4-Bromo-2-[(E)-(4-chloro-phen-yl)imino-meth-yl]phenol.

In the title compound, C(13)H(9)BrClNO, the dihedral angle between the substituted benzene rings is 43.90 (11)°. Strong intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs. The crystal structure features short intemolecular Br⋯Br [3.554 (2) Å] and Cl⋯Cl [3.412 (2) Å] contacts. The crystal packing is further stabilized by inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C13H9BrClNO

M = 310.57

Monoclinic,

a = 27.652 (11) Å

b = 7.011 (3) Å

c = 6.219 (3) Å

β = 96.38 (2)°

V = 1198.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.63 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.363, T max = 0.502

5719 measured reflections

2170 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.02

2170 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004417/jh2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004417/jh2265Isup2.hkl

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

C13H9BrClNO	F(000) = 616
Mr = 310.57	Dx = 1.722 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2520 reflections
a = 27.652 (11) Å	θ = 2.5–27.5°
b = 7.011 (3) Å	µ = 3.63 mm−1
c = 6.219 (3) Å	T = 296 K
β = 96.38 (2)°	Prism, light-yellow
V = 1198.2 (8) Å3	0.35 × 0.25 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2170 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→33
Tmin = 0.363, Tmax = 0.502	k = −8→5
5719 measured reflections	l = −7→6

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.3051P] where P = (Fo2 + 2Fc2)/3
2170 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.456428 (11)	0.43271 (5)	0.67549 (5)	0.05153 (14)
Cl1	0.03796 (3)	0.54095 (14)	0.23081 (16)	0.0684 (3)
O1	0.27742 (7)	0.5674 (3)	1.1170 (3)	0.0444 (5)
H1	0.2529	0.5423	1.0354	0.067*
N1	0.22712 (8)	0.4746 (3)	0.7551 (3)	0.0313 (5)
C1	0.31315 (10)	0.4668 (3)	0.7991 (4)	0.0289 (6)
C2	0.31691 (10)	0.5350 (3)	1.0152 (4)	0.0309 (6)
C3	0.36211 (11)	0.5707 (3)	1.1235 (4)	0.0361 (6)
H3	0.3647	0.6166	1.2646	0.043*
C4	0.40322 (11)	0.5392 (3)	1.0256 (4)	0.0363 (6)
H4	0.4336	0.5642	1.1000	0.044*
C5	0.39973 (10)	0.4695 (3)	0.8134 (4)	0.0331 (6)
C6	0.35529 (10)	0.4331 (3)	0.7031 (4)	0.0304 (6)
H6	0.3532	0.3855	0.5628	0.036*
C7	0.26674 (10)	0.4453 (3)	0.6737 (4)	0.0311 (6)
H7	0.2655	0.4091	0.5294	0.037*
C8	0.18255 (10)	0.4827 (3)	0.6229 (4)	0.0298 (6)
C9	0.17902 (10)	0.5621 (3)	0.4151 (4)	0.0332 (6)
H9	0.2069	0.6033	0.3578	0.040*
C10	0.13425 (11)	0.5790 (3)	0.2961 (4)	0.0365 (6)
H10	0.1315	0.6315	0.1579	0.044*
C11	0.09378 (11)	0.5175 (4)	0.3836 (5)	0.0390 (7)
C12	0.09647 (11)	0.4396 (3)	0.5890 (5)	0.0405 (7)
H12	0.0685	0.3987	0.6455	0.049*
C13	0.14112 (10)	0.4237 (3)	0.7077 (4)	0.0334 (6)
H13	0.1434	0.3727	0.8465	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.0284 (2)	0.0679 (2)	0.0599 (2)	−0.00058 (15)	0.01204 (13)	−0.00234 (15)
Cl1	0.0355 (5)	0.0899 (7)	0.0749 (6)	0.0049 (5)	−0.0157 (4)	0.0006 (5)
O1	0.0349 (12)	0.0649 (13)	0.0343 (10)	0.0008 (10)	0.0085 (8)	−0.0095 (9)
N1	0.0270 (13)	0.0334 (11)	0.0336 (11)	−0.0016 (10)	0.0041 (9)	0.0012 (9)
C1	0.0319 (16)	0.0250 (12)	0.0299 (13)	0.0014 (11)	0.0035 (10)	0.0002 (10)
C2	0.0323 (16)	0.0308 (13)	0.0305 (13)	0.0023 (12)	0.0080 (11)	0.0014 (11)
C3	0.0433 (18)	0.0353 (14)	0.0284 (13)	−0.0017 (13)	−0.0015 (11)	−0.0030 (11)
C4	0.0323 (17)	0.0362 (14)	0.0386 (14)	−0.0030 (12)	−0.0045 (12)	0.0012 (11)
C5	0.0273 (16)	0.0307 (13)	0.0417 (14)	0.0010 (11)	0.0055 (11)	0.0044 (11)
C6	0.0331 (16)	0.0297 (13)	0.0285 (12)	0.0022 (12)	0.0034 (10)	−0.0002 (10)
C7	0.0343 (16)	0.0293 (13)	0.0300 (12)	−0.0008 (11)	0.0043 (11)	−0.0025 (10)
C8	0.0314 (16)	0.0249 (12)	0.0336 (13)	0.0012 (11)	0.0057 (11)	−0.0015 (10)
C9	0.0321 (16)	0.0346 (14)	0.0338 (13)	−0.0017 (12)	0.0083 (11)	0.0022 (11)
C10	0.0381 (18)	0.0351 (14)	0.0358 (14)	0.0041 (12)	0.0014 (12)	0.0011 (11)
C11	0.0291 (17)	0.0362 (14)	0.0502 (16)	0.0038 (13)	−0.0029 (13)	−0.0057 (13)
C12	0.0298 (17)	0.0396 (15)	0.0531 (17)	−0.0042 (13)	0.0095 (13)	−0.0017 (13)
C13	0.0308 (16)	0.0348 (14)	0.0358 (13)	−0.0013 (12)	0.0087 (11)	0.0036 (11)

Br1—C5	1.886 (3)	C5—C6	1.363 (4)
Cl1—C11	1.728 (3)	C6—H6	0.9300
O1—C2	1.341 (3)	C7—H7	0.9300
O1—H1	0.8200	C8—C13	1.377 (4)
N1—C7	1.273 (3)	C8—C9	1.400 (3)
N1—C8	1.405 (3)	C9—C10	1.375 (4)
C1—C6	1.387 (4)	C9—H9	0.9300
C1—C2	1.420 (3)	C10—C11	1.367 (4)
C1—C7	1.434 (4)	C10—H10	0.9300
C2—C3	1.375 (4)	C11—C12	1.384 (4)
C3—C4	1.366 (4)	C12—C13	1.371 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.401 (4)	C13—H13	0.9300
C4—H4	0.9300
C2—O1—H1	109.5	N1—C7—H7	119.2
C7—N1—C8	120.8 (2)	C1—C7—H7	119.2
C6—C1—C2	119.2 (2)	C13—C8—C9	119.8 (3)
C6—C1—C7	119.5 (2)	C13—C8—N1	118.5 (2)
C2—C1—C7	121.1 (2)	C9—C8—N1	121.5 (2)
O1—C2—C3	118.8 (2)	C10—C9—C8	119.8 (3)
O1—C2—C1	121.7 (2)	C10—C9—H9	120.1
C3—C2—C1	119.5 (3)	C8—C9—H9	120.1
C4—C3—C2	120.6 (2)	C11—C10—C9	119.1 (3)
C4—C3—H3	119.7	C11—C10—H10	120.4
C2—C3—H3	119.7	C9—C10—H10	120.4
C3—C4—C5	120.2 (3)	C10—C11—C12	122.0 (3)
C3—C4—H4	119.9	C10—C11—Cl1	118.1 (2)
C5—C4—H4	119.9	C12—C11—Cl1	119.9 (2)
C6—C5—C4	120.2 (3)	C13—C12—C11	118.8 (3)
C6—C5—Br1	119.6 (2)	C13—C12—H12	120.6
C4—C5—Br1	120.2 (2)	C11—C12—H12	120.6
C5—C6—C1	120.3 (2)	C12—C13—C8	120.5 (2)
C5—C6—H6	119.8	C12—C13—H13	119.8
C1—C6—H6	119.8	C8—C13—H13	119.8
N1—C7—C1	121.7 (2)
C6—C1—C2—O1	−179.0 (2)	C6—C1—C7—N1	180.0 (2)
C7—C1—C2—O1	5.5 (4)	C2—C1—C7—N1	−4.6 (4)
C6—C1—C2—C3	1.5 (3)	C7—N1—C8—C13	149.2 (2)
C7—C1—C2—C3	−173.9 (2)	C7—N1—C8—C9	−35.6 (3)
O1—C2—C3—C4	179.9 (2)	C13—C8—C9—C10	−0.6 (4)
C1—C2—C3—C4	−0.7 (4)	N1—C8—C9—C10	−175.7 (2)
C2—C3—C4—C5	−0.2 (4)	C8—C9—C10—C11	0.0 (4)
C3—C4—C5—C6	0.2 (4)	C9—C10—C11—C12	0.3 (4)
C3—C4—C5—Br1	178.26 (19)	C9—C10—C11—Cl1	179.82 (19)
C4—C5—C6—C1	0.7 (4)	C10—C11—C12—C13	0.0 (4)
Br1—C5—C6—C1	−177.37 (17)	Cl1—C11—C12—C13	−179.53 (19)
C2—C1—C6—C5	−1.6 (4)	C11—C12—C13—C8	−0.6 (4)
C7—C1—C6—C5	174.0 (2)	C9—C8—C13—C12	0.9 (4)
C8—N1—C7—C1	169.8 (2)	N1—C8—C13—C12	176.1 (2)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.594 (3)	147
C9—H9···O1i	0.93	2.60	3.459 (4)	154.
C10—H10···Cg1ii	0.93	2.77	3.474 (3)	134
C13—H13···Cg1iii	0.03	2.80	3.501 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.594 (3)	147
C9—H9⋯O1i	0.93	2.60	3.459 (4)	154
C10—H10⋯Cg1ii	0.93	2.77	3.474 (3)	134
C13—H13⋯Cg1iii	0.03	2.80	3.501 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) .