Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity
Huang, Ying; Huang, Yi-Xin; Sun, Jing; Yan, Chao-Guo; RSC Advances 8 (2018) 23990–; doi:10.1039/C8RA04375B

data_7231064
_publ_section_title
;
 Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition
 of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their
 cytotoxicity
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              23990
_journal_paper_doi               10.1039/C8RA04375B
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C26 H25 N O8'
_chemical_formula_sum            'C26 H25 N O8'
_chemical_formula_weight         479.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-15 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.529(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1470(9)
_cell_length_b                   20.9021(16)
_cell_length_c                   11.8600(9)
_cell_measurement_reflns_used    8766
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.34
_cell_volume                     2370.7(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21159
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.066
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0967P)^2^+0.3599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3275
_reflns_number_total             4651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra04375b2.cif
_cod_data_source_block           1a
_cod_database_code               7231064
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              36071