3-Chloro-N′-(4-hy­droxy­benzyl­idene)benzohydrazide

Li, T.-Y.; Ran, X.-L.

doi:10.1107/S1600536811000699

organic compounds

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Volume 67| Part 2| February 2011| Page o331

doi:10.1107/S1600536811000699

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3-Chloro-N′-(4-hydroxybenzylidene)benzohydrazide

Tian-Yi Li ^a ^* and Xiao-Li Ran ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: cooperationwell@126.com

(Received 31 December 2010; accepted 6 January 2011; online 12 January 2011)

The title compound, C₁₄H₁₁ClN₂O₂, was prepared by the reaction of 4-hydroxybenzaldehyde with 3-chlorobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 38.2 (2)°. In the crystal, molecules are linked through intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming layers lying parallel to the bc plane.

Related literature

For background to Schiff base compounds derived from the reaction of aldehydes with benzohydrazides, see: Pouralimardan et al. (2007 ); Dinda et al. (2002 ). For the reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 274.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.547 (2) Å
b = 11.754 (3) Å
c = 14.912 (3) Å
V = 1322.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.937, T_max = 0.945
6281 measured reflections
2834 independent reflections
1754 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.094
S = 0.95
2834 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1163 Friedel pairs
Flack parameter: −0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.90 (3)	2.14 (2)	2.996 (3)	157 (3)
O1—H1⋯N1ⁱⁱ	0.82	2.55	3.004 (3)	116
O1—H1⋯O2ⁱⁱ	0.82	1.96	2.765 (3)	168
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000699/hg2786sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000699/hg2786Isup2.hkl

checkCIF report

Comment top

In the last few years, a number of Schiff bases derived from the reaction of aldehydes with benzohydrazides were prepared and structurally characterized (Pouralimardan et al., 2007; Dinda et al., 2002). As a continuation of the work, in the present paper, the title new Schiff base compound, Fig. 1, is reported.

The dihedral angle between the two benzene rings in the compound is 38.2 (2)°. All the bond lengths are within normal values (Allen et al., 1987). The molecules are linked through intermolecular N—H···O, O—H···N, and O—H···O hydrogen bonds (Table 1) to form two-dimensional layers along the bc plane (Fig. 2).

Related literature top

For background to Schiff base compounds derived from the reaction of

aldehydes with benzohydrazides, see: Pouralimardan et al. (2007); Dinda et al. (2002). For the reference bond lengths, see: Allen et al. (1987).

Experimental top

4-Hydroxybenzaldehyde (0.122 g, 1 mmol) and 3-chlorobenzohydrazide (0.171 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear colorless solution was left to slow evaporation in air for a week, yielding colorless block-shaped crystals, which were collected by filtration and washed with methanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. The molecular packing of the title compound. Hydrogen bonds are drawn as dashed lines.

3-Chloro-N'-(4-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 568
M_r = 274.70	D_x = 1.379 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 965 reflections
a = 7.547 (2) Å	θ = 2.6–25.0°
b = 11.754 (3) Å	µ = 0.29 mm⁻¹
c = 14.912 (3) Å	T = 298 K
V = 1322.8 (6) Å³	Block, colorless
Z = 4	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2834 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.937, T_max = 0.945	k = −12→15
6281 measured reflections	l = −19→16

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0302P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
2834 reflections	Δρ_max = 0.18 e Å⁻³
176 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1163 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (9)

