{8-[4-(Bromo­meth­yl)benzo­yl]-2,7-dimeth­oxy­naphthalen-1-yl}[4-(bromo­meth­yl)phen­yl]methanone

Sasagawa, K.; Hijikata, D.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536811029151

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2119

doi:10.1107/S1600536811029151

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{8-[4-(Bromomethyl)benzoyl]-2,7-dimethoxynaphthalen-1-yl}[4-(bromomethyl)phenyl]methanone

Kosuke Sasagawa,^a Daichi Hijikata,^a Akiko Okamoto,^a ^* Hideaki Oike ^a and Noriyuki Yonezawa ^a

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 13 July 2011; accepted 19 July 2011; online 23 July 2011)

In the title compound, C₂₈H₂₂Br₂O₄, the two 4-bromomethylbenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, 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, centrosymmetrically-related molecules are linked into dimeric units by intermolecular C—H⋯O interactions.

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_r = 582.28
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 1.14
4319 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.59 e Å⁻³

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) -x, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029151/rz2629sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811029151/rz2629Isup3.cml

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009). Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalene derivatives such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al., 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008), bis(4-bromophenyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe, Nakaema et al., 2010), (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone [1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe, Nagasawa et al., 2010), and 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2010). The aroyl groups in these compounds are attached to the naphthalene rings in an almost parallel fashion and oriented in opposite direction. As a part of our ongoing studies on the molecular structures of homologous aroylated 2,7-dimethoxynaphthalene molecules, the X-ray crystal structure of the title compound, bis(4-bromomethylbenzoylated) 2,7-dimethoxynaphthalene, is discussed in this article.

The molecular structure of the title compound is displayed in Fig 1. The two 4-bromomethylbenzoyl groups are twisted away from the attaching naphthalene ring and situated in anti orientation. The dihedral angle between the planes of the benzene rings is 2.94 (16)°. On the other hand, the dihedral angles of the benzene rings with the naphthalene ring system are 70.98 (13) and 72.89 (13)°, respectively. The torsion angles between the carbonyl groups and the naphthalene ring [C10—C1—C11—O1 = -68.9 (4)° and C10—C9—C18—O2 = -67.8 (4)°] are larger than those between the carbonyl groups and the benzene rings [O1—C11—C12—C13 = -177.3 (3)° and O2—C18—C19—C20 = -176.1 (3)°].

In the crystal packing, C—H···O hydrogen bonds between the oxygen atoms of the carbonyl groups and the hydrogen atoms of the benzene rings and between the oxygen atoms of the methoxy groups and the hydrogen atoms of the bromomethyl groups are also observed (Table 1), resulting in the formation of supramolecular dimeric units (Fig. 2) having crystallographic inversion centre.

Related literature top

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 top

To a 50 ml flask, 4-bromomethylbenzoic acid (22.0 mmol, 4.73 g) and phosphorus pentoxide–methanesulfonic acid (P₂O₅–MsOH, 40.0 ml) were placed and stirred at 333 K. To the mixture thus obtained, 2,7-dimethoxynaphthalene (10.0 mmol, 1.88 g) was added. After the reaction mixture was stirred at 333 K for 1 h, it was poured into ice-cold water (30 ml) and the mixture was extracted with CHCl₃ (15 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give the crude product (81% yield), which was purified by reprecipitation from CHCl₃-hexane (1:1 v/v; 57% isolated yield). The isolated product was crystallized from acetone to give single-crystal.

Spectroscopic Data:

¹H NMR δ (300 MHz, CDCl₃); 3.69 (6H, s), 4.49 (4H, s), 7.20 (2H, d, J = 9.0 Hz), 7.33 (4H, d, J = 8.0 Hz), 7.63 (4H, d, J = 8.0 Hz), 7.96 (2H, d, J = 9.0 Hz) p.p.m..

¹³C NMR δ (100 MHz, CDCl₃); 32.7, 56.5, 111.4, 121.4, 125.6, 128.7, 129.5, 129.8, 132.2, 138.6, 141.9, 156.5, 196.1 p.p.m..

IR (KBr); 1666 (C=O), 1606 (Ar), 1510 (Ar) cm^-1. C₂₈H₂₂O₄Br₂; Calcd. C, 57.76; H, 3.81 found C, 57.81; H, 4.01. m.p. = 239.0–245.0 K

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 title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Partial crystal packing of the title compound, showing the intermolecular C—H···O interactions as dashed lines.

{8-[4-(Bromomethyl)benzoyl]-2,7-dimethoxynaphthalen-1-yl}[4- (bromomethyl)phenyl]methanone top

Crystal data top

C₂₈H₂₂Br₂O₄	F(000) = 1168
M_r = 582.28	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	4319 independent reflections
Radiation source: rotating anode	3916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.6°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −10→10
T_min = 0.207, T_max = 0.460	l = −29→29
41450 measured reflections

Refinement top

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(F_o²) + (0.0277P)² + 4.5808P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
4319 reflections	Δρ_max = 0.85 e Å⁻³
310 parameters	Δρ_min = −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)

Crystal data top

C₂₈H₂₂Br₂O₄	V = 2379.29 (8) Å³
M_r = 582.28	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.5948 (2) Å	µ = 4.60 mm⁻¹
b = 8.37239 (15) Å	T = 193 K
c = 24.5352 (5) Å	0.50 × 0.40 × 0.20 mm
β = 92.617 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4319 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3916 reflections with I > 2σ(I)
T_min = 0.207, T_max = 0.460	R_int = 0.079
41450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.14	Δρ_max = 0.85 e Å⁻³
4319 reflections	Δρ_min = −0.59 e Å⁻³
310 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	−0.15947 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂Br₂O₄
M_r	582.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	11.5948 (2), 8.37239 (15), 24.5352 (5)
β (°)	92.617 (1)
V (Å³)	2379.29 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.60
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.207, 0.460
No. of measured, independent and observed [I > 2σ(I)] reflections	41450, 4319, 3916
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 1.14
No. of reflections	4319
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.59

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z.

Acknowledgements

The authors would express their gratitude to Master Yuichi Kato and Mr Toyokazu Muto, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture & Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for their technical advice.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Okamoto, A., Noguchi, K. & Yonezawa, N. (2007). Acta Cryst. E63, o4120. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329. Web of Science CSD CrossRef IUCr Journals Google Scholar
Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o403. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2119

doi:10.1107/S1600536811029151

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{8-[4-(Bromo­meth­yl)benzo­yl]-2,7-dimeth­­oxy­naphthalen-1-yl}[4-(bromo­meth­yl)phen­yl]methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{8-[4-(Bromomethyl)benzoyl]-2,7-dimethoxynaphthalen-1-yl}[4-(bromomethyl)phenyl]methanone