Regio- and stereoselective [3 + 2] cycloaddition reaction: access to isoxazole-dispirobisoxindoles featuring three contiguous stereocenters.
Chen, Shuang; Wang, Guan-Lian; Xu, Sheng-Wen; Tian, Min-Yi; Zhang, Min; Liu, Xiong-Li; Yuan, Wei-Cheng; Organic & biomolecular chemistry 17 (2019) 6551–6556; doi:10.1039/c9ob01203f

data_7156930
_publ_section_title
;
 Regio- and stereoselective [3 + 2] cycloaddition reaction: access to
 isoxazole-dispirobisoxindoles featuring three contiguous stereocenters.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6551
_journal_page_last               6556
_journal_paper_doi               10.1039/c9ob01203f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H21 N5 O5 S, 2(C2 H6 O)'
_chemical_formula_sum            'C33 H33 N5 O7 S'
_chemical_formula_weight         643.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-05-22 deposited with the CCDC.    2019-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1703(2)
_cell_length_b                   15.8824(3)
_cell_length_c                   18.1124(3)
_cell_measurement_reflns_used    12203
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4680
_cell_measurement_theta_min      2.4070
_cell_volume                     3213.34(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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   -121.00   0.00   1.00    1.00    --  -40.98 -19.00-150.00  121
  2  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00  60.00  101
  3  \w     23.00  97.00   1.00    1.00    --   40.98-125.00  90.00   74
  4  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  30.00   84
  5  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  90.00  104
  6  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00  60.00   99
  7  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  60.00  104
  8  \w     81.00 178.00   1.00    1.00    --  106.95  45.00-120.00   97
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
 10  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  60.00  109
 11  \w   -113.00 -90.00   1.00    1.00    --  -40.98 -57.00 150.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350362000
_diffrn_orient_matrix_UB_12      -0.0829703000
_diffrn_orient_matrix_UB_13      0.0384957000
_diffrn_orient_matrix_UB_21      0.0836976000
_diffrn_orient_matrix_UB_22      -0.0488105000
_diffrn_orient_matrix_UB_23      -0.0523214000
_diffrn_orient_matrix_UB_31      0.1038497000
_diffrn_orient_matrix_UB_32      0.0113049000
_diffrn_orient_matrix_UB_33      0.0550193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18187
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.806
_diffrn_reflns_theta_min         3.701
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0625P)^2^+0.3461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6169
_reflns_number_total             6341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01203f2.cif
_cod_data_source_block           wgl-f
_cod_depositor_comments
'Adding full bibliography for 7156929--7156930.cif.'
_cod_database_code               7156930
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2S(H2SA,H2SB), C4S(H4SA,H4SB)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C17(H17), C3(H3), C5(H5), C14(H14), C15(H15), C16(H16),
 C4(H4), C20(H20), C24(H24), C23(H23), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C3S(H3SA,H3SB,H3SC), C1S(H1SA,H1SB,
 H1SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O2S(H2S)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.635