2,3-Dibromo-3-(4-chloro-phen-yl)-1-(2-hy-droxy-phen-yl)propan-1-one.

In the title mol-ecule, C(15)H(11)Br(2)ClO(2), an S(6) ring motif is formed via an intra-molecular O-H⋯O hydrogen bond. The dihedral angle formed between the chloro- and hy-droxy-substituted benzene rings is 34.10 (15)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

For applications of chalcone compounds, see: Liu et al. (2003 ▶); Nielson et al. (1998 ▶); Rajas et al. (2002 ▶); Dinkova-Kostova et al. (1998 ▶); Goto et al. (1991 ▶); Uchida et al. (1998) ▶; Tam et al. (1989 ▶); Indira et al. (2002 ▶); Sarojini et al. (2006 ▶). For related structures, see: Butcher, Yathirajan, Anilkumar et al. (2006 ▶); Butcher, Yathirajan, Sarojini et al. (2006 ▶); Harrison et al. (2005 ▶); Yathirajan, Mayekar et al. (2007 ▶); Yathirajan, Vijesh et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11Br2ClO2

M = 418.51

Monoclinic,

a = 29.075 (3) Å

b = 9.2358 (10) Å

c = 11.4374 (12) Å

β = 103.290 (2)°

V = 2989.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 5.60 mm−1

T = 297 K

0.39 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.218, T max = 0.379

16663 measured reflections

5375 independent reflections

3337 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.122

S = 1.04

5375 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811036798/lh5331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036798/lh5331Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036798/lh5331Isup3.cml

