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_4028030
_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            'C9 H3 Br O S2'
_chemical_formula_weight         271.14
_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                84.27(2)
_cell_angle_beta                 84.91(2)
_cell_angle_gamma                82.84(2)
_cell_formula_units_Z            4
_cell_length_a                   7.802(10)
_cell_length_b                   7.872(11)
_cell_length_c                   15.48(2)
_cell_measurement_temperature    296(2)
_cell_volume                     936(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 0.921
_diffrn_measured_fraction_theta_max 0.921
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.1216
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    4.787
_exptl_absorpt_correction_T_max  0.5337
_exptl_absorpt_correction_T_min  0.4632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0739
_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^)+(0.0606P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                1695
_reflns_number_total             3039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302635y_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028030