3)	0.1353 (6)	1.14831 (15)	0.0289 (5)	0.629 (4)
H1A	0.1410	0.1947	1.1471	0.035*	0.629 (4)
C2	0.0461 (3)	−0.0654 (6)	1.19695 (14)	0.0289 (5)	0.629 (4)
H2A	0.0897	−0.1386	1.2285	0.035*	0.629 (4)
C3	−0.0489 (4)	−0.1543 (6)	1.19794 (14)	0.0262 (5)	0.629 (4)
C4	−0.1181 (3)	−0.0516 (6)	1.15221 (16)	0.0278 (5)	0.629 (4)
C5	−0.0843 (3)	0.1537 (7)	1.10453 (16)	0.0266 (6)	0.629 (4)
H5A	−0.1281	0.2301	1.0735	0.032*	0.629 (4)
C6	0.0110 (3)	0.2467 (7)	1.10173 (18)	0.0244 (5)	0.629 (4)
C7	0.0414 (3)	0.4654 (12)	1.0497 (3)	0.0319 (9)	0.629 (4)
H7A	0.1082	0.5185	1.0583	0.038*	0.629 (4)
H7B	0.0026	0.6404	1.0556	0.038*	0.629 (4)
C8	0.1361 (6)	0.136 (2)	0.9548 (6)	0.0258 (13)	0.629 (4)
C9	0.2662 (7)	−0.157 (3)	0.9161 (5)	0.0336 (14)	0.629 (4)
C10	0.3367 (8)	−0.341 (2)	0.8795 (5)	0.050 (2)	0.629 (4)
H10A	0.3740	−0.4522	0.9113	0.075*	0.629 (4)
H10B	0.3791	−0.2182	0.8535	0.075*	0.629 (4)
H10C	0.3029	−0.4718	0.8498	0.075*	0.629 (4)
S1A	0.0080 (3)	0.3638 (14)	0.9625 (4)	0.0331 (7)	0.371 (4)
S2A	0.1561 (5)	−0.0237 (15)	0.8860 (6)	0.0398 (14)	0.371 (4)
O2A	−0.0852 (4)	−0.5184 (9)	1.2745 (3)	0.0507 (12)	0.371 (4)
O3A	−0.2234 (4)	−0.4513 (11)	1.2302 (3)	0.0600 (14)	0.371 (4)
N1A	0.2532 (5)	−0.046 (2)	0.9912 (4)	0.0311 (14)	0.371 (4)
N2A	0.1738 (7)	0.115 (3)	1.0101 (6)	0.0321 (15)	0.371 (4)
N3A	−0.1378 (4)	−0.3973 (13)	1.2341 (3)	0.0327 (11)	0.371 (4)
C1A	0.0286 (4)	0.1374 (9)	1.1504 (2)	0.0254 (8)	0.371 (4)
H1B	0.0910	0.2118	1.1541	0.031*	0.371 (4)
C2A	−0.0029 (4)	−0.0698 (9)	1.1981 (2)	0.0196 (7)	0.371 (4)
C3A	−0.0968 (4)	−0.1718 (9)	1.1884 (2)	0.0232 (8)	0.371 (4)
C4A	−0.1560 (4)	−0.0847 (11)	1.1368 (3)	0.0292 (10)	0.371 (4)
H4B	−0.2178	−0.1628	1.1322	0.035*	0.371 (4)
C5A	−0.1220 (5)	0.1226 (12)	1.0913 (3)	0.0320 (11)	0.371 (4)
H5B	−0.1613	0.1869	1.0562	0.038*	0.371 (4)
C6A	−0.0289 (5)	0.2336 (11)	1.0987 (3)	0.0238 (10)	0.371 (4)
C7A	0.0060 (7)	0.479 (2)	1.0507 (5)	0.0379 (19)	0.371 (4)
H7C	0.0705	0.5389	1.0640	0.045*	0.371 (4)
H7D	−0.0365	0.6463	1.0553	0.045*	0.371 (4)
C8A	0.1157 (10)	0.166 (4)	0.9600 (8)	0.0220 (18)	0.371 (4)
C9A	0.2489 (11)	−0.138 (4)	0.9296 (7)	0.0294 (19)	0.371 (4)
C10A	0.3250 (10)	−0.317 (4)	0.8965 (8)	0.043 (3)	0.371 (4)
H10D	0.3736	−0.3676	0.9291	0.065*	0.371 (4)
H10E	0.3539	−0.2066	0.8606	0.065*	0.371 (4)
H10F	0.2966	−0.4921	0.8786	0.065*	0.371 (4)
C11	−0.2234 (2)	−0.1340 (8)	1.14972 (19)	0.0438 (7)	0.629 (4)
H11A	−0.2292	−0.3416	1.1436	0.066*	0.629 (4)
H11B	−0.2540	−0.0349	1.1127	0.066*	0.629 (4)
H11C	−0.2541	−0.0783	1.1913	0.066*	0.629 (4)
C11A	0.0647 (3)	−0.1528 (12)	1.2541 (2)	0.0357 (11)	0.371 (4)
H11D	0.1235	−0.0425	1.2500	0.053*	0.371 (4)
H11E	0.0790	−0.3579	1.2513	0.053*	0.371 (4)
H11F	0.0348	−0.1111	1.2968	0.053*	0.371 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0368 (8)	0.0311 (6)	0.0220 (4)	0.0045 (6)	−0.0004 (8)	0.0056 (4)
S2	0.0371 (10)	0.0316 (9)	0.0298 (14)	0.0018 (7)	−0.0078 (6)	0.0015 (6)
O2	0.0612 (16)	0.0623 (16)	0.0319 (13)	0.0179 (13)	0.0060 (11)	0.0219 (12)
O3	0.067 (2)	0.0426 (16)	0.0343 (17)	−0.0141 (14)	0.0107 (15)	0.0050 (11)
N1	0.032 (2)	0.051 (2)	0.043 (3)	0.0138 (15)	0.0031 (15)	0.0084 (18)
N2	0.027 (2)	0.050 (3)	0.027 (2)	−0.003 (2)	−0.0033 (17)	0.0076 (17)
N3	0.0559 (17)	0.0290 (12)	0.0197 (10)	0.0099 (10)	0.0105 (10)	0.0022 (9)
C1	0.0360 (15)	0.0260 (12)	0.0248 (12)	−0.0017 (11)	−0.0003 (11)	−0.0036 (9)
C2	0.0373 (16)	0.0297 (12)	0.0197 (11)	0.0073 (11)	−0.0029 (10)	−0.0019 (9)
C3	0.0370 (17)	0.0252 (12)	0.0163 (11)	0.0075 (13)	0.0031 (11)	0.0012 (9)
C4	0.0294 (14)	0.0300 (12)	0.0241 (13)	0.0047 (11)	0.0033 (11)	−0.0032 (11)
C5	0.0340 (18)	0.0252 (12)	0.0206 (12)	0.0064 (13)	−0.0037 (12)	−0.0014 (10)
C6	0.0324 (14)	0.0178 (10)	0.0230 (11)	−0.0012 (12)	0.0007 (13)	−0.0038 (9)
C7	0.052 (2)	0.0167 (14)	0.0273 (16)	0.0025 (17)	0.005 (2)	−0.0016 (11)
C8	0.030 (3)	0.019 (2)	0.029 (3)	−0.0045 (17)	0.0014 (19)	0.0020 (18)
C9	0.027 (3)	0.0321 (19)	0.041 (4)	−0.0015 (19)	0.0047 (19)	0.011 (2)
C10	0.044 (3)	0.038 (2)	0.068 (6)	0.0098 (17)	0.011 (3)	0.008 (3)
S1A	0.050 (2)	0.0273 (7)	0.0214 (7)	0.0055 (15)	0.0021 (18)	0.0007 (6)
S2A	0.054 (2)	0.042 (2)	0.0236 (17)	−0.0138 (14)	−0.0082 (9)	−0.0056 (12)
