(E)-N'-(2,4-Dihy-droxy-benzyl-idene)-4-nitro-benzohydrazide.

The title compound, C(14)H(11)N(3)O(5), is essentially planar, with an r.m.s. deviation for the non-H atoms of 0.0832 (3) Å. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link adjacent mol-ecules into layers parallel to (101). These layers are further connected into a three-dimensional network via C-H⋯O inter-actions. In addition, a π-π inter-action occurs between the aromatic rings [centroid-centroid distance = 3.5425 (8) Å]. An intra-molecular O-H⋯N hydrogen bond is also observed.

Related literature

For related structures, see: Han & Zhao (2010 ▶); Mohd Lair et al. (2009 ▶); Raj et al. (2008 ▶).

Experimental

Crystal data

C14H11N3O5

M = 301.26

Monoclinic,

a = 8.0248 (1) Å

b = 12.5674 (2) Å

c = 12.8770 (2) Å

β = 96.732 (1)°

V = 1289.70 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.21 × 0.15 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.990

10373 measured reflections

2398 independent reflections

2004 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.05

2398 reflections

208 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002224/is2667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002224/is2667Isup2.hkl

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

C14H11N3O5	F(000) = 624
Mr = 301.26	Dx = 1.552 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3471 reflections
a = 8.0248 (1) Å	θ = 3.2–30.4°
b = 12.5674 (2) Å	µ = 0.12 mm−1
c = 12.8770 (2) Å	T = 100 K
β = 96.732 (1)°	Block, orange
V = 1289.70 (3) Å3	0.21 × 0.15 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2398 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.975, Tmax = 0.990	k = −15→12
10373 measured reflections	l = −15→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.2741P] where P = (Fo2 + 2Fc2)/3
2398 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.22 e Å−3
3 restraints	Δρmin = −0.27 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
O1	0.01817 (13)	0.64009 (9)	1.21087 (8)	0.0250 (3)
H1	0.073 (2)	0.5985 (14)	1.1740 (14)	0.038*
O2	−0.25926 (12)	0.97321 (8)	1.19160 (8)	0.0200 (2)
H2A	−0.271 (2)	0.9547 (14)	1.2529 (12)	0.030*
O3	0.31162 (13)	0.40161 (8)	1.11922 (8)	0.0232 (3)
O4	0.70514 (13)	0.04460 (8)	0.83143 (8)	0.0287 (3)
O5	0.69197 (12)	0.15345 (9)	0.70111 (8)	0.0248 (3)
N1	0.15626 (13)	0.57805 (9)	1.04095 (9)	0.0180 (3)
N2	0.23932 (14)	0.50897 (9)	0.98041 (9)	0.0173 (3)
H2B	0.2412 (19)	0.5289 (12)	0.9163 (11)	0.021*
N3	0.66607 (14)	0.13011 (10)	0.79089 (9)	0.0193 (3)
C1	−0.02829 (16)	0.72791 (11)	1.15383 (11)	0.0170 (3)
C2	−0.11597 (16)	0.80504 (11)	1.20227 (11)	0.0171 (3)
H2	−0.1393	0.7950	1.2722	0.021*
C3	−0.16953 (16)	0.89687 (11)	1.14835 (11)	0.0168 (3)
C4	−0.13465 (16)	0.91253 (11)	1.04548 (11)	0.0182 (3)
H4	−0.1708	0.9756	1.0088	0.022*
C5	−0.04773 (16)	0.83605 (11)	0.99795 (11)	0.0178 (3)
H5	−0.0243	0.8472	0.9282	0.021*
C6	0.00759 (16)	0.74153 (11)	1.04988 (11)	0.0165 (3)
C7	0.09681 (16)	0.66335 (11)	0.99533 (11)	0.0178 (3)
H7	0.1119	0.6752	0.9242	0.021*
C8	0.31525 (16)	0.42271 (11)	1.02595 (11)	0.0162 (3)
C9	0.40734 (15)	0.35067 (11)	0.95936 (10)	0.0156 (3)
C10	0.44714 (16)	0.37683 (11)	0.85999 (11)	0.0171 (3)
H10	0.4134	0.4436	0.8299	0.020*
C11	0.53565 (16)	0.30596 (11)	0.80500 (11)	0.0178 (3)
H11	0.5651	0.3237	0.7378	0.021*
C12	0.58004 (16)	0.20868 (11)	0.85038 (11)	0.0171 (3)
C13	0.54399 (16)	0.18076 (11)	0.94917 (11)	0.0183 (3)
H13	0.5776	0.1138	0.9788	0.022*
C14	0.45772 (16)	0.25303 (11)	1.00359 (11)	0.0174 (3)
H14	0.4325	0.2359	1.0719	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0306 (6)	0.0227 (6)	0.0229 (6)	0.0100 (5)	0.0082 (4)	0.0054 (4)
O2	0.0261 (5)	0.0173 (5)	0.0178 (5)	0.0037 (4)	0.0071 (4)	−0.0005 (4)
O3	0.0320 (6)	0.0225 (6)	0.0170 (5)	0.0004 (4)	0.0110 (4)	0.0007 (4)
O4	0.0369 (6)	0.0231 (6)	0.0256 (6)	0.0117 (5)	0.0013 (5)	−0.0019 (5)
O5	0.0252 (5)	0.0326 (6)	0.0179 (5)	0.0014 (5)	0.0076 (4)	−0.0044 (4)
N1	0.0152 (5)	0.0186 (6)	0.0209 (6)	−0.0013 (5)	0.0057 (5)	−0.0055 (5)
N2	0.0182 (6)	0.0190 (6)	0.0156 (6)	0.0005 (5)	0.0063 (5)	−0.0032 (5)
N3	0.0165 (6)	0.0231 (7)	0.0180 (6)	0.0001 (5)	0.0003 (5)	−0.0053 (5)
C1	0.0145 (6)	0.0173 (7)	0.0190 (7)	−0.0017 (5)	0.0007 (5)	0.0010 (6)
C2	0.0169 (6)	0.0207 (7)	0.0142 (7)	−0.0020 (5)	0.0033 (5)	−0.0001 (6)
C3	0.0147 (6)	0.0165 (7)	0.0194 (7)	−0.0025 (5)	0.0027 (5)	−0.0030 (6)
C4	0.0184 (6)	0.0165 (7)	0.0196 (7)	−0.0003 (5)	0.0021 (5)	0.0027 (6)
C5	0.0179 (7)	0.0221 (8)	0.0139 (7)	−0.0035 (6)	0.0039 (5)	0.0001 (5)
C6	0.0135 (6)	0.0182 (7)	0.0182 (7)	−0.0028 (5)	0.0036 (5)	−0.0020 (6)
C7	0.0141 (6)	0.0212 (7)	0.0183 (7)	−0.0040 (5)	0.0029 (5)	−0.0021 (6)
C8	0.0158 (6)	0.0166 (7)	0.0167 (7)	−0.0056 (5)	0.0039 (5)	−0.0020 (6)
C9	0.0135 (6)	0.0163 (7)	0.0169 (7)	−0.0038 (5)	0.0016 (5)	−0.0029 (5)
C10	0.0178 (6)	0.0162 (7)	0.0172 (7)	−0.0016 (5)	0.0023 (5)	0.0004 (5)
C11	0.0171 (6)	0.0220 (7)	0.0147 (7)	−0.0029 (6)	0.0033 (5)	−0.0014 (6)
C12	0.0134 (6)	0.0193 (7)	0.0185 (7)	−0.0008 (5)	0.0023 (5)	−0.0062 (6)
C13	0.0180 (7)	0.0180 (7)	0.0183 (7)	−0.0006 (6)	−0.0005 (5)	−0.0009 (6)
C14	0.0171 (7)	0.0208 (7)	0.0146 (7)	−0.0030 (5)	0.0025 (5)	−0.0008 (6)

