1-(4-Chloro-butano-yl)-3-(2-nitro-phen-yl)thio-urea.

The asymmetric unit of the title compound, C(11)H(12)ClN(3)O(3)S, contains two independent mol-ecules with different conformations in which the benzene ring and the thio-urea fragment form dihedral angles of 87.28 (12) and 66.44 (10)°. The O atom of the thio-amide group is involved in bifurcated N-H⋯O intra- and inter-molecular hydrogen bonding; the latter inter-action links the independent mol-ecules into a dimer. In the crystal, N-H⋯S inter-actions link the mol-ecules into chains propagating along the c axis.

Related literature

For related structures, see: Yusof et al. (2011 ▶, 2012) ▶. For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12ClN3O3S

M = 301.75

Monoclinic,

a = 14.593 (4) Å

b = 11.288 (3) Å

c = 17.828 (5) Å

β = 110.765 (5)°

V = 2745.8 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.44 mm−1

T = 298 K

0.36 × 0.35 × 0.34 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.859, T max = 0.866

15815 measured reflections

5117 independent reflections

3968 reflections with I > 2/s(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.03

5117 reflections

343 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.44 e Å−3

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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202168X/bq2354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202168X/bq2354Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202168X/bq2354Isup3.cml

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

C11H12ClN3O3S	Z = 8
Mr = 301.75	F(000) = 1248
Monoclinic, P21/c	Dx = 1.460 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.593 (4) Å	θ = 2.1–25.5°
b = 11.288 (3) Å	µ = 0.44 mm−1
c = 17.828 (5) Å	T = 298 K
β = 110.765 (5)°	Block, light yellow
V = 2745.8 (12) Å3	0.36 × 0.35 × 0.34 mm

Bruker SMART APEX CCD area-detector diffractometer	5117 independent reflections
Radiation source: fine-focus sealed tube	3968 reflections with I > 2/s(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 2.1°
ω scan	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
Tmin = 0.859, Tmax = 0.866	l = −21→15
15815 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0667P)2 + 1.5901P] where P = (Fo2 + 2Fc2)/3
5117 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.73 e Å−3
18 restraints	Δρmin = −0.44 e Å−3

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	1.24412 (6)	0.79386 (9)	0.71487 (5)	0.0756 (3)
Cl2	0.47919 (7)	0.83444 (9)	0.03285 (6)	0.0889 (3)
S1	0.76404 (5)	0.50753 (6)	0.47256 (4)	0.0493 (2)
S2	1.03228 (4)	1.01443 (6)	0.16703 (4)	0.04415 (18)
O1	0.94192 (14)	0.81777 (18)	0.43547 (12)	0.0606 (6)
O2	0.5292 (2)	0.8151 (3)	0.3985 (2)	0.1216 (12)
O3	0.6705 (3)	0.8670 (3)	0.4071 (2)	0.1155 (11)
O4	0.80541 (12)	0.89874 (19)	0.27305 (11)	0.0522 (5)
O5	1.1880 (2)	1.2063 (2)	0.3510 (3)	0.1318 (15)
O6	1.04315 (17)	1.16326 (19)	0.34087 (16)	0.0728 (6)
N1	0.91463 (14)	0.65268 (19)	0.49776 (12)	0.0413 (5)
H1A	0.9404	0.6088	0.5394	0.050*
N2	0.78153 (14)	0.6862 (2)	0.38280 (13)	0.0455 (5)
H2A	0.8131	0.7465	0.3750	0.055*
N3	0.6020 (2)	0.8010 (3)	0.38258 (19)	0.0722 (8)
N4	0.85978 (13)	0.97251 (17)	0.17751 (12)	0.0364 (4)
H4A	0.8398	1.0006	0.1296	0.044*
N5	0.99262 (13)	0.93177 (18)	0.29187 (12)	0.0386 (5)
H5A	0.9500	0.9139	0.3132	0.046*
N6	1.12681 (18)	1.1360 (2)	0.35275 (16)	0.0560 (6)
C1	1.2274 (2)	0.8592 (3)	0.61931 (19)	0.0652 (9)
H1B	1.2546	0.9385	0.6274	0.078*
H1C	1.2628	0.8130	0.5926	0.078*
C2	1.12111 (19)	0.8653 (3)	0.56658 (17)	0.0510 (7)
H2B	1.1155	0.9037	0.5165	0.061*
H2C	1.0861	0.9132	0.5927	0.061*
C3	1.07414 (17)	0.7445 (2)	0.54881 (16)	0.0448 (6)
H3A	1.1143	0.6938	0.5290	0.054*
H3B	1.0731	0.7103	0.5984	0.054*
C4	0.97212 (17)	0.7454 (2)	0.48887 (15)	0.0413 (6)
C5	0.82146 (17)	0.6218 (2)	0.44845 (14)	0.0382 (5)
C6	0.68819 (17)	0.6588 (2)	0.32493 (15)	0.0426 (6)
C7	0.60209 (19)	0.7115 (3)	0.32442 (17)	0.0494 (7)
C8	0.5123 (2)	0.6819 (3)	0.2662 (2)	0.0657 (9)
H8A	0.4548	0.7167	0.2667	0.079*
C9	0.5099 (2)	0.6008 (4)	0.2084 (2)	0.0735 (10)
H9A	0.4504	0.5816	0.1688	0.088*
C10	0.5934 (2)	0.5483 (3)	0.2086 (2)	0.0709 (9)
H10A	0.5907	0.4929	0.1693	0.085*
C11	0.6824 (2)	0.5763 (3)	0.26647 (17)	0.0572 (7)
H11A	0.7391	0.5391	0.2660	0.069*
C12	0.5051 (2)	0.9274 (3)	0.11797 (19)	0.0635 (8)
H12A	0.4964	1.0095	0.1007	0.076*
H12B	0.4592	0.9105	0.1448	0.076*
C13	0.60803 (18)	0.9100 (3)	0.17614 (16)	0.0526 (7)
H13A	0.6158	0.9539	0.2248	0.063*
H13B	0.6175	0.8267	0.1902	0.063*
C14	0.68560 (17)	0.9485 (2)	0.14479 (15)	0.0441 (6)
H14A	0.6744	1.0307	0.1282	0.053*
H14B	0.6804	0.9016	0.0979	0.053*
C15	0.78730 (17)	0.9361 (2)	0.20533 (15)	0.0387 (5)
C16	0.96013 (16)	0.9697 (2)	0.21656 (14)	0.0349 (5)
C17	1.09327 (16)	0.9188 (2)	0.33935 (14)	0.0358 (5)
C18	1.15787 (17)	1.0128 (2)	0.36830 (15)	0.0384 (5)
C19	1.25516 (19)	0.9937 (3)	0.41403 (17)	0.0500 (7)
H19A	1.2975	1.0576	0.4321	0.060*
C20	1.2893 (2)	0.8798 (3)	0.43287 (18)	0.0557 (7)
H20A	1.3547	0.8664	0.4638	0.067*
C21	1.2264 (2)	0.7864 (3)	0.40572 (18)	0.0564 (7)
H21A	1.2492	0.7095	0.4189	0.068*
C22	1.12941 (19)	0.8053 (2)	0.35899 (16)	0.0464 (6)
H22A	1.0879	0.7408	0.3405	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0570 (5)	0.0986 (7)	0.0547 (5)	−0.0123 (4)	−0.0006 (4)	−0.0010 (4)
Cl2	0.0714 (6)	0.0930 (7)	0.0774 (6)	−0.0241 (5)	−0.0043 (5)	−0.0185 (5)
S1	0.0428 (4)	0.0587 (4)	0.0406 (4)	−0.0163 (3)	0.0077 (3)	0.0052 (3)
S2	0.0353 (3)	0.0575 (4)	0.0400 (3)	−0.0052 (3)	0.0138 (3)	0.0014 (3)
O1	0.0468 (11)	0.0608 (12)	0.0579 (12)	−0.0145 (9)	−0.0014 (9)	0.0186 (10)
O2	0.111 (2)	0.158 (3)	0.120 (3)	0.053 (2)	0.072 (2)	0.018 (2)
O3	0.124 (3)	0.106 (2)	0.126 (3)	−0.019 (2)	0.056 (2)	−0.044 (2)
O4	0.0342 (9)	0.0766 (14)	0.0419 (10)	−0.0042 (9)	0.0085 (8)	0.0142 (9)
O5	0.0838 (19)	0.0484 (14)	0.253 (5)	−0.0123 (14)	0.047 (2)	0.031 (2)
O6	0.0634 (14)	0.0513 (12)	0.1023 (18)	0.0153 (10)	0.0277 (13)	−0.0092 (12)
N1	0.0333 (10)	0.0483 (12)	0.0363 (11)	−0.0070 (9)	0.0048 (8)	0.0053 (9)
N2	0.0338 (11)	0.0521 (13)	0.0433 (12)	−0.0100 (9)	0.0046 (9)	0.0086 (10)
N3	0.0732 (19)	0.0735 (19)	0.079 (2)	0.0116 (15)	0.0388 (17)	0.0104 (15)
N4	0.0310 (10)	0.0401 (11)	0.0347 (10)	0.0000 (8)	0.0074 (8)	0.0044 (8)
N5	0.0280 (10)	0.0481 (12)	0.0373 (11)	−0.0027 (8)	0.0088 (8)	0.0055 (9)
N6	0.0536 (15)	0.0385 (12)	0.0713 (16)	−0.0029 (11)	0.0163 (12)	−0.0024 (11)
C1	0.0432 (16)	0.090 (2)	0.0577 (18)	−0.0242 (15)	0.0115 (14)	−0.0058 (16)
C2	0.0436 (15)	0.0568 (17)	0.0479 (15)	−0.0148 (12)	0.0104 (12)	−0.0011 (13)
C3	0.0315 (12)	0.0504 (15)	0.0471 (14)	−0.0041 (11)	0.0074 (11)	−0.0006 (12)
C4	0.0355 (13)	0.0455 (14)	0.0397 (13)	−0.0043 (11)	0.0094 (11)	−0.0023 (11)
C5	0.0321 (12)	0.0464 (14)	0.0340 (12)	−0.0016 (10)	0.0091 (10)	−0.0034 (10)
C6	0.0308 (12)	0.0524 (15)	0.0394 (13)	−0.0067 (11)	0.0061 (10)	0.0086 (11)
C7	0.0424 (14)	0.0545 (16)	0.0523 (16)	0.0018 (12)	0.0181 (12)	0.0155 (13)
C8	0.0303 (14)	0.088 (2)	0.074 (2)	0.0007 (14)	0.0128 (14)	0.0335 (19)
C9	0.0416 (17)	0.101 (3)	0.060 (2)	−0.0244 (17)	−0.0032 (14)	0.0148 (19)
C10	0.058 (2)	0.090 (2)	0.0549 (18)	−0.0229 (18)	0.0081 (15)	−0.0102 (17)
C11	0.0424 (15)	0.071 (2)	0.0540 (17)	−0.0072 (14)	0.0116 (13)	−0.0057 (15)
C12	0.0357 (14)	0.091 (2)	0.0580 (18)	−0.0044 (15)	0.0101 (13)	0.0002 (17)
C13	0.0335 (13)	0.076 (2)	0.0444 (15)	−0.0032 (13)	0.0094 (11)	0.0044 (13)
C14	0.0332 (12)	0.0538 (15)	0.0413 (14)	−0.0008 (11)	0.0084 (10)	0.0074 (12)
C15	0.0327 (12)	0.0411 (13)	0.0395 (13)	−0.0021 (10)	0.0092 (10)	0.0021 (11)
C16	0.0322 (12)	0.0326 (12)	0.0372 (13)	0.0004 (9)	0.0089 (10)	−0.0031 (9)
C17	0.0315 (12)	0.0413 (13)	0.0336 (12)	−0.0008 (10)	0.0105 (9)	0.0022 (10)
C18	0.0364 (12)	0.0370 (13)	0.0403 (13)	−0.0001 (10)	0.0116 (10)	0.0018 (10)
C19	0.0373 (13)	0.0549 (17)	0.0518 (16)	−0.0089 (12)	0.0082 (12)	−0.0027 (13)
C20	0.0358 (14)	0.0668 (19)	0.0558 (17)	0.0091 (13)	0.0056 (12)	0.0111 (14)
C21	0.0533 (17)	0.0462 (16)	0.0656 (18)	0.0154 (13)	0.0159 (14)	0.0118 (14)
C22	0.0442 (14)	0.0384 (14)	0.0521 (15)	−0.0009 (11)	0.0115 (12)	0.0001 (11)

