2-Fluoro-N-(4-methoxy-phen-yl)benzamide.

In the title compound, C(14)H(12)FNO(2), the fluoro-benzene and methoxy-benzene rings are inclined at 27.06 (7) and 23.86 (7)°, respectively, to the amide portion of the mol-ecule and at 3.46 (9)° to one another. The meth-oxy substituent lies close to the methoxy-benzene ring plane, with a maximum deviation of 0.152 (3) Å for the methyl C atom. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into rows along a. Weak C-H⋯O and C-H⋯F inter-actions further stabilize the packing, forming corrugated sheets in the bc plane.

Related literature

For the biological activity of benzamides and related compounds and their use in organic synthesis, see: Vega-Noverola et al. (1989 ▶); Yoo et al. (2005 ▶); Saeed et al. (2008 ▶). For related structures, see: Saeed et al. (2008 ▶); Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶); Cockroft et al. (2007 ▶); Spitaleri et al. (2004 ▶).

Experimental

Crystal data

C14H12FNO2

M = 245.25

Orthorhombic,

a = 5.2901 (2) Å

b = 6.6435 (3) Å

c = 31.7823 (11) Å

V = 1116.98 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 89 K

0.30 × 0.23 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.853, T max = 0.996

19727 measured reflections

2185 independent reflections

1980 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.06

2185 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.24 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 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; 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, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008927/si2159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008927/si2159Isup2.hkl

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

C14H12FNO2	F(000) = 512
Mr = 245.25	Dx = 1.458 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5036 reflections
a = 5.2901 (2) Å	θ = 3.1–31.4°
b = 6.6435 (3) Å	µ = 0.11 mm−1
c = 31.7823 (11) Å	T = 89 K
V = 1116.98 (8) Å3	Rectangular, colourless
Z = 4	0.30 × 0.23 × 0.04 mm

Bruker APEXII CCD area-detector diffractometer	2185 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω scans	θmax = 31.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
Tmin = 0.853, Tmax = 0.996	k = −8→9
19727 measured reflections	l = −46→45

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: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1314P] where P = (Fo2 + 2Fc2)/3
2185 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 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
N1	0.8287 (2)	0.30490 (19)	0.12515 (4)	0.0120 (2)
H1N	0.681 (4)	0.274 (3)	0.1327 (6)	0.018 (5)*
C1	1.0253 (3)	0.1910 (2)	0.13830 (4)	0.0122 (3)
O1	1.2460 (2)	0.21863 (18)	0.12733 (3)	0.0195 (2)
C2	0.9628 (3)	0.0195 (2)	0.16750 (4)	0.0113 (2)
C3	0.7617 (3)	0.0129 (2)	0.19568 (4)	0.0138 (3)
F1	0.60670 (19)	0.17461 (15)	0.19944 (3)	0.0211 (2)
C4	0.7144 (3)	−0.1504 (3)	0.22153 (4)	0.0172 (3)
H4	0.5746	−0.1494	0.2403	0.021*
C5	0.8740 (3)	−0.3153 (2)	0.21964 (5)	0.0175 (3)
H5	0.8427	−0.4295	0.2369	0.021*
C6	1.0809 (3)	−0.3137 (2)	0.19238 (5)	0.0176 (3)
H6	1.1921	−0.4259	0.1912	0.021*
C7	1.1234 (3)	−0.1472 (2)	0.16695 (4)	0.0151 (3)
H7	1.2656	−0.1467	0.1487	0.018*
C8	0.8450 (3)	0.4821 (2)	0.10044 (4)	0.0109 (2)
C9	0.6527 (3)	0.6247 (2)	0.10514 (4)	0.0124 (3)
H9	0.5154	0.5977	0.1236	0.015*
C10	0.6600 (3)	0.8048 (2)	0.08330 (4)	0.0127 (3)
H10	0.5290	0.9010	0.0869	0.015*
C11	0.8609 (3)	0.8447 (2)	0.05591 (4)	0.0113 (3)
C12	1.0490 (3)	0.7011 (2)	0.05019 (4)	0.0120 (3)
H12	1.1830	0.7261	0.0310	0.014*
C13	1.0418 (3)	0.5203 (2)	0.07255 (4)	0.0123 (3)
H13	1.1716	0.4232	0.0687	0.015*
O2	0.8549 (2)	1.02823 (15)	0.03604 (3)	0.0144 (2)
C14	1.0690 (3)	1.0759 (2)	0.01050 (5)	0.0159 (3)
H14A	1.2233	1.0662	0.0274	0.024*
H14B	1.0517	1.2132	−0.0004	0.024*
H14C	1.0788	0.9811	−0.0131	0.024*

