#------------------------------------------------------------------------------
#$Date: 2021-09-18 01:13:39 +0300 (Sat, 18 Sep 2021) $
#$Revision: 269187 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564680.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_1564680
loop_
_publ_author_name
'Wang, Hanqiang'
'Zhang, Jie'
'Xie, Zuowei'
_publ_section_title
;
 Ring-opening and ring-expansion reactions of carborane-fused borirane
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04453B
_journal_year                    2021
_chemical_formula_sum            'C42 H64 B11 Br N3 O1.5'
_chemical_formula_weight         833.78
_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
_audit_update_record
;
2021-08-09 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                93.8300(10)
_cell_angle_beta                 94.6180(10)
_cell_angle_gamma                105.7270(10)
_cell_formula_units_Z            2
_cell_length_a                   11.7707(4)
_cell_length_b                   11.9109(5)
_cell_length_c                   18.3230(8)
_cell_measurement_reflns_used    1664
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     2454.15(17)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      175(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            70032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.422
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       block
_exptl_crystal_F_000             878
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1438P)²+1.9546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7036
_reflns_number_total             8872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04453b2.cif
_cod_data_source_block           10
_cod_original_formula_sum        'C42 H64 B11 Br N3 O1.50'
_cod_database_code               1564680
_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   0.722
_shelx_estimated_absorpt_t_max   0.780
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
Br1 Br 0.68258(4) 0.34590(4) 0.36133(2) 0.0539(2) Uani 1 1 d . . . . .
N1 N 0.6860(3) 0.4781(2) 0.23220(18) 0.0367(7) Uani 1 1 d . . . . .
N2 N 0.4479(3) 0.4542(2) 0.28431(16) 0.0334(6) Uani 1 1 d . . . . .
N3 N 0.3856(3) 0.2658(2) 0.27244(16) 0.0318(6) Uani 1 1 d . . . . .
C1 C 0.7548(3) 0.3547(3) 0.15002(19) 0.0322(7) Uani 1 1 d . . . . .
C2 C 0.6602(3) 0.2655(3) 0.19760(19) 0.0299(7) Uani 1 1 d . . . . .
C11 C 0.7527(3) 0.4763(3) 0.1811(2) 0.0366(8) Uani 1 1 d . . . . .
C12 C 0.8221(3) 0.5851(3) 0.1527(2) 0.0442(9) Uani 1 1 d . . . . .
C13 C 0.8046(5) 0.6900(4) 0.1784(3) 0.0619(13) Uani 1 1 d . . . . .
H13A H 0.751127 0.690671 0.214503 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8641(5) 0.7946(4) 0.1525(4) 0.0764(16) Uani 1 1 d . . . . .
H14A H 0.850223 0.866006 0.170335 0.092 Uiso 1 1 calc R U . . .
C15 C 0.9424(5) 0.7950(4) 0.1013(3) 0.0729(16) Uani 1 1 d . . . . .
H15A H 0.984291 0.866890 0.084428 0.087 Uiso 1 1 calc R U . . .
C16 C 0.9608(6) 0.6920(5) 0.0743(4) 0.0853(19) Uani 1 1 d . . . . .
H16A H 1.014879 0.692615 0.038395 0.102 Uiso 1 1 calc R U . . .
C17 C 0.9007(5) 0.5870(4) 0.0992(3) 0.0705(15) Uani 1 1 d . . . . .
H17A H 0.912975 0.515753 0.079688 0.085 Uiso 1 1 calc R U . . .
C18 C 0.4809(3) 0.3558(3) 0.26334(18) 0.0291(7) Uani 1 1 d . . . . .
C19 C 0.3358(3) 0.4228(3) 0.3076(2) 0.0422(9) Uani 1 1 d . . . . .
H19A H 0.293933 0.474874 0.325607 0.051 Uiso 1 1 calc R U . . .
C20 C 0.2973(3) 0.3069(3) 0.3002(2) 0.0408(9) Uani 1 1 d . . . . .
H20A H 0.222759 0.260639 0.311939 0.049 Uiso 1 1 calc R U . . .
C21 C 0.5035(4) 0.5773(3) 0.2767(2) 0.0401(9) Uani 1 1 d . . . . .
C22 C 0.4755(5) 0.6185(4) 0.2096(3) 0.0563(12) Uani 1 1 d . . . . .
C23 C 0.5185(6) 0.7393(5) 0.2049(3) 0.0770(18) Uani 1 1 d . . . . .
H23A H 0.502637 0.771054 0.160269 0.092 Uiso 1 1 calc R U . . .
C24 C 0.5831(6) 0.8125(4) 0.2636(4) 0.0780(18) Uani 1 1 d . . . . .
H24A H 0.612631 0.893961 0.258974 0.094 Uiso 1 1 calc R U . . .
C25 C 0.6051(5) 0.7691(4) 0.3285(3) 0.0666(14) Uani 1 1 d . . . . .
H25A H 0.648961 0.821281 0.368828 0.080 Uiso 1 1 calc R U . . .
C26 C 0.5649(4) 0.6499(3) 0.3372(2) 0.0460(10) Uani 1 1 d . . . . .
C27 C 0.3965(7) 0.5396(5) 0.1454(3) 0.0832(19) Uani 1 1 d . . . . .
H27A H 0.389989 0.456747 0.155446 0.100 Uiso 1 1 calc R U . . .
C28 C 0.4533(9) 0.5598(10) 0.0731(3) 0.135(4) Uani 1 1 d . . . . .
H28A H 0.533622 0.550497 0.079155 0.203 Uiso 1 1 calc R U . . .
H28B H 0.405347 0.502572 0.033903 0.203 Uiso 1 1 calc R U . . .
H28C H 0.457106 0.639161 0.060220 0.203 Uiso 1 1 calc R U . . .
C29 C 0.2721(7) 0.5533(7) 0.1383(4) 0.102(2) Uani 1 1 d . . . . .
H29A H 0.225111 0.501068 0.096474 0.153 Uiso 1 1 calc R U . . .
H29B H 0.235191 0.532965 0.183427 0.153 Uiso 1 1 calc R U . . .
H29C H 0.275503 0.634574 0.130221 0.153 Uiso 1 1 calc R U . . .
C30 C 0.5845(4) 0.6067(4) 0.4114(2) 0.0551(11) Uani 1 1 d . . . . .
H30A H 0.562978 0.519204 0.404616 0.066 Uiso 1 1 calc R U . . .
C31 C 0.7124(6) 0.6500(6) 0.4448(4) 0.095(2) Uani 1 1 d . . . . .
H31A H 0.720057 0.619368 0.492794 0.143 Uiso 1 1 calc R U . . .
H31B H 0.763415 0.622738 0.412198 0.143 Uiso 1 1 calc R U . . .
H31C H 0.736587 0.735784 0.451173 0.143 Uiso 1 1 calc R U . . .
C32 C 0.5008(6) 0.6413(5) 0.4640(3) 0.0803(17) Uani 1 1 d . . . . .
H32A H 0.513980 0.613036 0.512063 0.120 Uiso 1 1 calc R U . . .
H32B H 0.517171 0.726786 0.469579 0.120 Uiso 1 1 calc R U . . .
H32C H 0.418227 0.606120 0.443550 0.120 Uiso 1 1 calc R U . . .
C33 C 0.3580(3) 0.1414(3) 0.2477(2) 0.0349(8) Uani 1 1 d . . . . .
C34 C 0.3008(3) 0.1057(3) 0.1766(2) 0.0426(9) Uani 1 1 d . . . . .
C35 C 0.2650(4) -0.0149(4) 0.1556(3) 0.0571(12) Uani 1 1 d . . . . .
H35A H 0.225986 -0.042987 0.107802 0.068 Uiso 1 1 calc R U . . .
C36 C 0.2858(5) -0.0932(4) 0.2034(3) 0.0666(14) Uani 1 1 d . . . . .
H36A H 0.262048 -0.174584 0.187942 0.080 Uiso 1 1 calc R U . . .
C37 C 0.3398(5) -0.0555(4) 0.2726(3) 0.0616(12) Uani 1 1 d . . . . .
H37A H 0.353156 -0.111560 0.304370 0.074 Uiso 1 1 calc R U . . .
C38 C 0.3764(4) 0.0635(3) 0.2983(2) 0.0417(9) Uani 1 1 d . . . . .
C39 C 0.2768(4) 0.1896(4) 0.1228(2) 0.0488(10) Uani 1 1 d . . . . .
H39A H 0.332679 0.268334 0.139453 0.059 Uiso 1 1 calc R U . . .
C40 C 0.2980(5) 0.1590(6) 0.0436(3) 0.0686(14) Uani 1 1 d . . . . .
