Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles <i>via</i> annulation involving isatylidene malononitriles and benzylamines.
Yavari, Issa; Ahmadi, Mahmoud; Ravaghi, Parisa; Mohsenzadeh, Ramin; Organic & biomolecular chemistry 23 (2025) 2712–2720; doi:10.1039/d4ob01811g

data_7160373
_publ_section_title
;
 Diastereoselective assembly of dispiro-cyclopentene-linked bisoxindoles
 <i>via</i> annulation involving isatylidene malononitriles and
 benzylamines.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2712
_journal_page_last               2720
_journal_paper_doi               10.1039/d4ob01811g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H20 N6 O3, C2 H3 N'
_chemical_formula_sum            'C32 H23 N7 O3'
_chemical_formula_weight         553.57
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.09(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.230(2)
_cell_length_b                   14.496(3)
_cell_length_c                   17.861(4)
_cell_measurement_reflns_used    20409
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      1.8
_cell_volume                     2853.3(10)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR-345dtb
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20409
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         1.823
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.03811
_exptl_absorpt_correction_T_min  0.95136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0807
_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^)+(0.0711P)^2^+2.0024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4537
_reflns_number_total             5642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01811g2.cif
_cod_data_source_block           2_pl
_cod_depositor_comments          'Adding full bibliography for 7160373.cif.'
_cod_database_code               7160373
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N2(H2), N5(H5), C4(H4), C28(H28), C18(H18), C24(H24), C19(H19),
 C27(H27), C16(H16), C26(H26), C5(H5A), C2(H2A), C25(H25), C17(H17), C3(H3)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'