Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines.
Liu, Hui; Yan, Yingkun; Zhang, Jiayan; Liu, Min; Cheng, Shaobing; Wang, Zhouyu; Zhang, Xiaomei; Chemical communications (Cambridge, England) 56 (2020) 13591–13594; doi:10.1039/d0cc05807f

data_7127415
_publ_section_title
;
 Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with
 quinone monoimines.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13591
_journal_page_last               13594
_journal_paper_doi               10.1039/d0cc05807f
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 N3 O5 S, H2 O'
_chemical_formula_sum            'C22 H25 N3 O6 S'
_chemical_formula_weight         459.51
_chemical_compound_source        'From datablock 201912334'
_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     direct
_audit_creation_date             2019-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-27 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.913(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6772(5)
_cell_length_b                   6.3645(4)
_cell_length_c                   15.4108(7)
_cell_measurement_reflns_used    3050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6120
_cell_measurement_theta_min      3.7820
_cell_volume                     1142.65(10)
_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    'ShelXS (Sheldrick, 2008)'
_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 1.000
_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      5.00  32.00   1.00    1.75    --  -33.50  57.00  60.00   27
  2  \w    -24.00  37.00   1.00    1.75    --  -33.50  19.00-180.00   61
  3  \w    -54.00 -27.00   1.00    1.75    --  -33.50  19.00-180.00   27
  4  \w    -39.00  -7.00   1.00    1.75    --  -33.50  57.00  60.00   32
  5  \w     58.00 109.00   1.00    1.75    --   36.47 178.00-120.00   51
  6  \w     18.00  70.00   1.00    1.75    --   36.47  37.00  30.00   52
  7  \w     71.00  99.00   1.00    1.75    --   36.47  77.00-150.00   28
  8  \w     23.00  59.00   1.00    1.75    --   36.47  57.00  90.00   36
  9  \w      3.00  30.00   1.00    1.75    --   36.47 -99.00-120.00   27
 10  \w     10.00  37.00   1.00    1.75    --   36.47  77.00-150.00   27
 11  \w     15.00  79.00   1.00    1.75    --   36.47  37.00 150.00   64
 12  \w     -3.00  76.00   1.00    1.75    --   36.47 -99.00 -90.00   79
 13  \w     37.00  64.00   1.00    1.75    --   36.47  57.00 -60.00   27
 14  \w      9.00  62.00   1.00    1.75    --   36.47  77.00 150.00   53
 15  \w      6.00 100.00   1.00    1.75    --   36.47  19.00  90.00   94
 16  \w     32.00  59.00   1.00    1.75    --   36.47  57.00  60.00   27
 17  \w     79.00 105.00   1.00    5.50    --  108.00  77.00 120.00   26
 18  \w     84.00 111.00   1.00    5.50    --  108.00  30.00-150.00   27
 19  \w     88.00 156.00   1.00    5.50    --  108.00  45.00 120.00   68
 20  \w     80.00 105.00   1.00    5.50    --  108.00  77.00  60.00   25
 21  \w     89.00 114.00   1.00    5.50    --  108.00  45.00  30.00   25
 22  \w     89.00 114.00   1.00    5.50    --  108.00  45.00-180.00   25
 23  \w     38.00  65.00   1.00    5.50    --  108.00 -94.00 -30.00   27
 24  \w     71.00 107.00   1.00    5.50    --  108.00 -94.00 -30.00   36
 25  \w     83.00 109.00   1.00    5.50    --  108.00  30.00  90.00   26
 26  \w     82.00 108.00   1.00    5.50    --  108.00  30.00-180.00   26
 27  \w     66.00  93.00   1.00    5.50    --  108.00 -94.00-180.00   27
 28  \w     88.00 115.00   1.00    5.50    --  108.00  61.00-180.00   27
 29  \w    149.00 175.00   1.00    5.50    --  108.00  30.00-150.00   26
 30  \w     88.00 120.00   1.00    5.50    --  108.00  61.00 120.00   32
 31  \w     79.00 105.00   1.00    5.50    --  108.00  77.00  30.00   26
 32  \w     89.00 114.00   1.00    5.50    --  108.00  61.00  90.00   25
 33  \w    122.00 157.00   1.00    5.50    --  108.00  77.00  90.00   35
 34  \w    139.00 172.00   1.00    5.50    --  108.00  77.00 150.00   33
 35  \w     81.00 107.00   1.00    5.50    --  108.00  77.00  90.00   26
 36  \w    150.00 175.00   1.00    5.50    --  108.00  30.00 150.00   25
 37  \w     82.00 114.00   1.00    5.50    --  108.00  30.00 150.00   32
 38  \w    123.00 175.00   1.00    5.50    --  108.00  77.00-180.00   52
 39  \w     79.00 105.00   1.00    5.50    --  108.00  77.00 150.00   26
 40  \w     89.00 114.00   1.00    5.50    --  108.00  61.00  60.00   25
 41  \w     90.00 117.00   1.00    5.50    --  108.00  61.00 150.00   27
 42  \w     83.00 110.00   1.00    5.50    --  108.00  30.00 120.00   27
 43  \w     80.00 107.00   1.00    5.50    --  108.00  77.00-180.00   27
 44  \w     86.00 113.00   1.00    5.50    --  108.00  30.00  60.00   27
 45  \w    111.00 172.00   1.00    5.50    --  108.00  77.00 120.00   61
 46  \w     93.00 120.00   1.00    5.50    --  108.00  61.00  30.00   27
 47  \w     37.00 112.00   1.00    5.50    --  108.00-111.00 -90.00   75
 48  \w     97.00 176.00   1.00    5.50    --  108.00  77.00-120.00   79
 49  \w     94.00 141.00   1.00    5.50    --  108.00  45.00  60.00   47
 50  \w    149.00 177.00   1.00    5.50    --  108.00  45.00  60.00   28
 51  \w     67.00  94.00   1.00    5.50    --  108.00  15.00-120.00   27
 52  \w     38.00  65.00   1.00    5.50    --  108.00 -94.00-180.00   27
;
_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      0.0681133000
_diffrn_orient_matrix_UB_12      0.0157038000
_diffrn_orient_matrix_UB_13      -0.0819142000
_diffrn_orient_matrix_UB_21      0.1128973000
_diffrn_orient_matrix_UB_22      -0.0313521000
_diffrn_orient_matrix_UB_23      0.0562794000
_diffrn_orient_matrix_UB_31      -0.0103502000
_diffrn_orient_matrix_UB_32      -0.2394479000
_diffrn_orient_matrix_UB_33      -0.0128207000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9411
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.794
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98483
_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    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0620P)^2^+0.1026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.755
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                3302
_reflns_number_total             3625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05807f2.cif
_cod_data_source_block           201912334
_cod_depositor_comments
'Adding full bibliography for 7127414--7127417.cif.'
_cod_database_code               7127415
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4S1
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.769
_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, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              38616
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.873