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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o444-o445

{2,7-Dimeth­­oxy-8-[4-(propan-2-yl­­oxy)benzo­yl]naphthalen-1-yl}[4-(propan-2-yl­­oxy)phen­yl]methanone

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 19 February 2013; accepted 20 February 2013; online 28 February 2013)

The title compound, C32H32O6, crystallized with two independent molecules in the asymmetric unit. Each molecule has essentially the same feature of non-coplanar aromatic rings whereby the two 4-isopropoxybenzoyl groups are twisted in a perpendicular manner to the naphthalene ring and oriented in the same direction (syn-orientation). The benzene rings of the aroyl groups make dihedral angles of 16.13 (7) and 25.31 (7)° in the two molecules. These benzene rings make dihedral angles of 88.38 (8) and 75.32 (7)° with the naphthalene ring system in one molecule, and 89.71 (7) and 82.11 (7)° in the other. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional network. In one independent molecule, the 2-propyl groups of both isoprop­oxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3).

Related literature

For the synthesis of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]); Okamoto et al. (2011[Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.]). For structures of closely related compounds, see: Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.]); Sasagawa et al. (2011[Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.], 2012a[Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012a). Acta Cryst. E68, o2596.],b[Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012b). Acta Cryst. E68, o3348.], 2013[Sasagawa, K., Sakamoto, R., Kusakabe, T., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o146.]).

[Scheme 1]

Experimental

Crystal data
  • C32H32O6

  • Mr = 512.58

  • Monoclinic, P 21 /n

  • a = 10.9988 (2) Å

  • b = 25.8702 (5) Å

  • c = 19.2062 (4) Å

  • β = 100.338 (1)°

  • V = 5376.27 (17) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.70 mm−1

  • T = 193 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.766, Tmax = 0.872

  • 98899 measured reflections

  • 9839 independent reflections

  • 8263 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.121

  • S = 0.94

  • 9839 reflections

  • 748 parameters

  • 9 restraints

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O7i 0.95 2.44 3.3240 (19) 155
C38—H38⋯O2ii 0.95 2.52 3.3888 (19) 152
C62—H62⋯O1iii 1.00 2.51 3.238 (2) 129
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridgeational Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the course of our studies 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 1,8-diaroylated 2,7-dimethoxynaphthalene derivatives, such as {8-[4-(butoxy)benzoyl]-2,7-dimethoxynaphthalen-1-yl}[4-(butoxy)phenyl]methanone [1,8-bis(4-butoxylbenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa, Muto et al., 2011), [2,7-dimethoxy-8-(4-methoxybenzoyl)-naphthalen-1-yl](4-methoxyphenyl)-methanone chloroform mono solvate [1,8-bis(4-methoxybenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa, Sakamoto et al., 2013), [2,7-dimethoxy-8-(4-propylbenzoyl)-naphthalen-1-yl](4-propylphenyl)-methanone [1,8-bis(4-propylbenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa, Hijikata et al., 2012a) and [2,7-dimethoxy-8-{4-(2-methylpropyl)benzoyl}-naphthalen-1-yl]{4-(2-methylpropyl)phenyl}-methanone [1,8-bis(4-isobutylbenzoyl)-2,7-dimethoxynaphthalene] (Sasagawa, Hijikata et al., 2012b).

The aroyl groups in these compounds are almost perpendicularly attached to the naphthalene ring system and oriented in opposite directions (anti-orientation). Accordingly, to the best of our knowledge, most 1,8-diaroylnaphthalene derivatives have anti-oriented structures. Recently, we have also clarified the structure of another 1,8-diaroylnaphthalene derivative in which the two aroyl groups are situated in the same direction (syn-orientation), that is, 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al., 2010). As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the crystal structure of the title compound, a 1,8-diaroylated naphthalene bearing isopropoxy groups on the aroyl moieties, is reported on herein.

The molecular structure of the title compound is displayed in Fig 1. It crystallizes with two independent molecules, A and B, in the asymmetric unit. In both molecules, the two 4-isopropoxybenzoyl groups are situated in a syn-orientation. The dihedral angles between the best planes of the two phenyl rings in molecules A and B are 16.13 (7) and 25.31 (7)°, respectively. The dihedral angles between the best planes of the 4-isopropoxyphenyl rings and the naphthalene ring system are 88.38 (8) and 75.32 (7)° in A, and 89.71 (7) and 82.11 (7)° in B.

The torsion angles between the carbonyl groups and the naphthalene ring system in the molecules A and B [C10—C1—C11—O1 = 96.99 (17)° and C8—C9—C18—O2 = 105.84 (16)° for A; C42—C33—C43—O7 = 106.99 (17)° and C42—C41—C50—O8 = -67.82 (19)° for B] are larger than those between the carbonyl groups and the 4-isopropoxyphenyl rings [O1—C11—C12—C13 = 174.68 (14)° and O2—C18—C19—C20 = -178.60 (14)° for A; O7—C43—C44—C45 = 157.34 (14)° and O8—C50—C51—C52 = 160.32 (14)° for B].

In the crystal, there are C—H···O interactions connecting the molecules so forming of a three-dimensional network (Table 1 and Fig. 2).

Related literature top

For the synthesis of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For structures of closely related compounds, see: Hijikata et al. (2010); Sasagawa et al. (2011, 2012a,b, 2013).

Experimental top

The title compound was prepared by SN2 reaction of 1,8-bis(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene (1.0 mmol, 428.5 mg), which was obtained via SNAr reaction of 1,8-bis(4-fluorobenzoyl)-2,7-dimethoxynaphthalene with sodium hydroxide, with 2-bromopropane (3.0 mmol, 369 mg) and potassium carbonate (2.8 mmol, 387 mg) in N,N-dimethylformamide (DMF; 2.5 ml). After the reaction mixture was stirred at 333 K for 6 h, it was poured into water (30 ml) and the mixture was extracted with CHCl3 (15 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 (93% yield). The crude product was purified by recrystallization from methanol (isolated yield 44%; M.p. = 438.8–441.9 K). The isolated product was crystallized from methanol to give colourless plate-like crystals of the title compound, suitable for X-ray diffraction analysis. Spectroscopic data for the title compound is available in the archived CIF.

