2-{(E)-1-[2-(4-Nitro-phen-yl)hydrazin-1-yl-idene]eth-yl}benzene-1,3-diol.

The title compound, C(14)H(13)N(3)O(4), is close to planar, the dihedral angle between the terminal benzene rings being 5.80 (16)°; the nitro group is coplanar with the benzene ring to which it is bonded [O-N-C-C torsion angle = -177.3 (3)°]. The hy-droxy group forms an intra-molecular hydrogen bond with the imine N atom, and the conformation about the imine bond is E. In the crystal, layers in the (101) plane with an undulating topology are formed by O-H⋯O and N-H⋯O hydrogen bonds along with C-H⋯O inter-actions. Centrosymmetrically related layers are connected via π-π inter-actions [ring centroid-centroid distance = 3.5739 (19) Å] into double layers.

Related literature

For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Wardell et al. (2007 ▶); Baddeley, de Souza França et al. (2009 ▶); Baddeley, Howie et al. (2009 ▶); de Souza et al. (2010 ▶); Howie, da Silva Lima et al. (2010 ▶); Howie, de Souza et al. (2010 ▶); Nogueira et al. (2011 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C14H13N3O4

M = 287.27

Monoclinic,

a = 7.9714 (3) Å

b = 13.5021 (7) Å

c = 12.1081 (5) Å

β = 90.186 (3)°

V = 1303.20 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.875, T max = 0.991

12144 measured reflections

2984 independent reflections

1987 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.184

S = 1.10

2984 reflections

200 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 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/S1600536812005399/bt5815sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005399/bt5815Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005399/bt5815Isup3.cml

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

C14H13N3O4	F(000) = 600
Mr = 287.27	Dx = 1.464 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8454 reflections
a = 7.9714 (3) Å	θ = 2.9–27.5°
b = 13.5021 (7) Å	µ = 0.11 mm−1
c = 12.1081 (5) Å	T = 120 K
β = 90.186 (3)°	Block, orange
V = 1303.20 (10) Å3	0.10 × 0.10 × 0.08 mm
Z = 4

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2984 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1987 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
Tmin = 0.875, Tmax = 0.991	l = −15→15
12144 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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0335P)2 + 2.8837P] where P = (Fo2 + 2Fc2)/3
2984 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

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	0.1354 (3)	0.71070 (18)	0.50069 (19)	0.0328 (6)
H1O	0.150 (5)	0.6502 (11)	0.514 (3)	0.049*
O2	−0.1888 (3)	0.68611 (19)	0.83331 (18)	0.0340 (6)
H2O	−0.241 (5)	0.721 (3)	0.880 (3)	0.051*
O3	0.6044 (3)	0.19192 (18)	0.30034 (19)	0.0360 (6)
O4	0.6016 (3)	0.32888 (19)	0.20547 (18)	0.0360 (6)
N1	0.1233 (3)	0.5509 (2)	0.6101 (2)	0.0257 (6)
N2	0.1909 (4)	0.4583 (2)	0.6225 (2)	0.0276 (6)
H2N	0.167 (4)	0.423 (2)	0.6812 (19)	0.033*
N3	0.5648 (3)	0.2804 (2)	0.2882 (2)	0.0273 (6)
C1	−0.0115 (4)	0.6950 (2)	0.6750 (2)	0.0252 (7)
C2	0.0357 (4)	0.7506 (3)	0.5807 (3)	0.0273 (7)
C3	−0.0168 (5)	0.8477 (3)	0.5650 (3)	0.0334 (8)
H3	0.0214	0.8845	0.5031	0.040*
C4	−0.1245 (5)	0.8902 (3)	0.6400 (3)	0.0357 (8)
H4	−0.1608	0.9566	0.6295	0.043*
C5	−0.1806 (4)	0.8372 (3)	0.7305 (3)	0.0337 (8)
H5	−0.2563	0.8670	0.7810	0.040*
C6	−0.1266 (4)	0.7405 (3)	0.7478 (3)	0.0279 (7)
C7	0.0573 (4)	0.5945 (2)	0.6957 (2)	0.0251 (7)
C8	0.0634 (5)	0.5472 (3)	0.8079 (3)	0.0326 (8)
H8A	−0.0272	0.4984	0.8141	0.049*
H8B	0.0495	0.5981	0.8648	0.049*
H8C	0.1718	0.5141	0.8181	0.049*
C9	0.2810 (4)	0.4167 (2)	0.5372 (2)	0.0235 (7)
C10	0.3233 (4)	0.4699 (2)	0.4419 (2)	0.0239 (7)
H10	0.2865	0.5363	0.4329	0.029*
C11	0.4188 (4)	0.4251 (2)	0.3614 (2)	0.0248 (7)
H11	0.4489	0.4608	0.2968	0.030*
C12	0.4704 (4)	0.3281 (2)	0.3751 (2)	0.0227 (7)
C13	0.4297 (4)	0.2742 (3)	0.4688 (3)	0.0273 (7)
H13	0.4659	0.2076	0.4768	0.033*
C14	0.3360 (4)	0.3191 (2)	0.5497 (2)	0.0260 (7)
H14	0.3084	0.2834	0.6148	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (14)	0.0285 (13)	0.0327 (13)	0.0032 (11)	0.0141 (10)	0.0013 (11)
O2	0.0387 (14)	0.0374 (15)	0.0258 (12)	0.0003 (12)	0.0129 (10)	−0.0060 (11)
O3	0.0443 (15)	0.0266 (13)	0.0371 (13)	0.0044 (12)	0.0125 (11)	−0.0032 (11)
O4	0.0424 (15)	0.0411 (15)	0.0246 (12)	0.0021 (12)	0.0121 (10)	0.0022 (11)
N1	0.0265 (15)	0.0245 (15)	0.0261 (13)	−0.0025 (12)	0.0036 (11)	−0.0012 (11)
N2	0.0351 (16)	0.0240 (15)	0.0238 (13)	0.0011 (12)	0.0106 (11)	0.0000 (11)
N3	0.0250 (14)	0.0327 (16)	0.0243 (13)	0.0006 (12)	0.0029 (11)	−0.0028 (12)
C1	0.0226 (16)	0.0266 (17)	0.0263 (15)	−0.0051 (13)	0.0035 (12)	−0.0053 (13)
C2	0.0293 (18)	0.0277 (18)	0.0251 (15)	−0.0045 (15)	0.0051 (13)	−0.0038 (13)
C3	0.043 (2)	0.0268 (19)	0.0308 (18)	−0.0026 (16)	0.0061 (15)	0.0012 (14)
C4	0.042 (2)	0.0274 (19)	0.0380 (19)	0.0026 (16)	−0.0010 (16)	−0.0075 (15)
C5	0.034 (2)	0.038 (2)	0.0289 (17)	0.0035 (16)	0.0042 (14)	−0.0112 (15)
C6	0.0280 (18)	0.0318 (19)	0.0239 (15)	−0.0044 (15)	0.0020 (13)	−0.0081 (14)
C7	0.0245 (17)	0.0243 (17)	0.0264 (16)	−0.0064 (13)	0.0061 (13)	−0.0061 (13)
C8	0.045 (2)	0.0270 (18)	0.0264 (17)	−0.0003 (16)	0.0109 (15)	−0.0036 (14)
C9	0.0235 (16)	0.0247 (17)	0.0224 (14)	−0.0024 (13)	0.0041 (12)	−0.0033 (13)
C10	0.0305 (18)	0.0170 (16)	0.0244 (15)	0.0013 (13)	0.0037 (13)	0.0008 (12)
C11	0.0268 (17)	0.0288 (18)	0.0188 (14)	−0.0039 (14)	0.0034 (12)	0.0004 (13)
C12	0.0221 (16)	0.0246 (16)	0.0215 (14)	−0.0011 (13)	0.0033 (12)	−0.0042 (12)
C13	0.0300 (18)	0.0239 (17)	0.0281 (16)	0.0030 (14)	0.0021 (13)	0.0009 (13)
C14	0.0308 (18)	0.0259 (17)	0.0213 (15)	−0.0026 (14)	0.0078 (13)	0.0033 (13)

O1—C2	1.366 (4)	C4—H4	0.9500
O1—H1O	0.841 (10)	C5—C6	1.390 (5)
O2—C6	1.364 (4)	C5—H5	0.9500
O2—H2O	0.844 (10)	C7—C8	1.503 (4)
O3—N3	1.244 (4)	C8—H8A	0.9800
O4—N3	1.233 (3)	C8—H8B	0.9800
N1—C7	1.304 (4)	C8—H8C	0.9800
N1—N2	1.369 (4)	C9—C14	1.398 (4)
N2—C9	1.380 (4)	C9—C10	1.401 (4)
N2—H2N	0.880 (10)	C10—C11	1.378 (4)
N3—C12	1.447 (4)	C10—H10	0.9500
C1—C6	1.414 (4)	C11—C12	1.383 (4)
C1—C2	1.418 (4)	C11—H11	0.9500
C1—C7	1.484 (5)	C12—C13	1.387 (4)
C2—C3	1.390 (5)	C13—C14	1.375 (4)
C3—C4	1.377 (5)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.385 (5)
C2—O1—H1O	109 (3)	N1—C7—C1	115.4 (3)
C6—O2—H2O	113 (3)	N1—C7—C8	121.0 (3)
C7—N1—N2	119.0 (3)	C1—C7—C8	123.5 (3)
N1—N2—C9	119.7 (3)	C7—C8—H8A	109.5
N1—N2—H2N	120 (2)	C7—C8—H8B	109.5
C9—N2—H2N	120 (2)	H8A—C8—H8B	109.5
O4—N3—O3	123.0 (3)	C7—C8—H8C	109.5
O4—N3—C12	118.7 (3)	H8A—C8—H8C	109.5
O3—N3—C12	118.3 (3)	H8B—C8—H8C	109.5
C6—C1—C2	116.5 (3)	N2—C9—C14	117.8 (3)
C6—C1—C7	122.2 (3)	N2—C9—C10	122.4 (3)
C2—C1—C7	121.4 (3)	C14—C9—C10	119.7 (3)
O1—C2—C3	116.8 (3)	C11—C10—C9	119.6 (3)
O1—C2—C1	121.3 (3)	C11—C10—H10	120.2
C3—C2—C1	122.0 (3)	C9—C10—H10	120.2
C4—C3—C2	119.4 (3)	C10—C11—C12	119.7 (3)
C4—C3—H3	120.3	C10—C11—H11	120.2
C2—C3—H3	120.3	C12—C11—H11	120.2
C3—C4—C5	120.7 (4)	C11—C12—C13	121.6 (3)
C3—C4—H4	119.7	C11—C12—N3	119.4 (3)
C5—C4—H4	119.7	C13—C12—N3	119.0 (3)
C6—C5—C4	120.3 (3)	C14—C13—C12	118.8 (3)
C6—C5—H5	119.9	C14—C13—H13	120.6
C4—C5—H5	119.9	C12—C13—H13	120.6
O2—C6—C5	120.4 (3)	C13—C14—C9	120.6 (3)
O2—C6—C1	118.5 (3)	C13—C14—H14	119.7
C5—C6—C1	121.0 (3)	C9—C14—H14	119.7
C7—N1—N2—C9	−171.3 (3)	C6—C1—C7—C8	−22.2 (5)
C6—C1—C2—O1	−174.7 (3)	C2—C1—C7—C8	157.6 (3)
C7—C1—C2—O1	5.5 (5)	N1—N2—C9—C14	−174.8 (3)
C6—C1—C2—C3	5.3 (5)	N1—N2—C9—C10	7.6 (5)
C7—C1—C2—C3	−174.5 (3)	N2—C9—C10—C11	177.7 (3)
O1—C2—C3—C4	176.7 (3)	C14—C9—C10—C11	0.1 (5)
C1—C2—C3—C4	−3.3 (5)	C9—C10—C11—C12	0.6 (5)
C2—C3—C4—C5	0.1 (5)	C10—C11—C12—C13	−0.5 (5)
C3—C4—C5—C6	1.0 (5)	C10—C11—C12—N3	177.5 (3)
C4—C5—C6—O2	−176.3 (3)	O4—N3—C12—C11	2.4 (4)
C4—C5—C6—C1	1.2 (5)	O3—N3—C12—C11	−177.3 (3)
C2—C1—C6—O2	173.3 (3)	O4—N3—C12—C13	−179.5 (3)
C7—C1—C6—O2	−6.8 (5)	O3—N3—C12—C13	0.9 (4)
C2—C1—C6—C5	−4.2 (5)	C11—C12—C13—C14	−0.2 (5)
C7—C1—C6—C5	175.6 (3)	N3—C12—C13—C14	−178.2 (3)
N2—N1—C7—C1	179.4 (3)	C12—C13—C14—C9	0.8 (5)
N2—N1—C7—C8	3.4 (5)	N2—C9—C14—C13	−178.5 (3)
C6—C1—C7—N1	161.9 (3)	C10—C9—C14—C13	−0.8 (5)
C2—C1—C7—N1	−18.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.84 (2)	1.79 (3)	2.534 (4)	147 (4)
N2—H2N···O3i	0.88 (2)	2.18 (3)	3.039 (4)	167 (2)
O2—H2O···O1ii	0.85 (4)	1.99 (4)	2.834 (3)	173 (4)
C14—H14···O4i	0.95	2.50	3.326 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.84 (2)	1.79 (3)	2.534 (4)	147 (4)
N2—H2N⋯O3i	0.88 (2)	2.18 (3)	3.039 (4)	167 (2)
O2—H2O⋯O1ii	0.85 (4)	1.99 (4)	2.834 (3)	173 (4)
C14—H14⋯O4i	0.95	2.50	3.326 (4)	146

Symmetry codes: (i) ; (ii) .