H40A H 0.280648 0.217173 0.012420 0.103 Uiso 1 1 calc R U . . .
H40B H 0.381018 0.158929 0.041936 0.103 Uiso 1 1 calc R U . . .
H40C H 0.245994 0.081171 0.025767 0.103 Uiso 1 1 calc R U . . .
C41 C 0.1512(5) 0.2015(6) 0.1245(3) 0.0809(17) Uani 1 1 d . . . . .
H41A H 0.137877 0.256160 0.089309 0.121 Uiso 1 1 calc R U . . .
H41B H 0.093777 0.124705 0.111317 0.121 Uiso 1 1 calc R U . . .
H41C H 0.141167 0.231198 0.174085 0.121 Uiso 1 1 calc R U . . .
C42 C 0.4234(4) 0.1008(3) 0.3772(2) 0.0473(10) Uani 1 1 d . . . . .
H42A H 0.453199 0.188253 0.382848 0.057 Uiso 1 1 calc R U . . .
C43 C 0.5267(5) 0.0521(5) 0.4016(3) 0.0632(12) Uani 1 1 d . . . . .
H43A H 0.554088 0.078942 0.453402 0.095 Uiso 1 1 calc R U . . .
H43B H 0.500146 -0.033654 0.395681 0.095 Uiso 1 1 calc R U . . .
H43C H 0.591902 0.079987 0.371434 0.095 Uiso 1 1 calc R U . . .
C44 C 0.3243(5) 0.0646(5) 0.4276(3) 0.0646(13) Uani 1 1 d . . . . .
H44A H 0.356660 0.089761 0.478868 0.097 Uiso 1 1 calc R U . . .
H44B H 0.261548 0.101762 0.414510 0.097 Uiso 1 1 calc R U . . .
H44C H 0.291248 -0.020697 0.421602 0.097 Uiso 1 1 calc R U . . .
O1 O 0.0613(5) 0.1343(5) 0.3495(4) 0.129(2) Uani 1 1 d D . . . .
C45 C 0.0219(8) 0.0140(7) 0.3212(6) 0.146(4) Uani 1 1 d D . . . .
H45A H 0.080315 -0.028193 0.336541 0.175 Uiso 1 1 calc R U . . .
H45B H 0.008421 0.006196 0.266833 0.175 Uiso 1 1 calc R U . . .
C46 C -0.0908(15) -0.0311(12) 0.3540(12) 0.284(12) Uani 1 1 d D . . . .
H46A H -0.089887 -0.103359 0.377578 0.341 Uiso 1 1 calc R U . . .
H46B H -0.158264 -0.050743 0.315077 0.341 Uiso 1 1 calc R U . . .
C47 C -0.1058(9) 0.0595(12) 0.4100(8) 0.176(5) Uani 1 1 d D . . . .
H47A H -0.092549 0.037108 0.460360 0.211 Uiso 1 1 calc R U . . .
H47B H -0.186464 0.069856 0.402655 0.211 Uiso 1 1 calc R U . . .
C48 C -0.0124(9) 0.1716(9) 0.3978(6) 0.155(4) Uani 1 1 d D . . . .
H48A H -0.049856 0.227751 0.375196 0.186 Uiso 1 1 calc R U . . .
H48B H 0.033742 0.209308 0.444781 0.186 Uiso 1 1 calc R U . . .
O2 O 0.1829(9) 0.5994(13) 0.3558(7) 0.147(6) Uani 0.5 1 d D . P . .
C49 C 0.0901(12) 0.601(2) 0.3013(7) 0.134(7) Uani 0.5 1 d D . P . .
H49A H 0.061506 0.524618 0.271199 0.161 Uiso 0.5 1 calc R U P . .
H49B H 0.117713 0.663352 0.268554 0.161 Uiso 0.5 1 calc R U P . .
C50 C -0.0057(14) 0.624(2) 0.3438(9) 0.153(9) Uani 0.5 1 d D . P . .
H50A H -0.065305 0.550437 0.351255 0.183 Uiso 0.5 1 calc R U P . .
H50B H -0.046000 0.676045 0.318655 0.183 Uiso 0.5 1 calc R U P . .
C51 C 0.062(2) 0.684(3) 0.4155(13) 0.227(16) Uani 0.5 1 d D . P . .
H51A H 0.010460 0.667430 0.455977 0.273 Uiso 0.5 1 calc R U P . .
H51B H 0.088651 0.769393 0.412937 0.273 Uiso 0.5 1 calc R U P . .
