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

The title compound, C11H11BrN4OS, crystallized as a racemic twin with two symmetry-independent mol-ecules in the asymmetric unit. The dihedral angles between the benzene and triazole rings of the two independent mol-ecules are 56.41 (18) and 54.48 (18)°. An intra-molecular O-H⋯N hydrogen bond occurs in each mol-ecule. In the crystal, pairs of symmetry-independent mol-ecules are linked by pairs of almost linear N-H⋯S hydrogen bonds, forming cyclic dimers characterized by an R 2 (2)(8) motif. There are weak π-π inter-actions between the benzene rings of symmetry-independent mol-ecules, with a centroid-centroid distance of 3.874 (3) Å.

Related literature

For background to the biological activity of related compounds, see: Demirbas (2004 ▶); Demirbas et al. (2009 ▶); Todoulou et al. (1994 ▶); Kumar et al. (2008 ▶); Kochikyan et al. (2011 ▶); Singhal et al. (2011 ▶); Popiołek et al. (2013 ▶); Sraa (2012 ▶). For similar structures, see: Wu et al. (2012 ▶); Pannu & Hundal (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For graph-sets of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H11BrN4OS

M = 327.21

Monoclinic,

a = 6.323 (4) Å

b = 16.459 (11) Å

c = 12.461 (8) Å

β = 90.330 (9)°

V = 1296.8 (15) Å3

Z = 4

Mo Kα radiation

μ = 3.32 mm−1

T = 298 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.350, T max = 0.435

14802 measured reflections

5222 independent reflections

4285 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.065

S = 1.01

5222 reflections

328 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), 2514 Friedel pairs

Absolute structure parameter: 0.581 (7)

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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814016833/fy2115sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016833/fy2115Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016833/fy2115Isup3.cml

CCDC reference: 1015277

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

C11H11BrN4OS	F(000) = 656
Mr = 327.21	Dx = 1.676 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4187 reflections
a = 6.323 (4) Å	θ = 2.5–25.3°
b = 16.459 (11) Å	µ = 3.32 mm−1
c = 12.461 (8) Å	T = 298 K
β = 90.330 (9)°	Block, yellow
V = 1296.8 (15) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker SMART APEXII diffractometer	5222 independent reflections
Radiation source: fine-focus sealed tube	4285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 26.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −7→7
Tmin = 0.350, Tmax = 0.435	k = −20→20
14802 measured reflections	l = −15→15

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) = 0.065	w = 1/[σ2(Fo2) + (0.031P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
5222 reflections	Δρmax = 0.28 e Å−3
328 parameters	Δρmin = −0.45 e Å−3
1 restraint	Absolute structure: Flack (1983), 2514 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.581 (7)

