Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of Bicyclo[3.2.1]oct-6-ene Frameworks via (4 + 3)-Cycloadditions
Tanpure, Sudhakar Dattatray; Kuo, Tung-Chun; Cheng, Mu-Jeng; Liu, Rai-Shung; ACS Catalysis  (2021) 536–543; doi:10.1021/acscatal.1c04483

data_4519235
_publ_section_title
;
 Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of
 Bicyclo[3.2.1]oct-6-ene Frameworks via (4 + 3)-Cycloadditions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              536
_journal_page_last               543
_journal_paper_doi               10.1021/acscatal.1c04483
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C32 H30 O'
_chemical_formula_sum            'C32 H30 O'
_chemical_formula_weight         430.56
_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     dual
_audit_creation_date             2021-12-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.183(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1480(5)
_cell_length_b                   10.0931(5)
_cell_length_c                   14.7699(8)
_cell_measurement_reflns_used    9705
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.8450
_cell_measurement_theta_min      3.0190
_cell_volume                     1182.65(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.33a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     52.00 112.00   0.30    0.38    --   74.39  15.00 -60.00  200
  2  \w     55.00 115.00   0.30    0.38    --   74.39  15.00-120.00  200
  3  \w     84.00 115.80   0.30    0.38    --   74.39  15.00-180.00  106
  4  \w     80.00 116.00   0.30    0.38    --   74.39  15.00 150.00  120
  5  \w     52.00  77.80   0.30    0.38    --   74.39  15.00 150.00   86
  6  \w     21.00  76.20   0.30    0.38    --   57.89-125.00 -60.00  184
  7  \w     24.00  59.10   0.30    0.38    --   57.89-125.00-120.00  117
  8  \w     66.00 100.20   0.30    0.38    --   78.57-125.00  28.33  114
  9  \w     33.00  67.80   0.30    0.38    --   74.39-125.00  90.00  116
 10  \w     18.00  43.80   0.30    0.38    --   57.89-125.00 120.00   86
 11  \w     48.00  98.10   0.30    0.38    --   78.57-124.00 100.05  167
 12  \w     57.00  93.00   0.30    0.38    --   74.00-119.00  51.23  120
 13  \w     39.00  87.00   0.30    0.38    --   78.57-103.00 -54.46  160
 14  \w     40.00  90.10   0.30    0.38    --   78.57-113.00 -95.68  167
 15  \w   -106.00 -55.00   0.30    0.38    --  -60.97 -15.00 -30.00  170
 16  \w   -105.00 -48.00   0.30    0.38    --  -60.97 -15.00  60.00  190
 17  \w    -90.00 -61.20   0.30    0.38    --  -73.68 -15.00 -30.00   96
 18  \w   -104.00 -44.90   0.30    0.38    --  -60.97 -15.00 -90.00  197
 19  \w   -115.00 -73.00   0.30    0.38    --  -73.68 -15.00-120.00  140
 20  \w    -95.00 -53.00   0.30    0.38    --  -60.97 -15.00-180.00  140
 21  \w    -78.00 -40.20   0.30    0.38    --  -78.57 140.00 -68.73  126
 22  \w    -95.00 -32.00   0.30    0.38    --  -74.02 125.00 -90.00  210
 23  \w    -65.00 -32.00   0.30    0.38    --  -73.68 125.00 -30.00  110
 24  \w    -98.00 -47.90   0.30    0.38    --  -78.57 119.00-142.20  167
 25  \w    -96.00 -39.90   0.30    0.38    --  -74.02 125.00  30.00  187
 26  \w    -99.00 -42.90   0.30    0.38    --  -78.57 121.00  61.17  187
 27  \w    -96.00 -30.90   0.30    0.38    --  -74.02 125.00  90.00  217
 28  \w    -96.00 -54.00   0.30    0.38    --  -74.02 125.00 150.00  140
 29  \w    -98.00 -38.90   0.30    0.38    --  -78.57 119.00 129.06  197
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0563377000
_diffrn_orient_matrix_UB_12      -0.1079632000
_diffrn_orient_matrix_UB_13      0.0602412000
_diffrn_orient_matrix_UB_21      0.1856658000
_diffrn_orient_matrix_UB_22      -0.0283255000
_diffrn_orient_matrix_UB_23      0.0470568000
_diffrn_orient_matrix_UB_31      -0.0083710000
_diffrn_orient_matrix_UB_32      0.1041999000
_diffrn_orient_matrix_UB_33      0.0749356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12592
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.050
_diffrn_reflns_theta_max         67.050
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.33a (Rigaku Oxford Diffraction, 2021)
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    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_coef       0.0075(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0541P)^2^+0.0246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3840
_reflns_number_total             4011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04483_si_005.cif
_cod_data_source_block           211215lt_auto
_cod_original_cell_volume        1182.64(12)
_cod_database_code               4519235
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O '
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.918
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_res_checksum              67733
_shelx_hkl_checksum              7461
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.560