Literature DB >> 24764958

2-[(E)-(4-Bromo-phenyl)imino-methyl]-4-chloro-phenol.

Xiao-Li Gao¹, Si-Si Feng², Cai-Xia Yuan², Miao-Li Zhu².

Abstract

In the title compound, C13H9BrClNO, the dihedral angle between the substituted benzene rings is 44.25 (11)°. There are strong intra-molecular O-H⋯N hydrogen bonds, which generate S(6) rings, and also inter-molecular Cl⋯Cl [3.431 (3) Å] and Br⋯ Br [3.846 (1) Å] contacts. The crystal packing a C-H⋯O and C-H⋯π inter-actions.

Entities: Chemical Disease Gene Species

Year: 2014 PMID： 24764958 PMCID： PMC3998382 DOI： 10.1107/S1600536814000981

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

Related literature

For background to the biological activity of Schiff bases, see: Akmal et al. (2007 ▶); Li et al. (2007 ▶, 2011 ▶); Lu et al. (2011 ▶); Ma et al. (2011 ▶); Rehmana et al. (2008 ▶); Ritter et al. (2009 ▶); Vanco et al. (2008 ▶); Yuan et al. (2009 ▶, 2010 ▶). For related structures, see: Ardakani et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9BrClNO M = 310.57 Orthorhombic, a = 6.9964 (15) Å b = 55.786 (12) Å c = 6.1443 (14) Å V = 2398.1 (9) Å3 Z = 8 Mo Kα radiation μ = 3.63 mm−1 T = 298 K 0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.409, T max = 0.530 30095 measured reflections 3013 independent reflections 2056 reflections with I > 2σ(I) R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.128 S = 1.14 3013 reflections 155 parameters H-atom parameters constrained Δρmax = 0.42 e Å−3 Δρmin = −0.95 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814000981/fj2653sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000981/fj2653Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814000981/fj2653Isup3.cml CCDC reference: Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₃H₉BrClNO	F(000) = 1232
M_r = 310.57	D_x = 1.720 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 4170 reflections
a = 6.9964 (15) Å	θ = 2.2–22.6°
b = 55.786 (12) Å	µ = 3.63 mm⁻¹
c = 6.1443 (14) Å	T = 298 K
V = 2398.1 (9) Å³	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker SMART 1K CCD area-detector diffractometer	3013 independent reflections
Radiation source: fine-focus sealed tube	2056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
T_min = 0.409, T_max = 0.530	k = −74→74
30095 measured reflections	l = −8→8

