N-Methyl-2-(1,2,3,4-tetra-hydro-naph-thalen-1-yl-idene)hydrazinecarbo-thio-amide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C12H15N3S, both of which display disorder of several C atoms in the N-bound ring (occupancy ratios of 0.75:0.25 in the first independent mol-ecule and 0.50:0.50 in the second) with the methyl H atoms also being disordered in the first mol-ecule (occupancy ratio of 0.70:0.30). The planes of the benzene ring and the N-N-C-N fragment make dihedral angles of 12.92 (14)° in the first independent mol-ecule and 7.60 (13)° in the second. In the crystal, mol-ecules are linked by weak N-H⋯S hydrogen bonds into chains along the a-axis direction. The crystal packing ressembles a herringbone arrangement.

Related literature

For the synthesis, coordination chemistry and biological activity of thio­semicarbazones, see: Lobana et al. (2009 ▶). For one of the first reports of the synthesis of thio­semicarbazone derivatives, see: Freund & Schander (1902 ▶).

Experimental

Crystal data

C12H15N3S

M = 233.33

Triclinic,

a = 10.6234 (6) Å

b = 10.9425 (6) Å

c = 11.0576 (6) Å

α = 73.685 (4)°

β = 79.152 (4)°

γ = 88.614 (4)°

V = 1211.04 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 200 K

0.2 × 0.1 × 0.1 mm

Data collection

Stoe IPDS-1 diffractometer

11521 measured reflections

5125 independent reflections

4111 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.06

5125 reflections

334 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.42 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003079/bt6960sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003079/bt6960Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003079/bt6960Isup3.cml

CCDC reference: 986205

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H15N3S	Z = 4
Mr = 233.33	F(000) = 496
Triclinic, P1	Dx = 1.280 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6234 (6) Å	Cell parameters from 11521 reflections
b = 10.9425 (6) Å	θ = 1.9–27.0°
c = 11.0576 (6) Å	µ = 0.24 mm−1
α = 73.685 (4)°	T = 200 K
β = 79.152 (4)°	Block, white
γ = 88.614 (4)°	0.2 × 0.1 × 0.1 mm
V = 1211.04 (12) Å3

