A Pd-catalyzed route to carborane-fused boron heterocycles.
Zhu, Mengjie; Wang, Puzhao; Wu, Zhengqiu; Zhong, Yangfa; Su, Laiman; Xin, Yuquan; Spokoyny, Alexander M.; Zou, Chao; Mu, Xin; Chemical science 15 (2024) 10392–10401; doi:10.1039/d4sc02214a

data_1571739
_publ_section_title
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 A Pd-catalyzed route to carborane-fused boron heterocycles.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10392
_journal_page_last               10401
_journal_paper_doi               10.1039/d4sc02214a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H26 B10 N2 O2'
_chemical_formula_sum            'C20 H26 B10 N2 O2'
_chemical_formula_weight         434.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-01-04 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0742(6)
_cell_length_b                   8.9131(5)
_cell_length_c                   11.9898(7)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.753
_cell_measurement_theta_min      3.237
_cell_volume                     1172.59(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9160
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.902
_diffrn_reflns_theta_min         4.439
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1612 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.5429.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0601
_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/[\s^2^(Fo^2^)+(0.0912P)^2^+0.0709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.800
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                2909
_reflns_number_total             3990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02214a2.cif
_cod_data_source_block           mj23466_0m
_cod_depositor_comments
'Adding full bibliography for 1571739--1571749.cif.'
_cod_database_code               1571739
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C12(H12), C3(H3), C7(H7), C13(H13), C10(H10), C8(H8),
 C19(H19), C4(H4)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C11(H11A,H11B,H11C)
2.c Boron cage BH refined with riding coordinates:
 C1(H1), C2(H2), B1(H1A), B8(H8A), B4(H4A), B3(H3A), B7(H7A), B5(H5), B2(H2A),
 B6(H6)
;
_shelx_res_checksum              51921
_olex2_submission_special_instructions 'No special instructions were received'