#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008366.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_2008366 loop_ _publ_author_name 'Shyamaprosad Goswami' 'Ajit Kumar Mahapatra' 'Gur Dayal Nigam' 'Kandasamy Chinnakali' 'Hoong-Kun Fun' 'Ibrahim Abdul Razak' _publ_section_title ; 2-Aminopyrimidine--fumaric acid cocrystal ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 583 _journal_page_last 585 _journal_paper_doi 10.1107/S0108270198014127 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac 'C4 H6 N3 + , 0.5C4 H2 O4 2- , 0.5C4 H4 O4' _chemical_formula_sum 'C8 H9 N3 O4' _chemical_formula_weight 211.18 _chemical_name_systematic ; 2-Aminopyrimidine-Fumaric Acid (1:2) co-crystal ; _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' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 96.8930(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.7946(2) _cell_length_b 19.1766(7) _cell_length_c 13.0641(6) _cell_measurement_reflns_used 3463 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.12 _cell_measurement_theta_min 3.14 _cell_volume 943.77(7) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w-scans _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 0.042 _diffrn_reflns_av_sigmaI/netI 0.055 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 7257 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 3.14 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.387 _refine_diff_density_min -0.227 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2752 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.103 _refine_ls_R_factor_gt 0.067 _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^)+(0.0917P)^2^+0.1819P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.184 _reflns_number_gt 1830 _reflns_number_total 2752 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ha1239.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0917P)^2^+0.1819P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0917P)^2^+0.1819P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008366 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 O1 0.1905(6) 0.62910(9) 0.61390(12) 0.0539(5) Uani d . 1 . . O O2 0.0801(6) 0.52917(9) 0.68871(13) 0.0548(5) Uani d . 1 . . O O3 0.1719(6) 0.62725(8) 1.01398(12) 0.0525(5) Uani d . 1 . . O O4 0.2351(5) 0.60162(8) 0.85166(11) 0.0474(5) Uani d . 1 . . O N1 0.3200(6) 0.76552(11) 0.96641(15) 0.0416(5) Uani d . 1 . . N N2 0.5257(5) 0.72713(9) 0.81691(13) 0.0326(4) Uani d . 1 . . N N3 0.5203(6) 0.84706(10) 0.85756(14) 0.0399(4) Uani d . 1 . . N C1 0.4566(6) 0.77998(10) 0.88042(15) 0.0310(4) Uani d . 1 . . C C2 0.6686(6) 0.73995(12) 0.72887(16) 0.0373(5) Uani d . 1 . . C C3 0.7389(7) 0.80689(13) 0.70255(17) 0.0421(5) Uani d . 1 . . C C4 0.6561(7) 0.85881(12) 0.77045(18) 0.0432(5) Uani d . 1 . . C C5 0.1165(6) 0.56777(11) 0.60825(16) 0.0362(5) Uani d . 1 . . C C6 0.0602(7) 0.53191(11) 0.50632(16) 0.0384(5) Uani d . 1 . . C C7 0.1541(6) 0.58576(10) 0.94145(15) 0.0341(5) Uani d . 1 . . C C8 0.0346(6) 0.51254(10) 0.95560(15) 0.0368(5) Uani d . 1 . . C H1N1 0.280(9) 0.7177(18) 0.983(2) 0.065(9) Uiso d . 1 . . H H2N1 0.283(7) 0.8029(14) 1.012(2) 0.045(7) Uiso d . 1 . . H H1N2 0.454(8) 0.6830(17) 0.831(2) 0.059(8) Uiso d . 1 . . H H1O2 0.115(8) 0.5552(16) 0.749(2) 0.059(8) Uiso d . 1 . . H H2 0.709(7) 0.6988(14) 0.6898(19) 0.041(6) Uiso d . 1 . . H H3 0.833(8) 0.8180(16) 0.639(2) 0.055(8) Uiso d . 1 . . H H4 0.685(7) 0.9075(16) 0.754(2) 0.047(7) Uiso d . 1 . . H H6 0.115(7) 0.5596(15) 0.444(2) 0.052(8) Uiso d . 1 . . H H8 0.006(9) 0.4797(17) 0.892(2) 0.066(9) 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 O1 0.0983(15) 0.0313(9) 0.0330(8) -0.0148(9) 0.0116(8) -0.0023(6) O2 0.1044(16) 0.0275(8) 0.0331(8) -0.0143(9) 0.0108(9) -0.0037(6) O3 0.0951(14) 0.0306(8) 0.0355(8) -0.0169(8) 0.0234(9) -0.0071(6) O4 0.0873(13) 0.0303(8) 0.0275(7) -0.0174(8) 0.0185(8) -0.0007(6) N1 0.0653(13) 0.0286(10) 0.0328(9) -0.0027(8) 0.0140(8) -0.0018(7) N2 0.0426(10) 0.0232(8) 0.0320(8) -0.0032(7) 0.0048(7) -0.0019(6) N3 0.0547(12) 0.0237(9) 0.0416(10) -0.0051(7) 0.0077(8) -0.0014(7) C1 0.0385(11) 0.0254(9) 0.0284(9) -0.0016(7) 0.0011(7) -0.0009(7) C2 0.0420(12) 0.0371(12) 0.0329(10) -0.0016(9) 0.0050(8) -0.0054(8) C3 0.0458(13) 0.0468(13) 0.0343(10) -0.0081(10) 0.0073(9) 0.0046(9) C4 0.0566(15) 0.0291(11) 0.0439(12) -0.0083(9) 0.0065(10) 0.0063(9) C5 0.0497(12) 0.0306(10) 0.0289(9) -0.0006(9) 0.0068(9) -0.0035(8) C6 0.0555(14) 0.0297(10) 0.0303(10) -0.0013(9) 0.0069(9) 0.0000(8) C7 0.0499(12) 0.0241(9) 0.0297(9) -0.0062(8) 0.0112(8) 0.0003(7) C8 0.0577(13) 0.0235(9) 0.0306(10) -0.0077(8) 0.0119(9) -0.0011(8) 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_site_symmetry_1 _geom_angle C5 O2 H1O2 . 111.0(18) C1 N1 H1N1 . 118.6(18) C1 N1 H2N1 . 118.4(16) H1N1 N1 H2N1 . 123(2) C2 N2 C1 . 120.79(18) C2 N2 H1N2 . 119.9(18) C1 N2 H1N2 . 119.0(18) C4 N3 C1 . 116.82(19) N1 C1 N3 . 119.15(19) N1 C1 N2 . 119.20(18) N3 C1 N2 . 121.65(18) N2 C2 C3 . 119.8(2) N2 C2 H2 . 114.1(15) C3 C2 H2 . 126.1(15) C2 C3 C4 . 116.5(2) C2 C3 H3 . 121.9(18) C4 C3 H3 . 121.6(18) N3 C4 C3 . 124.5(2) N3 C4 H4 . 114.8(16) C3 C4 H4 . 120.7(16) O1 C5 O2 . 123.2(2) O1 C5 C6 . 120.69(19) O2 C5 C6 . 116.07(19) C6 C6 C5 3_566 123.6(3) C6 C6 H6 3_566 119.2(15) C5 C6 H6 . 117.1(15) O3 C7 O4 . 123.51(19) O3 C7 C8 . 120.06(17) O4 C7 C8 . 116.43(17) C8 C8 C7 3_567 123.4(2) C8 C8 H8 3_567 118.1(18) C7 C8 H8 . 118.5(18) 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 O1 C5 . 1.209(3) yes O2 C5 . 1.306(3) yes O2 H1O2 . 0.92(3) ? O3 C7 . 1.233(2) yes O4 C7 . 1.284(2) yes N1 C1 . 1.322(3) yes N1 H1N1 . 0.96(3) ? N1 H2N1 . 0.95(3) ? N2 C2 . 1.352(3) yes N2 C1 . 1.355(3) yes N2 H1N2 . 0.91(3) ? N3 C4 . 1.324(3) yes N3 C1 . 1.349(3) yes C2 C3 . 1.364(3) yes C2 H2 . 0.96(3) ? C3 C4 . 1.394(3) yes C3 H3 . 0.96(3) ? C4 H4 . 0.97(3) ? C5 C6 . 1.491(3) yes C6 C6 3_566 1.310(4) yes C6 H6 . 1.02(3) ? C7 C8 . 1.494(3) yes C8 C8 3_567 1.311(4) yes C8 H8 . 1.03(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 N1 H1N1 O3 1_555 0.96(3) 1.84(3) 2.796(3) 176(3) yes N2 H1N2 O4 1_555 0.91(3) 1.80(3) 2.708(2) 170(3) yes O2 H1O2 O4 1_555 0.93(3) 1.63(3) 2.551(2) 172(3) yes C2 H2 O1 1_555 0.96(3) 2.48(3) 3.068(3) 119(2) yes C2 H2 O1 1_655 0.96(3) 2.56(3) 3.378(3) 143(2) yes N1 H2N1 O1 4_565 0.95(3) 1.93(3) 2.875(3) 174(2) yes C4 H4 O2 2_656 0.97(3) 2.58(3) 3.440(3) 149(2) yes C3 H3 O3 4_664 0.97(3) 2.43(3) 3.367(3) 162(2) 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_4 _geom_torsion C4 N3 C1 N1 . -179.8(2) C4 N3 C1 N2 . -0.5(3) C2 N2 C1 N1 . -179.3(2) C2 N2 C1 N3 . 1.4(3) C1 N2 C2 C3 . -1.1(3) N2 C2 C3 C4 . 0.1(3) C1 N3 C4 C3 . -0.6(4) C2 C3 C4 N3 . 0.8(4) O1 C5 C6 C6 3_566 -171.8(3) O2 C5 C6 C6 3_566 8.1(4) O3 C7 C8 C8 3_567 -4.4(5) O4 C7 C8 C8 3_567 175.4(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 67108266