[8-(4-Phen­oxy­benzo­yl)-2,7-bis­(propan-2-yl­oxy)naphthalen-1-yl](4-phen­oxy­phen­yl)methanone

Yoshiwaka, S.; Hijikata, D.; Sasagawa, K.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536813000913

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o242

doi:10.1107/S1600536813000913

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[8-(4-Phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone

Sayaka Yoshiwaka,^a Daichi Hijikata,^a Kosuke Sasagawa,^a Akiko Okamoto ^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 5 December 2012; accepted 10 January 2013; online 16 January 2013)

The entire title molecule, C₄₂H₃₆O₆, is completed by the application of a twofold axis. The 4-phenoxybenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel. 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 phenoxy groups and the naphthalene ring system is 27.80 (6)°. In the crystal, molecules are linked into a three-dimensional architecture by C—H⋯O and C—H⋯π interactions.

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_r = 636.71
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.04
3101 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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⋯Cgⁱⁱ	0.95	2.97	3.8383 (19)	152
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000913/pk2459sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813000913/pk2459Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of the naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the choice of suitable acidic mediators (Okamoto & Yonezawa, 2009 Okamoto et al., 2011). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene analogues exemplified by 1,8-dibenzoyl-2,7-dimethoxynaphtalene (Nakaema et al., 2008), [2,7-dimethoxy-8-(4-propylbenzoyl)naphthalene-1-yl]-(4-propylphenyl)methanone (Sasagawa et al., 2012) and [2,7-dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone (Muto et al. 2010). In the crystals of these compounds, two aroyl groups tend to attach to the naphthalene ring in nearly perpendicular manners and oriented in the opposite direction (anti-orientation). Recently, the crystal structure of 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene has been clarified to take syn-orientation, where two phenoxybenzoyl groups are positioned on the same side against the naphthalene ring plane (Hijikata et al. 2010). As a part of our continuing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound peri-aroylnaphthalene bearing isopropoxy groups at the 2,7-positions is discussed in this article.

The molecular structure of the title compounds is displayed in Fig 1. Two 4-phenoxybenzoyl groups are situated in anti-orientation and are twisted away from the attached naphthalene ring. This molecule lies on a crystallographic 2-fold axis so that the asymmetric unit consists of one-half of the molecule. The dihedral angle between the best plane of the inner benzene ring of the 4-phenoxybenzoyl groups and the naphthalene system is 70.52 (5)°.

Centrosymmetrically related molecules are linked into dimeric unit by pairs of C—H···π interactions between the hydrogen atom (H16) on the terminal phenoxy group and the π-system of the benzene ring in the benzoyl moiety (C8–C13) (C16—H16···Cgⁱⁱⁱ, Fig. 2). The molecules of the title compound are aligned in an antiparallel fashion with the adjacent molecule. The terminal benzene ring of the phenoxybenzoyl group interacts with the inner benzene ring of the phenoxybenzoyl group of the adjacent molecule. Both of the pairs of the facing benzene rings in the couple of the phenoxybenzoyl groups are situated almost perpendicularly to the benzene ring in the benzoyl moiety (C8–C13). Then two identical interactions are formed to give cyclic structure between the two phenoxybenzoyl groups.

Furthermore, an oxygen atom of the carbonyl group forms intermolecular C—H···O interaction with the m-hydrogen of the benzoyl benzene ring of the other adjacent molecule (C12—H12···O1 = 2.44 Å, Fig. 3).

Related literature top

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 top

1,8-(4-phenoxybenzoyl)-2,7-dihydroxynaphtalene (0.3 mmol, 157 mg), tetrabutylammonium iodide (0.03 mmol, 113 mg), potassium carbonate (0.9 mmol, 127 mg) and DMF (0.75 ml) were placed into a 10 ml flask, followed by stirring at room temperature under nitrogen for 1 h. 2-Bromopropane (1.8 mmol, 224 mg) was to the solution and heated at 70 °C for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-cold water (20 ml). The aqueous layer was extracted with ethyl acetate (20 ml × 2). The combined extracts were washed with 2 M aqueous NaOH followed by washing the brine. The extracts thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 22%). Colourless single crystals suitable for X-ray diffraction were obtained by repeated crystallization from methanol.

¹H NMR δ (300 MHz, CDCl₃): 1.04 (12H, d, J = 6.0 Hz), 4.51 (2H, sep, J = 6.0 Hz), 6.89 (4H, d, J = 8.1 Hz), 7.09 (4H, d, J = 8.1 Hz), 7.13 (2H, d, J = 9.0 Hz), 7.17 (2H, d, J = 8.1 Hz), 7.37 (4H, t, J = 8.1 Hz), 7.70 (4H, d, J = 8.1 Hz), 7.86 (2H, d, J = 9.0 Hz),

¹³C NMR δ (125 MHz, CDCl₃): 21.6, 71.5, 113.1, 116.7, 120.0, 122.6, 124.1, 125.2, 129.8, 130.4, 131.3, 131.6, 134.3, 154.6, 155.8, 161.1, 196.0 p.p.m.

IR (KBr): 1656 (C=O), 1601, 1505, 1452 (Ar), 1267 (C—O—C) cm^-1

HRMS (m/z): [M+H]⁺ called. for C₄₂H₃₇O₆, 637.2581, found, 637.2590.

m.p. = 450.2–451.4 K

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of compound (I), showing the intermolecular C—H···π interactions (dashed lines). Cg is the centroid of the C8—C13 ring. Symmetry code: (iii) 1 - x, -y, - z +2.
	Fig. 3. A partial packing diagram of compound (I), showing the C12–H12···O1 hydrogen interactions (dashed lines). Symmetry code: x, 1 - y, 1/2 + z.

[8-(4-Phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4- phenoxyphenyl)methanone top

Crystal data top

C₄₂H₃₆O₆	F(000) = 1344
M_r = 636.71	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	3101 independent reflections
Radiation source: rotaing anode	2749 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.3°, θ_min = 4.0°
ω scans	h = −27→27
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
T_min = 0.693, T_max = 0.734	l = −17→17
28911 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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0477P)² + 1.7648P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3101 reflections	Δρ_max = 0.21 e Å⁻³
221 parameters	Δρ_min = −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)

Crystal data top

C₄₂H₃₆O₆	V = 3407.58 (11) Å³
M_r = 636.71	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 22.7084 (4) Å	µ = 0.66 mm⁻¹
b = 10.3582 (2) Å	T = 193 K
c = 14.7152 (3) Å	0.60 × 0.60 × 0.50 mm
β = 100.106 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3101 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2749 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.734	R_int = 0.029
28911 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
3101 reflections	Δρ_min = −0.16 e Å⁻³
221 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C8–C13 ring.

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

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₄₂H₃₆O₆
M_r	636.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	22.7084 (4), 10.3582 (2), 14.7152 (3)
β (°)	100.106 (1)
V (Å³)	3407.58 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.60 × 0.60 × 0.50

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.693, 0.734
No. of measured, independent and observed [I > 2σ(I)] reflections	28911, 3101, 2749
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.04
No. of reflections	3101
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.16

Computer programs: PROCESS-AUTO (Rigaku, 1998), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

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···Cgⁱⁱ	0.95	2.97	3.8383 (19)	152

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y, −z+2.

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Shorai Foundation for Science and Technology.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. 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
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902–o2903. Web of Science CSD CrossRef CAS IUCr Journals 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., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283–1284. Web of Science CrossRef CAS 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
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2596. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 2| February 2013| Page o242

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

[8-(4-Phen­­oxy­benzo­yl)-2,7-bis­­(propan-2-yl­­oxy)naphthalen-1-yl](4-phen­­oxy­phen­yl)methanone

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organic compounds

[8-(4-Phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone