N-Cyclo-hexyl-3-fluoro-benzamide.

In the title mol-ecule, C(13)H(16)FNO, the amide (N-C=O) plane is oriented at an angle of 29.9 (2)° with respect to the aromatic ring. The cyclo-hexane ring adopts the usual chair conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along [100]. A weak C-H⋯F inter-action is also observed. The F atom is disordered over two positions with occupancy factors of 0.873 (3) and 0.127 (3).

Related literature

For related structures, see: Chopra & Guru Row (2005 ▶); Saeed et al. (2008a ▶,b ▶).

Experimental

Crystal data

C13H16FNO

M = 221.27

Monoclinic,

a = 5.267 (3) Å

b = 6.599 (4) Å

c = 16.755 (9) Å

β = 90.090 (17)°

V = 582.4 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 120 (2) K

0.45 × 0.40 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.962, T max = 0.978

5071 measured reflections

1492 independent reflections

1420 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.05

1492 reflections

150 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034478/ci2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034478/ci2689Isup2.hkl

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

C13H16FNO	F(000) = 236
Mr = 221.27	Dx = 1.262 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 796 reflections
a = 5.267 (3) Å	θ = 2.4–28.3°
b = 6.599 (4) Å	µ = 0.09 mm−1
c = 16.755 (9) Å	T = 120 K
β = 90.090 (17)°	Prism, colourless
V = 582.4 (6) Å3	0.45 × 0.40 × 0.21 mm
Z = 2

Bruker SMART APEX diffractometer	1492 independent reflections
Radiation source: sealed tube	1420 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.962, Tmax = 0.978	k = −8→8
5071 measured reflections	l = −22→19

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.0394P] where P = (Fo2 + 2Fc2)/3
1492 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.9633 (3)	0.6562 (2)	0.49344 (8)	0.0376 (4)	0.873 (3)
F2	0.249 (2)	0.9837 (17)	0.3846 (6)	0.043 (3)*	0.127 (3)
O1	0.2561 (2)	0.2922 (2)	0.25636 (8)	0.0316 (3)
N1	0.6841 (3)	0.2208 (2)	0.25218 (8)	0.0206 (3)
H1A	0.8356	0.2505	0.2710	0.025*
C1	0.4794 (3)	0.3278 (2)	0.27778 (10)	0.0208 (3)
C2	0.5341 (3)	0.5002 (2)	0.33504 (9)	0.0198 (3)
C3	0.7409 (3)	0.4971 (3)	0.38818 (10)	0.0229 (3)
H3A	0.8556	0.3860	0.3894	0.027*
C4	0.7720 (3)	0.6615 (3)	0.43877 (10)	0.0269 (4)
H4A	0.9080	0.6591	0.4760	0.032*	0.127 (3)
C5	0.6128 (4)	0.8300 (3)	0.43745 (10)	0.0288 (4)
H5A	0.6419	0.9416	0.4721	0.035*
C6	0.4084 (4)	0.8306 (3)	0.38366 (11)	0.0295 (4)
H6A	0.2973	0.9439	0.3817	0.035*	0.873 (3)
C7	0.3671 (3)	0.6659 (3)	0.33314 (10)	0.0253 (4)
H7A	0.2265	0.6658	0.2976	0.030*
C8	0.6571 (3)	0.0567 (2)	0.19365 (9)	0.0195 (3)
H8A	0.4853	−0.0054	0.2003	0.023*
C9	0.6786 (4)	0.1391 (3)	0.10784 (10)	0.0275 (4)
H9A	0.5431	0.2403	0.0984	0.033*
H9B	0.8445	0.2074	0.1011	0.033*
C10	0.6542 (4)	−0.0336 (3)	0.04667 (10)	0.0299 (4)
H10A	0.4813	−0.0920	0.0497	0.036*
H10B	0.6781	0.0216	−0.0078	0.036*
C11	0.8501 (4)	−0.2007 (3)	0.06182 (11)	0.0291 (4)
H11A	1.0228	−0.1466	0.0524	0.035*
H11B	0.8212	−0.3136	0.0240	0.035*
C12	0.8313 (4)	−0.2802 (3)	0.14799 (11)	0.0272 (4)
H12A	0.6653	−0.3480	0.1555	0.033*
H12B	0.9664	−0.3818	0.1573	0.033*
C13	0.8582 (3)	−0.1078 (3)	0.20882 (11)	0.0232 (3)
H13A	1.0299	−0.0476	0.2047	0.028*
H13B	0.8379	−0.1624	0.2635	0.028*

	U11	U22	U33	U12	U13	U23
F1	0.0405 (8)	0.0402 (7)	0.0322 (7)	−0.0017 (6)	−0.0107 (5)	−0.0067 (6)
O1	0.0177 (6)	0.0310 (7)	0.0460 (8)	0.0009 (5)	−0.0028 (5)	−0.0113 (6)
N1	0.0172 (6)	0.0198 (6)	0.0247 (7)	0.0003 (5)	−0.0015 (5)	−0.0024 (5)
C1	0.0197 (8)	0.0181 (7)	0.0246 (7)	0.0002 (6)	0.0004 (6)	−0.0004 (6)
C2	0.0197 (8)	0.0180 (7)	0.0217 (7)	−0.0015 (6)	0.0045 (6)	0.0002 (6)
C3	0.0231 (8)	0.0221 (7)	0.0235 (7)	0.0014 (6)	0.0018 (6)	0.0010 (6)
C4	0.0270 (9)	0.0306 (9)	0.0229 (8)	−0.0040 (7)	0.0018 (6)	−0.0012 (7)
C5	0.0314 (9)	0.0259 (9)	0.0292 (8)	−0.0041 (7)	0.0075 (7)	−0.0081 (8)
C6	0.0268 (9)	0.0233 (8)	0.0385 (9)	0.0044 (7)	0.0076 (7)	−0.0052 (8)
C7	0.0214 (8)	0.0253 (8)	0.0293 (8)	0.0023 (7)	0.0013 (6)	−0.0015 (7)
C8	0.0169 (7)	0.0173 (7)	0.0243 (8)	−0.0005 (6)	−0.0003 (6)	−0.0017 (6)
C9	0.0376 (10)	0.0205 (8)	0.0242 (8)	0.0018 (7)	−0.0026 (7)	0.0000 (6)
C10	0.0367 (10)	0.0281 (9)	0.0250 (8)	−0.0007 (8)	−0.0034 (7)	−0.0043 (7)
C11	0.0290 (9)	0.0249 (8)	0.0334 (9)	−0.0032 (8)	0.0051 (7)	−0.0085 (8)
C12	0.0284 (9)	0.0177 (8)	0.0356 (9)	0.0023 (7)	−0.0016 (7)	−0.0027 (7)
C13	0.0221 (8)	0.0192 (8)	0.0285 (8)	0.0014 (6)	−0.0010 (6)	−0.0003 (6)

