1-(4-Chloro­benzo­yl)-3-cyclo­hexyl-3-methyl­thio­urea

Al-abbasi, A.A.; Yamin, B.M.; Kassim, M.B.

doi:10.1107/S1600536811025013

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1891

doi:10.1107/S1600536811025013

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1-(4-Chlorobenzoyl)-3-cyclohexyl-3-methylthiourea

Aisha A. Al-abbasi,^a Bohari M. Yamin ^a and Mohammad B. Kassim ^a,^b ^*

^aSchool of Chemical Sciences & Food Technology, Faculty of Science & Technology, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia, and ^bFuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 17 June 2011; accepted 25 June 2011; online 2 July 2011)

In the title compound, C₁₅H₁₉ClN₂OS, the dihedral angle between the amide and thiourea fragments is 58.07 (17)°. The cyclohexane group adopts a chair conformation and is twisted relative to the thiourea fragment, forming a dihedral angle of 87.32 (18)°. In the crystal, N—H⋯S hydrogen bond links the molecules into chains running parallel to the a-axis direction.

Related literature

For related structures and background references, see: Al-abbasi & Kassim (2011 ); Nasir et al. (2011 ). For further synthetic details, see: Hassan et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₉ClN₂OS
M_r = 310.83
Triclinic, $[P \overline 1]$
a = 5.042 (2) Å
b = 11.368 (4) Å
c = 15.139 (6) Å
α = 69.865 (7)°
β = 82.698 (8)°
γ = 80.702 (8)°
V = 801.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 298 K
0.52 × 0.23 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.906, T_max = 0.989
9192 measured reflections
3149 independent reflections
1935 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.192
S = 1.10
3149 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.73	3.411 (4)	137
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025013/hb5920sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025013/hb5920Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025013/hb5920Isup3.cml

checkCIF report

Comment top

The title compound, (I), is a thiourea derivative analogous to our previously reported compounds (Al-abbasi & Kassim, 2011; Nasir et al., 2011). The thiono S and the carbonyl O adopt a gauche conformation at a partially double N1—C8 bond with C7—N1—C8—S1 torsion angle of -124.4 (3)°. The dihedral angle between the mean planes of the thiourea (S1/N1/N2/C8) and the amide group (O1/N1/C1/C7/C8) is 58.07 (17)°. The cyclohexane has a chair corformation and the mean planes of (C9/C10/C11/C12/C13/C14) and the 4-chlorobenzoyl (Cl1/C1/C2/C3/C4/C5/C6/C7) fragments make an angle of 26.8 (2)°.

In the crystal, intermolecular N1—H···S1 hydrogen bond links the molecules into a one dimentional polymeric structure parallel to the a-axis.

Related literature top

For related structures and background references, see: Al-abbasi & Kassim (2011); Nasir et al. (2011). For further synthetic details, see: Hassan et al. (2008).

Experimental top

The title compound was prepared according to a previously reported compound (Hassan et al., 2008). Colourless plates of (I) were obtained by a slow evaporation of ethanolic solution at room temperature (yield 80%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound down the c-axis showing the intermolecular hydrogen bonds N—H···S (-x+1, -y + 1, -z).

1-(4-Chlorobenzoyl)-3-cyclohexyl-3-methylthiourea top

Crystal data top

C₁₅H₁₉ClN₂OS	Z = 2
M_r = 310.83	F(000) = 328
Triclinic, P1	D_x = 1.288 Mg m⁻³
Hall symbol: -P 1	Melting point = 418–420 K
a = 5.042 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.368 (4) Å	Cell parameters from 1114 reflections
c = 15.139 (6) Å	θ = 1.9–26.0°
α = 69.865 (7)°	µ = 0.37 mm⁻¹
β = 82.698 (8)°	T = 298 K
γ = 80.702 (8)°	Plate, colourless
V = 801.7 (5) Å³	0.52 × 0.23 × 0.03 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scan	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
T_min = 0.906, T_max = 0.989	k = −14→14
9192 measured reflections	l = −18→18

Refinement top

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0826P)² + 0.0972P] where P = (F_o² + 2F_c²)/3
3149 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₉ClN₂OS	γ = 80.702 (8)°
M_r = 310.83	V = 801.7 (5) Å³
Triclinic, P1	Z = 2
a = 5.042 (2) Å	Mo Kα radiation
b = 11.368 (4) Å	µ = 0.37 mm⁻¹
c = 15.139 (6) Å	T = 298 K
α = 69.865 (7)°	0.52 × 0.23 × 0.03 mm
β = 82.698 (8)°

