# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_wj1075 _database_code_depnum_ccdc_archive 'CCDC 885645' #TrackingRef 'Pyrimethamine + carbamazepine+ methanol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethamine+carbamazepine+methanol _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O, C12 H13 Cl N4, 2(C H4 O)' _chemical_formula_sum 'C29 H33 Cl N6 O3' _chemical_formula_weight 549.06 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.96900(10) _cell_length_b 10.11220(10) _cell_length_c 17.9406(3) _cell_angle_alpha 92.9360(10) _cell_angle_beta 94.1630(10) _cell_angle_gamma 106.0620(10) _cell_volume 1381.78(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9187 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description 'Rectangular blocks' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 27354 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 32.07 _reflns_number_total 9577 _reflns_number_gt 6783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.6298P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9577 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1280(3) 0.0405(2) 0.10685(13) 0.0550(5) Uani 1 1 d . . . H53A H 0.0958 -0.0028 0.0558 0.066 Uiso 1 1 calc R . . H53B H 0.1534 -0.0267 0.1402 0.066 Uiso 1 1 calc R . . H53C H 0.2323 0.1196 0.1073 0.066 Uiso 1 1 calc R . . C2 C 0.2025(3) 0.1790(4) 0.32850(14) 0.0871(10) Uani 1 1 d . . . H52A H 0.3039 0.1822 0.3001 0.105 Uiso 1 1 calc R . . H52B H 0.2100 0.1279 0.3730 0.105 Uiso 1 1 calc R . . H52C H 0.2018 0.2732 0.3440 0.105 Uiso 1 1 calc R . . C3 C 0.3031(3) 0.4277(2) 0.18501(11) 0.0564(6) Uani 1 1 d . . . H1A H 0.3028 0.3389 0.2045 0.085 Uiso 1 1 calc R . . H1B H 0.1820 0.4314 0.1747 0.085 Uiso 1 1 calc R . . H1C H 0.3656 0.5028 0.2222 0.085 Uiso 1 1 calc R . . C4 C 0.3938(2) 0.44346(16) 0.11345(9) 0.0353(3) Uani 1 1 d . . . H4A H 0.5167 0.4418 0.1243 0.042 Uiso 1 1 calc R . . H4B H 0.3345 0.3645 0.0770 0.042 Uiso 1 1 calc R . . C5 C 0.39182(18) 0.57609(14) 0.07913(7) 0.0252(3) Uani 1 1 d . . . C6 C 0.24072(18) 0.68650(14) 0.00232(7) 0.0233(3) Uani 1 1 d . . . C7 C 0.51353(17) 0.81073(14) 0.05467(7) 0.0229(3) Uani 1 1 d . . . C8 C 0.53002(18) 0.69448(14) 0.09275(7) 0.0229(2) Uani 1 1 d . . . C9 C 0.69165(18) 0.70379(14) 0.14277(7) 0.0234(3) Uani 1 1 d . . . C10 C 0.7098(2) 0.75755(19) 0.21679(8) 0.0340(3) Uani 1 1 d . . . H3A H 0.6159 0.7851 0.2362 0.041 Uiso 1 1 calc R . . C11 C 0.8630(2) 0.77181(19) 0.26313(8) 0.0349(3) Uani 1 1 d . . . H2A H 0.8746 0.8098 0.3134 0.042 Uiso 1 1 calc R . . C12 C 0.99720(18) 0.72978(15) 0.23465(8) 0.0260(3) Uani 1 1 d . . . C13 C 0.9827(2) 0.67473(18) 0.16182(8) 0.0339(3) Uani 1 1 d . . . H6A H 1.0761 0.6456 0.1430 0.041 Uiso 1 1 calc R . . C14 C 0.8298(2) 0.66245(18) 0.11626(8) 0.0324(3) Uani 1 1 d . . . H5A H 0.8197 0.6250 0.0659 0.039 Uiso 1 1 calc R . . C15 C 0.3237(3) 0.5155(2) 0.45415(11) 0.0475(5) Uani 1 1 d . . . H21A H 0.2701 0.4188 0.4475 0.057 Uiso 1 1 calc R . . C16 C 0.4470(3) 0.5769(2) 0.40689(10) 0.0516(5) Uani 1 1 d . . . H22A H 0.4763 0.5224 0.3679 0.062 Uiso 1 1 calc R . . C17 C 0.5279(3) 0.7168(2) 0.41613(9) 0.0454(5) Uani 1 1 d . . . H25A H 0.6164 0.7580 0.3850 0.055 Uiso 1 1 calc R . . C18 C 0.4797(2) 0.79695(19) 0.47083(9) 0.0351(3) Uani 1 1 d . . . H31A H 0.5347 0.8935 0.4771 0.042 Uiso 1 1 calc R . . C19 C 0.35046(18) 0.73601(16) 0.51672(8) 0.0273(3) Uani 1 1 d . . . C20 C 0.32138(19) 0.81502(16) 0.64613(8) 0.0280(3) Uani 1 1 d . . . C21 C 0.4199(2) 0.93110(18) 0.68971(9) 0.0356(3) Uani 1 1 d . . . H28A H 0.4703 1.0138 0.6668 0.043 Uiso 1 1 calc R . . C22 C 0.4454(3) 0.9272(2) 0.76690(9) 0.0441(4) Uani 1 1 d . . . H24A H 0.5136 1.0069 0.7967 0.053 Uiso 1 1 calc R . . C23 C 0.3717(3) 0.8073(2) 0.80022(9) 0.0453(4) Uani 1 1 d . . . H23A H 0.3883 0.8048 0.8530 0.054 Uiso 1 1 calc R . . C24 C 0.2744(2) 0.6918(2) 0.75713(10) 0.0422(4) Uani 1 1 d . . . H29A H 0.2238 0.6101 0.7808 0.051 Uiso 1 1 calc R . . C25 C 0.2476(2) 0.69139(18) 0.67852(9) 0.0330(3) Uani 1 1 d . . . C26 C 0.1456(2) 0.56542(19) 0.63561(10) 0.0409(4) Uani 1 1 d . . . H27A H 0.0591 0.5051 0.6613 0.049 Uiso 1 1 calc R . . C27 C 0.1569(2) 0.52266(18) 0.56461(11) 0.0412(4) Uani 1 1 d . . . H26A H 0.0780 0.4362 0.5466 0.049 Uiso 1 1 calc R . . C28 C 0.2759(2) 