Bis(4-bromo­benzo­yl)(2,7-dimethoxy­naphthalene-1,8-di­yl)dimethanone

Watanabe, S.; Nakaema, K.; Muto, T.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810001819

Bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone

S. Watanabe, K. Nakaema, T. Muto, A. Okamoto and N. Yonezawa

In the title compound, C₂₆H₁₈Br₂O₄, the two 4-bromobenzoyl groups at the 1- and 8-positions of the naphthalene ring system are anti to each other. The dihedral angle between the two benzene rings is 50.92 (14)°. The dihedral angles between the two benzene rings and the naphthalene ring system are 70.18 (11) and 74.98 (12)°. A weak intermolecular C—H

O hydrogen bond exists between the methyl group and the carbonyl O atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810001819/is2516sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810001819/is2516Isup2.hkl Contains datablock I

CCDC reference: 765165

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.103
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22

Author Response: Assigned atomic sites was correct. And the molecular structure of the title compound has been confirmed by ^1^H and ^13^C NMR spectra, IR spectrum, as described in _publ_section_exptl_prep section.

PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.52 Ang.

Author Response: We think that there is some interaction between Br1 and Br2. However, this interaction is rather weak that it is not categorized as a so-called halogen-halogen bonding.


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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the course of our study on selective electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proved to be formed regioselectively with the aid of suitable acidic mediator (Okamoto & Yonezawa, 2009). The aroyl groups at 1,8-positions of the naphthalene rings in these compounds are oriented in opposite fashion and are found to be non-coplanar resulting in partial disruption in π-conjugation systems. Recently, we have reported the X-ray crystal structures of 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008) and (2,7-dimethoxynaphthalene-1,8-diyl)-bis(4-fluorobenzoyl)dimethanone (Watanabe et al., 2010). As a part of the course of our continuous study on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, peri-aroylnaphthalene bearing bromo groups, is discussed in this report.

The molecular structure of the title molecule is displayed in Fig. 1. The two 4-bromobenzoyl groups are situated in anti orientation. Furthermore, these 4-bromobenzoyl groups are twisted away from the attached naphthalene ring. The interplanar angle between the best planes of two benzene rings is 50.92 (14)°. On the other hand, the two interplanar angles between the best planes of the peri-bromophenyl rings and the naphthalene ring are 70.18 (11) and 74.98 (12)°. The torsion angles between the carbonyl groups and the naphthalene ring are relatively large [C10—C1—C11—O3 = -53.3 (3)° and C10—C9—C18—O1 = -47.3 (3)°] and those between 4-bromophenyl groups and carbonyl groups are rather small [O3—C11—C12—C17 = -16.8 (4)° and O1—C18—C19—C20 = -20.0 (4)°]. The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 1).

Related literature top

For general background to the regioselective formation of peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009). For related structures, see: Mitsui et al. (2009); Nakaema et al. (2007, 2008); Watanabe et al. (2010).

Experimental top

The title compound was prepared by electrophilic aromatic diaroylation reaction of 2,7-dimethoxynaphthalene with 4-bromobenzoic acid. Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol.

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃): δ 3.69 (6H, s), 7.19 (2H, d, J = 9.0 Hz), 7.47 (4H, d, J = 8.4 Hz), 7.54 (4H, d, J = 8.4 Hz), 7.95 (2H, d, J = 9.0 Hz); ¹³C NMR (75.0 MHz, CDCl₃): δ 56.3, 111.1, 120.6, 125.5, 127.9, 123.0, 130.6, 131.4, 132.5, 137.5, 156.5, 196.2; IR (KBr cm^-1): 1660, 1269; m.p. = 250 °C.

Structure description top

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids at 50% probability for non-H atoms.

Bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone top

Crystal data top

C₂₆H₁₈Br₂O₄	F(000) = 1104
M_r = 554.22	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 523 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 7.8748 (5) Å	Cell parameters from 40803 reflections
b = 25.7908 (16) Å	θ = 3.4–68.2°
c = 11.5618 (7) Å	µ = 4.71 mm⁻¹
β = 100.982 (4)°	T = 296 K
V = 2305.2 (2) Å³	Platelet, colorless
Z = 4	0.60 × 0.30 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4220 independent reflections
Radiation source: rotating anode	3825 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 3.4°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −31→31
T_min = 0.164, T_max = 0.452	l = −13→13
42468 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0451P)² + 1.8271P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4220 reflections	Δρ_max = 0.73 e Å⁻³
292 parameters	Δρ_min = −0.66 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00195 (13)

