3-Methyl-4-[(E)-3-thien-ylmethyl-idene-amino]-1H-1,2,4-triazole-5(4H)-thione.

The asymmetric unit of the title compound, C(8)H(8)N(4)S(2), contains two crystallographically independent mol-ecules. The thio-phene ring of one mol-ecule is disordered over two positions with refined site occupancies of 0.6375 (19) and 0.3625 (19). One mol-ecule is almost planar and the other one is twisted, the dihedral angles between the thio-phene and triazole rings being 7.28 (7) and 48.9 (2)° [48.5 (4)° for the minor component], respectively. An intra-molecular C-H⋯S hydrogen bond stabilizes the mol-ecular conformation of the planar molecule. In the crystal, the two mol-ecules are inter-connected by N-H⋯S hydrogen bonds into dimers, which are further consolidated into chains along the b axis by C-H⋯N hydrogen bonds. Weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.5149 (7) Å] are also observed.

Related literature

For general background and the biological activity of Schiff bases of 1,2,4-triazole derivatives, see: Ghazzali et al. (2010 ▶); Xia et al. (2010 ▶); Aytac et al. (2009 ▶); Siddiqui et al. (2006 ▶); Kucukguzel et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H8N4S2

M = 224.30

Triclinic,

a = 9.3108 (7) Å

b = 10.2848 (8) Å

c = 12.7798 (10) Å

α = 66.632 (2)°

β = 83.409 (2)°

γ = 63.974 (2)°

V = 1006.88 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 100 K

0.36 × 0.25 × 0.23 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.845, T max = 0.896

23519 measured reflections

8745 independent reflections

7500 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.06

8745 reflections

288 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.06 e Å−3

Δρmin = −0.50 e Å−3

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/S1600536810041152/rz2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041152/rz2500Isup2.hkl

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

C8H8N4S2	Z = 4
Mr = 224.30	F(000) = 464
Triclinic, P1	Dx = 1.480 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3108 (7) Å	Cell parameters from 9994 reflections
b = 10.2848 (8) Å	θ = 2.4–35.0°
c = 12.7798 (10) Å	µ = 0.49 mm−1
α = 66.632 (2)°	T = 100 K
β = 83.409 (2)°	Block, colourless
γ = 63.974 (2)°	0.36 × 0.25 × 0.23 mm
V = 1006.88 (13) Å3

Bruker APEXII DUO CCD area-detector diffractometer	8745 independent reflections
Radiation source: fine-focus sealed tube	7500 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→13
Tmin = 0.845, Tmax = 0.896	k = −16→16
23519 measured reflections	l = −17→20

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)] = 0.040	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) + (0.0606P)2 + 0.2963P] where P = (Fo2 + 2Fc2)/3
8745 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 1.06 e Å−3
1 restraint	Δρmin = −0.50 e Å−3

