Versatile chemistry of six-membered NHC with boranes: bromination at sp3 borane, activation of B–H bond of HBpin, and ring expansion of NHC
Kundu, Gargi; Dixit, Ruchi; Tothadi, Srinu; Vanka, Kumar; Sen, Sakya Singha; Dalton Transactions  (2022) –; doi:10.1039/D2DT01707E

data_7711057
_publ_section_title
;
 Versatile chemistry of six-membered NHC with boranes: bromination at sp3
 borane, activation of B--H bond of HBpin, and ring expansion of NHC
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01707E
_journal_year                    2022
_chemical_formula_moiety         '2(C28 H41 B Br1.50 N2)'
_chemical_formula_sum            'C56 H82 B2 Br3 N4'
_chemical_formula_weight         1072.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-06 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.104(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.529(5)
_cell_length_b                   19.135(10)
_cell_length_c                   13.705(6)
_cell_measurement_reflns_used    9491
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.33
_cell_measurement_theta_min      2.53
_cell_volume                     2726(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            98762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.317
_diffrn_reflns_theta_min         2.229
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.258
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1030 before and 0.0739 after correction. The Ratio of minimum to maximum transmission is 0.7554. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1122
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.462
_refine_diff_density_min         -2.141
_refine_diff_density_rms         0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         9669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0554
_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/[\s^2^(Fo^2^)+(0.0745P)^2^+7.1046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8027
_reflns_number_total             9669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01707e2.cif
_cod_data_source_block           mo_gk_bhno2_2_0m_a
_cod_database_code               7711057
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.661
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br2(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8), C15(H15), C22(H22), B1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              13543
_olex2_submission_special_instructions 'No special instructions were received'