(E)-N'-(3-Fluoro-benzyl-idene)-2-hydroxy-benzohydrazide.

The title compound, C(14)H(11)FN(2)O(2), adopts an E or trans configuration with respect to the C=N bond. An intra-molecular N-H⋯O hydrogen bond contributes to the relatively planarity of the mol-ecular conformation; the two benzene rings are inclined to one another by 12.5 (2)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains running parallel to the c axis.

Related literature

For the potential pharmacological and anti­tumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006 ▶); Khattab (2005 ▶); Kucukguzel et al. (2006 ▶); Okabe et al. (1993 ▶).

Experimental

Crystal data

C14H11FN2O2

M = 258.25

Monoclinic,

a = 4.8751 (15) Å

b = 22.188 (7) Å

c = 11.323 (3) Å

β = 96.717 (5)°

V = 1216.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 297 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.989

8534 measured reflections

2152 independent reflections

1205 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.240

S = 1.05

2152 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809006941/su2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006941/su2098Isup2.hkl

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

C14H11FN2O2	F(000) = 536
Mr = 258.25	Dx = 1.410 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 589 reflections
a = 4.8751 (15) Å	θ = 2.3–15°
b = 22.188 (7) Å	µ = 0.11 mm−1
c = 11.323 (3) Å	T = 297 K
β = 96.717 (5)°	Block, yellow
V = 1216.4 (6) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2152 independent reflections
Radiation source: fine-focus sealed tube	1205 reflections with I > 2σ(I)
graphite	Rint = 0.081
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.979, Tmax = 0.989	k = −26→26
8534 measured reflections	l = −13→13

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1113P)2 + 0.2945P] where P = (Fo2 + 2Fc2)/3
2152 reflections	(Δ/σ)max = 0.002
170 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
F1	−0.2554 (15)	0.0383 (3)	0.4844 (5)	0.103 (3)	0.500
F1'	−0.3673 (19)	0.0122 (3)	0.0916 (6)	0.136 (4)	0.500
O1	0.8661 (7)	0.26546 (15)	0.1078 (3)	0.0638 (11)
O2	0.7116 (7)	0.27530 (14)	0.4613 (2)	0.0643 (11)
N1	0.5969 (8)	0.23163 (16)	0.2828 (3)	0.0518 (12)
N2	0.4125 (7)	0.19142 (17)	0.3234 (3)	0.0490 (12)
C1	0.9330 (8)	0.31131 (19)	0.3001 (4)	0.0443 (12)
C2	1.0667 (10)	0.3559 (2)	0.3713 (4)	0.0563 (16)
C3	1.2548 (11)	0.3939 (2)	0.3302 (4)	0.0658 (19)
C4	1.3165 (10)	0.3890 (2)	0.2158 (4)	0.0601 (17)
C5	1.1869 (9)	0.34596 (19)	0.1418 (4)	0.0527 (17)
C6	0.9959 (8)	0.30710 (19)	0.1824 (3)	0.0433 (14)
C7	0.7399 (9)	0.27175 (19)	0.3545 (4)	0.0465 (17)
C8	0.2866 (9)	0.1604 (2)	0.2415 (4)	0.0524 (17)
C9	0.0844 (6)	0.11357 (12)	0.2623 (3)	0.0497 (17)
C10	0.0213 (6)	0.09879 (13)	0.3754 (2)	0.0520 (16)
C11	−0.1728 (7)	0.05426 (14)	0.3894 (3)	0.067 (2)
C12	−0.3037 (6)	0.02449 (13)	0.2905 (4)	0.0750 (19)
C13	−0.2406 (7)	0.03926 (15)	0.1774 (3)	0.083 (2)
C14	−0.0466 (7)	0.08380 (16)	0.1634 (2)	0.073 (2)
H1N	0.62100	0.23090	0.20870	0.0620*
H1O	0.96210	0.25770	0.05500	0.0950*
H2	1.02690	0.36010	0.44930	0.0680*
H3	1.34130	0.42320	0.38030	0.0790*
H4	1.44560	0.41470	0.18810	0.0720*
H5	1.22770	0.34290	0.06380	0.0630*
H8	0.32300	0.16740	0.16390	0.0630*
H10	0.10890	0.11870	0.44160	0.0620*
H11	−0.21500	0.04440	0.46510	0.0800*	0.500
H12	−0.43350	−0.00530	0.29990	0.0900*
H13	−0.32820	0.01930	0.11120	0.0990*	0.500
H14	−0.00440	0.09370	0.08770	0.0870*