Stoe IPDS-1 diffractometer	4111 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Stoe IPDS-1	Rint = 0.031
Graphite monochromator	θmax = 27.0°, θmin = 1.9°
φ scans	h = −13→12
11521 measured reflections	k = −13→13
5125 independent reflections	l = −14→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2784P] where P = (Fo2 + 2Fc2)/3
5125 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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)
C1	0.48672 (15)	0.18650 (14)	0.58968 (14)	0.0359 (3)
C2	0.5663 (2)	0.2436 (2)	0.65971 (16)	0.0585 (5)
H2A	0.5465	0.3348	0.6461	0.070*	0.75
H2B	0.6581	0.2385	0.6229	0.070*	0.75
H2C	0.5993	0.3292	0.6057	0.070*	0.25
H2D	0.6406	0.1896	0.6772	0.070*	0.25
C3	0.5434 (3)	0.1769 (3)	0.8050 (2)	0.0523 (6)	0.75
H3A	0.5785	0.0904	0.8205	0.063*	0.75
H3B	0.5878	0.2259	0.8483	0.063*	0.75
C4	0.4004 (7)	0.1680 (7)	0.8593 (8)	0.0515 (13)	0.75
H4A	0.3634	0.2536	0.8400	0.062*	0.75
H4B	0.3844	0.1303	0.9535	0.062*	0.75
C3'	0.4840 (13)	0.2542 (11)	0.7888 (8)	0.074 (3)	0.25
H3C	0.5398	0.2787	0.8411	0.088*	0.25
H3D	0.4196	0.3207	0.7715	0.088*	0.25
C4'	0.420 (3)	0.133 (2)	0.858 (3)	0.071 (7)	0.25
H4C	0.4868	0.0699	0.8806	0.085*	0.25
H4D	0.3683	0.1411	0.9392	0.085*	0.25
C5	0.34020 (17)	0.08243 (17)	0.79474 (15)	0.0456 (4)
C6	0.24021 (19)	−0.00422 (19)	0.86362 (18)	0.0570 (5)
H6	0.2117	−0.0132	0.9525	0.068*
C7	0.18239 (19)	−0.07657 (18)	0.8054 (2)	0.0582 (5)
H7	0.1152	−0.1359	0.8542	0.070*
C8	0.22184 (17)	−0.06331 (16)	0.67515 (19)	0.0497 (4)
H8	0.1809	−0.1126	0.6345	0.060*
C9	0.32074 (15)	0.02177 (14)	0.60490 (16)	0.0396 (3)
H9	0.3479	0.0307	0.5159	0.048*
C10	0.38118 (15)	0.09484 (13)	0.66391 (14)	0.0350 (3)
N1	0.50410 (13)	0.21270 (11)	0.46681 (12)	0.0354 (3)
N2	0.60085 (15)	0.29850 (14)	0.39563 (12)	0.0430 (3)
H2	0.652 (2)	0.3371 (19)	0.431 (2)	0.056 (6)*
C11	0.62069 (17)	0.32887 (15)	0.26515 (14)	0.0420 (4)
S1	0.73841 (6)	0.43493 (5)	0.17704 (4)	0.06437 (17)
N3	0.54320 (15)	0.27078 (15)	0.21718 (13)	0.0441 (3)
