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

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[Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008a). Acta Cryst. E64, o1610.],b[Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17Cl2NOS

  • Mr = 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[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.989

  • 7968 measured reflections

  • 2712 independent reflections

  • 1972 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.095

  • S = 1.05

  • 2712 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 m3
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 mm1
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)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1515
Tmin = 0.947, Tmax = 0.989k = 1515
7968 measured reflectionsl = 1010
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 Å3
173 parametersΔρmin = 0.27 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
2712 reflectionsΔρmin = 0.27 e Å3
173 parameters
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)
H13A0.34770.93110.02100.108*
H13B0.27720.83830.00150.108*
C140.4319 (2)0.8039 (3)0.0773 (4)0.0812 (10)
H14A0.42030.74600.13860.097*
H14B0.43890.77630.01780.097*
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, º) 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—C1154.3 (3)
S1—C7—C8—N1154.55 (17)C9—C10—C11—C1254.7 (4)
O1—C8—N1—C93.0 (4)C10—C11—C12—C1355.3 (4)
C7—C8—N1—C9176.6 (2)C11—C12—C13—C1455.8 (4)
C8—N1—C9—C1489.3 (3)N1—C9—C14—C13178.9 (3)
C8—N1—C9—C10147.0 (2)C10—C9—C14—C1355.5 (3)
N1—C9—C10—C11178.6 (2)C12—C13—C14—C956.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H0A···O2i0.862.012.867 (2)177
Symmetry code: (i) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H17Cl2NOS
Mr318.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.427 (2), 12.877 (2), 9.1807 (16)
β (°) 104.849 (3)
V3)1534.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.10 × 0.06 × 0.02
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.947, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
7968, 2712, 1972
Rint0.033
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.095, 1.05
No. of reflections2712
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N—H0A···O2i0.862.012.867 (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

First citationBruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, 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
First citationLi, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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