#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500040.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_4500040
loop_
_publ_author_name
'Fatima Helzy'
'Thierry Maris'
'James D. Wuest'
_publ_section_title
;
 Engineering Hydrogen-Bonded Molecular Crystals Built from
 1,3,5-Substituted Derivatives of Benzene:
 6,6',6''-(1,3,5-Phenylene)tris-1,3,5-triazine-2,4-diamines
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              1547
_journal_page_last               1553
_journal_paper_doi               10.1021/cg700798z
_journal_volume                  8
_journal_year                    2008
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H21 N15, 2(H2 O)'
_chemical_formula_sum            'C18 H25 N15 O2'
_chemical_formula_weight         483.53
_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                79.084(4)
_cell_angle_beta                 86.515(4)
_cell_angle_gamma                69.273(3)
_cell_formula_units_Z            2
_cell_length_a                   10.8239(5)
_cell_length_b                   12.0117(7)
_cell_length_c                   15.8500(9)
_cell_measurement_reflns_used    12254
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      72.97
_cell_measurement_theta_min      2.84
_cell_volume                     1892.42(18)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19111
_diffrn_reflns_theta_full        73.08
_diffrn_reflns_theta_max         73.08
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        0.04
_diffrn_standards_number         17
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  0.8510
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0766
_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)+(0.1498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2099
_refine_ls_wR_factor_ref         0.2256
_reflns_number_gt                5984
_reflns_number_total             7419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw498
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4500040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.48686(19) 0.82778(19) 0.33084(14) 0.0253(5) Uani 1 1 d .
N1 N 0.64308(17) 0.92926(19) 0.07431(13) 0.0349(5) Uani 1 1 d .
C2 C 0.54365(19) 0.8858(2) 0.26324(14) 0.0264(5) Uani 1 1 d .
N2 N 0.83201(17) 0.9793(2) 0.02172(13) 0.0390(5) Uani 1 1 d .
C3 C 0.64769(19) 0.8122(2) 0.21789(14) 0.0268(5) Uani 1 1 d .
N3 N 0.83445(17) 0.8642(2) 0.16219(12) 0.0362(5) Uani 1 1 d .
C4 C 0.6945(2) 0.6876(2) 0.23982(16) 0.0326(5) Uani 1 1 d .
N4 N 0.64131(19) 1.0462(2) -0.05899(14) 0.0483(6) Uani 1 1 d .
H4A H 0.6789 1.0830 -0.0993 0.058 Uiso 1 1 calc .
H4B H 0.5606 1.0502 -0.0658 0.058 Uiso 1 1 calc .
C5 C 0.6377(2) 0.6326(2) 0.30883(16) 0.0327(5) Uani 1 1 d .
N5 N 1.0163(2) 0.9061(3) 0.10652(15) 0.0556(7) Uani 1 1 d .
H5A H 1.0561 0.9405 0.0661 0.067 Uiso 1 1 calc .
H5B H 1.0580 0.8654 0.1541 0.067 Uiso 1 1 calc .
C6 C 0.5325(2) 0.7012(2) 0.35451(15) 0.0301(5) Uani 1 1 d .
N6 N 0.7947(2) 0.4554(2) 0.38965(19) 0.0575(7) Uani 1 1 d .
C7 C 0.4951(2) 1.0205(2) 0.24118(17) 0.0369(6) Uani 1 1 d .
H7A H 0.5445 1.0455 0.1928 0.055 Uiso 1 1 calc R
H7B H 0.5073 1.0532 0.2902 0.055 Uiso 1 1 calc R
H7C H 0.4021 1.0504 0.2262 0.055 Uiso 1 1 calc R
N7 N 0.7915(3) 0.2578(2) 0.39372(19) 0.0593(7) Uani 1 1 d .
C8 C 0.8074(3) 0.6098(3) 0.1908(2) 0.0527(8) Uani 1 1 d .
H8A H 0.8266 0.5251 0.2154 0.079 Uiso 1 1 calc R
H8B H 0.8854 0.6307 0.1948 0.079 Uiso 1 1 calc R
H8C H 0.7822 0.6241 0.1309 0.079 Uiso 1 1 calc R
N8 N 0.6298(3) 0.4331(2) 0.31146(18) 0.0602(7) Uani 1 1 d .
C9 C 0.4691(3) 0.6425(2) 0.42794(19) 0.0492(7) Uani 1 1 d .