H3	0.486 (2)	0.215 (2)	0.272 (2)	0.057 (6)*
C12	0.5478 (2)	0.2904 (2)	0.08134 (17)	0.0624 (5)
H12A	0.4843	0.2334	0.0693	0.094*	0.70
H12B	0.6336	0.2719	0.0410	0.094*	0.70
H12C	0.5285	0.3790	0.0418	0.094*	0.70
H12D	0.6133	0.3561	0.0321	0.094*	0.30
H12E	0.4640	0.3177	0.0604	0.094*	0.30
H12F	0.5691	0.2105	0.0596	0.094*	0.30
C21	1.03532 (14)	0.72157 (13)	0.43323 (14)	0.0345 (3)
C22	0.98459 (18)	0.80910 (17)	0.32295 (15)	0.0463 (4)
H22A	0.9799	0.8963	0.3330	0.056*	0.50
H22B	0.8968	0.7801	0.3238	0.056*	0.50
H22C	1.0370	0.8893	0.2905	0.056*	0.50
H22D	0.8954	0.8305	0.3536	0.056*	0.50
C23	1.0710 (4)	0.8118 (3)	0.1933 (3)	0.0439 (7)	0.50
H23A	1.0273	0.8583	0.1231	0.053*	0.50
H23B	1.1517	0.8596	0.1847	0.053*	0.50
C23'	0.9870 (4)	0.7468 (4)	0.2094 (3)	0.0527 (9)	0.50
H23C	0.9161	0.6824	0.2339	0.063*	0.50
H23D	0.9720	0.8135	0.1324	0.063*	0.50
C24	1.1012 (3)	0.6896 (3)	0.1790 (2)	0.0752 (7)
H24A	1.1638	0.6994	0.0981	0.090*	0.50
H24B	1.0225	0.6481	0.1713	0.090*	0.50
H24C	1.1662	0.7578	0.1307	0.090*	0.50
H24D	1.0891	0.6392	0.1202	0.090*	0.50
C25	1.15584 (17)	0.60384 (17)	0.28740 (17)	0.0451 (4)
C26	1.23846 (19)	0.50776 (19)	0.2683 (2)	0.0562 (5)
H26	1.2618	0.4967	0.1848	0.067*
C27	1.28696 (19)	0.42841 (18)	0.3681 (2)	0.0571 (5)
H27	1.3434	0.3633	0.3533	0.069*
C28	1.25370 (17)	0.44333 (17)	0.4896 (2)	0.0518 (4)
H28	1.2872	0.3885	0.5585	0.062*
C29	1.17199 (15)	0.53750 (15)	0.51113 (17)	0.0424 (4)
H29	1.1488	0.5468	0.5953	0.051*
C30	1.12244 (14)	0.61990 (14)	0.41059 (14)	0.0352 (3)
N21	1.00717 (13)	0.72885 (12)	0.54928 (12)	0.0378 (3)
N22	0.92325 (15)	0.81998 (13)	0.57445 (13)	0.0417 (3)
H22	0.883 (2)	0.8683 (19)	0.517 (2)	0.055 (6)*
C31	0.87550 (17)	0.81552 (16)	0.69932 (15)	0.0420 (4)
S21	0.76008 (5)	0.91523 (5)	0.73333 (5)	0.05696 (15)
N23	0.92760 (17)	0.73086 (15)	0.78559 (13)	0.0475 (3)
H23	0.985 (2)	0.683 (2)	0.762 (2)	0.059 (6)*
C32	0.8857 (2)	0.7063 (2)	0.92353 (17)	0.0637 (6)
H32A	0.8908	0.7858	0.9470	0.096*
H32B	0.9411	0.6437	0.9682	0.096*
H32C	0.7969	0.6730	0.9483	0.096*

