Literature DB >> 21587889

(E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-4-hy-droxy-3-meth-oxy-benzohydrazide methanol solvate.

Abstract

In the title compound, C(15)H(13)BrN(2)O(4)·CH(4)O, the two benzene rings form a dihedral angle of 3.2 (2)°. An intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, mol-ecules are linked through O-H⋯O and N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (10).

Entities: CellLine Chemical Disease Species

Year: 2010 PMID： 21587889 PMCID： PMC3006942 DOI： 10.1107/S1600536810022063

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

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 crystal structures of hydrazone compounds, 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

C15H13BrN2O4·CH4O M = 397.23 Monoclinic, a = 7.4412 (4) Å b = 17.5287 (9) Å c = 12.5555 (8) Å β = 91.200 (3)° V = 1637.31 (16) Å3 Z = 4 Mo Kα radiation μ = 2.54 mm−1 T = 298 K 0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.547, T max = 0.593 9411 measured reflections 3368 independent reflections 2230 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.082 S = 1.01 3368 reflections 225 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.24 e Å−3 Δρmin = −0.31 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/S1600536810022063/ci5098sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022063/ci5098Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₃BrN₂O₄·CH₄O	F(000) = 808
M_r = 397.23	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2105 reflections
a = 7.4412 (4) Å	θ = 2.3–24.0°
b = 17.5287 (9) Å	µ = 2.54 mm⁻¹
c = 12.5555 (8) Å	T = 298 K
β = 91.200 (3)°	Block, colourless
V = 1637.31 (16) Å³	0.27 × 0.23 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3368 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
graphite	R_int = 0.039
ω scans	θ_max = 26.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.547, T_max = 0.593	k = −19→21
9411 measured reflections	l = −13→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
3368 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.31 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	0.18595 (5)	0.149648 (15)	0.52921 (3)	0.05687 (14)
N1	0.2299 (3)	0.51490 (11)	0.46909 (16)	0.0362 (5)
N2	0.2800 (3)	0.57506 (11)	0.53449 (16)	0.0370 (5)
O1	0.0923 (3)	0.44648 (10)	0.29416 (14)	0.0550 (6)
H1	0.1171	0.4831	0.3324	0.083*
O2	0.2525 (3)	0.65966 (10)	0.40042 (15)	0.0508 (5)
O3	0.3700 (3)	0.91862 (9)	0.56842 (13)	0.0438 (5)
O4	0.5122 (3)	0.89035 (10)	0.75563 (14)	0.0513 (5)
H4	0.5720	0.8758	0.8073	0.077*
O5	0.3071 (3)	0.51702 (11)	0.75469 (16)	0.0561 (6)
H5	0.2163	0.4979	0.7793	0.084*
C1	0.1853 (4)	0.38040 (14)	0.4545 (2)	0.0363 (6)
C2	0.1173 (4)	0.38095 (15)	0.3500 (2)	0.0382 (6)
C3	0.0704 (4)	0.31294 (16)	0.3002 (2)	0.0468 (7)
H3	0.0236	0.3136	0.2309	0.056*
C4	0.0928 (4)	0.24469 (15)	0.3524 (2)	0.0489 (8)
H4A	0.0631	0.1992	0.3182	0.059*
C5	0.1593 (4)	0.24389 (14)	0.4555 (2)	0.0408 (7)
C6	0.2052 (4)	0.31014 (14)	0.5065 (2)	0.0393 (7)
H6	0.2498	0.3086	0.5763	0.047*
C7	0.2359 (4)	0.44864 (14)	0.5118 (2)	0.0386 (7)
H7	0.2743	0.4443	0.5824	0.046*
C8	0.2886 (3)	0.64661 (13)	0.4938 (2)	0.0329 (6)
C9	0.3473 (3)	0.70777 (13)	0.56902 (19)	0.0305 (6)
C10	0.3292 (3)	0.78280 (13)	0.5325 (2)	0.0328 (6)
H10	0.2810	0.7921	0.4648	0.039*
C11	0.3827 (3)	0.84311 (12)	0.5964 (2)	0.0317 (6)
C12	0.4587 (4)	0.82893 (14)	0.69653 (19)	0.0336 (6)
C13	0.4745 (4)	0.75503 (13)	0.7325 (2)	0.0357 (6)
H13	0.5227	0.7457	0.8002	0.043*
C14	0.4193 (3)	0.69455 (14)	0.66906 (19)	0.0350 (6)
H14	0.4310	0.6448	0.6941	0.042*
C15	0.3218 (4)	0.93558 (16)	0.4607 (2)	0.0530 (8)
H15A	0.4045	0.9110	0.4141	0.079*
H15B	0.3261	0.9898	0.4498	0.079*
H15C	0.2022	0.9174	0.4455	0.079*
C16	0.4575 (5)	0.4742 (2)	0.7866 (3)	0.0815 (11)
H16A	0.5649	0.5019	0.7707	0.122*
H16B	0.4572	0.4264	0.7491	0.122*
H16C	0.4536	0.4648	0.8618	0.122*
H2	0.291 (4)	0.5653 (18)	0.6041 (10)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0671 (2)	0.02604 (16)	0.0779 (3)	−0.00003 (14)	0.01145 (17)	0.00364 (15)
N1	0.0442 (14)	0.0265 (12)	0.0378 (13)	−0.0026 (10)	−0.0020 (10)	−0.0059 (10)
N2	0.0540 (15)	0.0219 (11)	0.0346 (12)	−0.0025 (10)	−0.0071 (12)	−0.0032 (10)
O1	0.0824 (16)	0.0330 (11)	0.0492 (12)	−0.0019 (11)	−0.0106 (11)	0.0004 (9)
O2	0.0814 (16)	0.0344 (11)	0.0359 (11)	−0.0045 (10)	−0.0189 (10)	0.0029 (8)
O3	0.0658 (14)	0.0215 (9)	0.0437 (11)	0.0019 (8)	−0.0123 (10)	0.0040 (8)
O4	0.0815 (17)	0.0257 (10)	0.0458 (13)	0.0000 (9)	−0.0218 (11)	−0.0052 (8)
O5	0.0667 (15)	0.0455 (12)	0.0558 (13)	−0.0083 (11)	−0.0048 (12)	0.0131 (10)
C1	0.0394 (17)	0.0283 (13)	0.0413 (16)	−0.0033 (12)	0.0036 (13)	−0.0056 (12)
C2	0.0431 (17)	0.0291 (13)	0.0424 (16)	−0.0010 (12)	0.0031 (13)	−0.0013 (12)
C3	0.052 (2)	0.0403 (17)	0.0474 (17)	−0.0067 (14)	−0.0019 (14)	−0.0107 (14)
C4	0.057 (2)	0.0309 (15)	0.059 (2)	−0.0117 (13)	0.0078 (16)	−0.0125 (14)
C5	0.0424 (17)	0.0249 (14)	0.0554 (19)	−0.0001 (11)	0.0095 (14)	−0.0025 (13)
C6	0.0464 (18)	0.0289 (14)	0.0428 (16)	−0.0031 (12)	0.0026 (14)	−0.0021 (12)
C7	0.0520 (18)	0.0277 (14)	0.0358 (15)	−0.0001 (12)	−0.0031 (13)	−0.0012 (12)
C8	0.0380 (16)	0.0268 (13)	0.0338 (15)	−0.0014 (11)	−0.0027 (12)	0.0006 (11)
C9	0.0362 (16)	0.0212 (12)	0.0341 (14)	−0.0007 (10)	0.0015 (12)	0.0009 (10)
C10	0.0365 (16)	0.0285 (13)	0.0331 (14)	0.0023 (11)	−0.0051 (12)	0.0039 (11)
C11	0.0375 (16)	0.0179 (12)	0.0396 (15)	0.0030 (10)	−0.0003 (12)	0.0015 (11)
C12	0.0395 (16)	0.0267 (13)	0.0343 (15)	−0.0007 (11)	−0.0030 (12)	−0.0031 (11)
C13	0.0483 (18)	0.0307 (14)	0.0277 (13)	−0.0004 (12)	−0.0081 (12)	0.0018 (11)
C14	0.0455 (17)	0.0242 (13)	0.0352 (15)	−0.0015 (11)	−0.0032 (13)	0.0059 (11)
C15	0.077 (2)	0.0306 (15)	0.0507 (19)	−0.0022 (15)	−0.0197 (16)	0.0146 (13)
C16	0.080 (3)	0.077 (3)	0.087 (3)	0.003 (2)	−0.015 (2)	0.018 (2)

Br1—C5	1.902 (3)	C4—H4A	0.93
N1—C7	1.279 (3)	C5—C6	1.367 (3)
N1—N2	1.383 (3)	C6—H6	0.93
N2—C8	1.356 (3)	C7—H7	0.93
N2—H2	0.893 (10)	C8—C9	1.489 (3)
O1—C2	1.357 (3)	C9—C14	1.375 (3)
O1—H1	0.82	C9—C10	1.399 (3)
O2—C8	1.218 (3)	C10—C11	1.381 (3)
O3—C11	1.372 (3)	C10—H10	0.93
O3—C15	1.423 (3)	C11—C12	1.390 (3)
O4—C12	1.362 (3)	C12—C13	1.376 (3)
O4—H4	0.82	C13—C14	1.383 (3)
O5—C16	1.400 (4)	C13—H13	0.93
O5—H5	0.82	C14—H14	0.93
C1—C2	1.395 (4)	C15—H15A	0.96
C1—C6	1.401 (4)	C15—H15B	0.96
C1—C7	1.442 (3)	C15—H15C	0.96
C2—C3	1.388 (4)	C16—H16A	0.96
C3—C4	1.373 (4)	C16—H16B	0.96
C3—H3	0.93	C16—H16C	0.96
C4—C5	1.376 (4)

C7—N1—N2	115.9 (2)	N2—C8—C9	116.2 (2)
C8—N2—N1	119.7 (2)	C14—C9—C10	119.4 (2)
C8—N2—H2	123 (2)	C14—C9—C8	124.2 (2)
N1—N2—H2	117 (2)	C10—C9—C8	116.4 (2)
C2—O1—H1	109.5	C11—C10—C9	120.3 (2)
C11—O3—C15	117.37 (19)	C11—C10—H10	119.9
C12—O4—H4	109.5	C9—C10—H10	119.9
C16—O5—H5	109.5	O3—C11—C10	124.9 (2)
C2—C1—C6	118.5 (2)	O3—C11—C12	115.4 (2)
C2—C1—C7	123.3 (2)	C10—C11—C12	119.7 (2)
C6—C1—C7	118.2 (2)	O4—C12—C13	122.9 (2)
O1—C2—C3	117.6 (2)	O4—C12—C11	117.4 (2)
O1—C2—C1	122.3 (2)	C13—C12—C11	119.7 (2)
C3—C2—C1	120.0 (3)	C12—C13—C14	120.6 (2)
C4—C3—C2	120.4 (3)	C12—C13—H13	119.7
C4—C3—H3	119.8	C14—C13—H13	119.7
C2—C3—H3	119.8	C9—C14—C13	120.2 (2)
C3—C4—C5	119.7 (3)	C9—C14—H14	119.9
C3—C4—H4A	120.1	C13—C14—H14	119.9
C5—C4—H4A	120.1	O3—C15—H15A	109.5
C6—C5—C4	120.9 (3)	O3—C15—H15B	109.5
C6—C5—Br1	119.1 (2)	H15A—C15—H15B	109.5
C4—C5—Br1	119.9 (2)	O3—C15—H15C	109.5
C5—C6—C1	120.3 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.8	H15B—C15—H15C	109.5
C1—C6—H6	119.8	O5—C16—H16A	109.5
N1—C7—C1	122.5 (2)	O5—C16—H16B	109.5
N1—C7—H7	118.7	H16A—C16—H16B	109.5
C1—C7—H7	118.7	O5—C16—H16C	109.5
O2—C8—N2	121.7 (2)	H16A—C16—H16C	109.5
O2—C8—C9	122.1 (2)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.89 (1)	2.07 (1)	2.949 (3)	167 (3)
O1—H1···N1	0.82	1.98	2.686 (3)	145
O4—H4···O2ⁱ	0.82	1.87	2.671 (3)	166
O5—H5···O3ⁱⁱ	0.82	2.46	3.125 (3)	139
O5—H5···O4ⁱⁱ	0.82	2.57	3.252 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.89 (1)	2.07 (1)	2.949 (3)	167 (3)
O1—H1⋯N1	0.82	1.98	2.686 (3)	145
O4—H4⋯O2ⁱ	0.82	1.87	2.671 (3)	166
O5—H5⋯O3ⁱⁱ	0.82	2.46	3.125 (3)	139
O5—H5⋯O4ⁱⁱ	0.82	2.57	3.252 (3)	141

Symmetry codes: (i) ; (ii) .

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