#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201978 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/22/2222233.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_2222233 loop_ _publ_author_name 'Meng, A-Lan' 'Huang, Jun-E' 'Zheng, Bin' 'Li, Zhen-Jiang' _publ_section_title ; 2-Amino-4,6-dimethylpyrimidine--benzoic acid (1/1) ; _journal_coeditor_code BI2374 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1595 _journal_paper_doi 10.1107/S1600536809020649 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C6 H9 N3, C7 H6 O2' _chemical_formula_moiety 'C6 H9 N3, C7 H6 O2' _chemical_formula_sum 'C13 H15 N3 O2' _chemical_formula_weight 245.28 _chemical_name_systematic ; 2-Amino-4,6-dimethylpyrimidine--benzoic acid (1/1) ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.360(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.7019(9) _cell_length_b 7.6466(10) _cell_length_c 25.285(3) _cell_measurement_reflns_used 167 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 25.04 _cell_measurement_theta_min 1.61 _cell_volume 1295.4(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '\f and \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 0.1044 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6594 _diffrn_reflns_theta_full 25.04 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 1.61 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.216 _refine_diff_density_min -0.192 _refine_ls_extinction_coef 0.0077(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2273 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0526 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.0120P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1234 _refine_ls_wR_factor_ref 0.1366 _reflns_number_gt 1228 _reflns_number_total 2273 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bi2374.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2222233 _cod_database_fobs_code 2222233 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_type_symbol _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 O O1 0.6583(2) 0.6591(2) 0.41923(6) 0.0678(5) Uani d . 1 . . H H1 0.5870 0.7100 0.4402 0.102 Uiso calc R 1 . . O O2 0.3940(3) 0.6933(3) 0.36625(7) 0.0787(6) Uani d . 1 . . N N1 0.4633(3) 0.7645(2) 0.50129(7) 0.0482(5) Uani d . 1 . . N N2 0.1976(3) 0.9074(2) 0.54612(8) 0.0560(6) Uani d . 1 . . N N3 0.1836(3) 0.8632(2) 0.45633(8) 0.0646(6) Uani d . 1 . . H H3A 0.2332 0.8250 0.4275 0.078 Uiso calc R 1 . . H H3B 0.0689 0.9137 0.4557 0.078 Uiso calc R 1 . . C C1 0.6891(4) 0.5714(3) 0.33125(9) 0.0540(6) Uani d . 1 . . C C2 0.8886(4) 0.5334(3) 0.34037(10) 0.0662(7) Uani d . 1 . . H H2 0.9484 0.5593 0.3730 0.079 Uiso calc R 1 . . C C3 0.9993(5) 0.4573(4) 0.30126(13) 0.0813(9) Uani d . 