Catalytic asymmetric <i>de novo</i> construction of 4-pyrrolin-2-ones <i>via</i> intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones.
Mo, Nan-Nan; Miao, Yu-Hang; Xiao, Xiao; Hua, Yuan-Zhao; Wang, Min-Can; Huang, Lihua; Mei, Guang-Jian; Chemical communications (Cambridge, England) 59 (2023) 5902–5905; doi:10.1039/d3cc01194a

data_7131575
_publ_section_title
;
 Catalytic asymmetric <i>de novo</i> construction of 4-pyrrolin-2-ones
 <i>via</i> intermolecular formal [3+2] cycloaddition of azoalkenes with
 azlactones.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5902
_journal_page_last               5905
_journal_paper_doi               10.1039/d3cc01194a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N3 O8'
_chemical_formula_sum            'C20 H23 N3 O8'
_chemical_formula_weight         433.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.027(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0745(7)
_cell_length_b                   12.0391(4)
_cell_length_c                   9.3014(3)
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4080
_cell_measurement_theta_min      4.2740
_cell_volume                     2256.49(13)
_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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -16.00  16.00   1.00    1.00    --    0.00 -57.00-180.00   32
  2  \w   -106.00 -80.00   1.00    3.00    --  -33.50 -19.00 -90.00   26
  3  \w    -31.00  10.00   1.00    3.00    --  -33.50  37.00 -90.00   41
  4  \w    -59.00 -25.00   1.00    3.00    --  -33.50 -19.00 -90.00   34
  5  \w    -71.00 -45.00   1.00    3.00    --  -33.50 178.00-120.00   26
  6  \w   -108.00 -82.00   1.00    3.00    --  -33.50 178.00-120.00   26
  7  \w     59.00  91.00   1.00    3.00    --   36.47 178.00-120.00   32
  8  \w     59.00 110.00   1.00    3.00    --   36.47 178.00-150.00   51
  9  \w     33.00  74.00   1.00    3.00    --   36.47  57.00  30.00   41
 10  \w     -3.00  22.00   1.00    3.00    --   36.47 100.00-136.80   25
 11  \w      9.00  49.00   1.00    3.00    --   36.47  77.00  30.00   40
 12  \w     21.00  47.00   1.00    3.00    --   36.47  37.00  30.00   26
 13  \w     12.00  47.00   1.00    3.00    --   36.47  77.00 -30.00   35
 14  \w     57.00 107.00   1.00    3.00    --   36.47 178.00   0.00   50
 15  \w     29.00  68.00   1.00    3.00    --   36.47  57.00 -60.00   39
 16  \w     49.00  94.00   1.00    3.00    --   36.47  57.00 120.00   45
 17  \w     54.00 105.00   1.00    3.00    --   36.47  77.00  30.00   51
 18  \w     -3.00  23.00   1.00    3.00    --   36.47 -99.00  30.00   26
 19  \w     80.00 105.00   1.00    3.00    --   36.47  57.00 -60.00   25
 20  \w     23.00  77.00   1.00    3.00    --   36.47 -99.00-180.00   54
 21  \w      1.00  40.00   1.00    3.00    --   36.47  19.00 -60.00   39
 22  \w     50.00  76.00   1.00    3.00    --   36.47  57.00  60.00   26
 23  \w     20.00  46.00   1.00    3.00    --   36.47  77.00 -60.00   26
 24  \w      1.00  27.00   1.00    3.00    --   36.47  95.00 -61.91   26
 25  \w     -8.00  17.00   1.00    3.00    --   36.47 106.00  93.56   25
 26  \w      0.00  76.00   1.00    3.00    --   36.47  19.00  60.00   76
 27  \w     68.00 104.00   1.00    3.00    --   36.47  57.00 -90.00   36
 28  \w     40.00  66.00   1.00    3.00    --   36.47  57.00-180.00   26
 29  \w     18.00  46.00   1.00    3.00    --   36.47  57.00  60.00   28
 30  \w     80.00 160.00   1.00   13.00    --  108.00  77.00-180.00   80
 31  \w     82.00 108.00   1.00   13.00    --  108.00  30.00  30.00   26
 32  \w     79.00 105.00   1.00   13.00    --  108.00  77.00   0.00   26
 33  \w     82.00 110.00   1.00   13.00    --  108.00  30.00  60.00   28
 34  \w     84.00 110.00   1.00   13.00    --  108.00  30.00  90.00   26
 35  \w    117.00 176.00   1.00   13.00    --  108.00  77.00  60.00   59
 36  \w     79.00 106.00   1.00   13.00    --  108.00  77.00  60.00   27
 37  \w     37.00 108.00   1.00   13.00    --  108.00-111.00  90.00   71
 38  \w     88.00 114.00   1.00   13.00    --  108.00  45.00  90.00   26
 39  \w    137.00 163.00   1.00   13.00    --  108.00  61.00   0.00   26
 40  \w    144.00 170.00   1.00   13.00    --  108.00  77.00  90.00   26
 41  \w     79.00 105.00   1.00   13.00    --  108.00  77.00  90.00   26
 42  \w     82.00 108.00   1.00   13.00    --  108.00  30.00 150.00   26
 43  \w    110.00 176.00   1.00   13.00    --  108.00  77.00 150.00   66
 44  \w     79.00 105.00   1.00   13.00    --  108.00  77.00 150.00   26
 45  \w    111.00 176.00   1.00   13.00    --  108.00  77.00  30.00   65
 46  \w     41.00 121.00   1.00   13.00    --  108.00 -61.00  60.00   80
 47  \w     88.00 114.00   1.00   13.00    --  108.00  45.00  60.00   26
 48  \w     79.00 105.00   1.00   13.00    --  108.00  77.00  30.00   26
 49  \w     88.00 114.00   1.00   13.00    --  108.00  61.00  60.00   26
 50  \w     79.00 105.00   1.00   13.00    --  108.00  77.00 120.00   26
 51  \w     88.00 114.00   1.00   13.00    --  108.00  45.00 120.00   26
 52  \w     80.00 155.00   1.00   13.00    --  108.00  77.00 -60.00   75
 53  \w     88.00 119.00   1.00   13.00    --  108.00  61.00  30.00   31
 54  \w     84.00 169.00   1.00   13.00    --  108.00  30.00 120.00   85
 55  \w     88.00 114.00   1.00   13.00    --  108.00  61.00 120.00   26
 56  \w     91.00 117.00   1.00   13.00    --  108.00  61.00 -30.00   26
 57  \w     93.00 144.00   1.00   13.00    --  108.00  45.00 -30.00   51
 58  \w     84.00 110.00   1.00   13.00    --  108.00  30.00   0.00   26
 59  \w     88.00 114.00   1.00   13.00    --  108.00  61.00  90.00   26
 60  \w     79.00 104.00   1.00   13.00    --  108.00  77.00 -30.00   25
 61  \w     88.00 114.00   1.00   13.00    --  108.00  61.00   0.00   26
 62  \w     70.00 109.00   1.00   13.00    --  108.00 -94.00 150.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0478029582
_diffrn_orient_matrix_UB_12      -0.0061207369
_diffrn_orient_matrix_UB_13      -0.1607290851
_diffrn_orient_matrix_UB_21      0.0595205248
_diffrn_orient_matrix_UB_22      -0.0142437450
_diffrn_orient_matrix_UB_23      -0.0628819169
_diffrn_orient_matrix_UB_31      -0.0043670009
_diffrn_orient_matrix_UB_32      -0.1269871787
_diffrn_orient_matrix_UB_33      0.0147813204
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11094
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.853
_diffrn_reflns_theta_min         4.278
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0693P)^2^+0.2933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                3483
_reflns_number_total             3802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01194a2.cif
_cod_data_source_block           20230221a
_cod_depositor_comments          'Adding full bibliography for 7131575.cif.'
_cod_original_cell_volume        2256.50(14)
_cod_database_code               7131575
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3N2O2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 100.00
_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. Restrained distances
 N3-H3
 0.87 with sigma of 0.02
 C7A-C6
 1.54 with sigma of 0.02
 C14-C15
 1.6 with sigma of 0.02
 C19-C20
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
4. Others
 Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=
 Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=
 Sof(H8)=FVAR(1)
 Sof(C7A)=1-FVAR(2)
 Sof(C7)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C8(H8), C12A(H12A), C11A(H11A),
 C10A(H10A), C9A(H9A), C8A(H8A)
5.c Fitted hexagon refined as free rotating group:
 C12(C11,C10,C9,C8,C7), C7A(C12A,C11A,C10A,C9A,C8A)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              90451
_shelx_hkl_checksum              79602
_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 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.888