Dimethyl Sulfoxide and N-Iodosuccinimide Promoted 5-exo-dig Oxidative Cyclization of Yne-Tethered Ynamide: Access to Pyrrolidones and Spiro-pyrrolidones.
Prabagar, B.; Nayak, Sanatan; Prasad, Rangu; Sahoo, Akhila K.; Organic letters 18 (2016) 3066–3069; doi:10.1021/acs.orglett.6b01149

data_1543806
_publ_section_title
;
 Dimethyl Sulfoxide and N-Iodosuccinimide Promoted 5-exo-dig Oxidative
 Cyclization of Yne-Tethered Ynamide: Access to Pyrrolidones and
 Spiro-pyrrolidones.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3066
_journal_page_last               3069
_journal_paper_doi               10.1021/acs.orglett.6b01149
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9577(13)
_cell_length_b                   33.256(3)
_cell_length_c                   8.9182(7)
_cell_measurement_reflns_used    7264
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      1.000
_cell_measurement_theta_min      0.810
_cell_volume                     3546.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.05
_diffrn_reflns_av_sigmaI/netI    0.1820
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29371
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       round
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.2090
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.1
_refine_ls_shift/su_mean         0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.5827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3438
_reflns_number_total             6896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01149_si_004.cif
_cod_data_source_block           praba44
_cod_original_cell_volume        3546.4(6)
_cod_database_code               1543806