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 1322.8 (6) Å³
M_r = 274.70	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.547 (2) Å	µ = 0.29 mm⁻¹
b = 11.754 (3) Å	T = 298 K
c = 14.912 (3) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2834 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1754 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.945	R_int = 0.051
6281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	Δρ_max = 0.18 e Å⁻³
S = 0.95	Δρ_min = −0.21 e Å⁻³
2834 reflections	Absolute structure: Flack (1983), 1163 Friedel pairs
176 parameters	Absolute structure parameter: −0.04 (9)
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	0.05610 (14)	0.59347 (8)	0.39379 (5)	0.0776 (4)
N1	0.1094 (3)	0.7672 (2)	−0.03391 (13)	0.0416 (7)
N2	0.1281 (4)	0.7085 (2)	0.04643 (14)	0.0412 (7)
O1	0.1358 (3)	1.14877 (15)	−0.33772 (12)	0.0440 (6)
H1	0.0707	1.1229	−0.3767	0.066*
O2	0.0407 (3)	0.54505 (15)	−0.02189 (11)	0.0471 (6)
C1	0.1340 (4)	1.0781 (2)	−0.26470 (16)	0.0335 (7)
C2	0.0762 (4)	0.9674 (2)	−0.26936 (16)	0.0363 (7)
H2A	0.0366	0.9377	−0.3236	0.044*
C3	0.0768 (4)	0.9002 (2)	−0.19341 (15)	0.0367 (7)
H3	0.0373	0.8254	−0.1967	0.044*
C4	0.1361 (4)	0.9437 (2)	−0.11182 (16)	0.0323 (7)
C5	0.1936 (4)	1.0556 (3)	−0.10858 (19)	0.0396 (8)
H5	0.2335	1.0855	−0.0545	0.047*
C6	0.1928 (4)	1.1235 (3)	−0.18415 (18)	0.0388 (8)
H6	0.2311	1.1986	−0.1811	0.047*
C7	0.1441 (4)	0.8728 (2)	−0.03118 (16)	0.0372 (7)
H7	0.1753	0.9059	0.0232	0.045*
C8	0.0932 (4)	0.5954 (3)	0.04547 (16)	0.0373 (7)
C9	0.1181 (4)	0.5358 (2)	0.13258 (17)	0.0348 (7)
C10	0.0839 (4)	0.5875 (3)	0.21398 (16)	0.0409 (7)
H10	0.0484	0.6632	0.2159	0.049*
C11	0.1026 (4)	0.5266 (3)	0.29184 (18)	0.0488 (9)
C12	0.1566 (4)	0.4149 (3)	0.2914 (2)	0.0557 (9)
H12	0.1686	0.3751	0.3450	0.067*
C13	0.1926 (4)	0.3627 (3)	0.2109 (2)	0.0588 (10)
H13	0.2307	0.2875	0.2097	0.071*
C14	0.1721 (4)	0.4225 (3)	0.1316 (2)	0.0468 (9)
H14	0.1945	0.3866	0.0772	0.056*
H2	0.186 (4)	0.739 (2)	0.0936 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1069 (8)	0.0920 (7)	0.0338 (4)	−0.0111 (7)	0.0067 (5)	0.0092 (4)
N1	0.059 (2)	0.0393 (16)	0.0268 (12)	−0.0055 (14)	−0.0054 (13)	0.0092 (10)
N2	0.0581 (18)	0.0387 (16)	0.0269 (13)	−0.0085 (14)	−0.0096 (13)	0.0095 (11)
O1	0.0605 (16)	0.0389 (12)	0.0327 (11)	−0.0056 (12)	−0.0066 (10)	0.0104 (9)
O2	0.0678 (15)	0.0399 (12)	0.0336 (10)	−0.0019 (12)	−0.0071 (10)	−0.0021 (9)
C1	0.0313 (16)	0.0413 (18)	0.0277 (14)	0.0012 (15)	0.0015 (12)	0.0068 (13)
C2	0.0437 (19)	0.0387 (18)	0.0265 (14)	−0.0017 (16)	−0.0044 (13)	0.0001 (12)
C3	0.0426 (19)	0.0351 (17)	0.0325 (14)	−0.0005 (16)	0.0003 (13)	0.0005 (13)
C4	0.0343 (17)	0.0340 (17)	0.0285 (14)	0.0024 (15)	−0.0012 (13)	0.0057 (12)
C5	0.049 (2)	0.042 (2)	0.0280 (15)	−0.0002 (15)	−0.0079 (13)	0.0001 (14)
C6	0.047 (2)	0.0332 (19)	0.0365 (17)	−0.0042 (15)	0.0003 (13)	0.0009 (14)
C7	0.0416 (19)	0.0413 (19)	0.0285 (15)	0.0012 (17)	−0.0040 (13)	0.0015 (13)
C8	0.041 (2)	0.0368 (18)	0.0338 (15)	−0.0008 (17)	0.0018 (13)	0.0028 (13)
C9	0.0347 (19)	0.0352 (17)	0.0344 (15)	−0.0011 (16)	−0.0020 (13)	0.0080 (12)
C10	0.0460 (19)	0.0417 (18)	0.0348 (15)	−0.0031 (16)	−0.0022 (13)	0.0090 (14)
C11	0.047 (2)	0.063 (2)	0.0371 (17)	−0.0115 (19)	−0.0014 (15)	0.0099 (15)
C12	0.052 (2)	0.062 (2)	0.054 (2)	−0.010 (2)	−0.0130 (17)	0.0299 (19)
C13	0.058 (3)	0.041 (2)	0.077 (3)	0.0030 (18)	−0.012 (2)	0.019 (2)
C14	0.049 (2)	0.039 (2)	0.052 (2)	0.0001 (17)	−0.0021 (15)	0.0042 (16)