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
Br1	0.19835 (6)	0.61341 (2)	−0.42475 (3)	0.05443 (12)
S1	0.10279 (14)	0.43885 (6)	0.11498 (7)	0.0394 (2)
O1	0.8327 (4)	0.49113 (17)	−0.10062 (19)	0.0511 (7)
H1A	0.8001	0.5035	−0.0391	0.077*
N1	0.2852 (5)	0.50342 (19)	0.2940 (2)	0.0425 (8)
H1	0.1906	0.4848	0.3368	0.051*
N2	0.4568 (5)	0.5484 (2)	0.3291 (2)	0.0423 (8)
N3	0.4567 (4)	0.53213 (17)	0.1540 (2)	0.0313 (7)
N4	0.5457 (4)	0.53192 (18)	0.0511 (2)	0.0360 (7)
C1	0.2787 (5)	0.4913 (2)	0.1880 (3)	0.0325 (8)
C2	0.5590 (5)	0.5653 (2)	0.2428 (3)	0.0337 (8)
C3	0.7562 (6)	0.6128 (3)	0.2360 (3)	0.0438 (9)
H3A	0.7331	0.6594	0.1898	0.053*
H3B	0.8655	0.5795	0.2039	0.053*
C4	0.8317 (7)	0.6420 (2)	0.3461 (3)	0.0529 (11)
H4A	0.7232	0.6744	0.3786	0.079*
H4B	0.9574	0.6741	0.3380	0.079*
H4C	0.8619	0.5960	0.3909	0.079*
C5	0.4165 (6)	0.5478 (2)	−0.0249 (3)	0.0332 (8)
H5	0.2777	0.5616	−0.0087	0.040*
C6	0.4824 (5)	0.5449 (2)	−0.1370 (3)	0.0305 (8)
C7	0.6786 (5)	0.5157 (2)	−0.1695 (3)	0.0343 (8)
C8	0.7249 (6)	0.5113 (2)	−0.2784 (3)	0.0404 (10)
H8	0.8531	0.4893	−0.3004	0.048*
C9	0.5816 (6)	0.5393 (2)	−0.3542 (3)	0.0390 (9)
H9	0.6142	0.5370	−0.4268	0.047*
C10	0.3887 (6)	0.5707 (2)	−0.3211 (3)	0.0362 (9)
C11	0.3376 (6)	0.5723 (2)	−0.2137 (3)	0.0342 (8)
H11	0.2063	0.5917	−0.1923	0.041*
Br2	0.85545 (7)	0.24611 (3)	0.99904 (3)	0.06106 (14)
S2	0.93822 (14)	0.42617 (6)	0.46355 (7)	0.0375 (2)
O2	0.2087 (4)	0.36500 (17)	0.6796 (2)	0.0480 (8)
H2	0.2556	0.3672	0.6184	0.072*
N5	0.7520 (5)	0.36383 (19)	0.2834 (2)	0.0390 (8)
H5A	0.8466	0.3827	0.2409	0.047*
N6	0.5811 (5)	0.3204 (2)	0.2478 (2)	0.0401 (8)
N7	0.5821 (4)	0.33383 (18)	0.4232 (2)	0.0314 (7)
N8	0.4955 (4)	0.33164 (19)	0.5266 (2)	0.0321 (7)
C12	0.7603 (5)	0.3746 (2)	0.3909 (3)	0.0319 (8)
C13	0.4769 (5)	0.3032 (2)	0.3348 (3)	0.0315 (8)
C14	0.2795 (5)	0.2556 (2)	0.3413 (3)	0.0400 (8)
H14A	0.1713	0.2884	0.3750	0.048*
H14B	0.3037	0.2083	0.3863	0.048*
C15	0.1996 (6)	0.2275 (2)	0.2317 (3)	0.0472 (10)
H15A	0.1887	0.2735	0.1845	0.071*
H15B	0.0630	0.2028	0.2393	0.071*
H15C	0.2967	0.1887	0.2023	0.071*
C16	0.6252 (6)	0.3124 (2)	0.6007 (3)	0.0353 (9)
H16	0.7633	0.2985	0.5832	0.042*
C17	0.5601 (6)	0.3117 (2)	0.7123 (3)	0.0328 (8)
C18	0.3609 (6)	0.3392 (2)	0.7470 (3)	0.0361 (9)
C19	0.3173 (6)	0.3417 (2)	0.8567 (3)	0.0443 (9)
H19	0.1881	0.3620	0.8797	0.053*
C20	0.4612 (6)	0.3147 (2)	0.9307 (3)	0.0462 (10)
H20	0.4296	0.3165	1.0034	0.055*
C21	0.6543 (6)	0.2846 (2)	0.8971 (3)	0.0423 (9)
C22	0.7078 (6)	0.2850 (2)	0.7897 (3)	0.0403 (9)
H22	0.8411	0.2675	0.7685	0.048*

