2-{(E)-1-[2-(2-Nitro-phen-yl)hydrazin-1-yl-idene]eth-yl}benzene-1,3-diol mono-hydrate.

The hydrazone mol-ecule in title monohydrate, C(14)H(13)N(3)O(4)·H(2)O, is almost coplanar, the dihedral angle between the terminal benzene rings being 3.22 (15)°; the nitro group is coplanar with the benzene ring to which it is bonded [O-N-C-C = -2.8 (4)°]. The hy-droxy group forms an intra-molecular hydrogen bond with the imine N atom, and the conformation about the imine bond [1.305 (3) Å] is E. In the crystal, supra-molecular layers in the (203) plane are connected into a double layer via water-nitro O-H⋯O hydrogen bonds, along with π-π inter-actions [ring centroid-centroid distance = 3.7859 (19) Å].

Related literature

For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Baddeley et al. (2009 ▶).

Experimental

Crystal data

C14H13N3O4·H2O

M = 305.29

Monoclinic,

a = 7.6448 (6) Å

b = 21.405 (2) Å

c = 8.5755 (7) Å

β = 106.976 (5)°

V = 1342.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 120 K

0.45 × 0.25 × 0.02 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.776, T max = 0.998

16295 measured reflections

3068 independent reflections

1492 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.194

S = 1.01

3068 reflections

221 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006241/pv2513sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006241/pv2513Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006241/pv2513Isup3.cml

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

C14H13N3O4·H2O	F(000) = 640
Mr = 305.29	Dx = 1.511 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19763 reflections
a = 7.6448 (6) Å	θ = 2.9–27.5°
b = 21.405 (2) Å	µ = 0.12 mm−1
c = 8.5755 (7) Å	T = 120 K
β = 106.976 (5)°	Plate, brown
V = 1342.1 (2) Å3	0.45 × 0.25 × 0.02 mm
Z = 4

Bruker-Nonius Roper CCD camera on κ-goniostat diffractometer	3068 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1492 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.110
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ & ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −27→27
Tmin = 0.776, Tmax = 0.998	l = −11→11
16295 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0914P)2] where P = (Fo2 + 2Fc2)/3
3068 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.37 e Å−3
6 restraints	Δρmin = −0.30 e Å−3

Experimental. IR (KBr, cm-1): ν 3600–2000 (v br), 3543, 3427, 3340, 1622, 1585, 1525. Anal. Found: C, 54.86; H, 5.03; N, 14.07. Calculated for C14H15N3O5: C, 55.08; H, 4.95; N, 13.76%.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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	0.6688 (3)	−0.09682 (11)	0.3317 (3)	0.0350 (6)
H1O	0.659 (5)	−0.0590 (7)	0.356 (5)	0.062 (13)*
O2	1.1256 (3)	−0.07064 (10)	0.8502 (3)	0.0340 (6)
H2O	1.189 (4)	−0.0952 (12)	0.921 (3)	0.034 (10)*
O3	0.6421 (3)	0.18198 (10)	0.5589 (3)	0.0353 (6)
O4	0.4717 (3)	0.25227 (10)	0.4047 (3)	0.0411 (7)
N1	0.7166 (3)	0.00802 (11)	0.4628 (3)	0.0247 (6)
N2	0.6577 (3)	0.06852 (12)	0.4550 (3)	0.0272 (6)
H2N	0.702 (4)	0.0956 (11)	0.534 (3)	0.033 (9)*
N3	0.5292 (3)	0.19801 (13)	0.4289 (3)	0.0315 (7)
C1	0.8928 (4)	−0.07782 (14)	0.5935 (4)	0.0238 (7)
C2	0.8060 (4)	−0.11805 (15)	0.4603 (4)	0.0288 (8)
C3	0.8560 (4)	−0.17972 (15)	0.4541 (4)	0.0337 (8)
H3	0.7969	−0.2048	0.3625	0.040*
C4	0.9922 (4)	−0.20473 (15)	0.5816 (4)	0.0322 (8)
H4	1.0262	−0.2473	0.5779	0.039*
C5	1.0795 (4)	−0.16848 (14)	0.7142 (4)	0.0285 (8)
H5	1.1721	−0.1863	0.8019	0.034*
C6	1.0333 (4)	−0.10608 (14)	0.7204 (4)	0.0256 (7)
C7	0.8350 (4)	−0.01181 (14)	0.5962 (3)	0.0228 (7)
C8	0.9016 (4)	0.03103 (14)	0.7387 (4)	0.0314 (8)
H8A	0.9969	0.0584	0.7212	0.043 (10)*
H8B	0.9522	0.0063	0.8380	0.043 (9)*
H8C	0.7996	0.0564	0.7506	0.067 (12)*
C9	0.5300 (4)	0.09005 (14)	0.3180 (3)	0.0246 (7)
C10	0.4639 (4)	0.15195 (14)	0.3020 (3)	0.0252 (7)
C11	0.3303 (4)	0.17195 (15)	0.1615 (4)	0.0285 (8)
H11	0.2881	0.2139	0.1538	0.034*
C12	0.2596 (4)	0.13127 (15)	0.0345 (4)	0.0307 (8)
H12	0.1681	0.1446	−0.0605	0.037*
C13	0.3240 (4)	0.07063 (15)	0.0477 (4)	0.0313 (8)
H13	0.2763	0.0424	−0.0399	0.038*
C14	0.4557 (4)	0.05009 (15)	0.1848 (4)	0.0268 (7)
H14	0.4973	0.0081	0.1895	0.032*
