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

The mol-ecule of the title compound, C(14)H(11)N(3)O(4), assumes an E conformation about the C=N double bond. The benzene rings form a dihedral angle of 3.9 (2)°. The crystal structure is stabilized by N-H⋯O, O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to (101). In addition, intra-layer π-π stacking inter-actions [centroid-centroid distance = 3.635 (2) Å] are observed.

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds of benzohydrazide derivatives, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For similar structures, see: Liu et al. (2011 ▶); Zhou et al. (2011 ▶); Meng et al. (2011 ▶).

Experimental

Crystal data

C14H11N3O4

M = 285.26

Monoclinic,

a = 10.362 (2) Å

b = 12.178 (3) Å

c = 10.468 (2) Å

β = 91.666 (2)°

V = 1320.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.984

10464 measured reflections

2884 independent reflections

2017 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.129

S = 1.03

2884 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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) I, global. DOI: 10.1107/S1600536811051233/rz2676sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051233/rz2676Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051233/rz2676Isup3.cml

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

C14H11N3O4	F(000) = 592
Mr = 285.26	Dx = 1.435 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3224 reflections
a = 10.362 (2) Å	θ = 2.5–27.2°
b = 12.178 (3) Å	µ = 0.11 mm−1
c = 10.468 (2) Å	T = 298 K
β = 91.666 (2)°	Block, yellow
V = 1320.3 (5) Å3	0.17 × 0.15 × 0.15 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	2884 independent reflections
Radiation source: fine-focus sealed tube	2017 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scan	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.982, Tmax = 0.984	k = −15→15
10464 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.233P] where P = (Fo2 + 2Fc2)/3
2884 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.20 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	0.05181 (12)	0.48482 (12)	0.34202 (13)	0.0426 (4)
N2	0.14827 (13)	0.55140 (12)	0.39294 (14)	0.0432 (4)
N3	0.56139 (14)	0.71802 (15)	0.60566 (14)	0.0521 (4)
O1	−0.27851 (12)	0.07966 (10)	0.13367 (13)	0.0548 (4)
H1	−0.3510	0.1064	0.1273	0.082*
O2	0.01462 (11)	0.69680 (10)	0.38555 (12)	0.0525 (4)
O3	0.57302 (14)	0.61913 (14)	0.62040 (16)	0.0768 (5)
O4	0.64912 (12)	0.78320 (13)	0.62796 (14)	0.0682 (4)
C1	0.01449 (16)	0.19488 (15)	0.27428 (16)	0.0451 (4)
H1A	0.0946	0.1703	0.3047	0.054*
C2	−0.07416 (16)	0.12048 (15)	0.22597 (17)	0.0481 (4)
H2	−0.0539	0.0461	0.2240	0.058*
C3	−0.19415 (15)	0.15658 (14)	0.18014 (15)	0.0403 (4)
C4	−0.22330 (16)	0.26705 (14)	0.18248 (16)	0.0418 (4)
H4	−0.3030	0.2916	0.1510	0.050*
C5	−0.13454 (15)	0.34089 (14)	0.23140 (15)	0.0414 (4)
H5	−0.1552	0.4152	0.2333	0.050*
C6	−0.01402 (15)	0.30600 (14)	0.27822 (14)	0.0383 (4)
C7	0.07926 (15)	0.38382 (14)	0.33207 (15)	0.0416 (4)
H7	0.1603	0.3590	0.3596	0.050*
C8	0.12135 (15)	0.65778 (14)	0.41169 (14)	0.0387 (4)
C9	0.22883 (15)	0.72875 (14)	0.46301 (14)	0.0387 (4)
C10	0.34487 (15)	0.68786 (14)	0.51232 (14)	0.0403 (4)
H10	0.3601	0.6126	0.5155	0.048*
C11	0.43746 (15)	0.76159 (15)	0.55668 (15)	0.0425 (4)
C12	0.41881 (18)	0.87291 (16)	0.55569 (17)	0.0524 (5)
H12	0.4824	0.9202	0.5875	0.063*
C13	0.30287 (19)	0.91322 (16)	0.5062 (2)	0.0599 (5)
H13	0.2880	0.9885	0.5038	0.072*
C14	0.20934 (17)	0.84119 (15)	0.46041 (17)	0.0499 (4)
H14	0.1317	0.8689	0.4272	0.060*
H2A	0.2202 (14)	0.5183 (17)	0.4207 (19)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0309 (7)	0.0467 (9)	0.0495 (8)	−0.0055 (6)	−0.0112 (6)	−0.0001 (6)
N2	0.0285 (7)	0.0449 (8)	0.0553 (8)	−0.0034 (6)	−0.0141 (6)	0.0009 (6)
N3	0.0346 (8)	0.0727 (12)	0.0487 (8)	−0.0096 (8)	−0.0060 (6)	0.0011 (8)
O1	0.0401 (7)	0.0508 (8)	0.0729 (8)	−0.0085 (6)	−0.0092 (6)	−0.0107 (6)
O2	0.0333 (7)	0.0542 (8)	0.0691 (8)	0.0028 (5)	−0.0139 (6)	−0.0007 (6)
O3	0.0500 (9)	0.0740 (11)	0.1050 (12)	−0.0048 (8)	−0.0232 (8)	0.0193 (9)
O4	0.0378 (7)	0.0908 (11)	0.0752 (9)	−0.0179 (7)	−0.0097 (6)	−0.0121 (8)
C1	0.0300 (8)	0.0517 (10)	0.0530 (10)	0.0035 (7)	−0.0052 (7)	−0.0029 (8)
C2	0.0411 (10)	0.0420 (10)	0.0612 (11)	0.0019 (8)	−0.0009 (8)	−0.0050 (8)
C3	0.0320 (8)	0.0477 (10)	0.0411 (8)	−0.0081 (7)	−0.0005 (6)	−0.0053 (7)
C4	0.0308 (8)	0.0495 (10)	0.0448 (9)	−0.0003 (7)	−0.0068 (7)	0.0010 (7)
C5	0.0351 (9)	0.0411 (9)	0.0475 (9)	−0.0014 (7)	−0.0055 (7)	−0.0011 (7)
C6	0.0304 (8)	0.0469 (10)	0.0373 (8)	−0.0033 (7)	−0.0009 (6)	−0.0028 (7)
C7	0.0279 (8)	0.0506 (11)	0.0460 (9)	−0.0017 (7)	−0.0060 (7)	−0.0011 (7)
C8	0.0307 (8)	0.0483 (10)	0.0368 (8)	−0.0015 (7)	−0.0055 (6)	0.0035 (7)
C9	0.0322 (8)	0.0474 (10)	0.0364 (8)	−0.0046 (7)	−0.0009 (6)	0.0006 (7)
C10	0.0325 (9)	0.0468 (10)	0.0415 (8)	−0.0050 (7)	−0.0038 (7)	0.0014 (7)
C11	0.0313 (9)	0.0594 (11)	0.0366 (8)	−0.0079 (8)	−0.0011 (6)	0.0007 (7)
C12	0.0457 (10)	0.0558 (12)	0.0554 (11)	−0.0154 (9)	−0.0028 (8)	−0.0068 (9)
C13	0.0567 (12)	0.0468 (11)	0.0757 (13)	−0.0052 (9)	−0.0052 (10)	−0.0059 (9)
C14	0.0432 (10)	0.0497 (11)	0.0563 (10)	0.0030 (8)	−0.0057 (8)	−0.0015 (8)

