3,4,5-Trihydr-oxy-N'-(2-hydr-oxy-5-nitro-benzyl-idene)benzohydrazide mono-hydrate.

The benzohydrazide mol-ecule of the title compound, C(14)H(11)N(3)O(7)·H(2)O, is planar (r.m.s. deviation = 0.068 Å). The benzohydrazide mol-ecule and the uncoordinated water mol-ecule inter-act through O-H⋯O hydrogen bonds; these together with O-H⋯N and N-H⋯O hydrogen bonds form a three-dimensional network.

Related literature

For the the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see: Lyubchova et al. (1995 ▶). For other N′-(2-hydr­oxy-5-nitro­benzyl­idene)benzohydrazides, see: Ali et al. (2005 ▶); Lyubchova et al. (1995 ▶); Xu & Liu (2006 ▶).

Experimental

Crystal data

C14H11N3O7·H2O

M = 351.27

Triclinic,

a = 7.0097 (2) Å

b = 7.8380 (2) Å

c = 13.2953 (3) Å

α = 75.597 (1)°

β = 88.826 (2)°

γ = 81.929 (2)°

V = 700.42 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 123 K

0.15 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

6629 measured reflections

3209 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.03

3209 reflections

254 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536809010563/tk2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010563/tk2399Isup2.hkl

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

C14H11N3O7·H2O	Z = 2
Mr = 351.27	F(000) = 364
Triclinic, P1	Dx = 1.666 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0097 (2) Å	Cell parameters from 2084 reflections
b = 7.8380 (2) Å	θ = 2.7–28.3°
c = 13.2953 (3) Å	µ = 0.14 mm−1
α = 75.597 (1)°	T = 123 K
β = 88.826 (2)°	Plate, yellow
γ = 81.929 (2)°	0.15 × 0.10 × 0.02 mm
V = 700.42 (3) Å3

