Palladium-Catalyzed Template Directed C-5 Selective Olefination of Thiazoles.
Achar, Tapas Kumar; Biswas, Jyoti Prasad; Porey, Sandip; Pal, Tapas; Ramakrishna, Kankanala; Maiti, Siddhartha; Maiti, Debabrata; The Journal of organic chemistry 84 (2019) 8315–8321; doi:10.1021/acs.joc.9b01074

data_4034660
_publ_section_title
;
 Palladium-Catalyzed Template Directed C-5 Selective Olefination of
 Thiazoles.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8315
_journal_page_last               8321
_journal_paper_doi               10.1021/acs.joc.9b01074
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C12 H6 F5 N S'
_chemical_formula_sum            'C12 H6 F5 N S'
_chemical_formula_weight         291.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-25
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                78.395(4)
_cell_angle_beta                 81.878(3)
_cell_angle_gamma                82.656(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4999(2)
_cell_length_b                   10.9169(6)
_cell_length_c                   14.4193(7)
_cell_measurement_reflns_used    10435
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.8340
_cell_measurement_theta_min      2.2320
_cell_volume                     1138.82(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -110.00  70.00   0.50    6.00    --  -20.00   0.00 108.00  360
  2  \w    -87.00  19.00   0.50    6.00    --  -20.00 -72.00 108.00  212
  3  \w    -63.00  19.00   0.50    6.00    --  -20.00 -72.00-108.00  164
  4  \w    -33.50  15.00   0.50    6.00    --  -20.00 -72.00 -36.00   97
  5  \w    -44.00 -14.00   0.50    6.00    --  -20.00 -72.00-180.00   60
  6  \w    -59.00 -28.50   0.50    6.00    --  -20.00  72.00 108.00   61
  7  \w    -59.00  70.00   0.50    6.00    --  -20.00  72.00 -36.00  258
  8  \w    -59.00  70.00   0.50    6.00    --  -20.00  72.00-108.00  258
  9  \w    -90.00 -70.00   0.50    6.00    --  -20.00 -72.00  36.00   40
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003343000
_diffrn_orient_matrix_UB_12      0.0477077000
_diffrn_orient_matrix_UB_13      -0.0414469000
_diffrn_orient_matrix_UB_21      0.0033811000
_diffrn_orient_matrix_UB_22      -0.0462744000
_diffrn_orient_matrix_UB_23      -0.0285734000
_diffrn_orient_matrix_UB_31      -0.0959787000
_diffrn_orient_matrix_UB_32      0.0053756000
_diffrn_orient_matrix_UB_33      0.0048696000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16310
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.914
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1221P)^2^+0.3992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1755
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             3997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01074_si_002.cif
_cod_data_source_block           dm-ta-361-e2_mo
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C12 H6 F5 N S)'
_cod_original_formula_sum        'C24 H12 F10 N2 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     582.48
_cod_database_code               4034660
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.933
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.16
_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.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00T(H00T), C00W(H00W), C00Z(H00Z), C010(H010), C012(H012)
2.b Idealised Me refined as rotating group:
 C00J(H00D,H00E,H00F), C00P(H00A,H00B,H00C)
;
_shelx_res_checksum              69714
_shelx_hkl_checksum              54426
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.736