#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008266.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_2008266 loop_ _publ_author_name 'Kandasamy Chinnakali' 'Hoong-Kun Fun' 'Shyamaprasad Goswami' 'Ajit Kumar Mahapatra' 'Gur Dayal Nigam' _publ_section_title ; 2-Aminopyrimidine and p-phenylenediacetic acid (1:1) co-crystal ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 399 _journal_page_last 401 _journal_paper_doi 10.1107/S0108270198013626 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac 'C4 H5 N3 , C10 H10 O4' _chemical_formula_sum 'C14 H15 N3 O4' _chemical_formula_weight 289.29 _chemical_name_systematic ; 2-Aminopyrimidine and p-phenylenediacetic acid ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.56860(10) _cell_length_b 15.7687(2) _cell_length_c 20.1621(4) _cell_measurement_reflns_used 3724 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.18 _cell_measurement_theta_min 2.77 _cell_volume 1452.50(5) _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 PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.033 _diffrn_reflns_av_sigmaI/netI 0.029 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 11260 _diffrn_reflns_theta_full 32 _diffrn_reflns_theta_max 32.00 _diffrn_reflns_theta_min 2.77 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.119 _refine_diff_density_min -0.096 _refine_ls_extinction_coef 0.026(3) _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2515 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.116 _refine_ls_R_factor_gt 0.059 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.2796P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.161 _reflns_number_gt 1286 _reflns_number_total 2515 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ha1242.cif _cod_data_source_block I _cod_original_sg_symbol_H-M Pbcn _cod_database_code 2008266 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' 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 0.1400(3) 0.35048(8) 0.64565(7) 0.0956(5) Uani d . 1 . . O O2 0.0011(4) 0.22373(9) 0.61149(8) 0.0961(5) Uani d . 1 . . O N1 0.3388(4) 0.15077(9) 0.70366(7) 0.0756(5) Uani d . 1 . . N N2 0.5000 0.27532(15) 0.7500 0.0903(8) Uani d S 1 . . N C1 -0.0970(4) 0.42296(11) 0.52668(9) 0.0692(5) Uani d . 1 . . C C2 -0.1812(5) 0.49945(14) 0.55305(11) 0.0881(6) Uani d . 1 . . C C3 0.0850(5) 0.42488(13) 0.47323(10) 0.0867(6) Uani d . 1 . . C C4 -0.1966(6) 0.33973(16) 0.55521(14) 0.0929(7) Uani d . 1 . . C C5 -0.0014(4) 0.30613(12) 0.60887(9) 0.0718(5) Uani d . 1 . . C C6 0.5000 0.19082(16) 0.7500 0.0680(6) Uani d S 1 . . C C7 0.3460(5) 0.06616(13) 0.70459(10) 0.0864(6) Uani d . 1 . . C C8 0.5000 0.0207(2) 0.7500 0.0928(9) Uani d S 1 . . C H1O2 0.132(6) 0.2014(15) 0.6486(14) 0.132(9) Uiso d . 1 . . H H1N2 0.389(4) 0.3021(13) 0.7193(10) 0.097(7) Uiso d . 1 . . H H2 -0.310(6) 0.4980(14) 0.5898(13) 0.122(8) Uiso d . 1 . . H H3 0.144(5) 0.3727(16) 0.4530(13) 0.121(8) Uiso d . 1 . . H H4A -0.228(6) 0.2977(17) 0.5228(13) 0.131(9) Uiso d . 1 . . H H4B -0.383(7) 0.3524(17) 0.5791(12) 0.131(10) Uiso d . 1 . . H H7 0.231(5) 0.0396(13) 0.6693(10) 0.096(6) Uiso d . 1 . . H H8 0.5000 -0.040(2) 0.7500 0.120(11) Uiso d S 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 0.1278(12) 0.0712(8) 0.0876(9) -0.0086(8) -0.0370(9) 0.0024(6) O2 0.1231(12) 0.0695(9) 0.0957(10) -0.0092(7) -0.0344(9) -0.0032(7) N1 0.0950(11) 0.0673(9) 0.0645(8) -0.0075(8) -0.0054(8) -0.0004(6) N2 0.133(2) 0.0651(14) 0.0730(14) 0.000 -0.0311(15) 0.000 C1 0.0645(9) 0.0733(11) 0.0698(10) 0.0055(8) -0.0183(8) -0.0033(8) C2 0.0928(14) 0.0935(15) 0.0781(12) 0.0194(12) 0.0162(11) -0.0026(10) C3 0.1071(15) 0.0711(13) 0.0820(12) 0.0234(11) 0.0027(11) -0.0143(10) C4 0.0862(16) 0.0888(15) 0.1037(16) -0.0126(12) -0.0293(13) 0.0106(12) C5 0.0753(11) 0.0713(11) 0.0689(10) -0.0091(9) -0.0038(9) 0.0003(8) C6 0.0843(16) 0.0660(14) 0.0537(12) 0.000 0.0034(11) 0.000 C7 0.1063(16) 0.0715(12) 0.0816(13) -0.0127(11) -0.0050(12) -0.0056(10) C8 0.120(3) 0.0634(16) 0.095(2) 0.000 -0.0102(18) 0.000 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_site_symmetry_3 _geom_angle C7 N1 C6 . . 116.45(18) C3 C1 C2 . . 117.26(18) C3 C1 C4 . . 120.5(2) C2 C1 C4 . . 122.3(2) C1 C2 C3 . 5_566 121.5(2) C1 C3 C2 . 5_566 121.24(18) C5 C4 C1 . . 113.87(17) O1 C5 O2 . . 123.32(18) O1 C5 C4 . . 123.87(19) O2 C5 C4 . . 112.81(17) N2 C6 N1 . 3_656 117.96(11) N2 C6 N1 . . 117.96(11) N1 C6 N1 3_656 . 124.1(2) N1 C7 C8 . . 123.4(2) C7 C8 C7 3_656 . 116.3(3) 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 . 1.207(2) yes O2 C5 . 1.300(2) yes N1 C7 . 1.335(2) yes N1 C6 . 1.3469(18) yes N2 C6 . 1.333(3) yes C1 C3 . 1.361(3) ? C1 C2 . 1.373(3) ? C1 C4 . 1.504(3) ? C2 C3 5_566 1.378(3) ? C3 C2 5_566 1.378(3) ? C4 C5 . 1.499(3) ? C6 N1 3_656 1.3469(18) ? C7 C8 . 1.359(3) ? C8 C7 3_656 1.359(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 O2 H1O2 N1 1_555 1.02(3) 1.66(3) 2.675(2) 171(2) yes N2 H1N2 O1 1_555 0.90(2) 2.02(2) 2.922(2) 174(2) yes C4 H4B O1 1_455 1.00(3) 2.56(3) 3.541(3) 168(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 C3 C1 C2 C3 5_566 -0.2(4) C4 C1 C2 C3 5_566 179.20(19) C2 C1 C3 C2 5_566 0.2(3) C4 C1 C3 C2 5_566 -179.21(19) C3 C1 C4 C5 . 90.8(3) C2 C1 C4 C5 . -88.6(3) C1 C4 C5 O1 . 29.9(3) C1 C4 C5 O2 . -149.7(2) C7 N1 C6 N2 . 179.32(13) C7 N1 C6 N1 3_656 -0.68(13) C6 N1 C7 C8 . 1.4(3) N1 C7 C8 C7 3_656 -0.75(14) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 67107797