Organocatalytic asymmetric synthesis of highly substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position.
Mukhopadhyay, Soumendranath; Pan, Subhas Chandra; Organic & biomolecular chemistry 16 (2018) 9349–9353; doi:10.1039/c8ob02648c

data_7156582
_publ_section_title
;
 Organocatalytic asymmetric synthesis of highly substituted pyrrolidines
 bearing a stereogenic quaternary centre at the 3-position.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9349
_journal_page_last               9353
_journal_paper_doi               10.1039/c8ob02648c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C33 H27 F N2 O4 S'
_chemical_formula_sum            'C33 H27 F N2 O4 S'
_chemical_formula_weight         566.66
_chemical_name_systematic        Unknown
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-08-15 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.002(4)
_cell_angle_beta                 91.798(4)
_cell_angle_gamma                112.093(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7629(4)
_cell_length_b                   11.7118(6)
_cell_length_c                   13.5050(7)
_cell_measurement_reflns_used    2754
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4050
_cell_measurement_theta_min      3.6880
_cell_volume                     1429.97(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_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    -50.00  83.00   1.00    7.50    --   20.84   0.00 -90.00  133
  2  \w     -4.00  35.00   1.00    7.50    --   20.84 -77.00   0.00   39
  3  \w    -15.00  25.00   1.00    7.50    --  -17.33 -99.00  90.00   40
  4  \w      6.00  84.00   1.00    7.50    --   20.84  38.00 120.00   78
  5  \w    -14.00  24.00   1.00    7.50    --  -17.33 -99.00-120.00   38
  6  \w    -64.00 -36.00   1.00    7.50    --  -17.33-178.00-180.00   28
  7  \w    -94.00 -55.00   1.00    7.50    --  -17.33 178.00 120.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0361123000
_diffrn_orient_matrix_UB_12      -0.0576867000
_diffrn_orient_matrix_UB_13      -0.0244292000
_diffrn_orient_matrix_UB_21      0.0090568000
_diffrn_orient_matrix_UB_22      0.0301178000
_diffrn_orient_matrix_UB_23      -0.0462920000
_diffrn_orient_matrix_UB_31      0.0690585000
_diffrn_orient_matrix_UB_32      -0.0061710000
_diffrn_orient_matrix_UB_33      -0.0046812000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11400
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3159
_exptl_crystal_description       block
_exptl_crystal_F_000             592.5485
_exptl_crystal_recrystallization_method
'From dichloromethane and methanol solvent mixture'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.5315
_refine_diff_density_min         -0.5795
_refine_diff_density_rms         0.0691
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.7486
_refine_ls_goodness_of_fit_ref   1.0679
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0679
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+1.1937P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3826
_reflns_number_total             5030
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02648c2.cif
_cod_data_source_block           sss-p2-3-F
_cod_depositor_comments          'Adding full bibliography for 7156582.cif.'
_cod_database_code               7156582
_chemical_oxdiff_formula         'C33 H27 N2 O4 S1 F1'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: F1B(0.5) F1A(0.5)
3.a Ternary CH refined with riding coordinates:
 N1(H1), C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C13(H13a,H13b)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C28(H28), C32(H32), C20(H20), C29(H29), C19(H19), C18(H18),
 C22(H22), C1(H1a), C26(H26), C17(H17), C31(H31), C2(H2), C5(H5), C24(H24),
 C3(H3), C4(H4)
3.d Idealised Me refined as rotating group:
 C33(H33a,H33b,H33c)
;
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.731