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#$Date: 2022-04-03 22:21:15 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274238 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519382.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4519382
loop_
_publ_author_name
'Xue, Sijing'
'Cristòfol, Àlex'
'Limburg, Bart'
'Zeng, Qian'
'Kleij, Arjan W.'
_publ_section_title
;
 Dual Cobalt/Organophotoredox Catalysis for Diastereo- and Regioselective
 1,2-Difunctionalization of 1,3-Diene Surrogates Creating Quaternary
 Carbon Centers
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3651
_journal_page_last               3659
_journal_paper_doi               10.1021/acscatal.2c00660
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                115.316(2)
_cell_angle_beta                 101.1724(17)
_cell_angle_gamma                101.3619(19)
_cell_formula_units_Z            4
_cell_length_a                   10.2627(2)
_cell_length_b                   13.4490(3)
_cell_length_c                   14.5521(3)
_cell_measurement_reflns_used    17974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2910
_cell_measurement_theta_min      2.6870
_cell_volume                     1690.21(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_molecular_graphics
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    Sir2019
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32073
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.713
_diffrn_reflns_theta_min         2.709
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         8181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7212
_reflns_number_total             8181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs2c00660_si_003.cif
_cod_data_source_block           sx7-53-1
_cod_original_cell_volume        1690.22(7)
_cod_database_code               4519382
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.17123(7) 0.43664(6) 0.57280(5) 0.01378(16) Uani 1 1 d . . . . .
H1AA H -0.1133(9) 0.4643(11) 0.5487(8) 0.021 Uiso 1 1 calc R U . . .
O2A O 0.10668(7) 0.47940(6) 0.57971(6) 0.01517(17) Uani 1 1 d . . . . .
H2AA H 0.1953(15) 0.5021(4) 0.5918(9) 0.023 Uiso 1 1 calc R U . . .
C1A C -0.02235(9) 0.32516(8) 0.61063(7) 0.0115(2) Uani 1 1 d . . . . .
C2A C -0.09720(10) 0.41892(8) 0.65618(7) 0.0125(2) Uani 1 1 d . . . . .
H2A H -0.023928 0.493844 0.711209 0.015 Uiso 1 1 calc R U . . .
C3A C -0.20171(10) 0.38738(8) 0.70811(8) 0.0143(2) Uani 1 1 d . . . . .
C4A C -0.15567(11) 0.40388(9) 0.81196(8) 0.0202(2) Uani 1 1 d . . . . .
H4A H -0.058419 0.435408 0.850324 0.024 Uiso 1 1 calc R U . . .
C5A C -0.25073(13) 0.37462(11) 0.85994(10) 0.0291(3) Uani 1 1 d . . . . .
H5A H -0.217756 0.384889 0.930076 0.035 Uiso 1 1 calc R U . . .
C6A C -0.39273(13) 0.33074(12) 0.80600(11) 0.0325(3) Uani 1 1 d . . . . .
H6A H -0.457406 0.311847 0.839254 0.039 Uiso 1 1 calc R U . . .
C7A C -0.44045(12) 0.31440(11) 0.70286(10) 0.0273(3) Uani 1 1 d . . . . .
H7A H -0.537953 0.284177 0.665409 0.033 Uiso 1 1 calc R U . . .
C8A C -0.34525(11) 0.34236(9) 0.65430(8) 0.0184(2) Uani 1 1 d . . . . .
H8A H -0.378597 0.330589 0.583640 0.022 Uiso 1 1 calc R U . . .
C9A C -0.13956(10) 0.20633(8) 0.53998(7) 0.0133(2) Uani 1 1 d . . . . .
H9AA H -0.183281 0.189097 0.588677 0.016 Uiso 1 1 calc R U . . .
H9AB H -0.211756 0.217882 0.493012 0.016 Uiso 1 1 calc R U . . .
C10A C -0.10996(10) 0.09539(8) 0.46756(8) 0.0147(2) Uani 1 1 d . . . . .
H10A H -0.014128 0.098650 0.502743 0.018 Uiso 1 1 calc R U . . .
C11A C -0.21720(11) -0.00961(9) 0.45611(9) 0.0213(2) Uani 1 1 d . . . . .
H11A H -0.206171 -0.081057 0.404351 0.032 Uiso 1 1 calc R U . . .
H11B H -0.311946 -0.007657 0.430968 0.032 Uiso 1 1 calc R U . . .
