#------------------------------------------------------------------------------ #$Date: 2026-06-09 19:12:11 +0100 (Tue, 09 Jun 2026) $ #$Revision: 306529 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577387.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_1577387 loop_ _publ_author_name 'Duy Tuan Doan' 'Thi Linh Giang Hoang' 'Thi Thom Nguyen' 'Thierry Maris' 'Phuong Nguyen-Triv' _publ_section_title ; Functional organic ligands tailored by carboxylic acid and diaminotriazinyl for metal-organic framework preparations ; _journal_name_full 'J Mol. Struct' _journal_page_first 144349 _journal_paper_doi 10.1016/j.molstruc.2025.144349 _journal_volume 1352 _journal_year 2026 _chemical_formula_moiety 'C11 H11 N5 O4, 2(Cl O4)' _chemical_formula_sum 'C11 H11 Cl2 N5 O12' _chemical_formula_weight 476.15 _chemical_name_systematic ; 2,4-diamino-6-(3,5-dicarboxyphenyl)-1,3,5-triazine-1,3-diium diperchlorate ; _space_group_crystal_system orthorhombic _space_group_IT_number 52 _space_group_name_Hall '-P 2a 2bc' _space_group_name_H-M_alt 'P n n a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2022-10-17 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 21.6216(7) _cell_length_b 11.8804(4) _cell_length_c 6.6638(2) _cell_measurement_reflns_used 2252 _cell_measurement_temperature 293 _cell_measurement_theta_max 71.0160 _cell_measurement_theta_min 5.5300 _cell_volume 1711.75(10) _computing_cell_refinement 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.0715 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -75.00 -32.00 1.00 5.00 -- -36.60 119.00 115.00 43 2 \w -30.00 51.00 1.00 5.00 -- 36.60 -20.00-128.00 81 3 \w 93.00 172.00 1.00 20.00 -- 107.46 20.00 38.00 79 4 \w 105.00 158.00 1.00 20.00 -- 107.46 108.00-146.00 53 5 \w 58.00 102.00 1.00 20.00 -- 107.46-119.00 30.00 44 6 \w -58.00 -20.00 1.00 5.00 -- -36.60 -57.00 30.00 38 7 \w -50.00 -22.00 1.00 5.00 -- -36.60 -57.00 -60.00 28 8 \w 18.00 44.00 1.00 5.00 -- 36.60 62.00 4.81 26 9 \w 29.00 54.00 1.00 5.00 -- 36.60 57.00-120.00 25 10 \w 104.00 157.00 1.00 20.00 -- 107.46 77.00 120.00 53 11 \w 39.00 100.00 1.00 20.00 -- 107.46-111.00 90.00 61 12 \w 37.00 82.00 1.00 20.00 -- 107.46-111.00 -30.00 45 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 4231 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.511 _diffrn_reflns_theta_min 4.089 _exptl_absorpt_coefficient_mu 4.204 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light white' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.848 _exptl_crystal_description prism _exptl_crystal_F_000 968 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.382 