1-Benzoyl­naphthalene-2,7-diyl dibenzoate

Sakamoto, R.; Sasagawa, K.; Hijikata, D.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536812052026

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o210

doi:10.1107/S1600536812052026

Open

access

1-Benzoylnaphthalene-2,7-diyl dibenzoate

Rei Sakamoto,^a Kosuke Sasagawa,^a Daichi Hijikata,^a Akiko Okamoto ^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 18 December 2012; accepted 29 December 2012; online 9 January 2013)

In the title compound, C₃₁H₂₀O₅, the phenyl rings of the benzoyloxy and benzoyl groups are twisted away from the naphthalene ring system by 64.27 (6), 73.62 (5) and 80.41 (6)°. In the crystal, C—H⋯O hydrogen bonds and C—H⋯π interactions link the molecules, forming tubular chains parallel to the b axis. The chains are further connected into a three-dimensional network by C—H⋯π interactions and π–π stacking contacts [centroid–centroid distances = 3.622 (10)–3.866 (12) Å].

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ); Okamoto et al. (2011 ). For structures of closely related compounds, see: Kato et al. (2010 ); Muto et al. (2011 ); Nakaema et al. (2008 ); Sakamoto et al. (2012 ); Watanabe et al. (2010 ).

Experimental

Crystal data

C₃₁H₂₀O₅
M_r = 472.47
Monoclinic, P 2₁ /n
a = 16.1318 (3) Å
b = 7.18561 (13) Å
c = 20.7333 (4) Å
β = 99.180 (1)°
V = 2372.56 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.73 mm⁻¹
T = 193 K
0.40 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.759, T_max = 0.811
40057 measured reflections
4282 independent reflections
3753 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.103
S = 1.07
4282 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C26–C31 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.30	3.2183 (16)	164
C14—H14⋯O5ⁱⁱ	0.95	2.60	3.520 (2)	164
C29—H29⋯Cg1ⁱⁱⁱ	0.95	2.72	3.6396 (18)	162
C15—H15⋯Cg2ⁱⁱ	0.95	2.78	3.6397 (19)	150
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812052026/rz5035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812052026/rz5035Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812052026/rz5035Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of the naphthalene 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 X-ray crystal structures of 1,8-diaroylnaphthalenes, e.g., 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al., 2008). The two aroyl groups at 1,8-positions of the naphthalene ring in these compounds are perpendicularly attached to the naphthalene ring and oriented in opposite directions. Furthermore, we have also clarified the crystal structures of 1-monoaroylated naphthalene compounds such as (2,7-dimethoxynaphthalene-1-yl)-(phenyl)methanone (Kato et al., 2010) and 2,7-dimethoxy-1-(4-nitrobenzoyl)naphthalene (Watanabe et al., 2010). These compounds also exhibit essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. Besides, the crystal structures of the aroylnaphthalene derivatives bearing benzoic ester moiety at the 2- or 2,7-positions on the naphthalene ring, 7-methoxy-1-(4-nitrobenzoyl)naphthalene-2-yl 4-nitrobenzoate (Muto et al., 2011) and 1,8-dibenzoylnaphthalene-2,7-diyl dibenzoate (Sakamoto et al., 2012) have been revealed.

The molecular structure of the title compound is displayed in Fig 1. The benzene ring of the benzoyl group is almost orthogonal to the naphthalene ring system forming a dihedral angle of 80.41 (6)° [C10—C1—C11—O1 torsion angle = 83.35 (15)°]. The two carbonyl moieties of the benzoyloxy groups at the 2,7-positions of the naphthalene ring system are in opposite directions relative to one another, as observed in the homologous compound 1,8-dibenzoylnaphthalene-2,7-diyl dibenzoate (Sakamoto et al., 2012). The phenyl ring of the benzoyloxy group at the 7-position is inclined to form a narrower dihedral angle with the naphthalene ring system [64.27 (6)° and O5—C25—C26—C27 torsion angle = -21.8 (2)°] than the phenyl ring of the benzoyloxy group at the 2-position adjacent to the benzoyl group [73.62 (5)° and O3—C18—C19—C24 torsion angle = -2.1 (2)°]. In the crystal, C–H···O hydrogen bonds between an hydrogen atom of the phenyl ring of the benzoyl group and a carbonyl oxygen of the benzoyloxy group and between an hydrogen atom of the naphthalene ring system and a carbonyl oxygen of the benzoyl group, and weak C–H···π interactions (Table 1) link the molecules into tubular chains running parallel to the b axis (Fig. 2 and 3). Furthermore, the chains are connected into a three-dimensional network by weak C–H···π interactions [C15–H15···Cg2 = 2.78 Å; Cg2 is the centroids of the C5–C10 ring] and π–π contacts [Cg2ⁱⁱⁱ···Cg3, 3.622 (10) Å; Cg4···Cg4^iv = 3.821 (12) Å; Cg4···Cg4^v = 3.866 (12) Å; Cg3 and Cg4 are the centroids of the C1/C4-C9-C10 and C19/C24 rings, respectively; symmetry codes: (iii) 1-x, 1-y, 1-z; (iv) -x, 1-y, 1-z; (v) -x, 2-y, 1-z).

Related literature top

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For structures of closely related compounds, see: Kato et al. (2010); Muto et al. (2011); Nakaema et al. (2008); Sakamoto et al. (2012); Watanabe et al. (2010).

Experimental top

The title compound was prepared via condensation reaction of 1-benzoyl-2,7-dihydroxynaphthalene (0.2 mmol, 52.86 mg) obtained by ethyl ether cleavage reaction of 1-benzoyl-2,7-diethoxynaphthalene, benzoyl chloride (0.4 mmol, 0.046 ml), and triethylamine (0.4 mmol, 0.056 ml) in dichloromethane (2.5 ml). After the reaction mixture was stirred at rt for 2 h, it was poured into water (30 ml) and the mixture was extracted with CHCl₃ (10 ml×3). The combined extracts were washed with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from ethyl acetate–hexane (3:1 v/v) and colorless single crystals suitable for X-ray diffraction were obtained (isolated yield 36%).

Spectroscopic data: ¹H NMR δ (400 MHz, CDCl₃): 7.24–7.38 (4H, m), 7.45–7.54 (6H, m), 7.59 (1H, d, J = 2.4 Hz), 7.63 (1H, t, J = 14.8 Hz), 7.74 (2H, d, J = 7.6 Hz), 7.85 (2H, d, J = 7.2 Hz), 8.02 (1H, d, J = 9.2 Hz), 8.08 (1H, d, J = 9.2 Hz), 8.18 (2H, d, J = 7.2 Hz) p.p.m.. ¹³C NMR δ (75 MHz, CDCl₃): 116.33, 121.37, 121.93, 127.64, 128.26, 128.38, 128.51, 128.61, 129.10, 129.52, 129.59, 129.76, 129.87, 130.13, 130.86, 132.06, 133.59, 133.66, 133.76, 137.49, 146.53, 150.09, 164.18, 164.95, 195.32 p.p.m.. IR (KBr): 1739 (OC=O), 1658 (C=O), 1596,1582, 1510 (Ar) cm^-1. m.p. = 422.0–422.8 K. HRMS (m/z): [M+H]⁺ calcd. for C₃₁H₂₀O₅, 473.1390, found, 473.1384.

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 compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Partial crystal packing of the title compound showing C—H···O and C—H···π interactions as dashed lines.
	Fig. 3. C–H···O interaction (dashed line) between naphthalene ring and ketonic carbonyl group.

1-Benzoylnaphthalene-2,7-diyl dibenzoate top

Crystal data top

C₃₁H₂₀O₅	F(000) = 984
M_r = 472.47	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 33959 reflections
a = 16.1318 (3) Å	θ = 3.2–68.2°
b = 7.18561 (13) Å	µ = 0.73 mm⁻¹
c = 20.7333 (4) Å	T = 193 K
β = 99.180 (1)°	Block, colorless
V = 2372.56 (7) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4282 independent reflections
Radiation source: fine-focus sealed tube	3753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.2°
ω scans	h = −19→19
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −8→8
T_min = 0.759, T_max = 0.811	l = −24→24
40057 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) = 0.103	w = 1/[σ²(F_o²) + (0.0548P)² + 0.4366P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4282 reflections	Δρ_max = 0.18 e Å⁻³
326 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: 0.0025 (2)

