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Acta Cryst. (2009). E65, o32    [ doi:10.1107/S1600536808040464 ]

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

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

Abstract top

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.

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.

Refinement top

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.97 Å (for CH2 groups).

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
[Figure 1] 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
C14H17Cl2NOSF(000) = 664
Mr = 318.25Dx = 1.378 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1963 reflections
a = 13.427 (2) Åθ = 2.8–23.3°
b = 12.877 (2) ŵ = 0.55 mm−1
c = 9.1807 (16) ÅT = 293 K
β = 104.849 (3)°Needle, colourless
V = 1534.3 (5) Å30.10 × 0.06 × 0.02 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2712 independent reflections
Radiation source: fine-focus sealed tube1972 reflections with I > 2σ(I)
graphiteRint = 0.033
φ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −15→15
Tmin = 0.947, Tmax = 0.989k = −15→15
7968 measured reflectionsl = −10→10
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.4415P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2712 reflectionsΔρmax = 0.26 e Å−3
173 parametersΔρmin = −0.27 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0083 (12)
Crystal data top
C14H17Cl2NOSV = 1534.3 (5) Å3
Mr = 318.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.427 (2) ŵ = 0.55 mm−1
b = 12.877 (2) ÅT = 293 K
c = 9.1807 (16) Å0.10 × 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)
Tmin = 0.947, Tmax = 0.989Rint = 0.033
7968 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.26 e Å−3
S = 1.05Δρmin = −0.27 e Å−3
2712 reflectionsAbsolute structure: ?
173 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.85908 (5)0.72227 (5)0.05020 (7)0.0493 (2)
Cl11.06216 (5)0.73736 (6)−0.03167 (9)0.0719 (3)
Cl21.24245 (6)0.58238 (7)0.09765 (11)0.0941 (3)
O10.66239 (12)0.81810 (13)−0.02975 (18)0.0506 (4)
C11.04846 (17)0.64033 (18)0.0911 (3)0.0455 (6)
C21.12759 (19)0.5724 (2)0.1488 (3)0.0549 (7)
C31.1172 (2)0.4955 (2)0.2479 (3)0.0647 (8)
H31.17120.45020.28750.078*
C41.0261 (2)0.4870 (2)0.2872 (3)0.0639 (7)
H41.01840.43520.35410.077*
C50.94551 (19)0.55371 (19)0.2295 (3)0.0528 (6)
H50.88380.54600.25670.063*
C60.95562 (17)0.63200 (17)0.1317 (3)0.0409 (5)
C70.75922 (16)0.69227 (18)0.1412 (3)0.0436 (6)
H7A0.73220.62320.11290.052*
H7B0.78620.69450.24980.052*
C80.67521 (16)0.77252 (17)0.0911 (3)0.0395 (5)
N10.61760 (14)0.78834 (15)0.1866 (2)0.0483 (5)
H10.63310.75570.27110.058*
C90.52927 (17)0.85822 (19)0.1558 (3)0.0461 (6)
H90.54180.91350.08930.055*
C100.5189 (2)0.9077 (2)0.2997 (3)0.0596 (7)
H10A0.58070.94720.34430.072*
H10B0.51210.85390.37040.072*
C110.4258 (3)0.9791 (3)0.2719 (4)0.0849 (10)
H11A0.41851.00550.36760.102*
H11B0.43681.03790.21180.102*
C120.3288 (3)0.9245 (3)0.1922 (4)0.0917 (11)
H12A0.27210.97360.17060.110*
H12B0.31330.87070.25710.110*
C130.3393 (2)0.8767 (3)0.0481 (4)0.0904 (11)
H13A0.34770.9311−0.02100.108*
H13B0.27720.83830.00150.108*
C140.4319 (2)0.8039 (3)0.0773 (4)0.0812 (10)
H14A0.42030.74600.13860.097*
H14B0.43890.7763−0.01780.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0419 (3)0.0507 (4)0.0586 (4)0.0076 (3)0.0191 (3)0.0136 (3)
Cl10.0579 (4)0.0733 (5)0.0933 (6)0.0049 (3)0.0355 (4)0.0264 (4)
Cl20.0492 (5)0.1011 (7)0.1388 (8)0.0170 (4)0.0364 (5)0.0111 (6)
O10.0577 (10)0.0588 (10)0.0387 (9)0.0133 (8)0.0183 (8)0.0075 (8)
