Literature DB >> 21587885

(E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-2-meth-oxy-benzohydrazide.

Abstract

In the title compound, C(15)H(13)BrN(2)O(3), the mol-ecule adopts an E configuration about the C=N bond and the two benzene rings form a dihedral angle of 20.3 (3)°. In the mol-ecule, there are two intra-molecular hydrogen bonds, viz. O-H⋯N and N-H⋯O, involving the hy-droxy substituent, the meth-oxy O atom and the hydrazide NH group and N atom. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains propagating along [010].

Entities: Chemical Disease Species

Year: 2010 PMID： 21587885 PMCID： PMC3006725 DOI： 10.1107/S1600536810022002

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

Related literature

For background to hydrazones and their medicinal applications, 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 similar compounds, see: Cao (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C15H13BrN2O3 M = 349.18 Orthorhombic, a = 15.587 (3) Å b = 9.1281 (19) Å c = 20.399 (4) Å V = 2902.3 (10) Å3 Z = 8 Mo Kα radiation μ = 2.84 mm−1 T = 298 K 0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.561, T max = 0.600 16311 measured reflections 3154 independent reflections 1496 reflections with I > 2σ(I) R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.127 S = 1.00 3154 reflections 195 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.64 e Å−3 Δρmin = −0.78 e Å−3 Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022002/su2186sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022002/su2186Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₃BrN₂O₃	D_x = 1.598 Mg m⁻³
M_r = 349.18	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1832 reflections
a = 15.587 (3) Å	θ = 2.5–24.0°
b = 9.1281 (19) Å	µ = 2.84 mm⁻¹
c = 20.399 (4) Å	T = 298 K
V = 2902.3 (10) Å³	Block, colourless
Z = 8	0.23 × 0.20 × 0.20 mm
F(000) = 1408

Bruker SMART CCD area-detector diffractometer	3154 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
graphite	R_int = 0.074
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→18
T_min = 0.561, T_max = 0.600	k = −11→11
16311 measured reflections	l = −26→23

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0528P)² + 0.6195P] where P = (F_o² + 2F_c²)/3
3154 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.64 e Å⁻³
1 restraint	Δρ_min = −0.78 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	U_iso*/U_eq
Br1	1.23601 (3)	0.49891 (6)	0.43968 (3)	0.0855 (2)
N1	0.8301 (2)	0.4179 (3)	0.38746 (13)	0.0464 (7)
N2	0.76415 (19)	0.4977 (3)	0.35837 (15)	0.0484 (7)
O1	0.89179 (19)	0.2082 (3)	0.46358 (15)	0.0674 (8)
H1	0.8543	0.2542	0.4443	0.101*
O2	0.67329 (16)	0.3058 (3)	0.36404 (13)	0.0598 (7)
O3	0.71532 (17)	0.6580 (3)	0.25197 (13)	0.0629 (8)
C1	0.9761 (2)	0.4067 (4)	0.42007 (16)	0.0425 (9)
C2	0.9676 (3)	0.2766 (4)	0.45609 (18)	0.0524 (10)
C3	1.0386 (3)	0.2181 (4)	0.4871 (2)	0.0659 (12)
H3	1.0329	0.1328	0.5117	0.079*
C4	1.1175 (3)	0.2842 (5)	0.4823 (2)	0.0662 (12)
H4	1.1644	0.2444	0.5041	0.079*
C5	1.1271 (2)	0.4091 (5)	0.44529 (18)	0.0547 (10)
C6	1.0566 (2)	0.4699 (4)	0.41518 (18)	0.0504 (10)
H6	1.0632	0.5554	0.3910	0.061*
C7	0.9037 (2)	0.4779 (4)	0.38856 (17)	0.0443 (9)
H7	0.9113	0.5689	0.3689	0.053*
C8	0.6876 (2)	0.4335 (4)	0.34843 (16)	0.0436 (9)
C9	0.6191 (2)	0.5270 (4)	0.31930 (18)	0.0446 (9)
C10	0.6332 (3)	0.6357 (4)	0.27206 (18)	0.0498 (9)
C11	0.5635 (3)	0.7133 (4)	0.2475 (2)	0.0636 (11)
H11	0.5723	0.7844	0.2155	0.076*
C12	0.4824 (3)	0.6865 (5)	0.2696 (2)	0.0698 (12)
H12	0.4368	0.7406	0.2530	0.084*
C13	0.4671 (3)	0.5804 (5)	0.3162 (2)	0.0674 (12)
H13	0.4117	0.5624	0.3311	0.081*
C14	0.5358 (3)	0.5011 (4)	0.34027 (18)	0.0557 (10)
H14	0.5259	0.4285	0.3714	0.067*
C15	0.7306 (3)	0.7746 (5)	0.2062 (2)	0.0778 (14)
H15A	0.7006	0.7548	0.1661	0.117*
H15B	0.7910	0.7816	0.1975	0.117*
H15C	0.7106	0.8653	0.2244	0.117*
H2	0.777 (3)	0.5907 (17)	0.3488 (19)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0504 (3)	0.1095 (5)	0.0967 (4)	0.0050 (3)	−0.0067 (2)	−0.0282 (3)
N1	0.051 (2)	0.0402 (18)	0.0483 (18)	0.0045 (16)	−0.0080 (15)	0.0006 (14)
N2	0.0499 (18)	0.0346 (17)	0.0607 (19)	−0.0031 (17)	−0.0110 (15)	0.0081 (17)
O1	0.077 (2)	0.0522 (18)	0.073 (2)	0.0002 (16)	0.0031 (16)	0.0167 (15)
O2	0.0614 (17)	0.0400 (16)	0.0781 (19)	−0.0060 (13)	−0.0051 (14)	0.0116 (14)
O3	0.0557 (18)	0.0630 (18)	0.0700 (18)	0.0012 (14)	−0.0027 (14)	0.0282 (15)
C1	0.048 (2)	0.039 (2)	0.040 (2)	0.0074 (18)	−0.0037 (17)	−0.0015 (17)
C2	0.066 (3)	0.047 (3)	0.045 (2)	0.006 (2)	0.000 (2)	−0.0005 (19)
C3	0.090 (3)	0.050 (3)	0.057 (3)	0.019 (3)	−0.010 (2)	0.007 (2)
C4	0.070 (3)	0.073 (3)	0.056 (3)	0.030 (3)	−0.017 (2)	−0.015 (2)
C5	0.048 (2)	0.064 (3)	0.052 (2)	0.011 (2)	−0.0031 (19)	−0.013 (2)
C6	0.053 (3)	0.047 (2)	0.051 (2)	0.0085 (19)	−0.0009 (18)	−0.0040 (19)
C7	0.053 (2)	0.035 (2)	0.045 (2)	0.0053 (18)	−0.0015 (17)	0.0026 (17)
C8	0.052 (3)	0.036 (2)	0.043 (2)	−0.0034 (18)	−0.0039 (17)	−0.0031 (18)
C9	0.045 (2)	0.038 (2)	0.051 (2)	−0.0002 (17)	−0.0100 (17)	−0.0037 (18)
C10	0.056 (3)	0.041 (2)	0.053 (2)	0.0036 (19)	−0.010 (2)	−0.001 (2)
C11	0.064 (3)	0.057 (3)	0.070 (3)	0.006 (2)	−0.012 (2)	0.010 (2)
C12	0.060 (3)	0.063 (3)	0.086 (3)	0.015 (2)	−0.016 (2)	−0.003 (3)
C13	0.046 (3)	0.073 (3)	0.083 (3)	0.005 (2)	−0.010 (2)	−0.016 (3)
C14	0.056 (3)	0.055 (3)	0.057 (2)	−0.006 (2)	−0.0048 (18)	−0.002 (2)
C15	0.079 (3)	0.077 (3)	0.077 (3)	−0.009 (2)	−0.006 (2)	0.029 (2)

Br1—C5	1.888 (4)	C5—C6	1.376 (5)
N1—C7	1.271 (4)	C6—H6	0.9300
N1—N2	1.393 (4)	C7—H7	0.9300
N2—C8	1.344 (4)	C8—C9	1.491 (5)
N2—H2	0.892 (10)	C9—C14	1.388 (5)
O1—C2	1.345 (5)	C9—C10	1.401 (5)
O1—H1	0.8200	C10—C11	1.390 (5)
O2—C8	1.229 (4)	C11—C12	1.364 (6)
O3—C10	1.359 (4)	C11—H11	0.9300
O3—C15	1.436 (4)	C12—C13	1.377 (6)
C1—C6	1.386 (5)	C12—H12	0.9300
C1—C2	1.403 (5)	C13—C14	1.382 (5)
C1—C7	1.451 (5)	C13—H13	0.9300
C2—C3	1.383 (5)	C14—H14	0.9300
C3—C4	1.372 (6)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.375 (5)	C15—H15C	0.9600
C4—H4	0.9300

C7—N1—N2	116.7 (3)	O2—C8—N2	122.4 (3)
C8—N2—N1	119.4 (3)	O2—C8—C9	121.1 (3)
C8—N2—H2	125 (3)	N2—C8—C9	116.5 (3)
N1—N2—H2	115 (3)	C14—C9—C10	118.7 (3)
C2—O1—H1	109.5	C14—C9—C8	116.7 (3)
C10—O3—C15	117.6 (3)	C10—C9—C8	124.6 (3)
C6—C1—C2	118.4 (3)	O3—C10—C11	123.4 (4)
C6—C1—C7	119.1 (3)	O3—C10—C9	117.5 (3)
C2—C1—C7	122.6 (4)	C11—C10—C9	119.1 (4)
O1—C2—C3	118.2 (4)	C12—C11—C10	120.9 (4)
O1—C2—C1	122.3 (4)	C12—C11—H11	119.5
C3—C2—C1	119.5 (4)	C10—C11—H11	119.5
C4—C3—C2	120.9 (4)	C11—C12—C13	120.9 (4)
C4—C3—H3	119.5	C11—C12—H12	119.5
C2—C3—H3	119.5	C13—C12—H12	119.5
C3—C4—C5	120.1 (4)	C12—C13—C14	118.7 (4)
C3—C4—H4	119.9	C12—C13—H13	120.7
C5—C4—H4	119.9	C14—C13—H13	120.7
C4—C5—C6	119.5 (4)	C13—C14—C9	121.7 (4)
C4—C5—Br1	119.5 (3)	C13—C14—H14	119.2
C6—C5—Br1	121.0 (3)	C9—C14—H14	119.2
C5—C6—C1	121.6 (4)	O3—C15—H15A	109.5
C5—C6—H6	119.2	O3—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	121.1 (3)	O3—C15—H15C	109.5
N1—C7—H7	119.5	H15A—C15—H15C	109.5
C1—C7—H7	119.5	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.89 (1)	2.14 (2)	2.978 (4)	157 (4)
N2—H2···O3	0.89 (1)	2.28 (4)	2.726 (4)	111 (3)
O1—H1···N1	0.82	1.93	2.646 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.89 (1)	2.14 (2)	2.978 (4)	157 (4)
N2—H2⋯O3	0.89 (1)	2.28 (4)	2.726 (4)	111 (3)
O1—H1⋯N1	0.82	1.93	2.646 (4)	146

Symmetry code: (i) .

10 in total

1. Synthesis of some bioactive 2-bromo-5-methoxy-N'-[4-(aryl)-1,3-thiazol-2-yl]benzohydrazide derivatives.

Authors: K K Vijaya Raj; B Narayana; B V Ashalatha; N Suchetha Kumari; B K Sarojini
Journal: Eur J Med Chem Date: 2006-10-30 Impact factor: 6.514

2. A short history of SHELX.

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

3. 2,4-Dihydr-oxy-N'-(3,4,5-trimethoxy-benzyl-idene)benzohydrazide.

Authors: Liang Xu; Shan-Shan Huang; Bao-Jing Zhang; Shou-Yu Wang; Hou-Li Zhang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-09

4. 3,4,5-Trihydr-oxy-N'-[(1-methyl-1H-indol-2-yl)methyl-idene]benzohydrazide.

Authors: Hamid Khaledi; Siti Munirah Saharin; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-07-18

5. N'-[(E)-4-Hydr-oxy-3-methoxy-benzyl-idene]benzohydrazide.

Authors: Zahid Shafiq; Muhammad Yaqub; M Nawaz Tahir; Abid Hussain; M Saeed Iqbal
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-28

6. Metal complexes with the ligand derived from 6-acetyl-1,3,7-trimethyllumazine and benzohydrazide. Molecular structures of two new Co(II) and Rh(III) complexes and analysis of in vitro antitumor activity.

Authors: Sonia B Jiménez-Pulido; Fátima M Linares-Ordóñez; Jose M Martínez-Martos; Miguel N Moreno-Carretero; Miguel Quirós-Olozábal; María J Ramírez-Expósito
Journal: J Inorg Biochem Date: 2008-04-26 Impact factor: 4.155

7. The crystal structures of copper(II), manganese(II), and nickel(II) complexes of a (Z)-2-hydroxy-N'-(2-oxoindolin-3-ylidene) benzohydrazide--potential antitumor agents.

Authors: Xia Zhong; Hu-Lai Wei; Wei-Sheng Liu; Da-Qi Wang; Xing Wang
Journal: Bioorg Med Chem Lett Date: 2007-04-10 Impact factor: 2.823

8. Converse modulation of toxic alpha-synuclein oligomers in living cells by N'-benzylidene-benzohydrazide derivates and ferric iron.

Authors: Andreas S Hillmer; Preeti Putcha; Johannes Levin; Tobias Högen; Bradley T Hyman; Hans Kretzschmar; Pamela J McLean; Armin Giese
Journal: Biochem Biophys Res Commun Date: 2009-11-13 Impact factor: 3.575

9. (E)-3-Bromo-N'-(4-methoxy-benzyl-idene)benzohydrazide methanol solvate.

Authors: Guo-Biao Cao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-08-08

10. N'-(Di-2-pyridylmethyl-ene)benzo-hydrazide.

Authors: Ismail Warad; Mohammed Al-Nuri; Saud Al-Resayes; Khalid Al-Farhan; Mohamed Ghazzali
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-06-17