3-Bromo-1-(2,4-dichloro­phen­yl)-2-meth­oxy-3-(4-methoxy­phen­yl)propan-1-one–2-bromo-3-(3-chloro-4-methoxy­phen­yl)-1-(4-chloro­phen­yl)-3-methoxy­propan-1-one (0.91/0.09)

The title co-crystal, 0.91C₁₇H₁₅BrCl₂O₃·0.09C₁₇H₁₅BrCl₂O₃, is a disordered mixture of two isomeric compounds. The ratio of the major and minor components in the co-crystal was obtained by refinement as 0.911 (3):0.089 (3). The dihedral angle between the two aromatic rings is 42.5 (2)°. Crystal packing is stabilized by inter­molecular C—H...O hydrogen-bonding inter­actions which link the mol­ecules into cyclic centrosymmetric R₂²(24) dimers.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.156
• Data-to-parameter ratio = 23.4

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C2     ..  Cl3     ..       3.12 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.53
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C6     ..  Cl3     ..       3.18 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.532
            Tmax scaled      0.532 Tmin scaled      0.305
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          R

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

For a structurally simple group of compounds, chalcones display an impressive array of biological activities, among which antimalarial, antiprotozoal, nitric oxide inhibition and anticancer activities have been reported in the literature (Liu et al., 2003; Nielson et al., 1998; Rajas et al., 2002; Dinkova-Kostova et al., 1998). Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are notable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show NLO properties, with two planar rings connected through a conjugated double bond. The substitution of a bromo group on either of the phenyl rings greatly influences the non-centrosymmetric crystal packing. The bromo group can obviously improve the molecular first-order hyperpolarizabilities and can effectively reduce dipole-dipole interactions between the molecules (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira et al., 2002; Sarojini et al., 2006). Chalcone derivatives usually have a lower melting temperature, which can be a drawback when these crystals are used in optical instruments. Chalcone dibromides usually have higher melting points and are thermally stable. The structures of chalcone dibromides viz., 2,3-dibromo-3-(4-bromo-6-methoxy-2-naphthyl)-1-(4-methoxyphenyl)propan-1-one (Sarojini et al., 2007), 2,3-dibromo-1-(2,4-dichlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)propan-1-one (Yathirajan, Mayekar et al., 2007a), 2,3-dibromo-3-(5-bromo-6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one (Yathirajan, Mayekar et al., 2007b), 2,3-dibromo-1-(3-bromo-2-thienyl)-3-(4-fluorophenyl)propan-1-one (Yathirajan, Vijesh et al., 2007), 2,3-dibromo-3-(4-methoxyphenyl)-1- phenylpropan-1-one (Butcher, Yathirajan, Anilkumar et al., 2006), 2,3-Dibromo-1-(4-methoxyphenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one (Butcher, Yathirajan, Sarojini et al., 2006), 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl] propan-1-one (Butcher, Yathirajan, Mithun et al., 2006), 2,3-dibromo-1,3-diphenylpropan-1-one (Harrison et al., 2005) have been reported. A new chalcone dibromide, was prepared by the bromination of the chalcone, (2E)-1-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one. The title compound, a cocrystal, was obtained, during repeated crystallization in a mixture of ethyl acetate and methanol due to the reaction of 2,3-dibromo-1-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)propan-1-one with methanol. We report here the crystal structure of the title compound.

The mean planes of the two benzene rings are twisted with a dihedral angle of 42.5 (9)° (Fig.1). In the cocrystal the major occupied chlorine atom [Cl1; 0.911 (3)] and minor occupied hydrogen atom [H2; 0.089 (3)] are located on atom C2 of the para-chlorophenyl ring while the minor occupied chlorine atom [Cl3; 0.089 (3)] and major occupied hydrogen atom [H12; 0.911 (3)] are located on atom C12 of the 4-methoxyphenyl ring. The Br1–C8–C9–C10 and C17–O3–C9–C10 torsion angles are 61.6 (3)° and -72.7 (3)°, respectively.

Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding interactions between the 4-methoxyphenyl oxygen atom (O2) of the molecule at (3 - x, 2 - y, 1 - z) and atom H5A of the molecule at (x, y, z), which form cyclic centrosymmetric R²₂(24) dimers (Fig. 2).

Related literature

For related structures, see: Harrison et al. (2005); Butcher, Yathirajan, Anilkumar et al. (2006); Butcher, Yathirajan, Sarojini et al. (2006); Butcher, Yathirajan, Mithun et al. (2006); Sarojini et al. (2007); Yathirajan, Mayekar et al. (2007a); Yathirajan, Mayekar et al. (2007b); Yathirajan, Vijesh et al. (2007). For related literature, see: Tam et al. (1989); Goto et al. (1991); Dinkova-Kostova et al. (1998); Nielson et al. (1998); Uchida et al. (1998); Liu et al. (2003); Indira et al. (2002); Rajas et al. (2002); Sarojini et al. (2006).

S2. Experimental

(2E)-1-(2,4-Dichlorophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one (3.07 g, 0.01 mole) was treated with bromine in acetic acid (30%) until the orange colour of the solution persisted (Fig.3). After stirring for half an hour, the contents were poured on to crushed ice. The resulting solid mass was collected by filtration. The compound was dried and recrystallized from ethanol. Crystals suitable for X-ray structure determination were obtained from a 1:1 mixture of ethyl acetate and methanol by slow evaporation (yield 70%; m.p. 365–369 K). Analysis found: C 44.74, H 3.58; C₃₄H₃₀Br₂Cl₄O₆ requires: C 48.83, H 3.62.

S3. Refinement

H atoms were placed in calculated positions and were refined using a riding model, with C—H = 0.93–0.98 Å, and U_iso(H) = 1.19–1.56U_eq(C). The ratio of the major [Cl1 and H12] and minor [Cl3 and H2] components in the cocrystal was obtained by refinement as 0.911 (3):0.089 (3). Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (46%).

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids. Both major [Cl1 and H12; 0.911 (3)] and minor [Cl3 and H2; 0.089 (3)] components of the cocrystal are displayed.
	Fig. 2. Packing diagram of the title compound, viewed down the a axis. Dashed lines indicate intermolecular C—H···O hydrogen bonds. Only the major component (Cl1 and H12) of the cocrystal is displayed.
	Fig. 3. Synthesis scheme for the title compound.

3-Bromo-1-(2,4-dichlorophenyl)-2-methoxy-3-(4-methoxyphenyl)propan-1-one–2-bromo-3-(3-chloro-4-methoxyphenyl)-1-(4-chlorophenyl)-3-methoxypropan-1-one (0.91/0.09)

Crystal data

0.91C17H15BrCl2O3·0.09C17H15BrCl2O3	Z = 2
Mr = 418.09	F(000) = 420
Triclinic, P1	Dx = 1.565 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8013 (12) Å	Cell parameters from 3589 reflections
b = 11.190 (2) Å	θ = 4.7–32.4°
c = 11.438 (3) Å	µ = 2.63 mm^−1
α = 113.88 (2)°	T = 296 K
β = 98.649 (16)°	Block, pale yellow
γ = 95.991 (14)°	0.47 × 0.43 × 0.24 mm
V = 887.4 (4) Å^3

Data collection

Oxford Diffraction Gemini R CCD diffractometer	5156 independent reflections
Radiation source: fine-focus sealed tube	2377 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.5°, θmin = 4.7°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −15→16
Tmin = 0.574, Tmax = 1.000	l = −16→17
10321 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0715P)^2] where P = (Fo^2 + 2Fc^2)/3
5156 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.82726 (6)	0.94242 (4)	0.28992 (5)	0.0906 (2)
Cl1	0.51820 (12)	0.64546 (13)	0.37858 (10)	0.0805 (4)	0.911 (3)
Cl2	0.93309 (16)	0.61933 (11)	0.78055 (9)	0.0795 (3)
Cl3	1.5542 (11)	1.1758 (9)	0.4443 (12)	0.070 (4)	0.089 (3)
O1	0.7642 (3)	0.6203 (3)	0.1876 (2)	0.0708 (7)
O2	1.5216 (3)	1.2295 (3)	0.2055 (3)	0.0773 (7)
O3	1.1774 (3)	0.6884 (2)	0.2033 (2)	0.0563 (6)
C1	0.8768 (4)	0.6819 (3)	0.4134 (3)	0.0482 (7)
C2	0.7306 (4)	0.6530 (4)	0.4590 (3)	0.0568 (8)
H2	0.6188	0.6455	0.4120	0.068*	0.089 (3)
C3	0.7463 (5)	0.6348 (3)	0.5725 (3)	0.0605 (8)
H3	0.6471	0.6162	0.6025	0.073*
C4	0.9128 (5)	0.6449 (3)	0.6396 (3)	0.0533 (7)
C5	1.0618 (5)	0.6736 (3)	0.5984 (3)	0.0596 (8)
H5	1.1734	0.6803	0.6453	0.072*
C6	1.0414 (4)	0.6920 (3)	0.4858 (3)	0.0555 (8)
H6	1.1413	0.7120	0.4571	0.067*
C7	0.8632 (4)	0.6976 (3)	0.2893 (3)	0.0528 (7)
C8	0.9821 (4)	0.8176 (3)	0.2949 (3)	0.0521 (7)
H8	1.0686	0.8582	0.3782	0.063*
C9	1.0791 (4)	0.7814 (3)	0.1826 (3)	0.0474 (7)
H9	0.9942	0.7374	0.0987	0.057*
C10	1.1983 (4)	0.9004 (3)	0.1866 (3)	0.0508 (7)
C11	1.3367 (5)	0.9743 (4)	0.2907 (3)	0.0606 (9)
H11	1.3590	0.9505	0.3598	0.073*
C12	1.4431 (5)	1.0832 (4)	0.2943 (4)	0.0651 (9)
H12	1.5350	1.1326	0.3659	0.078*	0.911 (3)
C13	1.4126 (4)	1.1185 (3)	0.1917 (3)	0.0557 (8)
C14	1.2783 (5)	1.0437 (4)	0.0851 (4)	0.0631 (9)
H14	1.2590	1.0654	0.0144	0.076*
C15	1.1711 (4)	0.9348 (3)	0.0838 (3)	0.0546 (8)
H15	1.0797	0.8848	0.0120	0.065*
C16	1.4996 (6)	1.2684 (5)	0.1019 (5)	0.0880 (13)
H16A	1.5773	1.3512	0.1274	0.132*
