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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o32.
Published online 2008 December 6. doi:  10.1107/S1600536808040464
PMCID: PMC2967950

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

Abstract

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 [triangle],b [triangle]).

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Object name is e-65-00o32-scheme1.jpg

Experimental

Crystal data

  • C14H17Cl2NOS
  • M r = 318.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o32-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 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

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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

Figures

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

Crystal data

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

Bruker SMART CCD area-detector diffractometer2712 independent reflections
Radiation source: fine-focus sealed tube1972 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] 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

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) = 0.095w = 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)

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2098).

References

  • 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. [PMC free article] [PubMed]
  • Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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