1-Cyclo-hexyl-3-{(E)-[1-(pyridin-2-yl)ethyl-idene]amino}-thio-urea.

In the title thio-urea derivative, C(14)H(20)N(4)S, the non-ring non-H atoms are approximately planar, with an r.m.s. deviation of 0.0720 Å. The pyridine ring is twisted out of this plane and makes a dihedral angle of 16.85 (13)° with it. The mean plane passing through the cyclo-hexyl ring is almost normal to the central plane [dihedral angle = 69.23 (8)°]. An intra-molecular N-H⋯N(imine) hydrogen bond occurs. Centrosymmetric dimers are formed in the crystal structure via pairs of N-H⋯S hydrogen bonds, and these are connected into a supra-molecular chain along the a axis via C-H⋯π(pyrid-yl) inter-actions.

Related literature

For related thio­urea structures, see: Tiekink (1989 ▶); Lai & Tiekink (2002 ▶); Muramulla et al. (2009 ▶).

Experimental

Crystal data

C14H20N4S

M = 276.40

Triclinic,

a = 5.8824 (6) Å

b = 10.2410 (9) Å

c = 12.3902 (14) Å

α = 94.718 (8)°

β = 90.427 (9)°

γ = 90.979 (8)°

V = 743.74 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ▶) T min = 0.842, T max = 1.000

5817 measured reflections

3292 independent reflections

2355 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.151

S = 1.04

3292 reflections

181 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent Technologies, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009317/hg5008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009317/hg5008Isup2.hkl

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

C14H20N4S	Z = 2
Mr = 276.40	F(000) = 296
Triclinic, P1	Dx = 1.234 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8824 (6) Å	Cell parameters from 2234 reflections
b = 10.2410 (9) Å	θ = 2.5–29.3°
c = 12.3902 (14) Å	µ = 0.21 mm−1
α = 94.718 (8)°	T = 295 K
β = 90.427 (9)°	Block, colourless
γ = 90.979 (8)°	0.25 × 0.20 × 0.15 mm
V = 743.74 (13) Å3

