N'-(2,4-Dichloro-benzyl-idene)-2-fluoro-benzohydrazide.

The mol-ecule of the title compound, C(14)H(9)Cl(2)FN(2)O, exists in a trans configuration with respect to the methyl-idene unit and the benzene rings form a dihedral angle of 8.1 (2)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds into C(4) chains propagating in [100].

Related literature

For related structures and background to the pharmacological properties of hydrazone compounds, see: Xu et al. (2011a ▶,b ▶). For reference bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H9Cl2FN2O

M = 311.13

Monoclinic,

a = 7.2310 (14) Å

b = 26.145 (5) Å

c = 8.0590 (16) Å

β = 115.033 (3)°

V = 1380.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.898, T max = 0.911

9842 measured reflections

2963 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.163

S = 1.05

2963 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810053249/hb5775sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053249/hb5775Isup2.hkl

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

C14H9Cl2FN2O	F(000) = 632
Mr = 311.13	Dx = 1.497 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2459 reflections
a = 7.2310 (14) Å	θ = 2.7–25.0°
b = 26.145 (5) Å	µ = 0.48 mm−1
c = 8.0590 (16) Å	T = 298 K
β = 115.033 (3)°	Block, colorless
V = 1380.5 (5) Å3	0.23 × 0.21 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	2963 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.898, Tmax = 0.911	k = −33→33
9842 measured reflections	l = −10→10

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0831P)2 + 0.4914P] where P = (Fo2 + 2Fc2)/3
2963 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.66 e Å−3
1 restraint	Δρmin = −0.27 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 > 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
Cl1	0.86585 (15)	0.06215 (3)	0.64036 (10)	0.0753 (3)
Cl2	0.71562 (15)	0.01533 (3)	−0.04771 (12)	0.0778 (3)
F1	0.7577 (4)	0.25674 (8)	0.9556 (3)	0.0964 (7)
N1	0.7523 (3)	0.21787 (8)	0.4805 (3)	0.0482 (5)
N2	0.7956 (3)	0.24975 (8)	0.6285 (3)	0.0506 (6)
O1	0.5927 (3)	0.31235 (8)	0.4527 (3)	0.0707 (6)
C1	0.7912 (4)	0.13485 (10)	0.3799 (3)	0.0439 (6)
C2	0.8097 (4)	0.08305 (11)	0.4195 (3)	0.0482 (6)
C3	0.7842 (4)	0.04630 (10)	0.2903 (4)	0.0523 (6)
H3	0.7953	0.0117	0.3203	0.063*
C4	0.7417 (4)	0.06205 (11)	0.1141 (4)	0.0526 (7)
C5	0.7245 (4)	0.11280 (11)	0.0675 (4)	0.0540 (7)
H5	0.6977	0.1228	−0.0513	0.065*
C6	0.7475 (4)	0.14872 (11)	0.1991 (4)	0.0517 (6)
H6	0.7336	0.1832	0.1675	0.062*
C7	0.8217 (4)	0.17291 (10)	0.5209 (3)	0.0479 (6)
H7	0.8938	0.1640	0.6434	0.058*
C8	0.7067 (4)	0.29579 (10)	0.6032 (3)	0.0479 (6)
C9	0.7558 (4)	0.32662 (10)	0.7740 (3)	0.0475 (6)
C10	0.7779 (4)	0.30700 (12)	0.9386 (4)	0.0581 (7)
C11	0.8167 (5)	0.33677 (16)	1.0910 (4)	0.0761 (10)
H11	0.8316	0.3221	1.2011	0.091*
C12	0.8328 (5)	0.38854 (17)	1.0753 (5)	0.0832 (11)
H12	0.8592	0.4095	1.1762	0.100*
C13	0.8106 (5)	0.40961 (14)	0.9143 (6)	0.0796 (10)
H13	0.8231	0.4448	0.9066	0.096*
C14	0.7696 (4)	0.37967 (11)	0.7614 (5)	0.0615 (8)
H14	0.7514	0.3947	0.6510	0.074*
H2	0.886 (4)	0.2381 (12)	0.736 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1180 (7)	0.0635 (5)	0.0493 (4)	0.0186 (4)	0.0401 (5)	0.0144 (3)
Cl2	0.1043 (7)	0.0760 (6)	0.0646 (5)	−0.0129 (5)	0.0469 (5)	−0.0227 (4)
F1	0.143 (2)	0.0761 (14)	0.0794 (14)	0.0124 (13)	0.0558 (14)	0.0170 (11)
N1	0.0445 (12)	0.0506 (13)	0.0370 (11)	0.0004 (10)	0.0050 (9)	−0.0031 (9)
N2	0.0505 (13)	0.0511 (13)	0.0332 (11)	0.0077 (10)	0.0012 (9)	−0.0017 (9)
O1	0.0788 (14)	0.0604 (12)	0.0421 (11)	0.0151 (11)	−0.0044 (10)	0.0048 (9)
C1	0.0374 (12)	0.0507 (14)	0.0375 (13)	0.0004 (11)	0.0099 (10)	0.0028 (11)
C2	0.0493 (14)	0.0553 (15)	0.0397 (13)	0.0055 (12)	0.0186 (11)	0.0053 (11)
C3	0.0584 (16)	0.0474 (15)	0.0552 (16)	−0.0029 (12)	0.0281 (14)	−0.0016 (12)
C4	0.0500 (15)	0.0631 (17)	0.0470 (15)	−0.0085 (12)	0.0227 (12)	−0.0117 (12)
C5	0.0581 (16)	0.0636 (17)	0.0360 (13)	−0.0107 (13)	0.0158 (12)	−0.0011 (12)
C6	0.0510 (15)	0.0538 (15)	0.0430 (14)	−0.0041 (12)	0.0127 (12)	0.0047 (12)
C7	0.0445 (14)	0.0536 (15)	0.0369 (13)	0.0043 (12)	0.0087 (11)	0.0011 (11)
C8	0.0409 (13)	0.0505 (15)	0.0410 (14)	0.0012 (11)	0.0064 (11)	0.0019 (11)
C9	0.0321 (12)	0.0548 (15)	0.0437 (14)	0.0054 (11)	0.0044 (10)	−0.0010 (11)
C10	0.0510 (16)	0.0625 (18)	0.0527 (16)	0.0142 (13)	0.0140 (13)	0.0033 (14)
C11	0.063 (2)	0.109 (3)	0.0447 (17)	0.0231 (19)	0.0124 (14)	−0.0059 (17)
C12	0.062 (2)	0.096 (3)	0.072 (2)	0.0140 (19)	0.0088 (18)	−0.035 (2)
C13	0.061 (2)	0.064 (2)	0.099 (3)	0.0019 (16)	0.0197 (19)	−0.025 (2)
C14	0.0491 (16)	0.0514 (16)	0.073 (2)	0.0019 (12)	0.0147 (14)	−0.0084 (14)

Cl1—C2	1.738 (3)	C5—C6	1.373 (4)
Cl2—C4	1.738 (3)	C5—H5	0.9300
F1—C10	1.336 (4)	C6—H6	0.9300
N1—C7	1.265 (3)	C7—H7	0.9300
N1—N2	1.379 (3)	C8—C9	1.503 (4)
N2—C8	1.339 (3)	C9—C10	1.367 (4)
N2—H2	0.893 (10)	C9—C14	1.397 (4)
O1—C8	1.222 (3)	C10—C11	1.379 (4)
C1—C2	1.385 (4)	C11—C12	1.369 (6)
C1—C6	1.401 (4)	C11—H11	0.9300
C1—C7	1.455 (3)	C12—C13	1.355 (6)
C2—C3	1.371 (4)	C12—H12	0.9300
C3—C4	1.382 (4)	C13—C14	1.382 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.370 (4)	C14—H14	0.9300
C7—N1—N2	114.8 (2)	N1—C7—H7	119.3
C8—N2—N1	119.5 (2)	C1—C7—H7	119.3
C8—N2—H2	124 (2)	O1—C8—N2	123.3 (2)
N1—N2—H2	116 (2)	O1—C8—C9	121.2 (2)
C2—C1—C6	116.8 (2)	N2—C8—C9	115.5 (2)
C2—C1—C7	121.4 (2)	C10—C9—C14	117.4 (3)
C6—C1—C7	121.9 (2)	C10—C9—C8	125.0 (3)
C3—C2—C1	122.8 (2)	C14—C9—C8	117.5 (2)
C3—C2—Cl1	117.1 (2)	F1—C10—C9	119.7 (3)
C1—C2—Cl1	120.1 (2)	F1—C10—C11	117.0 (3)
C2—C3—C4	118.1 (3)	C9—C10—C11	123.3 (3)
C2—C3—H3	120.9	C12—C11—C10	118.0 (3)
C4—C3—H3	120.9	C12—C11—H11	121.0
C5—C4—C3	121.7 (2)	C10—C11—H11	121.0
C5—C4—Cl2	120.4 (2)	C13—C12—C11	120.7 (3)
C3—C4—Cl2	117.9 (2)	C13—C12—H12	119.7
C4—C5—C6	118.9 (2)	C11—C12—H12	119.7
C4—C5—H5	120.5	C12—C13—C14	121.1 (3)
C6—C5—H5	120.5	C12—C13—H13	119.4
C5—C6—C1	121.8 (3)	C14—C13—H13	119.4
C5—C6—H6	119.1	C13—C14—C9	119.5 (3)
C1—C6—H6	119.1	C13—C14—H14	120.3
N1—C7—C1	121.4 (2)	C9—C14—H14	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	2.19 (1)	3.054 (3)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.89 (1)	2.19 (1)	3.054 (3)	162 (3)

Symmetry code: (i) .