2-[(2-Bromo-phen-yl)imino-meth-yl]-6-methyl-phenol.

In the title compound, C(14)H(12)BrNO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The dihedral angle between the two aromatic rings is 34.26 (9)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring.

Related literature

For Schiff bases and their applications, see: Calligaris et al. (1972 ▶); Singh et al. (1975 ▶). For a related structure, see: Temel et al. (2007 ▶).

Experimental

Crystal data

C14H12BrNO

M = 290.16

Orthorhombic,

a = 7.9407 (4) Å

b = 11.6754 (8) Å

c = 13.1960 (6) Å

V = 1223.41 (12) Å3

Z = 4

Mo Kα radiation

μ = 3.34 mm−1

T = 296 K

0.47 × 0.39 × 0.24 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.358, T max = 0.525

21115 measured reflections

2929 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.080

S = 1.07

2929 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1229 Friedel pairs

Flack parameter: −0.003 (10)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043072/bt5384sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043072/bt5384Isup2.hkl

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

C14H12BrNO	F(000) = 584
Mr = 290.16	Dx = 1.575 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23647 reflections
a = 7.9407 (4) Å	θ = 2.3–28.0°
b = 11.6754 (8) Å	µ = 3.34 mm−1
c = 13.1960 (6) Å	T = 296 K
V = 1223.41 (12) Å3	Prism, yellow
Z = 4	0.47 × 0.39 × 0.24 mm

Stoe IPDS 2 diffractometer	2929 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
graphite	Rint = 0.067
Detector resolution: 6.67 pixels mm-1	θmax = 28.0°, θmin = 2.3°
rotation method scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.358, Tmax = 0.525	l = −17→17
21115 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.0403P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.64 e Å−3
2929 reflections	Δρmin = −0.27 e Å−3
160 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0200 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1229 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.003 (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
H1	0.744 (4)	0.652 (3)	0.652 (3)	0.062 (9)*
Br1	0.79638 (5)	0.84452 (3)	0.81971 (3)	0.07572 (15)
C4	0.7065 (4)	0.5259 (2)	0.3545 (2)	0.0582 (7)
H4	0.6400	0.4945	0.3036	0.070*
N1	0.9650 (3)	0.68078 (17)	0.67303 (16)	0.0487 (5)
C7	1.0181 (3)	0.6620 (2)	0.58252 (19)	0.0477 (5)
H7	1.1302	0.6768	0.5669	0.057*
C5	0.8731 (4)	0.5467 (3)	0.3351 (2)	0.0609 (7)
H5	0.9181	0.5292	0.2719	0.073*
C1	0.9072 (3)	0.6182 (2)	0.50413 (18)	0.0452 (5)
O1	0.6641 (2)	0.62056 (19)	0.61369 (15)	0.0596 (5)
C2	0.7361 (3)	0.5966 (2)	0.52228 (18)	0.0457 (6)
C10	1.3450 (4)	0.7113 (3)	0.8347 (3)	0.0666 (8)
H10	1.4553	0.6848	0.8380	0.080*
C13	1.0198 (4)	0.7883 (2)	0.8254 (2)	0.0527 (6)
C9	1.2424 (4)	0.6774 (2)	0.7555 (2)	0.0569 (7)
H9	1.2843	0.6284	0.7060	0.068*
C6	0.9732 (4)	0.5931 (3)	0.40857 (19)	0.0568 (7)
H6	1.0860	0.6080	0.3949	0.068*
C3	0.6334 (4)	0.5500 (2)	0.4475 (2)	0.0503 (6)
C8	1.0769 (3)	0.7162 (2)	0.7491 (2)	0.0482 (6)
C11	1.2857 (5)	0.7834 (3)	0.9084 (3)	0.0683 (8)
H11	1.3557	0.8059	0.9613	0.082*
C14	0.4513 (4)	0.5289 (3)	0.4673 (3)	0.0710 (8)
H14A	0.4396	0.4770	0.5233	0.106*
H14B	0.4003	0.4960	0.4081	0.106*
H14C	0.3967	0.6000	0.4832	0.106*
C12	1.1230 (5)	0.8226 (3)	0.9041 (2)	0.0626 (8)
H12	1.0823	0.8718	0.9538	0.075*

	U11	U22	U33	U12	U13	U23
Br1	0.0655 (2)	0.0941 (2)	0.06760 (19)	0.01958 (17)	0.00516 (17)	−0.00921 (17)
C4	0.0647 (17)	0.0583 (15)	0.0515 (13)	0.0010 (15)	−0.0149 (14)	−0.0035 (11)
N1	0.0488 (11)	0.0516 (11)	0.0456 (10)	−0.0009 (8)	−0.0020 (10)	−0.0013 (10)
C7	0.0435 (12)	0.0506 (12)	0.0490 (13)	−0.0016 (12)	0.0018 (11)	0.0009 (12)
C5	0.0707 (18)	0.0695 (17)	0.0425 (14)	0.0056 (15)	0.0005 (13)	−0.0047 (13)
C1	0.0471 (13)	0.0462 (13)	0.0422 (11)	0.0007 (10)	0.0007 (11)	0.0048 (9)
O1	0.0456 (10)	0.0832 (14)	0.0500 (10)	−0.0008 (9)	0.0042 (9)	−0.0049 (9)
C2	0.0469 (14)	0.0450 (12)	0.0450 (12)	0.0035 (10)	0.0006 (10)	0.0046 (10)
C10	0.0527 (16)	0.0665 (17)	0.081 (2)	−0.0055 (13)	−0.0152 (15)	−0.0016 (16)
C13	0.0576 (15)	0.0524 (13)	0.0482 (13)	−0.0044 (12)	0.0004 (14)	0.0009 (13)
C9	0.0486 (15)	0.0564 (16)	0.0657 (16)	−0.0019 (11)	−0.0052 (12)	−0.0064 (12)
C6	0.0542 (15)	0.0695 (17)	0.0467 (14)	0.0024 (13)	0.0078 (13)	0.0004 (13)
C3	0.0466 (13)	0.0507 (13)	0.0536 (14)	0.0009 (11)	−0.0083 (12)	0.0049 (11)
C8	0.0492 (14)	0.0464 (13)	0.0489 (13)	−0.0062 (11)	−0.0030 (12)	0.0016 (11)
C11	0.073 (2)	0.0618 (17)	0.0697 (18)	−0.0122 (16)	−0.0224 (18)	0.0005 (14)
C14	0.0507 (17)	0.083 (2)	0.079 (2)	−0.0072 (15)	−0.0082 (16)	−0.0021 (18)
C12	0.077 (2)	0.0556 (17)	0.0554 (15)	−0.0096 (15)	−0.0013 (15)	−0.0058 (13)

Br1—C13	1.893 (3)	C10—C11	1.370 (5)
C4—C5	1.370 (5)	C10—C9	1.383 (4)
C4—C3	1.386 (4)	C10—H10	0.9300
C4—H4	0.9300	C13—C12	1.382 (4)
N1—C7	1.285 (3)	C13—C8	1.388 (4)
N1—C8	1.402 (3)	C9—C8	1.392 (4)
C7—C1	1.451 (4)	C9—H9	0.9300
C7—H7	0.9300	C6—H6	0.9300
C5—C6	1.366 (4)	C3—C14	1.490 (4)
C5—H5	0.9300	C11—C12	1.372 (5)
C1—C6	1.397 (4)	C11—H11	0.9300
C1—C2	1.403 (4)	C14—H14A	0.9600
O1—C2	1.364 (3)	C14—H14B	0.9600
O1—H1	0.89 (4)	C14—H14C	0.9600
C2—C3	1.390 (4)	C12—H12	0.9300
C5—C4—C3	122.3 (3)	C10—C9—H9	119.7
C5—C4—H4	118.9	C8—C9—H9	119.7
C3—C4—H4	118.9	C5—C6—C1	120.4 (3)
C7—N1—C8	120.5 (2)	C5—C6—H6	119.8
N1—C7—C1	121.6 (2)	C1—C6—H6	119.8
N1—C7—H7	119.2	C4—C3—C2	117.5 (3)
C1—C7—H7	119.2	C4—C3—C14	121.8 (3)
C6—C5—C4	120.0 (3)	C2—C3—C14	120.7 (3)
C6—C5—H5	120.0	C13—C8—C9	117.4 (3)
C4—C5—H5	120.0	C13—C8—N1	119.4 (3)
C6—C1—C2	118.7 (2)	C9—C8—N1	123.1 (2)
C6—C1—C7	119.3 (3)	C10—C11—C12	119.9 (3)
C2—C1—C7	122.0 (2)	C10—C11—H11	120.0
C2—O1—H1	107 (2)	C12—C11—H11	120.0
O1—C2—C3	117.5 (2)	C3—C14—H14A	109.5
O1—C2—C1	121.3 (2)	C3—C14—H14B	109.5
C3—C2—C1	121.2 (2)	H14A—C14—H14B	109.5
C11—C10—C9	120.7 (3)	C3—C14—H14C	109.5
C11—C10—H10	119.7	H14A—C14—H14C	109.5
C9—C10—H10	119.7	H14B—C14—H14C	109.5
C12—C13—C8	121.8 (3)	C11—C12—C13	119.5 (3)
C12—C13—Br1	119.0 (2)	C11—C12—H12	120.2
C8—C13—Br1	119.2 (2)	C13—C12—H12	120.2
C10—C9—C8	120.6 (3)
C8—N1—C7—C1	176.0 (2)	C1—C2—C3—C4	0.0 (4)
C3—C4—C5—C6	−0.2 (5)	O1—C2—C3—C14	0.7 (4)
N1—C7—C1—C6	−176.4 (3)	C1—C2—C3—C14	−179.2 (3)
N1—C7—C1—C2	1.4 (4)	C12—C13—C8—C9	1.1 (4)
C6—C1—C2—O1	−179.3 (2)	Br1—C13—C8—C9	179.5 (2)
C7—C1—C2—O1	2.9 (4)	C12—C13—C8—N1	177.7 (2)
C6—C1—C2—C3	0.6 (4)	Br1—C13—C8—N1	−4.0 (3)
C7—C1—C2—C3	−177.2 (2)	C10—C9—C8—C13	−0.7 (4)
C11—C10—C9—C8	0.1 (5)	C10—C9—C8—N1	−177.1 (3)
C4—C5—C6—C1	0.8 (5)	C7—N1—C8—C13	147.8 (2)
C2—C1—C6—C5	−1.0 (4)	C7—N1—C8—C9	−35.8 (4)
C7—C1—C6—C5	176.9 (3)	C9—C10—C11—C12	0.1 (5)
C5—C4—C3—C2	−0.2 (4)	C10—C11—C12—C13	0.3 (5)
C5—C4—C3—C14	179.0 (3)	C8—C13—C12—C11	−0.9 (4)
O1—C2—C3—C4	179.9 (2)	Br1—C13—C12—C11	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (4)	1.81 (3)	2.611 (3)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89 (4)	1.81 (3)	2.611 (3)	149 (3)