Refinement top

In molecule A, the propyl moiety of both isopropoxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3). Rigid bond restraints were applied to the Uij values of the naphthalene ring (C27—O5, C30—C32 and C30—C31') [3 restraints with the DELU command in SHELXL97]. Further restraints were used to generate similar Uij values for the atoms of the isopropoxy group (6 restraints with the SIMU command in SHELXL97). All H atoms were located in a difference Fourier map and were subsequently refined as riding atoms: C—H = 0.95 (aromatic), 0.98 (methyl) and 1.00 (methyne) Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

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: SHELXS97 (Sheldrick, 2008); 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
[Figure 1] Fig. 1. A view of the molecular structure of the two independent molecules, A and B, of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing title compound, showing the C—H···O hydrogen bonds as dashed lines [black molecule A; red molecule B; see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity].
{2,7-Dimethoxy-8-[4-(propan-2-yloxy)benzoyl]naphthalen-1-yl}[4-(propan-2-yloxy)phenyl]methanone top
Crystal data top
C32H32O6F(000) = 2176
Mr = 512.58Dx = 1.267 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ynCell parameters from 83451 reflections
a = 10.9988 (2) Åθ = 3.4–68.2°
b = 25.8702 (5) ŵ = 0.70 mm1
c = 19.2062 (4) ÅT = 193 K
β = 100.338 (1)°Plate, colourless
V = 5376.27 (17) Å30.40 × 0.30 × 0.20 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
9839 independent reflections
Radiation source: fine-focus sealed tube8263 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.000 pixels mm-1θmax = 68.2°, θmin = 3.4°
ω scansh = 1313
Absorption correction: numerical
(NUMABS; Higashi, 1999)
k = 3131
Tmin = 0.766, Tmax = 0.872l = 2323
98899 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0715P)2 + 1.6612P]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
9839 reflectionsΔρmax = 0.27 e Å3
748 parametersΔρmin = 0.22 e Å3
9 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00071 (6)
Crystal data top
C32H32O6V = 5376.27 (17) Å3
Mr = 512.58Z = 8
Monoclinic, P21/nCu Kα radiation
a = 10.9988 (2) ŵ = 0.70 mm1
b = 25.8702 (5) ÅT = 193 K
c = 19.2062 (4) Å0.40 × 0.30 × 0.20 mm
β = 100.338 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
9839 independent reflections
Absorption correction: numerical
(NUMABS; Higashi, 1999)
8263 reflections with I > 2σ(I)
Tmin = 0.766, Tmax = 0.872Rint = 0.027
98899 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0419 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 0.94Δρmax = 0.27 e Å3
9839 reflectionsΔρmin = 0.22 e Å3
748 parameters
Special details top

Experimental. Spectroscopic data for the title compound:

1H NMR δ (300 MHz, CDCl3);0.74(12H, s), 3.71(6H, s), 4.59(2H, m), 6.76(4H, br), 7.19(2H, d, J = 9.3 Hz), 7.63(4H, br), 7.92(2H, d, J = 9.3 Hz) p.p.m.. 13C NMR δ (100 MHz, CDCl3); 21.80, 30.70, 56.23, 69.56, 111.00, 114.20, 121.54, 125.24, 129.28, 131.32, 131.58, 155.71, 161.46, 194.86 p.p.m.. IR (KBr, cm-1); 1663(Ar, naphthalene), 1598(C=O), 1510(Ar, naphthalene). HRMS (m/z); [M + H]+ Calcd for C32H33O6, 513.2285; found, 513.2285

