(E)-2,4-Dihydr-oxy-N'-(2-hydr-oxy-3-meth-oxy-5-nitro-benzyl-idene)benzohydrazide dihydrate.

The asymmetric unit of the title compound, C(15)H(13)N(3)O(7)·2H(2)O, consists of a hydrazone mol-ecule and two solvent water mol-ecules. The mol-ecule adopts an E configuration with respect to the C=N bond. It is relatively planar, with a dihedral angle between the two benzene rings of 2.6 (1)°. There are intra-molecular O-H⋯N and O-H⋯O hydrogen bonds in the hydrazone mol-ecule. In the crystal structure, symmetry-related mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶). For the hydrazone compounds we have reported on recently, see: Han & Zhao (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C15H13N3O7·2H2O

M = 383.32

Triclinic,

a = 7.976 (2) Å

b = 9.325 (2) Å

c = 11.547 (3) Å

α = 95.43 (2)°

β = 96.21 (2)°

γ = 102.01 (2)°

V = 829.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.971, T max = 0.975

11747 measured reflections

4268 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.143

S = 0.94

4268 reflections

263 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013000/su2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013000/su2173Isup2.hkl

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

C15H13N3O7·2H2O	Z = 2
Mr = 383.32	F(000) = 400
Triclinic, P1	Dx = 1.536 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.976 (2) Å	Cell parameters from 1898 reflections
b = 9.325 (2) Å	θ = 2.6–25.6°
c = 11.547 (3) Å	µ = 0.13 mm−1
α = 95.43 (2)°	T = 298 K
β = 96.21 (2)°	Block, colourless
γ = 102.01 (2)°	0.23 × 0.20 × 0.20 mm
V = 829.0 (4) Å3

