N-(2-Fluoro­phen­yl)cinnamamide

Saeed, A.; Khera, R.A.; Simpson, J.

doi:10.1107/S1600536810003867

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o533-o534

doi:10.1107/S1600536810003867

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N-(2-Fluorophenyl)cinnamamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera ^a and Jim Simpson ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 29 January 2010; accepted 1 February 2010; online 6 February 2010)

The title compound, C₁₅H₁₂FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline and crystallizes with two molecules A and B in the asymmetric unit. The two unique molecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluorobenzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in molecules A and B. The amide C—N—C(O)—C portions of the molecules 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 fluorobenzene rings in molecules A and B. The 2-fluoroacetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, intermolecular N—H⋯O hydrogen bonds augmented by weak C—H⋯π interactions link molecules 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_r = 241.26
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.156
S = 1.07
4376 reflections
331 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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⋯CgA^iv	0.95	2.89	3.679 (2)	141
C5A—H5A⋯CgB^v	0.95	2.80	3.621 (2)	149
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+2, -z; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The background to this work has been described in a previous paper (Saeed et al. 2009). The title compound, C₁₅H₁₂FNO (I), was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline. The compound crystallises with two molecules A and B in the asymmetric unit of the monoclinic unit cell. These two unique molecules are closely similar and overlay with an rms deviation of 0.0819Å (Macrae et al., 2008). The fluorobenzene and benzene rings are inclined at 73.89 (7)° and 79.46 (7)° respectively in the two molecules. The amide C10–N1–C1(O1)–C2 portions of the molecules are planar (rms deviations 0.035 and 0.028 Å) and are inclined at 45.51 (9)° and 47.71 (9) respectively to the fluorobenzene rings. The 2-fluoroacetamide units and the benzene rings each adopt E configurations with respect to the C═C bonds. A search of the Cambridge Database (Allen, 2002) reveals only one closely related halobenzene derivative (Nilofar Nissa et al., 2004) but the structures of a number of other cinnamanilide compounds are known (Leiserowitz & Tuval 1978; Nilofar Nissa et al., 2002; Jones & Dix, 2008; Saeed et al., 2009).

In the crystal structure, intermolecular N1A—H1NA···O1B and N1B—H1NB···O1A hydrogen bonds, augmented by weak C–H···π interactions involving the two fluorobenzene rings, link molecules into rows along a, Fig. 2. Additional weak C—H···O contacts further stabilise the packing, forming a three-dimensional network stacked down a, Table 1 & Fig. 3.

Related literature top

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 top

Cinnamoyl chloride (5.4 mmol) in CHCl₃ was treated with 4-fluoroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 2 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aqueous 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl₃ afforded the title compound (87%) as colourless needles: Anal. calcd. for C₁₅H₁₂FNO,: C, 74.67; H, 5.01; N, 5.81%; found: C, 74.69; H, 5.16; N, 5.94%.

Computing details top

Data collection: APEX2 (Bruker 2006); cell refinement: APEX2 and SAINT (Bruker 2006); data reduction: SAINT (Bruker 2006); 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 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. N—H···O hydrogen bonds (dashed lines) and weak C–H···π interactions (dotted lines) forming chains down b.
	Fig. 3. Crystal packing for (I) viewed down the a axis with hydrogen bonds drawn as dashed lines.

N-(2-Fluorophenyl)cinnamamide top

Crystal data top

C₁₅H₁₂FNO	F(000) = 1008
M_r = 241.26	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4376 independent reflections
Radiation source: fine-focus sealed tube	3312 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω scans	θ_max = 25.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
T_min = 0.696, T_max = 1.000	k = −15→15
24964 measured reflections	l = −23→23

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)] = 0.050	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(F_o²) + (0.0869P)² + 1.0345P] where P = (F_o² + 2F_c²)/3
4376 reflections	(Δ/σ)_max < 0.001
331 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₅H₁₂FNO	V = 2421.0 (5) Å³
M_r = 241.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6634 (12) Å	µ = 0.09 mm⁻¹
b = 13.0838 (17) Å	T = 89 K
c = 19.404 (3) Å	0.64 × 0.30 × 0.16 mm
β = 99.297 (7)°

Data collection top

Bruker APEXII CCD diffractometer	4376 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3312 reflections with I > 2σ(I)
T_min = 0.696, T_max = 1.000	R_int = 0.068
24964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.30 e Å⁻³
4376 reflections	Δρ_min = −0.36 e Å⁻³
331 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···CgA^iv	0.95	2.89	3.679 (2)	141
C5A—H5A···CgB^v	0.95	2.80	3.621 (2)	149

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) x, −y+1/2, z+1/2; (v) x+1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂FNO
M_r	241.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	89
a, b, c (Å)	9.6634 (12), 13.0838 (17), 19.404 (3)
β (°)	99.297 (7)
V (Å³)	2421.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.64 × 0.30 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.696, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24964, 4376, 3312
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.156, 1.07
No. of reflections	4376
No. of parameters	331
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.36

Computer programs: APEX2 (Bruker 2006), APEX2 and SAINT (Bruker 2006), SAINT (Bruker 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)	159.8
C14B—H14B···O1Bⁱⁱⁱ	0.95	2.59	3.476 (3)	154.9
C9B—H9B···CgA^iv	0.95	2.89	3.679 (2)	141.0
C5A—H5A···CgB^v	0.95	2.80	3.621 (2)	149.0

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) x, −y+1/2, z+1/2; (v) x+1, −y+1/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge a research grant from the Higher Education Commission of Pakistan under project No. 20-Miscel/R&D/00/3834. We also thank the University of Otago for the purchase of the diffractometer.

References

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