[8-(4-But-oxy-benzo-yl)-2,7-dimeth-oxy-naphthalen-1-yl](4-but-oxy-phen-yl)methanone.

The mol-ecule of the title compound, C(34)H(36)O(6), is located on a twofold rotation axis. The two 4-but-oxy-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel. The dihedral angles between the benzene rings and the naphthalene ring system are 71.70 (4)°. In the crystal, the mol-ecules are connected via C-H⋯π inter-actions into a layer parallel to (010).

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Muto et al. (2010 ▶); Nakaema et al. (2008 ▶); Watanabe et al. (2010 ▶); Sasagawa et al. (2011 ▶).

Experimental

Crystal data

C34H36O6

M = 540.63

Orthorhombic,

a = 11.0930 (2) Å

b = 20.0537 (3) Å

c = 13.1409 (2) Å

V = 2923.26 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.67 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 = 0.689, T max = 0.878

50625 measured reflections

2679 independent reflections

2542 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.04

2679 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); 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) 1_8-obu-shelxl, global, I. DOI: 10.1107/S1600536811048550/gk2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048550/gk2430Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048550/gk2430Isup3.cml

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

C34H36O6	F(000) = 1152
Mr = 540.63	Dx = 1.228 Mg m−3
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2n 2ab	Cell parameters from 47089 reflections
a = 11.0930 (2) Å	θ = 3.4–68.2°
b = 20.0537 (3) Å	µ = 0.67 mm−1
c = 13.1409 (2) Å	T = 193 K
V = 2923.26 (8) Å3	Block, colorless
Z = 4	0.60 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2679 independent reflections
Radiation source: fine-focus sealed tube	2542 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.4°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −24→24
Tmin = 0.689, Tmax = 0.878	l = −15→15
50625 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.5804P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2679 reflections	Δρmax = 0.27 e Å−3
185 parameters	Δρmin = −0.16 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: 0.0027 (2)

