2-Cyclo-hexyl-idene-N-methyl-hydrazine-carbothio-amide.

The title compound C(8)H(15)N(3)S has two mol-ecules in the asymmetric unit in which cis-trans isomerism is exhibited around the N(NH)C=S bonds. The cyclo-hexyl rings in both mol-ecules adopt a chair conformation. In the crystal, N-H⋯S hydrogen bonding produces dimers, which are inter-connected 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 = 185.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 0.98

3740 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.21 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042018/bg2476sup1.cif

Click here for additional data file.

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

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

C8H15N3S	F(000) = 800
Mr = 185.29	Dx = 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

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

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(Fo2,0) + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3740 reflections	Δρmax = 0.42 e Å−3
217 parameters	Δρmin = −0.21 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .