4-Chloro-N-cyclo­hexyl­benzamide

Saeed, A.; Khera, R.A.; Latif, M.; Parvez, M.

doi:10.1107/S1600536809021217

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1539

doi:10.1107/S1600536809021217

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4-Chloro-N-cyclohexylbenzamide

Aamer Saeed,^a Rasheed Ahmad Khera,^a Muhammad Latif ^b and Masood Parvez ^c ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bDepartment of Chemistry, Hamdard Institute of Pharmaceutical Sciences, Hamdard University–Islamabad Campus, Islamabad, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 29 May 2009; accepted 4 June 2009; online 10 June 2009)

In the title compound, C₁₃H₁₆ClNO, the cyclohexyl ring adopts a chair conformation, with puckering parameters Q = 0.576 (3) Å, θ = 0.1 (3) and φ = 8 (15)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link molecules into one-dimensional chains propagating in [010].

Related literature

For applications of N-substituted benzamides, see: Beccalli et al. (2005 ); Calderone et al. (2006 ); Vega-Noverola et al. (1989 ); Zhichkin et al. (2007 ); Lindgren et al. (2001 ); Olsson et al. (2002 ). For related crystal structures, see: Jones & Kuś (2004 ); Saeed et al. (2008 ). For puckering parameters, see: Cremer & Pople (1975 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₃H₁₆ClNO
M_r = 237.72
Monoclinic, P 2₁ /c
a = 14.755 (14) Å
b = 5.043 (7) Å
c = 16.818 (16) Å
β = 96.13 (6)°
V = 1244 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.967, T_max = 0.983
3651 measured reflections
2388 independent reflections
1497 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.151
S = 1.06
2388 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.06	2.901 (5)	160
Symmetry code: (i) x, y-1, z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021217/lh2834sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021217/lh2834Isup2.hkl

checkCIF report

Comment top

N-Substituted benzamides, e.g., declopramideare, are well known anticancer compounds and the mechanism of benzamide-induced apoptosis has been studied, (Olsson et al., 2002). N-substituted benzamides inhibit the activity of nuclear factor-B and nuclear factor of activated T cells (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989), while heterocyclic benzanilide are potassium channel activators (Calderone et al., 2006). N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005). As part of our work on the structure of benzanilides and related compounds, in this paper, we report the crystal structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The molecular dimensions in (I) are normal (CSD version 5.30; Allen, 2002). The six-membered ring adopts a chair conformation with puckering parameters: Q = 0.576 (3) Å, θ = 0.1 (3)° and ϕ = 8(15)° (Cremer & Pople, 1975). The structure is stabilized by hydrogen bonding (N1–H1···O1) forming chains of molecules along the b-axis (details are in Table 1). The crystal structures of closely related compounds have been reported (Saeed et al., 2008; Jones & Kuś, 2004).

Related literature top

For applications of N-substituted benzamides, see: Beccalli et al. (2005); Calderone et al. (2006); Vega-Noverola et al. (1989); Zhichkin et al. (2007); Lindgren et al. (2001); Olsson et al. (2002). For related crystal structures, see: Jones & Kuś (2004); Saeed et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For a description of the Cambridge Structural Database, see: Allen (2002); .

Experimental top

4-Chlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with cyclohexylamine (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (87%) as colorless needles: Anal. calcd. for C₁₃H₁₆ClNO,: C, 65.68; H, 6.78; N, 5.89%; found: C, 65.61; H, 6.80; N, 5.91%.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 30% probability level.

4-Chloro-N-cyclohexylbenzamide top

Crystal data top

C₁₃H₁₆ClNO	F(000) = 504
M_r = 237.72	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3651 reflections
a = 14.755 (14) Å	θ = 3.9–26.0°
b = 5.043 (7) Å	µ = 0.29 mm⁻¹
c = 16.818 (16) Å	T = 173 K
β = 96.13 (6)°	Needle, colorless
V = 1244 (2) Å³	0.12 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2388 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 26.0°, θ_min = 3.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −18→17
T_min = 0.967, T_max = 0.983	k = −6→4
3651 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0665P)² + 0.3764P] where P = (F_o² + 2F_c²)/3
2388 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₆ClNO	V = 1244 (2) Å³
M_r = 237.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.755 (14) Å	µ = 0.29 mm⁻¹
b = 5.043 (7) Å	T = 173 K
c = 16.818 (16) Å	0.12 × 0.08 × 0.06 mm
β = 96.13 (6)°