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
xyzUiso*/UeqOcc. (<1)
O10.60693 (10)0.72303 (4)0.36326 (6)0.0497 (4)
O20.48829 (10)0.74405 (4)0.21488 (6)0.0467 (4)
O30.86555 (11)0.68059 (5)0.42031 (6)0.0554 (4)
O40.54422 (11)0.70364 (4)0.06137 (5)0.0512 (4)
O50.90620 (12)0.92918 (5)0.32676 (12)0.0954 (7)
O60.74253 (11)0.93487 (4)0.08944 (7)0.0544 (4)
C10.76067 (13)0.68814 (5)0.30413 (7)0.0361 (4)
C20.84952 (14)0.66254 (6)0.35207 (8)0.0425 (5)
C30.91844 (15)0.62125 (6)0.33124 (9)0.0483 (5)
C40.89840 (15)0.60671 (6)0.26233 (9)0.0475 (5)
C50.81015 (14)0.63187 (5)0.21088 (8)0.0408 (5)
C60.79227 (15)0.61570 (6)0.13952 (9)0.0474 (5)
C70.70616 (16)0.63802 (6)0.08864 (9)0.0484 (5)
C80.63481 (14)0.67918 (6)0.10793 (8)0.0411 (5)
C90.65217 (13)0.69810 (5)0.17632 (7)0.0346 (4)
C100.73873 (13)0.67378 (5)0.23110 (7)0.0348 (4)
C110.69586 (13)0.73178 (6)0.33529 (7)0.0372 (4)
C120.74894 (13)0.78416 (5)0.33299 (7)0.0356 (4)
C130.85671 (13)0.79273 (6)0.30592 (8)0.0389 (4)
C140.90612 (14)0.84140 (6)0.30505 (9)0.0461 (5)
C150.84830 (15)0.88319 (6)0.33003 (11)0.0551 (6)
C160.73928 (15)0.87583 (6)0.35594 (10)0.0521 (5)
C170.69173 (14)0.82654 (6)0.35791 (8)0.0437 (5)
C180.57814 (13)0.74625 (5)0.18612 (7)0.0351 (4)
C190.61980 (12)0.79548 (5)0.15887 (7)0.0338 (4)
C200.72121 (13)0.79873 (6)0.12430 (8)0.0385 (4)
C210.75761 (14)0.84540 (6)0.10076 (8)0.0412 (5)
C220.69634 (14)0.89068 (6)0.11305 (8)0.0408 (5)
C230.59485 (14)0.88847 (6)0.14727 (8)0.0410 (5)
C240.55734 (13)0.84092 (6)0.16882 (7)0.0373 (4)
C250.96293 (16)0.65966 (8)0.47107 (9)0.0566 (6)
C260.5251 (2)0.69005 (8)0.01125 (9)0.0681 (7)
C270.8623 (6)0.9742 (2)0.3725 (6)0.083 (3)0.512 (3)
C280.8710 (8)0.9676 (3)0.4514 (4)0.118 (3)0.512 (3)
C290.9435 (5)1.01873 (17)0.3551 (4)0.096 (2)0.512 (3)
C300.69254 (19)0.98401 (7)0.10301 (13)0.0672 (7)
C310.7586 (14)1.0240 (5)0.0743 (8)0.106 (5)0.512 (3)
C320.5743 (4)0.98772 (14)0.0342 (2)0.0628 (11)0.512 (3)
C29'0.9072 (5)1.01823 (16)0.2926 (3)0.0723 (18)0.488 (3)
C27'0.8509 (7)0.9777 (2)0.3317 (3)0.0587 (18)0.488 (3)
C28'0.8944 (7)0.9823 (3)0.4114 (5)0.087 (3)0.488 (3)
C31'0.7574 (5)0.98833 (17)0.1920 (3)0.0820 (14)0.488 (3)
C32'0.7797 (13)1.0236 (4)0.0810 (6)0.061 (2)0.488 (3)
O70.52631 (10)0.99841 (4)0.31284 (6)0.0509 (4)
O80.40037 (10)1.00696 (4)0.16112 (6)0.0510 (4)
O90.45137 (14)1.04647 (5)0.43687 (6)0.0718 (5)
O100.11665 (12)1.04293 (5)0.07925 (6)0.0604 (4)
O110.20901 (10)0.80048 (4)0.35548 (6)0.0469 (3)
O120.05574 (10)0.81001 (4)0.08665 (6)0.0463 (3)
C330.33939 (14)1.04269 (5)0.32204 (8)0.0387 (4)
C340.35879 (17)1.06694 (6)0.38724 (8)0.0502 (5)
C350.28477 (19)1.10852 (6)0.40178 (9)0.0575 (6)
C360.19387 (17)1.12627 (6)0.35009 (9)0.0511 (6)
C370.17281 (14)1.10447 (5)0.28170 (8)0.0412 (4)
C380.08108 (15)1.12542 (6)0.22844 (9)0.0472 (5)
C390.05962 (15)1.10602 (6)0.16186 (9)0.0495 (5)
C400.13021 (15)1.06377 (6)0.14563 (8)0.0439 (5)
C410.22066 (13)1.04114 (5)0.19615 (8)0.0368 (4)
C420.24586 (13)1.06143 (5)0.26639 (7)0.0355 (4)
C430.41773 (13)0.99499 (5)0.31764 (7)0.0374 (4)
C440.35907 (12)0.94405 (5)0.32422 (7)0.0337 (4)
C450.25260 (13)0.93868 (5)0.35358 (7)0.0376 (4)
C460.20605 (13)0.89039 (6)0.36397 (8)0.0401 (5)
C470.26250 (13)0.84606 (5)0.34327 (8)0.0379 (4)
C480.36787 (13)0.85103 (5)0.31252 (8)0.0391 (4)
C490.41534 (13)0.89952 (5)0.30440 (7)0.0365 (4)
C500.29425 (13)0.99896 (5)0.16853 (7)0.0379 (4)
C510.23169 (13)0.94911 (5)0.14746 (7)0.0357 (4)
C520.12774 (13)0.93272 (6)0.17363 (7)0.0386 (4)
C530.07346 (14)0.88584 (6)0.15349 (8)0.0413 (5)
C540.11889 (13)0.85469 (5)0.10467 (7)0.0382 (4)
C550.22100 (14)0.87104 (6)0.07710 (8)0.0419 (5)
C560.27687 (13)0.91749 (6)0.09950 (8)0.0404 (5)
C570.4899 (3)1.07333 (9)0.50069 (11)0.0873 (9)
C580.05196 (17)1.07207 (7)0.02149 (9)0.0539 (6)
C590.24601 (16)0.75272 (6)0.32414 (9)0.0478 (5)
C600.19015 (19)0.71001 (7)0.36188 (12)0.0653 (7)
C610.19847 (18)0.75223 (7)0.24587 (10)0.0592 (6)
C620.08681 (16)0.77827 (6)0.02938 (9)0.0510 (6)
C630.2018 (2)0.74668 (7)0.05348 (12)0.0681 (7)
C640.0252 (2)0.74458 (9)0.00674 (12)0.0778 (8)
H30.978100.603800.365000.0580*
H160.697900.904400.372100.0630*
H170.618400.821500.376700.0520*
H200.765500.768300.117000.0460*
H210.824900.846800.076000.0490*
H230.552100.919100.155700.0490*
H240.486900.839200.191000.0450*
H25A1.041000.662500.453500.0680*
H25B0.945800.623200.479200.0680*
H25C0.969200.678800.515600.0680*
H26A0.501500.653500.016700.0820*
H26B0.601600.695700.029700.0820*
