{2,7-Dieth­oxy-8-[(naphthalen-2-yl)carbon­yl]naphthalen-1-yl}(naphthalen-2-yl)methanone

Tsumuki, T.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536813003577

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o369

doi:10.1107/S1600536813003577

Open

access

{2,7-Diethoxy-8-[(naphthalen-2-yl)carbonyl]naphthalen-1-yl}(naphthalen-2-yl)methanone

Takehiro Tsumuki,^a Akiko Okamoto,^a ^* Hideaki Oike ^a and Noriyuki Yonezawa ^a

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 1 February 2013; accepted 5 February 2013; online 9 February 2013)

In the title compound, C₃₆H₂₈O₄, the two 2-naphthoyl groups at the 1- and 8-positions of the central 2,7-diethoxynaphthalene ring system are aligned almost antiparallel and make a dihedral angle of 48.35 (5)°. The dihedral angles between the central 2,7-diethoxynaphthalene ring system and the terminal naphthalene ring systems are 77.64 (4) and 73.73 (4)°. In the crystal, molecules are linked into chains along the a-axis direction by dual C—H⋯O interactions between naphthoyl groups.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 ). For the structures of closely related compounds, see: Nakaema et al. (2008 ); Tsumuki et al. (2011 ); Sasagawa et al. (2012 ); Isogai et al. (2013 ); Yoshiwaka et al. (2013 ).

Experimental

Crystal data

C₃₆H₂₈O₄
M_r = 524.58
Monoclinic, P 2₁ /c
a = 7.86946 (14) Å
b = 27.1458 (5) Å
c = 12.8490 (2) Å
β = 102.267 (1)°
V = 2682.16 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 193 K
0.50 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.732, T_max = 0.878
41696 measured reflections
4914 independent reflections
3996 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.09
4914 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O3ⁱ	0.95	2.45	3.3958 (18)	173
C25—H25⋯O4ⁱⁱ	0.95	2.45	3.3996 (18)	176
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003577/rz5043sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003577/rz5043Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003577/rz5043Isup3.cml

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of the naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the aid of a suitable acidic mediator (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-dimethoxynaphthalene (Nakaema et al., 2008), [2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone (Tsumuki et al., 2011), {2,7-dimethoxy-8-[4-(2-methylpropyl)benzoyl]naphthalen-1-yl}[4-(2-methylpropyl) phenyl]methanone (Sasagawa et al., 2012), (8-benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone (Isogai et al., 2013), and [8-(4-phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl) methanone (Yoshiwaka et al., 2013). The most simple analogues in these compounds, 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008) and [2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone (Tsumuki et al., 2011), lie across a crystallographic 2-fold axis and the molecular packing are stabilized by C—H···O interactions and π···π interactions between the aroyl groups. As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound is reported on herein.

The molecular structure of the title molecule is illustrated in Fig. 1. The two terminal naphthoyl groups are situated in an opposite direction and twisted away from the central 2,7-diethoxynaphthalene unit. The dihedral angles between the two naphthalene rings of the terminal naphthoyl groups (C13—C22 and C23—C32) is 48.35 (5)°. The dihedral angles between the terminal napthalene rings and the central naphthalene ring (C1—C10) are 77.64 (4) and 73.73 (4)°. The torsion angles between the carbonyl moieties and the central naphthalene ring are -52.63 (18)° [C9—C1—C11—O3] and -58.16 (17)° [C9—C8—C12—O4]. On the other hand, the carbonyl groups are slightly twisted away from the attached terminal naphthalene rings [torsion angles O3—C11—C13—C14 = -21.17 (19)° and O4—C12—C23—C32 = -14.10 (19)°]. In the crystal, the molecular packing of the title compound is mainly stabilized by two C—H···O interactions between the naphthoyl moieties leading to the formation of chains along the a axis (Table 1 and Fig. 2).

Related literature top

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Nakaema et al. (2008); Tsumuki et al. (2011); Sasagawa et al. (2012); Isogai et al. (2013); Yoshiwaka et al. (2013).

