Benzyl N'-(2-chloro-benzyl-idene)hydrazinecarbodithio-ate.

The asymmetric unit of the title compound, C(15)H(13)ClN(2)S(2), contains two independent mol-ecules, which are linked into a pseudo-centrosymmetric dimer by inter-molecular N-H⋯S hydrogen bonds. The aromatic rings form dihedral angles of 67.06 (3) and 81.85 (2)° in the two independent mol-ecules.

Related literature

For the biomedical properties of ligands derived from S-benzyl­dithio­carbaza­te, see: Ali et al. (2001 ▶, 2002 ▶); Tarafder et al. (2001 ▶, 2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13ClN2S2

M = 320.84

Triclinic,

a = 11.877 (2) Å

b = 11.906 (2) Å

c = 12.623 (3) Å

α = 68.242 (3)°

β = 71.116 (4)°

γ = 82.335 (4)°

V = 1568.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 295 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.971

8397 measured reflections

5524 independent reflections

3436 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 0.97

5524 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 and SAINT (Bruker, 2005 ▶); 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 .

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034892/cv2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034892/cv2453Isup2.hkl

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

C15H13ClN2S2	Z = 4
Mr = 320.84	F000 = 664
Triclinic, P1	Dx = 1.359 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.877 (2) Å	Cell parameters from 1618 reflections
b = 11.906 (2) Å	θ = 2.6–24.6º
c = 12.623 (3) Å	µ = 0.50 mm−1
α = 68.242 (3)º	T = 295 (2) K
β = 71.116 (4)º	Block, yellow
γ = 82.335 (4)º	0.12 × 0.10 × 0.06 mm
V = 1568.4 (5) Å3

Bruker APEXII CCD area-detector diffractometer	5524 independent reflections
Radiation source: fine-focus sealed tube	3436 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 295(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −11→14
Tmin = 0.942, Tmax = 0.971	k = −14→13
8397 measured reflections	l = −14→14

