N'-(2-Chloro-benzyl-idene)-2-fluoro-benzohydrazide.

The title hydrazone compound, C(14)H(10)ClFN(2)O, adopts an E configuration about the C=N double bond. The dihedral angle between the two substituted benzene rings is 11.6 (2)°. The F atom is disordered over two sites with occupancies of 0.488 (2) and 0.512 (2). In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the a axis. C-H⋯F and C-H⋯O inter-actions also occur.

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶); Horiuchi et al. (2009 ▶). For the crystal structures of hydrazone compounds, see: Ban (2010 ▶); Hussain et al. (2010 ▶); Shalash et al. (2010 ▶); Khaledi et al. (2009 ▶).

Experimental

Crystal data

C14H10ClFN2O

M = 276.69

Monoclinic,

a = 7.1110 (14) Å

b = 25.291 (3) Å

c = 7.6560 (15) Å

β = 111.472 (3)°

V = 1281.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.950

10805 measured reflections

2734 independent reflections

1771 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.123

S = 1.03

2734 reflections

185 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053043/om2388sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053043/om2388Isup2.hkl

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

C14H10ClFN2O	F(000) = 568
Mr = 276.69	Dx = 1.434 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1387 reflections
a = 7.1110 (14) Å	θ = 2.5–24.6°
b = 25.291 (3) Å	µ = 0.30 mm−1
c = 7.6560 (15) Å	T = 298 K
β = 111.472 (3)°	Block, colorless
V = 1281.3 (4) Å3	0.20 × 0.17 × 0.17 mm
Z = 4

Bruker APEXII diffractometer	2734 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.942, Tmax = 0.950	k = −32→32
10805 measured reflections	l = −9→9

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2578P] where P = (Fo2 + 2Fc2)/3
2734 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.17 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)
Cl1	0.79975 (13)	0.45321 (3)	0.51687 (11)	0.0759 (3)
F1A	0.6784 (6)	0.24779 (12)	0.8540 (4)	0.0821 (14)	0.512 (4)
F1B	0.7132 (5)	0.09899 (12)	0.5057 (4)	0.0719 (13)	0.488 (4)
O1	0.5332 (3)	0.19241 (6)	0.3381 (2)	0.0543 (5)
N1	0.6941 (3)	0.29004 (7)	0.3616 (2)	0.0414 (5)
N2	0.7342 (3)	0.25676 (8)	0.5135 (3)	0.0445 (5)
H2	0.826 (3)	0.2667 (9)	0.617 (3)	0.053*
C1	0.7557 (4)	0.42979 (10)	0.2922 (3)	0.0478 (6)
C2	0.7356 (3)	0.37588 (9)	0.2559 (3)	0.0401 (5)
C3	0.7001 (4)	0.35952 (10)	0.0726 (3)	0.0489 (6)
H3	0.6845	0.3237	0.0435	0.059*
C4	0.6877 (4)	0.39541 (13)	−0.0655 (4)	0.0642 (8)
H4	0.6663	0.3839	−0.1866	0.077*
C5	0.7070 (5)	0.44840 (13)	−0.0241 (4)	0.0753 (9)
H5	0.6971	0.4727	−0.1183	0.090*
C6	0.7407 (4)	0.46597 (11)	0.1538 (4)	0.0663 (8)
H6	0.7532	0.5019	0.1808	0.080*
C7	0.7584 (3)	0.33724 (9)	0.4035 (3)	0.0416 (6)
H7	0.8200	0.3470	0.5288	0.050*
C8	0.6477 (3)	0.20886 (9)	0.4899 (3)	0.0387 (5)
C9	0.6963 (3)	0.17703 (9)	0.6648 (3)	0.0375 (5)
C10	0.7213 (4)	0.12300 (10)	0.6606 (4)	0.0507 (6)
H10	0.7113	0.1071	0.5481	0.061*	0.512 (4)
C11	0.7599 (4)	0.09235 (12)	0.8154 (5)	0.0741 (9)
H11	0.7775	0.0561	0.8081	0.089*
C12	0.7729 (4)	0.11456 (17)	0.9811 (5)	0.0805 (11)
H12	0.7987	0.0934	1.0867	0.097*
C13	0.7482 (4)	0.16775 (16)	0.9932 (4)	0.0712 (9)
H13	0.7566	0.1833	1.1059	0.085*
C14	0.7105 (4)	0.19780 (11)	0.8342 (3)	0.0533 (7)
H14	0.6938	0.2341	0.8423	0.064*	0.488 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.1118 (7)	0.0547 (5)	0.0717 (6)	−0.0195 (4)	0.0461 (5)	−0.0190 (4)
F1A	0.137 (3)	0.059 (2)	0.068 (2)	−0.020 (2)	0.059 (2)	−0.0216 (16)
F1B	0.090 (3)	0.046 (2)	0.082 (3)	0.0040 (16)	0.034 (2)	−0.0095 (17)
O1	0.0658 (12)	0.0487 (10)	0.0334 (10)	−0.0124 (9)	0.0006 (8)	−0.0030 (8)
N1	0.0445 (11)	0.0424 (11)	0.0313 (10)	−0.0007 (9)	0.0066 (8)	0.0066 (9)
N2	0.0504 (13)	0.0412 (11)	0.0303 (11)	−0.0095 (9)	0.0011 (9)	0.0026 (9)
C1	0.0509 (15)	0.0456 (15)	0.0503 (16)	−0.0004 (12)	0.0224 (12)	0.0004 (12)
C2	0.0349 (13)	0.0450 (14)	0.0387 (13)	0.0013 (10)	0.0115 (10)	0.0033 (11)
C3	0.0513 (15)	0.0525 (15)	0.0407 (15)	0.0063 (12)	0.0141 (12)	0.0026 (12)
C4	0.0694 (19)	0.083 (2)	0.0387 (16)	0.0155 (16)	0.0182 (14)	0.0127 (15)
C5	0.089 (2)	0.077 (2)	0.065 (2)	0.0196 (18)	0.0336 (18)	0.0363 (18)
C6	0.080 (2)	0.0455 (16)	0.080 (2)	0.0077 (14)	0.0365 (18)	0.0146 (15)
C7	0.0449 (14)	0.0424 (14)	0.0332 (13)	−0.0030 (11)	0.0093 (10)	0.0003 (11)
C8	0.0381 (13)	0.0418 (13)	0.0332 (13)	−0.0006 (11)	0.0095 (11)	−0.0022 (10)
C9	0.0318 (12)	0.0447 (14)	0.0314 (12)	−0.0034 (10)	0.0062 (9)	0.0026 (10)
C10	0.0434 (15)	0.0472 (15)	0.0591 (17)	0.0026 (12)	0.0161 (13)	0.0076 (14)
C11	0.0605 (19)	0.0587 (19)	0.096 (3)	0.0067 (15)	0.0203 (18)	0.0356 (19)
C12	0.057 (2)	0.106 (3)	0.066 (2)	−0.0101 (18)	0.0085 (16)	0.044 (2)
C13	0.0576 (18)	0.117 (3)	0.0361 (16)	−0.0247 (18)	0.0141 (13)	0.0039 (17)
C14	0.0479 (15)	0.0685 (19)	0.0409 (16)	−0.0120 (13)	0.0131 (12)	−0.0060 (14)