H16B	1.3798	1.2789	0.0818	0.132*
H16C	1.5270	1.2015	0.0260	0.132*
C17	1.2483 (6)	0.6162 (4)	0.0951 (3)	0.0718 (10)
H17A	1.2922	0.5437	0.1065	0.108*
H17B	1.3430	0.6735	0.0884	0.108*
H17C	1.1581	0.5820	0.0168	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1155 (4)	0.0796 (3)	0.1043 (4)	0.0536 (3)	0.0558 (3)	0.0469 (3)
Cl1	0.0448 (5)	0.1334 (11)	0.0698 (7)	0.0109 (6)	0.0141 (4)	0.0504 (7)
Cl2	0.1141 (8)	0.0807 (7)	0.0548 (5)	0.0195 (6)	0.0207 (5)	0.0388 (5)
Cl3	0.038 (5)	0.041 (5)	0.107 (9)	−0.013 (4)	−0.009 (5)	0.022 (5)
O1	0.0804 (17)	0.0758 (17)	0.0433 (13)	−0.0065 (13)	0.0120 (12)	0.0181 (12)
O2	0.0675 (16)	0.0766 (18)	0.102 (2)	−0.0017 (13)	0.0239 (14)	0.0537 (16)
O3	0.0771 (15)	0.0559 (13)	0.0543 (13)	0.0260 (11)	0.0272 (11)	0.0340 (11)
C1	0.0504 (17)	0.0484 (17)	0.0520 (17)	0.0136 (13)	0.0217 (14)	0.0229 (14)
C2	0.0487 (17)	0.070 (2)	0.0563 (19)	0.0089 (15)	0.0155 (14)	0.0304 (17)
C3	0.066 (2)	0.065 (2)	0.062 (2)	0.0114 (17)	0.0291 (17)	0.0328 (17)
C4	0.066 (2)	0.0515 (18)	0.0498 (17)	0.0136 (15)	0.0212 (15)	0.0252 (14)
C5	0.061 (2)	0.060 (2)	0.068 (2)	0.0163 (16)	0.0141 (16)	0.0358 (18)
C6	0.0552 (19)	0.0548 (18)	0.065 (2)	0.0116 (15)	0.0243 (16)	0.0302 (16)
C7	0.0585 (19)	0.0526 (18)	0.0530 (18)	0.0177 (15)	0.0235 (15)	0.0223 (15)
C8	0.066 (2)	0.0511 (18)	0.0401 (15)	0.0113 (15)	0.0147 (14)	0.0185 (14)
C9	0.0609 (18)	0.0501 (17)	0.0349 (15)	0.0118 (15)	0.0129 (13)	0.0206 (13)
C10	0.0539 (18)	0.0575 (19)	0.0533 (18)	0.0174 (15)	0.0183 (15)	0.0318 (16)
C11	0.070 (2)	0.066 (2)	0.0474 (18)	0.0082 (18)	0.0003 (17)	0.0309 (17)
C12	0.066 (2)	0.065 (2)	0.065 (2)	0.0034 (18)	0.0036 (18)	0.0328 (18)
C13	0.0523 (18)	0.0565 (19)	0.065 (2)	0.0113 (16)	0.0214 (17)	0.0291 (17)
C14	0.070 (2)	0.076 (2)	0.069 (2)	0.021 (2)	0.0254 (19)	0.051 (2)
C15	0.064 (2)	0.058 (2)	0.0446 (17)	0.0087 (16)	0.0082 (14)	0.0258 (15)
C16	0.102 (3)	0.084 (3)	0.103 (3)	0.013 (2)	0.047 (3)	0.058 (3)
C17	0.100 (3)	0.068 (2)	0.059 (2)	0.035 (2)	0.036 (2)	0.0279 (18)

Geometric parameters (Å, º)

Br1—C8	1.952 (3)	C8—C9	1.523 (4)
Cl1—C2	1.746 (3)	C8—H8	0.98
Cl2—C4	1.736 (3)	C9—C10	1.523 (4)
Cl3—C12	1.641 (11)	C9—H9	0.98
O1—C7	1.213 (4)	C10—C15	1.372 (4)
O2—C13	1.368 (4)	C10—C11	1.377 (5)
O2—C16	1.412 (5)	C11—C12	1.383 (5)
O3—C17	1.407 (4)	C11—H11	0.93
O3—C9	1.427 (4)	C12—C13	1.379 (5)
C1—C2	1.383 (4)	C12—H12	0.93
C1—C6	1.386 (4)	C13—C14	1.375 (5)
C1—C7	1.490 (4)	C14—C15	1.398 (5)
C2—C3	1.383 (5)	C14—H14	0.93
C2—H2	0.93	C15—H15	0.93
C3—C4	1.374 (5)	C16—H16A	0.96
C3—H3	0.93	C16—H16B	0.96
C4—C5	1.374 (5)	C16—H16C	0.96
C5—C6	1.373 (5)	C17—H17A	0.96
C5—H5	0.93	C17—H17B	0.96
C6—H6	0.93	C17—H17C	0.96
C7—C8	1.523 (5)
C13—O2—C16	118.3 (3)	C10—C9—H9	110.0
C17—O3—C9	112.8 (2)	C8—C9—H9	110.0
C2—C1—C6	117.6 (3)	C15—C10—C11	118.4 (3)
C2—C1—C7	122.8 (3)	C15—C10—C9	120.1 (3)
C6—C1—C7	119.6 (3)	C11—C10—C9	121.5 (3)
C1—C2—C3	121.8 (3)	C10—C11—C12	121.2 (3)
C1—C2—Cl1	120.9 (2)	C10—C11—H11	119.4
C3—C2—Cl1	117.2 (2)	C12—C11—H11	119.4
C1—C2—H2	119.1	C13—C12—C11	119.9 (3)
C3—C2—H2	119.1	C13—C12—Cl3	127.8 (5)
C4—C3—C2	118.1 (3)	C11—C12—Cl3	109.9 (5)
C4—C3—H3	121.0	C13—C12—H12	120.0
C2—C3—H3	121.0	C11—C12—H12	120.0
C3—C4—C5	122.2 (3)	O2—C13—C14	124.5 (3)
C3—C4—Cl2	118.3 (2)	O2—C13—C12	115.7 (3)
C5—C4—Cl2	119.5 (3)	C14—C13—C12	119.8 (3)
C6—C5—C4	118.1 (3)	C13—C14—C15	119.4 (3)
C6—C5—H5	120.9	C13—C14—H14	120.3
C4—C5—H5	120.9	C15—C14—H14	120.3
C5—C6—C1	122.2 (3)	C10—C15—C14	121.2 (3)
C5—C6—H6	118.9	C10—C15—H15	119.4
C1—C6—H6	118.9	C14—C15—H15	119.4
O1—C7—C1	123.1 (3)	O2—C16—H16A	109.5
O1—C7—C8	120.5 (3)	O2—C16—H16B	109.5
C1—C7—C8	116.4 (3)	H16A—C16—H16B	109.5
C7—C8—C9	112.5 (3)	O2—C16—H16C	109.5
C7—C8—Br1	105.6 (2)	H16A—C16—H16C	109.5
C9—C8—Br1	111.3 (2)	H16B—C16—H16C	109.5
C7—C8—H8	109.1	O3—C17—H17A	109.5
C9—C8—H8	109.1	O3—C17—H17B	109.5
Br1—C8—H8	109.1	H17A—C17—H17B	109.5
O3—C9—C10	112.0 (3)	O3—C17—H17C	109.5
O3—C9—C8	101.5 (2)	H17A—C17—H17C	109.5
C10—C9—C8	113.2 (2)	H17B—C17—H17C	109.5
O3—C9—H9	110.0
C6—C1—C2—C3	0.1 (5)	C7—C8—C9—O3	−60.0 (3)
C7—C1—C2—C3	178.0 (3)	Br1—C8—C9—O3	−178.24 (19)
C6—C1—C2—Cl1	177.1 (3)	C7—C8—C9—C10	179.8 (2)
C7—C1—C2—Cl1	−5.0 (5)	Br1—C8—C9—C10	61.6 (3)
C1—C2—C3—C4	−0.6 (5)	O3—C9—C10—C15	125.6 (3)
Cl1—C2—C3—C4	−177.8 (3)	C8—C9—C10—C15	−120.4 (3)
C2—C3—C4—C5	0.7 (5)	O3—C9—C10—C11	−53.1 (4)
C2—C3—C4—Cl2	−178.9 (3)	C8—C9—C10—C11	60.8 (4)
C3—C4—C5—C6	−0.2 (5)	C15—C10—C11—C12	2.0 (5)
Cl2—C4—C5—C6	179.4 (3)	C9—C10—C11—C12	−179.2 (3)
C4—C5—C6—C1	−0.4 (5)	C10—C11—C12—C13	−0.8 (6)
C2—C1—C6—C5	0.4 (5)	C10—C11—C12—Cl3	162.9 (5)
C7—C1—C6—C5	−177.6 (3)	C16—O2—C13—C14	−2.2 (5)
C2—C1—C7—O1	−46.6 (5)	C16—O2—C13—C12	178.3 (4)
C6—C1—C7—O1	131.3 (3)	C11—C12—C13—O2	178.4 (3)
C2—C1—C7—C8	133.7 (3)	Cl3—C12—C13—O2	17.8 (7)
C6—C1—C7—C8	−48.4 (4)	C11—C12—C13—C14	−1.1 (5)
O1—C7—C8—C9	−47.3 (4)	Cl3—C12—C13—C14	−161.6 (6)
C1—C7—C8—C9	132.4 (3)	O2—C13—C14—C15	−177.7 (3)
O1—C7—C8—Br1	74.2 (3)	C12—C13—C14—C15	1.8 (5)
C1—C7—C8—Br1	−106.1 (2)	C11—C10—C15—C14	−1.3 (5)
C17—O3—C9—C10	−72.7 (3)	C9—C10—C15—C14	179.9 (3)
C17—O3—C9—C8	166.3 (3)	C13—C14—C15—C10	−0.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2^i	0.93	2.54	3.446 (4)	163

Symmetry code: (i) −x+3, −y+2, −z+1.