0.59315(17) 0.51174(9) 0.0337(3) Uani 1 1 d . . . C29 C 0.17221(18) 0.89336(16) 0.54210(8) 0.0262(3) Uani 1 1 d . . . N1 N 0.12641(18) 0.88310(15) 0.46791(7) 0.0353(3) Uani 1 1 d . . . H35A H 0.0547 0.9282 0.4497 0.042 Uiso 1 1 calc R . . H35B H 0.1682 0.8312 0.4376 0.042 Uiso 1 1 calc R . . N2 N 0.28741(16) 0.82229(13) 0.56694(6) 0.0266(2) Uani 1 1 d . . . N3 N 0.64177(16) 0.93000(13) 0.06205(7) 0.0312(3) Uani 1 1 d . . . H10A H 0.6296 1.0006 0.0377 0.037 Uiso 1 1 calc R . . H10B H 0.7381 0.9376 0.0912 0.037 Uiso 1 1 calc R . . N4 N 0.09503(16) 0.68064(14) -0.04282(7) 0.0315(3) Uani 1 1 d . . . H12A H 0.0873 0.7533 -0.0663 0.038 Uiso 1 1 calc R . . H12B H 0.0079 0.6042 -0.0487 0.038 Uiso 1 1 calc R . . N5 N 0.24369(15) 0.57047(12) 0.03540(6) 0.0257(2) Uani 1 1 d . . . N6 N 0.36950(15) 0.80604(12) 0.00910(6) 0.0244(2) Uani 1 1 d . . . O1 O -0.01213(16) 0.08582(14) 0.13184(7) 0.0428(3) Uani 1 1 d . . . H54 H 0.004(3) 0.095(2) 0.1770(14) 0.051 Uiso 1 1 d . . . O2 O 0.0587(2) 0.1174(3) 0.28651(8) 0.0799(6) Uani 1 1 d . . . H51 H -0.019(4) 0.086(3) 0.3102(19) 0.096 Uiso 1 1 d . . . O3 O 0.11627(15) 0.96525(13) 0.58653(6) 0.0345(3) Uani 1 1 d . . . Cl1 Cl 1.19012(5) 0.74519(5) 0.29178(2) 0.03731(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0455(11) 0.0580(13) 0.0594(12) 0.0058(10) 0.0033(9) 0.0114(10) C2 0.0562(14) 0.127(3) 0.0520(13) 0.0309(15) -0.0017(11) -0.0198(15) C3 0.0811(15) 0.0450(11) 0.0416(10) 0.0227(8) 0.0038(10) 0.0119(11) C4 0.0376(8) 0.0247(7) 0.0403(8) 0.0093(6) -0.0079(6) 0.0053(6) C5 0.0285(6) 0.0226(6) 0.0235(6) 0.0038(5) -0.0013(5) 0.0063(5) C6 0.0240(6) 0.0243(6) 0.0203(5) 0.0037(5) 0.0003(4) 0.0049(5) C7 0.0240(6) 0.0241(6) 0.0194(5) 0.0032(4) 0.0005(4) 0.0049(5) C8 0.0250(6) 0.0228(6) 0.0206(5) 0.0025(5) -0.0018(4) 0.0070(5) C9 0.0260(6) 0.0212(6) 0.0219(6) 0.0033(5) -0.0019(5) 0.0059(5) C10 0.0305(7) 0.0512(10) 0.0241(6) -0.0035(6) -0.0015(5) 0.0198(7) C11 0.0335(8) 0.0510(10) 0.0214(6) -0.0045(6) -0.0030(5) 0.0164(7) C12 0.0237(6) 0.0279(7) 0.0253(6) 0.0037(5) -0.0024(5) 0.0062(5) C13 0.0295(7) 0.0466(9) 0.0287(7) -0.0025(6) -0.0005(5) 0.0174(7) C14 0.0334(7) 0.0427(9) 0.0225(6) -0.0044(6) -0.0025(5) 0.0151(7) C15 0.0613(12) 0.0444(10) 0.0419(9) -0.0061(8) -0.0156(8) 0.0299(9) C16 0.0657(13) 0.0729(15) 0.0320(8) -0.0052(8) -0.0060(8) 0.0499(12) C17 0.0432(9) 0.0749(14) 0.0304(8) 0.0084(8) 0.0060(7) 0.0353(10) C18 0.0308(7) 0.0466(10) 0.0310(7) 0.0079(6) 0.0035(6) 0.0150(7) C19 0.0252(6) 0.0345(8) 0.0253(6) 0.0050(5) -0.0009(5) 0.0135(6) C20 0.0270(6) 0.0370(8) 0.0238(6) 0.0102(5) 0.0027(5) 0.0136(6) C21 0.0434(9) 0.0372(9) 0.0284(7) 0.0074(6) -0.0008(6) 0.0151(7) C22 0.0572(11) 0.0495(11) 0.0294(8) 0.0024(7) -0.0059(7) 0.0238(9) C23 0.0547(11) 0.0640(12) 0.0255(7) 0.0125(7) 0.0025(7) 0.0292(10) C24 0.0431(9) 0.0564(11) 0.0335(8) 0.0246(8) 0.0075(7) 0.0199(8) C25 0.0273(7) 0.0428(9) 0.0319(7) 0.0160(6) 0.0034(5) 0.0123(6) C26 0.0318(8) 0.0414(9) 0.0468(9) 0.0219(7) 0.0001(7) 0.0033(7) C27 0.0372(8) 0.0310(8) 0.0500(10) 0.0101(7) -0.0105(7) 0.0029(7) C28 0.0338(7) 0.0347(8) 0.0338(7) 0.0036(6) -0.0089(6) 0.0147(6) C29 0.0241(6) 0.0321(7) 0.0243(6) 0.0089(5) 0.0028(5) 0.0094(5) N1 0.0422(7) 0.0484(8) 0.0236(6) 0.0042(5) -0.0015(5) 0.0272(7) N2 0.0283(6) 0.0318(6) 0.0231(5) 0.0083(4) 0.0022(4) 0.0128(5) N3 0.0273(6) 0.0265(6) 0.0344(6) 0.0103(5) -0.0090(5) 0.0001(5) N4 0.0266(6) 0.0290(6) 0.0341(6) 0.0102(5) -0.0082(5) 0.0013(5) N5 0.0265(6) 0.0224(6) 0.0258(5) 0.0044(4) -0.0023(4) 0.0038(4) N6 0.0242(5) 0.0242(6) 0.0223(5) 0.0055(4) -0.0028(4) 0.0030(4) O1 0.0352(6) 0.0550(8) 0.0351(6) 0.0063(6) -0.0057(5) 0.0090(6) O2 0.0480(9) 0.1444(19) 0.0333(7) 0.0099(9) 0.0070(6) 0.0024(10) O3 0.0375(6) 0.0497(7) 0.0248(5) 0.0077(4) 0.0050(4) 0.0250(5) Cl1 0.02718(17) 0.0507(2) 0.03209(18) 0.00107(16) -0.00708(13) 0.01055(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.412(3) . ? C1 H53A 0.9800 . ? C1 H53B 0.9800 . ? C1 H53C 0.9800 . ? C2 O2 1.304(3) . ? C2 H52A 0.9800 . ? C2 H52B 0.9800 . ? C2 H52C 0.9800 . ? C3 C4 1.513(3) . ? C3 H1A 0.9800 . ? C3 H1B 0.9800 . ? C3 H1C 0.9800 . ? C4 C5 1.507(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N5 1.3550(17) . ? C5 C8 1.3810(19) . ? C6 N6 1.3452(17) . ? C6 N5 1.3469(17) . ? C6 N4 1.3520(17) . ? C7 