Highly regio- and diastereoselective construction of spirocyclic compounds <i>via</i> palladium-catalyzed [3 + 2] cycloaddition of vinyl methylene cyclic carbonates with pyrrolidinones.
Liu, Huizhi; Zong, Jiayi; Zhang, Boxuan; Wang, JiaHao; Zheng, Guohui; Ke, Miaolin; Chen, Fener; Organic & biomolecular chemistry 23 (2025) 7951–7955; doi:10.1039/d5ob01194a

data_7160693
_publ_section_title
;
 Highly regio- and diastereoselective construction of spirocyclic
 compounds <i>via</i> palladium-catalyzed [3 + 2] cycloaddition of vinyl
 methylene cyclic carbonates with pyrrolidinones.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7951
_journal_page_last               7955
_journal_paper_doi               10.1039/d5ob01194a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C29 H25 N O3'
_chemical_formula_sum            'C29 H25 N O3'
_chemical_formula_weight         435.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-12-27
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-12-29 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.102(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4530(4)
_cell_length_b                   22.8186(15)
_cell_length_c                   15.7558(10)
_cell_measurement_reflns_used    6926
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      67.992
_cell_measurement_theta_min      3.874
_cell_volume                     2284.0(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29726
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         3.445
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0913 after correction.
The Ratio of minimum to maximum transmission is 0.8339.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0860
_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^)+(0.1531P)^2^+0.6300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2373
_refine_ls_wR_factor_ref         0.2654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2645
_reflns_number_total             4031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01194a2.cif
_cod_data_source_block           dcm
_cod_depositor_comments          'Adding full bibliography for 7160693.cif.'
_cod_database_code               7160693
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_shelx_res_checksum              85843
_olex2_submission_special_instructions 'No special instructions were received'