#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:14:04 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567697.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_1567697
loop_
_publ_author_name
'Arkhypchuk, Anna I.'
'D'Imperio, Nicolas'
'Wells, Jordann A. L.'
'Ott, Sascha'
_publ_section_title
;
 [2 + 2] Cycloaddition of phosphaalkenes as a key step for the reductive
 coupling of diaryl ketones to tetraaryl olefins
;
_journal_issue                   41
_journal_name_full               'Chemical Science'
_journal_page_first              12239
_journal_page_last               12244
_journal_paper_doi               10.1039/D2SC03073J
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C36 H36 F2 O2'
_chemical_formula_sum            'C36 H36 F2 O2'
_chemical_formula_weight         538.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-04-17 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.010(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.356(3)
_cell_length_b                   31.286(8)
_cell_length_c                   9.517(2)
_cell_measurement_reflns_used    8055
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.17
_cell_volume                     2932.4(13)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            42869
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.068
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1374 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7267
_refine_ls_number_restraints     176
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²+1.9329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4443
_reflns_number_total             7267
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03073j2.cif
_cod_data_source_block           so2008
_cod_depositor_comments
'Adding full bibliography for 1567695--1567699.cif.'
_cod_original_cell_volume        2932.3(12)
_cod_database_code               1567697
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Rigid bond restraints
 C10, C11B, C11A, C12A, C12B, C13A, C13B, C14, C15B, C15A, C16B, C16A, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11B \\sim C11A \\sim C12A \\sim C12B \\sim C13A \\sim C13B \\sim C14
\\sim C15B \\sim C15A \\sim C16B \\sim C16A \\sim C17: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Fixed Sof: H10C(0.66) H10D(0.66) H10A(0.34) H10B(0.34) H14C(0.66) H14D(0.66)
 H14A(0.34) H14B(0.34) C11B(0.66) H11A(0.66) H11B(0.66) C16B(0.66) H16A(0.66)
 H16B(0.66) C15B(0.66) H15A(0.66) H15B(0.66) C16A(0.34) H16C(0.34) H16D(0.34)
 C15A(0.34) H15C(0.34) H15D(0.34) H17C(0.66) H17D(0.66) H17A(0.34) H17B(0.34)
 C13B(0.66) H13A(0.66) H13B(0.66) C12B(0.66) H12A(0.66) H12B(0.66) C13A(0.34)
 H13C(0.34) H13D(0.34) C12A(0.34) H12C(0.34) H12D(0.34) C11A(0.34) H11C(0.34)
 H11D(0.34)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C9(H9A,H9B), C10(H10C,H10D), C10(H10A,H10B), C14(H14C,H14D),
 C14(H14A,H14B), C11B(H11A,H11B), C16B(H16A,H16B), C15B(H15A,H15B), C16A(H16C,
 H16D), C15A(H15C,H15D), C17(H17C,H17D), C17(H17A,H17B), C13B(H13A,H13B),
 C12B(H12A,H12B), C13A(H13C,H13D), C12A(H12C,H12D), C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C21(H21), C20(H20), C30(H30), C32(H32), C4(H4), C26(H26),
 C36(H36), C8(H8), C33(H33), C5(H5), C7(H7), C35(H35), C27(H27), C29(H29)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.52018(17) 0.80455(5) 0.34565(19) 0.0484(4) Uani 1 1 d . . . . .
F2 F 0.84390(17) 0.43560(5) 0.3795(3) 0.0927(7) Uani 1 1 d . . . . .
F1 F 0.11053(17) 0.52405(6) 0.1201(3) 0.1077(8) Uani 1 1 d . . . . .
C22 C 0.55853(18) 0.67282(6) 0.2935(2) 0.0314(4) Uani 1 1 d . . . . .
C1 C 0.58089(19) 0.62619(6) 0.2761(2) 0.0327(4) Uani 1 1 d . . . . .
O2 O 1.16622(18) 0.71871(6) 0.3827(3) 0.0947(9) Uani 1 1 d . . . . .
C19 C 0.5270(2) 0.76132(6) 0.3215(2) 0.0359(5) Uani 1 1 d . . . . .
C25 C 0.4557(2) 0.59901(6) 0.2342(2) 0.0358(5) Uani 1 1 d . . . . .
C24 C 0.4499(2) 0.74029(7) 0.1960(2) 0.0389(5) Uani 1 1 d . . . . .
H24 H 0.386902 0.755680 0.118631 0.047 Uiso 1 1 calc R U . . .
C2 C 0.70814(19) 0.61003(6) 0.2990(2) 0.0339(4) Uani 1 1 d . . . . .
C23 C 0.4654(2) 0.69618(7) 0.1835(2) 0.0363(5) Uani 1 1 d . . . . .
H23 H 0.410820 0.681802 0.097772 0.044 Uiso 1 1 calc R U . . .
C31 C 0.7407(2) 0.56329(6) 0.3176(2) 0.0381(5) Uani 1 1 d . . . . .
C21 C 0.6332(2) 0.69487(7) 0.4206(2) 0.0390(5) Uani 1 1 d . . . . .
H21 H 0.696363 0.679638 0.498344 0.047 Uiso 1 1 calc R U . . .
C3 C 0.8277(2) 0.63865(6) 0.3140(3) 0.0381(5) Uani 1 1 d . . . . .
C20 C 0.6172(2) 0.73836(7) 0.4356(3) 0.0417(5) Uani 1 1 d . . . . .
H20 H 0.667615 0.752565 0.523721 0.050 Uiso 1 1 calc R U . . .
C30 C 0.3504(2) 0.60716(7) 0.2934(3) 0.0448(5) Uani 1 1 d . . . . .
H30 H 0.358311 0.630327 0.360082 0.054 Uiso 1 1 calc R U . . .
C32 C 0.8325(2) 0.54504(7) 0.2535(3) 0.0481(6) Uani 1 1 d . . . . .
H32 H 0.871241 0.562315 0.194874 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8216(2) 0.67325(7) 0.2195(3) 0.0433(5) Uani 1 1 d . . . . .
H4 H 0.741041 0.678020 0.139779 0.052 Uiso 1 1 calc R U . . .
C26 C 0.4389(2) 0.56553(7) 0.1321(3) 0.0458(6) Uani 1 1 d . . . . .
H26 H 0.507926 0.560050 0.087994 0.055 Uiso 1 1 calc R U . . .
C36 C 0.6867(2) 0.53743(7) 0.4045(3) 0.0470(6) Uani 1 1 d . . . . .
H36 H 0.625678 0.549363 0.450511 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9509(2) 0.63128(7) 0.4243(3) 0.0495(6) Uani 1 1 d . . . . .
H8 H 0.959608 0.607178 0.487306 0.059 Uiso 1 1 calc R U . . .
C18 C 0.4382(3) 0.83001(7) 0.2266(3) 0.0513(6) Uani 1 1 d . . . . .
H18A H 0.342607 0.820275 0.198332 0.062 Uiso 1 1 calc R U . . .
H18B H 0.470621 0.827223 0.139432 0.062 Uiso 1 1 calc R U . . .
C33 C 0.8681(2) 0.50210(7) 0.2741(3) 0.0586(8) Uani 1 1 d . . . . .
H33 H 0.930734 0.489922 0.230693 0.070 Uiso 1 1 calc R U . . .
C5 C 0.9313(2) 0.70096(8) 0.2399(3) 0.0551(7) Uani 1 1 d . . . . .
H5 H 0.924396 0.724752 0.175934 0.066 Uiso 1 1 calc R U . . .
C7 C 1.0607(2) 0.65857(8) 0.4435(4) 0.0623(8) Uani 1 1 d . . . . .
H7 H 1.143349 0.652907 0.519300 0.075 Uiso 1 1 calc R U . . .
C35 C 0.7211(3) 0.49421(8) 0.4251(3) 0.0591(7) Uani 1 1 d . . . . .
H35 H 0.683465 0.476567 0.483757 0.071 Uiso 1 1 calc R U . . .
C34 C 0.8104(3) 0.47784(7) 0.3584(4) 0.0618(8) Uani 1 1 d . . . . .
C6 C 1.0512(2) 0.69366(8) 0.3542(4) 0.0629(8) Uani 1 1 d . . . . .
C9 C 1.1523(3) 0.76204(8) 0.3357(4) 0.0598(7) Uani 1 1 d . . . . .
H9A H 1.097668 0.763196 0.230077 0.072 Uiso 1 1 calc R U . . .
