N-Cyclo-hexyl-2-fluoro-benzamide.

In the title compound, C(13)H(16)FNO, the fluoro-benzene ring plane and the plane through the amide unit are inclined at a dihedral angle of 29.92 (7)°. The cyclo-hexane ring adopts a chair conformation. In the crystal structure, N-H⋯O hydrogen bonds, augmented by weak C-H⋯O inter-actions, link the mol-ecules into transverse chains along a. These chains are linked into zigzag columns down a by C-H⋯F hydrogen bonds and C-H⋯π inter-actions.

Related literature

For background see: Saeed et al. (2008 ▶). For related structures, see: Kobal et al. (1990 ▶); Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶); Hou et al. (2004 ▶); Saeed et al. (2008 ▶). For information on the Cambridge Structural Database, see: Allen (2002 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H16FNO

M = 221.27

Monoclinic,

a = 5.1804 (6) Å

b = 6.5309 (8) Å

c = 16.6522 (19) Å

β = 91.336 (6)°

V = 563.24 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 91 (2) K

0.39 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.822, T max = 0.993

7905 measured reflections

2117 independent reflections

1884 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.114

S = 1.12

2117 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN; molecular graphics: ORTEPIII (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034090/lh2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034090/lh2713Isup2.hkl

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

C13H16FNO	F(000) = 236
Mr = 221.27	Dx = 1.305 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2700 reflections
a = 5.1804 (6) Å	θ = 3.4–32.5°
b = 6.5309 (8) Å	µ = 0.09 mm−1
c = 16.6522 (19) Å	T = 91 K
β = 91.336 (6)°	Needle, colourless
V = 563.24 (11) Å3	0.39 × 0.16 × 0.08 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2117 independent reflections
Radiation source: fine-focus sealed tube	1884 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 33.4°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
Tmin = 0.822, Tmax = 0.993	k = −8→9
7905 measured reflections	l = −25→24

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.0113P] where P = (Fo2 + 2Fc2)/3
2117 reflections	(Δ/σ)max = 0.002
148 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.26 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
O1	1.2369 (2)	0.9202 (2)	0.24742 (7)	0.0187 (3)
C1	1.0126 (3)	0.9513 (2)	0.22274 (9)	0.0122 (3)
C2	0.9598 (3)	1.1225 (2)	0.16419 (9)	0.0124 (3)
C3	0.7571 (3)	1.1292 (2)	0.10763 (9)	0.0142 (3)
F1	0.5940 (2)	0.96735 (18)	0.10014 (5)	0.0207 (2)
C4	0.7162 (3)	1.2929 (3)	0.05603 (9)	0.0187 (3)
H4	0.5765	1.2913	0.0180	0.022*
C5	0.8825 (3)	1.4593 (3)	0.06068 (10)	0.0207 (3)
H5	0.8553	1.5740	0.0264	0.025*
C6	1.0902 (3)	1.4580 (3)	0.11584 (10)	0.0203 (3)
H6	1.2055	1.5711	0.1188	0.024*
C7	1.1270 (3)	1.2908 (3)	0.16621 (9)	0.0162 (3)
H7	1.2697	1.2906	0.2031	0.019*
N1	0.8095 (3)	0.8430 (2)	0.24730 (8)	0.0129 (3)
HN1	0.655 (4)	0.883 (4)	0.2321 (12)	0.015*
C8	0.8378 (3)	0.6807 (2)	0.30746 (9)	0.0120 (3)
H8	1.0140	0.6199	0.3028	0.014*
C9	0.6393 (3)	0.5126 (2)	0.29046 (10)	0.0144 (3)
H9A	0.6632	0.4574	0.2358	0.017*
H9B	0.4631	0.5708	0.2927	0.017*
C10	0.6683 (3)	0.3397 (3)	0.35200 (10)	0.0181 (3)
H10A	0.8385	0.2730	0.3462	0.022*
H10B	0.5329	0.2354	0.3416	0.022*
C11	0.6456 (3)	0.4213 (3)	0.43778 (10)	0.0193 (3)
H11A	0.4685	0.4736	0.4455	0.023*
H11B	0.6765	0.3084	0.4765	0.023*
C12	0.8402 (3)	0.5932 (3)	0.45444 (10)	0.0184 (3)
H12A	0.8131	0.6494	0.5088	0.022*
H12B	1.0175	0.5368	0.4532	0.022*
C13	0.8128 (3)	0.7651 (3)	0.39258 (9)	0.0167 (3)
H13A	0.9481	0.8695	0.4029	0.020*
H13B	0.6425	0.8319	0.3977	0.020*