Cl1—C1	1.736 (3)	C5—C6	1.368 (4)
F1A—C14	1.303 (3)	C5—H5	0.9300
F1B—C10	1.315 (3)	C6—H6	0.9300
O1—C8	1.222 (2)	C7—H7	0.9300
N1—C7	1.276 (3)	C8—C9	1.491 (3)
N1—N2	1.379 (2)	C9—C14	1.368 (3)
N2—C8	1.340 (3)	C9—C10	1.380 (3)
N2—H2	0.861 (16)	C10—C11	1.357 (4)
C1—C6	1.374 (3)	C10—H10	0.9300
C1—C2	1.388 (3)	C11—C12	1.360 (4)
C2—C3	1.395 (3)	C11—H11	0.9300
C2—C7	1.457 (3)	C12—C13	1.364 (5)
C3—C4	1.372 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.376 (4)
C4—C5	1.372 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C7—N1—N2	114.48 (18)	O1—C8—N2	123.3 (2)
C8—N2—N1	119.66 (18)	O1—C8—C9	121.7 (2)
C8—N2—H2	123.0 (16)	N2—C8—C9	114.99 (19)
N1—N2—H2	116.9 (16)	C14—C9—C10	115.9 (2)
C6—C1—C2	121.7 (2)	C14—C9—C8	123.8 (2)
C6—C1—Cl1	118.2 (2)	C10—C9—C8	120.2 (2)
C2—C1—Cl1	120.10 (19)	F1B—C10—C11	116.9 (3)
C1—C2—C3	117.4 (2)	F1B—C10—C9	121.0 (3)
C1—C2—C7	122.0 (2)	C11—C10—C9	122.1 (3)
C3—C2—C7	120.6 (2)	C11—C10—H10	118.9
C4—C3—C2	121.1 (2)	C9—C10—H10	118.9
C4—C3—H3	119.5	C10—C11—C12	120.1 (3)
C2—C3—H3	119.5	C10—C11—H11	119.9
C3—C4—C5	119.7 (3)	C12—C11—H11	119.9
C3—C4—H4	120.1	C11—C12—C13	120.3 (3)
C5—C4—H4	120.1	C11—C12—H12	119.9
C6—C5—C4	120.9 (3)	C13—C12—H12	119.9
C6—C5—H5	119.6	C12—C13—C14	118.2 (3)
C4—C5—H5	119.6	C12—C13—H13	120.9
C5—C6—C1	119.2 (3)	C14—C13—H13	120.9
C5—C6—H6	120.4	F1A—C14—C9	121.8 (3)
C1—C6—H6	120.4	F1A—C14—C13	114.8 (3)
N1—C7—C2	120.3 (2)	C9—C14—C13	123.3 (3)
N1—C7—H7	119.9	C9—C14—H14	118.3
C2—C7—H7	119.9	C13—C14—H14	118.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86 (2)	2.07 (2)	2.912 (2)	167 (2)
N2—H2···F1A	0.86 (2)	2.45 (2)	2.785 (2)	104 (2)
C3—H3···F1Aii	0.93	2.40	3.259 (2)	154 (2)
C7—H7···O1i	0.93	2.50	3.270 (2)	140 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86 (2)	2.07 (2)	2.912 (2)	167 (2)
C3—H3⋯F1Aii	0.93	2.40	3.259 (2)	154 (2)
C7—H7⋯O1i	0.93	2.50	3.270 (2)	140 (2)

Symmetry codes: (i) ; (ii) .