New Phosphine-Functionalized NHC Ligands: Discovery of an Effective Catalyst for the Room-Temperature Amination of Aryl Chlorides with Primary and Secondary Amines
Wheaton, Craig A.; Bow, John-Paul J.; Stradiotto, Mark; Organometallics 32 (2013) 6148–; doi:10.1021/om400684n

data_4081857
_publ_section_title
;
 New Phosphine-Functionalized NHC Ligands: Discovery of an Effective
 Catalyst for the Room-Temperature Amination of Aryl Chlorides with
 Primary and Secondary Amines
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6148
_journal_paper_doi               10.1021/om400684n
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C43 H62 B F4 N2 O P'
_chemical_formula_weight         740.73
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.1680(10)
_cell_angle_beta                 100.5580(10)
_cell_angle_gamma                97.8890(10)
_cell_formula_units_Z            2
_cell_length_a                   10.63530(10)
_cell_length_b                   13.9417(2)
_cell_length_c                   14.0006(2)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.52
_cell_measurement_theta_min      3.28
_cell_volume                     1977.63(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            61462
_diffrn_reflns_theta_full        70.09
_diffrn_reflns_theta_max         70.09
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_T_max  0.8942
_exptl_absorpt_correction_T_min  0.7890
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.8046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                6500
_reflns_number_total             7080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400684n_si_002.cif
_cod_data_source_block           13
_cod_original_cell_volume        1977.63(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4081857