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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Dec 4;67(Pt 1):o1–o2. doi: 10.1107/S1600536810049056

(5SR,10SR,15SR)-Trimethyl 5H,10H,15H-diindeno­[1,2-a:1′,2′-c]fluorene-5,10,15-tricarboxyl­ate 0.167-hydrate

Melissa C Menard a, Frank R Fronczek a,*, Steven F Watkins a, Raj K Dhar a
PMCID: PMC3050226  PMID: 21522612

Abstract

The title compound, C33H24O6·0.17H2O, which is commonly known as (SR,SR,SR)-trimethyl 1,10,19-truxentricarboxyl­ate, crystallizes as a hydrate with the water mol­ecule encapsulated between three ester groups by O—H⋯O hydrogen bonding to two of them. The water mol­ecule site is not fully occupied in the crystal studied, with a refined site occupancy of 0.167 (5). The 27-atom ring system is approximately planar, with a maximum deviation of 0.148 (1) Å, and the three ester substituents are all on the same side of this plane.

Related literature

For general background to bucky balls and bucky bowls, see: Akada et al. (2006 ▶); Amick & Scott (2007 ▶); Berezkin (2006 ▶); Billups & Ciufolini (1993 ▶); Emsley (1980 ▶); Kroto et al. (1985 ▶); Narozhnyi et al. (2003 ▶); Mehta & Sarma (2002 ▶); Rao (1998 ▶); Takeda et al. (2006 ▶). For related structures, see: De Frutos et al. (1999 ▶, 2002 ▶).graphic file with name e-67-000o1-scheme1.jpg

Experimental

Crystal data

  • C33H24O6·0.17H2O

  • M r = 519.61

  • Monoclinic, Inline graphic

  • a = 11.8527 (3) Å

  • b = 17.3848 (5) Å

  • c = 12.6466 (3) Å

  • β = 96.857 (2)°

  • V = 2587.28 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 90 K

  • 0.47 × 0.35 × 0.22 mm

Data collection

  • Nonius KappaCCD diffractometer with an Oxford Cryostreams Cryostream cooler

  • 14739 measured reflections

  • 7544 independent reflections

  • 5513 reflections with I > 2sI)

  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054

  • wR(F 2) = 0.144

  • S = 1.04

  • 7544 reflections

  • 365 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.26 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049056/bh2320sup1.cif

e-67-000o1-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049056/bh2320Isup2.hkl

e-67-000o1-Isup2.hkl (361.7KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O7—H7A⋯O3 1.00 1.87 2.876 (9) 179
O7—H7B⋯O4 0.99 1.96 2.955 (9) 180
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Acknowledgments

The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

supplementary crystallographic information

Comment

In 1985, Kroto, Smalley, and coworkers (Kroto et al., 1985) discovered Buckminsterfullerene, also known as the bucky ball, C60, in the soot produced by a pulsed laser on a graphite disk. This truncated icosahedron has many interesting properties and applications that have led to the synthesis of doped and undoped C60 derivatives (Billups & Ciufolini, 1993; Berezkin, 2006; Takeda et al., 2006; Akada et al., 2006; Narozhnyi et al., 2003).

Bucky bowls can be generated by opening the C60 cage along different symmetry pathways with the appropriate attachment of hydrogen atoms. These high symmetry bucky ball intermediates could be involved in the evolution of flat graphite to the spherical C60. Bucky bowls have been recognized as an important intermediate in the synthesis of C60. In addition to their relation to bucky ball, bucky bowls also exhibit many interesting properties including surface selective chemistry (Mehta & Sarma, 2002; Rao, 1998).

As part of an investigation of bucky bowls, C33H24O6. 0.17H2O was prepared. Synthesis by aldol condensation of indanone with NaOH yielded the trisannulated benzene (Amick & Scott, 2007). This was accomplished in the one-pot, acid catalyzed, head-to-tail cyclotrimerization synthesis method detailed in a previous report (Amick & Scott, 2007). The star ester was synthesized by treating the trisannulated benzene with n-butyl lithium, followed by chloromethyl formate to introduce the three ester groups. The star esters were synthesized as possible bucky bowl precursors, which when sewed together make bucky balls.

The structure, shown in Figure 1, contains three ester groups on the same side of the 27-atom ring system, such that the configurations at the asymmetric C atoms C7, C16 and C25 are all the same, S in the asymmetric unit of the racemic crystal. The ring system is only slightly nonplanar, with maximum deviation from its best plane 0.148 (1) Å for C16, and mean deviation 0.050 Å. The nature of the distortion from planarity is such that all three peripheral benzene rings form small dihedral angles with the central benzene ring. The ring containing C10 bends away from the central plane, forming a dihedral angle of 4.19 (7)° with the central ring, while the ring containing C19 bends in the same direction, forming a dihedral angle of 2.80 (7)° with the central ring. The third peripheral ring, containing C1, twists above and below the central ring, forming a dihedral angle of 1.98 (7)° with the central ring. Out-of-plane bending is necessary for buckybowls, and adoption of the bowl shape reduces the angle strain that would result in the planar form (Rao, 1998; Mehta & Sarma, 2002; Billups & Ciufolini, 1993). There is considerable flexibility in buckybowls, which undergo rapid inversion in solution. Corannulene, C20H10, inverts about 2×105 times a second at room temperature (Rao, 1998).

One of the ester groups has the carbonyl oxygen atom O4 pointed inward, while the other two have their carbonyl oxygen atoms outward. A partially occupied [16.7 (5)%] water molecule has potential hydrogen bond contacts to the three ester groups. This water comes from the second step in the synthesis, where water is the solvent. The hydrogen bond distances are consistent with previously reported values (Emsley, 1980). Difference maps were consulted to determine the hydrogen positions. Although the disorder of the water molecule can be considered dynamic, the positional disorder of the water molecule was modeled with the two H atoms within hydrogen-bonding distance to the ester O atoms. A close contact, H29A···H7A, 2.03 Å, exists in this model, and it seems likely that when the water molecule is present, methyl group C29 probably rotates to alleviate the contact. We likely would not be able to detect the alternate positions of the methyl H atoms. The same crystal, freshly prepared, had been used in a room-temperature structure determination 15.5 years earlier. At that time, the occupancy of the water molecule refined to 45.0 (6)%, but its Ueq value was large, 0.215 (4) Å2, and the water H atoms could not be located.

Due to the observed stereochemistry (syn-SR,SR,SR)-trimethyl-1,10,19-truxentricarboxylate can be used as a bucky bowl precursor with all three ester groups on the same side of the trisannulated benzene plane. A bucky bowl could be produced by conversion of the ester groups to acid chloride groups followed by pyrolysis (Mehta & Sarma, 2002; Rao, 1998).

Experimental

The synthesis of the truxene backbone, a triply annulated benzene ring, was accomplished by a two-step aldol condensation. Indanone, p-toluenesulfonic acid monohydrate, propionic acid, and o-dichlorobenzene were mixed in a single pot. After heating for 16 h at 378 K (105 °C), the reaction mixture was poured into methanol and slowly neutralized with NaOH. The precipitate was collected by filtration and washed. The resulting truxene, a pale yellow solid, was treated with n-butyl lithium to generate an anion by deprotonating the three pentlyl groups. The corresponding anion was treated with chloromethyl formate to introduce the three ester groups (Amick & Scott, 2007; De Frutos et al., 1999, 2002). Crystals were grown by slow evaporation from a mixture of CH2Cl2 and methanol.

Refinement

H atoms on C were placed in idealized positions with C—H distances 0.95 - 1.00 Å and thereafter treated as riding. A torsional parameter was refined for each methyl group. Uiso for H were assigned as 1.2 times Ueq of the attached C atom (1.5 for CH3 and H2O). H atoms for the water molecule were placed guided by difference maps, based on hydrogen bonding considerations, with O—H distance 1.0 Å, and treated as riding. The water molecule is partially occupied, and its occupancy was refined.

Figures

Fig. 1.

Fig. 1.

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The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and H atoms with arbitrary radius.

Crystal data

C33H24O6·0.17H2O F(000) = 1087
Mr = 519.61 Dx = 1.334 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 7563 reflections
a = 11.8527 (3) Å θ = 2.6–30.0°
b = 17.3848 (5) Å µ = 0.09 mm−1
c = 12.6466 (3) Å T = 90 K
β = 96.857 (2)° Prism, yellow
V = 2587.28 (12) Å3 0.47 × 0.35 × 0.22 mm
Z = 4
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Data collection

Nonius KappaCCD diffractometer with an Oxford Cryostreams Cryostream cooler Rint = 0.031
ω and φ scans θmax = 30.0°, θmin = 2.8°
14739 measured reflections h = −16→16
7544 independent reflections k = −24→24
5513 reflections with I > 2s˘I) l = −17→17
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Refinement

Refinement on F2 0 restraints
Least-squares matrix: full 0 constraints
R[F2 > 2σ(F2)] = 0.054 H-atom parameters constrained
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.0635P)2 + 1.439P] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max < 0.001
7544 reflections Δρmax = 0.47 e Å−3
365 parameters Δρmin = −0.26 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
C1 0.79369 (14) 0.28910 (9) 0.31351 (13) 0.0230 (3)
H1 0.822 0.2455 0.2798 0.028*
C2 0.80979 (14) 0.29464 (9) 0.42416 (13) 0.0225 (3)
H2 0.8484 0.2547 0.465 0.027*
C3 0.76940 (13) 0.35885 (9) 0.47593 (12) 0.0193 (3)
H3 0.7802 0.3629 0.5514 0.023*
C4 0.71288 (12) 0.41658 (8) 0.41344 (12) 0.0156 (3)
C5 0.66194 (12) 0.48950 (8) 0.44248 (11) 0.0155 (3)
C6 0.65626 (12) 0.52438 (8) 0.54044 (11) 0.0152 (3)
C7 0.70284 (12) 0.49746 (9) 0.65152 (11) 0.0166 (3)
H7 0.6671 0.4473 0.6675 0.02*
C8 0.66286 (12) 0.56068 (9) 0.72253 (12) 0.0172 (3)
C9 0.67516 (13) 0.56468 (10) 0.83230 (12) 0.0215 (3)
H9 0.7141 0.5255 0.8744 0.026*
C10 0.62905 (15) 0.62756 (10) 0.87945 (13) 0.0248 (3)
H10 0.6358 0.6308 0.9549 0.03*
C11 0.57345 (15) 0.68576 (10) 0.81902 (13) 0.0251 (3)
H11 0.5437 0.7285 0.8534 0.03*
C12 0.56078 (14) 0.68193 (9) 0.70711 (13) 0.0217 (3)
H12 0.5229 0.7216 0.6652 0.026*
C13 0.60539 (12) 0.61825 (9) 0.65917 (11) 0.0160 (3)
C14 0.60109 (12) 0.59552 (8) 0.54651 (11) 0.0153 (3)
C15 0.55157 (12) 0.63095 (8) 0.45422 (11) 0.0150 (3)
C16 0.49278 (12) 0.70854 (8) 0.43846 (11) 0.0166 (3)
H16 0.4267 0.7127 0.4804 0.02*
C17 0.45486 (12) 0.70999 (9) 0.31791 (12) 0.0174 (3)
C18 0.39336 (14) 0.76566 (9) 0.25886 (13) 0.0225 (3)
H18 0.3672 0.8102 0.2919 0.027*
C19 0.37067 (14) 0.75483 (10) 0.14951 (13) 0.0236 (3)
H19 0.3284 0.7927 0.1075 0.028*
C20 0.40849 (13) 0.68979 (10) 0.10025 (12) 0.0224 (3)
H20 0.3917 0.6837 0.0254 0.027*
C21 0.47157 (13) 0.63294 (9) 0.16088 (12) 0.0191 (3)
H21 0.4974 0.5882 0.128 0.023*
C22 0.49511 (12) 0.64422 (8) 0.27088 (11) 0.0144 (3)
C23 0.55610 (11) 0.59590 (8) 0.35456 (11) 0.0141 (3)
C24 0.61163 (12) 0.52597 (8) 0.34860 (11) 0.0146 (3)
C25 0.63200 (12) 0.47831 (9) 0.25254 (11) 0.0171 (3)
H25 0.5577 0.461 0.2142 0.021*
C26 0.69733 (12) 0.40907 (9) 0.30261 (12) 0.0174 (3)
C27 0.73685 (13) 0.34636 (9) 0.25173 (13) 0.0213 (3)
H27 0.7256 0.3423 0.1763 0.026*
C28 0.70202 (13) 0.51795 (9) 0.17463 (12) 0.0205 (3)
C29 0.85240 (15) 0.60433 (11) 0.15745 (15) 0.0320 (4)
H29A 0.9046 0.6385 0.2012 0.048*
H29B 0.8088 0.6342 0.1009 0.048*
H29C 0.896 0.5644 0.1256 0.048*
C30 0.57751 (13) 0.77331 (9) 0.46472 (11) 0.0177 (3)
C31 0.60352 (18) 0.90226 (10) 0.51643 (17) 0.0366 (5)
H31G 0.5615 0.9461 0.5408 0.055*
H31H 0.6338 0.9159 0.4501 0.055*
H31I 0.6664 0.889 0.5709 0.055*
C32 0.83138 (13) 0.49074 (10) 0.67208 (12) 0.0208 (3)
C33 1.00581 (15) 0.54451 (13) 0.64120 (19) 0.0433 (5)
H33D 1.0363 0.5858 0.6002 0.065*
H33E 1.0372 0.4951 0.6216 0.065*
H33F 1.0269 0.5538 0.7174 0.065*
O1 0.88051 (11) 0.44471 (9) 0.73200 (11) 0.0396 (4)
O2 0.52757 (11) 0.83658 (7) 0.49782 (11) 0.0289 (3)
O3 0.77526 (10) 0.56870 (8) 0.22343 (9) 0.0277 (3)
O4 0.67626 (9) 0.76970 (6) 0.45266 (9) 0.0206 (2)
O5 0.88321 (10) 0.54280 (8) 0.61814 (11) 0.0322 (3)
O6 0.69483 (12) 0.50293 (8) 0.08116 (9) 0.0307 (3)
O7 0.8591 (7) 0.6664 (5) 0.3989 (7) 0.039 (3) 0.167 (5)
H7A 0.8306 0.6321 0.3376 0.047* 0.167 (5)
H7B 0.798 0.7012 0.4172 0.047* 0.167 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0248 (8) 0.0176 (7) 0.0281 (8) 0.0014 (6) 0.0099 (6) −0.0011 (6)
C2 0.0204 (7) 0.0191 (7) 0.0286 (8) 0.0035 (6) 0.0051 (6) 0.0074 (6)
C3 0.0170 (7) 0.0221 (7) 0.0192 (7) −0.0025 (6) 0.0040 (5) 0.0041 (6)
C4 0.0127 (6) 0.0146 (6) 0.0200 (7) −0.0009 (5) 0.0042 (5) 0.0022 (5)
C5 0.0114 (6) 0.0147 (6) 0.0206 (7) −0.0011 (5) 0.0036 (5) 0.0025 (5)
C6 0.0118 (6) 0.0183 (7) 0.0152 (6) −0.0028 (5) 0.0011 (5) 0.0049 (5)
C7 0.0157 (7) 0.0190 (7) 0.0153 (6) −0.0014 (5) 0.0024 (5) 0.0024 (5)
C8 0.0142 (6) 0.0196 (7) 0.0180 (7) −0.0028 (5) 0.0032 (5) 0.0011 (5)
C9 0.0215 (7) 0.0252 (8) 0.0171 (7) −0.0017 (6) 0.0000 (5) 0.0017 (6)
C10 0.0304 (9) 0.0278 (8) 0.0159 (7) −0.0024 (7) 0.0009 (6) −0.0023 (6)
C11 0.0306 (9) 0.0234 (8) 0.0221 (8) 0.0005 (7) 0.0057 (6) −0.0053 (6)
C12 0.0228 (8) 0.0202 (7) 0.0221 (7) −0.0007 (6) 0.0025 (6) 0.0005 (6)
C13 0.0153 (7) 0.0196 (7) 0.0134 (6) −0.0050 (5) 0.0028 (5) −0.0006 (5)
C14 0.0137 (6) 0.0182 (7) 0.0143 (6) −0.0049 (5) 0.0032 (5) 0.0000 (5)
C15 0.0119 (6) 0.0140 (6) 0.0197 (7) −0.0008 (5) 0.0045 (5) 0.0010 (5)
C16 0.0159 (7) 0.0179 (7) 0.0165 (7) 0.0008 (5) 0.0037 (5) 0.0013 (5)
C17 0.0140 (6) 0.0182 (7) 0.0203 (7) −0.0013 (5) 0.0030 (5) −0.0001 (5)
C18 0.0209 (8) 0.0201 (7) 0.0262 (8) 0.0029 (6) 0.0010 (6) 0.0006 (6)
C19 0.0200 (8) 0.0236 (8) 0.0258 (8) 0.0044 (6) −0.0027 (6) 0.0049 (6)
C20 0.0202 (7) 0.0287 (8) 0.0175 (7) 0.0006 (6) −0.0009 (5) 0.0010 (6)
C21 0.0180 (7) 0.0208 (7) 0.0187 (7) −0.0012 (6) 0.0035 (5) −0.0006 (6)
C22 0.0118 (6) 0.0154 (6) 0.0160 (7) −0.0010 (5) 0.0015 (5) 0.0028 (5)
C23 0.0111 (6) 0.0165 (6) 0.0149 (6) −0.0021 (5) 0.0021 (5) 0.0040 (5)
C24 0.0130 (6) 0.0179 (7) 0.0134 (6) −0.0037 (5) 0.0041 (5) −0.0008 (5)
C25 0.0168 (7) 0.0195 (7) 0.0155 (7) 0.0021 (5) 0.0035 (5) 0.0008 (5)
C26 0.0152 (7) 0.0191 (7) 0.0185 (7) −0.0010 (5) 0.0042 (5) 0.0021 (5)
C27 0.0212 (7) 0.0218 (8) 0.0214 (7) 0.0004 (6) 0.0053 (6) 0.0003 (6)
C28 0.0195 (7) 0.0227 (7) 0.0201 (7) 0.0053 (6) 0.0063 (5) 0.0032 (6)
C29 0.0229 (8) 0.0357 (10) 0.0401 (10) 0.0011 (7) 0.0145 (7) 0.0167 (8)
C30 0.0203 (7) 0.0166 (7) 0.0166 (7) 0.0001 (5) 0.0044 (5) 0.0013 (5)
C31 0.0420 (11) 0.0205 (8) 0.0513 (12) −0.0105 (8) 0.0227 (9) −0.0113 (8)
C32 0.0174 (7) 0.0258 (8) 0.0188 (7) −0.0008 (6) 0.0008 (5) 0.0026 (6)
C33 0.0139 (8) 0.0498 (13) 0.0657 (14) −0.0063 (8) 0.0023 (8) 0.0153 (11)
O1 0.0203 (6) 0.0542 (9) 0.0425 (8) 0.0028 (6) −0.0030 (5) 0.0264 (7)
O2 0.0298 (7) 0.0161 (5) 0.0441 (7) −0.0027 (5) 0.0183 (5) −0.0063 (5)
O3 0.0207 (6) 0.0375 (7) 0.0260 (6) −0.0079 (5) 0.0071 (4) 0.0051 (5)
O4 0.0171 (5) 0.0205 (5) 0.0241 (6) −0.0015 (4) 0.0020 (4) 0.0005 (4)
O5 0.0129 (5) 0.0367 (7) 0.0464 (8) −0.0053 (5) 0.0015 (5) 0.0181 (6)
O6 0.0430 (8) 0.0337 (7) 0.0175 (6) 0.0037 (6) 0.0124 (5) 0.0024 (5)
O7 0.029 (5) 0.048 (6) 0.040 (5) 0.002 (4) 0.003 (3) −0.006 (4)
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Geometric parameters (Å, °)

