1-(2-Bromo-phen-yl)-3-(4-chloro-butano-yl)thio-urea.

The asymmetric unit of the title compound, C(11)H(12)BrClN(2)OS, consists of two crystallographically independent mol-ecules. In each mol-ecule, the butano-ylthio-urea unit is nearly planar, with maximum deviations of 0.1292 (19) and 0.3352 (18) Å from the mean plane defined by nine non-H atoms, and is twisted relative to the terminal benzene ring with dihedral angles of 69.26 (7) and 82.41 (7)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif in each butano-ylthio-urea unit. In the crystal, N-H⋯O hydrogen bonds link the two independent mol-ecules together, forming an R(2) (2)(12) ring motif. The mol-ecules are further connected into a tape along the c axis via N-H⋯S and C-H⋯S hydrogen bonds.

Related literature

For related structures, see: Binzet et al. (2009 ▶); Khawar Rauf et al. (2006 ▶); Shoukat et al. (2007 ▶); Yesilkaynak et al. (2010 ▶); Yusof et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12BrClN2OS

M = 335.65

Monoclinic,

a = 14.1384 (2) Å

b = 11.1948 (1) Å

c = 17.7264 (2) Å

β = 107.955 (1)°

V = 2669.03 (5) Å3

Z = 8

Mo Kα radiation

μ = 3.42 mm−1

T = 100 K

0.39 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.350, T max = 0.696

34224 measured reflections

8749 independent reflections

6599 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.067

S = 1.02

8749 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.48 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 datablock(s) global, I. DOI: 10.1107/S160053681201327X/is5098sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201327X/is5098Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201327X/is5098Isup3.cml

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

C11H12BrClN2OS	F(000) = 1344
Mr = 335.65	Dx = 1.671 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9962 reflections
a = 14.1384 (2) Å	θ = 2.4–31.2°
b = 11.1948 (1) Å	µ = 3.42 mm−1
c = 17.7264 (2) Å	T = 100 K
β = 107.955 (1)°	Block, colourless
V = 2669.03 (5) Å3	0.39 × 0.17 × 0.11 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	8749 independent reflections
Radiation source: fine-focus sealed tube	6599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 31.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
Tmin = 0.350, Tmax = 0.696	k = −16→15
34224 measured reflections	l = −25→25