Crystal data top

C₂₆H₁₈Br₂O₄	V = 2305.2 (2) Å³
M_r = 554.22	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.8748 (5) Å	µ = 4.71 mm⁻¹
b = 25.7908 (16) Å	T = 296 K
c = 11.5618 (7) Å	0.60 × 0.30 × 0.20 mm
β = 100.982 (4)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4220 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3825 reflections with I > 2σ(I)
T_min = 0.164, T_max = 0.452	R_int = 0.064
42468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.73 e Å⁻³
4220 reflections	Δρ_min = −0.66 e Å⁻³
292 parameters

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	0.72128 (5)	0.437493 (13)	0.07373 (3)	0.07441 (16)
Br2	1.22096 (6)	0.071146 (15)	0.46717 (4)	0.08957 (19)
O1	0.7621 (2)	0.18244 (7)	−0.02615 (16)	0.0540 (4)
O2	0.7527 (3)	0.04184 (9)	−0.0577 (2)	0.0725 (6)
O3	0.5203 (3)	0.18565 (8)	0.17194 (16)	0.0626 (5)
O4	0.1847 (3)	0.25609 (10)	−0.0098 (2)	0.0817 (7)
C1	0.3713 (3)	0.18756 (10)	−0.0245 (2)	0.0478 (6)
C2	0.2137 (4)	0.21142 (12)	−0.0655 (3)	0.0591 (7)
C3	0.0891 (4)	0.18868 (15)	−0.1549 (3)	0.0706 (8)
H3	−0.0131	0.2061	−0.1852	0.085*
C4	0.1205 (4)	0.14116 (15)	−0.1958 (3)	0.0711 (9)
H4	0.0360	0.1256	−0.2523	0.085*
C5	0.2764 (4)	0.11461 (12)	−0.1558 (2)	0.0585 (7)
C6	0.3060 (5)	0.06490 (13)	−0.1987 (3)	0.0696 (9)
H6	0.2184	0.0492	−0.2526	0.083*
C7	0.4558 (5)	0.03943 (12)	−0.1646 (3)	0.0661 (8)
H7	0.4694	0.0062	−0.1927	0.079*
C8	0.5925 (4)	0.06332 (11)	−0.0859 (2)	0.0558 (7)
C9	0.5715 (3)	0.11220 (10)	−0.0403 (2)	0.0460 (6)
C10	0.4095 (3)	0.13854 (10)	−0.0715 (2)	0.0487 (6)
C11	0.4846 (3)	0.21101 (10)	0.0821 (2)	0.0483 (6)
C12	0.5453 (3)	0.26560 (10)	0.0768 (2)	0.0446 (5)
C13	0.5458 (3)	0.29065 (10)	−0.0294 (2)	0.0474 (6)
H13	0.5073	0.2731	−0.0999	0.057*
C14	0.6028 (4)	0.34120 (10)	−0.0320 (2)	0.0508 (6)
H14	0.6058	0.3576	−0.1032	0.061*
C15	0.6551 (3)	0.36681 (10)	0.0736 (2)	0.0498 (6)
C16	0.6569 (4)	0.34286 (11)	0.1802 (2)	0.0561 (7)
H16	0.6937	0.3607	0.2504	0.067*
C17	0.6036 (4)	0.29216 (11)	0.1813 (2)	0.0543 (6)
H17	0.6066	0.2754	0.2530	0.065*
C18	0.7312 (3)	0.14120 (10)	0.0171 (2)	0.0450 (5)
C19	0.8499 (3)	0.12117 (9)	0.1232 (2)	0.0463 (6)
C20	1.0174 (4)	0.14010 (12)	0.1497 (3)	0.0615 (7)
H20	1.0549	0.1636	0.0990	0.074*
C21	1.1292 (4)	0.12445 (13)	0.2506 (3)	0.0680 (8)
H21	1.2420	0.1369	0.2677	0.082*
C22	1.0712 (4)	0.09027 (10)	0.3249 (2)	0.0560 (7)
C23	0.9078 (4)	0.07017 (11)	0.3003 (3)	0.0595 (7)
H23	0.8718	0.0464	0.3511	0.071*
C24	0.7965 (4)	0.08571 (11)	0.1986 (2)	0.0559 (7)
H24	0.6851	0.0722	0.1809	0.067*
C25	0.0244 (4)	0.28190 (14)	−0.0380 (4)	0.0872 (12)
H25A	0.0302	0.3139	0.0050	0.105*
H25B	−0.0647	0.2604	−0.0173	0.105*
H25C	−0.0016	0.2890	−0.1210	0.105*
C26	0.7792 (6)	−0.00847 (14)	−0.1026 (4)	0.0892 (12)
H26A	0.8985	−0.0181	−0.0786	0.107*
H26B	0.7494	−0.0080	−0.1870	0.107*
H26C	0.7076	−0.0332	−0.0722	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0966 (3)	0.0548 (2)	0.0726 (2)	−0.01775 (16)	0.01798 (19)	−0.00874 (14)
Br2	0.0988 (3)	0.0691 (3)	0.0839 (3)	0.00526 (19)	−0.0253 (2)	0.01543 (18)
O1	0.0562 (11)	0.0522 (11)	0.0536 (10)	−0.0098 (8)	0.0102 (8)	0.0071 (8)
O2	0.0782 (15)	0.0593 (12)	0.0778 (14)	0.0047 (11)	0.0087 (11)	−0.0213 (11)
O3	0.0877 (15)	0.0586 (11)	0.0417 (10)	−0.0066 (10)	0.0131 (9)	0.0028 (8)
O4	0.0507 (12)	0.0856 (16)	0.1094 (19)	0.0056 (11)	0.0163 (12)	−0.0257 (14)
C1	0.0456 (14)	0.0549 (15)	0.0445 (13)	−0.0100 (11)	0.0128 (10)	−0.0023 (11)
C2	0.0474 (15)	0.0674 (18)	0.0639 (17)	−0.0093 (13)	0.0136 (13)	−0.0031 (14)
C3	0.0493 (17)	0.089 (2)	0.070 (2)	−0.0042 (15)	0.0039 (14)	0.0004 (17)
C4	0.0564 (18)	0.089 (2)	0.0636 (18)	−0.0159 (16)	−0.0006 (14)	−0.0074 (17)
C5	0.0576 (16)	0.0679 (18)	0.0488 (14)	−0.0176 (14)	0.0072 (12)	−0.0061 (13)
C6	0.074 (2)	0.070 (2)	0.0597 (18)	−0.0244 (16)	0.0006 (15)	−0.0150 (14)
C7	0.083 (2)	0.0525 (16)	0.0622 (18)	−0.0176 (15)	0.0118 (16)	−0.0150 (14)
C8	0.0675 (18)	0.0517 (15)	0.0490 (15)	−0.0093 (13)	0.0129 (13)	−0.0054 (11)
C9	0.0539 (14)	0.0482 (13)	0.0366 (12)	−0.0111 (11)	0.0102 (10)	−0.0019 (10)
C10	0.0540 (15)	0.0542 (14)	0.0391 (12)	−0.0152 (12)	0.0121 (11)	−0.0001 (10)
C11	0.0513 (14)	0.0553 (15)	0.0407 (13)	−0.0019 (11)	0.0150 (11)	−0.0037 (11)
C12	0.0443 (13)	0.0524 (14)	0.0378 (12)	−0.0012 (10)	0.0096 (10)	−0.0031 (10)
C13	0.0558 (15)	0.0502 (14)	0.0361 (12)	0.0004 (11)	0.0082 (10)	−0.0064 (10)
C14	0.0608 (16)	0.0518 (14)	0.0406 (13)	0.0014 (12)	0.0116 (11)	0.0028 (11)
C15	0.0507 (14)	0.0465 (13)	0.0526 (14)	−0.0023 (11)	0.0104 (11)	−0.0047 (11)
C16	0.0661 (17)	0.0624 (17)	0.0396 (13)	−0.0110 (13)	0.0093 (12)	−0.0113 (12)
C17	0.0645 (17)	0.0627 (16)	0.0359 (12)	−0.0072 (13)	0.0103 (11)	−0.0021 (11)
C18	0.0501 (14)	0.0464 (13)	0.0406 (12)	−0.0057 (11)	0.0137 (10)	−0.0023 (10)
C19	0.0521 (14)	0.0437 (13)	0.0439 (13)	−0.0056 (10)	0.0113 (11)	−0.0026 (10)
C20	0.0567 (17)	0.0619 (17)	0.0647 (17)	−0.0107 (13)	0.0087 (13)	0.0141 (14)
C21	0.0543 (17)	0.0665 (19)	0.078 (2)	−0.0080 (14)	−0.0012 (15)	0.0080 (15)
C22	0.0661 (17)	0.0436 (14)	0.0532 (15)	0.0060 (12)	−0.0016 (13)	−0.0005 (11)
C23	0.078 (2)	0.0497 (15)	0.0505 (15)	−0.0066 (13)	0.0105 (14)	0.0055 (12)
C24	0.0618 (17)	0.0538 (15)	0.0515 (15)	−0.0148 (13)	0.0091 (12)	0.0022 (12)
C25	0.065 (2)	0.0543 (18)	0.142 (4)	0.0001 (15)	0.021 (2)	0.015 (2)
C26	0.107 (3)	0.068 (2)	0.089 (3)	0.018 (2)	0.009 (2)	−0.0228 (19)

