# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005
data_global
_journal_coden_Cambridge 182
loop_
_publ_author_name
'G. Mehta'
'Kotapalli Pallavi'
'Jayant D. Umarye'
_publ_contact_author_name 'G. Mehta'
_publ_contact_author_address
;
Department of Organic Chemistry
Indian Institute of Science
Bangalore
560 012
INDIA
;
_publ_contact_author_email GM@ORGCHEM.IISC.ERNET.IN
_publ_requested_journal 'Chemical Communications'
_publ_section_title
;
A total synthesis of Guanacastepene C
;
_publ_section_references
;
Allen, F.H. & Kennard, O. (1993).
Chem. Des. Autom. News., 8, 31-37.
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C.
Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R.
(1999) J. Appl. Cryst. 32, 115-119.
Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P.,
Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. &
Smykalla, C. (1999) The DIRDIF99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.
Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.
Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.
Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.
Flack, H.D. (1983). Acta Cryst. A39, 876-881.
LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.
Mackay, A.L. (1984). Acta Cryst. A40, 165-166.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.
Nonius (1998). Collect Software, Nonius, Delft, The Netherlands.
North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326.
Sheldrick, G.M. SHELXL93. Program for crystal structure
refinement. University of Gottingen, Germany, 1993.
Sheldrick, G.M. SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany, 1997.
Sheldrick, G.M. SHELXS86. Program for Crystal Structure
solution. University of Gottingen, Germany, 1986.
Sheldrick, G.M. SHELXS97. Program for Crystal Structure
solution. University of Gottingen, Germany, 1997.
Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.
Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.
Spek, A.L. (1990). Acta Cryst. A46, C-34.
Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.
Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.
Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_acknowledgements
; ?
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
#===============================================================================
data_jdu1_m
_database_code_depnum_ccdc_archive 'CCDC 272916'
_audit_creation_date 'May 16 13:43:39 2005'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
?
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(1R*,2S*,3R*,6R*,8aR*,10aR*)-2,3,6-trihydroxy-1-isopropyl-8a,10a-dimethyl-
1,2,3,6,7,8,8a,9,10,10a-decahydrobenzo[f]azulen-5-yl acetate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H34 O5'
_chemical_formula_structural 'C22 H34 O5'
_chemical_formula_sum 'C22 H34 O5'
_chemical_formula_weight 378.49
_chemical_compound_source ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a 9.1602(16)
_cell_length_b 10.6414(19)
_cell_length_c 12.088(2)
_cell_angle_alpha 81.181(3)
_cell_angle_beta 80.027(3)
_cell_angle_gamma 66.679(3)
_cell_volume 1061.0(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 292(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_cell_special_details
; ?
;
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.49
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.10
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.185
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 412
_exptl_absorpt_coefficient_mu 0.082
_exptl_crystal_density_meas_temp ?
# Permitted for _exptl_absorpt_correction_type :
# analytical 'analytical from crystal shape'
# cylinder 'cylindrical'
# empirical 'empirical from intensities'
# gaussian 'Gaussian from crystal shape'
# integration 'integration from crystal shape'
# multi-scan 'symmetry-related measurements'
# none 'no absorption corr. applied'
# numerical 'numerical from crystal shape'
# psi-scan 'psi-scan corrections'
# refdelf 'refined from delta-F'
# sphere 'spherical'
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min 0.9518
_exptl_absorpt_correction_T_max 0.9918
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 292(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number 10617
_diffrn_reflns_av_R_equivalents 0.0202
_diffrn_reflns_av_sigmaI/netI 0.0267
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 1.72
_diffrn_reflns_theta_max 25.40
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.40
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process
;
?
;
_reflns_number_total 3891
_reflns_number_gt 3172
_reflns_threshold_expression I>2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SAINT (Bruker, 1998)'
_computing_data_reduction SAINT
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
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^ > 2sigma(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3891
_refine_ls_number_parameters 252
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0703
_refine_ls_R_factor_gt 0.0550
_refine_ls_wR_factor_ref 0.1328
_refine_ls_wR_factor_gt 0.1264
_refine_ls_goodness_of_fit_ref 1.102
_refine_ls_restrained_S_all 1.102
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.268
_refine_diff_density_min -0.134
_refine_diff_density_rms 0.037
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42532(17) 0.14576(13) 0.10165(11) 0.0447(4) Uani 1 1 d . . .
H1 H 0.4574 0.1546 0.0344 0.067 Uiso 1 1 calc R . .
O3 O 0.47304(19) 0.85908(13) 0.12726(11) 0.0492(4) Uani 1 1 d . . .
H3 H 0.4371 0.9410 0.1368 0.074 Uiso 1 1 calc R . .
O2 O 0.15739(19) 0.10130(14) 0.21174(12) 0.0484(4) Uani 1 1 d . . .
H2 H 0.1267 0.1086 0.1504 0.073 Uiso 1 1 calc R . .
O4 O 0.08428(17) 0.81146(15) 0.15354(12) 0.0505(4) Uani 1 1 d . . .
C1 C 0.3323(2) 0.36179(17) 0.18599(14) 0.0291(4) Uani 1 1 d . . .
C2 C 0.4364(2) 0.54864(18) 0.18061(14) 0.0307(4) Uani 1 1 d . . .
C3 C 0.3023(2) 0.33676(17) 0.31414(14) 0.0311(4) Uani 1 1 d . . .
C4 C 0.3639(2) 0.68528(18) 0.16072(14) 0.0344(4) Uani 1 1 d . . .
C5 C 0.5715(2) 0.48073(19) 0.25503(15) 0.0349(4) Uani 1 1 d . . .
C6 C 0.2880(2) 0.26572(18) 0.13059(15) 0.0338(4) Uani 1 1 d . . .
H6 H 0.2320 0.3129 0.0649 0.041 Uiso 1 1 calc R . .
C7 C 0.2578(2) 0.20714(18) 0.32989(15) 0.0342(4) Uani 1 1 d . . .
H7 H 0.3596 0.1283 0.3206 0.041 Uiso 1 1 calc R . .
C8 C 0.3870(2) 0.45446(17) 0.12928(14) 0.0316(4) Uani 1 1 d . . .
H8 H 0.3954 0.4615 0.0510 0.038 Uiso 1 1 calc R . .
C9 C 0.4534(2) 0.30340(19) 0.36960(15) 0.0377(4) Uani 1 1 d . . .
H9A H 0.4342 0.2684 0.4474 0.045 Uiso 1 1 calc R . .
H9B H 0.5397 0.2295 0.3322 0.045 Uiso 1 1 calc R . .
C10 C 0.3972(2) 0.78819(19) 0.21484(15) 0.0394(5) Uani 1 1 d . . .
H10 H 0.2949 0.8552 0.2460 0.047 Uiso 1 1 calc R . .
C11 C 0.1779(2) 0.22319(18) 0.22513(15) 0.0356(4) Uani 1 1 d . . .
H11 H 0.0727 0.2986 0.2321 0.043 Uiso 1 1 calc R . .
C12 C 0.1637(2) 0.46321(19) 0.36091(17) 0.0426(5) Uani 1 1 d . . .
H12A H 0.1465 0.4484 0.4417 0.064 Uiso 1 1 calc R . .
H12B H 0.0680 0.4770 0.3303 0.064 Uiso 1 1 calc R . .
H12C H 0.1904 0.5430 0.3399 0.064 Uiso 1 1 calc R . .
C13 C 0.6337(3) 0.5888(2) 0.27597(18) 0.0451(5) Uani 1 1 d . . .
H13A H 0.7023 0.5512 0.3355 0.054 Uiso 1 1 calc R . .
H13B H 0.6981 0.6080 0.2080 0.054 Uiso 1 1 calc R . .
C14 C 0.5005(3) 0.7218(2) 0.30891(17) 0.0460(5) Uani 1 1 d . . .
H14A H 0.4352 0.7036 0.3767 0.055 Uiso 1 1 calc R . .
H14B H 0.5462 0.7842 0.3251 0.055 Uiso 1 1 calc R . .
C15 C 0.2360(2) 0.7488(2) 0.08466(16) 0.0440(5) Uani 1 1 d . . .
H15A H 0.2590 0.8178 0.0304 0.053 Uiso 1 1 calc R . .
H15B H 0.2313 0.6792 0.0437 0.053 Uiso 1 1 calc R . .
C16 C 0.5120(2) 0.4194(2) 0.36945(15) 0.0390(5) Uani 1 1 d . . .
H16A H 0.5986 0.3858 0.4159 0.047 Uiso 1 1 calc R . .
H16B H 0.4252 0.4937 0.4061 0.047 Uiso 1 1 calc R . .
C17 C 0.1711(3) 0.1764(2) 0.44577(16) 0.0447(5) Uani 1 1 d . . .
H17 H 0.1984 0.2194 0.5010 0.054 Uiso 1 1 calc R . .
C18 C 0.7112(2) 0.3671(2) 0.19489(18) 0.0473(5) Uani 1 1 d . . .
H18A H 0.6737 0.3014 0.1764 0.071 Uiso 1 1 calc R . .
H18B H 0.7931 0.3219 0.2436 0.071 Uiso 1 1 calc R . .
H18C H 0.7545 0.4067 0.1270 0.071 Uiso 1 1 calc R . .
O5 O -0.0387(2) 0.8594(2) 0.00091(17) 0.0846(6) Uani 1 1 d . . .
C19 C -0.0445(3) 0.8643(2) 0.1002(2) 0.0589(6) Uani 1 1 d . . .
C20 C -0.0110(3) 0.2329(3) 0.4541(2) 0.0629(7) Uani 1 1 d . . .
H20A H -0.0426 0.1898 0.4035 0.094 Uiso 1 1 calc R . .
H20B H -0.0503 0.3304 0.4340 0.094 Uiso 1 1 calc R . .
H20C H -0.0548 0.2143 0.5300 0.094 Uiso 1 1 calc R . .
C21 C -0.1924(3) 0.9315(4) 0.1778(3) 0.1082(12) Uani 1 1 d . . .
H21A H -0.2835 0.9669 0.1368 0.162 Uiso 1 1 calc R . .
H21B H -0.1829 1.0055 0.2085 0.162 Uiso 1 1 calc R . .
H21C H -0.2060 0.8653 0.2380 0.162 Uiso 1 1 calc R . .
C22 C 0.2340(3) 0.0218(2) 0.4808(2) 0.0688(7) Uani 1 1 d . . .
H22A H 0.2108 -0.0242 0.4278 0.103 Uiso 1 1 calc R . .
H22B H 0.1831 0.0047 0.5546 0.103 Uiso 1 1 calc R . .
H22C H 0.3478 -0.0120 0.4819 0.103 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0578(9) 0.0342(7) 0.0359(7) -0.0098(6) 0.0016(6) -0.0118(7)
O3 0.0728(10) 0.0313(7) 0.0430(8) -0.0066(6) 0.0061(7) -0.0233(7)
O2 0.0705(10) 0.0418(8) 0.0467(8) -0.0021(6) -0.0161(7) -0.0329(8)
O4 0.0450(8) 0.0573(9) 0.0444(8) -0.0033(7) -0.0128(7) -0.0120(7)
C1 0.0300(9) 0.0270(9) 0.0276(9) -0.0036(7) -0.0073(7) -0.0059(7)
C2 0.0367(10) 0.0348(10) 0.0226(8) -0.0034(7) -0.0013(7) -0.0162(8)
C3 0.0392(10) 0.0292(9) 0.0259(9) -0.0030(7) -0.0034(7) -0.0140(8)
C4 0.0425(11) 0.0337(10) 0.0262(9) -0.0033(7) -0.0024(8) -0.0143(8)
C5 0.0381(10) 0.0360(10) 0.0329(10) -0.0047(8) -0.0075(8) -0.0147(8)
C6 0.0423(11) 0.0286(9) 0.0304(9) -0.0038(7) -0.0112(8) -0.0103(8)
C7 0.0402(11) 0.0302(9) 0.0327(10) -0.0029(7) -0.0051(8) -0.0135(8)
C8 0.0380(10) 0.0330(9) 0.0237(9) -0.0025(7) -0.0068(7) -0.0121(8)
C9 0.0509(12) 0.0390(10) 0.0269(9) 0.0034(8) -0.0121(8) -0.0204(9)
C10 0.0526(12) 0.0339(10) 0.0321(10) -0.0061(8) 0.0004(9) -0.0180(9)
C11 0.0420(11) 0.0299(9) 0.0392(10) -0.0048(8) -0.0091(8) -0.0158(8)
C12 0.0508(12) 0.0373(11) 0.0385(11) -0.0093(8) 0.0021(9) -0.0164(9)
C13 0.0497(12) 0.0508(12) 0.0440(12) -0.0008(9) -0.0148(9) -0.0264(10)
C14 0.0685(14) 0.0431(11) 0.0386(11) -0.0072(9) -0.0101(10) -0.0312(11)
C15 0.0564(13) 0.0364(11) 0.0332(10) -0.0042(8) -0.0077(9) -0.0100(9)
C16 0.0489(12) 0.0424(11) 0.0311(10) -0.0012(8) -0.0139(9) -0.0202(9)
C17 0.0623(14) 0.0469(12) 0.0328(10) -0.0023(9) -0.0008(9) -0.0317(11)
C18 0.0400(11) 0.0507(12) 0.0480(12) -0.0089(10) -0.0084(9) -0.0111(10)
O5 0.0885(14) 0.0941(14) 0.0784(14) -0.0039(11) -0.0497(11) -0.0277(11)
C19 0.0572(15) 0.0596(15) 0.0672(16) 0.0071(12) -0.0301(13) -0.0254(12)
C20 0.0629(16) 0.0700(16) 0.0573(14) -0.0066(12) 0.0140(12) -0.0353(13)
C21 0.0485(17) 0.142(3) 0.112(3) 0.005(2) -0.0154(18) -0.0156(18)
C22 0.095(2) 0.0562(15) 0.0525(14) 0.0145(11) -0.0041(14) -0.0353(14)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.431(2) . ?
O1 H1 0.8200 . ?
O3 C10 1.445(2) . ?
O3 H3 0.8200 . ?
O2 C11 1.418(2) . ?
O2 H2 0.8200 . ?
O4 C19 1.323(3) . ?
O4 C15 1.451(2) . ?
C1 C8 1.326(2) . ?
C1 C6 1.514(2) . ?
C1 C3 1.526(2) . ?
C2 C4 1.340(2) . ?
C2 C8 1.497(2) . ?
C2 C5 1.530(2) . ?
C3 C9 1.533(2) . ?
C3 C12 1.541(2) . ?
C3 C7 1.563(2) . ?
C4 C15 1.493(3) . ?
C4 C10 1.508(3) . ?
C5 C18 1.534(3) . ?
C5 C13 1.539(3) . ?
C5 C16 1.542(3) . ?
C6 C11 1.527(3) . ?
C6 H6 0.9800 . ?
C7 C11 1.524(2) . ?
C7 C17 1.543(3) . ?
C7 H7 0.9800 . ?
C8 H8 0.9300 . ?
C9 C16 1.529(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.512(3) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.523(3) . ?
C17 C22 1.529(3) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O5 C19 1.201(3) . ?
C19 C21 1.491(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 109.5 . . ?
C10 O3 H3 109.5 . . ?
C11 O2 H2 109.5 . . ?
C19 O4 C15 116.21(18) . . ?
C8 C1 C6 123.83(16) . . ?
C8 C1 C3 126.11(15) . . ?
C6 C1 C3 110.06(14) . . ?
C4 C2 C8 120.41(16) . . ?
C4 C2 C5 122.91(16) . . ?
C8 C2 C5 116.67(15) . . ?
C1 C3 C9 111.93(15) . . ?
C1 C3 C12 109.43(14) . . ?
C9 C3 C12 110.94(15) . . ?
C1 C3 C7 102.42(13) . . ?
C9 C3 C7 109.50(14) . . ?
C12 C3 C7 112.36(15) . . ?
C2 C4 C15 121.79(17) . . ?
C2 C4 C10 124.25(17) . . ?
C15 C4 C10 113.92(16) . . ?
C2 C5 C18 110.01(15) . . ?
C2 C5 C13 109.24(15) . . ?
C18 C5 C13 107.91(16) . . ?
C2 C5 C16 111.01(15) . . ?
C18 C5 C16 109.57(16) . . ?
C13 C5 C16 109.04(15) . . ?
O1 C6 C1 111.36(15) . . ?
O1 C6 C11 108.58(14) . . ?
C1 C6 C11 102.28(14) . . ?
O1 C6 H6 111.4 . . ?
C1 C6 H6 111.4 . . ?
C11 C6 H6 111.4 . . ?
C11 C7 C17 118.19(16) . . ?
C11 C7 C3 102.91(14) . . ?
C17 C7 C3 117.08(14) . . ?
C11 C7 H7 105.9 . . ?
C17 C7 H7 105.9 . . ?
C3 C7 H7 105.9 . . ?
C1 C8 C2 125.53(16) . . ?
C1 C8 H8 117.2 . . ?
C2 C8 H8 117.2 . . ?
C16 C9 C3 117.81(15) . . ?
C16 C9 H9A 107.9 . . ?
C3 C9 H9A 107.9 . . ?
C16 C9 H9B 107.9 . . ?
C3 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
O3 C10 C4 107.60(14) . . ?
O3 C10 C14 110.93(17) . . ?
C4 C10 C14 112.50(15) . . ?
O3 C10 H10 108.6 . . ?
C4 C10 H10 108.6 . . ?
C14 C10 H10 108.6 . . ?
O2 C11 C7 111.52(14) . . ?
O2 C11 C6 115.07(15) . . ?
C7 C11 C6 103.15(14) . . ?
O2 C11 H11 109.0 . . ?
C7 C11 H11 109.0 . . ?
C6 C11 H11 109.0 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C5 112.97(17) . . ?
C14 C13 H13A 109.0 . . ?
C5 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C5 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C10 C14 C13 110.51(16) . . ?
C10 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O4 C15 C4 108.19(15) . . ?
O4 C15 H15A 110.1 . . ?
C4 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
C4 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C9 C16 C5 118.21(15) . . ?
C9 C16 H16A 107.8 . . ?
C5 C16 H16A 107.8 . . ?
C9 C16 H16B 107.8 . . ?
C5 C16 H16B 107.8 . . ?
H16A C16 H16B 107.1 . . ?
C20 C17 C22 109.68(19) . . ?
C20 C17 C7 115.21(17) . . ?
C22 C17 C7 110.42(17) . . ?
C20 C17 H17 107.0 . . ?
C22 C17 H17 107.0 . . ?
C7 C17 H17 107.0 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O4 122.7(2) . . ?
O5 C19 C21 125.5(2) . . ?
O4 C19 C21 111.7(2) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C3 C9 -56.8(2) . . . . ?
C6 C1 C3 C9 123.98(16) . . . . ?
C8 C1 C3 C12 66.6(2) . . . . ?
C6 C1 C3 C12 -112.61(16) . . . . ?
C8 C1 C3 C7 -174.04(17) . . . . ?
C6 C1 C3 C7 6.78(18) . . . . ?
C8 C2 C4 C15 -1.9(3) . . . . ?
C5 C2 C4 C15 177.94(16) . . . . ?
C8 C2 C4 C10 175.58(16) . . . . ?
C5 C2 C4 C10 -4.5(3) . . . . ?
C4 C2 C5 C18 -131.96(19) . . . . ?
C8 C2 C5 C18 47.9(2) . . . . ?
C4 C2 C5 C13 -13.7(2) . . . . ?
C8 C2 C5 C13 166.20(15) . . . . ?
C4 C2 C5 C16 106.59(19) . . . . ?
C8 C2 C5 C16 -73.53(19) . . . . ?
C8 C1 C6 O1 84.7(2) . . . . ?
C3 C1 C6 O1 -96.10(17) . . . . ?
C8 C1 C6 C11 -159.51(17) . . . . ?
C3 C1 C6 C11 19.70(18) . . . . ?
C1 C3 C7 C11 -30.76(17) . . . . ?
C9 C3 C7 C11 -149.68(15) . . . . ?
C12 C3 C7 C11 86.55(17) . . . . ?
C1 C3 C7 C17 -162.17(16) . . . . ?
C9 C3 C7 C17 78.9(2) . . . . ?
C12 C3 C7 C17 -44.9(2) . . . . ?
C6 C1 C8 C2 -178.23(17) . . . . ?
C3 C1 C8 C2 2.7(3) . . . . ?
C4 C2 C8 C1 -120.9(2) . . . . ?
C5 C2 C8 C1 59.2(2) . . . . ?
C1 C3 C9 C16 70.5(2) . . . . ?
C12 C3 C9 C16 -52.0(2) . . . . ?
C7 C3 C9 C16 -176.63(16) . . . . ?
C2 C4 C10 O3 112.8(2) . . . . ?
C15 C4 C10 O3 -69.5(2) . . . . ?
C2 C4 C10 C14 -9.7(3) . . . . ?
C15 C4 C10 C14 167.99(17) . . . . ?
C17 C7 C11 O2 -61.2(2) . . . . ?
C3 C7 C11 O2 168.05(15) . . . . ?
C17 C7 C11 C6 174.75(15) . . . . ?
C3 C7 C11 C6 44.01(17) . . . . ?
O1 C6 C11 O2 -42.9(2) . . . . ?
C1 C6 C11 O2 -160.71(15) . . . . ?
O1 C6 C11 C7 78.78(16) . . . . ?
C1 C6 C11 C7 -39.02(17) . . . . ?
C2 C5 C13 C14 46.6(2) . . . . ?
C18 C5 C13 C14 166.16(16) . . . . ?
C16 C5 C13 C14 -74.9(2) . . . . ?
O3 C10 C14 C13 -79.09(19) . . . . ?
C4 C10 C14 C13 41.5(2) . . . . ?
C5 C13 C14 C10 -62.3(2) . . . . ?
C19 O4 C15 C4 -175.28(17) . . . . ?
C2 C4 C15 O4 109.3(2) . . . . ?
C10 C4 C15 O4 -68.4(2) . . . . ?
C3 C9 C16 C5 -65.3(2) . . . . ?
C2 C5 C16 C9 63.1(2) . . . . ?
C18 C5 C16 C9 -58.7(2) . . . . ?
C13 C5 C16 C9 -176.55(16) . . . . ?
C11 C7 C17 C20 -29.3(2) . . . . ?
C3 C7 C17 C20 94.7(2) . . . . ?
C11 C7 C17 C22 95.6(2) . . . . ?
C3 C7 C17 C22 -140.41(19) . . . . ?
C15 O4 C19 O5 1.3(3) . . . . ?
C15 O4 C19 C21 -177.4(2) . . . . ?
# End of Crystallographic Information File