[2,7-Dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone.

In the title compound, C(28)H(24)O(4), the two 4-methyl-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, the dihedral angle between the two phenyl rings being 9.64 (7)°. The dihedral angles between the two phenyl rings and the naphthalene ring system are 71.82 (6) and 71.58 (6)°. In the crystal, inter-molecular C-H⋯O inter-actions between the carbonyl oxygen and aromatic hydrogen are observed.

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimeth­oxy­naphth­alene, see: Okamoto & Yonezawa (2009 ▶). For related structures, see: Nakaema et al. (2007 ▶, 2008 ▶); Watanabe et al. (2010a ▶,b ▶).

Experimental

Crystal data

C28H24O4

M = 424.47

Orthorhombic,

a = 20.0334 (3) Å

b = 13.4311 (2) Å

c = 7.94771 (10) Å

V = 2138.49 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 193 K

0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.604, T max = 0.873

33150 measured reflections

2110 independent reflections

2041 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.17

2110 reflections

293 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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/S1600536810039620/om2367sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039620/om2367Isup2.hkl

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

C28H24O4	F(000) = 896
Mr = 424.47	Dx = 1.318 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2c -2n	Cell parameters from 31782 reflections
a = 20.0334 (3) Å	θ = 3.3–68.2°
b = 13.4311 (2) Å	µ = 0.70 mm−1
c = 7.94771 (10) Å	T = 193 K
V = 2138.49 (5) Å3	Block, colorless
Z = 4	0.60 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2110 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.0°
ω scans	h = −24→24
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −16→16
Tmin = 0.604, Tmax = 0.873	l = −9→9
33150 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.3088P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.002
2110 reflections	Δρmax = 0.18 e Å−3
293 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (5)

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	0.14819 (8)	0.11387 (12)	0.5115 (2)	0.0340 (4)
O2	0.14078 (8)	0.32719 (13)	0.2589 (2)	0.0368 (4)
O3	0.06372 (8)	−0.05143 (12)	0.2673 (3)	0.0449 (4)
O4	0.03319 (8)	0.46452 (13)	0.4971 (3)	0.0444 (4)
C1	0.05479 (10)	0.11760 (16)	0.3328 (3)	0.0300 (5)
C2	0.02338 (11)	0.02950 (17)	0.2891 (3)	0.0361 (5)
C3	−0.04660 (12)	0.0239 (2)	0.2705 (4)	0.0426 (6)
H3	−0.0672	−0.0361	0.2345	0.051*
C4	−0.08397 (11)	0.1059 (2)	0.3048 (3)	0.0420 (6)
H4	−0.1311	0.1020	0.2935	0.050*
C5	−0.05501 (10)	0.19654 (19)	0.3567 (3)	0.0369 (5)
C6	−0.09500 (11)	0.2789 (2)	0.4003 (4)	0.0436 (6)
H6	−0.1422	0.2727	0.3944	0.052*
C7	−0.06805 (12)	0.3673 (2)	0.4509 (4)	0.0428 (6)
H7	−0.0960	0.4215	0.4816	0.051*
C8	0.00175 (12)	0.37696 (17)	0.4567 (3)	0.0361 (5)
C9	0.04339 (10)	0.29876 (17)	0.4152 (3)	0.0303 (5)
C10	0.01624 (10)	0.20501 (17)	0.3670 (3)	0.0309 (5)
C11	0.12923 (11)	0.11221 (15)	0.3659 (3)	0.0282 (5)
C12	0.17684 (11)	0.10505 (15)	0.2237 (3)	0.0274 (5)
C13	0.15505 (11)	0.10444 (17)	0.0569 (3)	0.0330 (5)
H13	0.1086	0.1075	0.0330	0.040*
C14	0.20036 (12)	0.09938 (16)	−0.0735 (3)	0.0343 (5)
H14	0.1847	0.0991	−0.1863	0.041*
C15	0.26866 (11)	0.09473 (16)	−0.0420 (3)	0.0332 (5)
C16	0.29032 (11)	0.09517 (17)	0.1250 (3)	0.0343 (5)
H16	0.3367	0.0916	0.1486	0.041*
C17	0.24524 (11)	0.10078 (15)	0.2565 (3)	0.0314 (5)
H17	0.2609	0.1017	0.3693	0.038*
C18	0.11740 (11)	0.32131 (15)	0.4002 (3)	0.0286 (5)
C19	0.15908 (11)	0.33410 (15)	0.5519 (3)	0.0280 (5)
C20	0.13218 (11)	0.33242 (17)	0.7139 (3)	0.0326 (5)
H20	0.0855	0.3239	0.7283	0.039*
C21	0.17245 (12)	0.34296 (17)	0.8529 (3)	0.0356 (5)
H21	0.1532	0.3424	0.9621	0.043*
C22	0.24135 (12)	0.35449 (16)	0.8353 (3)	0.0335 (5)
C23	0.26816 (12)	0.35582 (17)	0.6736 (3)	0.0345 (5)
H23	0.3149	0.3638	0.6594	0.041*
C24	0.22803 (11)	0.34573 (16)	0.5340 (3)	0.0301 (5)
H24	0.2473	0.3467	0.4248	0.036*
C25	0.03540 (14)	−0.14711 (18)	0.2950 (4)	0.0489 (7)
H25A	0.0694	−0.1983	0.2755	0.059*
H25B	−0.0020	−0.1573	0.2173	0.059*
H25C	0.0193	−0.1516	0.4111	0.059*
C26	−0.00659 (15)	0.5493 (2)	0.5335 (5)	0.0575 (8)
H26A	0.0224	0.6057	0.5614	0.069*
H26B	−0.0358	0.5348	0.6292	0.069*
H26C	−0.0338	0.5661	0.4350	0.069*
C27	0.31772 (13)	0.0894 (2)	−0.1857 (4)	0.0450 (6)
H27A	0.2936	0.0769	−0.2909	0.054*
H27B	0.3495	0.0353	−0.1654	0.054*
H27C	0.3419	0.1527	−0.1942	0.054*
C28	0.28470 (13)	0.3658 (2)	0.9887 (4)	0.0442 (6)
H28A	0.2668	0.3247	1.0802	0.053*
H28B	0.2853	0.4357	1.0238	0.053*
H28C	0.3302	0.3442	0.9622	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0338 (8)	0.0407 (9)	0.0276 (9)	−0.0016 (6)	−0.0026 (7)	0.0006 (7)
O2	0.0351 (9)	0.0514 (10)	0.0238 (9)	−0.0047 (7)	0.0037 (7)	0.0015 (7)
O3	0.0372 (8)	0.0403 (9)	0.0573 (11)	−0.0093 (7)	0.0077 (8)	−0.0081 (9)
O4	0.0402 (9)	0.0398 (9)	0.0532 (12)	0.0093 (7)	0.0005 (9)	−0.0030 (8)
C1	0.0260 (10)	0.0401 (11)	0.0237 (10)	−0.0036 (8)	0.0020 (9)	0.0017 (9)
C2	0.0338 (11)	0.0455 (12)	0.0289 (12)	−0.0074 (9)	0.0028 (10)	−0.0013 (10)
C3	0.0353 (11)	0.0551 (14)	0.0374 (13)	−0.0168 (11)	−0.0020 (11)	−0.0008 (12)
C4	0.0258 (10)	0.0635 (16)	0.0368 (14)	−0.0094 (10)	−0.0037 (10)	0.0080 (12)
C5	0.0262 (10)	0.0545 (13)	0.0300 (12)	−0.0008 (10)	−0.0020 (10)	0.0094 (11)
C6	0.0239 (10)	0.0633 (15)	0.0437 (15)	0.0035 (10)	−0.0006 (10)	0.0122 (12)
C7	0.0313 (11)	0.0558 (14)	0.0414 (14)	0.0125 (10)	0.0054 (11)	0.0095 (12)
C8	0.0361 (11)	0.0434 (12)	0.0286 (12)	0.0050 (10)	0.0008 (10)	0.0041 (10)
C9	0.0263 (10)	0.0402 (11)	0.0244 (11)	0.0029 (8)	−0.0013 (9)	0.0046 (9)
C10	0.0267 (10)	0.0443 (12)	0.0218 (10)	−0.0018 (9)	−0.0003 (9)	0.0057 (9)
C11	0.0302 (11)	0.0267 (9)	0.0275 (12)	−0.0023 (8)	−0.0017 (10)	0.0005 (9)
C12	0.0264 (10)	0.0272 (9)	0.0286 (12)	−0.0021 (7)	−0.0009 (9)	−0.0001 (8)
C13	0.0281 (11)	0.0408 (12)	0.0303 (12)	−0.0005 (9)	−0.0048 (9)	0.0018 (10)
C14	0.0387 (12)	0.0381 (11)	0.0262 (11)	0.0005 (9)	−0.0004 (10)	0.0009 (9)
C15	0.0360 (12)	0.0292 (10)	0.0344 (13)	−0.0012 (9)	0.0046 (10)	0.0012 (9)
C16	0.0267 (11)	0.0370 (11)	0.0393 (13)	−0.0026 (8)	0.0011 (10)	0.0001 (10)
C17	0.0294 (10)	0.0331 (10)	0.0317 (12)	−0.0024 (8)	−0.0034 (9)	0.0007 (10)
C18	0.0304 (10)	0.0279 (9)	0.0276 (12)	0.0009 (8)	0.0023 (9)	0.0013 (8)
C19	0.0298 (10)	0.0264 (10)	0.0277 (11)	0.0009 (8)	0.0005 (9)	0.0010 (8)
C20	0.0291 (10)	0.0398 (12)	0.0289 (12)	−0.0008 (9)	0.0018 (9)	0.0002 (10)
C21	0.0404 (12)	0.0405 (12)	0.0259 (12)	−0.0007 (9)	0.0031 (10)	0.0032 (10)
C22	0.0389 (12)	0.0283 (10)	0.0331 (13)	0.0001 (8)	−0.0061 (11)	0.0012 (9)
C23	0.0300 (11)	0.0341 (11)	0.0393 (14)	−0.0002 (9)	−0.0024 (10)	−0.0005 (10)
C24	0.0310 (10)	0.0312 (10)	0.0280 (11)	0.0014 (8)	0.0044 (10)	−0.0004 (9)
C25	0.0531 (15)	0.0413 (12)	0.0523 (17)	−0.0147 (11)	0.0089 (14)	−0.0081 (12)
C26	0.0583 (16)	0.0509 (15)	0.063 (2)	0.0204 (13)	−0.0051 (16)	−0.0145 (15)
C27	0.0419 (13)	0.0522 (14)	0.0408 (15)	0.0002 (10)	0.0110 (12)	0.0014 (12)
C28	0.0500 (15)	0.0459 (13)	0.0368 (14)	−0.0022 (11)	−0.0114 (12)	0.0028 (12)

O1—C11	1.218 (3)	C15—C16	1.396 (4)
O2—C18	1.219 (3)	C15—C27	1.508 (3)
O3—C2	1.366 (3)	C16—C17	1.384 (3)
O3—C25	1.422 (3)	C16—H16	0.9500
O4—C8	1.372 (3)	C17—H17	0.9500
O4—C26	1.420 (3)	C18—C19	1.477 (3)
C1—C2	1.385 (3)	C19—C20	1.395 (3)
C1—C10	1.431 (3)	C19—C24	1.398 (3)
C1—C11	1.516 (3)	C20—C21	1.375 (3)
C2—C3	1.412 (3)	C20—H20	0.9500
C3—C4	1.359 (4)	C21—C22	1.396 (3)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.410 (4)	C22—C23	1.393 (3)
C4—H4	0.9500	C22—C28	1.505 (3)
C5—C6	1.409 (4)	C23—C24	1.377 (3)
C5—C10	1.434 (3)	C23—H23	0.9500
C6—C7	1.365 (4)	C24—H24	0.9500
C6—H6	0.9500	C25—H25A	0.9800
C7—C8	1.405 (3)	C25—H25B	0.9800
C7—H7	0.9500	C25—H25C	0.9800
C8—C9	1.381 (3)	C26—H26A	0.9800
C9—C10	1.424 (3)	C26—H26B	0.9800
C9—C18	1.518 (3)	C26—H26C	0.9800
C11—C12	1.482 (3)	C27—H27A	0.9800
C12—C13	1.396 (3)	C27—H27B	0.9800
C12—C17	1.396 (3)	C27—H27C	0.9800
C13—C14	1.379 (3)	C28—H28A	0.9800
C13—H13	0.9500	C28—H28B	0.9800
C14—C15	1.392 (3)	C28—H28C	0.9800
C14—H14	0.9500
C2—O3—C25	117.63 (18)	C15—C16—H16	119.5
C8—O4—C26	118.5 (2)	C16—C17—C12	120.1 (2)
C2—C1—C10	120.23 (19)	C16—C17—H17	119.9
C2—C1—C11	116.73 (18)	C12—C17—H17	119.9
C10—C1—C11	122.48 (18)	O2—C18—C19	121.84 (19)
O3—C2—C1	116.31 (18)	O2—C18—C9	117.41 (19)
O3—C2—C3	122.2 (2)	C19—C18—C9	120.75 (18)
C1—C2—C3	121.5 (2)	C20—C19—C24	118.5 (2)
C4—C3—C2	118.9 (2)	C20—C19—C18	122.2 (2)
C4—C3—H3	120.6	C24—C19—C18	119.2 (2)
C2—C3—H3	120.6	C21—C20—C19	120.8 (2)
C3—C4—C5	122.1 (2)	C21—C20—H20	119.6
C3—C4—H4	118.9	C19—C20—H20	119.6
C5—C4—H4	118.9	C20—C21—C22	120.7 (2)
C6—C5—C4	121.05 (19)	C20—C21—H21	119.6
C6—C5—C10	119.3 (2)	C22—C21—H21	119.6
C4—C5—C10	119.6 (2)	C23—C22—C21	118.4 (2)
C7—C6—C5	122.03 (19)	C23—C22—C28	121.6 (2)
C7—C6—H6	119.0	C21—C22—C28	120.0 (2)
C5—C6—H6	119.0	C24—C23—C22	121.1 (2)
C6—C7—C8	118.9 (2)	C24—C23—H23	119.4
C6—C7—H7	120.5	C22—C23—H23	119.4
C8—C7—H7	120.5	C23—C24—C19	120.4 (2)
O4—C8—C9	115.50 (19)	C23—C24—H24	119.8
O4—C8—C7	122.9 (2)	C19—C24—H24	119.8
C9—C8—C7	121.5 (2)	O3—C25—H25A	109.5
C8—C9—C10	120.40 (18)	O3—C25—H25B	109.5
C8—C9—C18	117.19 (19)	H25A—C25—H25B	109.5
C10—C9—C18	121.89 (18)	O3—C25—H25C	109.5
C9—C10—C1	124.76 (17)	H25A—C25—H25C	109.5
C9—C10—C5	117.74 (19)	H25B—C25—H25C	109.5
C1—C10—C5	117.5 (2)	O4—C26—H26A	109.5
O1—C11—C12	121.7 (2)	O4—C26—H26B	109.5
O1—C11—C1	118.1 (2)	H26A—C26—H26B	109.5
C12—C11—C1	120.25 (19)	O4—C26—H26C	109.5
C13—C12—C17	118.9 (2)	H26A—C26—H26C	109.5