Data collection top

Bruker SMART APEX CCD diffractometer	3149 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1935 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.989	R_int = 0.063
9192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.10	Δρ_max = 0.37 e Å⁻³
3149 reflections	Δρ_min = −0.21 e Å⁻³
182 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.3915 (2)	0.34433 (9)	0.12184 (8)	0.0545 (4)
Cl1	1.2888 (4)	0.63599 (15)	−0.45045 (10)	0.1074 (6)
N1	0.7565 (6)	0.3373 (3)	−0.0182 (2)	0.0470 (8)
H1	0.7996	0.4111	−0.0278	0.056*
N2	0.7860 (6)	0.1587 (3)	0.1141 (2)	0.0436 (8)
O1	0.7203 (6)	0.1941 (3)	−0.0894 (2)	0.0647 (9)
C1	0.9200 (8)	0.3791 (3)	−0.1813 (3)	0.0453 (10)
C8	0.6580 (8)	0.2720 (3)	0.0727 (3)	0.0434 (10)
C7	0.7916 (8)	0.2943 (4)	−0.0951 (3)	0.0496 (10)
C2	1.1049 (8)	0.4556 (4)	−0.1799 (3)	0.0511 (10)
H2	1.1513	0.4549	−0.1221	0.061*
C9	0.6886 (8)	0.0807 (3)	0.2086 (3)	0.0500 (10)
H9	0.4977	0.1115	0.2179	0.060*
C3	1.2217 (9)	0.5326 (4)	−0.2615 (3)	0.0593 (12)
H3	1.3486	0.5823	−0.2593	0.071*
C10	0.8322 (9)	0.0976 (4)	0.2850 (3)	0.0642 (12)
H10A	0.8101	0.1863	0.2789	0.077*
H10B	1.0233	0.0699	0.2772	0.077*
C6	0.8558 (9)	0.3803 (4)	−0.2693 (3)	0.0614 (12)
H6	0.7376	0.3271	−0.2722	0.074*
C15	1.0483 (8)	0.1113 (4)	0.0754 (3)	0.0561 (11)
H15A	1.0200	0.0601	0.0393	0.084*
H15B	1.1572	0.0614	0.1262	0.084*
H15C	1.1382	0.1813	0.0354	0.084*
C4	1.1485 (10)	0.5351 (4)	−0.3466 (3)	0.0668 (13)
C5	0.9673 (10)	0.4596 (5)	−0.3505 (3)	0.0718 (14)
H5	0.9201	0.4623	−0.4086	0.086*
C14	0.7051 (9)	−0.0591 (4)	0.2195 (4)	0.0708 (14)
H14A	0.6045	−0.0679	0.1721	0.085*
H14B	0.8915	−0.0930	0.2098	0.085*
C12	0.7376 (12)	−0.1166 (6)	0.3931 (4)	0.108 (2)
H12A	0.6573	−0.1624	0.4547	0.130*
H12B	0.9254	−0.1518	0.3886	0.130*
C13	0.5919 (11)	−0.1324 (5)	0.3164 (5)	0.100 (2)
H13A	0.6101	−0.2212	0.3229	0.120*
H13B	0.4015	−0.1031	0.3240	0.120*
C11	0.7191 (12)	0.0218 (6)	0.3827 (4)	0.0969 (18)
H11A	0.8191	0.0306	0.4303	0.116*
H11B	0.5322	0.0549	0.3927	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0603 (7)	0.0371 (6)	0.0621 (7)	0.0054 (5)	−0.0001 (5)	−0.0182 (5)
Cl1	0.1343 (14)	0.1065 (12)	0.0655 (9)	−0.0256 (10)	0.0032 (9)	−0.0077 (8)
N1	0.065 (2)	0.0364 (17)	0.045 (2)	−0.0057 (15)	−0.0051 (17)	−0.0215 (15)
N2	0.0444 (19)	0.0371 (17)	0.051 (2)	0.0010 (14)	−0.0094 (16)	−0.0180 (15)
O1	0.090 (2)	0.0534 (18)	0.065 (2)	−0.0119 (16)	−0.0157 (17)	−0.0333 (16)
C1	0.049 (2)	0.043 (2)	0.046 (2)	0.0083 (18)	−0.0065 (19)	−0.0231 (19)
C8	0.051 (2)	0.038 (2)	0.050 (2)	−0.0032 (18)	−0.010 (2)	−0.0238 (19)
C7	0.053 (3)	0.043 (2)	0.057 (3)	0.0087 (19)	−0.016 (2)	−0.025 (2)
C2	0.051 (3)	0.054 (2)	0.055 (3)	0.001 (2)	−0.006 (2)	−0.030 (2)
C9	0.042 (2)	0.039 (2)	0.067 (3)	−0.0003 (17)	−0.009 (2)	−0.016 (2)
C3	0.057 (3)	0.056 (3)	0.070 (3)	−0.003 (2)	−0.006 (2)	−0.029 (2)
C10	0.078 (3)	0.057 (3)	0.054 (3)	−0.015 (2)	−0.007 (2)	−0.010 (2)
C6	0.074 (3)	0.066 (3)	0.055 (3)	−0.004 (2)	−0.015 (2)	−0.033 (2)
C15	0.050 (3)	0.056 (2)	0.069 (3)	0.011 (2)	−0.014 (2)	−0.033 (2)
C4	0.073 (3)	0.064 (3)	0.056 (3)	0.002 (3)	−0.003 (3)	−0.017 (2)
C5	0.085 (4)	0.087 (4)	0.047 (3)	0.002 (3)	−0.018 (3)	−0.028 (3)
C14	0.059 (3)	0.037 (2)	0.112 (4)	−0.002 (2)	−0.019 (3)	−0.016 (3)
C12	0.080 (4)	0.093 (5)	0.103 (5)	−0.011 (3)	0.005 (4)	0.024 (4)
C13	0.062 (3)	0.045 (3)	0.163 (6)	−0.013 (2)	−0.003 (4)	0.003 (3)
C11	0.106 (5)	0.104 (5)	0.061 (3)	−0.018 (4)	−0.004 (3)	0.000 (3)

