4-Bromo-2-({4-[(hy-droxy-imino)-meth-yl]phen-yl}imino-meth-yl)phenol.

In the title compound, C(14)H(11)BrN(2)O(2), the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09 (1)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, inter-molecular O-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into a chain-like supra-molecular structure.

Related literature

For background to the use of Schiff bases as ligands in coord­ination chemistry, see: Biswas et al. (2008 ▶); Dong et al. (2010 ▶). For the synthesis of the title compound and related structures, see: Dong et al. (2007 ▶, 2009 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C14H11BrN2O2

M = 319.16

Orthorhombic,

a = 4.4279 (5) Å

b = 12.1790 (16) Å

c = 23.196 (2) Å

V = 1250.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.29 mm−1

T = 113 K

0.26 × 0.24 × 0.22 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.482, T max = 0.532

15336 measured reflections

4346 independent reflections

2818 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.054

S = 0.85

4346 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.88 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶), 1615 Friedel pairs

Flack parameter: −0.022 (7)

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002698X/pv2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002698X/pv2295Isup2.hkl

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

C14H11BrN2O2	Dx = 1.695 Mg m−3
Mr = 319.16	Melting point = 490–491 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4929 reflections
a = 4.4279 (5) Å	θ = 1.9–32.9°
b = 12.1790 (16) Å	µ = 3.29 mm−1
c = 23.196 (2) Å	T = 113 K
V = 1250.9 (3) Å3	Needle, pale-yellow
Z = 4	0.26 × 0.24 × 0.22 mm
F(000) = 640

Rigaku Saturn724 CCD diffractometer	4346 independent reflections
Radiation source: Rotating Anode	2818 reflections with I > 2σ(I)
multilayer	Rint = 0.048
Detector resolution: 14.222 pixels mm-1	θmax = 32.9°, θmin = 1.8°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −18→17
Tmin = 0.482, Tmax = 0.532	l = −34→33
15336 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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.0171P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85	(Δ/σ)max = 0.001
4346 reflections	Δρmax = 0.88 e Å−3
180 parameters	Δρmin = −0.44 e Å−3
0 restraints	Absolute structure: Flack (1983), 1615 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.022 (7)

Experimental. Anal. Calc. for C14H11BrN2O2: C, 52.69; H, 3.47; N, 8.78. Found: C, 52.67; H, 3.44; N, 8.81.

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	0.93894 (6)	0.310770 (17)	0.055477 (9)	0.02449 (6)
O1	0.5216 (4)	0.65997 (11)	0.22190 (6)	0.0219 (4)
O2	−0.9560 (4)	0.35901 (13)	0.51519 (6)	0.0228 (4)
N1	0.1808 (4)	0.51372 (14)	0.27053 (7)	0.0158 (4)
N2	−0.7439 (4)	0.34661 (14)	0.47039 (7)	0.0165 (4)
C1	0.6150 (5)	0.57912 (16)	0.18617 (8)	0.0156 (5)
C2	0.5081 (5)	0.46983 (15)	0.19213 (8)	0.0150 (5)
C3	0.6111 (5)	0.38957 (16)	0.15310 (8)	0.0174 (5)
H3	0.5429	0.3159	0.1565	0.021*
C4	0.8098 (5)	0.41758 (17)	0.11007 (9)	0.0181 (5)
C5	0.9174 (5)	0.52501 (16)	0.10466 (8)	0.0174 (4)
H5	1.0571	0.5431	0.0751	0.021*
C6	0.8195 (5)	0.60434 (17)	0.14244 (9)	0.0189 (5)
H6	0.8922	0.6774	0.1387	0.023*
C7	0.2943 (5)	0.44092 (17)	0.23670 (9)	0.0172 (5)
H7	0.2362	0.3663	0.2411	0.021*
C8	−0.0289 (5)	0.48808 (15)	0.31419 (8)	0.0142 (4)
C9	−0.1308 (5)	0.57570 (17)	0.34784 (9)	0.0181 (5)
H9	−0.0580	0.6477	0.3405	0.022*
C10	−0.3373 (5)	0.55866 (17)	0.39193 (9)	0.0185 (5)
H10	−0.4072	0.6195	0.4138	0.022*
C11	−0.4435 (5)	0.45385 (15)	0.40458 (8)	0.0154 (4)
C12	−0.3426 (5)	0.36586 (16)	0.37064 (9)	0.0175 (5)
H12	−0.4139	0.2938	0.3783	0.021*
C13	−0.1407 (5)	0.38292 (16)	0.32620 (8)	0.0170 (5)
H13	−0.0766	0.3225	0.3034	0.020*
C14	−0.6628 (5)	0.44081 (17)	0.45110 (9)	0.0171 (5)
H14	−0.7489	0.5048	0.4678	0.021*
H1	0.384 (5)	0.6368 (17)	0.2459 (9)	0.022 (7)*
H2	−1.018 (7)	0.302 (2)	0.5186 (12)	0.070 (12)*

	U11	U22	U33	U12	U13	U23
Br1	0.03228 (13)	0.02054 (9)	0.02065 (10)	0.00167 (11)	0.00598 (11)	−0.00300 (9)
O1	0.0290 (11)	0.0162 (7)	0.0204 (8)	−0.0007 (7)	0.0061 (8)	−0.0010 (6)
O2	0.0245 (10)	0.0219 (8)	0.0220 (8)	−0.0066 (8)	0.0081 (8)	−0.0010 (6)
N1	0.0149 (10)	0.0174 (9)	0.0150 (9)	0.0026 (8)	−0.0014 (8)	0.0015 (7)
N2	0.0123 (10)	0.0234 (10)	0.0138 (8)	−0.0013 (7)	0.0002 (8)	−0.0013 (7)
C1	0.0158 (13)	0.0163 (10)	0.0146 (10)	0.0027 (9)	−0.0017 (9)	−0.0003 (8)
C2	0.0134 (14)	0.0171 (9)	0.0146 (9)	0.0017 (8)	−0.0016 (9)	0.0026 (7)
C3	0.0174 (14)	0.0151 (10)	0.0196 (11)	−0.0007 (9)	−0.0048 (10)	0.0005 (8)
C4	0.0184 (13)	0.0202 (11)	0.0157 (10)	0.0042 (9)	−0.0025 (10)	−0.0015 (9)
C5	0.0149 (12)	0.0215 (10)	0.0157 (10)	0.0002 (10)	0.0016 (11)	0.0023 (8)
C6	0.0217 (13)	0.0148 (10)	0.0201 (11)	−0.0032 (9)	−0.0022 (10)	0.0014 (8)
C7	0.0159 (12)	0.0164 (10)	0.0194 (11)	−0.0005 (9)	−0.0019 (10)	0.0015 (9)
C8	0.0112 (12)	0.0177 (9)	0.0136 (9)	−0.0004 (9)	−0.0016 (9)	0.0009 (7)
C9	0.0186 (14)	0.0149 (10)	0.0209 (11)	0.0001 (9)	0.0010 (10)	0.0005 (8)
C10	0.0210 (13)	0.0168 (10)	0.0178 (11)	0.0031 (9)	−0.0005 (10)	−0.0037 (8)
C11	0.0129 (11)	0.0199 (10)	0.0134 (9)	−0.0015 (10)	−0.0030 (10)	−0.0001 (7)
C12	0.0195 (13)	0.0140 (10)	0.0190 (10)	0.0003 (9)	−0.0009 (10)	0.0027 (8)
C13	0.0189 (14)	0.0151 (10)	0.0170 (10)	0.0028 (9)	−0.0033 (9)	−0.0012 (8)
C14	0.0161 (11)	0.0184 (10)	0.0169 (11)	0.0001 (8)	−0.0019 (10)	−0.0024 (9)

