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_7134826
_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_moiety         'C21 H18 Cl N O3'
_chemical_formula_sum            'C21 H18 Cl N O3'
_chemical_formula_weight         367.81
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-10
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_audit_update_record
;
2024-01-20 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.286(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9050(6)
_cell_length_b                   10.3232(11)
_cell_length_c                   14.2771(16)
_cell_measurement_reflns_used    9775
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      3.73
_cell_volume                     865.08(16)
_computing_cell_refinement
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from \q/2\q scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30058
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.716
_diffrn_reflns_theta_min         5.424
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.402
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.204
_refine_ls_abs_structure_details
; 
 Flack x determined using 2246 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_coef       0.223(18)
_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   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0866P)^2^+0.0605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                4938
_reflns_number_total             4971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02323h2.cif
_cod_data_source_block           230505b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134826--7134828.cif.
;
_cod_database_code               7134826
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.817
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C16(H16), C17(H17), C19(H19), 
 C20(H20) 
2.c Idealised Me refined as rotating group: 
 C22(H22A,H22B,H22C) 
;
_shelx_res_checksum              7455
_shelx_hkl_checksum              49558
_olex2_submission_special_instructions 'No special instructions were received'