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.067 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 1638 _refine_ls_number_restraints 63 _refine_ls_restrained_S_all 1.133 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0521 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+1.5872P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1407 _refine_ls_wR_factor_ref 0.1434 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1515 _reflns_number_total 1638 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 5-TD-05.cif _cod_data_source_block td_05 _cod_database_code 1577387 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z' 3 '-x+1/2, y+1/2, -z+1/2' 4 'x, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z' 7 'x-1/2, -y-1/2, z-1/2' 8 '-x, y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.73290(11) 0.1990(2) 0.9011(4) 0.0311(6) Uani 1 1 d . . . . . O1 O 0.47400(8) 0.40094(18) 0.2903(3) 0.0358(5) Uani 1 1 d . U . . . H1 H 0.451(2) 0.436(4) 0.201(7) 0.067(12) Uiso 1 1 d . . . . . C2 C 0.64058(14) 0.250000 0.750000 0.0243(7) Uani 1 2 d S T P . . N2 N 0.76373(13) 0.250000 0.750000 0.0306(7) Uani 1 2 d DS T P . . H2 H 0.8023(19) 0.250000 0.750000 0.037(12) Uiso 1 2 d DS . P . . C3 C 0.57242(14) 0.250000 0.750000 0.0238(7) Uani 1 2 d S T P . . N3 N 0.67033(9) 0.1977(2) 0.8982(3) 0.0292(5) Uani 1 1 d D . . . . H3 H 0.654(3) 0.157(4) 0.985(7) 0.034(16) Uiso 0.5 1 d D . P . . C4 C 0.54051(11) 0.2993(2) 0.5918(4) 0.0248(5) Uani 1 1 d . . . . . H4 H 0.5614(15) 0.334(3) 0.488(5) 0.034(8) Uiso 1 1 d . . . . . C5 C 0.47608(11) 0.2991(2) 0.5929(4) 0.0252(5) Uani 1 1 d D U . . . N5 N 0.76244(10) 0.1520(2) 1.0472(4) 0.0366(6) Uani 1 1 d . . . . . H5A H 0.7431(14) 0.127(2) 1.142(5) 0.023(7) Uiso 1 1 d . . . . . H5B H 0.8015(19) 0.146(3) 1.043(5) 0.047(10) Uiso 1 1 d . . . . . C6 C 0.44420(14) 0.250000 0.750000 0.0232(7) Uani 1 2 d S T P A . H6 H 0.4013(17) 0.250000 0.750000 0.017(9) Uiso 1 2 d S . P . . C7A C 0.4403(8) 0.3671(9) 0.441(2) 0.0222(17) Uani 0.469(16) 1 d D U P A 1 O1A O 0.3855(2) 0.3732(9) 0.4422(10) 0.0313(18) Uani 0.469(16) 1 d . U P A 1 C7B C 0.4398(7) 0.3360(10) 0.4132(17) 0.0222(17) Uani 0.531(16) 1 d D U P A 2 O1B O 0.38432(18) 0.3176(8) 0.3899(9) 0.0320(16) Uani 0.531(16) 1 d . U P A 2 O5 O 0.59339(13) 0.0189(2) 0.5104(4) 0.0622(8) Uani 1 1 d . . . . . O6 O 0.66928(9) -0.1137(2) 0.4228(3) 0.0517(6) Uani 1 1 d . . . . . Cl1 Cl 0.64126(6) 0.01051(10) 0.3768(2) 0.0261(5) Uani 0.509(3) 1 d . . P B 1 O3 O 0.6849(2) 0.0997(4) 0.4093(8) 0.0405(11) Uani 0.509(3) 1 d . . P B 1 O4 O 0.62423(18) 0.0137(3) 0.1658(6) 0.0364(9) Uani 0.509(3) 1 d . . P B 1 Cl1A Cl 0.66446(7) -0.01672(11) 