3-Chloro-N′-(3-eth­oxy-2-hy­droxy­benzyl­idene)benzohydrazide monohydrate

Li, T.-Y.; Zeng, P.-T.

doi:10.1107/S160053681100122X

organic compounds

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Volume 67| Part 2| February 2011| Page o377

doi:10.1107/S160053681100122X

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3-Chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide monohydrate

Tian-Yi Li ^a ^* and Peng-Tao Zeng ^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 10 January 2011; online 15 January 2011)

In the title compound, C₁₆H₁₅ClN₂O₃·H₂O, the water molecule is linked to the Schiff base molecule via an O—H⋯O hydrogen bond. In the Schiff base molecule, an intramolecular O—H⋯N hydrogen bond occurs and the dihedral angle between the two benzene rings is 20.5 (5)°. In the crystal, the Schiff base and water molecules are linked by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming layers in the ab plane.

Related literature

For Schiff base compounds, see: Bessy et al. (2006 ); Podyachev et al. (2007 ); Raj & Kurup (2007 ); Pouralimardan et al. (2007 ); Bacchi et al. (2006 ); Dinda et al. (2002 ). For reference bond lengths, see: Allen et al. (1987 ). The title compound was prepared by the method described in Zhu (2010 ).

Experimental

Crystal data

C₁₆H₁₅ClN₂O₃·H₂O
M_r = 336.77
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.631 (2) Å
b = 13.558 (3) Å
c = 25.478 (3) Å
V = 1599.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 298 K
0.23 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.943, T_max = 0.950
8650 measured reflections
3460 independent reflections
1391 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.158
S = 1.00
3460 reflections
219 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1399 Friedel pairs
Flack parameter: 0.25 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.82	1.95	2.645 (5)	142
N2—H2⋯O4ⁱ	0.90 (1)	2.03 (1)	2.932 (5)	175 (5)
O4—H4A⋯O3	0.84 (3)	1.89 (2)	2.717 (5)	167 (5)
O4—H4B⋯O2ⁱⁱ	0.85 (4)	2.16 (2)	2.945 (5)	154 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S160053681100122X/om2396sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100122X/om2396Isup2.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 (Bessy et al., 2006; Podyachev et al., 2007; Raj & Kurup, 2007; Pouralimardan et al., 2007; Bacchi et al., 2006; 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 compound contains a Schiff base molecule and a water molecule of crystallization. The water molecule is linked to the Schiff base molecule via intermolecular O—H···O hydrogen bonds (Table 1). In the Schiff base molecule, there is an O—H···N hydrogen bond, which contributes to the planarity of the molecule. The dihedral angle between the two benzene rings is 20.5 (5)°. All the bond lengths are within normal values (Allen et al., 1987). The molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) to form two-dimensional layers along the ab plane (Fig. 2).

Related literature top

For Schiff base compounds, see: Bessy et al. (2006); Podyachev et al. (2007); Raj & Kurup (2007); Pouralimardan et al. (2007); Bacchi et al. (2006); Dinda et al. (2002). For the reference bond lengths, see: Allen et al. (1987). For the preparation of the title compound, see: Zhu (2010).

Experimental top

The compound was prepared and crystallized according to the literature method (Zhu, 2010). 3-Ethoxy-2-hydroxybenzaldehyde (0.166 g, 1 mmol) and 3-chlorobenzohydrazide (0.171 g, 1 mmol) were dissolved in 30 ml 95% ethanol. 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 ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 compound with 30% probability displacement ellipsoids for non-hydrogen atoms. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. The molecular packing of the title compound. Hydrogen bonds are drawn as dashed lines.

3-Chloro-N'-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₆H₁₅ClN₂O₃·H₂O	D_x = 1.398 Mg m⁻³
M_r = 336.77	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 705 reflections
a = 4.631 (2) Å	θ = 2.6–24.5°
b = 13.558 (3) Å	µ = 0.26 mm⁻¹
c = 25.478 (3) Å	T = 298 K
V = 1599.7 (8) Å³	Block, colorless
Z = 4	0.23 × 0.22 × 0.20 mm
F(000) = 704

Data collection top

Bruker APEXII CCD area-detector diffractometer	3460 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.943, T_max = 0.950	k = −12→17
8650 measured reflections	l = −32→29

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)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0181P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
3460 reflections	Δρ_max = 0.20 e Å⁻³
219 parameters	Δρ_min = −0.18 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1399 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.25 (16)

Crystal data top

C₁₆H₁₅ClN₂O₃·H₂O	V = 1599.7 (8) Å³
M_r = 336.77	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.631 (2) Å	µ = 0.26 mm⁻¹
b = 13.558 (3) Å	T = 298 K
c = 25.478 (3) Å	0.23 × 0.22 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3460 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1391 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.950	R_int = 0.085
8650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.158	Δρ_max = 0.20 e Å⁻³
S = 1.00	Δρ_min = −0.18 e Å⁻³
3460 reflections	Absolute structure: Flack (1983), 1399 Friedel pairs
219 parameters	Absolute structure parameter: 0.25 (16)
4 restraints

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	−0.1754 (4)	0.65889 (10)	0.04444 (6)	0.1007 (7)
N1	0.7745 (10)	0.8171 (3)	0.26638 (17)	0.0663 (13)
N2	0.5846 (11)	0.8403 (3)	0.22645 (18)	0.0638 (13)
O1	1.3750 (8)	0.6775 (2)	0.41318 (14)	0.0680 (10)
O2	1.0189 (9)	0.6980 (2)	0.33554 (13)	0.0656 (10)
H2A	0.8935	0.7128	0.3142	0.098*
O3	0.4905 (10)	0.6809 (3)	0.20923 (14)	0.0907 (13)
O4	0.4271 (12)	0.5540 (2)	0.29094 (15)	0.0892 (14)
C1	1.1199 (12)	0.8733 (4)	0.3283 (2)	0.0550 (14)
C2	1.1601 (12)	0.7804 (4)	0.3510 (2)	0.0541 (13)
C3	1.3572 (13)	0.7715 (4)	0.3925 (2)	0.0560 (14)
C4	1.5152 (12)	0.8508 (4)	0.4093 (2)	0.0636 (14)
H4	1.6523	0.8430	0.4357	0.076*
C5	1.4701 (14)	0.9427 (4)	0.3869 (2)	0.0714 (17)
H5	1.5733	0.9970	0.3989	0.086*
C6	1.2753 (14)	0.9537 (4)	0.3474 (2)	0.0704 (17)
H6	1.2452	1.0158	0.3329	0.085*
C7	1.5824 (12)	0.6631 (4)	0.4544 (2)	0.0704 (16)
H7A	1.5512	0.7105	0.4823	0.084*
H7B	1.7767	0.6717	0.4409	0.084*
C8	1.5442 (15)	0.5608 (3)	0.4746 (2)	0.0836 (19)
H8A	1.3503	0.5527	0.4873	0.125*
H8B	1.6777	0.5493	0.5028	0.125*
H8C	1.5801	0.5144	0.4469	0.125*
C9	0.9160 (13)	0.8890 (4)	0.2864 (2)	0.0655 (17)
H9	0.8865	0.9525	0.2737	0.079*
C10	0.4512 (14)	0.7692 (4)	0.1998 (2)	0.0634 (16)
C11	0.2476 (12)	0.7998 (4)	0.1579 (2)	0.0538 (13)
C12	0.1420 (14)	0.7273 (4)	0.1251 (2)	0.0660 (16)
H12	0.1992	0.6622	0.1297	0.079*
C13	−0.0471 (14)	0.7514 (4)	0.0857 (2)	0.0619 (16)
C14	−0.1410 (12)	0.8456 (4)	0.0778 (2)	0.0639 (15)
H14	−0.2718	0.8602	0.0512	0.077*
C15	−0.0362 (13)	0.9190 (4)	0.1104 (2)	0.0612 (15)
H15	−0.0954	0.9839	0.1055	0.073*
C16	0.1542 (13)	0.8968 (3)	0.1499 (2)	0.0568 (14)
H16	0.2222	0.9468	0.1716	0.068*
H2	0.569 (12)	0.9055 (11)	0.2203 (18)	0.080*
H4A	0.437 (12)	0.586 (3)	0.2626 (9)	0.080*
H4B	0.334 (10)	0.589 (3)	0.3130 (13)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1293 (16)	0.0775 (10)	0.0952 (12)	−0.0177 (11)	−0.0022 (11)	−0.0238 (9)
N1	0.062 (3)	0.088 (3)	0.049 (3)	0.024 (3)	0.009 (3)	0.009 (3)
N2	0.065 (4)	0.066 (3)	0.060 (3)	0.015 (3)	0.004 (3)	0.008 (3)
O1	0.066 (3)	0.062 (2)	0.076 (2)	−0.006 (2)	−0.018 (2)	0.0077 (19)
O2	0.059 (3)	0.063 (2)	0.074 (3)	0.001 (2)	−0.017 (2)	−0.0018 (19)
O3	0.124 (4)	0.061 (2)	0.086 (3)	0.020 (3)	−0.003 (3)	0.018 (2)
O4	0.138 (4)	0.055 (2)	0.075 (3)	0.009 (3)	0.017 (3)	0.004 (2)
C1	0.040 (3)	0.061 (3)	0.064 (4)	0.011 (3)	0.012 (3)	0.006 (3)
C2	0.041 (3)	0.063 (3)	0.058 (3)	−0.002 (3)	0.008 (3)	−0.005 (3)
C3	0.054 (4)	0.051 (3)	0.063 (4)	0.001 (3)	0.001 (3)	−0.004 (3)
C4	0.055 (4)	0.076 (4)	0.060 (3)	−0.006 (4)	0.007 (3)	−0.007 (3)
C5	0.068 (5)	0.057 (4)	0.089 (5)	−0.003 (3)	0.017 (4)	−0.011 (3)
C6	0.071 (5)	0.058 (3)	0.083 (5)	0.010 (4)	0.021 (4)	0.006 (3)
C7	0.063 (4)	0.079 (4)	0.069 (4)	0.001 (3)	−0.022 (4)	−0.003 (3)
C8	0.095 (5)	0.069 (4)	0.087 (4)	−0.007 (4)	−0.028 (4)	0.011 (3)
C9	0.056 (5)	0.076 (4)	0.064 (4)	0.016 (3)	0.012 (3)	0.010 (3)
C10	0.071 (5)	0.060 (4)	0.060 (4)	0.007 (4)	0.015 (3)	0.007 (3)
C11	0.058 (4)	0.051 (3)	0.053 (3)	0.001 (3)	0.008 (3)	0.002 (3)
C12	0.073 (4)	0.056 (3)	0.069 (4)	0.012 (4)	0.013 (4)	0.005 (3)
C13	0.070 (4)	0.052 (3)	0.063 (4)	−0.013 (3)	0.008 (4)	−0.008 (3)
C14	0.064 (4)	0.065 (3)	0.063 (4)	0.006 (4)	0.001 (3)	0.003 (3)
C15	0.066 (4)	0.051 (3)	0.067 (4)	0.000 (3)	−0.008 (4)	0.003 (3)
C16	0.066 (4)	0.049 (3)	0.055 (3)	−0.002 (3)	0.007 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.741 (5)	C5—H5	0.9300
N1—C9	1.281 (6)	C6—H6	0.9300
N1—N2	1.381 (6)	C7—C8	1.491 (6)
N2—C10	1.331 (6)	C7—H7A	0.9700
N2—H2	0.901 (10)	C7—H7B	0.9700
O1—C3	1.381 (5)	C8—H8A	0.9600
O1—C7	1.436 (5)	C8—H8B	0.9600
O2—C2	1.354 (5)	C8—H8C	0.9600
O2—H2A	0.8200	C9—H9	0.9300
O3—C10	1.234 (5)	C10—C11	1.485 (7)
O4—H4A	0.84 (3)	C11—C12	1.379 (6)
O4—H4B	0.85 (4)	C11—C16	1.399 (6)
C1—C6	1.394 (7)	C12—C13	1.371 (7)
C1—C2	1.399 (6)	C12—H12	0.9300
C1—C9	1.440 (7)	C13—C14	1.365 (6)
C2—C3	1.402 (7)	C14—C15	1.384 (6)
C3—C4	1.369 (6)	C14—H14	0.9300
C4—C5	1.386 (7)	C15—C16	1.370 (7)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.360 (7)	C16—H16	0.9300

C9—N1—N2	116.5 (5)	C7—C8—H8A	109.5
C10—N2—N1	120.4 (4)	C7—C8—H8B	109.5
C10—N2—H2	126 (3)	H8A—C8—H8B	109.5
N1—N2—H2	114 (4)	C7—C8—H8C	109.5
C3—O1—C7	116.4 (4)	H8A—C8—H8C	109.5
C2—O2—H2A	109.5	H8B—C8—H8C	109.5
H4A—O4—H4B	108 (2)	N1—C9—C1	121.2 (5)
C6—C1—C2	119.3 (5)	N1—C9—H9	119.4
C6—C1—C9	118.8 (5)	C1—C9—H9	119.4
C2—C1—C9	121.8 (5)	O3—C10—N2	122.4 (6)
O2—C2—C1	123.9 (5)	O3—C10—C11	120.3 (6)
O2—C2—C3	117.6 (5)	N2—C10—C11	117.3 (5)
C1—C2—C3	118.5 (5)	C12—C11—C16	118.1 (5)
C4—C3—O1	125.0 (5)	C12—C11—C10	117.5 (5)
C4—C3—C2	121.1 (5)	C16—C11—C10	124.4 (5)
O1—C3—C2	113.9 (5)	C13—C12—C11	120.0 (5)
C3—C4—C5	119.8 (5)	C13—C12—H12	120.0
C3—C4—H4	120.1	C11—C12—H12	120.0
C5—C4—H4	120.1	C14—C13—C12	122.3 (5)
C6—C5—C4	120.2 (6)	C14—C13—Cl1	118.4 (5)
C6—C5—H5	119.9	C12—C13—Cl1	119.3 (4)
C4—C5—H5	119.9	C13—C14—C15	118.2 (5)
C5—C6—C1	121.1 (5)	C13—C14—H14	120.9
C5—C6—H6	119.5	C15—C14—H14	120.9
C1—C6—H6	119.5	C16—C15—C14	120.6 (5)
O1—C7—C8	107.5 (4)	C16—C15—H15	119.7
O1—C7—H7A	110.2	C14—C15—H15	119.7
C8—C7—H7A	110.2	C15—C16—C11	120.8 (5)
O1—C7—H7B	110.2	C15—C16—H16	119.6
C8—C7—H7B	110.2	C11—C16—H16	119.6
H7A—C7—H7B	108.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	1.95	2.645 (6)	142
N2—H2···O4ⁱ	0.90 (1)	2.03 (1)	2.932 (5)	175 (5)
O4—H4A···O3	0.84 (3)	1.89 (2)	2.717 (5)	167 (5)
O4—H4B···O2ⁱⁱ	0.85 (4)	2.16 (2)	2.945 (5)	154 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅ClN₂O₃·H₂O
M_r	336.77
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	4.631 (2), 13.558 (3), 25.478 (3)
V (Å³)	1599.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.943, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	8650, 3460, 1391
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.158, 1.00
No. of reflections	3460
No. of parameters	219
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18
Absolute structure	Flack (1983), 1399 Friedel pairs
Absolute structure parameter	0.25 (16)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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—H2A···N1	0.82	1.95	2.645 (6)	142
N2—H2···O4ⁱ	0.901 (10)	2.034 (13)	2.932 (5)	175 (5)
O4—H4A···O3	0.84 (3)	1.886 (16)	2.717 (5)	167 (5)
O4—H4B···O2ⁱⁱ	0.85 (4)	2.16 (2)	2.945 (5)	154 (4)

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

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. CrossRef Web of Science Google Scholar
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Volume 67| Part 2| February 2011| Page o377

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