(E)-N'-(4-Hy-droxy-benzyl-idene)-2-nitro-benzohydrazide.

In the title compound, C(14)H(11)N(3)O(4), the two benzene rings form a dihedral angle of 45.3 (3)°. The nitro group is twisted out of the attached ring by a dihedral angle of 37.5 (3)°. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (100) by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Zhu et al. (2009 ▶); Jimenez-Pulido et al. (2008 ▶); Raj et al. (2007 ▶); Zhong et al. (2007 ▶). For the crystal structures of hydrazones, see: Khaledi et al. (2009 ▶); Warad et al. (2009 ▶); Back et al. (2009 ▶); Vijayakumar et al. (2009 ▶). For related structures, see: Cao (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C14H11N3O4

M = 285.26

Orthorhombic,

a = 7.720 (2) Å

b = 11.398 (3) Å

c = 15.072 (5) Å

V = 1326.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.979, T max = 0.981

7745 measured reflections

1602 independent reflections

961 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.125

S = 1.02

1602 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022075/ci5099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022075/ci5099Isup2.hkl

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

C14H11N3O4	F(000) = 592
Mr = 285.26	Dx = 1.429 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 633 reflections
a = 7.720 (2) Å	θ = 2.5–24.5°
b = 11.398 (3) Å	µ = 0.11 mm−1
c = 15.072 (5) Å	T = 298 K
V = 1326.3 (7) Å3	Block, colourless
Z = 4	0.20 × 0.18 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1602 independent reflections
Radiation source: fine-focus sealed tube	961 reflections with I > 2σ(I)
graphite	Rint = 0.085
ω scans	θmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.979, Tmax = 0.981	k = −14→13
7745 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3
1602 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.18 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
N1	0.1071 (5)	0.7318 (3)	1.03691 (19)	0.0490 (10)
N2	0.1251 (5)	0.7909 (3)	0.9568 (2)	0.0486 (9)
N3	0.2475 (6)	1.1354 (4)	0.9364 (3)	0.0729 (13)
O1	0.1478 (4)	0.3516 (2)	1.34410 (16)	0.0478 (8)
H1	0.0826	0.3784	1.3820	0.072*
O2	0.0109 (4)	0.9556 (2)	1.01482 (16)	0.0498 (8)
O3	0.3197 (5)	1.0807 (4)	0.9939 (2)	0.0846 (12)
O4	0.2255 (9)	1.2411 (4)	0.9389 (3)	0.151 (2)
C1	0.1311 (5)	0.5519 (3)	1.1159 (2)	0.0386 (9)
C2	0.0734 (5)	0.5986 (3)	1.1956 (2)	0.0415 (10)
H2	0.0306	0.6749	1.1971	0.050*
C3	0.0787 (5)	0.5334 (3)	1.2728 (3)	0.0411 (10)
H3	0.0418	0.5657	1.3262	0.049*
C4	0.1396 (5)	0.4197 (3)	1.2695 (2)	0.0362 (9)
C5	0.1956 (5)	0.3714 (3)	1.1908 (3)	0.0428 (10)
H5	0.2367	0.2948	1.1892	0.051*
C6	0.1902 (5)	0.4375 (3)	1.1148 (2)	0.0428 (10)
H6	0.2271	0.4047	1.0616	0.051*
C7	0.1348 (6)	0.6220 (4)	1.0351 (2)	0.0452 (10)
H7	0.1579	0.5856	0.9812	0.054*
C8	0.0819 (5)	0.9035 (3)	0.9539 (2)	0.0406 (10)
C9	0.1145 (5)	0.9615 (3)	0.8660 (2)	0.0385 (9)
C10	0.1817 (6)	1.0730 (4)	0.8584 (3)	0.0470 (11)
C11	0.1996 (6)	1.1296 (4)	0.7788 (3)	0.0570 (12)
H11	0.2446	1.2052	0.7762	0.068*
C12	0.1495 (7)	1.0721 (5)	0.7024 (3)	0.0649 (14)
H12	0.1618	1.1088	0.6477	0.078*
C13	0.0821 (6)	0.9617 (4)	0.7068 (3)	0.0609 (13)
H13	0.0495	0.9228	0.6552	0.073*
C14	0.0624 (5)	0.9078 (4)	0.7889 (2)	0.0468 (11)
H14	0.0127	0.8336	0.7917	0.056*
H2A	0.189 (5)	0.755 (4)	0.915 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.076 (3)	0.0396 (19)	0.0313 (18)	0.0082 (19)	0.0090 (19)	0.0098 (15)
N2	0.073 (3)	0.040 (2)	0.0327 (19)	0.008 (2)	0.016 (2)	0.0108 (15)
N3	0.095 (4)	0.056 (3)	0.067 (3)	−0.013 (3)	0.011 (3)	−0.006 (2)
O1	0.065 (2)	0.0454 (16)	0.0334 (15)	0.0081 (15)	0.0097 (14)	0.0069 (12)
O2	0.068 (2)	0.0442 (16)	0.0377 (15)	0.0063 (16)	0.0144 (15)	−0.0023 (13)
O3	0.087 (3)	0.112 (3)	0.055 (2)	−0.020 (3)	−0.0063 (19)	−0.009 (2)
O4	0.262 (7)	0.056 (3)	0.133 (4)	−0.013 (3)	−0.004 (4)	−0.027 (3)
C1	0.049 (2)	0.033 (2)	0.034 (2)	0.001 (2)	0.0034 (19)	0.0029 (16)
C2	0.055 (3)	0.035 (2)	0.034 (2)	0.006 (2)	0.0031 (19)	0.0018 (17)
C3	0.051 (3)	0.041 (2)	0.032 (2)	0.002 (2)	0.0087 (18)	−0.0002 (18)
C4	0.041 (2)	0.038 (2)	0.0303 (19)	−0.007 (2)	0.0019 (18)	0.0099 (17)
C5	0.057 (3)	0.031 (2)	0.041 (2)	0.002 (2)	−0.001 (2)	−0.0005 (18)
C6	0.056 (3)	0.041 (2)	0.032 (2)	0.000 (2)	0.0040 (18)	−0.0034 (18)
C7	0.059 (3)	0.046 (2)	0.031 (2)	0.003 (2)	0.005 (2)	0.0022 (17)
C8	0.050 (3)	0.039 (2)	0.033 (2)	0.001 (2)	0.0062 (19)	0.0045 (18)
C9	0.047 (2)	0.034 (2)	0.034 (2)	0.009 (2)	0.0043 (19)	−0.0001 (17)
C10	0.053 (3)	0.044 (2)	0.043 (2)	0.008 (2)	0.008 (2)	0.001 (2)
C11	0.060 (3)	0.045 (3)	0.067 (3)	−0.003 (2)	0.013 (2)	0.019 (2)
C12	0.073 (3)	0.072 (3)	0.049 (3)	0.017 (3)	0.011 (3)	0.030 (3)
C13	0.073 (3)	0.074 (3)	0.036 (3)	0.013 (3)	0.000 (2)	0.004 (2)
C14	0.056 (3)	0.045 (2)	0.039 (2)	0.003 (2)	0.0006 (19)	0.0037 (19)

