N-Cyclo­hexyl­benzamide

Khan, I.U.; Javaid, R.; Sharif, S.; Tiekink, E.R.T.

doi:10.1107/S1600536810022609

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1687

doi:10.1107/S1600536810022609

Open

access

N-Cyclohexylbenzamide

Islam Ullah Khan,^a ‡ Rashid Javaid,^a Shahzad Sharif ^a and Edward R. T. Tiekink ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College, University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 11 June 2010; accepted 12 June 2010; online 18 June 2010)

The structure of the title compound, C₁₃H₁₇NO, features an anti disposition of the N—H and carbonyl groups. The amide group is twisted with respect to the benzene ring [N–C(=O)–C–C torsion angle = −30.8 (4)°]. In the crystal, C(4) chains propagating in [100] are formed by intermolecular N–H⋯O hydrogen bonds. Weak C—H⋯π interactions link the chains into sheets.

Related literature

For biological applications of benzamides, see: Clark et al. (1988 ); Leander et al. (1988 ); Diouf et al. (1997 ).

Experimental

Crystal data

C₁₃H₁₇NO
M_r = 203.28
Monoclinic, P 2₁
a = 5.2372 (3) Å
b = 6.5841 (4) Å
c = 16.6029 (12) Å
β = 91.176 (2)°
V = 572.38 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.28 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
5479 measured reflections
1423 independent reflections
1105 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.163
S = 1.07
1423 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1ⁱ	0.80 (3)	2.32 (3)	3.065 (3)	157 (3)
C13—H13a⋯Cg1ⁱⁱ	0.97	2.82	3.722 (4)	154
C5—H5⋯Cg1ⁱⁱⁱ	0.93	2.96	3.729 (4)	141
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022609/hb5496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022609/hb5496Isup2.hkl

checkCIF report

Comment top

Benzamides are frequently used in the synthesis of new and potent anti-convulsant agents (Clark et al., 1988; Leander et al., 1988; Diouf et al., 1997). The structure of the title compound, (I), a benzamide derivative, is reported herein (Fig. 1).

The benzene ring, adjacent to the carbonyl group, twisted with respect to the plane formed through the central amide group; the N1–C1–C2–C3 torsion angle = -30.8 (4) °. In the same way, the putative mirror plane through the cyclohexyl ring (having a chair conformation) is twisted away from the central plane; the O1–N1–C8–C11 torsion angle is 151.3 (4) °. The anti-disposition of the NH and carbonyl groups allows for the formation of N–H···O hydrogen bonds which leads to the formation supramolecular chains aligned along the a axis, Fig. 2 and Table 1. These are connected into layers in the ab plane via C–H···π interactions, Fig. 2 and Table 1.

Related literature top

For biological applications of benzamides, see: Clark et al. (1988); Leander et al. (1988); Diouf et al. (1997).

Experimental top

A solution of cyclohexyl amine (0.458 µl, 4 mmol) in dichloromethane (15 ml) was treated dropwise with benzoyl chloride (0.463 µl, 4 mmol) in the presence of triethanol amine (5 ml) as a catalyst. The resulting mixture was stirred for 1 h. The precipitates that formed were filtered, dried and crystallized from methanol to yield colourless blocks of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view in projection down the b axis of the unit-cell contents for (I), highlighting the formation of layers in the ab plane. The N–H···O and C–H···π interactions are shown as orange and purple dashed lines, respectively. Colour code: O, red; N, blue; C, grey; and H, green.

