{8-[4-(Bromo-meth-yl)benzo-yl]-2,7-dimeth-oxy-naphthalen-1-yl}[4-(bromo-meth-yl)phen-yl]methanone.

In the title compound, C(28)H(22)Br(2)O(4), the two 4-bromo-methyl-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, the benzene rings forming a dihedral angle of 2.94 (16)°. The dihedral angles between the benzene rings and the naphthalene ring systems are 70.98 (13) and 72.89 (13)°. In the crystal, centrosymmetric-ally-related mol-ecules are linked into dimeric units by inter-molecular C-H⋯O inter-actions.

Related literature

For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene deriv­atives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Muto et al. (2010 ▶); Nakaema et al. (2007 ▶, 2008 ▶); Watanabe, Nagasawa et al. (2010 ▶); Watanabe, Nakaema et al. (2010 ▶).

Experimental

Crystal data

C28H22Br2O4

M = 582.28

Monoclinic,

a = 11.5948 (2) Å

b = 8.37239 (15) Å

c = 24.5352 (5) Å

β = 92.617 (1)°

V = 2379.29 (8) Å3

Z = 4

Cu Kα radiation

μ = 4.60 mm−1

T = 193 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.207, T max = 0.460

41450 measured reflections

4319 independent reflections

3916 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.14

4319 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.59 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 datablock(s) I, global. DOI: 10.1107/S1600536811029151/rz2629sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029151/rz2629Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029151/rz2629Isup3.cml

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

C28H22Br2O4	F(000) = 1168
Mr = 582.28	Dx = 1.626 Mg m−3
Monoclinic, P21/n	Melting point = 239.0–245.0 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 11.5948 (2) Å	Cell parameters from 30055 reflections
b = 8.37239 (15) Å	θ = 3.6–68.2°
c = 24.5352 (5) Å	µ = 4.60 mm−1
β = 92.617 (1)°	T = 193 K
V = 2379.29 (8) Å3	Block, yellow
Z = 4	0.50 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	4319 independent reflections
Radiation source: rotating anode	3916 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.6°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −10→10
Tmin = 0.207, Tmax = 0.460	l = −29→29
41450 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0277P)2 + 4.5808P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
4319 reflections	Δρmax = 0.85 e Å−3
310 parameters	Δρmin = −0.59 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: 0.00183 (10)

