(E)-N′-(3-Fluoro­benzyl­idene)-2-hydroxy­benzohydrazide

Xu, H.-J.; Sheng, L.-Q.; Liu, Z.-D.; Shao, S.-C.

doi:10.1107/S1600536809006941

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o666

doi:10.1107/S1600536809006941

Open

access

(E)-N′-(3-Fluorobenzylidene)-2-hydroxybenzohydrazide

Hua-Jie Xu,^a Liang-Quan Sheng,^a Zhao-Di Liu ^a and Si-Chang Shao ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang Anhui 236041, People's Republic of China
^*Correspondence e-mail: shaosic@fync.edu.cn

(Received 19 February 2009; accepted 25 February 2009; online 6 March 2009)

The title compound, C₁₄H₁₁FN₂O₂, adopts an E or trans configuration with respect to the C=N bond. An intramolecular N—H⋯O hydrogen bond contributes to the relatively planarity of the molecular conformation; the two benzene rings are inclined to one another by 12.5 (2)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules 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_r = 258.25
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.088
wR(F²) = 0.240
S = 1.05
2152 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006941/su2098sup1.cif

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

checkCIF report

Comment top

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As part of an ongoing study of such compounds, we report here on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. It can be seen to display a trans configuration about the C=N bond. There is an intramolecular N-H···O hydrogen bond, involving the NH H-atom and the O-atom of the hydroxyl substituent (Table 1), and the dihedral angle between the two benzene rings is 12.5 (2)°.

In the crystal molecules are linked by intermolecular O—H···O hydrongen bonds to form chains running parallel to the c axis (Fig. 2 and Table 1).

Related literature top

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 top

Equimolar amounts of 2-Hydroxybenzohydrazide and 3-fluorobenzohydrazide were reacted in ethanol (10 ml) for 1 h. After allowing the resulting solution to stand in air for 10 days yellow block-shaped crystals were formed, on slow evaporation of the solvent.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H-atoms have been omitted for clarity.
	Fig. 2. Crystal packing viewed along the A axis. The intra- and intermolecular hydrogen bonds are shown as dashed lines (details are given in Table 1).

(E)-N'-(3-Fluorobenzylidene)-2-hydroxybenzohydrazide top

Crystal data top

C₁₄H₁₁FN₂O₂	F(000) = 536
M_r = 258.25	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1113P)² + 0.2945P] where P = (F_o² + 2F_c²)/3
2152 reflections	(Δ/σ)_max = 0.002
170 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₁FN₂O₂	V = 1216.4 (6) Å³
M_r = 258.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8751 (15) Å	µ = 0.11 mm⁻¹
b = 22.188 (7) Å	T = 297 K
c = 11.323 (3) Å	0.20 × 0.10 × 0.10 mm
β = 96.717 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2152 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1205 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.989	R_int = 0.081
8534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.240	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
2152 reflections	Δρ_min = −0.30 e Å⁻³
170 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁FN₂O₂
M_r	258.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	297
a, b, c (Å)	4.8751 (15), 22.188 (7), 11.323 (3)
β (°)	96.717 (5)
V (Å³)	1216.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	8534, 2152, 1205
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.240, 1.05
No. of reflections	2152
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the Key Project of Science and Technology of Anhui, P. R. China (grant No. 08010302218).

References

Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Khattab, S. N. (2005). Molecules, 10, 1218–1228. Web of Science CrossRef PubMed CAS Google Scholar
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353–359. Web of Science CrossRef PubMed Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar