N-Cyclo­hexyl­carbonyl-N′-phenyl­thio­urea

The title compound, C₁₄H₁₈N₂OS, adopts a trans–cis configuration of the cyclo­hexyl­carbonyl and phenyl groups with respect to the thione S atom across the thio­urea C—N bonds. There is an intramolecular N—H...O hydrogen bond, and intermolecular N—H...S hydrogen bonds generate a dimer.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.092
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        500 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C8      ..       6.93 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H18 N2 O S

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Thiourea derivatives have received considerable attention because of their potential applications in materials science (Wei et al., 2004) and their biological activities (Baruah et al., 2002). The title compound, (I), is similar to N-benzoyl-N'-phenylthiourea (II) (Yamin & Yusof, 2003), except that one of the phenyl groups is replaced by a cyclohexane group (Fig. 1). The molecule maintains its trans-cis configuration with respect to the positions of the cyclohexylcarbonyl and phenyl groups relative to the thiono S1 atom across the two C—N bonds. The bond lengths and angles are in normal ranges and comparable to those in (II) and other thiourea derivatives (Yusof et al., 2007). The central carbonylthiourea (S1/N1/N2/C7/O1/C8) fragment and phenyl ring (C9—C14) are all planar, with a maximum deviation of 0.038 (1) Å from the least-squares plane for atom N1. The central carbonylthiourea fragment makes a dihedral angle of 62.68 (6)° with the phenyl ring, which is larger than the equivalent dihedral angle in (II) (28.78 (9)°).

There is an intramolecular hydrogen bond, N2—H2A···O1 (Table 1), which results in a pseudo-six-membered ring, O1···H2A—N2—C8—N1—C7—O1. In the crystal structure, the molecules are linked by two equivalent N—H···S intermolecular interactions, (symmetry codes as in Table 1) to form dimers (Fig. 2).

Related literature

For crystal structures of related compounds, see: Yamin & Yusof (2003); Yusof et al. (2007). For details of potential applications in materials and biological activities, see: Wei et al. (2004); Baruah et al. (2002).

S2. Experimental

To a stirred acetone solution (75 ml) of cyclohexylcarbonyl chloride (2.0 g, 14 mmol) and ammoniumthiocyanate (1.04 g, 14 mmol), aniline (1.27 g, 14 mmol) in 40 ml of acetone was added dropwise. The reaction mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol before drying under vacuum. Good quality crystals were obtained by recrystallization from methanol.

S3. Refinement

After their location in a difference map, all H-atoms were fixed geometrically at ideal positions and allowed to ride on the parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å with U_iso(H)= 1.2 (CH₂ and NH).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Packing diagram of (I) viewed down the a axis. The dashed lines denote the N—H···S hydrogen bonds.

N-Cyclohexylcarbonyl-N'-phenylthiourea

Crystal data

C14H18N2OS	Z = 2
Mr = 262.36	F(000) = 280
Triclinic, P1	Dx = 1.268 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.696 (2) Å	Cell parameters from 837 reflections
b = 9.395 (3) Å	θ = 1.7–25.4°
c = 12.578 (4) Å	µ = 0.23 mm^−1
α = 100.262 (5)°	T = 293 K
β = 104.720 (5)°	Block, colourless
γ = 110.075 (5)°	0.46 × 0.42 × 0.22 mm
V = 687.4 (4) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	2207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm^-1	θmax = 25.4°, θmin = 1.7°
ω scan	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
Tmin = 0.903, Tmax = 0.952	l = −15→15
6848 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.1063P] where P = (Fo^2 + 2Fc^2)/3
2547 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.34074 (6)	0.15250 (5)	0.11564 (3)	0.05336 (15)
N2	0.56387 (19)	0.24546 (14)	−0.02447 (10)	0.0459 (3)
H2A	0.5697	0.2301	−0.0929	0.055*
O1	0.37126 (19)	0.08767 (14)	−0.24588 (9)	0.0631 (3)
N1	0.21478 (19)	0.03681 (14)	−0.10875 (10)	0.0458 (3)
H1A	0.0942	−0.0228	−0.0995	0.055*
C9	0.7521 (2)	0.37186 (16)	0.06468 (12)	0.0414 (3)
C7	0.2163 (2)	0.00689 (17)	−0.21976 (12)	0.0462 (3)
C6	0.0093 (2)	−0.13047 (17)	−0.30580 (12)	0.0457 (3)
H6A	−0.0568	−0.2029	−0.2647	0.055*
C8	0.3803 (2)	0.14953 (16)	−0.01007 (12)	0.0416 (3)
C10	0.7245 (3)	0.49819 (19)	0.12396 (14)	0.0541 (4)
H10A	0.5819	0.4995	0.1082	0.065*
C14	0.9628 (2)	0.37063 (18)	0.08647 (13)	0.0477 (4)
H14A	0.9818	0.2867	0.0452	0.057*
C13	1.1471 (3)	0.4958 (2)	0.17066 (14)	0.0583 (4)
H13A	1.2899	0.4946	0.1868	0.070*
C1	0.0713 (3)	−0.2208 (2)	−0.39591 (14)	0.0575 (4)
H1B	0.1462	−0.1492	−0.4341	0.069*
H1C	0.1759	−0.2618	−0.3587	0.069*
C12	1.1208 (3)	0.6209 (2)	0.23018 (14)	0.0620 (5)
H12A	1.2451	0.7047	0.2863	0.074*
C3	−0.3147 (3)	−0.3017 (2)	−0.53876 (14)	0.0632 (5)
H3A	−0.4496	−0.3927	−0.5901	0.076*
H3B	−0.2580	−0.2347	−0.5842	0.076*
C5	−0.1659 (3)	−0.07249 (19)	−0.36170 (14)	0.0531 (4)
H5A	−0.1008	0.0042	−0.3992	0.064*
H5B	−0.2087	−0.0203	−0.3031	0.064*
C11	0.9092 (3)	0.6221 (2)	0.20657 (15)	0.0622 (4)
H11A	0.8910	0.7073	0.2467	0.075*
C2	−0.1381 (3)	−0.3573 (2)	−0.48445 (15)	0.0637 (5)
H2B	−0.0954	−0.4078	−0.5438	0.076*
H2C	−0.2018	−0.4354	−0.4477	0.076*
C4	−0.3753 (3)	−0.2105 (2)	−0.44985 (15)	0.0643 (5)
H4A	−0.4496	−0.2811	−0.4109	0.077*
H4B	−0.4805	−0.1703	−0.4877	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0464 (2)	0.0612 (3)	0.0426 (2)	0.01045 (19)	0.01690 (17)	0.01272 (18)
N2	0.0388 (6)	0.0484 (7)	0.0397 (6)	0.0069 (5)	0.0138 (5)	0.0089 (5)
O1	0.0529 (7)	0.0675 (7)	0.0465 (6)	−0.0014 (6)	0.0184 (5)	0.0149 (5)
N1	0.0371 (6)	0.0461 (7)	0.0422 (7)	0.0046 (5)	0.0134 (5)	0.0106 (5)
C9	0.0378 (7)	0.0429 (7)	0.0387 (7)	0.0104 (6)	0.0127 (6)	0.0134 (6)
C7	0.0425 (8)	0.0467 (8)	0.0431 (8)	0.0113 (7)	0.0133 (6)	0.0147 (7)
C6	0.0430 (8)	0.0441 (8)	0.0409 (8)	0.0078 (6)	0.0130 (6)	0.0130 (6)
C8	0.0364 (7)	0.0404 (7)	0.0449 (8)	0.0135 (6)	0.0119 (6)	0.0124 (6)
C10	0.0436 (8)	0.0550 (9)	0.0583 (10)	0.0184 (7)	0.0157 (7)	0.0098 (8)
C14	0.0431 (8)	0.0511 (8)	0.0514 (9)	0.0188 (7)	0.0180 (7)	0.0189 (7)
C13	0.0370 (8)	0.0733 (11)	0.0570 (10)	0.0152 (8)	0.0113 (7)	0.0226 (9)
C1	0.0529 (9)	0.0603 (10)	0.0541 (10)	0.0231 (8)	0.0147 (8)	0.0095 (8)
C12	0.0498 (10)	0.0605 (10)	0.0476 (9)	0.0013 (8)	0.0061 (7)	0.0085 (8)
C3	0.0563 (10)	0.0647 (11)	0.0449 (9)	0.0105 (8)	0.0059 (7)	0.0061 (8)
C5	0.0474 (9)	0.0518 (9)	0.0525 (9)	0.0155 (7)	0.0153 (7)	0.0099 (7)
C11	0.0659 (11)	0.0517 (9)	0.0569 (10)	0.0164 (8)	0.0202 (9)	0.0041 (8)
C2	0.0690 (11)	0.0554 (10)	0.0544 (10)	0.0208 (9)	0.0164 (8)	0.0035 (8)
C4	0.0448 (9)	0.0695 (11)	0.0622 (11)	0.0168 (8)	0.0078 (8)	0.0091 (9)

Geometric parameters (Å, º)