1 . . H H3 1.1337 0.4326 0.3075 0.098 Uiso calc R 1 . . C C4 0.9124(6) 0.4184(4) 0.25352(13) 0.0892(10) Uani d . 1 . . H H4 0.9866 0.3641 0.2276 0.107 Uiso calc R 1 . . C C5 0.7167(6) 0.4587(4) 0.24346(11) 0.0931(10) Uani d . 1 . . H H5 0.6586 0.4332 0.2106 0.112 Uiso calc R 1 . . C C6 0.6032(4) 0.5382(4) 0.28248(10) 0.0754(8) Uani d . 1 . . H H6 0.4708 0.5683 0.2754 0.090 Uiso calc R 1 . . C C7 0.5664(4) 0.6473(3) 0.37388(10) 0.0542(7) Uani d . 1 . . C C8 0.2837(4) 0.8443(3) 0.50166(10) 0.0497(6) Uani d . 1 . . C C9 0.5618(3) 0.7431(3) 0.54739(9) 0.0522(6) Uani d . 1 . . C C10 0.4805(4) 0.8019(3) 0.59401(10) 0.0620(7) Uani d . 1 . . H H10 0.5481 0.7868 0.6262 0.074 Uiso calc R 1 . . C C11 0.2973(4) 0.8831(3) 0.59146(10) 0.0579(7) Uani d . 1 . . C C12 0.7598(4) 0.6537(3) 0.54573(11) 0.0699(8) Uani d . 1 . . H H12A 0.7401 0.5309 0.5397 0.105 Uiso calc R 1 . . H H12B 0.8303 0.6706 0.5788 0.105 Uiso calc R 1 . . H H12C 0.8361 0.7022 0.5176 0.105 Uiso calc R 1 . . C C13 0.1975(4) 0.9484(3) 0.64045(10) 0.0793(9) Uani d . 1 . . H H13A 0.1886 1.0737 0.6393 0.119 Uiso calc R 1 . . H H13B 0.2743 0.9136 0.6712 0.119 Uiso calc R 1 . . H H13C 0.0658 0.8996 0.6421 0.119 Uiso calc R 1 . . 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 0.0593(11) 0.0969(15) 0.0473(11) 0.0084(10) 0.0053(9) -0.0141(10) O2 0.0568(12) 0.1232(16) 0.0564(12) 0.0167(11) 0.0055(9) -0.0012(10) N1 0.0425(11) 0.0546(12) 0.0480(12) -0.0031(9) 0.0092(9) -0.0005(9) N2 0.0584(13) 0.0594(13) 0.0510(13) -0.0063(10) 0.0179(10) -0.0042(11) N3 0.0552(13) 0.0919(16) 0.0472(13) 0.0168(11) 0.0084(10) -0.0057(11) C1 0.0620(17) 0.0566(15) 0.0439(15) -0.0070(13) 0.0109(12) 0.0003(12) C2 0.0670(19) 0.0707(18) 0.0617(17) -0.0002(14) 0.0157(14) -0.0015(14) C3 0.081(2) 0.085(2) 0.080(2) 0.0071(17) 0.0337(18) -0.0012(18) C4 0.119(3) 0.073(2) 0.078(2) -0.003(2) 0.056(2) -0.0027(18) C5 0.119(3) 0.113(3) 0.0486(19) -0.020(2) 0.0181(18) -0.0134(17) C6 0.0767(19) 0.098(2) 0.0513(17) -0.0100(16) 0.0084(14) -0.0062(16) C7 0.0529(16) 0.0653(17) 0.0448(16) -0.0014(13) 0.0080(13) 0.0025(12) C8 0.0524(15) 0.0516(14) 0.0456(15) -0.0068(12) 0.0121(12) -0.0030(12) C9 0.0502(15) 0.0550(16) 0.0516(16) -0.0112(12) 0.0041(12) 0.0032(12) C10 0.0705(19) 0.0703(17) 0.0454(16) -0.0090(15) 0.0058(13) 0.0030(13) C11 0.0694(18) 0.0566(16) 0.0486(16) -0.0128(14) 0.0196(13) -0.0031(12) C12 0.0561(17) 0.0836(18) 0.0700(18) 0.0001(14) 0.0004(13) 0.0025(15) C13 0.100(2) 0.0828(19) 0.0562(17) -0.0108(17) 0.0289(15) -0.0094(15) 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 _geom_angle_publ_flag C7 O1 H1 . . 109.5 ? C9 N1 C8 . . 118.13(19) ? C11 N2 C8 . . 116.7(2) ? C8 N3 H3A . . 120.0 ? C8 N3 H3B . . 120.0 ? H3A N3 H3B . . 120.0 ? C6 C1 C2 . . 119.6(2) ? C6 C1 C7 . . 