4-[(5-Chloro-2-hy-droxy-benzyl-idene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione.

The title compound, C11H11ClN4OS, crystallizes with two mol-ecules, A and B, in the asymmetric unit in which the dihedral angles between the triazole and benzene rings are 54.6 (3) and 56.0 (3)°. Both mol-ecules feature an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, A-B dimers are linked by pairs of weak C-H⋯S hydrogen bonds along with π-π stacking inter-actions between the triazole rings [centroid-centroid separations = 3.631 (3) and 3.981 (4)Å]. N-H⋯S hydrogen bonds link the dimers into [100] chains, which feature R 2 (2)(8) loops.

Related literature

For background to 1,2,4-triazoles fused to Schiff bases, see: Sumangala et al. (2013 ▶); Brandt et al. (2007 ▶). For related structures, see: Pannu et al. (2011 ▶); Wu et al. (2012 ▶).

Experimental

Crystal data

C11H11ClN4OS

M = 282.75

Monoclinic,

a = 6.297 (3) Å

b = 16.418 (8) Å

c = 12.290 (6) Å

β = 90.997 (7)°

V = 1270.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 298 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.914, T max = 0.935

14098 measured reflections

2451 independent reflections

1924 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.084

S = 1.03

2451 reflections

329 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 2274 Friedel pairs

Absolute structure parameter: 0.03 (10)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008320/hb7205sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008320/hb7205Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008320/hb7205Isup3.cml

CCDC reference: 997034

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

C11H11ClN4OS	F(000) = 584
Mr = 282.75	Dx = 1.478 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1893 reflections
a = 6.297 (3) Å	θ = 2.5–20.7°
b = 16.418 (8) Å	µ = 0.46 mm−1
c = 12.290 (6) Å	T = 298 K
β = 90.997 (7)°	Block, colorless
V = 1270.2 (10) Å3	0.20 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.914, Tmax = 0.935	k = −19→19
14098 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.183P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2451 reflections	Δρmax = 0.17 e Å−3
329 parameters	Δρmin = −0.27 e Å−3
1 restraint	Absolute structure: Flack (1983), 2274 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (10)

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
Cl1	0.3625 (2)	0.60813 (11)	1.00331 (11)	0.0760 (5)
N1	0.2557 (6)	0.7267 (3)	0.2890 (3)	0.0444 (10)
H1	0.3494	0.7463	0.2461	0.053*
N2	0.0832 (7)	0.6828 (3)	0.2520 (3)	0.0438 (11)
N3	0.0891 (6)	0.6948 (3)	0.4301 (3)	0.0347 (10)
N4	0.0053 (6)	0.6921 (3)	0.5349 (3)	0.0377 (10)
O1	−0.2784 (6)	0.7242 (3)	0.6907 (3)	0.0543 (11)
H1A	−0.2346	0.7258	0.6283	0.081*
S1	0.44562 (18)	0.78763 (8)	0.47087 (9)	0.0436 (3)
C1	0.2662 (7)	0.7364 (3)	0.3962 (3)	0.0364 (11)
C2	−0.0177 (8)	0.6646 (3)	0.3409 (4)	0.0377 (12)
C3	−0.2158 (8)	0.6175 (3)	0.3463 (4)	0.0453 (12)
H3A	−0.3226	0.6503	0.3816	0.054*
H3B	−0.1909	0.5695	0.3908	0.054*
C4	−0.3003 (8)	0.5911 (3)	0.2359 (4)	0.0518 (14)
H4A	−0.1964	0.5578	0.2009	0.078*
H4B	−0.3294	0.6383	0.1921	0.078*
H4C	−0.4287	0.5605	0.2447	0.078*
C5	0.1366 (8)	0.6718 (3)	0.6103 (4)	0.0393 (13)
H5	0.2741	0.6570	0.5923	0.047*
C6	0.0756 (8)	0.6715 (3)	0.7232 (4)	0.0368 (12)
C7	−0.1230 (8)	0.6988 (3)	0.7578 (4)	0.0411 (13)
C8	−0.1660 (8)	0.7003 (3)	0.8684 (4)	0.0523 (14)
H8	−0.2956	0.7203	0.8918	0.063*
C9	−0.0194 (9)	0.6725 (4)	0.9431 (4)	0.0572 (15)
H9	−0.0502	0.6730	1.0168	0.069*
C10	0.1759 (9)	0.6436 (3)	0.9084 (4)	0.0497 (14)
C11	0.2243 (8)	0.6449 (3)	0.8005 (4)	0.0456 (14)
H11	0.3576	0.6278	0.7785	0.055*
Cl2	−0.3045 (2)	0.97311 (11)	−0.41889 (11)	0.0672 (5)
N5	−0.2140 (6)	0.8673 (3)	0.2996 (3)	0.0477 (11)
H5A	−0.3078	0.8485	0.3430	0.057*
N6	−0.0421 (7)	0.9120 (3)	0.3347 (3)	0.0471 (11)
N7	−0.0462 (6)	0.8961 (2)	0.1579 (3)	0.0360 (10)
N8	0.0415 (6)	0.8959 (3)	0.0537 (3)	0.0404 (10)
O2	0.3237 (5)	0.8558 (3)	−0.1000 (3)	0.0567 (10)
H2	0.2853	0.8632	−0.0374	0.085*
S2	−0.40057 (19)	0.80215 (8)	0.11776 (9)	0.0453 (3)
C12	−0.2233 (7)	0.8553 (3)	0.1915 (4)	0.0365 (11)
C13	0.0582 (8)	0.9277 (3)	0.2478 (4)	0.0389 (12)
C14	0.2574 (8)	0.9764 (4)	0.2401 (4)	0.0488 (13)
H14A	0.2321	1.0232	0.1935	0.059*
H14B	0.3670	0.9434	0.2075	0.059*
C15	0.3339 (9)	1.0054 (3)	0.3517 (4)	0.0591 (15)
H15A	0.3540	0.9593	0.3988	0.089*
H15B	0.2298	1.0412	0.3820	0.089*
H15C	0.4659	1.0340	0.3448	0.089*
C16	−0.0890 (8)	0.9128 (3)	−0.0232 (4)	0.0376 (13)
H16	−0.2273	0.9275	−0.0064	0.045*
C17	−0.0282 (8)	0.9097 (3)	−0.1362 (4)	0.0363 (12)
C18	0.1690 (8)	0.8807 (3)	−0.1703 (4)	0.0400 (12)
C19	0.2111 (8)	0.8760 (3)	−0.2799 (4)	0.0463 (14)
H19	0.3395	0.8542	−0.3024	0.056*
C20	0.0655 (8)	0.9030 (3)	−0.3562 (4)	0.0440 (14)
H20	0.0955	0.8999	−0.4299	0.053*
C21	−0.1263 (9)	0.9350 (3)	−0.3228 (4)	0.0423 (13)
C22	−0.1739 (8)	0.9368 (3)	−0.2148 (4)	0.0417 (13)
H22	−0.3053	0.9563	−0.1935	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.0791 (11)	0.1054 (14)	0.0429 (8)	−0.0219 (10)	−0.0152 (7)	0.0181 (8)
N1	0.041 (2)	0.065 (3)	0.027 (2)	−0.005 (2)	0.0082 (18)	0.003 (2)
N2	0.042 (3)	0.061 (3)	0.029 (2)	−0.002 (2)	0.0026 (19)	−0.002 (2)
N3	0.036 (2)	0.044 (3)	0.024 (2)	0.000 (2)	0.0078 (17)	0.0003 (18)
N4	0.040 (2)	0.050 (3)	0.024 (2)	0.001 (2)	0.0079 (18)	0.0020 (19)
O1	0.048 (2)	0.078 (3)	0.037 (2)	0.010 (2)	0.0084 (18)	0.002 (2)
S1	0.0429 (7)	0.0589 (8)	0.0293 (6)	−0.0055 (6)	0.0057 (5)	−0.0008 (6)
C1	0.038 (3)	0.045 (3)	0.026 (3)	0.008 (2)	0.007 (2)	0.006 (2)
C2	0.039 (3)	0.041 (3)	0.033 (3)	0.009 (2)	0.000 (2)	0.000 (2)
C3	0.046 (3)	0.052 (3)	0.039 (3)	0.000 (3)	0.005 (2)	−0.004 (2)
C4	0.060 (3)	0.046 (3)	0.049 (3)	−0.007 (3)	−0.008 (3)	0.000 (3)
C5	0.043 (3)	0.043 (3)	0.032 (3)	−0.002 (2)	0.009 (2)	0.002 (2)
C6	0.042 (3)	0.041 (3)	0.027 (3)	−0.006 (2)	0.007 (2)	0.001 (2)
C7	0.049 (3)	0.046 (3)	0.029 (3)	−0.010 (3)	0.010 (2)	−0.002 (2)
C8	0.055 (3)	0.066 (4)	0.037 (3)	−0.005 (3)	0.014 (3)	−0.004 (3)
C9	0.069 (4)	0.072 (4)	0.031 (3)	−0.024 (3)	0.017 (3)	−0.005 (3)
C10	0.062 (4)	0.060 (4)	0.026 (3)	−0.021 (3)	−0.003 (2)	0.004 (2)
C11	0.048 (3)	0.050 (3)	0.039 (3)	−0.007 (3)	0.007 (2)	−0.001 (3)
Cl2	0.0642 (9)	0.1033 (13)	0.0339 (7)	0.0065 (9)	−0.0054 (6)	0.0041 (8)
N5	0.045 (3)	0.073 (3)	0.025 (2)	−0.002 (2)	0.0093 (19)	0.002 (2)
N6	0.045 (3)	0.066 (3)	0.030 (2)	0.000 (2)	0.003 (2)	−0.006 (2)
N7	0.040 (2)	0.048 (3)	0.020 (2)	0.006 (2)	0.0032 (17)	0.0036 (18)
N8	0.044 (2)	0.050 (3)	0.027 (2)	0.002 (2)	0.0106 (19)	0.0017 (19)
O2	0.051 (2)	0.082 (3)	0.037 (2)	0.018 (2)	0.0077 (17)	0.005 (2)
S2	0.0447 (7)	0.0605 (9)	0.0308 (6)	−0.0031 (7)	0.0049 (5)	0.0026 (6)
C12	0.036 (3)	0.045 (3)	0.029 (3)	0.005 (2)	0.005 (2)	0.002 (2)
C13	0.039 (3)	0.050 (3)	0.028 (3)	0.008 (2)	0.004 (2)	−0.004 (2)
C14	0.052 (3)	0.053 (3)	0.042 (3)	0.001 (3)	0.006 (2)	−0.002 (3)
C15	0.064 (4)	0.058 (4)	0.054 (3)	−0.014 (3)	−0.011 (3)	0.001 (3)
C16	0.041 (3)	0.037 (3)	0.034 (3)	0.001 (2)	0.009 (2)	0.006 (2)
C17	0.044 (3)	0.034 (3)	0.031 (3)	−0.009 (2)	0.010 (2)	−0.002 (2)
C18	0.045 (3)	0.042 (3)	0.034 (3)	0.001 (2)	0.007 (2)	0.001 (2)
C19	0.052 (3)	0.048 (3)	0.039 (3)	−0.004 (3)	0.017 (3)	−0.008 (3)
C20	0.056 (3)	0.051 (3)	0.025 (3)	−0.003 (3)	0.011 (2)	−0.005 (2)
C21	0.051 (3)	0.047 (3)	0.029 (3)	−0.005 (3)	−0.003 (2)	0.002 (2)
C22	0.040 (3)	0.052 (3)	0.034 (3)	0.003 (2)	0.005 (2)	0.001 (2)

Cl1—C10	1.741 (5)	Cl2—C21	1.732 (5)
N1—C1	1.327 (6)	N5—C12	1.342 (6)
N1—N2	1.375 (6)	N5—N6	1.371 (5)
N1—H1	0.8600	N5—H5A	0.8600
N2—C2	1.308 (7)	N6—C13	1.277 (7)
N3—C2	1.370 (6)	N7—C12	1.370 (6)
N3—C1	1.378 (6)	N7—C13	1.377 (6)
N3—N4	1.401 (5)	N7—N8	1.403 (5)
N4—C5	1.275 (6)	N8—C16	1.272 (6)
O1—C7	1.335 (6)	O2—C18	1.355 (5)
O1—H1A	0.8200	O2—H2	0.8200
S1—C1	1.670 (5)	S2—C12	1.672 (5)
C2—C3	1.470 (7)	C13—C14	1.492 (7)
C3—C4	1.512 (6)	C14—C15	1.522 (6)
C3—H3A	0.9700	C14—H14A	0.9700
C3—H3B	0.9700	C14—H14B	0.9700
C4—H4A	0.9600	C15—H15A	0.9600
C4—H4B	0.9600	C15—H15B	0.9600
C4—H4C	0.9600	C15—H15C	0.9600
C5—C6	1.446 (6)	C16—C17	1.448 (7)
C5—H5	0.9300	C16—H16	0.9300
C6—C11	1.392 (7)	C17—C22	1.394 (7)
C6—C7	1.402 (7)	C17—C18	1.400 (7)
C7—C8	1.390 (6)	C18—C19	1.380 (7)
C8—C9	1.369 (7)	C19—C20	1.373 (7)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.392 (8)	C20—C21	1.386 (7)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.366 (6)	C21—C22	1.366 (7)
C11—H11	0.9300	C22—H22	0.9300
C1—N1—N2	114.6 (4)	C12—N5—N6	114.2 (4)
C1—N1—H1	122.7	C12—N5—H5A	122.9
N2—N1—H1	122.7	N6—N5—H5A	122.9
C2—N2—N1	103.7 (4)	C13—N6—N5	104.2 (4)
C2—N3—C1	109.0 (4)	C12—N7—C13	108.8 (4)
C2—N3—N4	122.5 (4)	C12—N7—N8	127.5 (4)
C1—N3—N4	127.8 (4)	C13—N7—N8	122.8 (4)
C5—N4—N3	115.2 (4)	C16—N8—N7	114.8 (4)
C7—O1—H1A	109.5	C18—O2—H2	109.5
N1—C1—N3	102.4 (4)	N5—C12—N7	101.8 (4)
N1—C1—S1	128.8 (4)	N5—C12—S2	129.0 (4)
N3—C1—S1	128.8 (3)	N7—C12—S2	129.1 (3)
N2—C2—N3	110.3 (4)	N6—C13—N7	111.0 (5)
N2—C2—C3	125.7 (4)	N6—C13—C14	126.2 (5)
N3—C2—C3	124.0 (4)	N7—C13—C14	122.8 (4)
C2—C3—C4	113.3 (4)	C13—C14—C15	111.3 (4)
C2—C3—H3A	108.9	C13—C14—H14A	109.4
C4—C3—H3A	108.9	C15—C14—H14A	109.4
C2—C3—H3B	108.9	C13—C14—H14B	109.4
C4—C3—H3B	108.9	C15—C14—H14B	109.4
H3A—C3—H3B	107.7	H14A—C14—H14B	108.0
C3—C4—H4A	109.5	C14—C15—H15A	109.5
C3—C4—H4B	109.5	C14—C15—H15B	109.5
H4A—C4—H4B	109.5	H15A—C15—H15B	109.5
C3—C4—H4C	109.5	C14—C15—H15C	109.5
H4A—C4—H4C	109.5	H15A—C15—H15C	109.5
H4B—C4—H4C	109.5	H15B—C15—H15C	109.5
N4—C5—C6	121.2 (5)	N8—C16—C17	121.8 (5)
N4—C5—H5	119.4	N8—C16—H16	119.1
C6—C5—H5	119.4	C17—C16—H16	119.1
C11—C6—C7	119.0 (4)	C22—C17—C18	118.5 (5)
C11—C6—C5	118.0 (5)	C22—C17—C16	118.2 (5)
C7—C6—C5	122.9 (5)	C18—C17—C16	123.4 (5)
O1—C7—C8	116.4 (4)	O2—C18—C19	117.2 (4)
O1—C7—C6	124.1 (4)	O2—C18—C17	122.9 (4)
C8—C7—C6	119.5 (5)	C19—C18—C17	119.9 (5)
C9—C8—C7	120.6 (5)	C20—C19—C18	120.7 (5)
C9—C8—H8	119.7	C20—C19—H19	119.7
C7—C8—H8	119.7	C18—C19—H19	119.7
C8—C9—C10	119.8 (5)	C19—C20—C21	119.7 (5)
C8—C9—H9	120.1	C19—C20—H20	120.1
C10—C9—H9	120.1	C21—C20—H20	120.1
C11—C10—C9	120.4 (5)	C22—C21—C20	120.2 (5)
C11—C10—Cl1	119.8 (4)	C22—C21—Cl2	120.3 (4)
C9—C10—Cl1	119.9 (4)	C20—C21—Cl2	119.5 (4)
C10—C11—C6	120.6 (5)	C21—C22—C17	120.9 (5)
C10—C11—H11	119.7	C21—C22—H22	119.5
C6—C11—H11	119.7	C17—C22—H22	119.5
C1—N1—N2—C2	0.1 (6)	C12—N5—N6—C13	−0.4 (6)
C2—N3—N4—C5	137.3 (5)	C12—N7—N8—C16	52.0 (6)
C1—N3—N4—C5	−53.0 (7)	C13—N7—N8—C16	−139.5 (5)
N2—N1—C1—N3	0.8 (5)	N6—N5—C12—N7	−0.6 (5)
N2—N1—C1—S1	−178.1 (4)	N6—N5—C12—S2	177.7 (4)
C2—N3—C1—N1	−1.3 (5)	C13—N7—C12—N5	1.3 (5)
N4—N3—C1—N1	−172.1 (4)	N8—N7—C12—N5	171.1 (4)
C2—N3—C1—S1	177.6 (4)	C13—N7—C12—S2	−177.0 (4)
N4—N3—C1—S1	6.8 (7)	N8—N7—C12—S2	−7.2 (7)
N1—N2—C2—N3	−0.9 (5)	N5—N6—C13—N7	1.3 (5)
N1—N2—C2—C3	180.0 (5)	N5—N6—C13—C14	179.0 (5)
C1—N3—C2—N2	1.5 (6)	C12—N7—C13—N6	−1.7 (6)
N4—N3—C2—N2	172.8 (4)	N8—N7—C13—N6	−172.1 (4)
C1—N3—C2—C3	−179.4 (5)	C12—N7—C13—C14	−179.5 (5)
N4—N3—C2—C3	−8.0 (7)	N8—N7—C13—C14	10.1 (7)
N2—C2—C3—C4	−0.8 (7)	N6—C13—C14—C15	0.9 (8)
N3—C2—C3—C4	−179.8 (5)	N7—C13—C14—C15	178.4 (4)
N3—N4—C5—C6	176.1 (4)	N7—N8—C16—C17	−175.6 (4)
N4—C5—C6—C11	177.0 (5)	N8—C16—C17—C22	−173.7 (5)
N4—C5—C6—C7	−4.9 (8)	N8—C16—C17—C18	6.4 (8)
C11—C6—C7—O1	−178.7 (5)	C22—C17—C18—O2	177.7 (5)
C5—C6—C7—O1	3.2 (8)	C16—C17—C18—O2	−2.5 (8)
C11—C6—C7—C8	1.2 (8)	C22—C17—C18—C19	−3.0 (8)
C5—C6—C7—C8	−176.9 (5)	C16—C17—C18—C19	176.8 (5)
O1—C7—C8—C9	177.5 (5)	O2—C18—C19—C20	−177.5 (5)
C6—C7—C8—C9	−2.4 (8)	C17—C18—C19—C20	3.2 (8)
C7—C8—C9—C10	0.9 (9)	C18—C19—C20—C21	−0.4 (8)
C8—C9—C10—C11	1.8 (8)	C19—C20—C21—C22	−2.5 (8)
C8—C9—C10—Cl1	−179.9 (4)	C19—C20—C21—Cl2	177.2 (4)
C9—C10—C11—C6	−3.0 (8)	C20—C21—C22—C17	2.6 (8)
Cl1—C10—C11—C6	178.7 (4)	Cl2—C21—C22—C17	−177.1 (4)
C7—C6—C11—C10	1.5 (8)	C18—C17—C22—C21	0.2 (8)
C5—C6—C11—C10	179.7 (5)	C16—C17—C22—C21	−179.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.86	2.43	3.287 (4)	177
N5—H5A···S1ii	0.86	2.44	3.300 (4)	176
O1—H1A···N4	0.82	1.99	2.693 (5)	143
O2—H2···N8	0.82	1.99	2.699 (5)	144
C15—H15A···S1	0.96	3.01	3.922 (6)	160
C4—H4B···S2	0.96	2.87	3.805 (6)	164
Cg1···Cg2			3.631 (3)
Cg3···Cg4iii			3.981 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.86	2.43	3.287 (4)	177
N5—H5A⋯S1ii	0.86	2.44	3.300 (4)	176
O1—H1A⋯N4	0.82	1.99	2.693 (5)	143
O2—H2⋯N8	0.82	1.99	2.699 (5)	144
C15—H15A⋯S1	0.96	3.01	3.922 (6)	160
C4—H4B⋯S2	0.96	2.87	3.805 (6)	164

Symmetry codes: (i) ; (ii) .