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

Zuo, H.; Li, Z.-B.; Dong, W.-L.; Wang, L.-Y.

doi:10.1107/S1600536808036052

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2288

doi:10.1107/S1600536808036052

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

Hua Zuo,^a ^* Zhu-Bo Li,^a Wen-Liang Dong ^b and Li-Ying Wang ^a

^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 ,b ).

Experimental

Crystal data

C₁₄H₁₇Cl₂NO₂
M_r = 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 ) 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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.02
2610 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808036052/nc2117sup1.cif

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

checkCIF report

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.

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

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

(I) top

Crystal data top

C₁₄H₁₇Cl₂NO₂	F(000) = 632
M_r = 302.19	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.075 (3) Å	Cell parameters from 1582 reflections
b = 11.170 (2) Å	θ = 2.8–22.6°
c = 9.622 (2) Å	µ = 0.44 mm⁻¹
β = 102.945 (4)°	T = 273 K
V = 1474.3 (6) Å³	Neddle, colourless
Z = 4	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2610 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
phi and ω scans	θ_max = 25.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker 2005)	h = −10→16
T_min = 0.951, T_max = 0.978	k = −11→13
7597 measured reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0364P)² + 0.4415P] where P = (F_o² + 2F_c²)/3
2610 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₇Cl₂NO₂	V = 1474.3 (6) Å³
M_r = 302.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.075 (3) Å	µ = 0.44 mm⁻¹
b = 11.170 (2) Å	T = 273 K
c = 9.622 (2) Å	0.12 × 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)
T_min = 0.951, T_max = 0.978	R_int = 0.036
7597 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2610 reflections	Δρ_min = −0.23 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.33190 (6)	0.95724 (6)	0.17413 (8)	0.0681 (3)
Cl2	0.21347 (6)	0.76080 (8)	−0.02939 (8)	0.0782 (3)
O1	0.47634 (12)	0.86349 (14)	0.40289 (16)	0.0446 (4)
O2	0.65219 (13)	0.78839 (16)	0.35750 (16)	0.0498 (5)
N1	0.70962 (15)	0.74309 (18)	0.5904 (2)	0.0470 (5)
H1	0.6959	0.7411	0.6731	0.056*
C1	0.42841 (18)	0.7721 (2)	0.3221 (3)	0.0399 (6)
C2	0.35620 (18)	0.8068 (2)	0.2056 (3)	0.0442 (6)
C3	0.3039 (2)	0.7195 (3)	0.1162 (3)	0.0529 (7)