119.7(2) ? C2 C1 C7 . . 120.7(2) ? C3 C2 C1 . . 120.3(3) ? C3 C2 H2 . . 119.9 ? C1 C2 H2 . . 119.9 ? C4 C3 C2 . . 120.1(3) ? C4 C3 H3 . . 119.9 ? C2 C3 H3 . . 119.9 ? C3 C4 C5 . . 120.3(3) ? C3 C4 H4 . . 119.8 ? C5 C4 H4 . . 119.8 ? C4 C5 C6 . . 120.2(3) ? C4 C5 H5 . . 119.9 ? C6 C5 H5 . . 119.9 ? C1 C6 C5 . . 119.4(3) ? C1 C6 H6 . . 120.3 ? C5 C6 H6 . . 120.3 ? O2 C7 O1 . . 123.4(2) ? O2 C7 C1 . . 122.4(2) ? O1 C7 C1 . . 114.2(2) ? N3 C8 N1 . . 118.5(2) ? N3 C8 N2 . . 117.4(2) ? N1 C8 N2 . . 124.1(2) ? N1 C9 C10 . . 120.4(2) ? N1 C9 C12 . . 116.9(2) ? C10 C9 C12 . . 122.7(2) ? C11 C10 C9 . . 118.4(2) ? C11 C10 H10 . . 120.8 ? C9 C10 H10 . . 120.8 ? N2 C11 C10 . . 122.3(2) ? N2 C11 C13 . . 116.1(3) ? C10 C11 C13 . . 121.6(3) ? C9 C12 H12A . . 109.5 ? C9 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? C9 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? C11 C13 H13A . . 109.5 ? C11 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C11 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? 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 C7 . 1.292(3) ? O1 H1 . 0.820 ? O2 C7 . 1.218(3) ? N1 C9 . 1.336(3) ? N1 C8 . 1.350(3) ? N2 C11 . 1.326(3) ? N2 C8 . 1.364(3) ? N3 C8 . 1.322(3) ? N3 H3A . 0.860 ? N3 H3B . 0.860 ? C1 C6 . 1.372(3) ? C1 C2 . 1.382(3) ? C1 C7 . 1.489(3) ? C2 C3 . 1.379(4) ? C2 H2 . 0.930 ? C3 C4 . 1.361(4) ? C3 H3 . 0.930 ? C4 C5 . 1.365(4) ? C4 H4 . 0.930 ? C5 C6 . 1.399(4) ? C5 H5 . 0.930 ? C6 H6 . 0.930 ? C9 C10 . 1.385(3) ? C9 C12 . 1.494(3) ? C10 C11 . 1.376(3) ? C10 H10 . 0.930 ? C11 C13 . 1.507(3) ? C12 H12A . 0.960 ? C12 H12B . 0.960 ? C12 H12C . 0.960 ? C13 H13A . 0.960 ? C13 H13B . 0.960 ? C13 H13C . 0.960 ? 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 O1 H1 N1 . 0.82 1.82 2.606(2) 160 N3 H3A O2 . 0.86 2.16 3.003(3) 168 N3 H3B N2 3_576 0.86 2.25 3.098(3) 169 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_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -2.1(4) ? C7 C1 C2 C3 . . . . 177.7(2) ? C1 C2 C3 C4 . . . . -0.3(4) ? C2 C3 C4 C5 . . . . 1.8(5) ? C3 C4 C5 C6 . . . . -0.9(5) ? C2 C1 C6 C5 . . . . 3.0(4) ? C7 C1 C6 C5 . . . . -176.8(2) ? C4 C5 C6 C1 . . . . -1.5(4) ? C6 C1 C7 O2 . . . . -5.3(4) ? C2 C1 C7 O2 . . . . 175.0(2) ? C6 C1 C7 O1 . . . . 174.4(2) ? C2 C1 C7 O1 . . . . -5.3(3) ? C9 N1 C8 N3 . . . . -178.84(19) ? C9 N1 C8 N2 . . . . 1.2(3) ? C11 N2 C8 N3 . . . . 178.20(19) ? C11 N2 C8 N1 . . . . -1.8(3) ? C8 N1 C9 C10 . . . . -0.1(3) ? C8 N1 C9 C12 . . . . 179.75(19) ? N1 C9 C10 C11 . . . . -0.4(3) ? C12 C9 C10 C11 . . . . 179.9(2) ? C8 N2 C11 C10 . . . . 1.4(3) ? C8 N2 C11 C13 . . . . -178.11(19) ? C9 C10 C11 N2 . . . . -0.3(4) ? C9 C10 C11 C13 . . . . 179.1(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655802