N-(4-Cyano-phen-yl)-2,6-difluoro-benzamide.

In the title compound, C(14)H(8)F(2)N(2)O, the amide plane is inclined at dihedral angles of 28.12 (12) and 32.89 (12)° with respect to the two benzene rings; the dihedral angle between the two rings is 5.58 (5)°. In the crystal, inter-molecular N-H⋯O and C-H⋯F hydrogen bonds link adjacent mol-ecules into a double-chain structure along the b axis.

Related literature

For general background to and applications of the title compound, see: Ashwood et al. (1990 ▶); Kees et al. (1989 ▶); Ragavan et al. (2010 ▶); Carmellino et al. (1994 ▶); Rauko et al. (2001 ▶). For a closely related benzamide structure, see: Cronin et al. (2000 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H8F2N2O

M = 258.22

Monoclinic,

a = 9.3377 (11) Å

b = 5.0793 (6) Å

c = 24.500 (3) Å

β = 100.202 (3)°

V = 1143.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.27 × 0.14 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.984

27219 measured reflections

4135 independent reflections

3176 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.03

4135 reflections

204 parameters

All H-atom parameters refined

Δρmax = 0.39 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046507/is2630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046507/is2630Isup2.hkl

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

C14H8F2N2O	F(000) = 528
Mr = 258.22	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5020 reflections
a = 9.3377 (11) Å	θ = 2.2–31.3°
b = 5.0793 (6) Å	µ = 0.12 mm−1
c = 24.500 (3) Å	T = 100 K
β = 100.202 (3)°	Block, yellow
V = 1143.6 (2) Å3	0.27 × 0.14 × 0.14 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4135 independent reflections
Radiation source: fine-focus sealed tube	3176 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 32.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.968, Tmax = 0.984	k = −7→7
27219 measured reflections	l = −36→37

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.2429P] where P = (Fo2 + 2Fc2)/3
4135 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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	0.81277 (8)	0.06726 (14)	0.14252 (3)	0.03127 (18)
F2	1.02229 (7)	0.75952 (13)	0.05423 (3)	0.02670 (16)
O1	0.76102 (9)	0.12482 (15)	0.03141 (3)	0.02539 (18)
N1	0.75319 (9)	0.56187 (17)	0.01066 (3)	0.01774 (17)
N2	0.33842 (13)	0.5436 (2)	−0.24586 (5)	0.0384 (3)
C1	0.91364 (12)	0.2568 (2)	0.14216 (4)	0.0207 (2)
C2	1.01589 (13)	0.2889 (2)	0.18972 (5)	0.0252 (2)
C3	1.11850 (12)	0.4873 (2)	0.19138 (5)	0.0246 (2)
C4	1.11804 (11)	0.6494 (2)	0.14589 (5)	0.0228 (2)
C5	1.01538 (11)	0.6060 (2)	0.09898 (4)	0.01910 (19)
C6	0.90844 (10)	0.41080 (19)	0.09449 (4)	0.01688 (18)
C7	0.80070 (11)	0.35107 (19)	0.04285 (4)	0.01768 (19)
C8	0.66236 (11)	0.55108 (19)	−0.04175 (4)	0.01768 (19)
C9	0.67895 (12)	0.7489 (2)	−0.07969 (4)	0.0207 (2)
C10	0.59456 (12)	0.7492 (2)	−0.13217 (5)	0.0224 (2)
C11	0.49135 (11)	0.5511 (2)	−0.14682 (4)	0.0220 (2)
C12	0.47172 (12)	0.3569 (2)	−0.10873 (5)	0.0231 (2)
C13	0.55706 (11)	0.3555 (2)	−0.05623 (4)	0.0209 (2)
C14	0.40564 (13)	0.5474 (2)	−0.20187 (5)	0.0275 (2)
H1N1	0.7848 (16)	0.716 (3)	0.0216 (6)	0.031 (4)*
H2	1.0120 (16)	0.173 (3)	0.2194 (6)	0.031 (4)*
H3	1.1931 (16)	0.507 (3)	0.2249 (6)	0.031 (4)*
H4	1.1877 (17)	0.787 (3)	0.1456 (6)	0.028 (4)*
H9	0.7526 (15)	0.877 (3)	−0.0683 (6)	0.022 (3)*
H10	0.6115 (15)	0.879 (3)	−0.1573 (6)	0.026 (4)*
H12	0.3999 (17)	0.227 (3)	−0.1180 (6)	0.031 (4)*
H13	0.5408 (15)	0.221 (3)	−0.0309 (6)	0.026 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0336 (4)	0.0283 (4)	0.0293 (4)	−0.0134 (3)	−0.0015 (3)	0.0072 (3)
F2	0.0242 (3)	0.0266 (3)	0.0274 (3)	−0.0063 (3)	−0.0006 (3)	0.0092 (3)
O1	0.0327 (4)	0.0133 (3)	0.0260 (4)	−0.0007 (3)	−0.0061 (3)	−0.0027 (3)
N1	0.0212 (4)	0.0123 (4)	0.0175 (4)	−0.0004 (3)	−0.0026 (3)	−0.0018 (3)
N2	0.0415 (6)	0.0392 (6)	0.0283 (5)	0.0086 (5)	−0.0108 (5)	−0.0071 (5)
C1	0.0227 (5)	0.0172 (5)	0.0215 (5)	−0.0029 (4)	0.0021 (4)	0.0004 (3)
C2	0.0283 (5)	0.0265 (5)	0.0195 (5)	−0.0012 (4)	0.0011 (4)	0.0017 (4)
C3	0.0235 (5)	0.0285 (6)	0.0198 (5)	−0.0004 (4)	−0.0018 (4)	−0.0042 (4)
C4	0.0190 (5)	0.0222 (5)	0.0257 (5)	−0.0025 (4)	−0.0003 (4)	−0.0029 (4)
C5	0.0187 (4)	0.0174 (4)	0.0206 (4)	0.0002 (3)	0.0020 (3)	0.0004 (3)
C6	0.0173 (4)	0.0145 (4)	0.0179 (4)	0.0004 (3)	0.0007 (3)	−0.0023 (3)
C7	0.0188 (4)	0.0144 (4)	0.0187 (4)	0.0009 (3)	0.0002 (3)	−0.0014 (3)
C8	0.0186 (4)	0.0156 (4)	0.0176 (4)	0.0020 (3)	−0.0003 (3)	−0.0030 (3)
C9	0.0240 (5)	0.0170 (4)	0.0194 (5)	−0.0008 (4)	−0.0007 (4)	−0.0015 (3)
C10	0.0264 (5)	0.0202 (5)	0.0189 (5)	0.0021 (4)	−0.0002 (4)	−0.0006 (4)
C11	0.0214 (5)	0.0226 (5)	0.0195 (5)	0.0049 (4)	−0.0037 (4)	−0.0055 (4)
C12	0.0196 (5)	0.0206 (5)	0.0266 (5)	−0.0003 (4)	−0.0030 (4)	−0.0051 (4)
C13	0.0206 (5)	0.0181 (5)	0.0224 (5)	−0.0004 (4)	−0.0008 (4)	−0.0012 (4)
C14	0.0279 (5)	0.0259 (5)	0.0254 (5)	0.0056 (4)	−0.0043 (4)	−0.0057 (4)

F1—C1	1.3480 (12)	C4—H4	0.956 (15)
F2—C5	1.3563 (12)	C5—C6	1.3975 (14)
O1—C7	1.2246 (12)	C6—C7	1.5014 (13)
N1—C7	1.3569 (13)	C8—C9	1.3961 (14)
N1—C8	1.4091 (12)	C8—C13	1.3985 (14)
N1—H1N1	0.860 (16)	C9—C10	1.3839 (15)
N2—C14	1.1474 (15)	C9—H9	0.953 (14)
C1—C2	1.3791 (15)	C10—C11	1.3955 (15)
C1—C6	1.3992 (14)	C10—H10	0.933 (15)
C2—C3	1.3861 (16)	C11—C12	1.3922 (16)
C2—H2	0.943 (15)	C11—C14	1.4414 (15)
C3—C4	1.3849 (16)	C12—C13	1.3880 (15)
C3—H3	0.984 (15)	C12—H12	0.939 (15)
C4—C5	1.3777 (14)	C13—H13	0.952 (15)
C7—N1—C8	125.52 (8)	O1—C7—C6	120.86 (9)
C7—N1—H1N1	118.5 (10)	N1—C7—C6	115.57 (8)
C8—N1—H1N1	115.9 (10)	C9—C8—C13	119.89 (9)
F1—C1—C2	117.31 (9)	C9—C8—N1	117.32 (9)
F1—C1—C6	118.94 (9)	C13—C8—N1	122.78 (9)
C2—C1—C6	123.75 (10)	C10—C9—C8	120.48 (10)
C1—C2—C3	118.83 (10)	C10—C9—H9	122.3 (8)
C1—C2—H2	117.6 (9)	C8—C9—H9	117.2 (8)
C3—C2—H2	123.6 (9)	C9—C10—C11	119.47 (10)
C4—C3—C2	120.33 (10)	C9—C10—H10	118.6 (9)
C4—C3—H3	120.8 (9)	C11—C10—H10	121.9 (9)
C2—C3—H3	118.8 (9)	C12—C11—C10	120.36 (9)
C5—C4—C3	118.60 (10)	C12—C11—C14	120.06 (10)
C5—C4—H4	119.0 (9)	C10—C11—C14	119.58 (10)
C3—C4—H4	122.3 (9)	C13—C12—C11	120.18 (10)
F2—C5—C4	117.17 (9)	C13—C12—H12	119.3 (9)
F2—C5—C6	118.68 (9)	C11—C12—H12	120.5 (9)
C4—C5—C6	124.13 (10)	C12—C13—C8	119.60 (10)
C5—C6—C1	114.34 (9)	C12—C13—H13	118.5 (9)
C5—C6—C7	124.92 (9)	C8—C13—H13	121.9 (9)
C1—C6—C7	120.62 (9)	N2—C14—C11	179.41 (13)
O1—C7—N1	123.57 (9)
F1—C1—C2—C3	−178.04 (10)	C1—C6—C7—O1	−31.41 (15)
C6—C1—C2—C3	1.20 (18)	C5—C6—C7—N1	−35.04 (14)
C1—C2—C3—C4	−0.17 (18)	C1—C6—C7—N1	149.05 (10)
C2—C3—C4—C5	−1.07 (17)	C7—N1—C8—C9	−149.79 (11)
C3—C4—C5—F2	−176.83 (10)	C7—N1—C8—C13	31.27 (16)
C3—C4—C5—C6	1.43 (17)	C13—C8—C9—C10	−1.75 (16)
F2—C5—C6—C1	177.77 (9)	N1—C8—C9—C10	179.28 (10)
C4—C5—C6—C1	−0.47 (15)	C8—C9—C10—C11	0.62 (16)
F2—C5—C6—C7	1.63 (15)	C9—C10—C11—C12	0.98 (16)
C4—C5—C6—C7	−176.61 (10)	C9—C10—C11—C14	−178.58 (10)
F1—C1—C6—C5	178.35 (9)	C10—C11—C12—C13	−1.44 (16)
C2—C1—C6—C5	−0.88 (16)	C14—C11—C12—C13	178.11 (10)
F1—C1—C6—C7	−5.33 (15)	C11—C12—C13—C8	0.31 (16)
C2—C1—C6—C7	175.44 (10)	C9—C8—C13—C12	1.28 (16)
C8—N1—C7—O1	−5.34 (17)	N1—C8—C13—C12	−179.81 (10)
C8—N1—C7—C6	174.18 (9)	C7—O1—N1—H1N1	−1.4 (18)
C5—C6—C7—O1	144.50 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.863 (15)	2.107 (15)	2.9029 (12)	153.3 (14)
C12—H12···F1ii	0.940 (16)	2.473 (16)	3.4066 (14)	172.4 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.863 (15)	2.107 (15)	2.9029 (12)	153.3 (14)
C12—H12⋯F1ii	0.940 (16)	2.473 (16)	3.4066 (14)	172.4 (13)

Symmetry codes: (i) ; (ii) .