(E)-2-Chloro-N′-(4-hy­droxy­benzyl­idene)­benzohydrazide

Li, X.-Y.

doi:10.1107/S1600536812005661

organic compounds

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Volume 68| Part 3| March 2012| Page o709

doi:10.1107/S1600536812005661

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(E)-2-Chloro-N′-(4-hydroxybenzylidene)benzohydrazide

Xiao-Yan Li ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
^*Correspondence e-mail: lixiaoyan_zb@126.com

(Received 6 February 2012; accepted 8 February 2012; online 17 February 2012)

The title hydrazone molecule, C₁₄H₁₁ClN₂O₂, has a trans conformation with respect to the methylidene unit. The dihedral angle between the two benzene rings is 37.6 (3)°. In the crystal, the presence of O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds leads to the formation of a three-dimensional network. The title compound crystallized in the chiral orthorhombic space group P2₁2₁2₁ and was refined as an inversion twin [Flack parameter = −0.20 (18)].

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ); Lei (2011 ); Shalash et al. (2010 ). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ,b ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 274.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.627 (3) Å
b = 11.859 (2) Å
c = 14.297 (2) Å
V = 1293.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.952
6966 measured reflections
2408 independent reflections
1717 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.167
S = 1.07
2408 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 999 Friedel pairs
Flack parameter: −0.20 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.99	2.751 (4)	155
O2—H2⋯N2ⁱ	0.82	2.48	3.012 (4)	124
N1—H1⋯O2ⁱⁱ	0.90 (1)	2.12 (2)	2.987 (4)	164 (5)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536812005661/su2376sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005661/su2376Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005661/su2376Isup3.cml

checkCIF report

Comment top

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

The molecule of the title compound (Fig. 1) exists in a trans conformation with respect to the methylidene unit. The dihedral angle between the (C1–C6) and (C9–C1) benzene rings is 37.6 (3)°.

In the crystal, O–H···O, O–H···N, and N–H···O hydrogen bonds leads to the formation of a three-dimensional network (Table 1, Fig. 2).

Related literature top

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a,b).

Experimental top

A mixture of 4-hydroxybenzaldehyde (0.122 g, 1 mmol) and 2-chlorobenzohydrazide (0.171 g, 1 mmol) in 30 ml of methanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.

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, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The various hydrogen bonds are indicated by dashed lines (see Table 1 for details; C-bound H-atoms have been omitted for clarity)..

(E)-2-Chloro-N'-(4-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 568
M_r = 274.70	D_x = 1.411 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1608 reflections
a = 7.627 (3) Å	θ = 2.2–24.3°
b = 11.859 (2) Å	µ = 0.29 mm⁻¹
c = 14.297 (2) Å	T = 298 K
V = 1293.2 (5) Å³	Block, colourless
Z = 4	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	1717 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 = −9→8
T_min = 0.949, T_max = 0.952	k = −14→9
6966 measured reflections	l = −17→17

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0863P)² + 0.1245P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2408 reflections	Δρ_max = 0.74 e Å⁻³
176 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 999 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.20 (18)

