Palladium-catalysed ring-opening [3 + 2]-annulation of spirovinylcyclopropyl oxindole to diastereoselectively access spirooxindoles.
Xiao, Jun-An; Cheng, Xiu-Liang; Li, Yu-Chun; He, Yi-Miao; Li, Jin-Lian; Liu, Zhi-Ping; Xia, Peng-Ju; Su, Wei; Yang, Hua; Organic & biomolecular chemistry 17 (2018) 103–107; doi:10.1039/c8ob02859a

data_7156597
_publ_section_title
;
 Palladium-catalysed ring-opening [3 + 2]-annulation of
 spirovinylcyclopropyl oxindole to diastereoselectively access
 spirooxindoles.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              103
_journal_page_last               107
_journal_paper_doi               10.1039/c8ob02859a
_journal_volume                  17
_journal_year                    2018
_chemical_formula_sum            'C27 H23 Cl N2 O3'
_chemical_formula_weight         458.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc20bmkk
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-07-22 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                100.8225(11)
_cell_angle_beta                 90.1216(11)
_cell_angle_gamma                110.2565(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9496(3)
_cell_length_b                   9.6224(3)
_cell_length_c                   14.1054(5)
_cell_measurement_reflns_used    5119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.21
_cell_volume                     1116.34(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23598
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_correction_T_min  0.9096
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.3542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                4153
_reflns_number_total             5119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02859a2.cif
_cod_data_source_block           ja_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156596--7156597.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1116.34(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C54 H46 Cl2 N4 O6'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     917.85
_cod_database_code               7156597