#------------------------------------------------------------------------------ #$Date: 2026-06-09 19:11:48 +0100 (Tue, 09 Jun 2026) $ #$Revision: 306527 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577385.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_1577385 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 'C9 H10 N6 O2, 2(N O3)' _chemical_formula_sum 'C9 H10 N8 O8' _chemical_formula_weight 358.25 _chemical_name_systematic ; 2,6-diamino-4-(5-carboxypyridin-1-ium-2-yl)-1,3,5-triazin-1-ium dinitrate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2024-02-28 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _cell_angle_alpha 90 _cell_angle_beta 91.571(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.1086(11) _cell_length_b 10.2969(7) _cell_length_c 6.4819(5) _cell_measurement_reflns_used 2682 _cell_measurement_temperature 293 _cell_measurement_theta_max 71.7450 _cell_measurement_theta_min 4.3960 _cell_volume 1341.61(16) _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 293.00 _diffrn_detector_area_resol_mean 8.0715 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.961 _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 0.0263 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5693 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.961 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.488 _diffrn_reflns_theta_min 4.399 _exptl_absorpt_coefficient_mu 1.381 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85793 _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 yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.774 _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.540 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.061 _refine_ls_extinction_coef 0.00048(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 2540 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.126 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+1.1418P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1163 _refine_ls_wR_factor_ref 0.1200 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2279 _reflns_number_total 2540 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 3-TD-03.cif _cod_data_source_block td-03 _cod_database_code 1577385 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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 0.49972(10) 0.3816(2) 0.8129(3) 0.0162(4) Uani 1 1 d . . . . . C2 C 0.56954(10) 0.4003(2) 0.7420(3) 0.0147(4) Uani 1 1 d . . . . . N3 N 0.65799(9) 0.53225(17) 0.6407(3) 0.0160(4) Uani 1 1 d . . . . . H3 H 0.6752(16) 0.613(4) 0.619(5) 0.041(9) Uiso 1 1 d . . . . . C3 C 0.61004(10) 0.2920(2) 0.7227(3) 0.0152(4) Uani 1 1 d . . . . . H3A H 0.5927(13) 0.208(3) 0.745(4) 0.023(7) Uiso 1 1 d . . . . . N4 N 0.80179(8) 0.35275(17) 0.4911(3) 0.0153(4) Uani 1 1 d . . . . . O4 O 0.46060(7) 0.47943(16) 0.7586(3) 0.0222(4) Uani 1 1 d . . . . . H4 H 0.4227(19) 0.463(4) 0.805(6) 0.054(11) Uiso 1 1 d . . . . . C4 C 0.67485(10) 0.3061(2) 0.6584(3) 0.0157(4) Uani 1 1 d . . . . . H4A H 0.7030(14) 0.235(3) 0.639(4) 0.026(7) Uiso 1 1 d . . . . . O5 O 0.48399(7) 0.28752(16) 0.9103(2) 0.0220(4) Uani 1 1 d . . . . . N5 N 0.87937(8) 0.50969(17) 0.3844(3) 0.0145(4) Uani 1 1 d . . . . . H5 H 0.9186(17) 0.529(3) 0.335(5) 0.040(9) Uiso 1 1 d . . . . . C5 C 0.69801(10) 0.4283(2) 0.6168(3) 0.0142(4) Uani 1 1 d . . . . . C6 C 0.59490(10) 0.5224(2) 0.7000(3) 0.0155(4) Uani 1 1 d . . . . . H6 H 0.5724(14) 0.603(3) 0.704(4) 0.029(7) Uiso 1 1 d . . . . . N6 N 0.77812(8) 0.58031(17) 0.5171(3) 0.0148(4) Uani 1 1 d . . . . . N7 N 0.90344(9) 0.29179(19) 0.3668(3) 0.0178(4) Uani 1 1 d . . . . . H7A H 0.8919(14) 0.216(3) 0.384(4) 0.026(7) Uiso 1 1 d . . . . . H7B H 0.9428(16) 0.313(3) 0.321(5) 0.034(8) Uiso 1 1 d . . . . . C7 C 0.76499(10) 0.4555(2) 0.5368(3) 0.0142(4) Uani 1 1 d . . . . . C8 C 0.86128(10) 0.3830(2) 0.4145(3) 0.0145(4) Uani 1 1 d . . . . . N8 N 0.85414(9) 0.72869(17) 0.4080(3) 0.0160(4) Uani 1 1 d . . . . . H8A H 0.8268(14) 0.779(3) 0.441(4) 0.019(7) Uiso 1 1 d . . . . . H8B H 0.8935(14) 0.751(3) 0.358(4) 0.023(7) Uiso 1 1 d . . . . . C9 C 0.83755(9) 0.6078(2) 0.4359(3) 0.0130(4) Uani 1 1 d . . . . . N1 N 0.30345(9) 0.40368(19) 0.8859(3) 0.0212(4) Uani 1 1 d . . . . . O1 O 0.24834(8) 0.41510(17) 0.9647(3) 0.0266(4) Uani 1 1 d . . . . . O2 O 0.33833(8) 0.50390(16) 0.8570(3) 0.0266(4) Uani 1 1 d . . . . . O3A O 0.32560(10) 0.29825(18) 0.8165(4) 0.0304(5) Uani 0.879(4) 1 d . . P A 1 O3B O 0.3323(7) 0.3066(13) 0.963(3) 0.0304(5) Uani 0.121(4) 1 d . . P A 2 N2 N 1.04633(8) 0.48080(17) 0.2001(3) 0.0146(4) Uani 1 1 d . . . . . O6 O 1.03262(7) 0.36450(14) 0.2418(2) 0.0203(3) Uani 1 1 d . . . . . O7 O 1.10152(7) 0.50778(15) 0.1277(2) 0.0202(3) Uani 1 1 d . . . . . O8 O 1.00496(7) 0.56897(14) 0.2335(2) 0.0202(3) Uani 1 1 d . . . . . 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 0.0137(9) 0.0187(10) 0.0164(9) -0.0031(8) 0.0036(7) -0.0027(8) C2 0.0134(9) 0.0162(10) 0.0144(9) 0.0000(7) 0.0004(7) 0.0000(8) N3 0.0157(8) 0.0127(8) 0.0196(8) 0.0009(6) 0.0026(7) -0.0021(7) C3 0.0172(10) 0.0129(9) 0.0157(9) 0.0006(7) 0.0030(7) -0.0032(8) N4 0.0130(8) 0.0130(8) 0.0200(8) -0.0002(6) 0.0039(6) -0.0003(7) O4 0.0132(7) 0.0224(8) 0.0312(8) 0.0023(6) 0.0053(6) 0.0026(6) C4 0.0155(9) 0.0143(9) 0.0174(9) -0.0006(8) 0.0018(7) 0.0020(8) O5 0.0184(7) 0.0225(8) 0.0253(8) 0.0024(6) 0.0047(6) -0.0047(6) N5 0.0120(8) 0.0136(8) 0.0179(8) -0.0003(6) 0.0035(6) -0.0007(7) C5 0.0120(9) 0.0169(10) 0.0137(9) -0.0008(7) 0.0012(7) 0.0003(8) C6 0.0136(9) 0.0152(10) 0.0178(9) 0.0005(7) 0.0031(7) 0.0009(8) N6 0.0121(8) 0.0142(8) 0.0183(8) 0.0010(6) 0.0033(6) 0.0007(7) N7 0.0132(9) 0.0130(9) 0.0275(10) -0.0015(7) 0.0068(7) -0.0013(7) C7 0.0129(9) 0.0159(9) 0.0138(9) 0.0004(7) -0.0004(7) -0.0008(8) C8 0.0139(9) 0.0142(9) 0.0152(9) -0.0020(7) 0.0002(7) -0.0003(8) N8 0.0121(8) 0.0127(8) 0.0236(9) 0.0010(7) 0.0059(7) 0.0004(7) C9 0.0117(9) 0.0147(9) 0.0127(9) 0.0000(7) 0.0018(7) 0.0006(7) N1 0.0169(9) 0.0226(10) 0.0241(9) 0.0027(7) -0.0007(7) -0.0051(8) O1 0.0188(8) 0.0322(9) 0.0294(8) -0.0026(7) 0.0093(6) -0.0079(7) O2 0.0217(8) 0.0198(8) 0.0385(9) 0.0004(7) 0.0078(7) -0.0058(6) O3A 0.0317(10) 0.0156(9) 0.0444(14) -0.0002(8) 0.0104(9) 0.0039(8) O3B 0.0317(10) 0.0156(9) 0.0444(14) -0.0002(8) 0.0104(9) 0.0039(8) N2 0.0123(8) 0.0144(8) 0.0172(8) 0.0001(6) 0.0018(6) -0.0008(7) O6 0.0164(7) 0.0117(7) 0.0333(8) 0.0031(6) 0.0079(6) -0.0007(6) O7 0.0135(7) 0.0167(7) 0.0309(8) 0.0015(6) 0.0083(6) -0.0007(6) O8 0.0148(7) 0.0130(7) 0.0331(8) -0.0016(6) 0.0073(6) 0.0028(6) 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_site_symmetry_1 _geom_angle_site_symmetry_3 O4 C1 C2 112.06(17) . . O5 C1 C2 121.69(19) . . O5 C1 O4 126.24(18) . . C3 C2 C1 118.70(18) . . C6 C2 C1 121.90(18) . . C6 C2 C3 119.39(18) . . C5 N3 H3 118(2) . . C6 N3 H3 119(2) . . C6 N3 C5 123.01(18) . . C2 C3 H3A 120.0(16) . . C4 C3 C2 120.11(19) . . C4 C3 H3A 119.8(16) . . C7 N4 C8 113.88(17) . . C1 O4 H4 107(3) . . C3 C4 H4A 122.3(17) . . C5 C4 C3 118.81(19) . . C5 C4 H4A 118.9(17) . . C8 N5 H5 121(2) . . C9 N5 H5 119(2) . . C9 N5 C8 120.22(17) . . N3 C5 C4 119.88(18) . . N3 C5 C7 116.12(18) . . C4 C5 C7 123.94(18) . . C2 C6 H6 127.7(18) . . N3 C6 C2 118.77(19) . . N3 C6 H6 113.5(18) . . C7 N6 C9 115.08(17) . . H7A N7 H7B 123(3) . . C8 N7 H7A 117(2) . . C8 N7 H7B 120(2) . . N4 C7 C5 116.39(18) . . N6 C7 N4 129.78(18) . . N6 C7 C5 113.80(18) . . N4 C8 N5 121.04(18) . . N7 C8 N4 120.69(19) . . N7 C8 N5 118.27(18) . . H8A N8 H8B 124(3) . . C9 N8 H8A 114.3(19) . . C9 N8 H8B 121.8(19) . . N6 C9 N5 119.98(18) . . N8 C9 N5 120.84(18) . . N8 C9 N6 119.19(18) . . O1 N1 O2 119.32(19) . . O1 N1 O3A 123.89(19) . . O1 N1 O3B 108.7(7) . . O3A N1 O2 116.56(18) . . O3B N1 O2 117.3(7) . . O7 N2 O6 119.62(17) . . O7 N2 O8 120.31(17) . . O8 N2 O6 120.06(16) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.502(3) . C1 O4 1.320(3) . C1 O5 1.203(3) . C2 C3 1.388(3) . C2 C6 1.387(3) . N3 H3 0.92(4) . N3 C5 1.351(3) . N3 C6 1.339(3) . C3 H3A 0.94(3) . C3 C4 1.387(3) . N4 C7 1.329(3) . N4 C8 1.344(3) . O4 H4 0.85(4) . C4 H4A 0.94(3) . C4 C5 1.371(3) . N5 H5 0.88(3) . N5 C8 1.370(3) . N5 C9 1.362(3) . C5 C7 1.483(3) . C6 H6 0.95(3) . N6 C7 1.319(3) . N6 C9 1.349(3) . N7 H7A 0.82(3) . N7 H7B 0.88(3) . N7 C8 1.308(3) . N8 H8A 0.79(3) . N8 H8B 0.89(3) . N8 C9 1.303(3) . N1 O1 1.239(2) . N1 O2 1.265(2) . N1 O3A 1.261(3) . N1 O3B 1.252(15) . N2 O6 1.260(2) . N2 O7 1.248(2) . N2 O8 1.254(2) . 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 N3 H3 O3A 0.92(4) 1.95(4) 2.772(3) 148(3) 2_656 yes N3 H3 O3B 0.92(4) 2.07(4) 2.912(14) 153(3) 2_656 yes O4 H4 N1 0.85(4) 2.54(4) 3.379(2) 171(3) . yes O4 H4 O2 0.85(4) 1.79(4) 2.569(2) 153(4) . yes O4 H4 O3A 0.85(4) 2.59(4) 3.324(3) 146(3) . yes O4 H4 O3B 0.85(4) 2.65(4) 3.430(15) 154(3) . yes C4 H4A O2 0.94(3) 2.52(3) 3.124(3) 123(2) 2_646 yes N5 H5 O8 0.88(3) 1.92(3) 2.800(2) 178(3) . yes C6 H6 O5 0.95(3) 2.32(3) 3.228(3) 160(2) 2_656 yes N7 H7A O7 0.82(3) 2.15(3) 2.926(2) 157(3) 2_745 yes N7 H7B O6 0.88(3) 1.97(3) 2.843(2) 175(3) . yes N8 H8A O1 0.79(3) 2.16(3) 2.950(2) 179(3) 2_656 yes N8 H8B N2 0.89(3) 2.69(3) 3.363(2) 133(2) 2_755 yes N8 H8B O6 0.89(3) 2.01(3) 2.864(2) 159(3) 2_755 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 C1 C2 C3 C4 -179.72(18) . . . . C1 C2 C6 N3 178.86(18) . . . . C2 C3 C4 C5 0.6(3) . . . . N3 C5 C7 N4 -172.71(17) . . . . N3 C5 C7 N6 5.7(3) . . . . C3 C2 C6 N3 0.3(3) . . . . C3 C4 C5 N3 0.6(3) . . . . C3 C4 C5 C7 -176.69(18) . . . . O4 C1 C2 C3 -158.26(18) . . . . O4 C1 C2 C6 23.2(3) . . . . C4 C5 C7 N4 4.7(3) . . . . C4 C5 C7 N6 -176.93(19) . . . . O5 C1 C2 C3 22.8(3) . . . . O5 C1 C2 C6 -155.8(2) . . . . C5 N3 C6 C2 1.0(3) . . . . C6 C2 C3 C4 -1.1(3) . . . . C6 N3 C5 C4 -1.5(3) . . . . C6 N3 C5 C7 176.02(18) . . . . C7 N4 C8 N5 -1.5(3) . . . . C7 N4 C8 N7 178.47(19) . . . . C7 N6 C9 N5 -1.1(3) . . . . C7 N6 C9 N8 178.93(18) . . . . C8 N4 C7 C5 178.44(17) . . . . C8 N4 C7 N6 0.4(3) . . . . C8 N5 C9 N6 0.1(3) . . . . C8 N5 C9 N8 -179.98(18) . . . . C9 N5 C8 N4 1.4(3) . . . . C9 N5 C8 N7 -178.63(18) . . . . C9 N6 C7 N4 0.9(3) . . . . C9 N6 C7 C5 -177.16(16) . . . . _cod_database_fobs_code 1577385