Synthesis of Dithieno[2,3-b:4',3'-d]siloles and Their Selective Bromination
Jincan Zhao; Dongfang Qiu; Jianwu Shi; Hua Wang; Journal of Organic Chemistry 77 (2012) 2929–2934; doi:10.1021/jo202111z

data_4027059
_publ_section_title
;
 Synthesis of Dithieno[2,3-b:4',3'-d]siloles and Their Selective
 Bromination
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2929
_journal_page_last               2934
_journal_paper_doi               10.1021/jo202111z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H25 Br S2 Si3'
_chemical_formula_weight         445.66
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.458(11)
_cell_angle_beta                 110.078(11)
_cell_angle_gamma                117.942(7)
_cell_formula_units_Z            4
_cell_length_a                   13.753(7)
_cell_length_b                   14.627(7)
_cell_length_c                   14.647(12)
_cell_measurement_reflns_used    3177
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.53
_cell_measurement_theta_min      2.51
_cell_volume                     2270(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11572
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_T_max  0.7388
_exptl_absorpt_correction_T_min  0.5845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.844
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0150(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7924
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1352P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2138
_refine_ls_wR_factor_ref         0.2325
_reflns_number_gt                4915
_reflns_number_total             7924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202111z_si_004.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4027059