#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:24:38 +0300 (Wed, 05 May 2021) $
#$Revision: 264892 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/10/1561090.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_1561090
loop_
_publ_author_name
'Ouadoudi, Omar'
'Kaehler, Tanja'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped
 PAHs from boronic and borinic acids
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              5898
_journal_page_last               5909
_journal_paper_doi               10.1039/D1SC00543J
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         '2(C31 H31 B O), 0.5(C6 H14)'
_chemical_formula_sum            'C32.5 H34.5 B O'
_chemical_formula_weight         451.91
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-26 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.874(5)
_cell_angle_beta                 102.280(5)
_cell_angle_gamma                90.643(5)
_cell_formula_units_Z            4
_cell_length_a                   12.8766(8)
_cell_length_b                   14.0599(9)
_cell_length_c                   15.4098(10)
_cell_measurement_reflns_used    27209
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      3.25
_cell_volume                     2704.5(3)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36720
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.251
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       plate
_exptl_crystal_F_000             970
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     636
_refine_ls_number_reflns         9551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0862
_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)+(0.0512P)²+2.7670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.1902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6818
_reflns_number_total             9551
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00543j2.cif
_cod_data_source_block           wa2920
_cod_depositor_comments
'Adding full bibliography for 1561085--1561097.cif.'
_cod_original_formula_sum        'C32.50 H34.50 B O'
_cod_database_code               1561090
_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   0.991
_shelx_estimated_absorpt_t_max   0.998
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
B1 B 0.5155(4) 0.2420(3) 0.2653(3) 0.0486(11) Uani 1 1 d . . . . .
O1 O 0.5281(4) 0.2903(3) 0.3482(2) 0.1002(15) Uani 1 1 d . . . . .
H1 H 0.568(5) 0.268(4) 0.389(4) 0.11(2) Uiso 1 1 d . . . . .
C1 C 0.4417(3) 0.2885(2) 0.1875(2) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.3316(3) 0.2686(2) 0.1676(2) 0.0425(8) Uani 1 1 d . . . . .
C3 C 0.2662(3) 0.3100(3) 0.0998(2) 0.0449(9) Uani 1 1 d . . . . .
H3 H 0.191947 0.294771 0.086415 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3057(3) 0.3726(3) 0.0511(2) 0.0427(9) Uani 1 1 d . . . . .
C5 C 0.4141(3) 0.3927(2) 0.0716(2) 0.0430(8) Uani 1 1 d . . . . .
H5 H 0.442698 0.435595 0.038769 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4829(3) 0.3522(2) 0.1386(2) 0.0413(8) Uani 1 1 d . . . . .
C7 C 0.2844(4) 0.2036(3) 0.2215(3) 0.0690(12) Uani 1 1 d . . . . .
H7A H 0.290341 0.235539 0.282509 0.103 Uiso 1 1 calc R U . . .
H7B H 0.322998 0.143883 0.223408 0.103 Uiso 1 1 calc R U . . .
H7C H 0.209329 0.188982 0.193441 0.103 Uiso 1 1 calc R U . . .
C8 C 0.2338(3) 0.4178(3) -0.0220(3) 0.0619(12) Uani 1 1 d . . . . .
H8A H 0.271112 0.473141 -0.036091 0.093 Uiso 1 1 calc R U . . .
H8B H 0.169528 0.438744 -0.001952 0.093 Uiso 1 1 calc R U . . .
H8C H 0.213998 0.370733 -0.075653 0.093 Uiso 1 1 calc R U . . .
C9 C 0.6003(3) 0.3785(3) 0.1586(3) 0.0639(11) Uani 1 1 d . . . . .
H9A H 0.611884 0.435497 0.130520 0.096 Uiso 1 1 calc R U . . .
H9B H 0.638443 0.325007 0.134727 0.096 Uiso 1 1 calc R U . . .
H9C H 0.626726 0.391895 0.223487 0.096 Uiso 1 1 calc R U . . .
C11 C 0.5755(3) 0.1473(2) 0.2467(2) 0.0366(8) Uani 1 1 d . . . . .
C12 C 0.6322(3) 0.0939(2) 0.3152(2) 0.0380(8) Uani 1 1 d . . . . .
C13 C 0.6925(3) 0.0186(2) 0.2934(2) 0.0405(8) Uani 1 1 d . . . . .
H13 H 0.730565 -0.014655 0.339679 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6995(3) -0.0109(2) 0.2040(2) 0.0369(8) Uani 1 1 d . . . . .
C15 C 0.7616(3) -0.0883(3) 0.1805(3) 0.0464(9) Uani 1 1 d . . . . .
H15 H 0.803373 -0.120288 0.225988 0.056 Uiso 1 1 calc R U . . .
C16 C 0.7617(3) -0.1172(3) 0.0929(3) 0.0494(9) Uani 1 1 d . . . . .
H16 H 0.803018 -0.169630 0.077762 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7017(3) -0.0705(3) 0.0250(2) 0.0444(9) Uani 1 1 d . . . . .
H17 H 0.702195 -0.091900 -0.035743 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6424(3) 0.0055(2) 0.0454(2) 0.0395(8) Uani 1 1 d . . . . .
H18 H 0.602214 0.036816 -0.001319 0.047 Uiso 1 1 calc R U . . .
C19 C 0.6403(2) 0.0380(2) 0.1351(2) 0.0336(7) Uani 1 1 d . . . . .
C20 C 0.5805(2) 0.1160(2) 0.1599(2) 0.0353(7) Uani 1 1 d . . . . .
H20 H 0.541244 0.148719 0.113773 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6249(3) 0.1184(3) 0.4070(2) 0.0448(9) Uani 1 1 d . . . . .
C22 C 0.6141(3) 0.1393(3) 0.4822(2) 0.0481(9) Uani 1 1 d . . . . .
C31 C 0.5955(3) 0.1684(3) 0.5701(2) 0.0441(8) Uani 1 1 d . . . . .
C32 C 0.5828(3) 0.2648(3) 0.5974(2) 0.0461(9) Uani 1 1 d . . . . .
H32 H 0.589412 0.311239 0.558708 0.055 Uiso 1 1 calc R U . . .
C33 C 0.5608(3) 0.2933(3) 0.6801(2) 0.0433(8) Uani 1 1 d . . . . .
H33 H 0.552217 0.359394 0.697261 0.052 Uiso 1 1 calc R U . . .
C34 C 0.5508(2) 0.2278(2) 0.7396(2) 0.0368(8) Uani 1 1 d . . . . .
C35 C 0.5626(3) 0.1322(3) 0.7108(3) 0.0517(10) Uani 1 1 d . . . . .
H35 H 0.555570 0.085673 0.749341 0.062 Uiso 1 1 calc R U . . .
C36 C 0.5843(3) 0.1022(3) 0.6282(3) 0.0564(10) Uani 1 1 d . . . . .
H36 H 0.591582 0.035906 0.610718 0.068 Uiso 1 1 calc R U . . .
C37 C 0.5247(3) 0.2632(2) 0.8297(2) 0.0381(8) Uani 1 1 d . . . . .
C38 C 0.5329(3) 0.1846(3) 0.8910(3) 0.0543(10) Uani 1 1 d . . . . .
H38A H 0.484571 0.130487 0.861446 0.081 Uiso 1 1 calc R U . . .
H38B H 0.606088 0.163027 0.903719 0.081 Uiso 1 1 calc R U . . .
H38C H 0.513390 0.209981 0.947182 0.081 Uiso 1 1 calc R U . . .
C39 C 0.6008(3) 0.3451(3) 0.8783(3) 0.0603(11) Uani 1 1 d . . . . .
H39A H 0.582916 0.367027 0.935966 0.091 Uiso 1 1 calc R U . . .
H39B H 0.673790 0.323082 0.888395 0.091 Uiso 1 1 calc R U . . .
H39C H 0.594726 0.398226 0.841902 0.091 Uiso 1 1 calc R U . . .
C40 C 0.4103(3) 0.2985(4) 0.8131(3) 0.0683(13) Uani 1 1 d . . . . .
H40A H 0.361010 0.245686 0.781675 0.102 Uiso 1 1 calc R U . . .
H40B H 0.392111 0.320830 0.870493 0.102 Uiso 1 1 calc R U . . .
H40C H 0.404963 0.351297 0.776427 0.102 Uiso 1 1 calc R U . . .
B1A B -0.0092(3) 0.7097(3) 0.2640(3) 0.0382(9) Uani 1 1 d . . . . .
O1A O -0.0432(2) 0.7393(2) 0.18290(18) 0.0542(7) Uani 1 1 d . . . . .