Experimental top

To a solution of 2-naphthoyl chloride (14.3 g, 75.0 mmol) and TiCl₄ (42.7 g, 225 mmol) in CH₂Cl₂ (62.5 ml), 2,7-diethoxynaphthalene (5.4 g, 25.3 mmol) was added. The reaction mixture was stirred at r. t. for 24 h, then poured into ice-cold water (200 ml). The aqueous layer was extracted with CHCl₃ (60 ml × 3). The combined organic extracts were washed with 2M aqueous NaOH (80 ml × 3) followed by washing with brine (80 ml × 3). The organic layer was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 97%). The crude product was purified by recrystallization from chloroform/methanol (1:2 v/v) solution (isolated yield 70%). Furthermore, the isolated product was crystallized from chloroform to give single crystals suitable for X-ray analysis.

¹H NMR δ (500 MHz, CDCl₃): 0.86 (6H, t, J = 6.9 Hz), 3.96 (4H, q, J = 6.9), 7.21 (2H, d, J = 9.0 Hz), 7.39 (2H, t, J = 7.5 Hz), 7.47 (2H, t, J = 7.5 Hz), 7.69–7.93 (8H, m), 7.98 (2H, d, J = 9.0 Hz), 8.15 (2H, s) p.p.m.; ¹³C NMR δ (125 MHz, CDCl₃): 14.36, 64.93, 112.35, 122.03, 124.89, 125.56, 125.89, 127.47, 127.54, 127.70, 129.59, 130.44, 130.74, 132.08, 132.41, 135.43, 136.47, 155.97, 197.17 p.p.m.; IR (KBr): 1658, 1623, 1608, 1510, 1470, 1275 cm^-1; HRMS (m/z): [M+H]+ calcd. for C₃₆H₂₉O₄, 525.2066; found, 525.2031.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound, showing the intermolecular C—H···O hydrogen bonds (see Table 1 for details; symmetry codes: (i) -1 + x, y, z; (ii) 1 + x, y, z).

{2,7-Diethoxy-8-[(naphthalen-2-yl)carbonyl]naphthalen-1-yl}(naphthalen-2-yl)methanone top

Crystal data top

C₃₆H₂₈O₄	F(000) = 1104
M_r = 524.58	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 493.0–494.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 7.86946 (14) Å	Cell parameters from 33371 reflections
b = 27.1458 (5) Å	θ = 3.3–68.2°
c = 12.8490 (2) Å	µ = 0.67 mm⁻¹
β = 102.267 (1)°	T = 193 K
V = 2682.16 (8) Å³	Block, colourless
Z = 4	0.50 × 0.25 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4914 independent reflections
Radiation source: rotating anode	3996 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −31→32
T_min = 0.732, T_max = 0.878	l = −15→15
41696 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) = 0.097	w = 1/[σ²(F_o²) + (0.0448P)² + 0.4544P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4914 reflections	Δρ_max = 0.20 e Å⁻³
364 parameters	Δρ_min = −0.15 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: 0.00121 (13)

