Straightforward stereoselective synthesis of spiro-epoxyoxindoles.
Schulz, Verena; Davoust, Marion; Lemarié, Margareth; Lohier, Jean-François; Santos, Jana Sopkova de Oliveira; Metzner, Patrick; Brière, Jean-François; Organic letters 9 (2007) 1745–1748; doi:10.1021/ol070439x

data_1505375
_publ_section_title
;
 Straightforward stereoselective synthesis of spiro-epoxyoxindoles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1745
_journal_page_last               1748
_journal_paper_doi               10.1021/ol070439x
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        synthetised
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26
_chemical_melting_point          422(3)
_chemical_name_systematic
;
 3'-benzoylspiro[3H-indole-3,2'-oxiran]-2(1H)-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.3990(10)
_cell_angle_beta                 95.4780(10)
_cell_angle_gamma                98.8020(10)
_cell_formula_units_Z            2
_cell_length_a                   7.05350(10)
_cell_length_b                   8.5530(2)
_cell_length_c                   10.4821(2)
_cell_measurement_reflns_used    9432
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.27
_cell_measurement_theta_min      2.42
_cell_volume                     620.31(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'KAPPA APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30349
_diffrn_reflns_theta_full        39.27
_diffrn_reflns_theta_max         39.27
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.98458
_exptl_absorpt_correction_T_min  0.96395
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         7256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0777P)^2^+0.1328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                5351
_reflns_number_total             7256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070439xsi20070221_035638.cif
_cod_data_source_block           5a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '146-152\%C' was changed to '422(3)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was
estimated.

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1505375