Brønsted Acid Catalyzed Cyclization of Propargylic Alcohols with Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles
Xiaoxiang Zhang; Wan Teng Teo; Sally; Philip Wai Hong Chan; Journal of Organic Chemistry 75 (2010) 6290–6293; doi:10.1021/jo101292r

data_4025684
_publ_section_title
;
 Br\/onsted Acid Catalyzed Cyclization of Propargylic Alcohols with
 Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6290
_journal_page_last               6293
_journal_paper_doi               10.1021/jo101292r
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C25 H22 Cl N S'
_chemical_formula_sum            'C25 H22 Cl N S'
_chemical_formula_weight         403.95
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.725(6)
_cell_angle_beta                 100.635(6)
_cell_angle_gamma                115.204(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6923(11)
_cell_length_b                   10.0308(11)
_cell_length_c                   12.2838(14)
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.25
_cell_measurement_theta_min      2.37
_cell_volume                     1007.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20530
_diffrn_reflns_theta_full        31.91
_diffrn_reflns_theta_max         31.91
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^2^+0.0466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                4990
_reflns_number_total             6850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101292r_si_003.cif
_cod_data_source_block           chan75s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025684