H9B H 1.243271 0.773785 0.344881 0.072 Uiso 1 1 calc R U . . .
C27 C 0.3231(3) 0.54027(8) 0.0945(3) 0.0619(8) Uani 1 1 d . . . . .
H27 H 0.312522 0.517472 0.025906 0.074 Uiso 1 1 calc R U . . .
C28 C 0.2246(3) 0.54896(9) 0.1584(4) 0.0667(8) Uani 1 1 d . . . . .
C29 C 0.2340(2) 0.58188(9) 0.2563(4) 0.0604(7) Uani 1 1 d . . . . .
H29 H 0.163033 0.587285 0.297702 0.072 Uiso 1 1 calc R U . . .
C10 C 1.0868(3) 0.78911(9) 0.4216(4) 0.0662(8) Uani 1 1 d . U . . .
H10C H 1.002176 0.774496 0.422130 0.079 Uiso 0.66 1 calc R U P A 2
H10D H 1.147470 0.789371 0.525017 0.079 Uiso 0.66 1 calc R U P A 2
H10A H 1.133884 0.787459 0.529249 0.079 Uiso 0.34 1 calc R U P B 1
H10B H 0.989402 0.782247 0.400975 0.079 Uiso 0.34 1 calc R U P B 1
C14 C 0.8097(4) 0.91185(12) 0.2814(5) 0.0895(11) Uani 1 1 d . U . . .
H14C H 0.834721 0.910149 0.189261 0.107 Uiso 0.66 1 calc R U P C 2
H14D H 0.802487 0.942847 0.298621 0.107 Uiso 0.66 1 calc R U P C 2
H14A H 0.779795 0.924090 0.180556 0.107 Uiso 0.34 1 calc R U P D 1
H14B H 0.856099 0.933682 0.355042 0.107 Uiso 0.34 1 calc R U P D 1
C11B C 1.0515(8) 0.83382(18) 0.3785(11) 0.135(3) Uani 0.66 1 d . U P E 2
H11A H 1.137276 0.850102 0.415935 0.162 Uiso 0.66 1 calc R U P E 2
H11B H 1.026998 0.834393 0.269422 0.162 Uiso 0.66 1 calc R U P E 2
C16B C 0.6003(6) 0.89510(13) 0.3449(6) 0.0622(11) Uani 0.66 1 d . U P F 2
H16A H 0.596534 0.923484 0.389391 0.075 Uiso 0.66 1 calc R U P F 2
H16B H 0.654498 0.875827 0.423618 0.075 Uiso 0.66 1 calc R U P F 2
C15B C 0.6659(8) 0.8991(3) 0.2293(8) 0.122(3) Uani 0.66 1 d . U P F 2
H15A H 0.615019 0.920344 0.156021 0.146 Uiso 0.66 1 calc R U P F 2
H15B H 0.658896 0.871259 0.177874 0.146 Uiso 0.66 1 calc R U P F 2
C16A C 0.5531(9) 0.8978(2) 0.2242(11) 0.061(2) Uani 0.34 1 d . U P F 1
H16C H 0.544082 0.888491 0.122153 0.073 Uiso 0.34 1 calc R U P F 1
H16D H 0.540816 0.929147 0.223908 0.073 Uiso 0.34 1 calc R U P F 1
C15A C 0.6899(9) 0.8861(3) 0.3249(13) 0.065(2) Uani 0.34 1 d . U P F 1
H15C H 0.704031 0.854914 0.318613 0.078 Uiso 0.34 1 calc R U P F 1
H15D H 0.694887 0.892909 0.427990 0.078 Uiso 0.34 1 calc R U P F 1
C17 C 0.4480(3) 0.87627(8) 0.2771(4) 0.0675(8) Uani 1 1 d . U . . .
H17C H 0.401107 0.879047 0.352902 0.081 Uiso 0.66 1 calc R U P F 2
H17D H 0.398345 0.894236 0.191895 0.081 Uiso 0.66 1 calc R U P F 2
H17A H 0.359191 0.890667 0.235530 0.081 Uiso 0.34 1 calc R U P F 1
H17B H 0.473924 0.877661 0.386233 0.081 Uiso 0.34 1 calc R U P F 1
C13B C 0.9328(7) 0.9016(2) 0.3883(10) 0.116(2) Uani 0.66 1 d . U P E 2
H13A H 0.931666 0.913667 0.484115 0.139 Uiso 0.66 1 calc R U P E 2
H13B H 1.007102 0.915913 0.361273 0.139 Uiso 0.66 1 calc R U P E 2
C12B C 0.9651(8) 0.8555(2) 0.4092(14) 0.167(4) Uani 0.66 1 d . U P E 2
H12A H 0.981635 0.850499 0.516052 0.201 Uiso 0.66 1 calc R U P E 2
H12B H 0.878237 0.840886 0.358649 0.201 Uiso 0.66 1 calc R U P E 2
C13A C 0.8833(10) 0.8735(4) 0.2925(14) 0.090(3) Uani 0.34 1 d . U P E 1
H13C H 0.876775 0.864185 0.191097 0.108 Uiso 0.34 1 calc R U P E 1
H13D H 0.837514 0.851510 0.334864 0.108 Uiso 0.34 1 calc R U P E 1
C12A C 1.0317(10) 0.8739(3) 0.3825(16) 0.094(3) Uani 0.34 1 d . U P E 1
H12C H 1.072398 0.901230 0.364815 0.113 Uiso 0.34 1 calc R U P E 1
H12D H 1.039097 0.872706 0.488653 0.113 Uiso 0.34 1 calc R U P E 1
C11A C 1.1113(11) 0.8378(3) 0.3479(10) 0.062(2) Uani 0.34 1 d . U P E 1
H11C H 1.209047 0.845094 0.385254 0.075 Uiso 0.34 1 calc R U P E 1
H11D H 1.086643 0.834853 0.239200 0.075 Uiso 0.34 1 calc R U P E 1
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'
F F 0.0171 0.0103 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0440
0.00 1.00 0.00 0.0530
0.00 1.00 1.00 0.2220
0.00 -1.00 -1.00 0.2170
0.00 0.00 -1.00 0.2160
0.00 0.00 1.00 0.2260
-1.00 1.00 1.00 0.3090
1.00 -1.00 -1.00 0.2480
-1.00 1.00 0.00 0.1490
1.00 -1.00 0.00 0.1020
-1.00 0.00 1.00 0.3150
1.00 0.00 -1.00 0.2500
0.00 1.00 -1.00 0.1990
-1.00 1.00 -1.00 0.2130
1.00 -1.00 1.00 0.2050
1.00 0.00 1.00 0.2070
-1.00 -1.00 0.00 0.1360
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
C19 O1 C18 117.59(18) . . ?
C23 C22 C1 121.68(18) . . ?
C23 C22 C21 117.41(18) . . ?
C21 C22 C1 120.90(17) . . ?
C22 C1 C25 115.65(16) . . ?
C2 C1 C22 121.27(17) . . ?
C2 C1 C25 123.08(18) . . ?
C6 O2 C9 118.8(2) . . ?
O1 C19 C24 124.51(19) . . ?
O1 C19 C20 115.63(19) . . ?
C24 C19 C20 119.84(19) . . ?
C30 C25 C1 120.6(2) . . ?
C30 C25 C26 118.0(2) . . ?
C26 C25 C1 121.4(2) . . ?
C19 C24 H24 120.2 . . ?
C19 C24 C23 119.52(19) . . ?
C23 C24 H24 120.2 . . ?
C1 C2 C31 123.45(18) . . ?
C1 C2 C3 121.49(18) . . ?
C3 C2 C31 115.01(16) . . ?
C22 C23 C24 121.71(19) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C32 C31 C2 120.3(2) . . ?
C36 C31 C2 121.3(2) . . ?
C36 C31 C32 118.3(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.46(19) . . ?
C20 C21 H21 119.3 . . ?
C4 C3 C2 122.06(19) . . ?
C4 C3 C8 117.4(2) . . ?
C8 C3 C2 120.5(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C25 C30 H30 119.4 . . ?
C29 C30 C25 121.1(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.2(2) . . ?
C33 C32 H32 119.4 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.3 . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.1(2) . . ?
C27 C26 H26 119.4 . . ?
C31 C36 H36 119.5 . . ?
C31 C36 C35 121.0(2) . . ?
C35 C36 H36 119.5 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
O1 C18 H18A 110.0 . . ?
O1 C18 H18B 110.0 . . ?
O1 C18 C17 108.3(2) . . ?
H18A C18 H18B 108.4 . . ?
C17 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C32 C33 H33 120.9 . . ?
C34 C33 C32 118.3(2) . . ?
C34 C33 H33 120.9 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C36 C35 H35 120.8 . . ?
C34 C35 C36 118.4(3) . . ?
C34 C35 H35 120.8 . . ?
F2 C34 C33 119.1(3) . . ?
F2 C34 C35 118.1(3) . . ?
C33 C34 C35 122.9(2) . . ?
O2 C6 C5 124.5(3) . . ?
C7 C6 O2 116.1(3) . . ?
C7 C6 C5 119.4(2) . . ?
O2 C9 H9A 109.0 . . ?
O2 C9 H9B 109.0 . . ?
O2 C9 C10 113.1(2) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C26 C27 H27 120.8 . . ?
C28 C27 C26 118.4(3) . . ?
C28 C27 H27 120.8 . . ?
F1 C28 C29 118.9(3) . . ?
C27 C28 F1 118.1(3) . . ?
C27 C28 C29 123.1(2) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 C30 118.2(3) . . ?
C28 C29 H29 120.9 . . ?
C9 C10 H10C 107.2 . . ?
C9 C10 H10D 107.2 . . ?
C9 C10 H10A 112.3 . . ?
C9 C10 H10B 112.3 . . ?
C9 C10 C11A 97.5(4) . . ?
H10C C10 H10D 106.8 . . ?
H10A C10 H10B 109.9 . . ?
C11B C10 C9 120.5(4) . . ?
C11B C10 H10C 107.2 . . ?
C11B C10 H10D 107.2 . . ?
C11A C10 H10A 112.3 . . ?
C11A C10 H10B 112.3 . . ?
H14C C14 H14D 104.6 . . ?
H14A C14 H14B 110.9 . . ?
C15B C14 H14C 101.6 . . ?
C15B C14 H14D 101.6 . . ?
C15A C14 H14A 113.7 . . ?
C15A C14 H14B 113.7 . . ?
C13B C14 H14C 101.6 . . ?
C13B C14 H14D 101.6 . . ?
C13B C14 C15B 141.4(5) . . ?
C13A C14 H14A 113.7 . . ?
C13A C14 H14B 113.7 . . ?
C13A C14 C15A 89.8(7) . . ?
C10 C11B H11A 105.7 . . ?
C10 C11B H11B 105.7 . . ?
H11A C11B H11B 106.1 . . ?
C12B C11B C10 126.5(6) . . ?
C12B C11B H11A 105.7 . . ?
C12B C11B H11B 105.7 . . ?
H16A C16B H16B 108.1 . . ?
C15B C16B H16A 109.5 . . ?
C15B C16B H16B 109.5 . . ?
C15B C16B C17 110.6(4) . . ?
C17 C16B H16A 109.5 . . ?
C17 C16B H16B 109.5 . . ?
C14 C15B H15A 108.5 . . ?
C14 C15B H15B 108.5 . . ?
C16B C15B C14 115.2(6) . . ?
C16B C15B H15A 108.5 . . ?
C16B C15B H15B 108.5 . . ?
H15A C15B H15B 107.5 . . ?
H16C C16A H16D 108.3 . . ?
C15A C16A H16C 110.0 . . ?
C15A C16A H16D 110.0 . . ?
C15A C16A C17 108.7(7) . . ?
C17 C16A H16C 110.0 . . ?
C17 C16A H16D 110.0 . . ?
C14 C15A H15C 109.4 . . ?
C14 C15A H15D 109.4 . . ?
C16A C15A C14 111.1(7) . . ?
C16A C15A H15C 109.4 . . ?
C16A C15A H15D 109.4 . . ?
H15C C15A H15D 108.0 . . ?
C18 C17 C16B 115.7(2) . . ?
C18 C17 H17C 108.3 . . ?
C18 C17 H17D 108.3 . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
C16B C17 H17C 108.3 . . ?
C16B C17 H17D 108.3 . . ?
C16A C17 C18 107.9(4) . . ?
C16A C17 H17A 110.1 . . ?
C16A C17 H17B 110.1 . . ?
H17C C17 H17D 107.4 . . ?
H17A C17 H17B 108.4 . . ?
C14 C13B H13A 108.3 . . ?
C14 C13B H13B 108.3 . . ?
C14 C13B C12B 115.9(7) . . ?
H13A C13B H13B 107.4 . . ?
C12B C13B H13A 108.3 . . ?
C12B C13B H13B 108.3 . . ?
C11B C12B C13B 131.0(7) . . ?
C11B C12B H12A 104.5 . . ?
C11B C12B H12B 104.5 . . ?
C13B C12B H12A 104.5 . . ?
C13B C12B H12B 104.5 . . ?
H12A C12B H12B 105.7 . . ?
C14 C13A H13C 107.8 . . ?
C14 C13A H13D 107.8 . . ?
C14 C13A C12A 117.9(10) . . ?
H13C C13A H13D 107.2 . . ?
C12A C13A H13C 107.8 . . ?
C12A C13A H13D 107.8 . . ?
C13A C12A H12C 108.8 . . ?
C13A C12A H12D 108.8 . . ?
H12C C12A H12D 107.7 . . ?
C11A C12A C13A 113.7(9) . . ?
C11A C12A H12C 108.8 . . ?
C11A C12A H12D 108.8 . . ?
C10 C11A H11C 108.6 . . ?
C10 C11A H11D 108.6 . . ?
C12A C11A C10 114.6(8) . . ?
C12A C11A H11C 108.6 . . ?
C12A C11A H11D 108.6 . . ?
H11C C11A H11D 107.6 . . ?
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 C19 1.377(2) . ?
O1 C18 1.430(3) . ?
F2 C34 1.365(3) . ?
F1 C28 1.367(3) . ?
C22 C1 1.494(3) . ?
C22 C23 1.391(3) . ?
C22 C21 1.400(3) . ?
C1 C25 1.497(3) . ?
C1 C2 1.365(3) . ?
O2 C6 1.381(3) . ?
O2 C9 1.421(3) . ?
C19 C24 1.381(3) . ?
C19 C20 1.393(3) . ?
C25 C30 1.397(3) . ?
C25 C26 1.403(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.398(3) . ?
C2 C31 1.499(3) . ?
C2 C3 1.498(3) . ?
C23 H23 0.9500 . ?
C31 C32 1.400(3) . ?
C31 C36 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.383(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.399(3) . ?
C20 H20 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.393(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(3) . ?
C36 H36 0.9500 . ?
C36 C35 1.397(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.388(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.519(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.369(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.373(4) . ?
C35 H35 0.9500 . ?
C35 C34 1.372(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.479(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.367(4) . ?
C28 C29 1.372(4) . ?
C29 H29 0.9500 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11B 1.472(7) . ?
C10 C11A 1.729(9) . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15B 1.472(7) . ?
C14 C15A 1.637(11) . ?
C14 C13B 1.401(8) . ?
C14 C13A 1.408(12) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C11B C12B 1.227(9) . ?
C16B H16A 0.9900 . ?
C16B H16B 0.9900 . ?
C16B C15B 1.465(8) . ?
C16B C17 1.619(6) . ?
C15B H15A 0.9900 . ?
C15B H15B 0.9900 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C15A 1.490(13) . ?
C16A C17 1.493(9) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C13B C12B 1.482(9) . ?
C12B H12A 0.9900 . ?
C12B H12B 0.9900 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C12A 1.511(14) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C11A 1.494(14) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
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
O1 C19 C24 C23 -179.95(19) . . . . ?
O1 C19 C20 C21 -178.7(2) . . . . ?
O1 C18 C17 C16B 52.9(4) . . . . ?
O1 C18 C17 C16A 96.7(4) . . . . ?
F1 C28 C29 C30 -179.6(3) . . . . ?
C22 C1 C25 C30 -38.2(3) . . . . ?
C22 C1 C25 C26 140.0(2) . . . . ?
C22 C1 C2 C31 165.5(2) . . . . ?
C22 C1 C2 C3 -11.8(3) . . . . ?
C22 C21 C20 C19 -1.3(3) . . . . ?
C1 C22 C23 C24 -176.3(2) . . . . ?
C1 C22 C21 C20 177.5(2) . . . . ?
C1 C25 C30 C29 -179.4(2) . . . . ?
C1 C25 C26 C27 179.6(2) . . . . ?
C1 C2 C31 C32 140.5(2) . . . . ?
C1 C2 C31 C36 -42.9(3) . . . . ?
C1 C2 C3 C4 -44.4(3) . . . . ?
C1 C2 C3 C8 135.9(2) . . . . ?
O2 C9 C10 C11B -173.7(4) . . . . ?
O2 C9 C10 C11A 172.4(4) . . . . ?
C19 O1 C18 C17 -179.0(2) . . . . ?
C19 C24 C23 C22 -1.2(3) . . . . ?
C25 C1 C2 C31 -13.8(3) . . . . ?
C25 C1 C2 C3 168.9(2) . . . . ?
C25 C30 C29 C28 -0.8(4) . . . . ?
C25 C26 C27 C28 0.6(4) . . . . ?
C24 C19 C20 C21 2.5(3) . . . . ?
C2 C1 C25 C30 141.1(2) . . . . ?
C2 C1 C25 C26 -40.6(3) . . . . ?
C2 C31 C32 C33 177.5(2) . . . . ?
C2 C31 C36 C35 -177.9(2) . . . . ?
C2 C3 C4 C5 176.5(2) . . . . ?
C2 C3 C8 C7 -177.2(2) . . . . ?
C23 C22 C1 C25 -52.1(3) . . . . ?
C23 C22 C1 C2 128.5(2) . . . . ?
C23 C22 C21 C20 -1.2(3) . . . . ?
C31 C2 C3 C4 138.1(2) . . . . ?
C31 C2 C3 C8 -41.6(3) . . . . ?
C31 C32 C33 C34 0.3(4) . . . . ?
C31 C36 C35 C34 0.6(4) . . . . ?
C21 C22 C1 C25 129.2(2) . . . . ?
C21 C22 C1 C2 -50.1(3) . . . . ?
C21 C22 C23 C24 2.4(3) . . . . ?
C3 C2 C31 C32 -42.1(3) . . . . ?
C3 C2 C31 C36 134.5(2) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C3 C8 C7 C6 0.0(4) . . . . ?
C20 C19 C24 C23 -1.3(3) . . . . ?
C30 C25 C26 C27 -2.1(3) . . . . ?
C32 C31 C36 C35 -1.2(3) . . . . ?
C32 C33 C34 F2 179.9(2) . . . . ?
C32 C33 C34 C35 -1.0(4) . . . . ?
C4 C3 C8 C7 3.1(4) . . . . ?
C4 C5 C6 O2 179.1(3) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C26 C25 C30 C29 2.2(3) . . . . ?
C26 C27 C28 F1 179.7(3) . . . . ?
C26 C27 C28 C29 1.0(5) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C36 C35 C34 F2 179.7(2) . . . . ?
C36 C35 C34 C33 0.6(4) . . . . ?
C8 C3 C4 C5 -3.8(3) . . . . ?
C8 C7 C6 O2 180.0(3) . . . . ?
C8 C7 C6 C5 -2.3(4) . . . . ?
C18 O1 C19 C24 -6.7(3) . . . . ?
C18 O1 C19 C20 174.6(2) . . . . ?
C6 O2 C9 C10 70.4(4) . . . . ?
C9 O2 C6 C5 25.0(4) . . . . ?
C9 O2 C6 C7 -157.4(3) . . . . ?
C9 C10 C11B C12B 157.1(10) . . . . ?
C9 C10 C11A C12A 167.2(7) . . . . ?
C27 C28 C29 C30 -0.9(5) . . . . ?
C10 C11B C12B C13B 171.4(9) . . . . ?
C14 C13B C12B C11B 110.2(13) . . . . ?
C14 C13A C12A C11A -160.5(10) . . . . ?
C15B C14 C13B C12B 44.7(13) . . . . ?
C15B C16B C17 C18 68.5(6) . . . . ?
C15A C14 C13A C12A -131.0(12) . . . . ?
C15A C16A C17 C18 -79.0(8) . . . . ?
C17 C16B C15B C14 -174.2(5) . . . . ?
C17 C16A C15A C14 -175.1(6) . . . . ?
C13B C14 C15B C16B 49.3(13) . . . . ?
C13A C14 C15A C16A -133.7(9) . . . . ?
C13A C12A C11A C10 -76.4(13) . . . . ?
