(E)-N'-(3,4-Dihydroxy-benzyl-idene)-4-nitro-benzohydrazide.

In the title Schiff base compound, C(14)H(11)N(3)O(5), the dihedral angle between the two benzene rings is 1.6 (1)°. The mol-ecule displays an E configuration about the C=N bond. An intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into layers parallel to (101) by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. One of the hydroxyl groups is disordered over two positions, with occupancies of 0.643 (5) and 0.357 (5).

Related literature

For the biological properties of Schiff base compounds, see: Kucukguzel et al. (2006 ▶); Khattab (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶); Qiu & Zhao (2008 ▶).

Experimental

Crystal data

C14H11N3O5

M = 301.26

Monoclinic,

a = 7.666 (1) Å

b = 13.196 (2) Å

c = 13.176 (2) Å

β = 95.361 (3)°

V = 1327.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 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; Bruker, 2001 ▶) T min = 0.977, T max = 0.979

8322 measured reflections

3204 independent reflections

1364 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.161

S = 1.02

3204 reflections

210 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809029705/ci2865sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029705/ci2865Isup2.hkl

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

C14H11N3O5	F(000) = 624
Mr = 301.26	Dx = 1.508 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1038 reflections
a = 7.666 (1) Å	θ = 2.5–24.5°
b = 13.196 (2) Å	µ = 0.12 mm−1
c = 13.176 (2) Å	T = 298 K
β = 95.361 (3)°	Block, colourless
V = 1327.1 (3) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	1364 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.977, Tmax = 0.979	k = −16→17
8322 measured reflections	l = −17→10

