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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): m509–m510.
Published online 2010 April 10. doi:  10.1107/S1600536810012080
PMCID: PMC2979047

(5,10,15,20-Tetra­phenyl­porphyrinato-κ4 N)cobalt(II)–18-crown-6 (1/1)

Abstract

The asymmetric unit of the title compound, [Co(C44H28N4)]·C12H24O6, contains one half of a CoII(TPP) (TPP is tetra­phenyl­porphyrin) complex and one half of an 18-crown-6 mol­ecule of crystallization, both lying on inversion centers. The CoII(TPP) complex exhibits a nearly planar conformation of the porphyrinate core [maximum deviation = 0.069 (2) Å] with an average Co—N distance of 1.971 (4) Å. The distance between the Co atom and the closest O atom of the 18-crown-6 mol­ecule is 2.533 (2) Å, indicating a short non-bonded contact between the Co atom and the crown ether mol­ecule. An ethyl­ene group of the 18-crown-6 mol­ecule is disordered over two sites with occupancies of 0.565 (7) and 0.435 (7).

Related literature

For general background to cobalt porphyrin species and their applications, see: Sanders et al. (2000 [triangle]). For the synthesis of Co(II) tetra­phenyl­porphyrin, see: Madure & Scheidt (1976 [triangle]). For related structures, see: Konarev et al. (2003 [triangle], 2004 [triangle]); Nascimento et al. (2007 [triangle]); Smirnov et al. (1998 [triangle]); Lee et al. (2002 [triangle]); Iimura et al. (1988 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For the SIMU/ISOR restraints used in the refinement, see: McArdle (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m509-scheme1.jpg

Experimental

Crystal data

  • [Co(C44H28N4)]·C12H24O6
  • M r = 935.95
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m509-efi1.jpg
  • a = 10.1464 (4) Å
  • b = 11.0890 (6) Å
  • c = 11.7570 (5) Å
  • α = 104.327 (4)°
  • β = 105.842 (4)°
  • γ = 108.284 (4)°
  • V = 1125.12 (9) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 180 K
  • 0.25 × 0.24 × 0.21 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.927, T max = 1.000
  • 8862 measured reflections
  • 4589 independent reflections
  • 3977 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.100
  • S = 1.10
  • 4589 reflections
  • 323 parameters
  • 30 restraints
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012080/pv2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012080/pv2268Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the Ministry of Higher Education, Scientific Research and Technology of Tunisia.

supplementary crystallographic information

Comment

Cobalt atom in metalloporphyrines is commonly used as a qualitatively acceptable substitute for iron atom in high-spin five-coordinate hemes of deoxyhemoglobin and in the low-spin oxygenated hemes of oxyhemoglobin. The metalation of a porphyrin by cobalt (using CoCl2.6H2O salt) yields the stable [CoII(Porph)] (Porph = porphyrin) complex used as starting material in the preparation of five and six-coordinated Co(II) and Co(III) metalloporphyrines (Sanders et al., (2000). In the Cambridge Structural Database (CSD, version 5.31; Allen 2002) there are three structures of tetra-coordinated cobalt(II) tetraphenylporphyrin (TPP) complexes: IKUDOH (Konarev et al., 2003), IXIKIJ (Konarev et al., 2004) and TPORCP12 (Nascimento et al., 2007). Herein we report the struture of the title compound,(I), which has been prepared in our laboratory.

The asymmetric unit of (I), contains one half [CoII(TPP)] complex and one half crystallographically independent 18-crown-6 molecule of crystallization both lying on inversion centers (Fig. 1).

The distance between the cobalt(II) ion and the symmetry related O1 and O1' atoms (Fig. 2) of the two closest crown ether molecules is 2.533 (2 ) Å. This distance is significantly longer than the CoII—O(THF) bond length [2.204 (4) Å] in the [CoII(F8TPP)(THF)2] derivative (where F8TPP is the tetrakis(pentafluorophenylporphyrin)) (Smirnov et al., 1998) and the CoII—O(H2O) bond distance in the [CoII(H2O)6]2+ species [ 2.062 (4)- 2.141 (4) Å] (Lee et al., 2002). This indicates that in (I) there is a short non-bonded contact between the cobalt ion and the crown ether molecule.

It has been noticed that there is a relationship between the ruffling of the porphyrinato core and the mean equatorial Co(II)—Np distance (Np = pyrrol N atom); the porphyrinato core is ruffled as the Co—Np distance decreases, (Iimura et al., 1988). Thus, the average distance Co—Np in (I), 1.971 (4) Å, is longer than those of the three other reported [CoII(TPP)] structures quoted above [1.923 (3) – 1.969 (6) Å]. The porphyrin core in (I) presents a planar conformation with maximum and minimum deviations from the C20N4 least-squares plane of 0.069 (2) and -0.068 (2) Å for C6 and C8 atoms, respectively, while the Co2+ cation is basically in the porphyrin plane with a Co—Ct distance of 0.004 (1) Å (where Ct is the center of the C20N4 plane).

Experimental

To a solution of [CoII(TPP)] (Madure & Scheidt 1976) (100 mg, 0.067 mmol) in chlorobenzene (10 ml) was added an excess of 18-crown-6 (150 mg, 0.567 mmol) and sodium methanolate (100 mg, 3.225 mmol). The reaction mixture was stirred at room temperature until reddisd-green solution was formed. The resulting material was crystallized by diffusion of hexanes through the chlorobenzene solution which yielded [CoII(TPP)].(18-C-6) crystals as an impurity.

Refinement

All H atoms were placed in geometrically idealized positions (C—H = 0.93-0.97 Å) and constrained to ride on their parent atoms, with U(H) = 1.2Ueq(C). An ethylene group [C24 – C25] of the 18-crown-6 molecule was disordered over two sites with occupancies of 0.565 (7) and 0.435 (7). For this fragment, some anisotropic displacement ellipsoids were rather elongated which led us to use the SIMU/ISOR restraints (McArdle, 1995, Sheldrick, 2008). Alerts B and C for short intramolecular contacts H···H may be explained by the fact that C24 and C25 carbon atoms are disordered.

Figures

Fig. 1.
A view of the structure of (I), with the atom-numbering scheme. Unlabeled atoms are related by an inversion center to the labeled atoms. Displacement ellipsoids are drawn at 50%. The H atoms and the minor positions of the disordered C24 and C25 atoms ...
Fig. 2.
A unit-cell packing of (I). The short non-bonded contacts between the cobalt and the symmetry related O1 and O1' atoms of the two closest crown ether molecues, are drawn by dashed lines. The H atoms and the minor positions of the disordered C24 and C25 ...

Crystal data

[Co(C44H28N4)]·C12H24O6Z = 1
Mr = 935.95F(000) = 491
Triclinic, P1Dx = 1.381 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1464 (4) ÅCell parameters from 6796 reflections
b = 11.0890 (6) Åθ = 3.1–32.2°
c = 11.7570 (5) ŵ = 0.44 mm1
α = 104.327 (4)°T = 180 K
β = 105.842 (4)°Prism, dark purple
γ = 108.284 (4)°0.25 × 0.24 × 0.21 mm
V = 1125.12 (9) Å3

Data collection

Oxford Diffraction Xcalibur diffractometer4589 independent reflections
Radiation source: fine-focus sealed tube3977 reflections with I > 2σ(I)
graphiteRint = 0.019
Detector resolution: 8.2632 pixels mm-1θmax = 26.4°, θmin = 3.3°
ω and [var phi] scansh = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −13→9
Tmin = 0.927, Tmax = 1.000l = −14→14
8862 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.05322P)2 + 0.3421P] where P = (Fo2 + 2Fc2)/3
4589 reflections(Δ/σ)max < 0.001
323 parametersΔρmax = 0.79 e Å3
30 restraintsΔρmin = −0.44 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F\^2\^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F\^2\^, conventional R-factors R are based on F, with F set to zero for negative F\^2\^. The threshold expression of F\^2\^ > σ(F\^2\^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F\^2\^ 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)

xyzUiso*/UeqOcc. (<1)
Co0.00000.50000.50000.01992 (11)
N1−0.10600 (16)0.51602 (15)0.34011 (13)0.0205 (3)
N2−0.19511 (16)0.39511 (15)0.50211 (13)0.0202 (3)
C1−0.04208 (19)0.58671 (18)0.27400 (16)0.0207 (4)
C2−0.1554 (2)0.57948 (19)0.16553 (17)0.0250 (4)
H2−0.13980.61870.10640.030*
C3−0.2885 (2)0.50553 (19)0.16529 (17)0.0256 (4)
H3−0.38260.48380.10590.031*
C4−0.25852 (19)0.46615 (18)0.27385 (16)0.0213 (4)
C5−0.36903 (19)0.39375 (18)0.30882 (16)0.0217 (4)
C6−0.33699 (19)0.36035 (18)0.41648 (16)0.0216 (4)
C7−0.4490 (2)0.2741 (2)0.44746 (18)0.0268 (4)
H7−0.55250.23830.40420.032*
C8−0.3764 (2)0.2551 (2)0.55053 (18)0.0276 (4)
H8−0.41990.20240.59170.033*
C9−0.21943 (19)0.33090 (18)0.58552 (16)0.0217 (4)
C100.1099 (2)0.66163 (18)0.30894 (16)0.0213 (4)
C110.15851 (19)0.74003 (18)0.23032 (16)0.0224 (4)
C120.1820 (2)0.6798 (2)0.12439 (18)0.0293 (4)
H120.16560.58830.10030.035*
C130.2294 (2)0.7541 (2)0.05387 (19)0.0339 (5)
H130.24560.7125−0.01690.041*
C140.2529 (2)0.8891 (2)0.08771 (19)0.0322 (4)
H140.28480.93900.04010.039*
C150.2289 (3)0.9494 (2)0.1922 (2)0.0387 (5)
H150.24391.04060.21530.046*
C160.1824 (3)0.8759 (2)0.26378 (19)0.0347 (5)
H160.16720.91810.33490.042*
C17−0.52953 (19)0.34897 (18)0.22752 (17)0.0229 (4)
C18−0.5921 (2)0.2539 (2)0.10469 (18)0.0277 (4)
H18−0.53270.21830.07220.033*
C19−0.7417 (2)0.2114 (2)0.03001 (19)0.0346 (5)
H19−0.78230.1476−0.05220.042*
C20−0.8304 (2)0.2635 (2)0.0775 (2)0.0371 (5)
H20−0.93120.23430.02790.045*
C21−0.7694 (2)0.3590 (2)0.1985 (2)0.0372 (5)
H21−0.82890.39490.23040.045*
C22−0.6198 (2)0.4018 (2)0.27297 (19)0.0308 (4)
H22−0.57930.46680.35450.037*
O11.00507 (17)0.72687 (17)0.61845 (14)0.0415 (4)
O20.7723 (2)0.8744 (2)0.46275 (19)0.0633 (5)
O30.75479 (18)0.98421 (16)0.26483 (16)0.0438 (4)
C231.1145 (3)0.8022 (2)0.7438 (2)0.0399 (5)
H23A1.13400.73880.78280.048*
H23B1.07390.85340.79300.048*
C24A0.8779 (5)0.7518 (5)0.5733 (4)0.0333 (11)0.565 (7)
H24A0.84630.78170.64190.040*0.565 (7)
H24B0.79620.66910.50840.040*0.565 (7)
C25A0.9181 (5)0.8618 (5)0.5181 (5)0.0465 (14)0.565 (7)
H25A0.99360.94740.58370.056*0.565 (7)
H25B0.95570.83530.45280.056*0.565 (7)
C24B0.9331 (11)0.8256 (10)0.5946 (9)0.071 (2)0.435 (7)
H24C0.90260.85630.66390.085*0.435 (7)
H24D1.00630.90490.59210.085*0.435 (7)
C25B0.8162 (10)0.7669 (8)0.4875 (8)0.075 (3)0.435 (7)
H25C0.73470.69820.49420.089*0.435 (7)
H25D0.84150.72340.41930.089*0.435 (7)
C260.6814 (3)0.8027 (2)0.3354 (3)0.0493 (6)
H26A0.59470.72620.32640.059*
H26B0.73660.76760.29050.059*
C270.6318 (3)0.8965 (3)0.2809 (2)0.0465 (6)
H27A0.54810.84450.19980.056*
H27B0.59970.94930.33780.056*
C280.7410 (3)1.1016 (2)0.2499 (2)0.0396 (5)
H28A0.71351.14540.31640.048*
H28B0.66231.07680.16870.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co0.01575 (17)0.0281 (2)0.01649 (18)0.00707 (14)0.00525 (13)0.01245 (14)
N10.0169 (7)0.0242 (8)0.0186 (7)0.0062 (6)0.0053 (6)0.0095 (6)
N20.0202 (7)0.0235 (8)0.0168 (7)0.0083 (6)0.0053 (6)0.0097 (6)
C10.0227 (9)0.0237 (9)0.0171 (8)0.0096 (7)0.0075 (7)0.0100 (7)
C20.0272 (9)0.0296 (10)0.0191 (9)0.0111 (8)0.0067 (7)0.0136 (8)
C30.0230 (9)0.0310 (10)0.0207 (9)0.0104 (8)0.0037 (7)0.0120 (8)
C40.0204 (8)0.0243 (9)0.0177 (8)0.0092 (7)0.0043 (7)0.0086 (7)
C50.0185 (8)0.0234 (9)0.0194 (8)0.0072 (7)0.0039 (7)0.0073 (7)
C60.0173 (8)0.0242 (9)0.0199 (9)0.0063 (7)0.0050 (7)0.0077 (7)
C70.0176 (8)0.0329 (10)0.0262 (9)0.0054 (8)0.0068 (7)0.0132 (8)
C80.0220 (9)0.0337 (10)0.0260 (9)0.0057 (8)0.0097 (8)0.0161 (8)
C90.0201 (8)0.0248 (9)0.0199 (9)0.0070 (7)0.0084 (7)0.0098 (7)
C100.0244 (9)0.0231 (9)0.0187 (8)0.0094 (7)0.0095 (7)0.0100 (7)
C110.0193 (8)0.0274 (9)0.0194 (8)0.0066 (7)0.0056 (7)0.0124 (7)
C120.0378 (11)0.0312 (10)0.0279 (10)0.0178 (9)0.0161 (8)0.0163 (8)
C130.0407 (12)0.0461 (13)0.0285 (10)0.0223 (10)0.0206 (9)0.0215 (10)
C140.0288 (10)0.0374 (11)0.0275 (10)0.0053 (9)0.0080 (8)0.0211 (9)
C150.0509 (13)0.0244 (10)0.0315 (11)0.0065 (9)0.0108 (10)0.0123 (9)
C160.0486 (12)0.0299 (11)0.0245 (10)0.0126 (9)0.0159 (9)0.0103 (8)
C170.0196 (8)0.0249 (9)0.0233 (9)0.0071 (7)0.0049 (7)0.0138 (8)
C180.0258 (9)0.0305 (10)0.0242 (9)0.0102 (8)0.0063 (8)0.0113 (8)
C190.0292 (10)0.0346 (11)0.0259 (10)0.0033 (9)−0.0010 (8)0.0139 (9)
C200.0183 (9)0.0468 (13)0.0425 (12)0.0075 (9)0.0014 (8)0.0290 (11)
C210.0258 (10)0.0482 (13)0.0492 (13)0.0203 (10)0.0163 (9)0.0272 (11)
C220.0269 (10)0.0347 (11)0.0297 (10)0.0121 (8)0.0093 (8)0.0122 (9)
O10.0360 (8)0.0523 (10)0.0342 (8)0.0179 (7)0.0067 (7)0.0202 (7)
O20.0793 (12)0.0724 (11)0.0566 (10)0.0555 (10)0.0198 (9)0.0282 (9)
O30.0461 (9)0.0420 (9)0.0594 (11)0.0225 (8)0.0307 (8)0.0269 (8)
C230.0528 (14)0.0367 (12)0.0284 (11)0.0177 (11)0.0121 (10)0.0137 (9)
C24A0.032 (2)0.036 (2)0.035 (2)0.0101 (18)0.0153 (17)0.0186 (18)
C25A0.034 (2)0.042 (3)0.051 (3)0.0053 (19)0.0043 (19)0.024 (2)
C24B0.070 (3)0.066 (3)0.075 (3)0.030 (2)0.0147 (19)0.035 (2)
C25B0.074 (3)0.068 (3)0.080 (3)0.035 (2)0.0159 (19)0.032 (2)
C260.0573 (15)0.0349 (13)0.0629 (17)0.0176 (11)0.0343 (13)0.0181 (12)
C270.0293 (11)0.0565 (15)0.0486 (14)0.0107 (10)0.0121 (10)0.0230 (12)
C280.0430 (13)0.0389 (12)0.0328 (11)0.0201 (10)0.0071 (10)0.0104 (10)

Geometric parameters (Å, °)

Co—N21.9669 (14)C18—C191.385 (3)
Co—N2i1.9669 (14)C18—H180.9300
Co—N1i1.9757 (14)C19—C201.377 (3)
Co—N11.9757 (14)C19—H190.9300
N1—C11.377 (2)C20—C211.375 (3)
N1—C41.378 (2)C20—H200.9300
N2—C91.377 (2)C21—C221.383 (3)
N2—C61.379 (2)C21—H210.9300
C1—C101.385 (2)C22—H220.9300
C1—C21.430 (2)O1—C24A1.394 (4)
C2—C31.341 (3)O1—C231.420 (3)
C2—H20.9300O1—C24B1.534 (8)
C3—C41.435 (2)O2—C261.385 (3)
C3—H30.9300O2—C25B1.462 (7)
C4—C51.386 (2)O2—C25A1.510 (5)
C5—C61.388 (2)O3—C281.399 (3)
C5—C171.490 (2)O3—C271.413 (3)
C6—C71.434 (2)C23—C28ii1.488 (3)
C7—C81.339 (3)C23—H23A0.9700
C7—H70.9300C23—H23B0.9700
C8—C91.429 (2)C24A—C25A1.517 (6)
C8—H80.9300C24A—H24A0.9700
C9—C10i1.386 (2)C24A—H24B0.9700
C10—C9i1.386 (2)C25A—H25A0.9700
C10—C111.494 (2)C25A—H25B0.9700
C11—C121.380 (3)C24B—C25B1.308 (12)
C11—C161.381 (3)C24B—H24C0.9700
C12—C131.380 (3)C24B—H24D0.9700
C12—H120.9300C25B—H25C0.9700
C13—C141.373 (3)C25B—H25D0.9700
C13—H130.9300C26—C271.493 (3)
C14—C151.370 (3)C26—H26A0.9700
C14—H140.9300C26—H26B0.9700
C15—C161.382 (3)C27—H27A0.9700
C15—H150.9300C27—H27B0.9700
C16—H160.9300C28—C23ii1.488 (3)
C17—C221.384 (3)C28—H28A0.9700
C17—C181.388 (3)C28—H28B0.9700
N2—Co—N2i180.0C20—C19—C18119.9 (2)
N2—Co—N1i90.63 (6)C20—C19—H19120.0
N2i—Co—N1i89.37 (6)C18—C19—H19120.0
N2—Co—N189.37 (6)C21—C20—C19119.82 (18)
N2i—Co—N190.63 (6)C21—C20—H20120.1
N1i—Co—N1180.0C19—C20—H20120.1
C1—N1—C4104.78 (14)C20—C21—C22120.2 (2)
C1—N1—Co126.92 (12)C20—C21—H21119.9
C4—N1—Co128.22 (12)C22—C21—H21119.9
C9—N2—C6104.48 (14)C21—C22—C17120.75 (19)
C9—N2—Co126.91 (12)C21—C22—H22119.6
C6—N2—Co128.44 (12)C17—C22—H22119.6
N1—C1—C10125.90 (16)C24A—O1—C23122.1 (2)
N1—C1—C2110.67 (15)C23—O1—C24B102.2 (4)
C10—C1—C2123.35 (16)C26—O2—C25B97.5 (4)
C3—C2—C1107.06 (16)C26—O2—C25A120.3 (3)
C3—C2—H2126.5C28—O3—C27114.26 (18)
C1—C2—H2126.5O1—C23—C28ii113.86 (18)
C2—C3—C4107.11 (16)O1—C23—H23A108.8
C2—C3—H3126.4C28ii—C23—H23A108.8
C4—C3—H3126.4O1—C23—H23B108.8
N1—C4—C5125.58 (16)C28ii—C23—H23B108.8
N1—C4—C3110.38 (15)H23A—C23—H23B107.7
C5—C4—C3123.97 (16)O1—C24A—C25A107.9 (3)
C4—C5—C6122.88 (16)O1—C24A—H24A110.1
C4—C5—C17118.89 (16)C25A—C24A—H24A110.1
C6—C5—C17118.23 (16)O1—C24A—H24B110.1
N2—C6—C5125.50 (16)C25A—C24A—H24B110.1
N2—C6—C7110.62 (15)H24A—C24A—H24B108.4
C5—C6—C7123.69 (16)O2—C25A—C24A104.3 (3)
C8—C7—C6106.93 (16)O2—C25A—H25A110.9
C8—C7—H7126.5C24A—C25A—H25A110.9
C6—C7—H7126.5O2—C25A—H25B110.9
C7—C8—C9107.22 (16)C24A—C25A—H25B110.9
C7—C8—H8126.4H25A—C25A—H25B108.9
C9—C8—H8126.4C25B—C24B—O1111.0 (8)
N2—C9—C10i126.03 (16)C25B—C24B—H24C109.4
N2—C9—C8110.74 (15)O1—C24B—H24C109.4
C10i—C9—C8123.23 (16)C25B—C24B—H24D109.4
C1—C10—C9i123.25 (16)O1—C24B—H24D109.4
C1—C10—C11118.58 (15)H24C—C24B—H24D108.0
C9i—C10—C11118.16 (16)C24B—C25B—O2106.7 (7)
C12—C11—C16118.63 (17)C24B—C25B—H25C110.4
C12—C11—C10121.28 (17)O2—C25B—H25C110.4
C16—C11—C10120.09 (17)C24B—C25B—H25D110.4
C11—C12—C13120.67 (18)O2—C25B—H25D110.4
C11—C12—H12119.7H25C—C25B—H25D108.6
C13—C12—H12119.7O2—C26—C27108.8 (2)
C14—C13—C12120.34 (19)O2—C26—H26A109.9
C14—C13—H13119.8C27—C26—H26A109.9
C12—C13—H13119.8O2—C26—H26B109.9
C15—C14—C13119.39 (18)C27—C26—H26B109.9
C15—C14—H14120.3H26A—C26—H26B108.3
C13—C14—H14120.3O3—C27—C26107.81 (19)
C14—C15—C16120.54 (19)O3—C27—H27A110.1
C14—C15—H15119.7C26—C27—H27A110.1
C16—C15—H15119.7O3—C27—H27B110.1
C11—C16—C15120.43 (19)C26—C27—H27B110.1
C11—C16—H16119.8H27A—C27—H27B108.5
C15—C16—H16119.8O3—C28—C23ii110.08 (18)
C22—C17—C18118.42 (17)O3—C28—H28A109.6
C22—C17—C5120.57 (17)C23ii—C28—H28A109.6
C18—C17—C5121.01 (17)O3—C28—H28B109.6
C19—C18—C17120.81 (19)C23ii—C28—H28B109.6
C19—C18—H18119.6H28A—C28—H28B108.2
C17—C18—H18119.6

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2268).

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