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_4514837
_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         'C27 H27 N O4 S'
_chemical_formula_sum            'C27 H27 N O4 S'
_chemical_formula_weight         461.55
_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             2018-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.415(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.0525(8)
_cell_length_b                   12.0473(3)
_cell_length_c                   10.4128(2)
_cell_measurement_reflns_used    8450
_cell_measurement_temperature    297.2(3)
_cell_measurement_theta_max      72.9520
_cell_measurement_theta_min      3.8750
_cell_volume                     4647.97(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      297.2(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -53.00  31.00   1.00    7.26    --  -36.42  57.00  90.00   84
  2  \w   -106.00 -18.00   1.00    7.26    --  -36.42 -38.00 -90.00   88
  3  \w     23.00  90.00   1.00    7.26    --   36.42-125.00-150.00   67
  4  \w      1.00  75.00   1.00    7.26    --   36.42 -99.00  30.00   74
  5  \w     20.00 104.00   1.00    7.26    --   36.42  57.00-120.00   84
  6  \w     39.00 115.00   1.00   29.04    --  108.71-111.00  90.00   76
  7  \w     70.00 178.00   1.00   29.04    --  108.71  15.00 -90.00  108
  8  \w     40.00 126.00   1.00   29.04    --  108.71 -45.00 -90.00   86
  9  \w     91.00 177.00   1.00   29.04    --  108.71  45.00-180.00   86
 10  \w     87.00 178.00   1.00   29.04    --  108.71  30.00  90.00   91
 11  \w     40.00 126.00   1.00   29.04    --  108.71 -45.00 150.00   86
 12  \w     39.00 109.00   1.00   29.04    --  108.71 -94.00 120.00   70
 13  \w     39.00 115.00   1.00   29.04    --  108.71-111.00-120.00   76
 14  \w     57.00 111.00   1.00   29.04    --  108.71 178.00-120.00   54
 15  \w    120.00 178.00   1.00   29.04    --  108.71 111.00  30.00   58
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0285562000
_diffrn_orient_matrix_UB_12      0.0922814000
_diffrn_orient_matrix_UB_13      -0.0144761000
_diffrn_orient_matrix_UB_21      -0.0299474000
_diffrn_orient_matrix_UB_22      -0.0885202000
_diffrn_orient_matrix_UB_23      -0.0072378000
_diffrn_orient_matrix_UB_31      -0.0039490000
_diffrn_orient_matrix_UB_32      0.0046633000
_diffrn_orient_matrix_UB_33      0.1470120000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26116
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.953
_diffrn_reflns_theta_min         3.579
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1088P)^2^+0.6468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7318
_reflns_number_total             9125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02598_si_002.cif
_cod_data_source_block           lq-zr-180716
_cod_original_cell_volume        4647.96(19)
_cod_database_code               4514837
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.98
_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:
 C35(H35), C38(H38), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C39(H39A,H39B), C8(H8A,H8B), C36(H36A,H36B), C37(H37A,H37B),
 C14(H14A,H14B), C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C28(H28), C46(H46), C47(H47), C44(H44), C54(H54), C43(H43),
 C51(H51), C31(H31), C52(H52), C50(H50), C1(H1), C2(H2), C30(H30), C3(H3),
 C27(H27), C53(H53), C5(H5), C29(H29), C4(H4), C23(H23), C25(H25), C26(H26),
 C24(H24), C20(H20), C16(H16), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              5600
_shelx_hkl_checksum              40288
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.812
_oxdiff_exptl_absorpt_empirical_full_min 0.628