H9A H 0.3981 0.7043 0.4510 0.074 Uiso 1 1 calc R
H9B H 0.5345 0.5967 0.4725 0.074 Uiso 1 1 calc R
H9C H 0.4338 0.5884 0.4077 0.074 Uiso 1 1 calc R
N9 N 0.9454(4) 0.2891(3) 0.4674(4) 0.141(2) Uani 1 1 d .
H9D H 0.9804 0.2111 0.4837 0.169 Uiso 1 1 calc .
H9E H 0.9801 0.3366 0.4842 0.169 Uiso 1 1 calc .
C10 C 0.7126(2) 0.8724(2) 0.14642(15) 0.0285(5) Uani 1 1 d .
N10 N 0.6249(5) 0.2450(3) 0.3191(3) 0.1322(19) Uani 1 1 d .
H10A H 0.6559 0.1668 0.3354 0.159 Uiso 1 1 calc .
H10B H 0.5548 0.2786 0.2865 0.159 Uiso 1 1 calc .
C11 C 0.7083(2) 0.9829(2) 0.01408(15) 0.0352(6) Uani 1 1 d .
N11 N 0.25483(17) 0.90566(18) 0.35735(13) 0.0328(5) Uani 1 1 d .
C12 C 0.8931(2) 0.9159(3) 0.09567(16) 0.0388(6) Uani 1 1 d .
N12 N 0.17007(17) 1.0235(2) 0.46539(14) 0.0392(5) Uani 1 1 d .
C13 C 0.6917(2) 0.4972(2) 0.33932(18) 0.0390(6) Uani 1 1 d .
N13 N 0.40140(17) 0.94884(18) 0.44015(13) 0.0327(5) Uani 1 1 d .
C14 C 0.8396(3) 0.3356(3) 0.4172(3) 0.0634(9) Uani 1 1 d .
N14 N 0.03242(19) 0.9769(3) 0.38519(15) 0.0528(7) Uani 1 1 d .
H14A H -0.0351 1.0167 0.4134 0.063 Uiso 1 1 calc .
H14B H 0.0208 0.9417 0.3447 0.063 Uiso 1 1 calc .
C15 C 0.6837(4) 0.3120(3) 0.3435(2) 0.0668(10) Uani 1 1 d .
N15 N 0.3164(2) 1.0562(3) 0.54778(17) 0.0574(7) Uani 1 1 d .
H15A H 0.2518 1.0941 0.5789 0.069 Uiso 1 1 calc .
H15B H 0.3972 1.0477 0.5591 0.069 Uiso 1 1 calc .
C16 C 0.37306(19) 0.8996(2) 0.37920(15) 0.0266(5) Uani 1 1 d .
C17 C 0.1543(2) 0.9698(2) 0.40406(16) 0.0355(6) Uani 1 1 d .
C18 C 0.2919(2) 1.0116(2) 0.48356(17) 0.0370(6) Uani 1 1 d .
O10 O 0.9114(3) 0.8193(3) 0.33364(16) 0.0831(8) Uani 1 1 d .
H101 H 0.8740 0.7974 0.3792 0.100 Uiso 1 1 d R
H102 H 0.9265 0.8823 0.3393 0.100 Uiso 1 1 d R
O11 O 0.25654(17) 0.81172(19) 0.20191(12) 0.0503(5) Uani 1 1 d .
H111 H 0.2123 0.8686 0.1629 0.076 Uiso 1 1 d R
H112 H 0.3377 0.8023 0.1938 0.076 Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 121.54(19) y
C2 C1 C16 120.48(19) y
C6 C1 C16 117.97(18) y
C10 N1 C11 113.86(18) y
C1 C2 C3 117.6(2) y
C1 C2 C7 120.21(19) y
C3 C2 C7 122.16(19) y
C11 N2 C12 115.3(2) y
C4 C3 C2 122.0(2) y
C4 C3 C10 119.29(19) y
C2 C3 C10 118.7(2) y
C10 N3 C12 114.8(2) y
C3 C4 C5 119.0(2) y
C3 C4 C8 121.3(2) y
C5 C4 C8 119.7(2) y
C11 N4 H4A 120 ?
C11 N4 H4B 120 ?
H4A N4 H4B 120 ?
C4 C5 C6 121.2(2) y
C4 C5 C13 121.0(2) y
C6 C5 C13 117.7(2) y
C12 N5 H5A 120 ?
C12 N5 H5B 120 ?
H5A N5 H5B 120 ?
C5 C6 C1 118.6(2) y
C5 C6 C9 121.5(2) y
C1 C6 C9 119.8(2) y
C13 N6 C14 115.6(2) y
C2 C7 H7A 109.5 ?