N3 1.3410(18) . ? C7 N6 1.3483(16) . ? C7 C8 1.4215(18) . ? C8 C9 1.4931(18) . ? C9 C14 1.387(2) . ? C9 C10 1.3909(19) . ? C10 C11 1.395(2) . ? C10 H3A 0.9500 . ? C11 C12 1.376(2) . ? C11 H2A 0.9500 . ? C12 C13 1.378(2) . ? C12 Cl1 1.7495(14) . ? C13 C14 1.389(2) . ? C13 H6A 0.9500 . ? C14 H5A 0.9500 . ? C15 C16 1.381(3) . ? C15 C28 1.403(3) . ? C15 H21A 0.9500 . ? C16 C17 1.379(3) . ? C16 H22A 0.9500 . ? C17 C18 1.383(2) . ? C17 H25A 0.9500 . ? C18 C19 1.394(2) . ? C18 H31A 0.9500 . ? C19 C28 1.397(2) . ? C19 N2 1.4329(19) . ? C20 C21 1.383(2) . ? C20 C25 1.401(2) . ? C20 N2 1.4363(17) . ? C21 C22 1.389(2) . ? C21 H28A 0.9500 . ? C22 C23 1.379(3) . ? C22 H24A 0.9500 . ? C23 C24 1.372(3) . ? C23 H23A 0.9500 . ? C24 C25 1.411(2) . ? C24 H29A 0.9500 . ? C25 C26 1.453(3) . ? C26 C27 1.341(3) . ? C26 H27A 0.9500 . ? C27 C28 1.461(3) . ? C27 H26A 0.9500 . ? C29 O3 1.2385(18) . ? C29 N1 1.3454(18) . ? C29 N2 1.3771(18) . ? N1 H35A 0.8800 . ? N1 H35B 0.8800 . ? N3 H10A 0.8800 . ? N3 H10B 0.8800 . ? N4 H12A 0.8800 . ? N4 H12B 0.8800 . ? O1 H54 0.81(2) . ? O2 H51 0.78(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H53A 109.5 . . ? O1 C1 H53B 109.5 . . ? H53A C1 H53B 109.5 . . ? O1 C1 H53C 109.5 . . ? H53A C1 H53C 109.5 . . ? H53B C1 H53C 109.5 . . ? O2 C2 H52A 109.5 . . ? O2 C2 H52B 109.5 . . ? H52A C2 H52B 109.5 . . ? O2 C2 H52C 109.5 . . ? H52A C2 H52C 109.5 . . ? H52B C2 H52C 109.5 . . ? C4 C3 H1A 109.5 . . ? C4 C3 H1B 109.5 . . ? H1A C3 H1B 109.5 . . ? C4 C3 H1C 109.5 . . ? H1A C3 H1C 109.5 . . ? H1B C3 H1C 109.5 . . ? C5 C4 C3 111.86(15) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N5 C5 C8 122.99(12) . . ? N5 C5 C4 114.94(12) . . ? C8 C5 C4 122.06(12) . . ? N6 C6 N5 126.21(12) . . ? N6 C6 N4 117.34(12) . . ? N5 C6 N4 116.43(12) . . ? N3 C7 N6 116.95(12) . . ? N3 C7 C8 121.31(12) . . ? N6 C7 C8 121.74(12) . . ? C5 C8 C7 116.15(12) . . ? C5 C8 C9 123.71(12) . . ? C7 C8 C9 120.13(12) . . ? C14 C9 C10 118.07(13) . . ? C14 C9 C8 121.01(12) . . ? C10 C9 C8 120.90(13) . . ? C9 C10 C11 121.38(14) . . ? C9 C10 H3A 119.3 . . ? C11 C10 H3A 119.3 . . ? C12 C11 C10 118.74(13) . . ? C12 C11 H2A 120.6 . . ? C10 C11 H2A 120.6 . . ? C11 C12 C13 121.35(13) . . ? C11 C12 Cl1 119.68(11) . . ? C13 C12 Cl1 118.97(11) . . ? C12 C13 C14 119.14(14) . . ? C12 C13 H6A 120.4 . . ? C14 C13 H6A 120.4 . . ? C9 C14 C13 121.32(13) . . ? C9 C14 H5A 119.3 . . ? C13 C14 H5A 119.3 . . ? C16 C15 C28 121.33(19) . . ? C16 C15 H21A 119.3 . . ? C28 C15 H21A 119.3 . . ? C17 C16 C15 120.24(17) . . ? C17 C16 H22A 119.9 . . ? C15 C16 H22A 119.9 . . ? C16 C17 C18 119.85(18) . . ? C16 C17 H25A 120.1 . . ? C18 C17 H25A 120.1 . . ? C17 C18 C19 119.95(18) . . ? C17 C18 H31A 120.0 . . ? C19 C18 H31A 120.0 . . ? C18 C19 C28 120.98(15) . . ? C18 C19 N2 119.19(14) . . ? C28 C19 N2 119.76(13) . . ? C21 C20 C25 120.96(14) . . ? C21 C20 N2 119.77(13) . . ? C25 C20 N2 119.22(14) . . ? C20 C21 C22 120.18(16) . . ? C20 C21 H28A 119.9 . . ? C22 C21 H28A 119.9 . . ? C23 C22 C21 119.94(18) . . ? C23 C22 H24A 120.0 . . ? C21 C22 H24A 120.0 . . ? C24 C23 C22 120.03(15) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C25 121.65(16) . . ? C23 C24 H29A 119.2 . . ? C25 C24 H29A 119.2 . . ? C20 C25 C24 117.22(16) . . ? C20 C25 C26 123.52(14) . . ? C24 C25 C26 119.26(15) . . ? C27 C26 C25 128.84(16) . . ? C27 C26 H27A 115.6 . . ? C25 C26 H27A 115.6 . . ? C26 C27 C28 127.79(16) . . ? C26 C27 H26A 116.1 . . ? C28 C27 H26A 116.1 . . ? C19 C28 C15 117.38(17) . . ? C19 C28 C27 123.08(15) . . ? C15 C28 C27 119.52(17) . . ? O3 C29 N1 121.93(13) . . ? O3 C29 N2 120.89(12) . . ? N1 C29 N2 117.17(13) . . ? C29 N1 H35A 120.0 . . ? C29 N1 H35B 120.0 . . ? H35A N1 H35B 120.0 . . ? C29 N2 C19 121.76(11) . . ? C29 N2 C20 118.96(12) . . ? C19 N2 C20 118.38(11) . . ? C7 N3 H10A 120.0 . . ? C7 N3 H10B 120.0 . . ? H10A N3 H10B 120.0 . . ? C6 N4 H12A 120.0 . . ? C6 N4 H12B 120.0 . . ? H12A N4 H12B 120.0 . . ? C6 N5 C5 116.11(12) . . ? C6 N6 C7 116.71(11) . . ? C1 O1 H54 106.1(17) . . ? C2 O2 H51 112(2) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C4 C5 N5 -84.03(18) . . . . ? C3 C4 C5 C8 94.83(19) . . . . ? N5 C5 C8 C7 -3.4(2) . . . . ? C4 C5 C8 C7 177.83(14) . . . . ? N5 C5 C8 C9 177.92(13) . . . . ? C4 C5 C8 C9 -0.9(2) . . . . ? N3 C7 C8 C5 -178.15(14) . . . . ? N6 C7 C8 C5 1.3(2) . . . . ? N3 C7 C8 C9 0.6(2) . . . . ? N6 C7 C8 C9 180.00(13) . . . . ? C5 C8 C9 C14 84.29(19) . . . . ? C7 C8 C9 C14 -94.35(17) . . . . ? C5 C8 C9 C10 -97.40(18) . . . . ? C7 C8 C9 C10 83.96(18) . . . . ? C14 C9 C10 C11 0.9(2) . . . . ? C8 C9 C10 C11 -177.41(15) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C10 C11 C12 Cl1 -179.48(13) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? Cl1 C12 C13 C14 -179.94(13) . . . . ? C10 C9 C14 C13 -0.3(2) . . . . ? C8 C9 C14 C13 178.01(15) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C28 C15 C16 C17 0.8(3) . . . . ? C15 C16 C17 C18 -2.8(3) . . . . ? C16 C17 C18 C19 0.4(2) . . . . ? C17 C18 C19 C28 4.2(2) . . . . ? C17 C18 C19 N2 -172.64(13) . . . . ? C25 C20 C21 C22 -0.8(2) . . . . ? N2 C20 C21 C22 176.46(15) . . . . ? C20 C21 C22 C23 -0.3(3) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? C21 C20 C25 C24 1.6(2) . . . . ? N2 C20 C25 C24 -175.71(14) . . . . ? C21 C20 C25 C26 -178.83(16) . . . . ? N2 C20 C25 C26 3.9(2) . . . . ? C23 C24 C25 C20 -1.4(2) . . . . ? C23 C24 C25 C26 179.05(17) . . . . ? C20 C25 C26 C27 28.8(3) . . . . ? C24 C25 C26 C27 -151.66(19) . . . . ? C25 C26 C27 C28 -0.2(3) . . . . ? C18 C19 C28 C15 -6.1(2) . . . . ? N2 C19 C28 C15 170.74(13) . . . . ? C18 C19 C28 C27 171.98(14) . . . . ? N2 C19 C28 C27 -11.2(2) . . . . ? C16 C15 C28 C19 3.6(2) . . . . ? C16 C15 C28 C27 -174.50(16) . . . . ? C26 C27 C28 C19 -24.8(3) . . . . ? C26 C27 C28 C15 153.16(18) . . . . ? O3 C29 N2 C19 178.51(14) . . . . ? N1 C29 N2 C19 -2.7(2) . . . . ? O3 C29 N2 C20 9.5(2) . . . . ? N1 C29 N2 C20 -171.66(14) . . . . ? C18 C19 N2 C29 76.54(18) . . . . ? C28 C19 N2 C29 -100.31(16) . . . . ? C18 C19 N2 C20 -114.41(15) . . . . ? C28 C19 N2 C20 68.74(17) . . . . ? C21 C20 N2 C29 -71.89(19) . . . . ? C25 C20 N2 C29 105.44(17) . . . . ? C21 C20 N2 C19 118.74(16) . . . . ? C25 C20 N2 C19 -63.92(18) . . . . ? N6 C6 N5 C5 -0.4(2) . . . . ? N4 C6 N5 C5 178.48(13) . . . . ? C8 C5 N5 C6 3.0(2) . . . . ? C4 C5 N5 C6 -178.14(13) . . . . ? N5 C6 N6 C7 -1.5(2) . . . . ? N4 C6 N6 C7 179.57(13) . . . . ? N3 C7 N6 C6 -179.53(13) . . . . ? C8 C7 N6 C6 1.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.07 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.586 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.057 data_wj1064 _database_code_depnum_ccdc_archive 'CCDC 885646' #TrackingRef 'Pyrimethamine + theophylline.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethamine+theophylline _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 Cl N4, C7 H8 N4 O2' _chemical_formula_sum 'C19 H21 Cl N8 O2' _chemical_formula_weight 428.89 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9789(4) _cell_length_b 10.3092(5) _cell_length_c 13.6586(7) _cell_angle_alpha 68.186(3) _cell_angle_beta 87.884(2) _cell_angle_gamma 75.726(3) _cell_volume 1008.98(9) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 37113 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'multi-scan from symmetry-related measurements Sortav (Blessing 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14534 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5624 _reflns_number_gt 4183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.5442P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5624 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1561(2) 0.3780(2) 0.14714(13) 0.0280(4) Uani 1 1 d . . . C2 C 0.3764(2) 0.28089(19) 0.06304(13) 0.0259(3) Uani 1 1 d . . . C3 C 0.4795(2) 0.20893(19) 0.15676(13) 0.0253(3) Uani 1 1 d . . . C4 C 0.4023(2) 0.22654(19) 0.24782(13) 0.0258(3) Uani 1 1 d . . . C5 C 0.6627(2) 0.12458(19) 0.16281(13) 0.0263(3) Uani 1 1 d . . . C6 C 0.7080(2) 0.0067(2) 0.13114(14) 0.0299(4) Uani 1 1 d . . . H6 H 0.6192 -0.0229 0.1070 0.036 Uiso 1 1 calc R . . C7 C 0.8798(2) -0.0681(2) 0.13409(15) 0.0359(4) Uani 1 1 d . . . H7 H 0.9088 -0.1463 0.1105 0.043 Uiso 1 1 calc R . . C8 C 1.0071(2) -0.0266(2) 0.17193(15) 0.0367(4) Uani 1 1 d . . . C9 C 0.9675(2) 0.0876(2) 0.20559(17) 0.0387(4) Uani 1 1 d . . . H9 H 1.0568 0.1143 0.2320 0.046 Uiso 1 1 calc R . . C10 C 0.7955(2) 0.1630(2) 0.20038(15) 0.0335(4) Uani 1 1 d . . . H10 H 0.7680 0.2422 0.2229 0.040 Uiso 1 1 calc R . . C11 C 