Selectivity of Br/Li Exchange and Deprotonation of 4,4'-Dibromo-3,3'-bithiophene for Synthesis of Symmetrical and Unsymmetrical Dithienoheteroaromatic Rings
Hui Han; Wenling Zhao; Jinsheng Song; Chunli Li; Hua Wang; Journal of Organic Chemistry 78 (2013) 2726–2730; doi:10.1021/jo302635y

data_4028029
_publ_section_title
;
 Selectivity of Br/Li Exchange and Deprotonation of
 4,4'-Dibromo-3,3'-bithiophene for Synthesis of Symmetrical and
 Unsymmetrical Dithienoheteroaromatic Rings
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2726
_journal_page_last               2730
_journal_paper_doi               10.1021/jo302635y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C8 H3 Br S3'
_chemical_formula_weight         275.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.708(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.957(4)
_cell_length_b                   4.0031(10)
_cell_length_c                   15.819(4)
_cell_measurement_reflns_used    651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.95
_cell_measurement_theta_min      2.88
_cell_volume                     902.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1084
_diffrn_reflns_av_sigmaI/netI    0.2427
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3943
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    5.180
_exptl_absorpt_correction_T_max  0.6820
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       0.019(5)
_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   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.1372
_refine_ls_R_factor_gt           0.0858
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0128P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2367
_reflns_number_gt                949
_reflns_number_total             1577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302635y_si_001.cif
_cod_data_source_block           a
_cod_database_code               4028029