(E)-2-[(5-Bromo-2-hydroxy-benzyl-idene)amino]benzonitrile.

In the mol-ecule of the title compound, C(14)H(9)BrN(2)O, the dihedral angle between the aromatic rings is 1.09 (4)°. Intra-molecular O-H⋯N hydrogen bonding results in the formation of a planar (r.m.s. deviation = 0.0140 Å) six-membered ring. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into chains.

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Chen et al. (2008 ▶); May et al. (2004 ▶); Weber et al. (2007 ▶). For a related structure, see: Elmalı et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H9BrN2O

M = 301.14

Orthorhombic,

a = 25.609 (8) Å

b = 3.9299 (12) Å

c = 12.368 (4) Å

V = 1244.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.29 mm−1

T = 294 K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.518, T max = 0.518

9720 measured reflections

2771 independent reflections

1737 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.090

S = 1.01

2771 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1271 Friedel pairs

Flack parameter: 0.039 (14)

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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027950/hk2739sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027950/hk2739Isup2.hkl

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

C14H9BrN2O	F(000) = 600
Mr = 301.14	Dx = 1.607 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1688 reflections
a = 25.609 (8) Å	θ = 3.1–27.7°
b = 3.9299 (12) Å	µ = 3.29 mm−1
c = 12.368 (4) Å	T = 294 K
V = 1244.7 (7) Å3	Prism, yellow
Z = 4	0.2 × 0.2 × 0.2 mm

Bruker SMART CCD area-detector diffractometer	2771 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 27.6°, θmin = 1.6°
φ and ω scans	h = −33→33
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −5→5
Tmin = 0.518, Tmax = 0.518	l = −16→14
9720 measured reflections

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-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.0106P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2771 reflections	Δρmax = 0.23 e Å−3
163 parameters	Δρmin = −0.29 e Å−3
1 restraint	Absolute structure: Flack (1983), 1271 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.039 (14)

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	0.014802 (15)	0.46800 (11)	0.49637 (9)	0.0816 (2)
O1	0.15855 (14)	−0.0121 (8)	0.1439 (2)	0.0767 (9)
H1A	0.1892	0.0184	0.1605	0.115*
N1	0.23690 (11)	0.1858 (9)	0.2691 (3)	0.0471 (7)
N2	0.28448 (17)	−0.1697 (11)	0.0417 (3)	0.0800 (12)
C1	0.14763 (14)	0.2551 (10)	0.3176 (3)	0.0481 (9)
C2	0.12781 (19)	0.1038 (11)	0.2221 (4)	0.0567 (12)
C3	0.0737 (2)	0.0789 (11)	0.2121 (4)	0.0723 (13)
H3A	0.0598	−0.0122	0.1490	0.087*
C4	0.04062 (17)	0.1828 (11)	0.2912 (4)	0.0679 (12)
H4A	0.0047	0.1582	0.2825	0.081*
C5	0.06036 (14)	0.3244 (10)	0.3842 (4)	0.0576 (10)
C6	0.11302 (15)	0.3625 (11)	0.3970 (3)	0.0543 (10)
H6A	0.1259	0.4619	0.4598	0.065*
C7	0.20246 (14)	0.2971 (10)	0.3346 (3)	0.0488 (9)
H7A	0.2135	0.4110	0.3964	0.059*
C8	0.29066 (13)	0.2276 (9)	0.2900 (3)	0.0458 (9)
C9	0.32433 (17)	0.1123 (10)	0.2105 (3)	0.0523 (10)
C10	0.37810 (18)	0.1385 (12)	0.2213 (4)	0.0622 (12)
H10A	0.4001	0.0623	0.1666	0.075*
C11	0.39839 (16)	0.2791 (13)	0.3143 (4)	0.0735 (13)
H11A	0.4344	0.2974	0.3227	0.088*
C12	0.36610 (17)	0.3907 (12)	0.3933 (4)	0.0661 (12)
H12A	0.3802	0.4864	0.4556	0.079*
C13	0.31227 (16)	0.3646 (12)	0.3830 (4)	0.0613 (11)
H13A	0.2907	0.4392	0.4386	0.074*
C14	0.30179 (18)	−0.0458 (12)	0.1155 (4)	0.0598 (11)