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

C15H11Br2ClO2	F(000) = 1632
Mr = 418.51	Dx = 1.860 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4431 reflections
a = 29.075 (3) Å	θ = 2.9–29.1°
b = 9.2358 (10) Å	µ = 5.60 mm−1
c = 11.4374 (12) Å	T = 297 K
β = 103.290 (2)°	Block, yellow
V = 2989.0 (6) Å3	0.39 × 0.36 × 0.22 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	5375 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 32.6°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −43→39
Tmin = 0.218, Tmax = 0.379	k = −13→13
16663 measured reflections	l = −13→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3
5375 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.47 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
Cl1	0.04064 (3)	0.29705 (9)	0.14615 (9)	0.0677 (2)
Br1	0.191164 (10)	0.81997 (3)	0.36623 (3)	0.05335 (11)
Br2	0.046011 (11)	0.98145 (4)	0.41259 (3)	0.06342 (12)
O1	0.19186 (10)	1.3218 (2)	0.57890 (18)	0.0611 (6)
H1O1	0.1812	1.2476	0.5965	0.092*
O2	0.15388 (9)	1.0666 (2)	0.55101 (17)	0.0574 (5)
C1	0.06311 (12)	0.7159 (3)	0.2247 (3)	0.0545 (7)
H1A	0.0577	0.8040	0.1845	0.065*
C2	0.04955 (11)	0.5874 (3)	0.1622 (3)	0.0553 (7)
H2A	0.0355	0.5891	0.0805	0.066*
C3	0.05732 (10)	0.4580 (3)	0.2236 (3)	0.0480 (6)
C4	0.07828 (10)	0.4529 (3)	0.3435 (3)	0.0480 (6)
H4A	0.0835	0.3645	0.3832	0.058*
C5	0.09170 (10)	0.5816 (3)	0.4055 (3)	0.0469 (6)
H5A	0.1056	0.5791	0.4873	0.056*
C6	0.08443 (9)	0.7138 (3)	0.3460 (2)	0.0422 (5)
C7	0.10038 (10)	0.8494 (3)	0.4158 (3)	0.0444 (6)
H7A	0.1148	0.8237	0.4993	0.053*
C8	0.13502 (9)	0.9403 (3)	0.3658 (2)	0.0417 (5)
H8A	0.1204	0.9719	0.2839	0.050*
C9	0.15471 (10)	1.0703 (3)	0.4438 (2)	0.0421 (5)
C10	0.17415 (9)	1.1927 (2)	0.3898 (2)	0.0376 (5)
C11	0.17591 (11)	1.1946 (3)	0.2682 (2)	0.0481 (6)
H11A	0.1641	1.1165	0.2191	0.058*
C12	0.19496 (12)	1.3112 (3)	0.2210 (3)	0.0550 (7)
H12A	0.1959	1.3116	0.1403	0.066*
C13	0.21269 (11)	1.4279 (3)	0.2937 (3)	0.0545 (7)
H13A	0.2253	1.5066	0.2611	0.065*
C14	0.21187 (10)	1.4284 (3)	0.4115 (3)	0.0516 (7)
H14A	0.2242	1.5071	0.4593	0.062*
C15	0.19263 (10)	1.3118 (3)	0.4619 (2)	0.0428 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0831 (6)	0.0495 (4)	0.0769 (5)	−0.0197 (4)	0.0312 (4)	−0.0233 (4)
Br1	0.05194 (17)	0.04197 (15)	0.0691 (2)	0.00312 (11)	0.02003 (14)	−0.00637 (12)
Br2	0.05503 (19)	0.05123 (18)	0.0874 (3)	0.00816 (13)	0.02336 (16)	−0.00960 (15)
O1	0.0985 (17)	0.0433 (10)	0.0428 (11)	−0.0141 (10)	0.0186 (11)	−0.0098 (8)
O2	0.0898 (16)	0.0454 (10)	0.0388 (10)	−0.0148 (10)	0.0190 (10)	−0.0032 (8)
C1	0.0681 (18)	0.0395 (13)	0.0523 (17)	−0.0053 (13)	0.0062 (14)	0.0032 (12)
C2	0.0684 (18)	0.0489 (15)	0.0468 (16)	−0.0067 (13)	0.0092 (13)	−0.0065 (12)
C3	0.0495 (14)	0.0417 (13)	0.0570 (17)	−0.0074 (11)	0.0206 (12)	−0.0129 (12)
C4	0.0531 (15)	0.0315 (11)	0.0615 (18)	−0.0039 (10)	0.0174 (13)	0.0012 (11)
C5	0.0507 (14)	0.0390 (12)	0.0507 (15)	−0.0021 (11)	0.0111 (11)	0.0028 (11)
C6	0.0475 (13)	0.0345 (11)	0.0454 (14)	−0.0047 (10)	0.0121 (11)	−0.0022 (10)
C7	0.0536 (14)	0.0328 (11)	0.0476 (14)	−0.0016 (10)	0.0132 (11)	0.0000 (10)
C8	0.0507 (13)	0.0330 (11)	0.0418 (13)	−0.0013 (10)	0.0118 (11)	−0.0011 (9)
C9	0.0561 (14)	0.0320 (10)	0.0365 (13)	−0.0020 (10)	0.0076 (11)	−0.0007 (9)
C10	0.0464 (12)	0.0305 (10)	0.0354 (12)	−0.0008 (9)	0.0083 (10)	−0.0001 (9)
C11	0.0611 (16)	0.0437 (13)	0.0388 (14)	−0.0058 (12)	0.0100 (12)	−0.0031 (10)
C12	0.0691 (18)	0.0549 (16)	0.0433 (15)	−0.0072 (14)	0.0178 (13)	0.0084 (12)
C13	0.0631 (17)	0.0412 (13)	0.0581 (18)	−0.0073 (12)	0.0119 (14)	0.0105 (12)
C14	0.0586 (16)	0.0306 (11)	0.0623 (18)	−0.0067 (11)	0.0077 (13)	−0.0024 (11)
C15	0.0513 (14)	0.0319 (11)	0.0432 (14)	0.0005 (10)	0.0065 (11)	−0.0002 (9)