C4	0.3240 (2)	0.5997 (3)	0.1445 (3)	0.0628 (8)
H4	0.2891	0.5413	0.0852	0.075*
C5	0.3949 (2)	0.5672 (3)	0.2594 (3)	0.0622 (8)
H5	0.4081	0.4864	0.2776	0.075*
C6	0.4473 (2)	0.6517 (2)	0.3490 (3)	0.0492 (7)
H6	0.4952	0.6280	0.4273	0.059*
C7	0.55203 (18)	0.8342 (2)	0.5232 (2)	0.0443 (6)
H7A	0.5280	0.7747	0.5804	0.053*
H7B	0.5693	0.9052	0.5815	0.053*
C8	0.64268 (18)	0.7858 (2)	0.4814 (2)	0.0381 (6)
C9	0.80516 (18)	0.6994 (2)	0.5773 (2)	0.0452 (6)
H9	0.7997	0.6746	0.4781	0.054*
C10	0.8334 (2)	0.5906 (3)	0.6705 (3)	0.0676 (9)
H10A	0.7849	0.5283	0.6421	0.081*
H10B	0.8354	0.6113	0.7690	0.081*
C11	0.9331 (3)	0.5441 (3)	0.6577 (4)	0.0930 (12)
H11A	0.9517	0.4775	0.7228	0.112*
H11B	0.9287	0.5147	0.5616	0.112*
C12	1.0103 (2)	0.6389 (4)	0.6904 (4)	0.0973 (14)
H12A	1.0712	0.6072	0.6749	0.117*
H12B	1.0203	0.6620	0.7899	0.117*
C13	0.9811 (3)	0.7474 (3)	0.5972 (5)	0.0927 (12)
H13A	0.9783	0.7262	0.4986	0.111*
H13B	1.0299	0.8095	0.6243	0.111*
C14	0.8822 (2)	0.7954 (3)	0.6107 (4)	0.0721 (9)
H14A	0.8867	0.8246	0.7069	0.087*
H14B	0.8637	0.8621	0.5456	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0662 (5)	0.0580 (5)	0.0687 (5)	0.0111 (4)	−0.0087 (4)	0.0010 (4)
Cl2	0.0465 (5)	0.1188 (8)	0.0639 (5)	−0.0105 (4)	0.0008 (4)	−0.0180 (4)
O1	0.0433 (10)	0.0408 (10)	0.0467 (10)	0.0050 (8)	0.0037 (8)	−0.0051 (8)
O2	0.0546 (12)	0.0650 (12)	0.0331 (9)	0.0081 (9)	0.0172 (8)	0.0044 (8)
N1	0.0395 (12)	0.0742 (15)	0.0301 (10)	0.0093 (11)	0.0134 (9)	0.0043 (10)
C1	0.0378 (14)	0.0418 (15)	0.0447 (14)	−0.0011 (11)	0.0190 (12)	−0.0056 (11)
C2	0.0385 (14)	0.0494 (15)	0.0471 (14)	−0.0006 (12)	0.0143 (12)	−0.0050 (12)
C3	0.0413 (15)	0.072 (2)	0.0493 (16)	−0.0100 (14)	0.0171 (13)	−0.0125 (13)
C4	0.0540 (19)	0.063 (2)	0.077 (2)	−0.0235 (16)	0.0271 (17)	−0.0257 (16)
C5	0.065 (2)	0.0457 (17)	0.083 (2)	−0.0081 (15)	0.0309 (18)	−0.0068 (15)
C6	0.0488 (16)	0.0464 (16)	0.0572 (16)	−0.0010 (13)	0.0221 (13)	0.0010 (13)
C7	0.0431 (15)	0.0535 (15)	0.0365 (13)	0.0059 (12)	0.0091 (11)	−0.0027 (11)
C8	0.0415 (14)	0.0389 (13)	0.0355 (13)	−0.0004 (11)	0.0122 (11)	−0.0018 (10)
C9	0.0357 (14)	0.0663 (17)	0.0349 (13)	0.0041 (13)	0.0108 (11)	−0.0024 (12)
C10	0.0514 (19)	0.082 (2)	0.074 (2)	0.0149 (16)	0.0221 (16)	0.0184 (17)
C11	0.067 (2)	0.108 (3)	0.109 (3)	0.038 (2)	0.030 (2)	0.031 (2)
C12	0.044 (2)	0.172 (4)	0.071 (2)	0.020 (2)	0.0023 (17)	−0.026 (3)
C13	0.048 (2)	0.114 (3)	0.122 (3)	−0.020 (2)	0.033 (2)	−0.031 (3)
C14	0.055 (2)	0.073 (2)	0.093 (2)	−0.0116 (17)	0.0266 (18)	−0.0106 (17)

Geometric parameters (Å, º) top

Cl1—C2	1.728 (3)	C7—H7B	0.9700
Cl2—C3	1.731 (3)	C9—C14	1.508 (4)
O1—C1	1.366 (3)	C9—C10	1.510 (4)
O1—C7	1.425 (3)	C9—H9	0.9800
O2—C8	1.229 (3)	C10—C11	1.527 (4)
N1—C8	1.332 (3)	C10—H10A	0.9700
N1—C9	1.462 (3)	C10—H10B	0.9700
N1—H1	0.8600	C11—C12	1.499 (5)
C1—C6	1.385 (3)	C11—H11A	0.9700
C1—C2	1.389 (4)	C11—H11B	0.9700
C2—C3	1.396 (4)	C12—C13	1.509 (5)
C3—C4	1.382 (4)	C12—H12A	0.9700
C4—C5	1.362 (4)	C12—H12B	0.9700
C4—H4	0.9300	C13—C14	1.525 (5)
C5—C6	1.376 (4)	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.521 (3)	C14—H14B	0.9700
C7—H7A	0.9700

C1—O1—C7	118.35 (19)	N1—C9—H9	107.7
C8—N1—C9	123.64 (19)	C14—C9—H9	107.7
C8—N1—H1	118.2	C10—C9—H9	107.7
C9—N1—H1	118.2	C9—C10—C11	110.5 (2)
O1—C1—C6	124.8 (2)	C9—C10—H10A	109.5
O1—C1—C2	115.5 (2)	C11—C10—H10A	109.6
C6—C1—C2	119.8 (2)	C9—C10—H10B	109.5
C1—C2—C3	119.5 (2)	C11—C10—H10B	109.5
C1—C2—Cl1	119.52 (19)	H10A—C10—H10B	108.1
C3—C2—Cl1	121.0 (2)	C12—C11—C10	112.2 (3)
C4—C3—C2	119.9 (3)	C12—C11—H11A	109.2
C4—C3—Cl2	119.9 (2)	C10—C11—H11A	109.2
C2—C3—Cl2	120.2 (2)	C12—C11—H11B	109.2
C5—C4—C3	119.9 (3)	C10—C11—H11B	109.2
C5—C4—H4	120.1	H11A—C11—H11B	107.9
C3—C4—H4	120.1	C11—C12—C13	110.8 (3)
C4—C5—C6	121.2 (3)	C11—C12—H12A	109.5
C4—C5—H5	119.4	C13—C12—H12A	109.5
C6—C5—H5	119.4	C11—C12—H12B	109.5
C5—C6—C1	119.8 (3)	C13—C12—H12B	109.5
C5—C6—H6	120.1	H12A—C12—H12B	108.1
C1—C6—H6	120.1	C12—C13—C14	111.3 (3)
O1—C7—C8	112.66 (18)	C12—C13—H13A	109.4
O1—C7—H7A	109.1	C14—C13—H13A	109.4
C8—C7—H7A	109.1	C12—C13—H13B	109.4
O1—C7—H7B	109.1	C14—C13—H13B	109.4
C8—C7—H7B	109.1	H13A—C13—H13B	108.0
H7A—C7—H7B	107.8	C9—C14—C13	111.0 (3)
O2—C8—N1	124.1 (2)	C9—C14—H14A	109.4
O2—C8—C7	121.9 (2)	C13—C14—H14A	109.4
N1—C8—C7	113.97 (19)	C9—C14—H14B	109.4
N1—C9—C14	112.0 (2)	C13—C14—H14B	109.4
N1—C9—C10	110.0 (2)	H14A—C14—H14B	108.0
C14—C9—C10	111.4 (2)

C7—O1—C1—C6	0.6 (3)	C1—O1—C7—C8	71.2 (3)
C7—O1—C1—C2	−179.4 (2)	C9—N1—C8—O2	3.3 (4)
O1—C1—C2—C3	179.5 (2)	C9—N1—C8—C7	−175.8 (2)
C6—C1—C2—C3	−0.5 (4)	O1—C7—C8—O2	9.2 (3)
O1—C1—C2—Cl1	−1.0 (3)	O1—C7—C8—N1	−171.7 (2)
C6—C1—C2—Cl1	179.11 (18)	C8—N1—C9—C14	93.9 (3)
C1—C2—C3—C4	0.3 (4)	C8—N1—C9—C10	−141.5 (3)
Cl1—C2—C3—C4	−179.3 (2)	N1—C9—C10—C11	180.0 (3)
C1—C2—C3—Cl2	179.88 (19)	C14—C9—C10—C11	−55.1 (4)
Cl1—C2—C3—Cl2	0.3 (3)	C9—C10—C11—C12	55.2 (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—C14	55.4 (4)
C3—C4—C5—C6	0.2 (4)	N1—C9—C14—C13	179.7 (3)
C4—C5—C6—C1	−0.4 (4)	C10—C9—C14—C13	55.9 (4)
O1—C1—C6—C5	−179.4 (2)	C12—C13—C14—C9	−55.8 (4)
C2—C1—C6—C5	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.03	2.883 (3)	171

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇Cl₂NO₂
M_r	302.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.075 (3), 11.170 (2), 9.622 (2)
β (°)	102.945 (4)
V (Å³)	1474.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2005)
T_min, T_max	0.951, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	7597, 2610, 1803
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.02
No. of reflections	2610
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.03	2.883 (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

Bruker (2005). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, 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
Li, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar