Catalytic asymmetric synthesis of pyrrolidine derivatives bearing heteroatom-substituted quaternary stereocenters
Wang, Zhi-Peng; Wu, Qi; Jiang, Jia; Li, Zi-Rui; Peng, Xiao-Jiao; Shao, Pan-Lin; He, Yun; Organic Chemistry Frontiers 5 (2018) 36–; doi:10.1039/C7QO00692F

data_1553873
_publ_section_title
;
 Catalytic asymmetric synthesis of pyrrolidine derivatives bearing
 heteroatom-substituted quaternary stereocenters
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              36
_journal_paper_doi               10.1039/C7QO00692F
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H23 N O4 S'
_chemical_formula_sum            'C13 H23 N O4 S'
_chemical_formula_weight         289.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-03-18 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1598(3)
_cell_length_b                   8.1330(4)
_cell_length_c                   31.1006(15)
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4720
_cell_measurement_theta_min      3.6120
_cell_volume                     1558.07(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -35.00   -3.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.2804   77.0000  120.0000 64

  2 omega   27.00   52.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.2804   77.0000  120.0000 50

  3 omega    0.00   86.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       17.9992   57.0000  150.0000 172

  4 omega  -19.00   17.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.2804  -99.0000   30.0000 72

  5 omega   23.00   48.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       17.9992 -146.0000   48.0000 50

  6 omega  -62.00  -37.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.2804 -178.0000  -30.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0009073000
_diffrn_orient_matrix_UB_12      -0.0840398000
_diffrn_orient_matrix_UB_13      0.0060480000
_diffrn_orient_matrix_UB_21      0.0084719000
_diffrn_orient_matrix_UB_22      0.0229440000
_diffrn_orient_matrix_UB_23      0.0219373000
_diffrn_orient_matrix_UB_31      -0.1149139000
_diffrn_orient_matrix_UB_32      0.0023193000
_diffrn_orient_matrix_UB_33      0.0015377000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            7147
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.184
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0442P)^2^+0.0736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2659
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00692f2.cif
_cod_data_source_block           161120_s1_wz
_cod_database_code               1553873
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.928
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'