	U11	U22	U33	U12	U13	U23
C1	0.0370 (8)	0.0407 (7)	0.0292 (7)	−0.0037 (6)	−0.0035 (6)	−0.0102 (6)
C2	0.0602 (12)	0.0828 (13)	0.0308 (8)	−0.0339 (10)	−0.0013 (8)	−0.0151 (8)
C3	0.0488 (15)	0.0784 (19)	0.0313 (11)	−0.0160 (13)	−0.0046 (10)	−0.0188 (12)
C4	0.056 (2)	0.069 (4)	0.0309 (16)	−0.015 (2)	0.0027 (16)	−0.022 (2)
C3'	0.106 (9)	0.081 (6)	0.036 (4)	−0.049 (6)	0.009 (5)	−0.029 (4)
C4'	0.107 (14)	0.068 (12)	0.031 (5)	−0.022 (8)	0.022 (7)	−0.023 (7)
C5	0.0455 (10)	0.0531 (9)	0.0329 (8)	−0.0093 (7)	−0.0038 (7)	−0.0048 (7)
C6	0.0531 (11)	0.0669 (12)	0.0377 (9)	−0.0157 (9)	−0.0003 (8)	0.0026 (8)
C7	0.0479 (11)	0.0510 (10)	0.0615 (12)	−0.0149 (8)	−0.0065 (9)	0.0059 (8)
C8	0.0417 (9)	0.0410 (8)	0.0666 (11)	−0.0041 (7)	−0.0151 (9)	−0.0117 (8)
C9	0.0355 (8)	0.0406 (8)	0.0439 (8)	0.0026 (6)	−0.0093 (7)	−0.0127 (6)
C10	0.0343 (8)	0.0354 (7)	0.0327 (7)	0.0005 (6)	−0.0065 (6)	−0.0052 (6)
N1	0.0377 (7)	0.0373 (6)	0.0296 (6)	−0.0036 (5)	−0.0033 (5)	−0.0084 (5)
N2	0.0479 (8)	0.0508 (8)	0.0276 (6)	−0.0152 (6)	−0.0011 (6)	−0.0093 (5)
C11	0.0476 (10)	0.0462 (8)	0.0291 (7)	−0.0023 (7)	−0.0021 (7)	−0.0088 (6)
S1	0.0763 (4)	0.0707 (3)	0.0348 (2)	−0.0303 (3)	0.0012 (2)	−0.0016 (2)
N3	0.0461 (8)	0.0577 (8)	0.0271 (6)	−0.0038 (7)	−0.0032 (6)	−0.0119 (6)
C12	0.0653 (13)	0.0932 (15)	0.0298 (8)	−0.0070 (11)	−0.0084 (8)	−0.0189 (9)
C21	0.0342 (8)	0.0374 (7)	0.0304 (7)	−0.0045 (6)	−0.0047 (6)	−0.0078 (6)
C22	0.0542 (11)	0.0497 (9)	0.0317 (8)	0.0123 (8)	−0.0068 (7)	−0.0079 (7)
C23	0.0446 (19)	0.0546 (19)	0.0265 (14)	−0.0051 (15)	−0.0023 (13)	−0.0039 (13)
C23'	0.059 (2)	0.069 (2)	0.0328 (16)	0.016 (2)	−0.0152 (16)	−0.0156 (16)
C24	0.0950 (18)	0.0995 (17)	0.0404 (10)	0.0374 (14)	−0.0212 (11)	−0.0322 (11)
C25	0.0414 (9)	0.0532 (9)	0.0446 (9)	0.0016 (7)	−0.0067 (7)	−0.0210 (7)
C26	0.0478 (11)	0.0641 (11)	0.0641 (12)	0.0030 (9)	−0.0033 (9)	−0.0347 (10)
C27	0.0423 (10)	0.0481 (10)	0.0848 (14)	0.0060 (8)	−0.0100 (10)	−0.0267 (9)
C28	0.0390 (9)	0.0434 (9)	0.0697 (12)	0.0016 (7)	−0.0139 (9)	−0.0085 (8)
C29	0.0361 (9)	0.0424 (8)	0.0460 (9)	−0.0040 (6)	−0.0085 (7)	−0.0073 (7)
C30	0.0284 (7)	0.0380 (7)	0.0385 (8)	−0.0057 (6)	−0.0039 (6)	−0.0107 (6)
N21	0.0401 (7)	0.0409 (7)	0.0331 (6)	0.0004 (5)	−0.0065 (5)	−0.0118 (5)
N22	0.0489 (8)	0.0447 (7)	0.0316 (6)	0.0046 (6)	−0.0058 (6)	−0.0123 (5)
C31	0.0448 (9)	0.0472 (8)	0.0358 (8)	−0.0119 (7)	−0.0016 (7)	−0.0172 (7)
S21	0.0551 (3)	0.0707 (3)	0.0517 (3)	0.0034 (2)	−0.0019 (2)	−0.0334 (2)
N23	0.0555 (10)	0.0538 (8)	0.0313 (7)	−0.0079 (7)	−0.0036 (6)	−0.0114 (6)
C32	0.0733 (14)	0.0818 (14)	0.0308 (8)	−0.0207 (11)	−0.0003 (9)	−0.0119 (8)

C1—N1	1.2851 (19)	C12—H12E	0.9800
C1—C10	1.477 (2)	C12—H12F	0.9800
C1—C2	1.499 (2)	C21—N21	1.2863 (19)
C2—C3	1.541 (3)	C21—C30	1.475 (2)
C2—C3'	1.560 (9)	C21—C22	1.504 (2)
C2—H2A	0.9900	C22—C23	1.543 (3)
C2—H2B	0.9900	C22—C23'	1.584 (4)
C2—H2C	0.9900	C22—H22A	0.9900
C2—H2D	0.9900	C22—H22B	0.9900
C3—C4	1.519 (8)	C22—H22C	0.9900
C3—H3A	0.9900	C22—H22D	0.9900
C3—H3B	0.9900	C23—C24	1.412 (4)
C4—C5	1.540 (6)	C23—H23A	0.9900
C4—H4A	0.9900	C23—H23B	0.9900
C4—H4B	0.9900	C23'—C24	1.380 (4)
C3'—C4'	1.45 (3)	C23'—H23C	0.9900
C3'—H3C	0.9900	C23'—H23D	0.9900
C3'—H3D	0.9900	C24—C25	1.502 (3)
C4'—C5	1.41 (3)	C24—H24A	0.9900
C4'—H4C	0.9900	C24—H24B	0.9900
C4'—H4D	0.9900	C24—H24C	0.9900
C5—C6	1.395 (2)	C24—H24D	0.9900
C5—C10	1.399 (2)	C25—C26	1.390 (3)
C6—C7	1.370 (3)	C25—C30	1.401 (2)
C6—H6	0.9500	C26—C27	1.375 (3)
C7—C8	1.389 (3)	C26—H26	0.9500
C7—H7	0.9500	C27—C28	1.377 (3)
C8—C9	1.381 (2)	C27—H27	0.9500
C8—H8	0.9500	C28—C29	1.374 (3)
C9—C10	1.398 (2)	C28—H28	0.9500
C9—H9	0.9500	C29—C30	1.400 (2)
N1—N2	1.3727 (18)	C29—H29	0.9500
N2—C11	1.362 (2)	N21—N22	1.373 (2)
N2—H2	0.90 (2)	N22—C31	1.366 (2)
C11—N3	1.320 (2)	N22—H22	0.88 (2)
C11—S1	1.6841 (17)	C31—N23	1.324 (2)
N3—C12	1.448 (2)	C31—S21	1.6816 (18)
N3—H3	0.88 (2)	N23—C32	1.455 (2)
C12—H12A	0.9800	N23—H23	0.85 (2)
C12—H12B	0.9800	C32—H32A	0.9800
C12—H12C	0.9800	C32—H32B	0.9800
C12—H12D	0.9800	C32—H32C	0.9800
N1—C1—C10	116.87 (13)	H12D—C12—H12F	109.5
N1—C1—C2	123.86 (14)	H12E—C12—H12F	109.5
C10—C1—C2	119.27 (13)	N21—C21—C30	116.47 (13)
C1—C2—C3	113.13 (16)	N21—C21—C22	123.90 (14)
C1—C2—C3'	110.1 (4)	C30—C21—C22	119.63 (13)
C1—C2—H2A	109.0	C21—C22—C23	111.25 (18)
C3—C2—H2A	109.0	C21—C22—C23'	111.96 (18)
C1—C2—H2B	109.0	C21—C22—H22A	109.4
C3—C2—H2B	109.0	C23—C22—H22A	109.4
H2A—C2—H2B	107.8	C23'—C22—H22A	136.4
C1—C2—H2C	109.6	C21—C22—H22B	109.4
C3—C2—H2C	134.0	C23—C22—H22B	109.4
C3'—C2—H2C	109.6	C23'—C22—H22B	70.4
C1—C2—H2D	109.6	H22A—C22—H22B	108.0
C3'—C2—H2D	109.6	C21—C22—H22C	109.2
H2A—C2—H2D	136.7	C23—C22—H22C	70.8
H2C—C2—H2D	108.2	C23'—C22—H22C	109.2
C4—C3—C2	109.4 (4)	H22B—C22—H22C	137.9
C4—C3—H3A	109.8	C21—C22—H22D	109.2
C2—C3—H3A	109.8	C23'—C22—H22D	109.2
C4—C3—H3B	109.8	H22C—C22—H22D	107.9
C2—C3—H3B	109.8	C24—C23—C22	113.7 (2)
H3A—C3—H3B	108.2	C24—C23—H23A	108.8
C3—C4—C5	106.5 (4)	C22—C23—H23A	108.8
C3—C4—H4A	110.4	C24—C23—H23B	108.8
C5—C4—H4A	110.4	C22—C23—H23B	108.8
C3—C4—H4B	110.4	H23A—C23—H23B	107.7
