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

The title compound, C(14)H(11)N(3)O(4), was obtained by a condensation reaction between 3-nitro-benzaldehyde and 4-hy-droxy-benzohydrazide. The whole mol-ecule is approximately planar, with a dihedral angle of 9.2 (3)° between the benzene rings. The mol-ecule displays an E conformation about the C=N bond. In the crystal, mol-ecules are linked via N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds, generating sheets parallel to the bc plane.

Related literature

For the biological properties of hydrazone compounds, see: Cukurovali et al. (2006 ▶); Karthikeyan et al. (2006 ▶); Kucukguzel et al. (2006 ▶). For related hydrazone compounds, see: Hou (2009 ▶); Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Zhang et al. (2009 ▶); Khaledi et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C14H11N3O4

M = 285.26

Monoclinic,

a = 8.018 (2) Å

b = 11.156 (2) Å

c = 14.389 (2) Å

β = 91.773 (2)°

V = 1286.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.21 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.981

9218 measured reflections

2386 independent reflections

2020 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.10

2386 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014778/qm2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014778/qm2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014778/qm2061Isup3.cml

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

C14H11N3O4	F(000) = 592
Mr = 285.26	Dx = 1.473 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.018 (2) Å	Cell parameters from 4759 reflections
b = 11.156 (2) Å	θ = 2.8–27.0°
c = 14.389 (2) Å	µ = 0.11 mm−1
β = 91.773 (2)°	T = 298 K
V = 1286.4 (5) Å3	Block, yellow
Z = 4	0.21 × 0.20 × 0.17 mm

Bruker SMART 1000 CCD area-detector diffractometer	2386 independent reflections
Radiation source: fine-focus sealed tube	2020 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.977, Tmax = 0.981	k = −13→13
9218 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.347P] where P = (Fo2 + 2Fc2)/3
2386 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.18378 (15)	0.04393 (11)	0.44521 (8)	0.0361 (3)
N2	0.21274 (16)	−0.03537 (12)	0.51683 (8)	0.0372 (3)
N3	0.02101 (16)	0.30324 (12)	0.15979 (9)	0.0405 (3)
O1	−0.00751 (15)	0.39126 (11)	0.11049 (8)	0.0533 (3)
O2	−0.01799 (18)	0.20157 (11)	0.13697 (9)	0.0610 (4)
O3	0.14307 (14)	−0.19871 (10)	0.43108 (7)	0.0420 (3)
O4	0.43051 (15)	−0.43925 (11)	0.80509 (8)	0.0477 (3)
H4	0.4981	−0.4032	0.8386	0.072*
C1	0.18748 (18)	0.24891 (14)	0.39868 (10)	0.0357 (3)
C2	0.11420 (18)	0.22848 (13)	0.31117 (10)	0.0348 (3)
H2	0.0733	0.1532	0.2946	0.042*
C3	0.10429 (18)	0.32288 (13)	0.25017 (10)	0.0349 (3)
C4	0.1649 (2)	0.43600 (15)	0.27064 (12)	0.0435 (4)
H4A	0.1576	0.4974	0.2270	0.052*
C5	0.2364 (2)	0.45524 (15)	0.35766 (13)	0.0499 (4)
H5	0.2780	0.5306	0.3735	0.060*
C6	0.2463 (2)	0.36266 (15)	0.42129 (12)	0.0453 (4)
H6	0.2930	0.3767	0.4802	0.054*
C7	0.20456 (19)	0.15322 (14)	0.46738 (10)	0.0379 (4)
H7	0.2313	0.1727	0.5289	0.045*
C8	0.20226 (17)	−0.15485 (14)	0.50337 (9)	0.0329 (3)
C9	0.26711 (17)	−0.22804 (13)	0.58334 (9)	0.0331 (3)
C10	0.22900 (19)	−0.34905 (14)	0.58765 (10)	0.0389 (4)
H10	0.1649	−0.3839	0.5399	0.047*
C11	0.2843 (2)	−0.41868 (14)	0.66141 (11)	0.0415 (4)
H11	0.2574	−0.4997	0.6633	0.050*
C12	0.38050 (18)	−0.36750 (14)	0.73294 (10)	0.0358 (3)
C13	0.4214 (2)	−0.24795 (15)	0.72935 (11)	0.0447 (4)
H13	0.4862	−0.2135	0.7770	0.054*
C14	0.3661 (2)	−0.17939 (15)	0.65496 (11)	0.0446 (4)
H14	0.3956	−0.0989	0.6526	0.054*
H2A	0.231 (2)	−0.0045 (16)	0.5739 (8)	0.054*

	U11	U22	U33	U12	U13	U23
N1	0.0422 (7)	0.0365 (7)	0.0290 (6)	0.0028 (5)	−0.0068 (5)	0.0051 (5)
N2	0.0512 (7)	0.0345 (7)	0.0253 (6)	0.0020 (6)	−0.0102 (5)	0.0017 (5)
N3	0.0406 (7)	0.0410 (8)	0.0394 (7)	0.0042 (6)	−0.0070 (5)	0.0063 (6)
O1	0.0567 (7)	0.0501 (7)	0.0519 (7)	0.0071 (6)	−0.0149 (6)	0.0157 (6)
O2	0.0864 (10)	0.0441 (8)	0.0509 (7)	−0.0059 (7)	−0.0252 (7)	−0.0004 (6)
O3	0.0542 (7)	0.0405 (6)	0.0304 (5)	−0.0024 (5)	−0.0128 (5)	−0.0017 (5)
O4	0.0570 (7)	0.0467 (7)	0.0386 (6)	−0.0020 (5)	−0.0126 (5)	0.0146 (5)
C1	0.0363 (7)	0.0347 (8)	0.0357 (8)	0.0015 (6)	−0.0037 (6)	0.0021 (6)
C2	0.0366 (7)	0.0302 (8)	0.0372 (8)	0.0014 (6)	−0.0036 (6)	0.0014 (6)
C3	0.0345 (7)	0.0347 (8)	0.0353 (8)	0.0033 (6)	−0.0031 (6)	0.0026 (6)
C4	0.0497 (9)	0.0354 (9)	0.0453 (9)	−0.0014 (7)	−0.0030 (7)	0.0089 (7)
C5	0.0612 (10)	0.0340 (9)	0.0541 (10)	−0.0117 (8)	−0.0063 (8)	0.0002 (8)
C6	0.0522 (9)	0.0416 (9)	0.0415 (9)	−0.0062 (7)	−0.0093 (7)	−0.0016 (7)
C7	0.0423 (8)	0.0382 (9)	0.0324 (8)	−0.0004 (6)	−0.0091 (6)	0.0006 (6)
C8	0.0339 (7)	0.0373 (8)	0.0273 (7)	0.0000 (6)	−0.0033 (5)	0.0007 (6)
C9	0.0352 (7)	0.0359 (8)	0.0278 (7)	0.0013 (6)	−0.0038 (6)	0.0013 (6)
C10	0.0455 (8)	0.0364 (9)	0.0340 (8)	−0.0002 (6)	−0.0085 (6)	−0.0039 (6)
C11	0.0511 (9)	0.0313 (8)	0.0415 (9)	−0.0017 (7)	−0.0064 (7)	0.0029 (7)
C12	0.0374 (7)	0.0392 (9)	0.0305 (7)	0.0042 (6)	−0.0019 (6)	0.0068 (6)
C13	0.0524 (9)	0.0422 (9)	0.0382 (8)	−0.0051 (7)	−0.0178 (7)	0.0033 (7)
C14	0.0545 (9)	0.0357 (9)	0.0424 (9)	−0.0079 (7)	−0.0183 (7)	0.0062 (7)

N1—C7	1.270 (2)	C4—H4A	0.9300
N1—N2	1.3725 (17)	C5—C6	1.381 (2)
N2—C8	1.349 (2)	C5—H5	0.9300
N2—H2A	0.898 (9)	C6—H6	0.9300
N3—O2	1.2188 (18)	C7—H7	0.9300
N3—O1	1.2286 (17)	C8—C9	1.491 (2)
N3—C3	1.460 (2)	C9—C10	1.386 (2)
O3—C8	1.2312 (17)	C9—C14	1.392 (2)
O4—C12	1.3614 (17)	C10—C11	1.377 (2)
O4—H4	0.8200	C10—H10	0.9300
C1—C6	1.389 (2)	C11—C12	1.390 (2)
C1—C2	1.392 (2)	C11—H11	0.9300
C1—C7	1.458 (2)	C12—C13	1.375 (2)
C2—C3	1.372 (2)	C13—C14	1.378 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.381 (2)	C14—H14	0.9300
C4—C5	1.378 (2)
C7—N1—N2	114.35 (12)	C1—C6—H6	119.5
C8—N2—N1	121.38 (12)	N1—C7—C1	121.57 (14)
C8—N2—H2A	121.2 (12)	N1—C7—H7	119.2
N1—N2—H2A	117.3 (13)	C1—C7—H7	119.2
O2—N3—O1	123.13 (14)	O3—C8—N2	122.31 (13)
O2—N3—C3	119.08 (13)	O3—C8—C9	123.39 (14)
O1—N3—C3	117.79 (13)	N2—C8—C9	114.30 (12)
C12—O4—H4	109.5	C10—C9—C14	117.92 (14)
C6—C1—C2	119.49 (14)	C10—C9—C8	119.72 (13)
C6—C1—C7	119.08 (14)	C14—C9—C8	122.36 (14)
C2—C1—C7	121.44 (14)	C11—C10—C9	121.17 (14)
C3—C2—C1	117.89 (14)	C11—C10—H10	119.4
C3—C2—H2	121.1	C9—C10—H10	119.4
C1—C2—H2	121.1	C10—C11—C12	119.81 (15)
C2—C3—C4	123.52 (14)	C10—C11—H11	120.1
C2—C3—N3	118.08 (14)	C12—C11—H11	120.1
C4—C3—N3	118.38 (13)	O4—C12—C13	122.28 (14)
C5—C4—C3	118.04 (15)	O4—C12—C11	117.83 (14)
C5—C4—H4A	121.0	C13—C12—C11	119.89 (14)
C3—C4—H4A	121.0	C12—C13—C14	119.76 (15)
C4—C5—C6	119.98 (16)	C12—C13—H13	120.1
C4—C5—H5	120.0	C14—C13—H13	120.1
C6—C5—H5	120.0	C13—C14—C9	121.43 (15)
C5—C6—C1	121.07 (15)	C13—C14—H14	119.3
C5—C6—H6	119.5	C9—C14—H14	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.90 (1)	2.49 (2)	3.0406 (18)	120 (1)
N2—H2A···O4ii	0.90 (1)	2.32 (1)	3.0360 (17)	137 (2)
O4—H4···N1iii	0.82	2.63	3.0495 (17)	114
O4—H4···O3iii	0.82	2.08	2.8929 (16)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.90 (1)	2.49 (2)	3.0406 (18)	120 (1)
N2—H2A⋯O4ii	0.90 (1)	2.32 (1)	3.0360 (17)	137 (2)
O4—H4⋯N1iii	0.82	2.63	3.0495 (17)	114
O4—H4⋯O3iii	0.82	2.08	2.8929 (16)	173

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