Diastereoselective Construction of 6,8-Dioxabicyclo[3.2.1]octane Frameworks from Vinylethylene Carbonates via Palladium-Organo Relay Catalysis
Zeng, Rong; Li, Jun-Long; Zhang, Xiang; Liu, Yan-Qing; Jia, Zhi-Qiang; Leng, Hai-Jun; Huang, Qian-Wei; Liu, Yue; Li, Qing-Zhu; ACS Catalysis 9 (2019) 8256–; doi:10.1021/acscatal.9b02598

data_4514836
_publ_section_title
;
 Diastereoselective Construction of 6,8-Dioxabicyclo[3.2.1]octane
 Frameworks from Vinylethylene Carbonates via Palladium-Organo Relay
 Catalysis
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8256
_journal_paper_doi               10.1021/acscatal.9b02598
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C32 H29 N O4 S'
_chemical_formula_sum            'C32 H29 N O4 S'
_chemical_formula_weight         523.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.976(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6328(5)
_cell_length_b                   9.7259(4)
_cell_length_c                   19.2323(7)
_cell_measurement_reflns_used    6979
_cell_measurement_temperature    295.16(10)
_cell_measurement_theta_max      72.6270
_cell_measurement_theta_min      4.1780
_cell_volume                     2540.42(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.16(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000  -30.0000 88

  2 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000   30.0000 94

  3 omega    1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   92.0000 -122.8334 27

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  -90.0000 84

  5 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  150.0000 95

  6 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000 -120.0000 88

  7 omega   39.00  109.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

  8 omega   91.00  176.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

  9 omega   39.00  109.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 10 omega   40.00   98.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

 11 omega   38.00   91.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 12 omega   38.00   91.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 13 omega   90.00  175.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 14 omega   41.00  126.00   1.0000    1.4100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 15 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000 -180.0000 74

 16 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000    0.0000 84

 17 omega  -33.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000   60.0000 68

 18 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000   60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1123850000
_diffrn_orient_matrix_UB_12      0.0044377000
_diffrn_orient_matrix_UB_13      0.0180428000
_diffrn_orient_matrix_UB_21      -0.0153583000
_diffrn_orient_matrix_UB_22      -0.0205455000
_diffrn_orient_matrix_UB_23      0.0777171000
_diffrn_orient_matrix_UB_31      0.0051195000
_diffrn_orient_matrix_UB_32      -0.1569109000
_diffrn_orient_matrix_UB_33      -0.0096308000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.681
_diffrn_reflns_theta_min         4.616
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53026
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0602
_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^)+(0.1132P)^2^+0.8177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4500
_reflns_number_total             4944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02598_si_003.cif
_cod_data_source_block           cd-ljl-zr-181128
_cod_original_cell_volume        2540.44(16)
_cod_database_code               4514836
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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
2.a Ternary CH refined with riding coordinates:
 C24(H24), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C15(H15), C23(H23), C14(H14), C11(H11), C3(H3),
 C19(H19), C13(H13), C31(H31), C27(H27), C12(H12), C22(H22), C30(H30), C20(H20),
  C28(H28), C21(H21)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_shelx_res_checksum              80702
_shelx_hkl_checksum              51976
_olex2_submission_special_instructions 'No special instructions were received'