Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization.
Lu, Licheng; Lu, Ping; Chemical science 14 (2023) 8355–8359; doi:10.1039/d3sc02485g

data_1569539
_publ_section_title
;
 Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones:
 vicinal quaternary stereocenters construction and skeletal
 functionalization.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              8355
_journal_page_last               8359
_journal_paper_doi               10.1039/d3sc02485g
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H19 N O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_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_block_doi                 10.5517/ccdc.csd.cc2fz2m4
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.10160(10)
_cell_length_b                   9.87230(10)
_cell_length_c                   17.9089(2)
_cell_measurement_reflns_used    27766
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.0280
_cell_measurement_theta_min      4.5260
_cell_volume                     1609.18(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -81.00 -31.00   1.00    1.00    --    0.00 -61.00  22.00   50
  2  \w     79.00 120.00   1.00    1.00    --   95.80 -61.00  22.00   41
  3  \w     72.00 100.00   1.00    1.00    --   95.80  61.00 161.00   28
  4  \w     31.00  59.00   1.00    1.00    --   95.80 -61.00  22.00   28
  5  \w    -10.00  19.00   1.00    1.00    --    0.00 -37.00  60.00   29
  6  \w    -17.00  24.00   1.00    1.00    --    0.00  61.00 161.00   41
  7  \w    -32.00  85.00   1.00    1.00    --    0.00  82.00-180.00  117
  8  \w    -30.00  21.00   1.00    1.00    --    0.00  77.00 -60.00   51
  9  \w    -73.00 -47.00   1.00    1.00    --    0.00 -57.00-180.00   26
 10  \w     61.00  89.00   1.00    1.00    --    0.00  37.00  90.00   28
 11  \w    -13.00  44.00   1.00    1.00    --    0.00  37.00  90.00   57
 12  \w    -23.00  13.00   1.00    1.00    --    0.00  57.00  60.00   36
 13  \w     35.00  87.00   1.00    1.00    --    0.00  37.00 -90.00   52
 14  \w     31.00  73.00   1.00    1.00    --    0.00  77.00 -60.00   42
 15  \w    -63.00 -38.00   1.00    1.00    --    0.00 -37.00  60.00   25
 16  \w    -18.00  23.00   1.00    1.00    --    0.00  37.00 -90.00   41
 17  \w     26.00  82.00   1.00    1.00    --    0.00  57.00  60.00   56
 18  \w    -29.00  21.00   1.00    1.00    --    0.00 -57.00-180.00   50
 19  \w      6.00 126.00   1.00    1.00    --   95.80 -82.00-180.00  120
 20  \w     66.00 180.00   1.00    1.00    --   95.80  77.00-120.00  114
 21  \w    112.00 185.00   1.00    1.00    --   95.80  61.00  76.62   73
 22  \w     65.00 151.00   1.00    1.00    --   95.80  77.00 -60.00   86
 23  \w    113.00 157.00   1.00    1.00    --   95.80  82.00 -13.63   44
 24  \w     71.00 104.00   1.00    1.00    --   95.80  61.00  76.62   33
 25  \w    139.00 185.00   1.00    1.00    --   95.80  82.00  90.00   46
 26  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 27  \w     71.00  97.00   1.00    1.00    --   95.80  58.00  -6.65   26
 28  \w     67.00  97.00   1.00    1.00    --   95.80  73.00 -67.32   30
 29  \w    102.00 174.00   1.00    1.00    --   95.80  73.00 -67.32   72
 30  \w     73.00 106.00   1.00    1.00    --   95.80  54.00 118.89   33
 31  \w     66.00 126.00   1.00    1.00    --   95.80 -82.00 -60.00   60
 32  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  60.00   26
 33  \w    116.00 185.00   1.00    1.00    --   95.80  82.00  60.00   69
 34  \w     88.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   39
 35  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 36  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -13.63   25
 37  \w     76.00 185.00   1.00    1.00    --   95.80  45.00  30.00  109
 38  \w     63.00  93.00   1.00    1.00    --   95.80  82.00   0.00   30
 39  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00  30.00  121
 40  \w     96.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   30
 41  \w     65.00  91.00   1.00    1.00    --   95.80  82.00-120.00   26
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 43  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 44  \w     75.00 103.00   1.00    1.00    --   95.80  45.00   0.00   28
 45  \w     76.00 106.00   1.00    1.00    --   95.80  61.00  90.00   30
 46  \w     72.00 185.00   1.00    1.00    --   95.80  61.00-180.00  113
 47  \w     67.00  92.00   1.00    1.00    --   95.80  72.00 179.59   25
 48  \w    147.00 180.00   1.00    1.00    --   95.80  77.00 -30.00   33
 49  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 50  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 51  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 52  \w     70.00  96.00   1.00    1.00    --   95.80  63.00 -74.73   26
 53  \w     72.00 115.00   1.00    1.00    --   95.80  56.00 -72.41   43
 54  \w    112.00 139.00   1.00    1.00    --   95.80  82.00 -90.00   27
 55  \w     74.00 166.00   1.00    1.00    --   95.80  61.00-150.00   92
 56  \w     71.00  96.00   1.00    1.00    --   95.80  61.00   0.00   25
 57  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 58  \w     65.00 123.00   1.00    1.00    --   95.80  77.00  30.00   58
 59  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  12.57   26
 60  \w    131.00 184.00   1.00    1.00    --   95.80  82.00  12.57   53
 61  \w     63.00  88.00   1.00    1.00    --   95.80  81.00-165.94   25
 62  \w    122.00 168.00   1.00    1.00    --   95.80  77.00-132.70   46
 63  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 64  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-132.70   25
 65  \w     70.00 110.00   1.00    1.00    --   95.80  62.00 131.95   40
 66  \w     77.00 133.00   1.00    1.00    --   95.80  30.00-180.00   56
 67  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 68  \w     64.00  90.00   1.00    1.00    --   95.80  82.00-150.00   26
 69  \w    134.00 180.00   1.00    1.00    --   95.80  62.00 131.95   46
 70  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 71  \w     50.00  75.00   1.00    1.00    --   95.80 -82.00-120.00   25
 72  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1567217000
_diffrn_orient_matrix_UB_12      -0.0587038000
_diffrn_orient_matrix_UB_13      -0.0026312000
_diffrn_orient_matrix_UB_21      -0.0478241000
_diffrn_orient_matrix_UB_22      0.0994827000
_diffrn_orient_matrix_UB_23      0.0616291000
_diffrn_orient_matrix_UB_31      -0.0423700000
_diffrn_orient_matrix_UB_32      0.1049657000
_diffrn_orient_matrix_UB_33      -0.0599448000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37119
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.939
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       0.0113(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0392P)^2^+0.2348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2827
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02485g2.cif
_cod_data_source_block           exp_2574
_cod_depositor_comments
'Adding full bibliography for 1569539--1569545.cif.'
_cod_database_code               1569539
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.729
_reflns_odcompleteness_completeness 99.94
_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:
 C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              26262
_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.513