Crystal data top

C₃₁H₂₀O₅	V = 2372.56 (7) Å³
M_r = 472.47	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 16.1318 (3) Å	µ = 0.73 mm⁻¹
b = 7.18561 (13) Å	T = 193 K
c = 20.7333 (4) Å	0.40 × 0.40 × 0.30 mm
β = 99.180 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4282 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3753 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.811	R_int = 0.027
40057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
4282 reflections	Δρ_min = −0.16 e Å⁻³
326 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	0.26313 (6)	0.21093 (12)	0.46194 (4)	0.0438 (2)
O2	0.20361 (5)	0.66287 (13)	0.43467 (4)	0.0425 (2)
O3	0.21367 (7)	0.6819 (2)	0.54365 (5)	0.0750 (4)
O4	0.56034 (6)	0.12325 (13)	0.37018 (4)	0.0434 (2)
O5	0.52644 (9)	0.19992 (17)	0.26435 (5)	0.0712 (4)
C1	0.32080 (7)	0.47803 (17)	0.42157 (6)	0.0336 (3)
C2	0.29093 (8)	0.64552 (18)	0.43808 (6)	0.0378 (3)
C3	0.34234 (9)	0.80265 (18)	0.45251 (6)	0.0424 (3)
H3	0.3195	0.9172	0.4644	0.051*
C4	0.42574 (9)	0.78701 (17)	0.44913 (6)	0.0405 (3)
H4	0.4613	0.8917	0.4596	0.049*
C5	0.54650 (8)	0.60238 (19)	0.42507 (6)	0.0409 (3)
H5	0.5828	0.7056	0.4362	0.049*
C6	0.57842 (8)	0.4414 (2)	0.40428 (6)	0.0426 (3)
H6	0.6362	0.4326	0.4005	0.051*
C7	0.52458 (8)	0.28923 (18)	0.38861 (6)	0.0376 (3)
C8	0.44177 (8)	0.29459 (17)	0.39456 (6)	0.0350 (3)
H8	0.4074	0.1878	0.3845	0.042*
C9	0.46055 (8)	0.61883 (17)	0.43044 (6)	0.0354 (3)
C10	0.40728 (7)	0.46095 (16)	0.41582 (5)	0.0327 (3)
C11	0.26389 (7)	0.31006 (17)	0.41439 (6)	0.0341 (3)
C12	0.21077 (8)	0.27099 (18)	0.35081 (6)	0.0386 (3)
C13	0.16406 (9)	0.1071 (2)	0.34343 (7)	0.0495 (3)
H13	0.1692	0.0191	0.3780	0.059*
C14	0.11042 (10)	0.0725 (3)	0.28590 (8)	0.0637 (5)
H14	0.0785	−0.0391	0.2809	0.076*
C15	0.10333 (11)	0.1994 (3)	0.23606 (8)	0.0713 (5)
H15	0.0652	0.1768	0.1970	0.086*
C16	0.15089 (12)	0.3593 (3)	0.24206 (8)	0.0729 (5)
H16	0.1466	0.4446	0.2067	0.088*
C17	0.20496 (10)	0.3964 (2)	0.29958 (7)	0.0544 (4)
H17	0.2377	0.5068	0.3038	0.065*
C18	0.17106 (9)	0.68610 (19)	0.49101 (7)	0.0450 (3)
C19	0.07915 (8)	0.71619 (18)	0.47694 (7)	0.0413 (3)
C20	0.03506 (8)	0.72662 (19)	0.41374 (7)	0.0433 (3)
H20	0.0637	0.7108	0.3775	0.052*
C21	−0.05051 (9)	0.7600 (2)	0.40370 (8)	0.0506 (4)
H21	−0.0807	0.7679	0.3605	0.061*
C22	−0.09207 (9)	0.7819 (2)	0.45659 (8)	0.0556 (4)
H22	−0.1507	0.8059	0.4497	0.067*
C23	−0.04879 (10)	0.7690 (2)	0.51924 (8)	0.0560 (4)
H23	−0.0778	0.7826	0.5554	0.067*
C24	0.03664 (10)	0.7363 (2)	0.52965 (7)	0.0505 (4)
H24	0.0664	0.7276	0.5730	0.061*
C25	0.56198 (8)	0.0984 (2)	0.30540 (6)	0.0439 (3)
C26	0.61134 (8)	−0.06865 (19)	0.29340 (6)	0.0415 (3)
C27	0.59531 (11)	−0.1511 (2)	0.23219 (8)	0.0579 (4)
H27	0.5543	−0.0993	0.1991	0.069*
C28	0.63909 (12)	−0.3084 (2)	0.21950 (9)	0.0670 (5)
H28	0.6277	−0.3655	0.1777	0.080*
C29	0.69917 (10)	−0.3831 (2)	0.26699 (8)	0.0577 (4)
