Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene <i>N</i>-arylpyrrolidine-diones.
Dahiya, Pooja; Yadav, Anoop; Peddinti, Rama Krishna; Organic & biomolecular chemistry 21 (2023) 9192–9199; doi:10.1039/d3ob01629c

data_7159651
_publ_section_title
;
 Spirocyclization and Michael addition of 3-benzylidene succinimides:
 route to spirocyclopentapyrrolidine-tetraones and benzylidene
 <i>N</i>-arylpyrrolidine-diones.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9192
_journal_page_last               9199
_journal_paper_doi               10.1039/d3ob01629c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C33 H23 N O5 S'
_chemical_formula_sum            'C33 H22 N O5 S'
_chemical_formula_weight         544.57
_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_date             2022-11-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-12-17 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                114.144(6)
_cell_angle_beta                 108.931(7)
_cell_angle_gamma                92.315(7)
_cell_formula_units_Z            2
_cell_length_a                   10.988(2)
_cell_length_b                   11.648(2)
_cell_length_c                   12.588(3)
_cell_measurement_reflns_used    9083
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.19
_cell_volume                     1362.4(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      250.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46666
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.000
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9443.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       cubic
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.9165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4133
_reflns_number_total             4779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01629c2.cif
_cod_data_source_block           mo_jrk_pd_51a_0m
_cod_depositor_comments
'Adding full bibliography for 7159651--7159652.cif.'
_cod_database_code               7159651
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C1(H1)
2.c Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C)
;
_shelx_res_checksum              99823
_olex2_submission_special_instructions 'No special instructions were received'