1,8-Dibenzoyl-2,7-dimethoxy-naphthalene.

The mol-ecule of the title compound, C(26)H(20)O(4), is located on a twofold rotation axis. The two benzoyl groups are situated in an anti orientation. The dihedral angle between the mean planes of the phenyl ring and the naphthalene ring system is 80.25 (6)°. The phenyl and carbonyl groups in each benzoyl group are almost coplanar. The mol-ecular packing is stabilized by weak C-H⋯O hydrogen bonds and a π-π stacking inter-action between the phenyl rings [centroid-centroid and inter-planar distances of 3.6383 (10) and 3.294 Å, respectively].

Related literature

For related literature, see: Cohen et al. (2004 ▶); Gore & Henrick (1980 ▶); Nakaema et al. (2007 ▶).

Experimental

Crystal data

C26H20O4

M = 396.42

Monoclinic,

a = 13.9677 (4) Å

b = 10.2145 (3) Å

c = 14.6966 (4) Å

β = 109.711 (2)°

V = 1973.95 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 93 (2) K

0.50 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (; Higashi, 1999 ▶) T min = 0.838, T max = 0.930

17362 measured reflections

1807 independent reflections

1461 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.08

1807 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 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 global, I. DOI: 10.1107/S1600536808007009/is2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007009/is2282Isup2.hkl

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

C26H20O4	F000 = 832
Mr = 396.42	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Cu Kα radiation λ = 1.54187 Å
Hall symbol: -C 2yc	Cell parameters from 10115 reflections
a = 13.9677 (4) Å	θ = 3.2–68.1º
b = 10.2145 (3) Å	µ = 0.72 mm−1
c = 14.6966 (4) Å	T = 93 (2) K
β = 109.711 (2)º	Needle, colorless
V = 1973.95 (10) Å3	0.50 × 0.10 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1807 independent reflections
Radiation source: rotating anode	1461 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 10.00 pixels mm-1	θmax = 68.2º
T = 93(2) K	θmin = 5.5º
ω scans	h = −16→16
Absorption correction: numerical(NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.838, Tmax = 0.930	l = −17→17
17362 measured reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.9602P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.19 e Å−3
1807 reflections	Δρmin = −0.21 e Å−3
139 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00121 (18)
Secondary atom site location: difference Fourier map

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
O1	0.11104 (8)	0.59739 (10)	0.22559 (7)	0.0399 (3)
O2	0.26822 (8)	0.39816 (11)	0.37874 (9)	0.0530 (4)
C1	0.09424 (11)	0.39621 (13)	0.29711 (10)	0.0325 (3)
C2	0.18262 (12)	0.32529 (15)	0.33814 (11)	0.0393 (4)
C3	0.18231 (14)	0.18652 (16)	0.33535 (12)	0.0470 (4)
H3	0.2436	0.1385	0.3626	0.056*
C4	0.09246 (14)	0.12359 (15)	0.29280 (11)	0.0463 (4)
H4	0.0919	0.0306	0.2919	0.056*
C5	0.0000	0.19109 (19)	0.2500	0.0383 (5)
C6	0.0000	0.33146 (18)	0.2500	0.0319 (4)
C7	0.10671 (10)	0.54368 (14)	0.29822 (10)	0.0313 (3)
C8	0.11341 (10)	0.61894 (13)	0.38633 (10)	0.0316 (3)
C9	0.12438 (11)	0.75478 (14)	0.38552 (11)	0.0368 (4)
H9	0.1276	0.7970	0.3291	0.044*
C10	0.13055 (12)	0.82794 (16)	0.46611 (12)	0.0431 (4)
H10	0.1384	0.9203	0.4652	0.052*
C11	0.12535 (12)	0.76686 (17)	0.54845 (12)	0.0448 (4)
H11	0.1296	0.8173	0.6040	0.054*
C12	0.11397 (12)	0.63233 (17)	0.54997 (11)	0.0447 (4)
H12	0.1102	0.5906	0.6064	0.054*
C13	0.10816 (11)	0.55857 (15)	0.46934 (10)	0.0376 (4)
H13	0.1006	0.4662	0.4707	0.045*
C14	0.36309 (13)	0.3343 (2)	0.42144 (14)	0.0592 (5)
H14A	0.4171	0.3999	0.4447	0.071*
H14B	0.3771	0.2783	0.3733	0.071*
H14C	0.3606	0.2805	0.4758	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0505 (6)	0.0371 (6)	0.0351 (6)	−0.0020 (4)	0.0185 (5)	0.0020 (4)
O2	0.0393 (6)	0.0456 (7)	0.0658 (8)	0.0087 (5)	0.0068 (5)	−0.0046 (6)
C1	0.0421 (8)	0.0273 (7)	0.0311 (7)	0.0034 (6)	0.0161 (6)	0.0006 (5)
C2	0.0446 (9)	0.0366 (8)	0.0366 (8)	0.0058 (6)	0.0134 (7)	−0.0009 (6)
C3	0.0591 (10)	0.0375 (9)	0.0442 (9)	0.0160 (7)	0.0170 (8)	0.0021 (7)
C4	0.0708 (12)	0.0281 (8)	0.0428 (9)	0.0076 (7)	0.0227 (8)	0.0014 (6)
C5	0.0583 (13)	0.0268 (10)	0.0342 (11)	0.000	0.0212 (10)	0.000
C6	0.0454 (11)	0.0266 (9)	0.0278 (10)	0.000	0.0177 (9)	0.000
C7	0.0307 (7)	0.0306 (7)	0.0330 (8)	0.0011 (5)	0.0116 (6)	0.0022 (6)
C8	0.0300 (7)	0.0312 (7)	0.0333 (8)	−0.0003 (5)	0.0101 (6)	−0.0011 (6)
C9	0.0415 (8)	0.0320 (7)	0.0367 (8)	0.0012 (6)	0.0130 (6)	0.0018 (6)
C10	0.0453 (9)	0.0353 (8)	0.0478 (10)	0.0000 (6)	0.0143 (7)	−0.0069 (7)
C11	0.0426 (9)	0.0515 (10)	0.0415 (9)	−0.0001 (7)	0.0157 (7)	−0.0136 (7)
C12	0.0493 (9)	0.0534 (10)	0.0356 (9)	−0.0040 (7)	0.0199 (7)	−0.0013 (7)
C13	0.0408 (8)	0.0359 (8)	0.0381 (8)	−0.0025 (6)	0.0159 (6)	0.0013 (6)
C14	0.0465 (10)	0.0653 (11)	0.0578 (11)	0.0221 (9)	0.0070 (8)	−0.0151 (9)