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)
S1A	0.76095 (4)	−0.34744 (4)	0.39899 (2)	0.02948 (7)
S2A	0.22259 (3)	−0.11508 (3)	−0.03400 (2)	0.02363 (6)
N1A	0.35008 (11)	0.05807 (10)	0.09471 (7)	0.02091 (15)
N2A	0.24129 (11)	0.12778 (10)	0.00194 (7)	0.01941 (14)
N3A	0.07864 (12)	0.20250 (10)	−0.13672 (8)	0.02245 (16)
N4A	0.06835 (12)	0.33875 (11)	−0.13366 (8)	0.02392 (17)
C1A	0.63594 (14)	−0.31400 (13)	0.29387 (9)	0.02447 (19)
H1AA	0.6348	−0.3924	0.2755	0.029*
C2A	0.68112 (15)	−0.15163 (15)	0.37468 (10)	0.0279 (2)
H2AA	0.7137	−0.1108	0.4157	0.033*
C3A	0.56310 (14)	−0.06294 (13)	0.28710 (9)	0.02428 (19)
H3AA	0.5065	0.0456	0.2614	0.029*
C4A	0.53698 (12)	−0.15641 (12)	0.23970 (8)	0.02067 (16)
C5A	0.42312 (13)	−0.09238 (12)	0.14318 (8)	0.02136 (17)
H5AA	0.4042	−0.1571	0.1179	0.026*
C6A	0.18194 (12)	0.07072 (11)	−0.05621 (8)	0.01945 (16)
C7A	0.16892 (13)	0.29067 (12)	−0.04888 (8)	0.02199 (17)
C8A	0.20936 (16)	0.39193 (13)	−0.01317 (10)	0.0285 (2)
H8AA	0.1551	0.4992	−0.0654	0.043*
H8AB	0.3230	0.3597	−0.0134	0.043*
H8AC	0.1762	0.3825	0.0624	0.043*
S2B	0.88542 (4)	0.23323 (3)	0.64301 (2)	0.02461 (7)
N1B	0.78425 (11)	0.05827 (10)	0.51301 (7)	0.02158 (16)
N2B	0.85328 (11)	−0.01306 (10)	0.62466 (7)	0.01962 (15)
N3B	0.97744 (12)	−0.07490 (11)	0.77934 (8)	0.02242 (16)
N4B	0.98117 (13)	−0.21239 (11)	0.78403 (8)	0.02472 (17)
C4B	0.58641 (12)	0.28766 (11)	0.37606 (8)	0.01978 (16)
S1B	0.38121 (11)	0.51444 (11)	0.21591 (7)	0.02699 (15)	0.6375 (19)
C1B	0.4516 (4)	0.4333 (3)	0.3522 (3)	0.0172 (6)	0.6375 (19)
H1BA	0.4077	0.4784	0.4054	0.021*	0.6375 (19)
C2B	0.5300 (10)	0.3569 (8)	0.1808 (6)	0.0429 (15)	0.6375 (19)
H2BA	0.5390	0.3496	0.1099	0.051*	0.6375 (19)
C3B	0.6279 (10)	0.2492 (8)	0.2775 (7)	0.0299 (7)	0.6375 (19)
H3BA	0.7151	0.1577	0.2789	0.036*	0.6375 (19)
S1X	0.5125 (4)	0.3829 (3)	0.1634 (2)	0.0288 (4)	0.3625 (19)
C1X	0.6323 (13)	0.2441 (10)	0.2839 (10)	0.0172 (6)	0.3625 (19)
H1XA	0.7179	0.1506	0.2871	0.021*	0.3625 (19)
C2X	0.3997 (10)	0.5014 (10)	0.2362 (7)	0.0429 (15)	0.3625 (19)
H2XA	0.3132	0.5990	0.2040	0.051*	0.3625 (19)
C3X	0.4540 (11)	0.4332 (11)	0.3424 (8)	0.048 (2)	0.3625 (19)
H3XA	0.4062	0.4799	0.3943	0.057*	0.3625 (19)
C5B	0.66610 (12)	0.19528 (11)	0.49031 (8)	0.01976 (16)
H5BA	0.6319	0.2350	0.5472	0.024*
C6B	0.90351 (12)	0.04953 (11)	0.68276 (8)	0.01932 (16)
C7B	0.90578 (13)	−0.17204 (11)	0.68809 (8)	0.02196 (17)
C8B	0.87796 (17)	−0.27885 (13)	0.65086 (10)	0.0302 (2)
H8BA	0.9231	−0.3832	0.7087	0.045*
H8BB	0.9279	−0.2790	0.5809	0.045*
H8BC	0.7649	−0.2436	0.6389	0.045*
H3NA	0.025 (2)	0.210 (2)	−0.1941 (16)	0.035 (5)*
H3NB	1.027 (2)	−0.077 (2)	0.8312 (17)	0.037 (5)*

