Cycloaddition of Alkynyl Ketones with N-Tosylimines Catalyzed by Bu~3~P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
Ling-Guo Meng; Peijie Cai; Qingxiang Guo; Song Xue; Journal of Organic Chemistry 73 (2008) 8491–8496; doi:10.1021/jo801687v

data_4023823
_publ_section_title
;
 Cycloaddition of Alkynyl Ketones with N-Tosylimines
 Catalyzed by Bu~3~P and DMAP: Synthesis of Highly Functionalized
 Pyrrolidines and Azetidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8491
_journal_page_last               8496
_journal_paper_doi               10.1021/jo801687v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C26 H24 Br N O3 S'
_chemical_formula_sum            'C26 H24 Br N O3 S'
_chemical_formula_weight         510.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 99.734(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   39.435(5)
_cell_length_b                   15.399(2)
_cell_length_c                   15.384(2)
_cell_measurement_reflns_used    14671
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     9208(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            82353
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.905
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4192
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.406
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1161
_refine_ls_number_reflns         21895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                15481
_reflns_number_total             21895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801687v_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;

2020-11-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C416 H384 Br16 N16 O48 S16'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     8166.91
_cod_database_code               4023823