3-Fluoro-N-(p-tol-yl)benzamide.

In the crystal structure of the title compound, C(14)H(12)FNO, the amide -NHCO- mean plane makes dihedral angles of 28.6 (2) and 37.5 (2)° with the mean planes through the fluoro-benzene and methyl-benzene units, respectively. The dihedral angle between the two benzene ring mean planes is 65.69 (10)°. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonds and stack along the b axis.

Related literature

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

Experimental

Crystal data

C14H12FNO

M = 229.25

Monoclinic,

a = 27.645 (3) Å

b = 5.2618 (6) Å

c = 15.892 (2) Å

β = 93.519 (3)°

V = 2307.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 223 (1) K

0.40 × 0.35 × 0.18 mm

Data collection

Rigaku R-AXIS RAPIDII diffractometer

Absorption correction: numerical (; Higashi, 1999 ▶) T min = 0.968, T max = 0.983

13860 measured reflections

3357 independent reflections

1779 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.240

S = 1.01

3357 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803225X/su2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803225X/su2064Isup2.hkl

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

C14H12FNO	F(000) = 960.00
Mr = 229.25	Dx = 1.320 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 7127 reflections
a = 27.645 (3) Å	θ = 3.0–30.0°
b = 5.2618 (6) Å	µ = 0.09 mm−1
c = 15.892 (2) Å	T = 223 K
β = 93.519 (3)°	Block, colorless
V = 2307.3 (5) Å3	0.40 × 0.35 × 0.18 mm
Z = 8

Rigaku R-AXIS RAPIDII diffractometer	1779 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.055
ω scans	θmax = 30.0°
Absorption correction: numerical (ABSCOR; Higashi, 1999)	h = −38→38
Tmin = 0.968, Tmax = 0.983	k = −6→7
13860 measured reflections	l = −22→22
3357 independent reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.1335P)2] where P = (Fo2 + 2Fc2)/3
3357 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.20 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
F1	0.69906 (5)	0.5995 (3)	0.23465 (10)	0.0965 (5)
O1	0.52251 (5)	0.6096 (3)	0.14071 (11)	0.0781 (5)
N1	0.50521 (6)	0.1882 (4)	0.12722 (11)	0.0639 (5)
C1	0.58887 (6)	0.3226 (4)	0.14164 (11)	0.0594 (5)
C2	0.62009 (7)	0.4878 (4)	0.18591 (12)	0.0656 (5)
H2	0.6081	0.6327	0.2122	0.079*
C3	0.66868 (8)	0.4361 (4)	0.19066 (14)	0.0703 (5)
C4	0.68819 (7)	0.2292 (5)	0.15293 (14)	0.0745 (6)
H4	0.7217	0.1984	0.1576	0.089*
C5	0.65712 (7)	0.0677 (4)	0.10794 (14)	0.0732 (6)
H5	0.6697	−0.0741	0.0807	0.088*
C6	0.60772 (7)	0.1105 (4)	0.10214 (12)	0.0657 (5)
H6	0.5869	−0.0026	0.0718	0.079*
C7	0.53603 (7)	0.3860 (4)	0.13667 (11)	0.0608 (5)
C8	0.45358 (7)	0.2026 (4)	0.11934 (11)	0.0599 (5)
C9	0.42706 (7)	0.0146 (4)	0.15561 (13)	0.0675 (5)
H9	0.4431	−0.1164	0.1865	0.081*
C10	0.37703 (7)	0.0181 (4)	0.14673 (13)	0.0729 (6)
H10	0.3594	−0.1125	0.1712	0.087*
C11	0.35222 (7)	0.2093 (4)	0.10264 (11)	0.0675 (5)
C12	0.37940 (7)	0.3956 (4)	0.06655 (13)	0.0705 (6)
H12	0.3634	0.5269	0.0359	0.085*
C13	0.42967 (8)	0.3940 (4)	0.07434 (13)	0.0704 (5)
H13	0.4474	0.5228	0.0491	0.085*
C14	0.29774 (8)	0.2111 (6)	0.09397 (16)	0.0916 (8)
H14A	0.2850	0.2043	0.1495	0.137*
H14B	0.2864	0.0647	0.0613	0.137*
H14C	0.2867	0.3655	0.0655	0.137*
H1	0.5158 (7)	0.055 (4)	0.1353 (12)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
F1	0.0752 (8)	0.0995 (10)	0.1131 (11)	−0.0114 (7)	−0.0082 (7)	−0.0173 (8)
O1	0.0711 (9)	0.0616 (9)	0.1023 (12)	0.0027 (7)	0.0107 (7)	−0.0059 (7)
N1	0.0633 (9)	0.0566 (9)	0.0719 (10)	0.0009 (9)	0.0063 (7)	0.0030 (8)
C1	0.0655 (11)	0.0619 (10)	0.0518 (9)	−0.0016 (8)	0.0112 (7)	0.0049 (7)
C2	0.0692 (12)	0.0646 (11)	0.0636 (11)	−0.0002 (10)	0.0087 (8)	−0.0013 (9)
C3	0.0681 (12)	0.0758 (13)	0.0669 (11)	−0.0049 (10)	0.0035 (9)	0.0027 (9)
C4	0.0648 (11)	0.0822 (14)	0.0779 (13)	0.0043 (11)	0.0148 (9)	0.0089 (11)
C5	0.0746 (13)	0.0759 (13)	0.0709 (12)	0.0088 (11)	0.0190 (9)	−0.0006 (10)
C6	0.0705 (11)	0.0665 (11)	0.0610 (10)	0.0004 (9)	0.0127 (8)	−0.0028 (8)
C7	0.0625 (10)	0.0636 (11)	0.0570 (10)	0.0008 (9)	0.0088 (8)	−0.0002 (8)
C8	0.0605 (10)	0.0645 (10)	0.0551 (9)	−0.0013 (8)	0.0076 (7)	−0.0050 (8)
C9	0.0657 (11)	0.0717 (12)	0.0659 (11)	0.0011 (9)	0.0100 (8)	0.0067 (9)
C10	0.0717 (12)	0.0787 (13)	0.0694 (12)	−0.0049 (11)	0.0141 (9)	0.0063 (10)
C11	0.0635 (11)	0.0852 (14)	0.0540 (10)	0.0019 (10)	0.0058 (8)	−0.0085 (9)
C12	0.0712 (12)	0.0729 (13)	0.0663 (12)	0.0063 (10)	−0.0044 (9)	0.0028 (9)
C13	0.0763 (12)	0.0725 (12)	0.0626 (11)	−0.0045 (10)	0.0041 (9)	0.0088 (9)
C14	0.0683 (13)	0.126 (2)	0.0807 (15)	0.0047 (14)	0.0050 (11)	−0.0041 (14)

