(E)-4-Hydr-oxy-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)benzohydrazide monohydrate.

The Schiff base mol-ecule of the title compound, C(15)H(14)N(2)O(4)·H(2)O, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is almost planar (r.m.s. deviation for all non-H atoms = 0.040 Å). The amido N atom is the hydrogen-bond donor to the water mol-ecule, which is the hydrogen-bond donor to the hydr-oxy groups of two neighboring mol-ecules. One of the hydroxyl groups acts as an intra-molecular and the other as an inter-molecular hydrogen-bond donor.

Related literature

For the structure of (E)-4-chloro-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzo­hydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007 ▶). For a series of similar compounds, see: Lu et al. (2008a ▶,b ▶,c ▶). For this and other compounds with anti­malarial properties, see: Melnyk et al. (2006 ▶).

Experimental

Crystal data

C15H14N2O4·H2O

M = 304.30

Monoclinic,

a = 7.1763 (2) Å

b = 16.6507 (5) Å

c = 12.1828 (4) Å

β = 98.022 (2)°

V = 1441.48 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 (2) K

0.16 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

13327 measured reflections

3315 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.180

S = 1.05

3315 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042888/bt2836sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042888/bt2836Isup2.hkl

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

C15H14N2O4·H2O	F(000) = 640
Mr = 304.30	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1918 reflections
a = 7.1763 (2) Å	θ = 2.4–27.3°
b = 16.6507 (5) Å	µ = 0.11 mm−1
c = 12.1828 (4) Å	T = 100 K
β = 98.022 (2)°	Prism, yellow
V = 1441.48 (8) Å3	0.16 × 0.04 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 27.5°, θmin = 2.1°
ω scans	h = −9→9
13327 measured reflections	k = −21→21
3315 independent 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0687P)2 + 1.4764P] where P = (Fo2 + 2Fc2)/3
3315 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.7450 (3)	0.31702 (12)	1.09538 (15)	0.0271 (5)
H1	0.7745	0.2698	1.1150	0.041*
O2	0.3884 (3)	0.32742 (11)	0.58919 (15)	0.0246 (5)
O3	0.1758 (3)	0.41831 (13)	0.32215 (18)	0.0444 (6)
H3	0.2262	0.4067	0.3866	0.067*
O4	−0.1014 (3)	0.59721 (14)	0.05179 (16)	0.0359 (6)
O5	0.4249 (4)	0.61425 (14)	0.73043 (18)	0.0495 (7)
H51	0.4027	0.6363	0.7892	0.074*
H52	0.5420	0.6108	0.7317	0.074*
N1	0.3620 (3)	0.45875 (14)	0.62786 (18)	0.0208 (5)
H11	0.3800	0.4987	0.6754	0.025*
N2	0.2800 (3)	0.47111 (14)	0.51985 (17)	0.0218 (5)
C1	0.4997 (3)	0.36829 (15)	0.7739 (2)	0.0174 (5)
C2	0.5351 (4)	0.42869 (16)	0.8536 (2)	0.0204 (6)
H2	0.5012	0.4826	0.8345	0.024*