H11C H -0.202075 -0.007270 0.525701 0.032 Uiso 1 1 calc R U . . .
C12A C -0.11906(12) 0.07866(9) 0.35508(8) 0.0220(2) Uani 1 1 d . . . . .
H12A H -0.102458 0.005747 0.312683 0.033 Uiso 1 1 calc R U . . .
H12B H -0.048208 0.143355 0.360623 0.033 Uiso 1 1 calc R U . . .
H12C H -0.212334 0.076181 0.320128 0.033 Uiso 1 1 calc R U . . .
C13A C 0.05852(10) 0.35608(8) 0.54006(7) 0.0127(2) Uani 1 1 d . . . . .
H13A H -0.009990 0.320733 0.466862 0.015 Uiso 1 1 calc R U . . .
C14A C 0.17999(10) 0.30817(9) 0.52732(8) 0.0166(2) Uani 1 1 d . . . . .
H14A H 0.146817 0.224210 0.499800 0.025 Uiso 1 1 calc R U . . .
H14B H 0.252607 0.344930 0.596950 0.025 Uiso 1 1 calc R U . . .
H14C H 0.218904 0.324473 0.476977 0.025 Uiso 1 1 calc R U . . .
C15A C 0.07875(10) 0.33138(8) 0.70669(7) 0.0126(2) Uani 1 1 d . . . . .
C16A C 0.19135(10) 0.43342(9) 0.77626(8) 0.0165(2) Uani 1 1 d . . . . .
H16A H 0.202959 0.497281 0.762817 0.020 Uiso 1 1 calc R U . . .
C17A C 0.28592(11) 0.44278(9) 0.86420(8) 0.0206(2) Uani 1 1 d . . . . .
H17A H 0.362008 0.512178 0.909489 0.025 Uiso 1 1 calc R U . . .
C18A C 0.26968(11) 0.35105(10) 0.88620(8) 0.0208(2) Uani 1 1 d . . . . .
H18A H 0.334116 0.357385 0.946454 0.025 Uiso 1 1 calc R U . . .
C19A C 0.15878(12) 0.25049(9) 0.81950(8) 0.0206(2) Uani 1 1 d . . . . .
H19A H 0.146557 0.187602 0.834335 0.025 Uiso 1 1 calc R U . . .
C20A C 0.06469(11) 0.24066(9) 0.73056(8) 0.0167(2) Uani 1 1 d . . . . .
H20A H -0.010570 0.170675 0.685296 0.020 Uiso 1 1 calc R U . . .
O1B O 0.66210(7) 0.58347(6) 0.62053(5) 0.01607(17) Uani 1 1 d . . . . .
H1BA H 0.7119(14) 0.5349(11) 0.6084(2) 0.024 Uiso 1 1 calc R U . . .
O2B O 0.39594(7) 0.56796(6) 0.63734(6) 0.01784(17) Uani 1 1 d . . . . .
H2BA H 0.4394(11) 0.5249(7) 0.6010(11) 0.027 Uiso 1 1 calc R U . . .
C1B C 0.61074(10) 0.74249(8) 0.75278(8) 0.0135(2) Uani 1 1 d . . . . .
C2B C 0.67765(10) 0.64266(8) 0.73311(7) 0.0132(2) Uani 1 1 d . . . . .
H2B H 0.620984 0.586491 0.749476 0.016 Uiso 1 1 calc R U . . .
C3B C 0.82823(10) 0.68244(8) 0.80229(8) 0.0144(2) Uani 1 1 d . . . . .
C4B C 0.94039(10) 0.71684(9) 0.76996(8) 0.0181(2) Uani 1 1 d . . . . .
H4B H 0.923181 0.716480 0.703258 0.022 Uiso 1 1 calc R U . . .
C5B C 1.07710(11) 0.75162(10) 0.83485(10) 0.0250(3) Uani 1 1 d . . . . .
H5B H 1.152839 0.775348 0.812409 0.030 Uiso 1 1 calc R U . . .
C6B C 1.10386(12) 0.75197(10) 0.93203(10) 0.0285(3) Uani 1 1 d . . . . .
H6B H 1.197566 0.776539 0.976389 0.034 Uiso 1 1 calc R U . . .
C7B C 0.99343(12) 0.71635(10) 0.96423(9) 0.0269(3) Uani 1 1 d . . . . .
H7B H 1.011070 0.715375 1.030335 0.032 Uiso 1 1 calc R U . . .
C8B C 0.85657(11) 0.68202(9) 0.89940(8) 0.0197(2) Uani 1 1 d . . . . .
H8B H 0.781139 0.657855 0.921923 0.024 Uiso 1 1 calc R U . . .
C9B C 0.70339(10) 0.83389(8) 0.73462(8) 0.0154(2) Uani 1 1 d . . . . .
H9BA H 0.797024 0.864495 0.788197 0.018 Uiso 1 1 calc R U . . .
H9BB H 0.715106 0.791803 0.663493 0.018 Uiso 1 1 calc R U . . .
C10B C 0.66166(11) 0.93962(9) 0.73883(8) 0.0185(2) Uani 1 1 d . . . . .
H10B H 0.611912 0.964720 0.793359 0.022 Uiso 1 1 calc R U . . .
C11B C 0.56783(12) 0.91630(10) 0.63155(9) 0.0259(3) Uani 1 1 d . . . . .
H11D H 0.554042 0.988754 0.637892 0.039 Uiso 1 1 calc R U . . .
H11E H 0.477010 0.859716 0.611841 0.039 Uiso 1 1 calc R U . . .
H11F H 0.612351 0.885516 0.576227 0.039 Uiso 1 1 calc R U . . .
C12B C 0.79647(13) 1.03846(10) 0.77397(10) 0.0263(3) Uani 1 1 d . . . . .
H12D H 0.772462 1.106285 0.776167 0.039 Uiso 1 1 calc R U . . .
H12E H 0.848332 1.013267 0.722851 0.039 Uiso 1 1 calc R U . . .
H12F H 0.854576 1.058860 0.845300 0.039 Uiso 1 1 calc R U . . .
C13B C 0.46164(10) 0.68694(8) 0.66654(8) 0.0147(2) Uani 1 1 d . . . . .
H13B H 0.473320 0.688745 0.600572 0.018 Uiso 1 1 calc R U . . .
C14B C 0.35658(10) 0.74894(9) 0.69974(8) 0.0181(2) Uani 1 1 d . . . . .
H14D H 0.401459 0.832832 0.733282 0.027 Uiso 1 1 calc R U . . .
H14E H 0.323223 0.730221 0.750915 0.027 Uiso 1 1 calc R U . . .
H14F H 0.277212 0.723823 0.636462 0.027 Uiso 1 1 calc R U . . .
C15B C 0.60211(10) 0.79072(8) 0.86680(8) 0.0147(2) Uani 1 1 d . . . . .
C16B C 0.50822(10) 0.72268(9) 0.89152(8) 0.0173(2) Uani 1 1 d . . . . .
H16B H 0.452622 0.646376 0.837455 0.021 Uiso 1 1 calc R U . . .
C17B C 0.49467(12) 0.76435(10) 0.99330(9) 0.0219(2) Uani 1 1 d . . . . .
H17B H 0.428028 0.717460 1.007400 0.026 Uiso 1 1 calc R U . . .
C18B C 0.57773(14) 0.87386(11) 1.07438(9) 0.0284(3) Uani 1 1 d . . . . .
H18B H 0.568743 0.902403 1.144100 0.034 Uiso 1 1 calc R U . . .
C19B C 0.67429(14) 0.94132(10) 1.05235(9) 0.0304(3) Uani 1 1 d . . . . .
H19B H 0.733060 1.015967 1.107758 0.036 Uiso 1 1 calc R U . . .
C20B C 0.68572(12) 0.90047(9) 0.94970(8) 0.0221(2) Uani 1 1 d . . . . .
H20B H 0.751639 0.948182 0.935839 0.027 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2A O1A H1AA 109.5 . . ?
C13A O2A H2AA 109.5 . . ?
C15A C1A C9A 113.48(8) . . ?
C15A C1A C13A 111.15(7) . . ?
C9A C1A C13A 110.09(7) . . ?
C15A C1A C2A 107.19(7) . . ?
C9A C1A C2A 106.77(7) . . ?
C13A C1A C2A 107.87(7) . . ?
O1A C2A C3A 107.41(7) . . ?
O1A C2A C1A 110.89(7) . . ?
C3A C2A C1A 113.50(7) . . ?
O1A C2A H2A 108.3 . . ?
C3A C2A H2A 108.3 . . ?
C1A C2A H2A 108.3 . . ?
C8A C3A C4A 118.31(9) . . ?
C8A C3A C2A 121.27(9) . . ?
C4A C3A C2A 120.41(9) . . ?
C5A C4A C3A 120.77(10) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C6A C5A C4A 120.33(10) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C5A C6A C7A 119.66(10) . . ?
C5A C6A H6A 120.2 . . ?
C7A C6A H6A 120.2 . . ?
C6A C7A C8A 120.03(11) . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C3A 120.88(10) . . ?
C7A C8A H8A 119.6 . . ?
C3A C8A H8A 119.6 . . ?
C10A C9A C1A 122.31(8) . . ?
C10A C9A H9AA 106.8 . . ?
C1A C9A H9AA 106.8 . . ?
C10A C9A H9AB 106.8 . . ?
C1A C9A H9AB 106.8 . . ?
H9AA C9A H9AB 106.6 . . ?
C11A C10A C12A 108.28(8) . . ?
C11A C10A C9A 108.51(8) . . ?
C12A C10A C9A 113.61(8) . . ?
C11A C10A H10A 108.8 . . ?
C12A C10A H10A 108.8 . . ?
C9A C10A H10A 108.8 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O2A C13A C14A 109.62(7) . . ?
O2A C13A C1A 111.40(7) . . ?
C14A C13A C1A 114.42(8) . . ?
O2A C13A H13A 107.0 . . ?
C14A C13A H13A 107.0 . . ?
C1A C13A H13A 107.0 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C20A C15A C16A 117.27(9) . . ?
C20A C15A C1A 123.33(9) . . ?
C16A C15A C1A 119.40(8) . . ?
C17A C16A C15A 121.37(9) . . ?
C17A C16A H16A 119.3 . . ?
C15A C16A H16A 119.3 . . ?
C16A C17A C18A 120.24(10) . . ?
C16A C17A H17A 119.9 . . ?
C18A C17A H17A 119.9 . . ?
C19A C18A C17A 119.28(10) . . ?
C19A C18A H18A 120.4 . . ?
C17A C18A H18A 120.4 . . ?
C18A C19A C20A 120.47(10) . . ?
C18A C19A H19A 119.8 . . ?
C20A C19A H19A 119.8 . . ?
C15A C20A C19A 121.37(9) . . ?
C15A C20A H20A 119.3 . . ?
C19A C20A H20A 119.3 . . ?
C2B O1B H1BA 109.5 . . ?
C13B O2B H2BA 109.5 . . ?
C15B C1B C9B 113.23(8) . . ?
C15B C1B C2B 107.22(8) . . ?
C9B C1B C2B 107.95(8) . . ?
C15B C1B C13B 111.95(8) . . ?
C9B C1B C13B 109.22(8) . . ?
C2B C1B C13B 106.98(7) . . ?
O1B C2B C3B 112.14(8) . . ?
O1B C2B C1B 107.08(8) . . ?
C3B C2B C1B 114.47(8) . . ?
O1B C2B H2B 107.6 . . ?
C3B C2B H2B 107.6 . . ?
C1B C2B H2B 107.6 . . ?
C8B C3B C4B 118.59(9) . . ?
C8B C3B C2B 119.57(9) . . ?
C4B C3B C2B 121.82(9) . . ?
C5B C4B C3B 120.30(10) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6B C5B C4B 120.52(10) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C7B C6B C5B 119.71(10) . . ?
C7B C6B H6B 120.1 . . ?
C5B C6B H6B 120.1 . . ?
C6B C7B C8B 119.72(11) . . ?
C6B C7B H7B 120.1 . . ?
C8B C7B H7B 120.1 . . ?
C3B C8B C7B 121.16(10) . . ?
C3B C8B H8B 119.4 . . ?
C7B C8B H8B 119.4 . . ?
C10B C9B C1B 121.70(8) . . ?
C10B C9B H9BA 106.9 . . ?
C1B C9B H9BA 106.9 . . ?
C10B C9B H9BB 106.9 . . ?
C1B C9B H9BB 106.9 . . ?
H9BA C9B H9BB 106.7 . . ?
C11B C10B C12B 108.33(9) . . ?
C11B C10B C9B 113.79(9) . . ?
C12B C10B C9B 108.01(9) . . ?
C11B C10B H10B 108.9 . . ?
C12B C10B H10B 108.9 . . ?
C9B C10B H10B 108.9 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O2B C13B C14B 105.52(8) . . ?
O2B C13B C1B 113.21(8) . . ?
C14B C13B C1B 114.65(8) . . ?
O2B C13B H13B 107.7 . . ?
C14B C13B H13B 107.7 . . ?
C1B C13B H13B 107.7 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C20B C15B C16B 117.35(9) . . ?
C20B C15B C1B 122.97(9) . . ?
C16B C15B C1B 119.67(9) . . ?
C17B C16B C15B 121.44(10) . . ?
C17B C16B H16B 119.3 . . ?
C15B C16B H16B 119.3 . . ?
C18B C17B C16B 120.37(10) . . ?
C18B C17B H17B 119.8 . . ?
C16B C17B H17B 119.8 . . ?
C17B C18B C19B 119.07(10) . . ?
C17B C18B H18B 120.5 . . ?
C19B C18B H18B 120.5 . . ?
C18B C19B C20B 120.53(11) . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B H19B 119.7 . . ?
C19B C20B C15B 121.19(10) . . ?
C19B C20B H20B 119.4 . . ?
C15B C20B H20B 119.4 . . ?
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
O1A C2A 1.4380(11) . ?
O1A H1AA 0.849(14) . ?
O2A C13A 1.4408(11) . ?
O2A H2AA 0.856(14) . ?
C1A C15A 1.5302(12) . ?
C1A C9A 1.5544(12) . ?
C1A C13A 1.5734(13) . ?
C1A C2A 1.5760(13) . ?
C2A C3A 1.5199(13) . ?
C2A H2A 1.0000 . ?
C3A C8A 1.3949(14) . ?
C3A C4A 1.3971(14) . ?
C4A C5A 1.3934(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3820(18) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.3898(17) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.3947(14) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.5450(14) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A C11A 1.5325(14) . ?
C10A C12A 1.5349(14) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C14A 1.5191(14) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A C20A 1.3938(13) . ?
C15A C16A 1.4061(13) . ?
C16A C17A 1.3887(14) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3892(15) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.3818(15) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.3942(14) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
O1B C2B 1.4410(11) . ?
O1B H1BA 0.887(15) . ?
O2B C13B 1.4416(12) . ?
O2B H2BA 0.864(14) . ?
C1B C15B 1.5300(13) . ?
C1B C9B 1.5492(13) . ?
C1B C2B 1.5706(14) . ?
C1B C13B 1.5742(13) . ?
C2B C3B 1.5161(13) . ?
C2B H2B 1.0000 . ?
C3B C8B 1.3892(14) . ?
C3B C4B 1.3952(14) . ?
C4B C5B 1.3890(14) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3851(18) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3847(18) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.3909(15) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.5442(15) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B C11B 1.5306(15) . ?
C10B C12B 1.5371(15) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C14B 1.5175(14) . ?
C13B H13B 1.0000 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B C20B 1.3955(14) . ?
C15B C16B 1.4012(14) . ?
C16B C17B 1.3885(15) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3847(17) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3875(17) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3924(15) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
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
C15A C1A C2A O1A 167.63(7) . . . . ?
C9A C1A C2A O1A -70.44(9) . . . . ?
C13A C1A C2A O1A 47.86(9) . . . . ?
C15A C1A C2A C3A -71.35(9) . . . . ?
C9A C1A C2A C3A 50.58(10) . . . . ?
C13A C1A C2A C3A 168.88(7) . . . . ?
O1A C2A C3A C8A 21.76(12) . . . . ?
C1A C2A C3A C8A -101.20(10) . . . . ?
O1A C2A C3A C4A -157.74(9) . . . . ?
C1A C2A C3A C4A 79.31(11) . . . . ?
C8A C3A C4A C5A 0.83(15) . . . . ?
C2A C3A C4A C5A -179.66(9) . . . . ?
C3A C4A C5A C6A -1.25(17) . . . . ?
C4A C5A C6A C7A 0.85(18) . . . . ?
C5A C6A C7A C8A -0.08(18) . . . . ?
C6A C7A C8A C3A -0.32(17) . . . . ?
C4A C3A C8A C7A -0.06(15) . . . . ?
C2A C3A C8A C7A -179.56(10) . . . . ?
C15A C1A C9A C10A -71.55(11) . . . . ?
C13A C1A C9A C10A 53.74(11) . . . . ?
C2A C1A C9A C10A 170.58(8) . . . . ?
C1A C9A C10A C11A 151.25(9) . . . . ?
C1A C9A C10A C12A -88.26(11) . . . . ?
C15A C1A C13A O2A -85.83(9) . . . . ?
C9A C1A C13A O2A 147.55(8) . . . . ?
C2A C1A C13A O2A 31.40(10) . . . . ?
C15A C1A C13A C14A 39.20(11) . . . . ?
C9A C1A C13A C14A -87.41(9) . . . . ?
C2A C1A C13A C14A 156.44(8) . . . . ?
C9A C1A C15A C20A -1.92(13) . . . . ?
C13A C1A C15A C20A -126.65(9) . . . . ?
C2A C1A C15A C20A 115.71(10) . . . . ?
C9A C1A C15A C16A 178.89(8) . . . . ?
C13A C1A C15A C16A 54.16(11) . . . . ?
C2A C1A C15A C16A -63.48(10) . . . . ?
C20A C15A C16A C17A 0.98(14) . . . . ?
C1A C15A C16A C17A -179.78(9) . . . . ?
C15A C16A C17A C18A -0.94(16) . . . . ?
C16A C17A C18A C19A 0.19(16) . . . . ?
C17A C18A C19A C20A 0.49(16) . . . . ?
C16A C15A C20A C19A -0.29(14) . . . . ?
C1A C15A C20A C19A -179.50(9) . . . . ?
C18A C19A C20A C15A -0.44(16) . . . . ?
C15B C1B C2B O1B 169.61(7) . . . . ?
C9B C1B C2B O1B -68.09(9) . . . . ?
C13B C1B C2B O1B 49.35(9) . . . . ?
C15B C1B C2B C3B -65.43(10) . . . . ?
C9B C1B C2B C3B 56.87(10) . . . . ?
C13B C1B C2B C3B 174.31(8) . . . . ?
O1B C2B C3B C8B -145.32(9) . . . . ?
C1B C2B C3B C8B 92.43(11) . . . . ?
O1B C2B C3B C4B 32.92(13) . . . . ?
C1B C2B C3B C4B -89.33(11) . . . . ?
C8B C3B C4B C5B -1.05(15) . . . . ?
C2B C3B C4B C5B -179.31(9) . . . . ?
C3B C4B C5B C6B 0.37(16) . . . . ?
C4B C5B C6B C7B 0.59(17) . . . . ?
C5B C6B C7B C8B -0.86(17) . . . . ?
C4B C3B C8B C7B 0.78(16) . . . . ?
C2B C3B C8B C7B 179.08(9) . . . . ?
C6B C7B C8B C3B 0.17(17) . . . . ?
C15B C1B C9B C10B -66.25(12) . . . . ?
C2B C1B C9B C10B 175.21(8) . . . . ?
C13B C1B C9B C10B 59.23(11) . . . . ?
C1B C9B C10B C11B -87.66(11) . . . . ?
C1B C9B C10B C12B 152.03(9) . . . . ?
C15B C1B C13B O2B -85.04(10) . . . . ?
C9B C1B C13B O2B 148.75(8) . . . . ?
C2B C1B C13B O2B 32.14(10) . . . . ?
C15B C1B C13B C14B 36.10(11) . . . . ?
C9B C1B C13B C14B -90.12(10) . . . . ?
C2B C1B C13B C14B 153.28(8) . . . . ?
C9B C1B C15B C20B -9.09(14) . . . . ?
C2B C1B C15B C20B 109.88(11) . . . . ?
C13B C1B C15B C20B -133.09(10) . . . . ?
C9B C1B C15B C16B 171.84(9) . . . . ?
C2B C1B C15B C16B -69.20(11) . . . . ?
C13B C1B C15B C16B 47.83(12) . . . . ?
C20B C15B C16B C17B 2.53(15) . . . . ?
C1B C15B C16B C17B -178.34(9) . . . . ?
C15B C16B C17B C18B -2.09(17) . . . . ?
C16B C17B C18B C19B 0.16(18) . . . . ?
C17B C18B C19B C20B 1.23(19) . . . . ?
C18B C19B C20B C15B -0.74(19) . . . . ?
C16B C15B C20B C19B -1.12(16) . . . . ?
C1B C15B C20B C19B 179.78(11) . . . . ?
