2-Fluoro-N-o-tolyl-benzamide.

In the title compound, C(14)H(12)FNO, the ortho-F atom and corresponding H atom on the fluoro-benzene ring are disordered over two positions with occupancies of 0.856 (4) and 0.144 (4). The amide unit is planar with a maximum deviation of 0.0057 (16) Å and the amide plane makes dihedral angles of 38.27 (11)° with the fluoro-benzene ring plane and 37.53 (10)° with the tolyl ring. The two benzene rings are inclined at an angle of 4.17 (15)°. In the crystal structure, chains form along b through N-H⋯O hydrogen bonds augmented by C-H⋯π inter-actions. Additional inter-molecular C-H⋯O and C-H⋯F hydrogen bonds further stabilize the structure, forming layers in the ac plane.

Related literature

For related structures, see: Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶); Hou et al. (2004 ▶); Saeed et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12FNO

M = 229.25

Monoclinic,

a = 10.749 (4) Å

b = 4.8245 (17) Å

c = 21.580 (7) Å

β = 93.820 (19)°

V = 1116.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 93 (2) K

0.25 × 0.15 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.779, T max = 0.995

7896 measured reflections

1228 independent reflections

925 reflections with I > 2σ(I)

R int = 0.067

θmax = 21.3°

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.06

1228 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 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., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808043122/hb2882sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043122/hb2882Isup2.hkl

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

C14H12FNO	F(000) = 480
Mr = 229.25	Dx = 1.364 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1374 reflections
a = 10.749 (4) Å	θ = 3.3–21.2°
b = 4.8245 (17) Å	µ = 0.10 mm−1
c = 21.580 (7) Å	T = 93 K
β = 93.820 (19)°	Rectangular plate, colourless
V = 1116.6 (7) Å3	0.25 × 0.15 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	1228 independent reflections
Radiation source: fine-focus sealed tube	925 reflections with I > 2σ(I)
graphite	Rint = 0.067
ω scans	θmax = 21.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→10
Tmin = 0.779, Tmax = 0.995	k = −4→4
7896 measured reflections	l = −22→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3
1228 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 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)
C1	0.5852 (2)	1.1330 (5)	0.13062 (12)	0.0203 (7)
O1	0.57188 (16)	1.3797 (3)	0.11721 (8)	0.0291 (6)
C2	0.5376 (2)	1.0250 (4)	0.18985 (11)	0.0177 (7)
C7	0.4271 (2)	1.1328 (5)	0.20975 (13)	0.0229 (7)
H7	0.3828	1.2677	0.1850	0.027*	0.856 (4)
F1	0.71053 (15)	0.7317 (3)	0.21278 (8)	0.0296 (7)	0.856 (4)
C3	0.5996 (2)	0.8335 (5)	0.22854 (13)	0.0242 (7)
H3	0.6757	0.7577	0.2162	0.029*	0.144 (4)
F1'	0.3678 (10)	1.321 (2)	0.1771 (6)	0.046 (4)	0.144 (4)
C4	0.5566 (3)	0.7481 (5)	0.28378 (13)	0.0302 (7)
H4	0.6022	0.6179	0.3093	0.036*
C5	0.4450 (3)	0.8563 (5)	0.30152 (13)	0.0284 (7)
H5	0.4126	0.7979	0.3393	0.034*
C6	0.3806 (2)	1.0486 (5)	0.26455 (12)	0.0270 (7)
H6	0.3043	1.1228	0.2769	0.032*
N1	0.64105 (18)	0.9476 (5)	0.09499 (10)	0.0197 (6)
HN1	0.639 (2)	0.781 (5)	0.1077 (12)	0.028 (8)*
C8	0.6910 (2)	1.0053 (4)	0.03731 (11)	0.0173 (7)
C9	0.8010 (2)	0.8696 (4)	0.02298 (12)	0.0186 (7)
C14	0.8660 (2)	0.6685 (5)	0.06812 (12)	0.0243 (7)
H14A	0.8801	0.7574	0.1088	0.036*
H14B	0.9463	0.6140	0.0528	0.036*
H14C	0.8138	0.5037	0.0720	0.036*
C10	0.8481 (2)	0.9264 (5)	−0.03388 (12)	0.0242 (7)
H10	0.9220	0.8353	−0.0446	0.029*
C11	0.7908 (2)	1.1116 (5)	−0.07566 (12)	0.0264 (7)
H11	0.8257	1.1480	−0.1141	0.032*
C12	0.6822 (2)	1.2436 (5)	−0.06095 (13)	0.0235 (7)
H12	0.6421	1.3704	−0.0894	0.028*
C13	0.6326 (2)	1.1905 (5)	−0.00504 (12)	0.0205 (7)
H13	0.5579	1.2807	0.0049	0.025*

	U11	U22	U33	U12	U13	U23
C1	0.0195 (15)	0.0157 (16)	0.0256 (18)	−0.0019 (12)	0.0003 (13)	0.0007 (13)
O1	0.0434 (12)	0.0128 (11)	0.0326 (12)	0.0013 (8)	0.0142 (9)	0.0032 (8)
C2	0.0229 (15)	0.0104 (13)	0.0197 (16)	−0.0033 (12)	0.0005 (13)	−0.0007 (11)
C7	0.0246 (16)	0.0188 (15)	0.0253 (18)	−0.0012 (13)	0.0015 (14)	−0.0003 (12)
F1	0.0306 (11)	0.0303 (11)	0.0279 (12)	0.0111 (9)	0.0007 (9)	0.0041 (8)
C3	0.0245 (17)	0.0213 (16)	0.0268 (19)	−0.0004 (12)	0.0028 (14)	−0.0024 (12)
F1'	0.050 (8)	0.044 (8)	0.046 (9)	0.018 (6)	0.011 (6)	0.015 (6)
C4	0.0394 (18)	0.0271 (16)	0.0236 (19)	−0.0024 (14)	−0.0015 (15)	0.0038 (13)
C5	0.0409 (18)	0.0276 (16)	0.0170 (17)	−0.0117 (14)	0.0051 (14)	0.0006 (12)
C6	0.0278 (16)	0.0292 (16)	0.0246 (18)	−0.0018 (13)	0.0060 (13)	−0.0021 (13)
N1	0.0258 (13)	0.0101 (13)	0.0239 (15)	0.0023 (11)	0.0060 (11)	0.0022 (11)
C8	0.0203 (15)	0.0113 (14)	0.0206 (17)	−0.0051 (11)	0.0028 (13)	−0.0002 (11)
C9	0.0212 (15)	0.0125 (14)	0.0216 (17)	−0.0031 (11)	−0.0008 (13)	−0.0027 (11)
C14	0.0244 (15)	0.0227 (15)	0.0259 (18)	0.0031 (12)	0.0022 (13)	−0.0016 (12)
C10	0.0234 (15)	0.0241 (15)	0.0255 (18)	0.0002 (13)	0.0040 (13)	−0.0049 (13)
C11	0.0305 (17)	0.0291 (16)	0.0199 (17)	−0.0047 (13)	0.0043 (14)	−0.0017 (13)
C12	0.0295 (16)	0.0188 (15)	0.0216 (18)	−0.0042 (13)	−0.0033 (13)	0.0034 (12)
C13	0.0173 (14)	0.0163 (14)	0.0278 (19)	−0.0020 (11)	−0.0007 (13)	−0.0003 (12)

