Acetic Acid Promoted Tandem Cyclization of in situ Generated 1,3-Dipoles: Setereoselective Synthesis of Dispiroimidazolidinyl and Dispiropyrrolidinyl Oxindoles with Multiple Chiral Stereocenters
Koorathota, Suman; Thennarasu, Sathiah; RSC Adv.  (2015) –; doi:10.1039/C5RA17215B

data_7222114
_publ_section_title
;
 Acetic Acid Promoted Tandem Cyclization of in situ Generated 1,3-Dipoles:
 Setereoselective Synthesis of Dispiroimidazolidinyl and
 Dispiropyrrolidinyl Oxindoles with Multiple Chiral Stereocenters
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17215B
_journal_year                    2015
_chemical_formula_moiety         'C46 H40 N4 O2'
_chemical_formula_sum            'C46 H40 N4 O2'
_chemical_formula_weight         680.82
_chemical_name_systematic        3a
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                106.000(5)
_cell_angle_beta                 92.630(5)
_cell_angle_gamma                114.145(5)
_cell_formula_units_Z            2
_cell_length_a                   11.335(5)
_cell_length_b                   12.004(5)
_cell_length_c                   15.559(5)
_cell_measurement_reflns_used    7437
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      1.38
_cell_volume                     1826.4(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26982
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.2525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.2037
_reflns_number_gt                4189
_reflns_number_total             7437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17215b2.cif
_cod_data_source_block           shelxl
_cod_database_code               7222114