Diels-Alder Reactions of 4-Alkenylthiazoles: A New Approach to Thiazole Functionalization
Mateo Alajarín; José Cabrera; Aurelia Pastor; Pilar Sánchez-Andrada; Delia Bautista; Journal of Organic Chemistry 72 (2007) 2097–2105; doi:10.1021/jo062417e

data_4022772
_publ_section_title
;
 Diels-Alder Reactions of 4-Alkenylthiazoles: A New Approach
 to Thiazole Functionalization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2097
_journal_page_last               2105
_journal_paper_doi               10.1021/jo062417e
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C23.5 H19.5 Cl2.5 N2 O2 S'
_chemical_formula_weight         482.60
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.272(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6133(3)
_cell_length_b                   19.6445(8)
_cell_length_c                   16.8723(7)
_cell_measurement_reflns_used    8973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.40
_cell_volume                     2191.94(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w-scan
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25340
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.9065
_exptl_absorpt_correction_T_min  0.8508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0433P)^2^+1.1393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                4635
_reflns_number_total             5106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062417esi20061123_075801.cif
_cod_data_source_block           iijcc110s
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C23.50 H19.50 Cl2.50 N2 O2 S'
_cod_database_code               4022772