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 1293.2 (5) Å³
M_r = 274.70	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.627 (3) Å	µ = 0.29 mm⁻¹
b = 11.859 (2) Å	T = 298 K
c = 14.297 (2) Å	0.18 × 0.17 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2408 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1717 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.952	R_int = 0.045
6966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.167	Δρ_max = 0.74 e Å⁻³
S = 1.07	Δρ_min = −0.35 e Å⁻³
2408 reflections	Absolute structure: Flack (1983), 999 Friedel pairs
176 parameters	Absolute structure parameter: −0.20 (18)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.7790 (2)	1.15240 (11)	0.03121 (11)	0.0961 (6)
N1	0.8701 (5)	0.7962 (3)	0.0532 (2)	0.0446 (9)
N2	0.8920 (5)	0.7314 (3)	−0.0268 (2)	0.0442 (8)
O1	0.9755 (4)	0.9473 (2)	−0.02416 (18)	0.0479 (8)
O2	0.8755 (4)	0.3362 (2)	−0.32680 (17)	0.0439 (7)
H2	0.9466	0.3582	−0.3657	0.066*
C1	0.8856 (5)	0.9734 (3)	0.1347 (3)	0.0405 (10)
C2	0.8308 (6)	1.0829 (4)	0.1335 (3)	0.0521 (12)
C3	0.8123 (6)	1.1435 (5)	0.2166 (4)	0.0698 (15)
H3	0.7742	1.2180	0.2156	0.084*
C4	0.8506 (8)	1.0924 (6)	0.2987 (4)	0.0780 (18)
H4	0.8395	1.1328	0.3541	0.094*
C5	0.9046 (7)	0.9840 (6)	0.3022 (3)	0.0729 (16)
H5	0.9287	0.9510	0.3598	0.087*
C6	0.9240 (6)	0.9228 (5)	0.2230 (3)	0.0551 (12)
H6	0.9621	0.8484	0.2260	0.066*
C7	0.9150 (5)	0.9061 (3)	0.0472 (3)	0.0368 (9)
C8	0.8585 (5)	0.6256 (3)	−0.0187 (3)	0.0408 (9)
H8	0.8278	0.5966	0.0395	0.049*
C9	0.8678 (5)	0.5508 (3)	−0.0988 (2)	0.0375 (9)
C10	0.8151 (6)	0.4403 (3)	−0.0916 (3)	0.0430 (10)
H10	0.7773	0.4128	−0.0341	0.052*
C11	0.8172 (6)	0.3700 (3)	−0.1673 (3)	0.0433 (10)
H11	0.7812	0.2955	−0.1607	0.052*
C12	0.8724 (5)	0.4086 (3)	−0.2536 (2)	0.0335 (8)
C13	0.9259 (5)	0.5197 (3)	−0.2627 (3)	0.0387 (9)
H13	0.9637	0.5465	−0.3204	0.046*
C14	0.9231 (5)	0.5905 (3)	−0.1863 (3)	0.0413 (10)
H14	0.9581	0.6652	−0.1929	0.050*
H1	0.802 (6)	0.767 (4)	0.098 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1370 (15)	0.0600 (8)	0.0912 (11)	0.0223 (9)	0.0056 (10)	0.0157 (8)
N1	0.062 (2)	0.0378 (19)	0.0339 (18)	−0.0073 (18)	0.0079 (17)	−0.0053 (14)
N2	0.062 (2)	0.0404 (19)	0.0304 (17)	−0.0049 (17)	0.0069 (18)	−0.0085 (15)
O1	0.069 (2)	0.0401 (15)	0.0349 (14)	−0.0095 (14)	0.0108 (14)	−0.0016 (13)
O2	0.063 (2)	0.0377 (15)	0.0310 (14)	−0.0025 (15)	0.0058 (13)	−0.0083 (12)
C1	0.040 (2)	0.043 (2)	0.038 (2)	−0.007 (2)	0.0070 (18)	−0.0085 (18)
C2	0.054 (3)	0.047 (3)	0.055 (3)	−0.010 (2)	0.011 (2)	−0.012 (2)
C3	0.061 (3)	0.057 (3)	0.091 (4)	−0.013 (3)	0.025 (3)	−0.027 (3)
C4	0.074 (4)	0.094 (5)	0.066 (4)	−0.027 (4)	0.015 (3)	−0.041 (3)
C5	0.078 (4)	0.102 (5)	0.039 (3)	−0.013 (4)	−0.003 (2)	−0.013 (3)
C6	0.057 (3)	0.076 (3)	0.032 (2)	−0.010 (2)	0.0049 (19)	−0.014 (2)
C7	0.039 (2)	0.038 (2)	0.033 (2)	−0.0001 (18)	0.0004 (17)	−0.0018 (17)
C8	0.048 (2)	0.044 (2)	0.0309 (19)	−0.002 (2)	−0.0013 (19)	−0.0076 (17)
C9	0.042 (2)	0.037 (2)	0.0332 (19)	0.001 (2)	0.0016 (17)	−0.0013 (17)
C10	0.061 (3)	0.038 (2)	0.0300 (19)	0.002 (2)	0.0041 (18)	0.0006 (17)
C11	0.060 (3)	0.030 (2)	0.040 (2)	0.0002 (19)	0.006 (2)	0.0002 (16)
C12	0.038 (2)	0.0296 (19)	0.0330 (19)	0.0046 (17)	−0.0029 (16)	−0.0027 (15)
C13	0.044 (2)	0.044 (2)	0.0284 (19)	0.0010 (18)	0.0038 (16)	0.0011 (17)
C14	0.054 (3)	0.030 (2)	0.040 (2)	−0.0063 (19)	0.0028 (19)	−0.0012 (17)

Geometric parameters (Å, º) top

Cl1—C2	1.724 (5)	C5—C6	1.353 (6)
N1—C7	1.350 (5)	C5—H5	0.9300
N1—N2	1.388 (4)	C6—H6	0.9300
N1—H1	0.896 (10)	C8—C9	1.450 (5)
N2—C8	1.286 (5)	C8—H8	0.9300
O1—C7	1.222 (5)	C9—C10	1.375 (5)
O2—C12	1.354 (4)	C9—C14	1.402 (5)
O2—H2	0.8200	C10—C11	1.366 (5)
C1—C2	1.364 (6)	C10—H10	0.9300
C1—C6	1.429 (6)	C11—C12	1.382 (5)
C1—C7	1.500 (5)	C11—H11	0.9300
C2—C3	1.396 (7)	C12—C13	1.384 (5)
C3—C4	1.353 (8)	C13—C14	1.377 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.350 (9)	C14—H14	0.9300
C4—H4	0.9300

C7—N1—N2	116.9 (3)	O1—C7—C1	122.7 (3)
C7—N1—H1	125 (3)	N1—C7—C1	115.1 (3)
N2—N1—H1	116 (3)	N2—C8—C9	121.1 (4)
C8—N2—N1	116.2 (3)	N2—C8—H8	119.5
C12—O2—H2	109.5	C9—C8—H8	119.5
C2—C1—C6	118.3 (4)	C10—C9—C14	118.3 (3)
C2—C1—C7	122.8 (4)	C10—C9—C8	120.7 (3)
C6—C1—C7	118.8 (4)	C14—C9—C8	120.9 (3)
C1—C2—C3	120.7 (5)	C11—C10—C9	121.3 (4)
C1—C2—Cl1	122.4 (3)	C11—C10—H10	119.3
C3—C2—Cl1	116.9 (4)	C9—C10—H10	119.3
C4—C3—C2	119.1 (5)	C10—C11—C12	120.5 (3)
C4—C3—H3	120.5	C10—C11—H11	119.7
C2—C3—H3	120.5	C12—C11—H11	119.7
C5—C4—C3	121.6 (5)	O2—C12—C11	119.0 (3)
C5—C4—H4	119.2	O2—C12—C13	121.8 (3)
C3—C4—H4	119.2	C11—C12—C13	119.3 (3)
C4—C5—C6	120.9 (5)	C14—C13—C12	120.1 (3)
C4—C5—H5	119.6	C14—C13—H13	120.0
C6—C5—H5	119.6	C12—C13—H13	120.0
C5—C6—C1	119.5 (5)	C13—C14—C9	120.5 (4)
C5—C6—H6	120.3	C13—C14—H14	119.7
C1—C6—H6	120.3	C9—C14—H14	119.7
O1—C7—N1	122.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.99	2.751 (4)	155
O2—H2···N2ⁱ	0.82	2.48	3.012 (4)	124
N1—H1···O2ⁱⁱ	0.90 (1)	2.12 (2)	2.987 (4)	164 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂
M_r	274.70
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.627 (3), 11.859 (2), 14.297 (2)
V (Å³)	1293.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.18 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	6966, 2408, 1717
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.167, 1.07
No. of reflections	2408
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)	0.74, −0.35
Absolute structure	Flack (1983), 999 Friedel pairs
Absolute structure parameter	−0.20 (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
O2—H2···O1ⁱ	0.82	1.99	2.751 (4)	154.8
O2—H2···N2ⁱ	0.82	2.48	3.012 (4)	123.8
N1—H1···O2ⁱⁱ	0.896 (10)	2.117 (18)	2.987 (4)	164 (5)

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

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

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