2-[(E)-(4-Bromo­phenyl)imino­methyl]-4-chloro­phenol

Gao, X.-L.; Feng, S.-S.; Yuan, C.-X.; Zhu, M.-L.

doi:10.1107/S1600536814000981

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o235-o236

doi:10.1107/S1600536814000981

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2-[(E)-(4-Bromophenyl)iminomethyl]-4-chlorophenol

Xiao-Li Gao,^a Si-Si Feng,^b Cai-Xia Yuan ^b and Miao-Li Zhu ^b ^*

^aDepartment of Chemistry, Taiyuan Normal College, Taiyuan, Shanxi 030031, People's Republic of China, and ^bInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: miaoli@sxu.edu.cn

(Received 12 November 2013; accepted 15 January 2014; online 5 February 2014)

In the title compound, C₁₃H₉BrClNO, the dihedral angle between the substituted benzene rings is 44.25 (11)°. There are strong intramolecular O—H⋯N hydrogen bonds, which generate S(6) rings, and also intermolecular 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 interactions.

CCDC reference: 981552

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_r = 310.57
Orthorhombic, P c c n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.128
S = 1.14
3013 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.95 e Å⁻³

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) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y, z-{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y, z-{\script{3\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 981552

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814000981/fj2653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000981/fj2653Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000981/fj2653Isup3.cml

checkCIF report

Comment top

Schiff bases are condensed by primary amines and carbonyl compounds, containing strong electronegative with atoms O and N, thus it is easy to coordinate with the metal ions to form stable complexes (Akmal et al., 2007; Rehmana et al., 2008). It is reported that metal complexes of Schiff base derivatives have a variety of important biological activities, such as anti-bacterial, anti-cancer, anti-tumor, hypoglycemic and so on (Vanco et al., 2008; Li et al., 2007; Ritter et al., 2009). Our reports indicated that copper and vanadium complexes of Schiff bases are potential inhitors over protein tyrosine phosphatases (Li et al., 2011; Lu et al., 2011; Ma et al., 2011; Yuan et al., 2009, 2010).

We report here the synthesis and characterization a potentially bidentate Schiff base derivative, (I), and prepared from the condensation reaction of an equimolar proportion of 5-chloro-salicylaldehyde and 4-bromo-aniline in absolute ethanol. The molecular structure is depicted in Fig. 1. X-ray structural analysis confirmed that in the title compound, (I), the dihedral angle between the substituted benzene rings is nearly 44.25 (11)°, similar to the compound 4-bromo-2-[(E)-(4-chlorophenyl)iminomethyl]phenol (Ardakani et al., 2011). In the crystal, there are strong intramolecular O—H···N hydrogen bonds with a distance of 2.593 (5) Å between donor and acceptor, which generate S(6) ring and intermolecular Cl1···Cl1ⁱ [3.430 (2) Å, i -x, -y, -z] as well as Br1···Br1ⁱⁱ [3.846 (1) Å, ii 2 - x, -y, -z] contacts. The crystal packing is further stabilized by intermolecular C—H···O and C—H···π interactions (Table 1).

Related literature top

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 top

A 0.1566 g (1.0 mmol) 5-chloro-salicylaldehyde in 15 ml of absolute ethanol was heated until thoroughly dissolved and 0.1720 g (1.0 mmol) of 4-bromo-aniline in 5 ml of absolute ethanol was added dropwise with a constant stirring. The reaction mixture was heated under refluxing for 3 h. After cooling slowly, the orange powder was separated out. Orange–red crystal was obtained from filter after two weeks.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top

	Fig. 1. A view of the structure of (I), with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen-bonding interaction.
	Fig. 2. The packing diagram of the title compound, showing the intermolecular O—H···N and intermolecular Cl···Cl, Br···Br and C—H···O interactions (dotted lines).

2-[(E)-(4-Bromophenyl)iminomethyl]-4-chlorophenol top

Crystal data top

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

Data collection top

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 top

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

Crystal data top

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

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.14	Δρ_max = 0.42 e Å⁻³
3013 reflections	Δρ_min = −0.95 e Å⁻³
155 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y, z−1/2; (ii) −x+3/2, y, z−3/2; (iii) −x+1/2, y, z−3/2; (iv) −x+3/2, y, z−1/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y, z−1/2; (ii) −x+3/2, y, z−3/2; (iii) −x+1/2, y, z−3/2; (iv) −x+3/2, y, z−1/2.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 21001070 and 21171109), the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20111401110002) and the Natural Science Foundation of Shanxi Province (grant Nos. 2010011011-2, 2011011009-1 and 2011021006-2).

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o235-o236

doi:10.1107/S1600536814000981

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