C2 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C2 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C14 N7 C15 113.3(3) y
C4 C8 H8A 109.5 ?
C4 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C4 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C13 N8 C15 112.7(3) y
C6 C9 H9A 109.5 ?
C6 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C6 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C14 N9 H9D 120 ?
C14 N9 H9E 120 ?
H9D N9 H9E 120 ?
N3 C10 N1 126.4(2) y
N3 C10 C3 115.7(2) y
N1 C10 C3 117.91(17) y
C15 N10 H10A 120 ?
C15 N10 H10B 120 ?
H10A N10 H10B 120 ?
N2 C11 N4 117.9(2) y
N2 C11 N1 125.3(2) y
N4 C11 N1 116.71(19) y
C16 N11 C17 114.37(19) y
N5 C12 N2 118.4(2) y
N5 C12 N3 117.4(2) y
N2 C12 N3 124.14(19) y
C17 N12 C18 117.33(19) y
N6 C13 N8 126.8(2) y
N6 C13 C5 116.5(2) y
N8 C13 C5 116.8(2) y
C16 N13 C18 113.76(18) y
N9 C14 N7 117.0(3) y
N9 C14 N6 117.6(3) y
N7 C14 N6 125.3(3) y
C17 N14 H14A 120 ?
C17 N14 H14B 120 ?
H14A N14 H14B 120 ?
N10 C15 N7 118.7(3) y
N10 C15 N8 115.1(3) y
N7 C15 N8 126.1(3) y
C18 N15 H15A 120 ?
C18 N15 H15B 120 ?
H15A N15 H15B 120 ?
N11 C16 N13 126.92(19) y
N11 C16 C1 116.23(19) y
N13 C16 C1 116.84(17) y
N12 C17 N14 119.2(2) y
N12 C17 N11 124.19(19) y
N14 C17 N11 116.6(2) y
N15 C18 N12 120.9(2) y
N15 C18 N13 115.7(2) y
N12 C18 N13 123.4(2) y
H101 O10 H102 107.7 ?
H111 O11 H112 107.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.397(3) y
C1 C6 1.404(3) y
C1 C16 1.494(3) y
N1 C10 1.336(3) y
N1 C11 1.354(3) y
C2 C3 1.415(3) y
C2 C7 1.491(3) y
N2 C11 1.336(3) y
N2 C12 1.338(3) y
C3 C4 1.380(3) y
C3 C10 1.500(3) y
N3 C10 1.323(3) y
N3 C12 1.360(3) y
C4 C5 1.394(3) y
C4 C8 1.524(3) y
N4 C11 1.350(3) y
N4 H4a 0.87 ?
N4 H4b 0.87 ?
C5 C6 1.400(3) y
C5 C13 1.511(3) y
N5 C12 1.316(3) y
N5 H5a 0.87 ?
N5 H5b 0.87 ?
C6 C9 1.503(3) y
N6 C13 1.301(3) y
N6 C14 1.338(4) y
C7 H7a 0.97 ?
C7 H7b 0.97 ?
C7 H7c 0.97 ?
N7 C14 1.335(4) y
N7 C15 1.341(4) y
C8 H8a 0.97 ?
C8 H8b 0.97 ?
C8 H8c 0.97 ?
N8 C13 1.328(3) y
N8 C15 1.368(4) y
C9 H9a 0.97 ?
C9 H9b 0.97 ?
C9 H9c 0.97 ?
N9 C14 1.322(4) y
N9 H9d 0.87 ?
N9 H9e 0.87 ?
N10 C15 1.309(4) y
N10 H10a 0.87 ?
N10 H10b 0.87 ?
N11 C16 1.320(3) y
N11 C17 1.360(3) y
N12 C17 1.314(3) y
N12 C18 1.319(3) y
N13 C16 1.326(3) y
N13 C18 1.382(3) y
N14 C17 1.340(3) y
N14 H14a 0.87 ?
N14 H14b 0.87 ?
N15 C18 1.317(3) y
N15 H15a 0.87 ?
N15 H15b 0.87 ?
O10 H101 0.85 ?
O10 H102 0.8499 ?
O11 H111 0.8502 ?
O11 H112 0.85 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O11 0.87 2.11 2.972(3) 172.1 2_675
N4 H4B N1 0.87 2.14 3.008(2) 174.8 2_675
N5 H5A N2 0.87 2.11 2.976(3) 173.8 2_775
N5 H5B O11 0.87 2.15 2.840(3) 135.6 1_655
N9 H9D N12 0.87 2.51 3.261(4) 145.7 1_645
N14 H14A N12 0.87 2.42 3.128(3) 138.7 2_576
N14 H14B O10 0.87 2.23 2.906(3) 134.9 1_455
N15 H15A O10 0.87 2.25 3.121(3) 176.1 2_676
N15 H15B N13 0.87 2.20 3.050(3) 167.3 2_676
O10 H101 N15 0.85 2.57 3.121(3) 123.7 2_676
O10 H102 N14 0.85 2.12 2.906(3) 154.5 1_655
O11 H111 N5 0.85 2.21 2.840(3) 130.5 1_455
O11 H111 N4 0.85 2.54 2.972(3) 112.4 2_675
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
_geom_torsion_publ_flag
C6 C1 C2 C3 1.3(3) y
C16 C1 C2 C3 -177.55(19) y
C6 C1 C2 C7 -178.4(2) y
C16 C1 C2 C7 2.8(3) y
C1 C2 C3 C4 -1.3(3) y
C7 C2 C3 C4 178.4(2) y
C1 C2 C3 C10 -178.51(18) y
C7 C2 C3 C10 1.2(3) y
C2 C3 C4 C5 -0.1(3) y
C10 C3 C4 C5 177.1(2) y
C2 C3 C4 C8 -179.5(2) y
C10 C3 C4 C8 -2.3(3) y
C3 C4 C5 C6 1.6(4) y
C8 C4 C5 C6 -179.0(2) y
C3 C4 C5 C13 -175.7(2) y
C8 C4 C5 C13 3.7(4) y
C4 C5 C6 C1 -1.6(3) y
C13 C5 C6 C1 175.8(2) y
C4 C5 C6 C9 178.9(2) y
C13 C5 C6 C9 -3.8(3) y
C2 C1 C6 C5 0.1(3) y
C16 C1 C6 C5 179.0(2) y
C2 C1 C6 C9 179.7(2) y
C16 C1 C6 C9 -1.5(3) y
C12 N3 C10 N1 -2.7(4) y
C12 N3 C10 C3 178.0(2) y
C11 N1 C10 N3 -0.6(4) y
C11 N1 C10 C3 178.7(2) y
C4 C3 C10 N3 -68.3(3) y
C2 C3 C10 N3 109.0(2) y
C4 C3 C10 N1 112.4(2) y
C2 C3 C10 N1 -70.3(3) y
C12 N2 C11 N4 179.6(2) y
C12 N2 C11 N1 0.4(4) y
C10 N1 C11 N2 1.8(4) y
C10 N1 C11 N4 -177.4(2) y
C11 N2 C12 N5 178.4(3) y
C11 N2 C12 N3 -4.2(4) y
C10 N3 C12 N5 -177.3(2) y
C10 N3 C12 N2 5.3(4) y
C14 N6 C13 N8 -1.7(5) y
C14 N6 C13 C5 178.9(3) y
C15 N8 C13 N6 1.8(5) y
C15 N8 C13 C5 -178.8(3) y
C4 C5 C13 N6 81.3(3) y
C6 C5 C13 N6 -96.0(3) y
C4 C5 C13 N8 -98.1(3) y
C6 C5 C13 N8 84.6(3) y
C15 N7 C14 N9 179.4(4) y
C15 N7 C14 N6 -5.1(5) y
C13 N6 C14 N9 179.0(4) y
C13 N6 C14 N7 3.5(5) y
C14 N7 C15 N10 -177.5(4) y
C14 N7 C15 N8 5.2(6) y
C13 N8 C15 N10 179.0(4) y
C13 N8 C15 N7 -3.7(5) y
C17 N11 C16 N13 -0.2(4) y
C17 N11 C16 C1 178.7(2) y
C18 N13 C16 N11 0.3(4) y
C18 N13 C16 C1 -178.6(2) y
C2 C1 C16 N11 99.8(2) y
C6 C1 C16 N11 -79.1(3) y
C2 C1 C16 N13 -81.2(3) y
C6 C1 C16 N13 99.9(2) y
C18 N12 C17 N14 178.2(3) y
C18 N12 C17 N11 -1.5(4) y
C16 N11 C17 N12 0.8(4) y
C16 N11 C17 N14 -178.9(2) y
C17 N12 C18 N15 -175.7(3) y
C17 N12 C18 N13 1.7(4) y
C16 N13 C18 N15 176.4(2) y
C16 N13 C18 N12 -1.1(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661270
2 PubChem 139144286