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0274P)2 + 0.9931P] where P = (Fo2 + 2Fc2)/3
8749 reflections	(Δ/σ)max = 0.002
307 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.48 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
Br1A	1.094519 (14)	−0.172320 (16)	0.342402 (11)	0.02211 (5)
Cl1A	0.47347 (4)	0.16991 (5)	0.02259 (3)	0.02967 (11)
S1A	1.03184 (3)	−0.00037 (4)	0.16098 (2)	0.01644 (9)
O1A	0.79290 (8)	0.11587 (11)	0.26956 (7)	0.0185 (3)
N1A	0.98548 (10)	0.07140 (12)	0.28866 (8)	0.0140 (3)
H1NA	0.9419	0.0984	0.3077	0.017*
N2A	0.85365 (10)	0.03620 (12)	0.17480 (8)	0.0139 (3)
H2NA	0.8370	0.0175	0.1262	0.017*
C1A	1.12840 (13)	0.19682 (16)	0.35152 (11)	0.0179 (4)
H1AA	1.0881	0.2654	0.3337	0.022*
C2A	1.22766 (14)	0.20975 (17)	0.39607 (11)	0.0216 (4)
H2AA	1.2549	0.2874	0.4092	0.026*
C3A	1.28731 (13)	0.11006 (18)	0.42148 (11)	0.0230 (4)
H3AA	1.3554	0.1196	0.4510	0.028*
C4A	1.24741 (13)	−0.00344 (17)	0.40372 (11)	0.0198 (4)
H4AA	1.2881	−0.0719	0.4209	0.024*
C5A	1.14793 (13)	−0.01648 (15)	0.36076 (10)	0.0156 (3)
C6A	1.08826 (12)	0.08285 (16)	0.33317 (10)	0.0144 (3)
C7A	0.95520 (12)	0.03821 (15)	0.21252 (10)	0.0135 (3)
C8A	0.77776 (12)	0.07468 (15)	0.20308 (10)	0.0148 (3)
C9A	0.67578 (12)	0.05965 (17)	0.14407 (10)	0.0187 (4)
H9AA	0.6614	−0.0266	0.1349	0.022*
H9AB	0.6750	0.0960	0.0930	0.022*
C10A	0.59501 (12)	0.11665 (17)	0.17189 (10)	0.0181 (4)
H10A	0.5990	0.0843	0.2248	0.022*
H10B	0.6071	0.2038	0.1776	0.022*
C11A	0.49134 (13)	0.09517 (18)	0.11575 (11)	0.0215 (4)
H11A	0.4417	0.1246	0.1403	0.026*
H11B	0.4807	0.0083	0.1064	0.026*
Br1B	0.616014 (14)	0.168367 (17)	0.413043 (11)	0.02241 (5)
Cl1B	1.23151 (3)	0.18536 (4)	0.70479 (3)	0.02501 (10)
S1B	0.76428 (3)	0.49774 (4)	0.47511 (2)	0.01627 (9)
O1B	0.93871 (9)	0.18019 (11)	0.42755 (7)	0.0190 (3)
N1B	0.78048 (10)	0.32012 (13)	0.38055 (8)	0.0152 (3)
H1NB	0.8114	0.2595	0.3726	0.018*
N2B	0.91577 (10)	0.34933 (12)	0.49181 (8)	0.0132 (3)
H2NB	0.9403	0.3934	0.5313	0.016*
C1B	0.67353 (13)	0.43193 (17)	0.26902 (11)	0.0199 (4)
H1BA	0.7301	0.4736	0.2647	0.024*
C2B	0.58029 (13)	0.45596 (17)	0.21637 (11)	0.0231 (4)
H2BA	0.5731	0.5139	0.1758	0.028*
C3B	0.49745 (13)	0.39537 (18)	0.22292 (11)	0.0227 (4)
H3BA	0.4337	0.4121	0.1867	0.027*
C4B	0.50693 (13)	0.31080 (17)	0.28186 (11)	0.0206 (4)
H4BA	0.4502	0.2700	0.2867	0.025*
C5B	0.60057 (13)	0.28675 (16)	0.33370 (10)	0.0169 (3)
C6B	0.68418 (12)	0.34721 (15)	0.32795 (10)	0.0154 (3)
C7B	0.82121 (12)	0.38288 (15)	0.44613 (10)	0.0125 (3)
C8B	0.97074 (12)	0.25286 (16)	0.48090 (10)	0.0147 (3)
C9B	1.07364 (12)	0.24650 (16)	0.53928 (10)	0.0161 (3)
H9BA	1.0731	0.2844	0.5896	0.019*
H9BB	1.1197	0.2927	0.5182	0.019*
C10B	1.11242 (12)	0.11951 (16)	0.55635 (11)	0.0180 (4)
H10C	1.0698	0.0750	0.5817	0.022*
H10D	1.1082	0.0792	0.5057	0.022*
C11B	1.21905 (13)	0.11609 (19)	0.61013 (11)	0.0227 (4)
H11C	1.2622	0.1582	0.5841	0.027*
H11D	1.2416	0.0320	0.6187	0.027*

