(E)-2-(2-Methyl-cyclo-hexyl-idene)hydrazinecarbothio-amide.

In the crystal of the title compound, C(8)H(15)N(3)S, mol-ecules are linked by N-H⋯S hydrogen bonds, forming chains along [1[Formula: see text]0]. An intra-molecular N-H⋯N hydrogen bond is also present.

Related literature

The title compound, C8H15N3S, is a key inter­mediate for the preparation of hydrazinyl-5-aryl­thia­zole-based monoamine oxidase B (MAO-B) inhibitors. For the synthesis of hydrazinyl-5-aryl­thia­zoles and their MAO-B inhibitory activity, see: Chimenti et al. (2008 ▶, 2010 ▶). For background on our inter­est in radiolabelled mol­ecules targeting MAO-B, see: Vasdev et al. (2011a ▶,b ▶). For the preparation of 18F-labelled potassium cryptand fluoride, see: Vasdev et al. (2009 ▶).

Experimental

Crystal data

C8H15N3S

M = 185.29

Triclinic,

a = 6.0261 (5) Å

b = 8.0655 (4) Å

c = 10.9129 (9) Å

α = 83.904 (5)°

β = 89.386 (4)°

γ = 68.416 (4)°

V = 490.19 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 150 K

0.20 × 0.14 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.710, T max = 1.060

5938 measured reflections

2184 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 1.05

2184 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042486/pv2460sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042486/pv2460Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042486/pv2460Isup3.cml

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

C8H15N3S	Z = 2
Mr = 185.29	F(000) = 200
Triclinic, P1	Dx = 1.255 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0261 (5) Å	Cell parameters from 5938 reflections
b = 8.0655 (4) Å	θ = 2.6–27.5°
c = 10.9129 (9) Å	µ = 0.28 mm−1
α = 83.904 (5)°	T = 150 K
β = 89.386 (4)°	Plate, colourless
γ = 68.416 (4)°	0.20 × 0.14 × 0.04 mm
V = 490.19 (6) Å3

Nonius KappaCCD diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.077
Detector resolution: 9 pixels mm-1	θmax = 27.6°, θmin = 2.7°
φ scans and ω scans with κ offsets	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
Tmin = 0.710, Tmax = 1.060	l = −13→14
5938 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.1232P] where P = (Fo2 + 2Fc2)/3
2184 reflections	(Δ/σ)max < 0.001
122 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. 1H NMR (CDCl3, 400 MHz) δ p.p.m. 8.83 (br s, 1H), 7.25 (br s, 1H), 6.48 (br s, 1H), 2.66 (m, 1H), 2.29 - 2.40 (m, 1H), 1.84 - 2.00 (m, 3H), 1.75 - 1.83 (m, 1H), 1.41 - 1.66 (m, 2H), 1.23 - 1.36 (m, 1H), 1.10 (d, J= 6.6 Hz, 3H). HRMS (ESI) m/z calcd for C8H16N3S, 186.1059; found 186.1064 (M++H).

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
S1	0.17188 (9)	0.22748 (6)	0.01937 (5)	0.03606 (19)
N1	0.5032 (3)	0.4731 (2)	0.19337 (16)	0.0335 (4)
H1N	0.185 (5)	0.522 (3)	0.104 (2)	0.051 (7)*
N2	0.3306 (3)	0.4439 (2)	0.12560 (17)	0.0336 (4)
N3	0.6066 (3)	0.1654 (2)	0.10779 (19)	0.0428 (5)
H2N	0.708 (4)	0.195 (3)	0.137 (2)	0.047 (7)*
H3N	0.649 (4)	0.061 (3)	0.078 (2)	0.039 (6)*
C1	0.4559 (4)	0.6253 (2)	0.23460 (19)	0.0334 (5)
C2	0.6541 (4)	0.6475 (3)	0.3062 (2)	0.0370 (5)
H2A	0.7074	0.7344	0.2537	0.044*
C3	0.5603 (4)	0.7327 (3)	0.4246 (2)	0.0437 (5)
H3A	0.5190	0.6458	0.4822	0.052*
H3B	0.6883	0.7593	0.4646	0.052*
C4	0.3419 (4)	0.9048 (3)	0.4007 (2)	0.0476 (6)
H4A	0.2849	0.9524	0.4799	0.057*
H4B	0.3853	0.9959	0.3487	0.057*
C5	0.1440 (4)	0.8698 (3)	0.3362 (2)	0.0456 (6)
H5A	0.0066	0.9842	0.3177	0.055*
H5B	0.0899	0.7880	0.3919	0.055*
C6	0.2269 (4)	0.7867 (3)	0.2168 (2)	0.0407 (5)
H6A	0.1009	0.7509	0.1837	0.049*
H6B	0.2504	0.8778	0.1553	0.049*
C7	0.8715 (4)	0.4756 (3)	0.3314 (2)	0.0450 (6)
H7A	0.9305	0.4286	0.2532	0.067*
H7B	0.8275	0.3866	0.3837	0.067*
H7C	0.9968	0.5004	0.3735	0.067*
C8	0.3858 (3)	0.2802 (2)	0.08743 (18)	0.0311 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0358 (3)	0.0288 (3)	0.0448 (4)	−0.0112 (2)	−0.0042 (2)	−0.0115 (2)
N1	0.0343 (9)	0.0373 (9)	0.0338 (10)	−0.0170 (7)	0.0000 (8)	−0.0105 (7)
N2	0.0311 (9)	0.0303 (8)	0.0405 (11)	−0.0104 (7)	−0.0030 (8)	−0.0120 (7)
N3	0.0352 (10)	0.0337 (9)	0.0588 (14)	−0.0073 (8)	−0.0075 (9)	−0.0202 (9)
C1	0.0381 (11)	0.0348 (10)	0.0306 (11)	−0.0162 (9)	0.0041 (9)	−0.0089 (8)
C2	0.0385 (12)	0.0423 (11)	0.0371 (12)	−0.0210 (9)	0.0026 (10)	−0.0116 (9)
C3	0.0464 (13)	0.0503 (12)	0.0424 (14)	−0.0240 (10)	0.0000 (11)	−0.0173 (10)
C4	0.0531 (14)	0.0452 (12)	0.0505 (15)	−0.0199 (11)	0.0035 (12)	−0.0254 (11)
C5	0.0446 (13)	0.0413 (11)	0.0513 (15)	−0.0126 (10)	0.0001 (11)	−0.0190 (10)
C6	0.0478 (13)	0.0330 (10)	0.0422 (13)	−0.0137 (9)	−0.0056 (10)	−0.0116 (9)
C7	0.0378 (12)	0.0528 (13)	0.0481 (14)	−0.0185 (10)	0.0013 (10)	−0.0155 (11)
C8	0.0344 (11)	0.0291 (9)	0.0309 (11)	−0.0115 (8)	0.0031 (9)	−0.0091 (8)