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	−0.15947 (4)	0.20415 (5)	0.241294 (16)	0.04354 (16)
Br2	−0.11445 (4)	0.28738 (5)	−0.255555 (15)	0.04200 (15)
O1	0.1773 (2)	0.4762 (3)	0.01077 (9)	0.0310 (5)
O2	0.1901 (2)	0.0544 (3)	0.00410 (9)	0.0317 (5)
O3	0.33170 (19)	0.5296 (3)	0.13097 (9)	0.0331 (6)
O4	0.3673 (2)	0.0170 (3)	−0.10273 (9)	0.0352 (6)
C1	0.3426 (3)	0.3654 (4)	0.05473 (12)	0.0229 (6)
C2	0.3998 (3)	0.4487 (4)	0.09594 (12)	0.0268 (7)
C3	0.5212 (3)	0.4562 (4)	0.10035 (13)	0.0300 (7)
H3	0.5592	0.5116	0.1298	0.036*
C4	0.5834 (3)	0.3832 (4)	0.06193 (13)	0.0296 (7)
H4	0.6651	0.3932	0.0637	0.035*
C5	0.5291 (3)	0.2925 (4)	0.01916 (13)	0.0262 (7)
C6	0.5961 (3)	0.2128 (4)	−0.01911 (14)	0.0301 (7)
H6	0.6779	0.2216	−0.0163	0.036*
C7	0.5455 (3)	0.1239 (4)	−0.05987 (14)	0.0312 (7)
H7	0.5916	0.0719	−0.0855	0.037*
C8	0.4242 (3)	0.1090 (4)	−0.06393 (13)	0.0277 (7)
C9	0.3552 (3)	0.1836 (4)	−0.02723 (12)	0.0234 (7)
C10	0.4066 (3)	0.2799 (4)	0.01571 (12)	0.0230 (6)
C11	0.2132 (3)	0.3889 (4)	0.04739 (12)	0.0234 (6)
C12	0.1329 (3)	0.3064 (4)	0.08379 (12)	0.0230 (6)
C13	0.1743 (3)	0.2117 (4)	0.12720 (12)	0.0256 (7)
H13	0.2551	0.1999	0.1342	0.031*
C14	0.0980 (3)	0.1351 (4)	0.15989 (13)	0.0294 (7)
H14	0.1267	0.0730	0.1899	0.035*
C15	−0.0205 (3)	0.1477 (4)	0.14942 (13)	0.0280 (7)
C16	−0.0608 (3)	0.2401 (4)	0.10524 (14)	0.0310 (7)
H16	−0.1416	0.2481	0.0972	0.037*
C17	0.0147 (3)	0.3201 (4)	0.07308 (13)	0.0269 (7)
H17	−0.0141	0.3844	0.0436	0.032*
C18	0.2281 (3)	0.1422 (4)	−0.03013 (12)	0.0244 (7)
C19	0.1506 (3)	0.2140 (4)	−0.07415 (12)	0.0247 (7)
C20	0.1954 (3)	0.3069 (4)	−0.11521 (13)	0.0264 (7)
H20	0.2764	0.3231	−0.1161	0.032*
C21	0.1222 (3)	0.3757 (4)	−0.15465 (13)	0.0282 (7)
H21	0.1534	0.4372	−0.1830	0.034*
C22	0.0038 (3)	0.3556 (4)	−0.15305 (13)	0.0269 (7)
C23	−0.0412 (3)	0.2637 (4)	−0.11166 (14)	0.0303 (7)
H23	−0.1223	0.2499	−0.1103	0.036*
C24	0.0318 (3)	0.1926 (4)	−0.07264 (13)	0.0290 (7)
H24	0.0007	0.1290	−0.0448	0.035*
C25	0.3876 (3)	0.6214 (5)	0.17364 (14)	0.0388 (9)
H25A	0.4311	0.5499	0.1986	0.047*
H25B	0.3294	0.6790	0.1937	0.047*
H25C	0.4404	0.6981	0.1579	0.047*
C26	0.4333 (3)	−0.0513 (5)	−0.14481 (14)	0.0388 (9)
H26A	0.4684	0.0343	−0.1657	0.047*
H26B	0.3825	−0.1154	−0.1692	0.047*
H26C	0.4941	−0.1195	−0.1283	0.047*
C27	−0.1034 (3)	0.0618 (4)	0.18381 (15)	0.0362 (8)
H27A	−0.0648	−0.0323	0.2009	0.043*
H27B	−0.1697	0.0235	0.1605	0.043*
C28	−0.0739 (3)	0.4356 (4)	−0.19505 (14)	0.0346 (8)
H28A	−0.0348	0.5307	−0.2095	0.041*
H28B	−0.1452	0.4717	−0.1780	0.041*

	U11	U22	U33	U12	U13	U23
Br1	0.0452 (3)	0.0507 (3)	0.0359 (2)	−0.00291 (18)	0.01501 (18)	−0.00418 (17)
Br2	0.0488 (3)	0.0514 (3)	0.0252 (2)	0.00179 (18)	−0.00500 (16)	−0.00459 (16)
O1	0.0332 (13)	0.0350 (13)	0.0247 (11)	0.0049 (10)	−0.0006 (9)	0.0078 (10)
O2	0.0350 (13)	0.0305 (12)	0.0299 (12)	−0.0011 (10)	0.0063 (10)	0.0043 (10)
O3	0.0292 (12)	0.0422 (14)	0.0282 (12)	−0.0060 (11)	0.0036 (10)	−0.0113 (10)
O4	0.0355 (13)	0.0374 (14)	0.0330 (13)	0.0077 (11)	0.0051 (10)	−0.0102 (10)
C1	0.0228 (16)	0.0245 (16)	0.0212 (15)	−0.0007 (13)	0.0016 (12)	0.0044 (12)
C2	0.0308 (17)	0.0280 (16)	0.0217 (15)	−0.0033 (14)	0.0027 (13)	0.0043 (13)
C3	0.0293 (18)	0.0342 (18)	0.0260 (16)	−0.0056 (14)	−0.0037 (14)	0.0040 (14)
C4	0.0224 (16)	0.0318 (18)	0.0342 (18)	−0.0024 (14)	−0.0021 (14)	0.0111 (14)
C5	0.0260 (17)	0.0268 (16)	0.0260 (16)	0.0040 (13)	0.0017 (13)	0.0100 (13)
C6	0.0246 (17)	0.0317 (18)	0.0344 (18)	0.0068 (14)	0.0048 (14)	0.0100 (14)
C7	0.0321 (18)	0.0313 (18)	0.0310 (17)	0.0094 (15)	0.0091 (14)	0.0083 (14)
C8	0.0334 (18)	0.0258 (16)	0.0242 (16)	0.0053 (14)	0.0021 (13)	0.0057 (13)
C9	0.0255 (16)	0.0217 (15)	0.0231 (15)	0.0039 (12)	0.0025 (13)	0.0052 (12)
C10	0.0236 (16)	0.0227 (15)	0.0225 (15)	0.0009 (12)	0.0000 (12)	0.0073 (12)
C11	0.0271 (16)	0.0233 (15)	0.0197 (15)	0.0028 (13)	−0.0014 (12)	−0.0040 (12)
C12	0.0258 (16)	0.0225 (15)	0.0208 (15)	0.0015 (12)	0.0028 (12)	−0.0040 (12)
C13	0.0227 (16)	0.0304 (17)	0.0237 (16)	0.0000 (13)	−0.0009 (13)	−0.0007 (13)
C14	0.0346 (19)	0.0290 (17)	0.0245 (16)	−0.0020 (14)	0.0003 (14)	0.0006 (13)
C15	0.0312 (18)	0.0248 (16)	0.0287 (17)	−0.0027 (14)	0.0078 (14)	−0.0078 (13)
C16	0.0235 (17)	0.0353 (18)	0.0343 (18)	0.0014 (14)	0.0023 (14)	−0.0061 (14)
C17	0.0247 (17)	0.0308 (17)	0.0252 (16)	0.0026 (13)	−0.0002 (13)	−0.0016 (13)
C18	0.0292 (17)	0.0212 (15)	0.0230 (15)	0.0005 (13)	0.0031 (13)	−0.0034 (12)
C19	0.0292 (17)	0.0242 (16)	0.0208 (15)	0.0007 (13)	0.0007 (13)	−0.0050 (12)
C20	0.0246 (17)	0.0265 (16)	0.0282 (16)	0.0004 (13)	0.0027 (13)	−0.0023 (13)
C21	0.0351 (19)	0.0256 (16)	0.0241 (16)	−0.0001 (14)	0.0018 (13)	−0.0017 (13)
C22	0.0304 (17)	0.0236 (16)	0.0264 (16)	0.0021 (13)	−0.0012 (13)	−0.0077 (13)
C23	0.0236 (17)	0.0351 (19)	0.0322 (18)	0.0005 (14)	0.0021 (14)	−0.0067 (14)
C24	0.0294 (18)	0.0326 (18)	0.0252 (16)	−0.0026 (14)	0.0040 (14)	−0.0028 (13)
C25	0.044 (2)	0.047 (2)	0.0257 (17)	−0.0160 (18)	0.0029 (15)	−0.0096 (16)
C26	0.052 (2)	0.0338 (19)	0.0317 (19)	0.0043 (17)	0.0130 (16)	−0.0044 (15)
C27	0.038 (2)	0.0310 (18)	0.041 (2)	−0.0066 (15)	0.0120 (16)	−0.0063 (15)
C28	0.0372 (19)	0.0322 (18)	0.0336 (18)	0.0039 (15)	−0.0053 (15)	−0.0060 (15)

Br1—C27	1.979 (3)	C14—C15	1.390 (5)
Br2—C28	1.975 (3)	C14—H14	0.9500
O1—C11	1.216 (4)	C15—C16	1.395 (5)
O2—C18	1.214 (4)	C15—C27	1.492 (5)
O3—C2	1.372 (4)	C16—C17	1.379 (5)
O3—C25	1.430 (4)	C16—H16	0.9500
O4—C8	1.370 (4)	C17—H17	0.9500
O4—C26	1.432 (4)	C18—C19	1.499 (4)
C1—C2	1.374 (4)	C19—C20	1.392 (5)
C1—C10	1.430 (4)	C19—C24	1.392 (5)
C1—C11	1.516 (4)	C20—C21	1.383 (4)
C2—C3	1.409 (5)	C20—H20	0.9500
C3—C4	1.357 (5)	C21—C22	1.386 (5)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.419 (5)	C22—C23	1.395 (5)
C4—H4	0.9500	C22—C28	1.496 (4)
C5—C6	1.413 (5)	C23—C24	1.383 (5)
C5—C10	1.423 (4)	C23—H23	0.9500
C6—C7	1.358 (5)	C24—H24	0.9500
C6—H6	0.9500	C25—H25A	0.9800
C7—C8	1.411 (5)	C25—H25B	0.9800
C7—H7	0.9500	C25—H25C	0.9800
C8—C9	1.380 (4)	C26—H26A	0.9800
C9—C10	1.434 (4)	C26—H26B	0.9800
C9—C18	1.513 (4)	C26—H26C	0.9800
C11—C12	1.489 (4)	C27—H27A	0.9900
C12—C17	1.388 (4)	C27—H27B	0.9900
C12—C13	1.396 (4)	C28—H28A	0.9900
C13—C14	1.379 (5)	C28—H28B	0.9900
C13—H13	0.9500
C2—O3—C25	118.0 (3)	C15—C16—H16	119.5
C8—O4—C26	118.0 (3)	C16—C17—C12	119.9 (3)
C2—C1—C10	119.9 (3)	C16—C17—H17	120.0
C2—C1—C11	117.6 (3)	C12—C17—H17	120.0
C10—C1—C11	121.8 (3)	O2—C18—C19	121.1 (3)
O3—C2—C1	116.1 (3)	O2—C18—C9	119.3 (3)
O3—C2—C3	122.1 (3)	C19—C18—C9	119.5 (3)
C1—C2—C3	121.8 (3)	C20—C19—C24	119.6 (3)
C4—C3—C2	119.1 (3)	C20—C19—C18	121.0 (3)
C4—C3—H3	120.4	C24—C19—C18	119.4 (3)
C2—C3—H3	120.4	C21—C20—C19	120.1 (3)
C3—C4—C5	121.6 (3)	C21—C20—H20	119.9
C3—C4—H4	119.2	C19—C20—H20	119.9
C5—C4—H4	119.2	C20—C21—C22	120.4 (3)
C6—C5—C4	120.4 (3)	C20—C21—H21	119.8
C6—C5—C10	120.2 (3)	C22—C21—H21	119.8
C4—C5—C10	119.4 (3)	C21—C22—C23	119.5 (3)
C7—C6—C5	121.1 (3)	C21—C22—C28	119.5 (3)
C7—C6—H6	119.5	C23—C22—C28	121.0 (3)
C5—C6—H6	119.5	C24—C23—C22	120.3 (3)
C6—C7—C8	119.8 (3)	C24—C23—H23	119.9
C6—C7—H7	120.1	C22—C23—H23	119.9
C8—C7—H7	120.1	C23—C24—C19	120.1 (3)
O4—C8—C9	115.7 (3)	C23—C24—H24	120.0
O4—C8—C7	123.0 (3)	C19—C24—H24	120.0
C9—C8—C7	121.3 (3)	O3—C25—H25A	109.5
C8—C9—C10	120.0 (3)	O3—C25—H25B	109.5
C8—C9—C18	117.2 (3)	H25A—C25—H25B	109.5
C10—C9—C18	122.3 (3)	O3—C25—H25C	109.5
C5—C10—C1	118.1 (3)	H25A—C25—H25C	109.5
C5—C10—C9	117.7 (3)	H25B—C25—H25C	109.5
C1—C10—C9	124.2 (3)	O4—C26—H26A	109.5
O1—C11—C12	121.3 (3)	O4—C26—H26B	109.5
O1—C11—C1	118.0 (3)	H26A—C26—H26B	109.5
C12—C11—C1	120.7 (3)	O4—C26—H26C	109.5
C17—C12—C13	119.6 (3)	H26A—C26—H26C	109.5
C17—C12—C11	119.1 (3)	H26B—C26—H26C	109.5
C13—C12—C11	121.3 (3)	C15—C27—Br1	110.7 (2)