Cl1—C1	1.792 (3)	C3—H3A	0.9700
Cl2—C12	1.772 (3)	C3—H3B	0.9700
S1—C5	1.675 (3)	C6—C11	1.378 (4)
S2—C16	1.674 (2)	C6—C7	1.387 (4)
O1—C4	1.213 (3)	C7—C8	1.393 (4)
O2—N3	1.205 (4)	C8—C9	1.369 (5)
O3—N3	1.198 (4)	C8—H8A	0.9300
O4—C15	1.216 (3)	C9—C10	1.354 (5)
O5—N6	1.203 (3)	C9—H9A	0.9300
O6—N6	1.203 (3)	C10—C11	1.379 (4)
N1—C5	1.377 (3)	C10—H10A	0.9300
N1—C4	1.385 (3)	C11—H11A	0.9300
N1—H1A	0.8600	C12—C13	1.505 (4)
N2—C5	1.324 (3)	C12—H12A	0.9700
N2—C6	1.421 (3)	C12—H12B	0.9700
N2—H2A	0.8600	C13—C14	1.494 (4)
N3—C7	1.447 (4)	C13—H13A	0.9700
N4—C15	1.380 (3)	C13—H13B	0.9700
N4—C16	1.381 (3)	C14—C15	1.500 (3)
N4—H4A	0.8600	C14—H14A	0.9700
N5—C16	1.326 (3)	C14—H14B	0.9700
N5—C17	1.419 (3)	C17—C22	1.382 (3)
N5—H5A	0.8600	C17—C18	1.391 (3)
N6—C18	1.458 (3)	C18—C19	1.381 (4)
C1—C2	1.503 (4)	C19—C20	1.376 (4)
C1—H1B	0.9700	C19—H19A	0.9300
C1—H1C	0.9700	C20—C21	1.369 (4)
C2—C3	1.508 (4)	C20—H20A	0.9300
C2—H2B	0.9700	C21—C22	1.380 (4)
C2—H2C	0.9700	C21—H21A	0.9300
C3—C4	1.493 (3)	C22—H22A	0.9300
C5—N1—C4	128.3 (2)	C10—C9—C8	120.5 (3)
C5—N1—H1A	115.9	C10—C9—H9A	119.7
C4—N1—H1A	115.9	C8—C9—H9A	119.7
C5—N2—C6	122.0 (2)	C9—C10—C11	120.6 (3)
C5—N2—H2A	119.0	C9—C10—H10A	119.7
C6—N2—H2A	119.0	C11—C10—H10A	119.7
O3—N3—O2	121.6 (4)	C6—C11—C10	120.7 (3)
O3—N3—C7	118.9 (3)	C6—C11—H11A	119.7
O2—N3—C7	119.1 (3)	C10—C11—H11A	119.7
C15—N4—C16	128.5 (2)	C13—C12—Cl2	111.7 (2)
C15—N4—H4A	115.7	C13—C12—H12A	109.3
C16—N4—H4A	115.7	Cl2—C12—H12A	109.3
C16—N5—C17	124.1 (2)	C13—C12—H12B	109.3
C16—N5—H5A	118.0	Cl2—C12—H12B	109.3
C17—N5—H5A	118.0	H12A—C12—H12B	107.9
O6—N6—O5	122.9 (3)	C14—C13—C12	114.1 (2)
O6—N6—C18	120.3 (2)	C14—C13—H13A	108.7
O5—N6—C18	116.8 (3)	C12—C13—H13A	108.7
C2—C1—Cl1	112.1 (2)	C14—C13—H13B	108.7
C2—C1—H1B	109.2	C12—C13—H13B	108.7
Cl1—C1—H1B	109.2	H13A—C13—H13B	107.6
C2—C1—H1C	109.2	C13—C14—C15	113.0 (2)
Cl1—C1—H1C	109.2	C13—C14—H14A	109.0
H1B—C1—H1C	107.9	C15—C14—H14A	109.0
C1—C2—C3	112.4 (2)	C13—C14—H14B	109.0
C1—C2—H2B	109.1	C15—C14—H14B	109.0
C3—C2—H2B	109.1	H14A—C14—H14B	107.8
C1—C2—H2C	109.1	O4—C15—N4	122.4 (2)
C3—C2—H2C	109.1	O4—C15—C14	123.9 (2)
H2B—C2—H2C	107.9	N4—C15—C14	113.7 (2)
C4—C3—C2	114.1 (2)	N5—C16—N4	116.9 (2)
C4—C3—H3A	108.7	N5—C16—S2	124.43 (18)
C2—C3—H3A	108.7	N4—C16—S2	118.69 (17)
C4—C3—H3B	108.7	C22—C17—C18	117.7 (2)
C2—C3—H3B	108.7	C22—C17—N5	117.9 (2)
H3A—C3—H3B	107.6	C18—C17—N5	124.4 (2)
