TiIV-Mediated Reactions between Primary Amines and Secondary Carboxamides: Amidine Formation Versus Transamidation
Denis A. Kissounko; Justin M. Hoerter; Ilia A. Guzei; Qiang Cui; Samuel H. Gellman; Shannon S. Stahl; Journal of the American Chemical Society 129 (2007) 1776–1783; doi:10.1021/ja0650293

data_4109062
_publ_section_title
;
 TiIV-Mediated Reactions between Primary Amines and Secondary
 Carboxamides: Amidine Formation Versus Transamidation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1776
_journal_page_last               1783
_journal_paper_doi               10.1021/ja0650293
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C29 H39 N3 O2 Ti'
_chemical_formula_weight         509.53
_chemical_name_systematic
; 
 ? 
;
_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                78.616(2)
_cell_angle_beta                 79.770(2)
_cell_angle_gamma                71.566(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7866(12)
_cell_length_b                   9.9982(12)
_cell_length_c                   15.0810(18)
_cell_measurement_reflns_used    7359
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1361.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11101
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.8662
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0757P)^2^+0.6051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                4911
_reflns_number_total             5480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0650293si20060714_023358.cif
_cod_data_source_block           stahl42
_cod_database_code               4109062