0.4854(3) 0.0321(5) Uani 0.491(3) 1 d . . P B 2 O3A O 0.6838(3) 0.0533(5) 0.3204(10) 0.0531(14) Uani 0.491(3) 1 d . . P B 2 O5A O 0.7014(2) 0.0051(4) 0.6568(7) 0.0547(14) Uani 0.491(3) 1 d . . P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0175(11) 0.0470(15) 0.0287(13) -0.0056(12) 0.0004(9) -0.0036(10) O1 0.0238(8) 0.0484(11) 0.0350(11) 0.0173(9) -0.0012(8) 0.0031(8) C2 0.0173(15) 0.0328(17) 0.0229(16) -0.0020(14) 0.000 0.000 N2 0.0138(13) 0.0503(19) 0.0278(15) -0.0033(14) 0.000 0.000 C3 0.0172(15) 0.0267(16) 0.0273(17) -0.0048(14) 0.000 0.000 N3 0.0161(10) 0.0446(13) 0.0268(11) 0.0029(10) 0.0013(8) -0.0038(8) C4 0.0192(11) 0.0284(12) 0.0267(12) 0.0008(10) 0.0027(9) -0.0010(9) C5 0.0191(11) 0.0265(11) 0.0301(13) 0.0002(10) -0.0005(9) 0.0025(9) N5 0.0160(10) 0.0629(16) 0.0310(13) 0.0047(11) -0.0004(9) -0.0021(10) C6 0.0140(14) 0.0251(15) 0.0303(18) -0.0026(14) 0.000 0.000 C7A 0.0220(13) 0.017(5) 0.027(3) -0.005(3) 0.001(2) 0.006(4) O1A 0.0200(19) 0.040(4) 0.034(3) 0.005(3) -0.0012(17) 0.008(2) C7B 0.0220(13) 0.017(5) 0.027(3) -0.005(3) 0.001(2) 0.006(4) O1B 0.0177(17) 0.041(4) 0.037(3) 0.004(2) -0.0042(15) -0.0005(18) O5 0.0652(16) 0.0564(15) 0.0650(16) -0.0002(13) 0.0406(14) -0.0098(12) O6 0.0295(10) 0.0867(18) 0.0390(12) -0.0119(12) 0.0000(9) -0.0056(11) Cl1 0.0240(7) 0.0212(6) 0.0332(9) -0.0007(5) 0.0047(6) -0.0025(4) O3 0.047(2) 0.033(2) 0.042(3) -0.008(2) 0.009(2) -0.0137(19) O4 0.036(2) 0.037(2) 0.036(2) 0.0035(16) -0.0001(17) -0.0033(15) Cl1A 0.0313(8) 0.0312(7) 0.0337(10) -0.0019(6) 0.0141(7) -0.0050(5) O3A 0.055(3) 0.043(3) 0.062(4) 0.012(3) 0.038(3) -0.004(2) O5A 0.061(3) 0.058(3) 0.045(3) -0.025(2) 0.011(2) -0.022(2) 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' Cl Cl 0.3639 0.7018 '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_site_symmetry_1 _geom_angle_site_symmetry_3 N2 C1 N3 119.2(2) . . N5 C1 N2 120.8(2) . . N5 C1 N3 120.0(2) . . C7A O1 H1 110(3) . . C7B O1 H1 111(3) . . N3 C2 C3 118.88(15) 4_556 . N3 C2 C3 118.87(15) . . N3 C2 N3 122.3(3) . 4_556 C1 N2 C1 120.9(3) 4_556 . C1 N2 H2 119.55(15) 4_556 . C1 N2 H2 119.56(15) . . C4 C3 C2 119.78(15) . . C4 C3 C2 119.77(15) 4_556 . C4 C3 C4 120.5(3) 4_556 . C1 N3 H3 116(4) . . C2 N3 C1 119.2(2) . . C2 N3 H3 125(4) . . C3 C4 H4 121(2) . . C3 C4 C5 119.5(2) . . C5 C4 H4 119(2) . . C4 C5 C7A 120.6(7) . . C4 C5 C7B 121.3(6) . . C6 C5 C4 120.2(2) . . C6 C5 C7A 118.6(7) . . C6 C5 C7B 117.9(6) . . C1 N5 H5A 119(2) . . C1 N5 H5B 120(2) . . H5A N5 H5B 120(3) . . C5 C6 C5 120.2(3) . 