Diastereo- and Enantioselective Construction of Spirooxindole Scaffolds through a Catalytic Asymmetric [3+3] Cycloaddition
Li, Can; Lu, Han; Sun, Xiao-Xue; Mei, Guang-Jian; Shi, Feng; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01059A

data_7155639
_publ_section_title
;
 Diastereo- and Enantioselective Construction of Spirooxindole Scaffolds
 through a Catalytic Asymmetric [3+3] Cycloaddition
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01059A
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H31 N3 O5'
_chemical_formula_sum            'C32 H31 N3 O5'
_chemical_formula_weight         537.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-04-29 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   31.9591(4)
_cell_length_b                   33.2764(4)
_cell_length_c                   10.32080(10)
_cell_measurement_reflns_used    7394
_cell_measurement_temperature    130
_cell_measurement_theta_max      67.95
_cell_measurement_theta_min      3.84
_cell_volume                     10976.0(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20326
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.544
_diffrn_reflns_theta_min         3.835
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1134 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.7775.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             4544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+12.9212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4729
_reflns_number_total             4942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01059a2.cif
_cod_data_source_block           dm16902
_cod_database_code               7155639
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.869
_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 Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              7569
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'