Reactions of BICAAC with hydroboranes: propensity for Lewis adduct formation and carbene insertion into B-H bond
Manar, Krishna Kumar; porwal, vishal kumar; Kamte, Rohit S.; Adhikari, Manu; Thakur, Sandeep Kumar; Bawari, Deependra; Roychoudhury, Angshuman; Singh, Sanjay; Dalton Transactions  (2019) –; doi:10.1039/C9DT03382C

data_7701411
_publ_section_title
;
 Reactions of BICAAC with hydroboranes: propensity for Lewis adduct
 formation and carbene insertion into B-H bond
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03382C
_journal_year                    2019
_chemical_formula_moiety         '2(C22 H33 B Br3 N)'
_chemical_formula_sum            'C44 H66 B2 Br6 N2'
_chemical_formula_weight         1124.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-20 deposited with the CCDC.    2019-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.211(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6037(4)
_cell_length_b                   17.7087(3)
_cell_length_c                   17.5684(4)
_cell_measurement_reflns_used    12125
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      31.7350
_cell_measurement_theta_min      2.6890
_cell_volume                     4711.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9555
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00  60.00  624
  2  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00 -60.00  624
  3  \w    -69.00  10.20   0.30   15.00    --   29.89  54.00-180.00  264
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0203805000
_diffrn_orient_matrix_UB_12      -0.0127137000
_diffrn_orient_matrix_UB_13      0.0419180000
_diffrn_orient_matrix_UB_21      -0.0283046000
_diffrn_orient_matrix_UB_22      -0.0319054000
_diffrn_orient_matrix_UB_23      -0.0104785000
_diffrn_orient_matrix_UB_31      0.0312658000
_diffrn_orient_matrix_UB_32      -0.0205959000
_diffrn_orient_matrix_UB_33      -0.0096282000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            53391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.766
_diffrn_reflns_theta_min         2.628
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.303
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         16657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.7086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11225
_reflns_number_total             16657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt03382c2.cif
_cod_data_source_block           Compound5_200k
_cod_database_code               7701411
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.233
_shelx_estimated_absorpt_t_min   0.183
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C17(H17), C20(H20), C25(H25), C39(H39), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C26(H26A,H26B), C28(H28A,H28B),
 C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C35(H35), C36(H36), C37(H37)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.831