4-Bromo-2-{(E)-3-[1-(hydroxy-imino)eth-yl]phenyl-imino-meth-yl}phenol.

In the title compound, C(15)H(13)BrN(2)O(2), he oxime unit adopts an E conformation with respect to the O-H group. A classical intra-molecular O-H⋯N hydrogen bond results in the formation of a six-membered ring. The crystal structure is stabilized by inter-molecular O-H⋯N hydrogen bonds between the hydr-oxy groups and the oxime N atoms. In addition, the crystal structure also features short inter-molecular Br⋯Br short contacts with a distance of 3.8768 (5) Å.

Related literature

For background to Schiff bases, see: Dong et al. (2007 ▶, 2008 ▶); Wang et al. 2009 ▶). For background to oximes, see: Golovnia et al. (2009 ▶); Liu et al. (2008 ▶); Dong et al. (2009a ▶); Öztürk et al. (2009 ▶). For the synthesis, see: Dong et al. (2009b ▶).

Experimental

Crystal data

C15H13BrN2O2

M = 333.18

Monoclinic,

a = 17.020 (2) Å

b = 6.1676 (7) Å

c = 13.693 (1) Å

β = 96.461 (1)°

V = 1428.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.88 mm−1

T = 298 K

0.45 × 0.20 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.357, T max = 0.762

6906 measured reflections

2492 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 0.99

2492 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048855/lx2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048855/lx2124Isup2.hkl

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

C15H13BrN2O2	F(000) = 672
Mr = 333.18	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Melting point = 459–461 K
Hall symbol: -p 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.020 (2) Å	Cell parameters from 2173 reflections
b = 6.1676 (7) Å	θ = 2.7–23.8°
c = 13.693 (1) Å	µ = 2.88 mm−1
β = 96.461 (1)°	T = 298 K
V = 1428.3 (3) Å3	Needle-like, yellow
Z = 4	0.45 × 0.20 × 0.10 mm

Siemens SMART 1000 CCD area-detector diffractometer	2492 independent reflections
Radiation source: fine-focus sealed tube	1799 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm-1	Rint = 0.051
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→14
Tmin = 0.357, Tmax = 0.762	k = −7→7
6906 measured reflections	l = −15→16

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.100	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
2492 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.32 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
Br	0.46909 (2)	−0.34895 (6)	0.66885 (3)	0.05662 (19)
N1	0.04843 (18)	1.3049 (4)	0.46740 (19)	0.0451 (7)
N2	0.25065 (15)	0.4933 (4)	0.52712 (19)	0.0416 (7)
O1	0.01134 (16)	1.4311 (4)	0.38885 (16)	0.0609 (8)
H1	−0.0096	1.5373	0.4110	0.091*
O2	0.29339 (17)	0.2760 (5)	0.37605 (18)	0.0688 (8)
H2	0.2718	0.3726	0.4044	0.103*
C1	0.0818 (3)	1.0731 (7)	0.3317 (2)	0.0601 (11)
H1A	0.0385	1.1454	0.2940	0.090*
H1B	0.0753	0.9191	0.3247	0.090*
H1C	0.1306	1.1160	0.3084	0.090*
C2	0.0833 (2)	1.1340 (5)	0.4385 (2)	0.0355 (8)
C3	0.12600 (18)	0.9934 (5)	0.5170 (2)	0.0328 (7)
C4	0.16790 (19)	0.8077 (5)	0.4921 (2)	0.0361 (8)
H4	0.1683	0.7723	0.4261	0.043*
C5	0.2089 (2)	0.6749 (5)	0.5637 (2)	0.0372 (8)
C6	0.2088 (2)	0.7269 (6)	0.6638 (2)	0.0457 (9)
H6	0.2355	0.6402	0.7123	0.055*
C7	0.1674 (2)	0.9129 (6)	0.6892 (2)	0.0541 (10)
H7	0.1670	0.9486	0.7551	0.065*
C8	0.1272 (2)	1.0439 (6)	0.6175 (2)	0.0439 (9)
H8	0.1007	1.1664	0.6362	0.053*
C9	0.2887 (2)	0.3533 (5)	0.5848 (2)	0.0402 (8)
H9	0.2886	0.3675	0.6524	0.048*
C10	0.33200 (19)	0.1729 (5)	0.5462 (2)	0.0370 (8)
C11	0.3322 (2)	0.1382 (6)	0.4443 (3)	0.0455 (9)
C12	0.3730 (2)	−0.0397 (6)	0.4104 (3)	0.0554 (10)
H12	0.3726	−0.0625	0.3432	0.067*
C13	0.4141 (2)	−0.1828 (6)	0.4770 (3)	0.0520 (10)
H13	0.4413	−0.3000	0.4544	0.062*
C14	0.4138 (2)	−0.1477 (5)	0.5778 (2)	0.0391 (8)
C15	0.37336 (19)	0.0263 (5)	0.6123 (2)	0.0393 (8)
H15	0.3735	0.0467	0.6797	0.047*

	U11	U22	U33	U12	U13	U23
Br	0.0571 (3)	0.0476 (3)	0.0643 (3)	0.01472 (19)	0.0030 (2)	0.00954 (19)
N1	0.056 (2)	0.0395 (17)	0.0372 (15)	0.0112 (15)	−0.0063 (14)	0.0022 (13)
N2	0.0357 (17)	0.0356 (17)	0.0537 (17)	0.0027 (13)	0.0058 (14)	0.0020 (13)
O1	0.083 (2)	0.0526 (16)	0.0436 (13)	0.0295 (15)	−0.0089 (13)	0.0039 (12)
O2	0.078 (2)	0.079 (2)	0.0479 (14)	0.0289 (17)	0.0001 (15)	0.0108 (14)
C1	0.081 (3)	0.062 (2)	0.0367 (19)	0.028 (2)	0.0017 (19)	−0.0001 (18)
C2	0.036 (2)	0.0329 (19)	0.0373 (17)	−0.0002 (15)	0.0027 (15)	−0.0020 (14)
C3	0.0309 (19)	0.0315 (18)	0.0353 (16)	0.0001 (14)	0.0005 (14)	0.0005 (14)
C4	0.037 (2)	0.037 (2)	0.0338 (16)	−0.0039 (15)	0.0021 (15)	−0.0024 (14)
C5	0.0311 (19)	0.0339 (19)	0.0462 (19)	−0.0012 (14)	0.0031 (15)	0.0022 (15)
C6	0.051 (2)	0.043 (2)	0.043 (2)	0.0113 (18)	0.0038 (17)	0.0141 (16)
C7	0.071 (3)	0.058 (2)	0.0331 (18)	0.014 (2)	0.0074 (18)	0.0027 (17)
C8	0.052 (2)	0.040 (2)	0.0395 (18)	0.0097 (17)	0.0060 (17)	0.0024 (16)
C9	0.040 (2)	0.0346 (19)	0.0455 (19)	−0.0010 (16)	0.0020 (16)	−0.0017 (16)
C10	0.0321 (19)	0.0332 (19)	0.0443 (18)	−0.0013 (15)	−0.0016 (15)	0.0004 (15)
C11	0.037 (2)	0.050 (2)	0.048 (2)	0.0033 (17)	0.0018 (17)	0.0052 (18)
C12	0.057 (3)	0.070 (3)	0.0408 (19)	0.012 (2)	0.0101 (18)	−0.0030 (19)
C13	0.051 (3)	0.051 (2)	0.055 (2)	0.0117 (18)	0.0109 (19)	−0.0053 (18)
C14	0.034 (2)	0.0331 (19)	0.050 (2)	−0.0024 (16)	0.0022 (16)	0.0017 (15)
C15	0.038 (2)	0.038 (2)	0.0411 (18)	0.0003 (16)	0.0013 (16)	−0.0041 (15)

Br—C14	1.928 (3)	C4—H4	0.9300
Br—Bri	3.8768 (5)	C5—C6	1.409 (5)
Br—Brii	3.8768 (5)	C6—C7	1.410 (5)
N1—C2	1.293 (4)	C6—H6	0.9300
N1—O1	1.417 (3)	C7—C8	1.390 (5)
N2—C9	1.294 (4)	C7—H7	0.9300
N2—C5	1.446 (4)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.466 (4)
O2—C11	1.377 (4)	C9—H9	0.9300
O2—H2	0.8200	C10—C15	1.411 (4)
C1—C2	1.507 (4)	C10—C11	1.411 (5)
C1—H1A	0.9600	C11—C12	1.405 (5)
C1—H1B	0.9600	C12—C13	1.399 (5)
C1—H1C	0.9600	C12—H12	0.9300
C2—C3	1.504 (4)	C13—C14	1.398 (5)
C3—C8	1.409 (4)	C13—H13	0.9300
C3—C4	1.411 (4)	C14—C15	1.387 (4)
C4—C5	1.401 (4)	C15—H15	0.9300
C14—Br—Bri	86.56 (10)	C8—C7—C6	121.3 (3)
C14—Br—Brii	164.58 (10)	C8—C7—H7	119.4
Bri—Br—Brii	105.395 (19)	C6—C7—H7	119.4
C2—N1—O1	113.3 (3)	C7—C8—C3	120.9 (3)
C9—N2—C5	122.5 (3)	C7—C8—H8	119.6
N1—O1—H1	109.5	C3—C8—H8	119.6
C11—O2—H2	109.5	N2—C9—C10	121.6 (3)
C2—C1—H1A	109.5	N2—C9—H9	119.2
C2—C1—H1B	109.5	C10—C9—H9	119.2
H1A—C1—H1B	109.5	C15—C10—C11	118.7 (3)
C2—C1—H1C	109.5	C15—C10—C9	119.3 (3)
H1A—C1—H1C	109.5	C11—C10—C9	122.0 (3)
H1B—C1—H1C	109.5	O2—C11—C12	118.3 (3)
N1—C2—C3	116.9 (3)	O2—C11—C10	121.5 (3)
N1—C2—C1	122.8 (3)	C12—C11—C10	120.1 (3)
C3—C2—C1	120.2 (3)	C13—C12—C11	120.4 (3)
C8—C3—C4	117.6 (3)	C13—C12—H12	119.8
C8—C3—C2	121.6 (3)	C11—C12—H12	119.8
C4—C3—C2	120.8 (3)	C14—C13—C12	119.3 (3)
C5—C4—C3	122.0 (3)	C14—C13—H13	120.4
C5—C4—H4	119.0	C12—C13—H13	120.4
C3—C4—H4	119.0	C15—C14—C13	120.9 (3)
C4—C5—C6	119.5 (3)	C15—C14—Br	120.2 (2)
C4—C5—N2	115.8 (3)	C13—C14—Br	118.9 (2)
C6—C5—N2	124.6 (3)	C14—C15—C10	120.5 (3)
C5—C6—C7	118.7 (3)	C14—C15—H15	119.7
C5—C6—H6	120.6	C10—C15—H15	119.7
C7—C6—H6	120.6
O1—N1—C2—C3	178.5 (3)	N2—C9—C10—C15	179.2 (3)
O1—N1—C2—C1	−1.9 (5)	N2—C9—C10—C11	−2.2 (5)
N1—C2—C3—C8	0.8 (5)	C15—C10—C11—O2	−179.6 (3)
C1—C2—C3—C8	−178.8 (3)	C9—C10—C11—O2	1.8 (5)
N1—C2—C3—C4	−177.9 (3)	C15—C10—C11—C12	0.1 (5)
C1—C2—C3—C4	2.5 (5)	C9—C10—C11—C12	−178.5 (3)
C8—C3—C4—C5	0.6 (5)	O2—C11—C12—C13	179.2 (4)
C2—C3—C4—C5	179.4 (3)	C10—C11—C12—C13	−0.5 (6)
C3—C4—C5—C6	−0.1 (5)	C11—C12—C13—C14	0.4 (6)
C3—C4—C5—N2	−178.6 (3)	C12—C13—C14—C15	0.0 (5)
C9—N2—C5—C4	−177.6 (3)	C12—C13—C14—Br	178.9 (3)
C9—N2—C5—C6	4.0 (5)	Bri—Br—C14—C15	−39.2 (3)
C4—C5—C6—C7	−0.3 (5)	Brii—Br—C14—C15	102.3 (4)
N2—C5—C6—C7	178.1 (3)	Bri—Br—C14—C13	141.9 (3)
C5—C6—C7—C8	0.0 (6)	Brii—Br—C14—C13	−76.7 (5)
C6—C7—C8—C3	0.6 (6)	C13—C14—C15—C10	−0.4 (5)
C4—C3—C8—C7	−0.9 (5)	Br—C14—C15—C10	−179.3 (2)
C2—C3—C8—C7	−179.6 (3)	C11—C10—C15—C14	0.3 (5)
C5—N2—C9—C10	−178.8 (3)	C9—C10—C15—C14	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1iii	0.82	2.10	2.830 (4)	149
O2—H2···N2	0.82	1.91	2.635 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.10	2.830 (4)	149
O2—H2⋯N2	0.82	1.91	2.635 (4)	147

Symmetry code: (i) .