Synthesis of imidazo[1,2-c]thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides.
Peng, Xiangjun; Qin, Feng; Xu, Mengyue; Zhu, Shaojie; Pan, Yingming; Tang, Haitao; Meng, Xiujin; Wang, Hengshan; Organic & biomolecular chemistry 17 (2019) 8403–8407; doi:10.1039/c9ob01664c

data_7157059
_publ_section_title
;
 Synthesis of imidazo[1,2-c]thiazoles through Pd-catalyzed bicyclization
 of tert-butyl isonitrile with thioamides.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8403
_journal_page_last               8407
_journal_paper_doi               10.1039/c9ob01664c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C25 H28 F2 N4 S'
_chemical_formula_sum            'C25 H28 F2 N4 S'
_chemical_formula_weight         454.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-12 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.346(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3522(13)
_cell_length_b                   11.8099(8)
_cell_length_c                   10.9691(5)
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0720
_cell_measurement_theta_min      4.4390
_cell_volume                     2357.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     31.00  62.00   1.00    3.00    --   41.11 -37.00 -90.00   31
  2  \w     45.00  72.00   1.00    3.00    --   41.11 -77.00 -90.00   27
  3  \w     78.00 130.00   1.00    3.00    --  107.58 -77.00-150.00   52
  4  \w     84.00 173.00   1.00    3.00    --  107.58  45.00 -60.00   89
  5  \w    146.00 173.00   1.00    3.00    --  107.58 125.00  90.00   27
  6  \w     75.00 178.00   1.00    3.00    --  107.58  77.00 -30.00  103
  7  \w     95.00 167.00   1.00    3.00    --  107.58 125.00-120.00   72
  8  \w     57.00  96.00   1.00    3.00    --   41.11-125.00 150.00   39
  9  \w     36.00 122.00   1.00    3.00    --  107.58-125.00 -90.00   86
 10  \w    -31.00  -4.00   1.00    3.00    --   41.11 -77.00 -90.00   27
 11  \w    -32.00  16.00   1.00    3.00    --   41.11 -37.00 -90.00   48
 12  \w   -107.00 -49.00   1.00    3.00    --  -41.11 -37.00 120.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0844361000
_diffrn_orient_matrix_UB_12      -0.0082589000
_diffrn_orient_matrix_UB_13      -0.0231399000
_diffrn_orient_matrix_UB_21      -0.0059070000
_diffrn_orient_matrix_UB_22      0.1276025000
_diffrn_orient_matrix_UB_23      0.0259747000
_diffrn_orient_matrix_UB_31      0.0018666000
_diffrn_orient_matrix_UB_32      0.0254829000
_diffrn_orient_matrix_UB_33      -0.1373018000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8885
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.998
_diffrn_reflns_theta_min         2.427
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0844
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1921P)^2^+17.1024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3912
_refine_ls_wR_factor_ref         0.2450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3257
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01664c2.cif
_cod_data_source_block           exp_1558
_cod_depositor_comments          'Adding full bibliography for 7157059.cif.'
_cod_database_code               7157059
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C18, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C18 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C21) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C18) = Uanis(C21)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C16(H16), C2(H2), C6(H6), C3(H3), C5(H5)
4.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C21(H21A,H21B,
 H21C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.709
_oxdiff_exptl_absorpt_empirical_full_min 0.698