3-[(Cyclo-hexyl-idene)amino]-1-(4-methyl-phen-yl)thio-urea.

In the title compound, C(14)H(19)N(3)S, the cyclo-hexane ring has a chair conformation. The almost planar amino-thio-urea unit (r.m.s. deviation = 0.0062 Å) is aligned at a dihedral angle of 45.23 (8)° with respect to the benzene ring. Inter-molecular N-H⋯N and N-H⋯S hydrogen bonding stabilizes the crystal structure.

Related literature

For related structures and the biological applications of thio­semicarbazones, see: Hu et al. (2006 ▶).

Experimental

Crystal data

C14H19N3S

M = 261.38

Orthorhombic,

a = 14.9151 (4) Å

b = 22.5593 (5) Å

c = 17.1642 (3) Å

V = 5775.3 (2) Å3

Z = 16

Cu Kα radiation

μ = 1.87 mm−1

T = 291 K

0.40 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.521, T max = 0.652

7202 measured reflections

2583 independent reflections

2024 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.162

S = 1.02

2583 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015510/xu5197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015510/xu5197Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015510/xu5197Isup3.cml

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

C14H19N3S	F(000) = 2240
Mr = 261.38	Dx = 1.202 Mg m−3
Orthorhombic, Ibca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -I 2b 2c	Cell parameters from 2807 reflections
a = 14.9151 (4) Å	θ = 3.2–70.3°
b = 22.5593 (5) Å	µ = 1.87 mm−1
c = 17.1642 (3) Å	T = 291 K
V = 5775.3 (2) Å3	Prismatic, colorless
Z = 16	0.40 × 0.25 × 0.25 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2583 independent reflections
Radiation source: fine-focus sealed tube	2024 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 67.1°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −7→17
Tmin = 0.521, Tmax = 0.652	k = −26→26
7202 measured reflections	l = −19→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1042P)2 + 0.7804P] where P = (Fo2 + 2Fc2)/3
2583 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.25 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
S1	0.88952 (5)	0.07068 (3)	0.17935 (3)	0.0599 (3)
N1	0.84361 (13)	0.02381 (8)	0.04022 (10)	0.0481 (5)
N2	0.78485 (14)	−0.01953 (8)	0.14881 (10)	0.0498 (5)
N3	0.74084 (15)	−0.05790 (8)	0.09883 (10)	0.0514 (5)
C1	0.89252 (14)	0.06343 (9)	−0.00784 (12)	0.0450 (5)
C2	0.89188 (19)	0.12432 (11)	0.00239 (14)	0.0557 (6)
H2A	0.8572	0.1413	0.0414	0.067*
C3	0.94341 (19)	0.15961 (10)	−0.04609 (14)	0.0597 (6)
H3	0.9435	0.2004	−0.0385	0.072*
C4	0.99514 (19)	0.13567 (10)	−0.10592 (13)	0.0544 (6)
C5	0.99072 (18)	0.07526 (10)	−0.11773 (13)	0.0520 (5)
H5	1.0221	0.0585	−0.1590	0.062*
C6	0.94050 (17)	0.03922 (10)	−0.06944 (12)	0.0505 (5)
H6	0.9388	−0.0014	−0.0782	0.061*
C7	1.0565 (2)	0.17332 (13)	−0.15541 (18)	0.0741 (8)
H7A	1.0221	0.1928	−0.1951	0.111*
H7B	1.1011	0.1486	−0.1793	0.111*
H7C	1.0853	0.2025	−0.1233	0.111*
C8	0.83781 (15)	0.02349 (9)	0.11831 (12)	0.0460 (5)
C9	0.68926 (18)	−0.09724 (10)	0.12732 (14)	0.0538 (6)
C10	0.6399 (2)	−0.13589 (14)	0.07092 (18)	0.0749 (8)
H10A	0.6617	−0.1284	0.0186	0.090*
H10B	0.5765	−0.1262	0.0723	0.090*
C11	0.6526 (3)	−0.20137 (15)	0.0908 (2)	0.0911 (11)
H11A	0.6166	−0.2254	0.0559	0.109*
H11B	0.7149	−0.2122	0.0835	0.109*
C12	0.6250 (3)	−0.21354 (16)	0.1747 (2)	0.0961 (11)
H12A	0.5615	−0.2058	0.1808	0.115*
H12B	0.6358	−0.2549	0.1869	0.115*
C13	0.6773 (2)	−0.17499 (16)	0.2301 (2)	0.0873 (10)
H13A	0.7401	−0.1861	0.2279	0.105*
H13B	0.6563	−0.1820	0.2827	0.105*
C14	0.6686 (2)	−0.10938 (14)	0.21164 (16)	0.0694 (7)
H14A	0.6081	−0.0963	0.2232	0.083*
H14B	0.7096	−0.0870	0.2443	0.083*
H1	0.8188 (16)	−0.0081 (12)	0.0192 (16)	0.052 (7)*
H2	0.799 (2)	−0.0305 (14)	0.195 (2)	0.075 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0824 (5)	0.0632 (4)	0.0341 (3)	−0.0172 (3)	−0.0022 (3)	−0.0052 (2)
N1	0.0605 (11)	0.0528 (9)	0.0309 (8)	−0.0072 (9)	−0.0017 (8)	−0.0002 (7)
N2	0.0634 (11)	0.0556 (10)	0.0305 (8)	−0.0083 (9)	0.0003 (9)	0.0003 (7)
N3	0.0674 (12)	0.0519 (9)	0.0349 (9)	−0.0070 (9)	−0.0031 (9)	−0.0016 (7)
C1	0.0521 (12)	0.0514 (11)	0.0316 (10)	−0.0003 (9)	−0.0032 (9)	0.0030 (8)
C2	0.0735 (15)	0.0532 (11)	0.0403 (11)	0.0110 (11)	0.0104 (11)	0.0009 (9)
C3	0.0864 (17)	0.0448 (11)	0.0478 (12)	0.0051 (11)	0.0066 (13)	0.0030 (9)
C4	0.0675 (14)	0.0561 (12)	0.0395 (11)	0.0009 (11)	0.0037 (11)	0.0078 (9)
C5	0.0638 (13)	0.0580 (12)	0.0344 (10)	0.0066 (11)	0.0062 (10)	0.0002 (9)
C6	0.0673 (14)	0.0482 (10)	0.0358 (10)	0.0004 (10)	−0.0008 (10)	−0.0013 (8)
C7	0.094 (2)	0.0640 (14)	0.0641 (16)	−0.0064 (15)	0.0204 (16)	0.0083 (13)
C8	0.0529 (12)	0.0526 (11)	0.0323 (10)	0.0015 (9)	0.0001 (9)	−0.0013 (8)
C9	0.0626 (14)	0.0548 (11)	0.0441 (12)	−0.0055 (11)	−0.0049 (11)	0.0044 (9)
C10	0.092 (2)	0.0761 (16)	0.0568 (15)	−0.0252 (16)	−0.0137 (15)	0.0025 (13)
C11	0.114 (3)	0.0713 (17)	0.088 (2)	−0.0287 (19)	0.002 (2)	−0.0052 (16)
C12	0.109 (3)	0.0764 (19)	0.103 (3)	−0.0260 (19)	0.007 (2)	0.0240 (19)
C13	0.088 (2)	0.102 (2)	0.0714 (19)	−0.0172 (19)	0.0029 (17)	0.0367 (18)
C14	0.0722 (16)	0.0869 (18)	0.0490 (14)	−0.0193 (15)	0.0081 (13)	0.0049 (13)

S1—C8	1.681 (2)	C7—H7A	0.9600
N1—C8	1.343 (3)	C7—H7B	0.9600
N1—C1	1.418 (3)	C7—H7C	0.9600
N1—H1	0.89 (3)	C9—C10	1.497 (4)
N2—C8	1.356 (3)	C9—C14	1.505 (3)
N2—N3	1.384 (3)	C10—C11	1.528 (5)
N2—H2	0.86 (3)	C10—H10A	0.9700
N3—C9	1.272 (3)	C10—H10B	0.9700
C1—C2	1.385 (3)	C11—C12	1.523 (5)
C1—C6	1.389 (3)	C11—H11A	0.9700
C2—C3	1.385 (4)	C11—H11B	0.9700
C2—H2A	0.9300	C12—C13	1.506 (5)
C3—C4	1.393 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.379 (3)	C13—C14	1.519 (5)
C4—C7	1.510 (4)	C13—H13A	0.9700
C5—C6	1.382 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C8—N1—C1	128.10 (19)	N3—C9—C10	117.1 (2)
C8—N1—H1	112.0 (17)	N3—C9—C14	128.3 (2)
C1—N1—H1	119.4 (17)	C10—C9—C14	114.6 (2)
C8—N2—N3	118.98 (17)	C9—C10—C11	111.0 (3)
C8—N2—H2	115 (2)	C9—C10—H10A	109.4
N3—N2—H2	121 (2)	C11—C10—H10A	109.4
C9—N3—N2	119.01 (19)	C9—C10—H10B	109.4
C2—C1—C6	119.4 (2)	C11—C10—H10B	109.4
C2—C1—N1	123.2 (2)	H10A—C10—H10B	108.0
C6—C1—N1	117.39 (19)	C12—C11—C10	110.6 (3)
C3—C2—C1	119.4 (2)	C12—C11—H11A	109.5
C3—C2—H2A	120.3	C10—C11—H11A	109.5
C1—C2—H2A	120.3	C12—C11—H11B	109.5
C2—C3—C4	121.8 (2)	C10—C11—H11B	109.5
C2—C3—H3	119.1	H11A—C11—H11B	108.1
C4—C3—H3	119.1	C13—C12—C11	110.7 (3)
C5—C4—C3	117.7 (2)	C13—C12—H12A	109.5
C5—C4—C7	120.1 (2)	C11—C12—H12A	109.5
C3—C4—C7	122.1 (2)	C13—C12—H12B	109.5
C4—C5—C6	121.3 (2)	C11—C12—H12B	109.5
C4—C5—H5	119.4	H12A—C12—H12B	108.1
C6—C5—H5	119.4	C12—C13—C14	112.8 (3)
C5—C6—C1	120.3 (2)	C12—C13—H13A	109.0
C5—C6—H6	119.8	C14—C13—H13A	109.0
C1—C6—H6	119.8	C12—C13—H13B	109.0
C4—C7—H7A	109.5	C14—C13—H13B	109.0
C4—C7—H7B	109.5	H13A—C13—H13B	107.8
H7A—C7—H7B	109.5	C9—C14—C13	111.1 (3)
C4—C7—H7C	109.5	C9—C14—H14A	109.4
H7A—C7—H7C	109.5	C13—C14—H14A	109.4
H7B—C7—H7C	109.5	C9—C14—H14B	109.4
N1—C8—N2	115.25 (19)	C13—C14—H14B	109.4
N1—C8—S1	126.08 (17)	H14A—C14—H14B	108.0
N2—C8—S1	118.67 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.89 (3)	2.48 (3)	3.268 (3)	148 (2)
N2—H2···S1ii	0.86 (3)	2.70 (3)	3.531 (2)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.89 (3)	2.48 (3)	3.268 (3)	148 (2)
N2—H2⋯S1ii	0.86 (3)	2.70 (3)	3.531 (2)	164 (3)

Symmetry codes: (i) ; (ii) .