2,3-Dibromo-3-(4-bromo-6-meth­oxy-2-naphth­yl)-1-(4-methoxy­phen­yl)propan-1-one

Sarojini, B.K.; Narayana, B.; Yathirajan, H.S.; Mayekar, A.N.; Bolte, M.

doi:10.1107/S1600536807038883

2,3-Dibromo-3-(4-bromo-6-methoxy-2-naphthyl)-1-(4-methoxyphenyl)propan-1-one

B. K. Sarojini, B. Narayana, H. S. Yathirajan, A. N. Mayekar and M. Bolte

In the title compound, C₂₁H₁₇Br₃O₃, the two aromatic residues are almost coplanar with one another [dihedral angle = 9.92 (6)°]. The two Br atoms at the Csp³ atoms are in a trans conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038883/hb2503sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038883/hb2503Isup2.hkl Contains datablock I

CCDC reference: 660248

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.010 Å
R factor = 0.069
wR factor = 0.174
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Br1    -   C1      ..       7.87 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      2.682
            Test value =      2.625
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.03
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       2.68 e/A   
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Br2    -   C2      ..       5.19 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.93
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.52 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Comment top

As part of our ongoing studies of chalcones (Yathirajan et al., 2007), the title compound, (I), was serendipitiously prepapred by the bromination of ((2E)-3-(6-methoxy-2-naphthyl)-1-(4-methoxyphenyl)prop-2-en-1-one. As well the intended bromination as the central double bond, an excess of bromine also brominated of one of the naphthalene C atoms.

In the structure of (I) (Fig. 1) the two aromatic residues are almost coplanar to each other [dihedral angle 9.92 (6)°]. The two Br atoms at the sp³ C atoms are trans with respect to each other [Br1—C1—C2—Br2 = 177.6 (3)°].

Related literature top

For background, see: Yathirajan et al. (2007).

Experimental top

(2E)-3-(6-Methoxy-2-naphthyl)-1-(4-methoxyphenyl)prop-2-en-1-one (3.18 g, 0.01 mol) was treated with bromine in acetic acid (30%) until the orange colour of the solution persisted. 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. Colourless plates of (I) were obtained from acetone by slow evaporation (yield 78%; m.p.: 453–455 K). Analysis for C₂₁H₁₇Br₃O₃: found (calculated): C: 45.20 (45.28); H: 3.01% (3.08%).

Structure description top

For background, see: Yathirajan et al. (2007).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).

2,3-Dibromo-3-(4-bromo-6-methoxy-2-naphthyl)-1-(4-methoxyphenyl)propan-1-one top

Crystal data top

C₂₁H₁₇Br₃O₃	F(000) = 1088
M_r = 557.08	D_x = 1.842 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24485 reflections
a = 7.4989 (5) Å	θ = 3.5–24.9°
b = 20.3640 (16) Å	µ = 6.04 mm⁻¹
c = 13.6083 (8) Å	T = 173 K
β = 104.844 (5)°	Plate, colourless
V = 2008.7 (2) Å³	0.32 × 0.29 × 0.12 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	3531 independent reflections
Radiation source: fine-focus sealed tube	3048 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 25.0°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→8
T_min = 0.168, T_max = 0.471	k = −24→24
23062 measured reflections	l = −15→16

Refinement top

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0826P)² + 13.7141P] where P = (F_o² + 2F_c²)/3
3531 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 2.68 e Å⁻³
0 restraints	Δρ_min = −2.00 e Å⁻³

Crystal data top

C₂₁H₁₇Br₃O₃	V = 2008.7 (2) Å³
M_r = 557.08	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4989 (5) Å	µ = 6.04 mm⁻¹
b = 20.3640 (16) Å	T = 173 K
c = 13.6083 (8) Å	0.32 × 0.29 × 0.12 mm
β = 104.844 (5)°

Data collection top

Stoe IPDS II two-circle diffractometer	3531 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3048 reflections with I > 2σ(I)
T_min = 0.168, T_max = 0.471	R_int = 0.064
23062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0826P)² + 13.7141P] where P = (F_o² + 2F_c²)/3
3531 reflections	Δρ_max = 2.68 e Å⁻³
246 parameters	Δρ_min = −2.00 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.04941 (12)	0.47310 (4)	0.87074 (7)	0.0472 (3)
Br2	0.58929 (13)	0.42001 (5)	0.78473 (10)	0.0648 (4)
Br3	0.09601 (11)	0.63997 (3)	0.36243 (6)	0.0349 (2)
O1	0.4516 (10)	0.4089 (3)	1.0061 (5)	0.0581 (19)
O2	0.3380 (9)	0.1035 (2)	0.9474 (5)	0.0475 (15)
O3	0.0774 (8)	0.7748 (2)	0.4366 (4)	0.0349 (12)
C1	0.2970 (13)	0.4863 (4)	0.8360 (6)	0.044 (2)
H1	0.3871	0.5068	0.8952	0.053*
C2	0.3487 (11)	0.4177 (4)	0.8256 (6)	0.0387 (19)
H2	0.2513	0.3947	0.7728	0.046*
C3	0.3941 (11)	0.3787 (3)	0.9265 (6)	0.0359 (18)
C4	0.3719 (10)	0.3062 (3)	0.9250 (6)	0.0322 (16)
C5	0.3182 (11)	0.2688 (4)	0.8372 (6)	0.0374 (18)
H5	0.2901	0.2902	0.7731	0.045*
C6	0.3046 (11)	0.2016 (4)	0.8407 (7)	0.0397 (19)
H6	0.2688	0.1770	0.7794	0.048*
C7	0.3434 (10)	0.1697 (3)	0.9338 (7)	0.0344 (17)
C8	0.3954 (11)	0.2069 (4)	1.0235 (7)	0.0382 (18)
H8	0.4207	0.1856	1.0877	0.046*
C9	0.4098 (11)	0.2734 (4)	1.0188 (6)	0.0352 (17)
H9	0.4461	0.2980	1.0800	0.042*
C10	0.2919 (15)	0.0637 (4)	0.8566 (8)	0.054 (3)
H10A	0.1671	0.0746	0.8166	0.081*
H10B	0.2969	0.0171	0.8755	0.081*
H10C	0.3802	0.0722	0.8161	0.081*
C11	0.2671 (11)	0.5312 (3)	0.7452 (6)	0.0336 (17)
C12	0.2265 (11)	0.5082 (3)	0.6424 (6)	0.0323 (16)
H12	0.2283	0.4624	0.6291	0.039*
C13	0.1856 (10)	0.5515 (3)	0.5637 (6)	0.0301 (15)
H13	0.1582	0.5351	0.4961	0.036*
C14	0.1824 (9)	0.6204 (3)	0.5791 (5)	0.0250 (14)
C15	0.1381 (9)	0.6679 (3)	0.4997 (5)	0.0248 (14)
C16	0.1246 (9)	0.7336 (3)	0.5192 (5)	0.0266 (14)
C17	0.1612 (10)	0.7555 (3)	0.6202 (6)	0.0307 (16)
H17	0.1525	0.8009	0.6339	0.037*
C18	0.2090 (11)	0.7121 (3)	0.6987 (6)	0.0319 (16)
H18	0.2342	0.7280	0.7666	0.038*
C19	0.2223 (10)	0.6436 (3)	0.6815 (5)	0.0266 (14)
C20	0.2677 (10)	0.5978 (3)	0.7623 (5)	0.0290 (15)
H20	0.2996	0.6135	0.8303	0.035*
C21	0.0410 (12)	0.8423 (3)	0.4539 (7)	0.0372 (18)
H21A	−0.0518	0.8449	0.4930	0.056*
H21B	−0.0051	0.8646	0.3886	0.056*
H21C	0.1551	0.8635	0.4921	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0581 (5)	0.0379 (5)	0.0542 (6)	0.0082 (4)	0.0299 (4)	0.0133 (4)
Br2	0.0492 (5)	0.0560 (6)	0.0967 (9)	0.0227 (4)	0.0325 (5)	0.0411 (6)
Br3	0.0562 (5)	0.0206 (4)	0.0267 (4)	−0.0027 (3)	0.0083 (3)	−0.0007 (3)
O1	0.096 (5)	0.022 (3)	0.038 (3)	−0.014 (3)	−0.017 (3)	0.006 (3)
O2	0.068 (4)	0.011 (2)	0.067 (4)	−0.001 (2)	0.024 (3)	0.002 (3)
O3	0.060 (3)	0.012 (2)	0.032 (3)	0.005 (2)	0.010 (2)	0.005 (2)
C1	0.076 (6)	0.017 (4)	0.033 (4)	−0.009 (4)	0.001 (4)	0.004 (3)
C2	0.048 (4)	0.019 (4)	0.039 (5)	−0.001 (3)	−0.006 (3)	0.007 (3)
C3	0.046 (4)	0.017 (3)	0.036 (4)	−0.003 (3)	−0.004 (3)	0.003 (3)
C4	0.034 (4)	0.019 (4)	0.040 (4)	−0.003 (3)	0.004 (3)	0.008 (3)
C5	0.049 (4)	0.019 (4)	0.040 (4)	−0.002 (3)	0.004 (3)	0.007 (3)
C6	0.049 (5)	0.018 (4)	0.049 (5)	−0.006 (3)	0.008 (4)	−0.004 (3)
C7	0.038 (4)	0.016 (3)	0.052 (5)	0.000 (3)	0.016 (3)	0.003 (3)
C8	0.051 (5)	0.021 (4)	0.042 (5)	0.002 (3)	0.011 (4)	0.009 (3)
C9	0.047 (4)	0.026 (4)	0.030 (4)	0.002 (3)	0.005 (3)	0.003 (3)
C10	0.088 (7)	0.013 (4)	0.074 (7)	−0.009 (4)	0.046 (6)	−0.009 (4)
C11	0.052 (4)	0.014 (3)	0.030 (4)	−0.004 (3)	0.002 (3)	0.005 (3)
C12	0.048 (4)	0.010 (3)	0.036 (4)	−0.003 (3)	0.004 (3)	0.000 (3)
C13	0.039 (4)	0.023 (4)	0.028 (4)	−0.005 (3)	0.006 (3)	−0.001 (3)
C14	0.029 (3)	0.016 (3)	0.029 (4)	−0.004 (2)	0.007 (3)	0.000 (3)
C15	0.034 (3)	0.014 (3)	0.027 (4)	−0.004 (3)	0.007 (3)	−0.001 (3)
C16	0.035 (3)	0.016 (3)	0.030 (4)	−0.001 (3)	0.009 (3)	0.007 (3)
C17	0.048 (4)	0.011 (3)	0.036 (4)	0.001 (3)	0.016 (3)	−0.002 (3)
C18	0.056 (5)	0.016 (3)	0.025 (4)	−0.001 (3)	0.012 (3)	−0.004 (3)
C19	0.036 (4)	0.015 (3)	0.029 (4)	−0.004 (3)	0.009 (3)	−0.001 (3)
C20	0.045 (4)	0.017 (3)	0.024 (4)	−0.004 (3)	0.008 (3)	−0.001 (3)
C21	0.055 (5)	0.014 (3)	0.041 (5)	0.005 (3)	0.010 (4)	0.007 (3)

Geometric parameters (Å, º) top

Br1—C1	2.048 (10)	C9—H9	0.9500
Br2—C2	2.020 (9)	C10—H10A	0.9800
Br3—C15	1.900 (7)	C10—H10B	0.9800
O1—C3	1.223 (10)	C10—H10C	0.9800
O2—C7	1.363 (8)	C11—C20	1.376 (9)
O2—C10	1.444 (11)	C11—C12	1.433 (11)
O3—C16	1.374 (8)	C12—C13	1.360 (10)
O3—C21	1.432 (8)	C12—H12	0.9500
C1—C2	1.466 (11)	C13—C14	1.420 (10)
C1—C11	1.507 (10)	C13—H13	0.9500
C1—H1	1.0000	C14—C15	1.424 (10)
C2—C3	1.547 (11)	C14—C19	1.430 (10)
C2—H2	1.0000	C15—C16	1.374 (9)
C3—C4	1.485 (10)	C16—C17	1.403 (10)
C4—C5	1.387 (11)	C17—C18	1.362 (10)
C4—C9	1.403 (11)	C17—H17	0.9500
C5—C6	1.374 (10)	C18—C19	1.422 (9)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.386 (12)	C19—C20	1.416 (10)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.405 (12)	C21—H21A	0.9800
C8—C9	1.360 (10)	C21—H21B	0.9800
C8—H8	0.9500	C21—H21C	0.9800

C7—O2—C10	116.6 (7)	H10A—C10—H10C	109.5
C16—O3—C21	118.1 (6)	H10B—C10—H10C	109.5
C2—C1—C11	119.1 (8)	C20—C11—C12	118.5 (6)
C2—C1—Br1	100.1 (6)	C20—C11—C1	117.8 (7)
C11—C1—Br1	108.4 (6)	C12—C11—C1	123.5 (6)
C2—C1—H1	109.6	C13—C12—C11	120.4 (6)
C11—C1—H1	109.6	C13—C12—H12	119.8
Br1—C1—H1	109.6	C11—C12—H12	119.8
C1—C2—C3	114.0 (7)	C12—C13—C14	122.2 (7)
C1—C2—Br2	106.3 (6)	C12—C13—H13	118.9
C3—C2—Br2	104.3 (5)	C14—C13—H13	118.9
C1—C2—H2	110.6	C13—C14—C15	124.6 (6)
C3—C2—H2	110.6	C13—C14—C19	117.6 (6)
Br2—C2—H2	110.6	C15—C14—C19	117.7 (6)
O1—C3—C4	121.6 (7)	C16—C15—C14	122.0 (6)
O1—C3—C2	118.4 (6)	C16—C15—Br3	118.7 (5)
C4—C3—C2	120.0 (7)	C14—C15—Br3	119.4 (5)
C5—C4—C9	117.9 (7)	C15—C16—O3	116.9 (6)
C5—C4—C3	124.4 (7)	C15—C16—C17	119.5 (6)
C9—C4—C3	117.7 (7)	O3—C16—C17	123.5 (6)
C6—C5—C4	121.7 (7)	C18—C17—C16	120.6 (6)
C6—C5—H5	119.1	C18—C17—H17	119.7
C4—C5—H5	119.1	C16—C17—H17	119.7
C5—C6—C7	119.8 (8)	C17—C18—C19	121.5 (7)
C5—C6—H6	120.1	C17—C18—H18	119.3
C7—C6—H6	120.1	C19—C18—H18	119.3
O2—C7—C6	125.5 (7)	C20—C19—C18	122.1 (6)
O2—C7—C8	115.3 (7)	C20—C19—C14	119.2 (6)
C6—C7—C8	119.2 (6)	C18—C19—C14	118.6 (6)
C9—C8—C7	120.2 (7)	C11—C20—C19	122.0 (7)
C9—C8—H8	119.9	C11—C20—H20	119.0
C7—C8—H8	119.9	C19—C20—H20	119.0
C8—C9—C4	121.1 (7)	O3—C21—H21A	109.5
C8—C9—H9	119.4	O3—C21—H21B	109.5
C4—C9—H9	119.4	H21A—C21—H21B	109.5
O2—C10—H10A	109.5	O3—C21—H21C	109.5
O2—C10—H10B	109.5	H21A—C21—H21C	109.5
H10A—C10—H10B	109.5	H21B—C21—H21C	109.5
O2—C10—H10C	109.5

C11—C1—C2—C3	174.3 (7)	C20—C11—C12—C13	−1.5 (12)
Br1—C1—C2—C3	−68.0 (7)	C1—C11—C12—C13	174.4 (8)
C11—C1—C2—Br2	59.9 (9)	C11—C12—C13—C14	0.5 (12)
Br1—C1—C2—Br2	177.6 (3)	C12—C13—C14—C15	−179.1 (7)
C1—C2—C3—O1	−27.1 (12)	C12—C13—C14—C19	−0.6 (11)
Br2—C2—C3—O1	88.5 (9)	C13—C14—C15—C16	175.3 (7)
C1—C2—C3—C4	154.4 (8)	C19—C14—C15—C16	−3.2 (10)
Br2—C2—C3—C4	−90.0 (7)	C13—C14—C15—Br3	−4.6 (9)
O1—C3—C4—C5	−175.9 (9)	C19—C14—C15—Br3	176.9 (5)
C2—C3—C4—C5	2.5 (12)	C14—C15—C16—O3	−178.7 (6)
O1—C3—C4—C9	3.4 (12)	Br3—C15—C16—O3	1.2 (9)
C2—C3—C4—C9	−178.2 (7)	C14—C15—C16—C17	2.2 (10)
C9—C4—C5—C6	−1.0 (12)	Br3—C15—C16—C17	−177.9 (5)
C3—C4—C5—C6	178.3 (8)	C21—O3—C16—C15	172.8 (7)
C4—C5—C6—C7	0.6 (13)	C21—O3—C16—C17	−8.1 (10)
C10—O2—C7—C6	1.5 (11)	C15—C16—C17—C18	−0.3 (11)
C10—O2—C7—C8	−177.7 (7)	O3—C16—C17—C18	−179.4 (7)
C5—C6—C7—O2	−178.9 (8)	C16—C17—C18—C19	−0.5 (12)
C5—C6—C7—C8	0.3 (12)	C17—C18—C19—C20	−178.5 (7)
O2—C7—C8—C9	178.4 (7)	C17—C18—C19—C14	−0.6 (11)
C6—C7—C8—C9	−0.9 (12)	C13—C14—C19—C20	1.7 (10)
C7—C8—C9—C4	0.5 (13)	C15—C14—C19—C20	−179.7 (6)
C5—C4—C9—C8	0.4 (12)	C13—C14—C19—C18	−176.3 (7)
C3—C4—C9—C8	−179.0 (8)	C15—C14—C19—C18	2.3 (10)
C2—C1—C11—C20	−163.0 (8)	C12—C11—C20—C19	2.7 (12)
Br1—C1—C11—C20	83.7 (8)	C1—C11—C20—C19	−173.4 (7)
C2—C1—C11—C12	21.1 (13)	C18—C19—C20—C11	175.1 (7)
Br1—C1—C11—C12	−92.2 (9)	C14—C19—C20—C11	−2.8 (11)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇Br₃O₃
M_r	557.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.4989 (5), 20.3640 (16), 13.6083 (8)
β (°)	104.844 (5)
V (Å³)	2008.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.04
Crystal size (mm)	0.32 × 0.29 × 0.12

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.168, 0.471
No. of measured, independent and observed [I > 2σ(I)] reflections	23062, 3531, 3048
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.174, 1.08
No. of reflections	3531
No. of parameters	246
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0826P)² + 13.7141P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.68, −2.00

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.

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2,3-Dibromo-3-(4-bromo-6-meth­oxy-2-naphth­yl)-1-(4-methoxy­phen­yl)propan-1-one

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2,3-Dibromo-3-(4-bromo-6-methoxy-2-naphthyl)-1-(4-methoxyphenyl)propan-1-one