Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.
Badillo, Joseph J.; Ribeiro, Carlos J. A.; Olmstead, Marilyn M.; Franz, Annaliese K.; Organic letters 16 (2014) 6270–6273; doi:10.1021/ol5028128

data_1518397
_publ_section_title
;
 Titanium(IV)-catalyzed stereoselective synthesis of
 spirooxindole-1-pyrrolines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6270
_journal_page_last               6273
_journal_paper_doi               10.1021/ol5028128
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
'C25 H23 F N2 O7, 0.25(C7 H8), 0.25(C7 H8) 0.5(C7 H8)'
_chemical_formula_sum            'C32 H31 F N2 O7'
_chemical_formula_weight         574.59
_chemical_name_common            'cis-3a toluene solvate'
_chemical_name_systematic
;
 racemic 4'-ethyl 5'-methyl(3R,4'S,5'R)-1-acetyl-5-fluoro-2'-(4-methyoxyphenyl)-2-oxo-
4',5'-dihydrospiro[indoline-3,3'-pyrrole]-4',5'-dicarboxylate
;
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                81.6796(9)
_cell_angle_beta                 76.9516(8)
_cell_angle_gamma                86.6732(8)
_cell_formula_units_Z            2
_cell_length_a                   8.7859(2)
_cell_length_b                   12.7763(4)
_cell_length_c                   13.0960(3)
_cell_measurement_reflns_used    9192
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      72.4
_cell_measurement_theta_min      3.5
_cell_volume                     1416.52(6)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Apex DUO'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24676
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.465
_diffrn_reflns_theta_min         3.496
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0641P)^2^+0.9487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5191
_reflns_number_total             5357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5028128_si_002.cif
_cod_data_source_block           mn2191
_cod_depositor_comments
'Adding full bibliography for 1518396--1518398.cif.'
_cod_database_code               1518397
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.854
_shelxl_version_number           2013-4