2-Cyclo­hexyl­idene-N-methyl­hydrazine­carbothio­amide

Tayamon, S.; Mazlan, N.A.; Ravoof, T.B.S.A.; Mohamed Tahir, M.I.; Crouse, K.A.

doi:10.1107/S1600536812042018

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3104-o3105

doi:10.1107/S1600536812042018

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2-Cyclohexylidene-N-methylhydrazinecarbothioamide

Shahedeh Tayamon,^a Nurul Ain Mazlan,^a Thahira Begum S. A. Ravoof,^a ^* Mohamed Ibrahim Mohamed Tahir ^a and Karen A Crouse ^a

^aDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
^*Correspondence e-mail: thahira.begum@science.upm.edu.my

(Received 30 July 2012; accepted 8 October 2012; online 13 October 2012)

The title compound C₈H₁₅N₃S has two molecules in the asymmetric unit in which cis–trans isomerism is exhibited around the N(NH)C=S bonds. The cyclohexyl rings in both molecules adopt a chair conformation. In the crystal, N—H⋯S hydrogen bonding produces dimers, which are interconnected through further N—H⋯S hydrogen bonds, forming chains along the b-axis direction.

Related literature

For background to the coordination chemistry of dithiocarbazate derivatives, see: Zhang et al. (2011 ); Khoo et al. (2005 ); Ravoof et al. (2010 ). For the synthesis and methodology, see: Tian et al. (1997); Tarafder et al. (2000 ); Tan et al. (2012 ). For related structures, see: Paulus et al. (2011 ); Tayamon et al. (2012 ). For packing arrangements in other cyclohexyl compounds, see: Rohr et al. (2009 ). For riding constrints, see: Cooper et al. (2010 ). For charge delocalization, see: Sanderson (1967 ). For the synthesis, see: Tian et al. (1997 ).

Experimental

Crystal data

C₈H₁₅N₃S
M_r = 185.29
Monoclinic, P 2₁ /c
a = 10.0538 (3) Å
b = 11.0108 (3) Å
c = 17.9484 (5) Å
β = 102.132 (3)°
V = 1942.52 (10) Å³
Z = 8
Cu Kα radiation
μ = 2.56 mm⁻¹
T = 100 K
0.27 × 0.22 × 0.10 mm

Data collection

Agilent Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.58, T_max = 0.77
13859 measured reflections
3754 independent reflections
3414 reflections with I > 2.0σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 0.98
3740 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N205—H2051⋯S101ⁱ	0.89	2.57	3.4559 (13)	175
N105—H1051⋯S201ⁱⁱ	0.87	2.59	3.4484 (13)	169
N203—H2031⋯S201ⁱⁱ	0.87	2.76	3.4691 (13)	139
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042018/bg2476sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042018/bg2476Isup2.hkl

checkCIF report

Comment top

To initiate comparative studies between hydrazine carbothioamide Schiff bases (Zhang et al., 2011) and hydrazine carbodithioate derivatives synthesized in our laboratory in our on-going investigations (Khoo et al., 2005; Ravoof et al., 2010, Tan et al. 2012, Paulus et al. 2011, Tayamon et al. 2012), the title compound (C₈H₁₅N₃S) was synthesized and crystallographically characterized. The compound crystallizes in the monoclinic system, space group P 2₁/c. There are two independent molecules in the asymmetric unit (Fig. 1), in the thione form with C=S bond distances ranging from 1.6953 (15) Å to 1.6982 (15) Å. The values are intermediate between a C—S single bond (~1.82 Å) and a C=S double bond(~1.56 Å) due to charge delocalization (Sanderson, 1967). The C—N and C=N bond distances range from 1.3269 (19) to 1.3596 (19) Å and 1.281 (2) to 1.2818 (19) Å respectively. N—N bond distances vary from 1.3909 (17) to 1.3989 (17) Å, shorter than a single bond and indicating significant π delocalization along the NNC(S)N moiety.

Cis-trans isomerism is exhibited in the Schiff base around the N(NH)C=S bonds. In both molecules, the methyl group is cis to the thione sulfur along Cn02 – Nn03 (n: 1, 2), and the cyclohexyl group is trans to the thione sulfur along Cn02 – Nn05. Both cyclohexyl rings are in a chair conformation. The two molecules are twisted relative to one another, as shown by the angle between the planes defined by C108–C109–C111–C112 (largest deviation 0.000 Å) and C208–C209–C211–C212 (largest deviation 0.020 Å) in the respective cyclohexyl ring (83.47°), and S101–C102–N103–C104 (largest deviation 0.009 Å) and S201–C202–N203–C204 (largest deviation 0.013 Å) with a dihedral angle of 27.66°. Molecular packing viewed along the a axis shows this orthogonal arrangement of the cyclohexyl rings similar to other subsituted cyclohexyl compounds (Rohr et al., 2009).

The molecular packing is supported by hydrogen bonding through N—H···S interactions (first and second entries in Table 1) creating dimers, which in turn, are also linked through another N—H···S H-bond interaction between dimers (third entry in table 1) creating a chain-like structure along the b axis.

Related literature top

For background to the coordination chemistry of dithiocarbazate derivatives, see: Zhang et al. (2011); Khoo et al. (2005); Ravoof et al. (2010). For the synthesis and methodology, see: Tian et al. (1997); Tarafder et al. (2000); Tan et al. (2012). For related structures, see: Paulus et al. (2011); Tayamon et al. (2012). For on what subject(s)?, see: Cooper et al. (2010); Rohr et al. (2009); Sanderson (1967); Tian et al. (1997).

Experimental top

The title compound was synthesized following established literature procedures (Tian et al., 1997; Tarafder et al., 2000). 4-methyl-3-thiosemicarbazide (1.05 g, 0.01 mol) dissolved in hot absolute ethanol (30 ml) was added dropwise to an equimolar amount of cyclohexanone (1.04 ml) also in hot absolute ethanol (20 ml). The mixture was stirred for about half an hour at about 340 K and 3 h at room temperature. Pale yellow crystals of the Schiff base suitable for X-ray analysis were obtained after 3 days by keeping the solution at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level.

2-Cyclohexylidene-N-methylhydrazinecarbothioamide top

Crystal data top

C₈H₁₅N₃S	F(000) = 800
M_r = 185.29	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 6569 reflections
a = 10.0538 (3) Å	θ = 4–71°
b = 11.0108 (3) Å	µ = 2.56 mm⁻¹
c = 17.9484 (5) Å	T = 100 K
β = 102.132 (3)°	Plate, yellow
V = 1942.52 (10) Å³	0.27 × 0.22 × 0.10 mm
Z = 8

Data collection top

Agilent Gemini diffractometer	3414 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 71.3°, θ_min = 4.5°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −12→12
T_min = 0.58, T_max = 0.77	k = −12→13
13859 measured reflections	l = −22→20
3754 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.090	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.05P)² + 1.01P] , where P = (max(F_o²,0) + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
3740 reflections	Δρ_max = 0.42 e Å⁻³
217 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Crystal data top

C₈H₁₅N₃S	V = 1942.52 (10) Å³
M_r = 185.29	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.0538 (3) Å	µ = 2.56 mm⁻¹
b = 11.0108 (3) Å	T = 100 K
c = 17.9484 (5) Å	0.27 × 0.22 × 0.10 mm
β = 102.132 (3)°

Data collection top

Agilent Gemini diffractometer	3754 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3414 reflections with I > 2.0σ(I)
T_min = 0.58, T_max = 0.77	R_int = 0.025
13859 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 0.98	Δρ_max = 0.42 e Å⁻³
3740 reflections	Δρ_min = −0.21 e Å⁻³
217 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105–107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S201	0.58434 (4)	−0.01233 (3)	0.30376 (2)	0.0187
C202	0.60061 (14)	0.13128 (13)	0.27235 (8)	0.0162
N203	0.53742 (13)	0.22586 (11)	0.29493 (7)	0.0181
C204	0.44282 (16)	0.21726 (14)	0.34578 (9)	0.0209
N205	0.67851 (13)	0.15375 (11)	0.22056 (7)	0.0167
N206	0.70685 (13)	0.27513 (11)	0.20908 (7)	0.0172
C207	0.76628 (14)	0.30324 (13)	0.15489 (8)	0.0164
C208	0.80605 (16)	0.22007 (13)	0.09651 (8)	0.0185
C209	0.76595 (17)	0.27449 (14)	0.01581 (9)	0.0224
C210	0.81075 (18)	0.40699 (15)	0.01227 (9)	0.0253
C211	0.75322 (17)	0.48442 (14)	0.06856 (9)	0.0216
C212	0.80051 (16)	0.43550 (13)	0.14981 (9)	0.0189
H2042	0.4105	0.2974	0.3532	0.0328*
H2041	0.4865	0.1830	0.3941	0.0327*
H2043	0.3665	0.1658	0.3226	0.0325*
H2082	0.9047	0.2100	0.1102	0.0244*
H2081	0.7642	0.1400	0.0982	0.0221*
H2091	0.8084	0.2250	−0.0181	0.0289*
H2092	0.6676	0.2711	−0.0007	0.0289*
H2102	0.9105	0.4108	0.0260	0.0327*
H2101	0.7794	0.4379	−0.0396	0.0332*
H2111	0.7819	0.5687	0.0665	0.0267*
H2112	0.6522	0.4812	0.0542	0.0274*
H2121	0.8989	0.4423	0.1649	0.0247*
H2122	0.7612	0.4819	0.1862	0.0250*
H2051	0.7311	0.0945	0.2094	0.0237*
H2031	0.5539	0.2982	0.2789	0.0238*
S101	0.10077 (4)	0.43846 (3)	0.32431 (2)	0.0195
C102	0.09543 (14)	0.30514 (14)	0.27653 (8)	0.0162
N103	0.03196 (13)	0.20656 (11)	0.29422 (7)	0.0171
C104	−0.04378 (16)	0.20264 (14)	0.35483 (9)	0.0198
N105	0.15382 (12)	0.29552 (11)	0.21498 (7)	0.0168
N106	0.16479 (13)	0.17797 (11)	0.18731 (7)	0.0191
C107	0.20173 (15)	0.16549 (14)	0.12364 (9)	0.0180
C108	0.23688 (15)	0.26264 (14)	0.07247 (8)	0.0188
C109	0.38405 (16)	0.24444 (14)	0.06287 (9)	0.0201
C110	0.40502 (17)	0.11593 (14)	0.03518 (9)	0.0228
C111	0.36605 (16)	0.01991 (14)	0.08823 (9)	0.0206
C112	0.21911 (17)	0.03771 (15)	0.09779 (10)	0.0240
H1041	−0.0770	0.1213	0.3570	0.0331*
H1042	0.0137	0.2223	0.4028	0.0329*
H1043	−0.1208	0.2590	0.3436	0.0325*
H1081	0.2226	0.3447	0.0915	0.0246*
H1082	0.1745	0.2523	0.0229	0.0255*
H1092	0.4454	0.2578	0.1125	0.0256*
H1091	0.4047	0.3045	0.0275	0.0262*
H1101	0.5017	0.1051	0.0335	0.0290*
H1102	0.3480	0.1049	−0.0165	0.0286*
H1112	0.4287	0.0259	0.1391	0.0258*
H1111	0.3763	−0.0617	0.0669	0.0248*
H1121	0.1964	−0.0195	0.1338	0.0317*
H1122	0.1553	0.0268	0.0483	0.0307*
H1031	0.0352	0.1396	0.2682	0.0230*
H1051	0.2103	0.3519	0.2083	0.0243*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S201	0.0218 (2)	0.01267 (19)	0.0224 (2)	−0.00031 (13)	0.00684 (15)	0.00329 (13)
C202	0.0161 (7)	0.0153 (7)	0.0155 (7)	−0.0016 (5)	−0.0003 (5)	0.0006 (5)
N203	0.0214 (6)	0.0127 (6)	0.0214 (6)	0.0004 (5)	0.0069 (5)	0.0022 (5)
C204	0.0213 (8)	0.0199 (8)	0.0225 (8)	0.0000 (6)	0.0072 (6)	−0.0010 (6)
N205	0.0202 (6)	0.0112 (6)	0.0194 (6)	0.0009 (5)	0.0060 (5)	0.0014 (5)
N206	0.0187 (6)	0.0120 (6)	0.0200 (6)	0.0007 (5)	0.0020 (5)	0.0015 (5)
C207	0.0161 (7)	0.0150 (7)	0.0168 (7)	0.0006 (5)	0.0008 (5)	0.0020 (5)
C208	0.0216 (7)	0.0138 (7)	0.0209 (8)	0.0012 (6)	0.0060 (6)	0.0015 (6)
C209	0.0308 (8)	0.0195 (8)	0.0174 (7)	−0.0022 (6)	0.0059 (6)	−0.0001 (6)
C210	0.0362 (9)	0.0208 (8)	0.0199 (8)	−0.0026 (7)	0.0084 (7)	0.0046 (6)
C211	0.0257 (8)	0.0155 (7)	0.0234 (8)	−0.0004 (6)	0.0047 (6)	0.0043 (6)
C212	0.0218 (7)	0.0143 (7)	0.0205 (8)	−0.0010 (6)	0.0045 (6)	0.0004 (6)
S101	0.0230 (2)	0.0150 (2)	0.0221 (2)	−0.00106 (13)	0.00819 (15)	−0.00470 (13)
C102	0.0149 (7)	0.0158 (7)	0.0173 (7)	0.0027 (5)	0.0020 (5)	0.0003 (5)
N103	0.0195 (6)	0.0141 (6)	0.0189 (6)	−0.0002 (5)	0.0069 (5)	−0.0014 (5)
C104	0.0210 (7)	0.0208 (8)	0.0191 (7)	−0.0006 (6)	0.0072 (6)	0.0013 (6)
N105	0.0189 (6)	0.0120 (6)	0.0209 (6)	−0.0016 (5)	0.0070 (5)	−0.0016 (5)
N106	0.0196 (6)	0.0132 (6)	0.0264 (7)	−0.0010 (5)	0.0091 (5)	−0.0030 (5)
C107	0.0149 (7)	0.0176 (8)	0.0223 (7)	−0.0020 (6)	0.0055 (6)	−0.0031 (6)
C108	0.0222 (8)	0.0175 (7)	0.0162 (7)	0.0024 (6)	0.0032 (6)	−0.0008 (6)
C109	0.0232 (8)	0.0181 (8)	0.0211 (7)	−0.0016 (6)	0.0096 (6)	0.0007 (6)
C110	0.0249 (8)	0.0210 (8)	0.0255 (8)	−0.0007 (6)	0.0123 (6)	−0.0037 (6)
C111	0.0240 (8)	0.0150 (8)	0.0249 (8)	0.0004 (6)	0.0094 (6)	−0.0044 (6)
C112	0.0269 (8)	0.0176 (8)	0.0314 (9)	−0.0059 (6)	0.0152 (7)	−0.0069 (6)

