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_7156929
_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         'C30 H24 N5 O5 S, C2 H5.5 O, C2 H6 O'
_chemical_formula_sum            'C34 H35.51 N5 O7 S'
_chemical_formula_weight         658.24
_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             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_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                   10.69410(10)
_cell_length_b                   16.3625(2)
_cell_length_c                   18.2683(2)
_cell_measurement_reflns_used    20644
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4220
_cell_measurement_theta_min      2.6640
_cell_volume                     3196.63(6)
_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      100.01(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 0.992
_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    -66.00  33.00   1.00    1.00    --  -41.11  38.00 -90.00   99
  2  \w     16.00  52.00   1.00    1.00    --   41.11 -99.00  60.00   36
  3  \w     34.00 134.00   1.00    1.00    --  106.95 -30.00   0.00  100
  4  \w    106.00 165.00   1.00    1.00    --  106.95  30.00 -60.00   59
  5  \w    145.00 171.00   1.00    1.00    --  106.95 125.00 -60.00   26
  6  \w    108.00 161.00   1.00    1.00    --  106.95 125.00  90.00   53
  7  \w     97.00 137.00   1.00    1.00    --  106.95 125.00 120.00   40
  8  \w     87.00 167.00   1.00    1.00    --  106.95  30.00-120.00   80
  9  \w     81.00 172.00   1.00    1.00    --  106.95  45.00-180.00   91
 10  \w     60.00  97.00   1.00    1.00    --   41.11-125.00-150.00   37
 11  \w     46.00 115.00   1.00    1.00    --  106.95 -45.00-180.00   69
 12  \w     53.00 109.00   1.00    1.00    --  106.95 -95.00 -60.00   56
 13  \w     38.00 137.00   1.00    1.00    --  106.95 -77.00  30.00   99
 14  \w     95.00 121.00   1.00    1.00    --  106.95-125.00 150.00   26
 15  \w     37.00  96.00   1.00    1.00    --  106.95 -95.00  30.00   59
 16  \w     25.00 106.00   1.00    1.00    --  106.95 -95.00-150.00   81
 17  \w    -72.00  26.00   1.00    1.00    --  -41.11  77.00   0.00   98
 18  \w   -107.00 -17.00   1.00    1.00    --  -41.11 -38.00  90.00   90
 19  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00 -60.00  108
 20  \w   -117.00  -9.00   1.00    1.00    --  -41.23 -77.00-150.00  108
 21  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00   0.00  100
;
_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      -0.0332358000
_diffrn_orient_matrix_UB_12      -0.0880274000
_diffrn_orient_matrix_UB_13      -0.0228103000
_diffrn_orient_matrix_UB_21      -0.0253217000
_diffrn_orient_matrix_UB_22      0.0294845000
_diffrn_orient_matrix_UB_23      -0.0786637000
_diffrn_orient_matrix_UB_31      0.1378809000
_diffrn_orient_matrix_UB_32      -0.0158247000
_diffrn_orient_matrix_UB_33      -0.0199638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27624
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.626
_diffrn_reflns_theta_min         3.626
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54186
_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    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             1386
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         6388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.9697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                6250
_reflns_number_total             6388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01203f2.cif
_cod_data_source_block           exp_1403
_cod_depositor_comments
'Adding full bibliography for 7156929--7156930.cif.'
_cod_database_code               7156929
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H4SA,H4SB,H4S} of C4S, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, {H29A,H29B,H29C} of C29, {H3SA,H3SB,H3SC} of C3S, {H1SA,
  H1SB,H1SC} of C1S, {H30A,H30B,H30C} of C30
2. Others
 Sof(H4S)=Sof(C3T)=Sof(H3TA)=Sof(H3TB)=1-FVAR(1)
 Sof(H4SA)=Sof(H4SB)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C2S(H2SA,H2SB), C4S(H4SA,H4SB)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C2(H2A), C18(H18), C16(H16), C15(H15), C5(H5), C3(H3),
 C21(H21), C17(H17), C22(H22), C25(H25), C4(H4A), C24(H24), C23(H23), C4S(H4S)
3.d X=CH2 refined with riding coordinates:
 C3T(H3TA,H3TB)
3.e Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C1S(H1SA,H1SB,H1SC), C30(H30A,H30B,H30C), C3S(H3SA,H3SB,
 H3SC)
3.f Idealised tetrahedral OH refined as rotating group:
 O2S(H2S), O1S(H1S)
;
_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 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.615