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.027P)² + 7.4937P] where P = (F_o² + 2F_c²)/3
3013 reflections	(Δ/σ)_max = 0.001
155 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.95 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
Br1	−0.03618 (9)	0.228348 (8)	−0.07815 (11)	0.0634 (2)
C1	−0.0360 (6)	0.08714 (7)	0.5859 (7)	0.0339 (8)
C2	−0.0711 (6)	0.06455 (8)	0.6715 (7)	0.0404 (10)
H2	−0.1186	0.0631	0.8123	0.049*
C3	−0.0364 (6)	0.04435 (7)	0.5506 (8)	0.0426 (11)
H3	−0.0609	0.0293	0.6092	0.051*
C4	0.0346 (6)	0.04637 (7)	0.3425 (7)	0.0372 (10)
C5	0.0691 (6)	0.06843 (7)	0.2537 (7)	0.0333 (9)
H5	0.1169	0.0695	0.1129	0.040*
C6	0.0332 (6)	0.08932 (7)	0.3722 (6)	0.0306 (8)
C7	0.0538 (6)	0.11247 (7)	0.2675 (7)	0.0335 (9)
H7	0.0897	0.1132	0.1219	0.040*
C8	0.0157 (5)	0.15412 (7)	0.2599 (7)	0.0304 (8)
C9	−0.0626 (6)	0.15603 (7)	0.0518 (7)	0.0335 (9)
H9	−0.1044	0.1424	−0.0209	0.040*
C10	−0.0780 (6)	0.17821 (7)	−0.0459 (7)	0.0359 (9)
H10	−0.1315	0.1795	−0.1839	0.043*
C11	−0.0140 (6)	0.19838 (7)	0.0610 (8)	0.0392 (10)
C12	0.0610 (6)	0.19682 (7)	0.2681 (8)	0.0401 (10)
H12	0.1013	0.2106	0.3402	0.048*
C13	0.0759 (6)	0.17470 (7)	0.3676 (7)	0.0352 (9)
H13	0.1265	0.1736	0.5072	0.042*
Cl1	0.0736 (2)	0.02081 (2)	0.1879 (2)	0.0614 (4)
N1	0.0235 (5)	0.13186 (6)	0.3721 (5)	0.0322 (7)
O1	−0.0721 (5)	0.10666 (5)	0.7096 (5)	0.0474 (8)
H1	−0.0470	0.1188	0.6401	0.071*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0722 (4)	0.0352 (2)	0.0829 (4)	0.0069 (2)	−0.0019 (3)	0.0149 (3)
C1	0.035 (2)	0.038 (2)	0.029 (2)	−0.0004 (18)	−0.0007 (18)	−0.0038 (17)
C2	0.036 (2)	0.053 (3)	0.032 (2)	−0.004 (2)	0.002 (2)	0.007 (2)
C3	0.046 (2)	0.034 (2)	0.048 (3)	−0.0034 (19)	0.000 (2)	0.0120 (19)
C4	0.039 (2)	0.0318 (19)	0.041 (2)	0.0016 (18)	−0.001 (2)	−0.0023 (17)
C5	0.037 (2)	0.0304 (19)	0.032 (2)	0.0017 (17)	0.0008 (19)	−0.0019 (16)
C6	0.030 (2)	0.0345 (19)	0.028 (2)	0.0024 (17)	−0.0034 (17)	0.0023 (15)
C7	0.034 (2)	0.038 (2)	0.029 (2)	0.0013 (17)	0.0027 (19)	0.0018 (17)
C8	0.029 (2)	0.0299 (18)	0.032 (2)	0.0004 (15)	0.0030 (17)	−0.0019 (16)
C9	0.039 (2)	0.0289 (18)	0.033 (2)	−0.0029 (17)	−0.0012 (19)	−0.0041 (16)
C10	0.033 (2)	0.038 (2)	0.037 (2)	0.0031 (17)	0.0000 (19)	−0.0019 (18)
C11	0.036 (2)	0.0315 (19)	0.050 (3)	0.0041 (17)	0.006 (2)	0.0035 (19)
C12	0.042 (2)	0.0299 (19)	0.048 (3)	−0.0017 (18)	−0.003 (2)	−0.0077 (18)
C13	0.033 (2)	0.037 (2)	0.036 (2)	−0.0005 (17)	−0.0029 (18)	−0.0080 (17)
Cl1	0.0858 (10)	0.0333 (5)	0.0652 (8)	−0.0007 (6)	0.0074 (8)	−0.0081 (6)
N1	0.0343 (18)	0.0305 (15)	0.0318 (18)	−0.0003 (14)	−0.0008 (15)	−0.0009 (14)
O1	0.069 (2)	0.0394 (16)	0.0342 (17)	0.0003 (16)	0.0096 (17)	−0.0042 (13)

Br1—C11	1.884 (4)	C7—H7	0.9300
C1—O1	1.352 (5)	C8—C13	1.390 (5)
C1—C2	1.387 (6)	C8—C9	1.395 (6)
C1—C6	1.405 (6)	C8—N1	1.422 (5)
C2—C3	1.371 (6)	C9—C10	1.379 (5)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.377 (6)	C10—C11	1.378 (6)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.367 (6)	C11—C12	1.379 (7)
C4—Cl1	1.735 (4)	C12—C13	1.381 (6)
C5—C6	1.397 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.450 (5)	O1—H1	0.8200
C7—N1	1.276 (5)

O1—C1—C2	119.1 (4)	C13—C8—C9	119.5 (4)
O1—C1—C6	121.3 (4)	C13—C8—N1	118.6 (4)
C2—C1—C6	119.6 (4)	C9—C8—N1	121.7 (3)
C3—C2—C1	120.6 (4)	C10—C9—C8	119.8 (4)
C3—C2—H2	119.7	C10—C9—H9	120.1
C1—C2—H2	119.7	C8—C9—H9	120.1
C2—C3—C4	120.0 (4)	C11—C10—C9	120.0 (4)
C2—C3—H3	120.0	C11—C10—H10	120.0
C4—C3—H3	120.0	C9—C10—H10	120.0
C5—C4—C3	120.5 (4)	C10—C11—C12	120.8 (4)
C5—C4—Cl1	119.6 (3)	C10—C11—Br1	118.8 (3)
C3—C4—Cl1	119.9 (3)	C12—C11—Br1	120.4 (3)
C4—C5—C6	120.8 (4)	C11—C12—C13	119.6 (4)
C4—C5—H5	119.6	C11—C12—H12	120.2
C6—C5—H5	119.6	C13—C12—H12	120.2
C5—C6—C1	118.5 (4)	C12—C13—C8	120.3 (4)
C5—C6—C7	119.6 (4)	C12—C13—H13	119.9
C1—C6—C7	121.7 (4)	C8—C13—H13	119.9
N1—C7—C6	121.0 (4)	C7—N1—C8	120.2 (3)
N1—C7—H7	119.5	C1—O1—H1	109.5
C6—C7—H7	119.5

O1—C1—C2—C3	179.9 (4)	C1—C6—C7—N1	5.4 (6)
C6—C1—C2—C3	0.9 (6)	C13—C8—C9—C10	0.6 (6)
C1—C2—C3—C4	0.3 (7)	N1—C8—C9—C10	176.0 (4)
C2—C3—C4—C5	−0.8 (7)	C8—C9—C10—C11	0.7 (6)
C2—C3—C4—Cl1	−178.6 (4)	C9—C10—C11—C12	−1.8 (6)
C3—C4—C5—C6	0.1 (6)	C9—C10—C11—Br1	179.7 (3)
Cl1—C4—C5—C6	178.0 (3)	C10—C11—C12—C13	1.4 (7)
C4—C5—C6—C1	1.1 (6)	Br1—C11—C12—C13	179.9 (3)
C4—C5—C6—C7	−174.2 (4)	C11—C12—C13—C8	0.0 (6)
O1—C1—C6—C5	179.5 (4)	C9—C8—C13—C12	−1.0 (6)
C2—C1—C6—C5	−1.6 (6)	N1—C8—C13—C12	−176.6 (4)
O1—C1—C6—C7	−5.3 (6)	C6—C7—N1—C8	−170.4 (3)
C2—C1—C6—C7	173.6 (4)	C13—C8—N1—C7	−148.7 (4)
C5—C6—C7—N1	−179.4 (4)	C9—C8—N1—C7	35.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.593 (4)	147
C2—H2···Cg1ⁱ	0.93	2.82	3.489 (5)	129
C5—H5···Cg1ⁱⁱ	0.93	2.85	3.513 (5)	129
C10—H10···Cg2ⁱⁱⁱ	0.93	2.75	3.460 (5)	133
C13—H13···Cg2^iv	0.93	2.78	3.473 (5)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.593 (4)	147
C2—H2⋯Cg1ⁱ	0.93	2.82	3.489 (5)	129
C5—H5⋯Cg1ⁱⁱ	0.93	2.85	3.513 (5)	129
C10—H10⋯Cg2ⁱⁱⁱ	0.93	2.75	3.460 (5)	133
C13—H13⋯Cg2^iv	0.93	2.78	3.473 (5)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

9 in total

1. Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from salicylaldehyde, 2-furaldehyde and phenylenediamine.

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2. A short history of SHELX.

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

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4. Ternary oxovanadium(IV) complexes with amino acid-Schiff base and polypyridyl derivatives: synthesis, characterization, and protein tyrosine phosphatase 1B inhibition.

Authors: Liping Lu; Jinjun Yue; Caixia Yuan; Miaoli Zhu; Hong Han; Zhiwei Liu; Maolin Guo
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5. Synthesis, characterization, and protein tyrosine phosphatases inhibition activities of oxovanadium(IV) complexes with Schiff base and polypyridyl derivatives.

Authors: Caixia Yuan; Liping Lu; Yanbo Wu; Zhiwei Liu; Maolin Guo; Shu Xing; Xueqi Fu; Miaoli Zhu
Journal: J Inorg Biochem Date: 2010-05-15 Impact factor: 4.155

6. Mononuclear copper(II) complexes with 3,5-substituted-4-salicylidene-amino-3,5-dimethyl-1,2,4-triazole: synthesis, structure and potent inhibition of protein tyrosine phosphatases.

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Journal: Dalton Trans Date: 2011-05-24 Impact factor: 4.390

7. Ternary oxovanadium(IV) complexes of ONO-donor Schiff base and polypyridyl derivatives as protein tyrosine phosphatase inhibitors: synthesis, characterization, and biological activities.

Authors: Caixia Yuan; Liping Lu; Xiaoli Gao; Yanbo Wu; Maolin Guo; Ying Li; Xueqi Fu; Miaoli Zhu
Journal: J Biol Inorg Chem Date: 2009-03-17 Impact factor: 3.358

8. Synthesis, structural characterization, antiradical and antidiabetic activities of copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and beta-alanine.

Authors: Ján Vanco; Jaromír Marek; Zdenek Trávnícek; Eva Racanská; Jan Muselík; Ol'ga Svajlenová
Journal: J Inorg Biochem Date: 2007-10-24 Impact factor: 4.155

9. 4-Bromo-2-[(E)-(4-chloro-phen-yl)imino-meth-yl]phenol.

Authors: Amir Adabi Ardakani; Reza Kia; Hadi Kargar; Muhammad Nawaz Tahir
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-02-12

9 in total