N-(2-Fluoro-phen-yl)cinnamamide.

The title compound, C(15)H(12)FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoro-aniline and crystallizes with two mol-ecules A and B in the asymmetric unit. The two unique mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluoro-benzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in mol-ecules A and B. The amide C-N-C(O)-C portions of the mol-ecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluoro-benzene rings in mol-ecules A and B. The 2-fluoro-acetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds augmented by weak C-H⋯π inter-actions link mol-ecules into rows in a head-to-tail fashion along a. Additional weak C-H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a.

Related literature

For related structures see: Leiserowitz & Tuval (1978 ▶); Nilofar Nissa et al. (2002 ▶, 2004 ▶); Jones & Dix (2008 ▶); Saeed et al. (2009 ▶). For details of the Cambridge Structural Database: see Allen (2002 ▶).

Experimental

Crystal data

C15H12FNO

M = 241.26

Monoclinic,

a = 9.6634 (12) Å

b = 13.0838 (17) Å

c = 19.404 (3) Å

β = 99.297 (7)°

V = 2421.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 89 K

0.64 × 0.30 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.696, T max = 1.000

24964 measured reflections

4376 independent reflections

3312 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.156

S = 1.07

4376 reflections

331 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.36 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 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003867/hg2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003867/hg2641Isup2.hkl

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

C15H12FNO	F(000) = 1008
Mr = 241.26	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5945 reflections
a = 9.6634 (12) Å	θ = 2.6–25.1°
b = 13.0838 (17) Å	µ = 0.09 mm−1
c = 19.404 (3) Å	T = 89 K
β = 99.297 (7)°	Block, pale yellow
V = 2421.0 (5) Å3	0.64 × 0.30 × 0.16 mm
Z = 8

