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_1569541
_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         'C18 H21 N O5'
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fz2j1
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.102(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4486(3)
_cell_length_b                   18.6265(8)
_cell_length_c                   7.3386(3)
_cell_measurement_reflns_used    8014
_cell_measurement_temperature    175(6)
_cell_measurement_theta_max      74.1180
_cell_measurement_theta_min      4.7250
_cell_volume                     867.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      175(6)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -28.00  29.00   1.00    1.00    --    0.00 -77.00 -90.00   57
  2  \w    -75.00 -49.00   1.00    1.00    --    0.00 -77.00 -90.00   26
  3  \w    -88.00  19.00   1.00    1.00    --    0.00 -37.00 120.00  107
  4  \w    -89.00 -61.00   1.00    1.00    --    0.00 -37.00 -60.00   28
  5  \w      0.00  25.00   1.00    1.00    --    0.00  57.00  90.00   25
  6  \w     -8.00  18.00   1.00    1.00    --    0.00 -37.00-150.00   26
  7  \w    -85.00 -18.00   1.00    1.00    --    0.00 -37.00-150.00   67
  8  \w    -73.00  19.00   1.00    1.00    --    0.00 -37.00 -30.00   92
  9  \w     31.00  65.00   1.00    1.00    --    0.00  57.00  90.00   34
 10  \w    -47.00  14.00   1.00    1.00    --    0.00 -57.00  90.00   61
 11  \w    127.00 153.00   1.00    2.00    --   95.80  71.00  56.11   26
 12  \w      7.00 127.00   1.00    2.00    --   95.80 -82.00-150.00  120
 13  \w     71.00  99.00   1.00    2.00    --   95.80  61.00-150.00   28
 14  \w     63.00  89.00   1.00    2.00    --   95.80  82.00-150.00   26
 15  \w     66.00 161.00   1.00    2.00    --   95.80  82.00 -90.00   95
 16  \w     69.00  95.00   1.00    2.00    --   95.80  71.00  56.11   26
 17  \w     71.00  98.00   1.00    2.00    --   95.80  58.00 -38.89   27
 18  \w     79.00 105.00   1.00    2.00    --   95.80  45.00   0.00   26
 19  \w     75.00 114.00   1.00    2.00    --   95.80  45.00 -90.00   39
 20  \w    145.00 181.00   1.00    2.00    --   95.80  61.00-180.00   36
 21  \w     71.00  97.00   1.00    2.00    --   95.80  61.00  60.00   26
 22  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -60.00   26
 23  \w    110.00 185.00   1.00    2.00    --   95.80  82.00 -60.00   75
 24  \w     71.00 117.00   1.00    2.00    --   95.80  61.00 -90.00   46
 25  \w    119.00 159.00   1.00    2.00    --   95.80  61.00 -90.00   40
 26  \w     26.00  84.00   1.00    2.00    --   95.80 -77.00 120.00   58
 27  \w     76.00 173.00   1.00    2.00    --   95.80  45.00  60.00   97
 28  \w    106.00 184.00   1.00    2.00    --   95.80  61.00-150.00   78
 29  \w     65.00  93.00   1.00    2.00    --   95.80  77.00  90.00   28
 30  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -30.00   26
 31  \w     50.00 123.00   1.00    2.00    --   95.80 -82.00  90.00   73
 32  \w     69.00  98.00   1.00    2.00    --   95.80  72.00 140.00   29
 33  \w     77.00 122.00   1.00    2.00    --   95.80  61.00-180.00   45
 34  \w    140.00 166.00   1.00    2.00    --   95.80  45.00-120.00   26
 35  \w     76.00 132.00   1.00    2.00    --   95.80  45.00-120.00   56
 36  \w    141.00 167.00   1.00    2.00    --   95.80  61.00 120.00   26
 37  \w     76.00 152.00   1.00    2.00    --   95.80  45.00 120.00   76
 38  \w    157.00 183.00   1.00    2.00    --   95.80  45.00 120.00   26
 39  \w     74.00  99.00   1.00    2.00    --   95.80  61.00  30.00   25
 40  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 120.00   25
 41  \w    136.00 161.00   1.00    2.00    --   95.80  69.00  36.60   25
 42  \w     77.00 103.00   1.00    2.00    --   95.80  45.00 -30.00   26
 43  \w     65.00 113.00   1.00    2.00    --   95.80  77.00  60.00   48
 44  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 45  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 46  \w    111.00 137.00   1.00    2.00    --   95.80  77.00-180.00   26
 47  \w     67.00  93.00   1.00    2.00    --   95.80  82.00 150.00   26
 48  \w    135.00 168.00   1.00    2.00    --   95.80  82.00 150.00   33
 49  \w     71.00  96.00   1.00    2.00    --   95.80  61.00 120.00   25
 50  \w      6.00 123.00   1.00    2.00    --   95.80 -82.00 -30.00  117
 51  \w     76.00 103.00   1.00    2.00    --   95.80  45.00  30.00   27
 52  \w     65.00  91.00   1.00    2.00    --   95.80  77.00  30.00   26
 53  \w     64.00  90.00   1.00    2.00    --   95.80  82.00  60.00   26
 54  \w     80.00 151.00   1.00    2.00    --   95.80  45.00-180.00   71
 55  \w     65.00  91.00   1.00    2.00    --   95.80  77.00   0.00   26
 56  \w     17.00 103.00   1.00    2.00    --   95.80 -61.00-150.00   86
 57  \w     67.00  93.00   1.00    2.00    --   95.80  77.00-120.00   26
 58  \w    125.00 184.00   1.00    2.00    --   95.80  77.00-120.00   59
 59  \w     68.00  94.00   1.00    2.00    --   95.80  69.00  36.60   26
 60  \w    123.00 172.00   1.00    2.00    --   95.80  58.00 -38.89   49
 61  \w     72.00 106.00   1.00    2.00    --   95.80  60.00 138.09   34
 62  \w     74.00 102.00   1.00    2.00    --   95.80  51.00   0.91   28
;
_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      -0.0660375000
_diffrn_orient_matrix_UB_12      0.0448314000
_diffrn_orient_matrix_UB_13      -0.1770370000
_diffrn_orient_matrix_UB_21      -0.1040646000
_diffrn_orient_matrix_UB_22      -0.0667891000
_diffrn_orient_matrix_UB_23      -0.1008891000
_diffrn_orient_matrix_UB_31      -0.2090122000
_diffrn_orient_matrix_UB_32      0.0192097000
_diffrn_orient_matrix_UB_33      0.0628594000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15600
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         6.125
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0433P)^2^+0.0722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2924
_reflns_number_total             3078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02485g2.cif
_cod_data_source_block           exp_2772
_cod_depositor_comments
'Adding full bibliography for 1569539--1569545.cif.'
_cod_database_code               1569541
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.803
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              74256
_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 2.127
_oxdiff_exptl_absorpt_empirical_full_min 0.738