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

The title compound, C(14)H(11)BrClNO, is a Schiff base compound derived from the condensation of 3-bromo-5-chloro-salicyl-aldehyde and o-toluidine in methanol. The aromatic rings make a dihedral angle of 38.3 (1)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, generating an S(6) ring.

Related literature

For Schiff bases, see: Ali et al. (2002 ▶). For related structures, see: Li & Zhang (2005 ▶, 2006 ▶); Li et al. (2006 ▶).

Experimental

Crystal data

C14H11BrClNO

M = 324.60

Orthorhombic,

a = 7.5388 (9) Å

b = 12.2452 (11) Å

c = 14.2440 (16) Å

V = 1314.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.32 mm−1

T = 298 K

0.40 × 0.38 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.351, T max = 0.408

5422 measured reflections

2284 independent reflections

1815 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.057

S = 1.09

2284 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 938 Friedel pairs

Flack parameter: 0.006 (10)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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/S1600536810037931/bt5360sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037931/bt5360Isup2.hkl

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

C14H11BrClNO	Dx = 1.640 Mg m−3
Mr = 324.60	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2013 reflections
a = 7.5388 (9) Å	θ = 2.2–23.7°
b = 12.2452 (11) Å	µ = 3.32 mm−1
c = 14.2440 (16) Å	T = 298 K
V = 1314.9 (2) Å3	Block, yellow
Z = 4	0.40 × 0.38 × 0.33 mm
F(000) = 648

Bruker SMART CCD area-detector diffractometer	2284 independent reflections
Radiation source: fine-focus sealed tube	1815 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→8
Tmin = 0.351, Tmax = 0.408	k = −14→14
5422 measured reflections	l = −16→8

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) = 0.057	w = 1/[σ2(Fo2) + (0.0039P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2284 reflections	Δρmax = 0.25 e Å−3
164 parameters	Δρmin = −0.33 e Å−3
0 restraints	Absolute structure: Flack (1983), 938 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.006 (10)

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	0.04915 (6)	0.84654 (3)	−0.29615 (2)	0.06176 (15)
Cl1	0.26999 (17)	1.17472 (7)	−0.05785 (7)	0.0692 (3)
N1	0.1302 (3)	0.6835 (2)	0.05868 (17)	0.0362 (7)
O1	0.0835 (3)	0.71558 (18)	−0.11917 (15)	0.0500 (7)
H1	0.0929	0.6804	−0.0704	0.075*
C1	0.1777 (5)	0.7832 (3)	0.0667 (2)	0.0388 (9)
H1A	0.2136	0.8093	0.1250	0.047*
C2	0.1770 (4)	0.8568 (3)	−0.0137 (2)	0.0339 (8)
C3	0.1263 (4)	0.8203 (3)	−0.1027 (2)	0.0376 (9)
C4	0.1196 (5)	0.8952 (3)	−0.1764 (2)	0.0400 (9)
C5	0.1624 (5)	1.0029 (3)	−0.1627 (2)	0.0450 (10)
H5	0.1554	1.0522	−0.2122	0.054*
C6	0.2160 (5)	1.0382 (3)	−0.0746 (2)	0.0447 (10)
C7	0.2229 (5)	0.9665 (3)	−0.0010 (2)	0.0408 (9)
H7	0.2583	0.9909	0.0579	0.049*
C8	0.1220 (5)	0.6153 (3)	0.1403 (2)	0.0364 (9)
C9	0.1705 (5)	0.5059 (3)	0.1305 (2)	0.0360 (9)
C10	0.1639 (5)	0.4404 (3)	0.2096 (3)	0.0477 (9)
H10	0.1993	0.3678	0.2053	0.057*
C11	0.1059 (5)	0.4805 (3)	0.2947 (3)	0.0516 (11)
H11	0.1014	0.4348	0.3467	0.062*
C12	0.0553 (5)	0.5866 (3)	0.3027 (2)	0.0478 (9)
H12	0.0163	0.6133	0.3602	0.057*
C13	0.0618 (5)	0.6549 (3)	0.22552 (19)	0.0415 (8)
H13	0.0259	0.7273	0.2309	0.050*
C14	0.2313 (6)	0.4607 (3)	0.0376 (2)	0.0600 (12)
H14A	0.2589	0.3845	0.0445	0.090*
H14B	0.3352	0.4993	0.0171	0.090*
H14C	0.1387	0.4692	−0.0081	0.090*

	U11	U22	U33	U12	U13	U23
Br1	0.0701 (3)	0.0765 (3)	0.03869 (18)	0.0032 (3)	−0.0065 (2)	0.0004 (2)
Cl1	0.1052 (9)	0.0331 (5)	0.0692 (6)	−0.0064 (6)	−0.0041 (6)	0.0075 (5)
N1	0.0390 (18)	0.0323 (16)	0.0372 (15)	−0.0012 (14)	0.0006 (13)	0.0021 (14)
O1	0.064 (2)	0.0434 (14)	0.0423 (13)	−0.0024 (13)	−0.0035 (13)	−0.0011 (11)
C1	0.034 (2)	0.045 (2)	0.038 (2)	0.0001 (18)	0.0003 (18)	0.0037 (18)
C2	0.035 (2)	0.033 (2)	0.0335 (17)	0.0014 (19)	0.0021 (15)	0.0014 (18)
C3	0.033 (2)	0.034 (2)	0.046 (2)	0.0048 (17)	0.0093 (16)	−0.0010 (18)
C4	0.036 (2)	0.050 (2)	0.034 (2)	0.0074 (18)	0.0019 (16)	0.0027 (17)
C5	0.045 (3)	0.050 (2)	0.040 (2)	0.009 (2)	0.0088 (19)	0.0144 (19)
C6	0.045 (3)	0.038 (2)	0.050 (2)	0.001 (2)	0.0066 (19)	0.006 (2)
C7	0.045 (3)	0.041 (2)	0.0354 (19)	−0.002 (2)	0.0011 (17)	0.0011 (18)
C8	0.038 (2)	0.036 (2)	0.0354 (19)	−0.0042 (16)	−0.0018 (16)	0.0049 (16)
C9	0.039 (2)	0.030 (2)	0.0396 (19)	−0.0054 (18)	−0.0004 (18)	0.0001 (17)
C10	0.052 (3)	0.033 (2)	0.058 (2)	−0.0044 (18)	−0.001 (2)	0.004 (2)
C11	0.063 (3)	0.051 (3)	0.041 (2)	−0.010 (2)	−0.006 (2)	0.017 (2)
C12	0.054 (3)	0.053 (2)	0.0363 (19)	−0.012 (2)	0.005 (2)	0.0002 (19)
C13	0.049 (2)	0.0355 (19)	0.0402 (18)	0.002 (2)	0.0055 (17)	−0.0007 (17)
C14	0.075 (3)	0.050 (2)	0.055 (2)	0.000 (3)	0.015 (2)	0.000 (2)

Br1—C4	1.883 (3)	C7—H7	0.9300
Cl1—C6	1.737 (4)	C8—C13	1.383 (4)
N1—C1	1.277 (4)	C8—C9	1.395 (4)
N1—C8	1.433 (4)	C9—C10	1.385 (4)
O1—C3	1.343 (4)	C9—C14	1.506 (5)
O1—H1	0.8200	C10—C11	1.378 (5)
C1—C2	1.458 (4)	C10—H10	0.9300
C1—H1A	0.9300	C11—C12	1.359 (5)
C2—C7	1.398 (5)	C11—H11	0.9300
C2—C3	1.398 (4)	C12—C13	1.382 (4)
C3—C4	1.394 (4)	C12—H12	0.9300
C4—C5	1.373 (5)	C13—H13	0.9300
C5—C6	1.386 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.368 (4)	C14—H14C	0.9600
C1—N1—C8	119.8 (3)	C13—C8—N1	121.5 (3)
C3—O1—H1	109.5	C9—C8—N1	117.8 (3)
N1—C1—C2	121.3 (3)	C10—C9—C8	117.7 (3)
N1—C1—H1A	119.3	C10—C9—C14	120.8 (3)
C2—C1—H1A	119.3	C8—C9—C14	121.4 (3)
C7—C2—C3	119.4 (3)	C11—C10—C9	121.3 (3)
C7—C2—C1	119.5 (3)	C11—C10—H10	119.3
C3—C2—C1	121.1 (3)	C9—C10—H10	119.3
O1—C3—C4	119.2 (3)	C12—C11—C10	120.2 (3)
O1—C3—C2	121.9 (3)	C12—C11—H11	119.9
C4—C3—C2	118.9 (3)	C10—C11—H11	119.9
C5—C4—C3	121.0 (3)	C11—C12—C13	120.1 (3)
C5—C4—Br1	120.0 (3)	C11—C12—H12	119.9
C3—C4—Br1	119.0 (3)	C13—C12—H12	119.9
C4—C5—C6	119.8 (3)	C12—C13—C8	119.8 (3)
C4—C5—H5	120.1	C12—C13—H13	120.1
C6—C5—H5	120.1	C8—C13—H13	120.1
C7—C6—C5	120.3 (3)	C9—C14—H14A	109.5
C7—C6—Cl1	120.2 (3)	C9—C14—H14B	109.5
C5—C6—Cl1	119.5 (3)	H14A—C14—H14B	109.5
C6—C7—C2	120.5 (3)	C9—C14—H14C	109.5
C6—C7—H7	119.7	H14A—C14—H14C	109.5
C2—C7—H7	119.7	H14B—C14—H14C	109.5
C13—C8—C9	120.7 (3)
C8—N1—C1—C2	−176.1 (3)	Cl1—C6—C7—C2	179.0 (3)
N1—C1—C2—C7	177.3 (3)	C3—C2—C7—C6	0.9 (5)
N1—C1—C2—C3	−0.9 (5)	C1—C2—C7—C6	−177.3 (3)
C7—C2—C3—O1	179.0 (3)	C1—N1—C8—C13	38.4 (5)
C1—C2—C3—O1	−2.8 (5)	C1—N1—C8—C9	−144.0 (3)
C7—C2—C3—C4	−1.3 (5)	C13—C8—C9—C10	−2.8 (5)
C1—C2—C3—C4	176.9 (3)	N1—C8—C9—C10	179.5 (3)
O1—C3—C4—C5	−180.0 (3)	C13—C8—C9—C14	178.3 (3)
C2—C3—C4—C5	0.3 (5)	N1—C8—C9—C14	0.6 (5)
O1—C3—C4—Br1	0.4 (4)	C8—C9—C10—C11	2.1 (5)
C2—C3—C4—Br1	−179.4 (3)	C14—C9—C10—C11	−179.0 (3)
C3—C4—C5—C6	1.1 (5)	C9—C10—C11—C12	−0.7 (6)
Br1—C4—C5—C6	−179.3 (3)	C10—C11—C12—C13	0.0 (6)
C4—C5—C6—C7	−1.4 (6)	C11—C12—C13—C8	−0.8 (6)
C4—C5—C6—Cl1	180.0 (3)	C9—C8—C13—C12	2.2 (6)
C5—C6—C7—C2	0.4 (5)	N1—C8—C13—C12	179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.588 (3)	147

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	2.588 (3)	147