Bruker SMART CCD area-detector diffractometer	4268 independent reflections
Radiation source: fine-focus sealed tube	1790 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 29.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.971, Tmax = 0.975	k = −12→12
11747 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3
4268 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.16 e Å−3
7 restraints	Δρmin = −0.23 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 > 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
O1	0.8600 (2)	0.84330 (17)	1.02241 (12)	0.0573 (5)
H1	0.8627	0.7814	1.0681	0.086*
O2	0.6371 (2)	0.89359 (17)	0.64100 (13)	0.0605 (5)
H2	0.5636	0.8519	0.5863	0.091*
O3	0.4100 (2)	0.68584 (17)	0.52377 (12)	0.0534 (4)
O4	0.0820 (2)	0.45944 (17)	0.28656 (12)	0.0534 (4)
H4	0.1460	0.4812	0.3491	0.080*
O5	−0.3563 (2)	−0.1600 (2)	0.34555 (17)	0.0764 (6)
O6	−0.4541 (2)	−0.1357 (2)	0.16969 (16)	0.0838 (6)
O7	−0.1224 (2)	0.36004 (18)	0.09529 (12)	0.0555 (5)
O8	0.8842 (2)	0.6698 (2)	0.19713 (15)	0.0631 (5)
O9	0.8089 (2)	0.1954 (2)	0.65935 (17)	0.0796 (6)
N1	0.3056 (2)	0.4776 (2)	0.59954 (14)	0.0453 (5)
N2	0.1982 (2)	0.4267 (2)	0.49649 (14)	0.0441 (5)
N3	−0.3569 (3)	−0.0901 (2)	0.26028 (19)	0.0568 (6)
C1	0.5283 (3)	0.6659 (2)	0.71728 (17)	0.0384 (5)
C2	0.6353 (3)	0.8076 (2)	0.72930 (18)	0.0423 (6)
C3	0.7446 (3)	0.8642 (3)	0.83179 (19)	0.0472 (6)
H3	0.8159	0.9579	0.8379	0.057*
C4	0.7485 (3)	0.7825 (3)	0.92498 (17)	0.0427 (6)
C5	0.6437 (3)	0.6424 (3)	0.91557 (18)	0.0466 (6)
H5	0.6457	0.5871	0.9784	0.056*
C6	0.5371 (3)	0.5857 (2)	0.81357 (18)	0.0455 (6)
H6	0.4684	0.4909	0.8079	0.055*
C7	0.4131 (3)	0.6119 (2)	0.60768 (17)	0.0390 (5)
C8	0.0968 (3)	0.3000 (3)	0.48753 (18)	0.0464 (6)
H8	0.0971	0.2439	0.5500	0.056*
C9	−0.0187 (3)	0.2433 (2)	0.38010 (17)	0.0417 (5)
C10	−0.0196 (3)	0.3255 (2)	0.28470 (18)	0.0419 (5)
C11	−0.1331 (3)	0.2684 (3)	0.18101 (18)	0.0443 (6)
C12	−0.2421 (3)	0.1325 (3)	0.17254 (19)	0.0481 (6)
H12	−0.3166	0.0939	0.1040	0.058*
C13	−0.2392 (3)	0.0535 (3)	0.26850 (19)	0.0471 (6)
C14	−0.1305 (3)	0.1057 (3)	0.37055 (18)	0.0475 (6)
H14	−0.1315	0.0496	0.4330	0.057*
C15	−0.2229 (3)	0.3030 (3)	−0.01694 (19)	0.0638 (7)
H15A	−0.1958	0.2112	−0.0447	0.096*
H15B	−0.1962	0.3727	−0.0719	0.096*
H15C	−0.3438	0.2869	−0.0090	0.096*
H1A	0.296 (3)	0.418 (2)	0.6542 (17)	0.080*
H8A	0.977 (2)	0.715 (2)	0.2410 (19)	0.080*
H9A	0.759 (3)	0.1042 (12)	0.657 (2)	0.080*
H9B	0.743 (3)	0.234 (2)	0.615 (2)	0.080*
H8B	0.906 (3)	0.5873 (17)	0.172 (2)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0587 (11)	0.0548 (11)	0.0468 (9)	−0.0006 (9)	−0.0125 (8)	−0.0006 (7)
O2	0.0653 (12)	0.0487 (10)	0.0564 (10)	−0.0081 (9)	−0.0119 (8)	0.0186 (8)
O3	0.0516 (10)	0.0577 (10)	0.0434 (9)	−0.0048 (8)	−0.0026 (7)	0.0162 (8)
O4	0.0512 (11)	0.0499 (10)	0.0491 (9)	−0.0038 (8)	−0.0075 (8)	0.0046 (8)
O5	0.0741 (14)	0.0609 (12)	0.0809 (13)	−0.0103 (10)	−0.0060 (10)	0.0162 (10)
O6	0.0693 (13)	0.0863 (14)	0.0677 (11)	−0.0289 (11)	−0.0142 (10)	−0.0032 (10)
O7	0.0570 (11)	0.0588 (11)	0.0426 (9)	0.0020 (8)	−0.0081 (7)	0.0056 (8)
O8	0.0602 (12)	0.0694 (13)	0.0548 (11)	0.0087 (10)	−0.0054 (8)	0.0095 (9)
O9	0.0685 (14)	0.0679 (14)	0.0864 (13)	−0.0128 (11)	−0.0181 (10)	0.0234 (11)
N1	0.0466 (12)	0.0447 (12)	0.0358 (10)	−0.0027 (9)	−0.0075 (9)	0.0036 (8)
N2	0.0404 (12)	0.0486 (12)	0.0382 (10)	0.0044 (10)	−0.0029 (8)	0.0000 (8)
N3	0.0452 (13)	0.0540 (14)	0.0608 (13)	−0.0057 (10)	0.0010 (11)	−0.0022 (11)
C1	0.0361 (13)	0.0385 (13)	0.0380 (11)	0.0045 (10)	0.0016 (9)	0.0033 (9)
C2	0.0410 (14)	0.0402 (14)	0.0445 (12)	0.0056 (11)	0.0023 (10)	0.0099 (10)
C3	0.0446 (14)	0.0381 (13)	0.0519 (13)	−0.0001 (11)	−0.0025 (11)	0.0006 (10)
C4	0.0396 (13)	0.0459 (14)	0.0384 (11)	0.0067 (11)	−0.0025 (10)	−0.0013 (10)
C5	0.0470 (15)	0.0489 (15)	0.0397 (12)	0.0013 (12)	0.0012 (10)	0.0103 (10)
C6	0.0425 (14)	0.0429 (14)	0.0454 (12)	−0.0016 (11)	0.0005 (10)	0.0076 (10)
C7	0.0354 (13)	0.0392 (14)	0.0397 (12)	0.0027 (11)	0.0042 (10)	0.0035 (10)
C8	0.0448 (15)	0.0495 (15)	0.0410 (12)	0.0057 (12)	−0.0006 (11)	0.0044 (11)
C9	0.0376 (13)	0.0427 (14)	0.0405 (12)	0.0040 (11)	0.0009 (10)	−0.0005 (10)
C10	0.0342 (13)	0.0404 (14)	0.0469 (13)	0.0040 (11)	0.0033 (10)	−0.0034 (10)
C11	0.0391 (14)	0.0488 (15)	0.0415 (12)	0.0077 (11)	−0.0009 (10)	−0.0001 (11)
C12	0.0382 (14)	0.0541 (16)	0.0456 (12)	0.0065 (12)	−0.0042 (10)	−0.0070 (11)
C13	0.0381 (14)	0.0425 (14)	0.0533 (13)	−0.0009 (11)	0.0007 (11)	−0.0044 (11)
C14	0.0444 (14)	0.0475 (15)	0.0453 (12)	0.0028 (12)	0.0007 (11)	0.0014 (11)
C15	0.0625 (18)	0.082 (2)	0.0418 (13)	0.0149 (15)	−0.0093 (12)	−0.0008 (12)

