Literature DB >> 21201145

N'-(3-Bromo-5-chloro-2-hydroxy-benzyl-idene)-4-hydr-oxybenzohydrazide.

Ling-Wei Xue¹, Yong-Jun Han, Cheng-Jun Hao, Gan-Qing Zhao, Qiao-Ru Liu.

Abstract

The mol-ecule of the title compound, C(14)H(10)BrClN(2)O(3), is planar [dihedral angle between the aromatic rings = 3.0 (2)°] and shows a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds and an intramolecular O-H⋯N interaction also occurs.

Entities: Chemical Disease Species

Year: 2008 PMID： 21201145 PMCID： PMC2959268 DOI： 10.1107/S160053680802905X

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

Related literature

For the biological properties of Schiff bases, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶); Sondhi et al. (2006 ▶); Singh et al. (2006 ▶). For background on Schiff bases derived from aldehydes with benzohydrazides, see: He & Liu (2005 ▶); Zhen & Han (2005 ▶); Diao & Yu (2006 ▶); Shan et al. (2008 ▶); Fun et al. (2008 ▶). For related structures, see: Jing et al. (2005 ▶); Lu et al. (2008 ▶); Salhin et al. (2007 ▶).

Experimental

Crystal data

C14H10BrClN2O3 M = 369.60 Monoclinic, a = 8.279 (2) Å b = 11.446 (3) Å c = 14.998 (4) Å β = 99.002 (4)° V = 1403.7 (6) Å3 Z = 4 Mo Kα radiation μ = 3.13 mm−1 T = 298 (2) K 0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.618, T max = 0.651 10685 measured reflections 3006 independent reflections 2102 reflections with I > 2σ(I) R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.100 S = 1.03 3006 reflections 195 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.50 e Å−3 Δρmin = −0.36 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S160053680802905X/bx2178sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680802905X/bx2178Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₀BrClN₂O₃	F(000) = 736
M_r = 369.60	D_x = 1.749 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.279 (2) Å	Cell parameters from 2405 reflections
b = 11.446 (3) Å	θ = 2.3–24.6°
c = 14.998 (4) Å	µ = 3.13 mm⁻¹
β = 99.002 (4)°	T = 298 K
V = 1403.7 (6) Å³	Block, colourless
Z = 4	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	3006 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
graphite	R_int = 0.049
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.618, T_max = 0.651	k = −14→14
10685 measured reflections	l = −19→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0455P)² + 0.1022P] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.36 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	1.16504 (5)	0.88843 (3)	1.28591 (2)	0.05440 (17)
Cl1	1.19663 (10)	0.56024 (7)	1.02050 (6)	0.0436 (2)
N1	0.7282 (3)	0.9996 (2)	0.98662 (16)	0.0299 (6)
N2	0.6142 (3)	1.0530 (2)	0.92314 (15)	0.0303 (6)
O1	0.9168 (3)	0.98960 (19)	1.14418 (14)	0.0409 (5)
H1	0.8479	1.0183	1.1051	0.061*
O2	0.5803 (3)	1.20014 (17)	1.01833 (13)	0.0387 (5)
O3	0.0964 (3)	1.38132 (18)	0.68220 (14)	0.0426 (6)
H3	0.0978	1.3553	0.6314	0.064*
C1	0.9178 (3)	0.8455 (2)	1.02657 (18)	0.0275 (6)
C2	0.9719 (3)	0.8893 (2)	1.11358 (19)	0.0278 (6)
C3	1.0902 (4)	0.8268 (3)	1.17019 (18)	0.0314 (7)
C4	1.1560 (4)	0.7256 (3)	1.1431 (2)	0.0351 (7)
H4	1.2341	0.6847	1.1824	0.042*
C5	1.1051 (4)	0.6856 (3)	1.0573 (2)	0.0323 (7)
C6	0.9868 (4)	0.7438 (3)	0.9991 (2)	0.0324 (7)
H6	0.9532	0.7149	0.9412	0.039*
C7	0.7930 (4)	0.9061 (3)	0.9632 (2)	0.0327 (7)
H7	0.7610	0.8760	0.9056	0.039*
C8	0.5482 (4)	1.1559 (3)	0.94328 (19)	0.0283 (7)
C9	0.4350 (3)	1.2130 (2)	0.87016 (17)	0.0258 (6)
C10	0.3617 (4)	1.3161 (3)	0.89023 (19)	0.0344 (7)
H10	0.3888	1.3482	0.9476	0.041*
C11	0.2498 (4)	1.3723 (3)	0.8275 (2)	0.0375 (8)
H11	0.2009	1.4412	0.8426	0.045*
C12	0.2103 (4)	1.3258 (3)	0.74178 (18)	0.0287 (7)
C13	0.2856 (4)	1.2251 (3)	0.71958 (18)	0.0349 (7)
H13	0.2615	1.1948	0.6615	0.042*
C14	0.3965 (4)	1.1692 (3)	0.78333 (19)	0.0339 (7)
H14	0.4465	1.1009	0.7679	0.041*
H2	0.577 (5)	1.016 (3)	0.8710 (15)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0585 (3)	0.0637 (3)	0.0345 (2)	0.00635 (19)	−0.01299 (16)	−0.01098 (17)
Cl1	0.0499 (5)	0.0294 (4)	0.0502 (5)	0.0096 (4)	0.0043 (4)	−0.0043 (4)
N1	0.0290 (13)	0.0281 (14)	0.0296 (13)	−0.0019 (11)	−0.0045 (10)	0.0072 (11)
N2	0.0334 (14)	0.0286 (14)	0.0251 (13)	0.0009 (11)	−0.0071 (10)	0.0026 (11)
O1	0.0468 (14)	0.0366 (13)	0.0358 (13)	0.0113 (11)	−0.0046 (10)	−0.0055 (10)
O2	0.0562 (14)	0.0317 (12)	0.0229 (11)	−0.0037 (10)	−0.0105 (9)	0.0004 (9)
O3	0.0609 (15)	0.0360 (13)	0.0264 (11)	0.0180 (11)	−0.0070 (11)	0.0015 (9)
C1	0.0285 (16)	0.0244 (16)	0.0278 (15)	−0.0028 (13)	−0.0009 (12)	0.0029 (12)
C2	0.0281 (16)	0.0255 (16)	0.0288 (15)	−0.0008 (13)	0.0006 (12)	−0.0007 (12)
C3	0.0298 (16)	0.0368 (18)	0.0251 (15)	−0.0048 (14)	−0.0040 (12)	−0.0032 (13)
C4	0.0330 (17)	0.0341 (18)	0.0368 (18)	0.0013 (14)	0.0011 (13)	0.0044 (14)
C5	0.0335 (17)	0.0258 (17)	0.0376 (17)	−0.0019 (13)	0.0056 (13)	−0.0002 (13)
C6	0.0358 (17)	0.0311 (18)	0.0283 (16)	−0.0039 (14)	−0.0009 (13)	0.0006 (13)
C7	0.0356 (18)	0.0313 (18)	0.0288 (16)	−0.0059 (14)	−0.0023 (13)	0.0023 (13)
C8	0.0301 (16)	0.0251 (16)	0.0274 (16)	−0.0075 (13)	−0.0023 (12)	0.0043 (12)
C9	0.0300 (16)	0.0243 (16)	0.0214 (14)	−0.0063 (13)	−0.0009 (11)	0.0043 (12)
C10	0.052 (2)	0.0295 (18)	0.0191 (14)	0.0013 (15)	−0.0020 (13)	−0.0031 (12)
C11	0.056 (2)	0.0253 (17)	0.0296 (17)	0.0130 (15)	−0.0001 (15)	−0.0038 (13)
C12	0.0373 (17)	0.0239 (16)	0.0227 (15)	0.0020 (13)	−0.0023 (12)	0.0057 (12)
C13	0.051 (2)	0.0319 (18)	0.0185 (15)	0.0053 (15)	−0.0046 (13)	−0.0041 (12)
C14	0.0457 (19)	0.0232 (16)	0.0299 (16)	0.0090 (14)	−0.0031 (13)	−0.0029 (13)

Br1—C3	1.886 (3)	C4—C5	1.369 (4)
Cl1—C5	1.751 (3)	C4—H4	0.9300
N1—C7	1.271 (4)	C5—C6	1.378 (4)
N1—N2	1.375 (3)	C6—H6	0.9300
N2—C8	1.353 (4)	C7—H7	0.9300
N2—H2	0.90 (3)	C8—C9	1.478 (4)
O1—C2	1.343 (3)	C9—C10	1.381 (4)
O1—H1	0.8200	C9—C14	1.385 (4)
O2—C8	1.225 (3)	C10—C11	1.372 (4)
O3—C12	1.353 (3)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.383 (4)
C1—C6	1.387 (4)	C11—H11	0.9300
C1—C2	1.404 (4)	C12—C13	1.376 (4)
C1—C7	1.464 (4)	C13—C14	1.376 (4)
C2—C3	1.390 (4)	C13—H13	0.9300
C3—C4	1.368 (4)	C14—H14	0.9300

C7—N1—N2	117.2 (2)	N1—C7—C1	120.4 (3)
C8—N2—N1	119.4 (2)	N1—C7—H7	119.8
C8—N2—H2	120 (3)	C1—C7—H7	119.8
N1—N2—H2	120 (3)	O2—C8—N2	121.8 (3)
C2—O1—H1	109.5	O2—C8—C9	121.4 (3)
C12—O3—H3	109.5	N2—C8—C9	116.8 (2)
C6—C1—C2	119.3 (3)	C10—C9—C14	118.0 (3)
C6—C1—C7	119.1 (3)	C10—C9—C8	117.7 (2)
C2—C1—C7	121.6 (3)	C14—C9—C8	124.3 (3)
O1—C2—C3	118.4 (3)	C11—C10—C9	121.6 (3)
O1—C2—C1	123.2 (3)	C11—C10—H10	119.2
C3—C2—C1	118.4 (3)	C9—C10—H10	119.2
C4—C3—C2	122.0 (3)	C10—C11—C12	119.5 (3)
C4—C3—Br1	120.1 (2)	C10—C11—H11	120.2
C2—C3—Br1	117.9 (2)	C12—C11—H11	120.2
C3—C4—C5	119.0 (3)	O3—C12—C13	122.0 (3)
C3—C4—H4	120.5	O3—C12—C11	118.2 (3)
C5—C4—H4	120.5	C13—C12—C11	119.8 (3)
C4—C5—C6	121.2 (3)	C14—C13—C12	120.0 (3)
C4—C5—Cl1	119.1 (2)	C14—C13—H13	120.0
C6—C5—Cl1	119.7 (2)	C12—C13—H13	120.0
C5—C6—C1	120.2 (3)	C13—C14—C9	121.0 (3)
C5—C6—H6	119.9	C13—C14—H14	119.5
C1—C6—H6	119.9	C9—C14—H14	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.90 (3)	2.17 (3)	2.922 (3)	140 (3)
O1—H1···N1	0.82	1.91	2.623 (3)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.90 (3)	2.17 (3)	2.922 (3)	140 (3)
O1—H1⋯N1	0.82	1.91	2.623 (3)	146

Symmetry code: (i) .

8 in total

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8. 4-Chloro-N'-[(Z)-4-nitro-benzyl-idene]benzohydrazide monohydrate.

Authors: Hoong-Kun Fun; P S Patil; Jyothi N Rao; B Kalluraya; Suchada Chantrapromma
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-08-06