Bruker APEXII CCD diffractometer	4376 independent reflections
Radiation source: fine-focus sealed tube	3312 reflections with I > 2σ(I)
graphite	Rint = 0.068
ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
Tmin = 0.696, Tmax = 1.000	k = −15→15
24964 measured reflections	l = −23→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0869P)2 + 1.0345P] where P = (Fo2 + 2Fc2)/3
4376 reflections	(Δ/σ)max < 0.001
331 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1A	0.2567 (2)	0.71300 (15)	0.02767 (10)	0.0190 (4)
H1NA	0.342 (3)	0.735 (2)	0.0245 (12)	0.023*
C1A	0.1444 (2)	0.75857 (17)	−0.01166 (11)	0.0177 (5)
O1A	0.02319 (15)	0.72730 (12)	−0.01255 (8)	0.0220 (4)
C2A	0.1794 (2)	0.85024 (17)	−0.04971 (11)	0.0181 (5)
H2A	0.2725	0.8596	−0.0585	0.022*
C3A	0.0817 (2)	0.92016 (18)	−0.07189 (11)	0.0199 (5)
H3A	−0.0105	0.9048	−0.0639	0.024*
C4A	0.0985 (2)	1.01740 (18)	−0.10691 (11)	0.0191 (5)
C5A	−0.0136 (2)	1.08608 (18)	−0.11720 (12)	0.0229 (5)
H5A	−0.0991	1.0685	−0.1019	0.027*
C6A	−0.0017 (3)	1.18006 (19)	−0.14953 (12)	0.0251 (6)
H6A	−0.0792	1.2257	−0.1564	0.030*
C7A	0.1223 (3)	1.20718 (19)	−0.17169 (12)	0.0245 (5)
H7A	0.1303	1.2712	−0.1938	0.029*
C8A	0.2356 (2)	1.13992 (19)	−0.16129 (11)	0.0235 (5)
H8A	0.3214	1.1586	−0.1759	0.028*
C9A	0.2240 (2)	1.04614 (18)	−0.12984 (11)	0.0212 (5)
H9A	0.3015	1.0006	−0.1236	0.025*
C10A	0.2461 (2)	0.63122 (17)	0.07449 (12)	0.0179 (5)
C11A	0.3173 (2)	0.63675 (17)	0.14283 (12)	0.0201 (5)
F1A	0.39762 (14)	0.72109 (10)	0.16188 (7)	0.0294 (4)
C12A	0.3107 (2)	0.56122 (19)	0.19135 (12)	0.0244 (5)
H12A	0.3604	0.5676	0.2376	0.029*
C13A	0.2297 (2)	0.47516 (19)	0.17133 (12)	0.0241 (5)
H13A	0.2231	0.4222	0.2041	0.029*
C14A	0.1585 (2)	0.46671 (18)	0.10335 (12)	0.0216 (5)
H14A	0.1041	0.4075	0.0896	0.026*
C15A	0.1665 (2)	0.54433 (17)	0.05545 (12)	0.0194 (5)
H15A	0.1169	0.5380	0.0092	0.023*
N1B	0.7349 (2)	0.79010 (15)	−0.03553 (10)	0.0187 (4)
H1NB	0.814 (3)	0.769 (2)	−0.0341 (13)	0.022*
C1B	0.6485 (2)	0.74513 (17)	0.00412 (11)	0.0170 (5)
O1B	0.52817 (15)	0.77646 (12)	0.00522 (8)	0.0216 (4)
C2B	0.7098 (2)	0.65447 (17)	0.04371 (11)	0.0177 (5)
H2B	0.8086	0.6452	0.0519	0.021*
C3B	0.6277 (2)	0.58575 (17)	0.06798 (11)	0.0184 (5)
H3B	0.5299	0.5994	0.0594	0.022*
C4B	0.6714 (2)	0.49131 (18)	0.10655 (11)	0.0182 (5)
C5B	0.8115 (2)	0.47122 (19)	0.13481 (12)	0.0232 (5)
H5B	0.8819	0.5198	0.1293	0.028*
C6B	0.8485 (3)	0.3814 (2)	0.17071 (12)	0.0273 (6)
H6B	0.9439	0.3689	0.1897	0.033*
C7B	0.7465 (3)	0.30895 (19)	0.17912 (12)	0.0276 (6)
H7B	0.7723	0.2470	0.2034	0.033*
C8B	0.6072 (3)	0.32802 (19)	0.15172 (12)	0.0262 (6)
H8B	0.5371	0.2793	0.1575	0.031*
C9B	0.5701 (2)	0.41858 (18)	0.11572 (11)	0.0216 (5)
H9B	0.4745	0.4311	0.0971	0.026*
C10B	0.6938 (2)	0.87171 (17)	−0.08218 (11)	0.0173 (5)
C11B	0.7185 (2)	0.86597 (18)	−0.15059 (12)	0.0225 (5)
F1B	0.78197 (16)	0.78076 (11)	−0.17040 (7)	0.0351 (4)
C12B	0.6818 (2)	0.9429 (2)	−0.19871 (12)	0.0270 (6)
H12B	0.6997	0.9364	−0.2452	0.032*
C13B	0.6180 (2)	1.02988 (19)	−0.17770 (12)	0.0246 (5)
H13B	0.5918	1.0837	−0.2100	0.029*
C14B	0.5924 (2)	1.03851 (18)	−0.10960 (12)	0.0226 (5)
H14B	0.5490	1.0983	−0.0954	0.027*
C15B	0.6303 (2)	0.95959 (17)	−0.06203 (12)	0.0195 (5)
H15B	0.6126	0.9660	−0.0155	0.023*

