Copper- and Palladium-Catalyzed Cross-Coupling Reactions for the Synthesis of N-Fused Benzo[4,5]imidazo[2,1-b]thiazole Derivatives via Substituted trans-1,2-Diiodoalkenes, 1H-Benzo[d]imidazole-2-thiols, and Halobenzenes.
Shen, Guodong; Yang, Bingchuan; Huang, Xianqiang; Hou, Yaxin; Gao, Huan; Cui, Jichun; Cui, Chuansheng; Zhang, Tongxin; The Journal of organic chemistry 82 (2017) 3798–3805; doi:10.1021/acs.joc.7b00162

data_4032403
_publ_section_title
;
 Copper- and Palladium-Catalyzed Cross-Coupling Reactions for the
 Synthesis of N-Fused Benzo[4,5]imidazo[2,1-b]thiazole Derivatives via
 Substituted trans-1,2-Diiodoalkenes, 1H-Benzo[d]imidazole-2-thiols, and
 Halobenzenes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3798
_journal_page_last               3805
_journal_paper_doi               10.1021/acs.joc.7b00162
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C21 H14 N2 S'
_chemical_formula_weight         326.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.341(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1447(9)
_cell_length_b                   15.0655(19)
_cell_length_c                   17.331(2)
_cell_measurement_reflns_used    1044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.4330
_cell_measurement_theta_min      3.5800
_cell_volume                     1591.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.1443
_diffrn_reflns_av_sigmaI/netI    0.1643
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11702
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0864P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.2217
_reflns_number_gt                1365
_reflns_number_total             2816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00162_si_002.cif
_cod_data_source_block           exp_7567
_cod_depositor_comments          'Adding full bibliography for 4032403.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4032403