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_7127417
_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         'C23 H20 Br N3 O4 S'
_chemical_formula_sum            'C23 H20 Br N3 O4 S'
_chemical_formula_weight         514.39
_chemical_compound_source        'From datablock 201908210_CCDC1'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-05
_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                 101.185(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6217(9)
_cell_length_b                   9.3855(4)
_cell_length_c                   14.7978(6)
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6300
_cell_measurement_theta_min      4.8240
_cell_volume                     2537.1(2)
_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 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    -61.00 -35.00   1.00    2.00    --  -33.50 178.00 -60.00   26
  2  \w   -101.00 -74.00   1.00    2.00    --  -33.50 178.00 -60.00   27
  3  \w    -51.00 -17.00   1.00    2.00    --  -33.50 -57.00   0.00   34
  4  \w    -84.00 -57.00   1.00    2.00    --  -33.50 -37.00  60.00   27
  5  \w    -51.00 -12.00   1.00    2.00    --  -33.50 -37.00  60.00   39
  6  \w     61.00  90.00   1.00    2.00    --   36.47 178.00 120.00   29
  7  \w     20.00  45.00   1.00    2.00    --   36.47  57.00 -60.00   25
  8  \w     75.00 106.00   1.00    2.00    --   36.47  37.00 150.00   31
  9  \w     72.00 107.00   1.00    2.00    --   36.47  37.00  90.00   35
 10  \w     11.00  40.00   1.00    2.00    --   36.47  77.00 -30.00   29
 11  \w     58.00 102.00   1.00    2.00    --   36.47 178.00  60.00   44
 12  \w     -1.00  24.00   1.00    2.00    --   36.47  94.00   6.24   25
 13  \w    -33.00  11.00   1.00    2.00    --   36.47 -77.00   0.00   44
 14  \w    -32.00  11.00   1.00    2.00    --   36.47 -57.00 -90.00   43
 15  \w     21.00  82.00   1.00    2.00    --   36.47  57.00  30.00   61
 16  \w      9.00  68.00   1.00    2.00    --   36.47  77.00  30.00   59
 17  \w     39.00  64.00   1.00    2.00    --   36.47 -77.00   0.00   25
 18  \w     57.00 102.00   1.00    2.00    --   36.47  57.00-150.00   45
 19  \w     75.00 100.00   1.00    2.00    --   36.47  57.00 -60.00   25
 20  \w     21.00  47.00   1.00    2.00    --   36.47  37.00 150.00   26
 21  \w     44.00  90.00   1.00    2.00    --   36.47  37.00  30.00   46
 22  \w     82.00 119.00   1.00   12.50    --  108.00  77.00 -90.00   37
 23  \w     83.00 117.00   1.00   12.50    --  108.00  30.00  90.00   34
 24  \w    116.00 178.00   1.00   12.50    --  108.00  45.00  90.00   62
 25  \w     88.00 114.00   1.00   12.50    --  108.00  61.00 -60.00   26
 26  \w     82.00 108.00   1.00   12.50    --  108.00  30.00  30.00   26
 27  \w    110.00 172.00   1.00   12.50    --  108.00  77.00 -60.00   62
 28  \w     42.00 132.00   1.00   12.50    --  108.00 -30.00 -90.00   90
 29  \w     85.00 112.00   1.00   12.50    --  108.00  30.00   0.00   27
 30  \w     85.00 115.00   1.00   12.50    --  108.00  30.00  60.00   30
 31  \w     89.00 114.00   1.00   12.50    --  108.00  45.00 -30.00   25
 32  \w     79.00 106.00   1.00   12.50    --  108.00  77.00 -60.00   27
 33  \w     79.00 105.00   1.00   12.50    --  108.00  77.00 -30.00   26
 34  \w     88.00 114.00   1.00   12.50    --  108.00  61.00  30.00   26
 35  \w    137.00 163.00   1.00   12.50    --  108.00  61.00  60.00   26
 36  \w    124.00 170.00   1.00   12.50    --  108.00  77.00   0.00   46
 37  \w     88.00 114.00   1.00   12.50    --  108.00  61.00  60.00   26
 38  \w     65.00 112.00   1.00   12.50    --  108.00-111.00  60.00   47
 39  \w     79.00 105.00   1.00   12.50    --  108.00  77.00   0.00   26
 40  \w     40.00  79.00   1.00   12.50    --  108.00 -94.00  30.00   39
 41  \w     89.00 115.00   1.00   12.50    --  108.00  61.00   0.00   26
 42  \w     79.00 105.00   1.00   12.50    --  108.00  77.00  60.00   26
 43  \w    133.00 160.00   1.00   12.50    --  108.00  45.00 -60.00   27
 44  \w     88.00 114.00   1.00   12.50    --  108.00  45.00 -60.00   26
 45  \w     82.00 119.00   1.00   12.50    --  108.00  30.00 -30.00   37
 46  \w     83.00 109.00   1.00   12.50    --  108.00  30.00 -60.00   26
 47  \w     88.00 114.00   1.00   12.50    --  108.00  61.00 -30.00   26
 48  \w     43.00 106.00   1.00   12.50    --  108.00 -94.00  90.00   63
 49  \w     89.00 114.00   1.00   12.50    --  108.00  45.00  30.00   25
 50  \w    118.00 167.00   1.00   12.50    --  108.00  77.00 -30.00   49
 51  \w    122.00 177.00   1.00   12.50    --  108.00  77.00  30.00   55
 52  \w     80.00 106.00   1.00   12.50    --  108.00  77.00  30.00   26
;
_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      -0.0007361000
_diffrn_orient_matrix_UB_12      -0.0395124000
_diffrn_orient_matrix_UB_13      0.1008351000
_diffrn_orient_matrix_UB_21      -0.0843395000
_diffrn_orient_matrix_UB_22      -0.0016858000
_diffrn_orient_matrix_UB_23      -0.0218646000
_diffrn_orient_matrix_UB_31      0.0010507000
_diffrn_orient_matrix_UB_32      -0.1593295000
_diffrn_orient_matrix_UB_33      -0.0247573000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.012
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_min         4.842
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82100
_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    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+7.8478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.799
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                3285
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05807f2.cif
_cod_data_source_block           201908210_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7127414--7127417.cif.'
_cod_original_cell_volume        2537.2(2)
_cod_database_code               7127417
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c20h20n4o4S1Br1
_shelx_estimated_absorpt_t_max   0.737
_shelx_estimated_absorpt_t_min   0.659
_reflns_odcompleteness_completeness 99.79
_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 N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C8
 2.2 with sigma of 0.02
 C7-C8A
 1.5 with sigma of 0.02
 C8-N2
 1.4 with sigma of 0.02
 C8A-N2A
 1.4 with sigma of 0.02
 O4A-N2A
 2.2 with sigma of 0.02
 N3A-O4A
 1.4 with sigma of 0.02
 C9A-C7
 1.52 with sigma of 0.02
 N1-S1A
 1.68 with sigma of 0.02
 S1A-O2A
 1.5 with sigma of 0.02
 S1-O2
 1.5 with sigma of 0.02
 N1-S1
 1.65 with sigma of 0.02
 S1A-N1A
 1.65 with sigma of 0.02
 C7-C9
 1.5 with sigma of 0.02
 C7-C9A
 1.5 with sigma of 0.02
 C7-C8
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2A) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C12A)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C18A) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C21A)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23A) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(C8A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N3) = Uanis(N3A)
Uanis(O4) = Uanis(O4A)
Uanis(N2) = Uanis(N2A)
Uanis(C8) = Uanis(C8A)
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(Br1) = Uanis(Br1A)
Uanis(C23) = Uanis(C23A)
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C17) = Uanis(C17A)
Uanis(S1) = Uanis(S1A)
Uanis(O1) = Uanis(O1A)
Uanis(O2) = Uanis(O2A)
Uanis(N1) = Uanis(N1A)
4. Others
 Sof(Br1A)=Sof(C8A)=Sof(C9A)=Sof(C13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=
 Sof(C10A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=Sof(N2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(N3A)=Sof(O4A)=1-FVAR(1)
 Sof(Br1)=Sof(C8)=Sof(C9)=Sof(C13)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=
 Sof(C10)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(N3)=
 Sof(O4)=FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=
 Sof(C22A)=Sof(H22A)=Sof(C17A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(N1A)=
 Sof(H1AA)=Sof(O1A)=Sof(O2A)=Sof(S1A)=1-FVAR(2)
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=
 Sof(H22)=Sof(C17)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(N1)=Sof(H1A)=
 Sof(O1)=Sof(O2)=Sof(S1)=FVAR(2)
5.a Riding coordinates:
 N1(H1A), N1A(H1AA), N2(H2A,H2B), N2A(H2AA,H2AB)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C11(H11), C15(H15), C14(H14), C12A(H12A),
 C11A(H11A), C15A(H15A), C14A(H14A), C18(H18), C19(H19), C21(H21), C22(H22),
 C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A)
5.c Fitted hexagon refined as free rotating group:
 C13(C12,C11,C10,C15,C14), C13A(C12A,C11A,C10A,C15A,C14A), C18(C19,C20,C21,C22,
 C17), C18A(C19A,C20A,C21A,C22A,C17A)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F)
;
_olex2_date_sample_data_collection 2019-09-02
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.862