	U11	U22	U33	U12	U13	U23
S1A	0.02947 (14)	0.02718 (13)	0.02285 (12)	−0.01128 (11)	−0.00947 (10)	0.00081 (10)
S2A	0.02878 (13)	0.01789 (11)	0.02143 (11)	−0.00851 (9)	−0.00820 (9)	−0.00404 (8)
N1A	0.0232 (4)	0.0199 (3)	0.0164 (3)	−0.0082 (3)	−0.0052 (3)	−0.0033 (3)
N2A	0.0224 (4)	0.0171 (3)	0.0158 (3)	−0.0077 (3)	−0.0046 (3)	−0.0028 (3)
N3A	0.0257 (4)	0.0188 (3)	0.0196 (3)	−0.0092 (3)	−0.0074 (3)	−0.0025 (3)
N4A	0.0279 (4)	0.0187 (4)	0.0213 (4)	−0.0091 (3)	−0.0065 (3)	−0.0029 (3)
C1A	0.0253 (5)	0.0209 (4)	0.0227 (4)	−0.0103 (4)	−0.0057 (3)	−0.0018 (3)
C2A	0.0320 (5)	0.0301 (5)	0.0219 (4)	−0.0149 (4)	−0.0066 (4)	−0.0064 (4)
C3A	0.0295 (5)	0.0233 (4)	0.0187 (4)	−0.0119 (4)	−0.0053 (3)	−0.0044 (3)
C4A	0.0223 (4)	0.0200 (4)	0.0166 (3)	−0.0098 (3)	−0.0041 (3)	−0.0019 (3)
C5A	0.0230 (4)	0.0197 (4)	0.0187 (4)	−0.0088 (3)	−0.0051 (3)	−0.0035 (3)
C6A	0.0209 (4)	0.0187 (4)	0.0160 (3)	−0.0081 (3)	−0.0034 (3)	−0.0034 (3)
C7A	0.0260 (4)	0.0172 (4)	0.0190 (4)	−0.0084 (3)	−0.0043 (3)	−0.0028 (3)
C8A	0.0369 (6)	0.0209 (4)	0.0266 (5)	−0.0126 (4)	−0.0080 (4)	−0.0052 (4)
S2B	0.03028 (13)	0.01731 (11)	0.02452 (12)	−0.00988 (9)	−0.00816 (9)	−0.00420 (9)
N1B	0.0251 (4)	0.0173 (3)	0.0176 (3)	−0.0066 (3)	−0.0066 (3)	−0.0029 (3)
N2B	0.0229 (4)	0.0144 (3)	0.0173 (3)	−0.0064 (3)	−0.0061 (3)	−0.0019 (3)
N3B	0.0275 (4)	0.0197 (4)	0.0183 (3)	−0.0108 (3)	−0.0063 (3)	−0.0028 (3)
N4B	0.0316 (5)	0.0182 (3)	0.0205 (4)	−0.0107 (3)	−0.0081 (3)	−0.0011 (3)
C4B	0.0219 (4)	0.0163 (4)	0.0181 (4)	−0.0083 (3)	−0.0035 (3)	−0.0024 (3)
S1B	0.0283 (3)	0.0208 (2)	0.0227 (2)	−0.00926 (19)	−0.00948 (18)	0.00179 (17)
C1B	0.0168 (9)	0.0083 (7)	0.0140 (7)	0.0010 (6)	−0.0091 (7)	0.0030 (6)
C2B	0.0343 (17)	0.0261 (19)	0.063 (4)	−0.0096 (14)	−0.002 (2)	−0.014 (2)
C3B	0.0346 (15)	0.0358 (15)	0.0226 (16)	−0.0165 (12)	0.0019 (11)	−0.0131 (12)
S1X	0.0313 (8)	0.0265 (9)	0.0240 (5)	−0.0102 (7)	−0.0031 (5)	−0.0066 (5)
C1X	0.0168 (9)	0.0083 (7)	0.0140 (7)	0.0010 (6)	−0.0091 (7)	0.0030 (6)
C2X	0.0343 (17)	0.0261 (19)	0.063 (4)	−0.0096 (14)	−0.002 (2)	−0.014 (2)
C3X	0.053 (4)	0.056 (4)	0.069 (5)	−0.041 (3)	0.029 (3)	−0.044 (4)
C5B	0.0215 (4)	0.0172 (4)	0.0180 (4)	−0.0080 (3)	−0.0034 (3)	−0.0034 (3)
C6B	0.0202 (4)	0.0172 (4)	0.0184 (4)	−0.0075 (3)	−0.0034 (3)	−0.0041 (3)
C7B	0.0268 (4)	0.0152 (4)	0.0190 (4)	−0.0080 (3)	−0.0067 (3)	−0.0010 (3)
C8B	0.0433 (6)	0.0178 (4)	0.0266 (5)	−0.0125 (4)	−0.0124 (4)	−0.0027 (4)