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	0.75396 (7)	0.21648 (4)	0.08148 (6)	0.0440 (2)
O2	0.54194 (7)	0.32529 (4)	0.13838 (6)	0.0393 (2)
O3	0.98869 (7)	0.41391 (4)	0.40338 (6)	0.0393 (2)
C1	0.58364 (10)	0.07697 (5)	0.18871 (8)	0.0412 (3)
H1	0.5810	0.0296	0.1871	0.049*
C2	0.66800 (10)	0.10911 (6)	0.13181 (9)	0.0413 (3)
H2	0.7227	0.0847	0.0906	0.050*
C3	0.5000	0.11152 (7)	0.2500	0.0353 (3)
C4	0.67285 (10)	0.17957 (5)	0.13508 (8)	0.0357 (3)
C5	0.5000	0.18316 (7)	0.2500	0.0301 (3)
C6	0.59200 (9)	0.21598 (5)	0.19277 (7)	0.0308 (2)
C7	0.85144 (11)	0.18354 (7)	0.03189 (10)	0.0516 (3)
H7A	0.8196	0.1527	−0.0193	0.062*
H7B	0.8987	0.1586	0.0822	0.062*
H7C	0.9031	0.2167	−0.0013	0.062*
C8	0.60813 (9)	0.29099 (5)	0.19033 (7)	0.0304 (2)
C9	0.79477 (9)	0.28188 (5)	0.29938 (8)	0.0343 (3)
H9	0.7888	0.2347	0.2965	0.041*
C10	0.70756 (9)	0.32031 (5)	0.25103 (7)	0.0303 (2)
C11	0.89010 (10)	0.31051 (5)	0.35162 (8)	0.0361 (3)
H11	0.9489	0.2833	0.3837	0.043*
C12	0.71586 (9)	0.38984 (5)	0.25911 (8)	0.0339 (3)
H12	0.6561	0.4171	0.2283	0.041*
C13	0.89867 (9)	0.37990 (5)	0.35653 (8)	0.0335 (2)
C14	0.80960 (10)	0.41894 (5)	0.31120 (8)	0.0356 (3)
H14	0.8137	0.4661	0.3164	0.043*
C15	1.08084 (9)	0.37643 (5)	0.45496 (8)	0.0372 (3)
H15A	1.1186	0.3443	0.4075	0.045*
H15B	1.0454	0.3512	0.5124	0.045*
C16	1.17371 (10)	0.42488 (6)	0.49380 (9)	0.0426 (3)
H16A	1.1332	0.4600	0.5342	0.051*
H16B	1.2141	0.4466	0.4354	0.051*
C17	1.26786 (11)	0.39032 (8)	0.55954 (10)	0.0554 (4)
H17A	1.2301	0.3767	0.6246	0.067*
H17B	1.2955	0.3494	0.5244	0.067*
C18	1.37590 (14)	0.43398 (11)	0.58200 (19)	0.0991 (8)
H18A	1.4270	0.4122	0.6329	0.119*
H18B	1.3484	0.4771	0.6083	0.119*
H18C	1.4222	0.4409	0.5194	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0409 (4)	0.0484 (5)	0.0426 (4)	0.0008 (3)	0.0116 (3)	−0.0090 (3)
O2	0.0404 (4)	0.0392 (4)	0.0384 (4)	0.0020 (3)	−0.0056 (3)	0.0044 (3)
O3	0.0378 (4)	0.0335 (4)	0.0464 (5)	−0.0054 (3)	−0.0045 (3)	−0.0031 (3)
C1	0.0504 (7)	0.0292 (5)	0.0441 (6)	0.0062 (4)	−0.0142 (5)	−0.0048 (4)
C2	0.0433 (6)	0.0391 (6)	0.0415 (6)	0.0099 (5)	−0.0049 (5)	−0.0110 (5)
C3	0.0404 (8)	0.0297 (7)	0.0357 (7)	0.000	−0.0121 (6)	0.000
C4	0.0349 (6)	0.0395 (6)	0.0326 (5)	0.0017 (4)	−0.0035 (4)	−0.0062 (4)
C5	0.0314 (7)	0.0305 (7)	0.0285 (7)	0.000	−0.0068 (5)	0.000
C6	0.0313 (5)	0.0319 (5)	0.0292 (5)	0.0001 (4)	−0.0045 (4)	−0.0031 (4)
C7	0.0383 (6)	0.0677 (8)	0.0489 (7)	0.0064 (6)	0.0056 (5)	−0.0180 (6)
C8	0.0309 (5)	0.0337 (5)	0.0266 (5)	0.0006 (4)	0.0048 (4)	0.0007 (4)
C9	0.0373 (5)	0.0274 (5)	0.0381 (6)	−0.0016 (4)	−0.0001 (4)	0.0000 (4)
C10	0.0315 (5)	0.0310 (5)	0.0285 (5)	−0.0015 (4)	0.0046 (4)	0.0011 (4)
C11	0.0351 (5)	0.0326 (5)	0.0406 (6)	0.0006 (4)	−0.0039 (4)	0.0012 (4)
C12	0.0359 (5)	0.0316 (5)	0.0341 (5)	0.0012 (4)	0.0024 (4)	0.0030 (4)
C13	0.0336 (5)	0.0338 (5)	0.0331 (5)	−0.0054 (4)	0.0037 (4)	−0.0029 (4)
C14	0.0407 (6)	0.0270 (5)	0.0392 (6)	−0.0026 (4)	0.0038 (4)	0.0005 (4)
C15	0.0344 (5)	0.0382 (6)	0.0392 (6)	−0.0016 (4)	0.0018 (4)	−0.0031 (4)
C16	0.0382 (6)	0.0439 (6)	0.0456 (6)	−0.0028 (5)	0.0004 (5)	−0.0104 (5)
C17	0.0433 (7)	0.0710 (9)	0.0520 (7)	0.0103 (6)	−0.0045 (6)	−0.0159 (6)
C18	0.0470 (8)	0.1050 (14)	0.1453 (18)	0.0234 (9)	−0.0338 (10)	−0.0661 (13)

O1—C4	1.3615 (13)	C9—C10	1.3906 (14)
O1—C7	1.4249 (13)	C9—H9	0.9500
O2—C8	1.2159 (12)	C10—C12	1.4012 (14)
O3—C13	1.3570 (12)	C11—C13	1.3963 (14)
O3—C15	1.4384 (13)	C11—H11	0.9500
C1—C2	1.3602 (16)	C12—C14	1.3750 (15)
C1—C3	1.4106 (13)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.3942 (15)
C2—C4	1.4146 (16)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.5052 (15)
C3—C1i	1.4106 (13)	C15—H15A	0.9900
C3—C5	1.437 (2)	C15—H15B	0.9900
C4—C6	1.3828 (14)	C16—C17	1.5222 (17)
C5—C6	1.4284 (12)	C16—H16A	0.9900
C5—C6i	1.4284 (12)	C16—H16B	0.9900
C6—C8	1.5151 (14)	C17—C18	1.513 (2)
C7—H7A	0.9800	C17—H17A	0.9900
C7—H7B	0.9800	C17—H17B	0.9900
C7—H7C	0.9800	C18—H18A	0.9800
C8—C10	1.4828 (14)	C18—H18B	0.9800
C9—C11	1.3853 (14)	C18—H18C	0.9800
C4—O1—C7	119.09 (10)	C9—C11—H11	120.4
C13—O3—C15	118.31 (8)	C13—C11—H11	120.4
C2—C1—C3	122.25 (10)	C14—C12—C10	120.65 (10)
C2—C1—H1	118.9	C14—C12—H12	119.7
C3—C1—H1	118.9	C10—C12—H12	119.7
C1—C2—C4	118.87 (10)	O3—C13—C14	115.67 (9)
C1—C2—H2	120.6	O3—C13—C11	124.88 (10)
C4—C2—H2	120.6	C14—C13—C11	119.45 (9)
C1i—C3—C1	121.15 (13)	C12—C14—C13	120.68 (9)
C1i—C3—C5	119.42 (7)	C12—C14—H14	119.7
C1—C3—C5	119.42 (7)	C13—C14—H14	119.7
O1—C4—C6	115.16 (9)	O3—C15—C16	108.00 (9)
O1—C4—C2	123.54 (10)	O3—C15—H15A	110.1
C6—C4—C2	121.29 (10)	C16—C15—H15A	110.1
C6—C5—C6i	125.13 (13)	O3—C15—H15B	110.1
C6—C5—C3	117.44 (6)	C16—C15—H15B	110.1
C6i—C5—C3	117.44 (6)	H15A—C15—H15B	108.4
C4—C6—C5	120.58 (10)	C15—C16—C17	111.61 (10)
C4—C6—C8	115.85 (9)	C15—C16—H16A	109.3
C5—C6—C8	123.57 (9)	C17—C16—H16A	109.3
O1—C7—H7A	109.5	C15—C16—H16B	109.3
O1—C7—H7B	109.5	C17—C16—H16B	109.3
H7A—C7—H7B	109.5	H16A—C16—H16B	108.0
O1—C7—H7C	109.5	C18—C17—C16	113.00 (14)
H7A—C7—H7C	109.5	C18—C17—H17A	109.0
H7B—C7—H7C	109.5	C16—C17—H17A	109.0
O2—C8—C10	121.79 (9)	C18—C17—H17B	109.0
O2—C8—C6	120.15 (9)	C16—C17—H17B	109.0
C10—C8—C6	118.05 (8)	H17A—C17—H17B	107.8
C11—C9—C10	121.85 (9)	C17—C18—H18A	109.5
C11—C9—H9	119.1	C17—C18—H18B	109.5
C10—C9—H9	119.1	H18A—C18—H18B	109.5
C9—C10—C12	118.11 (9)	C17—C18—H18C	109.5
C9—C10—C8	122.92 (9)	H18A—C18—H18C	109.5
C12—C10—C8	118.97 (9)	H18B—C18—H18C	109.5
C9—C11—C13	119.21 (10)
C3—C1—C2—C4	0.70 (15)	C4—C6—C8—C10	−76.66 (11)
C2—C1—C3—C1i	−177.57 (11)	C5—C6—C8—C10	103.44 (10)
C2—C1—C3—C5	2.43 (11)	C11—C9—C10—C12	−2.11 (15)
C7—O1—C4—C6	170.91 (9)	C11—C9—C10—C8	176.85 (9)
C7—O1—C4—C2	−10.34 (15)	O2—C8—C10—C9	−170.62 (9)
C1—C2—C4—O1	179.73 (9)	C6—C8—C10—C9	8.16 (14)
C1—C2—C4—C6	−1.59 (16)	O2—C8—C10—C12	8.33 (14)
C1i—C3—C5—C6	175.43 (7)	C6—C8—C10—C12	−172.88 (9)
C1—C3—C5—C6	−4.57 (7)	C10—C9—C11—C13	0.42 (16)
C1i—C3—C5—C6i	−4.57 (7)	C9—C10—C12—C14	1.70 (15)
C1—C3—C5—C6i	175.43 (7)	C8—C10—C12—C14	−177.30 (9)
O1—C4—C6—C5	178.06 (7)	C15—O3—C13—C14	177.64 (9)
C2—C4—C6—C5	−0.73 (14)	C15—O3—C13—C11	−2.08 (14)
O1—C4—C6—C8	−1.84 (13)	C9—C11—C13—O3	−178.58 (9)
C2—C4—C6—C8	179.37 (9)	C9—C11—C13—C14	1.70 (15)
C6i—C5—C6—C4	−176.24 (10)	C10—C12—C14—C13	0.38 (15)
C3—C5—C6—C4	3.76 (10)	O3—C13—C14—C12	178.15 (9)
C6i—C5—C6—C8	3.65 (7)	C11—C13—C14—C12	−2.11 (15)
C3—C5—C6—C8	−176.35 (7)	C13—O3—C15—C16	176.09 (9)
C4—C6—C8—O2	102.15 (11)	O3—C15—C16—C17	173.78 (9)
C5—C6—C8—O2	−77.75 (12)	C15—C16—C17—C18	168.20 (12)

Cg is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cgii	0.98	2.68	3.5056 (14)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cgi	0.98	2.68	3.5056 (14)	142

Symmetry code: (i) .