N-Cyclohexylbenzamide top

Crystal data top

C₁₃H₁₇NO	Z = 2
M_r = 203.28	F(000) = 220
Monoclinic, P2₁	D_x = 1.179 Mg m⁻³
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.2372 (3) Å	µ = 0.07 mm⁻¹
b = 6.5841 (4) Å	T = 293 K
c = 16.6029 (12) Å	Block, colourless
β = 91.176 (2)°	0.28 × 0.17 × 0.12 mm
V = 572.38 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	1105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 27.5°, θ_min = 1.2°
ϕ and ω scans	h = −6→6
5479 measured reflections	k = −8→8
1423 independent reflections	l = −21→21

Refinement top

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.1083P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1423 reflections	Δρ_max = 0.22 e Å⁻³
140 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: unk
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₃H₁₇NO	V = 572.38 (6) Å³
M_r = 203.28	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.2372 (3) Å	µ = 0.07 mm⁻¹
b = 6.5841 (4) Å	T = 293 K
c = 16.6029 (12) Å	0.28 × 0.17 × 0.12 mm
β = 91.176 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1105 reflections with I > 2σ(I)
5479 measured reflections	R_int = 0.033
1423 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.22 e Å⁻³
1423 reflections	Δρ_min = −0.21 e Å⁻³
140 parameters	Absolute structure: unk

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.7158 (3)	0.9885 (4)	0.23591 (14)	0.0636 (8)
N1	0.2952 (5)	0.9238 (4)	0.24441 (15)	0.0424 (6)
H1n	0.157 (6)	0.969 (6)	0.2345 (18)	0.045 (9)*
C1	0.4923 (5)	1.0267 (4)	0.21584 (18)	0.0415 (7)
C2	0.4362 (5)	1.1979 (5)	0.15919 (15)	0.0381 (6)
C3	0.2245 (5)	1.2004 (6)	0.10682 (16)	0.0460 (7)
H3	0.1077	1.0941	0.1071	0.055*
C4	0.1894 (6)	1.3614 (7)	0.05468 (18)	0.0575 (9)
H4	0.0488	1.3620	0.0195	0.069*
C5	0.3571 (6)	1.5201 (6)	0.05375 (19)	0.0602 (10)
H5	0.3321	1.6270	0.0179	0.072*
C6	0.5654 (6)	1.5203 (6)	0.1069 (2)	0.0586 (9)
H6	0.6785	1.6292	0.1076	0.070*
C7	0.6038 (6)	1.3593 (6)	0.15818 (19)	0.0495 (8)
H7	0.7455	1.3591	0.1929	0.059*
C8	0.3233 (5)	0.7589 (4)	0.30240 (17)	0.0405 (7)
H8	0.4904	0.6958	0.2945	0.049*
C9	0.3184 (8)	0.8399 (6)	0.3885 (2)	0.0611 (9)
H9A	0.4570	0.9358	0.3968	0.073*
H9B	0.1588	0.9108	0.3969	0.073*
C10	0.3452 (8)	0.6680 (7)	0.4484 (2)	0.0683 (11)
H10A	0.5140	0.6088	0.4443	0.082*
H10B	0.3296	0.7218	0.5024	0.082*
C11	0.1481 (6)	0.5051 (6)	0.4349 (2)	0.0636 (10)
H11A	−0.0198	0.5593	0.4461	0.076*
H11B	0.1814	0.3937	0.4719	0.076*
C12	0.1507 (7)	0.4266 (6)	0.3493 (2)	0.0620 (9)
H12A	0.0120	0.3306	0.3413	0.074*
H12B	0.3100	0.3556	0.3405	0.074*
C13	0.1224 (6)	0.5985 (5)	0.2888 (2)	0.0482 (8)
H13A	0.1362	0.5444	0.2347	0.058*
H13B	−0.0455	0.6591	0.2934	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0330 (10)	0.0681 (17)	0.0893 (17)	0.0023 (11)	−0.0042 (10)	0.0243 (15)
N1	0.0333 (12)	0.0437 (14)	0.0500 (14)	0.0042 (11)	−0.0005 (9)	0.0077 (11)
C1	0.0359 (13)	0.0405 (16)	0.0479 (15)	0.0036 (13)	0.0009 (11)	−0.0004 (13)
C2	0.0356 (12)	0.0421 (15)	0.0368 (14)	0.0029 (12)	0.0050 (10)	−0.0031 (13)
C3	0.0398 (14)	0.0546 (18)	0.0436 (15)	0.0001 (14)	−0.0021 (11)	0.0020 (16)
C4	0.0471 (16)	0.080 (2)	0.0453 (16)	0.0045 (18)	−0.0018 (13)	0.0133 (19)
C5	0.0554 (17)	0.067 (2)	0.059 (2)	0.0138 (18)	0.0137 (15)	0.024 (2)
C6	0.0552 (17)	0.0512 (19)	0.070 (2)	−0.0060 (17)	0.0147 (15)	0.0140 (18)
C7	0.0426 (14)	0.0538 (19)	0.0523 (17)	−0.0035 (14)	0.0059 (12)	0.0047 (16)
C8	0.0354 (12)	0.0391 (15)	0.0470 (16)	0.0060 (12)	0.0010 (11)	0.0046 (13)
C9	0.084 (2)	0.051 (2)	0.0476 (17)	−0.0102 (19)	−0.0115 (16)	−0.0008 (16)
C10	0.082 (2)	0.071 (3)	0.0513 (19)	−0.001 (2)	−0.0104 (17)	0.010 (2)
C11	0.0624 (19)	0.062 (2)	0.067 (2)	0.010 (2)	0.0116 (16)	0.022 (2)
C12	0.0633 (19)	0.0396 (18)	0.083 (3)	−0.0053 (16)	0.0001 (17)	0.0068 (18)
C13	0.0457 (15)	0.0427 (17)	0.0560 (19)	−0.0010 (14)	−0.0021 (13)	−0.0011 (15)

