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ISSN: 2056-9890

N-Cyclo­hexyl-2-(2,3-di­chloro­phen­­oxy)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: zuohuabest@yahoo.com

(Received 19 September 2008; accepted 3 November 2008; online 8 November 2008)

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[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
  • C14H17Cl2NO2

  • Mr = 302.19

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.978

  • 7597 measured reflections

  • 2610 independent reflections

  • 1803 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.86 2.03 2.883 (3) 171
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (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 with labelling and displacement ellipsoids drawn at 50% probability level.
(I) top
Crystal data top
C14H17Cl2NO2F(000) = 632
Mr = 302.19Dx = 1.361 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.075 (3) ÅCell parameters from 1582 reflections
b = 11.170 (2) Åθ = 2.8–22.6°
c = 9.622 (2) ŵ = 0.44 mm1
β = 102.945 (4)°T = 273 K
V = 1474.3 (6) Å3Neddle, colourless
Z = 40.12 × 0.10 × 0.06 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2610 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
phi and ω scansθmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker 2005)
h = 1016
Tmin = 0.951, Tmax = 0.978k = 1113
7597 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.4415P]
where P = (Fo2 + 2Fc2)/3
2610 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C14H17Cl2NO2V = 1474.3 (6) Å3
Mr = 302.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.075 (3) ŵ = 0.44 mm1
b = 11.170 (2) ÅT = 273 K
c = 9.622 (2) Å0.12 × 0.10 × 0.06 mm
β = 102.945 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2610 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2005)
1803 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.978Rint = 0.036
7597 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
2610 reflectionsΔρmin = 0.23 e Å3
172 parameters
Special details top

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) top
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) top
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, º) top
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—C2179.4 (2)C9—N1—C8—O23.3 (4)
O1—C1—C2—C3179.5 (2)C9—N1—C8—C7175.8 (2)
C6—C1—C2—C30.5 (4)O1—C7—C8—O29.2 (3)
O1—C1—C2—Cl11.0 (3)O1—C7—C8—N1171.7 (2)
C6—C1—C2—Cl1179.11 (18)C8—N1—C9—C1493.9 (3)
C1—C2—C3—C40.3 (4)C8—N1—C9—C10141.5 (3)
Cl1—C2—C3—C4179.3 (2)N1—C9—C10—C11180.0 (3)
C1—C2—C3—Cl2179.88 (19)C14—C9—C10—C1155.1 (4)
Cl1—C2—C3—Cl20.3 (3)C9—C10—C11—C1255.2 (4)
C2—C3—C4—C50.1 (4)C10—C11—C12—C1355.4 (4)
Cl2—C3—C4—C5179.8 (2)C11—C12—C13—C1455.4 (4)
C3—C4—C5—C60.2 (4)N1—C9—C14—C13179.7 (3)
C4—C5—C6—C10.4 (4)C10—C9—C14—C1355.9 (4)
O1—C1—C6—C5179.4 (2)C12—C13—C14—C955.8 (4)
C2—C1—C6—C50.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.883 (3)171
Symmetry code: (i) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H17Cl2NO2
Mr302.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)14.075 (3), 11.170 (2), 9.622 (2)
β (°) 102.945 (4)
V3)1474.3 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.12 × 0.10 × 0.06
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2005)
Tmin, Tmax0.951, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
7597, 2610, 1803
Rint0.036
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.124, 1.02
No. of reflections2610
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.23

Computer programs: APEX2 (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
N1—H1···O2i0.862.032.883 (3)171
Symmetry code: (i) x, y+3/2, z+1/2.
 

Acknowledgements

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

References

First citationBruker (2005). SADABS, SAINT and APEX2. 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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