O1W	0.6617 (3)	0.14329 (12)	0.9035 (3)	0.0397 (6)
H1W	0.560 (3)	0.1348 (17)	0.836 (3)	0.060*
H2W	0.714 (4)	0.1722 (13)	0.867 (4)	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0414 (14)	0.0315 (15)	0.0260 (13)	0.0007 (11)	0.0000 (10)	−0.0022 (11)
O2	0.0382 (14)	0.0312 (14)	0.0253 (13)	0.0020 (10)	−0.0021 (11)	−0.0004 (10)
O3	0.0420 (14)	0.0314 (14)	0.0275 (13)	−0.0038 (10)	0.0022 (11)	0.0001 (10)
O4	0.0468 (15)	0.0224 (14)	0.0475 (15)	0.0026 (11)	0.0032 (11)	−0.0025 (11)
N1	0.0256 (14)	0.0238 (15)	0.0257 (14)	−0.0001 (11)	0.0088 (11)	0.0013 (11)
N2	0.0336 (16)	0.0224 (16)	0.0228 (15)	−0.0007 (12)	0.0037 (12)	−0.0022 (12)
N3	0.0348 (17)	0.0299 (17)	0.0292 (16)	−0.0038 (13)	0.0083 (13)	0.0002 (13)
C1	0.0198 (16)	0.0295 (18)	0.0244 (16)	−0.0015 (13)	0.0099 (13)	0.0024 (13)
C2	0.0312 (18)	0.030 (2)	0.0240 (17)	−0.0031 (14)	0.0069 (14)	0.0007 (14)
C3	0.043 (2)	0.029 (2)	0.0288 (18)	−0.0028 (15)	0.0103 (16)	−0.0062 (15)
C4	0.0382 (19)	0.0231 (19)	0.038 (2)	−0.0017 (15)	0.0150 (16)	−0.0007 (15)
C5	0.0317 (18)	0.0274 (19)	0.0275 (18)	0.0004 (14)	0.0103 (14)	0.0044 (14)
C6	0.0298 (18)	0.0255 (19)	0.0225 (16)	−0.0049 (14)	0.0092 (14)	−0.0029 (13)
C7	0.0193 (16)	0.0277 (19)	0.0215 (16)	−0.0010 (13)	0.0062 (13)	0.0021 (13)
C8	0.036 (2)	0.0264 (19)	0.0254 (18)	0.0007 (15)	−0.0015 (15)	−0.0014 (14)
C9	0.0279 (18)	0.0288 (19)	0.0168 (16)	−0.0020 (14)	0.0059 (13)	0.0003 (13)
C10	0.0294 (17)	0.0246 (19)	0.0226 (17)	−0.0046 (14)	0.0092 (14)	−0.0027 (13)
C11	0.0307 (18)	0.0254 (18)	0.0315 (18)	−0.0007 (14)	0.0124 (14)	0.0042 (14)
C12	0.0272 (18)	0.036 (2)	0.0265 (18)	0.0030 (15)	0.0040 (14)	0.0035 (15)
C13	0.0338 (19)	0.035 (2)	0.0239 (18)	0.0005 (15)	0.0061 (14)	−0.0035 (14)
C14	0.0263 (17)	0.0276 (18)	0.0253 (17)	0.0010 (14)	0.0059 (13)	−0.0004 (14)
O1W	0.0406 (15)	0.0385 (16)	0.0343 (14)	−0.0005 (12)	0.0019 (11)	0.0024 (12)

