Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles
Kang, Jing-Wen; Li, Xiang; Chen, Fei-Yu; Luo, Yuan; Zhang, Shu-Cang; Kang, Bin; Peng, Cheng; Tian, Xu; Han, Bo; RSC Advances 9 (2019) 12255–; doi:10.1039/C9RA02192B

data_7232636
_publ_section_title
;
 Protecting group-directed annulations of tetra-substituted oxindole
 olefins and sulfur ylides: regio- and chemoselective synthesis of
 cyclopropane- and dihydrofuran-fused spirooxindoles
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              12255
_journal_paper_doi               10.1039/C9RA02192B
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C28 H23 N O4'
_chemical_formula_sum            'C28 H23 N O4'
_chemical_formula_weight         437.47
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-07 deposited with the CCDC.    2019-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.286(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0593(3)
_cell_length_b                   14.8180(5)
_cell_length_c                   14.6664(6)
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    230
_cell_measurement_theta_max      72.4760
_cell_measurement_theta_min      5.0450
_cell_volume                     2168.50(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      air
_diffrn_ambient_temperature      230
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000  120.0000 84

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -57.0000   60.0000 84

  3 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171 -125.0000 -180.0000 66

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -99.0000   30.0000 74

  5 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171 -125.0000 -120.0000 66

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171  -99.0000  -60.0000 74

  7 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

  8 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

  9 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 10 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 11 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 12 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 14 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 15 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

 16 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 17 omega   19.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.9171   57.0000 -150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0447448000
_diffrn_orient_matrix_UB_12      -0.0627689000
_diffrn_orient_matrix_UB_13      0.0741512000
_diffrn_orient_matrix_UB_21      -0.0932361000
_diffrn_orient_matrix_UB_22      -0.0505831000
_diffrn_orient_matrix_UB_23      -0.0744361000
_diffrn_orient_matrix_UB_31      0.1146621000
_diffrn_orient_matrix_UB_32      -0.0655871000
_diffrn_orient_matrix_UB_33      -0.0134822000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.350
_diffrn_reflns_theta_min         5.047
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0984P)^2^+0.4842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3817
_reflns_number_total             4203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra02192b2.cif
_cod_data_source_block           ljl-kjw-1-230k
_cod_original_cell_volume        2168.50(14)
_cod_database_code               7232636
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.85
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C25(H25), C22(H22), C27(H27), C18(H18), C21(H21), C26(H26), C1(H1),
 C5(H5), C20(H20), C19(H19), C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C14(H14a,H14b,H14c)
;
_shelx_res_checksum              68107
_olex2_submission_special_instructions 'No special instructions were received'