O1—C7	1.2197 (16)	C8—C9	1.396 (2)
O2—C2	1.3633 (19)	C9—C10	1.378 (2)
O2—C14	1.4194 (19)	C9—H9	0.9500
C1—C2	1.382 (2)	C10—C11	1.385 (2)
C1—C6	1.4264 (17)	C10—H10	0.9500
C1—C7	1.5158 (19)	C11—C12	1.384 (2)
C2—C3	1.418 (2)	C11—H11	0.9500
C3—C4	1.360 (2)	C12—C13	1.383 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.4110 (19)	C13—H13	0.9500
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.434 (3)	C14—H14B	0.9800
C7—C8	1.4814 (19)	C14—H14C	0.9800
C8—C13	1.3908 (19)
C2—O2—C14	119.52 (13)	C13—C8—C7	122.02 (13)
C2—C1—C6	120.72 (14)	C9—C8—C7	118.88 (13)
C2—C1—C7	115.70 (13)	C10—C9—C8	120.44 (14)
C6—C1—C7	123.36 (13)	C10—C9—H9	119.8
O2—C2—C1	115.29 (13)	C8—C9—H9	119.8
O2—C2—C3	123.51 (14)	C9—C10—C11	120.00 (15)
C1—C2—C3	121.19 (15)	C9—C10—H10	120.0
C4—C3—C2	118.62 (15)	C11—C10—H10	120.0
C4—C3—H3	120.7	C12—C11—C10	120.09 (15)
C2—C3—H3	120.7	C12—C11—H11	120.0
C3—C4—C5	122.54 (15)	C10—C11—H11	120.0
C3—C4—H4	118.7	C13—C12—C11	120.05 (15)
C5—C4—H4	118.7	C13—C12—H12	120.0
C4i—C5—C4	121.50 (19)	C11—C12—H12	120.0
C4i—C5—C6	119.25 (10)	C12—C13—C8	120.31 (14)
C4—C5—C6	119.25 (10)	C12—C13—H13	119.8
C1—C6—C1i	124.75 (17)	C8—C13—H13	119.8
C1—C6—C5	117.62 (9)	O2—C14—H14A	109.5
C1i—C6—C5	117.62 (9)	O2—C14—H14B	109.5
O1—C7—C8	121.63 (13)	H14A—C14—H14B	109.5
O1—C7—C1	118.49 (12)	O2—C14—H14C	109.5
C8—C7—C1	119.88 (12)	H14A—C14—H14C	109.5
C13—C8—C9	119.10 (13)	H14B—C14—H14C	109.5
C14—O2—C2—C1	−179.05 (14)	C4—C5—C6—C1i	177.70 (9)
C14—O2—C2—C3	−0.3 (2)	C2—C1—C7—O1	97.99 (16)
C6—C1—C2—O2	178.29 (11)	C6—C1—C7—O1	−76.73 (16)
C7—C1—C2—O2	3.43 (18)	C2—C1—C7—C8	−81.97 (16)
C6—C1—C2—C3	−0.5 (2)	C6—C1—C7—C8	103.32 (14)
C7—C1—C2—C3	−175.33 (14)	O1—C7—C8—C13	179.76 (13)
O2—C2—C3—C4	−179.86 (14)	C1—C7—C8—C13	−0.29 (19)
C1—C2—C3—C4	−1.2 (2)	O1—C7—C8—C9	0.4 (2)
C2—C3—C4—C5	1.1 (2)	C1—C7—C8—C9	−179.69 (12)
C3—C4—C5—C4i	−179.31 (17)	C13—C8—C9—C10	0.4 (2)
C3—C4—C5—C6	0.69 (17)	C7—C8—C9—C10	179.81 (13)
C2—C1—C6—C1i	−177.80 (14)	C8—C9—C10—C11	−0.3 (2)
C7—C1—C6—C1i	−3.35 (9)	C9—C10—C11—C12	0.0 (2)
C2—C1—C6—C5	2.20 (14)	C10—C11—C12—C13	0.2 (2)
C7—C1—C6—C5	176.65 (9)	C11—C12—C13—C8	−0.2 (2)
C4i—C5—C6—C1	177.70 (9)	C9—C8—C13—C12	−0.1 (2)
C4—C5—C6—C1	−2.30 (9)	C7—C8—C13—C12	−179.53 (13)
C4i—C5—C6—C1i	−2.30 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ii	0.95	2.60	3.4987 (19)	159
C14—H14B···O1iii	0.98	2.39	3.344 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.95	2.60	3.4987 (19)	159
C14—H14B⋯O1ii	0.98	2.39	3.344 (2)	164

Symmetry codes: (i) ; (ii) .