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

The title mol-ecule, C(14)H(11)N(3)O(4), is approximately planar, with an inter-planar angle between the two benzene rings of 5.8 (2)°. In the crystal, four mol-ecules are linked by an R(4) (4)(12) motif with pairs of strong O-H⋯O and N-H⋯O hydrogen bonds. The motif is situated about the crystallographic centres of symmetry and it is composed of two pairs of parallel mol-ecules. This quadruplet of mol-ecules is further extended by symmetry-equivalent hydrogen bonds to form layers parallel to the (10) plane. In addition to the hydrogen bonds, there is also a weak π-π inter-action between the benzene rings.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶). For related structures, see: Ahmad et al. (2010 ▶); Huang & Wu (2010 ▶); Ji & Lu (2010 ▶); Khaledi et al. (2010 ▶); Singh & Singh (2010 ▶); Zhou & Yang (2010 ▶). For background to hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For hydrogen-bonding motifs, see: Etter et al. (1990 ▶). PLATON (Spek, 2009 ▶) was used to analyse the π–π inter­actions.

Experimental

Crystal data

C14H11N3O4

M = 285.26

Monoclinic,

a = 9.987 (3) Å

b = 8.967 (3) Å

c = 15.108 (4) Å

β = 106.560 (3)°

V = 1296.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.986, T max = 0.989

6579 measured reflections

2768 independent reflections

1787 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.03

2768 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 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/S1600536810043564/fb2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043564/fb2226Isup2.hkl

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

C14H11N3O4	F(000) = 592
Mr = 285.26	Dx = 1.461 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1436 reflections
a = 9.987 (3) Å	θ = 2.7–26.3°
b = 8.967 (3) Å	µ = 0.11 mm−1
c = 15.108 (4) Å	T = 298 K
β = 106.560 (3)°	Block, yellow
V = 1296.8 (6) Å3	0.13 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2768 independent reflections
Radiation source: fine-focus sealed tube	1787 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→12
Tmin = 0.986, Tmax = 0.989	k = −11→10
6579 measured reflections	l = −18→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.0632P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2768 reflections	Δρmax = 0.21 e Å−3
197 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
38 constraints	Extinction coefficient: 0.0088 (17)
Primary atom site location: structure-invariant direct methods

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	0.00619 (14)	0.30350 (16)	0.94081 (9)	0.0406 (4)
N2	0.12358 (14)	0.36267 (16)	1.00310 (10)	0.0398 (4)
N3	0.69398 (17)	0.6801 (2)	1.24192 (14)	0.0589 (5)
O1	−0.42069 (13)	0.13866 (16)	0.68671 (8)	0.0555 (4)
H1	−0.493 (2)	0.089 (2)	0.6608 (16)	0.083*
O2	0.16825 (12)	0.52109 (15)	0.89819 (8)	0.0533 (4)
O3	0.76141 (18)	0.7733 (2)	1.21577 (13)	0.0993 (6)
O4	0.72752 (16)	0.62850 (19)	1.31937 (12)	0.0842 (6)
C1	−0.18157 (16)	0.12789 (18)	0.91821 (11)	0.0359 (4)
C2	−0.24225 (16)	0.16628 (19)	0.82649 (11)	0.0372 (4)
H2A	−0.2025	0.2405	0.7992	0.045*
C3	−0.36203 (17)	0.0939 (2)	0.77569 (11)	0.0385 (4)
C4	−0.42103 (19)	−0.0178 (2)	0.81556 (13)	0.0452 (5)
H4	−0.5005	−0.0675	0.7810	0.054*
C5	−0.3613 (2)	−0.0546 (2)	0.90643 (14)	0.0502 (5)
H5	−0.4015	−0.1290	0.9334	0.060*
C6	−0.24222 (18)	0.0171 (2)	0.95848 (13)	0.0449 (5)
H6	−0.2029	−0.0086	1.0201	0.054*
C7	−0.05675 (17)	0.20413 (19)	0.97439 (12)	0.0393 (4)
H7	−0.0222	0.1794	1.0365	0.047*
C8	0.19947 (16)	0.4687 (2)	0.97659 (12)	0.0369 (4)
C9	0.32783 (16)	0.52089 (18)	1.04872 (11)	0.0341 (4)
C10	0.39976 (17)	0.64059 (19)	1.02656 (12)	0.0400 (4)
H10	0.3676	0.6855	0.9689	0.048*
C11	0.51947 (18)	0.6937 (2)	1.09002 (13)	0.0438 (5)
H11	0.5681	0.7742	1.0756	0.053*
C12	0.56488 (16)	0.62500 (19)	1.17461 (12)	0.0410 (5)
C13	0.49633 (17)	0.50675 (19)	1.19882 (12)	0.0437 (5)
H13	0.5292	0.4624	1.2566	0.052*
C14	0.37696 (16)	0.45478 (19)	1.13512 (11)	0.0407 (5)
H14	0.3289	0.3745	1.1503	0.049*
H2	0.1392 (19)	0.341 (2)	1.0640 (14)	0.061*