O1—C4	1.353 (2)	C1—C7	1.461 (3)
O1—H1	0.8200	C2—C3	1.381 (3)
O2—C2	1.355 (2)	C3—C4	1.377 (3)
O2—H2	0.8200	C3—H3	0.9300
O3—C7	1.242 (2)	C4—C5	1.384 (3)
O4—C10	1.337 (2)	C5—C6	1.367 (3)
O4—H4	0.8200	C5—H5	0.9300
O5—N3	1.232 (2)	C6—H6	0.9300
O6—N3	1.216 (2)	C8—C9	1.447 (3)
O7—C11	1.366 (3)	C8—H8	0.9300
O7—C15	1.439 (2)	C9—C14	1.389 (3)
O8—H8A	0.855 (19)	C9—C10	1.401 (3)
O8—H8B	0.855 (19)	C10—C11	1.407 (3)
O9—H9A	0.857 (9)	C11—C12	1.368 (3)
O9—H9B	0.85 (2)	C12—C13	1.388 (3)
N1—C7	1.352 (3)	C12—H12	0.9300
N1—N2	1.370 (2)	C13—C14	1.368 (3)
N1—H1A	0.881 (10)	C14—H14	0.9300
N2—C8	1.274 (3)	C15—H15A	0.9600
N3—C13	1.455 (3)	C15—H15B	0.9600
C1—C2	1.401 (3)	C15—H15C	0.9600
C1—C6	1.402 (3)
C4—O1—H1	109.5	O3—C7—N1	119.77 (18)
C2—O2—H2	109.5	O3—C7—C1	122.2 (2)
C10—O4—H4	109.5	N1—C7—C1	118.00 (19)
C11—O7—C15	117.01 (18)	N2—C8—C9	120.0 (2)
H8A—O8—H8B	104.2 (19)	N2—C8—H8	120.0
H9A—O9—H9B	106.7 (19)	C9—C8—H8	120.0
C7—N1—N2	117.96 (17)	C14—C9—C10	119.15 (19)
C7—N1—H1A	127.0 (17)	C14—C9—C8	120.0 (2)
N2—N1—H1A	115.1 (17)	C10—C9—C8	120.8 (2)
C8—N2—N1	118.57 (18)	O4—C10—C9	123.22 (18)
O6—N3—O5	122.4 (2)	O4—C10—C11	116.9 (2)
O6—N3—C13	118.6 (2)	C9—C10—C11	119.9 (2)
O5—N3—C13	118.98 (19)	O7—C11—C12	125.54 (19)
C2—C1—C6	117.07 (18)	O7—C11—C10	114.1 (2)
C2—C1—C7	118.85 (19)	C12—C11—C10	120.4 (2)
C6—C1—C7	124.1 (2)	C11—C12—C13	118.6 (2)
O2—C2—C3	117.5 (2)	C11—C12—H12	120.7
O2—C2—C1	121.57 (18)	C13—C12—H12	120.7
C3—C2—C1	120.9 (2)	C14—C13—C12	122.6 (2)
C4—C3—C2	120.3 (2)	C14—C13—N3	118.8 (2)
C4—C3—H3	119.9	C12—C13—N3	118.6 (2)
C2—C3—H3	119.9	C13—C14—C9	119.4 (2)
O1—C4—C3	117.5 (2)	C13—C14—H14	120.3
O1—C4—C5	122.60 (19)	C9—C14—H14	120.3
C3—C4—C5	119.93 (19)	O7—C15—H15A	109.5
C6—C5—C4	119.8 (2)	O7—C15—H15B	109.5
C6—C5—H5	120.1	H15A—C15—H15B	109.5
C4—C5—H5	120.1	O7—C15—H15C	109.5
C5—C6—C1	122.0 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.0	H15B—C15—H15C	109.5
C1—C6—H6	119.0

