N'-(2-Fluoro-benzo-yl)benzohydrazide.

In the crystal structure of the title compound, C(14)H(11)FN(2)O(2), the molecule is centrosymmetric. The F atom is disordered over four positions, on the two ortho positions of each ring, with occupancies of 0.287:0.213 (5). In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Silva et al. (2006 ▶); Chopra et al. (2006 ▶); de Souza et al. (2007 ▶); Ahmad et al. (2001 ▶); Al-Soud, et al. (2004 ▶); Al-Talib et al. (1990 ▶); El-Emam et al. (2004 ▶); Yousif et al. (1986 ▶); Zareef & Iqbal (2007 ▶); Zheng et al. (2003 ▶).

Experimental

Crystal data

C14H11FN2O2

M = 258.25

Monoclinic,

a = 4.7698 (10) Å

b = 5.2435 (10) Å

c = 23.913 (5) Å

β = 100.89 (3)°

V = 587.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 90.0 (1) K

0.25 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: none

3819 measured reflections

1205 independent reflections

1060 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.07

1205 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2002 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014645/bq2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014645/bq2073Isup2.hkl

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

C14H11FN2O2	F(000) = 268
Mr = 258.25	Dx = 1.460 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1205 reflections
a = 4.7698 (10) Å	θ = 3.5–26.5°
b = 5.2435 (10) Å	µ = 0.11 mm−1
c = 23.913 (5) Å	T = 90 K
β = 100.89 (3)°	Plate, colourless
V = 587.3 (2) Å3	0.25 × 0.20 × 0.10 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer	1060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 26.5°, θmin = 3.5°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1	h = −5→5
ω scans	k = −4→6
3819 measured reflections	l = −30→30
1205 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0555P)2 + 1.578P] where P = (Fo2 + 2Fc2)/3
1205 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.4363 (2)	0.5857 (2)	0.47949 (4)	0.0183 (3)
C2	0.5853 (2)	0.6622 (2)	0.44055 (5)	0.0166 (3)
O3	0.83154 (17)	0.58840 (19)	0.44180 (4)	0.0255 (3)
C4	0.4404 (2)	0.8420 (2)	0.39624 (5)	0.0163 (3)
C5	0.5167 (3)	0.8362 (2)	0.34288 (5)	0.0193 (3)
H5	0.6561	0.7149	0.3356	0.023*	0.77 (6)
C6	0.3958 (3)	1.0022 (3)	0.30033 (5)	0.0228 (3)
C7	0.1997 (3)	1.1812 (2)	0.31099 (5)	0.0237 (3)
C8	0.1226 (3)	1.1921 (2)	0.36398 (6)	0.0235 (3)
C9	0.2420 (2)	1.0224 (2)	0.40602 (5)	0.0189 (3)
H9	0.1862	1.0290	0.4425	0.023*	0.73 (6)
F10	0.1593 (5)	1.0332 (5)	0.45796 (13)	0.0224 (10)	0.287 (5)
F10'	0.6956 (8)	0.6688 (8)	0.33028 (14)	0.0240 (13)	0.213 (5)
H1	0.258 (4)	0.605 (3)	0.4759 (7)	0.037 (5)*
H6	0.456 (3)	0.995 (3)	0.2630 (7)	0.030 (4)*
H7	0.114 (3)	1.296 (3)	0.2808 (7)	0.034 (4)*
H8	−0.007 (3)	1.315 (3)	0.3730 (6)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0108 (5)	0.0275 (6)	0.0168 (5)	0.0041 (4)	0.0032 (4)	0.0053 (4)
C2	0.0118 (6)	0.0233 (6)	0.0149 (5)	0.0003 (4)	0.0029 (4)	−0.0014 (4)
O3	0.0128 (5)	0.0416 (6)	0.0234 (5)	0.0072 (4)	0.0066 (3)	0.0104 (4)
C4	0.0112 (5)	0.0201 (6)	0.0170 (6)	−0.0023 (4)	0.0011 (4)	−0.0004 (4)
C5	0.0167 (6)	0.0225 (6)	0.0185 (6)	0.0016 (5)	0.0030 (5)	−0.0002 (5)
C6	0.0233 (7)	0.0274 (7)	0.0171 (6)	−0.0013 (5)	0.0028 (5)	0.0017 (5)
C7	0.0205 (6)	0.0231 (6)	0.0251 (6)	−0.0002 (5)	−0.0019 (5)	0.0073 (5)
C8	0.0192 (6)	0.0191 (6)	0.0324 (7)	0.0032 (5)	0.0052 (5)	0.0007 (5)
C9	0.0171 (6)	0.0202 (6)	0.0200 (6)	−0.0013 (5)	0.0050 (5)	−0.0017 (4)
F10	0.0267 (15)	0.0234 (14)	0.0195 (16)	0.0052 (10)	0.0104 (10)	−0.0014 (10)
F10'	0.026 (2)	0.029 (2)	0.0184 (18)	0.0116 (15)	0.0068 (14)	0.0018 (13)