H29	0.7287	−0.4921	0.2581	0.069*
C30	0.71647 (9)	−0.2999 (2)	0.32736 (8)	0.0500 (4)
H30	0.7587	−0.3505	0.3598	0.060*
C31	0.67265 (8)	−0.1426 (2)	0.34107 (7)	0.0440 (3)
H31	0.6845	−0.0857	0.3829	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0459 (5)	0.0411 (5)	0.0436 (5)	0.0008 (4)	0.0050 (4)	0.0052 (4)
O2	0.0361 (5)	0.0463 (5)	0.0443 (5)	0.0103 (4)	0.0037 (4)	−0.0065 (4)
O3	0.0498 (6)	0.1293 (12)	0.0434 (6)	0.0096 (7)	0.0000 (5)	0.0035 (6)
O4	0.0428 (5)	0.0494 (5)	0.0397 (5)	0.0133 (4)	0.0120 (4)	0.0041 (4)
O5	0.1021 (9)	0.0679 (7)	0.0420 (6)	0.0397 (7)	0.0066 (6)	0.0050 (5)
C1	0.0337 (6)	0.0344 (6)	0.0314 (6)	0.0018 (5)	0.0014 (5)	−0.0007 (5)
C2	0.0354 (6)	0.0390 (7)	0.0376 (6)	0.0052 (5)	0.0020 (5)	−0.0014 (5)
C3	0.0509 (8)	0.0329 (6)	0.0413 (7)	0.0048 (5)	0.0015 (6)	−0.0033 (5)
C4	0.0486 (8)	0.0346 (7)	0.0359 (6)	−0.0053 (5)	−0.0009 (5)	−0.0003 (5)
C5	0.0384 (7)	0.0480 (7)	0.0351 (6)	−0.0088 (6)	0.0022 (5)	0.0047 (5)
C6	0.0334 (6)	0.0551 (8)	0.0398 (7)	−0.0001 (6)	0.0074 (5)	0.0081 (6)
C7	0.0379 (7)	0.0433 (7)	0.0320 (6)	0.0068 (5)	0.0063 (5)	0.0042 (5)
C8	0.0348 (6)	0.0366 (6)	0.0330 (6)	0.0007 (5)	0.0037 (5)	0.0006 (5)
C9	0.0387 (7)	0.0372 (6)	0.0291 (6)	−0.0037 (5)	0.0013 (5)	0.0027 (5)
C10	0.0338 (6)	0.0356 (6)	0.0276 (6)	0.0004 (5)	0.0016 (5)	0.0016 (5)
C11	0.0299 (6)	0.0349 (6)	0.0379 (6)	0.0056 (5)	0.0067 (5)	−0.0023 (5)
C12	0.0328 (6)	0.0457 (7)	0.0380 (7)	−0.0004 (5)	0.0074 (5)	−0.0069 (5)
C13	0.0448 (8)	0.0523 (8)	0.0518 (8)	−0.0068 (6)	0.0090 (6)	−0.0134 (7)
C14	0.0525 (9)	0.0782 (11)	0.0598 (10)	−0.0155 (8)	0.0068 (7)	−0.0281 (9)
C15	0.0553 (10)	0.1101 (15)	0.0453 (9)	−0.0065 (10)	−0.0017 (7)	−0.0271 (10)
C16	0.0739 (12)	0.1018 (15)	0.0393 (8)	−0.0034 (11)	−0.0025 (8)	0.0056 (9)
C17	0.0519 (8)	0.0668 (10)	0.0429 (8)	−0.0090 (7)	0.0031 (6)	0.0021 (7)
C18	0.0459 (8)	0.0463 (7)	0.0427 (7)	0.0049 (6)	0.0062 (6)	−0.0003 (6)
C19	0.0418 (7)	0.0378 (7)	0.0448 (7)	0.0010 (5)	0.0080 (6)	−0.0022 (5)
C20	0.0412 (7)	0.0434 (7)	0.0459 (7)	0.0023 (6)	0.0086 (6)	−0.0019 (6)
C21	0.0415 (7)	0.0532 (8)	0.0559 (9)	0.0024 (6)	0.0045 (6)	−0.0015 (7)
C22	0.0404 (8)	0.0544 (9)	0.0736 (10)	0.0009 (6)	0.0138 (7)	−0.0081 (8)
C23	0.0528 (9)	0.0593 (9)	0.0610 (9)	−0.0033 (7)	0.0246 (7)	−0.0117 (7)
C24	0.0519 (8)	0.0538 (8)	0.0470 (8)	−0.0025 (7)	0.0118 (7)	−0.0054 (6)
C25	0.0435 (7)	0.0481 (7)	0.0406 (7)	0.0051 (6)	0.0085 (6)	0.0029 (6)
C26	0.0393 (7)	0.0436 (7)	0.0440 (7)	0.0022 (6)	0.0141 (6)	0.0034 (6)
C27	0.0674 (10)	0.0573 (9)	0.0478 (8)	0.0123 (8)	0.0061 (7)	−0.0009 (7)
C28	0.0854 (13)	0.0589 (10)	0.0574 (10)	0.0143 (9)	0.0130 (9)	−0.0116 (8)
C29	0.0600 (9)	0.0462 (8)	0.0724 (11)	0.0096 (7)	0.0273 (8)	−0.0001 (7)
C30	0.0385 (7)	0.0516 (8)	0.0625 (9)	0.0070 (6)	0.0156 (7)	0.0083 (7)
C31	0.0370 (7)	0.0489 (8)	0.0480 (8)	0.0009 (6)	0.0130 (6)	0.0029 (6)