Bruker SMART APEX diffractometer	2373 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 27.5°, θmin = 1.6°
ω scans	h = −9→9
6629 measured reflections	k = −10→10
3209 independent reflections	l = −17→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1907P] where P = (Fo2 + 2Fc2)/3
3209 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.42 e Å−3
7 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.45792 (16)	0.65420 (15)	0.74975 (9)	0.0199 (3)
O2	−0.28084 (18)	0.28619 (17)	0.85473 (9)	0.0280 (3)
O3	−0.29787 (16)	0.35460 (16)	0.68665 (9)	0.0235 (3)
O4	0.75724 (17)	0.84619 (16)	0.53567 (9)	0.0241 (3)
O5	0.70666 (16)	1.00100 (17)	0.07165 (8)	0.0216 (3)
O6	1.05293 (16)	1.11263 (16)	0.08126 (8)	0.0195 (3)
O7	1.21628 (16)	1.10003 (17)	0.27137 (9)	0.0216 (3)
O1W	0.36719 (17)	1.26409 (18)	0.06982 (9)	0.0236 (3)
N1	−0.21856 (19)	0.35371 (18)	0.76939 (10)	0.0188 (3)
N2	0.43352 (19)	0.71596 (18)	0.55014 (10)	0.0174 (3)
N3	0.50987 (19)	0.77875 (19)	0.45456 (10)	0.0182 (3)
C1	0.2933 (2)	0.5835 (2)	0.75146 (12)	0.0170 (3)
C2	0.2175 (2)	0.5116 (2)	0.84825 (12)	0.0206 (3)
H2	0.2824	0.5136	0.9099	0.025*
C3	0.0492 (2)	0.4379 (2)	0.85482 (12)	0.0196 (3)
H3A	−0.0027	0.3890	0.9206	0.024*
C4	−0.0440 (2)	0.4361 (2)	0.76366 (12)	0.0173 (3)
C5	0.0277 (2)	0.5064 (2)	0.66704 (12)	0.0172 (3)
H5A	−0.0392	0.5042	0.6060	0.021*
C6	0.1980 (2)	0.5805 (2)	0.65926 (12)	0.0166 (3)
C7	0.2744 (2)	0.6509 (2)	0.55666 (12)	0.0179 (3)
H7A	0.2075	0.6485	0.4957	0.021*
C8	0.6794 (2)	0.8441 (2)	0.45388 (12)	0.0158 (3)
C9	0.7687 (2)	0.9115 (2)	0.35203 (11)	0.0152 (3)
C10	0.6888 (2)	0.9198 (2)	0.25525 (12)	0.0157 (3)
H10	0.5683	0.8798	0.2504	0.019*
C11	0.7882 (2)	0.9876 (2)	0.16644 (11)	0.0160 (3)
C12	0.9662 (2)	1.0473 (2)	0.17210 (12)	0.0154 (3)
C13	1.0437 (2)	1.0389 (2)	0.26925 (12)	0.0159 (3)
C14	0.9458 (2)	0.9706 (2)	0.35795 (12)	0.0164 (3)
H14	0.9998	0.9637	0.4240	0.020*
H1	0.482 (3)	0.691 (3)	0.6866 (9)	0.043 (7)*
H5	0.789 (3)	1.020 (3)	0.0256 (16)	0.060 (8)*
H6	1.151 (2)	1.158 (3)	0.0912 (18)	0.045 (7)*