O2A	0.063 (3)	0.037 (2)	0.052 (3)	0.0047 (17)	0.016 (2)	0.019 (2)
O3A	0.042 (2)	0.085 (3)	0.053 (3)	−0.029 (2)	0.008 (2)	0.006 (2)
N1A	0.028 (4)	0.038 (3)	0.027 (3)	0.007 (3)	−0.006 (2)	−0.002 (2)
N2A	0.035 (4)	0.036 (3)	0.025 (3)	−0.005 (4)	−0.004 (3)	0.001 (2)
N3A	0.032 (2)	0.035 (3)	0.031 (3)	−0.0079 (18)	0.0141 (19)	−0.0017 (19)
C1A	0.031 (2)	0.0239 (18)	0.0215 (19)	−0.0072 (17)	0.0047 (17)	−0.0059 (14)
C2A	0.0142 (18)	0.0248 (19)	0.0199 (17)	0.0023 (16)	0.0023 (14)	−0.0001 (13)
C3A	0.0221 (19)	0.0241 (18)	0.023 (2)	0.0049 (16)	0.0023 (16)	−0.0002 (15)
C4A	0.022 (2)	0.031 (2)	0.034 (3)	0.0036 (17)	−0.0040 (18)	−0.0013 (18)
C5A	0.039 (3)	0.025 (2)	0.032 (3)	0.010 (2)	−0.005 (2)	0.0006 (18)
C6A	0.034 (3)	0.0163 (17)	0.021 (2)	−0.003 (2)	0.005 (2)	−0.0015 (14)
C7A	0.070 (5)	0.020 (2)	0.024 (2)	0.014 (4)	0.015 (4)	−0.0003 (17)
C8A	0.039 (6)	0.015 (3)	0.012 (2)	−0.004 (3)	0.002 (4)	0.000 (2)
C9A	0.030 (5)	0.028 (4)	0.030 (5)	−0.008 (4)	0.003 (3)	0.010 (3)
C10A	0.030 (4)	0.046 (6)	0.053 (6)	−0.010 (4)	0.000 (4)	0.009 (4)
C11	0.0323 (13)	0.062 (2)	0.0372 (16)	−0.0044 (12)	0.0038 (11)	0.0024 (14)
C11A	0.0303 (18)	0.052 (3)	0.025 (2)	0.0046 (17)	−0.0020 (16)	0.0000 (18)

S1—C8	1.756 (7)	S2A—C8A	1.791 (17)
S1—C7	1.791 (8)	O2A—N3A	1.213 (9)
S2—C8	1.678 (12)	O3A—N3A	1.211 (7)
S2—C9	1.790 (12)	N1A—C9A	1.291 (16)
O2—N3	1.233 (4)	N1A—N2A	1.376 (11)
O3—N3	1.229 (5)	N2A—C8A	1.30 (2)
N1—C9	1.293 (11)	N3A—C3A	1.485 (7)
N1—N2	1.407 (7)	C1A—C6A	1.368 (8)
N2—C8	1.306 (14)	C1A—C2A	1.407 (6)
N3—C3	1.474 (4)	C1A—H1B	0.9300
C1—C6	1.390 (5)	C2A—C3A	1.391 (7)
C1—C2	1.396 (4)	C2A—C11A	1.498 (7)
C1—H1A	0.9300	C3A—C4A	1.369 (7)
C2—C3	1.374 (6)	C4A—C5A	1.389 (8)
C2—H2A	0.9300	C4A—H4B	0.9300
C3—C4	1.397 (5)	C5A—C6A	1.391 (8)
C4—C5	1.410 (4)	C5A—H5B	0.9300
C4—C11	1.504 (5)	C6A—C7A	1.546 (11)
C5—C6	1.385 (4)	C7A—H7C	0.9700
C5—H5A	0.9300	C7A—H7D	0.9700
C6—C7	1.495 (7)	C9A—C10A	1.48 (2)
C7—H7A	0.9700	C10A—H10D	0.9600
C7—H7B	0.9700	C10A—H10E	0.9600
C9—C10	1.476 (13)	C10A—H10F	0.9600
C10—H10A	0.9600	C11—H11A	0.9600
C10—H10B	0.9600	C11—H11B	0.9600