Data collection top

Bruker APEXII CCD diffractometer	2388 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	1497 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.983	R_int = 0.034
3651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	Δρ_max = 0.16 e Å⁻³
2388 reflections	Δρ_min = −0.21 e Å⁻³
145 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	0.77571 (5)	0.29595 (19)	0.35603 (5)	0.0739 (3)
O1	0.35835 (12)	0.8003 (3)	0.37556 (11)	0.0489 (5)
N1	0.32675 (14)	0.3654 (4)	0.38965 (14)	0.0491 (6)
H1	0.3492	0.2036	0.3922	0.059*
C1	0.48155 (15)	0.4944 (5)	0.37540 (13)	0.0369 (6)
C2	0.52269 (17)	0.2853 (5)	0.41805 (15)	0.0462 (6)
H2	0.4884	0.1813	0.4512	0.055*
C3	0.61349 (18)	0.2254 (6)	0.41296 (16)	0.0529 (7)
H3	0.6419	0.0831	0.4431	0.063*
C4	0.66205 (17)	0.3746 (6)	0.36373 (15)	0.0489 (7)
C5	0.62262 (18)	0.5866 (6)	0.32108 (16)	0.0539 (7)
H5	0.6569	0.6895	0.2876	0.065*
C6	0.53255 (18)	0.6464 (5)	0.32789 (15)	0.0474 (6)
H6	0.5051	0.7938	0.2996	0.057*
C7	0.38370 (16)	0.5666 (5)	0.38013 (13)	0.0388 (6)
C8	0.22970 (16)	0.3992 (5)	0.39603 (16)	0.0484 (7)
H8	0.2181	0.5912	0.4058	0.058*
C9	0.20142 (17)	0.2430 (7)	0.46572 (16)	0.0564 (8)
H9A	0.2371	0.3025	0.5157	0.068*
H9B	0.2142	0.0524	0.4582	0.068*
C10	0.0997 (2)	0.2819 (9)	0.4724 (2)	0.0789 (11)
H10A	0.0816	0.1731	0.5171	0.095*
H10B	0.0881	0.4702	0.4845	0.095*
C11	0.04290 (19)	0.2051 (7)	0.3968 (2)	0.0735 (10)
H11A	−0.0221	0.2421	0.4022	0.088*
H11B	0.0494	0.0126	0.3875	0.088*
C12	0.0718 (2)	0.3567 (8)	0.3267 (2)	0.0819 (11)
H12A	0.0588	0.5476	0.3333	0.098*
H12B	0.0360	0.2949	0.2770	0.098*
C13	0.1742 (2)	0.3193 (7)	0.31917 (18)	0.0699 (9)
H13A	0.1864	0.1313	0.3072	0.084*
H13B	0.1920	0.4289	0.2746	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0443 (4)	0.0948 (7)	0.0840 (6)	0.0035 (4)	0.0128 (4)	−0.0220 (5)
O1	0.0535 (11)	0.0273 (9)	0.0662 (12)	0.0040 (8)	0.0080 (9)	0.0016 (8)
N1	0.0406 (11)	0.0278 (12)	0.0806 (15)	0.0040 (9)	0.0135 (11)	0.0015 (10)
C1	0.0413 (12)	0.0304 (12)	0.0393 (12)	−0.0013 (10)	0.0055 (10)	−0.0056 (10)
C2	0.0445 (13)	0.0408 (14)	0.0535 (15)	0.0020 (12)	0.0069 (11)	0.0053 (12)
C3	0.0475 (15)	0.0517 (17)	0.0589 (16)	0.0078 (13)	0.0025 (12)	0.0025 (14)
C4	0.0410 (13)	0.0589 (18)	0.0472 (14)	−0.0017 (13)	0.0063 (11)	−0.0165 (13)
C5	0.0550 (16)	0.0583 (18)	0.0510 (15)	−0.0079 (14)	0.0183 (13)	−0.0018 (14)
C6	0.0527 (15)	0.0415 (16)	0.0486 (14)	−0.0019 (12)	0.0086 (12)	0.0051 (12)
C7	0.0462 (14)	0.0305 (14)	0.0399 (13)	0.0006 (11)	0.0058 (10)	−0.0009 (10)
C8	0.0396 (13)	0.0292 (13)	0.0768 (18)	0.0047 (11)	0.0074 (13)	−0.0048 (13)
C9	0.0407 (14)	0.078 (2)	0.0518 (15)	0.0046 (14)	0.0100 (12)	−0.0119 (14)
C10	0.0473 (16)	0.113 (3)	0.080 (2)	0.0028 (18)	0.0212 (15)	−0.016 (2)
C11	0.0400 (15)	0.067 (2)	0.113 (3)	−0.0003 (14)	0.0070 (17)	−0.018 (2)
C12	0.0597 (19)	0.088 (3)	0.091 (2)	0.0080 (18)	−0.0240 (17)	−0.005 (2)
C13	0.0609 (18)	0.088 (2)	0.0589 (17)	0.0027 (17)	−0.0039 (14)	0.0122 (17)

Geometric parameters (Å, º) top

Cl1—C4	1.742 (3)	C8—C13	1.510 (4)
O1—C7	1.236 (3)	C8—H8	1.0000
N1—C7	1.338 (3)	C9—C10	1.530 (4)
N1—C8	1.457 (3)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.379 (4)	C10—C11	1.496 (5)
C1—C6	1.386 (3)	C10—H10A	0.9900
C1—C7	1.499 (3)	C10—H10B	0.9900
C2—C3	1.385 (4)	C11—C12	1.505 (5)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.375 (4)	C11—H11B	0.9900
C3—H3	0.9500	C12—C13	1.541 (4)
C4—C5	1.381 (4)	C12—H12A	0.9900
C5—C6	1.379 (4)	C12—H12B	0.9900
C5—H5	0.9500	C13—H13A	0.9900
C6—H6	0.9500	C13—H13B	0.9900
C8—C9	1.508 (4)

C7—N1—C8	123.7 (2)	C8—C9—C10	110.2 (2)
C7—N1—H1	118.1	C8—C9—H9A	109.6
C8—N1—H1	118.1	C10—C9—H9A	109.6
C2—C1—C6	119.1 (2)	C8—C9—H9B	109.6
C2—C1—C7	122.1 (2)	C10—C9—H9B	109.6
C6—C1—C7	118.8 (2)	H9A—C9—H9B	108.1
C1—C2—C3	120.6 (2)	C11—C10—C9	111.7 (3)
C1—C2—H2	119.7	C11—C10—H10A	109.3
C3—C2—H2	119.7	C9—C10—H10A	109.3
C4—C3—C2	119.2 (3)	C11—C10—H10B	109.3
C4—C3—H3	120.4	C9—C10—H10B	109.3
C2—C3—H3	120.4	H10A—C10—H10B	107.9
C3—C4—C5	121.2 (3)	C10—C11—C12	110.8 (3)
C3—C4—Cl1	119.2 (2)	C10—C11—H11A	109.5
C5—C4—Cl1	119.6 (2)	C12—C11—H11A	109.5
C6—C5—C4	118.8 (2)	C10—C11—H11B	109.5
C6—C5—H5	120.6	C12—C11—H11B	109.5
C4—C5—H5	120.6	H11A—C11—H11B	108.1
C5—C6—C1	121.0 (3)	C11—C12—C13	111.3 (3)
C5—C6—H6	119.5	C11—C12—H12A	109.4
C1—C6—H6	119.5	C13—C12—H12A	109.4
O1—C7—N1	122.7 (2)	C11—C12—H12B	109.4
O1—C7—C1	121.0 (2)	C13—C12—H12B	109.4
N1—C7—C1	116.3 (2)	H12A—C12—H12B	108.0
N1—C8—C9	110.6 (2)	C8—C13—C12	110.1 (3)
N1—C8—C13	110.7 (2)	C8—C13—H13A	109.6
C9—C8—C13	110.9 (2)	C12—C13—H13A	109.6
N1—C8—H8	108.2	C8—C13—H13B	109.6
C9—C8—H8	108.2	C12—C13—H13B	109.6
C13—C8—H8	108.2	H13A—C13—H13B	108.1

C6—C1—C2—C3	−0.7 (4)	C6—C1—C7—O1	−32.8 (3)
C7—C1—C2—C3	−179.3 (2)	C2—C1—C7—N1	−34.0 (3)
C1—C2—C3—C4	−1.0 (4)	C6—C1—C7—N1	147.4 (2)
C2—C3—C4—C5	1.7 (4)	C7—N1—C8—C9	−132.2 (3)
C2—C3—C4—Cl1	−178.9 (2)	C7—N1—C8—C13	104.5 (3)
C3—C4—C5—C6	−0.6 (4)	N1—C8—C9—C10	179.5 (2)
Cl1—C4—C5—C6	−180.0 (2)	C13—C8—C9—C10	−57.3 (3)
C4—C5—C6—C1	−1.2 (4)	C8—C9—C10—C11	56.9 (4)
C2—C1—C6—C5	1.8 (4)	C9—C10—C11—C12	−56.0 (4)
C7—C1—C6—C5	−179.5 (2)	C10—C11—C12—C13	55.5 (4)
C8—N1—C7—O1	−0.3 (4)	N1—C8—C13—C12	−179.8 (3)
C8—N1—C7—C1	179.5 (2)	C9—C8—C13—C12	57.0 (3)
C2—C1—C7—O1	145.9 (2)	C11—C12—C13—C8	−56.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.06	2.901 (5)	160

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆ClNO
M_r	237.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.755 (14), 5.043 (7), 16.818 (16)
β (°)	96.13 (6)
V (Å³)	1244 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.12 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.967, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3651, 2388, 1497
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.06
No. of reflections	2388
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.21

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.06	2.901 (5)	159.9

Symmetry code: (i) x, y−1, z.

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Volume 65| Part 7| July 2009| Page o1539

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