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_1569545
_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_formula_moiety         'C23 H25 N O6'
_chemical_formula_sum            'C23 H25 N O6'
_chemical_formula_weight         411.46
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fz2l3
_audit_creation_date             2023-02-10
_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                89.169(2)
_cell_angle_beta                 76.315(2)
_cell_angle_gamma                69.111(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9746(3)
_cell_length_b                   9.7722(3)
_cell_length_c                   12.9941(4)
_cell_measurement_reflns_used    13812
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      74.1240
_cell_measurement_theta_min      3.5060
_cell_volume                     1031.41(6)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9897
_diffrn_measured_fraction_theta_max 0.9897
_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    -19.00  20.00   1.00    1.00    --    0.00  57.00 150.00   39
  2  \w     25.00  51.00   1.00    1.00    --    0.00  57.00 150.00   26
  3  \w     39.00  65.00   1.00    1.00    --    0.00  37.00  90.00   26
  4  \w    -31.00  42.00   1.00    1.00    --    0.00  82.00  90.00   73
  5  \w     32.00  86.00   1.00    1.00    --    0.00  57.00-120.00   54
  6  \w    -64.00 -38.00   1.00    1.00    --    0.00 -19.00  30.00   26
  7  \w    -24.00  17.00   1.00    1.00    --    0.00 -37.00 -30.00   41
  8  \w    -19.00  14.00   1.00    1.00    --    0.00  37.00  90.00   33
  9  \w    -19.00  28.00   1.00    1.00    --    0.00  57.00-120.00   47
 10  \w    -89.00 -12.00   1.00    1.00    --    0.00 -57.00 -60.00   77
 11  \w    -13.00  23.00   1.00    1.00    --    0.00 -19.00  30.00   36
 12  \w     37.00  87.00   1.00    1.00    --    0.00  57.00-180.00   50
 13  \w    -21.00  13.00   1.00    1.00    --    0.00  57.00-180.00   34
 14  \w    -88.00 -63.00   1.00    1.00    --    0.00 -37.00 -30.00   25
 15  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 16  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 17  \w     76.00 122.00   1.00    1.00    --   95.80  45.00 -90.00   46
 18  \w     73.00  98.00   1.00    1.00    --   95.80  61.00 -90.00   25
 19  \w    117.00 173.00   1.00    1.00    --   95.80  77.00  90.00   56
 20  \w     92.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   35
 21  \w     74.00 148.00   1.00    1.00    --   95.80  50.00-150.99   74
 22  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 23  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 24  \w    151.00 183.00   1.00    1.00    --   95.80  77.00 -90.00   32
 25  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 26  \w     71.00 128.00   1.00    1.00    --   95.80  61.00-180.00   57
 27  \w     72.00 127.00   1.00    1.00    --   95.80  61.00   0.00   55
 28  \w    140.00 184.00   1.00    1.00    --   95.80  61.00   0.00   44
 29  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 30  \w    123.00 148.00   1.00    1.00    --   95.80  82.00-150.00   25
 31  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 32  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 33  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  60.00   26
 34  \w     92.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   35
 35  \w      6.00  70.00   1.00    1.00    --   95.80 -82.00-120.00   64
 36  \w    134.00 167.00   1.00    1.00    --   95.80  61.00 -30.00   33
 37  \w     71.00 130.00   1.00    1.00    --   95.80  61.00 -30.00   59
 38  \w     61.00 128.00   1.00    1.00    --   95.80 -82.00 120.00   67
 39  \w     27.00  56.00   1.00    1.00    --   95.80 -82.00 120.00   29
 40  \w    112.00 185.00   1.00    1.00    --   95.80  82.00  60.00   73
 41  \w     74.00 103.00   1.00    1.00    --   95.80  61.00 -60.00   29
 42  \w     76.00 120.00   1.00    1.00    --   95.80  45.00 120.00   44
 43  \w     75.00 109.00   1.00    1.00    --   95.80  45.00  90.00   34
 44  \w    141.00 166.00   1.00    1.00    --   95.80  45.00  90.00   25
 45  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 46  \w     47.00 125.00   1.00    1.00    --   95.80 -82.00 -30.00   78
 47  \w     63.00  97.00   1.00    1.00    --   95.80  82.00   0.00   34
 48  \w     72.00  98.00   1.00    1.00    --   95.80  61.00-120.00   26
 49  \w    113.00 185.00   1.00    1.00    --   95.80  61.00-120.00   72
 50  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 51  \w     78.00 117.00   1.00    1.00    --   95.80  30.00  60.00   39
 52  \w    132.00 167.00   1.00    1.00    --   95.80  30.00  60.00   35
 53  \w    135.00 161.00   1.00    1.00    --   95.80  77.00  30.00   26
 54  \w     73.00 106.00   1.00    1.00    --   95.80  61.00 150.00   33
 55  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 56  \w    118.00 185.00   1.00    1.00    --   95.80  61.00-150.00   67
 57  \w      6.00  73.00   1.00    1.00    --   95.80 -82.00-180.00   67
 58  \w     80.00 124.00   1.00    1.00    --   95.80 -82.00-180.00   44
 59  \w     77.00 184.00   1.00    1.00    --   95.80  30.00-180.00  107
 60  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 61  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 62  \w    134.00 178.00   1.00    1.00    --   95.80  45.00 -90.00   44
 63  \w     65.00  99.00   1.00    1.00    --   95.80  82.00  30.00   34
 64  \w      6.00 110.00   1.00    1.00    --   95.80 -61.00 -30.00  104
 65  \w     66.00  92.00   1.00    1.00    --   95.80  77.00-180.00   26
 66  \w    111.00 136.00   1.00    1.00    --   95.80  65.00 120.94   25
 67  \w     70.00  96.00   1.00    1.00    --   95.80  65.00 120.94   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      0.1251834000
_diffrn_orient_matrix_UB_12      0.0237675000
_diffrn_orient_matrix_UB_13      0.0540417000
_diffrn_orient_matrix_UB_21      0.1414890000
_diffrn_orient_matrix_UB_22      -0.0866655000
_diffrn_orient_matrix_UB_23      -0.0949200000
_diffrn_orient_matrix_UB_31      -0.0165886000
_diffrn_orient_matrix_UB_32      0.1434099000
_diffrn_orient_matrix_UB_33      -0.0552063000
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22027
_diffrn_reflns_theta_full        67.0632
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66635
_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    1.3248
_exptl_crystal_description       block
_exptl_crystal_F_000             437.5210
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.2376
_refine_diff_density_min         -0.1534
_refine_diff_density_rms         0.0323
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             12.5878
_refine_ls_goodness_of_fit_ref   1.0394
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0394
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.3059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3414
_reflns_number_total             3656
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc02485g2.cif
_cod_data_source_block           exp_3027
_cod_depositor_comments
'Adding full bibliography for 1569539--1569545.cif.'
_cod_database_code               1569545
_reflns_odcompleteness_completeness 99.70
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1a), C2(H2), C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.d Aromatic/amide H refined with riding coordinates:
 C23(H23), C22(H22), C21(H21), C20(H20), C19(H19), C16(H16), C15(H15),
 C14(H14), C13(H13), C12(H12)
2.e Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C8(H8a,H8b,H8c), C11(H11a,H11b,H11c)
;
_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 2.140
_oxdiff_exptl_absorpt_empirical_full_min 0.514