C52 C 0.168(2) 0.635(3) 0.4288(8) 0.232(17) Uani 0.5 1 d D . P . .
H52A H 0.238492 0.696276 0.452355 0.279 Uiso 0.5 1 calc R U P . .
H52B H 0.150000 0.568296 0.459346 0.279 Uiso 0.5 1 calc R U P . .
B3 B 0.6197(4) 0.2754(4) 0.1067(2) 0.0380(9) Uani 1 1 d . . . . .
H3 H 0.546532 0.313442 0.087661 0.046 Uiso 1 1 calc R U . . .
B4 B 0.7523(4) 0.2974(4) 0.0623(2) 0.0422(10) Uani 1 1 d . . . . .
H4 H 0.767027 0.350133 0.013798 0.051 Uiso 1 1 calc R U . . .
B5 B 0.8703(4) 0.3014(4) 0.1294(3) 0.0415(10) Uani 1 1 d . . . . .
H5 H 0.962610 0.356515 0.124616 0.050 Uiso 1 1 calc R U . . .
B6 B 0.8128(4) 0.2838(4) 0.2159(3) 0.0390(9) Uani 1 1 d . . . . .
H6 H 0.866833 0.327299 0.268435 0.047 Uiso 1 1 calc R U . . .
B7 B 0.5914(4) 0.1385(4) 0.1438(3) 0.0397(10) Uani 1 1 d . . . . .
H7 H 0.498910 0.084432 0.149221 0.048 Uiso 1 1 calc R U . . .
B8 B 0.6486(4) 0.1556(5) 0.0564(3) 0.0485(11) Uani 1 1 d . . . . .
H8 H 0.594932 0.113447 0.003485 0.058 Uiso 1 1 calc R U . . .
B9 B 0.8040(4) 0.1712(4) 0.0716(3) 0.0465(11) Uani 1 1 d . . . . .
H9 H 0.852760 0.138439 0.028633 0.056 Uiso 1 1 calc R U . . .
B10 B 0.8408(4) 0.1640(4) 0.1670(3) 0.0459(11) Uani 1 1 d . . . . .
H10 H 0.913796 0.126521 0.187338 0.055 Uiso 1 1 calc R U . . .
B11 B 0.7080(4) 0.1446(4) 0.2110(3) 0.0404(10) Uani 1 1 d . . . . .
H11 H 0.692533 0.095172 0.260880 0.049 Uiso 1 1 calc R U . . .
B12 B 0.7034(4) 0.0736(4) 0.1216(3) 0.0473(11) Uani 1 1 d . . . . .
H12 H 0.685648 -0.023726 0.111554 0.057 Uiso 1 1 calc R U . . .
B13 B 0.6201(3) 0.3590(3) 0.2541(2) 0.0308(8) Uani 1 1 d . . . . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C11 N1 B13 115.5(3) . . ?
C18 N2 C19 110.0(3) . . ?
C18 N2 C21 130.8(3) . . ?
C19 N2 C21 118.6(3) . . ?
C18 N3 C20 110.8(3) . . ?
C18 N3 C33 130.2(3) . . ?
C20 N3 C33 118.2(3) . . ?
C11 C1 C2 103.1(3) . . ?
C11 C1 B4 131.5(3) . . ?
C2 C1 B4 112.3(3) . . ?
C11 C1 B5 130.9(3) . . ?
C2 C1 B5 112.5(3) . . ?
B4 C1 B5 62.5(3) . . ?
C11 C1 B3 112.0(3) . . ?
C2 C1 B3 61.1(2) . . ?
B4 C1 B3 63.0(2) . . ?
B5 C1 B3 114.3(3) . . ?
C11 C1 B6 110.9(3) . . ?
C2 C1 B6 62.4(2) . . ?
B4 C1 B6 114.4(3) . . ?
B5 C1 B6 62.5(2) . . ?
B3 C1 B6 114.2(3) . . ?
B13 C2 C1 102.1(2) . . ?
B13 C2 B11 132.9(3) . . ?
C1 C2 B11 109.1(3) . . ?
B13 C2 B7 136.8(3) . . ?
C1 C2 B7 109.5(3) . . ?
B11 C2 B7 61.7(3) . . ?
B13 C2 B3 113.2(3) . . ?
C1 C2 B3 60.9(2) . . ?
B11 C2 B3 112.6(3) . . ?
B7 C2 B3 62.1(2) . . ?
B13 C2 B6 109.1(3) . . ?
C1 C2 B6 60.4(2) . . ?
B11 C2 B6 61.5(2) . . ?
B7 C2 B6 111.9(3) . . ?
B3 C2 B6 112.3(3) . . ?
N1 C11 C12 122.2(3) . . ?
N1 C11 C1 115.6(3) . . ?
C12 C11 C1 122.2(3) . . ?
C13 C12 C17 118.0(4) . . ?
C13 C12 C11 118.1(4) . . ?
C17 C12 C11 123.8(4) . . ?
C12 C13 C14 121.1(5) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 120.5(5) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
N3 C18 N2 104.2(3) . . ?
N3 C18 B13 131.1(3) . . ?
N2 C18 B13 122.5(3) . . ?
C20 C19 N2 107.7(3) . . ?
C20 C19 H19A 126.2 . . ?
N2 C19 H19A 126.2 . . ?
C19 C20 N3 107.2(3) . . ?
C19 C20 H20A 126.4 . . ?
N3 C20 H20A 126.4 . . ?
C26 C21 C22 123.3(4) . . ?
C26 C21 N2 119.6(3) . . ?
C22 C21 N2 116.4(4) . . ?
C23 C22 C21 116.5(5) . . ?
C23 C22 C27 120.3(5) . . ?
C21 C22 C27 123.1(4) . . ?
C24 C23 C22 121.2(5) . . ?
C24 C23 H23A 119.4 . . ?
C22 C23 H23A 119.4 . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C24 C25 C26 121.6(5) . . ?
C24 C25 H25A 119.2 . . ?
C26 C25 H25A 119.2 . . ?
C21 C26 C25 117.1(4) . . ?
C21 C26 C30 123.1(3) . . ?
C25 C26 C30 119.8(4) . . ?
C29 C27 C22 112.6(5) . . ?
C29 C27 C28 111.0(5) . . ?
C22 C27 C28 111.0(7) . . ?
C29 C27 H27A 107.3 . . ?
C22 C27 H27A 107.3 . . ?
C28 C27 H27A 107.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 C31 113.0(5) . . ?
C26 C30 C32 109.8(4) . . ?
C31 C30 C32 110.8(5) . . ?
C26 C30 H30A 107.7 . . ?
C31 C30 H30A 107.7 . . ?
C32 C30 H30A 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 123.6(3) . . ?
C38 C33 N3 118.8(3) . . ?
C34 C33 N3 117.1(3) . . ?
C35 C34 C33 116.8(4) . . ?
C35 C34 C39 119.5(4) . . ?
C33 C34 C39 123.7(4) . . ?
C36 C35 C34 120.7(4) . . ?
C36 C35 H35A 119.6 . . ?
C34 C35 H35A 119.6 . . ?
C37 C36 C35 120.9(4) . . ?
C37 C36 H36A 119.5 . . ?
C35 C36 H36A 119.5 . . ?
C36 C37 C38 121.9(5) . . ?
C36 C37 H37A 119.0 . . ?
C38 C37 H37A 119.0 . . ?
C33 C38 C37 115.9(4) . . ?
C33 C38 C42 123.5(3) . . ?
C37 C38 C42 120.4(4) . . ?
C34 C39 C41 111.0(4) . . ?
C34 C39 C40 114.5(4) . . ?
C41 C39 C40 109.6(4) . . ?
C34 C39 H39A 107.1 . . ?
C41 C39 H39A 107.1 . . ?
C40 C39 H39A 107.1 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 C43 112.6(4) . . ?
C38 C42 C44 110.7(4) . . ?
C43 C42 C44 109.8(4) . . ?
C38 C42 H42A 107.8 . . ?
C43 C42 H42A 107.8 . . ?
C44 C42 H42A 107.8 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C48 O1 C45 115.6(6) . . ?
O1 C45 C46 103.6(8) . . ?
O1 C45 H45A 111.0 . . ?
C46 C45 H45A 111.0 . . ?
O1 C45 H45B 111.0 . . ?
C46 C45 H45B 111.0 . . ?
H45A C45 H45B 109.0 . . ?
C45 C46 C47 109.6(9) . . ?
C45 C46 H46A 109.7 . . ?
C47 C46 H46A 109.7 . . ?
C45 C46 H46B 109.7 . . ?
C47 C46 H46B 109.7 . . ?
H46A C46 H46B 108.2 . . ?
C46 C47 C48 105.0(9) . . ?
C46 C47 H47A 110.7 . . ?
C48 C47 H47A 110.7 . . ?
C46 C47 H47B 110.7 . . ?
C48 C47 H47B 110.7 . . ?
H47A C47 H47B 108.8 . . ?
O1 C48 C47 104.6(8) . . ?
O1 C48 H48A 110.8 . . ?
C47 C48 H48A 110.8 . . ?
O1 C48 H48B 110.8 . . ?
C47 C48 H48B 110.8 . . ?
H48A C48 H48B 108.9 . . ?
C52 O2 C49 115.7(9) . . ?
O2 C49 C50 104.8(9) . . ?
O2 C49 H49A 110.8 . . ?
C50 C49 H49A 110.8 . . ?
O2 C49 H49B 110.8 . . ?
C50 C49 H49B 110.8 . . ?
H49A C49 H49B 108.9 . . ?
C49 C50 C51 102.5(12) . . ?
C49 C50 H50A 111.3 . . ?
C51 C50 H50A 111.3 . . ?
C49 C50 H50B 111.3 . . ?
C51 C50 H50B 111.3 . . ?
H50A C50 H50B 109.2 . . ?
C50 C51 C52 107.3(12) . . ?
C50 C51 H51A 110.2 . . ?
C52 C51 H51A 110.2 . . ?
C50 C51 H51B 110.2 . . ?
C52 C51 H51B 110.3 . . ?
H51A C51 H51B 108.5 . . ?
O2 C52 C51 100.7(10) . . ?
O2 C52 H52A 111.6 . . ?
C51 C52 H52A 111.6 . . ?
O2 C52 H52B 111.6 . . ?
C51 C52 H52B 111.6 . . ?
H52A C52 H52B 109.4 . . ?
C1 B3 C2 58.1(2) . . ?
C1 B3 B7 104.7(3) . . ?
C2 B3 B7 58.8(2) . . ?
C1 B3 B8 104.9(3) . . ?
C2 B3 B8 106.6(3) . . ?
B7 B3 B8 60.8(3) . . ?
C1 B3 B4 58.1(2) . . ?
C2 B3 B4 106.0(3) . . ?
B7 B3 B4 108.5(3) . . ?
B8 B3 B4 60.3(3) . . ?
C1 B3 H3 124.8 . . ?
C2 B3 H3 123.3 . . ?
B7 B3 H3 122.0 . . ?
B8 B3 H3 122.1 . . ?
B4 B3 H3 121.9 . . ?
C1 B4 B5 59.0(2) . . ?
C1 B4 B9 104.6(3) . . ?
B5 B4 B9 59.8(3) . . ?
C1 B4 B3 58.9(2) . . ?
B5 B4 B3 108.1(3) . . ?
B9 B4 B3 107.3(3) . . ?
C1 B4 B8 104.9(3) . . ?
B5 B4 B8 108.2(3) . . ?
B9 B4 B8 60.0(3) . . ?
B3 B4 B8 59.5(2) . . ?
C1 B4 H4 124.5 . . ?
B5 B4 H4 121.3 . . ?
B9 B4 H4 122.7 . . ?
B3 B4 H4 121.8 . . ?
B8 B4 H4 122.3 . . ?
C1 B5 B4 58.5(2) . . ?
C1 B5 B9 104.7(3) . . ?
B4 B5 B9 60.5(3) . . ?
C1 B5 B10 104.3(3) . . ?
B4 B5 B10 108.5(3) . . ?
B9 B5 B10 60.3(3) . . ?
C1 B5 B6 59.1(2) . . ?
B4 B5 B6 108.4(3) . . ?
B9 B5 B6 107.8(3) . . ?
B10 B5 B6 59.2(2) . . ?
C1 B5 H5 124.9 . . ?
B4 B5 H5 121.0 . . ?
B9 B5 H5 122.2 . . ?
B10 B5 H5 122.5 . . ?
B6 B5 H5 121.6 . . ?
C1 B6 C2 57.3(2) . . ?
C1 B6 B10 104.8(3) . . ?
C2 B6 B10 105.5(3) . . ?
C1 B6 B11 103.8(3) . . ?
C2 B6 B11 58.0(2) . . ?
B10 B6 B11 60.8(3) . . ?
C1 B6 B5 58.4(2) . . ?
C2 B6 B5 105.2(3) . . ?
B10 B6 B5 60.4(3) . . ?
B11 B6 B5 108.4(3) . . ?
C1 B6 H6 125.0 . . ?
C2 B6 H6 124.3 . . ?
B10 B6 H6 122.3 . . ?
B11 B6 H6 122.4 . . ?
B5 B6 H6 121.8 . . ?
C2 B7 B11 59.1(2) . . ?
C2 B7 B12 106.6(3) . . ?
B11 B7 B12 61.0(3) . . ?
C2 B7 B3 59.1(2) . . ?
B11 B7 B3 108.1(3) . . ?
B12 B7 B3 108.0(3) . . ?
C2 B7 B8 106.1(3) . . ?
B11 B7 B8 109.0(3) . . ?
B12 B7 B8 60.2(3) . . ?
B3 B7 B8 59.7(3) . . ?
C2 B7 H7 123.6 . . ?
B11 B7 H7 120.9 . . ?
B12 B7 H7 121.6 . . ?
B3 B7 H7 121.8 . . ?
B8 B7 H7 121.9 . . ?
B3 B8 B12 106.9(3) . . ?
B3 B8 B9 107.6(3) . . ?
B12 B8 B9 59.9(3) . . ?
B3 B8 B4 60.1(2) . . ?
B12 B8 B4 107.5(4) . . ?
B9 B8 B4 59.8(3) . . ?
B3 B8 B7 59.5(2) . . ?
B12 B8 B7 59.1(3) . . ?
B9 B8 B7 106.8(4) . . ?
B4 B8 B7 107.2(3) . . ?
B3 B8 H8 122.0 . . ?
B12 B8 H8 122.3 . . ?
B9 B8 H8 122.0 . . ?
B4 B8 H8 121.8 . . ?
B7 B8 H8 122.6 . . ?
B5 B9 B12 108.2(3) . . ?
B5 B9 B4 59.7(3) . . ?
B12 B9 B4 107.8(3) . . ?
B5 B9 B10 60.1(3) . . ?
B12 B9 B10 60.2(3) . . ?
B4 B9 B10 107.7(3) . . ?
B5 B9 B8 108.3(3) . . ?
B12 B9 B8 60.0(3) . . ?
B4 B9 B8 60.2(3) . . ?
B10 B9 B8 108.3(3) . . ?
B5 B9 H9 121.6 . . ?
B12 B9 H9 121.7 . . ?
B4 B9 H9 122.0 . . ?
B10 B9 H9 121.6 . . ?
B8 B9 H9 121.5 . . ?
B6 B10 B5 60.4(2) . . ?
B6 B10 B9 108.3(3) . . ?
B5 B10 B9 59.6(3) . . ?
B6 B10 B11 60.1(2) . . ?
B5 B10 B11 107.9(3) . . ?
B9 B10 B11 107.7(3) . . ?
B6 B10 B12 108.3(3) . . ?
B5 B10 B12 107.5(4) . . ?
B9 B10 B12 59.8(3) . . ?
B11 B10 B12 59.9(3) . . ?
B6 B10 H10 121.3 . . ?
B5 B10 H10 121.9 . . ?
B9 B10 H10 121.9 . . ?
B11 B10 H10 121.9 . . ?
B12 B10 H10 121.8 . . ?
C2 B11 B7 59.2(2) . . ?
C2 B11 B6 60.5(2) . . ?
B7 B11 B6 109.1(3) . . ?
C2 B11 B12 105.7(3) . . ?
B7 B11 B12 59.8(3) . . ?
B6 B11 B12 107.7(3) . . ?
C2 B11 B10 106.2(3) . . ?
B7 B11 B10 108.2(3) . . ?
B6 B11 B10 59.2(2) . . ?
B12 B11 B10 60.1(3) . . ?
C2 B11 H11 123.2 . . ?
B7 B11 H11 121.2 . . ?
B6 B11 H11 121.2 . . ?
B12 B11 H11 122.5 . . ?
B10 B11 H11 122.3 . . ?
B7 B12 B9 108.4(3) . . ?
B7 B12 B8 60.8(3) . . ?
B9 B12 B8 60.2(3) . . ?
B7 B12 B11 59.2(2) . . ?
B9 B12 B11 107.8(3) . . ?
B8 B12 B11 108.0(3) . . ?
B7 B12 B10 107.6(3) . . ?
B9 B12 B10 60.0(3) . . ?
B8 B12 B10 108.2(3) . . ?
B11 B12 B10 60.0(3) . . ?
B7 B12 H12 121.7 . . ?
