Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an azomethine ylide with isatin-derived imines: diastereo- and enantioselective construction of a spiro[imidazolidine-2,3'-oxindole] framework.
Wang, Yue-Ming; Zhang, Hong-Hao; Li, Can; Fan, Tao; Shi, Feng; Chemical communications (Cambridge, England) 52 (2016) 1804–1807; doi:10.1039/c5cc07924a

data_7118560
_publ_section_title
;
 Catalytic asymmetric chemoselective 1,3-dipolar cycloadditions of an
 azomethine ylide with isatin-derived imines: diastereo- and
 enantioselective construction of a spiro[imidazolidine-2,3'-oxindole]
 framework.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1804
_journal_page_last               1807
_journal_paper_doi               10.1039/c5cc07924a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C36 H34 N4 O8'
_chemical_formula_sum            'C36 H34 N4 O8'
_chemical_formula_weight         650.67
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2015-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-21 deposited with the CCDC.
2015-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.96120(10)
_cell_length_b                   24.5627(4)
_cell_length_c                   16.5897(3)
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    130
_cell_measurement_theta_max      67.04
_cell_measurement_theta_min      4.48
_cell_volume                     3243.76(9)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24751
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.178
_diffrn_reflns_theta_min         3.215
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.7407.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 3200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     871
_refine_ls_number_reflns         10598
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0696P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                9121
_reflns_number_total             10598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07924a2.cif
_cod_data_source_block           cu_sf150409_0m
_cod_database_code               7118560
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1A(H1A)
2.b Ternary CH refined with riding coordinates:
 C23(H23), C23A(H23A)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C26(H26A,H26B), C29(H29A,H29B), C9A(H9AA,H9AB), C26A(H26C,H26D),
 C29A(H29C,H29D)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C32(H32), C33(H33),
  C35(H35), C36(H36), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C11A(H11A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C17A(H17A), C18A(H18A),
 C20A(H20A), C21A(H21A), C32A(H32A), C33A(H33A), C35A(H35A), C36A(H36A)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C22A(H22D,H22E,
 H22F), C27A(H27D,H27E,H27F), C30A(H30D,H30E,H30F)
;
_shelx_res_checksum              24631
_olex2_submission_special_instructions 'No special instructions were received'