Geometric parameters (Å, º) top

O1—C11	1.2180 (15)	C14—H14	0.9500
O2—C18	1.3653 (17)	C15—C16	1.377 (3)
O2—C2	1.4047 (15)	C15—H15	0.9500
O3—C18	1.1938 (17)	C16—C17	1.386 (2)
O4—C25	1.3594 (16)	C16—H16	0.9500
O4—C7	1.4041 (15)	C17—H17	0.9500
O5—C25	1.1957 (16)	C18—C19	1.4805 (19)
C1—C2	1.3602 (17)	C19—C24	1.387 (2)
C1—C10	1.4243 (17)	C19—C20	1.3897 (19)
C1—C11	1.5093 (17)	C20—C21	1.3837 (19)
C2—C3	1.4046 (18)	C20—H20	0.9500
C3—C4	1.363 (2)	C21—C22	1.382 (2)
C3—H3	0.9500	C21—H21	0.9500
C4—C9	1.4126 (18)	C22—C23	1.376 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.363 (2)	C23—C24	1.381 (2)
C5—C9	1.4136 (18)	C23—H23	0.9500
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.4021 (19)	C25—C26	1.4832 (19)
C6—H6	0.9500	C26—C27	1.387 (2)
C7—C8	1.3616 (18)	C26—C31	1.3876 (18)
C8—C10	1.4182 (17)	C27—C28	1.381 (2)
C8—H8	0.9500	C27—H27	0.9500
C9—C10	1.4262 (17)	C28—C29	1.375 (2)
C11—C12	1.4800 (17)	C28—H28	0.9500
C12—C17	1.384 (2)	C29—C30	1.375 (2)
C12—C13	1.3934 (19)	C29—H29	0.9500
C13—C14	1.380 (2)	C30—C31	1.386 (2)
C13—H13	0.9500	C30—H30	0.9500
C14—C15	1.369 (3)	C31—H31	0.9500