Cl1—C3	1.741 (3)	C6—C7	1.501 (3)
Br1—C8	1.974 (3)	C7—C8	1.520 (4)
Br2—C7	1.990 (3)	C7—H7A	0.9800
O1—C15	1.347 (3)	C8—C9	1.527 (3)
O1—H1O1	0.7971	C8—H8A	0.9800
O2—C9	1.232 (3)	C9—C10	1.463 (3)
C1—C6	1.383 (4)	C10—C11	1.403 (4)
C1—C2	1.395 (4)	C10—C15	1.406 (3)
C1—H1A	0.9300	C11—C12	1.376 (4)
C2—C3	1.378 (4)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.386 (4)
C3—C4	1.367 (4)	C12—H12A	0.9300
C4—C5	1.393 (4)	C13—C14	1.353 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.390 (4)	C14—C15	1.398 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C15—O1—H1O1	106.8	C7—C8—Br1	107.91 (17)
C6—C1—C2	120.7 (3)	C9—C8—Br1	104.04 (17)
C6—C1—H1A	119.6	C7—C8—H8A	110.2
C2—C1—H1A	119.6	C9—C8—H8A	110.2
C3—C2—C1	118.9 (3)	Br1—C8—H8A	110.2
C3—C2—H2A	120.6	O2—C9—C10	122.7 (2)
C1—C2—H2A	120.6	O2—C9—C8	118.0 (2)
C4—C3—C2	121.6 (2)	C10—C9—C8	119.3 (2)
C4—C3—Cl1	119.2 (2)	C11—C10—C15	118.4 (2)
C2—C3—Cl1	119.2 (2)	C11—C10—C9	122.3 (2)
C3—C4—C5	119.3 (3)	C15—C10—C9	119.3 (2)
C3—C4—H4A	120.3	C12—C11—C10	120.6 (3)
C5—C4—H4A	120.3	C12—C11—H11A	119.7
C6—C5—C4	120.4 (3)	C10—C11—H11A	119.7
C6—C5—H5A	119.8	C11—C12—C13	120.0 (3)
C4—C5—H5A	119.8	C11—C12—H12A	120.0
C1—C6—C5	119.1 (2)	C13—C12—H12A	120.0
C1—C6—C7	122.3 (2)	C14—C13—C12	120.7 (3)
C5—C6—C7	118.6 (2)	C14—C13—H13A	119.6
C6—C7—C8	114.2 (2)	C12—C13—H13A	119.6
C6—C7—Br2	110.76 (19)	C13—C14—C15	120.5 (3)
C8—C7—Br2	104.30 (16)	C13—C14—H14A	119.7
C6—C7—H7A	109.1	C15—C14—H14A	119.7
C8—C7—H7A	109.1	O1—C15—C14	117.2 (2)
Br2—C7—H7A	109.1	O1—C15—C10	123.0 (2)
C7—C8—C9	113.9 (2)	C14—C15—C10	119.7 (3)
C6—C1—C2—C3	0.7 (5)	Br1—C8—C9—O2	−94.9 (3)
C1—C2—C3—C4	−0.6 (5)	C7—C8—C9—C10	−158.4 (2)
C1—C2—C3—Cl1	−179.8 (3)	Br1—C8—C9—C10	84.4 (2)
C2—C3—C4—C5	0.7 (4)	O2—C9—C10—C11	178.6 (3)
Cl1—C3—C4—C5	179.9 (2)	C8—C9—C10—C11	−0.7 (4)
C3—C4—C5—C6	−0.8 (4)	O2—C9—C10—C15	−0.2 (4)
C2—C1—C6—C5	−0.8 (5)	C8—C9—C10—C15	−179.5 (2)
C2—C1—C6—C7	178.8 (3)	C15—C10—C11—C12	−0.5 (4)
C4—C5—C6—C1	0.9 (4)	C9—C10—C11—C12	−179.3 (3)
C4—C5—C6—C7	−178.7 (3)	C10—C11—C12—C13	0.1 (5)
C1—C6—C7—C8	−56.8 (4)	C11—C12—C13—C14	0.5 (5)
C5—C6—C7—C8	122.8 (3)	C12—C13—C14—C15	−0.7 (5)
C1—C6—C7—Br2	60.6 (3)	C13—C14—C15—O1	−178.2 (3)
C5—C6—C7—Br2	−119.8 (2)	C13—C14—C15—C10	0.3 (4)
C6—C7—C8—C9	−174.5 (2)	C11—C10—C15—O1	178.7 (3)
Br2—C7—C8—C9	64.5 (2)	C9—C10—C15—O1	−2.5 (4)
C6—C7—C8—Br1	−59.5 (3)	C11—C10—C15—C14	0.3 (4)
Br2—C7—C8—Br1	179.45 (11)	C9—C10—C15—C14	179.2 (3)
C7—C8—C9—O2	22.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.80	1.87	2.591 (3)	150
C11—H11A···O2i	0.93	2.53	3.416 (4)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.80	1.87	2.591 (3)	150
C11—H11A⋯O2i	0.93	2.53	3.416 (4)	160

Symmetry code: (i) .