N'-[(E)-1-(3,5-Dichloro-2-hy-droxy-phen-yl)ethyl-idene]-4-meth-oxy-benzo-hydrazide monohydrate.

The title compound, C(16)H(14)Cl(2)N(2)O(3)·H(2)O, displays a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is 4.98 (12)°. Intra-molecular O-H⋯N and O-H⋯O hydrogen bonds occur. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds. In addition, there are π-π inter-actions between the chemically distinct benzene rings of inversion-related mol-ecules [centroid-centroid separation = 3.715 (1) Å].

Related literature

For further details of the chemistry of the title compound, see: Carcelli et al. (1995 ▶); Salem (1998 ▶). For a related stucture, see: Chang et al. (2007 ▶).

Experimental

Crystal data

C16H14Cl2N2O3·H2O

M = 371.21

Triclinic,

a = 7.033 (5) Å

b = 7.516 (7) Å

c = 16.647 (10) Å

α = 85.105 (10)°

β = 81.386 (12)°

γ = 79.414 (10)°

V = 853.7 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 298 K

0.30 × 0.23 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.906, T max = 0.946

4423 measured reflections

2936 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.170

S = 1.00

2936 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.32 e Å−3

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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038328/pk2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038328/pk2270Isup2.hkl

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

C16H14Cl2N2O3·H2O	Z = 2
Mr = 371.21	F(000) = 384
Triclinic, P1	Dx = 1.444 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.033 (5) Å	Cell parameters from 1429 reflections
b = 7.516 (7) Å	θ = 3.0–25.5°
c = 16.647 (10) Å	µ = 0.40 mm−1
α = 85.105 (10)°	T = 298 K
β = 81.386 (12)°	Plate, yellow
γ = 79.414 (10)°	0.30 × 0.23 × 0.16 mm
V = 853.7 (11) Å3

Bruker APEXII CCD area-detector diffractometer	2936 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.906, Tmax = 0.946	k = −6→8
4423 measured reflections	l = −19→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.8688P] where P = (Fo2 + 2Fc2)/3
2936 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.32 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	1.0655 (2)	−0.37144 (18)	0.19059 (9)	0.0675 (5)
Cl2	0.8926 (3)	0.3075 (2)	0.05875 (8)	0.0774 (6)
O1	0.9149 (5)	−0.2090 (4)	0.34325 (19)	0.0462 (8)
H1	0.8675	−0.1599	0.3856	0.069*
O2	0.7613 (6)	−0.2102 (4)	0.5397 (2)	0.0611 (10)
O3	0.5111 (6)	0.0452 (6)	0.8985 (2)	0.0714 (12)
O4	0.7853 (6)	0.4252 (4)	0.5716 (3)	0.0710 (12)
N1	0.7805 (5)	0.0497 (5)	0.4303 (2)	0.0367 (9)
N2	0.7259 (5)	0.0879 (5)	0.5112 (2)	0.0392 (9)
H2	0.6983	0.1973	0.5264	0.047*
C1	0.8427 (6)	0.1022 (6)	0.2902 (3)	0.0360 (9)
C2	0.9122 (6)	−0.0844 (6)	0.2809 (3)	0.0374 (10)
C3	0.9789 (7)	−0.1428 (6)	0.2023 (3)	0.0442 (11)
C4	0.9757 (7)	−0.0251 (7)	0.1341 (3)	0.0488 (11)
H4	1.0221	−0.0668	0.0826	0.059*
C5	0.9020 (7)	0.1566 (7)	0.1441 (3)	0.0448 (11)
C6	0.8384 (7)	0.2200 (6)	0.2203 (3)	0.0419 (10)
H6	0.7918	0.3432	0.2255	0.050*
C7	0.7781 (6)	0.1720 (6)	0.3720 (3)	0.0357 (9)
C8	0.7186 (6)	−0.0562 (6)	0.5645 (3)	0.0387 (10)
C9	0.6577 (6)	−0.0211 (6)	0.6511 (3)	0.0387 (10)
C10	0.5662 (7)	0.1480 (7)	0.6775 (3)	0.0452 (11)
H10	0.5393	0.2442	0.6396	0.054*
C11	0.5141 (7)	0.1750 (7)	0.7606 (3)	0.0508 (12)
H11	0.4542	0.2887	0.7780	0.061*
C12	0.5526 (7)	0.0310 (7)	0.8165 (3)	0.0483 (11)
C13	0.6383 (7)	−0.1378 (7)	0.7914 (3)	0.0517 (12)
H13	0.6614	−0.2346	0.8294	0.062*
C14	0.6904 (7)	−0.1634 (7)	0.7088 (3)	0.0457 (11)
H14	0.7484	−0.2780	0.6919	0.055*
C15	0.4310 (10)	0.2206 (10)	0.9292 (4)	0.0819 (19)
H15A	0.5202	0.3029	0.9109	0.123*
H15B	0.4107	0.2103	0.9876	0.123*
H15C	0.3086	0.2657	0.9095	0.123*
C16	0.7148 (6)	0.3729 (4)	0.3805 (3)	0.0605 (15)
H16A	0.6850	0.3969	0.4371	0.091*
H16B	0.6008	0.4148	0.3542	0.091*
H16C	0.8183	0.4351	0.3555	0.091*
H15	0.7839	0.5382	0.5611	0.14 (3)*
H16	0.8905	0.3884	0.5919	0.09 (2)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0958 (12)	0.0380 (7)	0.0647 (9)	−0.0048 (7)	−0.0002 (8)	−0.0142 (6)
Cl2	0.1369 (15)	0.0568 (9)	0.0331 (7)	−0.0125 (9)	−0.0067 (8)	0.0091 (6)
O1	0.067 (2)	0.0312 (17)	0.0383 (18)	−0.0054 (15)	−0.0049 (16)	0.0012 (14)
O2	0.104 (3)	0.0296 (18)	0.046 (2)	−0.0090 (18)	−0.0052 (19)	0.0065 (15)
O3	0.089 (3)	0.084 (3)	0.034 (2)	−0.001 (2)	−0.0038 (19)	0.0013 (19)
O4	0.090 (3)	0.037 (2)	0.096 (3)	−0.0169 (19)	−0.044 (3)	0.007 (2)
N1	0.050 (2)	0.031 (2)	0.0279 (19)	−0.0080 (16)	−0.0040 (16)	0.0009 (15)
N2	0.053 (2)	0.0283 (19)	0.035 (2)	−0.0060 (16)	−0.0037 (17)	−0.0006 (16)
C1	0.038 (2)	0.039 (2)	0.032 (2)	−0.0095 (18)	−0.0057 (17)	−0.0004 (17)
C2	0.041 (2)	0.033 (2)	0.038 (2)	−0.0108 (18)	−0.0052 (18)	0.0006 (18)
C3	0.048 (2)	0.041 (2)	0.045 (2)	−0.0085 (19)	−0.005 (2)	−0.007 (2)
C4	0.057 (3)	0.049 (3)	0.040 (2)	−0.013 (2)	−0.003 (2)	−0.006 (2)
C5	0.058 (3)	0.043 (2)	0.034 (2)	−0.013 (2)	−0.007 (2)	0.0028 (19)
C6	0.048 (2)	0.038 (2)	0.038 (2)	−0.0076 (19)	−0.0049 (19)	0.0003 (19)
C7	0.043 (2)	0.031 (2)	0.033 (2)	−0.0059 (17)	−0.0058 (18)	0.0025 (17)
C8	0.047 (2)	0.029 (2)	0.039 (2)	−0.0067 (18)	−0.0073 (19)	0.0035 (18)
C9	0.040 (2)	0.040 (2)	0.037 (2)	−0.0101 (18)	−0.0062 (18)	0.0037 (18)
C10	0.051 (3)	0.043 (2)	0.039 (2)	−0.005 (2)	−0.005 (2)	0.002 (2)
C11	0.057 (3)	0.047 (3)	0.046 (3)	−0.006 (2)	−0.002 (2)	−0.002 (2)
C12	0.048 (3)	0.059 (3)	0.037 (2)	−0.008 (2)	−0.005 (2)	0.001 (2)
C13	0.051 (3)	0.058 (3)	0.043 (2)	−0.006 (2)	−0.008 (2)	0.011 (2)
C14	0.050 (3)	0.044 (2)	0.041 (2)	−0.006 (2)	−0.005 (2)	0.006 (2)
C15	0.100 (5)	0.092 (5)	0.048 (3)	−0.004 (4)	0.003 (3)	−0.018 (3)
C16	0.098 (4)	0.035 (3)	0.041 (3)	−0.001 (3)	−0.001 (3)	−0.001 (2)

Cl1—C3	1.731 (5)	C5—C6	1.376 (7)
Cl2—C5	1.742 (5)	C6—H6	0.9300
O1—C2	1.338 (5)	C7—C16	1.506 (5)
O1—H1	0.8200	C8—C9	1.474 (6)
O2—C8	1.231 (5)	C9—C14	1.385 (6)
O3—C12	1.362 (6)	C9—C10	1.391 (6)
O3—C15	1.440 (7)	C10—C11	1.399 (7)
O4—H15	0.8511	C10—H10	0.9300
O4—H16	0.8496	C11—C12	1.381 (7)
N1—C7	1.279 (5)	C11—H11	0.9300
N1—N2	1.383 (5)	C12—C13	1.372 (7)
N2—C8	1.344 (5)	C13—C14	1.389 (7)
N2—H2	0.8600	C13—H13	0.9300
C1—C6	1.401 (6)	C14—H14	0.9300
C1—C2	1.412 (6)	C15—H15A	0.9600
C1—C7	1.477 (6)	C15—H15B	0.9600
C2—C3	1.401 (6)	C15—H15C	0.9600
C3—C4	1.378 (7)	C16—H16A	0.9600
C4—C5	1.383 (7)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C2—O1—H1	109.5	C14—C9—C10	118.5 (4)
C12—O3—C15	118.7 (5)	C14—C9—C8	118.6 (4)
H15—O4—H16	104.1	C10—C9—C8	122.9 (4)
C7—N1—N2	123.2 (4)	C9—C10—C11	120.7 (5)
C8—N2—N1	115.9 (4)	C9—C10—H10	119.7
C8—N2—H2	122.0	C11—C10—H10	119.7
N1—N2—H2	122.0	C12—C11—C10	119.3 (5)
C6—C1—C2	118.5 (4)	C12—C11—H11	120.4
C6—C1—C7	120.8 (4)	C10—C11—H11	120.4
C2—C1—C7	120.7 (4)	O3—C12—C13	115.8 (5)
O1—C2—C3	118.2 (4)	O3—C12—C11	123.4 (5)
O1—C2—C1	123.3 (4)	C13—C12—C11	120.8 (5)
C3—C2—C1	118.5 (4)	C12—C13—C14	119.6 (5)
C4—C3—C2	122.3 (4)	C12—C13—H13	120.2
C4—C3—Cl1	119.1 (4)	C14—C13—H13	120.2
C2—C3—Cl1	118.6 (4)	C9—C14—C13	121.2 (5)
C3—C4—C5	118.5 (4)	C9—C14—H14	119.4
C3—C4—H4	120.8	C13—C14—H14	119.4
C5—C4—H4	120.8	O3—C15—H15A	109.5
C6—C5—C4	121.1 (4)	O3—C15—H15B	109.5
C6—C5—Cl2	119.6 (4)	H15A—C15—H15B	109.5
C4—C5—Cl2	119.3 (4)	O3—C15—H15C	109.5
C5—C6—C1	121.1 (4)	H15A—C15—H15C	109.5
C5—C6—H6	119.5	H15B—C15—H15C	109.5
C1—C6—H6	119.5	C7—C16—H16A	109.5
N1—C7—C1	114.5 (4)	C7—C16—H16B	109.5
N1—C7—C16	125.9 (4)	H16A—C16—H16B	109.5
C1—C7—C16	119.6 (4)	C7—C16—H16C	109.5
O2—C8—N2	119.6 (4)	H16A—C16—H16C	109.5
O2—C8—C9	122.8 (4)	H16B—C16—H16C	109.5
N2—C8—C9	117.6 (4)
C7—N1—N2—C8	173.8 (4)	C6—C1—C7—C16	−2.6 (6)
C6—C1—C2—O1	−177.2 (4)	C2—C1—C7—C16	176.7 (4)
C7—C1—C2—O1	3.5 (6)	N1—N2—C8—O2	0.7 (6)
C6—C1—C2—C3	1.7 (6)	N1—N2—C8—C9	−179.0 (4)
C7—C1—C2—C3	−177.5 (4)	O2—C8—C9—C14	14.7 (7)
O1—C2—C3—C4	177.9 (4)	N2—C8—C9—C14	−165.6 (4)
C1—C2—C3—C4	−1.1 (7)	O2—C8—C9—C10	−164.4 (5)
O1—C2—C3—Cl1	−1.4 (6)	N2—C8—C9—C10	15.3 (6)
C1—C2—C3—Cl1	179.7 (3)	C14—C9—C10—C11	2.0 (7)
C2—C3—C4—C5	−0.7 (7)	C8—C9—C10—C11	−178.9 (4)
Cl1—C3—C4—C5	178.5 (4)	C9—C10—C11—C12	−0.7 (7)
C3—C4—C5—C6	1.9 (7)	C15—O3—C12—C13	176.6 (5)
C3—C4—C5—Cl2	−178.9 (4)	C15—O3—C12—C11	−2.9 (8)
C4—C5—C6—C1	−1.3 (7)	C10—C11—C12—O3	178.5 (5)
Cl2—C5—C6—C1	179.6 (4)	C10—C11—C12—C13	−1.0 (8)
C2—C1—C6—C5	−0.6 (7)	O3—C12—C13—C14	−178.2 (4)
C7—C1—C6—C5	178.7 (4)	C11—C12—C13—C14	1.3 (8)
N2—N1—C7—C1	179.8 (4)	C10—C9—C14—C13	−1.7 (7)
N2—N1—C7—C16	−0.8 (7)	C8—C9—C14—C13	179.2 (4)
C6—C1—C7—N1	176.9 (4)	C12—C13—C14—C9	0.1 (7)
C2—C1—C7—N1	−3.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	2.15	2.926 (5)	150
O1—H1···O2	0.82	2.58	3.287 (5)	146
O1—H1···N1	0.82	1.77	2.484 (5)	145
O4—H16···O1i	0.85	2.09	2.887 (5)	156
O4—H15···O2ii	0.85	1.88	2.726 (5)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.86	2.15	2.926 (5)	150
O1—H1⋯O2	0.82	2.58	3.287 (5)	146
O1—H1⋯N1	0.82	1.77	2.484 (5)	145
O4—H16⋯O1i	0.85	2.09	2.887 (5)	156
O4—H15⋯O2ii	0.85	1.88	2.726 (5)	176

Symmetry codes: (i) ; (ii) .