Boron Tribromide as Reagent for Anti-Markovnikov Addition of HBr to Cyclopropanes
Gieuw, Matthew H.; Chen, Shuming; Ke, Zhihai; Houk, Kendall N.; Yeung, Ying-Yeung; Chemical Science  (2020) –; doi:10.1039/D0SC02567D

data_1558780
_publ_section_title
;
 Boron Tribromide as Reagent for Anti-Markovnikov Addition of HBr to
 Cyclopropanes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02567D
_journal_year                    2020
_chemical_formula_sum            'C16 H16 Br2'
_chemical_formula_weight         368.11
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-17 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.525(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2066(5)
_cell_length_b                   16.0484(10)
_cell_length_c                   5.6011(3)
_cell_measurement_reflns_used    93
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     725.27(7)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10259
_diffrn_reflns_point_group_measured_fraction_full 0.994
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.538
_exptl_absorpt_coefficient_mu    5.569
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2968
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0310P)^2^+0.4079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1199
_reflns_number_total             1306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02567d2.cif
_cod_data_source_block           79p
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558780
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.214
_shelx_estimated_absorpt_t_max   0.402
_shelx_res_checksum              26161