O1—C2	1.359 (4)	C5—C6	1.387 (4)
O1—H1O	0.844 (10)	C5—H5	0.9500
O2—C6	1.361 (3)	C7—C8	1.494 (4)
O2—H2O	0.844 (10)	C8—H8A	0.9800
O3—N3	1.242 (3)	C8—H8B	0.9800
O4—N3	1.238 (3)	C8—H8C	0.9800
N1—C7	1.305 (3)	C9—C14	1.407 (4)
N1—N2	1.366 (3)	C9—C10	1.411 (4)
N2—C9	1.370 (4)	C10—C11	1.399 (4)
N2—H2N	0.880 (10)	C11—C12	1.376 (4)
N3—C10	1.445 (4)	C11—H11	0.9500
C1—C6	1.422 (4)	C12—C13	1.381 (4)
C1—C2	1.430 (4)	C12—H12	0.9500
C1—C7	1.483 (4)	C13—C14	1.378 (4)
C2—C3	1.380 (4)	C13—H13	0.9500
C3—C4	1.379 (4)	C14—H14	0.9500
C3—H3	0.9500	O1W—H1W	0.841 (10)
C4—C5	1.377 (4)	O1W—H2W	0.845 (10)
C4—H4	0.9500
C2—O1—H1O	103 (3)	N1—C7—C8	120.1 (3)
C6—O2—H2O	107 (2)	C1—C7—C8	124.5 (2)
C7—N1—N2	119.1 (3)	C7—C8—H8A	109.5
N1—N2—C9	120.2 (2)	C7—C8—H8B	109.5
N1—N2—H2N	123 (2)	H8A—C8—H8B	109.5
C9—N2—H2N	117 (2)	C7—C8—H8C	109.5
O4—N3—O3	122.0 (3)	H8A—C8—H8C	109.5
O4—N3—C10	119.1 (3)	H8B—C8—H8C	109.5
O3—N3—C10	119.0 (3)	N2—C9—C14	120.6 (3)
C6—C1—C2	115.2 (3)	N2—C9—C10	123.0 (3)
C6—C1—C7	123.8 (3)	C14—C9—C10	116.3 (3)
C2—C1—C7	121.0 (3)	C11—C10—C9	121.5 (3)
O1—C2—C3	116.5 (3)	C11—C10—N3	116.4 (3)
O1—C2—C1	121.0 (3)	C9—C10—N3	122.2 (3)
C3—C2—C1	122.5 (3)	C12—C11—C10	120.5 (3)
C4—C3—C2	119.7 (3)	C12—C11—H11	119.8
C4—C3—H3	120.2	C10—C11—H11	119.8
C2—C3—H3	120.2	C11—C12—C13	118.8 (3)
C3—C4—C5	120.5 (3)	C11—C12—H12	120.6
C3—C4—H4	119.8	C13—C12—H12	120.6
C5—C4—H4	119.8	C14—C13—C12	121.6 (3)
C4—C5—C6	120.5 (3)	C14—C13—H13	119.2
C4—C5—H5	119.8	C12—C13—H13	119.2
C6—C5—H5	119.8	C13—C14—C9	121.3 (3)
O2—C6—C5	119.4 (3)	C13—C14—H14	119.3
O2—C6—C1	118.9 (3)	C9—C14—H14	119.3
C5—C6—C1	121.6 (3)	H1W—O1W—H2W	111 (3)
N1—C7—C1	115.5 (3)
C7—N1—N2—C9	−178.3 (3)	C6—C1—C7—C8	−7.0 (5)
C6—C1—C2—O1	179.6 (3)	C2—C1—C7—C8	172.1 (3)
C7—C1—C2—O1	0.5 (4)	N1—N2—C9—C14	0.9 (4)
C6—C1—C2—C3	−0.7 (4)	N1—N2—C9—C10	−179.8 (3)
C7—C1—C2—C3	−179.8 (3)	N2—C9—C10—C11	−178.6 (3)
O1—C2—C3—C4	−179.0 (3)	C14—C9—C10—C11	0.7 (4)
C1—C2—C3—C4	1.3 (5)	N2—C9—C10—N3	1.2 (5)
C2—C3—C4—C5	−0.5 (5)	C14—C9—C10—N3	−179.5 (3)
C3—C4—C5—C6	−0.8 (5)	O4—N3—C10—C11	−3.3 (4)
C4—C5—C6—O2	−177.8 (3)	O3—N3—C10—C11	177.0 (3)
C4—C5—C6—C1	1.5 (5)	O4—N3—C10—C9	176.9 (3)
C2—C1—C6—O2	178.6 (3)	O3—N3—C10—C9	−2.8 (4)
C7—C1—C6—O2	−2.3 (4)	C9—C10—C11—C12	0.0 (4)
C2—C1—C6—C5	−0.7 (4)	N3—C10—C11—C12	−179.8 (3)
C7—C1—C6—C5	178.4 (3)	C10—C11—C12—C13	−0.6 (5)
N2—N1—C7—C1	−179.4 (2)	C11—C12—C13—C14	0.4 (5)
N2—N1—C7—C8	1.2 (4)	C12—C13—C14—C9	0.3 (5)
C6—C1—C7—N1	173.6 (3)	N2—C9—C14—C13	178.5 (3)
C2—C1—C7—N1	−7.4 (4)	C10—C9—C14—C13	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.85 (2)	1.69 (2)	2.489 (3)	157 (4)
N2—H2N···O3	0.88 (2)	1.93 (2)	2.602 (3)	132 (2)
O2—H2O···O1Wi	0.84 (3)	1.90 (3)	2.742 (3)	174 (2)
O1W—H1W···O1ii	0.84 (2)	2.08 (3)	2.910 (3)	169 (3)
O1W—H2W···O4iii	0.85 (3)	2.50 (3)	3.256 (3)	150 (3)
C11—H11···O3iv	0.95	2.52	3.447 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.85 (2)	1.69 (2)	2.489 (3)	157 (4)
N2—H2N⋯O3	0.88 (2)	1.93 (2)	2.602 (3)	132 (2)
O2—H2O⋯O1wi	0.84 (3)	1.90 (3)	2.742 (3)	174 (2)
O1W—H1W⋯O1ii	0.84 (2)	2.08 (3)	2.910 (3)	169 (3)
O1W—H2W⋯O4iii	0.85 (3)	2.50 (3)	3.256 (3)	150 (3)
C11—H11⋯O3iv	0.95	2.52	3.447 (4)	166

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