F1—C4	1.361 (2)	C8—C13	1.538 (2)
F2—C6	1.315 (11)	C8—C9	1.541 (2)
O1—C1	1.252 (2)	C8—H8A	1.00
N1—C1	1.359 (2)	C9—C10	1.538 (2)
N1—C8	1.468 (2)	C9—H9A	0.99
N1—H1A	0.88	C9—H9B	0.99
C1—C2	1.515 (2)	C10—C11	1.531 (3)
C2—C7	1.404 (2)	C10—H10A	0.99
C2—C3	1.406 (2)	C10—H10B	0.99
C3—C4	1.386 (3)	C11—C12	1.540 (3)
C3—H3A	0.95	C11—H11A	0.99
C4—C5	1.393 (3)	C11—H11B	0.99
C4—H4A	0.95	C12—C13	1.534 (2)
C5—C6	1.403 (3)	C12—H12A	0.99
C5—H5A	0.95	C12—H12B	0.99
C6—C7	1.394 (3)	C13—H13A	0.99
C6—H6A	0.95	C13—H13B	0.99
C7—H7A	0.95
C1—N1—C8	121.23 (14)	C13—C8—H8A	108.4
C1—N1—H1A	119.4	C9—C8—H8A	108.4
C8—N1—H1A	119.4	C10—C9—C8	110.76 (15)
O1—C1—N1	123.89 (15)	C10—C9—H9A	109.5
O1—C1—C2	120.02 (14)	C8—C9—H9A	109.5
N1—C1—C2	116.09 (14)	C10—C9—H9B	109.5
C7—C2—C3	120.72 (15)	C8—C9—H9B	109.5
C7—C2—C1	116.85 (14)	H9A—C9—H9B	108.1
C3—C2—C1	122.42 (15)	C11—C10—C9	111.55 (14)
C4—C3—C2	117.78 (16)	C11—C10—H10A	109.3
C4—C3—H3A	121.1	C9—C10—H10A	109.3
C2—C3—H3A	121.1	C11—C10—H10B	109.3
F1—C4—C3	118.55 (17)	C9—C10—H10B	109.3
F1—C4—C5	118.43 (16)	H10A—C10—H10B	108.0
C3—C4—C5	123.00 (16)	C10—C11—C12	110.90 (15)
C3—C4—H4A	118.5	C10—C11—H11A	109.5
C5—C4—H4A	118.5	C12—C11—H11A	109.5
C4—C5—C6	118.30 (16)	C10—C11—H11B	109.5
C4—C5—H5A	120.9	C12—C11—H11B	109.5
C6—C5—H5A	120.9	H11A—C11—H11B	108.0
F2—C6—C7	120.5 (5)	C13—C12—C11	111.33 (15)
F2—C6—C5	119.0 (5)	C13—C12—H12A	109.4
C7—C6—C5	120.42 (16)	C11—C12—H12A	109.4
C7—C6—H6A	119.8	C13—C12—H12B	109.4
C5—C6—H6A	119.8	C11—C12—H12B	109.4
C6—C7—C2	119.75 (15)	H12A—C12—H12B	108.0
C6—C7—H7A	120.1	C12—C13—C8	110.55 (13)
C2—C7—H7A	120.1	C12—C13—H13A	109.5
N1—C8—C13	110.16 (13)	C8—C13—H13A	109.5
N1—C8—C9	110.86 (13)	C12—C13—H13B	109.5
C13—C8—C9	110.58 (13)	C8—C13—H13B	109.5
N1—C8—H8A	108.4	H13A—C13—H13B	108.1
C8—N1—C1—O1	2.5 (2)	F2—C6—C7—C2	−177.6 (5)
C8—N1—C1—C2	−177.01 (13)	C5—C6—C7—C2	−1.2 (3)
O1—C1—C2—C7	−29.1 (2)	C3—C2—C7—C6	0.9 (2)
N1—C1—C2—C7	150.37 (15)	C1—C2—C7—C6	−179.27 (15)
O1—C1—C2—C3	150.71 (16)	C1—N1—C8—C13	−148.28 (15)
N1—C1—C2—C3	−29.8 (2)	C1—N1—C8—C9	89.00 (18)
C7—C2—C3—C4	0.6 (2)	N1—C8—C9—C10	179.17 (14)
C1—C2—C3—C4	−179.20 (14)	C13—C8—C9—C10	56.69 (18)
C2—C3—C4—F1	176.62 (15)	C8—C9—C10—C11	−55.8 (2)
C2—C3—C4—C5	−1.9 (3)	C9—C10—C11—C12	55.0 (2)
F1—C4—C5—C6	−176.95 (16)	C10—C11—C12—C13	−55.56 (19)
C3—C4—C5—C6	1.6 (3)	C11—C12—C13—C8	56.76 (19)
C4—C5—C6—F2	176.4 (6)	N1—C8—C13—C12	179.90 (13)
C4—C5—C6—C7	0.1 (3)	C9—C8—C13—C12	−57.21 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88	2.25	3.050 (2)	152
C5—H5A···F1ii	0.95	2.58	3.310 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	2.25	3.050 (2)	152
C5—H5A⋯F1ii	0.95	2.58	3.310 (3)	134

Symmetry codes: (i) ; (ii) .