An asymmetric oxidative cyclization/Mannich-type addition cascade reaction for direct access to chiral pyrrolidin-3-ones
Zhou, Su; Xie, Xiongda; Xu, Xinxin; Dong, Shanliang; Hu, Wenhao; Xu, Xinfang; Chemical Communications  (2021) –; doi:10.1039/D1CC04830A

data_7129185
_publ_section_title
;
 An asymmetric oxidative cyclization/Mannich-type addition cascade
 reaction for direct access to chiral pyrrolidin-3-ones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04830A
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H25 Cl N2 O3 S'
_chemical_formula_sum            'C21 H25 Cl N2 O3 S'
_chemical_formula_weight         420.94
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.671(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1972(2)
_cell_length_b                   13.8507(2)
_cell_length_c                   11.1349(2)
_cell_measurement_reflns_used    6502
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.0250
_cell_measurement_theta_min      4.1780
_cell_volume                     1051.58(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 -27.00   0.50    2.50    -- -100.00  61.00  60.00   84
  2  \w    -24.00  29.00   0.50    0.50    --  -46.62  19.00   0.00  106
  3  \w    -24.00  29.00   0.50    0.50    --  -46.62  19.00 -90.00  106
  4  \w    -69.00 -27.00   0.50    2.50    -- -100.00  61.00 150.00   84
  5  \w   -108.00 -27.00   0.50    2.50    -- -100.00 111.00  66.00  162
  6  \w   -120.00 -32.00   0.50    0.50    --  -46.62 -39.00  53.00  176
  7  \w   -119.00 -74.00   0.50    0.50    --  -46.62-125.00 -60.00   90
  8  \w   -119.00 -74.00   0.50    0.50    --  -46.62-125.00-180.00   90
  9  \w   -173.00 -80.00   0.50    2.50    -- -100.00 -86.00-135.00  186
 10  \w   -173.00 -85.00   0.50    2.50    -- -100.00 -39.00  53.00  176
 11  \w   -119.00 -74.00   0.50    0.50    --  -46.62-125.00  90.00   90
 12  \w   -175.00 -82.00   0.50    2.50    -- -100.00 -15.00 -30.00  186
 13  \w     34.00 108.00   0.50    2.50    --  107.00-111.00 -27.00  148
 14  \w     34.00 106.00   0.50    2.50    --  107.00 -94.00  90.00  144
 15  \w     34.00  73.00   0.50    2.50    --  107.00 -61.00  90.00   78
 16  \w     34.00 112.00   0.50    2.50    --  107.00-125.00  30.00  156
 17  \w     34.00  73.00   0.50    2.50    --  107.00 -61.00 -90.00   78
 18  \w     34.00  73.00   0.50    2.50    --  107.00 -61.00-120.00   78
 19  \w     34.00  73.00   0.50    2.50    --  107.00 -61.00 -60.00   78
 20  \w     34.00 106.00   0.50    2.50    --  107.00 -94.00-120.00  144
 21  \w     34.00 102.00   0.50    2.50    --  107.00-125.00-150.00  136
 22  \w     92.00 178.00   0.50    2.50    --  107.00  30.00 -60.00  172
 23  \w     80.00 105.00   0.50    2.50    --  107.00 125.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2121478000
_diffrn_orient_matrix_UB_12      0.0365276000
_diffrn_orient_matrix_UB_13      0.0295072000
_diffrn_orient_matrix_UB_21      0.0061971000
_diffrn_orient_matrix_UB_22      -0.0411020000
_diffrn_orient_matrix_UB_23      -0.1272320000
_diffrn_orient_matrix_UB_31      -0.0775702000
_diffrn_orient_matrix_UB_32      0.0966659000
_diffrn_orient_matrix_UB_33      -0.0652340000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10375
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.172
_diffrn_reflns_theta_min         4.191
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0296P)^2^+0.2377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.686
_reflns_Friedel_fraction_max     0.628
_reflns_number_gt                3323
_reflns_number_total             3557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04830a2.cif
_cod_data_source_block           zhous_210409
_cod_database_code               7129185
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONCl
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.772
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00P(H00T)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00K,H00L), C00M(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 N006(H006), C008(H008), C00B(H00B), C00D(H00D), C00I(H00I), C00L(H00M),
 C00O(H00S), C00Q(H00U), C00R(H00V), C00S(H00W)
2.d Idealised Me refined as rotating group:
 C00G(H00C,H00E,H00F), C00J(H00G,H00H,H00J), C00N(H00P,H00Q,H00R)
;
_shelx_res_checksum              57322
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.113
_oxdiff_exptl_absorpt_empirical_full_min 0.471