H26C0.459100.711500.037600.0820*
H270.774500.982600.351700.0990*0.512 (3)
H28A0.958100.967800.474500.1770*0.512 (3)
H28B0.833100.934700.461000.1770*0.512 (3)
H28C0.827600.996100.470000.1770*0.512 (3)
H29A0.909201.051600.367800.1440*0.512 (3)
H29B0.946001.018500.304300.1440*0.512 (3)
H29C1.027501.014600.382000.1440*0.512 (3)
H300.673100.989800.151300.0810*0.512 (3)
H31A0.847701.018600.089300.1580*0.512 (3)
H31B0.735501.057700.091400.1580*0.512 (3)
H31C0.737901.023200.022500.1580*0.512 (3)
H32A0.531601.020800.035800.0950*0.512 (3)
H32B0.516400.959300.036900.0950*0.512 (3)
H32C0.606100.985200.010200.0950*0.512 (3)
H40.944900.578900.248200.0570*
H60.841800.588500.126700.0570*
H70.694300.626100.041100.0580*
H130.896500.764500.287800.0470*
H140.980400.846400.287200.0550*
H27'0.758800.976500.318200.0710*0.488 (3)
H28D0.865700.952200.435000.1290*0.488 (3)
H28E0.860401.013900.428600.1290*0.488 (3)
H28F0.984800.983700.421900.1290*0.488 (3)
H29D0.997401.015100.303200.1090*0.488 (3)
H29E0.882901.052500.307100.1090*0.488 (3)
H29F0.878201.013900.241600.1090*0.488 (3)
H30'0.601500.989600.088600.0810*0.488 (3)
H31D0.847000.983500.197900.1240*0.488 (3)
H31E0.722100.961500.218400.1240*0.488 (3)
H31F0.739801.022400.210000.1240*0.488 (3)
H32D0.793601.015700.033200.0920*0.488 (3)
H32E0.858601.022600.114100.0920*0.488 (3)
H32F0.743201.058100.081600.0920*0.488 (3)
H350.298301.124000.447400.0690*
H360.143201.154000.360200.0610*
H380.033201.153800.239500.0570*
H390.002301.120700.126600.0590*
H450.211800.968600.366500.0450*
H460.135000.887300.385400.0480*
H480.406400.821300.297400.0470*
H490.488400.902600.284800.0440*
H520.094100.954100.205600.0460*
H530.004500.874600.173000.0500*
H550.252100.850500.043200.0500*
H560.348100.928100.081600.0480*
H57A0.564801.057200.527000.1050*
H57B0.424301.072100.529100.1050*
H57C0.507301.109400.490400.1050*
H58A0.087801.106800.022000.0650*
H58B0.035301.074700.025700.0650*
H58C0.058801.054800.023100.0650*
H590.338100.749600.333600.0570*
H60A0.100300.714400.354600.0780*
H60B0.224300.711400.412600.0780*
H60C0.209700.676500.342900.0780*
H61A0.233600.781500.223800.0710*
H61B0.108200.755000.237000.0710*
H61C0.222600.719800.225700.0710*
H620.099100.801000.010900.0610*
H63A0.222900.727700.013100.0820*
H63B0.187000.722100.089900.0820*
H63C0.270200.769700.073100.0820*
H64A0.011700.722200.032300.0930*
H64B0.097800.766400.008900.0930*
H64C0.039000.723200.046700.0930*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0479 (6)0.0540 (7)0.0511 (6)0.0050 (5)0.0194 (5)0.0014 (5)
O20.0460 (6)0.0422 (6)0.0571 (7)0.0044 (5)0.0237 (5)0.0090 (5)
O30.0588 (7)0.0622 (7)0.0397 (6)0.0104 (6)0.0059 (5)0.0021 (5)
O40.0594 (7)0.0569 (7)0.0343 (5)0.0094 (5)0.0006 (5)0.0043 (5)
O50.0495 (8)0.0346 (6)0.2053 (19)0.0011 (5)0.0312 (10)0.0029 (9)
O60.0569 (7)0.0397 (6)0.0732 (8)0.0000 (5)0.0297 (6)0.0121 (5)
C10.0353 (7)0.0328 (7)0.0395 (7)0.0020 (6)0.0049 (6)0.0029 (6)
C20.0430 (8)0.0401 (8)0.0430 (8)0.0006 (6)0.0039 (7)0.0040 (6)
C30.0433 (9)0.0426 (8)0.0565 (10)0.0061 (7)0.0020 (7)0.0092 (7)
C40.0451 (9)0.0353 (8)0.0623 (10)0.0073 (6)0.0102 (7)0.0020 (7)
C50.0420 (8)0.0318 (7)0.0496 (9)0.0004 (6)0.0109 (7)0.0001 (6)
C60.0532 (10)0.0379 (8)0.0533 (9)0.0041 (7)0.0159 (8)0.0065 (7)
C70.0602 (10)0.0440 (8)0.0423 (8)0.0000 (7)0.0131 (7)0.0095 (7)
C80.0453 (8)0.0405 (8)0.0374 (8)0.0003 (6)0.0071 (6)0.0001 (6)
C90.0359 (7)0.0325 (7)0.0362 (7)0.0005 (6)0.0088 (6)0.0008 (5)
C100.0345 (7)0.0300 (7)0.0408 (8)0.0021 (5)0.0091 (6)0.0014 (5)
C110.0357 (8)0.0443 (8)0.0307 (7)0.0011 (6)0.0035 (6)0.0015 (6)
C120.0353 (7)0.0400 (7)0.0301 (7)0.0025 (6)0.0020 (5)0.0001 (6)
C130.0391 (8)0.0395 (8)0.0379 (7)0.0040 (6)0.0066 (6)0.0009 (6)
C140.0384 (8)0.0431 (8)0.0565 (9)0.0002 (6)0.0081 (7)0.0047 (7)
C150.0380 (9)0.0371 (8)0.0872 (13)0.0013 (6)0.0035 (8)0.0014 (8)
C160.0447 (9)0.0410 (8)0.0688 (11)0.0083 (7)0.0050 (8)0.0094 (8)
C170.0378 (8)0.0464 (8)0.0470 (8)0.0056 (6)0.0079 (6)0.0026 (7)
C180.0359 (7)0.0384 (7)0.0308 (7)0.0021 (6)0.0056 (6)0.0014 (5)
C190.0339 (7)0.0374 (7)0.0299 (7)0.0021 (6)0.0054 (5)0.0025 (5)
C200.0359 (7)0.0399 (8)0.0406 (8)0.0045 (6)0.0095 (6)0.0019 (6)
C210.0365 (8)0.0456 (8)0.0440 (8)0.0003 (6)0.0140 (6)0.0039 (6)
C220.0404 (8)0.0396 (8)0.0431 (8)0.0014 (6)0.0091 (6)0.0067 (6)
C230.0429 (8)0.0375 (8)0.0443 (8)0.0053 (6)0.0126 (6)0.0050 (6)
C240.0371 (8)0.0405 (7)0.0362 (7)0.0037 (6)0.0114 (6)0.0036 (6)
C250.0479 (10)0.0733 (12)0.0451 (9)0.0020 (8)0.0011 (7)0.0128 (8)