C10—H10C	0.9600	C11—H11C	0.9600
S1A—C8A	1.742 (12)	C11A—H11D	0.9600
S1A—C7A	1.822 (13)	C11A—H11E	0.9600
S2A—C9A	1.63 (2)	C11A—H11F	0.9600
C8—S1—C7	101.3 (5)	O2A—N3A—C3A	119.3 (5)
C8—S2—C9	86.1 (5)	C6A—C1A—C2A	122.5 (5)
C9—N1—N2	112.4 (7)	C6A—C1A—H1B	118.7
C8—N2—N1	111.0 (6)	C2A—C1A—H1B	118.7
O3—N3—O2	123.3 (3)	C3A—C2A—C1A	115.0 (4)
O3—N3—C3	119.2 (3)	C3A—C2A—C11A	126.8 (4)
O2—N3—C3	117.5 (3)	C1A—C2A—C11A	118.2 (5)
C6—C1—C2	120.1 (3)	C4A—C3A—C2A	124.3 (4)
C6—C1—H1A	120.0	C4A—C3A—N3A	115.4 (5)
C2—C1—H1A	120.0	C2A—C3A—N3A	120.3 (5)
C3—C2—C1	119.6 (3)	C3A—C4A—C5A	118.7 (5)
C3—C2—H2A	120.2	C3A—C4A—H4B	120.7
C1—C2—H2A	120.2	C5A—C4A—H4B	120.7
C2—C3—C4	123.0 (3)	C4A—C5A—C6A	119.6 (5)
C2—C3—N3	116.0 (3)	C4A—C5A—H5B	120.2
C4—C3—N3	121.0 (4)	C6A—C5A—H5B	120.2
C3—C4—C5	115.5 (3)	C1A—C6A—C5A	119.9 (5)
C3—C4—C11	126.8 (3)	C1A—C6A—C7A	120.8 (7)
C5—C4—C11	117.7 (3)	C5A—C6A—C7A	119.2 (7)
C6—C5—C4	123.1 (3)	C6A—C7A—S1A	112.6 (7)
C6—C5—H5A	118.5	C6A—C7A—H7C	109.1
C4—C5—H5A	118.5	S1A—C7A—H7C	109.1
C5—C6—C1	118.8 (3)	C6A—C7A—H7D	109.1
C5—C6—C7	120.0 (3)	S1A—C7A—H7D	109.1
C1—C6—C7	121.2 (3)	H7C—C7A—H7D	107.8
C6—C7—S1	115.7 (4)	N2A—C8A—S1A	126.9 (11)
C6—C7—H7A	108.3	N2A—C8A—S2A	110.2 (9)
S1—C7—H7A	108.3	S1A—C8A—S2A	122.8 (10)
C6—C7—H7B	108.3	N1A—C9A—C10A	124.2 (16)
S1—C7—H7B	108.3	N1A—C9A—S2A	115.5 (11)
H7A—C7—H7B	107.4	C10A—C9A—S2A	120.1 (12)
N2—C8—S2	117.3 (5)	C9A—C10A—H10D	109.5
N2—C8—S1	124.9 (8)	C9A—C10A—H10E	109.5
S2—C8—S1	117.7 (7)	H10D—C10A—H10E	109.5
N1—C9—C10	123.1 (10)	C9A—C10A—H10F	109.5
N1—C9—S2	113.1 (6)	H10D—C10A—H10F	109.5
C10—C9—S2	123.8 (9)	H10E—C10A—H10F	109.5
C8A—S1A—C7A	101.0 (7)	C2A—C11A—H11D	109.5
C9A—S2A—C8A	88.2 (8)	C2A—C11A—H11E	109.5
C9A—N1A—N2A	113.3 (10)	H11D—C11A—H11E	109.5
C8A—N2A—N1A	112.5 (10)	C2A—C11A—H11F	109.5
O3A—N3A—O2A	122.3 (6)	H11D—C11A—H11F	109.5
O3A—N3A—C3A	118.4 (6)	H11E—C11A—H11F	109.5
C9—N1—N2—C8	2.8 (11)	C9A—N1A—N2A—C8A	−6.5 (18)
C6—C1—C2—C3	0.7 (4)	C6A—C1A—C2A—C3A	0.6 (6)
C1—C2—C3—C4	−0.3 (4)	C6A—C1A—C2A—C11A	−178.0 (4)
C1—C2—C3—N3	179.7 (2)	C1A—C2A—C3A—C4A	0.5 (6)
