Pd-catalyzed asymmetric (6+2) dipolar cyclization for medium-sized spirooxindoles.
Xiao, Yu-Qing; Li, Zi-Qing; Hu, Fang; Li, Tian-Yu; Zhou, Zheng-Xin; Zhang, Zhihan; Tan, Ying; Xiao, Wen-Jing; Gavrilov, Konstantin Nikolaevich; Lu, Liang-Qiu; Chemical communications (Cambridge, England) 61 (2025) 12030–12033; doi:10.1039/d5cc02323h

data_7134827
_publ_section_title
;
 Pd-catalyzed asymmetric (6+2) dipolar cyclization for medium-sized
 spirooxindoles.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12030
_journal_page_last               12033
_journal_paper_doi               10.1039/d5cc02323h
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-03-21 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2247(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4802(4)
_cell_length_b                   13.0040(6)
_cell_length_c                   17.2546(9)
_cell_measurement_reflns_used    9062
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.49
_cell_measurement_theta_min      3.70
_cell_volume                     1677.13(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            65169
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        52.973
_diffrn_reflns_theta_max         52.973
_diffrn_reflns_theta_min         2.229
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.178
_refine_ls_abs_structure_details
; 
 Flack x determined using 2676 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_extinction_coef       0.078(6)
_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   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0853P)^2^+0.7676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5787
_reflns_number_total             5849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02323h2.cif
_cod_data_source_block           250303c_0m
_cod_depositor_comments
'Adding full bibliography for 7134826--7134828.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134827
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              18816
_shelx_hkl_checksum              22303