Phosphine-catalyzed [3 + 2] annulation of β-sulfonamido-substituted enones with trans-α-cyano-α,β-unsaturated ketones for the synthesis of highly substituted pyrrolidines
Gao, Zhenzhen; Xie, Lei; Ji, Lusha; Ma, Xin; Li, Xiaojing; Liu, Honglei; Guo, Hongchao; RSC Advances 11 (2021) 40136–40139; doi:10.1039/D1RA07881J

data_7244084
_publ_section_title
;
 Phosphine-catalyzed [3 + 2] annulation of \b-sulfonamido-substituted
 enones with trans-\a-cyano-\a,\b-unsaturated ketones for the synthesis of
 highly substituted pyrrolidines
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              40136
_journal_page_last               40139
_journal_paper_doi               10.1039/D1RA07881J
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_sum            'C33 H28 N2 O4 S'
_chemical_formula_weight         548.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-30 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.287(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7583(3)
_cell_length_b                   21.2841(7)
_cell_length_c                   13.5807(4)
_cell_measurement_reflns_used    5919
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0950
_cell_measurement_theta_min      3.8320
_cell_volume                     2818.42(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10591
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        67.236
_diffrn_reflns_theta_max         67.236
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(12)
_refine_ls_extinction_coef       0.0040(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         7300
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.404
_reflns_Friedel_fraction_full    0.428
_reflns_Friedel_fraction_max     0.428
_reflns_number_gt                6529
_reflns_number_total             7300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07881j2.cif
_cod_data_source_block           exp_11425
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C66 H56 N4 O8 S2'
_cod_original_formula_weight         1097.26
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244084
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.866
_shelx_res_checksum              23944