[8-(4-Phen-oxy-benzo-yl)-2,7-bis-(propan-2-yl-oxy)naphthalen-1-yl](4-phen-oxy-phen-yl)methanone.

The entire title mol-ecule, C(42)H(36)O(6), is completed by the application of a twofold axis. The 4-phen-oxy-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel. The dihedral angle between the best planes of the benzene rings of the benzoyl moieties and the naphthalene ring system is 70.52 (5)° and that between the best planes of the benzene rings of the phen-oxy groups and the naphthalene ring system is 27.80 (6)°. In the crystal, mol-ecules are linked into a three-dimensional architecture by C-H⋯O and C-H⋯π inter-actions.

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 ▶); Sasagawa et al. (2012 ▶); Muto et al. (2010 ▶); Nakaema et al. (2008 ▶).

Experimental

Crystal data

C42H36O6

M = 636.71

Monoclinic,

a = 22.7084 (4) Å

b = 10.3582 (2) Å

c = 14.7152 (3) Å

β = 100.106 (1)°

V = 3407.58 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.66 mm−1

T = 193 K

0.60 × 0.60 × 0.50 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.693, T max = 0.734

28911 measured reflections

3101 independent reflections

2749 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.04

3101 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000913/pk2459sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000913/pk2459Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000913/pk2459Isup3.cml

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

C42H36O6	F(000) = 1344
Mr = 636.71	Dx = 1.241 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -C 2yc	Cell parameters from 26902 reflections
a = 22.7084 (4) Å	θ = 3.1–68.3°
b = 10.3582 (2) Å	µ = 0.66 mm−1
c = 14.7152 (3) Å	T = 193 K
β = 100.106 (1)°	Block, colorless
V = 3407.58 (11) Å3	0.60 × 0.60 × 0.50 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3101 independent reflections
Radiation source: rotaing anode	2749 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.000 pixels mm-1	θmax = 68.3°, θmin = 4.0°
ω scans	h = −27→27
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.693, Tmax = 0.734	l = −17→17
28911 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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0477P)2 + 1.7648P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3101 reflections	Δρmax = 0.21 e Å−3
221 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: 0.00263 (12)