H1A H -0.001(4) 0.721(4) 0.149(4) 0.10(2) Uiso 1 1 d . . . . .
C1A C -0.0742(3) 0.7447(2) 0.3363(2) 0.0369(8) Uani 1 1 d . . . . .
C2A C -0.0544(3) 0.8376(3) 0.3829(2) 0.0465(9) Uani 1 1 d . . . . .
C3A C -0.1202(3) 0.8719(3) 0.4393(2) 0.0536(10) Uani 1 1 d . . . . .
H3A H -0.106647 0.934812 0.470445 0.064 Uiso 1 1 calc R U . . .
C4A C -0.2045(3) 0.8175(3) 0.4516(2) 0.0530(10) Uani 1 1 d . . . . .
C5A C -0.2213(3) 0.7258(3) 0.4076(2) 0.0502(10) Uani 1 1 d . . . . .
H5A H -0.278316 0.687044 0.415992 0.060 Uiso 1 1 calc R U . . .
C6A C -0.1570(3) 0.6888(3) 0.3512(2) 0.0405(8) Uani 1 1 d . . . . .
C7A C 0.0355(4) 0.8994(3) 0.3697(3) 0.0775(14) Uani 1 1 d . . . . .
H7A1 H 0.038675 0.961110 0.407439 0.116 Uiso 1 1 calc R U . . .
H7A2 H 0.023841 0.910193 0.306758 0.116 Uiso 1 1 calc R U . . .
H7A3 H 0.102681 0.867272 0.386372 0.116 Uiso 1 1 calc R U . . .
C8A C -0.2763(4) 0.8580(4) 0.5119(3) 0.0799(15) Uani 1 1 d . . . . .
H8A1 H -0.237174 0.908274 0.556810 0.120 Uiso 1 1 calc R U . . .
H8A2 H -0.299895 0.806703 0.541884 0.120 Uiso 1 1 calc R U . . .
H8A3 H -0.338363 0.885101 0.475883 0.120 Uiso 1 1 calc R U . . .
C9A C -0.1779(3) 0.5870(3) 0.3045(3) 0.0549(10) Uani 1 1 d . . . . .
H9A1 H -0.181048 0.586577 0.240386 0.082 Uiso 1 1 calc R U . . .
H9A2 H -0.245829 0.561890 0.313222 0.082 Uiso 1 1 calc R U . . .
H9A3 H -0.120504 0.546620 0.329826 0.082 Uiso 1 1 calc R U . . .
C11A C 0.0883(2) 0.6428(2) 0.2845(2) 0.0329(7) Uani 1 1 d . . . . .
C12A C 0.1440(2) 0.6002(2) 0.2188(2) 0.0324(7) Uani 1 1 d . . . . .
C13A C 0.2237(3) 0.5382(2) 0.2413(2) 0.0341(7) Uani 1 1 d . . . . .
H13A H 0.256843 0.508295 0.196196 0.041 Uiso 1 1 calc R U . . .
C14A C 0.2577(2) 0.5177(2) 0.3305(2) 0.0313(7) Uani 1 1 d . . . . .
C15A C 0.3438(3) 0.4574(2) 0.3559(2) 0.0390(8) Uani 1 1 d . . . . .
H15A H 0.377426 0.426117 0.311661 0.047 Uiso 1 1 calc R U . . .
C16A C 0.3783(3) 0.4443(3) 0.4429(2) 0.0467(9) Uani 1 1 d . . . . .
H16A H 0.435953 0.403847 0.459102 0.056 Uiso 1 1 calc R U . . .
C17A C 0.3303(3) 0.4894(3) 0.5089(2) 0.0482(9) Uani 1 1 d . . . . .
H17A H 0.356588 0.480706 0.569775 0.058 Uiso 1 1 calc R U . . .
C18A C 0.2457(3) 0.5459(3) 0.4867(2) 0.0438(9) Uani 1 1 d . . . . .
H18A H 0.212249 0.574829 0.532012 0.053 Uiso 1 1 calc R U . . .
C19A C 0.2074(2) 0.5616(2) 0.3967(2) 0.0333(7) Uani 1 1 d . . . . .
C20A C 0.1218(2) 0.6219(2) 0.3707(2) 0.0349(7) Uani 1 1 d . . . . .
H20A H 0.085951 0.649253 0.414942 0.042 Uiso 1 1 calc R U . . .
C21A C 0.1182(3) 0.6227(2) 0.1276(2) 0.0351(7) Uani 1 1 d . . . . .
C22A C 0.1040(3) 0.6413(2) 0.0518(2) 0.0368(8) Uani 1 1 d . . . . .
C31A C 0.0882(2) 0.6643(2) -0.0385(2) 0.0338(7) Uani 1 1 d . . . . .
C32A C 0.1413(3) 0.7432(3) -0.0580(2) 0.0489(9) Uani 1 1 d . . . . .
H32A H 0.188647 0.782278 -0.011323 0.059 Uiso 1 1 calc R U . . .
C33A C 0.1257(3) 0.7648(3) -0.1447(2) 0.0472(9) Uani 1 1 d . . . . .
H33A H 0.163170 0.818742 -0.156516 0.057 Uiso 1 1 calc R U . . .
C34A C 0.0569(2) 0.7103(2) -0.2153(2) 0.0341(7) Uani 1 1 d . . . . .
C35A C 0.0059(3) 0.6317(3) -0.1951(2) 0.0418(8) Uani 1 1 d . . . . .
H35A H -0.041010 0.592288 -0.241883 0.050 Uiso 1 1 calc R U . . .
C36A C 0.0212(3) 0.6087(3) -0.1082(2) 0.0433(8) Uani 1 1 d . . . . .
H36A H -0.015054 0.553916 -0.096726 0.052 Uiso 1 1 calc R U . . .
C37A C 0.0435(3) 0.7367(2) -0.3106(2) 0.0395(8) Uani 1 1 d . . . . .
C38A C -0.0366(3) 0.6696(3) -0.3784(2) 0.0595(11) Uani 1 1 d . . . . .
H38D H -0.106258 0.673186 -0.362256 0.089 Uiso 1 1 calc R U . . .
H38E H -0.042455 0.688833 -0.438238 0.089 Uiso 1 1 calc R U . . .
H38F H -0.012678 0.603708 -0.378161 0.089 Uiso 1 1 calc R U . . .
C39A C 0.1507(3) 0.7297(3) -0.3372(3) 0.0604(11) Uani 1 1 d . . . . .
H39D H 0.174715 0.663946 -0.335685 0.091 Uiso 1 1 calc R U . . .
H39E H 0.143699 0.747175 -0.397800 0.091 Uiso 1 1 calc R U . . .
H39F H 0.202789 0.773654 -0.295134 0.091 Uiso 1 1 calc R U . . .
C40A C 0.0069(4) 0.8393(3) -0.3131(3) 0.0636(12) Uani 1 1 d . . . . .
H40D H -0.062096 0.844268 -0.296096 0.095 Uiso 1 1 calc R U . . .
H40E H 0.059258 0.882975 -0.271143 0.095 Uiso 1 1 calc R U . . .
H40F H 0.000168 0.856496 -0.373809 0.095 Uiso 1 1 calc R U . . .
C41 C 0.1636(4) 0.9312(5) 0.1660(4) 0.0962(18) Uani 1 1 d . . . . .
H41A H 0.150485 0.906078 0.219506 0.144 Uiso 1 1 calc R U . . .
H41B H 0.199943 0.883448 0.132704 0.144 Uiso 1 1 calc R U . . .
H41C H 0.208315 0.990131 0.183914 0.144 Uiso 1 1 calc R U . . .
C42 C 0.0614(6) 0.9523(10) 0.1087(6) 0.209(6) Uani 1 1 d . . . . .
H42A H 0.018143 0.891621 0.096510 0.250 Uiso 1 1 calc R U . . .
H42B H 0.026423 0.997128 0.147155 0.250 Uiso 1 1 calc R U . . .
C43 C 0.0475(4) 0.9882(5) 0.0290(4) 0.0975(18) Uani 1 1 d . . . . .
H43A H 0.081918 0.942320 -0.008937 0.117 Uiso 1 1 calc R U . . .
H43B H 0.092867 1.047608 0.041740 0.117 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'
B B 0.0013 0.0007 '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
O1 B1 C11 121.9(4) . . ?
O1 B1 C1 116.2(3) . . ?
C11 B1 C1 121.9(3) . . ?
B1 O1 H1 117(4) . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 B1 119.8(3) . . ?
C6 C1 B1 121.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 C7 120.1(4) . . ?
C1 C2 C7 119.8(3) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C8 121.5(4) . . ?
C5 C4 C8 120.7(4) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C9 119.6(3) . . ?
C1 C6 C9 120.9(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C20 C11 C12 117.1(3) . . ?
C20 C11 B1 118.2(3) . . ?
C12 C11 B1 124.6(3) . . ?
C13 C12 C21 119.2(3) . . ?
C13 C12 C11 120.4(3) . . ?
C21 C12 C11 120.4(3) . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 122.3(3) . . ?
C13 C14 C19 118.6(3) . . ?
C15 C14 C19 119.0(3) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 122.9(3) . . ?
C20 C19 C14 118.3(3) . . ?
C18 C19 C14 118.8(3) . . ?
C11 C20 C19 123.8(3) . . ?
C11 C20 H20 118.1 . . ?
C19 C20 H20 118.1 . . ?
C22 C21 C12 177.1(4) . . ?
C21 C22 C31 176.1(4) . . ?
C32 C31 C36 118.2(3) . . ?
C32 C31 C22 119.8(3) . . ?
C36 C31 C22 121.9(4) . . ?
C33 C32 C31 120.5(3) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 122.0(3) . . ?
C32 C33 H33 119.0 . . ?
C34 C33 H33 119.0 . . ?
C35 C34 C33 116.7(3) . . ?
C35 C34 C37 123.6(3) . . ?
C33 C34 C37 119.7(3) . . ?
C36 C35 C34 122.2(3) . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
C35 C36 C31 120.5(4) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C39 C37 C34 110.5(3) . . ?
C39 C37 C38 107.4(3) . . ?
C34 C37 C38 112.3(3) . . ?
C39 C37 C40 109.3(3) . . ?
C34 C37 C40 108.5(3) . . ?
C38 C37 C40 108.7(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O1A B1A C1A 115.6(3) . . ?
O1A B1A C11A 122.4(3) . . ?
C1A B1A C11A 122.0(3) . . ?
B1A O1A H1A 109(4) . . ?
C6A C1A C2A 118.6(3) . . ?
C6A C1A B1A 121.6(3) . . ?
C2A C1A B1A 119.6(3) . . ?
C3A C2A C1A 119.3(4) . . ?
C3A C2A C7A 120.7(4) . . ?
C1A C2A C7A 120.0(3) . . ?
C4A C3A C2A 122.1(4) . . ?
C4A C3A H3A 119.0 . . ?
C2A C3A H3A 119.0 . . ?
C5A C4A C3A 118.1(4) . . ?
C5A C4A C8A 121.1(4) . . ?
C3A C4A C8A 120.7(4) . . ?
C4A C5A C6A 121.5(4) . . ?
C4A C5A H5A 119.2 . . ?
C6A C5A H5A 119.2 . . ?
C5A C6A C1A 120.4(3) . . ?
C5A C6A C9A 119.7(4) . . ?
C1A C6A C9A 119.9(3) . . ?
C2A C7A H7A1 109.5 . . ?
C2A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C2A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C4A C8A H8A1 109.5 . . ?
C4A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C4A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C6A C9A H9A1 109.5 . . ?
C6A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C6A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C20A C11A C12A 117.1(3) . . ?
C20A C11A B1A 118.2(3) . . ?
C12A C11A B1A 124.6(3) . . ?
C13A C12A C11A 120.8(3) . . ?
C13A C12A C21A 118.3(3) . . ?
C11A C12A C21A 120.9(3) . . ?
C12A C13A C14A 121.3(3) . . ?
C12A C13A H13A 119.3 . . ?
C14A C13A H13A 119.3 . . ?
C19A C14A C13A 118.9(3) . . ?
C19A C14A C15A 119.0(3) . . ?
C13A C14A C15A 122.0(3) . . ?
C16A C15A C14A 120.2(3) . . ?
C16A C15A H15A 119.9 . . ?
C14A C15A H15A 119.9 . . ?
C15A C16A C17A 120.9(3) . . ?
C15A C16A H16A 119.5 . . ?
C17A C16A H16A 119.5 . . ?
C18A C17A C16A 120.4(3) . . ?
C18A C17A H17A 119.8 . . ?
C16A C17A H17A 119.8 . . ?
C17A C18A C19A 120.5(3) . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A H18A 119.8 . . ?
C14A C19A C18A 118.9(3) . . ?
C14A C19A C20A 118.5(3) . . ?
C18A C19A C20A 122.6(3) . . ?
C11A C20A C19A 123.2(3) . . ?