O1—C1	1.3537 (17)	C4—C5	1.3729 (19)
O1—H1	0.860 (15)	C4—H4	0.9500
O2—C3	1.3576 (16)	C5—C6	1.409 (2)
O2—H2A	0.839 (14)	C5—H5	0.9500
O3—C8	1.2336 (16)	C6—C7	1.4454 (19)
O4—N3	1.2196 (16)	C7—H7	0.9500
O5—N3	1.2337 (15)	C8—C9	1.4999 (18)
N1—C7	1.2868 (19)	C9—C14	1.3927 (19)
N1—N2	1.3884 (16)	C9—C10	1.3939 (19)
N2—C8	1.3441 (19)	C10—C11	1.3847 (19)
N2—H2B	0.865 (13)	C10—H10	0.9500
N3—C12	1.4705 (17)	C11—C12	1.384 (2)
C1—C2	1.3880 (19)	C11—H11	0.9500
C1—C6	1.4121 (19)	C12—C13	1.3825 (19)
C2—C3	1.389 (2)	C13—C14	1.3817 (19)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.3996 (19)	C14—H14	0.9500
C1—O1—H1	108.8 (13)	C1—C6—C7	123.09 (13)
C3—O2—H2A	108.2 (12)	N1—C7—C6	121.51 (13)
C7—N1—N2	116.19 (12)	N1—C7—H7	119.2
C8—N2—N1	118.83 (12)	C6—C7—H7	119.2
C8—N2—H2B	126.4 (11)	O3—C8—N2	122.48 (12)
N1—N2—H2B	114.7 (11)	O3—C8—C9	119.76 (13)
O4—N3—O5	123.19 (12)	N2—C8—C9	117.77 (12)
O4—N3—C12	118.79 (12)	C14—C9—C10	119.77 (12)
O5—N3—C12	118.00 (12)	C14—C9—C8	115.90 (12)
O1—C1—C2	116.57 (12)	C10—C9—C8	124.31 (13)
O1—C1—C6	122.64 (12)	C11—C10—C9	120.27 (13)
C2—C1—C6	120.78 (13)	C11—C10—H10	119.9
C1—C2—C3	119.94 (13)	C9—C10—H10	119.9
C1—C2—H2	120.0	C12—C11—C10	118.33 (13)
C3—C2—H2	120.0	C12—C11—H11	120.8
O2—C3—C2	122.02 (12)	C10—C11—H11	120.8
O2—C3—C4	117.61 (12)	C13—C12—C11	122.80 (13)
C2—C3—C4	120.36 (12)	C13—C12—N3	118.07 (13)
C5—C4—C3	119.47 (13)	C11—C12—N3	119.12 (12)
C5—C4—H4	120.3	C14—C13—C12	118.11 (13)
C3—C4—H4	120.3	C14—C13—H13	120.9
C4—C5—C6	121.79 (13)	C12—C13—H13	120.9
C4—C5—H5	119.1	C13—C14—C9	120.69 (13)
C6—C5—H5	119.1	C13—C14—H14	119.7
C5—C6—C1	117.65 (12)	C9—C14—H14	119.7
C5—C6—C7	119.27 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.86 (2)	1.93 (2)	2.6818 (15)	146.(2)
O2—H2A···O3i	0.84 (1)	1.84 (2)	2.6759 (14)	173.(2)
N2—H2B···O5ii	0.87 (1)	2.28 (1)	3.0606 (16)	150.(1)
C2—H2···O3i	0.95	2.47	3.1730 (17)	131
C4—H4···O4iii	0.95	2.54	3.3428 (17)	143
C7—H7···O5ii	0.95	2.40	3.2082 (17)	143
C10—H10···O4ii	0.95	2.52	3.3627 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.86 (2)	1.93 (2)	2.6818 (15)	146 (2)
O2—H2A⋯O3i	0.84 (1)	1.84 (2)	2.6759 (14)	173 (2)
N2—H2B⋯O5ii	0.87 (1)	2.28 (1)	3.0606 (16)	150 (1)
C2—H2⋯O3i	0.95	2.47	3.1730 (17)	131
C4—H4⋯O4iii	0.95	2.54	3.3428 (17)	143
C7—H7⋯O5ii	0.95	2.40	3.2082 (17)	143
C10—H10⋯O4ii	0.95	2.52	3.3627 (18)	147

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