Geometric parameters (Å, º) top

O1—C1	1.236 (3)	C8—C9	1.526 (4)
N1—C1	1.331 (4)	C8—H8	0.9800
N1—C8	1.456 (4)	C9—C10	1.511 (5)
N1—H1n	0.80 (3)	C9—H9A	0.9700
C1—C2	1.493 (4)	C9—H9B	0.9700
C2—C7	1.379 (4)	C10—C11	1.502 (5)
C2—C3	1.395 (4)	C10—H10A	0.9700
C3—C4	1.379 (5)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.512 (5)
C4—C5	1.365 (5)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.389 (5)	C12—C13	1.519 (5)
C5—H5	0.9300	C12—H12A	0.9700
C6—C7	1.372 (5)	C12—H12B	0.9700
C6—H6	0.9300	C13—H13A	0.9700
C7—H7	0.9300	C13—H13B	0.9700
C8—C13	1.505 (4)

C1—N1—C8	123.1 (2)	C10—C9—C8	110.6 (3)
C1—N1—H1N	116 (3)	C10—C9—H9A	109.5
C8—N1—H1N	120 (2)	C8—C9—H9A	109.5
O1—C1—N1	122.5 (3)	C10—C9—H9B	109.5
O1—C1—C2	119.8 (2)	C8—C9—H9B	109.5
N1—C1—C2	117.7 (2)	H9A—C9—H9B	108.1
C7—C2—C3	118.8 (3)	C11—C10—C9	112.5 (3)
C7—C2—C1	118.2 (2)	C11—C10—H10A	109.1
C3—C2—C1	123.0 (3)	C9—C10—H10A	109.1
C4—C3—C2	119.7 (3)	C11—C10—H10B	109.1
C4—C3—H3	120.2	C9—C10—H10B	109.1
C2—C3—H3	120.2	H10A—C10—H10B	107.8
C5—C4—C3	121.2 (3)	C10—C11—C12	111.4 (3)
C5—C4—H4	119.4	C10—C11—H11A	109.4
C3—C4—H4	119.4	C12—C11—H11A	109.4
C4—C5—C6	119.4 (3)	C10—C11—H11B	109.4
C4—C5—H5	120.3	C12—C11—H11B	109.4
C6—C5—H5	120.3	H11A—C11—H11B	108.0
C7—C6—C5	119.8 (3)	C11—C12—C13	111.4 (3)
C7—C6—H6	120.1	C11—C12—H12A	109.4
C5—C6—H6	120.1	C13—C12—H12A	109.4
C6—C7—C2	121.2 (3)	C11—C12—H12B	109.4
C6—C7—H7	119.4	C13—C12—H12B	109.4
C2—C7—H7	119.4	H12A—C12—H12B	108.0
N1—C8—C13	111.3 (2)	C8—C13—C12	111.4 (2)
N1—C8—C9	110.8 (3)	C8—C13—H13A	109.3
C13—C8—C9	111.1 (3)	C12—C13—H13A	109.3
N1—C8—H8	107.8	C8—C13—H13B	109.3
C13—C8—H8	107.8	C12—C13—H13B	109.3
C9—C8—H8	107.8	H13A—C13—H13B	108.0