Agilent Supernova Dual diffractometer with an Atlas detector	3292 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2355 reflections with I > 2σ(I)
Mirror	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −12→11
Tmin = 0.842, Tmax = 1.000	l = −16→15
5817 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.2389P] where P = (Fo2 + 2Fc2)/3
3292 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.20 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	0.98373 (10)	0.38035 (6)	0.62998 (5)	0.0566 (2)
N1	0.6028 (3)	0.4301 (2)	0.73985 (16)	0.0516 (5)
N2	0.6780 (3)	0.56047 (19)	0.60354 (16)	0.0473 (5)
N3	0.4954 (3)	0.63316 (18)	0.63973 (15)	0.0443 (4)
N4	0.2260 (4)	0.9312 (2)	0.61127 (19)	0.0655 (6)
C1	0.6423 (4)	0.3310 (2)	0.81548 (18)	0.0509 (6)
H1A	0.7317	0.2612	0.7785	0.061*
C2	0.7750 (5)	0.3871 (3)	0.9131 (2)	0.0774 (9)
H2A	0.6945	0.4610	0.9476	0.093*
H2B	0.9219	0.4189	0.8903	0.093*
C3	0.8102 (6)	0.2857 (4)	0.9947 (3)	0.1056 (13)
H3A	0.9038	0.2159	0.9627	0.127*
H3B	0.8898	0.3264	1.0579	0.127*
C4	0.5863 (6)	0.2288 (4)	1.0287 (2)	0.0850 (10)
H4A	0.6135	0.1614	1.0776	0.102*
H4B	0.4981	0.2969	1.0668	0.102*
C5	0.4558 (5)	0.1713 (3)	0.9314 (3)	0.0797 (9)
H5A	0.3094	0.1388	0.9542	0.096*
H5B	0.5380	0.0976	0.8977	0.096*
C6	0.4189 (5)	0.2718 (3)	0.8486 (2)	0.0746 (8)
H6A	0.3421	0.2296	0.7851	0.090*
H6B	0.3222	0.3407	0.8796	0.090*
C7	0.7428 (4)	0.4599 (2)	0.66113 (17)	0.0436 (5)
C8	0.4457 (4)	0.7360 (2)	0.59286 (18)	0.0433 (5)
C9	0.5690 (4)	0.7871 (2)	0.4999 (2)	0.0575 (6)
H9A	0.5857	0.7177	0.4437	0.086*
H9B	0.7165	0.8197	0.5238	0.086*
H9C	0.4842	0.8567	0.4725	0.086*
C10	0.2493 (4)	0.8097 (2)	0.64002 (17)	0.0438 (5)
C11	0.1000 (4)	0.7543 (2)	0.70977 (19)	0.0516 (6)
H11	0.1192	0.6689	0.7279	0.062*
C12	−0.0774 (4)	0.8277 (3)	0.7519 (2)	0.0627 (7)
H12	−0.1794	0.7929	0.7993	0.075*
C13	−0.1011 (5)	0.9530 (3)	0.7227 (2)	0.0702 (8)
H13	−0.2191	1.0048	0.7500	0.084*
C14	0.0518 (5)	1.0001 (3)	0.6527 (3)	0.0768 (9)
H14	0.0339	1.0850	0.6327	0.092*
H1	0.478 (3)	0.474 (2)	0.743 (2)	0.065 (8)*
H2	0.768 (4)	0.579 (3)	0.5503 (14)	0.065 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0544 (4)	0.0507 (4)	0.0685 (4)	0.0198 (3)	0.0197 (3)	0.0228 (3)
N1	0.0532 (11)	0.0492 (12)	0.0560 (11)	0.0178 (9)	0.0174 (9)	0.0209 (9)
N2	0.0480 (10)	0.0408 (11)	0.0557 (11)	0.0121 (8)	0.0150 (9)	0.0165 (9)
N3	0.0448 (9)	0.0368 (10)	0.0527 (11)	0.0086 (7)	0.0091 (8)	0.0101 (8)
N4	0.0693 (13)	0.0387 (12)	0.0918 (16)	0.0159 (10)	0.0248 (12)	0.0197 (11)
C1	0.0587 (13)	0.0454 (13)	0.0517 (13)	0.0179 (10)	0.0168 (11)	0.0172 (11)
C2	0.0801 (19)	0.084 (2)	0.0717 (18)	−0.0111 (16)	0.0005 (15)	0.0302 (16)
C3	0.101 (3)	0.137 (3)	0.087 (2)	−0.018 (2)	−0.0175 (19)	0.062 (2)
C4	0.103 (2)	0.090 (2)	0.0679 (19)	0.0107 (19)	0.0187 (17)	0.0400 (17)
C5	0.088 (2)	0.067 (2)	0.089 (2)	−0.0019 (16)	0.0221 (17)	0.0356 (17)
C6	0.0723 (18)	0.078 (2)	0.0778 (19)	−0.0094 (15)	0.0030 (15)	0.0351 (16)
C7	0.0480 (12)	0.0358 (12)	0.0479 (12)	0.0066 (9)	0.0061 (10)	0.0085 (9)
C8	0.0479 (12)	0.0338 (11)	0.0495 (12)	0.0041 (9)	0.0055 (9)	0.0101 (9)
C9	0.0650 (15)	0.0477 (14)	0.0633 (15)	0.0124 (11)	0.0193 (12)	0.0206 (12)
C10	0.0480 (11)	0.0365 (12)	0.0479 (12)	0.0061 (9)	0.0031 (10)	0.0080 (10)
C11	0.0543 (13)	0.0455 (14)	0.0568 (14)	0.0105 (10)	0.0090 (11)	0.0120 (11)
C12	0.0603 (15)	0.0694 (19)	0.0594 (15)	0.0102 (13)	0.0161 (12)	0.0079 (13)
C13	0.0689 (17)	0.0608 (18)	0.0806 (19)	0.0243 (14)	0.0174 (15)	−0.0027 (15)
C14	0.0823 (19)	0.0418 (15)	0.109 (2)	0.0219 (13)	0.0256 (18)	0.0138 (15)