	U11	U22	U33	U12	U13	U23
Br1A	0.02895 (10)	0.01320 (9)	0.02297 (10)	0.00066 (8)	0.00623 (8)	0.00138 (7)
Cl1A	0.0230 (2)	0.0355 (3)	0.0255 (2)	0.0028 (2)	0.00004 (19)	0.0106 (2)
S1A	0.01481 (19)	0.0212 (2)	0.01338 (19)	0.00319 (17)	0.00442 (16)	0.00091 (17)
O1A	0.0152 (6)	0.0234 (7)	0.0159 (6)	0.0014 (5)	0.0035 (5)	−0.0053 (5)
N1A	0.0116 (6)	0.0157 (7)	0.0147 (7)	0.0013 (6)	0.0040 (5)	−0.0016 (6)
N2A	0.0133 (6)	0.0159 (7)	0.0111 (6)	0.0008 (6)	0.0015 (5)	−0.0018 (5)
C1A	0.0182 (8)	0.0184 (9)	0.0174 (9)	−0.0011 (7)	0.0056 (7)	−0.0015 (7)
C2A	0.0210 (9)	0.0218 (9)	0.0205 (9)	−0.0050 (8)	0.0044 (7)	−0.0039 (7)
C3A	0.0147 (8)	0.0321 (11)	0.0196 (9)	0.0008 (8)	0.0013 (7)	−0.0022 (8)
C4A	0.0183 (8)	0.0232 (10)	0.0166 (8)	0.0053 (8)	0.0032 (7)	0.0010 (7)
C5A	0.0189 (8)	0.0138 (8)	0.0141 (8)	0.0003 (7)	0.0049 (7)	0.0002 (6)
C6A	0.0128 (7)	0.0182 (9)	0.0118 (8)	0.0009 (7)	0.0029 (6)	0.0005 (6)
C7A	0.0149 (8)	0.0111 (8)	0.0136 (8)	0.0013 (6)	0.0030 (6)	0.0022 (6)
C8A	0.0141 (7)	0.0138 (8)	0.0157 (8)	0.0016 (7)	0.0032 (6)	0.0002 (6)
C9A	0.0135 (8)	0.0244 (10)	0.0160 (8)	0.0015 (7)	0.0011 (7)	−0.0044 (7)
C10A	0.0141 (8)	0.0233 (10)	0.0162 (8)	−0.0013 (7)	0.0036 (7)	−0.0019 (7)
C11A	0.0158 (8)	0.0290 (10)	0.0193 (9)	−0.0016 (8)	0.0048 (7)	0.0014 (8)
Br1B	0.02251 (9)	0.02434 (10)	0.02018 (9)	−0.00204 (8)	0.00630 (7)	0.00036 (8)
Cl1B	0.0219 (2)	0.0316 (3)	0.0171 (2)	0.00387 (19)	−0.00056 (17)	−0.00221 (19)
S1B	0.01620 (19)	0.0171 (2)	0.01410 (19)	0.00422 (17)	0.00255 (16)	−0.00142 (16)
O1B	0.0156 (6)	0.0193 (7)	0.0187 (6)	0.0034 (5)	0.0004 (5)	−0.0053 (5)
N1B	0.0119 (6)	0.0161 (7)	0.0153 (7)	0.0037 (6)	0.0009 (5)	−0.0024 (6)
N2B	0.0122 (6)	0.0138 (7)	0.0118 (6)	0.0007 (5)	0.0011 (5)	−0.0022 (5)
C1B	0.0158 (8)	0.0222 (10)	0.0200 (9)	0.0011 (7)	0.0029 (7)	0.0003 (7)
C2B	0.0221 (9)	0.0233 (10)	0.0190 (9)	0.0064 (8)	−0.0008 (7)	0.0039 (8)
C3B	0.0146 (8)	0.0274 (11)	0.0214 (9)	0.0052 (8)	−0.0012 (7)	−0.0041 (8)
C4B	0.0139 (8)	0.0238 (10)	0.0229 (9)	−0.0001 (7)	0.0040 (7)	−0.0071 (8)
C5B	0.0177 (8)	0.0173 (9)	0.0155 (8)	0.0020 (7)	0.0051 (7)	−0.0041 (7)
C6B	0.0125 (7)	0.0178 (9)	0.0137 (8)	0.0030 (7)	0.0008 (6)	−0.0044 (6)
C7B	0.0126 (7)	0.0134 (8)	0.0115 (7)	−0.0008 (6)	0.0038 (6)	0.0025 (6)
C8B	0.0131 (7)	0.0156 (9)	0.0149 (8)	0.0005 (7)	0.0034 (6)	0.0005 (6)
C9B	0.0116 (7)	0.0175 (9)	0.0171 (8)	0.0007 (7)	0.0013 (6)	−0.0010 (7)
C10B	0.0156 (8)	0.0200 (9)	0.0157 (8)	0.0030 (7)	0.0009 (7)	−0.0025 (7)
C11B	0.0199 (9)	0.0292 (11)	0.0176 (9)	0.0088 (8)	0.0040 (7)	−0.0017 (8)

Br1A—C5A	1.8889 (17)	Br1B—C5B	1.8955 (18)
Cl1A—C11A	1.7983 (19)	Cl1B—C11B	1.8071 (19)
S1A—C7A	1.6751 (17)	S1B—C7B	1.6792 (17)
O1A—C8A	1.221 (2)	O1B—C8B	1.224 (2)
N1A—C7A	1.337 (2)	N1B—C7B	1.328 (2)
N1A—C6A	1.430 (2)	N1B—C6B	1.426 (2)
N1A—H1NA	0.8445	N1B—H1NB	0.8421
N2A—C7A	1.385 (2)	N2B—C8B	1.379 (2)
N2A—C8A	1.386 (2)	N2B—C7B	1.384 (2)
N2A—H2NA	0.8465	N2B—H2NB	0.8391
C1A—C2A	1.390 (2)	C1B—C6B	1.384 (2)
C1A—C6A	1.394 (2)	C1B—C2B	1.387 (2)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—C3A	1.388 (3)	C2B—C3B	1.389 (3)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.386 (3)	C3B—C4B	1.385 (3)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.385 (2)	C4B—C5B	1.386 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.390 (2)	C5B—C6B	1.393 (2)
C8A—C9A	1.507 (2)	C8B—C9B	1.505 (2)
C9A—C10A	1.517 (2)	C9B—C10B	1.520 (2)
C9A—H9AA	0.9900	C9B—H9BA	0.9900
C9A—H9AB	0.9900	C9B—H9BB	0.9900
C10A—C11A	1.516 (2)	C10B—C11B	1.516 (2)
C10A—H10A	0.9900	C10B—H10C	0.9900
C10A—H10B	0.9900	C10B—H10D	0.9900
C11A—H11A	0.9900	C11B—H11C	0.9900
C11A—H11B	0.9900	C11B—H11D	0.9900
C7A—N1A—C6A	122.48 (14)	C7B—N1B—C6B	121.93 (14)
C7A—N1A—H1NA	117.2	C7B—N1B—H1NB	117.8
C6A—N1A—H1NA	119.3	C6B—N1B—H1NB	120.1
C7A—N2A—C8A	128.57 (14)	C8B—N2B—C7B	127.96 (14)
C7A—N2A—H2NA	114.6	C8B—N2B—H2NB	118.1
C8A—N2A—H2NA	116.3	C7B—N2B—H2NB	113.9
C2A—C1A—C6A	119.70 (17)	C6B—C1B—C2B	120.03 (17)
C2A—C1A—H1AA	120.2	C6B—C1B—H1BA	120.0
C6A—C1A—H1AA	120.2	C2B—C1B—H1BA	120.0
C3A—C2A—C1A	120.46 (18)	C1B—C2B—C3B	120.01 (18)
C3A—C2A—H2AA	119.8	C1B—C2B—H2BA	120.0
C1A—C2A—H2AA	119.8	C3B—C2B—H2BA	120.0
C4A—C3A—C2A	119.96 (17)	C4B—C3B—C2B	120.57 (16)
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	119.7
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	119.7
C5A—C4A—C3A	119.64 (17)	C3B—C4B—C5B	118.91 (17)
C5A—C4A—H4AA	120.2	C3B—C4B—H4BA	120.5
C3A—C4A—H4AA	120.2	C5B—C4B—H4BA	120.5
C4A—C5A—C6A	120.81 (16)	C4B—C5B—C6B	121.06 (17)
C4A—C5A—Br1A	118.44 (13)	C4B—C5B—Br1B	119.73 (14)
C6A—C5A—Br1A	120.73 (13)	C6B—C5B—Br1B	119.20 (13)
C5A—C6A—C1A	119.39 (15)	C1B—C6B—C5B	119.40 (15)
C5A—C6A—N1A	121.72 (15)	C1B—C6B—N1B	119.93 (15)
C1A—C6A—N1A	118.85 (15)	C5B—C6B—N1B	120.64 (16)
N1A—C7A—N2A	116.99 (15)	N1B—C7B—N2B	116.64 (15)
N1A—C7A—S1A	124.24 (13)	N1B—C7B—S1B	123.60 (13)
N2A—C7A—S1A	118.77 (12)	N2B—C7B—S1B	119.76 (12)
O1A—C8A—N2A	122.79 (15)	O1B—C8B—N2B	122.61 (15)
O1A—C8A—C9A	123.88 (15)	O1B—C8B—C9B	123.30 (15)
N2A—C8A—C9A	113.33 (14)	N2B—C8B—C9B	114.08 (14)
C8A—C9A—C10A	112.48 (14)	C8B—C9B—C10B	113.21 (14)
C8A—C9A—H9AA	109.1	C8B—C9B—H9BA	108.9
C10A—C9A—H9AA	109.1	C10B—C9B—H9BA	108.9
C8A—C9A—H9AB	109.1	C8B—C9B—H9BB	108.9
