N′-(2-Chloro­benzyl­idene)-4-hydroxy­benzohydrazide

Hao, Y.-M.

doi:10.1107/S1600536809030797

organic compounds

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Volume 65| Part 9| September 2009| Page o2098

doi:10.1107/S1600536809030797

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N′-(2-Chlorobenzylidene)-4-hydroxybenzohydrazide

Yu-Mei Hao ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: jyxygzb@163.com

(Received 1 August 2009; accepted 3 August 2009; online 8 August 2009)

In the molecule of the title compound, C₁₄H₁₁ClN₂O₂, the dihedral angle between the benzene rings is 30.53 (4)°. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a two-dimensional network. π–π contacts between benzene rings [centroid–centroid distance = 3.619 (1) Å] may further stabilize the structure. The crystal studied was found to be an inversion twin.

Related literature

For general background, see: Ali et al. (2008 ); Dao et al. (2000 ); Kargar et al. (2009 ); Karthikeyan et al. (2006 ); Sriram et al. (2006 ); Yeap et al. (2009 ). For related structures, see: Eltayeb et al. (2008 ); Fun et al. (2009 ); Hao (2009 ); Nadeem et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 274.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.2851 (17) Å
b = 11.716 (3) Å
c = 14.978 (3) Å
V = 1278.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.948
6989 measured reflections
2360 independent reflections
1617 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.105
S = 1.02
2360 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 963 Friedel pairs
Flack parameter: 0.45 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.84	2.657 (3)	179
N2—H2A⋯O2ⁱⁱ	0.90 (3)	2.106 (17)	2.951 (3)	157 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030797/hk2750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030797/hk2750Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are a class of important materials used in pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). As a part of our ongoing investigation (Hao, 2009), we report herein the crystal structure of the title new Schiff base compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar and the dihedral angle between them is A/B = 30.53 (4)°.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the benzene rings, Cg1—Cg2ⁱ [symmetry code: (i) 1/2 + x, 1/2 - y, 1 - z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C9-C14), respectively] may further stabilize the structure, with centroid-centroid distance of 3.619 (1) Å.

Related literature top

For general background, see: Ali et al. (2008); Dao et al. (2000); Kargar et al. (2009); Karthikeyan et al. (2006); Sriram et al. (2006); Yeap et al. (2009). For related structures, see: Eltayeb et al. (2008); Fun et al. (2009); Hao (2009); Nadeem et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2-chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 4-hydroxybenzohydrazide (0.1 mmol, 15.2 mg) were refluxed in a methanol solution (30 ml) for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

N'-(2-Chlorobenzylidene)-4-hydroxybenzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 568
M_r = 274.70	D_x = 1.427 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1016 reflections
a = 7.2851 (17) Å	θ = 2.4–24.5°
b = 11.716 (3) Å	µ = 0.30 mm⁻¹
c = 14.978 (3) Å	T = 298 K
V = 1278.4 (5) Å³	Block, yellow
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1617 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.943, T_max = 0.948	k = −14→13
6989 measured reflections	l = −16→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0459P)² + 0.0042P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2360 reflections	Δρ_max = 0.15 e Å⁻³
176 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 963 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.45 (12)

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 1278.4 (5) Å³
M_r = 274.70	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.2851 (17) Å	µ = 0.30 mm⁻¹
b = 11.716 (3) Å	T = 298 K
c = 14.978 (3) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2360 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1617 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.948	R_int = 0.045
6989 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	Δρ_max = 0.15 e Å⁻³
S = 1.02	Δρ_min = −0.26 e Å⁻³
2360 reflections	Absolute structure: Flack (1983), 963 Friedel pairs
176 parameters	Absolute structure parameter: 0.45 (12)
1 restraint

