4-Hydr-oxy-N'-(2-hydr-oxy-3-methoxy-benzyl-idene)benzohydrazide mono-hydrate.

In the title compound, C(15)H(14)N(2)O(4)·H(2)O, the dihedral angle between the two aromatic rings is 33.3 (5)°. The meth-oxy group is twisted slightly away from the attached benzene ring [C-O-C-C = 13.8 (9)°]. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, the mol-ecules are linked into a two-dimensional network parallel to the (010) plane by inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O4·H2O

M = 304.30

Monoclinic,

a = 4.891 (2) Å

b = 12.171 (5) Å

c = 12.371 (5) Å

β = 95.724 (7)°

V = 732.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.08 × 0.07 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.992, T max = 0.993

5972 measured reflections

1582 independent reflections

791 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.119

S = 0.92

1582 reflections

211 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.15 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/S1600536808030894/ci2678sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030894/ci2678Isup2.hkl

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

C15H14N2O4·H2O	F(000) = 320
Mr = 304.30	Dx = 1.379 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 623 reflections
a = 4.891 (2) Å	θ = 2.3–24.0°
b = 12.171 (5) Å	µ = 0.11 mm−1
c = 12.371 (5) Å	T = 298 K
β = 95.724 (7)°	Block, colourless
V = 732.8 (5) Å3	0.08 × 0.07 × 0.07 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1582 independent reflections
Radiation source: fine-focus sealed tube	791 reflections with I > 2σ(I)
graphite	Rint = 0.086
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.992, Tmax = 0.993	k = −15→15
5972 measured 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3
1582 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.14 e Å−3
6 restraints	Δρmin = −0.15 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
O1	0.2886 (8)	0.7446 (3)	0.9901 (3)	0.0588 (11)
H1	0.2167	0.8048	0.9782	0.088*
O2	0.6029 (9)	0.5752 (3)	1.0195 (4)	0.0747 (13)
O3	−0.1590 (7)	1.0380 (3)	0.9939 (3)	0.0564 (10)
O4	−0.9973 (10)	1.3626 (4)	0.7359 (3)	0.0823 (15)
H4	−1.0197	1.3619	0.6694	0.123*
O5	0.3665 (9)	1.0067 (4)	0.0948 (3)	0.0717 (13)
N1	0.1007 (8)	0.9097 (3)	0.8590 (3)	0.0460 (11)
N2	−0.0723 (9)	0.9954 (4)	0.8239 (3)	0.0454 (11)
C1	0.4174 (11)	0.7745 (4)	0.8075 (5)	0.0494 (14)
C2	0.4327 (11)	0.7168 (4)	0.9064 (5)	0.0463 (14)
C3	0.6063 (12)	0.6245 (5)	0.9194 (5)	0.0579 (17)
C4	0.7584 (13)	0.5927 (5)	0.8385 (6)	0.072 (2)
H4A	0.8732	0.5319	0.8484	0.087*
C5	0.7435 (13)	0.6500 (6)	0.7418 (6)	0.073 (2)
H5	0.8484	0.6279	0.6870	0.088*
C6	0.5746 (12)	0.7393 (5)	0.7267 (5)	0.0594 (16)
H6	0.5647	0.7771	0.6611	0.071*
C7	0.2392 (11)	0.8680 (4)	0.7868 (4)	0.0485 (14)
H7	0.2243	0.8993	0.7180	0.058*
C8	−0.2022 (10)	1.0526 (4)	0.8945 (5)	0.0421 (13)
C9	−0.4033 (10)	1.1358 (4)	0.8497 (4)	0.0410 (13)
C10	−0.5053 (12)	1.2129 (5)	0.9167 (5)	0.0589 (16)
H10	−0.4389	1.2138	0.9898	0.071*
C11	−0.6996 (13)	1.2877 (5)	0.8800 (5)	0.0694 (19)
H11	−0.7650	1.3381	0.9277	0.083*
C12	−0.7996 (11)	1.2885 (5)	0.7710 (5)	0.0558 (16)
C13	−0.7035 (13)	1.2128 (5)	0.7021 (5)	0.0655 (18)
H13	−0.7698	1.2125	0.6289	0.079*
C14	−0.5079 (11)	1.1370 (5)	0.7412 (4)	0.0549 (16)
H14	−0.4450	1.0857	0.6938	0.066*
C15	0.8230 (15)	0.4970 (7)	1.0500 (8)	0.107 (3)
H15A	0.7983	0.4329	1.0048	0.160*
H15B	0.8185	0.4763	1.1246	0.160*
H15C	0.9970	0.5302	1.0405	0.160*
H2	−0.076 (13)	1.017 (5)	0.7543 (17)	0.080*
H5A	0.211 (5)	0.997 (5)	0.058 (4)	0.080*
H5B	0.490 (7)	0.992 (5)	0.054 (4)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.063 (3)	0.055 (2)	0.057 (2)	0.014 (2)	0.001 (2)	0.002 (2)
O2	0.071 (3)	0.059 (2)	0.090 (3)	0.024 (2)	−0.013 (3)	0.007 (2)
O3	0.056 (3)	0.081 (3)	0.032 (2)	0.017 (2)	0.0050 (18)	0.007 (2)
O4	0.090 (4)	0.068 (3)	0.086 (3)	0.044 (3)	−0.002 (3)	−0.005 (2)
O5	0.054 (3)	0.122 (4)	0.038 (2)	−0.011 (3)	0.003 (2)	0.005 (2)
N1	0.042 (3)	0.043 (3)	0.051 (3)	0.004 (2)	−0.004 (2)	−0.003 (2)
N2	0.048 (3)	0.050 (3)	0.039 (3)	0.009 (2)	0.007 (2)	0.002 (2)
C1	0.043 (3)	0.046 (3)	0.057 (4)	0.004 (3)	−0.004 (3)	−0.022 (3)
C2	0.041 (4)	0.046 (3)	0.050 (3)	0.001 (3)	−0.001 (3)	−0.014 (3)
C3	0.047 (4)	0.047 (3)	0.076 (5)	0.010 (3)	−0.012 (4)	−0.010 (3)
C4	0.056 (5)	0.063 (4)	0.097 (6)	0.025 (4)	−0.001 (4)	−0.027 (4)
C5	0.052 (4)	0.076 (5)	0.091 (6)	0.011 (4)	0.011 (4)	−0.035 (4)
C6	0.048 (3)	0.065 (4)	0.064 (4)	0.001 (3)	0.000 (3)	−0.017 (3)
C7	0.050 (4)	0.055 (4)	0.041 (3)	0.003 (3)	0.001 (3)	−0.009 (3)
C8	0.034 (3)	0.042 (3)	0.051 (4)	−0.001 (3)	0.003 (3)	−0.005 (3)
C9	0.041 (3)	0.040 (3)	0.042 (3)	0.003 (3)	0.002 (3)	−0.002 (2)
C10	0.065 (4)	0.068 (4)	0.043 (3)	0.009 (4)	−0.001 (3)	−0.007 (3)
C11	0.078 (5)	0.070 (4)	0.059 (5)	0.037 (4)	0.008 (4)	−0.014 (3)
C12	0.052 (4)	0.049 (3)	0.064 (4)	0.017 (3)	−0.004 (3)	−0.001 (3)
C13	0.076 (5)	0.072 (4)	0.047 (4)	0.023 (4)	−0.003 (3)	0.004 (3)
C14	0.057 (4)	0.063 (4)	0.044 (3)	0.025 (3)	0.001 (3)	−0.007 (3)
C15	0.066 (5)	0.088 (5)	0.160 (8)	0.039 (4)	−0.015 (5)	0.028 (5)

