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

Tsumuki, T.; Takeuchi, R.; Kawano, H.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813005710

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o495-o496

doi:10.1107/S1600536813005710

Open

access

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

Takehiro Tsumuki,^a Ryo Takeuchi,^a Hiroyuki Kawano,^b Noriyuki Yonezawa ^a and Akiko Okamoto ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan, and ^bDivision of Liberal Arts, Kogakuin University, Hachioji, Tokyo 192-0015, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 14 February 2013; accepted 27 February 2013; online 6 March 2013)

In the title compound, C₃₆H₂₈O₄, the 1-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 76.59 (4)°. The dihedral angles between the central 2,7-diethoxynaphthalene ring system and the terminal naphthalene ring systems are 86.48 (4) and 83.97 (4)°. In the crystal, C—H⋯π interactions between the central naphthalene ring systems and the naphthoyl groups are observed along the a axis, with the molecules forming a columnar structure. The columns are linked into chains parallel to the b axis by C—H⋯O interactions.

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 ); Sakamoto et al. (2012 ); Isogai et al. (2013 ); Tsumuki et al. (2013 ); Yoshiwaka et al. (2013 ).

Experimental

Crystal data

C₃₆H₂₈O₄
M_r = 524.58
Triclinic, $[P \overline 1]$
a = 8.76532 (16) Å
b = 11.4266 (2) Å
c = 14.1972 (3) Å
α = 99.080 (1)°
β = 99.036 (1)°
γ = 104.277 (1)°
V = 1331.94 (4) Å³
Z = 2
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 = 0.877
24143 measured reflections
4800 independent reflections
4142 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.106
S = 1.07
4800 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg6 are the centroids of the C16–C21 and C27–C32 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg4ⁱ	0.95	2.77	3.5662 (15)	142
C7—H7⋯Cg6ⁱ	0.95	2.76	3.5662 (16)	143
C30—H30⋯O2ⁱⁱ	0.95	2.53	3.3289 (19)	142
C34—H34A⋯O1ⁱⁱⁱ	0.98	2.47	3.423 (2)	163
C35—H35B⋯O2^iv	0.99	2.59	3.5476 (17)	163
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+1, -z+1; (iv) -x, -y+2, -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/S1600536813005710/pk2467sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005710/pk2467Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005710/pk2467Isup3.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) and [2,7-dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone (Tsumuki et al., 2011). Furthermore, crystal structures of 1,8-diaroylnaphthalene analogues bearing various alkoxy and aryloxy groups at the 2,7-positions such as 1,8-dibenzoylnaphthalene-2,7-diyl dibenzoate (Sakamoto et al., 2012) and [8-(4-phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone (Yoshiwaka et al., 2013) have been also revealed. Some 1,8-diaroylnaphthalene compounds bearing the ethoxy group, {2,7-diethoxy-8-[(naphthalen-2-yl)-carbonyl]naphthalen-1-yl}(naphthalen-2-yl)methanone (Tsumuki et al., 2013) and (8-benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone (Isogai et al., 2013), are stabilized by the molecular packing of C—H···O 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, the 2,7-diethoxynaphthalene bearing α-naphthoyl groups at the 1,8-positions, is reported on herein.

The molecular structure of the title molecule is illustrated in Fig.1. The two terminal naphthoyl groups are oriented in opposite directions and are twisted away from the central 2,7-diethoxynaphthalene unit. The carbonyl moieties deviate slightly from the attached naphthalene rings. The dihedral angle between the two naphthalene rings of the terminal naphthoyl groups (C12–C21 and C23–C32) is 76.59 (4)°. The dihedral angles between the terminal naphthalene rings and the central naphthalene ring (C1–C10) are 86.48 (4) and 83.97 (4)°. The torsion angles between the carbonyl moieties and the central naphthalene ring are -60.91 (16)° (C10—C1—C11—O1) and -65.50 (17)° (C10—C9—C22—O2), and those between the carbonyl moieties and the terminal naphthalene rings are -47.50 (17)° (O1—C11—C12—C21) and -46.38 (17)° (O2—C22—C23—C32).