C1—C27 1.389 (2) C18—H18 0.95
C1—C2 1.393 (2) C19—C20 1.391 (2)
C1—H1 0.95 C19—H19 0.95
C2—C3 1.407 (2) C20—C21 1.410 (2)
C2—H2 0.95 C20—H20 0.95
C3—C4 1.398 (2) C21—C22 1.400 (2)
C3—H3 0.95 C21—H21 0.95
C4—C26 1.398 (2) C22—C23 1.4715 (19)
C4—C5 1.470 (2) C23—C24 1.389 (2)
C5—C6 1.388 (2) C24—C25 1.513 (2)
C5—C24 1.414 (2) C25—C28 1.526 (2)
C6—C14 1.405 (2) C25—C26 1.527 (2)
C6—C7 1.5205 (19) C25—H25 1
C7—C32 1.519 (2) C26—C27 1.376 (2)
C7—C8 1.530 (2) C27—H27 0.95
C7—H7 1 C28—O6 1.2036 (19)
C8—C9 1.380 (2) C28—O3 1.336 (2)
C8—C13 1.406 (2) C29—O3 1.4485 (19)
C9—C10 1.388 (2) C29—H29A 0.98
C9—H9 0.95 C29—H29B 0.98
C10—C11 1.386 (2) C29—H29C 0.98
C10—H10 0.95 C30—O4 1.1999 (18)
C11—C12 1.407 (2) C30—O2 1.3396 (18)
C11—H11 0.95 C31—O2 1.456 (2)
C12—C13 1.396 (2) C31—H31G 0.98
C12—H12 0.95 C31—H31H 0.98
C13—C14 1.4736 (19) C31—H31I 0.98
C14—C15 1.387 (2) C32—O1 1.204 (2)
C15—C23 1.407 (2) C32—O5 1.3274 (19)
C15—C16 1.520 (2) C33—O5 1.448 (2)
C16—C30 1.519 (2) C33—H33D 0.98
C16—C17 1.537 (2) C33—H33E 0.98
C16—H16 1 C33—H33F 0.98
C17—C18 1.377 (2) O7—H7A 1.00
C17—C22 1.399 (2) O7—H7B 0.99
C18—C19 1.390 (2)
C27—C1—C2 120.97 (15) C18—C19—H19 119.3
C27—C1—H1 119.5 C20—C19—H19 119.3
C2—C1—H1 119.5 C19—C20—C21 120.32 (14)
C1—C2—C3 120.59 (14) C19—C20—H20 119.8
C1—C2—H2 119.7 C21—C20—H20 119.8
C3—C2—H2 119.7 C22—C21—C20 118.18 (14)
C4—C3—C2 118.25 (14) C22—C21—H21 120.9
C4—C3—H3 120.9 C20—C21—H21 120.9
C2—C3—H3 120.9 C17—C22—C21 119.97 (13)
C26—C4—C3 119.79 (14) C17—C22—C23 108.91 (12)
C26—C4—C5 108.80 (12) C21—C22—C23 131.10 (14)
C3—C4—C5 131.42 (14) C24—C23—C15 119.79 (13)
C6—C5—C24 119.55 (13) C24—C23—C22 130.99 (13)
C6—C5—C4 131.68 (13) C15—C23—C22 109.21 (12)
C24—C5—C4 108.77 (12) C23—C24—C5 120.14 (13)
C5—C6—C14 120.37 (13) C23—C24—C25 130.15 (13)
C5—C6—C7 129.73 (13) C5—C24—C25 109.69 (13)
C14—C6—C7 109.90 (12) C24—C25—C28 114.97 (13)
C32—C7—C6 115.34 (12) C24—C25—C26 102.73 (11)
C32—C7—C8 109.23 (12) C28—C25—C26 109.61 (12)
C6—C7—C8 102.56 (12) C24—C25—H25 109.8
C32—C7—H7 109.8 C28—C25—H25 109.8
C6—C7—H7 109.8 C26—C25—H25 109.8
C8—C7—H7 109.8 C27—C26—C4 122.10 (14)
C9—C8—C13 121.54 (14) C27—C26—C25 127.92 (14)
C9—C8—C7 128.58 (14) C4—C26—C25 109.98 (12)
C13—C8—C7 109.86 (12) C26—C27—C1 118.29 (15)
C8—C9—C10 118.16 (15) C26—C27—H27 120.9
C8—C9—H9 120.9 C1—C27—H27 120.9