S1—C8	1.698 (2)	C3—H3A	0.9900
N1—C1	1.284 (2)	C3—H3B	0.9900
N1—N2	1.385 (2)	C4—C5	1.518 (3)
N2—C8	1.348 (2)	C4—H4A	0.9900
N2—H1N	0.88 (3)	C4—H4B	0.9900
N3—C8	1.317 (3)	C5—C6	1.523 (3)
N3—H2N	0.81 (3)	C5—H5A	0.9900
N3—H3N	0.88 (2)	C5—H5B	0.9900
C1—C6	1.506 (3)	C6—H6A	0.9900
C1—C2	1.508 (3)	C6—H6B	0.9900
C2—C7	1.518 (3)	C7—H7A	0.9800
C2—C3	1.532 (3)	C7—H7B	0.9800
C2—H2A	1.0000	C7—H7C	0.9800
C3—C4	1.521 (3)
C1—N1—N2	119.69 (16)	C5—C4—H4B	109.6
C8—N2—N1	117.61 (16)	C3—C4—H4B	109.6
C8—N2—H1N	115.7 (16)	H4A—C4—H4B	108.1
N1—N2—H1N	126.7 (16)	C4—C5—C6	111.68 (19)
C8—N3—H2N	121.1 (17)	C4—C5—H5A	109.3
C8—N3—H3N	118.9 (15)	C6—C5—H5A	109.3
H2N—N3—H3N	119 (2)	C4—C5—H5B	109.3
N1—C1—C6	127.45 (18)	C6—C5—H5B	109.3
N1—C1—C2	116.52 (17)	H5A—C5—H5B	107.9
C6—C1—C2	116.01 (16)	C1—C6—C5	112.49 (18)
C1—C2—C7	113.51 (16)	C1—C6—H6A	109.1
C1—C2—C3	110.67 (17)	C5—C6—H6A	109.1
C7—C2—C3	112.02 (19)	C1—C6—H6B	109.1
C1—C2—H2A	106.7	C5—C6—H6B	109.1
C7—C2—H2A	106.7	H6A—C6—H6B	107.8
C3—C2—H2A	106.7	C2—C7—H7A	109.5
C4—C3—C2	112.57 (19)	C2—C7—H7B	109.5
C4—C3—H3A	109.1	H7A—C7—H7B	109.5
C2—C3—H3A	109.1	C2—C7—H7C	109.5
C4—C3—H3B	109.1	H7A—C7—H7C	109.5
C2—C3—H3B	109.1	H7B—C7—H7C	109.5
H3A—C3—H3B	107.8	N3—C8—N2	117.45 (18)
C5—C4—C3	110.46 (16)	N3—C8—S1	122.61 (15)
C5—C4—H4A	109.6	N2—C8—S1	119.92 (15)
C3—C4—H4A	109.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···S1i	0.88 (3)	2.61 (3)	3.4645 (19)	162 (2)
N3—H3N···S1ii	0.88 (2)	2.52 (2)	3.3954 (19)	170.9 (19)
N3—H2N···N1	0.81 (3)	2.28 (2)	2.601 (2)	104.6 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯S1i	0.88 (3)	2.61 (3)	3.4645 (19)	162 (2)
N3—H3N⋯S1ii	0.88 (2)	2.52 (2)	3.3954 (19)	170.9 (19)
N3—H2N⋯N1	0.81 (3)	2.28 (2)	2.601 (2)	104.6 (19)

Symmetry codes: (i) ; (ii) .