(E)-4-Hydr-oxy-N'-(4-nitro-benzyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(14)H(11)N(3)O(4), is approximately planar, the dihedral angle between the planes of the two substituted benzene rings being 2.54 (7)°. The mol-ecule exists in a trans configuration with respect to the central methyl-idene unit. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to (101). The O/N-H⋯O and C-H⋯O inter-actions form a pair of bifurcated acceptor bonds involving the cabon-yl/nitro O atom, generating an R(2) (1)(6) motif.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C14H11N3O4

M = 285.26

Monoclinic,

a = 7.659 (1) Å

b = 13.587 (2) Å

c = 12.561 (2) Å

β = 92.784 (5)°

V = 1305.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.981

7862 measured reflections

2835 independent reflections

2109 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.04

2835 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.13 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 datablocks global, I. DOI: 10.1107/S1600536809020066/ci2812sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020066/ci2812Isup2.hkl

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

C14H11N3O4	F(000) = 592
Mr = 285.26	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2390 reflections
a = 7.659 (1) Å	θ = 3.0–30.5°
b = 13.587 (2) Å	µ = 0.11 mm−1
c = 12.561 (2) Å	T = 298 K
β = 92.784 (5)°	Block, colourless
V = 1305.6 (3) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2835 independent reflections
Radiation source: fine-focus sealed tube	2109 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.979, Tmax = 0.981	k = −17→15
7862 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3196P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2835 reflections	Δρmax = 0.21 e Å−3
195 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (15)

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	0.20673 (17)	0.97706 (9)	1.04460 (10)	0.0410 (3)
N2	0.26363 (19)	1.05171 (9)	0.98149 (10)	0.0431 (3)
N3	0.0157 (2)	0.54652 (10)	1.21921 (11)	0.0504 (4)
O1	0.18428 (15)	1.16731 (8)	1.09824 (8)	0.0472 (3)
O2	0.51173 (18)	1.44263 (8)	0.75115 (9)	0.0541 (3)
H2	0.5548	1.4194	0.6982	0.081*
O3	0.0321 (2)	0.46801 (10)	1.17422 (12)	0.0883 (6)
O4	−0.04623 (18)	0.55386 (9)	1.30667 (10)	0.0611 (4)
C1	0.1672 (2)	0.80400 (11)	1.06387 (12)	0.0391 (4)
C2	0.1011 (2)	0.80979 (11)	1.16524 (12)	0.0423 (4)
H2A	0.0898	0.8707	1.1980	0.051*
C3	0.0527 (2)	0.72557 (12)	1.21665 (12)	0.0418 (4)
H3	0.0085	0.7288	1.2842	0.050*
C4	0.0707 (2)	0.63608 (11)	1.16619 (12)	0.0402 (4)
C5	0.1366 (2)	0.62796 (12)	1.06648 (13)	0.0455 (4)
H5	0.1483	0.5668	1.0344	0.055*
C6	0.1845 (2)	0.71259 (12)	1.01580 (12)	0.0450 (4)
H6	0.2290	0.7087	0.9484	0.054*
C7	0.2198 (2)	0.89103 (11)	1.00586 (13)	0.0439 (4)
H7	0.2642	0.8835	0.9387	0.053*
C8	0.25098 (19)	1.14649 (11)	1.01458 (11)	0.0354 (3)
C9	0.32220 (19)	1.22217 (11)	0.94326 (11)	0.0348 (3)
C10	0.3187 (2)	1.32057 (11)	0.97329 (12)	0.0404 (4)
H10	0.2734	1.3378	1.0381	0.048*
C11	0.3812 (2)	1.39297 (11)	0.90850 (13)	0.0447 (4)
H11	0.3772	1.4585	0.9298	0.054*
C12	0.4503 (2)	1.36889 (11)	0.81144 (12)	0.0390 (4)
C13	0.4543 (2)	1.27096 (11)	0.78040 (12)	0.0410 (4)
H13	0.4995	1.2538	0.7156	0.049*
C14	0.3915 (2)	1.19946 (11)	0.84559 (12)	0.0403 (4)
H14	0.3952	1.1340	0.8240	0.048*
H2B	0.303 (3)	1.0358 (15)	0.9176 (10)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0486 (8)	0.0377 (7)	0.0377 (7)	−0.0014 (6)	0.0127 (6)	0.0081 (6)
N2	0.0616 (9)	0.0335 (7)	0.0359 (7)	−0.0021 (6)	0.0200 (6)	0.0028 (5)
N3	0.0650 (10)	0.0397 (8)	0.0477 (8)	−0.0055 (7)	0.0146 (7)	0.0081 (6)
O1	0.0630 (7)	0.0441 (6)	0.0364 (6)	0.0005 (5)	0.0217 (5)	−0.0009 (5)
O2	0.0760 (9)	0.0361 (6)	0.0525 (7)	−0.0056 (6)	0.0280 (6)	0.0047 (5)
O3	0.1579 (16)	0.0359 (7)	0.0749 (10)	−0.0156 (9)	0.0465 (10)	−0.0013 (7)
O4	0.0814 (9)	0.0505 (7)	0.0537 (7)	−0.0059 (6)	0.0289 (7)	0.0118 (6)
C1	0.0401 (8)	0.0381 (8)	0.0395 (8)	−0.0015 (6)	0.0068 (6)	0.0070 (6)
C2	0.0511 (10)	0.0350 (8)	0.0413 (9)	−0.0008 (7)	0.0087 (7)	0.0012 (6)
C3	0.0477 (9)	0.0425 (9)	0.0358 (8)	0.0001 (7)	0.0103 (7)	0.0051 (7)
C4	0.0440 (9)	0.0364 (8)	0.0408 (8)	−0.0029 (7)	0.0073 (7)	0.0076 (6)
C5	0.0563 (10)	0.0368 (8)	0.0446 (9)	−0.0019 (7)	0.0129 (8)	0.0002 (7)
C6	0.0546 (10)	0.0436 (9)	0.0379 (8)	−0.0008 (7)	0.0141 (7)	0.0029 (7)
C7	0.0526 (10)	0.0418 (9)	0.0384 (8)	−0.0023 (7)	0.0135 (7)	0.0047 (7)
C8	0.0375 (8)	0.0388 (8)	0.0307 (7)	0.0026 (6)	0.0091 (6)	0.0001 (6)
C9	0.0378 (8)	0.0342 (7)	0.0331 (7)	0.0017 (6)	0.0095 (6)	−0.0003 (6)
C10	0.0495 (9)	0.0379 (8)	0.0352 (8)	0.0012 (7)	0.0158 (7)	−0.0050 (6)
C11	0.0568 (10)	0.0313 (8)	0.0473 (9)	−0.0003 (7)	0.0161 (7)	−0.0051 (7)
C12	0.0432 (9)	0.0333 (7)	0.0414 (8)	−0.0014 (6)	0.0111 (7)	0.0027 (6)
C13	0.0516 (9)	0.0385 (8)	0.0345 (8)	−0.0003 (7)	0.0178 (7)	−0.0022 (6)
C14	0.0529 (9)	0.0302 (7)	0.0394 (8)	−0.0006 (6)	0.0165 (7)	−0.0034 (6)