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4623P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
5524 reflections	Δρmax = 0.44 e Å−3
361 parameters	Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl2	0.61916 (10)	0.15814 (11)	0.57081 (9)	0.0994 (4)
S3	0.36389 (7)	0.66976 (8)	0.21058 (7)	0.0541 (3)
S4	0.15028 (7)	0.61729 (8)	0.43141 (7)	0.0566 (3)
N3	0.3563 (2)	0.5043 (2)	0.4167 (2)	0.0514 (7)
H3A	0.3270	0.4634	0.4914	0.062*
N4	0.4704 (2)	0.4789 (2)	0.3570 (2)	0.0478 (7)
C16	0.6959 (3)	0.2483 (3)	0.4266 (3)	0.0544 (9)
C17	0.6419 (3)	0.3506 (3)	0.3648 (3)	0.0455 (8)
C18	0.7096 (3)	0.4188 (3)	0.2498 (3)	0.0554 (9)
H18	0.6770	0.4888	0.2056	0.066*
C19	0.8242 (3)	0.3835 (3)	0.2014 (3)	0.0606 (10)
H19	0.8678	0.4290	0.1244	0.073*
C20	0.8742 (3)	0.2812 (4)	0.2663 (3)	0.0617 (10)
H20	0.9518	0.2584	0.2332	0.074*
C21	0.8112 (3)	0.2133 (3)	0.3785 (3)	0.0631 (10)
H21	0.8452	0.1443	0.4224	0.076*
C22	0.5211 (3)	0.3882 (3)	0.4168 (3)	0.0504 (8)
H22	0.4802	0.3449	0.4955	0.061*
C23	0.2902 (3)	0.5914 (3)	0.3608 (3)	0.0441 (8)
C24	0.2502 (3)	0.7786 (3)	0.1668 (3)	0.0612 (10)
H24A	0.1772	0.7372	0.1861	0.073*
H24B	0.2335	0.8347	0.2097	0.073*
C25	0.2944 (3)	0.8461 (3)	0.0345 (3)	0.0480 (8)
C26	0.3717 (3)	0.9404 (3)	−0.0123 (3)	0.0609 (10)
H26	0.3981	0.9628	0.0389	0.073*
C27	0.4111 (3)	1.0026 (3)	−0.1335 (3)	0.0689 (11)
H27	0.4636	1.0661	−0.1634	0.083*
C28	0.3730 (3)	0.9712 (4)	−0.2098 (3)	0.0684 (11)
H28	0.3994	1.0132	−0.2916	0.082*
C29	0.2967 (3)	0.8785 (4)	−0.1655 (3)	0.0716 (11)
H29	0.2702	0.8573	−0.2172	0.086*
C30	0.2579 (3)	0.8152 (3)	−0.0442 (3)	0.0623 (10)
H30	0.2065	0.7509	−0.0151	0.075*
Cl1	−0.22425 (9)	0.74778 (9)	0.55632 (8)	0.0702 (3)
S1	0.06032 (8)	0.28590 (8)	0.93397 (7)	0.0589 (3)
S2	0.25595 (8)	0.30266 (9)	0.70505 (7)	0.0619 (3)
N1	0.0603 (2)	0.4336 (2)	0.7232 (2)	0.0497 (7)
H1	0.0857	0.4679	0.6469	0.060*
N2	−0.0472 (2)	0.4698 (2)	0.7859 (2)	0.0466 (7)
C1	−0.2804 (3)	0.6881 (3)	0.7111 (3)	0.0492 (8)
C2	−0.2159 (3)	0.6018 (3)	0.7786 (3)	0.0444 (8)
C3	−0.2674 (3)	0.5582 (3)	0.9025 (3)	0.0577 (9)
H3	−0.2269	0.5002	0.9504	0.069*
C4	−0.3772 (3)	0.5999 (4)	0.9548 (3)	0.0728 (11)
H4	−0.4098	0.5708	1.0375	0.087*
C5	−0.4383 (3)	0.6844 (4)	0.8849 (4)	0.0804 (13)
H5	−0.5128	0.7118	0.9205	0.097*
C6	−0.3909 (3)	0.7286 (4)	0.7634 (3)	0.0669 (10)
H6	−0.4329	0.7857	0.7164	0.080*
C7	−0.1006 (3)	0.5565 (3)	0.7233 (3)	0.0461 (8)
H7	−0.0652	0.5910	0.6413	0.055*
C8	0.1257 (3)	0.3461 (3)	0.7791 (3)	0.0446 (8)
C9	0.1668 (3)	0.1677 (3)	0.9769 (3)	0.0613 (10)
H9A	0.1802	0.1150	0.9308	0.074*
H9B	0.2421	0.2030	0.9614	0.074*
C10	0.1176 (3)	0.0961 (3)	1.1086 (3)	0.0476 (8)
C11	0.1692 (3)	0.1043 (3)	1.1888 (3)	0.0572 (9)
H11	0.2325	0.1561	1.1620	0.069*
C12	0.1273 (3)	0.0359 (3)	1.3090 (3)	0.0639 (10)
H12	0.1632	0.0415	1.3622	0.077*
C13	0.0338 (3)	−0.0398 (3)	1.3501 (3)	0.0632 (10)
H13	0.0060	−0.0854	1.4310	0.076*
C14	−0.0190 (3)	−0.0484 (3)	1.2711 (3)	0.0672 (11)
H14	−0.0827	−0.0999	1.2983	0.081*
C15	0.0231 (3)	0.0200 (3)	1.1512 (3)	0.0617 (10)
H15	−0.0132	0.0144	1.0982	0.074*