F1—C3	1.364 (2)	C6—H6	0.9400
O1—C7	1.238 (2)	C8—C9	1.378 (3)
N1—C7	1.347 (3)	C8—C13	1.380 (3)
N1—C8	1.427 (2)	C9—C10	1.382 (3)
N1—H1	0.77 (2)	C9—H9	0.9400
C1—C2	1.386 (3)	C10—C11	1.384 (3)
C1—C6	1.397 (3)	C10—H10	0.9400
C1—C7	1.496 (3)	C11—C12	1.381 (3)
C2—C3	1.368 (3)	C11—C14	1.504 (3)
C2—H2	0.9400	C12—C13	1.388 (3)
C3—C4	1.370 (3)	C12—H12	0.9400
C4—C5	1.377 (3)	C13—H13	0.9400
C4—H4	0.9400	C14—H14A	0.9700
C5—C6	1.382 (3)	C14—H14B	0.9700
C5—H5	0.9400	C14—H14C	0.9700
C7—N1—C8	126.25 (17)	C9—C8—C13	119.37 (18)
C7—N1—H1	117.0 (15)	C9—C8—N1	118.68 (17)
C8—N1—H1	115.6 (15)	C13—C8—N1	121.91 (17)
C2—C1—C6	119.43 (17)	C8—C9—C10	120.14 (19)
C2—C1—C7	117.56 (17)	C8—C9—H9	119.9
C6—C1—C7	122.99 (17)	C10—C9—H9	119.9
C3—C2—C1	118.83 (19)	C9—C10—C11	121.58 (19)
C3—C2—H2	120.6	C9—C10—H10	119.2
C1—C2—H2	120.6	C11—C10—H10	119.2
F1—C3—C2	118.34 (19)	C12—C11—C10	117.44 (17)
F1—C3—C4	118.61 (19)	C12—C11—C14	121.6 (2)
C2—C3—C4	123.05 (19)	C10—C11—C14	120.9 (2)
C3—C4—C5	117.92 (19)	C11—C12—C13	121.75 (18)
C3—C4—H4	121.0	C11—C12—H12	119.1
C5—C4—H4	121.0	C13—C12—H12	119.1
C4—C5—C6	121.1 (2)	C8—C13—C12	119.71 (18)
C4—C5—H5	119.4	C8—C13—H13	120.1
C6—C5—H5	119.4	C12—C13—H13	120.1
C5—C6—C1	119.65 (19)	C11—C14—H14A	109.5
C5—C6—H6	120.2	C11—C14—H14B	109.5
C1—C6—H6	120.2	H14A—C14—H14B	109.5
O1—C7—N1	123.30 (18)	C11—C14—H14C	109.5
O1—C7—C1	120.43 (17)	H14A—C14—H14C	109.5
N1—C7—C1	116.27 (17)	H14B—C14—H14C	109.5
C6—C1—C2—C3	−0.9 (3)	C2—C1—C7—N1	−152.62 (17)
C7—C1—C2—C3	−179.24 (17)	C6—C1—C7—N1	29.1 (3)
C1—C2—C3—F1	−179.77 (18)	C7—N1—C8—C9	−144.0 (2)
C1—C2—C3—C4	0.6 (3)	C7—N1—C8—C13	38.1 (3)
F1—C3—C4—C5	−179.27 (19)	C13—C8—C9—C10	0.1 (3)
C2—C3—C4—C5	0.3 (3)	N1—C8—C9—C10	−177.82 (17)
C3—C4—C5—C6	−1.0 (3)	C8—C9—C10—C11	−0.8 (3)
C4—C5—C6—C1	0.8 (3)	C9—C10—C11—C12	0.9 (3)
C2—C1—C6—C5	0.2 (3)	C9—C10—C11—C14	−179.65 (19)
C7—C1—C6—C5	178.47 (18)	C10—C11—C12—C13	−0.5 (3)
C8—N1—C7—O1	0.9 (3)	C14—C11—C12—C13	−179.9 (2)
C8—N1—C7—C1	−178.66 (15)	C9—C8—C13—C12	0.3 (3)
C2—C1—C7—O1	27.8 (3)	N1—C8—C13—C12	178.19 (17)
C6—C1—C7—O1	−150.5 (2)	C11—C12—C13—C8	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.77 (2)	2.35 (2)	3.087 (3)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.77 (2)	2.35 (2)	3.087 (3)	161 (2)

Symmetry code: (i) .