Crystal data top

C₃₆H₂₈O₄	V = 2682.16 (8) Å³
M_r = 524.58	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.86946 (14) Å	µ = 0.67 mm⁻¹
b = 27.1458 (5) Å	T = 193 K
c = 12.8490 (2) Å	0.50 × 0.25 × 0.20 mm
β = 102.267 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4914 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3996 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.878	R_int = 0.029
41696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.09	Δρ_max = 0.20 e Å⁻³
4914 reflections	Δρ_min = −0.15 e Å⁻³
364 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	0.07897 (13)	0.25900 (3)	0.51894 (8)	0.0457 (3)
O2	0.55755 (13)	0.32784 (3)	1.03877 (7)	0.0436 (2)
O3	0.39273 (11)	0.34984 (3)	0.63817 (7)	0.0400 (2)
O4	0.21986 (11)	0.37405 (3)	0.83968 (8)	0.0431 (2)
C1	0.24047 (16)	0.28182 (5)	0.68544 (10)	0.0338 (3)
C2	0.16047 (17)	0.24468 (5)	0.61849 (10)	0.0365 (3)
C3	0.17099 (18)	0.19490 (5)	0.65104 (11)	0.0403 (3)
H3	0.1137	0.1700	0.6047	0.048*
C4	0.26404 (18)	0.18312 (5)	0.74950 (11)	0.0400 (3)
H4	0.2736	0.1495	0.7705	0.048*
C5	0.44227 (18)	0.20619 (5)	0.92342 (11)	0.0402 (3)
H5	0.4541	0.1723	0.9422	0.048*
C6	0.51793 (18)	0.24052 (5)	0.99566 (11)	0.0401 (3)
H6	0.5833	0.2308	1.0634	0.048*
C7	0.49772 (17)	0.29080 (5)	0.96834 (10)	0.0360 (3)
C8	0.40829 (16)	0.30593 (5)	0.86876 (10)	0.0334 (3)
C9	0.33228 (16)	0.26999 (5)	0.79099 (10)	0.0334 (3)
C10	0.34690 (16)	0.21927 (5)	0.82158 (10)	0.0358 (3)
C11	0.24972 (17)	0.33218 (5)	0.63750 (10)	0.0339 (3)
C12	0.37086 (16)	0.36012 (5)	0.85329 (10)	0.0336 (3)
C13	0.08776 (17)	0.35910 (5)	0.58868 (10)	0.0357 (3)
C14	0.09312 (19)	0.39523 (5)	0.51522 (11)	0.0410 (3)
H14	0.1997	0.4019	0.4944	0.049*
C15	−0.0564 (2)	0.42290 (5)	0.46955 (11)	0.0443 (3)
C16	−0.0535 (2)	0.46069 (6)	0.39398 (13)	0.0585 (4)
H16	0.0507	0.4672	0.3703	0.070*
C17	−0.1985 (3)	0.48786 (7)	0.35494 (14)	0.0710 (5)
H17	−0.1945	0.5133	0.3047	0.085*
C18	−0.3539 (3)	0.47841 (7)	0.38869 (14)	0.0735 (6)
H18	−0.4544	0.4975	0.3608	0.088*
C19	−0.3623 (2)	0.44224 (7)	0.46071 (13)	0.0624 (5)
H19	−0.4684	0.4363	0.4826	0.075*
C20	−0.21336 (19)	0.41325 (6)	0.50351 (12)	0.0473 (4)
C21	−0.21620 (19)	0.37583 (6)	0.57927 (12)	0.0485 (4)