	U11	U22	U33	U12	U13	U23
Cl2	0.0801 (8)	0.0990 (9)	0.0654 (7)	0.0195 (6)	−0.0101 (6)	0.0142 (6)
S3	0.0454 (5)	0.0542 (6)	0.0410 (5)	0.0071 (4)	−0.0009 (4)	−0.0054 (4)
S4	0.0451 (5)	0.0626 (6)	0.0416 (5)	0.0100 (4)	−0.0017 (4)	−0.0085 (4)
N3	0.0410 (16)	0.0570 (18)	0.0386 (15)	0.0077 (13)	−0.0044 (12)	−0.0063 (13)
N4	0.0396 (15)	0.0508 (17)	0.0441 (16)	0.0053 (13)	−0.0071 (13)	−0.0135 (13)
C16	0.046 (2)	0.064 (2)	0.0444 (19)	0.0060 (17)	−0.0116 (16)	−0.0131 (17)
C17	0.0387 (18)	0.050 (2)	0.0456 (18)	0.0053 (15)	−0.0141 (15)	−0.0155 (16)
C18	0.051 (2)	0.056 (2)	0.054 (2)	0.0006 (17)	−0.0130 (17)	−0.0162 (17)
C19	0.056 (2)	0.069 (3)	0.052 (2)	−0.005 (2)	−0.0029 (18)	−0.0267 (19)
C20	0.045 (2)	0.077 (3)	0.070 (3)	0.012 (2)	−0.0156 (19)	−0.040 (2)
C21	0.057 (2)	0.071 (3)	0.063 (2)	0.019 (2)	−0.027 (2)	−0.025 (2)
C22	0.047 (2)	0.052 (2)	0.0402 (18)	0.0013 (17)	−0.0081 (16)	−0.0086 (16)
C23	0.0441 (18)	0.0427 (19)	0.0399 (17)	0.0017 (15)	−0.0081 (15)	−0.0126 (15)
C24	0.049 (2)	0.059 (2)	0.051 (2)	0.0140 (17)	−0.0038 (17)	−0.0065 (17)
C25	0.0372 (18)	0.045 (2)	0.0478 (19)	0.0061 (15)	−0.0070 (15)	−0.0073 (16)
C26	0.064 (2)	0.065 (2)	0.051 (2)	−0.010 (2)	−0.0216 (18)	−0.0108 (19)
C27	0.073 (3)	0.062 (3)	0.057 (2)	−0.020 (2)	−0.014 (2)	−0.002 (2)
C28	0.064 (2)	0.075 (3)	0.048 (2)	0.002 (2)	−0.0136 (19)	−0.004 (2)
C29	0.064 (2)	0.093 (3)	0.060 (2)	0.000 (2)	−0.026 (2)	−0.024 (2)
C30	0.044 (2)	0.060 (2)	0.077 (3)	−0.0071 (18)	−0.0144 (19)	−0.019 (2)
Cl1	0.0795 (7)	0.0724 (7)	0.0449 (5)	0.0055 (5)	−0.0195 (5)	−0.0065 (4)
S1	0.0544 (5)	0.0630 (6)	0.0368 (5)	0.0098 (4)	−0.0037 (4)	−0.0044 (4)
S2	0.0575 (6)	0.0645 (6)	0.0414 (5)	0.0168 (5)	−0.0038 (4)	−0.0092 (4)
N1	0.0471 (16)	0.0566 (18)	0.0324 (14)	0.0087 (14)	−0.0064 (12)	−0.0090 (13)
N2	0.0382 (15)	0.0541 (17)	0.0400 (15)	0.0016 (13)	−0.0064 (12)	−0.0133 (13)
C1	0.050 (2)	0.053 (2)	0.0430 (19)	0.0028 (17)	−0.0150 (16)	−0.0158 (16)
C2	0.0414 (18)	0.048 (2)	0.0406 (18)	−0.0013 (15)	−0.0083 (15)	−0.0144 (15)
C3	0.056 (2)	0.061 (2)	0.045 (2)	0.0045 (18)	−0.0118 (17)	−0.0111 (17)
C4	0.058 (2)	0.092 (3)	0.049 (2)	0.005 (2)	−0.0011 (19)	−0.019 (2)
C5	0.050 (2)	0.108 (4)	0.075 (3)	0.021 (2)	−0.010 (2)	−0.038 (3)
C6	0.057 (2)	0.078 (3)	0.065 (3)	0.019 (2)	−0.025 (2)	−0.025 (2)
C7	0.0427 (18)	0.050 (2)	0.0369 (17)	0.0004 (16)	−0.0086 (15)	−0.0086 (15)
C8	0.0452 (18)	0.0440 (19)	0.0380 (17)	0.0020 (15)	−0.0105 (15)	−0.0095 (15)
C9	0.059 (2)	0.061 (2)	0.044 (2)	0.0099 (18)	−0.0101 (17)	−0.0044 (17)
C10	0.053 (2)	0.044 (2)	0.0389 (17)	0.0089 (16)	−0.0134 (16)	−0.0101 (15)
C11	0.065 (2)	0.049 (2)	0.053 (2)	−0.0041 (18)	−0.0205 (18)	−0.0095 (17)
C12	0.076 (3)	0.070 (3)	0.047 (2)	0.009 (2)	−0.026 (2)	−0.0189 (19)
C13	0.077 (3)	0.060 (2)	0.0364 (19)	0.010 (2)	−0.0092 (19)	−0.0085 (17)
C14	0.066 (2)	0.065 (3)	0.055 (2)	−0.011 (2)	−0.007 (2)	−0.011 (2)
C15	0.066 (2)	0.069 (3)	0.050 (2)	−0.003 (2)	−0.0174 (19)	−0.0199 (19)

