N-Cyclo­hexyl-2-(2,3-dichloro­phenyl­sulfan­yl)acetamide

Li, Z.-B.; Li, J.; Dong, W.-L.; Zuo, H.; He, X.-Y.

doi:10.1107/S1600536808040464

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o32

doi:10.1107/S1600536808040464

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N-Cyclohexyl-2-(2,3-dichlorophenylsulfanyl)acetamide

Zhu-Bo Li,^a ^* Jing Li,^a Wen-Liang Dong,^b Hua Zuo ^a and Xiao-Yan He ^a

^aCollege of Pharmaceutical Sciences, Southwest University, Chongqing 400716, People's Republic of China, and ^bShandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China
^*Correspondence e-mail: lizhubo2007@163.com

(Received 20 September 2008; accepted 1 December 2008; online 6 December 2008)

In the crystal structure of title compound, C₁₄H₁₇Cl₂NOS, the cyclohexyl ring has a chair conformation and connects with an equatorial N atom. Molecules are connected via N—H⋯O hydrogen bonds into chains.

Related literature

For related literature, see: Li et al. (2008a ,b ).

Experimental

Crystal data

C₁₄H₁₇Cl₂NOS
M_r = 318.25
Monoclinic, P 2₁ /c
a = 13.427 (2) Å
b = 12.877 (2) Å
c = 9.1807 (16) Å
β = 104.849 (3)°
V = 1534.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 293 (2) K
0.10 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.989
7968 measured reflections
2712 independent reflections
1972 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.095
S = 1.05
2712 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2ⁱ	0.86	2.01	2.867 (2)	177
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040464/cs2098sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040464/cs2098Isup2.hkl

checkCIF report

Comment top

The structure determination was performed as a part of a project on the interactions of small molecules with proteins. The structures of the similar compounds N-benzyl-2-(2-chloro-4-methylphenoxy)acetamide (Li et al., 2008a) and N-benzyl-2-(2,6-dichlorophenoxy)acetamide (Li et al., 2008b) were reported previously.

In the crystal structure the cyclohexyl ring is in a chair conformation. The molecules are connected via N—H···O hydrogen bonding between the N—H H atom and the carbonyl O atom into chains, that extend in the direction of the c axis.

Related literature top

For related literature, see: Li et al. (2008a,b).

Experimental top

The solution of 2,3-dichlorobenzenethiol (1.0 mmol), N-cyclohexyl-2-chloroacetamide (1.1 mmol), K₂CO₃ (1.1 mmol) and CH₃CN (20 ml) was refluxed for 4 h. After completion of the reaction (by TLC monitoring), the solution was cooled and solvent was evaporated under reduced pressure. The residue was poured into water and adjusted the pH 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO₄ to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 80%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid dissolved in ethyl acetate/hexane at room temperatures for 6 d.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at 50% probability level. H atoms are omitted for clarity.

N-Cyclohexyl-2-(2,3-dichlorophenylsulfanyl)acetamide top

Crystal data top

C₁₄H₁₇Cl₂NOS	F(000) = 664
M_r = 318.25	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1963 reflections
a = 13.427 (2) Å	θ = 2.8–23.3°
b = 12.877 (2) Å	µ = 0.55 mm⁻¹
c = 9.1807 (16) Å	T = 293 K
β = 104.849 (3)°	Needle, colourless
V = 1534.3 (5) Å³	0.10 × 0.06 × 0.02 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2712 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→15
T_min = 0.947, T_max = 0.989	k = −15→15
7968 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0364P)² + 0.4415P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2712 reflections	Δρ_max = 0.26 e Å⁻³
173 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (12)

Crystal data top

C₁₄H₁₇Cl₂NOS	V = 1534.3 (5) Å³
M_r = 318.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.427 (2) Å	µ = 0.55 mm⁻¹
b = 12.877 (2) Å	T = 293 K
c = 9.1807 (16) Å	0.10 × 0.06 × 0.02 mm
β = 104.849 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2712 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1972 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.989	R_int = 0.033
7968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
2712 reflections	Δρ_min = −0.27 e Å⁻³
173 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.85908 (5)	0.72227 (5)	0.05020 (7)	0.0493 (2)
Cl1	1.06216 (5)	0.73736 (6)	−0.03167 (9)	0.0719 (3)
Cl2	1.24245 (6)	0.58238 (7)	0.09765 (11)	0.0941 (3)
O1	0.66239 (12)	0.81810 (13)	−0.02975 (18)	0.0506 (4)
C1	1.04846 (17)	0.64033 (18)	0.0911 (3)	0.0455 (6)
C2	1.12759 (19)	0.5724 (2)	0.1488 (3)	0.0549 (7)
C3	1.1172 (2)	0.4955 (2)	0.2479 (3)	0.0647 (8)
H3	1.1712	0.4502	0.2875	0.078*
C4	1.0261 (2)	0.4870 (2)	0.2872 (3)	0.0639 (7)
H4	1.0184	0.4352	0.3541	0.077*
C5	0.94551 (19)	0.55371 (19)	0.2295 (3)	0.0528 (6)
H5	0.8838	0.5460	0.2567	0.063*
C6	0.95562 (17)	0.63200 (17)	0.1317 (3)	0.0409 (5)
C7	0.75922 (16)	0.69227 (18)	0.1412 (3)	0.0436 (6)
H7A	0.7322	0.6232	0.1129	0.052*
H7B	0.7862	0.6945	0.2498	0.052*
C8	0.67521 (16)	0.77252 (17)	0.0911 (3)	0.0395 (5)
N1	0.61760 (14)	0.78834 (15)	0.1866 (2)	0.0483 (5)
H1	0.6331	0.7557	0.2711	0.058*
C9	0.52927 (17)	0.85822 (19)	0.1558 (3)	0.0461 (6)
H9	0.5418	0.9135	0.0893	0.055*
C10	0.5189 (2)	0.9077 (2)	0.2997 (3)	0.0596 (7)
H10A	0.5807	0.9472	0.3443	0.072*
H10B	0.5121	0.8539	0.3704	0.072*
C11	0.4258 (3)	0.9791 (3)	0.2719 (4)	0.0849 (10)
H11A	0.4185	1.0055	0.3676	0.102*
H11B	0.4368	1.0379	0.2118	0.102*
C12	0.3288 (3)	0.9245 (3)	0.1922 (4)	0.0917 (11)
H12A	0.2721	0.9736	0.1706	0.110*
H12B	0.3133	0.8707	0.2571	0.110*
C13	0.3393 (2)	0.8767 (3)	0.0481 (4)	0.0904 (11)
H13A	0.3477	0.9311	−0.0210	0.108*
H13B	0.2772	0.8383	0.0015	0.108*
C14	0.4319 (2)	0.8039 (3)	0.0773 (4)	0.0812 (10)
H14A	0.4203	0.7460	0.1386	0.097*
H14B	0.4389	0.7763	−0.0178	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0419 (3)	0.0507 (4)	0.0586 (4)	0.0076 (3)	0.0191 (3)	0.0136 (3)
Cl1	0.0579 (4)	0.0733 (5)	0.0933 (6)	0.0049 (3)	0.0355 (4)	0.0264 (4)
Cl2	0.0492 (5)	0.1011 (7)	0.1388 (8)	0.0170 (4)	0.0364 (5)	0.0111 (6)
O1	0.0577 (10)	0.0588 (10)	0.0387 (9)	0.0133 (8)	0.0183 (8)	0.0075 (8)
C1	0.0441 (13)	0.0426 (14)	0.0500 (15)	0.0009 (11)	0.0124 (11)	−0.0024 (12)
C2	0.0416 (14)	0.0547 (16)	0.0675 (18)	0.0065 (12)	0.0124 (12)	−0.0051 (14)
C3	0.0586 (17)	0.0533 (17)	0.076 (2)	0.0156 (14)	0.0058 (15)	0.0047 (15)
C4	0.0727 (19)	0.0484 (16)	0.0700 (19)	0.0114 (14)	0.0175 (15)	0.0152 (14)
C5	0.0537 (15)	0.0471 (14)	0.0599 (16)	0.0036 (12)	0.0189 (13)	0.0064 (13)
C6	0.0425 (13)	0.0366 (12)	0.0431 (13)	0.0022 (10)	0.0100 (10)	−0.0015 (11)
C7	0.0432 (13)	0.0476 (14)	0.0417 (13)	0.0029 (11)	0.0142 (10)	0.0024 (11)
C8	0.0374 (12)	0.0429 (13)	0.0383 (13)	−0.0024 (10)	0.0101 (10)	−0.0063 (11)
N1	0.0471 (11)	0.0620 (13)	0.0394 (11)	0.0143 (10)	0.0174 (9)	0.0104 (10)
C9	0.0431 (13)	0.0552 (15)	0.0429 (14)	0.0087 (11)	0.0165 (11)	0.0060 (12)
C10	0.0648 (17)	0.0590 (17)	0.0545 (16)	0.0130 (14)	0.0140 (14)	−0.0059 (14)
C11	0.100 (3)	0.084 (2)	0.070 (2)	0.044 (2)	0.0194 (19)	−0.0107 (18)
C12	0.068 (2)	0.113 (3)	0.105 (3)	0.034 (2)	0.042 (2)	0.009 (2)
C13	0.0447 (17)	0.106 (3)	0.111 (3)	0.0128 (17)	0.0022 (17)	−0.025 (2)
C14	0.0518 (17)	0.088 (2)	0.095 (2)	0.0106 (16)	0.0030 (16)	−0.0380 (19)

Geometric parameters (Å, º) top

S1—C6	1.759 (2)	N1—H1	0.8600
S1—C7	1.794 (2)	C9—C14	1.495 (4)
Cl1—C1	1.724 (2)	C9—C10	1.505 (3)
Cl2—C2	1.728 (3)	C9—H9	0.9800
O1—C8	1.228 (2)	C10—C11	1.520 (4)
C1—C2	1.373 (3)	C10—H10A	0.9700
C1—C6	1.394 (3)	C10—H10B	0.9700
C2—C3	1.376 (4)	C11—C12	1.496 (4)
C3—C4	1.365 (4)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.377 (3)	C12—C13	1.499 (4)
C4—H4	0.9300	C12—H12A	0.9700
C5—C6	1.380 (3)	C12—H12B	0.9700
C5—H5	0.9300	C13—C14	1.524 (4)
C7—C8	1.512 (3)	C13—H13A	0.9700
C7—H7A	0.9700	C13—H13B	0.9700
C7—H7B	0.9700	C14—H14A	0.9700
C8—N1	1.325 (3)	C14—H14B	0.9700
N1—C9	1.457 (3)

C6—S1—C7	102.52 (11)	N1—C9—H9	108.0
C2—C1—C6	120.3 (2)	C14—C9—H9	108.0
C2—C1—Cl1	120.80 (19)	C10—C9—H9	108.0
C6—C1—Cl1	118.90 (18)	C9—C10—C11	111.5 (2)
C1—C2—C3	120.9 (2)	C9—C10—H10A	109.3
C1—C2—Cl2	120.3 (2)	C11—C10—H10A	109.3
C3—C2—Cl2	118.8 (2)	C9—C10—H10B	109.3
C4—C3—C2	118.9 (2)	C11—C10—H10B	109.3
C4—C3—H3	120.6	H10A—C10—H10B	108.0
C2—C3—H3	120.6	C12—C11—C10	111.9 (3)
C3—C4—C5	121.1 (3)	C12—C11—H11A	109.2
C3—C4—H4	119.4	C10—C11—H11A	109.2
C5—C4—H4	119.4	C12—C11—H11B	109.2
C4—C5—C6	120.5 (2)	C10—C11—H11B	109.2
C4—C5—H5	119.7	H11A—C11—H11B	107.9
C6—C5—H5	119.7	C11—C12—C13	110.9 (3)
C5—C6—C1	118.3 (2)	C11—C12—H12A	109.4
C5—C6—S1	125.10 (18)	C13—C12—H12A	109.4
C1—C6—S1	116.58 (17)	C11—C12—H12B	109.4
C8—C7—S1	107.41 (15)	C13—C12—H12B	109.4
C8—C7—H7A	110.2	H12A—C12—H12B	108.0
S1—C7—H7A	110.2	C12—C13—C14	110.7 (3)
C8—C7—H7B	110.2	C12—C13—H13A	109.5
S1—C7—H7B	110.2	C14—C13—H13A	109.5
H7A—C7—H7B	108.5	C12—C13—H13B	109.5
O1—C8—N1	123.6 (2)	C14—C13—H13B	109.5
O1—C8—C7	121.53 (19)	H13A—C13—H13B	108.1
N1—C8—C7	114.8 (2)	C9—C14—C13	111.7 (2)
C8—N1—C9	123.41 (19)	C9—C14—H14A	109.3
C8—N1—H1	118.3	C13—C14—H14A	109.3
C9—N1—H1	118.3	C9—C14—H14B	109.3
N1—C9—C14	111.9 (2)	C13—C14—H14B	109.3
N1—C9—C10	110.20 (19)	H14A—C14—H14B	107.9
C14—C9—C10	110.7 (2)

S1—C7—C8—O1	25.9 (3)	C14—C9—C10—C11	−54.3 (3)
S1—C7—C8—N1	−154.55 (17)	C9—C10—C11—C12	54.7 (4)
O1—C8—N1—C9	3.0 (4)	C10—C11—C12—C13	−55.3 (4)
C7—C8—N1—C9	−176.6 (2)	C11—C12—C13—C14	55.8 (4)
C8—N1—C9—C14	89.3 (3)	N1—C9—C14—C13	178.9 (3)
C8—N1—C9—C10	−147.0 (2)	C10—C9—C14—C13	55.5 (3)
N1—C9—C10—C11	−178.6 (2)	C12—C13—C14—C9	−56.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.01	2.867 (2)	177

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇Cl₂NOS
M_r	318.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.427 (2), 12.877 (2), 9.1807 (16)
β (°)	104.849 (3)
V (Å³)	1534.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.10 × 0.06 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7968, 2712, 1972
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.095, 1.05
No. of reflections	2712
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.01	2.867 (2)	177

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

This study was supported by the Key Programme Projects of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2008AA1001)

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008a). Acta Cryst. E64, o1610. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar