Literature DB >> 21589112

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

Abstract

The title compound, C(14)H(11)N(3)O(4), was prepared by the reaction of 4-nitro-benzohydrazide with 4-hy-droxy-benz-alde-hyde. The whole mol-ecule of the compound is approximately planar, with a mean deviation from the least-squares plane through all the non-H atoms of 0.050 (2) Å; the dihedral angle between the two benzene rings is 2.0 (2)°. In the crystal, the benzohydrazide mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming layers in the bc plane.

Entities: Chemical Disease Species

Year: 2010 PMID： 21589112 PMCID： PMC3009258 DOI： 10.1107/S1600536810042364

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C14H11N3O4 M = 285.26 Monoclinic, a = 7.856 (3) Å b = 13.368 (5) Å c = 12.527 (5) Å β = 95.748 (4)° V = 1309.0 (9) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 298 K 0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.981, T max = 0.982 7505 measured reflections 2822 independent reflections 1736 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.119 S = 1.04 2822 reflections 194 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.16 e Å−3 Δρmin = −0.16 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/S1600536810042364/sj5045sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042364/sj5045Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁N₃O₄	F(000) = 592
M_r = 285.26	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1632 reflections
a = 7.856 (3) Å	θ = 2.2–26.0°
b = 13.368 (5) Å	µ = 0.11 mm⁻¹
c = 12.527 (5) Å	T = 298 K
β = 95.748 (4)°	Block, yellow
V = 1309.0 (9) Å³	0.18 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2822 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
graphite	R_int = 0.025
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
T_min = 0.981, T_max = 0.982	k = −17→14
7505 measured reflections	l = −16→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0494P)² + 0.1504P] where P = (F_o² + 2F_c²)/3
2822 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.16 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	U_iso*/U_eq
N1	0.20526 (19)	−0.05033 (11)	0.04617 (11)	0.0433 (4)
N2	0.2594 (2)	0.02540 (11)	−0.01727 (11)	0.0420 (4)
N3	0.4845 (2)	0.44506 (12)	−0.22229 (13)	0.0510 (4)
O1	0.0039 (2)	−0.46112 (9)	0.25453 (11)	0.0598 (4)
H1	−0.0521	−0.4411	0.3021	0.090*
O2	0.17995 (17)	0.13969 (9)	0.09997 (10)	0.0512 (4)
O3	0.4755 (2)	0.52833 (11)	−0.18407 (13)	0.0872 (6)
O4	0.54671 (18)	0.42836 (10)	−0.30610 (10)	0.0603 (4)
C1	0.1654 (2)	−0.22332 (13)	0.07612 (14)	0.0395 (4)
