Catalyst-controlled divergence in cycloisomerisation reactions of N-propargyl-N-vinyl sulfonamides: gold-catalysed synthesis of 2-sulfonylmethyl pyrroles and dihydropyridines
Sridhar Undeela; Srinivas Thadkapally; Jagadeesh Babu Nanubolu; Kiran Kumar Singarapu; Rajeev S. Menon; Chem.Commun. 51 (2015) 13748–; doi:10.1039/C5cc04871K

data_7117698
_publ_section_title
;
 Catalyst-controlled divergence in cycloisomerisation reactions of
 N-propargyl-N-vinyl sulfonamides: gold-catalysed synthesis of
 2-sulfonylmethyl pyrroles and dihydropyridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              13748
_journal_paper_doi               10.1039/C5cc04871K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C19 H19 N O4 S2'
_chemical_formula_sum            'C19 H19 N O4 S2'
_chemical_formula_weight         389.47
_chemical_name_systematic
2-Methyl-1-(methylsulfonyl)-3-phenyl-5-(phenylsulfonylmethyl)-1H-pyrrole
_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
_audit_update_record
;
2015-05-05 deposited with the CCDC.
2015-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                76.4330(10)
_cell_angle_beta                 74.7090(10)
_cell_angle_gamma                85.5280(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0274(5)
_cell_length_b                   8.1297(5)
_cell_length_c                   14.6961(8)
_cell_measurement_reflns_used    5512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.58
_cell_volume                     899.17(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8766
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_correction_T_min  0.8585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane  and Hexane'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0498P)^2^+0.3767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                2916
_reflns_number_total             3160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04871k2.cif
_cod_data_source_block           ay92m
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               7117698