O1—C2	1.352 (6)	C4—H4A	0.93
O1—H1	0.82	C5—C6	1.367 (8)
O2—C3	1.377 (7)	C5—H5	0.93
O2—C15	1.459 (7)	C6—H6	0.93
O3—C8	1.240 (6)	C7—H7	0.93
O4—C12	1.361 (6)	C8—C9	1.480 (7)
O4—H4	0.82	C9—C10	1.378 (7)
O5—H5A	0.86 (3)	C9—C14	1.388 (6)
O5—H5B	0.84 (4)	C10—C11	1.361 (7)
N1—C7	1.279 (6)	C10—H10	0.93
N1—N2	1.385 (6)	C11—C12	1.388 (8)
N2—C8	1.328 (6)	C11—H11	0.93
N2—H2	0.90 (3)	C12—C13	1.369 (7)
C1—C6	1.388 (7)	C13—C14	1.381 (7)
C1—C2	1.407 (7)	C13—H13	0.93
C1—C7	1.440 (7)	C14—H14	0.93
C2—C3	1.407 (7)	C15—H15A	0.96
C3—C4	1.362 (8)	C15—H15B	0.96
C4—C5	1.379 (8)	C15—H15C	0.96
C2—O1—H1	109.5	C1—C7—H7	118.5
C3—O2—C15	116.3 (5)	O3—C8—N2	122.1 (5)
C12—O4—H4	109.5	O3—C8—C9	120.7 (5)
H5A—O5—H5B	108 (3)	N2—C8—C9	117.1 (5)
C7—N1—N2	115.5 (4)	C10—C9—C14	117.0 (5)
C8—N2—N1	120.4 (4)	C10—C9—C8	120.5 (5)
C8—N2—H2	121 (4)	C14—C9—C8	122.5 (5)
N1—N2—H2	118 (4)	C11—C10—C9	122.5 (5)
C6—C1—C2	119.2 (5)	C11—C10—H10	118.8
C6—C1—C7	119.0 (6)	C9—C10—H10	118.8
C2—C1—C7	121.8 (5)	C10—C11—C12	119.7 (5)
O1—C2—C3	117.8 (5)	C10—C11—H11	120.2
O1—C2—C1	123.7 (5)	C12—C11—H11	120.2
C3—C2—C1	118.5 (5)	O4—C12—C13	121.6 (5)
C4—C3—O2	126.4 (6)	O4—C12—C11	119.0 (5)
C4—C3—C2	120.7 (6)	C13—C12—C11	119.4 (5)
O2—C3—C2	112.9 (5)	C12—C13—C14	120.0 (6)
C3—C4—C5	120.5 (6)	C12—C13—H13	120.0
C3—C4—H4A	119.7	C14—C13—H13	120.0
C5—C4—H4A	119.7	C13—C14—C9	121.5 (5)
C6—C5—C4	120.0 (6)	C13—C14—H14	119.3
C6—C5—H5	120.0	C9—C14—H14	119.3
C4—C5—H5	120.0	O2—C15—H15A	109.5
C5—C6—C1	121.1 (6)	O2—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O2—C15—H15C	109.5
N1—C7—C1	122.9 (5)	H15A—C15—H15C	109.5
N1—C7—H7	118.5	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.99	2.687 (5)	142
N2—H2···O5i	0.90 (3)	1.99 (3)	2.820 (5)	154 (5)
O4—H4···O2ii	0.82	2.15	2.872 (7)	147
O5—H5A···O3iii	0.86 (3)	1.97 (3)	2.769 (6)	156 (6)
O5—H5B···O3iv	0.84 (4)	2.01 (3)	2.769 (6)	148 (5)
C7—H7···O5i	0.93	2.48	3.229 (7)	138
C14—H14···O5i	0.93	2.34	3.218 (7)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.99	2.687 (5)	142
N2—H2⋯O5i	0.90 (3)	1.99 (3)	2.820 (5)	154 (5)
O4—H4⋯O2ii	0.82	2.15	2.872 (7)	147
O5—H5A⋯O3iii	0.86 (3)	1.97 (3)	2.769 (6)	156 (6)
O5—H5B⋯O3iv	0.84 (4)	2.01 (3)	2.769 (6)	148 (5)
C7—H7⋯O5i	0.93	2.48	3.229 (7)	138
C14—H14⋯O5i	0.93	2.34	3.218 (7)	158

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