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_4033283
_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_formula_moiety         'C20 H22 N2 O2'
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-05-30T15:18:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                99.468(3)
_cell_angle_beta                 94.704(3)
_cell_angle_gamma                92.002(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4362(2)
_cell_length_b                   10.8331(4)
_cell_length_c                   11.9492(4)
_cell_measurement_reflns_used    9621
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      73.166
_cell_measurement_theta_min      3.748
_cell_volume                     818.03(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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      0.2032467
_diffrn_orient_matrix_UB_12      -0.0492476
_diffrn_orient_matrix_UB_13      -0.0463559
_diffrn_orient_matrix_UB_21      -0.0021196
_diffrn_orient_matrix_UB_22      0.0989218
_diffrn_orient_matrix_UB_23      -0.0790702
_diffrn_orient_matrix_UB_31      0.1284519
_diffrn_orient_matrix_UB_32      0.0928532
_diffrn_orient_matrix_UB_33      0.0939077
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11079
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.858
_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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0547P)^2^+0.2393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0
_reflns_number_gt                2741
_reflns_number_total             2881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02665_si_003.cif
_cod_data_source_block           8a
_cod_database_code               4033283
_shelx_res_checksum              73657
_shelx_hkl_checksum              41631