C1—O1	1.231 (3)	N1—C8	1.416 (3)
C1—N1	1.347 (3)	N1—HN1	0.85 (3)
C1—C2	1.501 (3)	C8—C13	1.397 (3)
C2—C3	1.386 (3)	C8—C9	1.404 (3)
C2—C7	1.390 (3)	C9—C10	1.385 (4)
C7—F1'	1.292 (10)	C9—C14	1.512 (3)
C7—C6	1.375 (4)	C14—H14A	0.9800
C7—H7	0.9500	C14—H14B	0.9800
F1—C3	1.354 (3)	C14—H14C	0.9800
C3—C4	1.370 (4)	C10—C11	1.384 (3)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.385 (4)	C11—C12	1.385 (4)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.379 (4)	C12—C13	1.375 (4)
C5—H5	0.9500	C12—H12	0.9500
C6—H6	0.9500	C13—H13	0.9500
O1—C1—N1	123.9 (2)	C13—C8—N1	121.4 (2)
O1—C1—C2	119.7 (2)	C9—C8—N1	118.4 (2)
N1—C1—C2	116.5 (2)	C13—C8—C14i	76.61 (13)
C3—C2—C7	116.7 (2)	C9—C8—C14i	90.97 (14)
C3—C2—C1	124.5 (2)	N1—C8—C14i	103.13 (14)
C7—C2—C1	118.6 (2)	C10—C9—C8	117.7 (2)
F1'—C7—C6	118.8 (6)	C10—C9—C14	121.2 (2)
F1'—C7—C2	119.7 (6)	C8—C9—C14	121.1 (2)
C6—C7—C2	121.4 (2)	C9—C14—H14A	109.5
C6—C7—H7	119.3	C9—C14—H14B	109.5
C2—C7—H7	119.3	H14A—C14—H14B	109.5
F1—C3—C4	117.6 (2)	C9—C14—H14C	109.5
F1—C3—C2	119.1 (2)	H14A—C14—H14C	109.5
C4—C3—C2	123.2 (2)	H14B—C14—H14C	109.5
C4—C3—H3	118.4	C11—C10—C9	122.1 (2)
C2—C3—H3	118.4	C11—C10—H10	118.9
C3—C4—C5	118.4 (3)	C9—C10—H10	118.9
C3—C4—H4	120.8	C10—C11—C12	119.5 (3)
C5—C4—H4	120.8	C10—C11—H11	120.2
C6—C5—C4	120.2 (3)	C12—C11—H11	120.2
C6—C5—H5	119.9	C13—C12—C11	119.8 (2)
C4—C5—H5	119.9	C13—C12—H12	120.1
C5—C6—C7	120.0 (3)	C11—C12—H12	120.1
C5—C6—H6	120.0	C12—C13—C8	120.6 (2)
C7—C6—H6	120.0	C12—C13—C14i	88.08 (15)
C1—N1—C8	125.5 (2)	C8—C13—C14i	81.74 (14)
C1—N1—HN1	115.0 (18)	C12—C13—H13	119.7
C8—N1—HN1	119.2 (18)	C8—C13—H13	119.7
C13—C8—C9	120.2 (2)	C14i—C13—H13	100.3
O1—C1—C2—C3	−140.1 (3)	C1—N1—C8—C13	−37.4 (3)
N1—C1—C2—C3	39.8 (3)	C1—N1—C8—C9	143.2 (2)
O1—C1—C2—C7	36.3 (3)	C1—N1—C8—C14i	44.8 (3)
N1—C1—C2—C7	−143.8 (2)	C13—C8—C9—C10	0.0 (3)
C3—C2—C7—F1'	176.9 (6)	N1—C8—C9—C10	179.4 (2)
C1—C2—C7—F1'	0.3 (7)	C14i—C8—C9—C10	−75.1 (2)
C3—C2—C7—C6	−1.4 (3)	C13—C8—C9—C14	179.9 (2)
C1—C2—C7—C6	−178.0 (2)	N1—C8—C9—C14	−0.6 (3)
C7—C2—C3—F1	−176.9 (2)	C14i—C8—C9—C14	104.9 (2)
C1—C2—C3—F1	−0.5 (3)	C8—C9—C10—C11	0.6 (3)
C7—C2—C3—C4	0.5 (4)	C14—C9—C10—C11	−179.4 (2)
C1—C2—C3—C4	176.9 (2)	C9—C10—C11—C12	−0.7 (4)
F1—C3—C4—C5	178.2 (2)	C10—C11—C12—C13	0.3 (4)
C2—C3—C4—C5	0.7 (4)	C11—C12—C13—C8	0.3 (3)
C3—C4—C5—C6	−1.0 (4)	C11—C12—C13—C14i	79.5 (2)
C4—C5—C6—C7	0.2 (4)	C9—C8—C13—C12	−0.4 (3)
F1'—C7—C6—C5	−177.3 (6)	N1—C8—C13—C12	−179.8 (2)
C2—C7—C6—C5	1.0 (4)	C14i—C8—C13—C12	82.8 (2)
O1—C1—N1—C8	−0.8 (4)	C9—C8—C13—C14i	−83.2 (2)
C2—C1—N1—C8	179.30 (19)	N1—C8—C13—C14i	97.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ii	0.85 (3)	2.08 (3)	2.887 (3)	158 (2)
C6—H6···F1'iii	0.95	2.60	3.219 (11)	123
C12—H12···O1iv	0.95	2.63	3.434 (3)	143
C12—H12···F1'iv	0.95	2.40	3.287 (11)	154
C14—H14C···Cg1ii	0.98	2.98	3.702 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.85 (3)	2.08 (3)	2.887 (3)	158 (2)
C6—H6⋯F1′ii	0.95	2.60	3.219 (11)	123
C12—H12⋯O1iii	0.95	2.63	3.434 (3)	143
C12—H12⋯F1′iii	0.95	2.40	3.287 (11)	154
C14—H14C⋯Cg1i	0.98	2.98	3.702 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C8–C13 benzene ring.