	U11	U22	U33	U12	U13	U23
F1	0.145 (6)	0.094 (5)	0.080 (4)	−0.033 (5)	0.054 (4)	0.006 (4)
F1'	0.184 (8)	0.138 (6)	0.075 (4)	−0.103 (6)	−0.026 (5)	−0.006 (4)
O1	0.076 (2)	0.075 (2)	0.0473 (19)	−0.0178 (19)	0.0363 (16)	−0.0120 (17)
O2	0.081 (2)	0.075 (2)	0.0416 (18)	−0.0068 (18)	0.0274 (17)	−0.0018 (15)
N1	0.063 (2)	0.056 (2)	0.041 (2)	−0.005 (2)	0.0255 (19)	0.0029 (18)
N2	0.051 (2)	0.053 (2)	0.047 (2)	0.003 (2)	0.0222 (18)	0.0074 (19)
C1	0.045 (2)	0.042 (2)	0.048 (2)	0.011 (2)	0.014 (2)	0.006 (2)
C2	0.074 (3)	0.053 (3)	0.044 (2)	0.001 (3)	0.016 (2)	−0.002 (2)
C3	0.080 (4)	0.053 (3)	0.064 (3)	−0.013 (3)	0.007 (3)	0.000 (3)
C4	0.061 (3)	0.062 (3)	0.059 (3)	−0.008 (3)	0.014 (2)	0.011 (3)
C5	0.061 (3)	0.050 (3)	0.051 (3)	−0.002 (2)	0.023 (2)	0.007 (2)
C6	0.047 (3)	0.045 (2)	0.040 (2)	0.004 (2)	0.014 (2)	−0.004 (2)
C7	0.054 (3)	0.048 (3)	0.041 (3)	0.013 (2)	0.021 (2)	0.001 (2)
C8	0.058 (3)	0.059 (3)	0.042 (3)	0.009 (3)	0.014 (2)	0.009 (2)
C9	0.052 (3)	0.047 (3)	0.052 (3)	0.009 (2)	0.014 (2)	0.005 (2)
C10	0.061 (3)	0.041 (2)	0.057 (3)	0.002 (2)	0.019 (2)	0.000 (2)
C11	0.076 (4)	0.049 (3)	0.080 (4)	0.001 (3)	0.031 (3)	0.006 (3)
C12	0.060 (3)	0.055 (3)	0.111 (4)	−0.004 (3)	0.014 (3)	0.008 (3)
C13	0.085 (4)	0.077 (4)	0.085 (4)	−0.017 (3)	0.004 (3)	0.001 (3)
C14	0.078 (4)	0.084 (4)	0.055 (3)	−0.012 (3)	0.003 (3)	−0.005 (3)

F1'—C13	1.243 (8)	C9—C10	1.3908
F1—C11	1.243 (7)	C9—C14	1.3896
O1—C6	1.357 (5)	C10—C11	1.3899
O2—C7	1.236 (5)	C11—C12	1.3894
O1—H1O	0.8200	C12—C13	1.3908
N1—N2	1.383 (5)	C13—C14	1.3897
N1—C7	1.344 (6)	C2—H2	0.9300
N2—C8	1.256 (6)	C3—H3	0.9300
N1—H1N	0.8600	C4—H4	0.9300
C1—C7	1.474 (6)	C5—H5	0.9300
C1—C2	1.390 (6)	C8—H8	0.9300
C1—C6	1.405 (6)	C10—H10	0.9300
C2—C3	1.367 (7)	C11—H11	0.9300
C3—C4	1.368 (6)	C12—H12	0.9300
C4—C5	1.375 (6)	C13—H13	0.9300
C5—C6	1.386 (6)	C14—H14	0.9300
C8—C9	1.470 (5)
C6—O1—H1O	109.00	C11—C12—C13	120.00
N2—N1—C7	122.6 (3)	C12—C13—C14	119.96
N1—N2—C8	112.9 (3)	F1'—C13—C12	117.6 (5)
C7—N1—H1N	119.00	F1'—C13—C14	122.5 (4)
N2—N1—H1N	119.00	C9—C14—C13	120.06
C6—C1—C7	125.3 (4)	C1—C2—H2	119.00
C2—C1—C7	117.4 (4)	C3—C2—H2	119.00
C2—C1—C6	117.3 (4)	C2—C3—H3	120.00
C1—C2—C3	122.0 (4)	C4—C3—H3	120.00
C2—C3—C4	120.3 (4)	C3—C4—H4	120.00
C3—C4—C5	119.7 (4)	C5—C4—H4	120.00
C4—C5—C6	120.6 (4)	C4—C5—H5	120.00
C1—C6—C5	120.2 (4)	C6—C5—H5	120.00
O1—C6—C1	119.9 (4)	N2—C8—H8	118.00
O1—C6—C5	120.0 (3)	C9—C8—H8	118.00
O2—C7—N1	121.6 (4)	C9—C10—H10	120.00
O2—C7—C1	121.4 (4)	C11—C10—H10	120.00
N1—C7—C1	117.0 (4)	C10—C11—H11	120.00
N2—C8—C9	123.2 (4)	C12—C11—H11	120.00
C10—C9—C14	119.98	C11—C12—H12	120.00
C8—C9—C14	117.4 (3)	C13—C12—H12	120.00
C8—C9—C10	122.6 (3)	C12—C13—H13	120.00
C9—C10—C11	119.97	C14—C13—H13	120.00
F1—C11—C10	126.5 (4)	C9—C14—H14	120.00
C10—C11—C12	120.04	C13—C14—H14	120.00
F1—C11—C12	113.4 (4)
C7—N1—N2—C8	175.7 (4)	C4—C5—C6—O1	178.9 (4)
N2—N1—C7—O2	−0.8 (7)	C4—C5—C6—C1	−0.1 (6)
N2—N1—C7—C1	179.0 (4)	N2—C8—C9—C10	−1.7 (6)
N1—N2—C8—C9	178.6 (4)	N2—C8—C9—C14	178.1 (4)
C2—C1—C6—C5	0.8 (6)	C8—C9—C10—C11	179.7 (3)
C7—C1—C6—O1	2.7 (6)	C14—C9—C10—C11	−0.02
C7—C1—C6—C5	−178.3 (4)	C8—C9—C14—C13	−179.7 (3)
C2—C1—C7—O2	−4.8 (6)	C10—C9—C14—C13	−0.03
C2—C1—C7—N1	175.4 (4)	C9—C10—C11—F1	−177.2 (5)
C6—C1—C7—O2	174.3 (4)	C9—C10—C11—C12	0.03
C6—C1—C7—N1	−5.5 (6)	F1—C11—C12—C13	177.5 (4)
C2—C1—C6—O1	−178.2 (4)	C10—C11—C12—C13	−0.02
C6—C1—C2—C3	−0.8 (7)	C11—C12—C13—F1'	−178.6 (5)
C7—C1—C2—C3	178.3 (4)	C11—C12—C13—C14	−0.02
C1—C2—C3—C4	0.2 (7)	F1'—C13—C14—C9	178.5 (5)
C2—C3—C4—C5	0.5 (7)	C12—C13—C14—C9	0.03
C3—C4—C5—C6	−0.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.86	1.91	2.612 (5)	138
O1—H1O···O2i	0.82	1.86	2.657 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.86	1.91	2.612 (5)	138
O1—H1O⋯O2i	0.82	1.86	2.657 (5)	166

Symmetry code: (i) .