S1A—C1A	1.7085 (11)	N2B—C7B	1.3812 (12)
S1A—C2A	1.7170 (13)	N3B—C6B	1.3430 (12)
S2A—C6A	1.6838 (10)	N3B—N4B	1.3765 (13)
N1A—C5A	1.2859 (13)	N3B—H3NB	0.84 (2)
N1A—N2A	1.3820 (11)	N4B—C7B	1.3063 (13)
N2A—C6A	1.3881 (12)	C4B—C1X	1.381 (13)
N2A—C7A	1.3889 (13)	C4B—C3X	1.392 (10)
N3A—C6A	1.3408 (13)	C4B—C1B	1.410 (3)
N3A—N4A	1.3781 (13)	C4B—C3B	1.429 (8)
N3A—H3NA	0.896 (19)	C4B—C5B	1.4542 (13)
N4A—C7A	1.3026 (13)	S1B—C1B	1.670 (3)
C1A—C4A	1.3787 (15)	S1B—C2B	1.791 (9)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.3730 (15)	C2B—C3B	1.367 (9)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.4322 (15)	C3B—H3BA	0.9300
C3A—H3AA	0.9300	S1X—C1X	1.705 (9)
C4A—C5A	1.4568 (13)	S1X—C2X	1.734 (8)
C5A—H5AA	0.9300	C1X—H1XA	0.9300
C7A—C8A	1.4816 (15)	C2X—C3X	1.297 (13)
C8A—H8AA	0.9600	C2X—H2XA	0.9300
C8A—H8AB	0.9600	C3X—H3XA	0.9300
C8A—H8AC	0.9600	C5B—H5BA	0.9300
S2B—C6B	1.6837 (10)	C7B—C8B	1.4809 (15)
N1B—C5B	1.2917 (13)	C8B—H8BA	0.9600
N1B—N2B	1.3977 (11)	C8B—H8BB	0.9600
N2B—C6B	1.3811 (12)	C8B—H8BC	0.9600
C1A—S1A—C2A	92.44 (5)	C1X—C4B—C3X	109.6 (5)
C5A—N1A—N2A	120.12 (9)	C1X—C4B—C1B	114.6 (3)
N1A—N2A—C6A	134.03 (8)	C3X—C4B—C3B	107.0 (5)
N1A—N2A—C7A	117.69 (8)	C1B—C4B—C3B	112.0 (3)
C6A—N2A—C7A	108.28 (8)	C1X—C4B—C5B	124.8 (3)
C6A—N3A—N4A	114.25 (8)	C3X—C4B—C5B	125.6 (4)
C6A—N3A—H3NA	127.0 (12)	C1B—C4B—C5B	120.56 (16)
N4A—N3A—H3NA	118.5 (12)	C3B—C4B—C5B	127.5 (3)
C7A—N4A—N3A	104.29 (8)	C1B—S1B—C2B	94.2 (3)
C4A—C1A—S1A	111.67 (8)	C4B—C1B—S1B	111.2 (2)
C4A—C1A—H1AA	124.2	C4B—C1B—H1BA	124.4
S1A—C1A—H1AA	124.2	S1B—C1B—H1BA	124.4
C3A—C2A—S1A	111.42 (8)	C3B—C2B—S1B	107.5 (6)
C3A—C2A—H2AA	124.3	C3B—C2B—H2BA	126.3
S1A—C2A—H2AA	124.3	S1B—C2B—H2BA	126.3
C2A—C3A—C4A	112.42 (10)	C2B—C3B—C4B	115.1 (6)
C2A—C3A—H3AA	123.8	C2B—C3B—H3BA	122.4
