2-Fluoro-N′-(2-hy­droxy­benzyl­idene)benzohydrazide

Xu, C.-B.; Wang, Z.-G.; Nan, Y.; Yuan, L.; Wang, R.; Zhang, S.-X.

doi:10.1107/S1600536810050841

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o69

https://doi.org/10.1107/S1600536810050841

Open

access

2-Fluoro-N′-(2-hydroxybenzylidene)benzohydrazide

Cheng-Bi Xu,^a Zong-Gui Wang,^a ^* Yi Nan,^b Ling Yuan,^c,^d Rong Wang ^b and Shu-Xiang Zhang ^e

^aThe Second Hospital of Jilin University, Changchun Jilin 130041, People's Republic of China, ^bTraditional Chinese Medicine College of Ningxia Medical University, Yinchuan Ningxia 750004, People's Republic of China, ^cPharmacy College of Ningxia Medical University, Yinchuan Ningxia 750004, People's Republic of China, ^dMinority Traditional Medical Center of Minzu University of China, Beijing 100081, People's Republic of China, and ^eAffiliated Hospital of Ningxia Medical University, Yinchuan Ningxia 750004, People's Republic of China
^*Correspondence e-mail: nanyiailing10@yeah.net

(Received 2 December 2010; accepted 4 December 2010; online 11 December 2010)

In the title compound, C₁₄H₁₁FN₂O₂, an intramolecular O—H⋯N hydrogen bond influences the molecular conformation; the two benzene rings form a dihedral angle of 18.4 (3)°. The F atom is disordered over two positions in a 0.717 (5):0.283 (5) ratio. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains extending along the c axis.

Related literature

For the reference bond lengths, see: Allen et al. (1987 ). For structural studies of hydrazone compounds, see: Han & Zhao (2010 ); Zhou & Yang (2010 ); Huang & Wu (2010 ); Shalash et al. (2010 ). For a related structure, see: Xu et al. (2011 ).

Experimental

Crystal data

C₁₄H₁₁FN₂O₂
M_r = 258.25
Monoclinic, P 2₁ /c
a = 10.661 (3) Å
b = 13.515 (3) Å
c = 8.998 (3) Å
β = 98.150 (3)°
V = 1283.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.983
6829 measured reflections
2675 independent reflections
1093 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.198
S = 0.97
2675 reflections
180 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.637 (3)	146
N2—H2⋯O2ⁱ	0.86	2.02	2.841 (3)	158
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050841/cv5010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050841/cv5010Isup2.hkl

checkCIF report

Comment top

As a contribution to a structural study of hydrazone compounds (Han & Zhao, 2010; Zhou & Yang, 2010; Huang & Wu, 2010; Shalash et al., 2010), we present here the crystal structure of the title compound.

There is an intramolecular O—H···N hydrogen bond (Table 1) in the molecule of the title compound (Fig. 1). The molecule exists in a trans configuration with respect to the methylidene unit. The molecule is twisted, with the dihedral angle between the two benzene rings of 18.4 (3)°. The torsion angle C7—N1—N2—C8 is 8.1 (3)°. The bond lengths are within normal ranges (Allen et al., 1987) and are comparable with those observed in the similar compounds (Xu et al., 2011).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), to form chains down the c axis (Fig. 2).

Related literature top

For the reference bond lengths, see: Allen et al. (1987). For structural studies of hydrazone compounds, see: Han & Zhao (2010); Zhou & Yang (2010); Huang & Wu (2010); Shalash et al. (2010). For a related structure, see: Xu et al. (2011).

Experimental top

Salicylaldehyde (0.1 mmol, 12.2 mg) and 2-fluorobenzohydrazide (0.1 mmol, 15.4 mg) were mixed in ethanol (20 ml). The mixture was stirred at room temperature to give a clear colorless solution. Colorless well shaped crystals of the title compound were formed by gradual evaporation of the solvent over a period of three days at room temperature.

Structure description top

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), to form chains down the c axis (Fig. 2).

For the reference bond lengths, see: Allen et al. (1987). For structural studies of hydrazone compounds, see: Han & Zhao (2010); Zhou & Yang (2010); Huang & Wu (2010); Shalash et al. (2010). For a related structure, see: Xu et al. (2011).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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, with displacement ellipsoids drawn at the 30% probability level. The disordered fluorine atom F1 is shown in the major position. Dashed line denotes hydrogen bond.
	Fig. 2. A portion of the crystal packing showing hydrogen-bonded (dashed lines) one-dimensional chain of the molecules. H atoms not involved in hydrogen-bonding omitted for clarity.