C14—C13—C12	120.0 (3)	C15—C27—H27A	109.5
C14—C13—H13	120.0	Br1—C27—H27A	109.5
C12—C13—H13	120.0	C15—C27—H27B	109.5
C13—C14—C15	120.8 (3)	Br1—C27—H27B	109.5
C13—C14—H14	119.6	H27A—C27—H27B	108.1
C15—C14—H14	119.6	C22—C28—Br2	110.6 (2)
C14—C15—C16	118.6 (3)	C22—C28—H28A	109.5
C14—C15—C27	121.0 (3)	Br2—C28—H28A	109.5
C16—C15—C27	120.3 (3)	C22—C28—H28B	109.5
C17—C16—C15	121.0 (3)	Br2—C28—H28B	109.5
C17—C16—H16	119.5	H28A—C28—H28B	108.1
C25—O3—C2—C1	−178.4 (3)	C10—C1—C11—C12	110.7 (3)
C25—O3—C2—C3	−1.2 (5)	O1—C11—C12—C17	4.9 (4)
C10—C1—C2—O3	178.9 (3)	C1—C11—C12—C17	−174.7 (3)
C11—C1—C2—O3	8.1 (4)	O1—C11—C12—C13	−177.3 (3)
C10—C1—C2—C3	1.6 (5)	C1—C11—C12—C13	3.1 (4)
C11—C1—C2—C3	−169.1 (3)	C17—C12—C13—C14	−1.4 (5)
O3—C2—C3—C4	−175.0 (3)	C11—C12—C13—C14	−179.2 (3)
C1—C2—C3—C4	2.1 (5)	C12—C13—C14—C15	1.6 (5)
C2—C3—C4—C5	−3.5 (5)	C13—C14—C15—C16	−0.3 (5)
C3—C4—C5—C6	−177.6 (3)	C13—C14—C15—C27	178.4 (3)
C3—C4—C5—C10	1.2 (5)	C14—C15—C16—C17	−1.2 (5)
C4—C5—C6—C7	179.2 (3)	C27—C15—C16—C17	−180.0 (3)
C10—C5—C6—C7	0.4 (5)	C15—C16—C17—C12	1.4 (5)
C5—C6—C7—C8	−0.7 (5)	C13—C12—C17—C16	−0.1 (5)
C26—O4—C8—C9	174.4 (3)	C11—C12—C17—C16	177.8 (3)
C26—O4—C8—C7	−7.7 (4)	C8—C9—C18—O2	104.4 (3)
C6—C7—C8—O4	−177.7 (3)	C10—C9—C18—O2	−67.8 (4)
C6—C7—C8—C9	0.1 (5)	C8—C9—C18—C19	−77.4 (4)
O4—C8—C9—C10	178.7 (3)	C10—C9—C18—C19	110.3 (3)
C7—C8—C9—C10	0.7 (5)	O2—C18—C19—C20	−176.1 (3)
O4—C8—C9—C18	6.3 (4)	C9—C18—C19—C20	5.7 (4)
C7—C8—C9—C18	−171.7 (3)	O2—C18—C19—C24	6.4 (5)
C6—C5—C10—C1	−178.7 (3)	C9—C18—C19—C24	−171.7 (3)
C4—C5—C10—C1	2.4 (4)	C24—C19—C20—C21	−0.8 (5)
C6—C5—C10—C9	0.5 (4)	C18—C19—C20—C21	−178.3 (3)
C4—C5—C10—C9	−178.4 (3)	C19—C20—C21—C22	1.3 (5)
C2—C1—C10—C5	−3.8 (4)	C20—C21—C22—C23	−0.8 (5)
C11—C1—C10—C5	166.6 (3)	C20—C21—C22—C28	178.0 (3)
C2—C1—C10—C9	177.0 (3)	C21—C22—C23—C24	−0.3 (5)
C11—C1—C10—C9	−12.6 (5)	C28—C22—C23—C24	−179.0 (3)
C8—C9—C10—C5	−1.0 (4)	C22—C23—C24—C19	0.8 (5)
C18—C9—C10—C5	171.0 (3)	C20—C19—C24—C23	−0.2 (5)
C8—C9—C10—C1	178.2 (3)	C18—C19—C24—C23	177.3 (3)
C18—C9—C10—C1	−9.8 (5)	C14—C15—C27—Br1	96.1 (3)
C2—C1—C11—O1	101.7 (3)	C16—C15—C27—Br1	−85.1 (3)
C10—C1—C11—O1	−68.9 (4)	C21—C22—C28—Br2	95.9 (3)
C2—C1—C11—C12	−78.7 (4)	C23—C22—C28—Br2	−85.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.95	2.55	3.417 (4)	152
C28—H28B···O3i	0.99	2.50	3.453 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.95	2.55	3.417 (4)	152
C28—H28B⋯O3i	0.99	2.50	3.453 (4)	162

Symmetry code: (i) .