C8—N1—C1—O1	0.7 (5)	C3—C2—C7—C6	−0.1 (4)
C8—N1—C1—C2	−177.6 (2)	C1—C2—C7—C6	179.2 (3)
O1—C1—C2—C7	−28.3 (4)	C1—N1—C8—C13	−146.5 (3)
N1—C1—C2—C7	150.1 (3)	C1—N1—C8—C9	89.3 (3)
O1—C1—C2—C3	150.9 (3)	N1—C8—C9—C10	179.5 (3)
N1—C1—C2—C3	−30.8 (4)	C13—C8—C9—C10	55.2 (3)
C7—C2—C3—C4	1.0 (4)	C8—C9—C10—C11	−54.8 (4)
C1—C2—C3—C4	−178.2 (3)	C9—C10—C11—C12	54.6 (4)
C2—C3—C4—C5	−0.6 (5)	C10—C11—C12—C13	−54.1 (4)
C3—C4—C5—C6	−0.7 (5)	N1—C8—C13—C12	−179.8 (3)
C4—C5—C6—C7	1.6 (5)	C9—C8—C13—C12	−55.8 (3)
C5—C6—C7—C2	−1.2 (5)	C11—C12—C13—C8	55.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.80 (3)	2.32 (3)	3.065 (3)	157 (3)
C13—H13a···Cg1ⁱⁱ	0.97	2.82	3.722 (4)	154
C5—H5···Cg1ⁱⁱⁱ	0.93	2.96	3.729 (4)	141

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO
M_r	203.28
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.2372 (3), 6.5841 (4), 16.6029 (12)
β (°)	91.176 (2)
V (Å³)	572.38 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.28 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5479, 1423, 1105
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.163, 1.07
No. of reflections	1423
No. of parameters	140
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Absolute structure	Unk

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.80 (3)	2.32 (3)	3.065 (3)	157 (3)
C13—H13a···Cg1ⁱⁱ	0.97	2.82	3.722 (4)	154
C5—H5···Cg1ⁱⁱⁱ	0.93	2.96	3.729 (4)	141

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z.

Footnotes

‡Additional correspondence author, e-mail: iuklodhi@yahoo.com.

Acknowledgements

We are thankful to Mr Munawar Hussain, Engineering Cell Government College University, Lahore, for providing supportive services to the Materials Chemistry Laboratory.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 & SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Clark, C. R. (1988). Epilepsia, 29, 198–203. CrossRef CAS PubMed Web of Science Google Scholar
Diouf, O., Bourhim, M., Lambert, D. M., Poupaert, J. H., Stables, J. P. & Vamecq, J. (1997). Biomed. Pharmacother. 51, 131–136. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Leander, J. D., Robertson, D. W., Clark, C. R., Lawson, R. R. & Rathbun, R. C. (1988). Epilepsia, 29, 83–90. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1687

doi:10.1107/S1600536810022609

Open

access