4_556 C5 C6 H6 119.90(15) 4_556 . C5 C6 H6 119.90(15) . . O1 C7A C5 113.3(11) . . O1A C7A O1 122.8(9) . . O1A C7A C5 122.7(13) . . O1 C7B C5 111.4(9) . . O1B C7B O1 124.2(7) . . O1B C7B C5 124.1(11) . . O5 Cl1 O6 103.04(16) . . O5 Cl1 O3 110.2(3) . . O5 Cl1 O4 115.8(2) . . O3 Cl1 O6 113.4(2) . . O3 Cl1 O4 107.0(3) . . O4 Cl1 O6 107.51(19) . . O6 Cl1A O5 111.34(16) . . O6 Cl1A O3A 104.9(3) . . O6 Cl1A O5A 113.4(3) . . O3A Cl1A O5 101.8(3) . . O5A Cl1A O5 114.1(2) . . O5A Cl1A O3A 110.3(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N2 1.351(3) . C1 N3 1.353(3) . C1 N5 1.291(4) . O1 H1 0.88(5) . O1 C7A 1.305(18) . O1 C7B 1.347(15) . C2 C3 1.474(4) . C2 N3 1.332(3) 4_556 C2 N3 1.332(3) . N2 H2 0.83(4) . C3 C4 1.389(3) 4_556 C3 C4 1.389(3) . N3 H3 0.84(4) . C4 H4 0.93(3) . C4 C5 1.393(3) . C5 C6 1.383(3) . C5 C7A 1.507(10) . C5 C7B 1.498(9) . N5 H5A 0.81(3) . N5 H5B 0.85(4) . C6 H6 0.93(4) . C7A O1A 1.188(17) . C7B O1B 1.228(14) . O5 Cl1 1.369(3) . O5 Cl1A 1.603(3) . O6 Cl1 1.624(3) . O6 Cl1A 1.229(3) . Cl1 O3 1.435(4) . Cl1 O4 1.454(4) . Cl1A O3A 1.441(5) . Cl1A O5A 1.417(5) . 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 _geom_hbond_publ_flag O1 H1 O5 0.88(5) 1.87(5) 2.751(3) 175(4) 8_665 yes O1 H1 Cl1A 0.88(5) 2.93(5) 3.748(2) 155(4) 8_665 yes N2 H2 O1A 0.83(4) 2.65(3) 3.273(9) 132.8(7) 7_666 yes N2 H2 O1A 0.83(4) 2.65(3) 3.273(9) 132.8(7) 6_656 yes N2 H2 O1B 0.83(4) 2.16(3) 2.883(6) 145.3(7) 6_656 yes N2 H2 O1B 0.83(4) 2.16(3) 2.883(6) 145.3(7) 7_666 yes N3 H3 O4 0.84(4) 2.18(4) 2.992(4) 163(5) 1_556 yes N3 H3 O3A 0.84(4) 2.64(5) 3.308(6) 139(5) 1_556 yes N5 H5A O3 0.81(3) 2.21(3) 3.003(5) 167(3) 1_556 yes N5 H5A O3A 0.81(3) 1.96(3) 2.754(5) 167(3) 1_556 yes N5 H5B O1A 0.85(4) 1.95(4) 2.768(5) 162(3) 7_666 yes N5 H5B O1B 0.85(4) 2.10(4) 2.859(6) 148(3) 7_666 yes N5 H5B O4 0.85(4) 2.61(4) 3.241(5) 132(3) 2_656 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C3 C4 C5 -179.94(16) . . . . N2 C1 N3 C2 -2.2(3) . . . . C3 C2 N3 C1 -178.87(17) . . . . C3 C4 C5 C6 -0.1(3) . . . . C3 C4 C5 C7A 170.5(5) . . . . C3 C4 C5 C7B -171.1(6) . . . . N3 C1 N2 C1 1.12(17) . . . 4_556 N3 C2 C3 C4 3.12(16) 4_556 . . . N3 C2 C3 C4 3.12(16) . . . 4_556 N3 C2 C3 C4 -176.88(16) . . . . N3 C2 C3 C4 -176.88(16) 4_556 . . 4_556 N3 C2 N3 C1 1.13(17) 4_556 . . . C4 C3 C4 C5 0.06(16) 4_556 . . . C4 C5 C6 C5 0.06(17) . . . 4_556 C4 C5 C7A O1 15.1(10) . . . . C4 C5 C7A O1A -176.7(7) . . . . C4 C5 C7B O1 -20.7(11) . . . . C4 C5 C7B O1B 165.3(6) . . . . N5 C1 N2 C1 -178.8(3) . . . 4_556 N5 C1 N3 C2 177.7(2) . . . . C6 C5 C7A O1 -174.2(5) . . . . C6 C5 C7A O1A -5.9(11) . . . . C6 C5 C7B O1 168.1(6) . . . . C6 C5 C7B O1B -5.9(10) . . . . C7A C5 C6 C5 -170.7(5) . . . 4_556 C7B C5 C6 C5 171.3(6) . . . 4_556 _cod_database_fobs_code 1577387