	U11	U22	U33	U12	U13	U23
N1	0.0314 (7)	0.0502 (9)	0.0331 (8)	0.0010 (7)	−0.0021 (6)	−0.0075 (7)
N2	0.0340 (7)	0.0487 (9)	0.0295 (8)	−0.0019 (7)	−0.0027 (6)	−0.0017 (7)
N3	0.0419 (9)	0.0546 (11)	0.0707 (13)	−0.0056 (8)	0.0008 (9)	−0.0167 (10)
O1	0.0436 (8)	0.0827 (11)	0.0308 (7)	−0.0161 (7)	−0.0046 (6)	0.0000 (7)
O2	0.0411 (7)	0.0761 (10)	0.0353 (8)	0.0012 (6)	−0.0006 (6)	0.0098 (7)
O3	0.0719 (11)	0.1000 (14)	0.1113 (15)	−0.0481 (10)	0.0023 (10)	−0.0048 (11)
O4	0.0703 (10)	0.0935 (13)	0.0634 (11)	−0.0126 (9)	−0.0219 (8)	−0.0066 (10)
C1	0.0327 (9)	0.0371 (10)	0.0347 (10)	0.0047 (7)	0.0042 (7)	−0.0060 (8)
C2	0.0333 (9)	0.0449 (10)	0.0321 (10)	−0.0018 (7)	0.0074 (7)	−0.0039 (8)
C3	0.0331 (9)	0.0494 (11)	0.0302 (10)	−0.0001 (8)	0.0047 (7)	−0.0067 (8)
C4	0.0407 (10)	0.0486 (11)	0.0429 (11)	−0.0097 (8)	0.0064 (8)	−0.0084 (9)
C5	0.0558 (12)	0.0425 (11)	0.0509 (12)	−0.0084 (9)	0.0127 (10)	0.0050 (9)
C6	0.0484 (11)	0.0450 (11)	0.0354 (11)	0.0057 (8)	0.0022 (8)	0.0026 (8)
C7	0.0366 (9)	0.0434 (10)	0.0307 (10)	0.0063 (8)	−0.0021 (7)	−0.0041 (8)
C8	0.0303 (9)	0.0443 (10)	0.0332 (10)	0.0097 (8)	0.0041 (7)	−0.0018 (8)
C9	0.0273 (8)	0.0381 (9)	0.0347 (10)	0.0087 (7)	0.0053 (7)	−0.0034 (7)
C10	0.0402 (9)	0.0441 (11)	0.0367 (10)	0.0056 (8)	0.0126 (8)	0.0024 (8)
C11	0.0412 (10)	0.0405 (10)	0.0523 (12)	−0.0033 (8)	0.0174 (9)	−0.0041 (9)
C12	0.0285 (9)	0.0428 (10)	0.0464 (11)	0.0023 (8)	0.0021 (8)	−0.0098 (9)
C13	0.0379 (10)	0.0454 (11)	0.0395 (11)	0.0037 (8)	−0.0027 (8)	0.0022 (8)
C14	0.0342 (9)	0.0404 (10)	0.0406 (11)	−0.0016 (7)	−0.0002 (8)	0.0027 (8)

N1—C7	1.276 (2)	C4—H4	0.9300
N1—N2	1.3830 (18)	C5—C6	1.383 (3)
N2—C8	1.346 (2)	C5—H5	0.9300
N2—H2	0.91 (2)	C6—H6	0.9300
N3—O3	1.208 (2)	C7—H7	0.9300
N3—O4	1.213 (2)	C8—C9	1.501 (2)
N3—C12	1.481 (2)	C9—C10	1.385 (2)
O1—C3	1.365 (2)	C9—C14	1.390 (2)
O1—H1	0.85 (2)	C10—C11	1.386 (2)
O2—C8	1.229 (2)	C10—H10	0.9300
C1—C2	1.388 (2)	C11—C12	1.374 (2)
C1—C6	1.391 (2)	C11—H11	0.9300
C1—C7	1.462 (2)	C12—C13	1.367 (2)
C2—C3	1.385 (2)	C13—C14	1.382 (2)
C2—H2A	0.9300	C13—H13	0.9300
C3—C4	1.384 (2)	C14—H14	0.9300
C4—C5	1.372 (3)
C7—N1—N2	114.55 (14)	C1—C6—H6	120.2
C8—N2—N1	120.57 (14)	N1—C7—C1	122.05 (16)
C8—N2—H2	120.2 (12)	N1—C7—H7	119.0
N1—N2—H2	118.3 (12)	C1—C7—H7	119.0
O3—N3—O4	123.56 (18)	O2—C8—N2	123.16 (15)
O3—N3—C12	117.62 (19)	O2—C8—C9	120.68 (16)
O4—N3—C12	118.81 (18)	N2—C8—C9	116.16 (15)
C3—O1—H1	111.7 (16)	C10—C9—C14	119.29 (15)
C2—C1—C6	119.55 (15)	C10—C9—C8	117.42 (15)
C2—C1—C7	121.39 (16)	C14—C9—C8	123.29 (16)
C6—C1—C7	119.04 (15)	C9—C10—C11	120.24 (16)
C3—C2—C1	119.96 (17)	C9—C10—H10	119.9
C3—C2—H2A	120.0	C11—C10—H10	119.9
C1—C2—H2A	120.0	C12—C11—C10	118.70 (17)
O1—C3—C4	121.66 (15)	C12—C11—H11	120.7
O1—C3—C2	117.95 (16)	C10—C11—H11	120.7
C4—C3—C2	120.37 (16)	C13—C12—C11	122.60 (15)
C5—C4—C3	119.48 (16)	C13—C12—N3	118.64 (17)
C5—C4—H4	120.3	C11—C12—N3	118.75 (17)
C3—C4—H4	120.3	C12—C13—C14	118.26 (16)
C4—C5—C6	120.98 (18)	C12—C13—H13	120.9
C4—C5—H5	119.5	C14—C13—H13	120.9
C6—C5—H5	119.5	C13—C14—C9	120.91 (17)
C5—C6—C1	119.64 (17)	C13—C14—H14	119.5
C5—C6—H6	120.2	C9—C14—H14	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.91 (2)	2.11 (2)	2.931 (2)	149.3 (16)
O1—H1···O2ii	0.85 (2)	1.82 (2)	2.6573 (17)	167 (2)

Centroid–centroid*	Distance (Å)	Symmetry code
Cg1–Cg2	3.6803 (16)	1 - x, -y, 1 - z

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.91 (2)	2.11 (2)	2.931 (2)	149.3 (16)
O1—H1⋯O2ii	0.85 (2)	1.82 (2)	2.6573 (17)	167 (2)

Symmetry codes: (i) ; (ii) .

Table 2

Overview of π–π ring inter­actions in the structure

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 benzene rings, respectively.

Centroid–centroid	Distance (Å)	Symmetry code
Cg1–Cg2	3.6803 (16)	1 − x, −y, 1 − z