Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A(3)-Coupling in Batch and Continuous Flow.
Rassokhina, Irina V.; Tikhonova, Tatyana A.; Kobylskoy, Sergey G.; Babkin, Igor Yu; Shirinian, Valerii Z.; Gevorgyan, Vladimir; Zavarzin, Igor V.; Volkova, Yulia A.; The Journal of organic chemistry 82 (2017) 9682–9692; doi:10.1021/acs.joc.7b01762

data_4033075
_publ_section_title
;
 Synthesis of Imidazo[2,1-b]thiazoles via Copper-Catalyzed A(3)-Coupling
 in Batch and Continuous Flow.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9682
_journal_page_last               9692
_journal_paper_doi               10.1021/acs.joc.7b01762
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H15 Cl N2 O2 S'
_chemical_formula_sum            'C19 H15 Cl N2 O2 S'
_chemical_formula_weight         370.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                85.958(6)
_cell_angle_beta                 81.538(6)
_cell_angle_gamma                76.058(6)
_cell_formula_units_Z            4
_cell_length_a                   8.512(2)
_cell_length_b                   12.733(4)
_cell_length_c                   16.119(4)
_cell_measurement_reflns_used    514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1676.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_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, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19238
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.649
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.961
_exptl_transmission_factor_min   0.867
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5240
_reflns_number_total             8086
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo7b01762_si_002.cif
_cod_data_source_block           1_a
_cod_original_cell_volume        1675.8(8)
_cod_database_code               4033075
_shelx_estimated_absorpt_t_min   0.867
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           2014/6
_shelx_res_checksum              713
_shelx_hkl_checksum              43005