C260.0855 (14)0.0795 (13)0.0354 (9)0.0124 (11)0.0005 (9)0.0048 (8)
C270.049 (3)0.039 (3)0.153 (9)0.005 (2)0.001 (5)0.001 (4)
C280.123 (5)0.116 (6)0.121 (6)0.031 (4)0.039 (5)0.059 (5)
C290.073 (3)0.046 (2)0.166 (6)0.004 (2)0.011 (4)0.015 (3)
C300.0615 (11)0.0407 (9)0.1052 (14)0.0021 (8)0.0305 (10)0.0008 (10)
C310.093 (7)0.073 (6)0.171 (10)0.023 (4)0.079 (7)0.057 (5)
C320.071 (2)0.0461 (19)0.079 (2)0.0026 (17)0.0342 (12)0.0125 (17)
C29'0.077 (3)0.041 (2)0.104 (4)0.0067 (19)0.030 (3)0.009 (2)
C27'0.058 (3)0.036 (2)0.083 (4)0.0097 (17)0.015 (3)0.008 (2)
C28'0.092 (5)0.071 (4)0.098 (6)0.008 (4)0.021 (4)0.015 (4)
C31'0.082 (3)0.051 (2)0.112 (2)0.002 (2)0.015 (2)0.009 (2)
C32'0.078 (5)0.029 (3)0.079 (4)0.008 (3)0.020 (3)0.000 (3)
O70.0382 (6)0.0428 (6)0.0710 (8)0.0034 (5)0.0078 (5)0.0089 (5)
O80.0403 (6)0.0504 (6)0.0635 (7)0.0032 (5)0.0127 (5)0.0110 (5)
O90.1025 (11)0.0548 (7)0.0451 (7)0.0154 (7)0.0220 (7)0.0060 (6)
O100.0772 (8)0.0568 (7)0.0392 (6)0.0241 (6)0.0108 (6)0.0028 (5)
O110.0514 (6)0.0354 (5)0.0593 (7)0.0050 (5)0.0244 (5)0.0011 (5)
O120.0514 (6)0.0398 (6)0.0488 (6)0.0040 (5)0.0121 (5)0.0071 (5)
C330.0445 (8)0.0305 (7)0.0394 (8)0.0023 (6)0.0031 (6)0.0017 (6)
C340.0676 (11)0.0377 (8)0.0404 (8)0.0019 (7)0.0032 (8)0.0002 (6)
C350.0861 (13)0.0402 (9)0.0434 (9)0.0035 (8)0.0045 (9)0.0096 (7)
C360.0649 (11)0.0349 (8)0.0541 (10)0.0031 (7)0.0126 (8)0.0081 (7)
C370.0442 (8)0.0310 (7)0.0481 (8)0.0004 (6)0.0079 (7)0.0030 (6)
C380.0440 (9)0.0344 (7)0.0620 (10)0.0076 (6)0.0062 (7)0.0033 (7)
C390.0454 (9)0.0422 (8)0.0558 (10)0.0097 (7)0.0044 (7)0.0003 (7)
C400.0456 (9)0.0402 (8)0.0428 (8)0.0055 (6)0.0006 (7)0.0020 (6)
C410.0370 (8)0.0324 (7)0.0396 (8)0.0015 (6)0.0031 (6)0.0000 (6)
C420.0373 (7)0.0290 (7)0.0399 (8)0.0016 (6)0.0058 (6)0.0001 (5)
C430.0382 (8)0.0353 (7)0.0364 (7)0.0007 (6)0.0002 (6)0.0035 (6)
C440.0333 (7)0.0341 (7)0.0319 (7)0.0009 (5)0.0009 (5)0.0025 (5)
C450.0373 (8)0.0363 (7)0.0388 (7)0.0035 (6)0.0056 (6)0.0025 (6)
C460.0365 (8)0.0422 (8)0.0438 (8)0.0011 (6)0.0131 (6)0.0021 (6)
C470.0396 (8)0.0350 (7)0.0397 (7)0.0031 (6)0.0084 (6)0.0028 (6)
C480.0389 (8)0.0342 (7)0.0457 (8)0.0032 (6)0.0114 (6)0.0021 (6)
C490.0335 (7)0.0373 (7)0.0394 (7)0.0013 (6)0.0084 (6)0.0035 (6)
C500.0388 (8)0.0388 (7)0.0346 (7)0.0045 (6)0.0025 (6)0.0006 (6)
C510.0350 (7)0.0356 (7)0.0346 (7)0.0074 (6)0.0009 (6)0.0010 (6)
C520.0397 (8)0.0421 (8)0.0338 (7)0.0042 (6)0.0060 (6)0.0027 (6)
C530.0410 (8)0.0460 (8)0.0374 (8)0.0011 (6)0.0083 (6)0.0005 (6)
C540.0408 (8)0.0350 (7)0.0367 (7)0.0039 (6)0.0015 (6)0.0019 (6)
C550.0429 (8)0.0383 (8)0.0453 (8)0.0068 (6)0.0099 (7)0.0050 (6)
C560.0357 (8)0.0413 (8)0.0448 (8)0.0052 (6)0.0088 (6)0.0005 (6)
C570.1187 (19)0.0798 (15)0.0492 (11)0.0174 (13)0.0228 (12)0.0150 (10)
C580.0546 (10)0.0610 (10)0.0435 (9)0.0076 (8)0.0019 (7)0.0114 (8)
C590.0485 (9)0.0348 (8)0.0621 (10)0.0002 (6)0.0155 (8)0.0028 (7)
C600.0669 (12)0.0440 (9)0.0878 (14)0.0052 (8)0.0211 (10)0.0102 (9)
C610.0614 (11)0.0529 (10)0.0643 (11)0.0017 (8)0.0141 (9)0.0089 (8)
C620.0618 (11)0.0448 (9)0.0470 (9)0.0014 (8)0.0113 (8)0.0068 (7)
C630.0865 (14)0.0428 (9)0.0771 (13)0.0118 (9)0.0204 (11)0.0031 (9)
C640.0810 (15)0.0766 (14)0.0776 (14)0.0184 (11)0.0190 (12)0.0303 (11)
Geometric parameters (Å, º) top
O1—C111.2187 (18)C29—H29B0.9800
O2—C181.2169 (18)C29—H29A0.9800
O3—C21.3726 (19)C29'—H29F0.9800
O3—C251.420 (2)C29'—H29E0.9800
O4—C81.3686 (19)C29'—H29D0.9800
O4—C261.417 (2)C30—H301.0000
O5—C151.356 (2)C30—H30'1.0000
O5—C271.585 (8)C31—H31A0.9800
O5—C27'1.405 (6)C31—H31B0.9800
O6—C221.3614 (19)C31—H31C0.9800
O6—C301.428 (2)C31'—H31E0.9800
O7—C431.2174 (18)C31'—H31F0.9800
O8—C501.2186 (18)C31'—H31D0.9800
O9—C341.370 (2)C32—H32A0.9800
O9—C571.407 (2)C32—H32B0.9800
O10—C581.422 (2)C32—H32C0.9800
O10—C401.3675 (19)C32'—H32D0.9800
O11—C471.3569 (17)C32'—H32E0.9800
O11—C591.4637 (19)C32'—H32F0.9800
O12—C541.3609 (17)C33—C341.383 (2)
O12—C621.461 (2)C33—C421.429 (2)
C1—C21.385 (2)C33—C431.5161 (19)
C1—C101.4290 (19)C34—C351.407 (2)
C1—C111.515 (2)C35—C361.356 (3)
C2—C31.409 (2)C36—C371.410 (2)
C3—C41.355 (2)C37—C381.410 (2)
C4—C51.414 (2)C37—C421.434 (2)
C5—C61.413 (2)C38—C391.354 (2)
C5—C101.433 (2)C39—C401.408 (2)
C6—C71.361 (2)C40—C411.388 (2)
C7—C81.411 (2)C41—C421.428 (2)
C8—C91.383 (2)C41—C501.5104 (19)
C9—C181.5182 (19)C43—C441.4826 (19)
C9—C101.4317 (19)C44—C451.395 (2)
C11—C121.479 (2)C44—C491.3927 (19)
C12—C131.395 (2)C45—C461.378 (2)
