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

The title compound, C(17)H(16)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 30.77 (5)° and there is one intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by hydrogen bonding to the water molecules of crystallization, which acts as both an acceptor and a donor, into a three-dimensional network.

Related literature

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

Experimental

Crystal data

C17H16Cl2N2O3·H2O

M = 385.23

Monoclinic,

a = 32.925 (3) Å

b = 7.3733 (7) Å

c = 15.1252 (13) Å

β = 92.319 (2)°

V = 3668.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.38 mm−1

T = 295 K

0.21 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.925, T max = 0.960

9328 measured reflections

3242 independent reflections

2320 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.01

3242 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.39 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/S1600536810037293/fl2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037293/fl2314Isup2.hkl

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

C17H16Cl2N2O3·H2O	F(000) = 1600
Mr = 385.23	Dx = 1.395 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2261 reflections
a = 32.925 (3) Å	θ = 2.7–22.8°
b = 7.3733 (7) Å	µ = 0.38 mm−1
c = 15.1252 (13) Å	T = 295 K
β = 92.319 (2)°	Block, colourless
V = 3668.9 (6) Å3	0.21 × 0.16 × 0.11 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3242 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −38→31
Tmin = 0.925, Tmax = 0.960	k = −7→8
9328 measured reflections	l = −17→18

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0624P)2 + 2.1699P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3242 reflections	Δρmax = 0.28 e Å−3
230 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

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	0.90858 (2)	0.20782 (14)	0.56665 (4)	0.0858 (3)
Cl2	0.96867 (2)	0.10906 (15)	0.90003 (5)	0.0939 (4)
N1	0.78571 (6)	0.0580 (3)	0.76338 (12)	0.0430 (5)
N2	0.74565 (5)	0.0416 (3)	0.78172 (11)	0.0449 (5)
H2	0.7378	0.0201	0.8342	0.054*
O1	0.83142 (5)	0.1268 (2)	0.64024 (10)	0.0538 (5)
H1	0.8097	0.1104	0.6635	0.081*
O2	0.73122 (5)	0.0679 (2)	0.63564 (10)	0.0550 (5)
O3	0.55192 (6)	0.1318 (3)	0.76671 (15)	0.0877 (7)
O4	0.28854 (6)	0.0811 (2)	0.04707 (10)	0.0605 (5)
H18	0.2830	0.0895	−0.0081	0.091*
H19	0.3050	0.1670	0.0597	0.091*
C1	0.86185 (7)	0.1190 (3)	0.70224 (14)	0.0445 (6)
C2	0.90114 (8)	0.1561 (4)	0.67682 (15)	0.0528 (6)
C3	0.93372 (8)	0.1525 (4)	0.73556 (18)	0.0636 (7)
H3	0.9597	0.1786	0.7172	0.076*
C4	0.92734 (8)	0.1095 (4)	0.82283 (17)	0.0596 (7)
C5	0.88941 (7)	0.0692 (3)	0.85008 (16)	0.0503 (6)
H5	0.8860	0.0387	0.9090	0.060*
C6	0.85555 (7)	0.0729 (3)	0.79125 (14)	0.0409 (5)
C7	0.81465 (7)	0.0354 (3)	0.82230 (14)	0.0397 (5)
C8	0.80792 (7)	−0.0152 (3)	0.91630 (14)	0.0437 (5)
H8A	0.8310	−0.0844	0.9394	0.052*
H8B	0.7840	−0.0916	0.9186	0.052*
C9	0.80230 (9)	0.1511 (4)	0.97375 (16)	0.0606 (7)
H9A	0.8275	0.2160	0.9799	0.091*
H9B	0.7939	0.1141	1.0311	0.091*
H9C	0.7819	0.2284	0.9466	0.091*
C10	0.71868 (7)	0.0615 (3)	0.71071 (14)	0.0418 (5)
C11	0.67535 (7)	0.0788 (3)	0.72990 (14)	0.0422 (5)
C12	0.66180 (7)	0.1335 (3)	0.81114 (15)	0.0505 (6)
H12	0.6807	0.1569	0.8570	0.061*
C13	0.62131 (8)	0.1540 (4)	0.82595 (17)	0.0584 (7)
H13	0.6130	0.1909	0.8812	0.070*
C14	0.59297 (8)	0.1198 (4)	0.75892 (19)	0.0593 (7)
C15	0.60576 (8)	0.0678 (4)	0.67635 (18)	0.0621 (7)
H15	0.5867	0.0458	0.6306	0.075*
C16	0.64623 (7)	0.0488 (3)	0.66187 (16)	0.0522 (6)
H16	0.6545	0.0154	0.6061	0.063*
C17	0.53716 (10)	0.1785 (6)	0.8521 (2)	0.1014 (12)
H17A	0.5465	0.0903	0.8950	0.152*
H17B	0.5080	0.1802	0.8491	0.152*
H17C	0.5472	0.2962	0.8692	0.152*

	U11	U22	U33	U12	U13	U23
Cl1	0.0798 (6)	0.1289 (8)	0.0498 (4)	−0.0187 (5)	0.0173 (4)	−0.0021 (4)
Cl2	0.0387 (4)	0.1699 (10)	0.0722 (5)	0.0028 (4)	−0.0099 (3)	0.0112 (5)
N1	0.0393 (11)	0.0532 (12)	0.0363 (10)	0.0011 (9)	−0.0018 (8)	0.0007 (9)
N2	0.0402 (11)	0.0603 (13)	0.0340 (10)	−0.0005 (9)	−0.0003 (8)	0.0058 (9)
O1	0.0489 (10)	0.0745 (12)	0.0378 (9)	−0.0036 (9)	−0.0019 (7)	0.0026 (8)
O2	0.0523 (10)	0.0788 (12)	0.0337 (9)	0.0002 (9)	−0.0012 (7)	0.0023 (8)
O3	0.0422 (11)	0.1199 (19)	0.1009 (17)	0.0046 (11)	0.0012 (11)	−0.0046 (14)
O4	0.0738 (12)	0.0694 (12)	0.0379 (9)	−0.0159 (9)	−0.0028 (8)	0.0036 (8)
C1	0.0480 (14)	0.0468 (13)	0.0385 (12)	0.0019 (11)	−0.0019 (10)	−0.0035 (10)
C2	0.0504 (15)	0.0648 (16)	0.0439 (13)	0.0003 (12)	0.0082 (11)	−0.0045 (12)
C3	0.0432 (15)	0.085 (2)	0.0629 (17)	0.0017 (13)	0.0084 (13)	−0.0052 (15)
C4	0.0411 (14)	0.082 (2)	0.0554 (15)	0.0071 (13)	−0.0029 (12)	−0.0018 (14)
C5	0.0442 (14)	0.0633 (16)	0.0432 (13)	0.0097 (11)	−0.0017 (11)	0.0019 (11)
C6	0.0415 (13)	0.0423 (13)	0.0388 (12)	0.0050 (10)	−0.0013 (9)	−0.0020 (10)
C7	0.0445 (13)	0.0384 (12)	0.0359 (11)	0.0038 (10)	−0.0023 (10)	−0.0016 (9)
C8	0.0425 (13)	0.0489 (13)	0.0395 (12)	0.0017 (10)	−0.0031 (10)	0.0053 (10)
C9	0.0770 (18)	0.0666 (17)	0.0383 (13)	−0.0001 (14)	0.0055 (12)	−0.0033 (12)
C10	0.0462 (13)	0.0414 (13)	0.0374 (13)	−0.0004 (10)	−0.0044 (10)	0.0002 (10)
C11	0.0426 (13)	0.0409 (12)	0.0425 (12)	−0.0026 (10)	−0.0062 (10)	0.0040 (10)
C12	0.0459 (14)	0.0614 (16)	0.0436 (13)	0.0016 (12)	−0.0049 (11)	−0.0010 (11)
C13	0.0532 (16)	0.0683 (18)	0.0541 (15)	0.0056 (13)	0.0049 (13)	0.0004 (13)
C14	0.0417 (14)	0.0641 (17)	0.0719 (18)	0.0013 (12)	0.0004 (13)	0.0059 (14)
C15	0.0477 (16)	0.0732 (19)	0.0638 (17)	−0.0041 (13)	−0.0179 (13)	−0.0016 (14)
C16	0.0525 (15)	0.0557 (15)	0.0476 (14)	−0.0007 (12)	−0.0073 (11)	−0.0025 (11)
C17	0.0529 (19)	0.139 (3)	0.114 (3)	0.009 (2)	0.0225 (19)	−0.006 (3)

Cl1—C2	1.736 (2)	C7—C8	1.495 (3)
Cl2—C4	1.757 (3)	C8—C9	1.519 (3)
N1—C7	1.289 (3)	C8—H8A	0.9700
N1—N2	1.364 (3)	C8—H8B	0.9700
N2—C10	1.374 (3)	C9—H9A	0.9600
N2—H2	0.8600	C9—H9B	0.9600
O1—C1	1.346 (3)	C9—H9C	0.9600
O1—H1	0.8200	C10—C11	1.473 (3)
O2—C10	1.225 (3)	C11—C12	1.384 (3)
O3—C14	1.364 (3)	C11—C16	1.395 (3)
O3—C17	1.440 (4)	C12—C13	1.369 (3)
O4—H18	0.8499	C12—H12	0.9300
O4—H19	0.8500	C13—C14	1.373 (4)
C1—C2	1.392 (3)	C13—H13	0.9300
C1—C6	1.412 (3)	C14—C15	1.388 (4)
C2—C3	1.365 (3)	C15—C16	1.366 (4)
C3—C4	1.382 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.364 (3)	C17—H17A	0.9600
C5—C6	1.398 (3)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.470 (3)
C7—N1—N2	122.80 (18)	C8—C9—H9A	109.5
N1—N2—C10	115.55 (18)	C8—C9—H9B	109.5
N1—N2—H2	122.2	H9A—C9—H9B	109.5
C10—N2—H2	122.2	C8—C9—H9C	109.5
C1—O1—H1	109.5	H9A—C9—H9C	109.5
C14—O3—C17	117.7 (2)	H9B—C9—H9C	109.5
H18—O4—H19	106.0	O2—C10—N2	119.8 (2)
O1—C1—C2	118.2 (2)	O2—C10—C11	123.0 (2)
O1—C1—C6	122.7 (2)	N2—C10—C11	117.13 (19)
C2—C1—C6	119.0 (2)	C12—C11—C16	117.7 (2)
C3—C2—C1	122.1 (2)	C12—C11—C10	123.3 (2)
C3—C2—Cl1	119.4 (2)	C16—C11—C10	118.9 (2)
C1—C2—Cl1	118.50 (18)	C13—C12—C11	121.9 (2)
C2—C3—C4	118.7 (2)	C13—C12—H12	119.1
C2—C3—H3	120.6	C11—C12—H12	119.1
C4—C3—H3	120.6	C12—C13—C14	119.7 (2)
C5—C4—C3	121.0 (2)	C12—C13—H13	120.1
C5—C4—Cl2	119.5 (2)	C14—C13—H13	120.1
C3—C4—Cl2	119.5 (2)	O3—C14—C13	124.8 (3)
C4—C5—C6	121.3 (2)	O3—C14—C15	115.7 (2)
C4—C5—H5	119.3	C13—C14—C15	119.5 (2)
C6—C5—H5	119.3	C16—C15—C14	120.4 (2)
C5—C6—C1	117.9 (2)	C16—C15—H15	119.8
C5—C6—C7	120.7 (2)	C14—C15—H15	119.8
C1—C6—C7	121.45 (19)	C15—C16—C11	120.7 (2)
N1—C7—C6	114.57 (19)	C15—C16—H16	119.6
N1—C7—C8	123.8 (2)	C11—C16—H16	119.6
C6—C7—C8	121.57 (18)	O3—C17—H17A	109.5
C7—C8—C9	111.64 (19)	O3—C17—H17B	109.5
C7—C8—H8A	109.3	H17A—C17—H17B	109.5
C9—C8—H8A	109.3	O3—C17—H17C	109.5
C7—C8—H8B	109.3	H17A—C17—H17C	109.5
C9—C8—H8B	109.3	H17B—C17—H17C	109.5
H8A—C8—H8B	108.0
C7—N1—N2—C10	−177.1 (2)	C1—C6—C7—C8	179.4 (2)
O1—C1—C2—C3	179.5 (2)	N1—C7—C8—C9	−88.7 (3)
C6—C1—C2—C3	−1.2 (4)	C6—C7—C8—C9	88.0 (3)
O1—C1—C2—Cl1	−0.7 (3)	N1—N2—C10—O2	9.7 (3)
C6—C1—C2—Cl1	178.64 (18)	N1—N2—C10—C11	−168.88 (19)
C1—C2—C3—C4	0.4 (4)	O2—C10—C11—C12	−157.1 (2)
Cl1—C2—C3—C4	−179.4 (2)	N2—C10—C11—C12	21.4 (3)
C2—C3—C4—C5	0.7 (4)	O2—C10—C11—C16	19.2 (3)
C2—C3—C4—Cl2	−178.6 (2)	N2—C10—C11—C16	−162.3 (2)
C3—C4—C5—C6	−1.1 (4)	C16—C11—C12—C13	1.4 (4)
Cl2—C4—C5—C6	178.2 (2)	C10—C11—C12—C13	177.8 (2)
C4—C5—C6—C1	0.3 (4)	C11—C12—C13—C14	0.0 (4)
C4—C5—C6—C7	−177.8 (2)	C17—O3—C14—C13	−1.9 (4)
O1—C1—C6—C5	−179.9 (2)	C17—O3—C14—C15	177.7 (3)
C2—C1—C6—C5	0.8 (3)	C12—C13—C14—O3	178.4 (2)
O1—C1—C6—C7	−1.8 (3)	C12—C13—C14—C15	−1.1 (4)
C2—C1—C6—C7	178.9 (2)	O3—C14—C15—C16	−178.9 (3)
N2—N1—C7—C6	−175.44 (18)	C13—C14—C15—C16	0.7 (4)
N2—N1—C7—C8	1.4 (3)	C14—C15—C16—C11	0.8 (4)
C5—C6—C7—N1	174.4 (2)	C12—C11—C16—C15	−1.9 (4)
C1—C6—C7—N1	−3.6 (3)	C10—C11—C16—C15	−178.4 (2)
C5—C6—C7—C8	−2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.77	2.494 (2)	146
N2—H2···O4i	0.86	2.16	3.004 (2)	168
O4—H18···O2ii	0.85	1.97	2.815 (2)	171
O4—H19···O1iii	0.85	2.11	2.908 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.77	2.494 (2)	146
N2—H2⋯O4i	0.86	2.16	3.004 (2)	168
O4—H18⋯O2ii	0.85	1.97	2.815 (2)	171
O4—H19⋯O1iii	0.85	2.11	2.908 (2)	155

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