#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012084.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_2012084 loop_ _publ_author_name 'Daniel E. Lynch' 'Ian McClenaghan' _publ_section_title ; 2-Amino-4-(4-pyridyl)pyrimidine and the 1:1 adduct with 4-aminobenzoic acid ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 830 _journal_page_last 832 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C9 H8 N4' _chemical_formula_sum 'C9 H8 N4' _chemical_formula_weight 172.19 _chemical_melting_point 354.5(15) _chemical_name_systematic ; 2-Amino-4-(pyrid-4-yl)pyrimidine ; _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 _cell_angle_beta 103.35(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.450(2) _cell_length_b 13.689(3) _cell_length_c 6.4390(10) _cell_measurement_reflns_used 3577 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 47.8 _cell_measurement_theta_min 2.9 _cell_volume 810.4(3) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON97 (Spek, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .04 _diffrn_reflns_av_sigmaI/netI .044 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6415 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.0 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .092 _exptl_absorpt_correction_T_max .989 _exptl_absorpt_correction_T_min .976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_size_max .27 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .12 _refine_diff_density_max .25 _refine_diff_density_min -.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 1841 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all .065 _refine_ls_R_factor_gt .047 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.0128P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .132 _reflns_number_gt 1417 _reflns_number_total 1841 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gg1041.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '353-356 K' was changed to '354.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '353-356 K' was changed to '354.5(15)' - the average value was taken and precision was estimated. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012084 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 -.24503(12) .86156(8) -.25879(16) .0263(3) Uani d . 1 . . N C2 -.14313(14) .90228(9) -.35034(18) .0229(3) Uani d . 1 . . C N21 -.18924(13) .93476(9) -.55106(16) .0287(3) Uani d . 1 . . N H21 -.283(2) .9241(11) -.627(2) .040(4) Uiso d . 1 . . H H22 -.1250(18) .9663(11) -.615(2) .045(4) Uiso d . 1 . . H N3 -.00036(11) .91179(7) -.25774(15) .0227(3) Uani d . 1 . . N C4 .04501(14) .87496(8) -.06011(19) .0218(3) Uani d . 1 . . C C5 -.05131(14) .83165(9) .04571(19) .0265(3) Uani d . 1 . . C H5 -.0194 .8060 .1859 .033 Uiso calc R 1 . . H C6 -.19526(14) .82755(9) -.0619(2) .0272(3) Uani d . 1 . . C H6 -.2628 .7988 .0085 .034 Uiso calc R 1 . . H C7 .20356(15) .87872(9) .03404(19) .0232(3) Uani d . 1 . . C C8 .26123(16) .87555(10) .2533(2) .0302(3) Uani d . 1 . . C H8 .1988 .8711 .3492 .038 Uiso calc R 1 . . H C9 .41009(17) .87887(10) .3299(2) .0353(4) Uani d . 1 . . C H9 .4472 .8772 .4801 .044 Uiso calc R 1 . . H N10 .50522(13) .88427(9) .20589(19) .0350(3) Uani d . 1 . . N C11 .44911(16) .88593(10) -.0045(2) .0332(4) Uani d . 1 . . C H10 .5144 .8892 -.0965 .042 Uiso calc R 1 . . H C12 .30230(15) .88321(10) -.0957(2) .0286(3) Uani d . 1 . . C H12 .2686 .8844 -.2466 .036 Uiso calc R 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 .0204(6) .0303(6) .0285(6) .0002(4) .0061(4) .0022(4) C2 .0215(7) .0232(6) .0236(6) .0005(5) .0040(5) -.0017(5) N21 .0210(7) .0398(7) .0230(5) -.0022(5) .0002(5) .0041(5) N3 .0215(6) .0249(6) .0209(5) -.0005(4) .0031(4) .0001(4) C4 .0229(7) .0210(6) .0212(6) .0010(5) .0041(5) -.0018(4) C5 .0265(8) .0292(7) .0232(6) .0019(5) .0049(5) .0039(5) C6 .0250(8) .0288(7) .0294(7) .0005(5) .0093(5) .0042(5) C7 .0236(7) .0213(6) .0229(6) .0001(5) .0018(5) .0011(5) C8 .0281(8) .0376(8) .0236(6) -.0019(6) .0034(5) .0002(5) C9 .0330(9) .0451(9) .0237(7) -.0033(6) -.0018(6) .0014(6) N10 .0238(7) .0460(7) .0312(6) -.0010(5) -.0019(5) .0056(5) C11 .0228(8) .0445(8) .0309(7) .0034(6) .0034(6) .0057(6) C12 .0255(8) .0364(8) .0226(6) .0021(6) .0029(5) .0042(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 N1 C6 . 1.3303(16) ? N1 C2 . 1.3592(16) ? C2 N21 . 1.3408(15) ? C2 N3 . 1.3496(17) ? N21 H21 . .919(18) ? N21 H22 . .917(16) ? N3 C4 . 1.3436(16) ? C4 C5 . 1.3895(17) ? C4 C7 . 1.482(2) ? C5 C6 . 1.3779(19) ? C5 H5 . .95 ? C6 H6 . .95 ? C7 C12 . 1.3899(19) ? C7 C8 . 1.3914(17) ? C8 C9 . 1.380(2) ? C8 H8 . .95 ? C9 N10 . 1.3349(18) ? C9 H9 . .95 ? N10 C11 . 1.3358(18) ? C11 C12 . 1.377(2) ? C11 H10 . .95 ? C12 H12 . .95 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 '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 C6 N1 C2 115.26(11) N21 C2 N3 117.59(11) N21 C2 N1 116.67(12) N3 C2 N1 125.74(11) C2 N21 H21 121.4(9) C2 N21 H22 119.3(10) H21 N21 H22 119.3(13) C4 N3 C2 116.75(11) N3 C4 C5 121.50(12) N3 C4 C7 116.48(11) C5 C4 C7 121.96(11) C6 C5 C4 116.95(11) C6 C5 H5 121.5 C4 C5 H5 121.5 N1 C6 C5 123.77(11) N1 C6 H6 118.1 C5 C6 H6 118.1 C12 C7 C8 116.80(13) C12 C7 C4 120.76(11) C8 C7 C4 122.43(12) C9 C8 C7 119.33(13) C9 C8 H8 120.3 C7 C8 H8 120.3 N10 C9 C8 124.04(12) N10 C9 H9 118.0 C8 C9 H9 118.0 C9 N10 C11 116.27(13) N10 C11 C12 123.86(13) N10 C11 H10 118.1 C12 C11 H10 118.1 C11 C12 C7 119.68(12) C11 C12 H12 120.2 C7 C12 H12 120.2 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 N21 H22 N3 3_574 .917(16) 2.303(17) 3.1870(17) 161.7(13) yes N21 H21 N10 1_454 .919(18) 2.114(19) 3.0295(19) 174.1(14) 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 C6 N1 C2 N21 178.18(11) C6 N1 C2 N3 -1.11(19) N21 C2 N3 C4 -177.15(11) N1 C2 N3 C4 2.13(18) C2 N3 C4 C5 -1.73(17) C2 N3 C4 C7 175.40(9) N3 C4 C5 C6 .47(17) C7 C4 C5 C6 -176.50(11) C2 N1 C6 C5 -.34(19) C4 C5 C6 N1 .63(19) N3 C4 C7 C12 -24.13(16) C5 C4 C7 C12 152.98(12) N3 C4 C7 C8 157.49(12) C5 C4 C7 C8 -25.40(17) C12 C7 C8 C9 1.23(18) C4 C7 C8 C9 179.68(11) C7 C8 C9 N10 -.6(2) C8 C9 N10 C11 -.3(2) C9 N10 C11 C12 .5(2) N10 C11 C12 C7 .2(2) C8 C7 C12 C11 -1.06(19) C4 C7 C12 C11 -179.53(11)