H21	−0.3209	0.3692	0.6023	0.058*
C22	−0.07049 (18)	0.34901 (5)	0.62000 (11)	0.0421 (3)
H22	−0.0754	0.3234	0.6697	0.051*
C23	0.51548 (16)	0.39574 (5)	0.85724 (10)	0.0331 (3)
C24	0.68331 (17)	0.37994 (5)	0.84828 (11)	0.0406 (3)
H24	0.7053	0.3458	0.8409	0.049*
C25	0.81350 (19)	0.41323 (6)	0.85009 (12)	0.0483 (4)
H25	0.9250	0.4021	0.8431	0.058*
C26	0.78459 (18)	0.46415 (5)	0.86224 (11)	0.0442 (3)
C27	0.9164 (2)	0.50030 (7)	0.86551 (15)	0.0625 (5)
H27	1.0286	0.4907	0.8569	0.075*
C28	0.8826 (3)	0.54880 (7)	0.88092 (15)	0.0691 (5)
H28	0.9722	0.5725	0.8831	0.083*
C29	0.7192 (3)	0.56425 (6)	0.89353 (14)	0.0619 (5)
H29	0.6988	0.5981	0.9055	0.074*
C30	0.5895 (2)	0.53092 (5)	0.88874 (12)	0.0506 (4)
H30	0.4778	0.5418	0.8961	0.061*
C31	0.61786 (18)	0.48013 (5)	0.87293 (10)	0.0396 (3)
C32	0.48516 (17)	0.44475 (5)	0.86871 (10)	0.0367 (3)
H32	0.3722	0.4553	0.8740	0.044*
C33	−0.01793 (18)	0.22392 (5)	0.44723 (11)	0.0400 (3)
H33A	−0.1017	0.2063	0.4814	0.048*
H33B	0.0609	0.1995	0.4252	0.048*
C34	−0.11200 (19)	0.25281 (5)	0.35288 (11)	0.0445 (3)
H34A	−0.0272	0.2694	0.3190	0.053*
H34B	−0.1868	0.2775	0.3764	0.053*
H34C	−0.1835	0.2305	0.3016	0.053*
C35	0.65820 (18)	0.31522 (5)	1.14207 (10)	0.0419 (3)
H35A	0.7612	0.2956	1.1352	0.050*
H35B	0.5874	0.2956	1.1821	0.050*
C36	0.7138 (2)	0.36274 (6)	1.19899 (13)	0.0588 (4)
H36A	0.7934	0.3558	1.2671	0.071*
H36B	0.6113	0.3802	1.2121	0.071*
H36C	0.7729	0.3833	1.1550	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0550 (6)	0.0357 (5)	0.0401 (5)	−0.0040 (4)	−0.0040 (4)	−0.0021 (4)
O2	0.0533 (6)	0.0400 (5)	0.0338 (5)	−0.0012 (4)	0.0010 (4)	0.0004 (4)
O3	0.0368 (5)	0.0424 (5)	0.0414 (5)	−0.0046 (4)	0.0097 (4)	0.0002 (4)
O4	0.0330 (5)	0.0413 (5)	0.0545 (6)	0.0036 (4)	0.0084 (4)	−0.0037 (4)
C1	0.0329 (7)	0.0317 (7)	0.0369 (7)	0.0008 (5)	0.0080 (5)	0.0001 (5)
C2	0.0353 (7)	0.0371 (7)	0.0366 (7)	0.0010 (6)	0.0064 (6)	0.0002 (6)
C3	0.0423 (8)	0.0327 (7)	0.0450 (8)	−0.0016 (6)	0.0073 (6)	−0.0052 (6)
C4	0.0444 (8)	0.0303 (7)	0.0464 (8)	0.0019 (6)	0.0121 (6)	0.0018 (6)
C5	0.0442 (8)	0.0353 (7)	0.0421 (7)	0.0036 (6)	0.0116 (6)	0.0070 (6)
C6	0.0423 (8)	0.0409 (8)	0.0364 (7)	0.0020 (6)	0.0070 (6)	0.0057 (6)
