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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Mar 5;67(Pt 4):o785. doi: 10.1107/S1600536811007318

3,3,6,6-Tetra­methyl-9-[6-(3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthen-9-yl)pyridin-2-yl]-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

Antar A Abdelhamid a, Shaaban Kamel Mohamed b, Mirze A Allahverdiyev a, Atash V Gurbanov a, Seik Weng Ng c,*
PMCID: PMC3100053  PMID: 21754076

Abstract

In the title mol­ecule, C39H45NO6, the two tetra­methyl­octa­hydroxanthen-1,8-dione substituents are arranged approximately parallel to each other and approximately perpendicular to the plane of the pyridine ring. The six-membered xanthene rings adopt flattened boat conformations with the O and methine C atoms deviating from the plane of the other four atoms.

Related literature

For a related structure, see: Mohamed et al. (2011 ▶).graphic file with name e-67-0o785-scheme1.jpg

Experimental

Crystal data

  • C39H45NO6

  • M r = 623.76

  • Monoclinic, Inline graphic

  • a = 24.1384 (8) Å

  • b = 10.0371 (4) Å

  • c = 14.4408 (5) Å

  • β = 105.8460 (7)°

  • V = 3365.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.30 × 0.30 × 0.30 mm

Data collection

  • Bruker APEXII diffractometer

  • 35921 measured reflections

  • 7717 independent reflections

  • 6410 reflections with I > 2σ(I)

  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041

  • wR(F 2) = 0.111

  • S = 1.03

  • 7717 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007318/lh5213sup1.cif

e-67-0o785-sup1.cif (30.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007318/lh5213Isup2.hkl

e-67-0o785-Isup2.hkl (377.6KB, hkl)

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

Acknowledgments

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The reaction of pyridine-2,6-dicarboxaldehyde, amino-2-propanol and dimedone in ethanol yields the ethanol solvate of 4α-hydroxy-3,3,6,6-tetramethyl-9-[6-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-9-xanthenyl)-2-pyridyl]-2,3,4,4α,5,6,7,8,9,9α-decahydro-1,8-xanthenedione. The compound has two xanthenyldione portions but the carbon-carbon double bond of one is hydrated (Mohamed et al., 2011). The title compound is that without water adding across the double bond, and was obtained by using a light different synthetic route. The pyridine ring in C39H45NO6 is connected to two tetramethyloctahydroxanthen-1,8-dionyl substituents at the 2- and 6-positions of the ring; the six-membered xanthenyl rings adopt flattened boat-shaped conformations (with the O and methine C atoms deviating from the plane of the other four atoms. The other six-membered rings are in sofa conformations (Fig. 1). The xanthenyl units are stacked over each other (Fig. 2).

Experimental

A mixture of 1,2-ethanediammonium chloride (0.01 mol) and 2,6-pyridinedicarbaldehyde (0.01 mol) in aqueous ethanol (1:1) was heated for 30 minutes. To the mixture was added dimedone (0.04 mol). The mixture was heated for another 5 fhours. The solvent was evaporated to yield a pale yellow compound. This was recrystallized from ethanol in 60% yield; m.p. 473 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.99 Å; U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) of C39H45NO6 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Fig. 2.

Fig. 2.

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View of the molecule along the pyridyl plane. The pyridyl atoms are shown as 70% thermal ellipsoids in their van der Waals surfaces whereas the other atoms are shown in the ball-and-stick style.

Crystal data

C39H45NO6 F(000) = 1336
Mr = 623.76 Dx = 1.231 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 9997 reflections
a = 24.1384 (8) Å θ = 2.2–28.3°
b = 10.0371 (4) Å µ = 0.08 mm−1
c = 14.4408 (5) Å T = 100 K
β = 105.8460 (7)° Prism, yellow
V = 3365.8 (2) Å3 0.30 × 0.30 × 0.30 mm
Z = 4
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Data collection

Bruker APEXII diffractometer 6410 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.035
graphite θmax = 27.5°, θmin = 0.9°
φ and ω scans h = −31→31
35921 measured reflections k = −13→13
7717 independent reflections l = −18→18
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0516P)2 + 1.4985P] where P = (Fo2 + 2Fc2)/3
7717 reflections (Δ/σ)max = 0.001
415 parameters Δρmax = 0.35 e Å−3
0 restraints Δρmin = −0.25 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.25761 (4) 0.57513 (8) 0.57197 (6) 0.01520 (18)
O2 0.14471 (4) 0.79864 (10) 0.29720 (7) 0.0240 (2)
O3 0.36827 (4) 0.79429 (9) 0.39499 (7) 0.0219 (2)
O4 0.24055 (4) 0.16338 (10) 0.42959 (6) 0.0194 (2)
O5 0.35334 (4) 0.23059 (10) 0.21320 (7) 0.0235 (2)
O6 0.12820 (4) 0.24399 (11) 0.11215 (7) 0.0283 (2)
N1 0.24746 (4) 0.48227 (10) 0.31079 (7) 0.0153 (2)
C1 0.25467 (5) 0.61420 (12) 0.30329 (8) 0.0139 (2)
C2 0.26132 (5) 0.67429 (13) 0.22082 (9) 0.0171 (2)
H2 0.2668 0.7678 0.2187 0.020*
C3 0.25984 (5) 0.59557 (13) 0.14138 (9) 0.0185 (3)
H3 0.2644 0.6341 0.0838 0.022*
C4 0.25163 (5) 0.46041 (13) 0.14736 (9) 0.0163 (2)
H4 0.2498 0.4044 0.0936 0.020*
C5 0.24614 (5) 0.40734 (12) 0.23306 (8) 0.0142 (2)
C6 0.25609 (5) 0.70059 (12) 0.39089 (8) 0.0143 (2)
H6 0.2567 0.7960 0.3712 0.017*
C7 0.30987 (5) 0.67488 (12) 0.47187 (9) 0.0144 (2)
C8 0.36561 (5) 0.72160 (12) 0.46172 (9) 0.0160 (2)
C9 0.41928 (5) 0.67402 (13) 0.53518 (9) 0.0189 (3)
H9A 0.4512 0.7362 0.5355 0.023*
H9B 0.4300 0.5855 0.5151 0.023*
C10 0.41313 (5) 0.66312 (13) 0.63785 (9) 0.0196 (3)
C11 0.35893 (5) 0.58161 (13) 0.63655 (9) 0.0168 (2)
H11A 0.3680 0.4857 0.6343 0.020*
H11B 0.3484 0.5980 0.6972 0.020*
C12 0.30824 (5) 0.61373 (12) 0.55352 (9) 0.0139 (2)
C13 0.46594 (6) 0.59178 (16) 0.70204 (11) 0.0294 (3)
H13A 0.5007 0.6430 0.7034 0.044*
H13B 0.4690 0.5026 0.6763 0.044*
H13C 0.4619 0.5842 0.7675 0.044*
C14 0.40892 (6) 0.80262 (14) 0.67847 (10) 0.0260 (3)
H14A 0.4436 0.8535 0.6789 0.039*
H14B 0.4054 0.7951 0.7443 0.039*
H14C 0.3750 0.8484 0.6382 0.039*
C15 0.20391 (5) 0.68011 (12) 0.42723 (9) 0.0148 (2)
C16 0.14805 (5) 0.73105 (13) 0.36908 (9) 0.0172 (2)
C17 0.09520 (5) 0.69456 (13) 0.40051 (9) 0.0193 (3)
H17A 0.0811 0.6065 0.3731 0.023*
H17B 0.0646 0.7607 0.3737 0.023*
C18 0.10563 (5) 0.68897 (13) 0.51000 (9) 0.0181 (3)
C19 0.15724 (5) 0.59658 (12) 0.55268 (9) 0.0174 (2)
H19A 0.1704 0.6102 0.6232 0.021*
H19B 0.1446 0.5028 0.5409 0.021*
C20 0.20658 (5) 0.62020 (12) 0.51102 (9) 0.0144 (2)
C21 0.05265 (6) 0.63199 (15) 0.53434 (11) 0.0254 (3)
H21A 0.0194 0.6899 0.5076 0.038*
H21B 0.0599 0.6270 0.6044 0.038*