0.4386(2) 0.2814(2) -0.04277(14) 0.0308(4) Uani 1 1 d . . . H11A H 0.3412 0.2822 -0.0861 0.037 Uiso 1 1 calc R . . H11B H 0.5302 0.1920 -0.0320 0.037 Uiso 1 1 calc R . . C12 C 0.5093(4) 0.4109(3) -0.10124(19) 0.0566(7) Uani 1 1 d . . . H12A H 0.5365 0.4135 -0.1724 0.085 Uiso 1 1 calc R . . H12B H 0.6148 0.4038 -0.0630 0.085 Uiso 1 1 calc R . . H12D H 0.4225 0.4992 -0.1063 0.085 Uiso 1 1 calc R . . C13 C 0.3413(2) 0.5051(2) 0.40468(14) 0.0295(4) Uani 1 1 d . . . H13 H 0.4565 0.4522 0.4033 0.035 Uiso 1 1 calc R . . C14 C 0.0619(2) 0.58801(19) 0.37542(13) 0.0250(3) Uani 1 1 d . . . C15 C -0.1172(2) 0.6219(2) 0.34639(13) 0.0261(3) Uani 1 1 d . . . C16 C -0.1527(2) 0.79120(19) 0.44212(13) 0.0267(3) Uani 1 1 d . . . C17 C 0.1264(2) 0.64853(19) 0.43482(13) 0.0257(3) Uani 1 1 d . . . C18 C 0.0941(3) 0.8013(2) 0.53963(18) 0.0409(5) Uani 1 1 d . . . H18A H 0.0041 0.8298 0.5837 0.061 Uiso 1 1 calc R . . H18B H 0.1369 0.8850 0.4967 0.061 Uiso 1 1 calc R . . H18C H 0.1900 0.7254 0.5849 0.061 Uiso 1 1 calc R . . C19 C -0.4028(2) 0.7744(2) 0.35622(15) 0.0324(4) Uani 1 1 d . . . H19A H -0.4359 0.8786 0.3153 0.049 Uiso 1 1 calc R . . H19B H -0.4646 0.7527 0.4214 0.049 Uiso 1 1 calc R . . H19C H -0.4331 0.7233 0.3143 0.049 Uiso 1 1 calc R . . N1 N 0.24293(18) 0.31207(17) 0.24263(11) 0.0272(3) Uani 1 1 d . . . N2 N 0.21503(18) 0.36382(17) 0.05744(11) 0.0284(3) Uani 1 1 d . . . N3 N -0.00276(19) 0.4635(2) 0.14231(13) 0.0377(4) Uani 1 1 d . . . H3A H -0.0645 0.5080 0.0817 0.045 Uiso 1 1 calc R . . H3B H -0.0452 0.4751 0.1997 0.045 Uiso 1 1 calc R . . N4 N 0.48361(19) 0.16092(18) 0.34566(12) 0.0335(4) Uani 1 1 d . . . H4A H 0.4316 0.1759 0.3998 0.040 Uiso 1 1 calc R . . H4B H 0.5884 0.1033 0.3550 0.040 Uiso 1 1 calc R . . N5 N 0.30052(17) 0.59752(17) 0.45420(12) 0.0281(3) Uani 1 1 d . . . N6 N 0.20400(17) 0.49398(17) 0.35689(11) 0.0275(3) Uani 1 1 d . . . H6N H 0.2046 0.4383 0.3212 0.033 Uiso 1 1 calc R . . N7 N -0.21537(17) 0.72739(16) 0.38260(11) 0.0267(3) Uani 1 1 d . . . N8 N 0.02149(18) 0.74683(17) 0.47029(12) 0.0280(3) Uani 1 1 d . . . O1 O -0.18631(16) 0.56998(16) 0.29621(10) 0.0343(3) Uani 1 1 d . . . O2 O -0.25075(16) 0.88346(15) 0.46876(10) 0.0340(3) Uani 1 1 d . . . Cl1 Cl 1.22300(6) -0.11993(7) 0.17780(5) 0.05659(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0232(7) 0.0336(9) 0.0257(8) -0.0127(7) 0.0003(6) -0.0019(7) C2 0.0243(7) 0.0284(9) 0.0265(8) -0.0128(7) 0.0029(6) -0.0050(6) C3 0.0216(7) 0.0278(8) 0.0268(8) -0.0124(7) 0.0021(6) -0.0035(6) C4 0.0240(7) 0.0272(8) 0.0249(8) -0.0107(7) 0.0011(6) -0.0026(6) C5 0.0227(7) 0.0296(9) 0.0246(8) -0.0099(7) 0.0032(6) -0.0036(6) C6 0.0271(8) 0.0303(9) 0.0305(9) -0.0122(7) 0.0034(7) -0.0031(7) C7 0.0324(9) 0.0350(10) 0.0348(9) -0.0141(8) 0.0058(7) 0.0021(7) C8 0.0226(8) 0.0423(11) 0.0336(9) -0.0074(8) 0.0068(7) 0.0007(7) C9 0.0244(8) 0.0464(12) 0.0434(11) -0.0150(9) 0.0018(7) -0.0083(8) C10 0.0271(8) 0.0358(10) 0.0386(10) -0.0161(8) 0.0016(7) -0.0062(7) C11 0.0297(8) 0.0357(10) 0.0260(8) -0.0147(7) 0.0021(7) -0.0017(7) C12 0.0832(18) 0.0555(15) 0.0418(12) -0.0237(11) 0.0305(12) -0.0314(13) C13 0.0203(7) 0.0362(10) 0.0299(8) -0.0121(7) 0.0014(6) -0.0038(7) C14 0.0208(7) 0.0275(8) 0.0257(8) -0.0100(7) 0.0027(6) -0.0041(6) C15 0.0209(7) 0.0321(9) 0.0244(8) -0.0104(7) 0.0026(6) -0.0058(6) C16 0.0242(7) 0.0283(9) 0.0254(8) -0.0095(7) 0.0032(6) -0.0038(6) C17 0.0209(7) 0.0289(9) 0.0260(8) -0.0098(7) 0.0020(6) -0.0048(6) C18 0.0344(9) 0.0438(12) 0.0531(12) -0.0309(10) -0.0069(9) -0.0034(8) C19 0.0172(7) 0.0383(10) 0.0395(10) -0.0140(8) 0.0017(7) -0.0039(7) N1 0.0231(6) 0.0315(8) 0.0242(7) -0.0117(6) 0.0000(5) 0.0002(6) N2 0.0234(7) 0.0345(8) 0.0264(7) -0.0146(6) -0.0002(5) -0.0004(6) N3 0.0256(7) 0.0523(11) 0.0280(8) -0.0185(7) -0.0030(6) 0.0092(7) N4 0.0270(7) 0.0413(9) 0.0253(7) -0.0138(7) -0.0004(6) 0.0063(6) N5 0.0189(6) 0.0334(8) 0.0315(7) -0.0125(6) 0.0006(5) -0.0047(5) N6 0.0211(6) 0.0332(8) 0.0289(7) -0.0152(6) 0.0019(5) -0.0022(6) N7 0.0181(6) 0.0317(8) 0.0280(7) -0.0100(6) 0.0021(5) -0.0041(5) N8 0.0229(6) 0.0309(8) 0.0328(8) -0.0161(6) 0.0011(6) -0.0045(6) O1 0.0246(6) 0.0485(8) 0.0361(7) -0.0236(6) 0.0002(5) -0.0078(5) O2 0.0294(6) 0.0347(7) 0.0354(7) -0.0165(6) 0.0026(5) 0.0015(5) Cl1 0.0254(2) 0.0675(4) 0.0573(3) -0.0149(3) 