Geometric parameters (Å, º) top

S1—C8	1.687 (4)	C10—H10A	0.9700
Cl1—C4	1.739 (5)	C10—H10B	0.9700
N1—C8	1.391 (5)	C6—C5	1.365 (6)
N1—C7	1.391 (5)	C6—H6	0.9300
N1—H1	0.8600	C15—H15A	0.9600
N2—C8	1.321 (4)	C15—H15B	0.9600
N2—C9	1.470 (5)	C15—H15C	0.9600
N2—C15	1.474 (5)	C4—C5	1.370 (6)
O1—C7	1.221 (4)	C5—H5	0.9300
C1—C2	1.381 (5)	C14—C13	1.507 (7)
C1—C6	1.406 (5)	C14—H14A	0.9700
C1—C7	1.474 (5)	C14—H14B	0.9700
C2—C3	1.370 (6)	C12—C11	1.515 (8)
C2—H2	0.9300	C12—C13	1.524 (8)
C9—C10	1.520 (6)	C12—H12A	0.9700
C9—C14	1.530 (5)	C12—H12B	0.9700
C9—H9	0.9800	C13—H13A	0.9700
C3—C4	1.375 (6)	C13—H13B	0.9700
C3—H3	0.9300	C11—H11A	0.9700
C10—C11	1.524 (6)	C11—H11B	0.9700

C8—N1—C7	126.1 (3)	N2—C15—H15A	109.5
C8—N1—H1	117.0	N2—C15—H15B	109.5
C7—N1—H1	117.0	H15A—C15—H15B	109.5
C8—N2—C9	120.4 (3)	N2—C15—H15C	109.5
C8—N2—C15	122.6 (3)	H15A—C15—H15C	109.5
C9—N2—C15	116.5 (3)	H15B—C15—H15C	109.5
C2—C1—C6	118.3 (4)	C5—C4—C3	120.9 (4)
C2—C1—C7	123.2 (4)	C5—C4—Cl1	119.9 (4)
C6—C1—C7	118.5 (4)	C3—C4—Cl1	119.2 (4)
N2—C8—N1	116.8 (3)	C6—C5—C4	120.3 (4)
N2—C8—S1	125.5 (3)	C6—C5—H5	119.9
N1—C8—S1	117.8 (3)	C4—C5—H5	119.9
O1—C7—N1	121.5 (4)	C13—C14—C9	110.6 (4)
O1—C7—C1	124.2 (4)	C13—C14—H14A	109.5
N1—C7—C1	114.4 (3)	C9—C14—H14A	109.5
C3—C2—C1	121.6 (4)	C13—C14—H14B	109.5
C3—C2—H2	119.2	C9—C14—H14B	109.5
C1—C2—H2	119.2	H14A—C14—H14B	108.1
N2—C9—C10	111.3 (3)	C11—C12—C13	110.4 (5)
N2—C9—C14	113.4 (4)	C11—C12—H12A	109.6
C10—C9—C14	110.9 (4)	C13—C12—H12A	109.6
N2—C9—H9	107.0	C11—C12—H12B	109.6
C10—C9—H9	107.0	C13—C12—H12B	109.6
C14—C9—H9	107.0	H12A—C12—H12B	108.1
C2—C3—C4	119.0 (4)	C14—C13—C12	111.1 (4)
C2—C3—H3	120.5	C14—C13—H13A	109.4
C4—C3—H3	120.5	C12—C13—H13A	109.4
C9—C10—C11	110.8 (4)	C14—C13—H13B	109.4
C9—C10—H10A	109.5	C12—C13—H13B	109.4
C11—C10—H10A	109.5	H13A—C13—H13B	108.0
C9—C10—H10B	109.5	C12—C11—C10	111.0 (5)
C11—C10—H10B	109.5	C12—C11—H11A	109.4
H10A—C10—H10B	108.1	C10—C11—H11A	109.4
C5—C6—C1	120.0 (4)	C12—C11—H11B	109.4
C5—C6—H6	120.0	C10—C11—H11B	109.4
C1—C6—H6	120.0	H11A—C11—H11B	108.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.73	3.411 (4)	137

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉ClN₂OS
M_r	310.83
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.042 (2), 11.368 (4), 15.139 (6)
α, β, γ (°)	69.865 (7), 82.698 (8), 80.702 (8)
V (Å³)	801.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.52 × 0.23 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.906, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	9192, 3149, 1935
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.192, 1.10
No. of reflections	3149
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.73	3.411 (4)	137

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for grants UKM-GUP-BTT-07–30–190 and UKM-OUP-TK-16–73/2010 and sabbatical leave for MBK, and the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009. AAA thanks the Libyan Ministry of Higher Education and Sabha University for her PhD scholarship.

References

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