Photoredox B-H functionalization to selective B-N(sp<sup>3</sup>) coupling of nido-carborane with primary and secondary amines.
Huang, Ronghui; Zhao, Weijia; Xu, Shengwen; Xu, Jingkai; Li, Chunxiao; Lu, Changsheng; Yan, Hong; Chemical communications (Cambridge, England) 57 (2021) 8580–8583; doi:10.1039/d1cc03326c

data_7128696
_publ_section_title
;
 Photoredox B-H functionalization to selective B-N(sp<sup>3</sup>)
 coupling of nido-carborane with primary and secondary amines.
;
_journal_issue                   69
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8580
_journal_page_last               8583
_journal_paper_doi               10.1039/d1cc03326c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C H2 Cl2, C22 H30 B9 N'
_chemical_formula_sum            'C23 H32 B9 Cl2 N'
_chemical_formula_weight         490.68
_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     dual
_audit_creation_date             2020-12-01
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-12-01 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                81.973(2)
_cell_angle_beta                 88.116(2)
_cell_angle_gamma                82.705(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9564(3)
_cell_length_b                   11.0803(5)
_cell_length_c                   17.5164(8)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.34
_cell_volume                     1325.94(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11558
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.068
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9085.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0170P)^2^+1.1616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4160
_reflns_number_total             5950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03326c2.cif
_cod_data_source_block           2047487
_cod_depositor_comments
'Adding full bibliography for 7128695--7128697.cif.'
_cod_database_code               7128696
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C006, C005, C00K
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1A) \\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(Cl2A)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Sof(Cl1A)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C00K(H00N), C00L(H00O), C00Q(H00R), C00Y(H00Z)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              67112
_olex2_submission_special_instructions 'No special instructions were received'