2-Fluoro-N'-(2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁FN₂O₂	F(000) = 536
M_r = 258.25	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 620 reflections
a = 10.661 (3) Å	θ = 2.4–24.3°
b = 13.515 (3) Å	µ = 0.10 mm⁻¹
c = 8.998 (3) Å	T = 298 K
β = 98.150 (3)°	Block, colourless
V = 1283.4 (6) Å³	0.20 × 0.20 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	1093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
T_min = 0.980, T_max = 0.983	k = −17→15
6829 measured reflections	l = −11→10

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0776P)²] where P = (F_o² + 2F_c²)/3
2675 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₁FN₂O₂	V = 1283.4 (6) Å³
M_r = 258.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.661 (3) Å	µ = 0.10 mm⁻¹
b = 13.515 (3) Å	T = 298 K
c = 8.998 (3) Å	0.20 × 0.20 × 0.17 mm
β = 98.150 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2675 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1093 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.983	R_int = 0.066
6829 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.198	H-atom parameters constrained
S = 0.97	Δρ_max = 0.37 e Å⁻³
2675 reflections	Δρ_min = −0.18 e Å⁻³
180 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.7863 (3)	0.15833 (19)	1.0481 (3)	0.0527 (8)
N2	0.7326 (3)	0.23495 (19)	0.9579 (3)	0.0576 (8)
H2	0.7179	0.2280	0.8620	0.069*
O1	0.9198 (3)	0.08661 (17)	1.2936 (2)	0.0711 (8)
H1	0.8803	0.1289	1.2408	0.107*
O2	0.7248 (2)	0.33336 (17)	1.1581 (2)	0.0712 (8)
C1	0.8526 (3)	−0.0093 (2)	1.0701 (3)	0.0506 (9)
C2	0.9105 (3)	−0.0011 (2)	1.2207 (4)	0.0527 (9)
C3	0.9606 (3)	−0.0842 (3)	1.2979 (4)	0.0717 (11)
H3	1.0004	−0.0782	1.3964	0.086*
C4	0.9518 (4)	−0.1747 (3)	1.2298 (5)	0.0804 (12)
H4	0.9841	−0.2300	1.2835	0.096*
C5	0.8961 (4)	−0.1856 (3)	1.0833 (5)	0.0809 (12)
H5	0.8911	−0.2477	1.0382	0.097*
C6	0.8476 (3)	−0.1033 (3)	1.0036 (4)	0.0692 (11)
H6	0.8111	−0.1104	0.9040	0.083*
C7	0.7984 (3)	0.0748 (2)	0.9849 (3)	0.0554 (9)
H7	0.7720	0.0681	0.8824	0.067*
C8	0.7038 (3)	0.3200 (2)	1.0222 (3)	0.0499 (9)
C9	0.6465 (3)	0.3994 (2)	0.9199 (3)	0.0511 (9)
C11	0.5089 (4)	0.4606 (4)	0.7014 (4)	0.0849 (13)
H11	0.4522	0.4476	0.6152	0.102*
C12	0.5415 (4)	0.5549 (4)	0.7403 (5)	0.0922 (14)
H12	0.5064	0.6068	0.6805	0.111*
C13	0.6252 (3)	0.5749 (2)	0.8661 (3)	0.0853 (13)
H13	0.6484	0.6397	0.8912	0.102*
C10	0.5613 (3)	0.3835 (2)	0.7917 (3)	0.0668 (10)
H10	0.5381	0.3188	0.7649	0.080*	0.283 (5)
F1'	0.7513 (8)	0.5218 (5)	1.0737 (9)	0.100 (4)	0.283 (5)
C14	0.6747 (4)	0.4973 (3)	0.9556 (4)	0.0670 (10)
H14A	0.7291	0.5114	1.0432	0.080*	0.717 (5)
F1	0.5221 (3)	0.2946 (2)	0.7509 (3)	0.0909 (14)	0.717 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0652 (19)	0.0501 (16)	0.0403 (15)	0.0014 (14)	−0.0004 (13)	0.0089 (14)
N2	0.081 (2)	0.0543 (17)	0.0348 (14)	0.0059 (15)	−0.0007 (14)	0.0064 (13)
O1	0.092 (2)	0.0656 (16)	0.0514 (14)	0.0041 (14)	−0.0058 (13)	−0.0005 (12)
O2	0.098 (2)	0.0753 (17)	0.0376 (13)	0.0060 (13)	0.0017 (12)	−0.0036 (12)
C1	0.056 (2)	0.051 (2)	0.0455 (19)	−0.0016 (16)	0.0106 (16)	0.0028 (16)
C2	0.054 (2)	0.055 (2)	0.050 (2)	0.0039 (17)	0.0106 (17)	0.0028 (17)
C3	0.074 (3)	0.078 (3)	0.060 (2)	0.022 (2)	0.0000 (19)	0.012 (2)
C4	0.097 (3)	0.066 (3)	0.081 (3)	0.027 (2)	0.023 (3)	0.020 (2)
C5	0.105 (3)	0.055 (2)	0.085 (3)	0.010 (2)	0.022 (3)	−0.003 (2)
C6	0.086 (3)	0.062 (2)	0.059 (2)	0.001 (2)	0.006 (2)	−0.0040 (19)
C7	0.067 (2)	0.059 (2)	0.0388 (18)	−0.0080 (18)	−0.0002 (16)	0.0029 (17)
C8	0.063 (2)	0.050 (2)	0.0355 (18)	−0.0019 (16)	0.0023 (16)	0.0002 (15)
C9	0.059 (2)	0.058 (2)	0.0383 (17)	0.0054 (17)	0.0115 (16)	0.0036 (15)
C11	0.089 (3)	0.104 (4)	0.059 (2)	0.041 (3)	−0.001 (2)	0.011 (2)
C12	0.105 (4)	0.090 (4)	0.087 (3)	0.040 (3)	0.031 (3)	0.030 (3)
C13	0.101 (4)	0.059 (3)	0.100 (3)	0.009 (2)	0.025 (3)	0.008 (2)
C10	0.075 (3)	0.074 (3)	0.050 (2)	0.005 (2)	0.005 (2)	−0.0020 (19)
F1'	0.115 (7)	0.075 (6)	0.097 (7)	−0.002 (5)	−0.025 (5)	−0.006 (5)
C14	0.076 (3)	0.062 (2)	0.064 (2)	0.006 (2)	0.013 (2)	0.001 (2)
F1	0.096 (3)	0.074 (2)	0.088 (2)	0.0046 (17)	−0.0376 (18)	−0.0071 (17)

Geometric parameters (Å, º) top

N1—C7	1.278 (4)	C6—H6	0.9300
N1—N2	1.389 (3)	C7—H7	0.9300
N2—C8	1.342 (4)	C8—C9	1.487 (4)
N2—H2	0.8600	C9—C10	1.381 (4)
O1—C2	1.351 (4)	C9—C14	1.384 (5)
O1—H1	0.8200	C11—C12	1.354 (5)
O2—C8	1.225 (3)	C11—C10	1.389 (4)
C1—C6	1.402 (4)	C11—H11	0.9300
C1—C2	1.412 (4)	C12—C13	1.365 (5)
C1—C7	1.445 (4)	C12—H12	0.9300
C2—C3	1.387 (4)	C13—C14	1.380 (4)
C3—C4	1.366 (5)	C13—H13	0.9300
C3—H3	0.9300	C10—F1	1.307 (4)
C4—C5	1.375 (5)	C10—H10	0.9300
C4—H4	0.9300	F1'—C14	1.288 (7)
C5—C6	1.384 (5)	C14—H14A	0.9300
C5—H5	0.9300

C7—N1—N2	117.2 (2)	O2—C8—N2	122.4 (3)
C8—N2—N1	119.2 (2)	O2—C8—C9	120.8 (3)
C8—N2—H2	120.4	N2—C8—C9	116.8 (3)
N1—N2—H2	120.4	C10—C9—C14	116.0 (3)
C2—O1—H1	109.5	C10—C9—C8	124.6 (3)
C6—C1—C2	117.8 (3)	C14—C9—C8	119.3 (3)
C6—C1—C7	119.9 (3)	C12—C11—C10	119.2 (4)
C2—C1—C7	122.4 (3)	C12—C11—H11	120.4
O1—C2—C3	118.1 (3)	C10—C11—H11	120.4
O1—C2—C1	121.8 (3)	C11—C12—C13	120.9 (4)
C3—C2—C1	120.1 (3)	C11—C12—H12	119.5
C4—C3—C2	120.2 (3)	C13—C12—H12	119.5
C4—C3—H3	119.9	C12—C13—C14	119.0 (3)
C2—C3—H3	119.9	C12—C13—H13	120.5
C3—C4—C5	121.3 (4)	C14—C13—H13	120.5
C3—C4—H4	119.3	F1—C10—C9	121.6 (3)
C5—C4—H4	119.3	F1—C10—C11	116.1 (3)
C4—C5—C6	119.3 (4)	C9—C10—C11	122.3 (3)
C4—C5—H5	120.4	C9—C10—H10	118.9
C6—C5—H5	120.4	C11—C10—H10	118.9
C5—C6—C1	121.3 (3)	F1'—C14—C13	115.6 (5)
C5—C6—H6	119.4	F1'—C14—C9	121.9 (5)
C1—C6—H6	119.4	C13—C14—C9	122.5 (4)
N1—C7—C1	121.1 (3)	C13—C14—H14A	118.7
N1—C7—H7	119.5	C9—C14—H14A	118.7
C1—C7—H7	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.637 (3)	146
N2—H2···O2ⁱ	0.86	2.02	2.841 (3)	158.4

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁FN₂O₂
M_r	258.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.661 (3), 13.515 (3), 8.998 (3)
β (°)	98.150 (3)
V (Å³)	1283.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	6829, 2675, 1093
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.198, 0.97
No. of reflections	2675
No. of parameters	180
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
O1—H1···N1	0.82	1.92	2.637 (3)	145.9
N2—H2···O2ⁱ	0.86	2.02	2.841 (3)	158.4

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This project was supported by the 2008 Ningxia science and technology key projects (No. 222) and the 2009 Ningxia science and technology key projects (No. 232).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041. Web of Science CSD CrossRef IUCr Journals Google Scholar
Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729–o2730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126–o3127. Web of Science CSD CrossRef 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
Xu, C.-B., Wang, Z.-G., Nan, Y., Yuan, L., Wang, R. & Zhang, S.-X. (2011). Acta Cryst. E67, o70. Web of Science CrossRef IUCr Journals Google Scholar
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o752. Web of Science CrossRef IUCr Journals Google Scholar