	U11	U22	U33	U12	U13	U23
N1A	0.0104 (9)	0.0186 (11)	0.0287 (10)	−0.0008 (7)	0.0050 (8)	0.0038 (8)
C1A	0.0135 (11)	0.0178 (12)	0.0221 (11)	0.0005 (9)	0.0041 (8)	−0.0030 (9)
O1A	0.0112 (8)	0.0213 (9)	0.0336 (9)	−0.0002 (6)	0.0035 (6)	0.0019 (7)
C2A	0.0113 (10)	0.0205 (12)	0.0229 (11)	−0.0017 (9)	0.0041 (8)	−0.0005 (10)
C3A	0.0130 (11)	0.0206 (12)	0.0263 (11)	−0.0028 (9)	0.0038 (8)	−0.0009 (10)
C4A	0.0164 (11)	0.0199 (12)	0.0204 (11)	−0.0013 (9)	0.0014 (8)	−0.0009 (9)
C5A	0.0169 (11)	0.0238 (13)	0.0277 (12)	0.0015 (10)	0.0029 (9)	−0.0015 (11)
C6A	0.0250 (13)	0.0222 (13)	0.0271 (12)	0.0051 (10)	0.0006 (10)	−0.0016 (10)
C7A	0.0327 (14)	0.0178 (13)	0.0222 (12)	−0.0017 (10)	0.0015 (10)	0.0012 (10)
C8A	0.0213 (12)	0.0274 (14)	0.0222 (11)	−0.0066 (10)	0.0046 (9)	0.0001 (10)
C9A	0.0160 (11)	0.0238 (13)	0.0233 (11)	0.0007 (9)	0.0020 (9)	−0.0001 (10)
C10A	0.0092 (10)	0.0185 (12)	0.0273 (12)	0.0032 (8)	0.0072 (8)	0.0016 (10)
C11A	0.0157 (11)	0.0159 (12)	0.0288 (12)	0.0005 (9)	0.0037 (9)	−0.0022 (10)
F1A	0.0282 (8)	0.0204 (8)	0.0366 (8)	−0.0063 (6)	−0.0036 (6)	−0.0016 (6)
C12A	0.0248 (13)	0.0236 (13)	0.0242 (12)	0.0040 (10)	0.0024 (9)	0.0009 (10)
C13A	0.0231 (12)	0.0198 (13)	0.0306 (13)	0.0036 (10)	0.0080 (10)	0.0067 (10)
C14A	0.0171 (11)	0.0167 (12)	0.0327 (13)	0.0005 (9)	0.0094 (9)	−0.0009 (10)
C15A	0.0137 (11)	0.0196 (13)	0.0256 (12)	0.0009 (9)	0.0052 (9)	0.0003 (10)
N1B	0.0106 (9)	0.0186 (11)	0.0275 (10)	0.0030 (8)	0.0052 (8)	0.0026 (8)
C1B	0.0134 (11)	0.0169 (12)	0.0206 (11)	−0.0013 (9)	0.0024 (8)	−0.0041 (9)
O1B	0.0112 (8)	0.0215 (9)	0.0331 (9)	0.0014 (6)	0.0063 (6)	0.0022 (7)
C2B	0.0124 (10)	0.0204 (12)	0.0202 (11)	0.0019 (9)	0.0026 (8)	−0.0021 (9)
C3B	0.0136 (11)	0.0195 (12)	0.0222 (11)	0.0020 (9)	0.0034 (8)	−0.0017 (10)
C4B	0.0165 (11)	0.0216 (13)	0.0178 (11)	0.0021 (9)	0.0062 (8)	−0.0020 (9)
C5B	0.0203 (12)	0.0259 (14)	0.0245 (12)	0.0008 (10)	0.0071 (9)	0.0037 (10)
C6B	0.0230 (13)	0.0332 (15)	0.0264 (12)	0.0073 (11)	0.0064 (10)	0.0067 (11)
C7B	0.0350 (14)	0.0224 (14)	0.0264 (12)	0.0060 (11)	0.0085 (10)	0.0046 (10)
C8B	0.0309 (14)	0.0212 (13)	0.0279 (12)	−0.0049 (10)	0.0089 (10)	−0.0007 (11)
C9B	0.0205 (12)	0.0206 (13)	0.0241 (11)	−0.0006 (9)	0.0046 (9)	−0.0018 (10)
C10B	0.0106 (10)	0.0162 (12)	0.0246 (11)	−0.0028 (8)	0.0010 (8)	0.0018 (9)
C11B	0.0180 (12)	0.0197 (13)	0.0311 (12)	−0.0002 (9)	0.0082 (9)	−0.0026 (10)
F1B	0.0483 (10)	0.0259 (8)	0.0356 (8)	0.0089 (7)	0.0202 (7)	−0.0006 (7)
C12B	0.0280 (13)	0.0281 (14)	0.0254 (12)	−0.0025 (10)	0.0058 (10)	0.0028 (11)
C13B	0.0194 (12)	0.0208 (13)	0.0323 (13)	−0.0034 (9)	0.0009 (9)	0.0092 (11)
C14B	0.0145 (11)	0.0174 (12)	0.0352 (13)	−0.0007 (9)	0.0020 (9)	0.0005 (10)
C15B	0.0137 (11)	0.0191 (12)	0.0259 (11)	−0.0019 (9)	0.0038 (9)	−0.0005 (10)