C10—C9—H9 120.9 O6—C28—O3 124.25 (15)
C11—C10—C9 121.57 (15) O6—C28—C25 123.77 (15)
C11—C10—H10 119.2 O3—C28—C25 111.92 (13)
C9—C10—H10 119.2 O3—C29—H29A 109.5
C10—C11—C12 120.44 (15) O3—C29—H29B 109.5
C10—C11—H11 119.8 H29A—C29—H29B 109.5
C12—C11—H11 119.8 O3—C29—H29C 109.5
C13—C12—C11 118.29 (15) H29A—C29—H29C 109.5
C13—C12—H12 120.9 H29B—C29—H29C 109.5
C11—C12—H12 120.9 O4—C30—O2 123.84 (14)
C12—C13—C8 119.98 (13) O4—C30—C16 124.26 (14)
C12—C13—C14 131.40 (14) O2—C30—C16 111.82 (12)
C8—C13—C14 108.58 (13) O2—C31—H31G 109.5
C15—C14—C6 119.87 (13) O2—C31—H31H 109.5
C15—C14—C13 131.07 (14) H31G—C31—H31H 109.5
C6—C14—C13 109.04 (12) O2—C31—H31I 109.5
C14—C15—C23 120.27 (13) H31G—C31—H31I 109.5
C14—C15—C16 130.23 (13) H31H—C31—H31I 109.5
C23—C15—C16 109.43 (12) O1—C32—O5 123.93 (15)
C30—C16—C15 110.38 (12) O1—C32—C7 123.98 (14)
C30—C16—C17 108.19 (12) O5—C32—C7 112.08 (13)
C15—C16—C17 102.70 (12) O5—C33—H33D 109.5
C30—C16—H16 111.7 O5—C33—H33E 109.5
C15—C16—H16 111.7 H33D—C33—H33E 109.5
C17—C16—H16 111.7 O5—C33—H33F 109.5
C18—C17—C22 121.96 (14) H33D—C33—H33F 109.5
C18—C17—C16 128.51 (14) H33E—C33—H33F 109.5
C22—C17—C16 109.52 (12) C30—O2—C31 114.00 (13)
C17—C18—C19 118.14 (15) C28—O3—C29 115.87 (14)
C17—C18—H18 120.9 C32—O5—C33 115.18 (14)
C19—C18—H18 120.9 H7A—O7—H7B 110.8
C18—C19—C20 121.43 (15)
C27—C1—C2—C3 −0.5 (2) C18—C17—C22—C21 −1.1 (2)
C1—C2—C3—C4 0.0 (2) C16—C17—C22—C21 −179.71 (13)
C2—C3—C4—C26 0.4 (2) C18—C17—C22—C23 −179.42 (14)
C2—C3—C4—C5 −179.76 (15) C16—C17—C22—C23 1.93 (16)
C26—C4—C5—C6 −178.57 (15) C20—C21—C22—C17 0.9 (2)
C3—C4—C5—C6 1.6 (3) C20—C21—C22—C23 178.87 (14)
C26—C4—C5—C24 1.76 (16) C14—C15—C23—C24 −0.8 (2)
C3—C4—C5—C24 −178.07 (15) C16—C15—C23—C24 176.61 (12)
C24—C5—C6—C14 −0.1 (2) C14—C15—C23—C22 178.59 (12)
C4—C5—C6—C14 −179.74 (14) C16—C15—C23—C22 −4.01 (15)
C24—C5—C6—C7 180.00 (13) C17—C22—C23—C24 −179.42 (14)
C4—C5—C6—C7 0.4 (3) C21—C22—C23—C24 2.5 (3)
C5—C6—C7—C32 63.6 (2) C17—C22—C23—C15 1.29 (16)
C14—C6—C7—C32 −116.28 (14) C21—C22—C23—C15 −176.82 (15)
C5—C6—C7—C8 −177.77 (14) C15—C23—C24—C5 1.0 (2)
C14—C6—C7—C8 2.33 (15) C22—C23—C24—C5 −178.24 (14)
C32—C7—C8—C9 −61.07 (19) C15—C23—C24—C25 −177.60 (14)
C6—C7—C8—C9 176.11 (15) C22—C23—C24—C25 3.2 (3)
C32—C7—C8—C13 120.30 (13) C6—C5—C24—C23 −0.5 (2)
C6—C7—C8—C13 −2.53 (15) C4—C5—C24—C23 179.17 (12)
C13—C8—C9—C10 0.0 (2) C6—C5—C24—C25 178.31 (12)
C7—C8—C9—C10 −178.52 (15) C4—C5—C24—C25 −1.98 (16)
C8—C9—C10—C11 −1.0 (2) C23—C24—C25—C28 61.1 (2)
C9—C10—C11—C12 0.9 (3) C5—C24—C25—C28 −117.57 (14)
C10—C11—C12—C13 0.1 (2) C23—C24—C25—C26 −179.88 (14)
C11—C12—C13—C8 −1.0 (2) C5—C24—C25—C26 1.42 (15)
C11—C12—C13—C14 176.35 (15) C3—C4—C26—C27 −0.5 (2)
C9—C8—C13—C12 1.0 (2) C5—C4—C26—C27 179.63 (14)
C7—C8—C13—C12 179.78 (13) C3—C4—C26—C25 179.02 (13)
C9—C8—C13—C14 −176.90 (14) C5—C4—C26—C25 −0.83 (16)
C7—C8—C13—C14 1.85 (16) C24—C25—C26—C27 179.18 (15)
C5—C6—C14—C15 0.3 (2) C28—C25—C26—C27 −58.1 (2)
C7—C6—C14—C15 −179.79 (12) C24—C25—C26—C4 −0.33 (15)
C5—C6—C14—C13 178.73 (13) C28—C25—C26—C4 122.35 (13)
C7—C6—C14—C13 −1.36 (16) C4—C26—C27—C1 0.1 (2)
C12—C13—C14—C15 0.3 (3) C25—C26—C27—C1 −179.35 (14)
C8—C13—C14—C15 177.88 (14) C2—C1—C27—C26 0.4 (2)
C12—C13—C14—C6 −177.92 (15) C24—C25—C28—O6 −153.27 (15)
C8—C13—C14—C6 −0.32 (16) C26—C25—C28—O6 91.65 (18)
C6—C14—C15—C23 0.1 (2) C24—C25—C28—O3 29.38 (18)
C13—C14—C15—C23 −177.89 (14) C26—C25—C28—O3 −85.70 (15)
C6—C14—C15—C16 −176.64 (14) C15—C16—C30—O4 30.93 (19)
C13—C14—C15—C16 5.3 (3) C17—C16—C30—O4 −80.72 (18)
C14—C15—C16—C30 66.79 (19) C15—C16—C30—O2 −152.33 (12)
C23—C15—C16—C30 −110.26 (13) C17—C16—C30—O2 96.02 (14)
C14—C15—C16—C17 −178.06 (14) C6—C7—C32—O1 −148.97 (17)
C23—C15—C16—C17 4.89 (15) C8—C7—C32—O1 96.20 (19)
C30—C16—C17—C18 −65.91 (19) C6—C7—C32—O5 32.53 (19)
C15—C16—C17—C18 177.36 (15) C8—C7—C32—O5 −82.31 (16)
C30—C16—C17—C22 112.63 (14) O4—C30—O2—C31 1.1 (2)
C15—C16—C17—C22 −4.11 (15) C16—C30—O2—C31 −175.64 (14)
C22—C17—C18—C19 0.5 (2) O6—C28—O3—C29 −2.5 (2)
C16—C17—C18—C19 178.93 (15) C25—C28—O3—C29 174.81 (13)
C17—C18—C19—C20 0.1 (2) O1—C32—O5—C33 −3.9 (3)
C18—C19—C20—C21 −0.1 (3) C7—C32—O5—C33 174.59 (16)
C19—C20—C21—C22 −0.3 (2)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O7—H7A···O3 1.00 1.87 2.876 (9) 179
O7—H7B···O4 0.99 1.96 2.955 (9) 180
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2320).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049056/bh2320sup1.cif

e-67-000o1-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049056/bh2320Isup2.hkl

e-67-000o1-Isup2.hkl (361.7KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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