Ligand-free copper-catalyzed regioselective C-2 arylation of imidazo[2,1-b]thiazoles.
Huang, Guoli; Sun, Hongsheng; Qiu, Xiaojie; Jin, Can; Lin, Chen; Shen, Yingzhong; Jiang, Juli; Wang, Leyong; Organic letters 13 (2011) 5224–5227; doi:10.1021/ol2021109

data_1502480
_publ_section_title
;
 Ligand-free copper-catalyzed regioselective C-2 arylation of
 imidazo[2,1-b]thiazoles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5224
_journal_page_last               5227
_journal_paper_doi               10.1021/ol2021109
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C18 H14 N2 S'
_chemical_formula_sum            'C18 H14 N2 S'
_chemical_formula_weight         290.37
_space_group_IT_number           14
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4161(11)
_cell_length_b                   13.563(2)
_cell_length_c                   29.240(4)
_cell_measurement_reflns_used    5759
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      0.997
_cell_volume                     2941.1(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'fine-focus sealed tube'
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15731
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.386
_exptl_crystal_size_min          0.313
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0472P)^2^+1.5049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                3619
_reflns_number_total             5759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2021109_si_002.cif
_cod_data_source_block           hgl06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P_21/a
_cod_database_code               1502480