C18—O2—C2	119.17 (10)	C15—C16—H16	119.9
C25—O4—C7	117.01 (10)	C17—C16—H16	119.9
C2—C1—C10	119.22 (11)	C12—C17—C16	119.43 (15)
C2—C1—C11	119.88 (11)	C12—C17—H17	120.3
C10—C1—C11	120.75 (10)	C16—C17—H17	120.3
C1—C2—C3	122.96 (12)	O3—C18—O2	122.35 (13)
C1—C2—O2	117.29 (11)	O3—C18—C19	126.61 (14)
C3—C2—O2	119.51 (11)	O2—C18—C19	111.04 (11)
C4—C3—C2	118.48 (12)	C24—C19—C20	119.62 (13)
C4—C3—H3	120.8	C24—C19—C18	117.73 (13)
C2—C3—H3	120.8	C20—C19—C18	122.65 (13)
C3—C4—C9	121.57 (12)	C21—C20—C19	119.96 (13)
C3—C4—H4	119.2	C21—C20—H20	120.0
C9—C4—H4	119.2	C19—C20—H20	120.0
C6—C5—C9	121.36 (12)	C22—C21—C20	119.92 (14)
C6—C5—H5	119.3	C22—C21—H21	120.0
C9—C5—H5	119.3	C20—C21—H21	120.0
C5—C6—C7	118.93 (12)	C23—C22—C21	120.25 (14)
C5—C6—H6	120.5	C23—C22—H22	119.9
C7—C6—H6	120.5	C21—C22—H22	119.9
C8—C7—C6	122.50 (12)	C22—C23—C24	120.17 (15)
C8—C7—O4	120.02 (11)	C22—C23—H23	119.9
C6—C7—O4	117.35 (11)	C24—C23—H23	119.9
C7—C8—C10	119.43 (11)	C23—C24—C19	120.08 (14)
C7—C8—H8	120.3	C23—C24—H24	120.0
C10—C8—H8	120.3	C19—C24—H24	120.0
C4—C9—C5	122.07 (11)	O5—C25—O4	122.70 (13)
C4—C9—C10	119.10 (11)	O5—C25—C26	125.71 (13)
C5—C9—C10	118.82 (11)	O4—C25—C26	111.58 (11)
C8—C10—C1	122.46 (11)	C27—C26—C31	119.74 (13)
C8—C10—C9	118.92 (11)	C27—C26—C25	118.19 (12)
C1—C10—C9	118.60 (11)	C31—C26—C25	122.08 (12)
O1—C11—C12	122.06 (11)	C28—C27—C26	119.85 (15)
O1—C11—C1	118.18 (11)	C28—C27—H27	120.1
C12—C11—C1	119.75 (11)	C26—C27—H27	120.1
C17—C12—C13	119.77 (13)	C29—C28—C27	120.41 (16)
C17—C12—C11	121.24 (12)	C29—C28—H28	119.8
C13—C12—C11	118.96 (12)	C27—C28—H28	119.8
C14—C13—C12	120.03 (15)	C30—C29—C28	119.99 (14)
C14—C13—H13	120.0	C30—C29—H29	120.0
C12—C13—H13	120.0	C28—C29—H29	120.0
C15—C14—C13	119.88 (16)	C29—C30—C31	120.33 (14)
C15—C14—H14	120.1	C29—C30—H30	119.8
C13—C14—H14	120.1	C31—C30—H30	119.8
C14—C15—C16	120.63 (15)	C30—C31—C26	119.66 (14)
C14—C15—H15	119.7	C30—C31—H31	120.2
C16—C15—H15	119.7	C26—C31—H31	120.2
C15—C16—C17	120.21 (17)

