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_4034658
_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         'C8 H5 Cl F3 N O2 S'
_chemical_formula_sum            'C8 H5 Cl F3 N O2 S'
_chemical_formula_weight         271.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2188(5)
_cell_length_b                   19.2559(9)
_cell_length_c                   6.6689(4)
_cell_measurement_reflns_used    3435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7850
_cell_measurement_theta_min      2.0920
_cell_volume                     1055.42(10)
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -106.00  67.00   0.50    8.00    --  -20.00   0.00  36.00  346
  2  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00  36.00   61
  3  \w    -98.00  -2.50   0.50    8.00    --  -20.00   0.00-108.00  191
;
_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      0.0706685000
_diffrn_orient_matrix_UB_12      -0.0038216000
_diffrn_orient_matrix_UB_13      0.0600159000
_diffrn_orient_matrix_UB_21      0.0226595000
_diffrn_orient_matrix_UB_22      0.0346703000
_diffrn_orient_matrix_UB_23      -0.0223699000
_diffrn_orient_matrix_UB_31      -0.0439457000
_diffrn_orient_matrix_UB_32      0.0118140000
_diffrn_orient_matrix_UB_33      0.0850277000
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5622
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.986
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_min         3.259
_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    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54278
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0454P)^2^+0.3277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                875
_reflns_number_total             1013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01074_si_004.cif
_cod_data_source_block           dm-ta-365-e2_mo
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         135.82
_cod_original_formula_moiety         'C4 H2.5 Cl0.5 F1.5 N0.5 O S0.5'
_cod_original_formula_units_Z            8
_cod_original_formula_sum        'C4 H2.50 Cl0.50 F1.50 N0.50 O S0.50'
_cod_database_code               4034658
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 92.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.96
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H7A(0.5) H7B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C1(H1)
;
_shelx_res_checksum              78871
_shelx_hkl_checksum              64711
_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 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.723