2-Bromo-4-chloro-6-[(E)-(2-chloro-phen-yl)imino-meth-yl]phenol.

The title compound, C(13)H(8)BrCl(2)NO, was obtained by reaction of 3-bromo-5-chloro-salicylaldehyde and 2-chloro-benzenamine in methanol. The mol-ecule displays an E configuration with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 4.57 (11)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯O hydrogen-bonding inter-actions into zigzag chains running parallel to the b axis. Inter-molecular Br⋯Cl [3.5289 (11) Å] and Cl⋯Cl [3.5042 (12) Å] inter-actions are present.

Related literature

For the biological activities of Schiff base complexes, see: Cukurovali et al. (2002 ▶); Tarafder et al. (2002 ▶); Ali et al. (2002 ▶). For halogen–halogen inter­actions, see: Saruma et al. (1986 ▶); Moorthy et al. (2002 ▶).

Experimental

Crystal data

C13H8BrCl2NO

M = 345.01

Monoclinic,

a = 8.4299 (10) Å

b = 14.0115 (16) Å

c = 11.4194 (14) Å

β = 104.5120 (10)°

V = 1305.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.54 mm−1

T = 298 K

0.45 × 0.38 × 0.36 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.230, T max = 0.279

6450 measured reflections

2295 independent reflections

1726 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.077

S = 1.03

2295 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536809007181/rz2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007181/rz2298Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H8BrCl2NO	F(000) = 680
Mr = 345.01	Dx = 1.755 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2353 reflections
a = 8.4299 (10) Å	θ = 2.4–25.2°
b = 14.0115 (16) Å	µ = 3.54 mm−1
c = 11.4194 (14) Å	T = 298 K
β = 104.512 (1)°	Block, yellow
V = 1305.8 (3) Å3	0.45 × 0.38 × 0.36 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	2295 independent reflections
Radiation source: fine-focus sealed tube	1726 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −10→9
Tmin = 0.230, Tmax = 0.279	k = −14→16
6450 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0256P)2 + 0.9771P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2295 reflections	Δρmax = 0.39 e Å−3
164 parameters	Δρmin = −0.57 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (8)

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	Uiso*/Ueq
Br1	0.54350 (5)	0.75675 (2)	0.54203 (4)	0.06096 (18)
Cl1	0.70198 (11)	0.53128 (7)	0.95100 (8)	0.0596 (3)
Cl2	−0.01427 (12)	0.49417 (8)	0.22925 (8)	0.0767 (3)
N1	0.1581 (3)	0.43674 (18)	0.4723 (2)	0.0434 (7)
O1	0.3040 (3)	0.59685 (15)	0.45663 (19)	0.0500 (6)
H1	0.2386	0.5532	0.4344	0.075*
C1	0.2481 (4)	0.4266 (2)	0.5798 (3)	0.0436 (8)
H1A	0.2359	0.3725	0.6238	0.052*
C2	0.3687 (4)	0.4978 (2)	0.6346 (3)	0.0381 (7)
C3	0.3916 (4)	0.5800 (2)	0.5697 (3)	0.0387 (7)
C4	0.5108 (4)	0.6456 (2)	0.6259 (3)	0.0420 (8)
C5	0.6058 (4)	0.6305 (2)	0.7418 (3)	0.0461 (8)
H5	0.6860	0.6744	0.7777	0.055*
C6	0.5809 (4)	0.5499 (2)	0.8042 (3)	0.0453 (8)
C7	0.4644 (4)	0.4838 (2)	0.7520 (3)	0.0436 (8)
H7	0.4492	0.4296	0.7950	0.052*
C8	0.0439 (4)	0.3675 (2)	0.4143 (3)	0.0457 (8)
C9	−0.0435 (4)	0.3866 (3)	0.2963 (3)	0.0528 (9)
C10	−0.1548 (5)	0.3222 (4)	0.2313 (4)	0.0741 (13)
H10	−0.2122	0.3362	0.1524	0.089*
C11	−0.1804 (5)	0.2369 (3)	0.2839 (5)	0.0814 (14)
H11	−0.2550	0.1931	0.2403	0.098*
C12	−0.0967 (5)	0.2165 (3)	0.3997 (5)	0.0751 (12)
H12	−0.1145	0.1589	0.4349	0.090*
C13	0.0149 (5)	0.2818 (3)	0.4650 (4)	0.0622 (10)
H13	0.0711	0.2677	0.5440	0.075*

	U11	U22	U33	U12	U13	U23
Br1	0.0721 (3)	0.0385 (2)	0.0755 (3)	−0.00233 (18)	0.0246 (2)	0.00929 (18)
Cl1	0.0696 (6)	0.0611 (6)	0.0377 (5)	0.0104 (5)	−0.0059 (4)	−0.0064 (4)
Cl2	0.0649 (6)	0.1111 (9)	0.0489 (6)	−0.0086 (6)	0.0043 (5)	0.0204 (6)
N1	0.0443 (15)	0.0433 (15)	0.0400 (16)	−0.0012 (12)	0.0058 (13)	−0.0021 (13)
O1	0.0568 (14)	0.0463 (13)	0.0419 (14)	−0.0019 (11)	0.0033 (11)	0.0102 (11)
C1	0.053 (2)	0.0336 (17)	0.045 (2)	0.0022 (15)	0.0139 (17)	0.0005 (15)
C2	0.0456 (18)	0.0347 (16)	0.0339 (16)	0.0025 (14)	0.0100 (14)	−0.0008 (14)
C3	0.0413 (18)	0.0372 (17)	0.0376 (18)	0.0075 (14)	0.0100 (15)	0.0012 (14)
C4	0.0472 (19)	0.0302 (16)	0.051 (2)	0.0046 (14)	0.0159 (16)	0.0037 (14)
C5	0.0457 (19)	0.0396 (18)	0.051 (2)	0.0001 (15)	0.0078 (17)	−0.0093 (16)
C6	0.052 (2)	0.0444 (19)	0.0365 (18)	0.0114 (16)	0.0050 (15)	−0.0022 (15)
C7	0.056 (2)	0.0365 (17)	0.0375 (18)	0.0046 (16)	0.0096 (16)	0.0017 (15)
C8	0.0420 (18)	0.048 (2)	0.047 (2)	0.0008 (15)	0.0108 (16)	−0.0116 (16)
C9	0.042 (2)	0.073 (2)	0.043 (2)	0.0002 (18)	0.0108 (16)	−0.0120 (18)
C10	0.057 (2)	0.111 (4)	0.052 (2)	−0.013 (2)	0.011 (2)	−0.029 (3)
C11	0.066 (3)	0.088 (3)	0.091 (4)	−0.021 (2)	0.020 (3)	−0.052 (3)
C12	0.073 (3)	0.055 (2)	0.099 (4)	−0.018 (2)	0.023 (3)	−0.022 (3)
C13	0.065 (2)	0.051 (2)	0.065 (3)	−0.0089 (19)	0.006 (2)	−0.0048 (19)

Br1—C4	1.885 (3)	C5—H5	0.9300
Cl1—C6	1.750 (3)	C6—C7	1.373 (5)
Cl2—C9	1.736 (4)	C7—H7	0.9300
N1—C1	1.279 (4)	C8—C13	1.381 (5)
N1—C8	1.409 (4)	C8—C9	1.390 (5)
O1—C3	1.338 (3)	C9—C10	1.377 (5)
O1—H1	0.8200	C10—C11	1.379 (6)
C1—C2	1.449 (4)	C10—H10	0.9300
C1—H1A	0.9300	C11—C12	1.364 (7)
C2—C7	1.394 (4)	C11—H11	0.9300
C2—C3	1.409 (4)	C12—C13	1.388 (5)
C3—C4	1.394 (4)	C12—H12	0.9300
C4—C5	1.381 (4)	C13—H13	0.9300
C5—C6	1.378 (4)
C1—N1—C8	123.1 (3)	C6—C7—H7	120.0
C3—O1—H1	109.5	C2—C7—H7	120.0
N1—C1—C2	121.4 (3)	C13—C8—C9	117.8 (3)
N1—C1—H1A	119.3	C13—C8—N1	125.0 (3)
C2—C1—H1A	119.3	C9—C8—N1	117.2 (3)
C7—C2—C3	119.9 (3)	C10—C9—C8	121.4 (4)
C7—C2—C1	119.5 (3)	C10—C9—Cl2	118.9 (3)
C3—C2—C1	120.6 (3)	C8—C9—Cl2	119.7 (3)
O1—C3—C4	119.2 (3)	C9—C10—C11	119.5 (4)
O1—C3—C2	122.4 (3)	C9—C10—H10	120.3
C4—C3—C2	118.3 (3)	C11—C10—H10	120.3
C5—C4—C3	121.2 (3)	C12—C11—C10	120.3 (4)
C5—C4—Br1	119.4 (2)	C12—C11—H11	119.8
C3—C4—Br1	119.4 (2)	C10—C11—H11	119.8
C6—C5—C4	119.6 (3)	C11—C12—C13	119.9 (4)
C6—C5—H5	120.2	C11—C12—H12	120.1
C4—C5—H5	120.2	C13—C12—H12	120.1
C7—C6—C5	120.9 (3)	C8—C13—C12	121.1 (4)
C7—C6—Cl1	119.8 (3)	C8—C13—H13	119.5
C5—C6—Cl1	119.3 (3)	C12—C13—H13	119.5
C6—C7—C2	120.1 (3)
C8—N1—C1—C2	177.5 (3)	Cl1—C6—C7—C2	−179.4 (2)
N1—C1—C2—C7	−179.9 (3)	C3—C2—C7—C6	−0.2 (5)
N1—C1—C2—C3	−0.8 (5)	C1—C2—C7—C6	178.9 (3)
C7—C2—C3—O1	179.6 (3)	C1—N1—C8—C13	0.1 (5)
C1—C2—C3—O1	0.6 (4)	C1—N1—C8—C9	−178.6 (3)
C7—C2—C3—C4	0.0 (4)	C13—C8—C9—C10	−0.4 (5)
C1—C2—C3—C4	−179.1 (3)	N1—C8—C9—C10	178.4 (3)
O1—C3—C4—C5	−179.1 (3)	C13—C8—C9—Cl2	178.9 (3)
C2—C3—C4—C5	0.6 (4)	N1—C8—C9—Cl2	−2.3 (4)
O1—C3—C4—Br1	0.8 (4)	C8—C9—C10—C11	0.0 (6)
C2—C3—C4—Br1	−179.6 (2)	Cl2—C9—C10—C11	−179.3 (3)
C3—C4—C5—C6	−1.0 (5)	C9—C10—C11—C12	0.3 (6)
Br1—C4—C5—C6	179.2 (2)	C10—C11—C12—C13	−0.1 (7)
C4—C5—C6—C7	0.8 (5)	C9—C8—C13—C12	0.6 (6)
C4—C5—C6—Cl1	180.0 (2)	N1—C8—C13—C12	−178.1 (3)
C5—C6—C7—C2	−0.2 (5)	C11—C12—C13—C8	−0.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.586 (3)	147
C11—H11···O1i	0.93	2.56	3.324 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.586 (3)	147
C11—H11⋯O1i	0.93	2.56	3.324 (5)	139

Symmetry code: (i) .