H7	1.228 (3)	1.117 (3)	0.3308 (10)	0.045 (7)*
H11	0.452 (3)	1.191 (3)	0.0523 (19)	0.047 (7)*
H12	0.408 (3)	1.278 (3)	0.1260 (12)	0.055 (8)*
H3	0.453 (3)	0.769 (2)	0.3981 (10)	0.022 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0212 (6)	0.0250 (6)	0.0149 (6)	−0.0097 (5)	−0.0003 (5)	−0.0041 (5)
O2	0.0256 (6)	0.0346 (7)	0.0205 (6)	−0.0096 (5)	0.0064 (5)	0.0017 (5)
O3	0.0212 (6)	0.0307 (7)	0.0219 (6)	−0.0077 (5)	0.0003 (5)	−0.0102 (5)
O4	0.0268 (6)	0.0361 (7)	0.0116 (5)	−0.0148 (5)	0.0000 (5)	−0.0040 (5)
O5	0.0172 (6)	0.0399 (7)	0.0094 (5)	−0.0089 (5)	0.0009 (4)	−0.0067 (5)
O6	0.0184 (6)	0.0301 (7)	0.0117 (5)	−0.0098 (5)	0.0032 (4)	−0.0053 (5)
O7	0.0186 (6)	0.0368 (7)	0.0134 (6)	−0.0132 (5)	0.0016 (5)	−0.0087 (5)
O1W	0.0215 (6)	0.0334 (7)	0.0169 (6)	−0.0077 (5)	0.0004 (5)	−0.0060 (5)
N1	0.0174 (7)	0.0206 (7)	0.0181 (7)	−0.0030 (5)	0.0028 (5)	−0.0041 (6)
N2	0.0194 (7)	0.0200 (7)	0.0123 (6)	−0.0046 (5)	0.0033 (5)	−0.0023 (5)
N3	0.0186 (7)	0.0271 (8)	0.0095 (6)	−0.0077 (6)	0.0015 (5)	−0.0034 (5)
C1	0.0184 (7)	0.0166 (8)	0.0163 (8)	−0.0028 (6)	0.0003 (6)	−0.0045 (6)
C2	0.0251 (8)	0.0233 (9)	0.0133 (8)	−0.0045 (7)	−0.0013 (6)	−0.0038 (6)
C3	0.0241 (8)	0.0213 (8)	0.0124 (7)	−0.0042 (7)	0.0032 (6)	−0.0016 (6)
C4	0.0176 (7)	0.0166 (8)	0.0173 (8)	−0.0031 (6)	0.0027 (6)	−0.0036 (6)
C5	0.0185 (7)	0.0192 (8)	0.0135 (7)	−0.0019 (6)	−0.0007 (6)	−0.0036 (6)
C6	0.0181 (8)	0.0178 (8)	0.0134 (7)	−0.0024 (6)	0.0009 (6)	−0.0032 (6)
C7	0.0202 (8)	0.0215 (8)	0.0124 (7)	−0.0043 (6)	−0.0001 (6)	−0.0044 (6)
C8	0.0177 (7)	0.0169 (8)	0.0127 (7)	−0.0029 (6)	0.0005 (6)	−0.0034 (6)
C9	0.0174 (7)	0.0170 (8)	0.0110 (7)	−0.0024 (6)	0.0022 (6)	−0.0034 (6)
C10	0.0131 (7)	0.0202 (8)	0.0145 (7)	−0.0031 (6)	0.0008 (6)	−0.0051 (6)
C11	0.0166 (7)	0.0207 (8)	0.0112 (7)	−0.0014 (6)	−0.0002 (6)	−0.0056 (6)
C12	0.0154 (7)	0.0183 (8)	0.0121 (7)	−0.0024 (6)	0.0028 (6)	−0.0034 (6)
C13	0.0143 (7)	0.0196 (8)	0.0147 (7)	−0.0045 (6)	0.0004 (6)	−0.0048 (6)
C14	0.0185 (7)	0.0198 (8)	0.0116 (7)	−0.0039 (6)	−0.0018 (6)	−0.0043 (6)