C12—C171.391 (2)C46—C471.396 (2)
C13—C141.373 (2)C47—C481.398 (2)
C14—C151.383 (2)C48—C491.3783 (19)
C15—C161.391 (2)C50—C511.4834 (19)
C16—C171.381 (2)C51—C521.395 (2)
C18—C191.4805 (19)C51—C561.389 (2)
C19—C201.399 (2)C52—C531.376 (2)
C19—C241.392 (2)C53—C541.395 (2)
C20—C211.374 (2)C54—C551.391 (2)
C21—C221.393 (2)C55—C561.383 (2)
C22—C231.395 (2)C59—C601.511 (3)
C23—C241.384 (2)C59—C611.500 (3)
C27—C291.531 (8)C62—C631.507 (3)
C27—C281.511 (14)C62—C641.508 (3)
C27'—C29'1.488 (8)C35—H350.9500
C27'—C28'1.524 (11)C36—H360.9500
C30—C31'1.734 (6)C38—H380.9500
C30—C32'1.514 (13)C39—H390.9500
C30—C321.682 (5)C45—H450.9500
C30—C311.430 (14)C46—H460.9500
C3—H30.9500C48—H480.9500
C4—H40.9500C49—H490.9500
C6—H60.9500C52—H520.9500
C7—H70.9500C53—H530.9500
C13—H130.9500C55—H550.9500
C14—H140.9500C56—H560.9500
C16—H160.9500C57—H57A0.9800
C17—H170.9500C57—H57B0.9800
C20—H200.9500C57—H57C0.9800
C21—H210.9500C58—H58A0.9800
C23—H230.9500C58—H58B0.9800
C24—H240.9500C58—H58C0.9800
C25—H25A0.9800C59—H591.0000
C25—H25B0.9800C60—H60A0.9800
C25—H25C0.9800C60—H60B0.9800
C26—H26B0.9800C60—H60C0.9800
C26—H26C0.9800C61—H61A0.9800
C26—H26A0.9800C61—H61B0.9800
C27—H271.0000C61—H61C0.9800
C27'—H27'1.0000C62—H621.0000
C28—H28B0.9800C63—H63A0.9800
C28—H28C0.9800C63—H63B0.9800
C28—H28A0.9800C63—H63C0.9800
C28'—H28D0.9800C64—H64A0.9800
C28'—H28E0.9800C64—H64B0.9800
C28'—H28F0.9800C64—H64C0.9800
C29—H29C0.9800
C2—O3—C25118.54 (13)C30—C31—H31C110.00
C8—O4—C26119.37 (13)H31A—C31—H31B109.00
C15—O5—C27115.3 (3)C30—C31—H31B109.00
C15—O5—C27'124.6 (3)H31A—C31—H31C109.00
C22—O6—C30120.53 (14)C30—C31'—H31E109.00
C34—O9—C57119.04 (16)C30—C31'—H31F110.00
C40—O10—C58118.29 (13)C30—C31'—H31D109.00
C47—O11—C59120.09 (12)H31D—C31'—H31F109.00
C54—O12—C62119.41 (12)H31E—C31'—H31F109.00
C2—C1—C11114.82 (12)H31D—C31'—H31E109.00
C10—C1—C11124.96 (12)C30—C32—H32A109.00
C2—C1—C10120.19 (13)C30—C32—H32B109.00
O3—C2—C3123.07 (14)H32A—C32—H32B110.00
C1—C2—C3121.68 (14)H32A—C32—H32C109.00
O3—C2—C1115.25 (13)H32B—C32—H32C109.00
C2—C3—C4119.09 (15)C30—C32—H32C109.00
C3—C4—C5121.72 (15)H32D—C32'—H32F110.00
C4—C5—C6120.03 (14)H32E—C32'—H32F109.00
C4—C5—C10120.01 (13)H32D—C32'—H32E109.00
C6—C5—C10119.96 (13)C30—C32'—H32D110.00
C5—C6—C7121.92 (15)C30—C32'—H32E109.00
C6—C7—C8118.66 (15)C30—C32'—H32F109.00
O4—C8—C7123.46 (14)C34—C33—C42119.80 (13)
O4—C8—C9114.67 (13)C34—C33—C43115.02 (13)
C7—C8—C9121.88 (14)C42—C33—C43125.08 (12)
C10—C9—C18124.76 (12)O9—C34—C33115.43 (14)
C8—C9—C10120.19 (13)O9—C34—C35122.80 (14)
C8—C9—C18115.00 (12)C33—C34—C35121.73 (15)
C1—C10—C9125.45 (12)C34—C35—C36119.36 (15)
C5—C10—C9117.26 (12)C35—C36—C37121.52 (15)
C1—C10—C5117.29 (12)C36—C37—C38119.92 (14)
O1—C11—C1120.51 (13)C36—C37—C42119.81 (14)
O1—C11—C12122.39 (13)C38—C37—C42120.27 (13)
C1—C11—C12117.05 (12)C37—C38—C39121.56 (15)
C11—C12—C17120.42 (13)C38—C39—C40119.16 (15)
C13—C12—C17118.04 (13)O10—C40—C39122.71 (14)
C11—C12—C13121.54 (13)O10—C40—C41115.46 (14)
C12—C13—C14121.00 (14)C39—C40—C41121.82 (14)
C13—C14—C15120.34 (15)C40—C41—C42119.91 (13)
O5—C15—C16125.35 (15)C40—C41—C50114.91 (13)
O5—C15—C14114.88 (15)C42—C41—C50124.90 (13)
C14—C15—C16119.77 (15)C33—C42—C37117.70 (12)
C15—C16—C17119.40 (15)C33—C42—C41125.02 (13)
C12—C17—C16121.42 (14)C37—C42—C41117.28 (12)
O2—C18—C19121.92 (12)O7—C43—C33121.34 (12)
C9—C18—C19117.07 (12)O7—C43—C44121.26 (12)
O2—C18—C9121.01 (12)C33—C43—C44117.28 (12)
C18—C19—C20122.89 (12)C43—C44—C45122.19 (12)
C18—C19—C24119.10 (12)C43—C44—C49119.37 (12)
C20—C19—C24118.00 (13)C45—C44—C49118.34 (12)
C19—C20—C21120.88 (14)C44—C45—C46120.63 (13)
C20—C21—C22120.33 (14)C45—C46—C47120.52 (13)
O6—C22—C23124.72 (14)O11—C47—C46115.85 (13)
C21—C22—C23119.87 (14)O11—C47—C48124.82 (12)
O6—C22—C21115.41 (14)C46—C47—C48119.33 (12)
C22—C23—C24118.95 (14)C47—C48—C49119.41 (12)
C19—C24—C23121.91 (13)C44—C49—C48121.73 (13)
C28—C27—C29111.7 (7)O8—C50—C41120.21 (12)
O5—C27—C28120.1 (5)O8—C50—C51121.53 (12)
O5—C27—C29100.6 (5)C41—C50—C51118.19 (12)
C28'—C27'—C29'111.6 (5)C50—C51—C52122.41 (12)
O5—C27'—C29'111.8 (5)C50—C51—C56119.30 (13)
O5—C27'—C28'94.4 (5)C52—C51—C56118.29 (13)
O6—C30—C31'97.7 (2)C51—C52—C53120.59 (13)
O6—C30—C32'105.5 (5)C52—C53—C54120.55 (14)
O6—C30—C32100.15 (19)O12—C54—C53115.69 (13)
C31'—C30—C32'93.6 (5)O12—C54—C55124.87 (13)
C31—C30—C3291.7 (6)C53—C54—C55119.43 (13)
O6—C30—C31109.6 (6)C54—C55—C56119.34 (14)
C2—C3—H3121.00C51—C56—C55121.76 (14)
C4—C3—H3120.00O11—C59—C60104.65 (14)
C5—C4—H4119.00O11—C59—C61110.28 (13)
C3—C4—H4119.00C60—C59—C61112.08 (15)
C5—C6—H6119.00O12—C62—C63111.73 (14)
C7—C6—H6119.00O12—C62—C64104.62 (15)
C8—C7—H7121.00C63—C62—C64111.86 (15)
C6—C7—H7121.00C34—C35—H35120.00
C14—C13—H13119.00C36—C35—H35120.00
C12—C13—H13120.00C35—C36—H36119.00
C13—C14—H14120.00C37—C36—H36119.00
C15—C14—H14120.00C37—C38—H38119.00
C15—C16—H16120.00C39—C38—H38119.00
C17—C16—H16120.00C38—C39—H39120.00
C16—C17—H17119.00C40—C39—H39120.00
C12—C17—H17119.00C44—C45—H45120.00
C19—C20—H20120.00C46—C45—H45120.00
C21—C20—H20120.00C45—C46—H46120.00
C20—C21—H21120.00C47—C46—H46120.00
C22—C21—H21120.00C47—C48—H48120.00
C24—C23—H23120.00C49—C48—H48120.00
C22—C23—H23121.00C44—C49—H49119.00
C23—C24—H24119.00C48—C49—H49119.00
C19—C24—H24119.00C51—C52—H52120.00
O3—C25—H25A110.00C53—C52—H52120.00
O3—C25—H25B109.00C52—C53—H53120.00
O3—C25—H25C109.00C54—C53—H53120.00
H25A—C25—H25B109.00C54—C55—H55120.00
H25A—C25—H25C110.00C56—C55—H55120.00
H25B—C25—H25C109.00C51—C56—H56119.00
O4—C26—H26B109.00C55—C56—H56119.00
O4—C26—H26C109.00O9—C57—H57A109.00
O4—C26—H26A110.00O9—C57—H57B109.00
H26B—C26—H26C109.00O9—C57—H57C110.00
H26A—C26—H26C109.00H57A—C57—H57B110.00
H26A—C26—H26B109.00H57A—C57—H57C109.00
O5—C27—H27108.00H57B—C57—H57C109.00
C29—C27—H27108.00O10—C58—H58A110.00
C28—C27—H27108.00O10—C58—H58B109.00
C29'—C27'—H27'113.00O10—C58—H58C109.00
O5—C27'—H27'113.00H58A—C58—H58B109.00
C28'—C27'—H27'113.00H58A—C58—H58C109.00
H28A—C28—H28B109.00H58B—C58—H58C109.00
C27—C28—H28C109.00O11—C59—H59110.00
C27—C28—H28A110.00C60—C59—H59110.00
C27—C28—H28B110.00C61—C59—H59110.00
H28A—C28—H28C109.00C59—C60—H60A109.00
H28B—C28—H28C109.00C59—C60—H60B109.00
H28D—C28'—H28F109.00C59—C60—H60C109.00
H28E—C28'—H28F110.00H60A—C60—H60B110.00
C27'—C28'—H28D109.00H60A—C60—H60C109.00
C27'—C28'—H28E109.00H60B—C60—H60C109.00
C27'—C28'—H28F110.00C59—C61—H61A109.00
H28D—C28'—H28E109.00C59—C61—H61B109.00
H29A—C29—H29B110.00C59—C61—H61C109.00
H29A—C29—H29C109.00H61A—C61—H61B110.00
C27—C29—H29C110.00H61A—C61—H61C110.00
C27—C29—H29A109.00H61B—C61—H61C109.00
C27—C29—H29B110.00O12—C62—H62110.00
H29B—C29—H29C109.00C63—C62—H62110.00
C27'—C29'—H29D110.00C64—C62—H62109.00
C27'—C29'—H29E110.00C62—C63—H63A109.00
H29D—C29'—H29F110.00C62—C63—H63B109.00
H29E—C29'—H29F109.00C62—C63—H63C109.00
H29D—C29'—H29E109.00H63A—C63—H63B109.00
C27'—C29'—H29F109.00H63A—C63—H63C110.00
C32—C30—H30117.00H63B—C63—H63C110.00
C31—C30—H30117.00C62—C64—H64A110.00
O6—C30—H30117.00C62—C64—H64B110.00
C31'—C30—H30'119.00C62—C64—H64C109.00
C32'—C30—H30'119.00H64A—C64—H64B109.00
O6—C30—H30'119.00H64A—C64—H64C109.00
C30—C31—H31A109.00H64B—C64—H64C109.00
H31B—C31—H31C109.00
C25—O3—C2—C1174.05 (14)C9—C18—C19—C24177.82 (12)
C25—O3—C2—C35.4 (2)C9—C18—C19—C201.06 (19)
C26—O4—C8—C74.6 (2)C18—C19—C20—C21179.08 (14)
C26—O4—C8—C9175.17 (15)C24—C19—C20—C210.2 (2)
C27—O5—C15—C14164.8 (4)C18—C19—C24—C23177.24 (13)
C27—O5—C15—C1615.1 (5)C20—C19—C24—C231.7 (2)
C15—O5—C27—C2858.1 (7)C19—C20—C21—C222.1 (2)
C15—O5—C27—C29179.0 (4)C20—C21—C22—C232.2 (2)
C30—O6—C22—C21175.94 (16)C20—C21—C22—O6177.99 (14)
C30—O6—C22—C234.3 (2)C21—C22—C23—C240.4 (2)
C22—O6—C30—C31178.7 (7)O6—C22—C23—C24179.85 (14)
C22—O6—C30—C3285.8 (2)C22—C23—C24—C191.6 (2)
C57—O9—C34—C33170.37 (18)C42—C33—C34—O9179.32 (14)
C57—O9—C34—C3512.0 (3)C42—C33—C34—C353.0 (2)
C58—O10—C40—C3915.6 (2)C43—C33—C34—O94.1 (2)
C58—O10—C40—C41163.06 (14)C43—C33—C34—C35173.55 (15)
C59—O11—C47—C4811.9 (2)C34—C33—C42—C371.7 (2)
C47—O11—C59—C60167.64 (14)C34—C33—C42—C41177.20 (15)
C59—O11—C47—C46168.50 (13)C43—C33—C42—C37174.46 (13)
C47—O11—C59—C6171.65 (18)C43—C33—C42—C416.6 (2)
C62—O12—C54—C53172.24 (13)C34—C33—C43—O776.67 (18)
C62—O12—C54—C556.4 (2)C34—C33—C43—C4499.37 (16)
C54—O12—C62—C64160.28 (14)C42—C33—C43—O7106.99 (17)
C54—O12—C62—C6378.51 (17)C42—C33—C43—C4476.98 (18)
C10—C1—C2—C31.5 (2)O9—C34—C35—C36179.22 (17)
C11—C1—C2—O30.13 (19)C33—C34—C35—C361.7 (3)
C10—C1—C2—O3178.01 (13)C34—C35—C36—C370.9 (3)
C2—C1—C10—C9178.23 (14)C35—C36—C37—C38177.19 (16)
C11—C1—C10—C5179.07 (13)C35—C36—C37—C422.1 (2)
C11—C1—C10—C90.3 (2)C36—C37—C38—C39178.93 (16)
C2—C1—C11—O184.97 (17)C42—C37—C38—C390.3 (2)
C2—C1—C11—C1292.26 (15)C36—C37—C42—C330.7 (2)
C11—C1—C2—C3179.63 (14)C36—C37—C42—C41179.74 (14)
C2—C1—C10—C51.1 (2)C38—C37—C42—C33178.52 (14)
C10—C1—C11—C1285.78 (17)C38—C37—C42—C410.5 (2)
C10—C1—C11—O196.99 (17)C37—C38—C39—C400.3 (2)