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8B···O4i	0.86 (2)	2.39 (2)	2.953 (2)	124 (2)
O8—H8B···O7i	0.86 (2)	2.17 (1)	3.001 (3)	163 (2)
O9—H9B···O3ii	0.85 (2)	2.19 (1)	3.032 (2)	170 (3)
O9—H9A···O2iii	0.86 (1)	1.98 (1)	2.840 (2)	176 (2)
O8—H8A···O9iv	0.86 (2)	1.93 (1)	2.786 (2)	176 (2)
N1—H1A···O5v	0.88 (1)	2.55 (2)	3.183 (3)	130 (2)
N1—H1A···O8ii	0.88 (1)	2.44 (2)	3.195 (3)	143 (2)
O4—H4···N2	0.82	1.85	2.569 (2)	146
O2—H2···O3	0.82	1.80	2.526 (2)	147
O1—H1···O8vi	0.82	1.91	2.718 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8B⋯O4i	0.86 (2)	2.39 (2)	2.953 (2)	124 (2)
O8—H8B⋯O7i	0.86 (2)	2.18 (1)	3.001 (3)	163 (2)
O9—H9B⋯O3ii	0.85 (2)	2.19 (1)	3.032 (2)	170 (3)
O9—H9A⋯O2iii	0.86 (1)	1.98 (1)	2.840 (2)	176 (2)
O8—H8A⋯O9iv	0.86 (2)	1.93 (1)	2.786 (2)	176 (2)
N1—H1A⋯O5v	0.88 (1)	2.55 (2)	3.183 (3)	130 (2)
N1—H1A⋯O8ii	0.88 (1)	2.45 (2)	3.195 (3)	143 (2)
O4—H4⋯N2	0.82	1.85	2.569 (2)	146
O2—H2⋯O3	0.82	1.80	2.526 (2)	147
O1—H1⋯O8vi	0.82	1.91	2.718 (2)	169

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