Bis(4-bromo-benzo-yl)(2,7-dimethoxy-naphthalene-1,8-di-yl)dimethanone.

In the title compound, C(26)H(18)Br(2)O(4), the two 4-bromo-benzoyl 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 inter-molecular C-H⋯O hydrogen bond exists between the methyl group and the carbonyl O atom.

Related literature

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

Crystal data

C26H18Br2O4

M = 554.22

Monoclinic,

a = 7.8748 (5) Å

b = 25.7908 (16) Å

c = 11.5618 (7) Å

β = 100.982 (4)°

V = 2305.2 (2) Å3

Z = 4

Cu Kα radiation

μ = 4.71 mm−1

T = 296 K

0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.164, T max = 0.452

42468 measured reflections

4220 independent reflections

3825 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

4220 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.66 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001819/is2516sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001819/is2516Isup2.hkl

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

C26H18Br2O4	F(000) = 1104
Mr = 554.22	Dx = 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

Rigaku R-AXIS RAPID diffractometer	4220 independent reflections
Radiation source: rotating anode	3825 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.4°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −31→31
Tmin = 0.164, Tmax = 0.452	l = −13→13
42468 measured reflections

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(Fo2) + (0.0451P)2 + 1.8271P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4220 reflections	Δρmax = 0.73 e Å−3
292 parameters	Δρmin = −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)

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
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .