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_4109064
_publ_contact_author_address
;
   2124 Chemistry Department
   University of Wisconsin-Madison
   1101 University Ave
   Madison, WI  53706
   USA
;
_publ_contact_author_email       iguzei@chem.wisc.edu
_publ_contact_author_fax         608-262-0381
_publ_contact_author_name
;
Ilia A. Guzei
;
_publ_contact_author_phone       608-263-4694
_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_moiety         'C34 H39 N3 O3 Ti'
_chemical_formula_sum            'C34 H39 N3 O3 Ti'
_chemical_formula_weight         585.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.234(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.214(5)
_cell_length_b                   8.651(3)
_cell_length_c                   21.519(7)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.87
_cell_volume                     2882.9(16)
_computing_cell_refinement       'Bruker SAINT Ver. 6.22'
_computing_data_collection       'Bruker SMART Ver. 5.622'
_computing_data_reduction        'Bruker SAINT Ver. 6.22'
_computing_molecular_graphics    'Bruker SHELXTL Ver. 6.10'
_computing_publication_material  'Bruker SHELXTL Ver. 6.10'
_computing_structure_refinement  'Bruker SHELXTL Ver. 6.10'
_computing_structure_solution    'Bruker SHELXTL Ver. 6.10'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker CCD-1000 area detector'
_diffrn_measurement_method       '0.30 degree 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  0.0993
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21005
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan with SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+6.6452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1854
_reflns_number_gt                3518
_reflns_number_total             5646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0650293si20060720_043741.cif
_cod_data_source_block           stahl46
_cod_original_cell_volume        2883.0(16)
_cod_database_code               4109064