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	0.43879 (4)	0.44016 (8)	0.67336 (6)	0.0378 (2)
O2	0.34771 (4)	0.63044 (8)	0.78791 (7)	0.0418 (3)
O3	0.40230 (5)	0.16418 (9)	1.04457 (6)	0.0475 (3)
C3	0.5000	0.83092 (15)	0.7500	0.0279 (4)
C8	0.42720 (5)	0.40189 (11)	0.82730 (8)	0.0288 (3)
C7	0.43753 (5)	0.48524 (11)	0.74958 (8)	0.0290 (3)
C2	0.5000	0.69308 (15)	0.7500	0.0263 (3)
C5	0.39876 (6)	0.83609 (12)	0.78052 (9)	0.0341 (3)
H5	0.3651	0.8834	0.7926	0.041*
C1	0.44642 (5)	0.62900 (11)	0.76338 (8)	0.0281 (3)
C6	0.39740 (5)	0.70012 (11)	0.77734 (8)	0.0317 (3)
C9	0.41352 (6)	0.27221 (11)	0.81026 (8)	0.0312 (3)
H9	0.4104	0.2394	0.7493	0.037*
C13	0.43221 (6)	0.44792 (11)	0.91753 (8)	0.0340 (3)
H13	0.4417	0.5362	0.9301	0.041*
C10	0.40443 (6)	0.19034 (11)	0.88074 (8)	0.0326 (3)
H10	0.3947	0.1022	0.8683	0.039*
C11	0.40974 (6)	0.23839 (12)	0.96986 (8)	0.0330 (3)
C12	0.42366 (6)	0.36733 (12)	0.98865 (9)	0.0369 (3)
H12	0.4272	0.3996	1.0498	0.044*
C14	0.38932 (6)	0.03327 (12)	1.03096 (8)	0.0374 (3)
C15	0.43487 (7)	−0.05536 (14)	1.05092 (9)	0.0429 (3)
H15	0.4750	−0.0273	1.0699	0.052*
C20	0.28915 (6)	0.68545 (14)	0.75933 (11)	0.0458 (4)
H20	0.2858	0.7664	0.7951	0.055*
C16	0.42179 (8)	−0.18549 (14)	1.04313 (10)	0.0509 (4)
H16	0.4530	−0.2472	1.0576	0.061*
C19	0.33118 (7)	−0.00546 (14)	1.00293 (11)	0.0475 (4)
H19	0.2999	0.0563	0.9898	0.057*
C17	0.36410 (8)	−0.22609 (14)	1.01469 (11)	0.0554 (4)
H17	0.3553	−0.3157	1.0092	0.066*
C18	0.31893 (8)	−0.13676 (16)	0.99415 (12)	0.0568 (4)
H18	0.2790	−0.1650	0.9738	0.068*
C21	0.24694 (7)	0.58531 (18)	0.78572 (15)	0.0677 (5)
H21A	0.2491	0.5069	0.7492	0.102*
H21B	0.2060	0.6190	0.7736	0.102*
H21C	0.2583	0.5650	0.8515	0.102*
C22	0.27768 (9)	0.7160 (2)	0.65854 (14)	0.0779 (6)
H22B	0.3046	0.7852	0.6462	0.117*
H22C	0.2361	0.7439	0.6398	0.117*
H22A	0.2848	0.6388	0.6235	0.117*
C4	0.44890 (5)	0.89855 (11)	0.76600 (8)	0.0310 (3)
H4	0.4496	0.9903	0.7667	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0591 (6)	0.0264 (4)	0.0288 (5)	−0.0060 (4)	0.0102 (4)	−0.0024 (3)
O2	0.0344 (5)	0.0291 (5)	0.0639 (6)	−0.0017 (4)	0.0141 (4)	0.0045 (4)
O3	0.0838 (7)	0.0299 (5)	0.0307 (5)	−0.0094 (5)	0.0151 (5)	0.0025 (4)
C3	0.0356 (9)	0.0225 (8)	0.0252 (8)	0.000	0.0040 (7)	0.000
C8	0.0332 (6)	0.0226 (6)	0.0307 (6)	−0.0009 (5)	0.0062 (5)	−0.0004 (5)
C7	0.0330 (6)	0.0238 (6)	0.0300 (6)	−0.0019 (5)	0.0047 (5)	−0.0010 (5)
C2	0.0356 (9)	0.0211 (8)	0.0217 (8)	0.000	0.0041 (6)	0.000
C5	0.0372 (7)	0.0263 (6)	0.0402 (7)	0.0041 (5)	0.0102 (5)	−0.0019 (5)
C1	0.0368 (6)	0.0215 (6)	0.0260 (6)	−0.0007 (5)	0.0053 (5)	0.0009 (4)
C6	0.0351 (6)	0.0264 (6)	0.0342 (6)	−0.0033 (5)	0.0079 (5)	0.0005 (5)
C9	0.0414 (7)	0.0249 (6)	0.0282 (6)	−0.0028 (5)	0.0082 (5)	−0.0030 (5)
C13	0.0459 (7)	0.0220 (6)	0.0339 (7)	−0.0032 (5)	0.0071 (5)	−0.0037 (5)
C10	0.0445 (7)	0.0203 (6)	0.0336 (7)	−0.0039 (5)	0.0091 (5)	−0.0015 (5)
C11	0.0424 (7)	0.0276 (6)	0.0299 (6)	−0.0008 (5)	0.0090 (5)	0.0036 (5)
C12	0.0528 (8)	0.0301 (6)	0.0280 (6)	−0.0022 (6)	0.0079 (5)	−0.0035 (5)
C14	0.0569 (8)	0.0298 (6)	0.0274 (6)	−0.0047 (6)	0.0120 (6)	0.0054 (5)
C15	0.0485 (8)	0.0450 (8)	0.0350 (7)	−0.0007 (6)	0.0067 (6)	0.0031 (6)
C20	0.0350 (7)	0.0392 (7)	0.0631 (9)	−0.0008 (6)	0.0086 (6)	0.0002 (7)
C16	0.0712 (10)	0.0380 (8)	0.0445 (8)	0.0107 (7)	0.0131 (7)	0.0081 (6)
C19	0.0496 (8)	0.0442 (8)	0.0497 (8)	0.0024 (6)	0.0114 (7)	0.0080 (6)
C17	0.0856 (12)	0.0317 (7)	0.0525 (9)	−0.0101 (8)	0.0222 (8)	0.0046 (6)
C18	0.0566 (9)	0.0569 (10)	0.0590 (10)	−0.0201 (8)	0.0159 (8)	0.0014 (8)
C21	0.0414 (8)	0.0627 (11)	0.1020 (15)	−0.0074 (8)	0.0205 (9)	0.0098 (10)
C22	0.0671 (12)	0.0893 (14)	0.0687 (12)	−0.0250 (10)	−0.0120 (9)	0.0140 (11)
C4	0.0408 (7)	0.0190 (5)	0.0332 (6)	0.0015 (5)	0.0064 (5)	−0.0017 (5)

O1—C7	1.2198 (14)	C11—C12	1.3891 (17)
O2—C6	1.3711 (14)	C12—H12	0.9500
O2—C20	1.4401 (16)	C14—C19	1.372 (2)
O3—C11	1.3760 (14)	C14—C15	1.376 (2)
O3—C14	1.3947 (15)	C15—C16	1.381 (2)
C3—C4	1.4101 (14)	C15—H15	0.9500
C3—C4i	1.4102 (14)	C20—C22	1.494 (2)
C3—C2	1.428 (2)	C20—C21	1.509 (2)
C8—C9	1.3916 (16)	C20—H20	1.0000
C8—C13	1.3966 (17)	C16—C17	1.370 (2)
C8—C7	1.4841 (16)	C16—H16	0.9500
C7—C1	1.5116 (16)	C19—C18	1.390 (2)
C2—C1i	1.4295 (13)	C19—H19	0.9500
C2—C1	1.4295 (13)	C17—C18	1.375 (2)
C5—C4	1.3586 (17)	C17—H17	0.9500
C5—C6	1.4094 (17)	C18—H18	0.9500
C5—H5	0.9500	C21—H21A	0.9800
C1—C6	1.3800 (17)	C21—H21B	0.9800
C9—C10	1.3829 (17)	C21—H21C	0.9800
C9—H9	0.9500	C22—H22B	0.9800
C13—C12	1.3788 (18)	C22—H22C	0.9800
C13—H13	0.9500	C22—H22A	0.9800
C10—C11	1.3881 (17)	C4—H4	0.9500
C10—H10	0.9500
C6—O2—C20	119.65 (10)	C19—C14—O3	119.69 (13)
C11—O3—C14	118.75 (10)	C15—C14—O3	119.09 (13)
C4—C3—C4i	120.42 (15)	C14—C15—C16	119.40 (14)
C4—C3—C2	119.79 (7)	C14—C15—H15	120.3
C4i—C3—C2	119.79 (7)	C16—C15—H15	120.3
C9—C8—C13	118.63 (11)	O2—C20—C22	111.41 (14)
C9—C8—C7	118.90 (10)	O2—C20—C21	104.39 (12)
C13—C8—C7	122.45 (10)	C22—C20—C21	113.15 (15)
O1—C7—C8	121.21 (10)	O2—C20—H20	109.3
O1—C7—C1	118.46 (10)	C22—C20—H20	109.3
C8—C7—C1	120.33 (10)	C21—C20—H20	109.3
C3—C2—C1i	117.67 (7)	C17—C16—C15	120.36 (15)
C3—C2—C1	117.67 (7)	C17—C16—H16	119.8
C1i—C2—C1	124.67 (14)	C15—C16—H16	119.8
C4—C5—C6	119.00 (11)	C14—C19—C18	118.71 (14)
C4—C5—H5	120.5	C14—C19—H19	120.6
C6—C5—H5	120.5	C18—C19—H19	120.6
C6—C1—C2	120.06 (11)	C16—C17—C18	119.81 (14)
C6—C1—C7	116.97 (10)	C16—C17—H17	120.1
C2—C1—C7	122.40 (11)	C18—C17—H17	120.1
O2—C6—C1	115.93 (10)	C17—C18—C19	120.58 (15)
O2—C6—C5	122.41 (11)	C17—C18—H18	119.7
C1—C6—C5	121.65 (11)	C19—C18—H18	119.7
C10—C9—C8	120.99 (11)	C20—C21—H21A	109.5
C10—C9—H9	119.5	C20—C21—H21B	109.5
C8—C9—H9	119.5	H21A—C21—H21B	109.5
C12—C13—C8	121.08 (11)	C20—C21—H21C	109.5
C12—C13—H13	119.5	H21A—C21—H21C	109.5
C8—C13—H13	119.5	H21B—C21—H21C	109.5
C9—C10—C11	119.28 (11)	C20—C22—H22B	109.5
C9—C10—H10	120.4	C20—C22—H22C	109.5
C11—C10—H10	120.4	H22B—C22—H22C	109.5
O3—C11—C10	123.51 (11)	C20—C22—H22A	109.5
O3—C11—C12	115.70 (11)	H22B—C22—H22A	109.5
C10—C11—C12	120.79 (11)	H22C—C22—H22A	109.5
C13—C12—C11	119.24 (11)	C5—C4—C3	121.77 (11)
C13—C12—H12	120.4	C5—C4—H4	119.1
C11—C12—H12	120.4	C3—C4—H4	119.1
C19—C14—C15	121.12 (13)
C9—C8—C7—O1	−5.73 (18)	C9—C8—C13—C12	−0.21 (19)
C13—C8—C7—O1	172.58 (12)	C7—C8—C13—C12	−178.51 (12)
C9—C8—C7—C1	173.94 (11)	C8—C9—C10—C11	−0.71 (19)
C13—C8—C7—C1	−7.76 (17)	C14—O3—C11—C10	0.68 (19)
C4—C3—C2—C1i	−177.89 (7)	C14—O3—C11—C12	−178.86 (12)
C4i—C3—C2—C1i	2.11 (7)	C9—C10—C11—O3	−179.14 (12)
C4—C3—C2—C1	2.11 (7)	C9—C10—C11—C12	0.38 (19)
C4i—C3—C2—C1	−177.89 (7)	C8—C13—C12—C11	−0.1 (2)
C3—C2—C1—C6	−1.15 (12)	O3—C11—C12—C13	179.58 (12)
C1i—C2—C1—C6	178.85 (12)	C10—C11—C12—C13	0.0 (2)
C3—C2—C1—C7	169.94 (8)	C11—O3—C14—C19	−84.84 (16)
C1i—C2—C1—C7	−10.06 (8)	C11—O3—C14—C15	98.74 (15)
O1—C7—C1—C6	110.54 (13)	C19—C14—C15—C16	−0.4 (2)
C8—C7—C1—C6	−69.13 (14)	O3—C14—C15—C16	175.98 (12)
O1—C7—C1—C2	−60.81 (15)	C6—O2—C20—C22	60.29 (17)
C8—C7—C1—C2	119.52 (11)	C6—O2—C20—C21	−177.26 (13)
C20—O2—C6—C1	−150.33 (12)	C14—C15—C16—C17	0.8 (2)
C20—O2—C6—C5	29.72 (18)	C15—C14—C19—C18	−0.5 (2)
C2—C1—C6—O2	178.90 (9)	O3—C14—C19—C18	−176.89 (13)
C7—C1—C6—O2	7.34 (16)	C15—C16—C17—C18	−0.3 (2)
C2—C1—C6—C5	−1.14 (17)	C16—C17—C18—C19	−0.7 (2)
C7—C1—C6—C5	−172.70 (11)	C14—C19—C18—C17	1.1 (2)
C4—C5—C6—O2	−177.55 (11)	C6—C5—C4—C3	−1.49 (18)
C4—C5—C6—C1	2.49 (19)	C4i—C3—C4—C5	179.19 (13)
C13—C8—C9—C10	0.62 (18)	C2—C3—C4—C5	−0.81 (13)
C7—C8—C9—C10	178.99 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ii	0.95	2.44	3.3398 (15)	158
C16—H16···Cgiii	0.95	2.97	3.8383 (19)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.95	2.44	3.3398 (15)	158
C16—H16⋯Cg ii	0.95	2.97	3.8383 (19)	152

Symmetry codes: (i) ; (ii) .