	U11	U22	U33	U12	U13	U23
N1	0.0097 (5)	0.0108 (5)	0.0155 (5)	0.0003 (5)	0.0019 (4)	0.0030 (4)
C1	0.0124 (6)	0.0103 (6)	0.0138 (6)	−0.0004 (5)	0.0005 (5)	0.0013 (5)
O1	0.0117 (5)	0.0212 (6)	0.0255 (5)	0.0005 (4)	0.0013 (4)	0.0099 (5)
C2	0.0125 (6)	0.0102 (6)	0.0112 (5)	−0.0008 (5)	−0.0003 (5)	0.0000 (5)
C3	0.0124 (6)	0.0157 (6)	0.0132 (6)	0.0011 (5)	−0.0009 (5)	−0.0002 (5)
F1	0.0214 (5)	0.0231 (5)	0.0189 (4)	0.0094 (4)	0.0071 (4)	0.0027 (4)
C4	0.0154 (6)	0.0228 (8)	0.0134 (6)	−0.0033 (6)	0.0003 (5)	0.0036 (6)
C5	0.0194 (7)	0.0161 (7)	0.0169 (6)	−0.0054 (6)	−0.0028 (5)	0.0056 (6)
C6	0.0198 (7)	0.0132 (7)	0.0200 (6)	0.0019 (6)	−0.0024 (6)	0.0027 (6)
C7	0.0159 (6)	0.0139 (6)	0.0156 (6)	0.0020 (6)	0.0005 (5)	0.0006 (5)
C8	0.0117 (6)	0.0087 (5)	0.0122 (5)	0.0001 (5)	−0.0013 (5)	0.0005 (5)
C9	0.0108 (6)	0.0125 (6)	0.0140 (6)	0.0000 (5)	0.0022 (5)	−0.0004 (5)
C10	0.0116 (6)	0.0114 (6)	0.0150 (6)	0.0013 (5)	0.0006 (5)	−0.0002 (5)
C11	0.0124 (6)	0.0091 (6)	0.0123 (5)	−0.0005 (5)	−0.0018 (5)	0.0008 (5)
C12	0.0110 (5)	0.0123 (6)	0.0127 (5)	0.0003 (5)	0.0010 (5)	0.0009 (5)
C13	0.0119 (6)	0.0112 (6)	0.0139 (6)	0.0020 (5)	0.0013 (5)	0.0001 (5)
O2	0.0145 (5)	0.0108 (5)	0.0178 (5)	0.0019 (4)	0.0029 (4)	0.0042 (4)
C14	0.0146 (6)	0.0133 (6)	0.0199 (6)	−0.0009 (6)	0.0029 (6)	0.0047 (5)

N1—C1	1.3522 (19)	C8—C13	1.3909 (18)
N1—C8	1.4177 (17)	C8—C9	1.3980 (19)
N1—H1N	0.84 (2)	C9—C10	1.3835 (19)
C1—O1	1.2317 (17)	C9—H9	0.9500
C1—C2	1.5066 (19)	C10—C11	1.3992 (19)
C2—C3	1.3914 (19)	C10—H10	0.9500
C2—C7	1.396 (2)	C11—O2	1.3734 (16)
C3—F1	1.3567 (17)	C11—C12	1.3902 (19)
C3—C4	1.384 (2)	C12—C13	1.3959 (19)
C4—C5	1.384 (2)	C12—H12	0.9500
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.396 (2)	O2—C14	1.4289 (18)
C5—H5	0.9500	C14—H14A	0.9800
C6—C7	1.388 (2)	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C7—H7	0.9500
C1—N1—C8	126.09 (12)	C13—C8—N1	123.38 (12)
C1—N1—H1N	119.3 (14)	C9—C8—N1	117.36 (12)
C8—N1—H1N	114.6 (14)	C10—C9—C8	120.82 (13)
O1—C1—N1	123.93 (13)	C10—C9—H9	119.6
O1—C1—C2	119.66 (13)	C8—C9—H9	119.6
N1—C1—C2	116.40 (12)	C9—C10—C11	119.81 (13)
C3—C2—C7	116.65 (13)	C9—C10—H10	120.1
C3—C2—C1	126.02 (13)	C11—C10—H10	120.1
C7—C2—C1	117.31 (12)	O2—C11—C12	124.45 (12)
F1—C3—C4	117.34 (13)	O2—C11—C10	115.90 (12)
F1—C3—C2	119.61 (13)	C12—C11—C10	119.66 (12)
C4—C3—C2	123.02 (14)	C11—C12—C13	120.29 (13)
C3—C4—C5	118.98 (14)	C11—C12—H12	119.9
C3—C4—H4	120.5	C13—C12—H12	119.9
C5—C4—H4	120.5	C8—C13—C12	120.13 (13)
C4—C5—C6	119.95 (14)	C8—C13—H13	119.9
C4—C5—H5	120.0	C12—C13—H13	119.9
C6—C5—H5	120.0	C11—O2—C14	116.09 (11)
C7—C6—C5	119.60 (14)	O2—C14—H14A	109.5
C7—C6—H6	120.2	O2—C14—H14B	109.5
C5—C6—H6	120.2	H14A—C14—H14B	109.5
C6—C7—C2	121.77 (14)	O2—C14—H14C	109.5
C6—C7—H7	119.1	H14A—C14—H14C	109.5
C2—C7—H7	119.1	H14B—C14—H14C	109.5
C13—C8—C9	119.26 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.34 (2)	3.1366 (17)	158.5 (17)
C4—H4···F1ii	0.95	2.44	3.2472 (17)	143
C14—H14B···O2iii	0.98	2.61	3.3753 (18)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.34 (2)	3.1366 (17)	158.5 (17)
C4—H4⋯F1ii	0.95	2.44	3.2472 (17)	143
C14—H14B⋯O2iii	0.98	2.61	3.3753 (18)	135

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C3–C8 benzene ring.