B9 B12 H12 121.6 . . ?
B8 B12 H12 121.3 . . ?
B11 B12 H12 122.1 . . ?
B10 B12 H12 121.8 . . ?
N1 B13 C18 109.5(3) . . ?
N1 B13 C2 103.7(3) . . ?
C18 B13 C2 124.0(3) . . ?
N1 B13 Br1 108.1(2) . . ?
C18 B13 Br1 101.4(2) . . ?
C2 B13 Br1 109.6(2) . . ?
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
Br1 B13 2.072(4) . ?
N1 C11 1.271(5) . ?
N1 B13 1.518(5) . ?
N2 C18 1.372(4) . ?
N2 C19 1.380(5) . ?
N2 C21 1.457(4) . ?
N3 C18 1.355(4) . ?
N3 C20 1.380(5) . ?
N3 C33 1.461(4) . ?
C1 C11 1.527(5) . ?
C1 C2 1.664(4) . ?
C1 B4 1.699(6) . ?
C1 B5 1.707(5) . ?
C1 B3 1.713(6) . ?
C1 B6 1.719(5) . ?
C2 B13 1.657(5) . ?
C2 B11 1.708(5) . ?
C2 B7 1.709(5) . ?
C2 B3 1.716(5) . ?
C2 B6 1.752(5) . ?
C11 C12 1.485(5) . ?
C12 C13 1.379(6) . ?
C12 C17 1.399(6) . ?
C13 C14 1.389(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.367(9) . ?
C14 H14A 0.9500 . ?
C15 C16 1.370(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.387(7) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 B13 1.651(5) . ?
C19 C20 1.325(5) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 C26 1.380(6) . ?
C21 C22 1.401(6) . ?
C22 C23 1.400(7) . ?
C22 C27 1.528(8) . ?
C23 C24 1.370(9) . ?
C23 H23A 0.9500 . ?
C24 C25 1.362(9) . ?
C24 H24A 0.9500 . ?
C25 C26 1.393(6) . ?
C25 H25A 0.9500 . ?
C26 C30 1.509(6) . ?
C27 C29 1.512(10) . ?
C27 C28 1.535(9) . ?
C27 H27A 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.515(8) . ?
C30 C32 1.545(7) . ?
C30 H30A 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C38 1.400(6) . ?
C33 C34 1.400(6) . ?
C34 C35 1.400(6) . ?
C34 C39 1.513(6) . ?
C35 C36 1.377(8) . ?
C35 H35A 0.9500 . ?
C36 C37 1.361(8) . ?
C36 H36A 0.9500 . ?
C37 C38 1.402(6) . ?
C37 H37A 0.9500 . ?
C38 C42 1.498(6) . ?
C39 C41 1.526(6) . ?
C39 C40 1.529(7) . ?
C39 H39A 1.0000 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.531(7) . ?
C42 C44 1.534(6) . ?
C42 H42A 1.0000 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
O1 C48 1.418(7) . ?
O1 C45 1.428(7) . ?
C45 C46 1.482(8) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.494(9) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.524(8) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
O2 C52 1.417(9) . ?
O2 C49 1.423(9) . ?
C49 C50 1.496(9) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.503(9) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.520(9) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
B3 B7 1.767(6) . ?
B3 B8 1.772(6) . ?
B3 B4 1.783(6) . ?
B3 H3 1.1200 . ?
B4 B5 1.767(7) . ?
B4 B9 1.780(7) . ?
B4 B8 1.787(7) . ?
B4 H4 1.1200 . ?
B5 B9 1.769(7) . ?
B5 B10 1.777(6) . ?
B5 B6 1.777(6) . ?
B5 H5 1.1200 . ?
B6 B10 1.755(6) . ?
B6 B11 1.771(6) . ?
B6 H6 1.1200 . ?
B7 B11 1.751(7) . ?
B7 B12 1.761(6) . ?
B7 B8 1.791(6) . ?
B7 H7 1.1200 . ?
B8 B12 1.781(8) . ?
B8 B9 1.784(7) . ?
B8 H8 1.1200 . ?
B9 B12 1.779(6) . ?
B9 B10 1.781(7) . ?
B9 H9 1.1200 . ?
B10 B11 1.783(6) . ?
B10 B12 1.786(7) . ?
B10 H10 1.1200 . ?
B11 B12 1.783(7) . ?
B11 H11 1.1200 . ?
B12 H12 1.1200 . ?
