Carbon Dioxide-Mediated C(sp<sup>3</sup>)-H Arylation of Amine Substrates.
Kapoor, Mohit; Liu, Daniel; Young, Michael C.; Journal of the American Chemical Society 140 (2018) 6818–6822; doi:10.1021/jacs.8b05061

data_4132604
_publ_section_title
;
 Carbon Dioxide-Mediated C(sp<sup>3</sup>)-H Arylation of Amine
 Substrates.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6818
_journal_page_last               6822
_journal_paper_doi               10.1021/jacs.8b05061
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H17.50 N0.50 O2'
_chemical_formula_sum            'C13 H17.5 N0.5 O2'
_chemical_formula_weight         212.77
_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   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 102.884(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9712(10)
_cell_length_b                   7.0406(5)
_cell_length_c                   13.2586(9)
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    100
_cell_measurement_theta_max      46.10
_cell_measurement_theta_min      3.42
_cell_volume                     1180.36(15)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3450
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        46.099
_diffrn_reflns_theta_max         46.099
_diffrn_reflns_theta_min         3.419
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       Block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   0.7507
_exptl_transmission_factor_min   0.6531
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         1759
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          6.295
_refine_ls_shift/su_mean         0.022
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                1652
_reflns_number_total             1759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05061_si_002.cif
_cod_data_source_block           cu_MK_002_182_0m_a_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C13 H17.50 N0.50 O2'
_cod_database_code               4132604
_shelx_shelxl_version_number     2016/6
_exptl_absorpt_special_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_shelx_res_checksum              22484
_shelx_hkl_checksum              96765