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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228215
loop_
_publ_author_name
'Elizondo García, Mariana'
'Bernès, Sylvain'
'Pérez Rodríguez, Nancy'
'Elizondo Martínez, Perla'
_publ_section_title
;
 Tris{2-[(2-aminobenzylidene)amino]ethyl}amine
;
_journal_coeditor_code           BQ2243
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3054
_journal_page_last               o3055
_journal_paper_doi               10.1107/S1600536810043783
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C27 H33 N7'
_chemical_formula_moiety         'C27 H33 N7'
_chemical_formula_sum            'C27 H33 N7'
_chemical_formula_weight         455.60
_chemical_melting_point          416
_chemical_name_common
;
Tris{2-[(2-aminobenzylidene)amino]ethyl}amine
;
_chemical_name_systematic
;
2-[({2-[bis(2-{[(2-
aminophenyl)methylidene]amino}ethyl)amino]ethyl}imino)methyl]aniline
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   13.1075(18)
_cell_length_b                   13.1075(18)
_cell_length_c                   25.985(6)
_cell_measurement_reflns_used    70
_cell_measurement_temperature    300.0(10)
_cell_measurement_theta_max      12.27
_cell_measurement_theta_min      4.80
_cell_volume                     3866.3(12)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300.0(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6668
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.207
_refine_ls_extinction_coef       0.0057(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.811
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.811
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0578
_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/[σ²(Fo²)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                838
_reflns_number_total             1507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2243.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2228215
_cod_database_fobs_code          2228215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 1.0000 1.0000 0.17108(11) 0.0773(10) Uani d S 1 . .
C C2 0.9753(3) 0.8840(2) 0.15415(9) 0.0952(9) Uani d . 1 . .
H H2A 1.0068 0.8904 0.1198 0.114 Uiso calc R 1 . .
H H2B 0.8906 0.8322 0.1524 0.114 Uiso calc R 1 . .
C C3 1.0266(3) 0.8305(3) 0.18909(10) 0.0990(10) Uani d . 1 . .
H H3A 1.0287 0.7663 0.1714 0.119 Uiso calc R 1 . .
H H3B 1.1069 0.8892 0.1978 0.119 Uiso calc R 1 . .
N N4 0.95737(19) 0.78635(19) 0.23590(8) 0.0821(7) Uani d . 1 . .
C C5 1.0077(2) 0.8295(2) 0.27831(10) 0.0741(7) Uani d . 1 . .
H H5A 1.0862 0.8891 0.2776 0.089 Uiso calc R 1 . .
C C6 0.9507(2) 0.79175(19) 0.32820(9) 0.0680(7) Uani d . 1 . .
C C7 1.0149(2) 0.8459(2) 0.37218(10) 0.0825(8) Uani d . 1 . .
H H7A 1.0933 0.9045 0.3688 0.099 Uiso calc R 1 . .
C C8 0.9669(3) 0.8163(3) 0.42032(11) 0.0985(9) Uani d . 1 . .
H H8A 1.0120 0.8540 0.4492 0.118 Uiso calc R 1 . .
C C9 0.8505(3) 0.7297(3) 0.42536(10) 0.0915(9) Uani d . 1 . .
H H9A 0.8165 0.7096 0.4579 0.110 Uiso calc R 1 . .
C C10 0.7853(3) 0.6738(2) 0.38354(10) 0.0820(8) Uani d . 1 . .
H H10A 0.7073 0.6147 0.3879 0.098 Uiso calc R 1 . .
C C11 0.8319(2) 0.7026(2) 0.33419(9) 0.0696(7) Uani d . 1 . .
N N12 0.7651(2) 0.6450(2) 0.29267(9) 0.0958(8) Uani d . 1 . .
H H12A 0.792(3) 0.670(3) 0.2599(10) 0.115 Uiso d . 1 . .
H H12B 0.692(3) 0.597(3) 0.2993(11) 0.115 Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 1 6
-3 4 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C2 . 2_765 111.28(14) ?
C2 N1 C2 . 3_675 111.28(14) ?
C2 N1 C2 2_765 3_675 111.28(14) ?
N1 C2 C3 . . 112.9(2) ?
N1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
N1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N4 C3 C2 . . 110.9(2) ?
N4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
N4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C5 N4 C3 . . 118.0(2) ?
N4 C5 C6 . . 124.1(2) ?
N4 C5 H5A . . 117.9 ?
C6 C5 H5A . . 117.9 ?
C7 C6 C11 . . 117.9(2) ?
C7 C6 C5 . . 119.0(2) ?
C11 C6 C5 . . 123.1(2) ?
C8 C7 C6 . . 122.3(3) ?
C8 C7 H7A . . 118.8 ?
C6 C7 H7A . . 118.8 ?
C7 C8 C9 . . 118.9(3) ?
C7 C8 H8A . . 120.5 ?
C9 C8 H8A . . 120.5 ?
C10 C9 C8 . . 120.7(3) ?
C10 C9 H9A . . 119.7 ?
C8 C9 H9A . . 119.7 ?
C9 C10 C11 . . 121.5(3) ?
C9 C10 H10A . . 119.2 ?
C11 C10 H10A . . 119.2 ?
N12 C11 C10 . . 120.6(2) ?
N12 C11 C6 . . 120.7(2) ?
C10 C11 C6 . . 118.7(2) ?
C11 N12 H12A . . 120.7(19) ?
C11 N12 H12B . . 115(2) ?
H12A N12 H12B . . 123(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.455(3) ?
N1 C2 2_765 1.455(3) ?
N1 C2 3_675 1.455(3) ?
C2 C3 . 1.498(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.454(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C5 . 1.264(3) ?
C5 C6 . 1.454(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.386(3) ?
C6 C11 . 1.413(3) ?
C7 C8 . 1.366(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.379(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.350(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.389(3) ?
C10 H10A . 0.9300 ?
C11 N12 . 1.356(3) ?
N12 H12A . 0.92(3) ?
N12 H12B . 0.86(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N12 H12A N4 . 0.92(3) 2.02(3) 2.700(3) 129(2) yes
N12 H12B Cg 18_545 0.86(3) 2.70(3) 3.430(2) 143(3) yes
C7 H7A Cg 2_765 0.93 2.71 3.494(3) 142.6 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C2 C3 2_765 . . . 83.1(3) ?
C2 N1 C2 C3 3_675 . . . -152.1(3) ?
N1 C2 C3 N4 . . . . 76.1(3) ?
C2 C3 N4 C5 . . . . -119.7(3) ?
C3 N4 C5 C6 . . . . -178.2(2) ?
N4 C5 C6 C7 . . . . -179.8(2) ?
N4 C5 C6 C11 . . . . -0.3(4) ?
C11 C6 C7 C8 . . . . -0.3(4) ?
C5 C6 C7 C8 . . . . 179.1(2) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
C7 C8 C9 C10 . . . . 0.9(4) ?
C8 C9 C10 C11 . . . . -1.1(4) ?
C9 C10 C11 N12 . . . . 179.7(2) ?
C9 C10 C11 C6 . . . . 0.6(3) ?
C7 C6 C11 N12 . . . . -178.9(2) ?
C5 C6 C11 N12 . . . . 1.6(3) ?
C7 C6 C11 C10 . . . . 0.1(3) ?
C5 C6 C11 C10 . . . . -179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139080039
