(E)-N'-(5-Chloro-2-hydroxy-benzyl-idene)-3,5-dihydroxy-benzohydrazide mono-hydrate.

In the title compound, C(14)H(11)ClN(2)O(4)·H(2)O, the dihedral angle between the two benzene rings is 8.5 (2)° and an intra-molecular O-H⋯N hydrogen bond is observed in the Schiff base mol-ecule. In the crystal structure, the water mol-ecule accepts an N-H⋯O hydrogen bond and makes O-H⋯O hydrogen bonds to two further Schiff base mol-ecules. Further inter-molecular O-H⋯O hydrogen bonds lead to the formation of layers parallel to the bc plane.

Related literature

For background to the synthesis of Schiff base compounds, see: Herrick et al. (2008 ▶); Suresh et al. (2007 ▶). For the biological activity of Schiff base compounds, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶). For a related structure, see: Jiang et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11ClN2O4·H2O

M = 324.71

Monoclinic,

a = 14.106 (3) Å

b = 8.0090 (16) Å

c = 13.127 (3) Å

β = 108.26 (3)°

V = 1408.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.943, T max = 0.948

6975 measured reflections

2496 independent reflections

1437 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.142

S = 1.04

2496 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007788/hb2921sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007788/hb2921Isup2.hkl

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

C14H11ClN2O4·H2O	F(000) = 672
Mr = 324.71	Dx = 1.531 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 575 reflections
a = 14.106 (3) Å	θ = 3.1–20.4°
b = 8.0090 (16) Å	µ = 0.30 mm−1
c = 13.127 (3) Å	T = 298 K
β = 108.26 (3)°	Block, light yellow
V = 1408.3 (6) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Siemens SMART CCD diffractometer	2496 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
graphite	Rint = 0.084
ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −16→13
Tmin = 0.943, Tmax = 0.948	k = −9→7
6975 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0453P)2 + 1.0153P] where P = (Fo2 + 2Fc2)/3
2496 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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	0.45135 (9)	1.22680 (17)	0.91318 (10)	0.0558 (4)
N1	0.8522 (2)	0.8948 (4)	0.8966 (3)	0.0295 (8)
N2	0.9299 (2)	0.8091 (4)	0.9689 (2)	0.0291 (8)
H2	0.9246	0.7758	1.0291	0.035*
O1	0.7409 (2)	1.0093 (4)	0.7040 (2)	0.0439 (8)
H1	0.7853	0.9523	0.7442	0.066*
O2	1.02312 (19)	0.8242 (4)	0.8572 (2)	0.0380 (8)
O3	1.3085 (2)	0.4281 (4)	1.0233 (2)	0.0491 (9)
H3	1.2983	0.4456	0.9592	0.074*
O4	1.1915 (2)	0.5757 (4)	1.3090 (2)	0.0400 (8)
H4	1.1481	0.6308	1.3229	0.060*
O5	0.8783 (2)	0.7575 (4)	0.6646 (2)	0.0434 (8)
H5A	0.9196	0.7761	0.7263	0.065*
H5B	0.8435	0.6765	0.6750	0.065*
C1	0.6935 (3)	1.0274 (5)	0.8653 (3)	0.0274 (9)
C2	0.6769 (3)	1.0606 (5)	0.7568 (3)	0.0309 (10)
C3	0.5923 (3)	1.1451 (6)	0.6983 (3)	0.0426 (12)
H3A	0.5819	1.1666	0.6260	0.051*
C4	0.5231 (3)	1.1979 (6)	0.7450 (4)	0.0437 (12)
H4A	0.4662	1.2550	0.7050	0.052*
C5	0.5392 (3)	1.1652 (6)	0.8520 (3)	0.0364 (11)
C6	0.6229 (3)	1.0829 (5)	0.9126 (3)	0.0354 (11)
H6	0.6330	1.0638	0.9851	0.042*
C7	0.7800 (3)	0.9389 (5)	0.9314 (3)	0.0298 (10)
H7	0.7838	0.9127	1.0016	0.036*
C8	1.0139 (3)	0.7786 (5)	0.9438 (3)	0.0254 (9)
C9	1.0938 (3)	0.6850 (5)	1.0242 (3)	0.0252 (9)
C10	1.1629 (3)	0.6018 (5)	0.9869 (3)	0.0291 (10)
H10	1.1574	0.6065	0.9145	0.035*
C11	1.2398 (3)	0.5122 (5)	1.0569 (3)	0.0304 (10)
C12	1.2492 (3)	0.5052 (5)	1.1645 (3)	0.0334 (10)
H12	1.3011	0.4455	1.2117	0.040*
C13	1.1801 (3)	0.5882 (5)	1.2015 (3)	0.0285 (10)
C14	1.1025 (3)	0.6788 (5)	1.1327 (3)	0.0297 (10)
H14	1.0570	0.7345	1.1587	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0391 (7)	0.0748 (10)	0.0587 (8)	0.0186 (7)	0.0226 (6)	−0.0009 (7)
N1	0.0256 (18)	0.032 (2)	0.0297 (19)	0.0018 (16)	0.0075 (15)	0.0043 (16)
N2	0.0262 (18)	0.039 (2)	0.0238 (17)	0.0072 (16)	0.0095 (15)	0.0089 (16)
O1	0.0415 (18)	0.061 (2)	0.0333 (17)	0.0121 (17)	0.0175 (15)	0.0069 (16)
O2	0.0337 (17)	0.057 (2)	0.0252 (15)	0.0057 (15)	0.0122 (13)	0.0097 (15)
O3	0.0467 (19)	0.069 (2)	0.0379 (18)	0.0283 (18)	0.0223 (16)	0.0028 (17)
O4	0.0422 (19)	0.053 (2)	0.0282 (16)	0.0143 (16)	0.0160 (14)	0.0059 (14)
O5	0.0438 (18)	0.058 (2)	0.0298 (16)	−0.0058 (17)	0.0131 (14)	−0.0021 (15)
C1	0.022 (2)	0.031 (3)	0.026 (2)	0.0015 (19)	0.0036 (17)	0.0020 (19)
C2	0.029 (2)	0.037 (3)	0.029 (2)	0.000 (2)	0.0129 (19)	0.000 (2)
C3	0.041 (3)	0.057 (3)	0.027 (2)	0.010 (2)	0.006 (2)	0.009 (2)
C4	0.034 (3)	0.050 (3)	0.042 (3)	0.012 (2)	0.004 (2)	0.009 (2)
C5	0.026 (2)	0.044 (3)	0.041 (3)	0.008 (2)	0.014 (2)	−0.002 (2)
C6	0.035 (2)	0.043 (3)	0.031 (2)	0.000 (2)	0.015 (2)	−0.001 (2)
C7	0.028 (2)	0.036 (3)	0.028 (2)	−0.003 (2)	0.0116 (18)	0.0002 (19)
C8	0.025 (2)	0.028 (2)	0.025 (2)	−0.0002 (19)	0.0087 (17)	0.0024 (18)
C9	0.024 (2)	0.029 (2)	0.025 (2)	−0.0001 (18)	0.0104 (17)	−0.0021 (18)
C10	0.031 (2)	0.034 (3)	0.025 (2)	0.002 (2)	0.0119 (18)	−0.0024 (19)
C11	0.029 (2)	0.035 (3)	0.028 (2)	0.005 (2)	0.0111 (19)	−0.002 (2)
C12	0.032 (2)	0.039 (3)	0.029 (2)	0.008 (2)	0.0097 (19)	0.003 (2)
C13	0.028 (2)	0.032 (3)	0.026 (2)	−0.001 (2)	0.0088 (18)	0.0033 (19)
C14	0.027 (2)	0.037 (3)	0.028 (2)	0.003 (2)	0.0145 (19)	−0.001 (2)

Cl1—C5	1.746 (4)	C3—C4	1.372 (6)
N1—C7	1.290 (4)	C3—H3A	0.9300
N1—N2	1.386 (4)	C4—C5	1.376 (6)
N2—C8	1.348 (4)	C4—H4A	0.9300
N2—H2	0.8600	C5—C6	1.368 (6)
O1—C2	1.364 (4)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.238 (4)	C8—C9	1.484 (5)
O3—C11	1.362 (4)	C9—C10	1.391 (5)
O3—H3	0.8200	C9—C14	1.392 (5)
O4—C13	1.373 (4)	C10—C11	1.382 (5)
O4—H4	0.8200	C10—H10	0.9300
O5—H5A	0.8500	C11—C12	1.378 (5)
O5—H5B	0.8500	C12—C13	1.387 (5)
C1—C2	1.395 (5)	C12—H12	0.9300
C1—C6	1.401 (5)	C13—C14	1.386 (5)
C1—C7	1.442 (5)	C14—H14	0.9300
C2—C3	1.377 (6)
C7—N1—N2	115.8 (3)	C1—C6—H6	120.0
C8—N2—N1	119.3 (3)	N1—C7—C1	122.3 (4)
C8—N2—H2	120.4	N1—C7—H7	118.8
N1—N2—H2	120.4	C1—C7—H7	118.8
C2—O1—H1	109.5	O2—C8—N2	121.6 (3)
C11—O3—H3	109.5	O2—C8—C9	121.8 (3)
C13—O4—H4	109.5	N2—C8—C9	116.6 (3)
H5A—O5—H5B	103.8	C10—C9—C14	119.7 (4)
C2—C1—C6	118.5 (4)	C10—C9—C8	116.8 (3)
C2—C1—C7	123.3 (4)	C14—C9—C8	123.4 (3)
C6—C1—C7	118.3 (4)	C11—C10—C9	120.4 (4)
O1—C2—C3	117.5 (4)	C11—C10—H10	119.8
O1—C2—C1	122.4 (4)	C9—C10—H10	119.8
C3—C2—C1	120.1 (4)	O3—C11—C12	117.6 (4)
C4—C3—C2	121.1 (4)	O3—C11—C10	122.1 (3)
C4—C3—H3A	119.5	C12—C11—C10	120.3 (4)
C2—C3—H3A	119.5	C11—C12—C13	119.2 (4)
C3—C4—C5	119.0 (4)	C11—C12—H12	120.4
C3—C4—H4A	120.5	C13—C12—H12	120.4
C5—C4—H4A	120.5	O4—C13—C14	121.5 (3)
C6—C5—C4	121.4 (4)	O4—C13—C12	117.2 (4)
C6—C5—Cl1	118.5 (3)	C14—C13—C12	121.4 (4)
C4—C5—Cl1	120.1 (3)	C13—C14—C9	119.0 (4)
C5—C6—C1	119.9 (4)	C13—C14—H14	120.5
C5—C6—H6	120.0	C9—C14—H14	120.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.98	2.685 (4)	144
O1—H1···O5	0.82	2.47	2.952 (4)	119
O3—H3···O1i	0.82	2.10	2.916 (4)	173
O4—H4···O2ii	0.82	1.99	2.762 (4)	158
N2—H2···O5ii	0.86	2.09	2.931 (4)	164
O5—H5A···O2	0.85	1.91	2.760 (4)	174
O5—H5B···O4iii	0.85	2.11	2.902 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.98	2.685 (4)	144
O1—H1⋯O5	0.82	2.47	2.952 (4)	119
O3—H3⋯O1i	0.82	2.10	2.916 (4)	173
O4—H4⋯O2ii	0.82	1.99	2.762 (4)	158
N2—H2⋯O5ii	0.86	2.09	2.931 (4)	164
O5—H5A⋯O2	0.85	1.91	2.760 (4)	174
O5—H5B⋯O4iii	0.85	2.11	2.902 (4)	156

Symmetry codes: (i) ; (ii) ; (iii) .