S1—C7	1.678 (2)	C4—H4A	0.9700
N1—C7	1.332 (3)	C4—H4B	0.9700
N1—C1	1.457 (3)	C5—C6	1.529 (4)
N1—H1	0.870 (10)	C5—H5A	0.9700
N2—C7	1.359 (3)	C5—H5B	0.9700
N2—N3	1.374 (2)	C6—H6A	0.9700
N2—H2	0.878 (10)	C6—H6B	0.9700
N3—C8	1.281 (3)	C8—C10	1.488 (3)
N4—C10	1.331 (3)	C8—C9	1.491 (3)
N4—C14	1.336 (3)	C9—H9A	0.9600
C1—C2	1.503 (4)	C9—H9B	0.9600
C1—C6	1.512 (3)	C9—H9C	0.9600
C1—H1A	0.9800	C10—C11	1.384 (3)
C2—C3	1.523 (4)	C11—C12	1.377 (3)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C13	1.370 (4)
C3—C4	1.508 (5)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.364 (4)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.498 (5)	C14—H14	0.9300
C7—N1—C1	125.56 (19)	C6—C5—H5B	109.2
C7—N1—H1	114.1 (18)	H5A—C5—H5B	107.9
C1—N1—H1	120.3 (18)	C1—C6—C5	111.2 (2)
C7—N2—N3	118.18 (18)	C1—C6—H6A	109.4
C7—N2—H2	115.9 (18)	C5—C6—H6A	109.4
N3—N2—H2	125.6 (18)	C1—C6—H6B	109.4
C8—N3—N2	119.02 (18)	C5—C6—H6B	109.4
C10—N4—C14	117.7 (2)	H6A—C6—H6B	108.0
N1—C1—C2	111.2 (2)	N1—C7—N2	115.73 (19)
N1—C1—C6	110.3 (2)	N1—C7—S1	124.18 (17)
C2—C1—C6	110.8 (2)	N2—C7—S1	120.08 (16)
N1—C1—H1A	108.1	N3—C8—C10	114.81 (19)
C2—C1—H1A	108.1	N3—C8—C9	126.0 (2)
C6—C1—H1A	108.1	C10—C8—C9	119.19 (19)
C1—C2—C3	111.7 (3)	C8—C9—H9A	109.5
C1—C2—H2A	109.3	C8—C9—H9B	109.5
C3—C2—H2A	109.3	H9A—C9—H9B	109.5
C1—C2—H2B	109.3	C8—C9—H9C	109.5
C3—C2—H2B	109.3	H9A—C9—H9C	109.5
H2A—C2—H2B	107.9	H9B—C9—H9C	109.5
C4—C3—C2	111.2 (3)	N4—C10—C11	122.2 (2)
C4—C3—H3A	109.4	N4—C10—C8	116.23 (19)
C2—C3—H3A	109.4	C11—C10—C8	121.5 (2)
C4—C3—H3B	109.4	C12—C11—C10	119.0 (2)
C2—C3—H3B	109.4	C12—C11—H11	120.5
H3A—C3—H3B	108.0	C10—C11—H11	120.5
C5—C4—C3	110.2 (3)	C13—C12—C11	118.8 (2)
C5—C4—H4A	109.6	C13—C12—H12	120.6
C3—C4—H4A	109.6	C11—C12—H12	120.6
C5—C4—H4B	109.6	C12—C13—C14	118.7 (3)
C3—C4—H4B	109.6	C12—C13—H13	120.7
H4A—C4—H4B	108.1	C14—C13—H13	120.7
C4—C5—C6	111.9 (3)	N4—C14—C13	123.6 (3)
C4—C5—H5A	109.2	N4—C14—H14	118.2
C6—C5—H5A	109.2	C13—C14—H14	118.2
C4—C5—H5B	109.2
C7—N2—N3—C8	173.2 (2)	N2—N3—C8—C10	−178.40 (18)
C7—N1—C1—C2	87.7 (3)	N2—N3—C8—C9	0.0 (3)
C7—N1—C1—C6	−149.0 (2)	C14—N4—C10—C11	0.3 (4)
N1—C1—C2—C3	178.0 (3)	C14—N4—C10—C8	−179.7 (2)
C6—C1—C2—C3	54.9 (3)	N3—C8—C10—N4	164.7 (2)
C1—C2—C3—C4	−56.3 (4)	C9—C8—C10—N4	−13.9 (3)
C2—C3—C4—C5	56.3 (4)	N3—C8—C10—C11	−15.3 (3)
C3—C4—C5—C6	−56.3 (4)	C9—C8—C10—C11	166.1 (2)
N1—C1—C6—C5	−177.8 (2)	N4—C10—C11—C12	−0.7 (4)
C2—C1—C6—C5	−54.2 (3)	C8—C10—C11—C12	179.3 (2)
C4—C5—C6—C1	55.7 (4)	C10—C11—C12—C13	0.4 (4)
C1—N1—C7—N2	−176.6 (2)	C11—C12—C13—C14	0.2 (4)
C1—N1—C7—S1	4.3 (3)	C10—N4—C14—C13	0.3 (5)
N3—N2—C7—N1	8.8 (3)	C12—C13—C14—N4	−0.6 (5)
N3—N2—C7—S1	−172.17 (15)

Cg1 is the centroid of the pyridyl ring [ok as edited?]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.87 (2)	2.16 (2)	2.592 (3)	111 (2)
C9—H9C···N4	0.96	2.39	2.822 (3)	107
N2—H2···S1i	0.88 (2)	2.73 (2)	3.610 (2)	174 (2)
C9—H9B···Cg1ii	0.96	2.89	3.776 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.87 (2)	2.16 (2)	2.592 (3)	111 (2)
N2—H2⋯S1i	0.88 (2)	2.73 (2)	3.610 (2)	174 (2)
C9—H9b⋯Cg1ii	0.96	2.89	3.776 (3)	155

Symmetry codes: (i) ; (ii) .