Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates.
Gharpure, Santosh J.; Prasath, V.; Organic & biomolecular chemistry 12 (2014) 7397–7409; doi:10.1039/c4ob01387e

data_7154048
_publ_section_title
;
 Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and
 pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of
 vinylogous carbonates.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7397
_journal_page_last               7409
_journal_paper_doi               10.1039/c4ob01387e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C22 H23 N O7 S'
_chemical_formula_sum            'C22 H23 N O7 S'
_chemical_formula_weight         445.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                83.084(17)
_cell_angle_beta                 86.07(2)
_cell_angle_gamma                86.796(18)
_cell_formula_units_Z            2
_cell_length_a                   7.440(5)
_cell_length_b                   10.513(7)
_cell_length_c                   13.472(9)
_cell_measurement_reflns_used    1626
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.30
_cell_measurement_theta_min      3.10
_cell_volume                     1042.4(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b23'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b23'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7918
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0769
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.6790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                2680
_reflns_number_total             3594
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_duplicate_entry             7153972
_cod_data_source_file            c4ob01387e2.cif
_cod_data_source_block           SJG-VPS-84-B
_cod_database_code               7154048