N1A—C1A	1.360 (3)	N1B—C1B	1.357 (3)
N1A—C10A	1.418 (3)	N1B—C10B	1.414 (3)
N1A—H1NA	0.88 (3)	N1B—H1NB	0.81 (3)
C1A—O1A	1.238 (3)	C1B—O1B	1.237 (3)
C1A—C2A	1.476 (3)	C1B—C2B	1.483 (3)
C2A—C3A	1.335 (3)	C2B—C3B	1.334 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.464 (3)	C3B—C4B	1.471 (3)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.397 (3)	C4B—C9B	1.397 (3)
C4A—C9A	1.408 (3)	C4B—C5B	1.401 (3)
C5A—C6A	1.394 (3)	C5B—C6B	1.384 (3)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.384 (3)	C6B—C7B	1.396 (4)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.393 (3)	C7B—C8B	1.388 (3)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.383 (3)	C8B—C9B	1.393 (3)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C15A	1.389 (3)	C10B—C11B	1.388 (3)
C10A—C11A	1.393 (3)	C10B—C15B	1.389 (3)
C11A—F1A	1.365 (3)	C11B—F1B	1.358 (3)
C11A—C12A	1.373 (3)	C11B—C12B	1.380 (3)
C12A—C13A	1.390 (3)	C12B—C13B	1.386 (4)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.390 (3)	C13B—C14B	1.388 (3)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.387 (3)	C14B—C15B	1.394 (3)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500
C1A—N1A—C10A	123.83 (19)	C1B—N1B—C10B	123.75 (19)
C1A—N1A—H1NA	119.1 (16)	C1B—N1B—H1NB	119.8 (19)
C10A—N1A—H1NA	117.1 (16)	C10B—N1B—H1NB	116.4 (19)
O1A—C1A—N1A	122.1 (2)	O1B—C1B—N1B	122.1 (2)
O1A—C1A—C2A	123.66 (19)	O1B—C1B—C2B	123.6 (2)
N1A—C1A—C2A	114.22 (19)	N1B—C1B—C2B	114.22 (19)
C3A—C2A—C1A	120.7 (2)	C3B—C2B—C1B	120.8 (2)
C3A—C2A—H2A	119.6	C3B—C2B—H2B	119.6
C1A—C2A—H2A	119.6	C1B—C2B—H2B	119.6
C2A—C3A—C4A	128.3 (2)	C2B—C3B—C4B	127.4 (2)
C2A—C3A—H3A	115.9	C2B—C3B—H3B	116.3
C4A—C3A—H3A	115.9	C4B—C3B—H3B	116.3
C5A—C4A—C9A	118.1 (2)	C9B—C4B—C5B	118.4 (2)
C5A—C4A—C3A	118.9 (2)	C9B—C4B—C3B	119.18 (19)
C9A—C4A—C3A	123.0 (2)	C5B—C4B—C3B	122.5 (2)
C6A—C5A—C4A	120.9 (2)	C6B—C5B—C4B	120.8 (2)
C6A—C5A—H5A	119.6	C6B—C5B—H5B	119.6
C4A—C5A—H5A	119.6	C4B—C5B—H5B	119.6
C7A—C6A—C5A	120.3 (2)	C5B—C6B—C7B	120.4 (2)
C7A—C6A—H6A	119.8	C5B—C6B—H6B	119.8
C5A—C6A—H6A	119.8	C7B—C6B—H6B	119.8
C6A—C7A—C8A	119.5 (2)	C8B—C7B—C6B	119.5 (2)
C6A—C7A—H7A	120.2	C8B—C7B—H7B	120.2
C8A—C7A—H7A	120.2	C6B—C7B—H7B	120.2
C9A—C8A—C7A	120.4 (2)	C7B—C8B—C9B	120.0 (2)
C9A—C8A—H8A	119.8	C7B—C8B—H8B	120.0
C7A—C8A—H8A	119.8	C9B—C8B—H8B	120.0
C8A—C9A—C4A	120.8 (2)	C8B—C9B—C4B	120.9 (2)
C8A—C9A—H9A	119.6	C8B—C9B—H9B	119.5
C4A—C9A—H9A	119.6	C4B—C9B—H9B	119.5
C15A—C10A—C11A	117.6 (2)	C11B—C10B—C15B	117.8 (2)
C15A—C10A—N1A	122.8 (2)	C11B—C10B—N1B	119.8 (2)
C11A—C10A—N1A	119.7 (2)	C15B—C10B—N1B	122.4 (2)
F1A—C11A—C12A	118.89 (19)	F1B—C11B—C12B	119.1 (2)
F1A—C11A—C10A	118.1 (2)	F1B—C11B—C10B	118.1 (2)
C12A—C11A—C10A	123.0 (2)	C12B—C11B—C10B	122.8 (2)
C11A—C12A—C13A	118.5 (2)	C11B—C12B—C13B	118.6 (2)
C11A—C12A—H12A	120.7	C11B—C12B—H12B	120.7
C13A—C12A—H12A	120.7	C13B—C12B—H12B	120.7
C14A—C13A—C12A	120.0 (2)	C12B—C13B—C14B	120.2 (2)
C14A—C13A—H13A	120.0	C12B—C13B—H13B	119.9
C12A—C13A—H13A	120.0	C14B—C13B—H13B	119.9
C15A—C14A—C13A	120.3 (2)	C13B—C14B—C15B	120.1 (2)
C15A—C14A—H14A	119.8	C13B—C14B—H14B	119.9
C13A—C14A—H14A	119.8	C15B—C14B—H14B	119.9
C14A—C15A—C10A	120.6 (2)	C10B—C15B—C14B	120.5 (2)
C14A—C15A—H15A	119.7	C10B—C15B—H15B	119.7
C10A—C15A—H15A	119.7	C14B—C15B—H15B	119.7

CgA and CgB are the centroids of the fluorobenzene rings in molecules A and B respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1B	0.88 (3)	1.98 (3)	2.851 (2)	173 (2)
N1B—H1NB···O1Ai	0.81 (3)	2.07 (3)	2.870 (2)	170 (2)
C14A—H14A···O1Aii	0.95	2.50	3.410 (3)	160
C14B—H14B···O1Biii	0.95	2.59	3.476 (3)	155
C9B—H9B···CgAiv	0.95	2.89	3.679 (2)	141
C5A—H5A···CgBv	0.95	2.80	3.621 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

CgA and CgB are the centroids of the fluoro­benzene rings in mol­ecules A and B respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1B	0.88 (3)	1.98 (3)	2.851 (2)	173 (2)
N1B—H1NB⋯O1Ai	0.81 (3)	2.07 (3)	2.870 (2)	170 (2)
C14A—H14A⋯O1Aii	0.95	2.50	3.410 (3)	160
C14B—H14B⋯O1Biii	0.95	2.59	3.476 (3)	155
C9B—H9B⋯CgAiv	0.95	2.89	3.679 (2)	141
C5A—H5A⋯CgBv	0.95	2.80	3.621 (2)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .