3-Chloro-N'-(3-eth-oxy-2-hy-droxy-benzyl-idene)benzohydrazide monohydrate.

In the title compound, C(16)H(15)ClN(2)O(3)·H(2)O, the water mol-ecule is linked to the Schiff base mol-ecule via an O-H⋯O hydrogen bond. In the Schiff base mol-ecule, 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 mol-ecules are linked by inter-molecular 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 = 336.77

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.158

S = 1.00

3460 reflections

219 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1399 Friedel pairs

Flack parameter: 0.25 (16)

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100122X/om2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100122X/om2396Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H15ClN2O3·H2O	Dx = 1.398 Mg m−3
Mr = 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

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

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(Fo2) + (0.0181P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
3460 reflections	Δρmax = 0.20 e Å−3
219 parameters	Δρmin = −0.18 e Å−3
4 restraints	Absolute structure: Flack (1983), 1399 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.25 (16)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) .