Cl2—C16	1.742 (3)	Cl1—C1	1.738 (3)
S3—C23	1.750 (3)	S1—C8	1.751 (3)
S3—C24	1.815 (3)	S1—C9	1.810 (3)
S4—C23	1.662 (3)	S2—C8	1.657 (3)
N3—C23	1.337 (4)	N1—C8	1.334 (4)
N3—N4	1.376 (3)	N1—N2	1.375 (3)
N3—H3A	0.8600	N1—H1	0.8600
N4—C22	1.271 (4)	N2—C7	1.279 (4)
C16—C17	1.384 (4)	C1—C6	1.377 (5)
C16—C21	1.384 (5)	C1—C2	1.390 (4)
C17—C18	1.399 (4)	C2—C3	1.398 (4)
C17—C22	1.458 (4)	C2—C7	1.455 (4)
C18—C19	1.380 (5)	C3—C4	1.376 (5)
C18—H18	0.9300	C3—H3	0.9300
C19—C20	1.375 (5)	C4—C5	1.371 (5)
C19—H19	0.9300	C4—H4	0.9300
C20—C21	1.358 (5)	C5—C6	1.366 (5)
C20—H20	0.9300	C5—H5	0.9300
C21—H21	0.9300	C6—H6	0.9300
C22—H22	0.9300	C7—H7	0.9300
C24—C25	1.503 (4)	C9—C10	1.512 (4)
C24—H24A	0.9700	C9—H9A	0.9700
C24—H24B	0.9700	C9—H9B	0.9700
C25—C26	1.373 (4)	C10—C15	1.374 (4)
C25—C30	1.379 (5)	C10—C11	1.378 (4)
C26—C27	1.377 (5)	C11—C12	1.384 (5)
C26—H26	0.9300	C11—H11	0.9300
C27—C28	1.366 (5)	C12—C13	1.364 (5)
C27—H27	0.9300	C12—H12	0.9300
C28—C29	1.355 (5)	C13—C14	1.377 (5)
C28—H28	0.9300	C13—H13	0.9300
C29—C30	1.381 (5)	C14—C15	1.382 (5)
C29—H29	0.9300	C14—H14	0.9300
C30—H30	0.9300	C15—H15	0.9300
C23—S3—C24	101.41 (15)	C8—S1—C9	101.13 (15)
C23—N3—N4	121.2 (2)	C8—N1—N2	121.0 (2)
C23—N3—H3A	119.4	C8—N1—H1	119.5
N4—N3—H3A	119.4	N2—N1—H1	119.5
C22—N4—N3	115.6 (3)	C7—N2—N1	115.5 (3)
C17—C16—C21	122.5 (3)	C6—C1—C2	121.8 (3)
C17—C16—Cl2	120.3 (3)	C6—C1—Cl1	117.5 (3)
C21—C16—Cl2	117.3 (3)	C2—C1—Cl1	120.7 (3)
C16—C17—C18	116.9 (3)	C1—C2—C3	117.1 (3)
C16—C17—C22	122.2 (3)	C1—C2—C7	121.8 (3)
C18—C17—C22	120.9 (3)	C3—C2—C7	121.0 (3)
C19—C18—C17	120.8 (3)	C4—C3—C2	121.1 (3)
C19—C18—H18	119.6	C4—C3—H3	119.5
C17—C18—H18	119.6	C2—C3—H3	119.5
C20—C19—C18	120.3 (3)	C5—C4—C3	119.9 (4)
C20—C19—H19	119.9	C5—C4—H4	120.1
C18—C19—H19	119.9	C3—C4—H4	120.1
C21—C20—C19	120.5 (3)	C6—C5—C4	120.6 (4)
C21—C20—H20	119.8	C6—C5—H5	119.7
C19—C20—H20	119.8	C4—C5—H5	119.7
C20—C21—C16	119.2 (3)	C5—C6—C1	119.5 (4)
C20—C21—H21	120.4	C5—C6—H6	120.3
C16—C21—H21	120.4	C1—C6—H6	120.3
N4—C22—C17	121.6 (3)	N2—C7—C2	120.9 (3)
N4—C22—H22	119.2	N2—C7—H7	119.6
C17—C22—H22	119.2	C2—C7—H7	119.6
N3—C23—S4	121.1 (2)	N1—C8—S2	121.6 (2)
N3—C23—S3	114.0 (2)	N1—C8—S1	113.4 (2)
S4—C23—S3	124.88 (19)	S2—C8—S1	125.03 (19)
C25—C24—S3	108.6 (2)	C10—C9—S1	108.5 (2)
C25—C24—H24A	110.0	C10—C9—H9A	110.0
S3—C24—H24A	110.0	S1—C9—H9A	110.0
C25—C24—H24B	110.0	C10—C9—H9B	110.0
S3—C24—H24B	110.0	S1—C9—H9B	110.0