C10A—C9A—H9AB	109.1	C10B—C9B—H9BB	108.9
H9AA—C9A—H9AB	107.8	H9BA—C9B—H9BB	107.8
C11A—C10A—C9A	113.10 (15)	C11B—C10B—C9B	112.12 (15)
C11A—C10A—H10A	109.0	C11B—C10B—H10C	109.2
C9A—C10A—H10A	109.0	C9B—C10B—H10C	109.2
C11A—C10A—H10B	109.0	C11B—C10B—H10D	109.2
C9A—C10A—H10B	109.0	C9B—C10B—H10D	109.2
H10A—C10A—H10B	107.8	H10C—C10B—H10D	107.9
C10A—C11A—Cl1A	111.27 (13)	C10B—C11B—Cl1B	111.50 (12)
C10A—C11A—H11A	109.4	C10B—C11B—H11C	109.3
Cl1A—C11A—H11A	109.4	Cl1B—C11B—H11C	109.3
C10A—C11A—H11B	109.4	C10B—C11B—H11D	109.3
Cl1A—C11A—H11B	109.4	Cl1B—C11B—H11D	109.3
H11A—C11A—H11B	108.0	H11C—C11B—H11D	108.0
C6A—C1A—C2A—C3A	0.9 (3)	C6B—C1B—C2B—C3B	0.3 (3)
C1A—C2A—C3A—C4A	−1.2 (3)	C1B—C2B—C3B—C4B	0.1 (3)
C2A—C3A—C4A—C5A	−0.1 (3)	C2B—C3B—C4B—C5B	−0.6 (3)
C3A—C4A—C5A—C6A	1.9 (3)	C3B—C4B—C5B—C6B	0.9 (3)
C3A—C4A—C5A—Br1A	−176.78 (14)	C3B—C4B—C5B—Br1B	−178.30 (14)
C4A—C5A—C6A—C1A	−2.3 (3)	C2B—C1B—C6B—C5B	0.0 (3)
Br1A—C5A—C6A—C1A	176.36 (13)	C2B—C1B—C6B—N1B	178.15 (16)
C4A—C5A—C6A—N1A	179.92 (16)	C4B—C5B—C6B—C1B	−0.6 (3)
Br1A—C5A—C6A—N1A	−1.4 (2)	Br1B—C5B—C6B—C1B	178.63 (13)
C2A—C1A—C6A—C5A	0.9 (3)	C4B—C5B—C6B—N1B	−178.72 (16)
C2A—C1A—C6A—N1A	178.74 (16)	Br1B—C5B—C6B—N1B	0.5 (2)
C7A—N1A—C6A—C5A	−75.6 (2)	C7B—N1B—C6B—C1B	86.2 (2)
C7A—N1A—C6A—C1A	106.65 (19)	C7B—N1B—C6B—C5B	−95.7 (2)
C6A—N1A—C7A—N2A	−176.84 (14)	C6B—N1B—C7B—N2B	−178.95 (14)
C6A—N1A—C7A—S1A	3.1 (2)	C6B—N1B—C7B—S1B	1.1 (2)
C8A—N2A—C7A—N1A	6.6 (3)	C8B—N2B—C7B—N1B	−5.2 (2)
C8A—N2A—C7A—S1A	−173.40 (14)	C8B—N2B—C7B—S1B	174.71 (13)
C7A—N2A—C8A—O1A	−1.3 (3)	C7B—N2B—C8B—O1B	−2.2 (3)
C7A—N2A—C8A—C9A	179.18 (16)	C7B—N2B—C8B—C9B	176.77 (15)
O1A—C8A—C9A—C10A	7.8 (3)	O1B—C8B—C9B—C10B	−30.9 (2)
N2A—C8A—C9A—C10A	−172.60 (15)	N2B—C8B—C9B—C10B	150.22 (15)
C8A—C9A—C10A—C11A	−176.15 (15)	C8B—C9B—C10B—C11B	175.45 (15)
C9A—C10A—C11A—Cl1A	−66.74 (19)	C9B—C10B—C11B—Cl1B	60.18 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1A	0.84	2.01	2.6847 (19)	136
N1B—H1NB···O1B	0.84	1.97	2.6464 (19)	136
N1A—H1NA···O1B	0.84	2.33	2.9976 (18)	137
N1B—H1NB···O1A	0.84	2.39	3.0566 (19)	137
N2A—H2NA···S1Bi	0.85	2.56	3.3931 (15)	168
N2B—H2NB···S1Aii	0.84	2.56	3.3928 (14)	171
C9B—H9BA···S1Aii	0.99	2.87	3.7237 (18)	145
C9B—H9BB···S1Biii	0.99	2.84	3.7248 (18)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1A	0.84	2.01	2.6847 (19)	136
N1B—H1NB⋯O1B	0.84	1.97	2.6464 (19)	136
N1A—H1NA⋯O1B	0.84	2.33	2.9976 (18)	137
N1B—H1NB⋯O1A	0.84	2.39	3.0566 (19)	137
N2A—H2NA⋯S1Bi	0.85	2.56	3.3931 (15)	168
N2B—H2NB⋯S1Aii	0.84	2.56	3.3928 (14)	171
C9B—H9BA⋯S1Aii	0.99	2.87	3.7237 (18)	145
C9B—H9BB⋯S1Biii	0.99	2.84	3.7248 (18)	149

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