C7	0.0353 (7)	0.0365 (7)	0.0369 (7)	−0.0010 (5)	0.0093 (6)	−0.0004 (6)
C8	0.0314 (7)	0.0341 (7)	0.0359 (7)	0.0003 (5)	0.0096 (5)	0.0006 (5)
C9	0.0306 (7)	0.0333 (7)	0.0379 (7)	0.0016 (5)	0.0106 (5)	0.0007 (5)
C10	0.0363 (7)	0.0329 (7)	0.0403 (7)	0.0018 (5)	0.0129 (6)	0.0008 (6)
C11	0.0377 (7)	0.0332 (7)	0.0313 (6)	−0.0023 (6)	0.0080 (5)	−0.0038 (5)
C12	0.0345 (7)	0.0359 (7)	0.0299 (6)	0.0026 (5)	0.0059 (5)	−0.0019 (5)
C13	0.0388 (7)	0.0319 (7)	0.0354 (7)	−0.0014 (5)	0.0052 (6)	−0.0023 (5)
C14	0.0442 (8)	0.0379 (7)	0.0405 (7)	−0.0013 (6)	0.0081 (6)	−0.0002 (6)
C15	0.0536 (9)	0.0372 (8)	0.0383 (7)	0.0054 (6)	0.0014 (6)	−0.0027 (6)
C16	0.0757 (11)	0.0484 (9)	0.0467 (9)	0.0077 (8)	0.0025 (8)	0.0062 (7)
C17	0.1020 (16)	0.0568 (11)	0.0466 (10)	0.0234 (10)	−0.0011 (10)	0.0063 (8)
C18	0.0869 (14)	0.0723 (12)	0.0513 (10)	0.0402 (11)	−0.0081 (10)	−0.0061 (9)
C19	0.0580 (10)	0.0704 (11)	0.0524 (10)	0.0232 (9)	−0.0027 (8)	−0.0097 (9)
C20	0.0497 (9)	0.0462 (8)	0.0415 (8)	0.0089 (7)	−0.0003 (7)	−0.0087 (6)
C21	0.0388 (8)	0.0562 (9)	0.0499 (9)	0.0008 (7)	0.0079 (7)	−0.0064 (7)
C22	0.0397 (8)	0.0423 (8)	0.0442 (8)	−0.0018 (6)	0.0085 (6)	0.0011 (6)
C23	0.0343 (7)	0.0331 (7)	0.0309 (6)	0.0025 (5)	0.0050 (5)	0.0017 (5)
C24	0.0379 (7)	0.0387 (8)	0.0451 (8)	0.0051 (6)	0.0090 (6)	−0.0004 (6)
C25	0.0355 (8)	0.0557 (9)	0.0550 (9)	0.0011 (7)	0.0126 (7)	−0.0009 (7)
C26	0.0448 (8)	0.0470 (8)	0.0409 (8)	−0.0075 (6)	0.0096 (6)	0.0013 (6)
C27	0.0538 (10)	0.0681 (12)	0.0683 (11)	−0.0161 (9)	0.0188 (8)	0.0019 (9)
C28	0.0800 (13)	0.0545 (11)	0.0735 (12)	−0.0304 (10)	0.0180 (10)	0.0014 (9)
C29	0.0816 (13)	0.0412 (9)	0.0642 (11)	−0.0145 (8)	0.0184 (9)	0.0015 (8)
C30	0.0653 (10)	0.0363 (8)	0.0507 (9)	−0.0037 (7)	0.0133 (7)	0.0025 (7)
C31	0.0463 (8)	0.0384 (7)	0.0334 (7)	−0.0030 (6)	0.0067 (6)	0.0027 (6)
C32	0.0369 (7)	0.0365 (7)	0.0358 (7)	0.0027 (6)	0.0058 (6)	0.0023 (6)
C33	0.0406 (7)	0.0390 (7)	0.0402 (7)	−0.0054 (6)	0.0084 (6)	−0.0063 (6)
C34	0.0436 (8)	0.0497 (9)	0.0393 (8)	−0.0073 (6)	0.0067 (6)	−0.0009 (6)
C35	0.0422 (8)	0.0483 (8)	0.0336 (7)	0.0020 (6)	0.0046 (6)	0.0024 (6)
C36	0.0677 (11)	0.0549 (10)	0.0465 (9)	−0.0021 (8)	−0.0043 (8)	−0.0030 (7)

Geometric parameters (Å, º) top

O1—C2	1.3602 (16)	C19—C20	1.422 (2)
O1—C33	1.4278 (16)	C19—H19	0.9500
O2—C7	1.3676 (16)	C20—C21	1.410 (2)
O2—C35	1.4351 (16)	C21—C22	1.365 (2)
O3—C11	1.2217 (15)	C21—H21	0.9500
O4—C12	1.2237 (15)	C22—H22	0.9500
C1—C2	1.3867 (18)	C23—C32	1.3653 (18)
C1—C9	1.4310 (18)	C23—C24	1.4164 (18)
C1—C11	1.5075 (17)	C24—C25	1.363 (2)
C2—C3	1.4117 (19)	C24—H24	0.9500
C3—C4	1.3583 (19)	C25—C26	1.415 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C10	1.4103 (19)	C26—C31	1.416 (2)
C4—H4	0.9500	C26—C27	1.422 (2)
C5—C6	1.3600 (19)	C27—C28	1.366 (3)
C5—C10	1.4086 (19)	C27—H27	0.9500
C5—H5	0.9500	C28—C29	1.394 (3)
C6—C7	1.4099 (19)	C28—H28	0.9500
C6—H6	0.9500	C29—C30	1.356 (2)
C7—C8	1.3852 (18)	C29—H29	0.9500
C8—C9	1.4332 (18)	C30—C31	1.418 (2)
C8—C12	1.5049 (18)	C30—H30	0.9500
C9—C10	1.4300 (18)	C31—C32	1.4112 (19)
C11—C13	1.4874 (18)	C32—H32	0.9500
C12—C23	1.4860 (18)	C33—C34	1.5004 (19)
C13—C14	1.3680 (19)	C33—H33A	0.9900
C13—C22	1.4145 (19)	C33—H33B	0.9900
C14—C15	1.414 (2)	C34—H34A	0.9800
C14—H14	0.9500	C34—H34B	0.9800
C15—C16	1.416 (2)	C34—H34C	0.9800
C15—C20	1.419 (2)	C35—C36	1.501 (2)
C16—C17	1.361 (2)	C35—H35A	0.9900
C16—H16	0.9500	C35—H35B	0.9900
C17—C18	1.406 (3)	C36—H36A	0.9800
C17—H17	0.9500	C36—H36B	0.9800
C18—C19	1.360 (3)	C36—H36C	0.9800
C18—H18	0.9500

C2—O1—C33	119.78 (10)	C15—C20—C19	118.60 (15)
C7—O2—C35	118.77 (10)	C22—C21—C20	120.90 (14)
C2—C1—C9	119.74 (12)	C22—C21—H21	119.6
C2—C1—C11	117.44 (11)	C20—C21—H21	119.6
C9—C1—C11	122.15 (11)	C21—C22—C13	120.41 (13)
O1—C2—C1	115.90 (11)	C21—C22—H22	119.8
O1—C2—C3	122.58 (12)	C13—C22—H22	119.8
C1—C2—C3	121.45 (12)	C32—C23—C24	119.41 (12)
C4—C3—C2	119.16 (13)	C32—C23—C12	119.19 (11)
C4—C3—H3	120.4	C24—C23—C12	121.39 (12)
C2—C3—H3	120.4	C25—C24—C23	120.57 (13)
C3—C4—C10	122.03 (13)	C25—C24—H24	119.7
C3—C4—H4	119.0	C23—C24—H24	119.7
C10—C4—H4	119.0	C24—C25—C26	120.79 (13)
C6—C5—C10	122.08 (13)	C24—C25—H25	119.6
C6—C5—H5	119.0	C26—C25—H25	119.6
C10—C5—H5	119.0	C25—C26—C31	118.94 (13)
C5—C6—C7	118.92 (13)	C25—C26—C27	122.96 (14)
C5—C6—H6	120.5	C31—C26—C27	118.09 (14)
C7—C6—H6	120.5	C28—C27—C26	120.42 (17)
O2—C7—C8	115.41 (11)	C28—C27—H27	119.8
O2—C7—C6	122.84 (12)	C26—C27—H27	119.8
C8—C7—C6	121.69 (12)	C27—C28—C29	121.30 (16)
C7—C8—C9	119.81 (12)	C27—C28—H28	119.4
C7—C8—C12	117.29 (11)	C29—C28—H28	119.4
C9—C8—C12	122.16 (11)	C30—C29—C28	119.88 (16)
C10—C9—C1	118.13 (12)	C30—C29—H29	120.1
C10—C9—C8	117.81 (12)	C28—C29—H29	120.1
C1—C9—C8	124.05 (12)	C29—C30—C31	121.01 (16)
C5—C10—C4	121.03 (12)	C29—C30—H30	119.5
C5—C10—C9	119.59 (12)	C31—C30—H30	119.5
C4—C10—C9	119.37 (12)	C32—C31—C26	118.77 (13)
O3—C11—C13	121.04 (11)	C32—C31—C30	121.95 (13)
O3—C11—C1	118.52 (11)	C26—C31—C30	119.28 (13)
C13—C11—C1	120.43 (11)	C23—C32—C31	121.50 (12)
O4—C12—C23	121.13 (12)	C23—C32—H32	119.3
O4—C12—C8	118.55 (11)	C31—C32—H32	119.3
C23—C12—C8	120.30 (11)	O1—C33—C34	106.08 (11)
C14—C13—C22	119.55 (13)	O1—C33—H33A	110.5
C14—C13—C11	119.60 (12)	C34—C33—H33A	110.5
C22—C13—C11	120.81 (12)	O1—C33—H33B	110.5
C13—C14—C15	121.49 (13)	C34—C33—H33B	110.5
C13—C14—H14	119.3	H33A—C33—H33B	108.7
C15—C14—H14	119.3	C33—C34—H34A	109.5
C14—C15—C16	122.46 (15)	C33—C34—H34B	109.5
C14—C15—C20	118.43 (13)	H34A—C34—H34B	109.5
C16—C15—C20	119.08 (14)	C33—C34—H34C	109.5
C17—C16—C15	120.76 (18)	H34A—C34—H34C	109.5
C17—C16—H16	119.6	H34B—C34—H34C	109.5
C15—C16—H16	119.6	O2—C35—C36	106.97 (12)
C16—C17—C18	120.22 (18)	O2—C35—H35A	110.3
C16—C17—H17	119.9	C36—C35—H35A	110.3
C18—C17—H17	119.9	O2—C35—H35B	110.3
C19—C18—C17	120.83 (17)	C36—C35—H35B	110.3
C19—C18—H18	119.6	H35A—C35—H35B	108.6
C17—C18—H18	119.6	C35—C36—H36A	109.5
C18—C19—C20	120.51 (18)	C35—C36—H36B	109.5
C18—C19—H19	119.7	H36A—C36—H36B	109.5
C20—C19—H19	119.7	C35—C36—H36C	109.5
C21—C20—C15	119.19 (13)	H36A—C36—H36C	109.5
C21—C20—C19	122.21 (15)	H36B—C36—H36C	109.5

C33—O1—C2—C1	−175.31 (11)	C22—C13—C14—C15	0.0 (2)
C33—O1—C2—C3	7.58 (19)	C11—C13—C14—C15	−177.80 (12)
C9—C1—C2—O1	−178.78 (11)	C13—C14—C15—C16	179.53 (14)
C11—C1—C2—O1	−7.94 (17)	C13—C14—C15—C20	1.5 (2)
C9—C1—C2—C3	−1.64 (19)	C14—C15—C16—C17	−177.36 (15)
C11—C1—C2—C3	169.20 (12)	C20—C15—C16—C17	0.7 (2)
O1—C2—C3—C4	175.83 (12)	C15—C16—C17—C18	−0.5 (3)
C1—C2—C3—C4	−1.1 (2)	C16—C17—C18—C19	0.1 (3)
C2—C3—C4—C10	1.7 (2)	C17—C18—C19—C20	0.1 (3)
C10—C5—C6—C7	1.1 (2)	C14—C15—C20—C21	−1.5 (2)
C35—O2—C7—C8	−177.25 (11)	C16—C15—C20—C21	−179.60 (14)
C35—O2—C7—C6	5.50 (18)	C14—C15—C20—C19	177.69 (13)
C5—C6—C7—O2	174.74 (12)	C16—C15—C20—C19	−0.4 (2)
C5—C6—C7—C8	−2.3 (2)	C18—C19—C20—C21	179.21 (16)
O2—C7—C8—C9	−176.70 (11)	C18—C19—C20—C15	0.0 (2)
C6—C7—C8—C9	0.58 (19)	C15—C20—C21—C22	0.0 (2)
O2—C7—C8—C12	−6.34 (16)	C19—C20—C21—C22	−179.14 (14)
C6—C7—C8—C12	170.94 (12)	C20—C21—C22—C13	1.5 (2)
C2—C1—C9—C10	3.69 (17)	C14—C13—C22—C21	−1.5 (2)
C11—C1—C9—C10	−166.70 (11)	C11—C13—C22—C21	176.23 (12)
C2—C1—C9—C8	−175.25 (12)	O4—C12—C23—C32	14.09 (18)
C11—C1—C9—C8	14.35 (18)	C8—C12—C23—C32	−164.40 (12)
C7—C8—C9—C10	2.31 (17)	O4—C12—C23—C24	−165.25 (12)
C12—C8—C9—C10	−167.56 (11)	C8—C12—C23—C24	16.25 (18)
C7—C8—C9—C1	−178.74 (11)	C32—C23—C24—C25	−0.6 (2)
C12—C8—C9—C1	11.38 (19)	C12—C23—C24—C25	178.77 (13)
C6—C5—C10—C4	−177.56 (13)	C23—C24—C25—C26	0.8 (2)
C6—C5—C10—C9	1.8 (2)	C24—C25—C26—C31	0.2 (2)
C3—C4—C10—C5	179.80 (12)	C24—C25—C26—C27	179.46 (15)
C3—C4—C10—C9	0.4 (2)	C25—C26—C27—C28	−177.82 (16)
C1—C9—C10—C5	177.50 (11)	C31—C26—C27—C28	1.4 (2)
C8—C9—C10—C5	−3.49 (18)	C26—C27—C28—C29	−0.2 (3)
C1—C9—C10—C4	−3.10 (18)	C27—C28—C29—C30	−1.1 (3)
C8—C9—C10—C4	175.91 (11)	C28—C29—C30—C31	1.1 (3)
C2—C1—C11—O3	−117.99 (13)	C25—C26—C31—C32	−1.4 (2)
C9—C1—C11—O3	52.62 (17)	C27—C26—C31—C32	179.34 (14)
C2—C1—C11—C13	60.82 (16)	C25—C26—C31—C30	177.88 (14)
C9—C1—C11—C13	−128.58 (13)	C27—C26—C31—C30	−1.4 (2)
C7—C8—C12—O4	−111.96 (14)	C29—C30—C31—C32	179.38 (14)
C9—C8—C12—O4	58.15 (17)	C29—C30—C31—C26	0.1 (2)
C7—C8—C12—C23	66.57 (15)	C24—C23—C32—C31	−0.64 (19)
C9—C8—C12—C23	−123.31 (13)	C12—C23—C32—C31	180.00 (12)
O3—C11—C13—C14	21.18 (19)	C26—C31—C32—C23	1.62 (19)
C1—C11—C13—C14	−157.60 (12)	C30—C31—C32—C23	−177.63 (13)
O3—C11—C13—C22	−156.59 (13)	C2—O1—C33—C34	171.47 (11)
C1—C11—C13—C22	24.64 (18)	C7—O2—C35—C36	176.89 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3ⁱ	0.95	2.45	3.3958 (18)	173
C25—H25···O4ⁱⁱ	0.95	2.45	3.3996 (18)	176

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

Experimental details

Crystal data
Chemical formula	C₃₆H₂₈O₄
M_r	524.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	7.86946 (14), 27.1458 (5), 12.8490 (2)
β (°)	102.267 (1)
V (Å³)	2682.16 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.50 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.732, 0.878
No. of measured, independent and observed [I > 2σ(I)] reflections	41696, 4914, 3996
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.09
No. of reflections	4914
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3ⁱ	0.95	2.45	3.3958 (18)	173
C25—H25···O4ⁱⁱ	0.95	2.45	3.3996 (18)	176

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

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 an Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. 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
Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71. 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. & 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
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o3348. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yoshiwaka, S., Hijikata, D., Sasagawa, K., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o242. CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o369

doi:10.1107/S1600536813003577

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

{2,7-Dieth­­oxy-8-[(naphthalen-2-yl)carbon­yl]naphthalen-1-yl}(naphthalen-2-yl)methanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{2,7-Diethoxy-8-[(naphthalen-2-yl)carbonyl]naphthalen-1-yl}(naphthalen-2-yl)methanone