Enantioselective formal [3+2]-cycloadditions to access spirooxindoles bearing four contiguous stereocenters through synergistic catalysis.
Xiao, Jun-An; Li, Jin-Lian; Cheng, Xiu-Liang; Chen, Kai; Peng, Hai; Chen, Wen-Qiang; Su, Wei; Huang, Yan-Min; Yang, Hua; Chemical communications (Cambridge, England) 57 (2021) 4456–4459; doi:10.1039/d0cc07957j

data_7128109
_publ_section_title
;
 Enantioselective formal [3+2]-cycloadditions to access spirooxindoles
 bearing four contiguous stereocenters through synergistic catalysis.
;
_journal_issue                   36
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4456
_journal_page_last               4459
_journal_paper_doi               10.1039/d0cc07957j
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 Cl N O2'
_chemical_formula_sum            'C28 H24 Cl N O2'
_chemical_formula_weight         441.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc257c60
_audit_creation_date             2020-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-29 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3579(8)
_cell_length_b                   13.8057(13)
_cell_length_c                   19.3031(19)
_cell_measurement_reflns_used    9630
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.034
_cell_measurement_theta_min      3.038
_cell_volume                     2227.3(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35348
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0717 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.9278.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3561
_reflns_number_total             5093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc07957j2.cif
_cod_data_source_block           xiaojan509_10b_0m
_cod_depositor_comments
;
Adding full bibliography for 7128109--7128111.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C112 H96 Cl4 N4 O8'
_cod_original_formula_weight         1767.73
_cod_original_formula_moiety         '4(C28 H24 Cl N O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7128109
_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:
 C19(H19), C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C28(H28), C4(H4), C3(H3), C1(H1), C13(H13), C2(H2), C20(H20),
 C9(H9), C26(H26), C27(H27), C11(H11), C21(H21), C12(H12), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
;
_olex2_submission_special_instructions 'No special instructions were received'