N'-(3-Eth-oxy-2-hydroxy-benzyl-idene)-4-hydr-oxy-3-methoxy-benzohydrazide monohydrate.

In the title compound, C(17)H(18)N(2)O(5)·H(2)O, the dihedral angle between the two aromatic rings is 7.86 (7)° and an intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Abdul Alhadi et al. (2009 ▶); Mohd Lair et al. (2009 ▶); Narayana et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H18N2O5·H2O

M = 348.35

Monoclinic,

a = 9.4063 (11) Å

b = 10.0598 (12) Å

c = 17.667 (2) Å

β = 93.702 (2)°

V = 1668.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.976, T max = 0.979

9554 measured reflections

3606 independent reflections

2530 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.05

3606 reflections

239 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536809033236/ci2887sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033236/ci2887Isup2.hkl

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

C17H18N2O5·H2O	F(000) = 736
Mr = 348.35	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2358 reflections
a = 9.4063 (11) Å	θ = 2.3–24.5°
b = 10.0598 (12) Å	µ = 0.11 mm−1
c = 17.667 (2) Å	T = 298 K
β = 93.702 (2)°	Block, colourless
V = 1668.3 (3) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→6
Tmin = 0.976, Tmax = 0.979	k = −12→12
9554 measured reflections	l = −19→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.153P] where P = (Fo2 + 2Fc2)/3
3606 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.14 e Å−3
4 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.10205 (14)	0.58113 (13)	0.92228 (7)	0.0430 (3)
N2	0.02746 (14)	0.49793 (13)	0.87165 (7)	0.0439 (3)
O1	0.33352 (11)	0.69470 (12)	0.98717 (7)	0.0540 (3)
H1	0.2897	0.6377	0.9621	0.081*
O2	0.44363 (11)	0.88030 (11)	1.07376 (6)	0.0500 (3)
O3	0.22665 (12)	0.38467 (12)	0.84788 (6)	0.0540 (3)
O4	−0.35636 (11)	0.22118 (12)	0.71623 (6)	0.0519 (3)
O5	−0.21352 (12)	0.07248 (12)	0.62606 (6)	0.0495 (3)
H5	−0.1832	0.0803	0.5838	0.074*
O6	0.87031 (16)	0.12628 (18)	0.49098 (7)	0.0831 (5)
C1	0.09270 (16)	0.76123 (14)	1.00984 (8)	0.0386 (4)
C2	0.23985 (16)	0.77422 (14)	1.02122 (8)	0.0381 (3)
C3	0.29798 (17)	0.87517 (15)	1.06851 (8)	0.0401 (4)
C4	0.20833 (19)	0.95870 (16)	1.10488 (9)	0.0461 (4)
H4	0.2463	1.0260	1.1361	0.055*
C5	0.06202 (19)	0.94300 (17)	1.09513 (9)	0.0491 (4)
H5A	0.0024	0.9986	1.1207	0.059*
C6	0.00461 (18)	0.84627 (16)	1.04808 (9)	0.0455 (4)
H6	−0.0938	0.8371	1.0415	0.055*
C7	0.02778 (17)	0.66469 (15)	0.95732 (8)	0.0432 (4)
H7	−0.0708	0.6636	0.9489	0.052*
C8	0.09772 (16)	0.40175 (15)	0.83586 (8)	0.0384 (4)
C9	0.01099 (15)	0.31662 (14)	0.78123 (8)	0.0351 (3)
C10	−0.13784 (16)	0.31459 (14)	0.77666 (8)	0.0365 (3)
H10	−0.1878	0.3686	0.8084	0.044*
C11	−0.21102 (15)	0.23219 (15)	0.72488 (8)	0.0366 (3)
C12	−0.13654 (17)	0.15245 (14)	0.67632 (8)	0.0377 (3)
C13	0.01011 (17)	0.15321 (15)	0.68193 (8)	0.0420 (4)
H13	0.0602	0.0985	0.6506	0.050*
C14	0.08347 (16)	0.23511 (15)	0.73412 (8)	0.0397 (4)
H14	0.1825	0.2351	0.7374	0.048*
C15	0.50926 (19)	0.98456 (17)	1.11853 (11)	0.0572 (5)
H15A	0.4796	0.9801	1.1701	0.069*
H15B	0.4817	1.0705	1.0974	0.069*
C16	0.66733 (19)	0.9667 (2)	1.11801 (12)	0.0642 (5)
H16A	0.6931	0.8805	1.1379	0.096*
H16B	0.7144	1.0340	1.1489	0.096*
H16C	0.6958	0.9740	1.0670	0.096*
C17	−0.44022 (17)	0.30663 (19)	0.75946 (10)	0.0555 (5)
H17A	−0.4195	0.2898	0.8125	0.083*
H17B	−0.5394	0.2902	0.7466	0.083*
H17C	−0.4184	0.3975	0.7484	0.083*
H2	−0.0640 (12)	0.519 (2)	0.8616 (11)	0.080*
H6A	0.8271 (18)	0.119 (2)	0.4483 (7)	0.080*
H6B	0.9512 (13)	0.161 (2)	0.4869 (11)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0430 (8)	0.0417 (7)	0.0424 (7)	−0.0028 (6)	−0.0102 (6)	−0.0046 (6)
N2	0.0378 (7)	0.0425 (7)	0.0495 (7)	−0.0006 (6)	−0.0130 (6)	−0.0076 (6)
O1	0.0423 (7)	0.0555 (7)	0.0638 (8)	0.0032 (6)	−0.0008 (6)	−0.0259 (6)
O2	0.0426 (7)	0.0509 (7)	0.0560 (7)	−0.0028 (5)	−0.0007 (5)	−0.0188 (5)
O3	0.0348 (6)	0.0661 (8)	0.0591 (7)	0.0020 (6)	−0.0115 (5)	−0.0130 (6)
O4	0.0321 (6)	0.0615 (7)	0.0616 (7)	−0.0057 (5)	−0.0012 (5)	−0.0146 (6)
O5	0.0477 (7)	0.0577 (7)	0.0426 (6)	−0.0144 (6)	0.0003 (5)	−0.0110 (5)
O6	0.0632 (9)	0.1350 (14)	0.0491 (7)	−0.0436 (9)	−0.0107 (7)	0.0188 (8)
C1	0.0404 (9)	0.0381 (8)	0.0367 (8)	0.0013 (7)	−0.0030 (7)	0.0019 (6)
C2	0.0421 (9)	0.0359 (8)	0.0360 (7)	0.0038 (7)	0.0012 (7)	−0.0027 (6)
C3	0.0393 (9)	0.0415 (8)	0.0391 (8)	0.0004 (7)	−0.0014 (7)	−0.0028 (7)
C4	0.0549 (11)	0.0411 (9)	0.0420 (8)	0.0016 (8)	−0.0001 (8)	−0.0104 (7)
C5	0.0500 (10)	0.0490 (10)	0.0488 (9)	0.0113 (8)	0.0060 (8)	−0.0058 (7)
C6	0.0416 (9)	0.0481 (9)	0.0465 (9)	0.0043 (8)	0.0008 (7)	0.0004 (7)
C7	0.0396 (9)	0.0448 (9)	0.0442 (9)	0.0001 (7)	−0.0061 (7)	0.0000 (7)
C8	0.0367 (9)	0.0412 (9)	0.0362 (8)	−0.0015 (7)	−0.0055 (7)	0.0024 (6)
C9	0.0349 (8)	0.0366 (8)	0.0328 (7)	−0.0019 (7)	−0.0047 (6)	0.0039 (6)
C10	0.0364 (8)	0.0378 (8)	0.0350 (7)	0.0002 (7)	−0.0006 (6)	−0.0010 (6)
C11	0.0302 (8)	0.0400 (8)	0.0391 (8)	−0.0041 (7)	−0.0017 (6)	0.0048 (6)
C12	0.0408 (8)	0.0382 (8)	0.0334 (7)	−0.0085 (7)	−0.0024 (6)	0.0001 (6)
C13	0.0399 (9)	0.0457 (9)	0.0407 (8)	−0.0014 (7)	0.0057 (7)	−0.0030 (7)
C14	0.0314 (8)	0.0449 (9)	0.0422 (8)	−0.0019 (7)	−0.0009 (7)	0.0017 (7)
C15	0.0513 (11)	0.0513 (10)	0.0682 (11)	−0.0078 (9)	−0.0016 (9)	−0.0219 (9)
C16	0.0497 (11)	0.0614 (12)	0.0804 (13)	−0.0063 (9)	−0.0032 (10)	−0.0139 (10)
C17	0.0362 (9)	0.0684 (12)	0.0622 (11)	0.0030 (9)	0.0043 (8)	−0.0016 (9)

N1—C7	1.278 (2)	C5—H5A	0.93
N1—N2	1.3827 (17)	C6—H6	0.93
N2—C8	1.352 (2)	C7—H7	0.93
N2—H2	0.891 (9)	C8—C9	1.493 (2)
O1—C2	1.3589 (18)	C9—C14	1.380 (2)
O1—H1	0.82	C9—C10	1.397 (2)
O2—C3	1.3681 (19)	C10—C11	1.384 (2)
O2—C15	1.4296 (18)	C10—H10	0.93
O3—C8	1.2297 (18)	C11—C12	1.396 (2)
O4—C11	1.3703 (17)	C12—C13	1.377 (2)
O4—C17	1.422 (2)	C13—C14	1.387 (2)
O5—C12	1.3700 (17)	C13—H13	0.93
O5—H5	0.82	C14—H14	0.93
O6—H6A	0.836 (9)	C15—C16	1.498 (2)
O6—H6B	0.844 (9)	C15—H15A	0.97
C1—C2	1.392 (2)	C15—H15B	0.97
C1—C6	1.395 (2)	C16—H16A	0.96
C1—C7	1.450 (2)	C16—H16B	0.96
C2—C3	1.403 (2)	C16—H16C	0.96
C3—C4	1.378 (2)	C17—H17A	0.96
C4—C5	1.385 (2)	C17—H17B	0.96
C4—H4	0.93	C17—H17C	0.96
C5—C6	1.368 (2)
C7—N1—N2	116.17 (13)	C10—C9—C8	123.32 (13)
C8—N2—N1	119.54 (13)	C11—C10—C9	120.03 (14)
C8—N2—H2	124.6 (13)	C11—C10—H10	120.0
N1—N2—H2	115.6 (13)	C9—C10—H10	120.0
C2—O1—H1	109.5	O4—C11—C10	124.89 (14)
C3—O2—C15	117.38 (12)	O4—C11—C12	114.95 (12)
C11—O4—C17	118.38 (12)	C10—C11—C12	120.16 (13)
C12—O5—H5	109.5	O5—C12—C13	122.36 (14)
H6A—O6—H6B	110.4 (17)	O5—C12—C11	118.08 (13)
C2—C1—C6	119.25 (14)	C13—C12—C11	119.53 (13)
C2—C1—C7	121.93 (14)	C12—C13—C14	120.30 (14)
C6—C1—C7	118.79 (14)	C12—C13—H13	119.8
O1—C2—C1	123.22 (13)	C14—C13—H13	119.8
O1—C2—C3	116.79 (14)	C9—C14—C13	120.67 (14)
C1—C2—C3	119.97 (14)	C9—C14—H14	119.7
O2—C3—C4	125.84 (14)	C13—C14—H14	119.7
O2—C3—C2	114.69 (13)	O2—C15—C16	107.56 (14)
C4—C3—C2	119.48 (15)	O2—C15—H15A	110.2
C3—C4—C5	120.36 (15)	C16—C15—H15A	110.2
C3—C4—H4	119.8	O2—C15—H15B	110.2
C5—C4—H4	119.8	C16—C15—H15B	110.2
C6—C5—C4	120.45 (15)	H15A—C15—H15B	108.5
C6—C5—H5A	119.8	C15—C16—H16A	109.5
C4—C5—H5A	119.8	C15—C16—H16B	109.5
C5—C6—C1	120.45 (16)	H16A—C16—H16B	109.5
C5—C6—H6	119.8	C15—C16—H16C	109.5
C1—C6—H6	119.8	H16A—C16—H16C	109.5
N1—C7—C1	121.97 (14)	H16B—C16—H16C	109.5
N1—C7—H7	119.0	O4—C17—H17A	109.5
C1—C7—H7	119.0	O4—C17—H17B	109.5
O3—C8—N2	121.72 (14)	H17A—C17—H17B	109.5
O3—C8—C9	121.55 (14)	O4—C17—H17C	109.5
N2—C8—C9	116.73 (13)	H17A—C17—H17C	109.5
C14—C9—C10	119.27 (13)	H17B—C17—H17C	109.5
C14—C9—C8	117.40 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.6529 (16)	144
O5—H5···O6i	0.82	1.81	2.6177 (17)	170
O6—H6A···O3ii	0.84 (1)	1.96 (1)	2.7908 (17)	176 (2)
O6—H6B···O1iii	0.84 (1)	2.08 (1)	2.8714 (18)	157 (2)
N2—H2···O4iv	0.89 (1)	2.54 (2)	3.1181 (17)	123 (2)
N2—H2···O5iv	0.89 (1)	2.19 (1)	3.0496 (18)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.94	2.6529 (16)	144
O5—H5⋯O6i	0.82	1.81	2.6177 (17)	170
O6—H6A⋯O3ii	0.84 (1)	1.96 (1)	2.7908 (17)	176 (2)
O6—H6B⋯O1iii	0.84 (1)	2.08 (1)	2.8714 (18)	157 (2)
N2—H2⋯O4iv	0.89 (1)	2.54 (2)	3.1181 (17)	123 (2)
N2—H2⋯O5iv	0.89 (1)	2.19 (1)	3.0496 (18)	163 (2)

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