	U11	U22	U33	U12	U13	U23
Br1	0.0537 (2)	0.0799 (3)	0.02963 (19)	0.0011 (2)	−0.00409 (16)	0.0045 (2)
S1	0.0403 (5)	0.0497 (6)	0.0281 (4)	−0.0051 (4)	0.0038 (4)	0.0017 (4)
O1	0.0457 (16)	0.074 (2)	0.0334 (14)	0.0183 (14)	0.0076 (12)	0.0048 (14)
N1	0.0402 (18)	0.064 (2)	0.0238 (16)	−0.0095 (16)	0.0092 (13)	0.0011 (15)
N2	0.0442 (18)	0.058 (2)	0.0251 (15)	−0.0021 (16)	0.0042 (14)	−0.0043 (14)
N3	0.0337 (16)	0.0378 (18)	0.0226 (15)	0.0022 (14)	0.0057 (12)	0.0023 (13)
N4	0.0364 (17)	0.047 (2)	0.0252 (16)	0.0010 (14)	0.0102 (13)	0.0031 (14)
C1	0.034 (2)	0.036 (2)	0.0277 (19)	0.0065 (16)	0.0038 (15)	0.0053 (15)
C2	0.035 (2)	0.036 (2)	0.0300 (19)	0.0093 (16)	0.0040 (15)	−0.0019 (15)
C3	0.047 (2)	0.044 (2)	0.041 (2)	−0.002 (2)	0.0050 (16)	0.003 (2)
C4	0.062 (3)	0.047 (3)	0.049 (2)	−0.013 (2)	−0.008 (2)	0.0012 (19)
C5	0.0341 (19)	0.033 (2)	0.033 (2)	0.0020 (16)	0.0075 (16)	0.0027 (16)
C6	0.0342 (19)	0.031 (2)	0.0260 (18)	−0.0051 (16)	0.0071 (15)	0.0024 (15)
C7	0.036 (2)	0.035 (2)	0.0315 (19)	0.0044 (16)	0.0048 (16)	0.0009 (15)
C8	0.043 (2)	0.043 (2)	0.035 (2)	0.0007 (18)	0.0164 (19)	−0.0040 (17)
C9	0.048 (2)	0.047 (2)	0.0228 (18)	−0.0021 (19)	0.0103 (16)	−0.0042 (16)
C10	0.043 (2)	0.040 (2)	0.0249 (18)	−0.0066 (17)	0.0016 (16)	0.0001 (16)
C11	0.0327 (19)	0.043 (2)	0.0275 (19)	−0.0011 (16)	0.0046 (15)	−0.0031 (16)
Br2	0.0659 (3)	0.0819 (3)	0.0352 (2)	−0.0148 (2)	−0.01050 (19)	0.0139 (2)
S2	0.0369 (5)	0.0487 (6)	0.0268 (4)	−0.0048 (4)	0.0045 (4)	−0.0016 (4)
O2	0.0395 (16)	0.067 (2)	0.0380 (16)	0.0097 (14)	0.0065 (12)	0.0014 (14)
N5	0.0415 (19)	0.053 (2)	0.0224 (16)	−0.0015 (15)	0.0075 (13)	0.0009 (14)
N6	0.0423 (19)	0.055 (2)	0.0233 (16)	−0.0035 (16)	0.0007 (14)	−0.0044 (14)
N7	0.0297 (16)	0.0400 (18)	0.0248 (15)	0.0023 (14)	0.0068 (12)	−0.0010 (13)
N8	0.0317 (16)	0.0435 (19)	0.0213 (16)	−0.0013 (14)	0.0081 (13)	−0.0012 (13)
C12	0.0308 (19)	0.042 (2)	0.0233 (17)	0.0038 (16)	0.0039 (14)	0.0010 (15)
C13	0.034 (2)	0.037 (2)	0.0237 (18)	0.0016 (16)	−0.0003 (15)	−0.0048 (15)
C14	0.0397 (19)	0.043 (2)	0.0373 (19)	−0.0010 (18)	0.0062 (15)	−0.0065 (17)
C15	0.054 (2)	0.041 (3)	0.047 (2)	−0.0062 (19)	−0.0110 (19)	−0.0010 (19)
C16	0.042 (2)	0.038 (2)	0.0264 (19)	0.0009 (17)	0.0117 (17)	0.0011 (16)
C17	0.039 (2)	0.034 (2)	0.0251 (18)	−0.0053 (16)	0.0059 (15)	0.0012 (15)
C18	0.043 (2)	0.033 (2)	0.032 (2)	−0.0094 (17)	0.0074 (17)	−0.0015 (16)
C19	0.049 (2)	0.052 (2)	0.032 (2)	−0.0018 (19)	0.0139 (18)	−0.0057 (18)
C20	0.059 (3)	0.053 (3)	0.0261 (19)	−0.015 (2)	0.0159 (18)	−0.0049 (17)
C21	0.053 (2)	0.049 (2)	0.0247 (18)	−0.0162 (19)	−0.0019 (17)	0.0030 (16)
C22	0.041 (2)	0.043 (2)	0.037 (2)	0.0005 (18)	0.0072 (17)	0.0034 (17)