Br1—C4	1.903 (2)	C5—H5	0.9500
O1—C1	1.352 (2)	C6—H6	0.9500
O1—H1	0.87 (2)	C7—H7	0.9500
O2—N2	1.409 (2)	C8—C9	1.397 (3)
O2—H2	0.75 (3)	C8—C13	1.401 (3)
N1—C7	1.286 (2)	C9—C10	1.387 (3)
N1—C8	1.409 (3)	C9—H9	0.9500
N2—C14	1.283 (2)	C10—C11	1.392 (3)
C1—C6	1.394 (3)	C10—H10	0.9500
C1—C2	1.419 (3)	C11—C12	1.403 (3)
C2—C3	1.408 (3)	C11—C14	1.460 (3)
C2—C7	1.445 (3)	C12—C13	1.380 (3)
C3—C4	1.374 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.398 (3)	C14—H14	0.9500
C5—C6	1.375 (3)
C1—O1—H1	111.7 (14)	N1—C7—H7	119.2
N2—O2—H2	103 (2)	C2—C7—H7	119.2
C7—N1—C8	122.91 (18)	C9—C8—C13	118.23 (19)
C14—N2—O2	110.38 (17)	C9—C8—N1	116.44 (18)
O1—C1—C6	118.97 (18)	C13—C8—N1	125.33 (18)
O1—C1—C2	121.43 (19)	C10—C9—C8	120.70 (19)
C6—C1—C2	119.60 (18)	C10—C9—H9	119.6
C3—C2—C1	118.72 (19)	C8—C9—H9	119.6
C3—C2—C7	120.18 (18)	C9—C10—C11	121.0 (2)
C1—C2—C7	121.09 (18)	C9—C10—H10	119.5
C4—C3—C2	120.14 (19)	C11—C10—H10	119.5
C4—C3—H3	119.9	C10—C11—C12	118.3 (2)
C2—C3—H3	119.9	C10—C11—C14	118.71 (18)
C3—C4—C5	121.05 (19)	C12—C11—C14	122.92 (18)
C3—C4—Br1	120.41 (16)	C13—C12—C11	120.70 (19)
C5—C4—Br1	118.53 (16)	C13—C12—H12	119.7
C6—C5—C4	119.5 (2)	C11—C12—H12	119.7
C6—C5—H5	120.2	C12—C13—C8	120.99 (19)
C4—C5—H5	120.2	C12—C13—H13	119.5
C5—C6—C1	120.93 (19)	C8—C13—H13	119.5
C5—C6—H6	119.5	N2—C14—C11	122.78 (18)
C1—C6—H6	119.5	N2—C14—H14	118.6
N1—C7—C2	121.63 (19)	C11—C14—H14	118.6
O1—C1—C2—C3	179.22 (19)	C7—N1—C8—C9	179.5 (2)
C6—C1—C2—C3	−0.5 (3)	C7—N1—C8—C13	−0.4 (3)
O1—C1—C2—C7	0.1 (3)	C13—C8—C9—C10	0.0 (3)
C6—C1—C2—C7	−179.5 (2)	N1—C8—C9—C10	−179.95 (19)
C1—C2—C3—C4	−0.3 (3)	C8—C9—C10—C11	1.3 (3)
C7—C2—C3—C4	178.75 (19)	C9—C10—C11—C12	−1.6 (3)
C2—C3—C4—C5	1.0 (3)	C9—C10—C11—C14	−179.44 (19)
C2—C3—C4—Br1	−177.75 (16)	C10—C11—C12—C13	0.6 (3)
C3—C4—C5—C6	−1.0 (3)	C14—C11—C12—C13	178.34 (19)
Br1—C4—C5—C6	177.87 (17)	C11—C12—C13—C8	0.7 (3)
C4—C5—C6—C1	0.1 (3)	C9—C8—C13—C12	−1.0 (3)
O1—C1—C6—C5	−179.1 (2)	N1—C8—C13—C12	178.95 (19)
C2—C1—C6—C5	0.5 (3)	O2—N2—C14—C11	179.74 (18)
C8—N1—C7—C2	179.75 (19)	C10—C11—C14—N2	−171.1 (2)
C3—C2—C7—N1	−175.3 (2)	C12—C11—C14—N2	11.2 (3)
C1—C2—C7—N1	3.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87 (2)	1.84 (2)	2.593 (2)	143 (2)
O2—H2···N2i	0.75 (3)	2.08 (3)	2.830 (2)	173 (2)
C5—H5···O2ii	0.95	2.54	3.463 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.87 (2)	1.84 (2)	2.593 (2)	143 (2)
O2—H2⋯N2i	0.75 (3)	2.08 (3)	2.830 (2)	173 (2)
C5—H5⋯O2ii	0.95	2.54	3.463 (3)	163

Symmetry codes: (i) ; (ii) .