	U11	U22	U33	U12	U13	U23
Br1	0.0607 (2)	0.0846 (3)	0.0995 (4)	0.0101 (2)	0.0174 (3)	0.0112 (4)
O1	0.086 (2)	0.096 (3)	0.0480 (19)	−0.0127 (17)	−0.0052 (17)	−0.0184 (16)
N1	0.0530 (19)	0.054 (2)	0.0344 (18)	−0.0040 (14)	0.0005 (15)	−0.0044 (16)
N2	0.106 (3)	0.081 (3)	0.054 (3)	0.002 (2)	0.007 (2)	−0.024 (2)
C1	0.055 (2)	0.044 (2)	0.045 (2)	−0.0054 (19)	−0.005 (2)	0.0047 (19)
C2	0.073 (3)	0.050 (3)	0.047 (3)	−0.009 (2)	−0.004 (3)	−0.005 (2)
C3	0.075 (3)	0.076 (3)	0.067 (3)	−0.015 (3)	−0.024 (3)	0.004 (3)
C4	0.052 (2)	0.060 (3)	0.091 (4)	−0.010 (2)	−0.015 (3)	0.009 (3)
C5	0.049 (2)	0.048 (2)	0.076 (3)	0.0014 (18)	−0.001 (2)	0.016 (2)
C6	0.056 (2)	0.056 (3)	0.052 (3)	−0.0010 (19)	−0.003 (2)	−0.006 (2)
C7	0.059 (2)	0.049 (2)	0.038 (2)	−0.0061 (18)	−0.006 (2)	−0.002 (2)
C8	0.057 (2)	0.042 (2)	0.038 (2)	−0.0070 (17)	0.000 (2)	0.0003 (19)
C9	0.066 (3)	0.046 (2)	0.045 (3)	0.0001 (19)	0.005 (2)	0.004 (2)
C10	0.062 (3)	0.061 (3)	0.064 (3)	0.000 (2)	0.012 (3)	−0.003 (3)
C11	0.054 (2)	0.077 (3)	0.089 (4)	−0.003 (2)	0.010 (3)	0.000 (3)
C12	0.065 (3)	0.069 (3)	0.064 (3)	−0.009 (2)	−0.018 (2)	−0.008 (2)
C13	0.057 (2)	0.076 (3)	0.051 (3)	−0.006 (2)	0.001 (2)	−0.009 (2)
C14	0.076 (3)	0.059 (3)	0.045 (3)	0.005 (2)	0.014 (2)	−0.007 (2)

Br1—C5	1.898 (4)	C7—C1	1.429 (5)
O1—C2	1.328 (6)	C7—H7A	0.9300
O1—H1A	0.8200	C8—C9	1.385 (5)
N1—C7	1.275 (4)	C8—C13	1.384 (5)
N1—C8	1.411 (4)	C9—C10	1.387 (6)
C2—C1	1.416 (6)	C10—C11	1.377 (6)
C3—C2	1.393 (7)	C10—H10A	0.9300
C3—C4	1.358 (7)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C11	1.354 (6)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C4	1.374 (6)	C13—C12	1.388 (6)
C6—C1	1.388 (5)	C13—H13A	0.9300
C6—C5	1.366 (5)	C14—N2	1.125 (5)
C6—H6A	0.9300	C14—C9	1.449 (7)
C2—O1—H1A	109.5	N1—C7—H7A	118.5
C7—N1—C8	121.2 (3)	C1—C7—H7A	118.5
C2—C1—C7	121.6 (4)	C9—C8—N1	116.0 (3)
C6—C1—C2	119.2 (4)	C9—C8—C13	117.9 (3)
C6—C1—C7	119.2 (4)	C13—C8—N1	126.0 (3)
O1—C2—C1	122.6 (4)	C8—C9—C10	121.7 (4)
O1—C2—C3	120.0 (4)	C8—C9—C14	118.0 (4)
C3—C2—C1	117.4 (4)	C10—C9—C14	120.4 (4)
C2—C3—H3A	118.8	C9—C10—H10A	120.5
C4—C3—C2	122.4 (5)	C11—C10—C9	119.0 (4)
C4—C3—H3A	118.8	C11—C10—H10A	120.5
C3—C4—C5	119.7 (4)	C10—C11—H11A	119.9
C3—C4—H4A	120.2	C12—C11—C10	120.2 (4)
C5—C4—H4A	120.2	C12—C11—H11A	119.9
C4—C5—Br1	120.4 (3)	C11—C12—C13	121.0 (4)
C6—C5—Br1	119.3 (3)	C11—C12—H12A	119.5
C6—C5—C4	120.3 (4)	C13—C12—H12A	119.5
C1—C6—H6A	119.5	C8—C13—C12	120.2 (4)
C5—C6—C1	121.0 (4)	C8—C13—H13A	119.9
C5—C6—H6A	119.5	C12—C13—H13A	119.9
N1—C7—C1	123.1 (3)	N2—C14—C9	179.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.93	2.651 (4)	146
C7—H7A···N2i	0.93	2.44	3.326 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.93	2.651 (4)	146
C7—H7A⋯N2i	0.93	2.44	3.326 (4)	160

Symmetry code: (i) .