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_1518398
_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         'C22 H19 N O7'
_chemical_formula_sum            'C22 H19 N O7'
_chemical_formula_weight         409.38
_chemical_name_common            'coumarin 10'
_chemical_name_systematic
;
 racemic dimethyl(1S,3aR,9bS)-3-(4-methyoyphenyl)-4-oxo-1,9b-dihydro-
chromeno[3,4-c]pyrrole-1,3a(4H)-dicarboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.250(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.736(3)
_cell_length_b                   12.166(2)
_cell_length_c                   17.785(4)
_cell_measurement_reflns_used    6991
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      2.8
_cell_volume                     3836.7(13)
_computing_cell_refinement       'SAINT (Bruker, v6.45A)'
_computing_data_collection       'SMART (Bruker, v5.054)'
_computing_data_reduction        'SAINT (Bruker, v6.45A)'
_computing_molecular_graphics    'XP (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       \s
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39895
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         8768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0723P)^2^+1.2177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5977
_reflns_number_total             8768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5028128_si_002.cif
_cod_data_source_block           mn2188
_cod_depositor_comments
'Adding full bibliography for 1518396--1518398.cif.'
_cod_database_code               1518398
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4