Br1—C10	1.896 (4)	Br2—C21	1.901 (4)
S1—C1	1.673 (4)	S2—C12	1.672 (4)
O1—C7	1.356 (4)	O2—C18	1.343 (4)
O1—H1A	0.8200	O2—H2	0.8200
N1—C1	1.336 (4)	N5—C12	1.352 (4)
N1—N2	1.383 (4)	N5—N6	1.367 (4)
N1—H1	0.8600	N5—H5A	0.8600
N2—C2	1.288 (4)	N6—C13	1.303 (4)
N3—C1	1.380 (4)	N7—C12	1.374 (4)
N3—C2	1.391 (4)	N7—C13	1.379 (4)
N3—N4	1.403 (4)	N7—N8	1.404 (4)
N4—C5	1.275 (4)	N8—C16	1.271 (4)
C2—C3	1.474 (5)	C13—C14	1.476 (5)
C3—C4	1.527 (5)	C14—C15	1.525 (5)
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	1.461 (5)	C16—C17	1.453 (5)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.393 (5)	C17—C18	1.408 (5)
C6—C11	1.394 (5)	C17—C22	1.409 (5)
C7—C8	1.392 (5)	C18—C19	1.396 (5)
C8—C9	1.384 (5)	C19—C20	1.366 (5)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.390 (5)	C20—C21	1.384 (5)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.379 (5)	C21—C22	1.382 (5)
C11—H11	0.9300	C22—H22	0.9300
C7—O1—H1A	109.5	C18—O2—H2	109.5
C1—N1—N2	114.3 (3)	C12—N5—N6	114.6 (3)
C1—N1—H1	122.8	C12—N5—H5A	122.7
N2—N1—H1	122.8	N6—N5—H5A	122.7
C2—N2—N1	104.4 (3)	C13—N6—N5	104.3 (3)
C1—N3—C2	108.9 (3)	C12—N7—C13	109.7 (3)
C1—N3—N4	127.7 (3)	C12—N7—N8	127.4 (3)
C2—N3—N4	122.8 (3)	C13—N7—N8	122.3 (3)
C5—N4—N3	114.8 (3)	C16—N8—N7	114.8 (3)
N1—C1—N3	102.2 (3)	N5—C12—N7	101.5 (3)
N1—C1—S1	129.1 (3)	N5—C12—S2	128.7 (3)
N3—C1—S1	128.7 (3)	N7—C12—S2	129.8 (3)
N2—C2—N3	110.2 (3)	N6—C13—N7	109.9 (3)
N2—C2—C3	126.3 (3)	N6—C13—C14	126.4 (3)
N3—C2—C3	123.5 (3)	N7—C13—C14	123.7 (3)
C2—C3—C4	112.1 (3)	C13—C14—C15	112.8 (3)
C2—C3—H3A	109.2	C13—C14—H14A	109.0
C4—C3—H3A	109.2	C15—C14—H14A	109.0
C2—C3—H3B	109.2	C13—C14—H14B	109.0
C4—C3—H3B	109.2	C15—C14—H14B	109.0
H3A—C3—H3B	107.9	H14A—C14—H14B	107.8
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	121.3 (3)	N8—C16—C17	120.8 (3)
N4—C5—H5	119.4	N8—C16—H16	119.6
C6—C5—H5	119.4	C17—C16—H16	119.6
C7—C6—C11	119.7 (3)	C18—C17—C22	118.7 (3)
C7—C6—C5	123.2 (3)	C18—C17—C16	123.3 (3)
C11—C6—C5	117.0 (3)	C22—C17—C16	117.9 (3)
O1—C7—C8	116.6 (3)	O2—C18—C19	117.3 (3)
O1—C7—C6	123.9 (3)	O2—C18—C17	123.3 (3)
C8—C7—C6	119.6 (3)	C19—C18—C17	119.4 (4)
C9—C8—C7	120.5 (3)	C20—C19—C18	121.1 (4)
C9—C8—H8	119.7	C20—C19—H19	119.4
C7—C8—H8	119.7	C18—C19—H19	119.4
C8—C9—C10	119.6 (3)	C19—C20—C21	119.8 (3)
