Highly diastereoselective synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through [2 + 1] annulation of 2-ylideneoxindoles and sulfonium bromides.
Tang, Xue; Zhu, Hong-Ping; Zhou, Jin; Chen, Yang; Pan, Xiao-Li; Guo, Li; Li, Jun-Long; Peng, Cheng; Huang, Wei; Organic & biomolecular chemistry 16 (2018) 8169–8174; doi:10.1039/c8ob02034e

data_7156512
_publ_section_title
;
 Highly diastereoselective synthesis of cyclopropane-fused
 spiro-pseudoindoxyl derivatives through [2 + 1] annulation of
 2-ylideneoxindoles and sulfonium bromides.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8169
_journal_page_last               8174
_journal_paper_doi               10.1039/c8ob02034e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C29 H20 Br N O4 S'
_chemical_formula_sum            'C29 H20 Br N O4 S'
_chemical_formula_weight         558.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-18
_audit_creation_method
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Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
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_audit_update_record
;
2018-06-07 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                86.407(4)
_cell_angle_beta                 74.525(4)
_cell_angle_gamma                72.819(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8247(5)
_cell_length_b                   11.5260(6)
_cell_length_c                   11.6543(5)
_cell_measurement_reflns_used    6461
_cell_measurement_temperature    266(10)
_cell_measurement_theta_max      72.3080
_cell_measurement_theta_min      3.9880
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_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
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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      N~2~
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_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 0.975
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega    7.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -30.0000 74

  4 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -120.0000 95

  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  150.0000 84

  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  150.0000 66

  7 omega  -32.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -150.0000 95

  8 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 95

  9 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -30.0000 95

 10 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

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

 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   30.0000 53

 14 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 15 omega   40.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

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

 17 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

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

 19 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 20 omega   70.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

 21 omega  100.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

 22 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

 23 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 24 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -180.0000 95

 25 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -60.0000 88

 26 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   60.0000 95

 27 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  120.0000 84

 28 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -30.0000 84

 29 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000 -120.0000 88

 30 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000 -150.0000 88

 31 omega    9.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   90.0000 62

 32 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  120.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0126901000
_diffrn_orient_matrix_UB_12      -0.1149596000
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_diffrn_orient_matrix_UB_21      -0.1568780000
_diffrn_orient_matrix_UB_22      0.0693596000
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_diffrn_orient_matrix_UB_31      -0.0642349000
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_diffrn_orient_matrix_UB_33      -0.0929360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_number            13326
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.801
_diffrn_reflns_theta_min         4.880
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30858
_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    1.526
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.430
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0578
_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^)+(0.1014P)^2^+0.2124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4257
_reflns_number_total             4725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02034e2.cif
_cod_data_source_block           lq-0411
_cod_depositor_comments          'Adding full bibliography for 7156512.cif.'
_cod_database_code               7156512
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C4(H4), C5(H5), C16(H16), C29(H29), C19(H19), C12(H12),
 C25(H25), C22(H22), C20(H20), C13(H13), C15(H15), C28(H28), C27(H27), C26(H26),
  C14(H14), C21(H21)
;
_shelx_res_checksum              18088
_olex2_date_sample_data_collection 2018-04-17
_olex2_submission_special_instructions 'No special instructions were received'