C10.0441 (13)0.0426 (14)0.0500 (15)0.0009 (11)0.0124 (11)−0.0024 (12)
C20.0416 (14)0.0547 (16)0.0675 (18)0.0065 (12)0.0124 (12)−0.0051 (14)
C30.0586 (17)0.0533 (17)0.076 (2)0.0156 (14)0.0058 (15)0.0047 (15)
C40.0727 (19)0.0484 (16)0.0700 (19)0.0114 (14)0.0175 (15)0.0152 (14)
C50.0537 (15)0.0471 (14)0.0599 (16)0.0036 (12)0.0189 (13)0.0064 (13)
C60.0425 (13)0.0366 (12)0.0431 (13)0.0022 (10)0.0100 (10)−0.0015 (11)
C70.0432 (13)0.0476 (14)0.0417 (13)0.0029 (11)0.0142 (10)0.0024 (11)
C80.0374 (12)0.0429 (13)0.0383 (13)−0.0024 (10)0.0101 (10)−0.0063 (11)
N10.0471 (11)0.0620 (13)0.0394 (11)0.0143 (10)0.0174 (9)0.0104 (10)
C90.0431 (13)0.0552 (15)0.0429 (14)0.0087 (11)0.0165 (11)0.0060 (12)
C100.0648 (17)0.0590 (17)0.0545 (16)0.0130 (14)0.0140 (14)−0.0059 (14)
C110.100 (3)0.084 (2)0.070 (2)0.044 (2)0.0194 (19)−0.0107 (18)
C120.068 (2)0.113 (3)0.105 (3)0.034 (2)0.042 (2)0.009 (2)
C130.0447 (17)0.106 (3)0.111 (3)0.0128 (17)0.0022 (17)−0.025 (2)
C140.0518 (17)0.088 (2)0.095 (2)0.0106 (16)0.0030 (16)−0.0380 (19)
Geometric parameters (Å, °) top
S1—C61.759 (2)N1—H10.8600
S1—C71.794 (2)C9—C141.495 (4)
Cl1—C11.724 (2)C9—C101.505 (3)
Cl2—C21.728 (3)C9—H90.9800
O1—C81.228 (2)C10—C111.520 (4)
C1—C21.373 (3)C10—H10A0.9700
C1—C61.394 (3)C10—H10B0.9700
C2—C31.376 (4)C11—C121.496 (4)
C3—C41.365 (4)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.377 (3)C12—C131.499 (4)
C4—H40.9300C12—H12A0.9700
C5—C61.380 (3)C12—H12B0.9700
C5—H50.9300C13—C141.524 (4)
C7—C81.512 (3)C13—H13A0.9700
C7—H7A0.9700C13—H13B0.9700
C7—H7B0.9700C14—H14A0.9700
C8—N11.325 (3)C14—H14B0.9700
N1—C91.457 (3)
C6—S1—C7102.52 (11)N1—C9—H9108.0
C2—C1—C6120.3 (2)C14—C9—H9108.0
C2—C1—Cl1120.80 (19)C10—C9—H9108.0
C6—C1—Cl1118.90 (18)C9—C10—C11111.5 (2)
C1—C2—C3120.9 (2)C9—C10—H10A109.3
C1—C2—Cl2120.3 (2)C11—C10—H10A109.3
C3—C2—Cl2118.8 (2)C9—C10—H10B109.3
C4—C3—C2118.9 (2)C11—C10—H10B109.3
C4—C3—H3120.6H10A—C10—H10B108.0
C2—C3—H3120.6C12—C11—C10111.9 (3)
C3—C4—C5121.1 (3)C12—C11—H11A109.2
C3—C4—H4119.4C10—C11—H11A109.2
C5—C4—H4119.4C12—C11—H11B109.2
C4—C5—C6120.5 (2)C10—C11—H11B109.2
C4—C5—H5119.7H11A—C11—H11B107.9
C6—C5—H5119.7C11—C12—C13110.9 (3)
C5—C6—C1118.3 (2)C11—C12—H12A109.4
C5—C6—S1125.10 (18)C13—C12—H12A109.4
C1—C6—S1116.58 (17)C11—C12—H12B109.4
C8—C7—S1107.41 (15)C13—C12—H12B109.4
C8—C7—H7A110.2H12A—C12—H12B108.0
S1—C7—H7A110.2C12—C13—C14110.7 (3)
C8—C7—H7B110.2C12—C13—H13A109.5
S1—C7—H7B110.2C14—C13—H13A109.5
H7A—C7—H7B108.5C12—C13—H13B109.5
O1—C8—N1123.6 (2)C14—C13—H13B109.5
O1—C8—C7121.53 (19)H13A—C13—H13B108.1
N1—C8—C7114.8 (2)C9—C14—C13111.7 (2)
C8—N1—C9123.41 (19)C9—C14—H14A109.3
C8—N1—H1118.3C13—C14—H14A109.3
C9—N1—H1118.3C9—C14—H14B109.3
N1—C9—C14111.9 (2)C13—C14—H14B109.3
N1—C9—C10110.20 (19)H14A—C14—H14B107.9
C14—C9—C10110.7 (2)
S1—C7—C8—O125.9 (3)C14—C9—C10—C11−54.3 (3)
S1—C7—C8—N1−154.55 (17)C9—C10—C11—C1254.7 (4)
O1—C8—N1—C93.0 (4)C10—C11—C12—C13−55.3 (4)
C7—C8—N1—C9−176.6 (2)C11—C12—C13—C1455.8 (4)
C8—N1—C9—C1489.3 (3)N1—C9—C14—C13178.9 (3)
C8—N1—C9—C10−147.0 (2)C10—C9—C14—C1355.5 (3)
N1—C9—C10—C11−178.6 (2)C12—C13—C14—C9−56.5 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O2i0.862.012.867 (2)177
Symmetry codes: (i) x, −y+3/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O2i0.862.012.867 (2)177
Symmetry codes: (i) x, −y+3/2, z+1/2.
Acknowledgements top

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

references
References top

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008a). Acta Cryst. E64, o1610.

Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.