C4A—C3A—H3AA	123.8	C4B—C3B—H3BA	122.4
C1A—C4A—C3A	112.04 (9)	C1X—S1X—C2X	91.4 (5)
C1A—C4A—C5A	123.85 (10)	C4B—C1X—S1X	111.6 (5)
C3A—C4A—C5A	124.08 (9)	C4B—C1X—H1XA	124.2
N1A—C5A—C4A	116.66 (9)	S1X—C1X—H1XA	124.2
N1A—C5A—H5AA	121.7	C3X—C2X—S1X	109.7 (7)
C4A—C5A—H5AA	121.7	C3X—C2X—H2XA	125.1
N3A—C6A—N2A	102.63 (8)	S1X—C2X—H2XA	125.1
N3A—C6A—S2A	126.98 (8)	C2X—C3X—C4B	117.6 (8)
N2A—C6A—S2A	130.38 (7)	C2X—C3X—H3XA	121.2
N4A—C7A—N2A	110.54 (9)	C4B—C3X—H3XA	121.2
N4A—C7A—C8A	125.91 (9)	N1B—C5B—C4B	120.21 (9)
N2A—C7A—C8A	123.48 (9)	N1B—C5B—H5BA	119.9
C7A—C8A—H8AA	109.5	C4B—C5B—H5BA	119.9
C7A—C8A—H8AB	109.5	N3B—C6B—N2B	102.76 (8)
H8AA—C8A—H8AB	109.5	N3B—C6B—S2B	127.50 (8)
C7A—C8A—H8AC	109.5	N2B—C6B—S2B	129.69 (7)
H8AA—C8A—H8AC	109.5	N4B—C7B—N2B	110.39 (9)
H8AB—C8A—H8AC	109.5	N4B—C7B—C8B	125.79 (9)
C5B—N1B—N2B	113.61 (9)	N2B—C7B—C8B	123.82 (9)
C6B—N2B—C7B	108.61 (8)	C7B—C8B—H8BA	109.5
C6B—N2B—N1B	128.38 (8)	C7B—C8B—H8BB	109.5
C7B—N2B—N1B	122.26 (8)	H8BA—C8B—H8BB	109.5
C6B—N3B—N4B	113.86 (8)	C7B—C8B—H8BC	109.5
C6B—N3B—H3NB	126.2 (13)	H8BA—C8B—H8BC	109.5
N4B—N3B—H3NB	119.7 (13)	H8BB—C8B—H8BC	109.5
C7B—N4B—N3B	104.32 (8)
C5A—N1A—N2A—C6A	2.18 (18)	S1B—C2B—C3B—C4B	0.9 (10)
C5A—N1A—N2A—C7A	−178.40 (10)	C1X—C4B—C3B—C2B	178 (100)
C6A—N3A—N4A—C7A	0.28 (13)	C3X—C4B—C3B—C2B	−1.7 (9)
C2A—S1A—C1A—C4A	1.06 (10)	C1B—C4B—C3B—C2B	−1.1 (9)
C1A—S1A—C2A—C3A	−0.79 (10)	C5B—C4B—C3B—C2B	178.9 (5)
S1A—C2A—C3A—C4A	0.34 (14)	C3X—C4B—C1X—S1X	0.3 (10)
S1A—C1A—C4A—C3A	−1.04 (13)	C1B—C4B—C1X—S1X	1.0 (10)
S1A—C1A—C4A—C5A	177.06 (9)	C3B—C4B—C1X—S1X	0(19)
C2A—C3A—C4A—C1A	0.45 (15)	C5B—C4B—C1X—S1X	−179.1 (3)
C2A—C3A—C4A—C5A	−177.65 (11)	C2X—S1X—C1X—C4B	0.1 (9)
N2A—N1A—C5A—C4A	179.43 (9)	C1X—S1X—C2X—C3X	−0.6 (9)
C1A—C4A—C5A—N1A	−173.55 (11)	S1X—C2X—C3X—C4B	1.0 (11)