C2	0.1046 (2)	−0.20626 (13)	0.17594 (14)	0.0433 (5)
H2A	0.1006	−0.1412	0.2020	0.052*
C3	0.0511 (2)	−0.28366 (13)	0.23572 (14)	0.0444 (5)
H3	0.0107	−0.2708	0.3017	0.053*
C4	0.0567 (2)	−0.38146 (13)	0.19834 (14)	0.0424 (5)
C5	0.1185 (2)	−0.39987 (13)	0.10044 (15)	0.0463 (5)
H5	0.1240	−0.4651	0.0753	0.056*
C6	0.1721 (2)	−0.32147 (13)	0.04010 (14)	0.0446 (5)
H6	0.2132	−0.3346	−0.0256	0.053*
C7	0.2197 (2)	−0.13939 (13)	0.01282 (14)	0.0422 (4)
H7	0.2649	−0.1512	−0.0519	0.051*
C8	0.2426 (2)	0.12013 (13)	0.01678 (13)	0.0372 (4)
C9	0.3070 (2)	0.20201 (12)	−0.05002 (13)	0.0352 (4)
C10	0.2986 (2)	0.29875 (13)	−0.01120 (14)	0.0454 (5)
H10	0.2541	0.3099	0.0538	0.055*
C11	0.3552 (2)	0.37861 (13)	−0.06733 (15)	0.0482 (5)
H11	0.3492	0.4435	−0.0411	0.058*
C12	0.4209 (2)	0.36016 (13)	−0.16304 (14)	0.0395 (4)
C13	0.4312 (2)	0.26543 (14)	−0.20412 (14)	0.0449 (5)
H13	0.4760	0.2548	−0.2691	0.054*
C14	0.3738 (2)	0.18647 (13)	−0.14713 (14)	0.0446 (5)
H14	0.3799	0.1219	−0.1740	0.054*
H2	0.299 (3)	0.0083 (16)	−0.0797 (11)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0554 (10)	0.0363 (9)	0.0402 (9)	−0.0019 (7)	0.0149 (7)	0.0061 (7)
N2	0.0593 (10)	0.0337 (8)	0.0360 (8)	−0.0025 (7)	0.0187 (7)	0.0034 (7)
N3	0.0596 (11)	0.0466 (10)	0.0482 (10)	−0.0082 (8)	0.0127 (8)	0.0080 (8)
O1	0.0868 (11)	0.0365 (7)	0.0615 (9)	−0.0022 (7)	0.0338 (8)	0.0061 (7)
O2	0.0688 (9)	0.0451 (8)	0.0442 (8)	0.0005 (7)	0.0273 (6)	−0.0002 (6)
O3	0.1470 (17)	0.0418 (9)	0.0802 (12)	−0.0201 (10)	0.0472 (11)	0.0006 (8)
O4	0.0700 (10)	0.0636 (9)	0.0511 (9)	−0.0088 (7)	0.0247 (7)	0.0110 (7)
C1	0.0415 (10)	0.0392 (10)	0.0385 (10)	0.0004 (8)	0.0075 (8)	0.0030 (8)
C2	0.0554 (11)	0.0332 (10)	0.0429 (10)	−0.0023 (8)	0.0127 (9)	−0.0005 (8)
C3	0.0553 (11)	0.0411 (10)	0.0390 (10)	0.0011 (9)	0.0154 (9)	−0.0003 (9)
C4	0.0467 (11)	0.0362 (10)	0.0453 (11)	0.0007 (8)	0.0100 (9)	0.0077 (9)
C5	0.0585 (12)	0.0326 (9)	0.0495 (11)	0.0012 (9)	0.0135 (9)	−0.0022 (9)
C6	0.0524 (11)	0.0432 (11)	0.0400 (10)	0.0015 (9)	0.0142 (9)	−0.0008 (9)
C7	0.0472 (11)	0.0441 (11)	0.0367 (10)	−0.0006 (9)	0.0123 (8)	0.0042 (9)
C8	0.0394 (10)	0.0405 (10)	0.0327 (9)	0.0025 (8)	0.0084 (8)	0.0015 (8)
C9	0.0367 (9)	0.0369 (9)	0.0330 (9)	0.0032 (7)	0.0083 (7)	0.0026 (8)
C10	0.0589 (12)	0.0430 (11)	0.0373 (10)	−0.0008 (9)	0.0197 (9)	−0.0045 (8)
C11	0.0632 (12)	0.0353 (10)	0.0481 (11)	−0.0029 (9)	0.0159 (10)	−0.0030 (9)
C12	0.0424 (10)	0.0371 (10)	0.0400 (10)	−0.0021 (8)	0.0088 (8)	0.0068 (8)
C13	0.0554 (11)	0.0457 (11)	0.0363 (10)	0.0012 (9)	0.0180 (9)	0.0024 (9)
C14	0.0605 (12)	0.0343 (9)	0.0417 (10)	0.0032 (9)	0.0186 (9)	−0.0013 (8)

N1—C7	1.271 (2)	C4—C5	1.386 (2)
N1—N2	1.3803 (19)	C5—C6	1.382 (2)
N2—C8	1.347 (2)	C5—H5	0.9300
N2—H2	0.899 (9)	C6—H6	0.9300
N3—O3	1.217 (2)	C7—H7	0.9300
N3—O4	1.2220 (19)	C8—C9	1.496 (2)
N3—C12	1.471 (2)	C9—C10	1.386 (2)
O1—C4	1.364 (2)	C9—C14	1.388 (2)
O1—H1	0.8200	C10—C11	1.376 (2)
O2—C8	1.2247 (19)	C10—H10	0.9300
C1—C6	1.390 (2)	C11—C12	1.374 (2)
C1—C2	1.401 (2)	C11—H11	0.9300
C1—C7	1.462 (2)	C12—C13	1.372 (2)
C2—C3	1.368 (2)	C13—C14	1.375 (2)
C2—H2A	0.9300	C13—H13	0.9300
C3—C4	1.391 (2)	C14—H14	0.9300
C3—H3	0.9300

C7—N1—N2	117.08 (14)	C1—C6—H6	119.5
C8—N2—N1	117.50 (13)	N1—C7—C1	120.02 (15)
C8—N2—H2	124.6 (15)	N1—C7—H7	120.0
N1—N2—H2	117.9 (15)	C1—C7—H7	120.0
O3—N3—O4	123.30 (16)	O2—C8—N2	122.05 (15)
O3—N3—C12	118.13 (16)	O2—C8—C9	120.45 (15)
O4—N3—C12	118.55 (16)	N2—C8—C9	117.49 (14)
C4—O1—H1	109.5	C10—C9—C14	118.85 (15)
C6—C1—C2	118.08 (16)	C10—C9—C8	117.14 (14)
C6—C1—C7	121.71 (15)	C14—C9—C8	124.01 (15)
C2—C1—C7	120.20 (16)	C11—C10—C9	121.04 (16)
C3—C2—C1	121.08 (16)	C11—C10—H10	119.5
C3—C2—H2A	119.5	C9—C10—H10	119.5
C1—C2—H2A	119.5	C12—C11—C10	118.37 (17)
C2—C3—C4	120.32 (16)	C12—C11—H11	120.8
C2—C3—H3	119.8	C10—C11—H11	120.8
C4—C3—H3	119.8	C13—C12—C11	122.28 (16)
O1—C4—C5	118.02 (16)	C13—C12—N3	119.15 (15)
O1—C4—C3	122.60 (15)	C11—C12—N3	118.56 (16)
C5—C4—C3	119.38 (16)	C12—C13—C14	118.62 (15)
C6—C5—C4	120.15 (17)	C12—C13—H13	120.7
C6—C5—H5	119.9	C14—C13—H13	120.7
C4—C5—H5	119.9	C13—C14—C9	120.83 (16)
C5—C6—C1	120.97 (16)	C13—C14—H14	119.6
C5—C6—H6	119.5	C9—C14—H14	119.6

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.98	2.7841 (18)	166
N2—H2···O4ⁱⁱ	0.90 (1)	2.24 (1)	3.094 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.98	2.7841 (18)	166
N2—H2⋯O4ⁱⁱ	0.90 (1)	2.24 (1)	3.094 (2)	159 (2)

Symmetry codes: (i) ; (ii) .

8 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. New Cu(II), Co(II), Ni(II) complexes with aroyl-hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation.

Authors: Madalina Veronica Angelusiu; Stefania-Felicia Barbuceanu; Constantin Draghici; Gabriela Laura Almajan
Journal: Eur J Med Chem Date: 2010-01-25 Impact factor: 6.514

3. 4-Nitro-N'-[(1E,2E)-3-phenyl-prop-2-en-1-yl-idene]benzohydrazide.

Authors: Tanveer Ahmad; Muhammad Zia-Ur-Rehman; Hamid Latif Siddiqui; Shahid Mahmud; Masood Parvez
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-02

4. 2-Chloro-N'-(4-nitro-benzyl-idene)benzo-hydrazide.

Authors: Cong-Shan Zhou; Tao Yang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-01-09

5. 4-Hy-droxy-N'-[1-(2-hy-droxy-phen-yl)ethyl-idene]benzohydrazide.

Authors: Xiao-Hui Ji; Jiu-Fu Lu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-05-29

6. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives.

Authors: Olayinka O Ajani; Craig A Obafemi; Obinna C Nwinyi; David A Akinpelu
Journal: Bioorg Med Chem Date: 2009-11-06 Impact factor: 3.641

7. N'-[1-(2-Amino-phen-yl)ethyl-idene]benzo-hydrazide.

Authors: Vinod P Singh; Shweta Singh
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-24

8. 4-Chloro-N'-(4-meth-oxy-benzyl-idene)benzohydrazide methanol monosolvate.

Authors: Hai-Tao Huang; Hong-Yuan Wu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-10-09