Geometric parameters (Å, º) top

S201—C202	1.6982 (15)	S101—C102	1.6953 (15)
C202—N203	1.3269 (19)	C102—N103	1.331 (2)
C202—N205	1.3582 (19)	C102—N105	1.3596 (19)
N203—C204	1.4531 (19)	N103—C104	1.4537 (18)
N203—H2031	0.874	N103—H1031	0.877
C204—H2042	0.959	C104—H1041	0.959
C204—H2041	0.962	C104—H1042	0.955
C204—H2043	0.974	C104—H1043	0.980
N205—N206	1.3909 (17)	N105—N106	1.3989 (17)
N205—H2051	0.889	N105—H1051	0.866
N206—C207	1.2818 (19)	N106—C107	1.281 (2)
C207—C208	1.508 (2)	C107—C108	1.500 (2)
C207—C212	1.504 (2)	C107—C112	1.503 (2)
C208—C209	1.541 (2)	C108—C109	1.538 (2)
C208—H2082	0.977	C108—H1081	0.987
C208—H2081	0.980	C108—H1082	0.982
C209—C210	1.532 (2)	C109—C110	1.529 (2)
C209—H2091	0.979	C109—H1092	0.982
C209—H2092	0.971	C109—H1091	0.969
C210—C211	1.526 (2)	C110—C111	1.528 (2)
C210—H2102	0.982	C110—H1101	0.986
C210—H2101	0.980	C110—H1102	0.990
C211—C212	1.534 (2)	C111—C112	1.535 (2)
C211—H2111	0.975	C111—H1112	0.997
C211—H2112	0.995	C111—H1111	0.990
C212—H2121	0.972	C112—H1121	0.964
C212—H2122	0.975	C112—H1122	0.987

S201—C202—N203	122.94 (11)	S101—C102—N103	123.45 (11)
S201—C202—N205	120.43 (11)	S101—C102—N105	120.35 (11)
N203—C202—N205	116.62 (13)	N103—C102—N105	116.16 (13)
C202—N203—C204	124.01 (13)	C102—N103—C104	123.75 (13)
C202—N203—H2031	118.6	C102—N103—H1031	119.0
C204—N203—H2031	117.4	C104—N103—H1031	117.2
N203—C204—H2042	108.2	N103—C104—H1041	107.4
N203—C204—H2041	110.8	N103—C104—H1042	110.7
H2042—C204—H2041	109.9	H1041—C104—H1042	109.0
N203—C204—H2043	109.3	N103—C104—H1043	110.0
H2042—C204—H2043	109.5	H1041—C104—H1043	109.4
H2041—C204—H2043	109.1	H1042—C104—H1043	110.2
C202—N205—N206	116.23 (12)	C102—N105—N106	116.12 (12)
C202—N205—H2051	118.5	C102—N105—H1051	117.6
N206—N205—H2051	121.5	N106—N105—H1051	120.8
N205—N206—C207	119.15 (12)	N105—N106—C107	118.37 (13)
N206—C207—C208	127.94 (13)	N106—C107—C108	128.28 (14)
N206—C207—C212	115.41 (13)	N106—C107—C112	116.74 (14)
C208—C207—C212	116.66 (13)	C108—C107—C112	114.90 (13)
C207—C208—C209	111.22 (12)	C107—C108—C109	109.37 (12)
C207—C208—H2082	107.3	C107—C108—H1081	111.7
C209—C208—H2082	109.4	C109—C108—H1081	111.8
C207—C208—H2081	110.2	C107—C108—H1082	106.5
C209—C208—H2081	110.5	C109—C108—H1082	109.2
H2082—C208—H2081	108.1	H1081—C108—H1082	108.0
C208—C209—C210	112.84 (13)	C108—C109—C110	111.01 (13)
C208—C209—H2091	107.8	C108—C109—H1092	108.3
C210—C209—H2091	109.5	C110—C109—H1092	109.3
C208—C209—H2092	108.6	C108—C109—H1091	109.1
C210—C209—H2092	108.3	C110—C109—H1091	110.9
H2091—C209—H2092	109.8	H1092—C109—H1091	108.2
C209—C210—C211	110.43 (13)	C109—C110—C111	111.52 (12)
C209—C210—H2102	108.9	C109—C110—H1101	109.0
C211—C210—H2102	108.7	C111—C110—H1101	108.6
C209—C210—H2101	109.3	C109—C110—H1102	109.0
C211—C210—H2101	110.2	C111—C110—H1102	109.0
H2102—C210—H2101	109.3	H1101—C110—H1102	109.7
C210—C211—C212	110.40 (13)	C110—C111—C112	111.11 (13)
C210—C211—H2111	110.5	C110—C111—H1112	109.2
C212—C211—H2111	109.6	C112—C111—H1112	109.1
C210—C211—H2112	108.5	C110—C111—H1111	109.0
C212—C211—H2112	109.2	C112—C111—H1111	109.9
H2111—C211—H2112	108.5	H1112—C111—H1111	108.5
C211—C212—C207	111.64 (12)	C111—C112—C107	109.33 (13)
C211—C212—H2121	109.4	C111—C112—H1121	111.2
C207—C212—H2121	106.9	C107—C112—H1121	110.2
C211—C212—H2122	111.4	C111—C112—H1122	110.0
C207—C212—H2122	109.6	C107—C112—H1122	107.2
H2121—C212—H2122	107.7	H1121—C112—H1122	108.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N205—H2051···S101ⁱ	0.89	2.57	3.4559 (13)	175
N105—H1051···S201ⁱⁱ	0.87	2.59	3.4484 (13)	169
N203—H2031···S201ⁱⁱ	0.87	2.76	3.4691 (13)	139

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₁₅N₃S
M_r	185.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.0538 (3), 11.0108 (3), 17.9484 (5)
β (°)	102.132 (3)
V (Å³)	1942.52 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.56
Crystal size (mm)	0.27 × 0.22 × 0.10

Data collection
Diffractometer	Agilent Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.58, 0.77
No. of measured, independent and observed [I > 2.0σ(I)] reflections	13859, 3754, 3414
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 0.98
No. of reflections	3740
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.21

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N205—H2051···S101ⁱ	0.89	2.57	3.4559 (13)	175
N105—H1051···S201ⁱⁱ	0.87	2.59	3.4484 (13)	169
N203—H2031···S201ⁱⁱ	0.87	2.76	3.4691 (13)	139

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 05–01–11–1243RU) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01–13–11–986FR). We also thank Siti Khadijah Densabali for collecting the X-ray data. ST and NAM wish to acknowledge the Malaysian Government for sponsorship under the FRGS/RUGS Scheme.

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