Catalytic Asymmetric Synthesis of Tetrahydrofuran Spirooxindoles via Dinuclear Zinc Catalyst.
Guo, Ya-Jun; Guo, Xin; Kong, De-Zhi; Lu, Huijie; Liu, Lantao; Hua, Yuan-Zhao; Wang, Min-Can; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03378

data_4038001
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Tetrahydrofuran Spirooxindoles via
 Dinuclear Zinc Catalyst.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03378
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H21 Br N2 O3'
_chemical_formula_sum            'C25 H21 Br N2 O3'
_chemical_formula_weight         477.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.088(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7361(3)
_cell_length_b                   9.4099(3)
_cell_length_c                   12.0507(4)
_cell_measurement_reflns_used    3887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9140
_cell_measurement_theta_min      4.6440
_cell_volume                     1111.42(7)
_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)'
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega -101.00  -57.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  3 omega  -95.00  -50.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  4 omega  -41.00  -14.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  5 omega  -57.00  -15.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  6 omega   54.00   81.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  7 omega  -31.00   32.00   0.5000    1.2500
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  8 omega   15.00   42.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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  9 omega   29.00   87.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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 10 omega  -29.00   54.00   0.5000    1.2500
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 11 omega   12.00   37.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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 12 omega   24.00  107.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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 13 omega   26.00   66.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
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 14 omega   40.00   65.00   0.5000    1.2500
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 16 omega   18.00   71.00   0.5000    1.2500
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 17 omega   13.00   40.00   0.5000    1.2500
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 18 omega  121.00  174.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   85.00  112.00   0.5000   11.0000
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 20 omega   80.00  116.00   0.5000   11.0000
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 21 omega  111.00  172.00   0.5000   11.0000
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 22 omega   66.00  101.00   0.5000   11.0000
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 23 omega   88.00  114.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
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 24 omega   79.00  105.00   0.5000   11.0000
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    -      108.0000   77.0000  -90.0000 52

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    -      108.0000  -30.0000 -180.0000 52

 26 omega   82.00  115.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 66

 27 omega  100.00  125.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega   85.00  110.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
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 29 omega   89.00  114.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 50

 30 omega  118.00  176.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 116

 31 omega   88.00  115.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 54

 32 omega   89.00  114.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 50

 33 omega   79.00  112.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 66

 34 omega   42.00   98.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 112

 35 omega   89.00  115.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 52

 36 omega   38.00   99.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
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 37 omega  126.00  160.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 68

 38 omega  128.00  170.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 84

 39 omega   89.00  159.00   0.5000   11.0000
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    -      108.0000   61.0000    0.0000 140

 40 omega   84.00  109.00   0.5000   11.0000
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    -      108.0000   30.0000  -90.0000 50

 41 omega   79.00  104.00   0.5000   11.0000
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    -      108.0000   77.0000 -120.0000 50

 42 omega   88.00  122.00   0.5000   11.0000
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 43 omega  118.00  145.00   0.5000   11.0000
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 44 omega   89.00  123.00   0.5000   11.0000
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 45 omega   91.00  117.00   0.5000   11.0000
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 46 omega   89.00  125.00   0.5000   11.0000
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 47 omega   89.00  115.00   0.5000   11.0000
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 48 omega   80.00  105.00   0.5000   11.0000
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 49 omega   37.00   91.00   0.5000   11.0000
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 50 omega   39.00   98.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 118
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_diffrn_orient_matrix_UB_21      0.1026924000
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_diffrn_orient_matrix_UB_32      -0.1540216000
_diffrn_orient_matrix_UB_33      -0.0067622000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0420
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_diffrn_reflns_number            8746
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68436
_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    1.426
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0767P)^2^+0.2054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
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_reflns_Friedel_fraction_max     0.831
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03378_si_001.cif
_cod_data_source_block           201905141
_cod_database_code               4038001
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Br1
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.622
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'