N-Cyclo­hexyl-3-fluoro­benzamide

Saeed, A.; Khera, R.A.; Abbas, N.; Flörke, U.

doi:10.1107/S1600536808034478

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2209

doi:10.1107/S1600536808034478

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N-Cyclohexyl-3-fluorobenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Naeem Abbas ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 15 October 2008; accepted 22 October 2008; online 25 October 2008)

In the title molecule, C₁₃H₁₆FNO, the amide (N—C=O) plane is oriented at an angle of 29.9 (2)° with respect to the aromatic ring. The cyclohexane ring adopts the usual chair conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along [100]. A weak C—H⋯F interaction 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_r = 221.27
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.05
1492 reflections
150 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x+1, y, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The background to this study has been described in an earlier paper (Saeed et al., 2008b).

The molecular structure of the title compound is related to that of the 2,4-dichloro compound (Saeed et al., 2008a). The cyclohexane ring is in the most stable chair conformation. In general, bond lengths and angles are within normal ranges. The aromatic ring C2–C7 is oriented with respect to the N1/O1/C1 plane at a dihedral angle of 29.9 (2)°. The N1–C1–C2–C7 torsion angle is 150.37 (15)°, for the reported dichloro compound the corresponding angle is 130.16 (18)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the [100] direction (Fig. 2), in which they may be effective in the stabilization of the structure. Another intermolecular interaction is C—H···F (Table 1), as found in 4-fluoro-N-(2-fluorophenyl)benzamide (Chopra & Row, 2005).

Related literature top

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

Experimental top

3,5-Difluorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with cyclohexylamine (21.6 mmol) under a nitrogen atmosphere at reflux for 4 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 sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%). Analysis calculated for C₁₃H₁₅F₂NO: C 65.26, H 6.32, N 5.85%; found: C 65.31, H 6.39, N 5.77%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of title compound, showing the rotational disorder of the fluorophenyl ring. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along [100] with intermolecular N–H···O hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

N-Cyclohexyl-3-fluorobenzamide top

Crystal data top

C₁₃H₁₆FNO	F(000) = 236
M_r = 221.27	D_x = 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

Data collection top

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

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0686P)² + 0.0394P] where P = (F_o² + 2F_c²)/3
1492 reflections	(Δ/σ)_max = 0.001
150 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₃H₁₆FNO	V = 582.4 (6) Å³
M_r = 221.27	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.267 (3) Å	µ = 0.09 mm⁻¹
b = 6.599 (4) Å	T = 120 K
c = 16.755 (9) Å	0.45 × 0.40 × 0.21 mm
β = 90.090 (17)°

Data collection top

Bruker SMART APEX diffractometer	1492 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1420 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.978	R_int = 0.034
5071 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.098	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
1492 reflections	Δρ_min = −0.17 e Å⁻³
150 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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆FNO
M_r	221.27
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	5.267 (3), 6.599 (4), 16.755 (9)
β (°)	90.090 (17)
V (Å³)	582.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.40 × 0.21

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.962, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	5071, 1492, 1420
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.05
No. of reflections	1492
No. of parameters	150
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+2, y+1/2, −z+1.

Acknowledgements

NA is grateful to the Higher Education Commission of Pakistan for financial support for a PhD programme.

References

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