4-Bromo-N-(4-hy-droxy-benzyl-idene)-aniline.

In the title compound, C(13)H(10)BrNO, the benzene ring planes are inclined at an angle of 48.85 (17)°, resulting in a nonplanar mol-ecule. A characteristic of aromatic Schiff bases with N-aryl substituents is that the terminal phenyl rings are twisted relative to the HC=N plane. In this case, the HC=N unit makes dihedral angles of 11.1 (4) and 38.5 (3)° with the hy-droxy-benzene and bromo-benzene rings, respectively. In the crystal, the molecules are linked by O-H⋯N hydrogen bonds to form infinite (C8) chains along the b axis.

Related literature

For applications of Schiff base compounds and related structures, see: Li et al. (2008 ▶); Zhang (2010 ▶). For other related structures, see: Kaitner & Pavlovic (1995 ▶); Yeap et al. (1993 ▶). For an early determination of the lattice parameters of this compound, see: Bürgi et al. (1968 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10BrNO

M = 276.13

Orthorhombic,

a = 21.9588 (10) Å

b = 11.0866 (5) Å

c = 9.3132 (4) Å

V = 2267.28 (17) Å3

Z = 8

Mo Kα radiation

μ = 3.60 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.452, T max = 0.571

20366 measured reflections

2001 independent reflections

1494 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.174

S = 1.03

2001 reflections

145 parameters

H-atom parameters constrained

Δρmax = 1.32 e Å−3

Δρmin = −1.62 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006101/sj5193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006101/sj5193Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006101/sj5193Isup3.cml

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

C13H10BrNO	F(000) = 1104
Mr = 276.13	Dx = 1.618 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6133 reflections
a = 21.9588 (10) Å	θ = 2.7–24.7°
b = 11.0866 (5) Å	µ = 3.60 mm−1
c = 9.3132 (4) Å	T = 293 K
V = 2267.28 (17) Å3	Block, brown
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2001 independent reflections
Radiation source: fine-focus sealed tube	1494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −26→26
Tmin = 0.452, Tmax = 0.571	k = −12→13
20366 measured reflections	l = −8→11

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0898P)2 + 6.133P] where P = (Fo2 + 2Fc2)/3
2001 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 1.32 e Å−3
0 restraints	Δρmin = −1.62 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
C1	0.3296 (2)	0.1888 (4)	−0.1451 (5)	0.0340 (10)
C2	0.3501 (2)	0.0799 (4)	−0.0885 (5)	0.0398 (11)
H2	0.3879	0.0493	−0.1156	0.048*
C3	0.3145 (2)	0.0181 (4)	0.0074 (5)	0.0407 (11)
H3	0.3283	−0.0551	0.0437	0.049*
C4	0.2586 (2)	0.0620 (4)	0.0514 (5)	0.0333 (10)
C5	0.2389 (2)	0.1715 (4)	−0.0048 (4)	0.0340 (10)
H5	0.2014	0.2027	0.0231	0.041*
C6	0.2743 (2)	0.2341 (4)	−0.1012 (5)	0.0340 (10)
H6	0.2607	0.3076	−0.1370	0.041*
C7	0.2200 (2)	−0.0109 (4)	0.1437 (5)	0.0360 (10)
H7	0.2321	−0.0899	0.1619	0.043*
C8	0.1337 (2)	−0.0598 (4)	0.2718 (5)	0.0342 (10)
C9	0.1277 (2)	−0.1783 (5)	0.2249 (6)	0.0456 (12)
H9	0.1487	−0.2041	0.1439	0.055*
C10	0.0909 (3)	−0.2569 (5)	0.2975 (6)	0.0518 (13)
H10	0.0870	−0.3359	0.2654	0.062*
C11	0.0598 (2)	−0.2199 (5)	0.4172 (6)	0.0526 (14)
C12	0.0639 (2)	−0.1040 (5)	0.4635 (6)	0.0518 (13)
H12	0.0426	−0.0793	0.5445	0.062*
C13	0.1002 (2)	−0.0229 (5)	0.3893 (5)	0.0450 (12)
H13	0.1020	0.0571	0.4189	0.054*
N1	0.17101 (17)	0.0253 (3)	0.2012 (4)	0.0342 (9)
O1	0.36520 (16)	0.2436 (3)	−0.2426 (4)	0.0465 (9)
H1	0.3522	0.3116	−0.2583	0.070*
Br1	0.01108 (4)	−0.33090 (9)	0.51718 (9)	0.0918 (4)

	U11	U22	U33	U12	U13	U23
C1	0.034 (2)	0.032 (2)	0.036 (2)	−0.0054 (19)	0.0006 (19)	−0.0038 (19)
C2	0.032 (2)	0.037 (2)	0.050 (3)	−0.001 (2)	0.000 (2)	−0.003 (2)
C3	0.042 (3)	0.031 (2)	0.050 (3)	0.000 (2)	−0.006 (2)	0.005 (2)
C4	0.039 (2)	0.028 (2)	0.033 (2)	−0.0046 (19)	−0.0062 (19)	−0.0008 (19)
C5	0.036 (3)	0.032 (2)	0.034 (2)	−0.0006 (19)	−0.0022 (19)	−0.0030 (18)
C6	0.039 (3)	0.028 (2)	0.035 (2)	0.0001 (18)	−0.001 (2)	0.0015 (19)
C7	0.044 (3)	0.027 (2)	0.037 (3)	−0.003 (2)	−0.008 (2)	0.0033 (19)
C8	0.040 (3)	0.031 (2)	0.031 (2)	−0.0040 (19)	−0.0046 (19)	0.0030 (18)
C9	0.052 (3)	0.043 (3)	0.041 (3)	−0.010 (2)	0.000 (2)	−0.002 (2)
C10	0.057 (3)	0.041 (3)	0.058 (3)	−0.015 (2)	−0.008 (3)	0.005 (3)
C11	0.040 (3)	0.064 (4)	0.053 (3)	−0.014 (3)	−0.006 (2)	0.021 (3)
C12	0.040 (3)	0.069 (4)	0.047 (3)	0.002 (3)	0.006 (2)	0.004 (3)
C13	0.046 (3)	0.046 (3)	0.043 (3)	−0.001 (2)	0.000 (2)	−0.001 (2)
N1	0.041 (2)	0.0301 (19)	0.0314 (19)	−0.0041 (16)	−0.0036 (17)	0.0006 (16)
O1	0.046 (2)	0.0398 (19)	0.053 (2)	−0.0006 (15)	0.0120 (16)	0.0066 (16)
Br1	0.0712 (6)	0.1138 (7)	0.0904 (6)	−0.0442 (4)	0.0008 (4)	0.0423 (5)

C1—O1	1.343 (5)	C8—C13	1.380 (7)
C1—C6	1.376 (6)	C8—C9	1.390 (7)
C1—C2	1.392 (6)	C8—N1	1.412 (6)
C2—C3	1.371 (7)	C9—C10	1.367 (7)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.382 (7)	C10—C11	1.370 (9)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.391 (6)	C11—C12	1.358 (8)
C4—C7	1.454 (6)	C11—Br1	1.878 (5)
C5—C6	1.375 (6)	C12—C13	1.386 (7)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.267 (6)	O1—H1	0.8200
C7—H7	0.9300
O1—C1—C6	123.4 (4)	C13—C8—C9	118.6 (4)
O1—C1—C2	117.4 (4)	C13—C8—N1	118.7 (4)
C6—C1—C2	119.3 (4)	C9—C8—N1	122.6 (4)
C3—C2—C1	119.7 (4)	C10—C9—C8	120.2 (5)
C3—C2—H2	120.2	C10—C9—H9	119.9
C1—C2—H2	120.2	C8—C9—H9	119.9
C2—C3—C4	121.6 (4)	C9—C10—C11	120.4 (5)
C2—C3—H3	119.2	C9—C10—H10	119.8
C4—C3—H3	119.2	C11—C10—H10	119.8
C3—C4—C5	118.2 (4)	C12—C11—C10	120.5 (5)
C3—C4—C7	119.8 (4)	C12—C11—Br1	120.0 (4)
C5—C4—C7	121.8 (4)	C10—C11—Br1	119.4 (4)
C6—C5—C4	120.6 (4)	C11—C12—C13	119.6 (5)
C6—C5—H5	119.7	C11—C12—H12	120.2
C4—C5—H5	119.7	C13—C12—H12	120.2
C5—C6—C1	120.6 (4)	C8—C13—C12	120.6 (5)
C5—C6—H6	119.7	C8—C13—H13	119.7
C1—C6—H6	119.7	C12—C13—H13	119.7
N1—C7—C4	124.7 (4)	C7—N1—C8	118.6 (4)
N1—C7—H7	117.7	C1—O1—H1	109.5
C4—C7—H7	117.7
O1—C1—C2—C3	−177.6 (4)	N1—C8—C9—C10	179.9 (5)
C6—C1—C2—C3	1.5 (7)	C8—C9—C10—C11	−0.2 (8)
C1—C2—C3—C4	−0.9 (7)	C9—C10—C11—C12	1.5 (8)
C2—C3—C4—C5	0.2 (7)	C9—C10—C11—Br1	−178.6 (4)
C2—C3—C4—C7	174.8 (4)	C10—C11—C12—C13	−0.4 (8)
C3—C4—C5—C6	−0.1 (6)	Br1—C11—C12—C13	179.7 (4)
C7—C4—C5—C6	−174.6 (4)	C9—C8—C13—C12	3.4 (7)
C4—C5—C6—C1	0.7 (6)	N1—C8—C13—C12	−178.7 (4)
O1—C1—C6—C5	177.6 (4)	C11—C12—C13—C8	−2.2 (8)
C2—C1—C6—C5	−1.4 (7)	C4—C7—N1—C8	171.2 (4)
C3—C4—C7—N1	172.7 (4)	C13—C8—N1—C7	147.7 (4)
C5—C4—C7—N1	−12.9 (7)	C9—C8—N1—C7	−34.5 (6)
C13—C8—C9—C10	−2.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.92	2.734	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.92	2.734	175

Symmetry code: (i) .