C5—C4—H4B	110.4	C24—C23'—C22	113.0 (3)
H4A—C4—H4B	108.6	C24—C23'—H23C	109.0
C4'—C3'—C2	109.1 (11)	C22—C23'—H23C	109.0
C4'—C3'—H3C	109.9	C24—C23'—H23D	109.0
C2—C3'—H3C	109.9	C22—C23'—H23D	109.0
C4'—C3'—H3D	109.9	H23C—C23'—H23D	107.8
C2—C3'—H3D	109.9	C23'—C24—C25	117.8 (2)
H3C—C3'—H3D	108.3	C23—C24—C25	114.3 (2)
C5—C4'—C3'	116.9 (19)	C23'—C24—H24A	133.1
C5—C4'—H4C	108.1	C23—C24—H24A	108.7
C3'—C4'—H4C	108.1	C25—C24—H24A	108.7
C5—C4'—H4D	108.1	C23—C24—H24B	108.7
C3'—C4'—H4D	108.1	C25—C24—H24B	108.7
H4C—C4'—H4D	107.3	H24A—C24—H24B	107.6
C6—C5—C10	118.82 (16)	C23'—C24—H24C	107.9
C6—C5—C4'	121.1 (11)	C25—C24—H24C	107.9
C10—C5—C4'	118.1 (11)	H24B—C24—H24C	141.8
C6—C5—C4	120.9 (3)	C23'—C24—H24D	107.9
C10—C5—C4	120.2 (3)	C23—C24—H24D	137.6
C4'—C5—C4	16.3 (11)	C25—C24—H24D	107.9
C7—C6—C5	121.20 (17)	H24C—C24—H24D	107.2
C7—C6—H6	119.4	C26—C25—C30	119.05 (17)
C5—C6—H6	119.4	C26—C25—C24	121.30 (17)
C6—C7—C8	120.10 (16)	C30—C25—C24	119.65 (16)
C6—C7—H7	119.9	C27—C26—C25	121.11 (19)
C8—C7—H7	119.9	C27—C26—H26	119.4
C9—C8—C7	119.78 (16)	C25—C26—H26	119.4
C9—C8—H8	120.1	C26—C27—C28	120.03 (17)
C7—C8—H8	120.1	C26—C27—H27	120.0
C8—C9—C10	120.45 (16)	C28—C27—H27	120.0
C8—C9—H9	119.8	C29—C28—C27	120.02 (18)
C10—C9—H9	119.8	C29—C28—H28	120.0
C9—C10—C5	119.64 (14)	C27—C28—H28	120.0
C9—C10—C1	120.94 (14)	C28—C29—C30	120.82 (17)
C5—C10—C1	119.41 (14)	C28—C29—H29	119.6
C1—N1—N2	117.98 (13)	C30—C29—H29	119.6
C11—N2—N1	119.22 (14)	C29—C30—C25	118.97 (15)
C11—N2—H2	117.8 (13)	C29—C30—C21	120.96 (14)
N1—N2—H2	123.0 (13)	C25—C30—C21	120.07 (14)
N3—C11—N2	115.75 (14)	C21—N21—N22	117.99 (13)
N3—C11—S1	124.70 (12)	C31—N22—N21	118.72 (14)
N2—C11—S1	119.54 (13)	C31—N22—H22	115.9 (14)
C11—N3—C12	124.39 (15)	N21—N22—H22	123.3 (14)
C11—N3—H3	117.7 (14)	N23—C31—N22	115.30 (16)
C12—N3—H3	117.9 (14)	N23—C31—S21	124.95 (13)
N3—C12—H12A	109.5	N22—C31—S21	119.74 (13)
N3—C12—H12B	109.5	C31—N23—C32	123.87 (18)
H12A—C12—H12B	109.5	C31—N23—H23	120.0 (15)
N3—C12—H12C	109.5	C32—N23—H23	116.0 (15)
H12A—C12—H12C	109.5	N23—C32—H32A	109.5
H12B—C12—H12C	109.5	N23—C32—H32B	109.5
N3—C12—H12D	109.5	H32A—C32—H32B	109.5
N3—C12—H12E	109.5	N23—C32—H32C	109.5
H12D—C12—H12E	109.5	H32A—C32—H32C	109.5
N3—C12—H12F	109.5	H32B—C32—H32C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S21i	0.88 (2)	3.03 (2)	3.7226 (15)	138.0

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S21i	0.88 (2)	3.03 (2)	3.7226 (15)	138.0

Symmetry code: (i) .