H21C 0.0446 0.5426 0.5067 0.038*
C22 0.11671 (6) 0.82998 (13) 0.55179 (10) 0.0212 (3)
H22A 0.0832 0.8864 0.5234 0.032*
H22B 0.1508 0.8673 0.5369 0.032*
H22C 0.1232 0.8264 0.6218 0.032*
C23 0.24111 (5) 0.25647 (12) 0.24168 (8) 0.0152 (2)
H23 0.2399 0.2159 0.1779 0.018*
C24 0.29335 (5) 0.20300 (12) 0.31524 (9) 0.0158 (2)
C25 0.34866 (6) 0.19442 (12) 0.29151 (9) 0.0174 (3)
C26 0.39889 (5) 0.13376 (13) 0.36653 (9) 0.0185 (3)
H26A 0.4353 0.1653 0.3551 0.022*
H26B 0.3975 0.0356 0.3592 0.022*
C27 0.39860 (5) 0.16943 (13) 0.46965 (9) 0.0184 (3)
C28 0.34085 (5) 0.12467 (13) 0.48417 (9) 0.0188 (3)
H28A 0.3407 0.0264 0.4899 0.023*
H28B 0.3365 0.1628 0.5451 0.023*
C29 0.29112 (5) 0.16688 (12) 0.40344 (9) 0.0163 (2)
C30 0.44699 (6) 0.09678 (15) 0.54235 (10) 0.0252 (3)
H30A 0.4462 0.1207 0.6078 0.038*
H30B 0.4841 0.1226 0.5326 0.038*
H30C 0.4417 0.0004 0.5334 0.038*
C31 0.40642 (6) 0.31961 (14) 0.48608 (11) 0.0253 (3)
H31A 0.4061 0.3410 0.5522 0.038*
H31B 0.3749 0.3669 0.4408 0.038*
H31C 0.4432 0.3472 0.4758 0.038*
C32 0.18784 (5) 0.21360 (12) 0.26884 (9) 0.0160 (2)
C33 0.13235 (6) 0.20954 (13) 0.19479 (9) 0.0195 (3)
C34 0.08132 (6) 0.15408 (15) 0.22403 (9) 0.0237 (3)
H34A 0.0800 0.0564 0.2142 0.028*
H34B 0.0456 0.1920 0.1811 0.028*
C35 0.08224 (5) 0.18284 (13) 0.32849 (9) 0.0186 (3)
C36 0.13980 (5) 0.13223 (13) 0.39325 (9) 0.0180 (3)
H36A 0.1451 0.1668 0.4593 0.022*
H36B 0.1388 0.0337 0.3962 0.022*
C37 0.18971 (5) 0.17401 (12) 0.35799 (9) 0.0159 (2)
C38 0.03288 (6) 0.10894 (15) 0.35365 (10) 0.0254 (3)
H38A −0.0040 0.1410 0.3124 0.038*
H38B 0.0345 0.1253 0.4213 0.038*
H38C 0.0365 0.0132 0.3434 0.038*
C39 0.07642 (6) 0.33236 (14) 0.34388 (11) 0.0258 (3)
H39A 0.0396 0.3640 0.3023 0.039*
H39B 0.1081 0.3797 0.3278 0.039*
H39C 0.0779 0.3491 0.4114 0.039*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0141 (4) 0.0163 (4) 0.0153 (4) −0.0004 (3) 0.0043 (3) 0.0024 (3)
O2 0.0251 (5) 0.0286 (5) 0.0178 (5) 0.0065 (4) 0.0048 (4) 0.0037 (4)
O3 0.0244 (5) 0.0234 (5) 0.0190 (5) −0.0044 (4) 0.0078 (4) 0.0021 (4)
O4 0.0159 (4) 0.0302 (5) 0.0131 (4) 0.0013 (4) 0.0055 (3) 0.0037 (4)
O5 0.0300 (5) 0.0246 (5) 0.0205 (5) 0.0050 (4) 0.0149 (4) 0.0045 (4)
O6 0.0298 (5) 0.0392 (6) 0.0140 (4) −0.0012 (4) 0.0030 (4) 0.0029 (4)
N1 0.0178 (5) 0.0161 (5) 0.0124 (5) 0.0001 (4) 0.0049 (4) 0.0005 (4)
C1 0.0120 (5) 0.0160 (6) 0.0129 (5) 0.0011 (4) 0.0021 (4) −0.0003 (4)
C2 0.0189 (6) 0.0157 (6) 0.0166 (6) 0.0001 (5) 0.0048 (5) 0.0031 (5)
C3 0.0205 (6) 0.0224 (6) 0.0137 (6) 0.0013 (5) 0.0066 (5) 0.0043 (5)
C4 0.0172 (6) 0.0206 (6) 0.0114 (5) 0.0016 (5) 0.0043 (5) −0.0002 (5)
C5 0.0136 (5) 0.0159 (6) 0.0131 (5) 0.0008 (4) 0.0036 (4) 0.0008 (4)
C6 0.0168 (6) 0.0132 (5) 0.0130 (5) 0.0004 (4) 0.0044 (5) 0.0011 (4)
C7 0.0154 (6) 0.0135 (5) 0.0142 (6) −0.0002 (4) 0.0039 (5) −0.0024 (4)
C8 0.0194 (6) 0.0147 (6) 0.0153 (6) −0.0020 (5) 0.0069 (5) −0.0031 (5)
C9 0.0156 (6) 0.0203 (6) 0.0215 (6) −0.0018 (5) 0.0060 (5) 0.0005 (5)
C10 0.0163 (6) 0.0235 (7) 0.0175 (6) −0.0036 (5) 0.0019 (5) 0.0019 (5)
C11 0.0169 (6) 0.0183 (6) 0.0147 (6) −0.0004 (5) 0.0035 (5) 0.0022 (5)
C12 0.0145 (6) 0.0112 (5) 0.0162 (6) −0.0009 (4) 0.0049 (5) −0.0025 (4)
C13 0.0180 (7) 0.0394 (8) 0.0266 (7) −0.0042 (6) −0.0009 (6) 0.0108 (6)
C14 0.0300 (7) 0.0274 (7) 0.0200 (7) −0.0103 (6) 0.0057 (6) −0.0044 (5)
C15 0.0164 (6) 0.0135 (5) 0.0144 (6) 0.0002 (4) 0.0040 (5) −0.0034 (4)
C16 0.0199 (6) 0.0160 (6) 0.0149 (6) 0.0019 (5) 0.0033 (5) −0.0033 (5)
C17 0.0156 (6) 0.0201 (6) 0.0205 (6) 0.0013 (5) 0.0021 (5) −0.0028 (5)
C18 0.0158 (6) 0.0185 (6) 0.0209 (6) 0.0004 (5) 0.0066 (5) 0.0001 (5)
C19 0.0171 (6) 0.0169 (6) 0.0189 (6) −0.0016 (5) 0.0064 (5) 0.0014 (5)
C20 0.0144 (6) 0.0125 (5) 0.0161 (6) 0.0000 (4) 0.0038 (5) −0.0023 (4)
C21 0.0171 (6) 0.0269 (7) 0.0345 (8) 0.0006 (5) 0.0109 (6) 0.0036 (6)
C22 0.0227 (6) 0.0204 (6) 0.0218 (6) 0.0016 (5) 0.0083 (5) −0.0011 (5)
C23 0.0208 (6) 0.0152 (6) 0.0104 (5) 0.0007 (5) 0.0057 (5) −0.0006 (4)
C24 0.0193 (6) 0.0141 (6) 0.0151 (6) 0.0009 (5) 0.0065 (5) −0.0006 (4)
C25 0.0239 (6) 0.0132 (6) 0.0175 (6) 0.0009 (5) 0.0095 (5) −0.0014 (5)
C26 0.0200 (6) 0.0179 (6) 0.0207 (6) 0.0030 (5) 0.0109 (5) 0.0007 (5)
C27 0.0176 (6) 0.0203 (6) 0.0183 (6) 0.0025 (5) 0.0066 (5) 0.0006 (5)
C28 0.0187 (6) 0.0239 (6) 0.0148 (6) 0.0021 (5) 0.0063 (5) 0.0036 (5)
C29 0.0173 (6) 0.0166 (6) 0.0166 (6) 0.0004 (5) 0.0074 (5) 0.0000 (5)
C30 0.0185 (6) 0.0341 (8) 0.0235 (7) 0.0037 (6) 0.0061 (5) 0.0046 (6)
C31 0.0233 (7) 0.0233 (7) 0.0292 (7) −0.0004 (5) 0.0072 (6) −0.0052 (6)
C32 0.0195 (6) 0.0140 (6) 0.0146 (6) 0.0000 (5) 0.0051 (5) −0.0011 (4)
C33 0.0235 (7) 0.0195 (6) 0.0147 (6) −0.0002 (5) 0.0039 (5) −0.0021 (5)
C34 0.0201 (6) 0.0320 (7) 0.0173 (6) −0.0059 (6) 0.0022 (5) −0.0038 (5)
C35 0.0186 (6) 0.0196 (6) 0.0174 (6) −0.0009 (5) 0.0046 (5) −0.0008 (5)
C36 0.0202 (6) 0.0197 (6) 0.0151 (6) −0.0002 (5) 0.0065 (5) 0.0024 (5)
C37 0.0172 (6) 0.0152 (6) 0.0149 (6) 0.0007 (5) 0.0035 (5) −0.0010 (5)
C38 0.0201 (7) 0.0301 (7) 0.0262 (7) −0.0035 (6) 0.0066 (5) 0.0000 (6)
C39 0.0266 (7) 0.0212 (7) 0.0311 (8) 0.0034 (5) 0.0102 (6) 0.0001 (6)
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Geometric parameters (Å, °)

O1—C12 1.3757 (14) C19—C20 1.4926 (17)
O1—C20 1.3800 (14) C19—H19A 0.9900
O2—C16 1.2242 (16) C19—H19B 0.9900
O3—C8 1.2242 (15) C21—H21A 0.9800
O4—C29 1.3732 (15) C21—H21B 0.9800
O4—C37 1.3761 (15) C21—H21C 0.9800
O5—C25 1.2220 (15) C22—H22A 0.9800
O6—C33 1.2200 (16) C22—H22B 0.9800
N1—C1 1.3438 (16) C22—H22C 0.9800
N1—C5 1.3443 (15) C23—C32 1.5060 (17)
C1—C2 1.3829 (17) C23—C24 1.5082 (17)
C1—C6 1.5264 (16) C23—H23 1.0000
C2—C3 1.3853 (18) C24—C29 1.3393 (17)
C2—H2 0.9500 C24—C25 1.4688 (17)
C3—C4 1.3771 (18) C25—C26 1.5157 (18)
C3—H3 0.9500 C26—C27 1.5335 (17)
C4—C5 1.3865 (16) C26—H26A 0.9900
C4—H4 0.9500 C26—H26B 0.9900
C5—C23 1.5270 (17) C27—C30 1.5261 (18)
C6—C15 1.5051 (17) C27—C31 1.5296 (19)
C6—C7 1.5133 (16) C27—C28 1.5325 (17)
C6—H6 1.0000 C28—C29 1.4884 (17)
C7—C12 1.3393 (17) C28—H28A 0.9900
C7—C8 1.4696 (17) C28—H28B 0.9900
C8—C9 1.5103 (17) C30—H30A 0.9800
C9—C10 1.5338 (18) C30—H30B 0.9800
C9—H9A 0.9900 C30—H30C 0.9800
C9—H9B 0.9900 C31—H31A 0.9800
C10—C14 1.5321 (19) C31—H31B 0.9800
C10—C13 1.5336 (18) C31—H31C 0.9800
C10—C11 1.5387 (17) C32—C37 1.3363 (17)
C11—C12 1.4958 (17) C32—C33 1.4687 (17)
C11—H11A 0.9900 C33—C34 1.5129 (18)
C11—H11B 0.9900 C34—C35 1.5301 (18)
C13—H13A 0.9800 C34—H34A 0.9900
C13—H13B 0.9800 C34—H34B 0.9900
C13—H13C 0.9800 C35—C38 1.5293 (18)
C14—H14A 0.9800 C35—C39 1.5292 (18)
C14—H14B 0.9800 C35—C36 1.5341 (18)
C14—H14C 0.9800 C36—C37 1.4903 (17)
C15—C20 1.3368 (17) C36—H36A 0.9900
C15—C16 1.4719 (17) C36—H36B 0.9900
C16—C17 1.5111 (18) C38—H38A 0.9800
C17—C18 1.5328 (18) C38—H38B 0.9800
C17—H17A 0.9900 C38—H38C 0.9800
C17—H17B 0.9900 C39—H39A 0.9800
C18—C21 1.5269 (17) C39—H39B 0.9800
C18—C22 1.5332 (18) C39—H39C 0.9800
C18—C19 1.5403 (17)
C12—O1—C20 118.01 (9) C18—C21—H21C 109.5
C29—O4—C37 117.95 (9) H21A—C21—H21C 109.5
C1—N1—C5 117.26 (10) H21B—C21—H21C 109.5
N1—C1—C2 123.18 (11) C18—C22—H22A 109.5
N1—C1—C6 117.84 (10) C18—C22—H22B 109.5
C2—C1—C6 118.97 (11) H22A—C22—H22B 109.5
C1—C2—C3 118.79 (12) C18—C22—H22C 109.5
C1—C2—H2 120.6 H22A—C22—H22C 109.5
C3—C2—H2 120.6 H22B—C22—H22C 109.5
C4—C3—C2 118.78 (11) C32—C23—C24 108.91 (10)
C4—C3—H3 120.6 C32—C23—C5 113.40 (10)
C2—C3—H3 120.6 C24—C23—C5 109.91 (10)
C3—C4—C5 119.01 (11) C32—C23—H23 108.2
C3—C4—H4 120.5 C24—C23—H23 108.2
C5—C4—H4 120.5 C5—C23—H23 108.2
N1—C5—C4 122.97 (11) C29—C24—C25 118.76 (11)
N1—C5—C23 118.10 (10) C29—C24—C23 121.54 (11)
C4—C5—C23 118.87 (11) C25—C24—C23 119.66 (10)
C15—C6—C7 109.28 (10) O5—C25—C24 121.22 (12)
C15—C6—C1 112.32 (10) O5—C25—C26 121.50 (11)
C7—C6—C1 111.35 (10) C24—C25—C26 117.23 (10)
C15—C6—H6 107.9 C25—C26—C27 112.66 (10)
C7—C6—H6 107.9 C25—C26—H26A 109.1
C1—C6—H6 107.9 C27—C26—H26A 109.1
C12—C7—C8 118.80 (11) C25—C26—H26B 109.1
C12—C7—C6 122.23 (11) C27—C26—H26B 109.1
C8—C7—C6 118.95 (10) H26A—C26—H26B 107.8
O3—C8—C7 120.99 (11) C30—C27—C31 108.98 (11)
O3—C8—C9 121.47 (11) C30—C27—C28 108.65 (11)
C7—C8—C9 117.52 (10) C31—C27—C28 110.25 (11)
C8—C9—C10 114.25 (10) C30—C27—C26 110.53 (11)
C8—C9—H9A 108.7 C31—C27—C26 110.34 (11)
C10—C9—H9A 108.7 C28—C27—C26 108.06 (10)
C8—C9—H9B 108.7 C29—C28—C27 112.24 (10)
C10—C9—H9B 108.7 C29—C28—H28A 109.2
H9A—C9—H9B 107.6 C27—C28—H28A 109.2
C14—C10—C13 109.05 (11) C29—C28—H28B 109.2
C14—C10—C9 109.82 (11) C27—C28—H28B 109.2
C13—C10—C9 109.49 (11) H28A—C28—H28B 107.9
C14—C10—C11 110.21 (11) C24—C29—O4 122.55 (11)
C13—C10—C11 108.83 (11) C24—C29—C28 126.06 (11)
C9—C10—C11 109.42 (10) O4—C29—C28 111.39 (10)
C12—C11—C10 113.69 (10) C27—C30—H30A 109.5
C12—C11—H11A 108.8 C27—C30—H30B 109.5
C10—C11—H11A 108.8 H30A—C30—H30B 109.5
C12—C11—H11B 108.8 C27—C30—H30C 109.5
C10—C11—H11B 108.8 H30A—C30—H30C 109.5
H11A—C11—H11B 107.7 H30B—C30—H30C 109.5
C7—C12—O1 122.73 (11) C27—C31—H31A 109.5
C7—C12—C11 126.18 (11) C27—C31—H31B 109.5
O1—C12—C11 111.07 (10) H31A—C31—H31B 109.5
C10—C13—H13A 109.5 C27—C31—H31C 109.5
C10—C13—H13B 109.5 H31A—C31—H31C 109.5
H13A—C13—H13B 109.5 H31B—C31—H31C 109.5
C10—C13—H13C 109.5 C37—C32—C33 118.51 (11)
H13A—C13—H13C 109.5 C37—C32—C23 121.95 (11)
H13B—C13—H13C 109.5 C33—C32—C23 119.49 (11)
C10—C14—H14A 109.5 O6—C33—C32 121.28 (12)
C10—C14—H14B 109.5 O6—C33—C34 121.44 (12)
H14A—C14—H14B 109.5 C32—C33—C34 117.21 (11)
C10—C14—H14C 109.5 C33—C34—C35 114.32 (11)
H14A—C14—H14C 109.5 C33—C34—H34A 108.7
H14B—C14—H14C 109.5 C35—C34—H34A 108.7
C20—C15—C16 118.88 (11) C33—C34—H34B 108.7
C20—C15—C6 122.60 (11) C35—C34—H34B 108.7
C16—C15—C6 118.50 (11) H34A—C34—H34B 107.6
O2—C16—C15 120.94 (12) C38—C35—C39 109.44 (11)
O2—C16—C17 121.57 (11) C38—C35—C34 109.89 (11)
C15—C16—C17 117.48 (11) C39—C35—C34 110.57 (11)
C16—C17—C18 113.85 (10) C38—C35—C36 109.23 (11)
C16—C17—H17A 108.8 C39—C35—C36 109.89 (11)
C18—C17—H17A 108.8 C34—C35—C36 107.79 (10)
C16—C17—H17B 108.8 C37—C36—C35 112.36 (10)
C18—C17—H17B 108.8 C37—C36—H36A 109.1
H17A—C17—H17B 107.7 C35—C36—H36A 109.1
C21—C18—C17 109.83 (11) C37—C36—H36B 109.1
C21—C18—C22 108.80 (11) C35—C36—H36B 109.1
C17—C18—C22 109.51 (11) H36A—C36—H36B 107.9
C21—C18—C19 108.62 (10) C32—C37—O4 122.38 (11)
C17—C18—C19 108.78 (10) C32—C37—C36 126.52 (11)
C22—C18—C19 111.30 (10) O4—C37—C36 111.08 (10)
C20—C19—C18 112.98 (10) C35—C38—H38A 109.5
C20—C19—H19A 109.0 C35—C38—H38B 109.5
C18—C19—H19A 109.0 H38A—C38—H38B 109.5
C20—C19—H19B 109.0 C35—C38—H38C 109.5
C18—C19—H19B 109.0 H38A—C38—H38C 109.5
H19A—C19—H19B 107.8 H38B—C38—H38C 109.5
C15—C20—O1 122.60 (11) C35—C39—H39A 109.5
C15—C20—C19 126.13 (11) C35—C39—H39B 109.5
O1—C20—C19 111.25 (10) H39A—C39—H39B 109.5
C18—C21—H21A 109.5 C35—C39—H39C 109.5
C18—C21—H21B 109.5 H39A—C39—H39C 109.5
H21A—C21—H21B 109.5 H39B—C39—H39C 109.5
C5—N1—C1—C2 −0.78 (18) C6—C15—C20—C19 179.61 (11)
C5—N1—C1—C6 179.85 (10) C12—O1—C20—C15 11.41 (16)
N1—C1—C2—C3 0.82 (19) C12—O1—C20—C19 −166.90 (10)
C6—C1—C2—C3 −179.82 (11) C18—C19—C20—C15 −20.41 (18)
C1—C2—C3—C4 0.18 (18) C18—C19—C20—O1 157.83 (10)
C2—C3—C4—C5 −1.12 (18) N1—C5—C23—C32 58.96 (14)
C1—N1—C5—C4 −0.24 (17) C4—C5—C23—C32 −123.78 (12)
C1—N1—C5—C23 176.90 (10) N1—C5—C23—C24 −63.20 (14)
C3—C4—C5—N1 1.19 (19) C4—C5—C23—C24 114.06 (12)
C3—C4—C5—C23 −175.93 (11) C32—C23—C24—C29 −20.88 (16)
N1—C1—C6—C15 −54.14 (14) C5—C23—C24—C29 103.91 (13)
C2—C1—C6—C15 126.46 (12) C32—C23—C24—C25 161.34 (10)
N1—C1—C6—C7 68.80 (14) C5—C23—C24—C25 −73.87 (13)
C2—C1—C6—C7 −110.60 (12) C29—C24—C25—O5 −177.42 (12)
C15—C6—C7—C12 14.18 (16) C23—C24—C25—O5 0.42 (18)
C1—C6—C7—C12 −110.48 (13) C29—C24—C25—C26 5.01 (17)
C15—C6—C7—C8 −164.21 (10) C23—C24—C25—C26 −177.15 (11)
C1—C6—C7—C8 71.13 (13) O5—C25—C26—C27 146.24 (12)
C12—C7—C8—O3 −169.42 (12) C24—C25—C26—C27 −36.19 (15)
C6—C7—C8—O3 9.03 (17) C25—C26—C27—C30 175.29 (11)
C12—C7—C8—C9 11.97 (17) C25—C26—C27—C31 −64.09 (14)
C6—C7—C8—C9 −169.59 (10) C25—C26—C27—C28 56.52 (14)
O3—C8—C9—C10 143.94 (12) C30—C27—C28—C29 −167.43 (11)
C7—C8—C9—C10 −37.46 (15) C31—C27—C28—C29 73.20 (14)
C8—C9—C10—C14 −70.02 (14) C26—C27—C28—C29 −47.46 (14)
C8—C9—C10—C13 170.28 (11) C25—C24—C29—O4 −175.58 (11)
C8—C9—C10—C11 51.08 (14) C23—C24—C29—O4 6.62 (19)
C14—C10—C11—C12 79.67 (13) C25—C24—C29—C28 3.67 (19)
C13—C10—C11—C12 −160.79 (11) C23—C24—C29—C28 −174.13 (12)
C9—C10—C11—C12 −41.18 (14) C37—O4—C29—C24 11.94 (18)
C8—C7—C12—O1 175.34 (10) C37—O4—C29—C28 −167.41 (10)
C6—C7—C12—O1 −3.05 (18) C27—C28—C29—C24 19.21 (18)
C8—C7—C12—C11 −2.85 (19) C27—C28—C29—O4 −161.47 (10)
C6—C7—C12—C11 178.76 (11) C24—C23—C32—C37 19.29 (16)
C20—O1—C12—C7 −10.61 (16) C5—C23—C32—C37 −103.42 (14)
C20—O1—C12—C11 167.82 (10) C24—C23—C32—C33 −158.13 (11)
C10—C11—C12—C7 18.90 (18) C5—C23—C32—C33 79.16 (14)
C10—C11—C12—O1 −159.47 (10) C37—C32—C33—O6 −179.69 (13)
C7—C6—C15—C20 −13.46 (16) C23—C32—C33—O6 −2.18 (19)
C1—C6—C15—C20 110.63 (13) C37—C32—C33—C34 −2.84 (18)
C7—C6—C15—C16 165.04 (10) C23—C32—C33—C34 174.67 (11)
C1—C6—C15—C16 −70.86 (13) O6—C33—C34—C35 −149.70 (13)
C20—C15—C16—O2 172.25 (12) C32—C33—C34—C35 33.45 (17)
C6—C15—C16—O2 −6.31 (17) C33—C34—C35—C38 −173.37 (12)
C20—C15—C16—C17 −8.86 (17) C33—C34—C35—C39 65.70 (15)
C6—C15—C16—C17 172.58 (10) C33—C34—C35—C36 −54.43 (15)
O2—C16—C17—C18 −144.91 (12) C38—C35—C36—C37 166.01 (11)
C15—C16—C17—C18 36.21 (15) C39—C35—C36—C37 −73.91 (14)
C16—C17—C18—C21 −171.76 (11) C34—C35—C36—C37 46.65 (14)
C16—C17—C18—C22 68.82 (13) C33—C32—C37—O4 174.15 (11)
C16—C17—C18—C19 −53.01 (14) C23—C32—C37—O4 −3.29 (19)
C21—C18—C19—C20 163.90 (11) C33—C32—C37—C36 −3.85 (19)
C17—C18—C19—C20 44.39 (14) C23—C32—C37—C36 178.71 (11)
C22—C18—C19—C20 −76.35 (13) C29—O4—C37—C32 −13.67 (17)
C16—C15—C20—O1 −176.94 (10) C29—O4—C37—C36 164.61 (10)
C6—C15—C20—O1 1.56 (18) C35—C36—C37—C32 −19.89 (18)
C16—C15—C20—C19 1.11 (19) C35—C36—C37—O4 161.92 (10)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5213).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  2. Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Mohamed, S. K., Abdelhamid, A. A., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o850–o851. [DOI] [PMC free article] [PubMed]
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  5. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

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/S1600536811007318/lh5213sup1.cif

e-67-0o785-sup1.cif (30.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007318/lh5213Isup2.hkl

e-67-0o785-Isup2.hkl (377.6KB, 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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