#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012768.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012768 loop_ _publ_author_name 'Janczak, Jan' 'Perp\'etuo, Genivaldo Julio' _publ_section_title ; Melaminium glutarate monohydrate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o339 _journal_page_last o341 _journal_paper_doi 10.1107/S0108270102007266 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C3 H7 N6 + , C5 H7 O4 - , H2 O' _chemical_formula_moiety 'C3 H7 N6 + , C5 H7 O4 - , H2 O' _chemical_formula_sum 'C8 H16 N6 O5' _chemical_formula_weight 276.27 _chemical_melting_point dehydrated _chemical_name_common ; melaminium glutarate monohydrate ; _chemical_name_systematic ; 2,4,6-triamino-1,3,5-triazine-1-ium glutarate monohydrate ; _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 _cell_angle_alpha 90 _cell_angle_beta 97.57(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.5390(10) _cell_length_b 28.544(6) _cell_length_c 9.863(2) _cell_measurement_reflns_used 1600 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28 _cell_measurement_theta_min 3 _cell_volume 1266.7(5) _computing_cell_refinement 'KM-4 CCD Software' _computing_data_collection 'KM-4 CCD Software (Kuma Diffraction, 2000)' _computing_data_reduction 'KM-4 CCD Software' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2' _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_device_type 'Kuma KM-4 with CCD area-detector' _diffrn_measurement_method '\w scan' _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 0.019 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11010 _diffrn_reflns_theta_full 27.99 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_min 2.85 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'face-indexed (SHELXTL; Sheldrick, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_meas 1.444 _exptl_crystal_density_method flotation _exptl_crystal_description parallelepiped _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.14 _refine_diff_density_min -0.12 _refine_ls_extinction_coef 0.0084(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2920 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all 0.075 _refine_ls_R_factor_gt 0.029 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0274P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.058 _refine_ls_wR_factor_ref 0.070 _reflns_number_gt 1605 _reflns_number_total 2920 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1570.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012768 _cod_database_fobs_code 2012768 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _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 _atom_site_type_symbol N1 0.3304(2) 0.48729(3) 0.14798(10) 0.0362(3) Uani d . 1 . . N N2 0.7210(2) 0.48827(3) 0.33912(10) 0.0372(3) Uani d . 1 . . N N3 0.4139(2) 0.55352(4) 0.28920(11) 0.0394(3) Uani d . 1 . . N H3 0.364(3) 0.5831(5) 0.3114(13) 0.047 Uiso d . 1 . . H C1 0.5606(3) 0.46749(4) 0.22968(12) 0.0359(3) Uani d . 1 . . C C2 0.6430(3) 0.53172(4) 0.36590(12) 0.0355(3) Uani d . 1 . . C C3 0.2611(3) 0.53069(4) 0.17996(12) 0.0356(3) Uani d . 1 . . C N4 0.6369(3) 0.42445(4) 0.20079(12) 0.0464(3) Uani d . 1 . . N H41 0.538(3) 0.4089(4) 0.1233(13) 0.056 Uiso d . 1 . . H H42 0.793(3) 0.4105(5) 0.2586(13) 0.056 Uiso d . 1 . . H N5 0.7921(3) 0.55529(4) 0.46793(12) 0.0477(3) Uani d . 1 . . N H51 0.930(3) 0.5404(5) 0.5198(14) 0.057 Uiso d . 1 . . H H52 0.743(3) 0.5834(5) 0.4846(14) 0.057 Uiso d . 1 . . H N6 0.0379(3) 0.55329(4) 0.10906(12) 0.0448(3) Uani d . 1 . . N H61 -0.052(3) 0.5403(4) 0.0303(14) 0.054 Uiso d . 1 . . H H62 0.012(3) 0.5823(5) 0.1306(13) 0.054 Uiso d . 1 . . H O1 1.0579(2) 0.84827(3) 0.68347(10) 0.0539(3) Uani d . 1 . . O O2 1.3274(2) 0.85847(3) 0.88434(10) 0.0564(3) Uani d . 1 . . O O3 0.8772(2) 0.63348(3) 0.64853(10) 0.0611(3) Uani d . 1 . . O O4 0.5275(2) 0.68672(3) 0.60591(11) 0.0635(3) Uani d . 1 . . O H4 0.443(4) 0.6680(6) 0.5261(18) 0.095 Uiso d . 1 . . H C4 1.1598(3) 0.83364(4) 0.80016(14) 0.0411(3) Uani d . 1 . . C C5 1.0881(3) 0.78512(4) 0.84331(13) 0.0487(4) Uani d . 1 . . C H5A 0.9546 0.7875 0.9121 0.058 Uiso calc R 1 . . H H5B 1.2702 0.7707 0.8864 0.058 Uiso calc R 1 . . H C6 0.9484(3) 0.75291(4) 0.73177(13) 0.0447(3) Uani d . 1 . . C H6A 1.0730 0.7518 0.6591 0.054 Uiso calc R 1 . . H H6B 0.7564 0.7654 0.6937 0.054 Uiso calc R 1 . . H C7 0.9081(3) 0.70353(4) 0.78398(13) 0.0445(3) Uani d . 1 . . C H7A 1.1000 0.6914 0.8234 0.053 Uiso calc R 1 . . H H7B 0.7817 0.7047 0.8559 0.053 Uiso calc R 1 . . H C8 0.7741(3) 0.67098(4) 0.67485(13) 0.0410(3) Uani d . 1 . . C O5W 0.4736(3) 0.35602(4) 0.98748(11) 0.0658(3) Uani d . 1 . . O H5W1 0.314(4) 0.3486(6) 0.9284(19) 0.099 Uiso d . 1 . . H H5W2 0.633(4) 0.3536(6) 0.9389(19) 0.099 Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0397(6) 0.0300(5) 0.0364(6) 0.0043(4) -0.0041(5) -0.0040(4) N2 0.0401(6) 0.0310(5) 0.0375(6) 0.0021(4) -0.0063(5) -0.0038(4) N3 0.0431(6) 0.0299(5) 0.0418(6) 0.0044(5) -0.0069(5) -0.0067(5) C1 0.0370(7) 0.0309(6) 0.0381(7) -0.0002(5) -0.0017(6) -0.0032(5) C2 0.0370(7) 0.0301(5) 0.0378(7) -0.0016(5) -0.0017(6) -0.0020(6) C3 0.0358(7) 0.0324(6) 0.0370(6) -0.0021(5) -0.0013(6) 0.0007(5) N4 0.0505(7) 0.0350(6) 0.0489(7) 0.0088(5) -0.0111(6) -0.0086(5) N5 0.0530(7) 0.0346(5) 0.0501(7) 0.0057(5) -0.0132(6) -0.0115(6) N6 0.0485(7) 0.0333(5) 0.0476(7) 0.0063(5) -0.0120(6) -0.0048(5) O1 0.0609(6) 0.0449(5) 0.0502(6) -0.0108(4) -0.0143(5) 0.0129(4) O2 0.0675(7) 0.0389(5) 0.0556(6) -0.0158(5) -0.0189(5) 0.0083(5) O3 0.0632(7) 0.0411(5) 0.0721(7) 0.0099(5) -0.0172(6) -0.0140(5) O4 0.0646(7) 0.0500(6) 0.0664(7) 0.0159(5) -0.0270(6) -0.0190(5) C4 0.0419(7) 0.0368(6) 0.0427(7) -0.0039(6) -0.0011(7) 0.0058(6) C5 0.0672(9) 0.0360(7) 0.0398(7) -0.0118(6) -0.0044(7) 0.0005(6) C6 0.0593(9) 0.0348(6) 0.0384(7) -0.0055(6) 0.0003(7) 0.0001(6) C7 0.0523(8) 0.0350(6) 0.0423(7) -0.0039(6) -0.0080(7) -0.0013(6) C8 0.0439(8) 0.0332(6) 0.0434(8) -0.0003(5) -0.0032(7) 0.0010(6) O5W 0.0577(7) 0.0820(7) 0.0554(7) -0.0094(6) -0.0009(5) -0.0191(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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 C3 N1 C1 115.90(10) y C2 N2 C1 116.00(10) y C2 N3 C3 119.60(10) y C2 N3 H3 119.3(8) ? C3 N3 H3 121.1(8) ? N4 C1 N1 117.60(10) ? N4 C1 N2 116.80(10) ? N1 C1 N2 125.60(10) y N5 C2 N2 120.30(10) ? N5 C2 N3 118.10(10) ? N2 C2 N3 121.60(10) y N6 C3 N1 121.30(10) ? N6 C3 N3 117.30(10) ? N1 C3 N3 121.40(10) y C1 N4 H41 120.2(8) ? C1 N4 H42 117.6(8) ? H41 N4 H42 122.2(11) ? C2 N5 H51 117.3(9) ? C2 N5 H52 120.4(9) ? H51 N5 H52 122.2(13) ? C3 N6 H61 118.6(8) ? C3 N6 H62 117.1(9) ? H61 N6 H62 122.8(12) ? C8 O4 H4 116.3(10) ? O1 C4 O2 122.20(10) y O1 C4 C5 120.10(10) y O2 C4 C5 117.80(10) y C4 C5 C6 116.30(10) y C4 C5 H5A 108.2 ? C6 C5 H5A 108.2 ? C4 C5 H5B 108.2 ? C6 C5 H5B 108.2 ? H5A C5 H5B 107.4 ? C5 C6 C7 112.10(10) y C5 C6 H6A 109.2 ? C7 C6 H6A 109.2 ? C5 C6 H6B 109.2 ? C7 C6 H6B 109.2 ? H6A C6 H6B 107.9 ? C8 C7 C6 112.90(10) y C8 C7 H7A 109.0 ? C6 C7 H7A 109.0 ? C8 C7 H7B 109.0 ? C6 C7 H7B 109.0 ? H7A C7 H7B 107.8 ? O3 C8 O4 121.30(10) y O3 C8 C7 125.10(10) y O4 C8 C7 113.60(10) y H5W1 O5W H5W2 105.5(16) ? 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 C3 . 1.327(2) y N1 C1 . 1.356(2) y N2 C2 . 1.326(2) y N2 C1 . 1.356(2) y N3 C2 . 1.354(2) y N3 C3 . 1.367(2) y N3 H3 . 0.907(13) ? C1 N4 . 1.318(2) y C2 N5 . 1.321(2) y C3 N6 . 1.321(2) y N4 H41 . 0.945(13) ? N4 H42 . 0.938(14) ? N5 H51 . 0.865(14) ? N5 H52 . 0.853(13) ? N6 H61 . 0.908(14) ? N6 H62 . 0.867(13) ? O1 C4 . 1.254(2) y O2 C4 . 1.266(2) y O3 C8 . 1.210(2) y O4 C8 . 1.310(2) y O4 H4 . 0.986(18) ? C4 C5 . 1.497(2) y C5 C6 . 1.508(2) y C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.520(2) y C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C8 . 1.490(2) y C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? O5W H5W1 . 0.89(2) ? O5W H5W2 . 0.92(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 N3 H3 O2 1_555 1_555 4_475 0.91(2) 1.83(2) 2.728(2) 168.0(10) yes N4 H41 O5W 1_555 1_555 1_554 0.95(2) 2.01(2) 2.895(2) 155.0(10) yes N4 H42 O3 1_555 1_555 3_766 0.94(2) 2.07(2) 2.991(2) 166.0(10) yes N5 H51 N2 1_555 1_555 3_766 0.87(2) 2.13(2) 2.991(2) 173.0(10) yes N5 H52 O3 1_555 1_555 1_555 0.85(2) 2.18(2) 2.850(2) 135.0(10) yes N6 H61 N1 1_555 1_555 3_565 0.91(2) 2.17(2) 3.074(2) 171.0(10) yes N6 H62 O1 1_555 1_555 4_475 0.87(2) 2.05(2) 2.903(2) 167.0(10) yes O4 H4 O2 1_555 1_555 4_475 0.99(2) 1.62(2) 2.597(2) 173(2) yes O5W H5W1 O1 1_555 1_555 2_646 0.89(2) 1.89(2) 2.764(2) 165(2) yes O5W H5W2 O1 1_555 1_555 2_746 0.92(2) 1.97(2) 2.891(2) 174(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21134840 2 PubChem 139058589