l-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the Regio- and Diastereoselective Synthesis of Highly Substituted Thienothiopyrans Containing Three or Four Stereocenters
Sethuraman Indumathi; Subbu Perumal; J. Carlos Menéndez; Journal of Organic Chemistry 75 (2010) 472–475; doi:10.1021/jo9021327

data_4025162
_publ_contact_author_address
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
_publ_contact_author_email       subbu.perum@gmail.com
_publ_contact_author_name        'Prof.Subbu Perumal'
_publ_contact_author_phone       '0452 2459845'
_publ_section_title
;
 l-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the
 Regio- and Diastereoselective Synthesis of Highly Substituted
 Thienothiopyrans Containing Three or Four Stereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              472
_journal_page_last               475
_journal_paper_doi               10.1021/jo9021327
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C31 H29 Cl O5 S2'
_chemical_formula_sum            'C31 H29 Cl O5 S2'
_chemical_formula_weight         581.11
_chemical_melting_point          186
_chemical_name_systematic
;
 Ethyl 4-(4-chlorobenzoyl)-2,7-di(4-methylphenyl)-5,5-dioxo-
2,3,4,5,6,7-hexahydro-5-thieno[3,2-c]thiopyran-6-carboxylate 
;
_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_date             16.12.07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.01
_cell_angle_beta                 91.64
_cell_angle_gamma                108.81
_cell_formula_units_Z            2
_cell_length_a                   10.937
_cell_length_b                   12.082
_cell_length_c                   12.285
_cell_measurement_reflns_used    5971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.12
_cell_volume                     1455.812
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP & PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MACH3-Nonius sealed tube'
_diffrn_measurement_method       \w-2\q
_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  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5971
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '[North et al., 1968]'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0456
_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^)+(0.1020P)^2^+0.9441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                3681
_reflns_number_total             5096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9021327_si_001.cif
_cod_data_source_block           mi1
_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_original_cell_volume        1455.6
_cod_database_code               4025162