#------------------------------------------------------------------------------ #$Date: 2014-10-25 20:23:10 +0300 (Sat, 25 Oct 2014) $ #$Revision: 125873 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018300.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_2018300 loop_ _publ_author_name 'Tutughamiarso, Maya' 'Bolte, Michael' _publ_section_title ; A new polymorph and two pseudopolymorphs of pyrimethamine ; _journal_coeditor_code SK3416 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o428 _journal_page_last o434 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C12 H13 Cl N4' _chemical_formula_moiety 'C12 H13 Cl N4' _chemical_formula_sum 'C12 H13 Cl N4' _chemical_formula_weight 248.71 _chemical_name_systematic ; 2,4-diamino-5(4-chlorophenyl)-6-ethylpyrimidine ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 107.279(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.4471(18) _cell_length_b 7.5774(7) _cell_length_c 11.7526(15) _cell_measurement_reflns_used 6581 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.92 _cell_measurement_theta_min 3.25 _cell_volume 1228.5(3) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2001)' _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction 'X-AREA (Stoe & Cie, 2001)' _computing_molecular_graphics ; Mercury (Version 2.2; Macrae et al., 2008) and XP (Sheldrick, 2008) ; _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Stoe IPDS II two-circle' _diffrn_measurement_method \w _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 0.2214 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 15453 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.24 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.582 _refine_diff_density_min -0.529 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 2149 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.107 _refine_ls_R_factor_all 0.1469 _refine_ls_R_factor_gt 0.1310 _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^)+(0.1194P)^2^+7.1236P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3237 _refine_ls_wR_factor_ref 0.3333 _reflns_number_gt 1616 _reflns_number_total 2149 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL I in P2(1)/c REM Zwillingsgesetz 1 0 0.73 0 -1 0 0 0 -1 CELL 0.71073 14.4471 7.5774 11.7526 90.000 107.279 90.000 ZERR 4.00 0.0018 0.0007 0.0015 0.000 0.010 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H CL N UNIT 48 52 4 16 SIZE 0.2 0.4 0.5 REM farbloser Block ACTA MERG 0 OMIT -10 3 7 OMIT -2 1 3 OMIT 9 2 4 OMIT -1 1 1 OMIT -1 1 3 OMIT -12 0 4 SHEL 999 0.84 L.S. 10 BOND $H CONF FMAP 2 PLAN 10 TEMP -100 EQIV_$1 -x+1, y+1/2, -z+1/2 EQIV_$2 -x+1, y-1/2, -z+1/2 EQIV_$3 -x+1, -y+2, -z+1 HTAB N21 N1_$1 HTAB N21 N3_$2 HTAB N41 N3_$3 DFIX 0.88 0.02 N41 H411 N41 H412 WGHT 0.119400 7.123600 BASF 0.37837 FVAR 11.73954 N1 4 0.401122 0.534670 0.302747 11.00000 0.02199 0.02318 = 0.04073 -0.00350 0.01816 -0.00540 C2 1 0.456366 0.679655 0.319867 11.00000 0.02570 0.01963 = 0.02917 0.00148 0.00558 -0.00066 N3 4 0.449034 0.822705 0.384595 11.00000 0.02090 0.02143 = 0.03269 -0.00257 0.01071 -0.00399 C4 1 0.379744 0.817269 0.438646 11.00000 0.01538 0.02768 = 0.02590 0.00083 0.00413 0.00001 C5 1 0.316180 0.669934 0.427617 11.00000 0.01813 0.02882 = 0.02705 0.00318 0.00810 -0.00185 C6 1 0.331782 0.533005 0.358372 11.00000 0.02024 0.02751 = 0.03515 0.00375 0.00943 0.00032 N21 4 0.529302 0.684048 0.268075 11.00000 0.03260 0.02739 = 0.05224 -0.00485 0.02686 -0.00453 H211 2 0.552428 0.790627 0.254284 11.00000 -1.20000 H212 2 0.532484 0.603800 0.217628 11.00000 -1.20000 N41 4 0.369870 0.962663 0.502349 11.00000 0.03084 0.03161 = 0.03749 -0.01100 0.02138 -0.01102 H411 2 0.342587 0.940472 0.559105 11.00000 -1.20000 H412 2 0.416776 1.039223 0.530549 11.00000 -1.20000 C51 1 0.236682 0.673251 0.485107 11.00000 0.01998 0.02746 = 0.02620 -0.00060 0.00330 -0.00206 C52 1 0.241251 0.576262 0.586537 11.00000 0.04297 0.03223 = 0.03632 -0.00075 0.02114 0.00478 AFIX 43 H52 2 0.297219 0.507746 0.623308 11.00000 -1.20000 AFIX 0 C53 1 0.164303 0.578780 0.634717 11.00000 0.06150 0.03586 = 0.04048 -0.00572 0.03134 -0.01272 AFIX 43 H53 2 0.167677 0.511433 0.704014 11.00000 -1.20000 AFIX 0 C54 1 0.083739 0.677895 0.582698 11.00000 0.02875 0.06866 = 0.04580 -0.01518 0.02286 -0.02161 C55 1 0.077567 0.775775 0.483689 11.00000 0.02818 0.08720 = 0.05036 0.00387 0.01288 0.01189 AFIX 43 H55 2 0.021797 0.845527 0.448284 11.00000 -1.20000 AFIX 0 C56 1 0.154295 0.771786 0.435395 11.00000 0.02236 0.07072 = 0.03391 0.00932 0.00672 0.00816 AFIX 43 H56 2 0.149936 0.839128 0.365813 11.00000 -1.20000 AFIX 0 C61 1 0.265987 0.372680 0.331361 11.00000 0.03502 0.02444 = 0.05770 -0.00446 0.02605 -0.00927 AFIX 23 H61A 2 0.305185 0.265418 0.331663 11.00000 -1.20000 H61B 2 0.233345 0.359165 0.393953 11.00000 -1.20000 AFIX 0 C62 1 0.190575 0.391920 0.211033 11.00000 0.04096 0.04538 = 0.06459 -0.00450 0.00918 -0.02064 AFIX 33 H62A 2 0.148746 0.287392 0.194994 11.00000 -1.20000 H62B 2 0.222952 0.403620 0.149017 11.00000 -1.20000 H62C 2 0.151220 0.497202 0.211211 11.00000 -1.20000 AFIX 0 CL1 3 -0.013454 0.678589 0.642193 11.00000 0.04277 0.12847 = 0.06179 -0.03879 0.03608 -0.03710 HKLF 5 REM I in P2(1)/c REM R1 = 0.1310 for 1616 Fo > 4sig(Fo) and 0.1469 for all 2149 data REM 167 parameters refined using 2 restraints END ; _[local]_cod_data_source_file sk3416.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1228.5(2) _cod_database_code 2018300 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_symmetry_multiplicity N N1 0.4011(4) 0.5347(8) 0.3027(6) 0.0267(14) Uani d . 1 1 C C2 0.4564(5) 0.6797(9) 0.3199(7) 0.0254(15) Uani d . 1 1 N N3 0.4490(4) 0.8227(7) 0.3846(6) 0.0244(13) Uani d . 1 1 C C4 0.3797(4) 0.8173(9) 0.4386(6) 0.0234(15) Uani d . 1 1 C C5 0.3162(5) 0.6699(9) 0.4276(6) 0.0244(15) Uani d . 1 1 C C6 0.3318(5) 0.5330(10) 0.3584(7) 0.0274(16) Uani d . 1 1 N N21 0.5293(5) 0.6840(10) 0.2681(7) 0.0343(16) Uani d . 1 1 H H211 0.552(7) 0.791(14) 0.254(8) 0.041 Uiso d . 1 1 H H212 0.532(7) 0.604(14) 0.218(9) 0.041 Uiso d . 1 1 N N41 0.3699(5) 0.9627(9) 0.5023(6) 0.0309(15) Uani d D 1 1 H H411 0.343(6) 0.940(11) 0.559(6) 0.037 Uiso d D 1 1 H H412 0.417(4) 1.039(9) 0.531(8) 0.037 Uiso d D 1 1 C C51 0.2367(5) 0.6733(9) 0.4851(6) 0.0253(15) Uani d . 1 1 C C52 0.2413(6) 0.5763(11) 0.5865(7) 0.0351(19) Uani d . 1 1 H H52 0.2972 0.5077 0.6233 0.042 Uiso calc R 1 1 C C53 0.1643(7) 0.5788(12) 0.6347(8) 0.042(2) Uani d . 1 1 H H53 0.1677 0.5114 0.7040 0.051 Uiso calc R 1 1 C C54 0.0837(6) 0.6779(13) 0.5827(8) 0.045(2) Uani d . 1 1 C C55 0.0776(6) 0.7758(16) 0.4837(9) 0.055(3) Uani d . 1 1 H H55 0.0218 0.8455 0.4483 0.066 Uiso calc R 1 1 C C56 0.1543(5) 0.7718(14) 0.4354(8) 0.043(2) Uani d . 1 1 H H56 0.1499 0.8391 0.3658 0.051 Uiso calc R 1 1 C C61 0.2660(6) 0.3727(10) 0.3314(8) 0.0364(19) Uani d . 1 1 H H61A 0.3052 0.2654 0.3317 0.044 Uiso calc R 1 1 H H61B 0.2333 0.3592 0.3940 0.044 Uiso calc R 1 1 C C62 0.1906(7) 0.3919(13) 0.2110(9) 0.052(2) Uani d . 1 1 H H62A 0.1487 0.2874 0.1950 0.062 Uiso calc R 1 1 H H62B 0.2230 0.4036 0.1490 0.062 Uiso calc R 1 1 H H62C 0.1512 0.4972 0.2112 0.062 Uiso calc R 1 1 Cl Cl1 -0.01345(18) 0.6786(5) 0.6422(2) 0.0732(11) Uani d . 1 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 N1 0.022(3) 0.023(3) 0.041(4) -0.005(2) 0.018(3) -0.004(3) C2 0.026(3) 0.020(3) 0.029(4) -0.001(3) 0.006(3) 0.001(3) N3 0.021(3) 0.021(3) 0.033(3) -0.004(2) 0.011(2) -0.003(3) C4 0.015(3) 0.028(4) 0.026(4) 0.000(3) 0.004(3) 0.001(3) C5 0.018(3) 0.029(4) 0.027(4) -0.002(3) 0.008(3) 0.003(3) C6 0.020(3) 0.028(4) 0.035(4) 0.000(3) 0.009(3) 0.004(3) N21 0.033(3) 0.027(3) 0.052(4) -0.005(3) 0.027(3) -0.005(3) N41 0.031(3) 0.032(3) 0.037(4) -0.011(3) 0.021(3) -0.011(3) C51 0.020(3) 0.027(4) 0.026(4) -0.002(3) 0.003(3) -0.001(3) C52 0.043(4) 0.032(4) 0.036(5) 0.005(3) 0.021(4) -0.001(3) C53 0.061(6) 0.036(5) 0.040(5) -0.013(4) 0.031(4) -0.006(4) C54 0.029(4) 0.069(6) 0.046(5) -0.022(4) 0.023(4) -0.015(5) C55 0.028(4) 0.087(8) 0.050(6) 0.012(5) 0.013(4) 0.004(5) C56 0.022(4) 0.071(6) 0.034(5) 0.008(4) 0.007(3) 0.009(4) C61 0.035(4) 0.024(4) 0.058(6) -0.009(3) 0.026(4) -0.004(4) C62 0.041(5) 0.045(5) 0.065(7) -0.021(4) 0.009(5) -0.004(5) Cl1 0.0428(13) 