O1—C1	1.3456 (19)	C1—C6	1.415 (2)
O1—H1	0.840 (10)	C2—C3	1.377 (2)
O2—N1	1.2263 (17)	C2—H2	0.9500
O3—N1	1.2408 (17)	C3—C4	1.393 (2)
O4—C8	1.2313 (18)	C3—H3A	0.9500
O5—C11	1.3684 (18)	C4—C5	1.380 (2)
O5—H5	0.835 (10)	C5—C6	1.391 (2)
O6—C12	1.3567 (18)	C5—H5A	0.9500
O6—H6	0.844 (10)	C6—C7	1.460 (2)
O7—C13	1.3654 (18)	C7—H7A	0.9500
O7—H7	0.842 (10)	C8—C9	1.486 (2)
O1W—H11	0.837 (10)	C9—C14	1.394 (2)
O1W—H12	0.843 (10)	C9—C10	1.397 (2)
N1—C4	1.454 (2)	C10—C11	1.386 (2)
N2—C7	1.283 (2)	C10—H10	0.9500
N2—N3	1.3705 (18)	C11—C12	1.402 (2)
N3—C8	1.358 (2)	C12—C13	1.394 (2)
N3—H3	0.882 (9)	C13—C14	1.380 (2)
C1—C2	1.397 (2)	C14—H14	0.9500
C1—O1—H1	105.4 (16)	C5—C6—C1	118.80 (14)
C11—O5—H5	109.5 (19)	C5—C6—C7	119.23 (14)
C12—O6—H6	111.2 (16)	C1—C6—C7	121.96 (14)
C13—O7—H7	106.8 (16)	N2—C7—C6	118.88 (14)
H11—O1W—H12	105 (2)	N2—C7—H7A	120.6
O2—N1—O3	122.81 (13)	C6—C7—H7A	120.6
O2—N1—C4	119.27 (13)	O4—C8—N3	120.72 (14)
O3—N1—C4	117.92 (13)	O4—C8—C9	121.07 (14)
C7—N2—N3	119.72 (13)	N3—C8—C9	118.21 (13)
C8—N3—N2	116.36 (13)	C14—C9—C10	119.94 (13)
C8—N3—H3	123.5 (13)	C14—C9—C8	114.80 (13)
N2—N3—H3	120.0 (13)	C10—C9—C8	125.25 (14)
O1—C1—C2	117.78 (14)	C11—C10—C9	118.85 (14)
O1—C1—C6	122.00 (14)	C11—C10—H10	120.6
C2—C1—C6	120.21 (14)	C9—C10—H10	120.6
C3—C2—C1	120.36 (15)	O5—C11—C10	118.74 (13)
C3—C2—H2	119.8	O5—C11—C12	119.86 (13)
C1—C2—H2	119.8	C10—C11—C12	121.36 (14)
C2—C3—C4	119.02 (14)	O6—C12—C13	123.45 (13)
C2—C3—H3A	120.5	O6—C12—C11	117.42 (13)
C4—C3—H3A	120.5	C13—C12—C11	119.13 (13)
C5—C4—C3	121.78 (14)	O7—C13—C14	122.96 (14)
C5—C4—N1	118.55 (14)	O7—C13—C12	117.31 (13)
C3—C4—N1	119.64 (14)	C14—C13—C12	119.73 (14)
C4—C5—C6	119.81 (14)	C13—C14—C9	120.99 (14)
C4—C5—H5A	120.1	C13—C14—H14	119.5
C6—C5—H5A	120.1	C9—C14—H14	119.5
C7—N2—N3—C8	−179.41 (15)	N2—N3—C8—C9	179.23 (13)
O1—C1—C2—C3	179.85 (15)	O4—C8—C9—C14	1.7 (2)
C6—C1—C2—C3	−0.3 (2)	N3—C8—C9—C14	−177.85 (14)
C1—C2—C3—C4	0.0 (3)	O4—C8—C9—C10	−177.86 (16)
C2—C3—C4—C5	−0.1 (3)	N3—C8—C9—C10	2.6 (2)
C2—C3—C4—N1	178.09 (15)	C14—C9—C10—C11	−0.1 (2)
O2—N1—C4—C5	177.95 (14)	C8—C9—C10—C11	179.45 (15)
O3—N1—C4—C5	−1.8 (2)	C9—C10—C11—O5	−177.89 (14)
O2—N1—C4—C3	−0.3 (2)	C9—C10—C11—C12	0.0 (2)
O3—N1—C4—C3	179.95 (14)	O5—C11—C12—O6	−1.7 (2)
C3—C4—C5—C6	0.4 (2)	C10—C11—C12—O6	−179.59 (14)
N1—C4—C5—C6	−177.79 (14)	O5—C11—C12—C13	177.58 (14)
C4—C5—C6—C1	−0.7 (2)	C10—C11—C12—C13	−0.3 (2)
C4—C5—C6—C7	178.65 (14)	O6—C12—C13—O7	−0.1 (2)
O1—C1—C6—C5	−179.54 (14)	C11—C12—C13—O7	−179.35 (14)
C2—C1—C6—C5	0.6 (2)	O6—C12—C13—C14	179.91 (15)
O1—C1—C6—C7	1.2 (2)	C11—C12—C13—C14	0.7 (2)
C2—C1—C6—C7	−178.71 (15)	O7—C13—C14—C9	179.26 (15)
N3—N2—C7—C6	178.44 (14)	C12—C13—C14—C9	−0.8 (2)
C5—C6—C7—N2	−178.70 (15)	C10—C9—C14—C13	0.5 (2)
C1—C6—C7—N2	0.6 (2)	C8—C9—C14—C13	−179.11 (14)
N2—N3—C8—O4	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84 (1)	1.81 (1)	2.581 (2)	152 (2)
O5—H5···O6i	0.84 (1)	2.16 (2)	2.847 (2)	139 (2)
O6—H6···O1wii	0.84 (1)	1.81 (1)	2.630 (2)	162 (2)
O7—H7···O4iii	0.84 (1)	1.87 (1)	2.715 (2)	177 (2)
O1w—H11···O5	0.84 (1)	2.13 (1)	2.918 (2)	156 (2)
O1w—H12···O1iv	0.84 (1)	2.13 (1)	2.962 (2)	169 (2)
N3—H3···O3v	0.88 (1)	2.07 (1)	2.890 (2)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.84 (1)	1.81 (1)	2.581 (2)	152 (2)
O5—H5⋯O6i	0.84 (1)	2.16 (2)	2.847 (2)	139 (2)
O6—H6⋯O1wii	0.84 (1)	1.81 (1)	2.630 (2)	162 (2)
O7—H7⋯O4iii	0.84 (1)	1.87 (1)	2.715 (2)	177 (2)
O1w—H11⋯O5	0.84 (1)	2.13 (1)	2.918 (2)	156 (2)
O1w—H12⋯O1iv	0.84 (1)	2.13 (1)	2.962 (2)	169 (2)
N3—H3⋯O3v	0.88 (1)	2.07 (1)	2.890 (2)	155 (2)

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