C11A C20A H20A 118.4 . . ?
C19A C20A H20A 118.4 . . ?
C22A C21A C12A 175.6(3) . . ?
C21A C22A C31A 179.2(4) . . ?
C36A C31A C32A 118.0(3) . . ?
C36A C31A C22A 121.3(3) . . ?
C32A C31A C22A 120.8(3) . . ?
C33A C32A C31A 120.4(3) . . ?
C33A C32A H32A 119.8 . . ?
C31A C32A H32A 119.8 . . ?
C32A C33A C34A 122.1(3) . . ?
C32A C33A H33A 118.9 . . ?
C34A C33A H33A 118.9 . . ?
C35A C34A C33A 116.8(3) . . ?
C35A C34A C37A 123.1(3) . . ?
C33A C34A C37A 120.1(3) . . ?
C34A C35A C36A 121.7(3) . . ?
C34A C35A H35A 119.1 . . ?
C36A C35A H35A 119.1 . . ?
C31A C36A C35A 120.9(3) . . ?
C31A C36A H36A 119.5 . . ?
C35A C36A H36A 119.5 . . ?
C39A C37A C40A 109.0(3) . . ?
C39A C37A C38A 108.4(3) . . ?
C40A C37A C38A 109.1(3) . . ?
C39A C37A C34A 108.4(3) . . ?
C40A C37A C34A 109.6(3) . . ?
C38A C37A C34A 112.3(3) . . ?
C37A C38A H38D 109.5 . . ?
C37A C38A H38E 109.5 . . ?
H38D C38A H38E 109.5 . . ?
C37A C38A H38F 109.5 . . ?
H38D C38A H38F 109.5 . . ?
H38E C38A H38F 109.5 . . ?
C37A C39A H39D 109.5 . . ?
C37A C39A H39E 109.5 . . ?
H39D C39A H39E 109.5 . . ?
C37A C39A H39F 109.5 . . ?
H39D C39A H39F 109.5 . . ?
H39E C39A H39F 109.5 . . ?
C37A C40A H40D 109.5 . . ?
C37A C40A H40E 109.5 . . ?
H40D C40A H40E 109.5 . . ?
C37A C40A H40F 109.5 . . ?
H40D C40A H40F 109.5 . . ?
H40E C40A H40F 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C41 126.6(6) . . ?
C43 C42 H42A 105.7 . . ?
C41 C42 H42A 105.7 . . ?
C43 C42 H42B 105.7 . . ?
C41 C42 H42B 105.7 . . ?
H42A C42 H42B 106.1 . . ?
C42 C43 C43 129.9(7) . 2_575 ?
C42 C43 H43A 104.8 . . ?
C43 C43 H43A 104.8 2_575 . ?
C42 C43 H43B 104.8 . . ?
C43 C43 H43B 104.8 2_575 . ?
H43A C43 H43B 105.8 . . ?
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
B1 O1 1.351(5) . ?
B1 C11 1.574(5) . ?
B1 C1 1.576(5) . ?
O1 H1 0.82(6) . ?
C1 C2 1.403(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.386(5) . ?
C2 C7 1.509(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 C8 1.507(5) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C9 1.509(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C20 1.372(5) . ?
C11 C12 1.444(5) . ?
C12 C13 1.372(5) . ?
C12 C21 1.438(5) . ?
C13 C14 1.413(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.415(5) . ?
C14 C19 1.422(4) . ?
C15 C16 1.363(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.366(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.409(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.408(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.199(5) . ?
C22 C31 1.438(5) . ?
C31 C32 1.391(5) . ?
C31 C36 1.393(5) . ?
C32 C33 1.379(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.397(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(5) . ?
C34 C37 1.526(5) . ?
C35 C36 1.380(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C39 1.518(5) . ?
C37 C38 1.528(5) . ?
C37 C40 1.538(5) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
B1A O1A 1.350(5) . ?
B1A C1A 1.569(5) . ?
B1A C11A 1.578(5) . ?
O1A H1A 0.85(6) . ?
C1A C6A 1.391(5) . ?
C1A C2A 1.406(5) . ?
C2A C3A 1.388(5) . ?
C2A C7A 1.502(6) . ?
C3A C4A 1.379(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.374(6) . ?
C4A C8A 1.514(5) . ?
C5A C6A 1.385(5) . ?
C5A H5A 0.9500 . ?