O1—C4—N1	122.2 (2)	C19—C18—C17	121.3 (2)
O1—C4—C3	124.0 (2)	C19—C18—N6	116.5 (2)
N1—C4—C3	113.8 (2)	C17—C18—N6	122.2 (2)
N2—C5—N1	116.8 (2)	C20—C19—C18	119.8 (2)
N2—C5—S1	123.08 (18)	C20—C19—H19A	120.1
N1—C5—S1	120.11 (18)	C18—C19—H19A	120.1
C11—C6—C7	118.2 (2)	C21—C20—C19	119.6 (2)
C11—C6—N2	118.8 (2)	C21—C20—H20A	120.2
C7—C6—N2	123.0 (3)	C19—C20—H20A	120.2
C6—C7—C8	120.8 (3)	C20—C21—C22	120.7 (3)
C6—C7—N3	121.7 (3)	C20—C21—H21A	119.7
C8—C7—N3	117.5 (3)	C22—C21—H21A	119.7
C9—C8—C7	119.2 (3)	C21—C22—C17	120.9 (2)
C9—C8—H8A	120.4	C21—C22—H22A	119.6
C7—C8—H8A	120.4	C17—C22—H22A	119.6
Cl1—C1—C2—C3	−60.9 (3)	Cl2—C12—C13—C14	66.4 (3)
C1—C2—C3—C4	−173.1 (2)	C12—C13—C14—C15	177.0 (3)
C5—N1—C4—O1	4.6 (4)	C16—N4—C15—O4	2.7 (4)
C5—N1—C4—C3	−173.4 (2)	C16—N4—C15—C14	−177.9 (2)
C2—C3—C4—O1	29.3 (4)	C13—C14—C15—O4	0.0 (4)
C2—C3—C4—N1	−152.8 (2)	C13—C14—C15—N4	−179.4 (2)
C6—N2—C5—N1	176.2 (2)	C17—N5—C16—N4	177.3 (2)
C6—N2—C5—S1	−3.7 (4)	C17—N5—C16—S2	−3.1 (3)
C4—N1—C5—N2	1.9 (4)	C15—N4—C16—N5	−2.9 (4)
C4—N1—C5—S1	−178.2 (2)	C15—N4—C16—S2	177.4 (2)
C5—N2—C6—C11	−84.7 (3)	C16—N5—C17—C22	−110.9 (3)
C5—N2—C6—C7	95.3 (3)	C16—N5—C17—C18	69.9 (3)
C11—C6—C7—C8	−0.1 (4)	C22—C17—C18—C19	1.0 (4)
N2—C6—C7—C8	179.8 (2)	N5—C17—C18—C19	−179.8 (2)
C11—C6—C7—N3	−178.6 (3)	C22—C17—C18—N6	−178.5 (2)
N2—C6—C7—N3	1.4 (4)	N5—C17—C18—N6	0.7 (4)
O3—N3—C7—C6	32.9 (5)	O6—N6—C18—C19	−152.6 (3)
O2—N3—C7—C6	−154.8 (3)	O5—N6—C18—C19	28.9 (4)
O3—N3—C7—C8	−145.6 (4)	O6—N6—C18—C17	27.0 (4)
O2—N3—C7—C8	26.7 (4)	O5—N6—C18—C17	−151.6 (3)
C6—C7—C8—C9	−0.9 (4)	C17—C18—C19—C20	−1.1 (4)
N3—C7—C8—C9	177.6 (3)	N6—C18—C19—C20	178.4 (3)
C7—C8—C9—C10	1.2 (5)	C18—C19—C20—C21	0.3 (4)
C8—C9—C10—C11	−0.6 (5)	C19—C20—C21—C22	0.7 (5)
C7—C6—C11—C10	0.8 (4)	C20—C21—C22—C17	−0.8 (4)
N2—C6—C11—C10	−179.2 (3)	C18—C17—C22—C21	0.0 (4)
C9—C10—C11—C6	−0.5 (5)	N5—C17—C22—C21	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.98	2.647 (3)	134
N5—H5A···O4	0.86	1.98	2.658 (3)	135
N2—H2A···O4	0.86	2.47	3.192 (3)	141
N5—H5A···O1	0.86	2.47	3.178 (3)	139
N1—H1A···S2i	0.86	2.60	3.455 (2)	175
N4—H4A···S1ii	0.86	2.62	3.425 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S2i	0.86	2.60	3.455 (2)	175
N2—H2A⋯O1	0.86	1.98	2.647 (3)	134
N2—H2A⋯O4	0.86	2.47	3.192 (3)	141
N4—H4A⋯S1ii	0.86	2.62	3.425 (2)	156
N5—H5A⋯O1	0.86	2.47	3.178 (3)	139
N5—H5A⋯O4	0.86	1.98	2.658 (3)	135

Symmetry codes: (i) ; (ii) .