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

The mol-ecule of the title compound, C(14)H(11)N(3)O(5), assumes an E configuration with respect to the methyl-idene unit. An intra-molecular O-H⋯O hydrogen bond is present in the mol-ecule. The dihedral angle between the mean planes of the two benzene rings is 5.46 (15)°. The crystal structure is stabilized by inter-molecular O-H⋯O, O-H⋯N, and N-H⋯O hydrogen bonds.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Fan et al. (2010 ▶); Rasras et al. (2010 ▶). For similar hydrazone compounds, see: Ahmad et al. (2010 ▶); Ban (2010 ▶); Ji & Lu (2010 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C14H11N3O5

M = 301.26

Monoclinic,

a = 8.786 (3) Å

b = 14.882 (2) Å

c = 10.3064 (17) Å

β = 91.100 (2)°

V = 1347.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.32 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.967

7079 measured reflections

2952 independent reflections

1353 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.137

S = 1.06

2952 reflections

204 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811000195/su2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000195/su2243Isup2.hkl

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

C14H11N3O5	F(000) = 624
Mr = 301.26	Dx = 1.485 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.786 (3) Å	Cell parameters from 1674 reflections
b = 14.882 (2) Å	θ = 2.4–26.9°
c = 10.3064 (17) Å	µ = 0.12 mm−1
β = 91.100 (2)°	T = 298 K
V = 1347.3 (5) Å3	Block, yellow
Z = 4	0.32 × 0.30 × 0.29 mm

Bruker SMART APEX CCD area-detector diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	1353 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→11
Tmin = 0.964, Tmax = 0.967	k = −19→19
7079 measured reflections	l = −13→7

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0262P)2 + 0.9404P] where P = (Fo2 + 2Fc2)/3
2952 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.21 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	0.4602 (3)	0.40859 (16)	0.1386 (3)	0.0442 (7)
N2	0.3606 (3)	0.34194 (16)	0.0989 (3)	0.0419 (7)
O1	1.0054 (2)	0.64891 (13)	0.3680 (3)	0.0577 (7)
H1A	0.9704	0.6998	0.3614	0.087*
O2	0.6482 (2)	0.30744 (13)	0.1654 (2)	0.0521 (7)
O3	−0.2256 (3)	0.12672 (15)	−0.0998 (3)	0.0675 (8)
H3	−0.3047	0.1529	−0.1200	0.101*
O4	−0.3830 (3)	0.26935 (19)	−0.1553 (3)	0.0766 (9)
O5	−0.2875 (3)	0.40196 (19)	−0.1256 (3)	0.0801 (9)
C1	0.7049 (3)	0.45812 (18)	0.2226 (3)	0.0344 (7)
C2	0.6644 (3)	0.54841 (18)	0.2232 (3)	0.0411 (8)
H2	0.5691	0.5655	0.1909	0.049*
C3	0.7623 (3)	0.61274 (19)	0.2707 (3)	0.0432 (8)
H3A	0.7332	0.6728	0.2699	0.052*
C4	0.9033 (3)	0.58892 (19)	0.3194 (3)	0.0398 (8)
C5	0.9456 (4)	0.49917 (19)	0.3202 (3)	0.0503 (10)
H5	1.0406	0.4824	0.3534	0.060*
C6	0.8471 (3)	0.4349 (2)	0.2720 (3)	0.0503 (10)
H6	0.8766	0.3749	0.2726	0.060*
C7	0.6036 (3)	0.38575 (19)	0.1743 (3)	0.0382 (8)
C8	0.2280 (4)	0.3678 (2)	0.0654 (3)	0.0444 (9)
H8	0.2047	0.4287	0.0685	0.053*
C9	0.1110 (3)	0.3044 (2)	0.0222 (3)	0.0398 (8)
C10	−0.0244 (3)	0.3372 (2)	−0.0261 (3)	0.0428 (8)
H10	−0.0398	0.3989	−0.0301	0.051*
C11	−0.1385 (3)	0.2798 (2)	−0.0692 (3)	0.0410 (8)
C12	−0.1193 (4)	0.1874 (2)	−0.0631 (3)	0.0455 (9)
C13	0.0193 (4)	0.1544 (2)	−0.0147 (3)	0.0486 (9)
H13	0.0347	0.0926	−0.0102	0.058*
C14	0.1324 (4)	0.2110 (2)	0.0262 (3)	0.0446 (9)
H14	0.2243	0.1875	0.0569	0.053*
N3	−0.2779 (3)	0.3202 (2)	−0.1195 (3)	0.0561 (8)
H1	0.424 (3)	0.4649 (10)	0.144 (3)	0.067*