N1—C7	1.267 (2)	C4—H4	0.9300
N1—N2	1.3819 (18)	C5—C6	1.394 (2)
N2—C8	1.341 (2)	C5—H5	0.9300
N2—H2A	0.888 (9)	C6—C7	1.456 (2)
N3—O3	1.220 (2)	C7—H7	0.9300
N3—O4	1.224 (2)	C8—C9	1.497 (2)
N3—C11	1.468 (2)	C9—C14	1.384 (2)
O1—C3	1.3614 (19)	C9—C10	1.387 (2)
O1—H1	0.8200	C10—C11	1.384 (2)
O2—C8	1.2272 (18)	C10—H10	0.9300
C1—C2	1.376 (2)	C11—C12	1.369 (3)
C1—C6	1.386 (2)	C12—C13	1.384 (3)
C1—H1A	0.9300	C12—H12	0.9300
C2—C3	1.391 (2)	C13—C14	1.383 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.379 (2)	C14—H14	0.9300
C4—C5	1.375 (2)
C7—N1—N2	116.07 (13)	C5—C6—C7	121.03 (15)
C8—N2—N1	118.17 (13)	N1—C7—C6	121.04 (15)
C8—N2—H2A	124.5 (15)	N1—C7—H7	119.5
N1—N2—H2A	116.8 (15)	C6—C7—H7	119.5
O3—N3—O4	123.09 (17)	O2—C8—N2	122.10 (15)
O3—N3—C11	118.90 (15)	O2—C8—C9	120.85 (16)
O4—N3—C11	118.00 (17)	N2—C8—C9	117.03 (14)
C3—O1—H1	109.5	C14—C9—C10	119.13 (15)
C2—C1—C6	120.87 (15)	C14—C9—C8	117.22 (15)
C2—C1—H1A	119.6	C10—C9—C8	123.65 (15)
C6—C1—H1A	119.6	C11—C10—C9	118.48 (16)
C1—C2—C3	119.95 (16)	C11—C10—H10	120.8
C1—C2—H2	120.0	C9—C10—H10	120.8
C3—C2—H2	120.0	C12—C11—C10	122.91 (16)
O1—C3—C4	122.60 (15)	C12—C11—N3	118.83 (15)
O1—C3—C2	117.65 (16)	C10—C11—N3	118.26 (16)
C4—C3—C2	119.75 (15)	C11—C12—C13	118.34 (16)
C5—C4—C3	120.01 (15)	C11—C12—H12	120.8
C5—C4—H4	120.0	C13—C12—H12	120.8
C3—C4—H4	120.0	C14—C13—C12	119.78 (18)
C4—C5—C6	120.95 (16)	C14—C13—H13	120.1
C4—C5—H5	119.5	C12—C13—H13	120.1
C6—C5—H5	119.5	C13—C14—C9	121.35 (17)
C1—C6—C5	118.46 (14)	C13—C14—H14	119.3
C1—C6—C7	120.50 (14)	C9—C14—H14	119.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	2.02	2.8341 (18)	170.
O1—H1···N1i	0.82	2.58	3.0757 (19)	120.
N2—H2A···O1ii	0.89 (1)	2.53 (2)	3.0597 (19)	119.(2)
C5—H5···O1iii	0.93	2.54	3.367 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	2.02	2.8341 (18)	170
O1—H1⋯N1i	0.82	2.58	3.0757 (19)	120
N2—H2A⋯O1ii	0.89 (1)	2.53 (2)	3.0597 (19)	119 (2)
C5—H5⋯O1iii	0.93	2.54	3.367 (2)	147

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