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

The mol-ecule of the title compound, C(14)H(11)BrClNO, displays an E configuration with respect to the imine C=N double bond. The two aromatic rings are essentially coplanar, forming a dihedral angle of 7.9 (2)°. An intra-molecular O-H⋯N hydrogen bond stabilizes the crystal structure.

Related literature

For the role of Schiff base ligands in catalysis and electron transfer in living organisms, see: Ueno et al. (2006 ▶).

Experimental

Crystal data

C14H11BrClNO

M = 324.60

Triclinic,

a = 8.1354 (14) Å

b = 8.6844 (17) Å

c = 11.3740 (18) Å

α = 76.040 (2)°

β = 73.652 (12)°

γ = 62.458 (12)°

V = 677.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.22 mm−1

T = 298 (2) K

0.43 × 0.18 × 0.09 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.332, T max = 0.745

3500 measured reflections

2351 independent reflections

1412 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.00

2351 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.43 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/S1600536809003912/rz2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003912/rz2287Isup2.hkl

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

C14H11BrClNO	Z = 2
Mr = 324.60	F(000) = 324
Triclinic, P1	Dx = 1.590 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1354 (14) Å	Cell parameters from 1148 reflections
b = 8.6844 (17) Å	θ = 2.7–24.9°
c = 11.3740 (18) Å	µ = 3.22 mm−1
α = 76.040 (2)°	T = 298 K
β = 73.652 (12)°	Block-shaped, yellow
γ = 62.458 (12)°	0.43 × 0.18 × 0.09 mm
V = 677.9 (2) Å3

Siemens SMART CCD area-detector diffractometer	2351 independent reflections
Radiation source: fine-focus sealed tube	1412 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −9→9
Tmin = 0.332, Tmax = 0.745	k = −6→10
3500 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
2351 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.42 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	Uiso*/Ueq
Br1	0.62666 (9)	0.48664 (8)	0.11313 (5)	0.0881 (3)
Cl1	0.2620 (2)	1.09756 (16)	0.31821 (13)	0.0714 (4)
O1	0.7924 (4)	0.3591 (4)	0.3427 (3)	0.0554 (9)
H1	0.8367	0.3272	0.4054	0.083*
N1	0.8449 (5)	0.3835 (5)	0.5491 (3)	0.0414 (9)
C1	0.7224 (6)	0.5406 (6)	0.5417 (4)	0.0434 (11)
H1A	0.6902	0.6050	0.6058	0.052*
C2	0.6298 (6)	0.6243 (6)	0.4356 (4)	0.0381 (10)
C3	0.6708 (6)	0.5270 (6)	0.3398 (4)	0.0387 (10)
C4	0.5770 (6)	0.6130 (6)	0.2422 (4)	0.0439 (11)
C5	0.4522 (6)	0.7843 (6)	0.2351 (4)	0.0457 (11)
H5	0.3916	0.8380	0.1683	0.055*
C6	0.4168 (6)	0.8776 (6)	0.3294 (4)	0.0467 (11)
C7	0.5034 (6)	0.7974 (6)	0.4289 (4)	0.0476 (11)
H7	0.4763	0.8608	0.4925	0.057*
C8	0.9370 (6)	0.3016 (6)	0.6518 (4)	0.0416 (11)
C9	0.9271 (7)	0.3898 (7)	0.7423 (4)	0.0553 (13)
H9	0.8552	0.5102	0.7394	0.066*
C10	1.0267 (7)	0.2956 (8)	0.8377 (4)	0.0619 (14)
H10	1.0201	0.3549	0.8981	0.074*
C11	1.1339 (7)	0.1177 (7)	0.8446 (4)	0.0541 (13)
C12	1.1407 (7)	0.0343 (7)	0.7539 (4)	0.0604 (14)
H12	1.2122	−0.0862	0.7571	0.072*
C13	1.0454 (6)	0.1229 (6)	0.6584 (4)	0.0522 (12)
H13	1.0540	0.0623	0.5981	0.063*
C14	1.2405 (8)	0.0205 (8)	0.9481 (4)	0.0813 (18)
H14A	1.2169	0.1011	1.0021	0.122*
H14B	1.3735	−0.0336	0.9144	0.122*
H14C	1.1990	−0.0679	0.9938	0.122*

	U11	U22	U33	U12	U13	U23
Br1	0.1111 (6)	0.0784 (5)	0.0686 (4)	−0.0123 (4)	−0.0436 (4)	−0.0269 (3)
Cl1	0.0773 (9)	0.0392 (7)	0.0848 (9)	−0.0057 (7)	−0.0321 (8)	−0.0064 (6)
O1	0.058 (2)	0.0406 (19)	0.0586 (19)	−0.0026 (17)	−0.0275 (16)	−0.0109 (15)
N1	0.037 (2)	0.042 (2)	0.046 (2)	−0.0165 (19)	−0.0143 (17)	0.0014 (17)
C1	0.047 (3)	0.046 (3)	0.042 (2)	−0.023 (3)	−0.010 (2)	−0.005 (2)
C2	0.036 (2)	0.041 (3)	0.043 (2)	−0.021 (2)	−0.010 (2)	−0.002 (2)
C3	0.033 (2)	0.039 (3)	0.046 (2)	−0.015 (2)	−0.011 (2)	−0.004 (2)
C4	0.043 (3)	0.047 (3)	0.042 (2)	−0.015 (2)	−0.011 (2)	−0.011 (2)
C5	0.042 (3)	0.048 (3)	0.048 (3)	−0.020 (2)	−0.017 (2)	0.004 (2)
C6	0.045 (3)	0.042 (3)	0.053 (3)	−0.020 (2)	−0.015 (2)	0.002 (2)
C7	0.051 (3)	0.040 (3)	0.055 (3)	−0.018 (2)	−0.015 (2)	−0.009 (2)
C8	0.034 (2)	0.052 (3)	0.041 (2)	−0.023 (2)	−0.012 (2)	0.004 (2)
C9	0.056 (3)	0.053 (3)	0.055 (3)	−0.019 (3)	−0.024 (2)	0.002 (2)
C10	0.062 (3)	0.087 (4)	0.052 (3)	−0.040 (3)	−0.019 (3)	−0.008 (3)
C11	0.049 (3)	0.068 (4)	0.047 (3)	−0.031 (3)	−0.020 (2)	0.016 (3)
C12	0.061 (3)	0.047 (3)	0.069 (3)	−0.021 (3)	−0.029 (3)	0.016 (3)
C13	0.053 (3)	0.048 (3)	0.055 (3)	−0.018 (3)	−0.019 (2)	−0.003 (2)
C14	0.080 (4)	0.110 (5)	0.061 (3)	−0.052 (4)	−0.037 (3)	0.028 (3)

Br1—C4	1.885 (4)	C7—H7	0.9300
Cl1—C6	1.732 (5)	C8—C13	1.381 (6)
O1—C3	1.329 (5)	C8—C9	1.389 (6)
O1—H1	0.8200	C9—C10	1.399 (6)
N1—C1	1.263 (5)	C9—H9	0.9300
N1—C8	1.425 (5)	C10—C11	1.374 (7)
C1—C2	1.462 (5)	C10—H10	0.9300
C1—H1A	0.9300	C11—C12	1.372 (7)
C2—C7	1.372 (6)	C11—C14	1.506 (6)
C2—C3	1.411 (5)	C12—C13	1.376 (6)
C3—C4	1.387 (5)	C12—H12	0.9300
C4—C5	1.357 (6)	C13—H13	0.9300
C5—C6	1.386 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.370 (6)	C14—H14C	0.9600
C3—O1—H1	109.5	C13—C8—N1	116.6 (4)
C1—N1—C8	122.3 (4)	C9—C8—N1	124.4 (4)
N1—C1—C2	121.9 (4)	C8—C9—C10	119.3 (5)
N1—C1—H1A	119.0	C8—C9—H9	120.4
C2—C1—H1A	119.0	C10—C9—H9	120.4
C7—C2—C3	120.0 (4)	C11—C10—C9	121.8 (5)
C7—C2—C1	120.0 (4)	C11—C10—H10	119.1
C3—C2—C1	119.9 (4)	C9—C10—H10	119.1
O1—C3—C4	120.8 (4)	C12—C11—C10	117.6 (4)
O1—C3—C2	121.9 (4)	C12—C11—C14	122.0 (5)
C4—C3—C2	117.3 (4)	C10—C11—C14	120.4 (5)
C5—C4—C3	122.8 (4)	C11—C12—C13	122.2 (5)
C5—C4—Br1	118.7 (3)	C11—C12—H12	118.9
C3—C4—Br1	118.5 (3)	C13—C12—H12	118.9
C4—C5—C6	118.7 (4)	C12—C13—C8	120.2 (5)
C4—C5—H5	120.7	C12—C13—H13	119.9
C6—C5—H5	120.7	C8—C13—H13	119.9
C7—C6—C5	120.5 (4)	C11—C14—H14A	109.5
C7—C6—Cl1	120.9 (4)	C11—C14—H14B	109.5
C5—C6—Cl1	118.5 (3)	H14A—C14—H14B	109.5
C6—C7—C2	120.6 (4)	C11—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	119.0 (4)
C8—N1—C1—C2	179.4 (4)	Cl1—C6—C7—C2	−178.2 (3)
N1—C1—C2—C7	−177.3 (4)	C3—C2—C7—C6	−0.4 (6)
N1—C1—C2—C3	2.6 (6)	C1—C2—C7—C6	179.5 (4)
C7—C2—C3—O1	179.9 (4)	C1—N1—C8—C13	170.2 (4)
C1—C2—C3—O1	0.1 (6)	C1—N1—C8—C9	−11.1 (6)
C7—C2—C3—C4	−0.8 (6)	C13—C8—C9—C10	−0.2 (7)
C1—C2—C3—C4	179.3 (4)	N1—C8—C9—C10	−178.8 (4)
O1—C3—C4—C5	−179.8 (4)	C8—C9—C10—C11	−0.1 (7)
C2—C3—C4—C5	1.0 (6)	C9—C10—C11—C12	0.1 (7)
O1—C3—C4—Br1	−0.2 (6)	C9—C10—C11—C14	179.5 (4)
C2—C3—C4—Br1	−179.5 (3)	C10—C11—C12—C13	0.2 (7)
C3—C4—C5—C6	0.1 (7)	C14—C11—C12—C13	−179.2 (4)
Br1—C4—C5—C6	−179.5 (3)	C11—C12—C13—C8	−0.5 (7)
C4—C5—C6—C7	−1.3 (6)	C9—C8—C13—C12	0.5 (7)
C4—C5—C6—Cl1	178.4 (3)	N1—C8—C13—C12	179.2 (4)
C5—C6—C7—C2	1.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.574 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.574 (4)	148