N1—C7	1.272 (2)	C4—C5	1.377 (2)
N1—N2	1.3714 (17)	C5—C6	1.373 (2)
N2—C8	1.3581 (19)	C5—H5	0.93
N2—H2B	0.899 (9)	C6—H6	0.93
N3—O3	1.2164 (18)	C7—H7	0.93
N3—O4	1.2219 (17)	C8—C9	1.4848 (19)
N3—C4	1.4590 (19)	C9—C10	1.390 (2)
O1—C8	1.2237 (16)	C9—C14	1.395 (2)
O2—C12	1.3539 (17)	C10—C11	1.377 (2)
O2—H2	0.82	C10—H10	0.93
C1—C6	1.390 (2)	C11—C12	1.392 (2)
C1—C2	1.395 (2)	C11—H11	0.93
C1—C7	1.456 (2)	C12—C13	1.387 (2)
C2—C3	1.374 (2)	C13—C14	1.373 (2)
C2—H2A	0.93	C13—H13	0.93
C3—C4	1.381 (2)	C14—H14	0.93
C3—H3	0.93
C7—N1—N2	115.18 (12)	C1—C6—H6	119.5
C8—N2—N1	119.67 (12)	N1—C7—C1	121.73 (14)
C8—N2—H2B	122.3 (14)	N1—C7—H7	119.1
N1—N2—H2B	117.9 (14)	C1—C7—H7	119.1
O3—N3—O4	122.86 (14)	O1—C8—N2	121.40 (13)
O3—N3—C4	118.74 (14)	O1—C8—C9	122.61 (13)
O4—N3—C4	118.40 (14)	N2—C8—C9	115.99 (12)
C12—O2—H2	109.5	C10—C9—C14	117.70 (13)
C6—C1—C2	119.55 (14)	C10—C9—C8	119.34 (13)
C6—C1—C7	118.28 (14)	C14—C9—C8	122.96 (13)
C2—C1—C7	122.18 (14)	C11—C10—C9	120.99 (14)
C3—C2—C1	120.02 (14)	C11—C10—H10	119.5
C3—C2—H2A	120.0	C9—C10—H10	119.5
C1—C2—H2A	120.0	C10—C11—C12	120.51 (14)
C2—C3—C4	118.84 (14)	C10—C11—H11	119.7
C2—C3—H3	120.6	C12—C11—H11	119.7
C4—C3—H3	120.6	O2—C12—C13	122.66 (13)
C5—C4—C3	122.48 (14)	O2—C12—C11	118.25 (13)
C5—C4—N3	118.35 (14)	C13—C12—C11	119.09 (14)
C3—C4—N3	119.16 (13)	C14—C13—C12	119.87 (13)
C6—C5—C4	118.20 (15)	C14—C13—H13	120.1
C6—C5—H5	120.9	C12—C13—H13	120.1
C4—C5—H5	120.9	C13—C14—C9	121.84 (14)
C5—C6—C1	120.91 (14)	C13—C14—H14	119.1
C5—C6—H6	119.5	C9—C14—H14	119.1

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.02	2.8131 (15)	164
N2—H2B···O4ii	0.90 (1)	2.22 (1)	3.0513 (17)	155 (2)
C7—H7···O4ii	0.93	2.41	3.235 (2)	148
C13—H13···O1i	0.93	2.35	3.0713 (19)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.02	2.8131 (15)	164
N2—H2B⋯O4ii	0.90 (1)	2.22 (1)	3.0513 (17)	155 (2)
C7—H7⋯O4ii	0.93	2.41	3.235 (2)	148
C13—H13⋯O1i	0.93	2.35	3.0713 (19)	134

Symmetry codes: (i) ; (ii) .