Geometric parameters (Å, º) top

Cl1—C11	1.747 (3)	C5—C6	1.381 (4)
N1—C7	1.270 (3)	C5—H5	0.9300
N1—N2	1.390 (3)	C6—H6	0.9300
N2—C8	1.355 (4)	C7—H7	0.9300
N2—H2	0.90 (3)	C8—C9	1.488 (3)
O1—C1	1.370 (3)	C9—C10	1.382 (3)
O1—H1	0.8200	C9—C14	1.393 (4)
O2—C8	1.231 (3)	C10—C11	1.371 (4)
C1—C2	1.375 (4)	C10—H10	0.9300
C1—C6	1.387 (4)	C11—C12	1.375 (4)
C2—C3	1.380 (3)	C12—C13	1.376 (5)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.393 (3)	C13—C14	1.383 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.386 (4)	C14—H14	0.9300
C4—C7	1.464 (3)

C7—N1—N2	115.9 (2)	N1—C7—H7	119.3
C8—N2—N1	117.3 (2)	C4—C7—H7	119.3
C8—N2—H2	120 (2)	O2—C8—N2	122.9 (2)
N1—N2—H2	121 (2)	O2—C8—C9	121.8 (3)
C1—O1—H1	109.5	N2—C8—C9	115.4 (2)
O1—C1—C2	122.5 (2)	C10—C9—C14	119.0 (3)
O1—C1—C6	116.9 (3)	C10—C9—C8	122.4 (3)
C2—C1—C6	120.6 (2)	C14—C9—C8	118.6 (2)
C1—C2—C3	119.9 (2)	C11—C10—C9	119.7 (3)
C1—C2—H2A	120.0	C11—C10—H10	120.1
C3—C2—H2A	120.0	C9—C10—H10	120.1
C2—C3—C4	120.5 (3)	C10—C11—C12	121.7 (3)
C2—C3—H3	119.7	C10—C11—Cl1	118.8 (3)
C4—C3—H3	119.7	C12—C11—Cl1	119.5 (2)
C5—C4—C3	118.6 (2)	C11—C12—C13	119.2 (3)
C5—C4—C7	119.9 (2)	C11—C12—H12	120.4
C3—C4—C7	121.5 (3)	C13—C12—H12	120.4
C6—C5—C4	121.2 (3)	C12—C13—C14	119.8 (3)
C6—C5—H5	119.4	C12—C13—H13	120.1
C4—C5—H5	119.4	C14—C13—H13	120.1
C5—C6—C1	119.1 (3)	C13—C14—C9	120.6 (3)
C5—C6—H6	120.5	C13—C14—H14	119.7
C1—C6—H6	120.5	C9—C14—H14	119.7
N1—C7—C4	121.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (3)	2.14 (2)	2.996 (3)	157 (3)
O1—H1···N1ⁱⁱ	0.82	2.55	3.004 (3)	116
O1—H1···O2ⁱⁱ	0.82	1.96	2.765 (3)	168

Symmetry codes: (i) −x+1/2, −y+2, z+1/2; (ii) −x, y+1/2, −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)	7.547 (2), 11.754 (3), 14.912 (3)
V (Å³)	1322.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.937, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	6281, 2834, 1754
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.094, 0.95
No. of reflections	2834
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)	0.18, −0.21
Absolute structure	Flack (1983), 1163 Friedel pairs
Absolute structure parameter	−0.04 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (3)	2.144 (16)	2.996 (3)	157 (3)
O1—H1···N1ⁱⁱ	0.82	2.55	3.004 (3)	116
O1—H1···O2ⁱⁱ	0.82	1.96	2.765 (3)	168

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

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–S19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dinda, R., Sengupta, P., Ghosh, S., Mayer-Figge, H. & Sheldrick, W. S. (2002). J. Chem. Soc. Dalton Trans. pp. 4434–4439. Web of Science CSD CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Pouralimardan, O., Chamayou, A.-C., Janiak, C. & Hosseini-Monfared, H. (2007). Inorg. Chim. Acta, 360, 1599–1608. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o331

doi:10.1107/S1600536811000699

Open

access