Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids.
Liu, Zhao-Jing; Lu, Xi; Wang, Guan; Li, Lei; Jiang, Wei-Tao; Wang, Yu-Dong; Xiao, Bin; Fu, Yao; Journal of the American Chemical Society 138 (2016) 9714–9719; doi:10.1021/jacs.6b05788

data_4130694
_publ_section_title
;
 Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed
 Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic
 Acids.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9714
_journal_page_last               9719
_journal_paper_doi               10.1021/jacs.6b05788
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C15 H20 N2 O'
_chemical_formula_weight         244.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.621(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7063(3)
_cell_length_b                   17.9769(7)
_cell_length_c                   8.8307(3)
_cell_measurement_reflns_used    3093
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.3800
_cell_measurement_theta_min      5.2240
_cell_volume                     1343.24(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5371
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.566
_diffrn_reflns_theta_min         5.227
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2255
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05788_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4130694
_shelx_estimated_absorpt_t_min   0.804
_shelx_estimated_absorpt_t_max   0.836
_shelxl_version_number           2013-4
_shelx_res_checksum              53430
_shelx_hkl_checksum              79071