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_7222115
_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_sum            'C40 H33 N3 O4'
_chemical_formula_weight         619.69
_chemical_name_systematic        15a
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.100(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.523(2)
_cell_length_b                   8.9345(7)
_cell_length_c                   32.983(3)
_cell_measurement_reflns_used    6187
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      2.34
_cell_volume                     6408.1(10)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            22466
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        23.481
_diffrn_reflns_theta_max         23.481
_diffrn_reflns_theta_min         0.987
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             2608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     859
_refine_ls_number_reflns         22466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0757
_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^)+(0.0988P)^2^+10.6788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14693
_reflns_number_total             22466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra17215b2.cif
_cod_data_source_block           15a
_cod_original_cell_volume        6408.2(10)
_cod_database_code               7222115
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              71576