	U11	U22	U33	U12	U13	U23
N1	0.0310 (16)	0.0268 (13)	0.075 (2)	0.0000 (12)	−0.0032 (14)	−0.0041 (14)
N2	0.0364 (17)	0.0336 (14)	0.0558 (19)	−0.0036 (12)	0.0034 (14)	−0.0015 (13)
O1	0.0463 (15)	0.0301 (12)	0.0962 (19)	−0.0006 (11)	−0.0149 (14)	−0.0028 (13)
O2	0.0450 (14)	0.0267 (11)	0.0845 (18)	0.0024 (10)	−0.0015 (12)	−0.0041 (12)
O3	0.0593 (17)	0.0626 (16)	0.081 (2)	−0.0226 (13)	−0.0018 (15)	−0.0094 (15)
O4	0.0474 (17)	0.094 (2)	0.088 (2)	−0.0095 (16)	−0.0138 (15)	−0.0119 (17)
O5	0.0598 (18)	0.0628 (18)	0.117 (2)	0.0151 (15)	−0.0165 (16)	0.0017 (17)
C1	0.0307 (18)	0.0281 (15)	0.045 (2)	−0.0001 (13)	0.0075 (15)	0.0008 (14)
C2	0.033 (2)	0.0310 (17)	0.060 (2)	0.0037 (14)	0.0008 (17)	0.0031 (15)
C3	0.040 (2)	0.0259 (16)	0.064 (2)	0.0021 (14)	0.0000 (17)	0.0058 (16)
C4	0.0373 (19)	0.0296 (16)	0.052 (2)	−0.0024 (14)	0.0029 (17)	−0.0002 (15)
C5	0.036 (2)	0.0318 (17)	0.082 (3)	0.0063 (16)	−0.0109 (19)	−0.0018 (18)
C6	0.043 (2)	0.0273 (17)	0.080 (3)	0.0083 (15)	−0.004 (2)	−0.0029 (17)
C7	0.037 (2)	0.0315 (17)	0.046 (2)	0.0021 (14)	0.0081 (16)	0.0033 (15)
C8	0.041 (2)	0.0315 (17)	0.061 (2)	0.0032 (15)	0.0027 (18)	0.0009 (16)
C9	0.0335 (19)	0.0374 (17)	0.049 (2)	−0.0010 (14)	0.0075 (16)	0.0014 (16)
C10	0.037 (2)	0.0374 (18)	0.054 (2)	0.0014 (15)	0.0057 (17)	−0.0008 (16)
C11	0.034 (2)	0.048 (2)	0.042 (2)	0.0007 (15)	0.0065 (16)	−0.0042 (16)
C12	0.044 (2)	0.050 (2)	0.042 (2)	−0.0134 (17)	0.0061 (17)	−0.0068 (17)
C13	0.055 (2)	0.0335 (17)	0.057 (2)	−0.0027 (17)	0.0083 (19)	−0.0020 (17)
C14	0.041 (2)	0.0375 (19)	0.056 (2)	−0.0010 (15)	0.0033 (17)	0.0012 (16)
N3	0.0403 (19)	0.071 (2)	0.057 (2)	0.0008 (17)	0.0035 (16)	−0.0043 (17)

N1—C7	1.349 (4)	C3—H3A	0.9300
N1—N2	1.380 (3)	C4—C5	1.387 (4)
N1—H1	0.899 (10)	C5—C6	1.376 (4)
N2—C8	1.269 (4)	C5—H5	0.9300
O1—C4	1.355 (3)	C6—H6	0.9300
O1—H1A	0.8200	C8—C9	1.458 (4)
O2—C7	1.234 (3)	C8—H8	0.9300
O3—C12	1.347 (4)	C9—C10	1.371 (4)
O3—H3	0.8200	C9—C14	1.403 (4)
O4—N3	1.244 (3)	C10—C11	1.383 (4)
O5—N3	1.222 (4)	C10—H10	0.9300
C1—C6	1.383 (4)	C11—C12	1.387 (4)
C1—C2	1.390 (4)	C11—N3	1.451 (4)
C1—C7	1.478 (4)	C12—C13	1.396 (4)
C2—C3	1.371 (4)	C13—C14	1.363 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.374 (4)	C14—H14	0.9300
C7—N1—N2	118.9 (2)	N1—C7—C1	117.5 (3)
C7—N1—H1	123 (2)	N2—C8—C9	121.7 (3)
N2—N1—H1	118 (2)	N2—C8—H8	119.2
C8—N2—N1	115.9 (2)	C9—C8—H8	119.2
C4—O1—H1A	109.5	C10—C9—C14	118.5 (3)
C12—O3—H3	109.5	C10—C9—C8	118.9 (3)
C6—C1—C2	118.0 (3)	C14—C9—C8	122.6 (3)
C6—C1—C7	118.4 (3)	C9—C10—C11	121.0 (3)
C2—C1—C7	123.6 (3)	C9—C10—H10	119.5
C3—C2—C1	121.1 (3)	C11—C10—H10	119.5
C3—C2—H2	119.4	C10—C11—C12	120.8 (3)
C1—C2—H2	119.4	C10—C11—N3	117.4 (3)
C2—C3—C4	120.4 (3)	C12—C11—N3	121.9 (3)
C2—C3—H3A	119.8	O3—C12—C11	124.7 (3)
C4—C3—H3A	119.8	O3—C12—C13	117.3 (3)
O1—C4—C3	123.4 (3)	C11—C12—C13	118.0 (3)
O1—C4—C5	117.2 (3)	C14—C13—C12	121.2 (3)
C3—C4—C5	119.4 (3)	C14—C13—H13	119.4
C6—C5—C4	120.0 (3)	C12—C13—H13	119.4
C6—C5—H5	120.0	C13—C14—C9	120.5 (3)
C4—C5—H5	120.0	C13—C14—H14	119.8
C5—C6—C1	121.1 (3)	C9—C14—H14	119.8
C5—C6—H6	119.4	O5—N3—O4	122.7 (3)
C1—C6—H6	119.4	O5—N3—C11	119.2 (3)
O2—C7—N1	120.9 (3)	O4—N3—C11	118.1 (3)
O2—C7—C1	121.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.82	1.93	2.736 (3)	169
O1—H1A···N2i	0.82	2.61	3.121 (3)	122
O3—H3···O4	0.82	1.90	2.592 (4)	142
N1—H1···O5ii	0.90 (1)	2.32 (1)	3.203 (4)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.82	1.93	2.736 (3)	169
O1—H1A⋯N2i	0.82	2.61	3.121 (3)	122
O3—H3⋯O4	0.82	1.90	2.592 (4)	142
N1—H1⋯O5ii	0.90 (1)	2.32 (1)	3.203 (4)	167 (3)

Symmetry codes: (i) ; (ii) .