C3A—C4A—C5A—N1A	4.33 (16)	C1X—C4B—C3X—C2X	−0.9 (11)
N4A—N3A—C6A—N2A	−0.02 (12)	C1B—C4B—C3X—C2X	−174 (6)
N4A—N3A—C6A—S2A	179.17 (8)	C3B—C4B—C3X—C2X	−0.9 (10)
N1A—N2A—C6A—N3A	179.21 (11)	C5B—C4B—C3X—C2X	178.6 (6)
C7A—N2A—C6A—N3A	−0.24 (11)	N2B—N1B—C5B—C4B	177.18 (9)
N1A—N2A—C6A—S2A	0.07 (18)	C1X—C4B—C5B—N1B	−3.5 (7)
C7A—N2A—C6A—S2A	−179.39 (9)	C3X—C4B—C5B—N1B	177.1 (5)
N3A—N4A—C7A—N2A	−0.43 (12)	C1B—C4B—C5B—N1B	176.36 (19)
N3A—N4A—C7A—C8A	176.66 (11)	C3B—C4B—C5B—N1B	−3.6 (5)
N1A—N2A—C7A—N4A	−179.11 (9)	N4B—N3B—C6B—N2B	1.89 (12)
C6A—N2A—C7A—N4A	0.44 (13)	N4B—N3B—C6B—S2B	−175.95 (9)
N1A—N2A—C7A—C8A	3.72 (16)	C7B—N2B—C6B—N3B	−2.32 (12)
C6A—N2A—C7A—C8A	−176.73 (11)	N1B—N2B—C6B—N3B	−172.46 (10)
C5B—N1B—N2B—C6B	−49.59 (15)	C7B—N2B—C6B—S2B	175.46 (9)
C5B—N1B—N2B—C7B	141.48 (10)	N1B—N2B—C6B—S2B	5.31 (17)
C6B—N3B—N4B—C7B	−0.69 (13)	N3B—N4B—C7B—N2B	−0.87 (13)
C1X—C4B—C1B—S1B	0.7 (6)	N3B—N4B—C7B—C8B	179.50 (12)
C3X—C4B—C1B—S1B	7(5)	C6B—N2B—C7B—N4B	2.09 (13)
C3B—C4B—C1B—S1B	0.7 (5)	N1B—N2B—C7B—N4B	172.96 (10)
C5B—C4B—C1B—S1B	−179.23 (13)	C6B—N2B—C7B—C8B	−178.27 (11)
C2B—S1B—C1B—C4B	−0.2 (4)	N1B—N2B—C7B—C8B	−7.40 (17)
C1B—S1B—C2B—C3B	−0.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3NA···S2Bi	0.894 (19)	2.46 (2)	3.3494 (11)	177.7 (18)
N3B—H3NB···S2Aii	0.84 (2)	2.45 (2)	3.2728 (12)	167.7 (19)
C5A—H5AA···S2A	0.93	2.50	3.2311 (12)	135
C8B—H8BA···N4Aiii	0.96	2.59	3.5503 (16)	175
C5B—H5BA···Cg1iv	0.93	2.91	3.4955 (12)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3NA⋯S2Bi	0.894 (19)	2.46 (2)	3.3494 (11)	177.7 (18)
N3B—H3NB⋯S2Aii	0.84 (2)	2.45 (2)	3.2728 (12)	167.7 (19)
C5A—H5AA⋯S2A	0.93	2.50	3.2311 (12)	135
C8B—H8BA⋯N4Aiii	0.96	2.59	3.5503 (16)	175
C5B—H5BA⋯Cg1iv	0.93	2.91	3.4955 (12)	122

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