2-(2-Chloro-phen-yl)-N-cyclo-hexyl-2-oxoacetamide.

In the title compound, C14H16ClNO2, the cyclo-hexyl ring has a chair conformation. The dihedral angle between the benzene ring and the mean plane of the four planar C atoms of the cyclo-hexyl ring is 45.2 (3)°. The two carbonyl groups are trans to one another, with an O=C-C=O torsion angle of -137.1 (3)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds forming chains propagating along [001]. A region of disordered electron density, situated near the unit-cell corners, was treated using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155]. It gave a solvent-accessible void of ca 400 Å(3) for only 21 electrons. It is probably due to traces of the solvent of crystallization and was not taken into account during structure refinement.

Related literature

For the crystal structures of substituted phenyl­glyoxamides, see: Boryczka et al. (1998 ▶); Dai & Wu (2011 ▶); Jia & Wu (2012 ▶).

Experimental

Crystal data

C14H16ClNO2

M = 265.73

Hexagonal,

a = 17.075 (3) Å

c = 9.4536 (13) Å

V = 2387.0 (7) Å3

Z = 6

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.48 × 0.26 × 0.20 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.896, T max = 0.955

15794 measured reflections

3101 independent reflections

2344 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.149

S = 1.01

3101 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1422 Friedel pairs

Flack parameter: −0.05 (3)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005904/su2558sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005904/su2558Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005904/su2558Isup3.cml

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

C14H16ClNO2	Dx = 1.109 Mg m−3
Mr = 265.73	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 2933 reflections
Hall symbol: P 61	θ = 3.2–29.4°
a = 17.075 (3) Å	µ = 0.24 mm−1
c = 9.4536 (13) Å	T = 293 K
V = 2387.0 (7) Å3	Needle, colourless
Z = 6	0.48 × 0.26 × 0.20 mm
F(000) = 840

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3101 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 10.3592 pixels mm-1	θmax = 26.1°, θmin = 3.2°
ω scans	h = −16→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→19
Tmin = 0.896, Tmax = 0.955	l = −11→11
15794 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3101 reflections	Δρmax = 0.19 e Å−3
163 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 1422 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Cl1	0.69837 (7)	0.67833 (8)	0.10734 (15)	0.1067 (4)
O1	0.43847 (15)	0.60191 (15)	0.0815 (2)	0.0736 (8)
O2	0.52877 (16)	0.55421 (14)	0.3612 (2)	0.0672 (8)
N1	0.48258 (16)	0.46907 (14)	0.1620 (2)	0.0538 (8)
C1	0.6611 (2)	0.7465 (2)	0.1859 (4)	0.0703 (11)
C2	0.7225 (3)	0.8325 (3)	0.2271 (6)	0.1002 (16)
C3	0.6930 (4)	0.8869 (3)	0.2830 (6)	0.1072 (18)
C4	0.6038 (3)	0.8566 (2)	0.2982 (5)	0.0948 (16)
C5	0.5408 (2)	0.7700 (2)	0.2549 (4)	0.0705 (11)
C6	0.5693 (2)	0.71274 (18)	0.2003 (3)	0.0539 (9)
C7	0.5009 (2)	0.61862 (19)	0.1599 (3)	0.0508 (9)
C8	0.50637 (18)	0.54310 (18)	0.2353 (3)	0.0481 (8)
C9	0.4826 (2)	0.38896 (18)	0.2192 (3)	0.0541 (9)
C10	0.5628 (2)	0.3843 (2)	0.1677 (4)	0.0786 (14)
C11	0.5633 (3)	0.3014 (3)	0.2262 (5)	0.0919 (17)
C12	0.4763 (3)	0.2157 (2)	0.1922 (4)	0.0913 (16)
C13	0.3966 (3)	0.2207 (3)	0.2424 (7)	0.112 (2)
C14	0.3952 (2)	0.3033 (2)	0.1816 (6)	0.0897 (14)
H1	0.46610	0.46740	0.07550	0.0650*
H2	0.78410	0.85380	0.21720	0.1210*
H3	0.73480	0.94550	0.31080	0.1280*
H4	0.58450	0.89400	0.33780	0.1140*
H5	0.47930	0.75020	0.26230	0.0840*
H9	0.48640	0.39430	0.32250	0.0650*
H10A	0.61760	0.43850	0.19660	0.0940*
H10B	0.56180	0.38200	0.06510	0.0940*
H11A	0.61380	0.29800	0.18590	0.1100*
H11B	0.57150	0.30720	0.32790	0.1100*
H12A	0.47190	0.20590	0.09070	0.1100*
H12B	0.47680	0.16480	0.23670	0.1100*
H13A	0.39770	0.22400	0.34490	0.1350*
H13B	0.34180	0.16620	0.21460	0.1350*
H14A	0.38860	0.29780	0.07960	0.1080*
H14B	0.34410	0.30640	0.21980	0.1080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0872 (6)	0.1113 (7)	0.1394 (9)	0.0629 (6)	0.0331 (6)	−0.0112 (7)
O1	0.0885 (15)	0.0802 (14)	0.0662 (14)	0.0527 (12)	−0.0205 (12)	−0.0011 (11)
O2	0.1098 (16)	0.0723 (12)	0.0345 (11)	0.0567 (12)	−0.0018 (10)	−0.0010 (9)
N1	0.0815 (16)	0.0613 (13)	0.0317 (11)	0.0455 (13)	−0.0049 (10)	0.0001 (10)
C1	0.078 (2)	0.0719 (19)	0.0720 (19)	0.0458 (17)	0.0126 (16)	0.0028 (16)
C2	0.071 (2)	0.080 (2)	0.134 (4)	0.026 (2)	0.012 (2)	0.000 (2)
C3	0.118 (3)	0.059 (2)	0.131 (4)	0.034 (2)	0.011 (3)	−0.005 (2)
C4	0.125 (3)	0.065 (2)	0.107 (3)	0.057 (2)	0.017 (3)	−0.002 (2)
C5	0.085 (2)	0.0680 (19)	0.075 (2)	0.0507 (17)	0.0183 (18)	0.0131 (17)
C6	0.0733 (18)	0.0610 (16)	0.0410 (15)	0.0437 (15)	0.0088 (12)	0.0106 (12)
C7	0.0668 (16)	0.0663 (16)	0.0346 (13)	0.0448 (14)	0.0051 (12)	0.0015 (11)
C8	0.0634 (15)	0.0629 (15)	0.0294 (14)	0.0402 (13)	0.0065 (11)	0.0036 (11)
C9	0.0799 (18)	0.0569 (15)	0.0362 (13)	0.0422 (14)	0.0037 (12)	0.0053 (11)
C10	0.073 (2)	0.073 (2)	0.101 (3)	0.0449 (17)	0.0086 (18)	0.0180 (19)
C11	0.100 (3)	0.095 (3)	0.109 (3)	0.070 (2)	0.008 (2)	0.019 (2)
C12	0.145 (4)	0.070 (2)	0.078 (2)	0.068 (2)	−0.015 (2)	−0.0055 (19)
C13	0.096 (3)	0.064 (2)	0.161 (5)	0.028 (2)	0.001 (3)	0.040 (3)
C14	0.072 (2)	0.068 (2)	0.128 (3)	0.0342 (18)	0.003 (2)	0.026 (2)

Cl1—C1	1.747 (4)	C12—C13	1.484 (8)
O1—C7	1.210 (4)	C13—C14	1.534 (6)
O2—C8	1.235 (3)	C2—H2	0.9300
N1—C8	1.315 (3)	C3—H3	0.9300
N1—C9	1.471 (4)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
C1—C6	1.380 (5)	C9—H9	0.9800
C1—C2	1.367 (6)	C10—H10A	0.9700
C2—C3	1.365 (8)	C10—H10B	0.9700
C3—C4	1.349 (9)	C11—H11A	0.9700
C4—C5	1.386 (5)	C11—H11B	0.9700
C5—C6	1.391 (5)	C12—H12A	0.9700
C6—C7	1.489 (4)	C12—H12B	0.9700
C7—C8	1.517 (4)	C13—H13A	0.9700
C9—C14	1.520 (5)	C13—H13B	0.9700
C9—C10	1.493 (5)	C14—H14A	0.9700
C10—C11	1.524 (6)	C14—H14B	0.9700
C11—C12	1.509 (6)
C8—N1—C9	123.8 (2)	C5—C4—H4	120.00
C9—N1—H1	118.00	C4—C5—H5	120.00
C8—N1—H1	118.00	C6—C5—H5	120.00
Cl1—C1—C6	118.7 (2)	N1—C9—H9	108.00
Cl1—C1—C2	119.9 (3)	C10—C9—H9	108.00
C2—C1—C6	121.4 (4)	C14—C9—H9	108.00
C1—C2—C3	119.7 (5)	C9—C10—H10A	109.00
C2—C3—C4	120.7 (4)	C9—C10—H10B	109.00
C3—C4—C5	120.2 (4)	C11—C10—H10A	109.00
C4—C5—C6	120.1 (4)	C11—C10—H10B	109.00
C1—C6—C7	122.7 (3)	H10A—C10—H10B	108.00
C1—C6—C5	117.8 (3)	C10—C11—H11A	109.00
C5—C6—C7	119.5 (3)	C10—C11—H11B	109.00
C6—C7—C8	116.7 (3)	C12—C11—H11A	109.00
O1—C7—C8	120.6 (3)	C12—C11—H11B	109.00
O1—C7—C6	122.4 (3)	H11A—C11—H11B	108.00
O2—C8—N1	125.3 (3)	C11—C12—H12A	109.00
O2—C8—C7	117.9 (2)	C11—C12—H12B	109.00
N1—C8—C7	116.7 (2)	C13—C12—H12A	109.00
N1—C9—C10	110.9 (2)	C13—C12—H12B	109.00
C10—C9—C14	111.0 (3)	H12A—C12—H12B	108.00
N1—C9—C14	110.6 (3)	C12—C13—H13A	109.00
C9—C10—C11	111.3 (3)	C12—C13—H13B	109.00
C10—C11—C12	111.3 (4)	C14—C13—H13A	109.00
C11—C12—C13	111.3 (4)	C14—C13—H13B	109.00
C12—C13—C14	111.7 (4)	H13A—C13—H13B	108.00
C9—C14—C13	109.8 (4)	C9—C14—H14A	110.00
C1—C2—H2	120.00	C9—C14—H14B	110.00
C3—C2—H2	120.00	C13—C14—H14A	110.00
C2—C3—H3	120.00	C13—C14—H14B	110.00
C4—C3—H3	120.00	H14A—C14—H14B	108.00
C3—C4—H4	120.00
C8—N1—C9—C14	133.5 (4)	C1—C6—C7—C8	59.6 (4)
C9—N1—C8—O2	−2.4 (5)	C5—C6—C7—O1	52.5 (4)
C9—N1—C8—C7	−179.1 (3)	C5—C6—C7—C8	−120.4 (3)
C8—N1—C9—C10	−103.0 (3)	O1—C7—C8—N1	39.9 (5)
C6—C1—C2—C3	−0.4 (7)	C6—C7—C8—O2	36.0 (4)
Cl1—C1—C6—C5	−176.0 (3)	C6—C7—C8—N1	−147.0 (3)
Cl1—C1—C6—C7	3.9 (4)	O1—C7—C8—O2	−137.1 (3)
Cl1—C1—C2—C3	177.3 (4)	N1—C9—C10—C11	−179.9 (3)
C2—C1—C6—C5	1.7 (6)	C14—C9—C10—C11	−56.5 (4)
C2—C1—C6—C7	−178.4 (4)	N1—C9—C14—C13	−179.9 (4)
C1—C2—C3—C4	0.1 (8)	C10—C9—C14—C13	56.6 (5)
C2—C3—C4—C5	−1.1 (8)	C9—C10—C11—C12	55.2 (4)
C3—C4—C5—C6	2.4 (6)	C10—C11—C12—C13	−54.8 (5)
C4—C5—C6—C7	177.4 (3)	C11—C12—C13—C14	55.9 (6)
C4—C5—C6—C1	−2.6 (5)	C12—C13—C14—C9	−56.5 (6)
C1—C6—C7—O1	−127.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.07	2.864 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.07	2.864 (3)	153

Symmetry code: (i) .