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

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

doi:10.1107/S1600536810050853

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o70

https://doi.org/10.1107/S1600536810050853

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2-Fluoro-N′-(2-methoxybenzylidene)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)

The molecule of the title compound, C₁₅H₁₃FN₂O₂, exists in a trans configuration with respect to the methylidene unit. The two benzene rings form a dihedral angle of of 64.7 (2)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains propagating 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

C₁₅H₁₃FN₂O₂
M_r = 272.27
Monoclinic, P 2₁ /c
a = 13.612 (2) Å
b = 12.278 (2) Å
c = 7.925 (1) Å
β = 92.802 (3)°
V = 1322.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.988
10047 measured reflections
2821 independent reflections
1643 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.164
S = 1.03
2821 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.08	2.866 (2)	152
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536810050853/cv5011sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050853/cv5011Isup2.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.

The molecule of the title compound exists in a trans configuration with respect to the methylidene unit (Fig. 1). The molecule is twisted, with the dihedral angle between the two benzene rings of 64.7 (2)°. The torsion angle C7—N1—N2—C8 is 8.6 (2)°. The bond lengths are within normal ranges (Allen et al., 1987) and are comparable with those observed in the similar compound (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

2-Methoxybenzaldehyde (0.1 mmol, 13.6 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. Colourless well shaped crystals of the title compound were formed by gradual evaporation of the solvent over a period of five 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.
	Fig. 2. A portion of the crystal packing showing the hydrogen-bonded (dashed lines) chains of the molecules. H atoms omitted for clarity/

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

Crystal data top

C₁₅H₁₃FN₂O₂	F(000) = 568
M_r = 272.27	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1625 reflections
a = 13.612 (2) Å	θ = 2.2–26.4°
b = 12.278 (2) Å	µ = 0.10 mm⁻¹
c = 7.925 (1) Å	T = 298 K
β = 92.802 (3)°	Block, colorless
V = 1322.9 (3) Å³	0.17 × 0.13 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 27.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
T_min = 0.983, T_max = 0.988	k = −15→15
10047 measured reflections	l = −10→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0839P)²] where P = (F_o² + 2F_c²)/3
2821 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₃FN₂O₂	V = 1322.9 (3) Å³
M_r = 272.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.612 (2) Å	µ = 0.10 mm⁻¹
b = 12.278 (2) Å	T = 298 K
c = 7.925 (1) Å	0.17 × 0.13 × 0.12 mm
β = 92.802 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2821 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1643 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.988	R_int = 0.047
10047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	Δρ_max = 0.47 e Å⁻³
2821 reflections	Δρ_min = −0.26 e Å⁻³
182 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
F1	0.89639 (10)	0.58503 (11)	0.9614 (2)	0.0657 (5)
N1	0.72769 (12)	0.71726 (15)	0.9490 (2)	0.0409 (5)
H1	0.7427	0.6742	0.8687	0.049*
N2	0.63391 (12)	0.71379 (15)	1.0089 (2)	0.0392 (5)
O1	0.77942 (11)	0.85629 (12)	1.1218 (2)	0.0442 (4)
O2	0.43863 (11)	0.55230 (14)	0.7104 (2)	0.0561 (5)
C1	0.89489 (15)	0.77601 (18)	0.9435 (3)	0.0369 (5)
C2	0.94195 (16)	0.67840 (18)	0.9204 (3)	0.0414 (6)
C3	1.03448 (17)	0.6706 (2)	0.8625 (3)	0.0546 (7)
H3	1.0642	0.6030	0.8504	0.065*
C4	1.08295 (18)	0.7651 (3)	0.8224 (4)	0.0603 (8)
H4	1.1458	0.7614	0.7817	0.072*
C5	1.03917 (19)	0.8636 (2)	0.8423 (4)	0.0615 (8)
H5	1.0721	0.9269	0.8143	0.074*
C6	0.94636 (17)	0.8701 (2)	0.9034 (3)	0.0508 (7)
H6	0.9177	0.9379	0.9182	0.061*
C7	0.79557 (15)	0.78675 (18)	1.0143 (3)	0.0367 (6)
C8	0.57425 (15)	0.65389 (18)	0.9208 (3)	0.0384 (6)
H8	0.5954	0.6201	0.8240	0.046*
C9	0.47321 (15)	0.63784 (17)	0.9704 (3)	0.0376 (6)
C10	0.40509 (16)	0.58424 (17)	0.8620 (3)	0.0418 (6)
C11	0.31043 (16)	0.56584 (19)	0.9121 (4)	0.0504 (7)
H11	0.2652	0.5297	0.8403	0.061*
C12	0.28342 (17)	0.6008 (2)	1.0670 (4)	0.0591 (8)
H12	0.2197	0.5881	1.0996	0.071*
C13	0.34873 (18)	0.6544 (2)	1.1753 (4)	0.0607 (8)
H13	0.3295	0.6781	1.2801	0.073*
C14	0.44315 (17)	0.6725 (2)	1.1266 (3)	0.0500 (7)
H14	0.4876	0.7086	1.1998	0.060*
C15	0.3743 (2)	0.4906 (3)	0.6007 (4)	0.0838 (10)
H15A	0.3546	0.4257	0.6575	0.126*
H15B	0.4076	0.4711	0.5010	0.126*
H15C	0.3172	0.5333	0.5694	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0498 (9)	0.0509 (9)	0.0966 (13)	−0.0034 (7)	0.0045 (8)	0.0114 (9)
N1	0.0280 (10)	0.0526 (12)	0.0425 (12)	−0.0043 (8)	0.0072 (9)	−0.0084 (9)
N2	0.0299 (10)	0.0461 (11)	0.0420 (12)	−0.0021 (8)	0.0045 (9)	0.0006 (9)
O1	0.0435 (9)	0.0482 (9)	0.0412 (10)	−0.0005 (7)	0.0046 (8)	−0.0040 (8)
O2	0.0504 (10)	0.0698 (12)	0.0480 (11)	−0.0142 (9)	0.0016 (9)	−0.0147 (9)
C1	0.0306 (11)	0.0478 (13)	0.0323 (13)	−0.0031 (10)	0.0004 (10)	0.0015 (11)
C2	0.0331 (13)	0.0460 (14)	0.0449 (15)	−0.0051 (11)	−0.0007 (11)	0.0034 (12)
C3	0.0377 (14)	0.0665 (17)	0.0593 (18)	0.0072 (12)	0.0019 (13)	−0.0005 (14)
C4	0.0358 (14)	0.083 (2)	0.0631 (19)	−0.0034 (14)	0.0111 (13)	0.0023 (16)
C5	0.0482 (16)	0.0693 (19)	0.068 (2)	−0.0163 (14)	0.0163 (14)	0.0086 (16)
C6	0.0441 (14)	0.0538 (15)	0.0550 (17)	−0.0073 (12)	0.0078 (13)	0.0024 (13)
C7	0.0349 (12)	0.0434 (13)	0.0319 (13)	−0.0011 (10)	0.0016 (10)	0.0050 (11)
C8	0.0322 (12)	0.0444 (13)	0.0387 (14)	0.0013 (10)	0.0029 (10)	0.0020 (11)
C9	0.0313 (12)	0.0347 (12)	0.0470 (15)	0.0000 (9)	0.0021 (11)	0.0021 (11)
C10	0.0393 (13)	0.0362 (13)	0.0497 (16)	−0.0007 (10)	0.0009 (12)	−0.0001 (11)
C11	0.0333 (13)	0.0487 (15)	0.069 (2)	−0.0054 (11)	−0.0012 (13)	−0.0069 (13)
C12	0.0325 (13)	0.0613 (16)	0.085 (2)	−0.0047 (12)	0.0172 (14)	−0.0060 (16)
C13	0.0435 (15)	0.0712 (18)	0.069 (2)	−0.0037 (13)	0.0179 (14)	−0.0168 (16)
C14	0.0390 (14)	0.0585 (16)	0.0531 (17)	−0.0051 (11)	0.0087 (12)	−0.0129 (13)
C15	0.080 (2)	0.112 (3)	0.059 (2)	−0.0263 (19)	−0.0072 (17)	−0.0299 (19)

Geometric parameters (Å, º) top

F1—C2	1.351 (2)	C5—H5	0.9300
N1—C7	1.343 (3)	C6—H6	0.9300
N1—N2	1.384 (2)	C8—C9	1.462 (3)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.278 (3)	C9—C14	1.390 (3)
O1—C7	1.234 (3)	C9—C10	1.397 (3)
O2—C10	1.364 (3)	C10—C11	1.385 (3)
O2—C15	1.422 (3)	C11—C12	1.368 (4)
C1—C2	1.375 (3)	C11—H11	0.9300
C1—C6	1.395 (3)	C12—C13	1.373 (4)
C1—C7	1.495 (3)	C12—H12	0.9300
C2—C3	1.365 (3)	C13—C14	1.378 (3)
C3—C4	1.379 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.361 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.377 (3)	C15—H15C	0.9600

C7—N1—N2	121.09 (19)	N2—C8—H8	119.6
C7—N1—H1	119.5	C9—C8—H8	119.6
N2—N1—H1	119.5	C14—C9—C10	118.4 (2)
C8—N2—N1	113.74 (19)	C14—C9—C8	121.3 (2)
C10—O2—C15	117.99 (19)	C10—C9—C8	120.2 (2)
C2—C1—C6	116.6 (2)	O2—C10—C11	124.2 (2)
C2—C1—C7	124.2 (2)	O2—C10—C9	115.86 (19)
C6—C1—C7	119.1 (2)	C11—C10—C9	120.0 (2)
F1—C2—C3	117.6 (2)	C12—C11—C10	120.0 (2)
F1—C2—C1	119.0 (2)	C12—C11—H11	120.0
C3—C2—C1	123.3 (2)	C10—C11—H11	120.0
C2—C3—C4	118.6 (2)	C11—C12—C13	121.1 (2)
C2—C3—H3	120.7	C11—C12—H12	119.4
C4—C3—H3	120.7	C13—C12—H12	119.4
C5—C4—C3	120.3 (2)	C12—C13—C14	119.1 (3)
C5—C4—H4	119.9	C12—C13—H13	120.4
C3—C4—H4	119.9	C14—C13—H13	120.4
C4—C5—C6	120.4 (2)	C13—C14—C9	121.3 (2)
C4—C5—H5	119.8	C13—C14—H14	119.4
C6—C5—H5	119.8	C9—C14—H14	119.4
C5—C6—C1	120.8 (2)	O2—C15—H15A	109.5
C5—C6—H6	119.6	O2—C15—H15B	109.5
C1—C6—H6	119.6	H15A—C15—H15B	109.5
O1—C7—N1	124.29 (19)	O2—C15—H15C	109.5
O1—C7—C1	121.0 (2)	H15A—C15—H15C	109.5
N1—C7—C1	114.7 (2)	H15B—C15—H15C	109.5
N2—C8—C9	120.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.866 (2)	152

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃FN₂O₂
M_r	272.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.612 (2), 12.278 (2), 7.925 (1)
β (°)	92.802 (3)
V (Å³)	1322.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10047, 2821, 1643
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.164, 1.03
No. of reflections	2821
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

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
N1—H1···O1ⁱ	0.86	2.08	2.866 (2)	152.3

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

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

References

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