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4176P] where P = (Fo2 + 2Fc2)/3
3204 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.23 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	Occ. (<1)
O1	0.6818 (3)	1.15446 (15)	0.09056 (17)	0.0606 (6)
O2	0.5123 (3)	0.56081 (15)	0.27427 (16)	0.0661 (7)
H2A	0.4520	0.5825	0.3177	0.099*
O3	0.6235 (5)	0.5128 (2)	0.0971 (3)	0.0814 (15)	0.643 (5)
H3A	0.6013	0.4782	0.1460	0.122*	0.643 (5)
O4	1.0449 (3)	1.43595 (18)	−0.3087 (2)	0.0749 (7)
O5	0.9668 (4)	1.5401 (2)	−0.1968 (2)	0.1037 (10)
N1	0.9797 (4)	1.4543 (2)	−0.2301 (2)	0.0648 (8)
N2	0.7625 (3)	1.03529 (18)	−0.01803 (18)	0.0508 (7)
H2B	0.7895	1.0090	−0.0778	0.061*
N3	0.7082 (3)	0.9614 (2)	0.04686 (19)	0.0524 (7)
C1	0.9174 (4)	1.3697 (2)	−0.1705 (2)	0.0513 (8)
C2	0.8561 (4)	1.3914 (2)	−0.0783 (3)	0.0601 (9)
H2	0.8517	1.4579	−0.0552	0.072*
C3	0.8013 (4)	1.3123 (2)	−0.0209 (2)	0.0572 (9)
H3	0.7599	1.3255	0.0419	0.069*
C4	0.8072 (4)	1.2134 (2)	−0.0558 (2)	0.0438 (7)
C5	0.8690 (4)	1.1948 (2)	−0.1500 (2)	0.0521 (8)
H5	0.8723	1.1288	−0.1745	0.063*
C6	0.9252 (4)	1.2736 (2)	−0.2070 (2)	0.0558 (9)
H6	0.9679	1.2613	−0.2696	0.067*
C7	0.7446 (4)	1.1325 (2)	0.0104 (2)	0.0475 (8)
C8	0.7224 (4)	0.8695 (2)	0.0199 (2)	0.0501 (8)
H8	0.7655	0.8536	−0.0418	0.060*
C9	0.6702 (4)	0.7893 (2)	0.0869 (2)	0.0468 (8)
C10	0.6126 (4)	0.8135 (2)	0.1810 (2)	0.0522 (9)
H10	0.6094	0.8811	0.2008	0.063*
C11	0.5601 (4)	0.7403 (2)	0.2447 (2)	0.0544 (9)
H11	0.5232	0.7582	0.3076	0.065*	0.643 (5)
C12	0.5617 (4)	0.6395 (2)	0.2157 (2)	0.0480 (8)
C13	0.6193 (4)	0.6140 (2)	0.1230 (2)	0.0532 (8)
H13	0.6224	0.5464	0.1034	0.064*	0.357 (5)
C14	0.6724 (4)	0.6884 (2)	0.0591 (2)	0.0522 (9)
H14	0.7103	0.6705	−0.0034	0.063*
O3'	0.5167 (10)	0.7811 (5)	0.3302 (5)	0.076 (3)	0.357 (5)
H3'	0.4225	0.7579	0.3439	0.115*	0.357 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0805 (16)	0.0506 (14)	0.0549 (14)	0.0031 (12)	0.0283 (12)	−0.0007 (11)
O2	0.0902 (17)	0.0484 (14)	0.0645 (15)	0.0031 (12)	0.0320 (13)	0.0033 (11)
O3	0.140 (4)	0.037 (2)	0.073 (3)	0.005 (2)	0.046 (2)	−0.0088 (18)
O4	0.0773 (17)	0.0780 (18)	0.0740 (18)	−0.0035 (14)	0.0315 (14)	0.0168 (14)
O5	0.155 (3)	0.0525 (17)	0.111 (2)	−0.0188 (18)	0.056 (2)	0.0086 (16)
N1	0.072 (2)	0.052 (2)	0.072 (2)	−0.0078 (16)	0.0208 (17)	0.0113 (17)
N2	0.0662 (18)	0.0403 (16)	0.0484 (16)	−0.0003 (13)	0.0187 (14)	−0.0016 (13)
N3	0.0616 (17)	0.0433 (16)	0.0541 (16)	−0.0017 (13)	0.0149 (14)	0.0068 (13)
C1	0.052 (2)	0.051 (2)	0.053 (2)	0.0002 (16)	0.0145 (17)	0.0112 (16)
C2	0.072 (2)	0.043 (2)	0.068 (2)	0.0001 (17)	0.022 (2)	−0.0005 (18)
C3	0.067 (2)	0.051 (2)	0.056 (2)	0.0041 (18)	0.0228 (18)	−0.0038 (17)
C4	0.0455 (18)	0.0404 (19)	0.0466 (19)	0.0010 (14)	0.0104 (15)	0.0028 (15)
C5	0.066 (2)	0.0407 (19)	0.053 (2)	0.0041 (16)	0.0205 (17)	0.0017 (15)
C6	0.062 (2)	0.056 (2)	0.052 (2)	0.0038 (17)	0.0179 (17)	0.0021 (17)
C7	0.0461 (19)	0.049 (2)	0.048 (2)	0.0023 (15)	0.0087 (16)	−0.0006 (16)
C8	0.054 (2)	0.047 (2)	0.051 (2)	0.0012 (16)	0.0123 (16)	0.0010 (16)
C9	0.0479 (19)	0.0414 (19)	0.052 (2)	−0.0001 (15)	0.0093 (16)	0.0005 (16)
C10	0.064 (2)	0.0330 (18)	0.062 (2)	−0.0018 (15)	0.0148 (18)	−0.0035 (15)
C11	0.066 (2)	0.047 (2)	0.052 (2)	0.0009 (17)	0.0120 (18)	−0.0043 (17)
C12	0.056 (2)	0.0382 (19)	0.052 (2)	−0.0007 (15)	0.0152 (17)	0.0068 (15)
C13	0.062 (2)	0.0387 (19)	0.060 (2)	0.0011 (16)	0.0156 (18)	−0.0049 (17)
C14	0.057 (2)	0.050 (2)	0.052 (2)	0.0006 (16)	0.0160 (17)	−0.0035 (16)
O3'	0.116 (7)	0.066 (5)	0.053 (4)	−0.018 (4)	0.040 (4)	−0.011 (3)

O1—C7	1.236 (3)	C4—C7	1.487 (4)
O2—C12	1.367 (3)	C5—C6	1.375 (4)
O2—H2A	0.82	C5—H5	0.93
O3—C13	1.379 (4)	C6—H6	0.93
O3—H3A	0.82	C8—C9	1.458 (4)
O4—N1	1.216 (3)	C8—H8	0.93
O5—N1	1.221 (3)	C9—C14	1.382 (4)
N1—C1	1.469 (4)	C9—C10	1.390 (4)
N2—C7	1.346 (4)	C10—C11	1.365 (4)
N2—N3	1.386 (3)	C10—H10	0.93
N2—H2B	0.90	C11—O3'	1.319 (5)
N3—C8	1.271 (3)	C11—C12	1.385 (4)
C1—C6	1.360 (4)	C11—H11	0.93
C1—C2	1.373 (4)	C12—C13	1.380 (4)
C2—C3	1.377 (4)	C13—C14	1.379 (4)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.387 (4)	C14—H14	0.93
C3—H3	0.93	O3'—H3'	0.82
C4—C5	1.390 (4)
C12—O2—H2A	109.5	O1—C7—C4	120.4 (3)
C13—O3—H3A	109.5	N2—C7—C4	118.3 (3)
O4—N1—O5	123.0 (3)	N3—C8—C9	119.2 (3)
O4—N1—C1	118.9 (3)	N3—C8—H8	120.4
O5—N1—C1	118.1 (3)	C9—C8—H8	120.4
C7—N2—N3	117.0 (2)	C14—C9—C10	118.1 (3)
C7—N2—H2B	130.3	C14—C9—C8	121.8 (3)
N3—N2—H2B	112.0	C10—C9—C8	120.1 (3)
C8—N3—N2	117.4 (3)	C11—C10—C9	121.5 (3)
C6—C1—C2	122.4 (3)	C11—C10—H10	119.2
C6—C1—N1	119.5 (3)	C9—C10—H10	119.2
C2—C1—N1	118.0 (3)	O3'—C11—C10	110.5 (4)
C1—C2—C3	118.4 (3)	O3'—C11—C12	129.6 (4)
C1—C2—H2	120.8	C10—C11—C12	119.9 (3)
C3—C2—H2	120.8	C10—C11—H11	120.0
C2—C3—C4	120.7 (3)	C12—C11—H11	120.0
C2—C3—H3	119.7	O2—C12—C13	116.3 (3)
C4—C3—H3	119.7	O2—C12—C11	124.3 (3)
C3—C4—C5	119.1 (3)	C13—C12—C11	119.4 (3)
C3—C4—C7	117.4 (3)	C14—C13—O3	121.6 (3)
C5—C4—C7	123.5 (3)	C14—C13—C12	120.3 (3)
C6—C5—C4	120.3 (3)	O3—C13—C12	118.1 (3)
C6—C5—H5	119.9	C14—C13—H13	119.8
C4—C5—H5	119.9	C12—C13—H13	119.8
C1—C6—C5	119.1 (3)	C13—C14—C9	120.8 (3)
C1—C6—H6	120.4	C13—C14—H14	119.6
C5—C6—H6	120.4	C9—C14—H14	119.5
O1—C7—N2	121.3 (3)	C11—O3'—H3'	109.5
C7—N2—N3—C8	179.0 (3)	C5—C4—C7—N2	5.9 (4)
O4—N1—C1—C6	−3.5 (5)	N2—N3—C8—C9	178.7 (3)
O5—N1—C1—C6	178.1 (3)	N3—C8—C9—C14	176.0 (3)
O4—N1—C1—C2	175.3 (3)	N3—C8—C9—C10	−2.7 (5)
O5—N1—C1—C2	−3.1 (5)	C14—C9—C10—C11	0.2 (5)
C6—C1—C2—C3	0.2 (5)	C8—C9—C10—C11	178.9 (3)
N1—C1—C2—C3	−178.5 (3)	C9—C10—C11—O3'	178.0 (4)
C1—C2—C3—C4	−0.3 (5)	C9—C10—C11—C12	−0.7 (5)
C2—C3—C4—C5	−0.2 (5)	O3'—C11—C12—O2	1.3 (7)
C2—C3—C4—C7	−179.6 (3)	C10—C11—C12—O2	179.7 (3)
C3—C4—C5—C6	0.7 (5)	O3'—C11—C12—C13	−177.4 (5)
C7—C4—C5—C6	−179.8 (3)	C10—C11—C12—C13	1.1 (5)
C2—C1—C6—C5	0.3 (5)	O2—C12—C13—C14	−179.8 (3)
N1—C1—C6—C5	179.1 (3)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−0.8 (5)	O2—C12—C13—O3	−0.3 (5)
N3—N2—C7—O1	−0.3 (4)	C11—C12—C13—O3	178.5 (3)
N3—N2—C7—C4	178.0 (2)	O3—C13—C14—C9	−178.9 (3)
C3—C4—C7—O1	3.6 (4)	C12—C13—C14—C9	0.5 (5)
C5—C4—C7—O1	−175.8 (3)	C10—C9—C14—C13	−0.1 (5)
C3—C4—C7—N2	−174.6 (3)	C8—C9—C14—C13	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	2.17	2.636 (4)	116
O2—H2A···O1i	0.82	1.91	2.722 (3)	171
O3'—H3'···O1i	0.82	1.84	2.548 (7)	144
N2—H2B···O4ii	0.90	2.26	3.121 (3)	158
C5—H5···O5ii	0.93	2.48	3.210 (4)	135
C10—H10···O2iii	0.93	2.58	3.467 (3)	159
C11—H11···O1i	0.93	2.56	3.192 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	2.17	2.636 (4)	116
O2—H2A⋯O1i	0.82	1.91	2.722 (3)	171
O3′—H3′⋯O1i	0.82	1.84	2.548 (7)	144
N2—H2B⋯O4ii	0.90	2.26	3.121 (3)	158
C5—H5⋯O5ii	0.93	2.48	3.210 (4)	135
C10—H10⋯O2iii	0.93	2.58	3.467 (3)	159
C11—H11⋯O1i	0.93	2.56	3.192 (4)	126

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