In the molecular packing, C—H···π interactions between the central naphthalene rings and the naphthoyl groups are observed along the a axis, and form columnar structures (Fig. 2, 3 and Table 1). Each column is linked into chains along the b axis by C—H···O interactions (Fig. 4 and Table 1).

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); Sakamoto et al. (2012); Isogai et al. (2013); Tsumuki et al. (2013); Yoshiwaka et al. (2013).

Experimental top

To a solution of 1-naphthoyl chloride (630 mg, 3.3 mmol) and TiCl₄ (1.88 g, 9.9 mmol) in CH₂Cl₂ (2.5 ml), 2,7-diethoxynaphthalene (220 mg, 1.0 mmol) was added. The reaction mixture was stirred at r.t. for 3 h, then poured into ice-cold water (20 ml). The aqueous layer was extracted with CHCl₃ (20 ml × 3). The combined organic extracts were washed with 2 M aqueous NaOH (25 ml × 3) followed by washing with brine (25 ml × 3). The organic layer was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 95%). The crude product was purified by recrystallization from chloroform (isolated yield 60%). Colorless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from chloroform.

¹H NMR δ (500 MHz, CDCl₃): 0.57 (6H, broad), 3.78 (4H, broad), 7.13 (2H, d, J = 9.0 Hz), 7.27–7.33 (6H, m), 7.71–7.83 (6H, m), 7.91 (2H, d, J = 9.0 Hz), 8.15 (2H, broad) p.p.m.; ¹³C NMR δ (125 MHz, CDCl₃): 14.12, 64.99, 112.73, 124.29, 124.70,125.53, 125.65, 126.45, 127.26, 127.88, 130.31, 130.52, 130.85, 132.33, 132.39,133.61, 137.15, 156.87, 199.49 p.p.m.; IR (KBr): 1658, 1607, 1512, 1471, 1275 cm^-1; HRMS (m/z): [M+H]⁺ calcd. for C₃₆H₂₉O₄, 525.2066, found, 525.2032.

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 the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The arrangement of the molecules in the crystal structure, viewed down the a axis.
	Fig. 3. A partial view of the crystal packing of the title compound, showing the intermolecular C—H···π interactions. Cg4 and Cg6 are centroid of the C16–C21 and C27–C32 (see Table 1 for details; symmetry codes: (i) 1 + x, y, z).
	Fig. 4. A partial view of the crystal packing of the title compound, showing the intermolecular C—H···O interactions (see Table 1 for details; symmetry codes: (ii) 1 - x, 2 - y, 2 - z; (iii) - x, - 1 - y, - 1 - z (iv); - x, 2 - y, 2 - z).

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

Crystal data top

C₃₆H₂₈O₄	Z = 2
M_r = 524.58	F(000) = 552
Triclinic, P1	D_x = 1.308 Mg m⁻³
Hall symbol: -P 1	Melting point = 506.6–508.4 K
a = 8.76532 (16) Å	Cu Kα radiation, λ = 1.54187 Å
b = 11.4266 (2) Å	Cell parameters from 20940 reflections
c = 14.1972 (3) Å	θ = 3.2–68.2°
α = 99.080 (1)°	µ = 0.67 mm⁻¹
β = 99.036 (1)°	T = 193 K
γ = 104.277 (1)°	Platelet, colorless
V = 1331.94 (4) Å³	0.60 × 0.40 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4800 independent reflections
Radiation source: rotating anode	4142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.2°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −13→13
T_min = 0.689, T_max = 0.877	l = −17→17
24143 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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.058P)² + 0.2087P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4800 reflections	Δρ_max = 0.20 e Å⁻³
364 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: 0.0072 (5)

Crystal data top

C₃₆H₂₈O₄	γ = 104.277 (1)°
M_r = 524.58	V = 1331.94 (4) Å³
Triclinic, P1	Z = 2
a = 8.76532 (16) Å	Cu Kα radiation
b = 11.4266 (2) Å	µ = 0.67 mm⁻¹
c = 14.1972 (3) Å	T = 193 K
α = 99.080 (1)°	0.60 × 0.40 × 0.20 mm
β = 99.036 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4800 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	4142 reflections with I > 2σ(I)
T_min = 0.689, T_max = 0.877	R_int = 0.043
24143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
4800 reflections	Δρ_min = −0.16 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	0.08739 (10)	0.64809 (8)	0.66867 (6)	0.0379 (2)
O2	0.19599 (10)	0.86929 (8)	0.83185 (6)	0.0388 (2)
O3	−0.20151 (10)	0.67148 (9)	0.48478 (6)	0.0419 (2)
O4	−0.01872 (10)	0.83966 (9)	1.00812 (6)	0.0429 (2)
C1	−0.13726 (14)	0.73032 (10)	0.65387 (9)	0.0312 (3)
C2	−0.25357 (15)	0.70050 (11)	0.56859 (9)	0.0345 (3)
C3	−0.41501 (15)	0.69700 (12)	0.56983 (10)	0.0399 (3)
H3	−0.4924	0.6770	0.5106	0.048*
C4	−0.45851 (15)	0.72264 (12)	0.65675 (10)	0.0407 (3)
H4	−0.5671	0.7211	0.6576	0.049*
C5	−0.34659 (14)	0.75145 (11)	0.74590 (9)	0.0360 (3)
C6	−0.39763 (15)	0.77691 (13)	0.83424 (10)	0.0429 (3)
H6	−0.5073	0.7742	0.8325	0.052*
C7	−0.29423 (16)	0.80531 (13)	0.92212 (10)	0.0430 (3)
H7	−0.3305	0.8231	0.9810	0.052*
C8	−0.13216 (15)	0.80769 (12)	0.92383 (9)	0.0364 (3)
C9	−0.07595 (14)	0.78095 (11)	0.83942 (9)	0.0313 (3)
C10	−0.18165 (14)	0.75431 (10)	0.74623 (9)	0.0313 (3)
C11	0.02752 (14)	0.72402 (10)	0.63903 (8)	0.0306 (3)
C12	0.11099 (14)	0.81261 (11)	0.58353 (9)	0.0327 (3)
C13	0.11822 (17)	0.93448 (12)	0.61063 (10)	0.0440 (3)
H13	0.0676	0.9596	0.6617	0.053*
C14	0.1996 (2)	1.02299 (13)	0.56390 (13)	0.0560 (4)
H14	0.2063	1.1076	0.5848	0.067*
C15	0.26881 (18)	0.98776 (14)	0.48875 (12)	0.0530 (4)
H15	0.3246	1.0484	0.4581	0.064*
C16	0.25873 (15)	0.86244 (12)	0.45584 (9)	0.0402 (3)
C17	0.31914 (16)	0.82289 (15)	0.37281 (10)	0.0489 (4)
H17	0.3743	0.8826	0.3412	0.059*
C18	0.29954 (16)	0.70146 (15)	0.33786 (10)	0.0481 (4)
H18	0.3374	0.6766	0.2809	0.058*
C19	0.22326 (15)	0.61257 (13)	0.38595 (9)	0.0427 (3)
H19	0.2106	0.5277	0.3615	0.051*
C20	0.16714 (14)	0.64674 (11)	0.46737 (9)	0.0351 (3)
H20	0.1180	0.5853	0.4997	0.042*
C21	0.18097 (13)	0.77222 (11)	0.50452 (8)	0.0325 (3)
C22	0.10078 (14)	0.78898 (10)	0.85622 (8)	0.0307 (3)
C23	0.15239 (14)	0.69517 (11)	0.90702 (8)	0.0321 (3)
C24	0.06855 (16)	0.57328 (11)	0.87330 (9)	0.0385 (3)
H24	−0.0238	0.5518	0.8222	0.046*
C25	0.11646 (19)	0.47971 (13)	0.91269 (11)	0.0484 (3)
H25	0.0583	0.3957	0.8873	0.058*
C26	0.2463 (2)	0.50928 (14)	0.98733 (11)	0.0515 (4)
H26	0.2797	0.4455	1.0128	0.062*
C27	0.33248 (16)	0.63426 (14)	1.02763 (9)	0.0426 (3)
C28	0.46076 (18)	0.66683 (18)	1.10997 (11)	0.0558 (4)
H28	0.4948	0.6036	1.1360	0.067*
C29	0.53555 (17)	0.78660 (18)	1.15211 (10)	0.0583 (4)
H29	0.6198	0.8066	1.2080	0.070*
C30	0.48893 (16)	0.88165 (16)	1.11340 (10)	0.0518 (4)
H30	0.5410	0.9654	1.1437	0.062*
C31	0.36913 (15)	0.85385 (13)	1.03242 (9)	0.0408 (3)
H31	0.3408	0.9188	1.0061	0.049*
C32	0.28633 (14)	0.72967 (12)	0.98702 (8)	0.0351 (3)
C33	−0.31667 (16)	0.62668 (13)	0.39438 (9)	0.0426 (3)
H33A	−0.3755	0.6882	0.3820	0.051*
H33B	−0.3954	0.5489	0.3965	0.051*
C34	−0.2252 (2)	0.60500 (16)	0.31584 (10)	0.0560 (4)
H34A	−0.1664	0.5449	0.3294	0.067*
H34B	−0.1490	0.6829	0.3138	0.067*
H34C	−0.3005	0.5730	0.2529	0.067*
C35	−0.06724 (16)	0.86450 (12)	1.09918 (9)	0.0395 (3)
H35A	−0.1508	0.7922	1.1063	0.047*
H35B	−0.1118	0.9364	1.1028	0.047*
C36	0.07978 (18)	0.89118 (14)	1.17804 (10)	0.0472 (3)
H36A	0.1255	0.8209	1.1717	0.057*
H36B	0.0504	0.9048	1.2419	0.057*
H36C	0.1595	0.9652	1.1721	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0401 (5)	0.0440 (5)	0.0379 (5)	0.0200 (4)	0.0118 (4)	0.0157 (4)
O2	0.0334 (5)	0.0402 (5)	0.0419 (5)	0.0070 (4)	0.0067 (4)	0.0117 (4)
O3	0.0345 (5)	0.0570 (6)	0.0308 (5)	0.0128 (4)	0.0012 (4)	0.0042 (4)
O4	0.0364 (5)	0.0645 (6)	0.0302 (5)	0.0211 (4)	0.0071 (4)	0.0055 (4)
C1	0.0292 (6)	0.0307 (6)	0.0343 (6)	0.0085 (5)	0.0052 (5)	0.0093 (5)
C2	0.0336 (6)	0.0352 (6)	0.0346 (6)	0.0094 (5)	0.0049 (5)	0.0094 (5)
C3	0.0307 (6)	0.0474 (7)	0.0384 (7)	0.0080 (5)	−0.0011 (5)	0.0119 (6)
C4	0.0268 (6)	0.0497 (8)	0.0474 (7)	0.0108 (5)	0.0055 (5)	0.0169 (6)
C5	0.0287 (6)	0.0412 (7)	0.0405 (7)	0.0112 (5)	0.0070 (5)	0.0132 (5)
C6	0.0296 (6)	0.0597 (8)	0.0467 (8)	0.0186 (6)	0.0125 (5)	0.0177 (6)
C7	0.0386 (7)	0.0600 (8)	0.0387 (7)	0.0223 (6)	0.0144 (5)	0.0144 (6)
C8	0.0337 (6)	0.0440 (7)	0.0345 (6)	0.0150 (5)	0.0059 (5)	0.0108 (5)
C9	0.0301 (6)	0.0331 (6)	0.0337 (6)	0.0122 (5)	0.0073 (5)	0.0091 (5)
C10	0.0292 (6)	0.0313 (6)	0.0353 (6)	0.0099 (5)	0.0059 (5)	0.0104 (5)
C11	0.0311 (6)	0.0336 (6)	0.0257 (5)	0.0091 (5)	0.0033 (4)	0.0041 (5)
C12	0.0274 (6)	0.0352 (6)	0.0343 (6)	0.0083 (5)	0.0016 (5)	0.0088 (5)
C13	0.0447 (7)	0.0376 (7)	0.0500 (8)	0.0126 (6)	0.0082 (6)	0.0093 (6)
C14	0.0584 (9)	0.0336 (7)	0.0743 (11)	0.0085 (6)	0.0098 (8)	0.0168 (7)
C15	0.0466 (8)	0.0470 (8)	0.0667 (10)	0.0039 (6)	0.0119 (7)	0.0298 (7)
C16	0.0292 (6)	0.0499 (8)	0.0415 (7)	0.0067 (5)	0.0026 (5)	0.0206 (6)
C17	0.0341 (7)	0.0743 (10)	0.0429 (8)	0.0104 (6)	0.0093 (6)	0.0312 (7)
C18	0.0372 (7)	0.0768 (11)	0.0331 (7)	0.0175 (7)	0.0084 (5)	0.0155 (7)
C19	0.0342 (7)	0.0552 (8)	0.0363 (7)	0.0126 (6)	0.0048 (5)	0.0044 (6)
C20	0.0283 (6)	0.0410 (7)	0.0340 (6)	0.0067 (5)	0.0042 (5)	0.0084 (5)
C21	0.0233 (5)	0.0415 (7)	0.0317 (6)	0.0071 (5)	0.0006 (4)	0.0128 (5)
C22	0.0300 (6)	0.0348 (6)	0.0265 (6)	0.0098 (5)	0.0049 (5)	0.0034 (5)
C23	0.0303 (6)	0.0391 (6)	0.0311 (6)	0.0136 (5)	0.0102 (5)	0.0089 (5)
C24	0.0417 (7)	0.0396 (7)	0.0356 (6)	0.0119 (5)	0.0100 (5)	0.0086 (5)
C25	0.0640 (9)	0.0384 (7)	0.0488 (8)	0.0193 (6)	0.0170 (7)	0.0132 (6)
C26	0.0662 (10)	0.0569 (9)	0.0508 (8)	0.0367 (8)	0.0221 (7)	0.0259 (7)
C27	0.0406 (7)	0.0661 (9)	0.0345 (7)	0.0275 (6)	0.0158 (5)	0.0210 (6)
C28	0.0453 (8)	0.0967 (13)	0.0415 (8)	0.0351 (8)	0.0136 (6)	0.0318 (8)
C29	0.0339 (7)	0.1093 (14)	0.0337 (7)	0.0193 (8)	0.0065 (6)	0.0219 (8)
C30	0.0329 (7)	0.0773 (10)	0.0369 (7)	0.0036 (7)	0.0087 (6)	0.0046 (7)
C31	0.0311 (6)	0.0548 (8)	0.0358 (7)	0.0099 (6)	0.0092 (5)	0.0079 (6)
C32	0.0309 (6)	0.0505 (7)	0.0303 (6)	0.0171 (5)	0.0125 (5)	0.0116 (5)
C33	0.0426 (7)	0.0432 (7)	0.0364 (7)	0.0109 (6)	−0.0042 (5)	0.0059 (5)
C34	0.0647 (10)	0.0738 (10)	0.0340 (7)	0.0399 (8)	−0.0017 (6)	0.0034 (7)
C35	0.0448 (7)	0.0451 (7)	0.0345 (7)	0.0209 (6)	0.0129 (6)	0.0074 (5)
C36	0.0519 (8)	0.0569 (8)	0.0339 (7)	0.0207 (7)	0.0083 (6)	0.0042 (6)