C13—C12—C11	121.6 (2)	H26B—C26—H26C	109.5
C17—C12—C11	119.5 (2)	C15—C27—H27A	109.5
C14—C13—C12	120.5 (2)	C15—C27—H27B	109.5
C14—C13—H13	119.7	H27A—C27—H27B	109.5
C12—C13—H13	119.7	C15—C27—H27C	109.5
C13—C14—C15	120.9 (2)	H27A—C27—H27C	109.5
C13—C14—H14	119.5	H27B—C27—H27C	109.5
C15—C14—H14	119.5	C22—C28—H28A	109.5
C14—C15—C16	118.4 (2)	C22—C28—H28B	109.5
C14—C15—C27	120.4 (2)	H28A—C28—H28B	109.5
C16—C15—C27	121.2 (2)	C22—C28—H28C	109.5
C17—C16—C15	121.0 (2)	H28A—C28—H28C	109.5
C17—C16—H16	119.5	H28B—C28—H28C	109.5
C25—O3—C2—C1	153.3 (3)	C10—C1—C11—O1	67.9 (3)
C25—O3—C2—C3	−25.9 (4)	C2—C1—C11—C12	76.4 (3)
C10—C1—C2—O3	−176.7 (2)	C10—C1—C11—C12	−112.1 (2)
C11—C1—C2—O3	−5.0 (3)	O1—C11—C12—C13	−179.2 (2)
C10—C1—C2—C3	2.5 (4)	C1—C11—C12—C13	0.9 (3)
C11—C1—C2—C3	174.1 (2)	O1—C11—C12—C17	−0.5 (3)
O3—C2—C3—C4	175.7 (3)	C1—C11—C12—C17	179.60 (18)
C1—C2—C3—C4	−3.4 (4)	C17—C12—C13—C14	0.2 (3)
C2—C3—C4—C5	0.7 (4)	C11—C12—C13—C14	178.9 (2)
C3—C4—C5—C6	−176.6 (3)	C12—C13—C14—C15	0.0 (3)
C3—C4—C5—C10	2.8 (4)	C13—C14—C15—C16	0.1 (3)
C4—C5—C6—C7	−180.0 (3)	C13—C14—C15—C27	−179.9 (2)
C10—C5—C6—C7	0.6 (4)	C14—C15—C16—C17	−0.4 (3)
C5—C6—C7—C8	1.1 (4)	C27—C15—C16—C17	179.5 (2)
C26—O4—C8—C9	177.1 (3)	C15—C16—C17—C12	0.7 (3)
C26—O4—C8—C7	−0.4 (4)	C13—C12—C17—C16	−0.6 (3)
C6—C7—C8—O4	176.4 (2)	C11—C12—C17—C16	−179.3 (2)
C6—C7—C8—C9	−1.1 (4)	C8—C9—C18—O2	−104.1 (3)
O4—C8—C9—C10	−178.4 (2)	C10—C9—C18—O2	67.6 (3)
C7—C8—C9—C10	−0.8 (4)	C8—C9—C18—C19	76.7 (3)
O4—C8—C9—C18	−6.6 (3)	C10—C9—C18—C19	−111.6 (2)
C7—C8—C9—C18	171.0 (2)	O2—C18—C19—C20	176.7 (2)
C8—C9—C10—C1	−175.5 (2)	C9—C18—C19—C20	−4.1 (3)
C18—C9—C10—C1	13.1 (4)	O2—C18—C19—C24	−5.0 (3)
C8—C9—C10—C5	2.5 (3)	C9—C18—C19—C24	174.19 (18)
C18—C9—C10—C5	−169.0 (2)	C24—C19—C20—C21	0.6 (3)
C2—C1—C10—C9	179.0 (2)	C18—C19—C20—C21	178.9 (2)
C11—C1—C10—C9	7.9 (4)	C19—C20—C21—C22	−0.7 (3)
C2—C1—C10—C5	1.1 (4)	C20—C21—C22—C23	0.5 (3)
C11—C1—C10—C5	−170.1 (2)	C20—C21—C22—C28	−179.9 (2)
C6—C5—C10—C9	−2.4 (4)	C21—C22—C23—C24	−0.2 (3)
C4—C5—C10—C9	178.2 (2)	C28—C22—C23—C24	−179.8 (2)
C6—C5—C10—C1	175.8 (2)	C22—C23—C24—C19	0.1 (3)
C4—C5—C10—C1	−3.7 (4)	C20—C19—C24—C23	−0.4 (3)
C2—C1—C11—O1	−103.5 (3)	C18—C19—C24—C23	−178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.95	2.52	3.465 (3)	175
C21—H21···O2ii	0.95	2.38	3.295 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.95	2.52	3.465 (3)	175
C21—H21⋯O2ii	0.95	2.38	3.295 (3)	162

Symmetry codes: (i) ; (ii) .