Enantioselective Synthesis of Biaryl Atropisomers via Pd/Norbornene-Catalyzed Three-Component Cross-Couplings
Ding, Linlin; Sui, Xianwei; Gu, Zhenhua; ACS Catalysis 8 (2018) 5630–; doi:10.1021/acscatal.8b01037

data_4515641
_publ_section_title
;
 Enantioselective Synthesis of Biaryl Atropisomers via
 Pd/Norbornene-Catalyzed Three-Component Cross-Couplings
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5630
_journal_paper_doi               10.1021/acscatal.8b01037
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H46 Cl2 N P Pd, 2(C H2 Cl2)'
_chemical_formula_sum            'C41 H50 Cl6 N P Pd'
_chemical_formula_weight         906.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8095(6)
_cell_length_b                   15.6122(6)
_cell_length_c                   19.5369(9)
_cell_measurement_reflns_used    6734
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.0220
_cell_measurement_theta_min      2.2290
_cell_volume                     4212.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -35.00  63.00   1.00   15.00    --  -11.59  37.00  90.00   98
  2  \w    -42.00   7.00   1.00   15.00    --   11.74 -37.00 -90.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0000075000
_diffrn_orient_matrix_UB_12      -0.0291841000
_diffrn_orient_matrix_UB_13      0.0278496000
_diffrn_orient_matrix_UB_21      0.0306722000
_diffrn_orient_matrix_UB_22      0.0279546000
_diffrn_orient_matrix_UB_23      0.0186974000
_diffrn_orient_matrix_UB_31      -0.0411477000
_diffrn_orient_matrix_UB_32      0.0208404000
_diffrn_orient_matrix_UB_33      0.0138862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14206
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 2643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0335P)^2^+1.2289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                6733
_reflns_number_total             7333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01037_si_003.cif
_cod_data_source_block           exp_1201
_cod_database_code               4515641
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C36(H36), C25(H25), C2(H2), C33(H33), C29(H29), C4(H4), C6(H6),
 C30(H30), C34(H34), C35(H35), C20(H20), C23(H23), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C16(H16A,H16B,H16C), C38(H38A,H38B,H38C), C12(H12A,H12B,
 H12C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C8(H8A,H8B,
 H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              43322
_shelx_hkl_checksum              4304
_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 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.835