O3—N3—C3—C2	−172.5 (3)	C11A—C2A—C3A—C4A	178.9 (4)
O2—N3—C3—C2	8.4 (4)	C1A—C2A—C3A—N3A	178.3 (4)
O3—N3—C3—C4	7.4 (4)	C11A—C2A—C3A—N3A	−3.3 (7)
O2—N3—C3—C4	−171.6 (3)	O3A—N3A—C3A—C4A	−12.1 (7)
C2—C3—C4—C5	−0.5 (4)	O2A—N3A—C3A—C4A	168.7 (5)
N3—C3—C4—C5	179.6 (2)	O3A—N3A—C3A—C2A	169.9 (5)
C2—C3—C4—C11	−179.5 (3)	O2A—N3A—C3A—C2A	−9.3 (7)
N3—C3—C4—C11	0.6 (4)	C2A—C3A—C4A—C5A	−1.2 (7)
C3—C4—C5—C6	0.9 (4)	N3A—C3A—C4A—C5A	−179.1 (5)
C11—C4—C5—C6	−180.0 (3)	C3A—C4A—C5A—C6A	0.8 (8)
C4—C5—C6—C1	−0.6 (5)	C2A—C1A—C6A—C5A	−1.0 (7)
C4—C5—C6—C7	−179.9 (3)	C2A—C1A—C6A—C7A	175.3 (5)
C2—C1—C6—C5	−0.3 (4)	C4A—C5A—C6A—C1A	0.2 (8)
C2—C1—C6—C7	179.1 (3)	C4A—C5A—C6A—C7A	−176.1 (6)
C5—C6—C7—S1	−63.8 (4)	C1A—C6A—C7A—S1A	121.8 (6)
C1—C6—C7—S1	116.9 (4)	C5A—C6A—C7A—S1A	−61.9 (7)
C8—S1—C7—C6	−79.8 (5)	C8A—S1A—C7A—C6A	−79.6 (9)
N1—N2—C8—S2	−1.9 (12)	N1A—N2A—C8A—S1A	−179.7 (12)
N1—N2—C8—S1	−179.9 (7)	N1A—N2A—C8A—S2A	5.2 (17)
C9—S2—C8—N2	0.4 (9)	C7A—S1A—C8A—N2A	2.0 (18)
C9—S2—C8—S1	178.6 (7)	C7A—S1A—C8A—S2A	176.5 (10)
C7—S1—C8—N2	−0.7 (11)	C9A—S2A—C8A—N2A	−2.4 (14)
C7—S1—C8—S2	−178.7 (6)	C9A—S2A—C8A—S1A	−177.7 (12)
N2—N1—C9—C10	179.0 (9)	N2A—N1A—C9A—C10A	179.9 (13)
N2—N1—C9—S2	−2.5 (10)	N2A—N1A—C9A—S2A	4.6 (16)
C8—S2—C9—N1	1.3 (8)	C8A—S2A—C9A—N1A	−1.3 (13)
C8—S2—C9—C10	179.7 (10)	C8A—S2A—C9A—C10A	−176.8 (14)

Cg1, Cg2 and Cg3 are the centroids of the S2/C9/N1/N2/C8, C1–C6 and C1A–C6A rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2i	0.96	2.58	3.534 (11)	171
C7—H7B···Cg2ii	0.97	2.65	3.417 (6)	134
C7—H7B···Cg3ii	0.97	2.65	3.489 (6)	145
C7A—H7D···Cg2ii	0.97	2.63	3.269 (10)	124
C7A—H7D···Cg3ii	0.97	2.50	3.258 (10)	135
C10A—H10F···Cg1iii	0.96	2.98	3.683 (18)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the S2/C9/N1/N2/C8, C1–C6 and C1A–C6A rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2i	0.96	2.58	3.534 (11)	171
C7—H7B⋯Cg2ii	0.97	2.65	3.417 (6)	134
C7—H7B⋯Cg3ii	0.97	2.65	3.489 (6)	145
C7A—H7D⋯Cg2ii	0.97	2.63	3.269 (10)	124
C7A—H7D⋯Cg3ii	0.97	2.50	3.258 (10)	135
C10A—H10F⋯Cg1iii	0.96	2.98	3.683 (18)	132

Symmetry codes: (i) ; (ii) ; (iii) .