4-Bromo-2-{(E)-[(3,4-dimethyl-phen-yl)imino]-meth-yl}phenol.

In the title compound, C(15)H(14)BrNO, the dihedral angle between the aromatic rings is 4.10 (11)° and the mol-ecule is close to planar (r.m.s. deviation for the non-H atoms = 0.053 Å). An intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, very weak C-H⋯π inter-actions are observed.

Related literature

For related structures, see: Unver et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H14BrNO

M = 304.18

Monoclinic,

a = 12.2633 (10) Å

b = 7.4805 (6) Å

c = 14.5767 (11) Å

β = 101.576 (4)°

V = 1310.00 (18) Å3

Z = 4

Mo Kα radiation

μ = 3.13 mm−1

T = 296 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.454, T max = 0.546

9488 measured reflections

2545 independent reflections

1931 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.04

2545 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035635/hb6936sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035635/hb6936Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035635/hb6936Isup3.cml

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

C15H14BrNO	F(000) = 616
Mr = 304.18	Dx = 1.542 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1931 reflections
a = 12.2633 (10) Å	θ = 2.0–26.0°
b = 7.4805 (6) Å	µ = 3.13 mm−1
c = 14.5767 (11) Å	T = 296 K
β = 101.576 (4)°	Prism, yellow
V = 1310.00 (18) Å3	0.30 × 0.25 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2545 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −10→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→8
Tmin = 0.454, Tmax = 0.546	l = −17→17
9488 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.1325P] where P = (Fo2 + 2Fc2)/3
2545 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.18394 (2)	0.52508 (4)	0.05809 (2)	0.0611 (1)
O1	0.04873 (13)	0.3558 (3)	0.42252 (10)	0.0649 (7)
N1	0.23707 (15)	0.4902 (2)	0.50899 (13)	0.0433 (6)
C1	0.30890 (17)	0.5327 (3)	0.59525 (15)	0.0377 (7)
C2	0.26822 (18)	0.4991 (3)	0.67585 (15)	0.0402 (7)
C3	0.32937 (18)	0.5327 (3)	0.76461 (15)	0.0386 (7)
C4	0.43689 (17)	0.6028 (3)	0.77377 (14)	0.0413 (7)
C5	0.47658 (17)	0.6376 (3)	0.69271 (14)	0.0445 (8)
C6	0.41546 (16)	0.6041 (3)	0.60481 (15)	0.0437 (7)
C7	0.2812 (2)	0.4915 (3)	0.85007 (17)	0.0559 (9)
C8	0.50899 (19)	0.6368 (3)	0.86868 (15)	0.0595 (9)
C9	0.26191 (19)	0.5199 (3)	0.42938 (15)	0.0411 (7)
C10	0.18689 (18)	0.4725 (3)	0.34246 (15)	0.0384 (7)
C11	0.08370 (17)	0.3910 (3)	0.34249 (15)	0.0442 (7)
C12	0.01435 (18)	0.3464 (3)	0.25816 (16)	0.0495 (8)
C13	0.04434 (18)	0.3849 (3)	0.17425 (15)	0.0462 (7)
C14	0.14496 (18)	0.4672 (3)	0.17412 (15)	0.0407 (7)
C15	0.21649 (18)	0.5098 (3)	0.25677 (15)	0.0406 (7)
H1	0.09704	0.38542	0.46739	0.0974*
H2	0.19695	0.45203	0.66987	0.0483*
H5	0.54756	0.68561	0.69831	0.0534*
H6	0.44489	0.62870	0.55214	0.0524*
H7A	0.32881	0.40851	0.88946	0.0838*
H7B	0.20851	0.44010	0.83078	0.0838*
H7C	0.27580	0.59987	0.88418	0.0838*
H8A	0.47412	0.72447	0.90136	0.0893*
H8B	0.58039	0.68003	0.86120	0.0893*
H8C	0.51838	0.52756	0.90395	0.0893*
H9	0.32978	0.57328	0.42700	0.0493*
H12	−0.05316	0.28997	0.25835	0.0594*
H13	−0.00291	0.35554	0.11803	0.0554*
H15	0.28458	0.56350	0.25552	0.0487*

	U11	U22	U33	U12	U13	U23
Br1	0.0679 (2)	0.0809 (2)	0.0349 (2)	−0.0060 (1)	0.0114 (1)	0.0038 (1)
O1	0.0642 (11)	0.0893 (14)	0.0442 (9)	−0.0253 (10)	0.0179 (8)	0.0017 (9)
N1	0.0464 (10)	0.0475 (11)	0.0355 (10)	−0.0011 (8)	0.0073 (8)	−0.0028 (8)
C1	0.0431 (12)	0.0358 (11)	0.0349 (11)	0.0024 (9)	0.0094 (9)	−0.0005 (9)
C2	0.0409 (12)	0.0401 (13)	0.0407 (12)	−0.0035 (9)	0.0105 (10)	−0.0015 (9)
C3	0.0461 (12)	0.0359 (12)	0.0359 (11)	0.0004 (10)	0.0135 (9)	0.0012 (9)
C4	0.0468 (12)	0.0348 (12)	0.0411 (12)	0.0005 (10)	0.0059 (10)	0.0003 (10)
C5	0.0379 (12)	0.0455 (14)	0.0498 (14)	−0.0034 (10)	0.0080 (10)	0.0022 (10)
C6	0.0436 (13)	0.0494 (13)	0.0413 (12)	−0.0001 (10)	0.0160 (10)	0.0036 (10)
C7	0.0664 (16)	0.0653 (17)	0.0388 (13)	−0.0078 (12)	0.0173 (12)	0.0006 (10)
C8	0.0621 (15)	0.0662 (18)	0.0460 (14)	−0.0063 (13)	0.0005 (12)	−0.0015 (12)
C9	0.0439 (12)	0.0426 (13)	0.0371 (12)	−0.0022 (10)	0.0091 (9)	−0.0008 (9)
C10	0.0435 (12)	0.0362 (12)	0.0352 (12)	0.0007 (9)	0.0074 (9)	0.0001 (9)
C11	0.0487 (13)	0.0442 (13)	0.0420 (12)	−0.0054 (11)	0.0146 (10)	0.0032 (10)
C12	0.0444 (13)	0.0498 (15)	0.0529 (14)	−0.0121 (10)	0.0063 (11)	−0.0003 (11)
C13	0.0487 (13)	0.0445 (13)	0.0414 (12)	−0.0010 (11)	−0.0006 (10)	−0.0014 (10)
C14	0.0460 (13)	0.0399 (12)	0.0365 (12)	0.0045 (10)	0.0089 (10)	−0.0001 (9)
C15	0.0414 (12)	0.0416 (13)	0.0391 (12)	−0.0006 (9)	0.0091 (10)	0.0009 (9)

Br1—C14	1.898 (2)	C12—C13	1.377 (3)
O1—C11	1.347 (3)	C13—C14	1.379 (3)
O1—H1	0.8200	C14—C15	1.378 (3)
N1—C1	1.419 (3)	C2—H2	0.9300
N1—C9	1.277 (3)	C5—H5	0.9300
C1—C6	1.393 (3)	C6—H6	0.9300
C1—C2	1.388 (3)	C7—H7A	0.9600
C2—C3	1.382 (3)	C7—H7B	0.9600
C3—C4	1.400 (3)	C7—H7C	0.9600
C3—C7	1.514 (3)	C8—H8A	0.9600
C4—C8	1.507 (3)	C8—H8B	0.9600
C4—C5	1.390 (3)	C8—H8C	0.9600
C5—C6	1.372 (3)	C9—H9	0.9300
C9—C10	1.452 (3)	C12—H12	0.9300
C10—C15	1.397 (3)	C13—H13	0.9300
C10—C11	1.405 (3)	C15—H15	0.9300
C11—C12	1.388 (3)
C11—O1—H1	109.00	C1—C2—H2	119.00
C1—N1—C9	123.19 (19)	C3—C2—H2	119.00
N1—C1—C6	125.30 (19)	C4—C5—H5	119.00
C2—C1—C6	118.3 (2)	C6—C5—H5	119.00
N1—C1—C2	116.41 (19)	C1—C6—H6	120.00
C1—C2—C3	122.7 (2)	C5—C6—H6	120.00
C2—C3—C7	120.4 (2)	C3—C7—H7A	109.00
C4—C3—C7	120.89 (19)	C3—C7—H7B	109.00
C2—C3—C4	118.8 (2)	C3—C7—H7C	109.00
C3—C4—C8	121.25 (19)	H7A—C7—H7B	110.00
C5—C4—C8	120.53 (19)	H7A—C7—H7C	109.00
C3—C4—C5	118.22 (19)	H7B—C7—H7C	109.00
C4—C5—C6	122.8 (2)	C4—C8—H8A	109.00
C1—C6—C5	119.3 (2)	C4—C8—H8B	109.00
N1—C9—C10	121.7 (2)	C4—C8—H8C	109.00
C9—C10—C11	121.2 (2)	H8A—C8—H8B	109.00
C9—C10—C15	119.9 (2)	H8A—C8—H8C	109.00
C11—C10—C15	118.9 (2)	H8B—C8—H8C	109.00
O1—C11—C10	121.90 (19)	N1—C9—H9	119.00
O1—C11—C12	118.36 (19)	C10—C9—H9	119.00
C10—C11—C12	119.7 (2)	C11—C12—H12	120.00
C11—C12—C13	120.8 (2)	C13—C12—H12	120.00
C12—C13—C14	119.6 (2)	C12—C13—H13	120.00
Br1—C14—C13	119.24 (16)	C14—C13—H13	120.00
C13—C14—C15	121.0 (2)	C10—C15—H15	120.00
Br1—C14—C15	119.77 (17)	C14—C15—H15	120.00
C10—C15—C14	120.1 (2)
C9—N1—C1—C2	177.4 (2)	N1—C9—C10—C11	−0.3 (3)
C9—N1—C1—C6	−2.7 (3)	N1—C9—C10—C15	179.0 (2)
C1—N1—C9—C10	179.2 (2)	C9—C10—C11—O1	1.1 (3)
N1—C1—C2—C3	179.5 (2)	C9—C10—C11—C12	−179.6 (2)
C6—C1—C2—C3	−0.4 (3)	C15—C10—C11—O1	−178.2 (2)
N1—C1—C6—C5	−179.5 (2)	C15—C10—C11—C12	1.1 (3)
C2—C1—C6—C5	0.4 (3)	C9—C10—C15—C14	−179.2 (2)
C1—C2—C3—C4	−0.3 (3)	C11—C10—C15—C14	0.2 (3)
C1—C2—C3—C7	−179.3 (2)	O1—C11—C12—C13	177.8 (2)
C2—C3—C4—C5	0.8 (3)	C10—C11—C12—C13	−1.5 (3)
C2—C3—C4—C8	−178.0 (2)	C11—C12—C13—C14	0.6 (3)
C7—C3—C4—C5	179.9 (2)	C12—C13—C14—Br1	−178.45 (17)
C7—C3—C4—C8	1.0 (3)	C12—C13—C14—C15	0.7 (3)
C3—C4—C5—C6	−0.8 (3)	Br1—C14—C15—C10	178.07 (17)
C8—C4—C5—C6	178.1 (2)	C13—C14—C15—C10	−1.1 (3)
C4—C5—C6—C1	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.601 (2)	147
C7—H7B···Cg1i	0.96	2.95	3.668 (3)	133
C12—H12···Cg1ii	0.93	2.96	3.612 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.601 (2)	147
C7—H7B⋯Cg1i	0.96	2.95	3.668 (3)	133
C12—H12⋯Cg1ii	0.93	2.96	3.612 (2)	128

Symmetry codes: (i) ; (ii) .