S1—C8	1.6653 (15)	C13—H13A	0.9300
N2—C8	1.3292 (18)	C1—C2	1.521 (2)
N2—C9	1.4268 (17)	C1—H1B	0.9700
N2—H2A	0.8600	C1—H1C	0.9700
O1—C7	1.2172 (17)	C12—C11	1.376 (3)
N1—C7	1.3777 (19)	C12—H12A	0.9300
N1—C8	1.3846 (18)	C3—C2	1.509 (3)
N1—H1A	0.8600	C3—C4	1.509 (2)
C9—C14	1.372 (2)	C3—H3A	0.9700
C9—C10	1.380 (2)	C3—H3B	0.9700
C7—C6	1.507 (2)	C5—C4	1.525 (2)
C6—C1	1.522 (2)	C5—H5A	0.9700
C6—C5	1.524 (2)	C5—H5B	0.9700
C6—H6A	0.9800	C11—H11A	0.9300
C10—C11	1.376 (2)	C2—H2B	0.9700
C10—H10A	0.9300	C2—H2C	0.9700
C14—C13	1.387 (2)	C4—H4A	0.9700
C14—H14A	0.9300	C4—H4B	0.9700
C13—C12	1.367 (3)
C8—N2—C9	125.13 (12)	C2—C1—H1C	109.4
C8—N2—H2A	117.4	C6—C1—H1C	109.4
C9—N2—H2A	117.4	H1B—C1—H1C	108.0
C7—N1—C8	129.00 (12)	C13—C12—C11	119.65 (15)
C7—N1—H1A	115.5	C13—C12—H12A	120.2
C8—N1—H1A	115.5	C11—C12—H12A	120.2
C14—C9—C10	120.34 (14)	C2—C3—C4	111.90 (14)
C14—C9—N2	119.24 (13)	C2—C3—H3A	109.2
C10—C9—N2	120.33 (13)	C4—C3—H3A	109.2
O1—C7—N1	122.25 (13)	C2—C3—H3B	109.2
O1—C7—C6	123.07 (13)	C4—C3—H3B	109.2
N1—C7—C6	114.66 (12)	H3A—C3—H3B	107.9
C7—C6—C1	110.87 (13)	C6—C5—C4	110.71 (13)
C7—C6—C5	110.31 (12)	C6—C5—H5A	109.5
C1—C6—C5	111.02 (13)	C4—C5—H5A	109.5
C7—C6—H6A	108.2	C6—C5—H5B	109.5
C1—C6—H6A	108.2	C4—C5—H5B	109.5
C5—C6—H6A	108.2	H5A—C5—H5B	108.1
N2—C8—N1	115.78 (13)	C10—C11—C12	120.41 (16)
N2—C8—S1	125.19 (11)	C10—C11—H11A	119.8
N1—C8—S1	119.00 (10)	C12—C11—H11A	119.8
C11—C10—C9	119.65 (15)	C3—C2—C1	111.72 (14)
C11—C10—H10A	120.2	C3—C2—H2B	109.3
C9—C10—H10A	120.2	C1—C2—H2B	109.3
C9—C14—C13	119.36 (15)	C3—C2—H2C	109.3
C9—C14—H14A	120.3	C1—C2—H2C	109.3
C13—C14—H14A	120.3	H2B—C2—H2C	107.9
C12—C13—C14	120.57 (15)	C3—C4—C5	111.35 (14)
C12—C13—H13A	119.7	C3—C4—H4A	109.4
C14—C13—H13A	119.7	C5—C4—H4A	109.4
C2—C1—C6	110.98 (14)	C3—C4—H4B	109.4
C2—C1—H1B	109.4	C5—C4—H4B	109.4
C6—C1—H1B	109.4	H4A—C4—H4B	108.0
C8—N2—C9—C14	120.74 (16)	C10—C9—C14—C13	1.6 (2)
C8—N2—C9—C10	−62.8 (2)	N2—C9—C14—C13	178.01 (13)
C8—N1—C7—O1	−3.9 (2)	C9—C14—C13—C12	−1.2 (2)
C8—N1—C7—C6	177.58 (13)	C7—C6—C1—C2	−178.70 (13)
O1—C7—C6—C1	37.5 (2)	C5—C6—C1—C2	−55.71 (18)
N1—C7—C6—C1	−143.95 (14)	C14—C13—C12—C11	0.2 (3)
O1—C7—C6—C5	−85.88 (18)	C7—C6—C5—C4	179.44 (13)
N1—C7—C6—C5	92.65 (15)	C1—C6—C5—C4	56.13 (18)
C9—N2—C8—N1	178.47 (12)	C9—C10—C11—C12	0.1 (3)
C9—N2—C8—S1	−3.4 (2)	C13—C12—C11—C10	0.3 (3)
C7—N1—C8—N2	2.1 (2)	C4—C3—C2—C1	−54.5 (2)
C7—N1—C8—S1	−176.13 (12)	C6—C1—C2—C3	54.8 (2)
C14—C9—C10—C11	−1.0 (2)	C2—C3—C4—C5	54.9 (2)
N2—C9—C10—C11	−177.45 (14)	C6—C5—C4—C3	−55.56 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.95	2.6471 (18)	137
N1—H1A···S1^i	0.86	2.68	3.4997 (19)	160

Symmetry code: (i) −x, −y, −z.