C10—C1—C2—C3	−2.69 (19)	C1—C11—C12—C13	174.58 (12)
C11—C1—C2—C3	172.90 (11)	C17—C12—C13—C14	−1.8 (2)
C10—C1—C2—O2	171.67 (10)	C11—C12—C13—C14	176.31 (13)
C11—C1—C2—O2	−12.74 (17)	C12—C13—C14—C15	0.1 (2)
C18—O2—C2—C1	112.74 (13)	C13—C14—C15—C16	1.7 (3)
C18—O2—C2—C3	−72.69 (16)	C14—C15—C16—C17	−1.8 (3)
C1—C2—C3—C4	0.7 (2)	C13—C12—C17—C16	1.7 (2)
O2—C2—C3—C4	−173.51 (11)	C11—C12—C17—C16	−176.40 (14)
C2—C3—C4—C9	1.19 (19)	C15—C16—C17—C12	0.1 (3)
C9—C5—C6—C7	−0.61 (19)	C2—O2—C18—O3	−4.3 (2)
C5—C6—C7—C8	−1.32 (19)	C2—O2—C18—C19	175.60 (11)
C5—C6—C7—O4	−177.23 (11)	O3—C18—C19—C24	−2.1 (2)
C25—O4—C7—C8	92.97 (14)	O2—C18—C19—C24	178.03 (12)
C25—O4—C7—C6	−91.01 (14)	O3—C18—C19—C20	177.25 (16)
C6—C7—C8—C10	1.59 (18)	O2—C18—C19—C20	−2.63 (18)
O4—C7—C8—C10	177.40 (10)	C24—C19—C20—C21	1.1 (2)
C3—C4—C9—C5	178.27 (12)	C18—C19—C20—C21	−178.25 (13)
C3—C4—C9—C10	−1.06 (18)	C19—C20—C21—C22	−0.4 (2)
C6—C5—C9—C4	−177.17 (12)	C20—C21—C22—C23	−0.5 (2)
C6—C5—C9—C10	2.16 (18)	C21—C22—C23—C24	0.8 (2)
C7—C8—C10—C1	178.38 (11)	C22—C23—C24—C19	0.0 (2)
C7—C8—C10—C9	0.03 (17)	C20—C19—C24—C23	−0.9 (2)
C2—C1—C10—C8	−175.64 (11)	C18—C19—C24—C23	178.49 (14)
C11—C1—C10—C8	8.81 (17)	C7—O4—C25—O5	−8.6 (2)
C2—C1—C10—C9	2.72 (17)	C7—O4—C25—C26	172.23 (11)
C11—C1—C10—C9	−172.83 (10)	O5—C25—C26—C27	−21.8 (2)
C4—C9—C10—C8	177.51 (10)	O4—C25—C26—C27	157.33 (13)
C5—C9—C10—C8	−1.84 (16)	O5—C25—C26—C31	157.80 (16)
C4—C9—C10—C1	−0.91 (16)	O4—C25—C26—C31	−23.11 (18)
C5—C9—C10—C1	179.74 (10)	C31—C26—C27—C28	1.4 (2)
C2—C1—C11—O1	−92.16 (14)	C25—C26—C27—C28	−179.01 (15)
C10—C1—C11—O1	83.36 (14)	C26—C27—C28—C29	−0.6 (3)
C2—C1—C11—C12	87.46 (14)	C27—C28—C29—C30	−0.6 (3)
C10—C1—C11—C12	−97.02 (13)	C28—C29—C30—C31	1.1 (2)
O1—C11—C12—C17	172.31 (13)	C29—C30—C31—C26	−0.3 (2)
C1—C11—C12—C17	−7.30 (18)	C27—C26—C31—C30	−0.9 (2)
O1—C11—C12—C13	−5.81 (18)	C25—C26—C31—C30	179.50 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C26–C31 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.30	3.2183 (16)	164
C14—H14···O5ⁱⁱ	0.95	2.60	3.520 (2)	164
C29—H29···Cg1ⁱⁱⁱ	0.95	2.72	3.6396 (18)	162
C15—H15···Cg2ⁱⁱ	0.95	2.78	3.6397 (19)	150

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₁H₂₀O₅
M_r	472.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	16.1318 (3), 7.18561 (13), 20.7333 (4)
β (°)	99.180 (1)
V (Å³)	2372.56 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.759, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	40057, 4282, 3753
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.103, 1.07
No. of reflections	4282
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

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

Cg1 and Cg2 are the centroids of the C26–C31 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.30	3.2183 (16)	164
C14—H14···O5ⁱⁱ	0.95	2.60	3.520 (2)	164
C29—H29···Cg1ⁱⁱⁱ	0.95	2.72	3.6396 (18)	162
C15—H15···Cg2ⁱⁱ	0.95	2.78	3.6397 (19)	150

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors would like to 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 Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant, Tokyo, Japan.

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
Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Muto, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2040. 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
Rigaku (2010). CrystalStructure. 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
Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615. Web of Science 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 2| February 2013| Page o210

doi:10.1107/S1600536812052026

Open

access