Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3?-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions
Wei Tan; Xin Li; Yu-Xin Gong; Meng-Di Ge; Feng Shi; Chem.Commun. 50 (2014) 15901–; doi:10.1039/C4cc07246D

data_7116123
_publ_section_title
;
 Highly diastereo- and enantioselective construction of a
 spiro[cyclopenta[b]indole-1,3?-oxindole] scaffold via catalytic
 asymmetric formal [3+2] cycloadditions
;
_journal_name_full               Chem.Commun.
_journal_page_first              15901
_journal_paper_doi               10.1039/C4cc07246D
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H30 Cl N3 O'
_chemical_formula_weight         604.12
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3755(14)
_cell_length_b                   12.5125(15)
_cell_length_c                   22.536(3)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      2.31
_cell_volume                     3489.7(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  '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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47288
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         8144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1593
_reflns_number_gt                5829
_reflns_number_total             8144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07246d2.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7116123