H24A—C24—H24B	108.4	H9A—C9—H9B	108.4
C26—C25—C30	117.7 (3)	C15—C10—C11	118.4 (3)
C26—C25—C24	121.6 (3)	C15—C10—C9	121.5 (3)
C30—C25—C24	120.8 (3)	C11—C10—C9	120.0 (3)
C25—C26—C27	121.3 (3)	C10—C11—C12	120.4 (3)
C25—C26—H26	119.4	C10—C11—H11	119.8
C27—C26—H26	119.4	C12—C11—H11	119.8
C28—C27—C26	120.1 (3)	C13—C12—C11	120.6 (3)
C28—C27—H27	119.9	C13—C12—H12	119.7
C26—C27—H27	119.9	C11—C12—H12	119.7
C29—C28—C27	119.6 (3)	C12—C13—C14	119.6 (3)
C29—C28—H28	120.2	C12—C13—H13	120.2
C27—C28—H28	120.2	C14—C13—H13	120.2
C28—C29—C30	120.5 (4)	C13—C14—C15	119.6 (3)
C28—C29—H29	119.8	C13—C14—H14	120.2
C30—C29—H29	119.8	C15—C14—H14	120.2
C25—C30—C29	120.9 (3)	C10—C15—C14	121.3 (3)
C25—C30—H30	119.6	C10—C15—H15	119.3
C29—C30—H30	119.6	C14—C15—H15	119.3
C23—N3—N4—C22	−174.7 (3)	C8—N1—N2—C7	178.3 (3)
C21—C16—C17—C18	−0.1 (5)	C6—C1—C2—C3	−0.5 (5)
Cl2—C16—C17—C18	179.5 (3)	Cl1—C1—C2—C3	−179.9 (3)
C21—C16—C17—C22	−178.8 (3)	C6—C1—C2—C7	178.3 (3)
Cl2—C16—C17—C22	0.8 (5)	Cl1—C1—C2—C7	−1.0 (4)
C16—C17—C18—C19	0.7 (5)	C1—C2—C3—C4	−0.3 (5)
C22—C17—C18—C19	179.4 (3)	C7—C2—C3—C4	−179.2 (3)
C17—C18—C19—C20	−0.9 (5)	C2—C3—C4—C5	0.8 (6)
C18—C19—C20—C21	0.5 (6)	C3—C4—C5—C6	−0.6 (6)
C19—C20—C21—C16	0.1 (6)	C4—C5—C6—C1	−0.2 (6)
C17—C16—C21—C20	−0.3 (6)	C2—C1—C6—C5	0.8 (6)
Cl2—C16—C21—C20	−179.9 (3)	Cl1—C1—C6—C5	−179.8 (3)
N3—N4—C22—C17	179.8 (3)	N1—N2—C7—C2	179.0 (3)
C16—C17—C22—N4	−176.4 (3)	C1—C2—C7—N2	−174.0 (3)
C18—C17—C22—N4	5.0 (5)	C3—C2—C7—N2	4.8 (5)
N4—N3—C23—S4	176.9 (2)	N2—N1—C8—S2	−179.3 (2)
N4—N3—C23—S3	−2.0 (4)	N2—N1—C8—S1	0.3 (4)
C24—S3—C23—N3	−179.2 (3)	C9—S1—C8—N1	177.0 (2)
C24—S3—C23—S4	1.8 (3)	C9—S1—C8—S2	−3.5 (3)
C23—S3—C24—C25	−174.0 (2)	C8—S1—C9—C10	−174.1 (2)
S3—C24—C25—C26	−80.4 (4)	S1—C9—C10—C15	71.2 (4)
S3—C24—C25—C30	99.9 (3)	S1—C9—C10—C11	−110.1 (3)
C30—C25—C26—C27	0.4 (5)	C15—C10—C11—C12	0.9 (5)
C24—C25—C26—C27	−179.4 (3)	C9—C10—C11—C12	−177.8 (3)
C25—C26—C27—C28	0.2 (6)	C10—C11—C12—C13	−0.6 (6)
C26—C27—C28—C29	−0.1 (6)	C11—C12—C13—C14	0.2 (6)
C27—C28—C29—C30	−0.5 (6)	C12—C13—C14—C15	−0.1 (6)
C26—C25—C30—C29	−0.9 (5)	C11—C10—C15—C14	−0.9 (6)
C24—C25—C30—C29	178.8 (3)	C9—C10—C15—C14	177.8 (3)
C28—C29—C30—C25	1.0 (6)	C13—C14—C15—C10	0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S4	0.86	2.56	3.405 (3)	166
N3—H3A···S2	0.86	2.60	3.451 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S4	0.86	2.56	3.405 (3)	166
N3—H3A⋯S2	0.86	2.60	3.451 (3)	169