Geometric parameters (Å, º) top

Br1—C15	1.896 (3)	C12—C17	1.389 (3)
Br2—C22	1.897 (3)	C13—C14	1.381 (4)
O1—C18	1.219 (3)	C13—H13	0.9300
O2—C8	1.359 (4)	C14—C15	1.381 (4)
O2—C26	1.427 (4)	C14—H14	0.9300
O3—C11	1.214 (3)	C15—C16	1.376 (4)
O4—C2	1.361 (4)	C16—C17	1.374 (4)
O4—C25	1.409 (4)	C16—H16	0.9300
C1—C2	1.386 (4)	C17—H17	0.9300
C1—C10	1.430 (4)	C18—C19	1.487 (4)
C1—C11	1.505 (4)	C19—C20	1.384 (4)
C2—C3	1.409 (4)	C19—C24	1.383 (4)
C3—C4	1.354 (5)	C20—C21	1.381 (4)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.405 (5)	C21—C22	1.369 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.410 (4)	C22—C23	1.366 (4)
C5—C10	1.429 (4)	C23—C24	1.385 (4)
C6—C7	1.342 (5)	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.412 (4)	C25—H25A	0.9600
C7—H7	0.9300	C25—H25B	0.9600
C8—C9	1.389 (4)	C25—H25C	0.9600
C9—C10	1.429 (4)	C26—H26A	0.9600
C9—C18	1.504 (3)	C26—H26B	0.9600
C11—C12	1.492 (4)	C26—H26C	0.9600
C12—C13	1.389 (3)

C8—O2—C26	118.4 (3)	C13—C14—H14	120.8
C2—O4—C25	120.9 (3)	C16—C15—C14	121.9 (2)
C2—C1—C10	120.1 (2)	C16—C15—Br1	118.37 (19)
C2—C1—C11	117.0 (2)	C14—C15—Br1	119.8 (2)
C10—C1—C11	122.1 (2)	C17—C16—C15	119.0 (2)
O4—C2—C1	115.7 (3)	C17—C16—H16	120.5
O4—C2—C3	122.9 (3)	C15—C16—H16	120.5
C1—C2—C3	121.3 (3)	C16—C17—C12	120.8 (2)
C4—C3—C2	119.0 (3)	C16—C17—H17	119.6
C4—C3—H3	120.5	C12—C17—H17	119.6
C2—C3—H3	120.5	O1—C18—C19	119.9 (2)
C3—C4—C5	122.1 (3)	O1—C18—C9	117.9 (2)
C3—C4—H4	118.9	C19—C18—C9	122.2 (2)
C5—C4—H4	118.9	C20—C19—C24	119.0 (3)
C4—C5—C6	121.3 (3)	C20—C19—C18	118.9 (2)
C4—C5—C10	119.7 (3)	C24—C19—C18	122.1 (2)
C6—C5—C10	118.9 (3)	C21—C20—C19	120.7 (3)
C7—C6—C5	122.5 (3)	C21—C20—H20	119.6
C7—C6—H6	118.8	C19—C20—H20	119.6
C5—C6—H6	118.8	C22—C21—C20	118.9 (3)
C6—C7—C8	119.7 (3)	C22—C21—H21	120.6
C6—C7—H7	120.2	C20—C21—H21	120.6
C8—C7—H7	120.2	C23—C22—C21	121.8 (3)
O2—C8—C9	116.8 (2)	C23—C22—Br2	119.2 (2)
O2—C8—C7	122.4 (3)	C21—C22—Br2	119.0 (2)
C9—C8—C7	120.6 (3)	C22—C23—C24	119.1 (3)
C8—C9—C10	120.1 (2)	C22—C23—H23	120.5
C8—C9—C18	117.9 (2)	C24—C23—H23	120.5
C10—C9—C18	120.4 (2)	C19—C24—C23	120.5 (3)
C5—C10—C9	118.1 (2)	C19—C24—H24	119.8
C5—C10—C1	117.4 (3)	C23—C24—H24	119.8
C9—C10—C1	124.5 (2)	O4—C25—H25A	109.5
O3—C11—C12	121.3 (2)	O4—C25—H25B	109.5
O3—C11—C1	119.3 (2)	H25A—C25—H25B	109.5
C12—C11—C1	119.3 (2)	O4—C25—H25C	109.5
C13—C12—C17	118.9 (2)	H25A—C25—H25C	109.5
C13—C12—C11	122.1 (2)	H25B—C25—H25C	109.5
C17—C12—C11	119.0 (2)	O2—C26—H26A	109.5
C14—C13—C12	120.9 (2)	O2—C26—H26B	109.5
C14—C13—H13	119.5	H26A—C26—H26B	109.5
C12—C13—H13	119.5	O2—C26—H26C	109.5
C15—C14—C13	118.4 (2)	H26A—C26—H26C	109.5
C15—C14—H14	120.8	H26B—C26—H26C	109.5

C25—O4—C2—C1	−175.5 (3)	C10—C1—C11—O3	−53.2 (4)
C25—O4—C2—C3	1.0 (5)	C2—C1—C11—C12	−60.4 (3)
C10—C1—C2—O4	175.6 (2)	C10—C1—C11—C12	129.1 (3)
C11—C1—C2—O4	4.9 (4)	O3—C11—C12—C13	163.0 (3)
C10—C1—C2—C3	−1.0 (4)	C1—C11—C12—C13	−19.4 (4)
C11—C1—C2—C3	−171.6 (3)	O3—C11—C12—C17	−16.8 (4)
O4—C2—C3—C4	−172.1 (3)	C1—C11—C12—C17	160.8 (2)
C1—C2—C3—C4	4.1 (5)	C17—C12—C13—C14	−0.2 (4)
C2—C3—C4—C5	−2.7 (5)	C11—C12—C13—C14	−179.9 (2)
C3—C4—C5—C6	179.4 (3)	C12—C13—C14—C15	−1.7 (4)
C3—C4—C5—C10	−1.8 (5)	C13—C14—C15—C16	2.1 (4)
C4—C5—C6—C7	177.9 (3)	C13—C14—C15—Br1	−176.3 (2)
C10—C5—C6—C7	−1.0 (5)	C14—C15—C16—C17	−0.6 (4)
C5—C6—C7—C8	−2.2 (5)	Br1—C15—C16—C17	177.8 (2)
C26—O2—C8—C9	179.7 (3)	C15—C16—C17—C12	−1.3 (4)
C26—O2—C8—C7	−4.8 (5)	C13—C12—C17—C16	1.7 (4)
C6—C7—C8—O2	−173.1 (3)	C11—C12—C17—C16	−178.6 (3)
C6—C7—C8—C9	2.2 (5)	C8—C9—C18—O1	118.2 (3)
O2—C8—C9—C10	176.5 (2)	C10—C9—C18—O1	−47.3 (3)
C7—C8—C9—C10	0.9 (4)	C8—C9—C18—C19	−61.8 (3)
O2—C8—C9—C18	10.9 (4)	C10—C9—C18—C19	132.6 (3)
C7—C8—C9—C18	−164.7 (3)	O1—C18—C19—C20	−20.0 (4)
C4—C5—C10—C9	−174.9 (3)	C9—C18—C19—C20	160.0 (3)
C6—C5—C10—C9	4.0 (4)	O1—C18—C19—C24	157.6 (3)
C4—C5—C10—C1	4.8 (4)	C9—C18—C19—C24	−22.4 (4)
C6—C5—C10—C1	−176.3 (3)	C24—C19—C20—C21	−0.8 (5)
C8—C9—C10—C5	−4.0 (4)	C18—C19—C20—C21	176.8 (3)
C18—C9—C10—C5	161.3 (2)	C19—C20—C21—C22	−0.7 (5)
C8—C9—C10—C1	176.4 (2)	C20—C21—C22—C23	1.9 (5)
C18—C9—C10—C1	−18.3 (4)	C20—C21—C22—Br2	−177.1 (3)
C2—C1—C10—C5	−3.4 (4)	C21—C22—C23—C24	−1.5 (5)
C11—C1—C10—C5	166.7 (2)	Br2—C22—C23—C24	177.5 (2)
C2—C1—C10—C9	176.2 (2)	C20—C19—C24—C23	1.3 (4)
C11—C1—C10—C9	−13.7 (4)	C18—C19—C24—C23	−176.3 (3)
C2—C1—C11—O3	117.2 (3)	C22—C23—C24—C19	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25B···O1ⁱ	0.96	2.42	3.313 (4)	155

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Br₂O₄
M_r	554.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.8748 (5), 25.7908 (16), 11.5618 (7)
β (°)	100.982 (4)
V (Å³)	2305.2 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.71
Crystal size (mm)	0.60 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.164, 0.452
No. of measured, independent and observed [I > 2σ(I)] reflections	42468, 4220, 3825
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.05
No. of reflections	4220
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.66

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).