Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole-Aniline Coupling: Psychotrimine and Kapakahines B and F
Timothy Newhouse; Chad A. Lewis; Kyle J. Eastman; Phil S. Baran; Journal of the American Chemical Society 132 (2010) 7119–7137; doi:10.1021/ja1009458

data_4102422
_publ_section_title
;
 Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct
 Indole-Aniline Coupling: Psychotrimine and Kapakahines B and F
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7119
_journal_page_last               7137
_journal_paper_doi               10.1021/ja1009458
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C25 H25 I2 N4 O3'
_chemical_formula_weight         683.29
_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                69.470(6)
_cell_angle_beta                 78.957(5)
_cell_angle_gamma                65.684(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5748(9)
_cell_length_b                   10.8805(10)
_cell_length_c                   13.2040(12)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.47
_cell_measurement_theta_min      3.58
_cell_volume                     1294.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.994
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18740
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         66.25
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    19.353
_exptl_absorpt_correction_T_max  0.3444
_exptl_absorpt_correction_T_min  0.0586
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+2.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                3797
_reflns_number_total             4323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1009458_si_005.cif
_cod_data_source_block           baran118
_cod_database_code               4102422