O3—C2—C3—C4178.53 (15)C38—C39—C40—O10178.07 (15)
C1—C2—C3—C40.9 (2)C38—C39—C40—C410.5 (2)
C2—C3—C4—C50.0 (2)O10—C40—C41—C42177.33 (13)
C3—C4—C5—C6179.77 (15)O10—C40—C41—C503.2 (2)
C3—C4—C5—C100.3 (2)C39—C40—C41—C421.4 (2)
C10—C5—C6—C71.6 (2)C39—C40—C41—C50175.50 (14)
C4—C5—C10—C10.3 (2)C40—C41—C42—C33177.63 (14)
C4—C5—C6—C7178.35 (16)C40—C41—C42—C371.3 (2)
C4—C5—C10—C9179.14 (14)C50—C41—C42—C334.1 (2)
C6—C5—C10—C1179.69 (14)C50—C41—C42—C37174.83 (13)
C6—C5—C10—C90.9 (2)C40—C41—C50—O8106.00 (16)
C5—C6—C7—C81.3 (2)C40—C41—C50—C5170.86 (17)
C6—C7—C8—C91.6 (2)C42—C41—C50—O867.82 (19)
C6—C7—C8—O4178.65 (15)C42—C41—C50—C51115.32 (15)
O4—C8—C9—C10176.07 (13)O7—C43—C44—C45157.34 (14)
O4—C8—C9—C186.44 (19)O7—C43—C44—C4918.8 (2)
C7—C8—C9—C104.2 (2)C33—C43—C44—C4518.70 (19)
C7—C8—C9—C18173.30 (14)C33—C43—C44—C49165.13 (12)
C18—C9—C10—C15.9 (2)C43—C44—C45—C46174.88 (13)
C18—C9—C10—C5173.52 (13)C49—C44—C45—C461.3 (2)
C8—C9—C18—O2105.84 (16)C43—C44—C49—C48176.92 (13)
C8—C9—C10—C1176.93 (14)C45—C44—C49—C480.6 (2)
C8—C9—C10—C53.7 (2)C44—C45—C46—C472.0 (2)
C10—C9—C18—C19103.53 (16)C45—C46—C47—O11179.63 (13)
C8—C9—C18—C1973.82 (17)C45—C46—C47—C480.7 (2)
C10—C9—C18—O276.80 (19)O11—C47—C48—C49178.44 (14)
O1—C11—C12—C13174.68 (14)C46—C47—C48—C491.2 (2)
O1—C11—C12—C175.5 (2)C47—C48—C49—C441.9 (2)
C1—C11—C12—C132.50 (19)O8—C50—C51—C52160.32 (14)
C1—C11—C12—C17177.35 (13)O8—C50—C51—C5620.2 (2)
C13—C12—C17—C160.2 (2)C41—C50—C51—C5222.86 (19)
C11—C12—C13—C14179.00 (14)C41—C50—C51—C56156.59 (13)
C17—C12—C13—C141.2 (2)C50—C51—C52—C53179.08 (13)
C11—C12—C17—C16179.66 (15)C56—C51—C52—C531.5 (2)
C12—C13—C14—C151.1 (2)C50—C51—C56—C55178.90 (14)
C13—C14—C15—O5179.68 (17)C52—C51—C56—C550.6 (2)
C13—C14—C15—C160.2 (3)C51—C52—C53—C542.2 (2)
C14—C15—C16—C171.5 (3)C52—C53—C54—O12177.80 (13)
O5—C15—C16—C17178.35 (19)C52—C53—C54—C550.9 (2)
C15—C16—C17—C121.5 (3)O12—C54—C55—C56179.67 (13)
O2—C18—C19—C20178.60 (14)C53—C54—C55—C561.1 (2)
O2—C18—C19—C242.5 (2)C54—C55—C56—C511.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O7i0.952.443.3240 (19)155
C38—H38···O2ii0.952.523.3888 (19)152
C62—H62···O1iii1.002.513.238 (2)129
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC32H32O6
Mr512.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)193
a, b, c (Å)10.9988 (2), 25.8702 (5), 19.2062 (4)
β (°) 100.338 (1)
V3)5376.27 (17)
Z8
Radiation typeCu Kα
µ (mm1)0.70
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionNumerical
(NUMABS; Higashi, 1999)
Tmin, Tmax0.766, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
98899, 9839, 8263
Rint0.027
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.121, 0.94
No. of reflections9839
No. of parameters748
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.22

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O7i0.952.443.3240 (19)155
C38—H38···O2ii0.952.523.3888 (19)152
C62—H62···O1iii1.002.513.238 (2)129
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+3/2, z1/2.
 

Acknowledgements

The authors express their gratitude to Atsushi Nagasawa and Toyokazu Muto, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture & Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice. This work was partially supported by the Shorai Foundation for Science and Technology (Tokyo, Japan).

References

First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridgeational Laboratory, Tennessee, USA.
First citationHigashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
First citationHijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902–o2903.  Web of Science CSD CrossRef CAS IUCr Journals
First citationOkamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.  Web of Science CrossRef CAS
First citationOkamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915.  Web of Science CrossRef CAS
First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationSasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012a). Acta Cryst. E68, o2596.  CSD CrossRef IUCr Journals
First citationSasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012b). Acta Cryst. E68, o3348.  CSD CrossRef IUCr Journals
First citationSasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.  Web of Science CSD CrossRef IUCr Journals
First citationSasagawa, K., Sakamoto, R., Kusakabe, T., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o146.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o444-o445
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds