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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2288.
Published online 2008 November 8. doi:  10.1107/S1600536808036052
PMCID: PMC2959980

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

Abstract

In the crystal structure of title compound, C14H17Cl2NO2, the cyclo­hexyl ring is in a chair conformation and the mol­ecules are connected via N—H(...)O hydrogen bonding into chains.

Related literature

For related structures, see: Li et al. (2008a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2288-scheme1.jpg

Experimental

Crystal data

  • C14H17Cl2NO2
  • M r = 302.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2288-efi1.jpg
  • a = 14.075 (3) Å
  • b = 11.170 (2) Å
  • c = 9.622 (2) Å
  • β = 102.945 (4)°
  • V = 1474.3 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 273 (2) K
  • 0.12 × 0.10 × 0.06 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker 2005 [triangle]) T min = 0.951, T max = 0.978
  • 7597 measured reflections
  • 2610 independent reflections
  • 1803 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.124
  • S = 1.02
  • 2610 reflections
  • 172 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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, New_Global_Publ_Block. DOI: 10.1107/S1600536808036052/nc2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036052/nc2117Isup2.hkl

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

Acknowledgments

This study was supported by the Research Fund for the Doctoral Program of Southwest University, China (grant No. SWUB2008027).

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 by our group.

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 elongate in the direction of the c-axis.

Experimental

A solution of 2,3-dichlorophenol (1.0 mmol), N-cyclohexyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) and CH3CN (20 ml) was refluxed for 3 h. After completion of the reaction (by TLC monitoring), the solution was cooled and the solvent was evaporated under reduced pressure. The residue was poured into water and adjusted to pH 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO4. And then the mixture was filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 90%). Crystals suitable for X-ray diffraction were obtained by slow evaparation of a solution of the solid dissolved in ethyl acetate/hexane at room temperature for 7 days.

Refinement

All H atoms were placed in geometrically calculated positions with C—H = 0.97 Å for CH~2~ H atoms, C—H = 0.93 Å for CH H atoms and 0.86 Å for N-H H atoms and were refined isotropic with Uiso(H) = 1.2 Ueq of the parent atom using a riding model.

Figures

Fig. 1.
The molecular structure of the title compound with labelling and displacement ellipsoids drawn at 50% probability level.

Crystal data

C14H17Cl2NO2F000 = 632
Mr = 302.19Dx = 1.361 Mg m3
Monoclinic, P2(1)/cMo Kα radiation λ = 0.71073 Å
a = 14.075 (3) ÅCell parameters from 1582 reflections
b = 11.170 (2) Åθ = 2.8–22.6º
c = 9.622 (2) ŵ = 0.44 mm1
β = 102.945 (4)ºT = 273 (2) K
V = 1474.3 (6) Å3Neddle, colourless
Z = 40.12 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer2610 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
T = 273(2) Kθmax = 25.1º
phi and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker 2005)h = −10→16
Tmin = 0.951, Tmax = 0.978k = −11→13
7597 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.124  w = 1/[σ2(Fo2) + (0.0364P)2 + 0.4415P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2610 reflectionsΔρmax = 0.20 e Å3
172 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cl10.33190 (6)0.95724 (6)0.17413 (8)0.0681 (3)
Cl20.21347 (6)0.76080 (8)−0.02939 (8)0.0782 (3)
O10.47634 (12)0.86349 (14)0.40289 (16)0.0446 (4)
O20.65219 (13)0.78839 (16)0.35750 (16)0.0498 (5)
N10.70962 (15)0.74309 (18)0.5904 (2)0.0470 (5)
H10.69590.74110.67310.056*
C10.42841 (18)0.7721 (2)0.3221 (3)0.0399 (6)
C20.35620 (18)0.8068 (2)0.2056 (3)0.0442 (6)
C30.3039 (2)0.7195 (3)0.1162 (3)0.0529 (7)
C40.3240 (2)0.5997 (3)0.1445 (3)0.0628 (8)
H40.28910.54130.08520.075*
C50.3949 (2)0.5672 (3)0.2594 (3)0.0622 (8)
H50.40810.48640.27760.075*
C60.4473 (2)0.6517 (2)0.3490 (3)0.0492 (7)
H60.49520.62800.42730.059*
C70.55203 (18)0.8342 (2)0.5232 (2)0.0443 (6)
H7A0.52800.77470.58040.053*
H7B0.56930.90520.58150.053*
C80.64268 (18)0.7858 (2)0.4814 (2)0.0381 (6)
C90.80516 (18)0.6994 (2)0.5773 (2)0.0452 (6)
H90.79970.67460.47810.054*
C100.8334 (2)0.5906 (3)0.6705 (3)0.0676 (9)
H10A0.78490.52830.64210.081*
H10B0.83540.61130.76900.081*
C110.9331 (3)0.5441 (3)0.6577 (4)0.0930 (12)
H11A0.95170.47750.72280.112*
H11B0.92870.51470.56160.112*
C121.0103 (2)0.6389 (4)0.6904 (4)0.0973 (14)
H12A1.07120.60720.67490.117*
H12B1.02030.66200.78990.117*
C130.9811 (3)0.7474 (3)0.5972 (5)0.0927 (12)
H13A0.97830.72620.49860.111*
H13B1.02990.80950.62430.111*
C140.8822 (2)0.7954 (3)0.6107 (4)0.0721 (9)
H14A0.88670.82460.70690.087*
H14B0.86370.86210.54560.087*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0662 (5)0.0580 (5)0.0687 (5)0.0111 (4)−0.0087 (4)0.0010 (4)
Cl20.0465 (5)0.1188 (8)0.0639 (5)−0.0105 (4)0.0008 (4)−0.0180 (4)
O10.0433 (10)0.0408 (10)0.0467 (10)0.0050 (8)0.0037 (8)−0.0051 (8)
O20.0546 (12)0.0650 (12)0.0331 (9)0.0081 (9)0.0172 (8)0.0044 (8)
N10.0395 (12)0.0742 (15)0.0301 (10)0.0093 (11)0.0134 (9)0.0043 (10)
C10.0378 (14)0.0418 (15)0.0447 (14)−0.0011 (11)0.0190 (12)−0.0056 (11)
C20.0385 (14)0.0494 (15)0.0471 (14)−0.0006 (12)0.0143 (12)−0.0050 (12)
C30.0413 (15)0.072 (2)0.0493 (16)−0.0100 (14)0.0171 (13)−0.0125 (13)
C40.0540 (19)0.063 (2)0.077 (2)−0.0235 (16)0.0271 (17)−0.0257 (16)
C50.065 (2)0.0457 (17)0.083 (2)−0.0081 (15)0.0309 (18)−0.0068 (15)
C60.0488 (16)0.0464 (16)0.0572 (16)−0.0010 (13)0.0221 (13)0.0010 (13)
C70.0431 (15)0.0535 (15)0.0365 (13)0.0059 (12)0.0091 (11)−0.0027 (11)
C80.0415 (14)0.0389 (13)0.0355 (13)−0.0004 (11)0.0122 (11)−0.0018 (10)
C90.0357 (14)0.0663 (17)0.0349 (13)0.0041 (13)0.0108 (11)−0.0024 (12)
C100.0514 (19)0.082 (2)0.074 (2)0.0149 (16)0.0221 (16)0.0184 (17)
C110.067 (2)0.108 (3)0.109 (3)0.038 (2)0.030 (2)0.031 (2)
C120.044 (2)0.172 (4)0.071 (2)0.020 (2)0.0023 (17)−0.026 (3)
C130.048 (2)0.114 (3)0.122 (3)−0.020 (2)0.033 (2)−0.031 (3)
C140.055 (2)0.073 (2)0.093 (2)−0.0116 (17)0.0266 (18)−0.0106 (17)

Geometric parameters (Å, °)

Cl1—C21.728 (3)C7—H7B0.9700
Cl2—C31.731 (3)C9—C141.508 (4)
O1—C11.366 (3)C9—C101.510 (4)
O1—C71.425 (3)C9—H90.9800
O2—C81.229 (3)C10—C111.527 (4)
N1—C81.332 (3)C10—H10A0.9700
N1—C91.462 (3)C10—H10B0.9700
N1—H10.8600C11—C121.499 (5)
C1—C61.385 (3)C11—H11A0.9700
C1—C21.389 (4)C11—H11B0.9700
C2—C31.396 (4)C12—C131.509 (5)
C3—C41.382 (4)C12—H12A0.9700
C4—C51.362 (4)C12—H12B0.9700
C4—H40.9300C13—C141.525 (5)
C5—C61.376 (4)C13—H13A0.9700
C5—H50.9300C13—H13B0.9700
C6—H60.9300C14—H14A0.9700
C7—C81.521 (3)C14—H14B0.9700
C7—H7A0.9700
C1—O1—C7118.35 (19)N1—C9—H9107.7
C8—N1—C9123.64 (19)C14—C9—H9107.7
C8—N1—H1118.2C10—C9—H9107.7
C9—N1—H1118.2C9—C10—C11110.5 (2)
O1—C1—C6124.8 (2)C9—C10—H10A109.5
O1—C1—C2115.5 (2)C11—C10—H10A109.6
C6—C1—C2119.8 (2)C9—C10—H10B109.5
C1—C2—C3119.5 (2)C11—C10—H10B109.5
C1—C2—Cl1119.52 (19)H10A—C10—H10B108.1
C3—C2—Cl1121.0 (2)C12—C11—C10112.2 (3)
C4—C3—C2119.9 (3)C12—C11—H11A109.2
C4—C3—Cl2119.9 (2)C10—C11—H11A109.2
C2—C3—Cl2120.2 (2)C12—C11—H11B109.2
C5—C4—C3119.9 (3)C10—C11—H11B109.2
C5—C4—H4120.1H11A—C11—H11B107.9
C3—C4—H4120.1C11—C12—C13110.8 (3)
C4—C5—C6121.2 (3)C11—C12—H12A109.5
C4—C5—H5119.4C13—C12—H12A109.5
C6—C5—H5119.4C11—C12—H12B109.5
C5—C6—C1119.8 (3)C13—C12—H12B109.5
C5—C6—H6120.1H12A—C12—H12B108.1
C1—C6—H6120.1C12—C13—C14111.3 (3)
O1—C7—C8112.66 (18)C12—C13—H13A109.4
O1—C7—H7A109.1C14—C13—H13A109.4
C8—C7—H7A109.1C12—C13—H13B109.4
O1—C7—H7B109.1C14—C13—H13B109.4
C8—C7—H7B109.1H13A—C13—H13B108.0
H7A—C7—H7B107.8C9—C14—C13111.0 (3)
O2—C8—N1124.1 (2)C9—C14—H14A109.4
O2—C8—C7121.9 (2)C13—C14—H14A109.4
N1—C8—C7113.97 (19)C9—C14—H14B109.4
N1—C9—C14112.0 (2)C13—C14—H14B109.4
N1—C9—C10110.0 (2)H14A—C14—H14B108.0
C14—C9—C10111.4 (2)
C7—O1—C1—C60.6 (3)C1—O1—C7—C871.2 (3)
C7—O1—C1—C2−179.4 (2)C9—N1—C8—O23.3 (4)
O1—C1—C2—C3179.5 (2)C9—N1—C8—C7−175.8 (2)
C6—C1—C2—C3−0.5 (4)O1—C7—C8—O29.2 (3)
O1—C1—C2—Cl1−1.0 (3)O1—C7—C8—N1−171.7 (2)
C6—C1—C2—Cl1179.11 (18)C8—N1—C9—C1493.9 (3)
C1—C2—C3—C40.3 (4)C8—N1—C9—C10−141.5 (3)
Cl1—C2—C3—C4−179.3 (2)N1—C9—C10—C11180.0 (3)
C1—C2—C3—Cl2179.88 (19)C14—C9—C10—C11−55.1 (4)
Cl1—C2—C3—Cl20.3 (3)C9—C10—C11—C1255.2 (4)
C2—C3—C4—C5−0.1 (4)C10—C11—C12—C13−55.4 (4)
Cl2—C3—C4—C5−179.8 (2)C11—C12—C13—C1455.4 (4)
C3—C4—C5—C60.2 (4)N1—C9—C14—C13179.7 (3)
C4—C5—C6—C1−0.4 (4)C10—C9—C14—C1355.9 (4)
O1—C1—C6—C5−179.4 (2)C12—C13—C14—C9−55.8 (4)
C2—C1—C6—C50.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.883 (3)171

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: NC2117).

References

  • Bruker (2005). SADABS,SAINT and APEX2 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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