0.128(3) 0.0618(17) -0.0371(15) 0.0361(12) -0.0388(17) 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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C6 115.5(6) N1 C2 N3 127.1(6) N1 C2 N21 117.3(7) N3 C2 N21 115.7(7) C4 N3 C2 116.1(6) N3 C4 N41 116.8(6) N3 C4 C5 122.3(6) N41 C4 C5 120.8(6) C6 C5 C4 115.4(6) C6 C5 C51 124.2(6) C4 C5 C51 120.4(6) N1 C6 C5 123.7(7) N1 C6 C61 114.5(7) C5 C6 C61 121.6(6) C2 N21 H211 118(6) C2 N21 H212 120(6) H211 N21 H212 114(9) C4 N41 H411 114(6) C4 N41 H412 123(6) H411 N41 H412 108(8) C56 C51 C52 117.8(7) C56 C51 C5 120.0(7) C52 C51 C5 122.2(7) C51 C52 C53 120.3(8) C51 C52 H52 119.9 C53 C52 H52 119.9 C54 C53 C52 120.2(8) C54 C53 H53 119.9 C52 C53 H53 119.9 C55 C54 C53 120.8(8) C55 C54 Cl1 119.0(8) C53 C54 Cl1 120.1(7) C54 C55 C56 118.7(9) C54 C55 H55 120.6 C56 C55 H55 120.6 C51 C56 C55 122.2(9) C51 C56 H56 118.9 C55 C56 H56 118.9 C62 C61 C6 110.5(7) C62 C61 H61A 109.5 C6 C61 H61A 109.5 C62 C61 H61B 109.5 C6 C61 H61B 109.5 H61A C61 H61B 108.1 C61 C62 H62A 109.5 C61 C62 H62B 109.5 H62A C62 H62B 109.5 C61 C62 H62C 109.5 H62A C62 H62C 109.5 H62B C62 H62C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.338(9) N1 C6 1.349(9) C2 N3 1.346(9) C2 N21 1.365(10) N3 C4 1.336(9) C4 N41 1.363(9) C4 C5 1.427(10) C5 C6 1.378(10) C5 C51 1.496(10) C6 C61 1.517(10) N21 H211 0.91(11) N21 H212 0.86(10) N41 H411 0.89(2) N41 H412 0.88(2) C51 C56 1.379(11) C51 C52 1.385(11) C52 C53 1.390(11) C52 H52 0.9500 C53 C54 1.367(14) C53 H53 0.9500 C54 C55 1.360(14) C54 Cl1 1.745(8) C55 C56 1.388(12) C55 H55 0.9500 C56 H56 0.9500 C61 C62 1.514(13) C61 H61A 0.9900 C61 H61B 0.9900 C62 H62A 0.9800 C62 H62B 0.9800 C62 H62C 0.9800 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 N21 H211 N1 2_655 0.91(11) 2.14(11) 3.043(10) 172(8) N21 H212 N3 2_645 0.86(10) 2.50(11) 3.339(10) 166(8) N41 H412 N3 3_676 0.88(2) 2.17(3) 3.032(8) 167(8) 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 N3 -1.0(11) C6 N1 C2 N21 178.0(7) N1 C2 N3 C4 1.0(11) N21 C2 N3 C4 -178.0(7) C2 N3 C4 N41 -178.6(6) C2 N3 C4 C5 -0.8(10) N3 C4 C5 C6 0.6(10) N41 C4 C5 C6 178.3(7) N3 C4 C5 C51 -177.1(7) N41 C4 C5 C51 0.6(10) C2 N1 C6 C5 0.7(11) C2 N1 C6 C61 176.3(7) C4 C5 C6 N1 -0.6(11) C51 C5 C6 N1 177.0(7) C4 C5 C6 C61 -175.8(7) C51 C5 C6 C61 1.8(12) C6 C5 C51 C56 -102.0(10) C4 C5 C51 C56 75.5(10) C6 C5 C51 C52 76.4(10) C4 C5 C51 C52 -106.1(9) C56 C51 C52 C53 0.5(12) C5 C51 C52 C53 -177.9(8) C51 C52 C53 C54 -0.4(13) C52 C53 C54 C55 -0.2(14) C52 C53 C54 Cl1 179.2(7) C53 C54 C55 C56 0.7(15) Cl1 C54 C55 C56 -178.7(8) C52 C51 C56 C55 0.0(14) C5 C51 C56 C55 178.4(9) C54 C55 C56 C51 -0.6(16) N1 C6 C61 C62 -78.7(9) C5 C6 C61 C62 97.0(9) _cod_database_fobs_code 2018300 _journal_paper_doi 10.1107/S0108270111038868