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_4033285
_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         'C23 H28 N2 O2'
_chemical_formula_sum            'C23 H28 N2 O2'
_chemical_formula_weight         364.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-05-30T14:28:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.5610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.30940(10)
_cell_length_b                   10.53060(10)
_cell_length_c                   17.0804(2)
_cell_measurement_reflns_used    18048
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      73.326
_cell_measurement_theta_min      4.018
_cell_volume                     1968.85(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 0.999
_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      0.0432168
_diffrn_orient_matrix_UB_12      0.0599526
_diffrn_orient_matrix_UB_13      -0.0702534
_diffrn_orient_matrix_UB_21      -0.131863
_diffrn_orient_matrix_UB_22      0.0426656
_diffrn_orient_matrix_UB_23      -0.0394085
_diffrn_orient_matrix_UB_31      0.0241737
_diffrn_orient_matrix_UB_32      0.1263042
_diffrn_orient_matrix_UB_33      0.0467765
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28886
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_min         4.039
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.844
_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
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
;
 Flack x determined using 2858 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.0444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6648
_reflns_number_total             7118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02665_si_002.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033285
_shelx_res_checksum              65663
_shelx_hkl_checksum              92894