N1—C2	1.3354 (16)	C6—C7	1.3824 (19)
N1—N1i	1.384 (2)	C6—H6	0.989 (15)
N1—H1	0.84 (2)	C7—C8	1.3856 (19)
C2—O3	1.2315 (14)	C7—H7	0.971 (17)
C2—C4	1.4875 (16)	C8—C9	1.3822 (18)
C4—C9	1.3890 (17)	C8—H8	0.945 (17)
C4—C5	1.3916 (17)	C9—F10	1.373 (4)
C5—F10'	1.299 (5)	C9—H9	0.9600
C5—C6	1.3797 (18)	F10—H9	0.4136
C5—H5	0.9600	F10'—H5	0.3448
C2—N1—N1i	117.97 (12)	C5—C6—C7	119.69 (12)
C2—N1—H1	123.5 (11)	C5—C6—H6	119.3 (10)
N1i—N1—H1	116.7 (12)	C7—C6—H6	121.0 (10)
O3—C2—N1	121.31 (11)	C6—C7—C8	120.16 (12)
O3—C2—C4	121.94 (11)	C6—C7—H7	119.4 (10)
N1—C2—C4	116.75 (10)	C8—C7—H7	120.4 (10)
C9—C4—C5	118.28 (11)	C9—C8—C7	119.64 (12)
C9—C4—C2	123.46 (11)	C9—C8—H8	118.0 (9)
C5—C4—C2	118.20 (10)	C7—C8—H8	122.3 (9)
F10'—C5—C6	117.16 (18)	F10—C9—C8	118.83 (14)
F10'—C5—C4	121.64 (17)	F10—C9—C4	120.10 (14)
C6—C5—C4	121.15 (11)	C8—C9—C4	121.07 (11)
C6—C5—H5	119.4	C8—C9—H9	119.4
C4—C5—H5	119.5	C4—C9—H9	119.5
N1i—N1—C2—O3	−1.9 (2)	F10'—C5—C6—C7	178.7 (2)
N1i—N1—C2—C4	178.67 (12)	C4—C5—C6—C7	1.29 (19)
O3—C2—C4—C9	−147.25 (13)	C5—C6—C7—C8	−0.64 (19)
N1—C2—C4—C9	32.16 (16)	C6—C7—C8—C9	−0.29 (19)
O3—C2—C4—C5	29.97 (17)	C7—C8—C9—F10	−178.88 (16)
N1—C2—C4—C5	−150.62 (11)	C7—C8—C9—C4	0.61 (19)
C9—C4—C5—F10'	−178.3 (2)	C5—C4—C9—F10	179.49 (16)
C2—C4—C5—F10'	4.3 (3)	C2—C4—C9—F10	−3.3 (2)
C9—C4—C5—C6	−0.97 (18)	C5—C4—C9—C8	0.01 (18)
C2—C4—C5—C6	−178.33 (11)	C2—C4—C9—C8	177.23 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ii	0.84 (2)	2.05 (2)	2.8549 (16)	160.4 (16)
N1—H1···O3i	0.84 (2)	2.325 (16)	2.6302 (14)	101.8 (14)
C8—H8···O3iii	0.945 (17)	2.416 (16)	3.2687 (17)	150.0 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.84 (2)	2.05 (2)	2.8549 (16)	160.4 (16)
N1—H1⋯O3ii	0.84 (2)	2.325 (16)	2.6302 (14)	101.8 (14)
C8—H8⋯O3iii	0.945 (17)	2.416 (16)	3.2687 (17)	150.0 (12)

Symmetry codes: (i) ; (ii) ; (iii) .