N-Cyclo-hexyl-benzamide.

The structure of the title compound, C(13)H(17)NO, 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 inter-molecular N-H⋯O hydrogen bonds. Weak C-H⋯π inter-actions 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 = 203.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.163

S = 1.07

1423 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

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

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

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

C13H17NO	Z = 2
Mr = 203.28	F(000) = 220
Monoclinic, P21	Dx = 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

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

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(Fo2) + (0.1083P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1423 reflections	Δρmax = 0.22 e Å−3
140 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: unk
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .