4-Bromo-2-[(phenyl-imino)-meth-yl]phenol.

The title compound, C13H10BrNO, is essentially planar (r.m.s. deviation = 0.026 Å) and the dihedral angle between the planes of the two aryl rings is 1.5 (3)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring.

Related literature

For background to the biological activity of Schiff bases, see: Han et al. (2012 ▶); Rehman et al. (2008 ▶); Ritter et al. (2009 ▶); Vanco et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10BrNO

M = 276.13

Orthorhombic,

a = 12.353 (3) Å

b = 4.5092 (9) Å

c = 19.778 (4) Å

V = 1101.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.71 mm−1

T = 298 K

0.20 × 0.15 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.524, T max = 0.836

4926 measured reflections

1674 independent reflections

1444 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.078

S = 1.04

1674 reflections

149 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 924 Friedel pairs

Absolute structure parameter: 0.039 (18)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814015268/nk2224sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015268/nk2224Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015268/nk2224Isup3.cml

CCDC reference: 1010948

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H10BrNO	F(000) = 552
Mr = 276.13	Dx = 1.665 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2025 reflections
a = 12.353 (3) Å	θ = 2.1–26.0°
b = 4.5092 (9) Å	µ = 3.71 mm−1
c = 19.778 (4) Å	T = 298 K
V = 1101.7 (4) Å3	Block, orange-red
Z = 4	0.20 × 0.15 × 0.05 mm

Bruker SMART CCD area-detector diffractometer	1674 independent reflections
Radiation source: fine-focus sealed tube	1444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
phi and ω scans	θmax = 25.1°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −13→14
Tmin = 0.524, Tmax = 0.836	k = −5→5
4926 measured reflections	l = −23→17

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0329P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1674 reflections	Δρmax = 0.47 e Å−3
149 parameters	Δρmin = −0.33 e Å−3
1 restraint	Absolute structure: Flack (1983), 924 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.039 (18)

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	0.57515 (4)	1.03271 (10)	0.49809 (4)	0.04069 (18)
C1	0.6938 (4)	0.5393 (12)	0.3358 (3)	0.0283 (13)
C2	0.8024 (4)	0.6143 (12)	0.3347 (3)	0.0310 (14)
C3	0.8434 (5)	0.8206 (15)	0.3824 (3)	0.0401 (16)
H3	0.9163	0.8720	0.3817	0.048*
C4	0.7755 (5)	0.9449 (13)	0.4299 (3)	0.0394 (14)
H4	0.8022	1.0819	0.4608	0.047*
C5	0.6671 (5)	0.8650 (13)	0.4313 (3)	0.0340 (14)
C6	0.6257 (5)	0.6708 (12)	0.3845 (3)	0.0315 (13)
H6	0.5523	0.6255	0.3850	0.038*
C7	0.6489 (4)	0.3280 (12)	0.2878 (3)	0.0305 (13)
H7	0.5750	0.2881	0.2882	0.037*
C8	0.6684 (4)	−0.0149 (12)	0.1984 (3)	0.0314 (13)
C9	0.5609 (5)	−0.1095 (13)	0.1966 (3)	0.0379 (15)
H9	0.5108	−0.0327	0.2271	0.045*
C10	0.5286 (5)	−0.3203 (13)	0.1487 (3)	0.0428 (17)
H10	0.4573	−0.3866	0.1481	0.051*
C11	0.6026 (5)	−0.4316 (12)	0.1020 (3)	0.0401 (15)
H11	0.5810	−0.5689	0.0695	0.048*
C12	0.7067 (6)	−0.3361 (15)	0.1046 (4)	0.0445 (16)
H12	0.7565	−0.4105	0.0736	0.053*
C13	0.7409 (5)	−0.1310 (12)	0.1521 (3)	0.0373 (14)
H13	0.8130	−0.0710	0.1528	0.045*
N1	0.7101 (4)	0.1963 (10)	0.2449 (2)	0.0304 (12)
O1	0.8726 (3)	0.4998 (10)	0.2894 (2)	0.0398 (10)
H1	0.840 (4)	0.348 (13)	0.269 (3)	0.029 (17)*

	U11	U22	U33	U12	U13	U23
Br1	0.0408 (3)	0.0520 (3)	0.0293 (3)	0.0062 (3)	0.0020 (4)	−0.0049 (6)
C1	0.033 (3)	0.028 (3)	0.023 (3)	0.000 (3)	−0.002 (2)	0.006 (3)
C2	0.032 (3)	0.033 (3)	0.029 (4)	−0.001 (3)	0.000 (3)	0.003 (3)
C3	0.034 (4)	0.047 (4)	0.039 (4)	−0.006 (3)	−0.005 (3)	0.000 (3)
C4	0.042 (3)	0.046 (3)	0.030 (4)	−0.002 (3)	−0.007 (3)	−0.002 (3)
C5	0.040 (3)	0.034 (3)	0.028 (4)	0.002 (3)	0.000 (3)	0.004 (3)
C6	0.031 (3)	0.033 (3)	0.031 (4)	0.003 (3)	0.001 (3)	0.003 (3)
C7	0.031 (3)	0.032 (3)	0.029 (4)	−0.001 (3)	−0.002 (3)	0.005 (3)
C8	0.039 (3)	0.029 (3)	0.026 (3)	0.000 (3)	0.000 (2)	0.003 (3)
C9	0.035 (3)	0.044 (3)	0.034 (4)	−0.003 (3)	−0.005 (3)	−0.002 (3)
C10	0.039 (4)	0.038 (4)	0.051 (5)	−0.010 (3)	−0.014 (3)	0.008 (3)
C11	0.056 (4)	0.034 (3)	0.029 (4)	−0.004 (3)	−0.010 (3)	0.001 (3)
C12	0.057 (4)	0.044 (4)	0.032 (4)	0.001 (4)	0.007 (3)	−0.004 (3)
C13	0.039 (4)	0.036 (3)	0.037 (4)	−0.007 (3)	0.001 (3)	0.001 (3)
N1	0.030 (3)	0.032 (2)	0.029 (3)	−0.002 (2)	−0.002 (3)	0.000 (2)
O1	0.027 (2)	0.054 (3)	0.038 (3)	0.000 (2)	0.0047 (19)	−0.012 (2)

Br1—C5	1.899 (6)	C8—C13	1.385 (8)
C1—C2	1.383 (7)	C8—C9	1.396 (7)
C1—C6	1.411 (8)	C8—N1	1.421 (7)
C1—C7	1.454 (8)	C9—C10	1.400 (8)
C2—O1	1.350 (7)	C9—H9	0.9300
C2—C3	1.419 (9)	C10—C11	1.394 (9)
C3—C4	1.378 (9)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.358 (9)
C4—C5	1.387 (8)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.384 (8)
C5—C6	1.372 (8)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.283 (7)	O1—H1	0.89 (6)
C7—H7	0.9300
C2—C1—C6	119.1 (5)	C13—C8—C9	118.9 (5)
C2—C1—C7	121.4 (5)	C13—C8—N1	116.6 (5)
C6—C1—C7	119.6 (5)	C9—C8—N1	124.5 (5)
O1—C2—C1	122.6 (5)	C8—C9—C10	119.7 (6)
O1—C2—C3	117.6 (5)	C8—C9—H9	120.1
C1—C2—C3	119.8 (6)	C10—C9—H9	120.1
C4—C3—C2	120.1 (6)	C11—C10—C9	120.4 (6)
C4—C3—H3	119.9	C11—C10—H10	119.8
C2—C3—H3	119.9	C9—C10—H10	119.8
C3—C4—C5	119.8 (6)	C12—C11—C10	118.8 (6)
C3—C4—H4	120.1	C12—C11—H11	120.6
C5—C4—H4	120.1	C10—C11—H11	120.6
C6—C5—C4	120.7 (6)	C11—C12—C13	121.8 (7)
C6—C5—Br1	120.0 (4)	C11—C12—H12	119.1
C4—C5—Br1	119.2 (5)	C13—C12—H12	119.1
C5—C6—C1	120.5 (5)	C12—C13—C8	120.3 (6)
C5—C6—H6	119.8	C12—C13—H13	119.8
C1—C6—H6	119.8	C8—C13—H13	119.8
N1—C7—C1	120.6 (5)	C7—N1—C8	121.6 (5)
N1—C7—H7	119.7	C2—O1—H1	108 (4)
C1—C7—H7	119.7
C6—C1—C2—O1	−179.6 (5)	C2—C1—C7—N1	2.9 (8)
C7—C1—C2—O1	0.5 (9)	C6—C1—C7—N1	−177.0 (5)
C6—C1—C2—C3	0.1 (8)	C13—C8—C9—C10	0.6 (9)
C7—C1—C2—C3	−179.8 (5)	N1—C8—C9—C10	−179.7 (5)
O1—C2—C3—C4	180.0 (5)	C8—C9—C10—C11	−1.4 (9)
C1—C2—C3—C4	0.3 (9)	C9—C10—C11—C12	1.2 (9)
C2—C3—C4—C5	0.8 (9)	C10—C11—C12—C13	−0.3 (10)
C3—C4—C5—C6	−2.2 (9)	C11—C12—C13—C8	−0.5 (10)
C3—C4—C5—Br1	178.8 (5)	C9—C8—C13—C12	0.4 (9)
C4—C5—C6—C1	2.6 (9)	N1—C8—C13—C12	−179.4 (5)
Br1—C5—C6—C1	−178.4 (4)	C1—C7—N1—C8	178.8 (5)
C2—C1—C6—C5	−1.6 (8)	C13—C8—N1—C7	176.6 (5)
C7—C1—C6—C5	178.4 (5)	C9—C8—N1—C7	−3.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.89 (6)	1.81 (5)	2.583 (6)	144 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.89 (6)	1.81 (5)	2.583 (6)	144 (5)