	U11	U22	U33	U12	U13	U23
O1	0.0108 (5)	0.0210 (6)	0.0242 (6)	−0.0001 (4)	−0.0012 (4)	0.0060 (5)
C1	0.0126 (6)	0.0105 (6)	0.0135 (6)	0.0003 (5)	0.0004 (5)	0.0002 (5)
C2	0.0123 (6)	0.0121 (6)	0.0127 (6)	0.0005 (5)	0.0017 (5)	0.0002 (5)
C3	0.0137 (6)	0.0154 (7)	0.0134 (6)	−0.0003 (6)	0.0008 (5)	0.0008 (6)
F1	0.0216 (5)	0.0223 (5)	0.0178 (4)	−0.0069 (4)	−0.0065 (4)	0.0005 (4)
C4	0.0184 (7)	0.0235 (8)	0.0143 (6)	0.0043 (7)	0.0022 (5)	0.0036 (6)
C5	0.0218 (7)	0.0200 (8)	0.0207 (7)	0.0060 (6)	0.0061 (6)	0.0080 (7)
C6	0.0204 (7)	0.0151 (7)	0.0256 (8)	−0.0007 (6)	0.0061 (6)	0.0043 (7)
C7	0.0151 (7)	0.0149 (7)	0.0186 (7)	−0.0016 (6)	0.0012 (5)	0.0012 (6)
N1	0.0103 (5)	0.0135 (6)	0.0149 (6)	−0.0007 (5)	−0.0013 (4)	0.0032 (5)
C8	0.0114 (6)	0.0108 (6)	0.0136 (6)	0.0003 (5)	−0.0010 (5)	0.0021 (5)
C9	0.0133 (6)	0.0115 (7)	0.0183 (7)	−0.0011 (5)	−0.0006 (5)	−0.0004 (5)
C10	0.0191 (7)	0.0121 (7)	0.0230 (8)	−0.0011 (6)	−0.0002 (6)	0.0026 (6)
C11	0.0188 (7)	0.0177 (8)	0.0215 (7)	0.0016 (6)	0.0029 (6)	0.0071 (6)
C12	0.0224 (7)	0.0175 (8)	0.0152 (7)	0.0007 (6)	−0.0011 (6)	0.0028 (6)
C13	0.0234 (7)	0.0122 (7)	0.0142 (6)	−0.0008 (6)	−0.0023 (6)	0.0004 (5)

