(E)-N'-(2-Chloro-benzyl-idene)-3,5-di-hydroxy-benzohydrazide dihydrate.

In the Schiff base mol-ecule of the title compound, C(14)H(11)ClN(2)O(3)·2H(2)O, the benzene rings form a dihedral angle of 20.6 (1)°. The water molecules of crystallization are involved in the formation of a three-dimensional hydrogen-bonding network via O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al.(2003 ▶); Zhang et al. (2008 ▶). For related structures, see: Diao et al. (2007 ▶); Jiang et al. (2008 ▶); Huang et al. (2008 ▶); Deng et al. (2009 ▶).

Experimental

Crystal data

C14H11ClN2O3·2H2O

M = 326.73

Monoclinic,

a = 8.023 (2) Å

b = 11.852 (4) Å

c = 16.318 (5) Å

β = 100.387 (4)°

V = 1526.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.44 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

12729 measured reflections

3522 independent reflections

2286 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.03

3522 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042681/cv5172sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042681/cv5172Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042681/cv5172Isup3.cml

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

C14H11ClN2O3·2H2O	F(000) = 680
Mr = 326.73	Dx = 1.422 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 4061 reflections
a = 8.023 (2) Å	θ = 2.5–27.1°
b = 11.852 (4) Å	µ = 0.28 mm−1
c = 16.318 (5) Å	T = 296 K
β = 100.387 (4)°	Stick, yellow
V = 1526.1 (8) Å3	0.44 × 0.12 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	2286 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 27.6°, θmin = 2.1°
φ and ω scans	h = −10→10
12729 measured reflections	k = −15→15
3522 independent reflections	l = −20→21

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.044P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
3522 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.33 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	0.07549 (13)	0.73732 (7)	0.46696 (6)	0.0836 (3)
O1	0.4482 (3)	0.20583 (16)	0.45642 (10)	0.0555 (5)
O2	0.7564 (2)	0.07180 (15)	0.22642 (10)	0.0508 (5)
H2B	0.7932	0.0426	0.2716	0.076*
O3	0.3480 (3)	0.33745 (18)	0.10033 (10)	0.0615 (6)
H3A	0.3864	0.3177	0.0593	0.092*
N1	0.3161 (2)	0.41028 (17)	0.48357 (10)	0.0374 (4)
N2	0.3589 (2)	0.37857 (17)	0.40850 (10)	0.0368 (4)
H2A	0.3450	0.4252	0.3674	0.044*
C1	0.1081 (3)	0.6554 (2)	0.55602 (17)	0.0472 (6)
C2	0.0554 (4)	0.6968 (3)	0.6271 (2)	0.0621 (8)
H2	0.0022	0.7666	0.6257	0.074*
C3	0.0818 (4)	0.6351 (3)	0.6986 (2)	0.0678 (9)
H3	0.0483	0.6635	0.7462	0.081*
C4	0.1571 (4)	0.5318 (3)	0.70062 (18)	0.0687 (9)
H4	0.1738	0.4897	0.7495	0.082*
C5	0.2090 (4)	0.4891 (3)	0.63044 (16)	0.0550 (7)
H5	0.2596	0.4184	0.6326	0.066*
C6	0.1866 (3)	0.5505 (2)	0.55659 (14)	0.0382 (5)
C7	0.2396 (3)	0.5047 (2)	0.48164 (14)	0.0371 (5)
H7	0.2171	0.5453	0.4321	0.044*
C8	0.4220 (3)	0.2757 (2)	0.39941 (12)	0.0353 (5)
C9	0.4635 (3)	0.25014 (19)	0.31552 (12)	0.0326 (5)
C10	0.5859 (3)	0.16929 (19)	0.31167 (12)	0.0347 (5)
H10	0.6357	0.1302	0.3592	0.042*
C11	0.6334 (3)	0.14750 (19)	0.23525 (13)	0.0351 (5)
C12	0.5573 (3)	0.2046 (2)	0.16457 (12)	0.0387 (5)
H12	0.5916	0.1910	0.1140	0.046*
C13	0.4305 (3)	0.2818 (2)	0.16880 (12)	0.0387 (5)
C14	0.3828 (3)	0.3059 (2)	0.24457 (13)	0.0393 (5)
H14	0.2981	0.3585	0.2477	0.047*
O4	0.2697 (4)	−0.0135 (3)	0.4316 (2)	0.1159 (11)
H4A	0.3177	−0.0688	0.4595	0.174*
H4B	0.3266	0.0473	0.4339	0.174*
O5	0.9176 (3)	−0.00817 (18)	0.37266 (13)	0.0690 (6)
H5A	1.0182	−0.0070	0.4001	0.104*
H5B	0.8554	−0.0465	0.3993	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.1051 (7)	0.0521 (5)	0.0969 (7)	0.0157 (5)	0.0274 (6)	0.0134 (4)
O1	0.0881 (14)	0.0572 (11)	0.0272 (8)	0.0154 (10)	0.0261 (9)	0.0084 (8)
O2	0.0624 (12)	0.0562 (11)	0.0360 (9)	0.0213 (9)	0.0146 (8)	−0.0016 (8)
O3	0.0820 (14)	0.0817 (14)	0.0224 (8)	0.0345 (12)	0.0139 (8)	0.0076 (8)
N1	0.0404 (11)	0.0505 (12)	0.0244 (8)	0.0010 (9)	0.0141 (8)	−0.0046 (8)
N2	0.0438 (11)	0.0479 (11)	0.0217 (8)	0.0006 (9)	0.0140 (8)	−0.0011 (8)
C1	0.0379 (14)	0.0438 (14)	0.0619 (16)	−0.0085 (11)	0.0146 (12)	−0.0153 (12)
C2	0.0455 (16)	0.0534 (17)	0.093 (2)	−0.0089 (13)	0.0284 (16)	−0.0352 (17)
C3	0.0585 (19)	0.087 (2)	0.067 (2)	−0.0154 (17)	0.0349 (16)	−0.0362 (18)
C4	0.071 (2)	0.097 (3)	0.0449 (15)	0.0004 (19)	0.0279 (14)	−0.0074 (16)
C5	0.0568 (17)	0.0714 (19)	0.0414 (14)	0.0092 (14)	0.0212 (12)	−0.0046 (13)
C6	0.0311 (12)	0.0477 (13)	0.0384 (12)	−0.0053 (10)	0.0131 (9)	−0.0095 (10)
C7	0.0366 (12)	0.0455 (13)	0.0311 (11)	−0.0054 (11)	0.0114 (9)	−0.0022 (9)
C8	0.0394 (12)	0.0451 (13)	0.0240 (10)	0.0002 (10)	0.0129 (9)	−0.0016 (9)
C9	0.0368 (12)	0.0419 (12)	0.0209 (9)	−0.0035 (10)	0.0103 (8)	−0.0017 (8)
C10	0.0403 (13)	0.0412 (12)	0.0235 (9)	0.0004 (10)	0.0081 (9)	0.0006 (9)
C11	0.0406 (13)	0.0376 (12)	0.0290 (10)	−0.0009 (10)	0.0112 (9)	−0.0055 (9)
C12	0.0497 (14)	0.0474 (13)	0.0220 (9)	0.0015 (11)	0.0146 (9)	−0.0062 (9)
C13	0.0464 (13)	0.0481 (13)	0.0222 (10)	0.0042 (11)	0.0076 (9)	0.0001 (9)
C14	0.0464 (14)	0.0480 (13)	0.0257 (10)	0.0100 (11)	0.0124 (9)	−0.0005 (9)
O4	0.099 (2)	0.098 (2)	0.138 (3)	−0.0265 (18)	−0.0111 (19)	0.0009 (19)
O5	0.0685 (14)	0.0749 (14)	0.0616 (12)	0.0020 (11)	0.0063 (10)	0.0216 (11)

Cl1—C1	1.728 (3)	C5—C6	1.391 (4)
O1—C8	1.235 (3)	C5—H5	0.9300
O2—C11	1.361 (3)	C6—C7	1.469 (3)
O2—H2B	0.8200	C7—H7	0.9300
O3—C13	1.362 (3)	C8—C9	1.497 (3)
O3—H3A	0.8200	C9—C10	1.382 (3)
N1—C7	1.274 (3)	C9—C14	1.388 (3)
N1—N2	1.383 (2)	C10—C11	1.392 (3)
N2—C8	1.338 (3)	C10—H10	0.9300
N2—H2A	0.8600	C11—C12	1.381 (3)
C1—C6	1.392 (4)	C12—C13	1.379 (3)
C1—C2	1.393 (4)	C12—H12	0.9300
C2—C3	1.361 (5)	C13—C14	1.388 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.363 (5)	O4—H4A	0.8500
C3—H3	0.9300	O4—H4B	0.8500
C4—C5	1.383 (4)	O5—H5A	0.8500
C4—H4	0.9300	O5—H5B	0.8500
C11—O2—H2B	109.5	N1—C7—H7	119.5
C13—O3—H3A	109.5	C6—C7—H7	119.5
C7—N1—N2	114.36 (19)	O1—C8—N2	122.96 (18)
C8—N2—N1	120.34 (18)	O1—C8—C9	121.1 (2)
C8—N2—H2A	119.8	N2—C8—C9	115.90 (19)
N1—N2—H2A	119.8	C10—C9—C14	121.39 (18)
C6—C1—C2	120.9 (3)	C10—C9—C8	117.35 (19)
C6—C1—Cl1	120.46 (19)	C14—C9—C8	121.3 (2)
C2—C1—Cl1	118.6 (2)	C9—C10—C11	118.7 (2)
C3—C2—C1	120.1 (3)	C9—C10—H10	120.6
C3—C2—H2	120.0	C11—C10—H10	120.6
C1—C2—H2	120.0	O2—C11—C12	117.05 (18)
C2—C3—C4	120.2 (3)	O2—C11—C10	122.6 (2)
C2—C3—H3	119.9	C12—C11—C10	120.4 (2)
C4—C3—H3	119.9	C13—C12—C11	120.16 (18)
C3—C4—C5	120.4 (3)	C13—C12—H12	119.9
C3—C4—H4	119.8	C11—C12—H12	119.9
C5—C4—H4	119.8	O3—C13—C12	122.25 (18)
C4—C5—C6	121.0 (3)	O3—C13—C14	117.4 (2)
C4—C5—H5	119.5	C12—C13—C14	120.3 (2)
C6—C5—H5	119.5	C9—C14—C13	118.9 (2)
C5—C6—C1	117.4 (2)	C9—C14—H14	120.6
C5—C6—C7	121.1 (2)	C13—C14—H14	120.6
C1—C6—C7	121.5 (2)	H4A—O4—H4B	116.3
N1—C7—C6	120.9 (2)	H5A—O5—H5B	109.2
C7—N1—N2—C8	−172.3 (2)	O1—C8—C9—C10	−24.0 (3)
C6—C1—C2—C3	0.6 (4)	N2—C8—C9—C10	154.7 (2)
Cl1—C1—C2—C3	−178.9 (2)	O1—C8—C9—C14	156.3 (2)
C1—C2—C3—C4	−1.1 (5)	N2—C8—C9—C14	−25.0 (3)
C2—C3—C4—C5	0.6 (5)	C14—C9—C10—C11	2.8 (3)
C3—C4—C5—C6	0.4 (5)	C8—C9—C10—C11	−176.9 (2)
C4—C5—C6—C1	−0.9 (4)	C9—C10—C11—O2	178.0 (2)
C4—C5—C6—C7	−179.2 (3)	C9—C10—C11—C12	−1.0 (3)
C2—C1—C6—C5	0.4 (4)	O2—C11—C12—C13	179.4 (2)
Cl1—C1—C6—C5	179.9 (2)	C10—C11—C12—C13	−1.6 (4)
C2—C1—C6—C7	178.7 (2)	C11—C12—C13—O3	−177.8 (2)
Cl1—C1—C6—C7	−1.7 (3)	C11—C12—C13—C14	2.4 (4)
N2—N1—C7—C6	−179.62 (19)	C10—C9—C14—C13	−2.0 (4)
C5—C6—C7—N1	−3.9 (4)	C8—C9—C14—C13	177.7 (2)
C1—C6—C7—N1	177.8 (2)	O3—C13—C14—C9	179.6 (2)
N1—N2—C8—O1	−1.5 (4)	C12—C13—C14—C9	−0.6 (4)
N1—N2—C8—C9	179.82 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O5	0.82	1.87	2.674 (3)	168.
O3—H3A···O1i	0.82	1.85	2.665 (2)	169.
N2—H2A···O2ii	0.86	2.36	3.196 (3)	164.
O4—H4B···O1	0.85	2.12	2.960 (4)	171.
O5—H5A···O4iii	0.85	1.99	2.816 (4)	163.
O5—H5B···O3iv	0.85	2.14	2.902 (3)	150.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O5	0.82	1.87	2.674 (3)	168
O3—H3A⋯O1i	0.82	1.85	2.665 (2)	169
N2—H2A⋯O2ii	0.86	2.36	3.196 (3)	164
O4—H4B⋯O1	0.85	2.12	2.960 (4)	171
O5—H5A⋯O4iii	0.85	1.99	2.816 (4)	163
O5—H5B⋯O3iv	0.85	2.14	2.902 (3)	150

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