Catalyst-Free and Regioconvergent Substitution Reactions of Bromothiophenes with a BH3-Substituted Phosphide Anion.
Imamoto, Tsuneo; Horiuchi, Yumi; Tamura, Ken; Sugiya, Masashi; Masu, Hyuma; Organic letters 18 (2016) 4132–4135; doi:10.1021/acs.orglett.6b02094

data_1555691
_publ_section_title
;
 Catalyst-Free and Regioconvergent Substitution Reactions of
 Bromothiophenes with a BH3-Substituted Phosphide Anion.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4132
_journal_page_last               4135
_journal_paper_doi               10.1021/acs.orglett.6b02094
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C9 H16 B Br2 P S'
_chemical_formula_weight         357.88
_chemical_name_common            ThioBr2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1372(4)
_cell_length_b                   12.6521(7)
_cell_length_c                   31.0391(17)
_cell_measurement_reflns_used    3800
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.7726
_cell_measurement_theta_min      2.6248
_cell_volume                     2802.8(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            15013
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.625
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.012
_exptl_absorpt_correction_T_max  0.58
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0353P)^2^+1.9061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                2487
_reflns_number_total             3223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02094_si_003.cif
_cod_data_source_block           a151105mas1
_cod_database_code               1555691
_shelx_res_checksum              68250
_shelx_hkl_checksum              91471