Construction of Spiro-Fused 2-Oxindole/α-Methylene- γ-Butyrolactone Systems with Extremely High Enantioselectivity via Indium-Catalyzed Amide Allylation of N-Methyl Isatin.
Murata, Yusuke; Takahashi, Masaki; Yagishita, Fumitoshi; Sakamoto, Masami; Sengoku, Tetsuya; Yoda, Hidemi; Organic letters 15 (2013) 6182–6185; doi:10.1021/ol403014u

data_1513232
_publ_section_title
;
 Construction of Spiro-Fused 2-Oxindole/\a-Methylene- \g-Butyrolactone
 Systems with Extremely High Enantioselectivity via Indium-Catalyzed Amide
 Allylation of N-Methyl Isatin.
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_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6182
_journal_page_last               6185
_journal_paper_doi               10.1021/ol403014u
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H10 I N O3'
_chemical_formula_weight         355.12
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.314(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.2766(10)
_cell_length_b                   11.0112(6)
_cell_length_c                   13.5295(6)
_cell_measurement_reflns_used    7787
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.61
_cell_measurement_theta_min      3.91
_cell_volume                     2524.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8652
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.08
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    19.953
_exptl_absorpt_correction_T_max  0.6910
_exptl_absorpt_correction_T_min  0.1087
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         3.317
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.225
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.098(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0716
_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^)+(0.1458P)^2^+7.4713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1960
_reflns_number_gt                3514
_reflns_number_total             3680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403014u_si_002.cif
_cod_data_source_block           u130613yag_c2_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1513232