O1—C1	1.2402 (18)	C8—C13	1.529 (2)
C1—N1	1.3395 (19)	C8—H8	1.0000
C1—C2	1.504 (2)	C9—C10	1.530 (2)
C2—C3	1.395 (2)	C9—H9A	0.9900
C2—C7	1.399 (2)	C9—H9B	0.9900
C3—F1	1.3571 (19)	C10—C11	1.532 (2)
C3—C4	1.384 (2)	C10—H10A	0.9900
C4—C5	1.388 (3)	C10—H10B	0.9900
C4—H4	0.9500	C11—C12	1.530 (2)
C5—C6	1.398 (2)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.387 (2)	C12—C13	1.528 (2)
C6—H6	0.9500	C12—H12A	0.9900
C7—H7	0.9500	C12—H12B	0.9900
N1—C8	1.4632 (19)	C13—H13A	0.9900
N1—HN1	0.87 (2)	C13—H13B	0.9900
C8—C9	1.526 (2)
O1—C1—N1	123.26 (14)	C8—C9—C10	110.57 (12)
O1—C1—C2	119.42 (13)	C8—C9—H9A	109.5
N1—C1—C2	117.29 (12)	C10—C9—H9A	109.5
C3—C2—C7	116.58 (14)	C8—C9—H9B	109.5
C3—C2—C1	125.69 (14)	C10—C9—H9B	109.5
C7—C2—C1	117.74 (13)	H9A—C9—H9B	108.1
F1—C3—C4	117.29 (13)	C9—C10—C11	111.03 (14)
F1—C3—C2	119.65 (14)	C9—C10—H10A	109.4
C4—C3—C2	123.03 (15)	C11—C10—H10A	109.4
C3—C4—C5	118.96 (14)	C9—C10—H10B	109.4
C3—C4—H4	120.5	C11—C10—H10B	109.4
C5—C4—H4	120.5	H10A—C10—H10B	108.0
C4—C5—C6	119.94 (15)	C12—C11—C10	111.09 (14)
C4—C5—H5	120.0	C12—C11—H11A	109.4
C6—C5—H5	120.0	C10—C11—H11A	109.4
C7—C6—C5	119.64 (16)	C12—C11—H11B	109.4
C7—C6—H6	120.2	C10—C11—H11B	109.4
C5—C6—H6	120.2	H11A—C11—H11B	108.0
C6—C7—C2	121.84 (14)	C13—C12—C11	111.48 (13)
C6—C7—H7	119.1	C13—C12—H12A	109.3
C2—C7—H7	119.1	C11—C12—H12A	109.3
C1—N1—C8	121.65 (12)	C13—C12—H12B	109.3
C1—N1—HN1	118.4 (16)	C11—C12—H12B	109.3
C8—N1—HN1	119.3 (15)	H12A—C12—H12B	108.0
N1—C8—C9	109.73 (12)	C12—C13—C8	110.57 (13)
N1—C8—C13	111.36 (12)	C12—C13—H13A	109.5
C9—C8—C13	111.09 (13)	C8—C13—H13A	109.5
N1—C8—H8	108.2	C12—C13—H13B	109.5
C9—C8—H8	108.2	C8—C13—H13B	109.5
C13—C8—H8	108.2	H13A—C13—H13B	108.1
O1—C1—C2—C3	152.45 (16)	C1—C2—C7—C6	−178.45 (14)
N1—C1—C2—C3	−29.4 (2)	O1—C1—N1—C8	1.5 (2)
O1—C1—C2—C7	−27.8 (2)	C2—C1—N1—C8	−176.60 (13)
N1—C1—C2—C7	150.43 (14)	C1—N1—C8—C9	−147.62 (14)
C7—C2—C3—F1	177.27 (13)	C1—N1—C8—C13	88.97 (17)
C1—C2—C3—F1	−2.9 (2)	N1—C8—C9—C10	179.13 (12)
C7—C2—C3—C4	−0.8 (2)	C13—C8—C9—C10	−57.29 (16)
C1—C2—C3—C4	179.00 (14)	C8—C9—C10—C11	56.43 (17)
F1—C3—C4—C5	−178.59 (14)	C9—C10—C11—C12	−55.36 (18)
C2—C3—C4—C5	−0.5 (2)	C10—C11—C12—C13	55.12 (19)
C3—C4—C5—C6	1.2 (2)	C11—C12—C13—C8	−55.66 (18)
C4—C5—C6—C7	−0.7 (3)	N1—C8—C13—C12	179.44 (13)
C5—C6—C7—C2	−0.7 (2)	C9—C8—C13—C12	56.80 (17)
C3—C2—C7—C6	1.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.87 (2)	2.20 (2)	3.0092 (18)	153.8 (19)
C9—H9B···O1i	0.99	2.67	3.446 (2)	136
C4—H4···F1ii	0.95	2.43	3.2326 (19)	142
C5—H5···Cg1iii	0.95	2.96	3.759 (2)	142
C9—H9A···Cg1iv	0.99	2.71	3.644 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.87 (2)	2.20 (2)	3.0092 (18)	153.8 (19)
C9—H9B⋯O1i	0.99	2.67	3.446 (2)	136
C4—H4⋯F1ii	0.95	2.43	3.2326 (19)	142
C5—H5⋯Cg1iii	0.95	2.96	3.759 (2)	142
C9—H9A⋯Cg1iv	0.99	2.71	3.644 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C2–C7 benzene ring.