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_4514838
_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         'C25 H23 N O2'
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         369.44
_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             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.012(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0757(7)
_cell_length_b                   14.6438(6)
_cell_length_c                   7.2015(3)
_cell_measurement_reflns_used    4535
_cell_measurement_temperature    294.9(6)
_cell_measurement_theta_max      72.6700
_cell_measurement_theta_min      5.7970
_cell_volume                     1871.12(13)
_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      294.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.958
_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   -106.00  33.00   1.00    8.01    --  -36.29   0.00-120.00  139
  2  \w     23.00  90.00   1.00    8.01    --   36.29-125.00-150.00   67
  3  \w     23.00  90.00   1.00    8.01    --   36.29-125.00 -30.00   67
  4  \w    -31.00  53.00   1.00    8.01    --   36.29 -57.00 -60.00   84
  5  \w     39.00 115.00   1.00   32.02    --  108.71-111.00-120.00   76
  6  \w     39.00 109.00   1.00   32.02    --  108.71 -94.00 -60.00   70
  7  \w     82.00 176.00   1.00   32.02    --  108.71  77.00 150.00   94
  8  \w     40.00 126.00   1.00   32.02    --  108.71 -45.00 -30.00   86
  9  \w     82.00 176.00   1.00   32.02    --  108.71  77.00 -90.00   94
 10  \w     42.00 127.00   1.00   32.02    --  108.71 -61.00  60.00   85
 11  \w    100.00 178.00   1.00   32.02    --  108.71 111.00-120.00   78
 12  \w     82.00 176.00   1.00   32.02    --  108.71  77.00  30.00   94
 13  \w   -104.00 -21.00   1.00    8.01    --  -36.29 -77.00-150.00   83
 14  \w   -104.00 -10.00   1.00    8.01    --  -36.29 -77.00  90.00   94
;
_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      0.0091602000
_diffrn_orient_matrix_UB_12      -0.1025048000
_diffrn_orient_matrix_UB_13      -0.0383956000
_diffrn_orient_matrix_UB_21      -0.0864694000
_diffrn_orient_matrix_UB_22      -0.0110664000
_diffrn_orient_matrix_UB_23      -0.0457215000
_diffrn_orient_matrix_UB_31      -0.0001166000
_diffrn_orient_matrix_UB_32      0.0211674000
_diffrn_orient_matrix_UB_33      -0.2095073000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10142
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.922
_diffrn_reflns_theta_min         3.914
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82651
_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    1.311
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0606
_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^)+(0.1146P)^2^+0.2196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3153
_reflns_number_total             3581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02598_si_004.cif
_cod_data_source_block           ljl-0410
_cod_database_code               4514838
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.31
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C1(H1A), C13(H13), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C3(H3), C19(H19), C15(H15), C25(H25), C4(H4), C5(H5),
 C17(H17), C18(H18), C16(H16), C24(H24), C21(H21), C23(H23), C22(H22)
;
_shelx_res_checksum              46137
_shelx_hkl_checksum              45542
_olex2_date_sample_data_collection 2019-04-10
_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 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.715