Silver-Free Palladium Catalyzed C(sp3)-H Arylation of Saturated Bicyclic Amine Scaffolds.
Coomber, Charlotte E.; Benhamou, Laure; Bučar, Dejan-Krešimir; Smith, Peter D.; Porter, Michael J.; Sheppard, Tom David; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02665

data_4033284
_publ_section_title
;
 Silver-Free Palladium Catalyzed C(sp3)-H Arylation of Saturated Bicyclic
 Amine Scaffolds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02665
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C34 H35 N2 O P Pd, 2(C H Cl3)'
_chemical_formula_sum            'C36 H37 Cl6 N2 O P Pd'
_chemical_formula_weight         863.74
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-30T12:50:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.7600(10)
_cell_angle_beta                 105.3020(10)
_cell_angle_gamma                112.1750(10)
_cell_formula_units_Z            2
_cell_length_a                   11.43580(10)
_cell_length_b                   13.4434(2)
_cell_length_c                   14.17280(10)
_cell_measurement_reflns_used    87323
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      74.22
_cell_measurement_theta_min      4.374
_cell_volume                     1919.36(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.136920463
_diffrn_orient_matrix_UB_12      -0.053280617
_diffrn_orient_matrix_UB_13      -0.0792078114
_diffrn_orient_matrix_UB_21      0.0654314329
_diffrn_orient_matrix_UB_22      0.0358574045
_diffrn_orient_matrix_UB_23      -0.0817511658
_diffrn_orient_matrix_UB_31      0.0174624964
_diffrn_orient_matrix_UB_32      -0.1077908827
_diffrn_orient_matrix_UB_33      -0.0101207851
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            107520
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        68
_diffrn_reflns_theta_max         74.511
_diffrn_reflns_theta_min         3.6
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.381
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_correction_T_min  0.129
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over a 
multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       prism
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.798
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.010(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     934
_refine_ls_number_reflns         14362
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1068P)^2^+1.5847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.138
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                14073
_reflns_number_total             14362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02665_si_004.cif
_cod_data_source_block           8b
_cod_database_code               4033284