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_7232635
_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         'C27 H27 N O7'
_chemical_formula_sum            'C27 H27 N O7'
_chemical_formula_weight         477.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1261(6)
_cell_length_b                   24.8124(6)
_cell_length_c                   9.1976(2)
_cell_measurement_reflns_used    6189
_cell_measurement_temperature    230
_cell_measurement_theta_max      72.6110
_cell_measurement_theta_min      4.0830
_cell_volume                     4821.3(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    5.3700
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -180.0000 84

  2 omega    1.00   75.00   1.0000    5.3700
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  150.0000 74

  3 omega    1.00   75.00   1.0000    5.3700
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  120.0000 74

  4 omega   18.00  106.00   1.0000    5.3700
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  -90.0000 88

  5 omega   22.00   74.00   1.0000    5.3700
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000    0.0000 52

  6 omega   41.00   89.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 48

  7 omega   58.00   85.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 27

  8 omega   70.00  107.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 37

  9 omega   40.00   80.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 40

 10 omega   64.00   90.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 26

 11 omega   44.00   95.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 51

 12 omega   44.00   69.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 25

 13 omega  100.00  178.00   1.0000   21.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 78
;
_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      0.0340707000
_diffrn_orient_matrix_UB_12      0.0329581000
_diffrn_orient_matrix_UB_13      0.0535350000
_diffrn_orient_matrix_UB_21      0.0638965000
_diffrn_orient_matrix_UB_22      -0.0392983000
_diffrn_orient_matrix_UB_23      -0.0261495000
_diffrn_orient_matrix_UB_31      0.0086974000
_diffrn_orient_matrix_UB_32      0.1594178000
_diffrn_orient_matrix_UB_33      -0.0174843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            14596
_diffrn_reflns_point_group_measured_fraction_full 0.666
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.636
_diffrn_reflns_theta_min         5.129
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51882
_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    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.29(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0568
_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^)+(0.1053P)^2^+0.9914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.238
_reflns_Friedel_fraction_full    0.286
_reflns_Friedel_fraction_max     0.265
_reflns_number_gt                5623
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra02192b2.cif
_cod_data_source_block           ljl-kjw-2-230k
_cod_database_code               7232635
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.75
_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:
 C41(H41), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C17(H17), C44(H44), C38(H38), C8(H8), C11(H11), C37(H37),
 C36(H36), C20(H20), C35(H35), C21(H21), C48(H48), C19(H19), C46(H46), C45(H45),
  C47(H47), C18(H18)
2.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C54(H54A,H54B,H54C),
 C3(H3A,H3B,H3C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C),
  C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              12975
_olex2_submission_special_instructions 'No special instructions were received'