Polar Hetero-Diels-Alder Reactions of 4-Alkenylthiazoles with 1,2,4-Triazoline-3,5-diones: An Experimental and Computational Study
Mateo Alajarín; José Cabrera; Aurelia Pastor; Pilar Sánchez-Andrada; Delia Bautista; Journal of Organic Chemistry 73 (2008) 963–973; doi:10.1021/jo7021668

data_4023243
_publ_section_title
;
 Polar Hetero-Diels-Alder Reactions of 4-Alkenylthiazoles with
 1,2,4-Triazoline-3,5-diones: An Experimental and Computational Study
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              963
_journal_page_last               973
_journal_paper_doi               10.1021/jo7021668
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C36 H28 Cl3 N7 O4 S'
_chemical_formula_weight         761.06
_chemical_name_systematic
; 
 ? 
;
_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                81.004(2)
_cell_angle_beta                 87.258(2)
_cell_angle_gamma                67.033(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6653(6)
_cell_length_b                   12.9166(7)
_cell_length_c                   13.2350(7)
_cell_measurement_reflns_used    1556
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.84
_cell_measurement_theta_min      2.40
_cell_volume                     1813.34(17)
_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 0.994
_diffrn_measured_fraction_theta_max 0.991
_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  0.0909
_diffrn_reflns_av_sigmaI/netI    0.1538
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20701
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         7636
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.0959
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2484
_refine_ls_wR_factor_ref         0.2868
_reflns_number_gt                4213
_reflns_number_total             7636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7021668-File003.cif
_cod_data_source_block           vjjc103btm
_cod_database_code               4023243