C6A C9A 1.517(5) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C11A C20A 1.374(4) . ?
C11A C12A 1.440(4) . ?
C12A C13A 1.369(4) . ?
C12A C21A 1.448(4) . ?
C13A C14A 1.416(4) . ?
C13A H13A 0.9500 . ?
C14A C19A 1.408(4) . ?
C14A C15A 1.420(4) . ?
C15A C16A 1.355(5) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.393(5) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.364(5) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.415(4) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.417(4) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.205(4) . ?
C22A C31A 1.438(4) . ?
C31A C36A 1.379(5) . ?
C31A C32A 1.392(5) . ?
C32A C33A 1.380(5) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.389(5) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.380(5) . ?
C34A C37A 1.532(4) . ?
C35A C36A 1.389(5) . ?
C35A H35A 0.9500 . ?
C36A H36A 0.9500 . ?
C37A C39A 1.523(5) . ?
C37A C40A 1.524(5) . ?
C37A C38A 1.526(5) . ?
C38A H38D 0.9800 . ?
C38A H38E 0.9800 . ?
C38A H38F 0.9800 . ?
C39A H39D 0.9800 . ?
C39A H39E 0.9800 . ?
C39A H39F 0.9800 . ?
C40A H40D 0.9800 . ?
C40A H40E 0.9800 . ?
C40A H40F 0.9800 . ?
C41 C42 1.476(9) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.361(9) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C43 1.420(11) 2_575 ?
C43 H43A 0.9900 . ?
C43 H43B 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 B1 C1 C2 -86.9(5) . . . . ?
C11 B1 C1 C2 96.0(4) . . . . ?
O1 B1 C1 C6 91.1(5) . . . . ?
C11 B1 C1 C6 -85.9(5) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
B1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C7 -177.5(3) . . . . ?
B1 C1 C2 C7 0.5(5) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C7 C2 C3 C4 177.6(4) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C8 -179.5(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C8 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 C9 -179.0(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
B1 C1 C6 C5 -178.9(3) . . . . ?
C2 C1 C6 C9 178.3(3) . . . . ?
B1 C1 C6 C9 0.3(5) . . . . ?
O1 B1 C11 C20 -163.7(4) . . . . ?
C1 B1 C11 C20 13.2(6) . . . . ?
O1 B1 C11 C12 12.0(6) . . . . ?
C1 B1 C11 C12 -171.1(3) . . . . ?
C20 C11 C12 C13 3.4(5) . . . . ?
B1 C11 C12 C13 -172.4(3) . . . . ?
C20 C11 C12 C21 -175.7(3) . . . . ?
B1 C11 C12 C21 8.5(5) . . . . ?
C21 C12 C13 C14 177.7(3) . . . . ?
C11 C12 C13 C14 -1.5(5) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C12 C13 C14 C19 -1.4(5) . . . . ?
C13 C14 C15 C16 176.7(3) . . . . ?
C19 C14 C15 C16 -2.1(5) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 -179.9(3) . . . . ?
C17 C18 C19 C14 -1.2(5) . . . . ?
C13 C14 C19 C20 2.3(5) . . . . ?
C15 C14 C19 C20 -178.9(3) . . . . ?
C13 C14 C19 C18 -176.5(3) . . . . ?
C15 C14 C19 C18 2.3(5) . . . . ?
C12 C11 C20 C19 -2.5(5) . . . . ?
B1 C11 C20 C19 173.5(3) . . . . ?
C18 C19 C20 C11 178.5(3) . . . . ?
C14 C19 C20 C11 -0.3(5) . . . . ?
C36 C31 C32 C33 0.6(5) . . . . ?
C22 C31 C32 C33 177.5(4) . . . . ?
C31 C32 C33 C34 0.3(6) . . . . ?
C32 C33 C34 C35 -0.9(5) . . . . ?
C32 C33 C34 C37 -179.0(3) . . . . ?
C33 C34 C35 C36 0.6(6) . . . . ?
C37 C34 C35 C36 178.7(4) . . . . ?
C34 C35 C36 C31 0.2(6) . . . . ?
C32 C31 C36 C35 -0.9(6) . . . . ?
C22 C31 C36 C35 -177.6(4) . . . . ?
C35 C34 C37 C39 130.3(4) . . . . ?
C33 C34 C37 C39 -51.6(4) . . . . ?
C35 C34 C37 C38 10.4(5) . . . . ?
C33 C34 C37 C38 -171.6(3) . . . . ?
C35 C34 C37 C40 -109.8(4) . . . . ?
C33 C34 C37 C40 68.2(4) . . . . ?
O1A B1A C1A C6A 94.4(4) . . . . ?
C11A B1A C1A C6A -84.6(4) . . . . ?
O1A B1A C1A C2A -80.7(4) . . . . ?
C11A B1A C1A C2A 100.4(4) . . . . ?
C6A C1A C2A C3A -2.4(5) . . . . ?
B1A C1A C2A C3A 172.8(3) . . . . ?
C6A C1A C2A C7A 178.9(4) . . . . ?
B1A C1A C2A C7A -5.9(5) . . . . ?
C1A C2A C3A C4A 0.2(5) . . . . ?
C7A C2A C3A C4A 178.9(4) . . . . ?
C2A C3A C4A C5A 1.5(5) . . . . ?
C2A C3A C4A C8A -178.5(3) . . . . ?
C3A C4A C5A C6A -1.0(5) . . . . ?
C8A C4A C5A C6A 179.0(3) . . . . ?
C4A C5A C6A C1A -1.2(5) . . . . ?
C4A C5A C6A C9A 179.5(3) . . . . ?
C2A C1A C6A C5A 2.9(5) . . . . ?
B1A C1A C6A C5A -172.2(3) . . . . ?
C2A C1A C6A C9A -177.8(3) . . . . ?
B1A C1A C6A C9A 7.1(5) . . . . ?
O1A B1A C11A C20A 175.4(3) . . . . ?
C1A B1A C11A C20A -5.7(5) . . . . ?
O1A B1A C11A C12A -5.7(5) . . . . ?
C1A B1A C11A C12A 173.2(3) . . . . ?
C20A C11A C12A C13A 2.9(5) . . . . ?
B1A C11A C12A C13A -176.0(3) . . . . ?
C20A C11A C12A C21A -176.3(3) . . . . ?
B1A C11A C12A C21A 4.9(5) . . . . ?
C11A C12A C13A C14A -3.3(5) . . . . ?
C21A C12A C13A C14A 175.9(3) . . . . ?
C12A C13A C14A C19A 0.6(5) . . . . ?
C12A C13A C14A C15A -176.7(3) . . . . ?
C19A C14A C15A C16A -1.5(5) . . . . ?
C13A C14A C15A C16A 175.9(3) . . . . ?
C14A C15A C16A C17A 0.0(6) . . . . ?
C15A C16A C17A C18A 1.6(6) . . . . ?
C16A C17A C18A C19A -1.7(6) . . . . ?
C13A C14A C19A C18A -176.1(3) . . . . ?
C15A C14A C19A C18A 1.3(5) . . . . ?
C13A C14A C19A C20A 2.3(5) . . . . ?
C15A C14A C19A C20A 179.7(3) . . . . ?
C17A C18A C19A C14A 0.3(5) . . . . ?
C17A C18A C19A C20A -178.1(3) . . . . ?
C12A C11A C20A C19A 0.1(5) . . . . ?
B1A C11A C20A C19A 179.1(3) . . . . ?
C14A C19A C20A C11A -2.7(5) . . . . ?
C18A C19A C20A C11A 175.7(3) . . . . ?
C36A C31A C32A C33A 0.7(6) . . . . ?
C22A C31A C32A C33A -179.9(3) . . . . ?
C31A C32A C33A C34A 0.4(6) . . . . ?
C32A C33A C34A C35A -1.2(6) . . . . ?
C32A C33A C34A C37A -179.2(3) . . . . ?
C33A C34A C35A C36A 0.9(5) . . . . ?
C37A C34A C35A C36A 178.8(3) . . . . ?
C32A C31A C36A C35A -1.0(5) . . . . ?
C22A C31A C36A C35A 179.6(3) . . . . ?
C34A C35A C36A C31A 0.2(6) . . . . ?
C35A C34A C37A C39A -116.6(4) . . . . ?
C33A C34A C37A C39A 61.3(4) . . . . ?
C35A C34A C37A C40A 124.5(4) . . . . ?
C33A C34A C37A C40A -57.6(4) . . . . ?
C35A C34A C37A C38A 3.1(5) . . . . ?
C33A C34A C37A C38A -179.0(3) . . . . ?
C41 C42 C43 C43 -178.8(10) . . . 2_575 ?
