Asymmetric Synthesis of Congested Spiro-cyclopentaneoxindoles via an Organocatalytic Cascade Reaction
Artur Noole; Kaja Ilmarinen; Ivar Järving; Margus Lopp; Tõnis Kanger; Journal of Organic Chemistry 78 (2013) 8117–8122; doi:10.1021/jo4008223

data_4028483
_publ_section_title
;
 Asymmetric Synthesis of Congested Spiro-cyclopentaneoxindoles via an
 Organocatalytic Cascade Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8117
_journal_page_last               8122
_journal_paper_doi               10.1021/jo4008223
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H17 Br N2 O6'
_chemical_formula_weight         413.23
_chemical_melting_point          442
_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                   10.5504(7)
_cell_length_b                   12.7378(9)
_cell_length_c                   12.8597(9)
_cell_measurement_temperature    200(2)
_cell_volume                     1728.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10965
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.5122
_exptl_absorpt_correction_T_min  0.2647
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0049P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0478
_reflns_number_gt                2837
_reflns_number_total             3019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4008223_si_002.cif
_cod_data_source_block           ki2
_cod_database_code               4028483