Dinuclear zinc cooperative catalytic three-component reactions for highly enantioselective synthesis of 3,3'-dihydrofuran spirooxindoles.
Miao, Yu-Hang; Hua, Yuan-Zhao; Wang, Min-Can; Organic & biomolecular chemistry 17 (2019) 7172–7181; doi:10.1039/c9ob01233h

data_7156969
_publ_section_title
;
 Dinuclear zinc cooperative catalytic three-component reactions for highly
 enantioselective synthesis of 3,3'-dihydrofuran spirooxindoles.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7172
_journal_page_last               7181
_journal_paper_doi               10.1039/c9ob01233h
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C21 H17 N3 O5), C4 H8 O'
_chemical_formula_sum            'C46 H42 N6 O11'
_chemical_formula_weight         854.85
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1242(3)
_cell_length_b                   14.3980(3)
_cell_length_c                   20.2906(6)
_cell_measurement_reflns_used    5133
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4960
_cell_measurement_theta_min      3.7530
_cell_volume                     4126.30(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -104.00  -13.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000   30.0000 91

  2 omega  -34.00   72.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   60.0000 106

  3 omega   18.00   63.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 45

  4 omega   66.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 26

  5 omega   57.00   88.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 31

  6 omega   13.00   60.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   30.0000 47

  7 omega   63.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 29

  8 omega   57.00  102.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 45

  9 omega   58.00   84.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 26

 10 omega   47.00  108.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 61

 11 omega   54.00   79.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 25

 12 omega   56.00   88.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 32

 13 omega   49.00   89.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 40

 14 omega   46.00   87.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 41

 15 omega   43.00   93.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 50

 16 omega  103.00  176.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 73

 17 omega   40.00   79.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 39

 18 omega   38.00   91.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 19 omega   79.00  154.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0296482000
_diffrn_orient_matrix_UB_12      -0.1029590000
_diffrn_orient_matrix_UB_13      0.0005928000
_diffrn_orient_matrix_UB_21      0.0310683000
_diffrn_orient_matrix_UB_22      0.0079246000
_diffrn_orient_matrix_UB_23      -0.0724250000
_diffrn_orient_matrix_UB_31      0.1003935000
_diffrn_orient_matrix_UB_32      0.0280651000
_diffrn_orient_matrix_UB_33      0.0224733000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.041
_diffrn_reflns_theta_max         67.041
_diffrn_reflns_theta_min         3.764
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     573
_refine_ls_number_reflns         7264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0816P)^2^+0.5886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                6255
_reflns_number_total             7264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01233h2.cif
_cod_data_source_block           201807329
_cod_depositor_comments          'Adding full bibliography for 7156969.cif.'
_cod_original_cell_volume        4126.30(18)
_cod_database_code               7156969
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.858
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3'(H3'A,H3'B)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C12'(H12')
2.c Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C19(H19), N1(H1A),
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C16'(H16'), C17'(H17'), C19'(H19'),
 N1'(H1'A)
2.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.f Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C20'(H20D,H20E,H20F), C21'(H21D,
 H21E,H21F)
;
_olex2_date_sample_data_collection 1531443134.44
_olex2_submission_special_instructions 'No special instructions were received'