(E)-N′-(4-Hy­droxy­benzyl­idene)-2-nitro­benzohydrazide

Liu, S.-Y.; You, Z.

doi:10.1107/S1600536810022075

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1652

doi:10.1107/S1600536810022075

Open

access

(E)-N′-(4-Hydroxybenzylidene)-2-nitrobenzohydrazide

Shi-Yong Liu ^a ^* and Zhonglu You ^b

^aCollege of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and ^bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 7 June 2010; accepted 9 June 2010; online 16 June 2010)

In the title compound, C₁₄H₁₁N₃O₄, the two benzene rings form a dihedral angle of 45.3 (3)°. The nitro group is twisted out of the attached ring by a dihedral angle of 37.5 (3)°. In the crystal structure, molecules are linked into a two-dimensional network parallel to (100) by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ); Zhu et al. (2009 ); Jimenez-Pulido et al. (2008 ); Raj et al. (2007 ); Zhong et al. (2007 ). For the crystal structures of hydrazones, see: Khaledi et al. (2009 ); Warad et al. (2009 ); Back et al. (2009 ); Vijayakumar et al. (2009 ). For related structures, see: Cao (2009 ); Xu et al. (2009 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M_r = 285.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.720 (2) Å
b = 11.398 (3) Å
c = 15.072 (5) Å
V = 1326.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.979, T_max = 0.981
7745 measured reflections
1602 independent reflections
961 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.125
S = 1.02
1602 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.93	2.725 (3)	164
N2—H2A⋯O1ⁱⁱ	0.90 (1)	2.05 (2)	2.932 (4)	166 (4)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022075/ci5099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022075/ci5099Isup2.hkl

checkCIF report

Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Zhu et al., 2009; Jimenez-Pulido et al., 2008; Raj et al., 2007; Zhong et al., 2007). The study on the crystal structures of such compounds is of particular interest (Khaledi et al., 2009; Warad et al., 2009; Back et al., 2009; Vijayakumar et al., 2009). We report herein the crystal structure of the title new hydrazone.

In the title molecule (Fig. 1), the dihedral angle between the two benzene rings is 45.3 (3)°, indicating that the molecule is twisted. The dihedral angle between the N3/O3/O4 nitro group and the C9–C14 benzene ring is 37.5 (3)°. All the bond lengths are comparable to those observed in related structures (Cao, 2009; Xu et al., 2009; Shafiq et al., 2009).

In the crystal structure, molecules are linked through O—H···O and N—H···O hydrogen bonds, to form a two-dimensional network parallel to the (100) (Fig. 2 and Table 1).

Related literature top

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010); Zhu et al. (2009); Jimenez-Pulido et al. (2008); Raj et al. (2007); Zhong et al. (2007). For the crystal structures of hydrazones, see: Khaledi et al. (2009); Warad et al. (2009); Back et al. (2009); Vijayakumar et al. (2009). For related structures, see: Cao (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 4-hydroxybenzaldehyde (0.05 mol, 6 g) and 2-nitrobenzohydrazide (0.05 mol, 9 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structure determination were obtained by slow evaporation of the methanol solution for a period of 8 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(4-Hydroxybenzylidene)-2-nitrobenzohydrazide top

Crystal data top

C₁₄H₁₁N₃O₄	F(000) = 592
M_r = 285.26	D_x = 1.429 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 633 reflections
a = 7.720 (2) Å	θ = 2.5–24.5°
b = 11.398 (3) Å	µ = 0.11 mm⁻¹
c = 15.072 (5) Å	T = 298 K
V = 1326.3 (7) Å³	Block, colourless
Z = 4	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1602 independent reflections
Radiation source: fine-focus sealed tube	961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
ω scans	θ_max = 26.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.979, T_max = 0.981	k = −14→13
7745 measured reflections	l = −18→18

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
1602 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₄	V = 1326.3 (7) Å³
M_r = 285.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.720 (2) Å	µ = 0.11 mm⁻¹
b = 11.398 (3) Å	T = 298 K
c = 15.072 (5) Å	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1602 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	961 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.981	R_int = 0.085
7745 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.25 e Å⁻³
1602 reflections	Δρ_min = −0.18 e Å⁻³
194 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.1071 (5)	0.7318 (3)	1.03691 (19)	0.0490 (10)
N2	0.1251 (5)	0.7909 (3)	0.9568 (2)	0.0486 (9)
N3	0.2475 (6)	1.1354 (4)	0.9364 (3)	0.0729 (13)
O1	0.1478 (4)	0.3516 (2)	1.34410 (16)	0.0478 (8)
H1	0.0826	0.3784	1.3820	0.072*
O2	0.0109 (4)	0.9556 (2)	1.01482 (16)	0.0498 (8)
O3	0.3197 (5)	1.0807 (4)	0.9939 (2)	0.0846 (12)
O4	0.2255 (9)	1.2411 (4)	0.9389 (3)	0.151 (2)
C1	0.1311 (5)	0.5519 (3)	1.1159 (2)	0.0386 (9)
C2	0.0734 (5)	0.5986 (3)	1.1956 (2)	0.0415 (10)
H2	0.0306	0.6749	1.1971	0.050*
C3	0.0787 (5)	0.5334 (3)	1.2728 (3)	0.0411 (10)
H3	0.0418	0.5657	1.3262	0.049*
C4	0.1396 (5)	0.4197 (3)	1.2695 (2)	0.0362 (9)
C5	0.1956 (5)	0.3714 (3)	1.1908 (3)	0.0428 (10)
H5	0.2367	0.2948	1.1892	0.051*
C6	0.1902 (5)	0.4375 (3)	1.1148 (2)	0.0428 (10)
H6	0.2271	0.4047	1.0616	0.051*
C7	0.1348 (6)	0.6220 (4)	1.0351 (2)	0.0452 (10)
H7	0.1579	0.5856	0.9812	0.054*
C8	0.0819 (5)	0.9035 (3)	0.9539 (2)	0.0406 (10)
C9	0.1145 (5)	0.9615 (3)	0.8660 (2)	0.0385 (9)
C10	0.1817 (6)	1.0730 (4)	0.8584 (3)	0.0470 (11)
C11	0.1996 (6)	1.1296 (4)	0.7788 (3)	0.0570 (12)
H11	0.2446	1.2052	0.7762	0.068*
C12	0.1495 (7)	1.0721 (5)	0.7024 (3)	0.0649 (14)
H12	0.1618	1.1088	0.6477	0.078*
C13	0.0821 (6)	0.9617 (4)	0.7068 (3)	0.0609 (13)
H13	0.0495	0.9228	0.6552	0.073*
C14	0.0624 (5)	0.9078 (4)	0.7889 (2)	0.0468 (11)
H14	0.0127	0.8336	0.7917	0.056*
H2A	0.189 (5)	0.755 (4)	0.915 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.076 (3)	0.0396 (19)	0.0313 (18)	0.0082 (19)	0.0090 (19)	0.0098 (15)
N2	0.073 (3)	0.040 (2)	0.0327 (19)	0.008 (2)	0.016 (2)	0.0108 (15)
N3	0.095 (4)	0.056 (3)	0.067 (3)	−0.013 (3)	0.011 (3)	−0.006 (2)
O1	0.065 (2)	0.0454 (16)	0.0334 (15)	0.0081 (15)	0.0097 (14)	0.0069 (12)
O2	0.068 (2)	0.0442 (16)	0.0377 (15)	0.0063 (16)	0.0144 (15)	−0.0023 (13)
O3	0.087 (3)	0.112 (3)	0.055 (2)	−0.020 (3)	−0.0063 (19)	−0.009 (2)
O4	0.262 (7)	0.056 (3)	0.133 (4)	−0.013 (3)	−0.004 (4)	−0.027 (3)
C1	0.049 (2)	0.033 (2)	0.034 (2)	0.001 (2)	0.0034 (19)	0.0029 (16)
C2	0.055 (3)	0.035 (2)	0.034 (2)	0.006 (2)	0.0031 (19)	0.0018 (17)
C3	0.051 (3)	0.041 (2)	0.032 (2)	0.002 (2)	0.0087 (18)	−0.0002 (18)
C4	0.041 (2)	0.038 (2)	0.0303 (19)	−0.007 (2)	0.0019 (18)	0.0099 (17)
C5	0.057 (3)	0.031 (2)	0.041 (2)	0.002 (2)	−0.001 (2)	−0.0005 (18)
C6	0.056 (3)	0.041 (2)	0.032 (2)	0.000 (2)	0.0040 (18)	−0.0034 (18)
C7	0.059 (3)	0.046 (2)	0.031 (2)	0.003 (2)	0.005 (2)	0.0022 (17)
C8	0.050 (3)	0.039 (2)	0.033 (2)	0.001 (2)	0.0062 (19)	0.0045 (18)
C9	0.047 (2)	0.034 (2)	0.034 (2)	0.009 (2)	0.0043 (19)	−0.0001 (17)
C10	0.053 (3)	0.044 (2)	0.043 (2)	0.008 (2)	0.008 (2)	0.001 (2)
C11	0.060 (3)	0.045 (3)	0.067 (3)	−0.003 (2)	0.013 (2)	0.019 (2)
C12	0.073 (3)	0.072 (3)	0.049 (3)	0.017 (3)	0.011 (3)	0.030 (3)
C13	0.073 (3)	0.074 (3)	0.036 (3)	0.013 (3)	0.000 (2)	0.004 (2)
C14	0.056 (3)	0.045 (2)	0.039 (2)	0.003 (2)	0.0006 (19)	0.0037 (19)

Geometric parameters (Å, º) top

N1—C7	1.270 (4)	C4—C5	1.377 (5)
N1—N2	1.389 (4)	C5—C6	1.372 (5)
N2—C8	1.327 (5)	C5—H5	0.93
N2—H2A	0.90 (1)	C6—H6	0.93
N3—O3	1.204 (5)	C7—H7	0.93
N3—O4	1.217 (5)	C8—C9	1.501 (5)
N3—C10	1.466 (6)	C9—C14	1.374 (5)
O1—C4	1.368 (4)	C9—C10	1.377 (5)
O1—H1	0.82	C10—C11	1.369 (5)
O2—C8	1.224 (4)	C11—C12	1.379 (6)
C1—C6	1.381 (5)	C11—H11	0.93
C1—C2	1.388 (5)	C12—C13	1.363 (7)
C1—C7	1.457 (5)	C12—H12	0.93
C2—C3	1.381 (5)	C13—C14	1.390 (5)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.380 (5)	C14—H14	0.93
C3—H3	0.93

C7—N1—N2	116.2 (3)	C1—C6—H6	119.4
C8—N2—N1	118.2 (3)	N1—C7—C1	121.3 (3)
C8—N2—H2A	123 (3)	N1—C7—H7	119.3
N1—N2—H2A	117 (3)	C1—C7—H7	119.3
O3—N3—O4	123.7 (5)	O2—C8—N2	123.9 (3)
O3—N3—C10	119.1 (4)	O2—C8—C9	121.5 (3)
O4—N3—C10	117.2 (5)	N2—C8—C9	114.4 (3)
C4—O1—H1	109.5	C14—C9—C10	116.8 (4)
C6—C1—C2	118.6 (3)	C14—C9—C8	120.0 (4)
C6—C1—C7	120.1 (3)	C10—C9—C8	123.0 (3)
C2—C1—C7	121.3 (3)	C11—C10—C9	123.2 (4)
C3—C2—C1	120.9 (3)	C11—C10—N3	116.0 (4)
C3—C2—H2	119.6	C9—C10—N3	120.7 (4)
C1—C2—H2	119.6	C10—C11—C12	118.6 (4)
C4—C3—C2	119.0 (3)	C10—C11—H11	120.7
C4—C3—H3	120.5	C12—C11—H11	120.7
C2—C3—H3	120.5	C13—C12—C11	120.4 (4)
O1—C4—C5	117.8 (3)	C13—C12—H12	119.8
O1—C4—C3	121.3 (3)	C11—C12—H12	119.8
C5—C4—C3	120.9 (3)	C12—C13—C14	119.5 (4)
C6—C5—C4	119.4 (3)	C12—C13—H13	120.2
C6—C5—H5	120.3	C14—C13—H13	120.2
C4—C5—H5	120.3	C9—C14—C13	121.6 (4)
C5—C6—C1	121.2 (4)	C9—C14—H14	119.2
C5—C6—H6	119.4	C13—C14—H14	119.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.93	2.725 (3)	164
N2—H2A···O1ⁱⁱ	0.90 (1)	2.05 (2)	2.932 (4)	166 (4)

Symmetry codes: (i) −x, y−1/2, −z+5/2; (ii) −x+1/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₄
M_r	285.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.720 (2), 11.398 (3), 15.072 (5)
V (Å³)	1326.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.979, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	7745, 1602, 961
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.125, 1.02
No. of reflections	1602
No. of parameters	194
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.93	2.725 (3)	164
N2—H2A···O1ⁱⁱ	0.90 (1)	2.05 (2)	2.932 (4)	166 (4)

Symmetry codes: (i) −x, y−1/2, −z+5/2; (ii) −x+1/2, −y+1, z−1/2.

Acknowledgements

The authors acknowledge Taizhou University for financial support.

References

Back, D. F., Ballin, M. A. & de Oliveira, G. M. (2009). J. Mol. Struct. 935, 151–155. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, G.-B. (2009). Acta Cryst. E65, o2086. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hillmer, A. S., Putcha, P., Levin, J., Hogen, T., Hyman, B. T., Kretzschmar, H., McLean, P. J. & Giese, A. (2010). Biochem. Biophys. Res. Commun. 391, 461–466. Web of Science CrossRef PubMed CAS Google Scholar
Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677–1683. Web of Science CSD CrossRef PubMed CAS Google Scholar
Khaledi, H., Saharin, S. M., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2009). Acta Cryst. E65, o1920. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564–1569. Web of Science CrossRef CAS Google Scholar
Warad, I., Al-Nuri, M., Al-Resayes, S., Al-Farhan, K. & Ghazzali, M. (2009). Acta Cryst. E65, o1597. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774–3777. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhu, Q.-Y., Wei, Y.-J. & Wang, F.-W. (2009). Pol. J. Chem. 83, 1233–1240. CAS Google Scholar