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_1569542
_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         'C17 H17 N O5'
_chemical_formula_sum            'C17 H17 N O5'
_chemical_formula_weight         315.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fz2gz
_audit_creation_date             2023-03-24
_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                 103.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.03880(10)
_cell_length_b                   31.5073(3)
_cell_length_c                   7.15720(10)
_cell_measurement_reflns_used    16802
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.3950
_cell_measurement_theta_min      2.8130
_cell_volume                     1544.32(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 0.998
_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    -29.00  19.00   1.00    1.00    --    0.00 -57.00-180.00   48
  2  \w    -23.00  80.00   1.00    1.00    --    0.00  57.00  30.00  103
  3  \w     52.00  88.00   1.00    1.00    --    0.00  37.00-150.00   36
  4  \w    -30.00  49.00   1.00    1.00    --    0.00  77.00 150.00   79
  5  \w     55.00  80.00   1.00    1.00    --    0.00  77.00 150.00   25
  6  \w     22.00  62.00   1.00    1.00    --    0.00  37.00 120.00   40
  7  \w    -15.00  10.00   1.00    1.00    --    0.00  37.00 120.00   25
  8  \w    -18.00  44.00   1.00    1.00    --    0.00  37.00-150.00   62
  9  \w    -24.00  86.00   1.00    1.00    --    0.00  19.00   0.00  110
 10  \w     65.00  91.00   1.00    1.00    --   95.80  78.00 -45.27   26
 11  \w    114.00 172.00   1.00    1.00    --   95.80  77.00 -90.00   58
 12  \w     65.00 105.00   1.00    1.00    --   95.80  77.00 -90.00   40
 13  \w      7.00 128.00   1.00    1.00    --   95.80 -82.00-120.00  121
 14  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 15  \w     64.00  89.00   1.00    1.00    --   95.80  80.00-172.88   25
 16  \w     96.00 185.00   1.00    1.00    --   95.80  75.00  79.80   89
 17  \w    127.00 153.00   1.00    1.00    --   95.80  82.00-120.00   26
 18  \w      8.00 126.00   1.00    1.00    --   95.80 -77.00 120.00  118
 19  \w     63.00 103.00   1.00    1.00    --   95.80  82.00-120.00   40
 20  \w    135.00 183.00   1.00    1.00    --   95.80  66.00 123.66   48
 21  \w     63.00  98.00   1.00    1.00    --   95.80  82.00 150.00   35
 22  \w     63.00  98.00   1.00    1.00    --   95.80  82.00  30.00   35
 23  \w      7.00 116.00   1.00    1.00    --   95.80 -82.00 -30.00  109
 24  \w     71.00 185.00   1.00    1.00    --   95.80  61.00  30.00  114
 25  \w    114.00 185.00   1.00    1.00    --   95.80  82.00-150.00   71
 26  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 27  \w     72.00 106.00   1.00    1.00    --   95.80  61.00 150.00   34
 28  \w     41.00 126.00   1.00    1.00    --   95.80 -82.00  60.00   85
 29  \w     75.00 162.00   1.00    1.00    --   95.80  45.00-120.00   87
 30  \w      6.00  74.00   1.00    1.00    --   95.80 -77.00-180.00   68
 31  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 32  \w     63.00  88.00   1.00    1.00    --   95.80  81.00  23.78   25
 33  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 34  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 35  \w     76.00 168.00   1.00    1.00    --   95.80  45.00   0.00   92
 36  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 37  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 39  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 40  \w     72.00 104.00   1.00    1.00    --   95.80  61.00-120.00   32
 41  \w     76.00 159.00   1.00    1.00    --   95.80  45.00-150.00   83
 42  \w     75.00 102.00   1.00    1.00    --   95.80  45.00  90.00   27
 43  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 44  \w    160.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   25
 45  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 46  \w     75.00 101.00   1.00    1.00    --   95.80  45.00 -30.00   26
 47  \w    121.00 178.00   1.00    1.00    --   95.80  45.00 -30.00   57
 48  \w     93.00 126.00   1.00    1.00    --   95.80 -77.00-180.00   33
 49  \w     71.00 114.00   1.00    1.00    --   95.80  61.00 120.00   43
 50  \w     71.00  96.00   1.00    1.00    --   95.80  61.00   0.00   25
 51  \w    119.00 149.00   1.00    1.00    --   95.80  77.00  60.00   30
 52  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -13.47   25
 53  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 54  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 55  \w     69.00  95.00   1.00    1.00    --   95.80  66.00 123.66   26
 56  \w    115.00 185.00   1.00    1.00    --   95.80  61.00 150.00   70
 57  \w     66.00  92.00   1.00    1.00    --   95.80  75.00  79.80   26
 58  \w     74.00 182.00   1.00    1.00    --   95.80  48.00 179.51  108
;
_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      -0.0140449000
_diffrn_orient_matrix_UB_12      0.0342552000
_diffrn_orient_matrix_UB_13      -0.1562407000
_diffrn_orient_matrix_UB_21      0.0670122000
_diffrn_orient_matrix_UB_22      0.0338806000
_diffrn_orient_matrix_UB_23      0.1565555000
_diffrn_orient_matrix_UB_31      0.2142595000
_diffrn_orient_matrix_UB_32      -0.0083550000
_diffrn_orient_matrix_UB_33      -0.0054934000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32400
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         5.617
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40086
_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    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.6661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2599
_reflns_number_total             2759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02485g2.cif
_cod_data_source_block           exp_3132
_cod_depositor_comments
'Adding full bibliography for 1569539--1569545.cif.'
_cod_database_code               1569542
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.736
_reflns_odcompleteness_completeness 99.96
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              44277
_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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.484