C3	0.6192 (4)	0.41082 (16)	0.9602 (2)	0.0216 (6)
H3A	0.6449	0.4524	1.0135	0.026*
C4	0.6653 (3)	0.33229 (16)	0.9886 (2)	0.0197 (6)
C5	0.6322 (4)	0.27144 (16)	0.9108 (2)	0.0214 (6)
H5A	0.6655	0.2176	0.9305	0.026*
C6	0.5504 (4)	0.28976 (16)	0.8043 (2)	0.0208 (6)
H6	0.5284	0.2481	0.7508	0.025*
C7	0.4134 (3)	0.38292 (16)	0.6579 (2)	0.0191 (6)
C8	0.2221 (4)	0.54217 (18)	0.4913 (2)	0.0231 (6)
H8	0.2362	0.5848	0.5436	0.028*
C9	0.1350 (4)	0.55631 (18)	0.3780 (2)	0.0235 (6)
C10	0.1117 (4)	0.49462 (18)	0.2982 (2)	0.0289 (7)
C11	0.0295 (4)	0.5107 (2)	0.1905 (2)	0.0329 (7)
H11A	0.0125	0.4689	0.1371	0.040*
C12	−0.0278 (4)	0.5882 (2)	0.1614 (2)	0.0281 (7)
C13	−0.0097 (4)	0.64983 (19)	0.2380 (2)	0.0290 (7)
H13	−0.0519	0.7025	0.2177	0.035*
C14	0.0714 (4)	0.63284 (18)	0.3450 (2)	0.0270 (6)
H14	0.0843	0.6749	0.3982	0.032*
C15	−0.1581 (4)	0.6759 (2)	0.0151 (3)	0.0385 (8)
H15A	−0.2026	0.6749	−0.0647	0.058*
H15B	−0.0508	0.7127	0.0299	0.058*
H15C	−0.2598	0.6944	0.0549	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0379 (11)	0.0266 (11)	0.0146 (9)	0.0096 (9)	−0.0039 (8)	0.0015 (8)
O2	0.0309 (10)	0.0230 (10)	0.0188 (10)	−0.0048 (8)	−0.0008 (8)	−0.0005 (8)
O3	0.0701 (17)	0.0318 (13)	0.0264 (12)	−0.0012 (12)	−0.0107 (11)	0.0029 (10)
O4	0.0320 (12)	0.0538 (15)	0.0203 (10)	0.0041 (10)	−0.0018 (9)	0.0118 (10)
O5	0.0772 (18)	0.0431 (14)	0.0259 (12)	0.0265 (13)	−0.0009 (12)	−0.0119 (11)
N1	0.0228 (12)	0.0233 (12)	0.0152 (11)	0.0005 (9)	−0.0016 (9)	0.0003 (9)
N2	0.0209 (11)	0.0306 (13)	0.0132 (11)	−0.0014 (10)	0.0004 (9)	0.0039 (9)
C1	0.0136 (12)	0.0223 (13)	0.0164 (13)	−0.0033 (10)	0.0020 (10)	−0.0001 (11)
C2	0.0201 (13)	0.0213 (14)	0.0197 (13)	0.0023 (10)	0.0027 (10)	0.0031 (11)
C3	0.0260 (14)	0.0207 (14)	0.0172 (13)	0.0012 (11)	0.0001 (10)	−0.0035 (11)
C4	0.0192 (13)	0.0249 (14)	0.0144 (12)	0.0032 (11)	0.0007 (10)	0.0034 (11)
C5	0.0221 (13)	0.0201 (14)	0.0214 (13)	0.0022 (11)	0.0006 (11)	0.0011 (11)
C6	0.0217 (13)	0.0228 (14)	0.0170 (13)	−0.0005 (11)	−0.0004 (11)	−0.0033 (11)
C7	0.0173 (13)	0.0225 (14)	0.0176 (13)	−0.0027 (10)	0.0029 (10)	0.0000 (11)
C8	0.0197 (13)	0.0303 (15)	0.0195 (14)	0.0004 (11)	0.0035 (11)	0.0013 (12)
C9	0.0184 (13)	0.0327 (16)	0.0198 (14)	−0.0033 (11)	0.0043 (11)	0.0066 (12)
C10	0.0333 (16)	0.0286 (16)	0.0242 (14)	−0.0018 (13)	0.0013 (12)	0.0074 (13)
C11	0.0371 (17)	0.0391 (18)	0.0211 (15)	−0.0053 (14)	−0.0013 (12)	0.0008 (13)
C12	0.0192 (14)	0.0471 (19)	0.0177 (14)	−0.0008 (13)	0.0011 (11)	0.0108 (13)
C13	0.0237 (14)	0.0358 (17)	0.0269 (16)	0.0055 (12)	0.0018 (12)	0.0123 (13)
C14	0.0235 (14)	0.0327 (16)	0.0249 (15)	0.0039 (12)	0.0043 (12)	0.0033 (12)
C15	0.0314 (17)	0.057 (2)	0.0263 (16)	0.0062 (16)	0.0018 (13)	0.0173 (16)

O1—C4	1.370 (3)	C3—H3A	0.9500
O1—H1	0.8400	C4—C5	1.385 (4)
O2—C7	1.243 (3)	C5—C6	1.382 (4)
O3—C10	1.369 (4)	C5—H5A	0.9500
O3—H3	0.8400	C6—H6	0.9500
O4—C12	1.374 (3)	C8—C9	1.452 (4)
O4—C15	1.426 (4)	C8—H8	0.9500
O5—H51	0.8400	C9—C14	1.394 (4)
O5—H52	0.8400	C9—C10	1.408 (4)
N1—C7	1.351 (3)	C10—C11	1.387 (4)
N1—N2	1.380 (3)	C11—C12	1.385 (4)
N1—H11	0.8800	C11—H11A	0.9500
N2—C8	1.286 (4)	C12—C13	1.381 (4)
C1—C6	1.393 (4)	C13—C14	1.381 (4)
C1—C2	1.396 (4)	C13—H13	0.9500
C1—C7	1.482 (3)	C14—H14	0.9500
C2—C3	1.386 (4)	C15—H15A	0.9800
C2—H2	0.9500	C15—H15B	0.9800
C3—C4	1.381 (4)	C15—H15C	0.9800
C4—O1—H1	119.9	N1—C7—C1	118.3 (2)
C10—O3—H3	120.0	N2—C8—C9	119.1 (3)
C12—O4—C15	117.3 (3)	N2—C8—H8	120.5
H51—O5—H52	108.8	C9—C8—H8	120.5
C7—N1—N2	117.5 (2)	C14—C9—C10	117.7 (3)
C7—N1—H11	121.3	C14—C9—C8	120.2 (3)
N2—N1—H11	121.3	C10—C9—C8	122.1 (3)
C8—N2—N1	118.3 (2)	O3—C10—C11	117.8 (3)
C6—C1—C2	118.4 (2)	O3—C10—C9	121.7 (3)
C6—C1—C7	117.8 (2)	C11—C10—C9	120.4 (3)
C2—C1—C7	123.8 (2)	C12—C11—C10	119.6 (3)
C3—C2—C1	120.7 (2)	C12—C11—H11A	120.2
C3—C2—H2	119.7	C10—C11—H11A	120.2
C1—C2—H2	119.7	O4—C12—C13	124.3 (3)
C4—C3—C2	119.8 (2)	O4—C12—C11	114.2 (3)
C4—C3—H3A	120.1	C13—C12—C11	121.5 (3)
C2—C3—H3A	120.1	C12—C13—C14	118.3 (3)
O1—C4—C3	117.9 (2)	C12—C13—H13	120.9
O1—C4—C5	121.5 (2)	C14—C13—H13	120.9
C3—C4—C5	120.5 (2)	C13—C14—C9	122.5 (3)
C6—C5—C4	119.4 (2)	C13—C14—H14	118.7
C6—C5—H5A	120.3	C9—C14—H14	118.7
C4—C5—H5A	120.3	O4—C15—H15A	109.5
C5—C6—C1	121.2 (2)	O4—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O4—C15—H15C	109.5
O2—C7—N1	120.3 (2)	H15A—C15—H15C	109.5
O2—C7—C1	121.4 (2)	H15B—C15—H15C	109.5
C7—N1—N2—C8	176.8 (2)	N2—C8—C9—C14	−179.9 (3)
C6—C1—C2—C3	0.2 (4)	N2—C8—C9—C10	0.0 (4)
C7—C1—C2—C3	−178.9 (2)	C14—C9—C10—O3	177.7 (3)
C1—C2—C3—C4	−1.2 (4)	C8—C9—C10—O3	−2.2 (4)
C2—C3—C4—O1	−178.8 (2)	C14—C9—C10—C11	0.6 (4)
C2—C3—C4—C5	1.5 (4)	C8—C9—C10—C11	−179.3 (3)
O1—C4—C5—C6	179.6 (2)	O3—C10—C11—C12	−176.4 (3)
C3—C4—C5—C6	−0.7 (4)	C9—C10—C11—C12	0.8 (4)
C4—C5—C6—C1	−0.3 (4)	C15—O4—C12—C13	1.6 (4)
C2—C1—C6—C5	0.6 (4)	C15—O4—C12—C11	−178.2 (3)
C7—C1—C6—C5	179.7 (2)	C10—C11—C12—O4	178.0 (3)
N2—N1—C7—O2	0.7 (4)	C10—C11—C12—C13	−1.8 (4)
N2—N1—C7—C1	−179.3 (2)	O4—C12—C13—C14	−178.4 (3)
C6—C1—C7—O2	−0.7 (4)	C11—C12—C13—C14	1.4 (4)
C2—C1—C7—O2	178.4 (2)	C12—C13—C14—C9	0.0 (4)
C6—C1—C7—N1	179.3 (2)	C10—C9—C14—C13	−1.0 (4)
C2—C1—C7—N1	−1.6 (4)	C8—C9—C14—C13	178.9 (3)
N1—N2—C8—C9	−179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.86	2.621 (3)	150
O3—H3···N2	0.84	1.94	2.575 (3)	132
O5—H51···O1ii	0.84	2.03	2.833 (3)	160
O5—H52···O3iii	0.84	2.27	3.070 (4)	160
N1—H11···O5	0.88	2.05	2.883 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.86	2.621 (3)	150
O3—H3⋯N2	0.84	1.94	2.575 (3)	132
O5—H51⋯O1ii	0.84	2.03	2.833 (3)	160
O5—H52⋯O3iii	0.84	2.27	3.070 (4)	160
N1—H11⋯O5	0.88	2.05	2.883 (3)	158

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