A Versatile Synthesis of Unsymmetrical 3,3'-Bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins
Ellis, J. Michael; Overman, Larry E.; Tanner, Huw R.; Wang, Jocelyn; The Journal of Organic Chemistry 73 (2008) 9151–9154; doi:10.1021/jo801867w

data_4023869
_publ_section_title
;
 A Versatile Synthesis of Unsymmetrical 3,3'-Bioxindoles: Stereoselective
 Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins
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_journal_coden_ASTM              JOCEAH
_journal_issue                   22
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              9151
_journal_page_last               9154
_journal_paper_doi               10.1021/jo801867w
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                111.929(2)
_cell_angle_beta                 108.080(2)
_cell_angle_gamma                93.745(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1562(12)
_cell_length_b                   10.6764(14)
_cell_length_c                   12.1295(16)
_cell_measurement_temperature    155(2)
_cell_volume                     1023.3(2)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      155(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10666
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.3914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                3903
_reflns_number_total             4498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801867w_si_001.cif
_cod_data_source_block           leo212
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-10
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_cod_database_code               4023869