(E)-N'-(3-Hy-droxy-benzyl-idene)-3-nitro-benzohydrazide.

The title compound, C(14)H(11)N(3)O(4), was prepared by the reaction of 3-nitro-benzohydrazide with 3-hy-droxy-benzalde-hyde. The mol-ecule adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 32.3 (2)°. In the crystal, the mol-ecules are linked through inter-molecular N-H⋯O, O-H⋯N, and O-H⋯O hydrogen bonds, forming chains in the a-axis direction.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For similar compounds that we have reported recently, see: Dai & Mao (2010a ▶,b ▶).

Experimental

Crystal data

C14H11N3O4

M = 285.26

Monoclinic,

a = 16.154 (3) Å

b = 13.295 (3) Å

c = 13.537 (2) Å

β = 120.324 (2)°

V = 2509.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.28 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.969, T max = 0.974

6631 measured reflections

2738 independent reflections

1588 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.144

S = 1.03

2738 reflections

196 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.25 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/S1600536810049482/sj5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049482/sj5070Isup2.hkl

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

C14H11N3O4	F(000) = 1184
Mr = 285.26	Dx = 1.510 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1285 reflections
a = 16.154 (3) Å	θ = 2.3–25.0°
b = 13.295 (3) Å	µ = 0.11 mm−1
c = 13.537 (2) Å	T = 298 K
β = 120.324 (2)°	Block, yellow
V = 2509.5 (8) Å3	0.28 × 0.27 × 0.23 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2738 independent reflections
Radiation source: fine-focus sealed tube	1588 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→20
Tmin = 0.969, Tmax = 0.974	k = −15→16
6631 measured reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0639P)2] where P = (Fo2 + 2Fc2)/3
2738 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.25 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	1.05387 (12)	0.55191 (13)	0.15027 (16)	0.0401 (5)
N2	0.95666 (13)	0.55067 (14)	0.10982 (17)	0.0422 (5)
N3	0.59440 (14)	0.63671 (15)	−0.07753 (18)	0.0489 (5)
O1	1.36619 (12)	0.85288 (13)	0.36202 (19)	0.0695 (6)
O2	0.95061 (11)	0.38209 (12)	0.09885 (16)	0.0594 (5)
O3	0.50831 (13)	0.62855 (15)	−0.1151 (2)	0.0883 (8)
O4	0.63203 (12)	0.71586 (13)	−0.07821 (16)	0.0605 (5)
C1	1.19663 (15)	0.65018 (16)	0.22714 (18)	0.0371 (5)
C2	1.23682 (17)	0.74283 (17)	0.2723 (2)	0.0455 (6)
H2	1.1981	0.7940	0.2736	0.055*
C3	1.33314 (17)	0.76106 (16)	0.3155 (2)	0.0427 (6)
C4	1.39012 (16)	0.68658 (17)	0.3115 (2)	0.0458 (6)
H4	1.4547	0.6986	0.3377	0.055*
C5	1.35046 (16)	0.59342 (18)	0.2679 (2)	0.0482 (6)
H5	1.3892	0.5425	0.2662	0.058*
C6	1.25507 (16)	0.57453 (18)	0.22723 (19)	0.0433 (6)
H6	1.2299	0.5110	0.1998	0.052*
C7	1.09381 (16)	0.63653 (17)	0.1815 (2)	0.0435 (6)
H7	1.0567	0.6922	0.1753	0.052*
C8	0.91039 (16)	0.46268 (17)	0.08701 (19)	0.0386 (5)
C9	0.80596 (15)	0.46724 (16)	0.04857 (18)	0.0368 (5)
C10	0.75046 (15)	0.55308 (16)	0.00497 (18)	0.0385 (5)
H10	0.7774	0.6130	−0.0008	0.046*
C11	0.65446 (15)	0.54756 (16)	−0.02961 (19)	0.0383 (5)
C12	0.61190 (17)	0.46063 (17)	−0.0223 (2)	0.0458 (6)
H12	0.5469	0.4590	−0.0461	0.055*
C13	0.66761 (17)	0.37664 (18)	0.0209 (2)	0.0501 (6)
H13	0.6403	0.3169	0.0264	0.060*
C14	0.76350 (16)	0.37974 (17)	0.0561 (2)	0.0444 (6)
H14	0.8005	0.3220	0.0856	0.053*
H2A	0.9284 (18)	0.6098 (12)	0.104 (2)	0.080*
H1	1.4208 (11)	0.863 (2)	0.369 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0246 (10)	0.0399 (11)	0.0500 (11)	0.0010 (8)	0.0146 (9)	0.0013 (9)
N2	0.0263 (11)	0.0385 (11)	0.0560 (12)	0.0005 (8)	0.0166 (10)	−0.0001 (9)
N3	0.0351 (12)	0.0409 (12)	0.0686 (14)	0.0015 (9)	0.0245 (11)	−0.0006 (10)
O1	0.0477 (12)	0.0428 (10)	0.1195 (16)	−0.0136 (9)	0.0433 (12)	−0.0173 (10)
O2	0.0378 (10)	0.0387 (10)	0.0931 (14)	0.0057 (8)	0.0267 (10)	0.0032 (9)
O3	0.0312 (11)	0.0640 (13)	0.151 (2)	0.0091 (9)	0.0322 (13)	0.0204 (12)
O4	0.0478 (11)	0.0405 (10)	0.0916 (14)	0.0029 (8)	0.0340 (11)	0.0033 (9)
C1	0.0282 (12)	0.0364 (12)	0.0427 (13)	−0.0002 (10)	0.0150 (11)	0.0027 (10)
C2	0.0370 (14)	0.0357 (13)	0.0662 (16)	0.0035 (10)	0.0279 (13)	0.0048 (11)
C3	0.0364 (14)	0.0335 (12)	0.0550 (15)	−0.0060 (10)	0.0208 (12)	−0.0018 (11)
C4	0.0274 (13)	0.0472 (15)	0.0556 (15)	−0.0001 (11)	0.0157 (12)	0.0010 (12)
C5	0.0363 (14)	0.0464 (15)	0.0580 (16)	0.0055 (11)	0.0210 (13)	−0.0037 (12)
C6	0.0358 (14)	0.0396 (13)	0.0488 (15)	−0.0033 (10)	0.0171 (12)	−0.0062 (10)
C7	0.0347 (13)	0.0345 (13)	0.0579 (15)	0.0033 (10)	0.0208 (12)	0.0025 (11)
C8	0.0299 (13)	0.0370 (13)	0.0438 (13)	0.0017 (10)	0.0149 (11)	0.0019 (10)
C9	0.0305 (12)	0.0370 (12)	0.0392 (13)	−0.0017 (10)	0.0148 (11)	−0.0035 (10)
C10	0.0318 (13)	0.0341 (12)	0.0473 (14)	−0.0022 (9)	0.0183 (11)	−0.0024 (10)
C11	0.0307 (13)	0.0369 (12)	0.0444 (13)	0.0010 (10)	0.0168 (11)	−0.0037 (10)
C12	0.0316 (13)	0.0480 (14)	0.0556 (16)	−0.0052 (11)	0.0205 (12)	−0.0018 (12)
C13	0.0389 (15)	0.0419 (14)	0.0668 (17)	−0.0062 (11)	0.0247 (13)	0.0061 (12)
C14	0.0373 (14)	0.0363 (13)	0.0524 (15)	0.0009 (10)	0.0173 (12)	0.0049 (11)

N1—C7	1.259 (3)	C4—H4	0.9300
N1—N2	1.378 (2)	C5—C6	1.372 (3)
N2—C8	1.338 (3)	C5—H5	0.9300
N2—H2A	0.892 (10)	C6—H6	0.9300
N3—O4	1.218 (2)	C7—H7	0.9300
N3—O3	1.221 (2)	C8—C9	1.495 (3)
N3—C11	1.460 (3)	C9—C14	1.380 (3)
O1—C3	1.354 (3)	C9—C10	1.386 (3)
O1—H1	0.850 (10)	C10—C11	1.377 (3)
O2—C8	1.221 (2)	C10—H10	0.9300
C1—C6	1.379 (3)	C11—C12	1.374 (3)
C1—C2	1.383 (3)	C12—C13	1.366 (3)
C1—C7	1.462 (3)	C12—H12	0.9300
C2—C3	1.379 (3)	C13—C14	1.372 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.372 (3)	C14—H14	0.9300
C4—C5	1.382 (3)
C7—N1—N2	115.61 (18)	C1—C6—H6	120.1
C8—N2—N1	119.61 (18)	N1—C7—C1	122.2 (2)
C8—N2—H2A	123.3 (19)	N1—C7—H7	118.9
N1—N2—H2A	117.0 (19)	C1—C7—H7	118.9
O4—N3—O3	122.8 (2)	O2—C8—N2	122.6 (2)
O4—N3—C11	118.86 (19)	O2—C8—C9	120.9 (2)
O3—N3—C11	118.3 (2)	N2—C8—C9	116.47 (19)
C3—O1—H1	110 (2)	C14—C9—C10	119.1 (2)
C6—C1—C2	118.7 (2)	C14—C9—C8	117.1 (2)
C6—C1—C7	122.8 (2)	C10—C9—C8	123.7 (2)
C2—C1—C7	118.5 (2)	C11—C10—C9	118.4 (2)
C3—C2—C1	121.4 (2)	C11—C10—H10	120.8
C3—C2—H2	119.3	C9—C10—H10	120.8
C1—C2—H2	119.3	C12—C11—C10	122.6 (2)
O1—C3—C4	123.7 (2)	C12—C11—N3	118.1 (2)
O1—C3—C2	116.8 (2)	C10—C11—N3	119.30 (19)
C4—C3—C2	119.5 (2)	C13—C12—C11	118.2 (2)
C3—C4—C5	119.2 (2)	C13—C12—H12	120.9
C3—C4—H4	120.4	C11—C12—H12	120.9
C5—C4—H4	120.4	C12—C13—C14	120.5 (2)
C6—C5—C4	121.3 (2)	C12—C13—H13	119.7
C6—C5—H5	119.3	C14—C13—H13	119.7
C4—C5—H5	119.3	C13—C14—C9	121.0 (2)
C5—C6—C1	119.8 (2)	C13—C14—H14	119.5
C5—C6—H6	120.1	C9—C14—H14	119.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.85 (1)	2.58 (3)	2.986 (2)	111 (2)
O1—H1···O2i	0.85 (1)	1.91 (1)	2.758 (2)	174 (3)
N2—H2A···O4ii	0.89 (1)	2.47 (1)	3.354 (3)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.85 (1)	2.58 (3)	2.986 (2)	111 (2)
O1—H1⋯O2i	0.85 (1)	1.91 (1)	2.758 (2)	174 (3)
N2—H2A⋯O4ii	0.89 (1)	2.47 (1)	3.354 (3)	171 (2)

Symmetry codes: (i) ; (ii) .