2-Bromo-4-chloro-6-(cyclo-hexyl-imino-meth-yl)phenol.

The title compound, C(13)H(15)BrClNO, was prepared by the condensation of equimolar quanti-ties of 3-bromo-5-chloro-salicyl-aldehyde with cyclo-hexyl-amine in methanol. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule. The cyclo-hexyl ring adopts a chair conformation.

Related literature

For the coordination chemistry of Schiff base compounds, see: Xu et al. (2011 ▶); Suleiman Gwaram et al. (2011 ▶); Assey et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For similar structures, see: Miura et al. (2009 ▶); Damous et al. (2011 ▶); Şahin et al. (2009 ▶); Orona et al. (2011 ▶).

Experimental

Crystal data

C13H15BrClNO

M = 316.62

Monoclinic,

a = 12.296 (2) Å

b = 16.359 (3) Å

c = 6.969 (1) Å

β = 101.634 (2)°

V = 1373.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.17 mm−1

T = 298 K

0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.450, T max = 0.481

10912 measured reflections

2982 independent reflections

1705 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.227

S = 1.04

2982 reflections

157 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.40 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811045053/qm2039sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045053/qm2039Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045053/qm2039Isup3.cml

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

C13H15BrClNO	F(000) = 640
Mr = 316.62	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.296 (2) Å	Cell parameters from 2374 reflections
b = 16.359 (3) Å	θ = 2.5–24.1°
c = 6.969 (1) Å	µ = 3.17 mm−1
β = 101.634 (2)°	T = 298 K
V = 1373.0 (4) Å3	Block, yellow
Z = 4	0.30 × 0.30 × 0.27 mm

Bruker SMART 1K CCD area-detector diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	1705 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scan	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.450, Tmax = 0.481	k = −20→19
10912 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1329P)2 + 0.243P] where P = (Fo2 + 2Fc2)/3
2982 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 1.40 e Å−3
1 restraint	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	0.36373 (6)	0.05122 (4)	−0.11130 (11)	0.0888 (4)
Cl1	0.09344 (12)	0.31936 (13)	−0.2918 (3)	0.0948 (6)
N1	0.6092 (4)	0.3288 (3)	0.0492 (7)	0.0594 (11)
O1	0.5335 (3)	0.1823 (2)	0.0130 (6)	0.0619 (9)
C1	0.4189 (4)	0.3005 (3)	−0.0749 (6)	0.0479 (11)
C2	0.4337 (4)	0.2154 (3)	−0.0606 (6)	0.0490 (11)
C3	0.3424 (4)	0.1648 (3)	−0.1214 (7)	0.0550 (12)
C4	0.2398 (4)	0.1959 (4)	−0.1955 (7)	0.0624 (14)
H4	0.1801	0.1612	−0.2402	0.075*
C5	0.2255 (4)	0.2799 (4)	−0.2032 (7)	0.0616 (14)
C6	0.3129 (4)	0.3316 (3)	−0.1472 (7)	0.0576 (13)
H6	0.3020	0.3878	−0.1572	0.069*
C7	0.5119 (4)	0.3548 (3)	−0.0185 (7)	0.0564 (12)
H7	0.5003	0.4109	−0.0322	0.068*
C8	0.7014 (4)	0.3862 (3)	0.0990 (8)	0.0601 (13)
H8	0.6719	0.4419	0.0785	0.072*
C9	0.7837 (5)	0.3731 (4)	−0.0324 (9)	0.0809 (18)
H9A	0.7478	0.3837	−0.1672	0.097*
H9B	0.8083	0.3167	−0.0231	0.097*
C10	0.8835 (6)	0.4293 (5)	0.0252 (12)	0.095 (2)
H10A	0.9367	0.4179	−0.0569	0.114*
H10B	0.8598	0.4857	0.0036	0.114*
C11	0.9385 (5)	0.4176 (4)	0.2383 (11)	0.089 (2)
H11A	0.9677	0.3625	0.2579	0.107*
H11B	1.0000	0.4555	0.2730	0.107*
C12	0.8578 (5)	0.4318 (5)	0.3658 (9)	0.0772 (18)
H12A	0.8343	0.4885	0.3550	0.093*
H12B	0.8937	0.4218	0.5010	0.093*
C13	0.7562 (5)	0.3768 (4)	0.3122 (8)	0.0674 (14)
H13A	0.7782	0.3203	0.3381	0.081*
H13B	0.7033	0.3907	0.3934	0.081*
H1	0.576 (4)	0.227 (2)	0.035 (9)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0837 (6)	0.0650 (5)	0.1181 (7)	−0.0128 (3)	0.0212 (4)	−0.0034 (3)
Cl1	0.0463 (8)	0.1216 (15)	0.1084 (13)	0.0132 (8)	−0.0034 (8)	0.0139 (11)
N1	0.050 (2)	0.062 (3)	0.063 (3)	−0.004 (2)	0.0047 (19)	−0.006 (2)
O1	0.0451 (19)	0.063 (2)	0.076 (2)	0.0007 (16)	0.0071 (17)	−0.0017 (18)
C1	0.045 (2)	0.059 (3)	0.039 (2)	0.003 (2)	0.0040 (19)	0.003 (2)
C2	0.039 (2)	0.071 (3)	0.038 (2)	0.004 (2)	0.0115 (18)	0.002 (2)
C3	0.054 (3)	0.064 (3)	0.050 (3)	−0.009 (2)	0.016 (2)	−0.004 (2)
C4	0.042 (3)	0.089 (4)	0.054 (3)	−0.015 (3)	0.005 (2)	0.002 (3)
C5	0.042 (3)	0.091 (4)	0.052 (3)	0.007 (3)	0.007 (2)	0.006 (3)
C6	0.051 (3)	0.066 (3)	0.054 (3)	0.011 (3)	0.009 (2)	0.006 (2)
C7	0.055 (3)	0.056 (3)	0.057 (3)	0.000 (2)	0.010 (2)	0.002 (2)
C8	0.050 (3)	0.048 (3)	0.076 (4)	−0.006 (2)	−0.001 (2)	−0.001 (2)
C9	0.082 (4)	0.088 (4)	0.075 (4)	−0.025 (3)	0.022 (3)	−0.019 (3)
C10	0.082 (5)	0.108 (5)	0.104 (6)	−0.033 (4)	0.039 (4)	−0.026 (4)
C11	0.048 (3)	0.088 (4)	0.127 (6)	−0.008 (3)	0.009 (4)	−0.006 (4)
C12	0.064 (4)	0.086 (4)	0.077 (4)	−0.020 (3)	0.003 (3)	−0.011 (3)
C13	0.062 (3)	0.073 (4)	0.067 (3)	−0.016 (3)	0.015 (3)	−0.008 (3)

