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_1555692
_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            3-4Br2
_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
_cell_angle_alpha                90
_cell_angle_beta                 101.9463(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1556(6)
_cell_length_b                   12.2943(7)
_cell_length_c                   11.2898(6)
_cell_measurement_reflns_used    3283
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.9614
_cell_measurement_theta_min      2.4571
_cell_volume                     1379.07(13)
_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 0.996
_diffrn_measured_fraction_theta_max 0.973
_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  0.0162
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7750
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.457
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.109
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.369
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0314P)^2^+1.1232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                2626
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02094_si_002.cif
_cod_data_source_block           a151125mas1
_cod_database_code               1555692
_shelx_res_checksum              30094
_shelx_hkl_checksum              34940