Efficient construction of spirocyclopentane-1,3-dioxindoles <i>via</i> an annulation reaction of isocyanides and 3-methyleneoxindoles.
Huang, Li; Ma, Wei-Qing; Sun, Jing; Han, Ying; Yan, Chao-Guo; Organic & biomolecular chemistry 23 (2025) 3224–3230; doi:10.1039/d5ob00206k

data_7160478
_publ_section_title
;
 Efficient construction of spirocyclopentane-1,3-dioxindoles <i>via</i> an
 annulation reaction of isocyanides and 3-methyleneoxindoles.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3224
_journal_page_last               3230
_journal_paper_doi               10.1039/d5ob00206k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C35 H28 Cl N3 O2, C H Cl3'
_chemical_formula_sum            'C36 H29 Cl4 N3 O2'
_chemical_formula_weight         677.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                72.714(11)
_cell_angle_beta                 82.722(14)
_cell_angle_gamma                86.047(13)
_cell_formula_units_Z            2
_cell_length_a                   8.313(4)
_cell_length_b                   13.728(5)
_cell_length_c                   15.146(6)
_cell_measurement_reflns_used    4902
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.45
_cell_measurement_theta_min      2.39
_cell_volume                     1636.2(12)
_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 0.997
_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_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23365
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.389
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0752
_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^)+(0.0812P)^2^+1.8823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3182
_reflns_number_total             6407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00206k2.cif
_cod_data_source_block           5jj
_cod_original_cell_volume        1636.3(12)
_cod_database_code               7160478
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              70969