Asymmetric [3 + 2] Cycloaddition of 2,2′-Diester Aziridines To Synthesize Pyrrolidine Derivatives
Liao, Yuting; Zhou, Baixin; Xia, Yong; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; ACS Catalysis 7 (2017) 3934–; doi:10.1021/acscatal.7b00787

data_4514115
_publ_section_title
;
 Asymmetric [3 + 2] Cycloaddition of 2,2&#x2032;-Diester Aziridines To
 Synthesize Pyrrolidine Derivatives
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3934
_journal_paper_doi               10.1021/acscatal.7b00787
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H61 N O10 S Si'
_chemical_formula_sum            'C44 H61 N O10 S Si'
_chemical_formula_weight         824.08
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5278(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.04501(7)
_cell_length_b                   9.77593(9)
_cell_length_c                   25.19795(17)
_cell_measurement_reflns_used    15393
_cell_measurement_temperature    175
_cell_measurement_theta_max      72.4180
_cell_measurement_theta_min      4.8900
_cell_volume                     2225.92(3)
_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_environment      air
_diffrn_ambient_temperature      175
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
  1 omega  -17.00   71.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -        2.0000   39.0000  -73.2153 88

  2 omega  -64.00   23.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -        2.0000  -66.0000 -104.7697 87

  3 omega    1.00   75.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -120.0000 74

  4 omega  -33.00   55.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

  5 omega  -31.00   63.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

  6 omega    1.00   75.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  7 omega   23.00   90.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   30.0000 67

  8 omega    3.00   29.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   91.0000   17.7780 26

  9 omega    4.00   32.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000   89.2019 28

 10 omega    3.00   29.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   91.0000  -39.2034 26

 11 omega   12.00   45.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   82.0000   61.5153 33

 12 omega   11.00   38.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000 -141.1007 27

 13 omega   11.00   38.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   84.0000  163.6322 27

 14 omega   16.00   45.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000   93.7715 29

 15 omega   18.00   46.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -93.0642 28

 16 omega   18.00   46.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000 -158.3601 28

 17 omega   17.00   46.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000  -34.0998 29

 18 omega   24.00  117.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   76.0000  167.2162 93

 19 omega   29.00  121.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   73.0000  127.8326 92

 20 omega   28.00  121.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   75.0000 -155.6282 93

 21 omega   41.00  125.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   57.0000   93.0124 84

 22 omega   41.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   52.0000 -118.4590 85

 23 omega   32.00  125.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -44.1677 93

 24 omega   31.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   26.1811 95

 25 omega   32.00  125.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -20.4988 93

 26 omega   37.00  125.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   67.0000  -74.5548 88

 27 omega   43.00  131.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   38.0000    7.3307 88

 28 omega   42.00  128.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   65.0000   32.1958 86

 29 omega   52.00  137.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   61.0000  -89.3577 85

 30 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95

 31 omega   90.00  175.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 32 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 33 omega   39.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 34 omega   90.00  175.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 85

 35 omega   40.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 36 omega   38.00  116.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 37 omega   90.00  175.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 38 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 39 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 40 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 41 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 42 omega   90.00  140.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1002860000
_diffrn_orient_matrix_UB_12      -0.0083248000
_diffrn_orient_matrix_UB_13      0.0509219000
_diffrn_orient_matrix_UB_21      -0.1374251000
_diffrn_orient_matrix_UB_22      0.0067021000
_diffrn_orient_matrix_UB_23      0.0339290000
_diffrn_orient_matrix_UB_31      -0.0111872000
_diffrn_orient_matrix_UB_32      -0.1572047000
_diffrn_orient_matrix_UB_33      -0.0012515000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32451
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_min         3.511
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42240
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       needle
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7715
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0770P)^2^+1.6150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                7481
_reflns_number_total             7715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00787_si_004.cif
_cod_data_source_block           fxm-lyt-16tips-175k
_cod_depositor_comments          'Adding full bibliography for 4514115.cif.'
_cod_database_code               4514115
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00Q(H00Q),
 C00T(H00T), C00X(H00X), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C00W(H00C,H00H), C00Y(H00J,H00K), C011(H01A,H01B), C01K(H01Z,
 HA)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00P(H00P), C00S(H00S), C00U(H00U), C00V(H00V), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C018(H018), C019(H019),
 C01B(H01F), C01D(H01J), C01E(H01K)
2.d Idealised Me refined as rotating group:
 C00Z(H00L,H00M,H00O), C01A(H01C,H01D,H01E), C01C(H01G,H01H,H01I), C01F(H01L,
 H01M,H01N), C01G(H01O,H01P,H01Q), C01H(H01R,H01S,H01T), C01I(H01U,H01V,H01W),
 C01J(H01X,H01Y,H), C01L(H01,HB,HC)
;
_shelx_res_checksum              13279
_shelx_hkl_checksum              84800
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-01-11
_olex2_submission_special_instructions 'No special instructions were received'