Geometric parameters (Å, º) top

O1—C11	1.2148 (14)	C18—H18	0.9500
O2—C22	1.2131 (14)	C19—C20	1.3644 (18)
O3—C2	1.3617 (15)	C19—H19	0.9500
O3—C33	1.4350 (14)	C20—C21	1.4157 (18)
O4—C8	1.3650 (15)	C20—H20	0.9500
O4—C35	1.4315 (15)	C22—C23	1.5015 (16)
C1—C2	1.3901 (16)	C23—C24	1.3723 (17)
C1—C10	1.4301 (17)	C23—C32	1.4266 (16)
C1—C11	1.5093 (16)	C24—C25	1.4031 (18)
C2—C3	1.4088 (18)	C24—H24	0.9500
C3—C4	1.3576 (19)	C25—C26	1.361 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.4113 (17)	C26—C27	1.418 (2)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.4081 (18)	C27—C28	1.419 (2)
C5—C10	1.4373 (17)	C27—C32	1.4239 (18)
C6—C7	1.3621 (19)	C28—C29	1.355 (2)
C6—H6	0.9500	C28—H28	0.9500
C7—C8	1.4104 (18)	C29—C30	1.409 (2)
C7—H7	0.9500	C29—H29	0.9500
C8—C9	1.3843 (17)	C30—C31	1.3661 (19)
C9—C10	1.4319 (16)	C30—H30	0.9500
C9—C22	1.5073 (16)	C31—C32	1.4185 (19)
C11—C12	1.4994 (16)	C31—H31	0.9500
C12—C13	1.3678 (18)	C33—C34	1.496 (2)
C12—C21	1.4283 (17)	C33—H33A	0.9900
C13—C14	1.406 (2)	C33—H33B	0.9900
C13—H13	0.9500	C34—H34A	0.9800
C14—C15	1.363 (2)	C34—H34B	0.9800
C14—H14	0.9500	C34—H34C	0.9800
C15—C16	1.411 (2)	C35—C36	1.5008 (19)
C15—H15	0.9500	C35—H35A	0.9900
C16—C17	1.421 (2)	C35—H35B	0.9900
C16—C21	1.4251 (17)	C36—H36A	0.9800
C17—C18	1.356 (2)	C36—H36B	0.9800
C17—H17	0.9500	C36—H36C	0.9800
C18—C19	1.404 (2)

C2—O3—C33	119.13 (10)	C21—C20—H20	119.5
C8—O4—C35	118.97 (10)	C20—C21—C16	118.15 (12)
C2—C1—C10	119.84 (11)	C20—C21—C12	123.61 (10)
C2—C1—C11	114.61 (10)	C16—C21—C12	118.08 (11)
C10—C1—C11	125.36 (10)	O2—C22—C23	122.19 (10)
O3—C2—C1	115.41 (11)	O2—C22—C9	121.24 (10)
O3—C2—C3	122.72 (11)	C23—C22—C9	116.54 (10)
C1—C2—C3	121.84 (12)	C24—C23—C32	120.11 (11)
C4—C3—C2	119.11 (11)	C24—C23—C22	118.12 (11)
C4—C3—H3	120.4	C32—C23—C22	121.76 (11)
C2—C3—H3	120.4	C23—C24—C25	121.34 (13)
C3—C4—C5	121.73 (12)	C23—C24—H24	119.3
C3—C4—H4	119.1	C25—C24—H24	119.3
C5—C4—H4	119.1	C26—C25—C24	119.97 (13)
C6—C5—C4	119.63 (11)	C26—C25—H25	120.0
C6—C5—C10	120.35 (11)	C24—C25—H25	120.0
C4—C5—C10	120.01 (12)	C25—C26—C27	120.78 (12)
C7—C6—C5	121.85 (12)	C25—C26—H26	119.6
C7—C6—H6	119.1	C27—C26—H26	119.6
C5—C6—H6	119.1	C26—C27—C28	121.37 (13)
C6—C7—C8	118.56 (12)	C26—C27—C32	119.59 (12)
C6—C7—H7	120.7	C28—C27—C32	119.00 (14)
C8—C7—H7	120.7	C29—C28—C27	121.08 (14)
O4—C8—C9	115.18 (11)	C29—C28—H28	119.5
O4—C8—C7	122.69 (11)	C27—C28—H28	119.5
C9—C8—C7	122.11 (11)	C28—C29—C30	120.29 (13)
C8—C9—C10	120.16 (11)	C28—C29—H29	119.9
C8—C9—C22	114.25 (10)	C30—C29—H29	119.9
C10—C9—C22	125.53 (10)	C31—C30—C29	120.27 (15)
C1—C10—C9	125.67 (11)	C31—C30—H30	119.9
C1—C10—C5	117.42 (11)	C29—C30—H30	119.9
C9—C10—C5	116.91 (11)	C30—C31—C32	121.15 (14)
O1—C11—C12	121.76 (11)	C30—C31—H31	119.4
O1—C11—C1	121.13 (10)	C32—C31—H31	119.4
C12—C11—C1	117.07 (10)	C31—C32—C27	118.16 (12)
C13—C12—C21	120.45 (11)	C31—C32—C23	123.58 (11)
C13—C12—C11	117.95 (11)	C27—C32—C23	118.12 (12)
C21—C12—C11	121.60 (10)	O3—C33—C34	107.15 (11)
C12—C13—C14	120.83 (14)	O3—C33—H33A	110.3
C12—C13—H13	119.6	C34—C33—H33A	110.3
C14—C13—H13	119.6	O3—C33—H33B	110.3
C15—C14—C13	120.21 (14)	C34—C33—H33B	110.3
C15—C14—H14	119.9	H33A—C33—H33B	108.5
C13—C14—H14	119.9	C33—C34—H34A	109.5
C14—C15—C16	120.85 (12)	C33—C34—H34B	109.5
C14—C15—H15	119.6	H34A—C34—H34B	109.5
C16—C15—H15	119.6	C33—C34—H34C	109.5
C15—C16—C17	121.61 (12)	H34A—C34—H34C	109.5
C15—C16—C21	119.50 (13)	H34B—C34—H34C	109.5
C17—C16—C21	118.84 (13)	O4—C35—C36	107.01 (11)
C18—C17—C16	121.22 (12)	O4—C35—H35A	110.3
C18—C17—H17	119.4	C36—C35—H35A	110.3
C16—C17—H17	119.4	O4—C35—H35B	110.3
C17—C18—C19	119.91 (13)	C36—C35—H35B	110.3
C17—C18—H18	120.0	H35A—C35—H35B	108.6
C19—C18—H18	120.0	C35—C36—H36A	109.5
C20—C19—C18	120.76 (13)	C35—C36—H36B	109.5
C20—C19—H19	119.6	H36A—C36—H36B	109.5
C18—C19—H19	119.6	C35—C36—H36C	109.5
C19—C20—C21	121.07 (12)	H36A—C36—H36C	109.5
C19—C20—H20	119.5	H36B—C36—H36C	109.5

C33—O3—C2—C1	173.31 (10)	C14—C15—C16—C21	−2.7 (2)
C33—O3—C2—C3	−4.73 (17)	C15—C16—C17—C18	−175.60 (13)
C10—C1—C2—O3	−175.91 (10)	C21—C16—C17—C18	2.06 (19)
C11—C1—C2—O3	−0.66 (15)	C16—C17—C18—C19	−2.2 (2)
C10—C1—C2—C3	2.16 (18)	C17—C18—C19—C20	0.5 (2)
C11—C1—C2—C3	177.41 (11)	C18—C19—C20—C21	1.36 (18)
O3—C2—C3—C4	177.47 (11)	C19—C20—C21—C16	−1.48 (17)
C1—C2—C3—C4	−0.46 (19)	C19—C20—C21—C12	173.70 (11)
C2—C3—C4—C5	−0.7 (2)	C15—C16—C21—C20	177.51 (11)
C3—C4—C5—C6	−179.75 (12)	C17—C16—C21—C20	−0.20 (17)
C3—C4—C5—C10	0.06 (19)	C15—C16—C21—C12	2.06 (17)
C4—C5—C6—C7	−179.93 (12)	C17—C16—C21—C12	−175.65 (10)
C10—C5—C6—C7	0.3 (2)	C13—C12—C21—C20	−174.76 (12)
C5—C6—C7—C8	−0.7 (2)	C11—C12—C21—C20	5.09 (17)
C35—O4—C8—C9	−177.76 (10)	C13—C12—C21—C16	0.42 (16)
C35—O4—C8—C7	3.98 (18)	C11—C12—C21—C16	−179.73 (10)
C6—C7—C8—O4	177.47 (12)	C8—C9—C22—O2	−111.50 (13)
C6—C7—C8—C9	−0.7 (2)	C10—C9—C22—O2	65.60 (17)
O4—C8—C9—C10	−175.82 (10)	C8—C9—C22—C23	66.74 (14)
C7—C8—C9—C10	2.45 (19)	C10—C9—C22—C23	−116.16 (12)
O4—C8—C9—C22	1.45 (16)	O2—C22—C23—C24	−132.46 (12)
C7—C8—C9—C22	179.73 (11)	C9—C22—C23—C24	49.32 (15)
C2—C1—C10—C9	177.29 (11)	O2—C22—C23—C32	46.38 (17)
C11—C1—C10—C9	2.59 (18)	C9—C22—C23—C32	−131.84 (11)
C2—C1—C10—C5	−2.66 (17)	C32—C23—C24—C25	−3.29 (18)
C11—C1—C10—C5	−177.36 (10)	C22—C23—C24—C25	175.57 (12)
C8—C9—C10—C1	177.30 (11)	C23—C24—C25—C26	1.5 (2)
C22—C9—C10—C1	0.36 (19)	C24—C25—C26—C27	1.4 (2)
C8—C9—C10—C5	−2.76 (17)	C25—C26—C27—C28	175.37 (13)
C22—C9—C10—C5	−179.70 (10)	C25—C26—C27—C32	−2.4 (2)
C6—C5—C10—C1	−178.61 (11)	C26—C27—C28—C29	−175.54 (13)
C4—C5—C10—C1	1.59 (17)	C32—C27—C28—C29	2.3 (2)
C6—C5—C10—C9	1.45 (17)	C27—C28—C29—C30	−1.3 (2)
C4—C5—C10—C9	−178.35 (11)	C28—C29—C30—C31	−0.7 (2)
C2—C1—C11—O1	−114.04 (12)	C29—C30—C31—C32	1.7 (2)
C10—C1—C11—O1	60.90 (16)	C30—C31—C32—C27	−0.59 (18)
C2—C1—C11—C12	64.06 (14)	C30—C31—C32—C23	175.03 (11)
C10—C1—C11—C12	−121.00 (12)	C26—C27—C32—C31	176.52 (12)
O1—C11—C12—C13	−132.64 (13)	C28—C27—C32—C31	−1.34 (17)
C1—C11—C12—C13	49.27 (15)	C26—C27—C32—C23	0.66 (18)
O1—C11—C12—C21	47.51 (16)	C28—C27—C32—C23	−177.21 (11)
C1—C11—C12—C21	−130.58 (11)	C24—C23—C32—C31	−173.48 (12)
C21—C12—C13—C14	−2.40 (19)	C22—C23—C32—C31	7.71 (17)
C11—C12—C13—C14	177.75 (12)	C24—C23—C32—C27	2.15 (17)
C12—C13—C14—C15	1.9 (2)	C22—C23—C32—C27	−176.67 (11)
C13—C14—C15—C16	0.7 (2)	C2—O3—C33—C34	179.03 (11)
C14—C15—C16—C17	175.00 (14)	C8—O4—C35—C36	177.51 (11)

Hydrogen-bond geometry (Å, º) top

Cg4 and Cg6 are the centroids of the C16–C21 and C27–C32 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg4ⁱ	0.95	2.77	3.5662 (15)	142
C7—H7···Cg6ⁱ	0.95	2.76	3.5662 (16)	143
C30—H30···O2ⁱⁱ	0.95	2.53	3.3289 (19)	142
C34—H34A···O1ⁱⁱⁱ	0.98	2.47	3.423 (2)	163
C35—H35B···O2^iv	0.99	2.59	3.5476 (17)	163

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

Experimental details

Crystal data
Chemical formula	C₃₆H₂₈O₄
M_r	524.58
Crystal system, space group	Triclinic, P1
Temperature (K)	193
a, b, c (Å)	8.76532 (16), 11.4266 (2), 14.1972 (3)
α, β, γ (°)	99.080 (1), 99.036 (1), 104.277 (1)
V (Å³)	1331.94 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.60 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.689, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	24143, 4800, 4142
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.106, 1.07
No. of reflections	4800
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −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

Cg4 and Cg6 are the centroids of the C16–C21 and C27–C32 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg4ⁱ	0.95	2.77	3.5662 (15)	142
C7—H7···Cg6ⁱ	0.95	2.76	3.5662 (16)	143
C30—H30···O2ⁱⁱ	0.95	2.53	3.3289 (19)	142
C34—H34A···O1ⁱⁱⁱ	0.98	2.47	3.423 (2)	163
C35—H35B···O2^iv	0.99	2.59	3.5476 (17)	163

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −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 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., 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
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
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454. 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
Tsumuki, T., Okamoto, A., Oike, H. & Yonezawa, N. (2013). Acta Cryst. E69, o369. 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 4| April 2013| Pages o495-o496

doi:10.1107/S1600536813005710

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-1-yl)carbon­yl]naph­thalen-1-yl}(naphthalen-1-yl)methanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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