N1—C7	1.270 (4)	C4—C5	1.377 (5)
N1—N2	1.389 (4)	C5—C6	1.372 (5)
N2—C8	1.327 (5)	C5—H5	0.93
N2—H2A	0.90 (1)	C6—H6	0.93
N3—O3	1.204 (5)	C7—H7	0.93
N3—O4	1.217 (5)	C8—C9	1.501 (5)
N3—C10	1.466 (6)	C9—C14	1.374 (5)
O1—C4	1.368 (4)	C9—C10	1.377 (5)
O1—H1	0.82	C10—C11	1.369 (5)
O2—C8	1.224 (4)	C11—C12	1.379 (6)
C1—C6	1.381 (5)	C11—H11	0.93
C1—C2	1.388 (5)	C12—C13	1.363 (7)
C1—C7	1.457 (5)	C12—H12	0.93
C2—C3	1.381 (5)	C13—C14	1.390 (5)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.380 (5)	C14—H14	0.93
C3—H3	0.93
C7—N1—N2	116.2 (3)	C1—C6—H6	119.4
C8—N2—N1	118.2 (3)	N1—C7—C1	121.3 (3)
C8—N2—H2A	123 (3)	N1—C7—H7	119.3
N1—N2—H2A	117 (3)	C1—C7—H7	119.3
O3—N3—O4	123.7 (5)	O2—C8—N2	123.9 (3)
O3—N3—C10	119.1 (4)	O2—C8—C9	121.5 (3)
O4—N3—C10	117.2 (5)	N2—C8—C9	114.4 (3)
C4—O1—H1	109.5	C14—C9—C10	116.8 (4)
C6—C1—C2	118.6 (3)	C14—C9—C8	120.0 (4)
C6—C1—C7	120.1 (3)	C10—C9—C8	123.0 (3)
C2—C1—C7	121.3 (3)	C11—C10—C9	123.2 (4)
C3—C2—C1	120.9 (3)	C11—C10—N3	116.0 (4)
C3—C2—H2	119.6	C9—C10—N3	120.7 (4)
C1—C2—H2	119.6	C10—C11—C12	118.6 (4)
C4—C3—C2	119.0 (3)	C10—C11—H11	120.7
C4—C3—H3	120.5	C12—C11—H11	120.7
C2—C3—H3	120.5	C13—C12—C11	120.4 (4)
O1—C4—C5	117.8 (3)	C13—C12—H12	119.8
O1—C4—C3	121.3 (3)	C11—C12—H12	119.8
C5—C4—C3	120.9 (3)	C12—C13—C14	119.5 (4)
C6—C5—C4	119.4 (3)	C12—C13—H13	120.2
C6—C5—H5	120.3	C14—C13—H13	120.2
C4—C5—H5	120.3	C9—C14—C13	121.6 (4)
C5—C6—C1	121.2 (4)	C9—C14—H14	119.2
C5—C6—H6	119.4	C13—C14—H14	119.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.93	2.725 (3)	164
N2—H2A···O1ii	0.90 (1)	2.05 (2)	2.932 (4)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.93	2.725 (3)	164
N2—H2A⋯O1ii	0.90 (1)	2.05 (2)	2.932 (4)	166 (4)

Symmetry codes: (i) ; (ii) .