Br1—C3	1.875 (5)	C8—C13	1.510 (7)
Cl1—C5	1.741 (5)	C8—H8	0.9800
N1—C7	1.268 (6)	C9—C10	1.521 (8)
N1—C8	1.460 (6)	C9—H9A	0.9700
O1—C2	1.344 (5)	C9—H9B	0.9700
O1—H1	0.900 (10)	C10—C11	1.515 (10)
C1—C6	1.395 (7)	C10—H10A	0.9700
C1—C2	1.405 (7)	C10—H10B	0.9700
C1—C7	1.440 (7)	C11—C12	1.478 (9)
C2—C3	1.391 (7)	C11—H11A	0.9700
C3—C4	1.363 (7)	C11—H11B	0.9700
C4—C5	1.384 (8)	C12—C13	1.524 (7)
C4—H4	0.9300	C12—H12A	0.9700
C5—C6	1.362 (7)	C12—H12B	0.9700
C6—H6	0.9300	C13—H13A	0.9700
C7—H7	0.9300	C13—H13B	0.9700
C8—C9	1.510 (8)
C7—N1—C8	120.1 (5)	C8—C9—H9A	109.4
C2—O1—H1	101 (4)	C10—C9—H9A	109.4
C6—C1—C2	119.1 (4)	C8—C9—H9B	109.4
C6—C1—C7	120.4 (5)	C10—C9—H9B	109.4
C2—C1—C7	120.5 (4)	H9A—C9—H9B	108.0
O1—C2—C3	119.7 (5)	C11—C10—C9	111.0 (6)
O1—C2—C1	121.4 (4)	C11—C10—H10A	109.4
C3—C2—C1	118.9 (4)	C9—C10—H10A	109.4
C4—C3—C2	121.5 (5)	C11—C10—H10B	109.4
C4—C3—Br1	119.7 (4)	C9—C10—H10B	109.4
C2—C3—Br1	118.7 (4)	H10A—C10—H10B	108.0
C3—C4—C5	119.1 (5)	C12—C11—C10	110.4 (5)
C3—C4—H4	120.5	C12—C11—H11A	109.6
C5—C4—H4	120.5	C10—C11—H11A	109.6
C6—C5—C4	121.3 (4)	C12—C11—H11B	109.6
C6—C5—Cl1	119.8 (5)	C10—C11—H11B	109.6
C4—C5—Cl1	118.9 (4)	H11A—C11—H11B	108.1
C5—C6—C1	120.1 (5)	C11—C12—C13	112.2 (5)
C5—C6—H6	119.9	C11—C12—H12A	109.2
C1—C6—H6	119.9	C13—C12—H12A	109.2
N1—C7—C1	122.2 (5)	C11—C12—H12B	109.2
N1—C7—H7	118.9	C13—C12—H12B	109.2
C1—C7—H7	118.9	H12A—C12—H12B	107.9
N1—C8—C9	110.4 (4)	C8—C13—C12	111.2 (5)
N1—C8—C13	109.8 (4)	C8—C13—H13A	109.4
C9—C8—C13	111.2 (5)	C12—C13—H13A	109.4
N1—C8—H8	108.4	C8—C13—H13B	109.4
C9—C8—H8	108.4	C12—C13—H13B	109.4
C13—C8—H8	108.4	H13A—C13—H13B	108.0
C8—C9—C10	111.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (1)	1.71 (2)	2.564 (6)	159 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90 (1)	1.71 (2)	2.564 (6)	159 (6)