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
Cl1	0.01997 (17)	0.34021 (7)	1.00869 (6)	0.0874 (4)
O1	0.1624 (4)	0.92529 (17)	1.04651 (12)	0.0549 (6)
O2	0.1212 (3)	1.16180 (18)	0.67205 (12)	0.0510 (6)
H2	0.1881	1.1358	0.6330	0.077*
N1	0.1278 (4)	0.69987 (19)	1.04360 (14)	0.0437 (7)
N2	0.1146 (4)	0.7642 (2)	0.96676 (14)	0.0440 (7)
C1	0.1105 (4)	0.5194 (2)	1.11448 (19)	0.0410 (7)
C2	0.0682 (4)	0.4040 (3)	1.1104 (2)	0.0512 (9)
C3	0.0627 (4)	0.3368 (3)	1.1861 (3)	0.0616 (10)
H3	0.0335	0.2597	1.1817	0.074*
C4	0.1006 (5)	0.3842 (3)	1.2681 (2)	0.0640 (10)
H4	0.0949	0.3394	1.3192	0.077*
C5	0.1472 (5)	0.4985 (3)	1.2746 (2)	0.0588 (10)
H5	0.1749	0.5303	1.3298	0.071*
C6	0.1523 (4)	0.5648 (3)	1.19849 (19)	0.0473 (8)
H6	0.1841	0.6415	1.2032	0.057*
C7	0.1054 (4)	0.5933 (2)	1.03614 (19)	0.0439 (8)
H7	0.0855	0.5617	0.9800	0.053*
C8	0.1310 (4)	0.8794 (2)	0.97441 (17)	0.0377 (7)
C9	0.1139 (4)	0.9470 (2)	0.89145 (17)	0.0352 (7)
C10	0.1551 (4)	0.9036 (2)	0.80756 (17)	0.0394 (7)
H10	0.1814	0.8263	0.8012	0.047*
C11	0.1576 (4)	0.9737 (2)	0.73349 (18)	0.0416 (8)
H11	0.1876	0.9443	0.6777	0.050*
C12	0.1154 (4)	1.0875 (2)	0.74280 (16)	0.0364 (7)
C13	0.0671 (4)	1.1313 (2)	0.82502 (17)	0.0412 (7)
H13	0.0335	1.2075	0.8306	0.049*
C14	0.0692 (4)	1.0614 (2)	0.89873 (18)	0.0409 (8)
H14	0.0401	1.0915	0.9544	0.049*
H2A	0.074 (5)	0.729 (3)	0.9172 (14)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1341 (10)	0.0427 (5)	0.0854 (7)	−0.0074 (6)	−0.0095 (7)	−0.0113 (5)
O1	0.0965 (19)	0.0376 (12)	0.0307 (11)	0.0005 (12)	−0.0119 (12)	−0.0021 (10)
O2	0.0687 (16)	0.0474 (13)	0.0370 (11)	0.0128 (13)	0.0090 (11)	0.0133 (10)
N1	0.0627 (18)	0.0340 (15)	0.0344 (13)	−0.0020 (13)	−0.0077 (14)	0.0041 (11)
N2	0.067 (2)	0.0337 (14)	0.0308 (13)	−0.0053 (13)	−0.0059 (15)	0.0026 (11)
C1	0.0396 (19)	0.0398 (18)	0.0435 (17)	0.0050 (15)	0.0051 (16)	0.0050 (14)
C2	0.054 (2)	0.0396 (19)	0.0604 (19)	0.0031 (15)	0.0022 (18)	0.0074 (16)
C3	0.052 (2)	0.043 (2)	0.089 (3)	−0.0012 (18)	0.008 (2)	0.026 (2)
C4	0.057 (2)	0.068 (3)	0.067 (2)	0.0149 (19)	0.011 (2)	0.0335 (19)
C5	0.064 (2)	0.065 (3)	0.048 (2)	0.011 (2)	0.0036 (19)	0.0125 (18)
C6	0.049 (2)	0.049 (2)	0.0434 (18)	0.0043 (16)	0.0009 (17)	0.0087 (16)
C7	0.056 (2)	0.0378 (18)	0.0378 (16)	0.0035 (16)	0.0009 (17)	−0.0018 (14)
C8	0.0477 (19)	0.0360 (16)	0.0294 (15)	−0.0026 (14)	−0.0012 (15)	0.0003 (12)
C9	0.0418 (18)	0.0320 (16)	0.0317 (14)	−0.0026 (13)	−0.0054 (15)	0.0005 (12)
C10	0.052 (2)	0.0340 (17)	0.0325 (15)	0.0014 (15)	0.0012 (15)	−0.0014 (13)
C11	0.052 (2)	0.0432 (19)	0.0297 (16)	0.0042 (16)	0.0012 (15)	−0.0009 (13)
C12	0.0416 (18)	0.0381 (17)	0.0295 (15)	0.0000 (15)	−0.0015 (15)	0.0083 (13)
C13	0.055 (2)	0.0309 (16)	0.0377 (16)	0.0052 (14)	0.0017 (15)	0.0004 (13)
C14	0.057 (2)	0.0345 (17)	0.0316 (15)	−0.0006 (14)	0.0032 (15)	−0.0025 (13)

Geometric parameters (Å, º) top

Cl1—C2	1.732 (3)	C5—C6	1.380 (4)
O1—C8	1.228 (3)	C5—H5	0.9300
O2—C12	1.372 (3)	C6—H6	0.9300
O2—H2	0.8200	C7—H7	0.9300
N1—N2	1.379 (3)	C8—C9	1.479 (4)
N1—C7	1.264 (3)	C9—C14	1.383 (4)
N2—C8	1.360 (3)	C9—C10	1.388 (4)
N2—H2A	0.90 (3)	C10—C11	1.381 (4)
C1—C2	1.388 (4)	C10—H10	0.9300
C1—C6	1.400 (4)	C11—C12	1.375 (4)
C1—C7	1.459 (4)	C11—H11	0.9300
C2—C3	1.381 (4)	C12—C13	1.380 (4)
C3—C4	1.376 (5)	C13—C14	1.375 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (5)	C14—H14	0.9300
C4—H4	0.9300

C12—O2—H2	109.5	N1—C7—H7	119.6
C7—N1—N2	117.2 (2)	C1—C7—H7	119.6
N1—N2—H2A	118 (2)	O1—C8—N2	121.7 (2)
C8—N2—N1	117.8 (2)	O1—C8—C9	121.4 (2)
C8—N2—H2A	123 (2)	N2—C8—C9	117.0 (2)
C2—C1—C6	117.3 (3)	C14—C9—C10	118.5 (2)
C2—C1—C7	122.5 (3)	C14—C9—C8	118.2 (2)
C6—C1—C7	120.2 (3)	C10—C9—C8	123.1 (3)
C3—C2—C1	121.7 (3)	C11—C10—C9	120.8 (3)
C3—C2—Cl1	118.0 (3)	C11—C10—H10	119.6
C1—C2—Cl1	120.3 (2)	C9—C10—H10	119.6
C4—C3—C2	119.8 (3)	C12—C11—C10	119.5 (2)
C4—C3—H3	120.1	C12—C11—H11	120.2
C2—C3—H3	120.1	C10—C11—H11	120.2
C3—C4—C5	120.2 (3)	O2—C12—C11	122.0 (2)
C3—C4—H4	119.9	O2—C12—C13	117.5 (2)
C5—C4—H4	119.9	C11—C12—C13	120.5 (2)
C6—C5—C4	119.6 (3)	C14—C13—C12	119.5 (3)
C6—C5—H5	120.2	C14—C13—H13	120.2
C4—C5—H5	120.2	C12—C13—H13	120.2
C5—C6—C1	121.5 (3)	C13—C14—C9	121.1 (3)
C5—C6—H6	119.2	C13—C14—H14	119.5
C1—C6—H6	119.2	C9—C14—H14	119.5
N1—C7—C1	120.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.657 (3)	179
N2—H2A···O2ⁱⁱ	0.90 (3)	2.11 (2)	2.951 (3)	157 (3)

Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂
M_r	274.70
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.2851 (17), 11.716 (3), 14.978 (3)
V (Å³)	1278.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	6989, 2360, 1617
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.105, 1.02
No. of reflections	2360
No. of parameters	176
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.26
Absolute structure	Flack (1983), 963 Friedel pairs
Absolute structure parameter	0.45 (12)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O2—H2···O1ⁱ	0.82	1.84	2.657 (3)	178.9
N2—H2A···O2ⁱⁱ	0.90 (3)	2.106 (17)	2.951 (3)	157 (3)

Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x, y−1/2, −z+3/2.

References

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