C8—C9—H9	120.2	C19—C20—H20	120.1
C10—C9—H9	120.2	C21—C20—H20	120.1
C11—C10—C9	120.4 (3)	C22—C21—C20	120.8 (4)
C11—C10—Br1	120.2 (3)	C22—C21—Br2	118.8 (3)
C9—C10—Br1	119.4 (3)	C20—C21—Br2	120.3 (3)
C10—C11—C6	120.1 (3)	C21—C22—C17	119.9 (3)
C10—C11—H11	119.9	C21—C22—H22	120.0
C6—C11—H11	119.9	C17—C22—H22	120.0
C1—N1—N2—C2	0.5 (4)	C12—N5—N6—C13	0.2 (4)
C1—N3—N4—C5	51.3 (5)	C12—N7—N8—C16	−51.8 (5)
C2—N3—N4—C5	−139.1 (4)	C13—N7—N8—C16	138.0 (4)
N2—N1—C1—N3	−0.7 (4)	N6—N5—C12—N7	0.7 (4)
N2—N1—C1—S1	178.4 (3)	N6—N5—C12—S2	−177.9 (3)
C2—N3—C1—N1	0.6 (4)	C13—N7—C12—N5	−1.3 (4)
N4—N3—C1—N1	171.4 (3)	N8—N7—C12—N5	−172.5 (3)
C2—N3—C1—S1	−178.5 (3)	C13—N7—C12—S2	177.3 (3)
N4—N3—C1—S1	−7.7 (5)	N8—N7—C12—S2	6.1 (5)
N1—N2—C2—N3	−0.1 (4)	N5—N6—C13—N7	−1.0 (4)
N1—N2—C2—C3	179.9 (3)	N5—N6—C13—C14	−179.0 (3)
C1—N3—C2—N2	−0.4 (4)	C12—N7—C13—N6	1.6 (4)
N4—N3—C2—N2	−171.7 (3)	N8—N7—C13—N6	173.3 (3)
C1—N3—C2—C3	179.7 (3)	C12—N7—C13—C14	179.6 (3)
N4—N3—C2—C3	8.3 (5)	N8—N7—C13—C14	−8.7 (5)
N2—C2—C3—C4	−0.3 (6)	N6—C13—C14—C15	−1.0 (6)
N3—C2—C3—C4	179.6 (3)	N7—C13—C14—C15	−178.7 (3)
N3—N4—C5—C6	−176.1 (3)	N7—N8—C16—C17	176.8 (3)
N4—C5—C6—C7	7.9 (6)	N8—C16—C17—C18	−6.3 (6)
N4—C5—C6—C11	−172.8 (3)	N8—C16—C17—C22	176.1 (3)
C11—C6—C7—O1	177.0 (3)	C22—C17—C18—O2	−179.2 (3)
C5—C6—C7—O1	−3.7 (6)	C16—C17—C18—O2	3.3 (6)
C11—C6—C7—C8	−2.4 (5)	C22—C17—C18—C19	2.0 (6)
C5—C6—C7—C8	176.9 (3)	C16—C17—C18—C19	−175.6 (4)
O1—C7—C8—C9	−176.4 (3)	O2—C18—C19—C20	178.4 (4)
C6—C7—C8—C9	3.1 (6)	C17—C18—C19—C20	−2.8 (6)
C7—C8—C9—C10	−1.1 (6)	C18—C19—C20—C21	0.3 (6)
C8—C9—C10—C11	−1.6 (6)	C19—C20—C21—C22	3.0 (6)
C8—C9—C10—Br1	177.2 (3)	C19—C20—C21—Br2	−179.5 (3)
C9—C10—C11—C6	2.2 (6)	C20—C21—C22—C17	−3.7 (6)
Br1—C10—C11—C6	−176.5 (3)	Br2—C21—C22—C17	178.8 (3)
C7—C6—C11—C10	−0.2 (5)	C18—C17—C22—C21	1.2 (5)
C5—C6—C11—C10	−179.5 (3)	C16—C17—C22—C21	178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.86	2.45	3.309 (3)	176
N5—H5A···S1ii	0.86	2.44	3.302 (3)	177
O1—H1A···N4	0.82	2.02	2.712 (4)	141
O2—H2···N8	0.82	1.99	2.695 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.86	2.45	3.309 (3)	176
N5—H5A⋯S1ii	0.86	2.44	3.302 (3)	177
O1—H1A⋯N4	0.82	2.02	2.712 (4)	141
O2—H2⋯N8	0.82	1.99	2.695 (4)	143

Symmetry codes: (i) ; (ii) .