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_4102421
_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            'C26 H31 N4 O5'
_chemical_formula_weight         479.55
_chemical_name_common            TRN-2-173
_chemical_name_systematic
;
 ?
;
_space_group.centring_type       P
_space_group_IT_number           14
_space_group.IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.062(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8642(19)
_cell_length_b                   20.417(3)
_cell_length_c                   9.1652(13)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.17
_cell_measurement_theta_min      3.44
_cell_volume                     2407.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.951
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_sigmaI/netI    0.1142
_diffrn_refln_scan_rate          60
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15363
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.55
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.8946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0833P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1873
_reflns_number_gt                2244
_reflns_number_total             4211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1009458_si_004.cif
_cod_data_source_block           baran02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        2407.3(6)
_cod_database_code               4102421