0.0075(2) 0.0088(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.342(2) . ? C1 N3 1.342(2) . ? C1 N1 1.348(2) . ? C2 N2 1.345(2) . ? C2 C3 1.392(2) . ? C2 C11 1.509(2) . ? C3 C4 1.420(2) . ? C3 C5 1.493(2) . ? C4 N1 1.344(2) . ? C4 N4 1.357(2) . ? C5 C10 1.393(3) . ? C5 C6 1.399(2) . ? C6 C7 1.391(2) . ? C6 H6 0.9500 . ? C7 C8 1.378(3) . ? C7 H7 0.9500 . ? C8 C9 1.381(3) . ? C8 Cl1 1.7419(18) . ? C9 C10 1.391(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.511(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12D 0.9800 . ? C13 N5 1.334(2) . ? C13 N6 1.345(2) . ? C13 H13 0.9500 . ? C14 C17 1.370(2) . ? C14 N6 1.381(2) . ? C14 C15 1.419(2) . ? C15 O1 1.227(2) . ? C15 N7 1.412(2) . ? C16 O2 1.232(2) . ? C16 N8 1.373(2) . ? C16 N7 1.390(2) . ? C17 N5 1.356(2) . ? C17 N8 1.371(2) . ? C18 N8 1.464(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N7 1.468(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N6 H6N 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N3 117.72(15) . . ? N2 C1 N1 125.36(15) . . ? N3 C1 N1 116.91(15) . . ? N2 C2 C3 122.93(15) . . ? N2 C2 C11 113.62(14) . . ? C3 C2 C11 123.34(14) . . ? C2 C3 C4 115.56(14) . . ? C2 C3 C5 123.45(14) . . ? C4 C3 C5 120.92(14) . . ? N1 C4 N4 115.05(14) . . ? N1 C4 C3 121.97(15) . . ? N4 C4 C3 122.97(15) . . ? C10 C5 C6 117.78(16) . . ? C10 C5 C3 120.00(16) . . ? C6 C5 C3 122.21(16) . . ? C7 C6 C5 121.62(18) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 118.70(18) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C9 121.44(17) . . ? C7 C8 Cl1 119.57(16) . . ? C9 C8 Cl1 118.99(16) . . ? C8 C9 C10 119.20(19) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C5 121.25(18) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? C2 C11 C12 111.65(16) . . ? C2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C2 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12D 109.5 . . ? H12A C12 H12D 109.5 . . ? H12B C12 H12D 109.5 . . ? N5 C13 N6 113.74(15) . . ? N5 C13 H13 123.1 . . ? N6 C13 H13 123.1 . . ? C17 C14 N6 105.24(14) . . ? C17 C14 C15 122.73(15) . . ? N6 C14 C15 132.02(16) . . ? O1 C15 N7 121.25(15) . . ? O1 C15 C14 127.00(16) . . ? N7 C15 C14 111.74(15) . . ? O2 C16 N8 121.60(17) . . ? O2 C16 N7 120.93(15) . . ? N8 C16 N7 117.47(14) . . ? N5 C17 C14 112.05(15) . . ? N5 C17 N8 125.90(16) . . ? C14 C17 N8 122.04(15) . . ? N8 C18 H18A 109.5 . . ? N8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4 N1 C1 117.13(14) . . ? C1 N2 C2 116.98(14) . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C13 N5 C17 103.16(14) . . ? C13 N6 C14 105.81(14) . . ? C13 N6 H6N 127.1 . . ? C14 N6 H6N 127.1 . . ? C16 N7 C15 126.52(14) . . ? C16 N7 C19 116.10(14) . . ? C15 N7 C19 117.38(15) . . ? C17 N8 C16 119.40(15) . . ? C17 N8 C18 120.21(14) . . ? C16 N8 C18 120.38(15) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 C4 1.0(3) . . . . ? C11 C2 C3 C4 176.84(16) . . . . ? N2 C2 C3 C5 -175.80(17) . . . . ? C11 C2 C3 C5 0.1(3) . . . . ? C2 C3 C4 N1 -2.7(3) . . . . ? C5 C3 C4 N1 174.15(17) . . . . ? C2 C3 C4 N4 178.36(17) . . . . ? C5 C3 C4 N4 -4.8(3) . . . . ? C2 C3 C5 C10 119.9(2) . . . . ? C4 C3 C5 C10 -56.7(2) . . . . ? C2 C3 C5 C6 -59.6(2) . . . . ? C4 C3 C5 C6 123.75(19) . . . . ? C10 C5 C6 C7 -1.6(3) . . . . ? C3 C5 C6 C7 177.95(17) . . . . ? C5 C6 C7 C8 1.7(3) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? C6 C7 C8 Cl1 179.29(14) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? Cl1 C8 C9 C10 179.56(15) . . . . ? C8 C9 C10 C5 0.6(3) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? C3 C5 C10 C9 -179.15(17) . . . . ? N2 C2 C11 C12 82.8(2) . . . . ? C3 C2 C11 C12 -93.4(2) . . . . ? C17 C14 C15 O1 -177.76(18) . . . . ? N6 C14 C15 O1 0.6(3) . . . . ? C17 C14 C15 N7 2.3(2) . . . . ? N6 C14 C15 N7 -179.39(17) . . . . ? N6 C14 C17 N5 0.0(2) . . . . ? C15 C14 C17 N5 178.78(16) . . . . ? N6 C14 C17 N8 -178.87(16) . . . . ? C15 C14 C17 N8 -0.1(3) . . . . ? N4 C4 N1 C1 -179.09(17) . . . . ? C3 C4 N1 C1 1.9(3) . . . . ? N2 C1 N1 C4 0.8(3) . . . . ? N3 C1 N1 C4 -179.85(18) . . . . ? N3 C1 N2 C2 178.20(18) . . . . ? N1 C1 N2 C2 -2.4(3) . . . . ? C3 C2 N2 C1 1.4(3) . . . . ? C11 C2 N2 C1 -174.81(16) . . . . ? N6 C13 N5 C17 -0.7(2) . . . . ? C14 C17 N5 C13 0.4(2) . . . . ? N8 C17 N5 C13 179.28(17) . . . . ? N5 C13 N6 C14 0.8(2) . . . . ? C17 C14 N6 C13 -0.48(19) . . . . ? C15 C14 N6 C13 -179.05(19) . . . . ? O2 C16 N7 C15 179.43(17) . . . . ? N8 C16 N7 C15 -0.9(3) . . . . ? O2 C16 N7 C19 -1.2(2) . . . . ? N8 C16 N7 C19 178.42(15) . . . . ? O1 C15 N7 C16 178.27(17) . . . . ? C14 C15 N7 C16 -1.7(2) . . . . ? O1 C15 N7 C19 -1.1(2) . . . . ? C14 C15 N7 C19 178.91(15) . . . . ? N5 C17 N8 C16 178.44(17) . . . . ? C14 C17 N8 C16 -2.8(3) . . . . ? N5 C17 N8 C18 -3.0(3) . . . . ? C14 C17 N8 C18 175.75(18) . . . . ? O2 C16 N8 C17 -177.15(17) . . . . ? N7 C16 N8 C17 3.2(2) . . . . ? O2 C16 N8 C18 4.3(3) . . . . ? N7 C16 N8 C18 -175.32(17) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.357 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.055 data_wj1074 _database_code_depnum_ccdc_archive 'CCDC 885647' #TrackingRef 'Pyrimethaminium + saccharinate+ methanol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethaminium+saccharinate+methanol _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 Cl N4 1+, C7 H4 N O3 S 1-, C H4 O' _chemical_formula_sum 'C20 H22 Cl N5 O4 S' _chemical_formula_weight 463.94 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.90400(10) _cell_length_b 7.58660(10) _cell_length_c 21.2823(3) _cell_angle_alpha 85.3640(10) _cell_angle_beta 81.0520(10) _cell_angle_gamma 79.0070(10) _cell_volume 1079.44(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14456 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'multi-scan from symmetry-related measurements Sortav (Blessing 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 18300 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 30.06 _reflns_number_total 6251 _reflns_number_gt 5179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.5530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6251 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.24456(19) 0.30032(18) 0.41784(6) 0.0219(2) Uani 1 1 d . . . C2 C 0.05701(19) 0.22504(17) 0.43377(6) 0.0216(2) Uani 1 1 d . . . C3 C -0.0763(2) 0.23658(19) 0.48969(7) 0.0263(3) Uani 1 1 d . . . H23A H -0.0549 0.2975 0.5246 0.032 Uiso 1 1 calc R . . C4 C -0.2430(2) 0.1558(2) 0.49312(8) 0.0309(3) Uani 1 1 d . . . H22A H -0.3368 0.1616 0.5310 0.037 Uiso 1 1 calc R . . C5 C -0.2740(2) 0.0668(2) 0.44192(8) 0.0314(3) Uani 1 1 d . . . H21A H -0.3900 0.0145 0.4452 0.038 Uiso 1 1 calc R . . C6 C -0.1389(2) 0.05244(19) 0.38594(7) 0.0280(3) Uani 1 1 d . . . H20A H -0.1588 -0.0095 0.3511 0.034 Uiso 1 1 calc R . . C7 C 0.02583(19) 0.13293(18) 0.38367(6) 0.0228(2) Uani 1 1 d . . . C8 C 0.71427(19) 0.49936(18) 0.25082(6) 0.0227(3) Uani 1 1 d . . . C9 C 0.8712(2) 0.58523(18) 0.23107(6) 0.0226(2) Uani 1 1 d . . . C10 C 0.9619(2) 0.64404(18) 0.28014(6) 0.0228(3) Uani 1 1 d . . . C11 C 0.7266(2) 0.55704(17) 0.35810(6) 0.0215(2) Uani 1 1 d . . . C12 C 0.9517(2) 0.61142(18) 0.16255(6) 0.0235(3) Uani 1 1 d . . . C13 C 1.1333(2) 0.5115(2) 0.13683(7) 0.0280(3) Uani 1 1 d . . . H8A H 1.2046 0.4229 0.1630 0.034 Uiso 1 1 calc R . . C14 C 1.2117(2) 0.5396(2) 0.07339(7) 0.0318(3) Uani 1 1 d . . . H7A H 1.3361 0.4715 0.0561 0.038 Uiso 1 1 calc R . . C15 C 1.1063(2) 0.6674(2) 0.03603(7) 0.0297(3) Uani 1 1 d . . . C16 C 0.9242(3) 0.7671(2) 0.05970(7) 0.0344(3) Uani 1 1 d . . . H3A H 0.8525 0.8535 0.0329 0.041 Uiso 1 1 calc R . . C17 C 0.8476(2) 0.7390(2) 0.12328(7) 0.0308(3) Uani 1 1 d . . . H6A H 0.7231 0.8075 0.1402 0.037 Uiso 1 1 calc R . . C18 C 0.6156(2) 0.4056(2) 0.20876(6) 0.0288(3) Uani 1 1 d . . . H9A H 0.6312 0.4614 0.1650 0.035 Uiso 1 1 calc R . . H9B H 0.4712 0.4197 0.2248 0.035 Uiso 1 1 calc R . . C19 C 0.7069(3) 0.2063(2) 0.20733(8) 0.0391(4) Uani 1 1 d . . . H4A H 0.6431 0.1484 0.1786 0.059 Uiso 1 1 calc R . . H4B H 0.6860 0.1500 0.2503 0.059 Uiso 1 1 calc R . . H4C H 0.8501 0.1925 0.1921 0.059 Uiso 1 1 calc R . . C20 C 0.3170(3) 1.0123(3) 0.10650(10) 0.0526(5) Uani 1 1 d . . . H1A H 0.3549 0.9211 0.0746 0.063 Uiso 1 1 calc R . . H1B H 0.4027 1.1030 0.0967 0.063 Uiso 1 1 calc R . . H1C H 0.1776 1.0701 0.1060 0.063 Uiso 1 1 calc R . . N1 N 0.34435(17) 0.26245(16) 0.35912(5) 0.0247(2) Uani 1 1 d . . . N2 N 0.64436(17) 0.48492(16) 0.31440(5) 0.0235(2) Uani 1 1 d . . . H18 H 0.5444 0.4279 0.3273 0.028 Uiso 1 1 calc R . . N3 N 0.63863(18) 0.55402(16) 0.41793(5) 0.0256(2) Uani 1 1 d . . . H15A H 0.6876 0.6004 0.4473 0.031 Uiso 1 1 calc R . . H15B H 0.5311 0.5056 0.4284 0.031 Uiso 1 1 calc R . . N4 N 0.88943(17) 0.63014(16) 0.34204(5) 0.0238(2) Uani 1 1 d . . . N5 N 1.12577(19) 0.71667(18) 0.26526(6) 0.0311(3) Uani 1 1 d . . . H10A H 1.1804 0.7525 0.2955 0.037 Uiso 1 1 calc R . . H10B H 1.1792 0.7287 0.2252 0.037 Uiso 1 1 calc R . . O1 O 0.30094(15) 0.38982(14) 0.45544(5) 0.0284(2) Uani 1 1 d . . . O2 O 0.35381(16) -0.04976(15) 0.32318(5) 0.0332(2) Uani 1 1 d . . . O3 O 0.18940(17) 0.20744(16) 0.26403(5) 0.0338(2) Uani 1 1 d . . . O4 O 0.3399(2) 0.9300(2) 0.16729(6) 0.0496(3) Uani 1 1 d . . . H2 H 0.310(4) 1.009(3) 0.1931(12) 0.060 Uiso 1 1 d . . . S1 S 0.23882(5) 0.13075(5) 0.325286(15) 0.02340(8) Uani 1 1 d . . . Cl1 Cl 1.20516(7) 0.70716(7) -0.043387(18) 0.04497(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0217(6) 0.0240(6) 0.0207(6) -0.0021(5) -0.0028(5) -0.0057(5) C2 0.0210(6) 0.0205(6) 0.0229(6) 0.0003(5) -0.0021(5) -0.0045(5) C3 0.0260(6) 0.0244(6) 0.0257(6) -0.0015(5) 0.0019(5) -0.0017(5) C4 0.0243(6) 0.0272(7) 0.0363(8) 0.0027(6) 0.0057(6) -0.0026(5) C5 0.0217(6) 0.0285(7) 0.0436(8) 0.0051(6) -0.0020(6) -0.0085(5) C6 0.0259(6) 0.0271(7) 0.0336(7) 0.0010(6) -0.0073(5) -0.0097(5) C7 0.0221(6) 0.0234(6) 0.0233(6) 0.0007(5) -0.0030(5) -0.0061(5) C8 0.0230(6) 0.0282(6) 0.0182(6) -0.0030(5) -0.0022(5) -0.0076(5) C9 0.0245(6) 0.0257(6) 0.0185(6) -0.0020(5) -0.0015(5) -0.0077(5) C10 0.0252(6) 0.0224(6) 0.0218(6) -0.0026(5) -0.0017(5) -0.0081(5) C11 0.0253(6) 0.0211(6) 0.0191(6) -0.0017(5) -0.0039(5) -0.0055(5) C12 0.0259(6) 0.0277(6) 0.0189(6) -0.0022(5) -0.0018(5) -0.0109(5) C13 0.0261(6) 0.0341(7) 0.0235(6) 0.0003(5) -0.0034(5) -0.0055(6) C14 0.0279(7) 0.0394(8) 0.0264(7) -0.0041(6) 0.0033(5) -0.0066(6) C15 0.0366(8) 0.0352(7) 0.0187(6) -0.0011(5) 0.0012(5) -0.0145(6) C16 0.0407(8) 0.0353(8) 0.0247(7) 0.0046(6) -0.0036(6) -0.0043(7) C17 0.0322(7) 0.0316(7) 0.0254(7) 0.0002(6) -0.0003(6) -0.0018(6) C18 0.0279(7) 0.0432(8) 0.0199(6) -0.0047(6) -0.0038(5) -0.0164(6) C19 0.0449(9) 0.0427(9) 0.0345(8) -0.0137(7) -0.0020(7) -0.0183(8) C20 0.0583(12) 0.0544(12) 0.0487(11) -0.0045(9) -0.0102(9) -0.0161(10) N1 0.0241(5) 0.0320(6) 0.0208(5) -0.0054(4) 0.0001(4) -0.0129(5) N2 0.0251(5) 0.0300(6) 0.0181(5) -0.0027(4) -0.0017(4) -0.0127(5) N3 0.0291(6) 0.0325(6) 0.0178(5) -0.0041(4) -0.0013(4) -0.0123(5) N4 0.0274(6) 0.0260(6) 0.0203(5) -0.0033(4) -0.0025(4) -0.0103(5) N5 0.0344(6) 0.0407(7) 0.0237(6) -0.0063(5) -0.0004(5) -0.0220(6) O1 0.0296(5) 0.0347(5) 0.0241(5) -0.0096(4) -0.0014(4) -0.0119(4) O2 0.0312(5) 0.0326(6) 0.0364(6) -0.0130(5) -0.0008(4) -0.0059(4) O3 0.0402(6) 0.0464(6) 0.0194(5) 0.0011(4) -0.0069(4) -0.0185(5) O4 0.0661(9) 0.0520(8) 0.0332(6) -0.0115(6) 0.0094(6) -0.0265(7) S1 0.02454(16) 0.02918(17) 0.01893(15) -0.00456(12) -0.00179(11) -0.01066(13) Cl1 0.0550(3) 0.0569(3) 0.02116(17) 0.00201(16) 0.00667(16) -0.0170(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2403(15) . ? C1 N1 1.3540(17) . ? C1 C2 1.4940(17) . ? C2 C3 1.3846(18) . ? C2 C7 1.3859(18) . ? C3 C4 1.393(2) . ? C3 H23A 0.9500 . ? C4 C5 1.392(2) . ? C4 H22A 0.9500 . ? C5 C6 1.392(2) . ? C5 H21A 0.9500 . ? C6 C7 1.3823(18) . ? C6 H20A 0.9500 . ? C7 S1 1.7698(13) . ? C8 C9 1.3630(18) . ? C8 N2 1.3672(16) . ? C8 C18 1.4996(18) . ? C9 C10 1.4380(18) . ? C9 C12 1.4894(17) . ? C10 N5 1.3346(17) . ? C10 N4 1.3379(17) . ? C11 N3 1.3231(16) . ? C11 N4 1.3326(16) . ? C11 N2 1.3607(16) . ? C12 C13 1.392(2) . ? C12 C17 1.394(2) . ? C13 C14 1.390(2) . ? C13 H8A 0.9500 . ? C14 C15 1.374(2) . ? C14 H7A 0.9500 . ? C15 C16 1.382(2) . ? C15 Cl1 1.7466(14) . ? C16 C17 1.389(2) . ? C16 H3A 0.9500 . ? C17 H6A 0.9500 . ? C18 C19 1.524(2) . ? C18 H9A 0.9900 . ? C18 H9B 0.9900 . ? C19 H4A 0.9800 . ? C19 H4B 0.9800 . ? C19 H4C 0.9800 . ? C20 O4 1.409(2) . ? C20 H1A 0.9800 . ? C20 H1B 0.9800 . ? C20 H1C 0.9800 . ? N1 S1 1.6139(11) . ? N2 H18 0.8800 . ? N3 H15A 0.8800 . ? N3 H15B 0.8800 . ? N5 H10A 0.8800 . ? N5 H10B 0.8800 . ? O2 S1 1.4464(11) . ? O3 S1 1.4472(11) . ? O4 H2 0.82(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 123.87(12) . . ? O1 C1 C2 122.28(12) . . ? N1 C1 C2 113.85(11) . . ? C3 C2 C7 120.54(12) . . ? C3 C2 C1 128.35(12) . . ? C7 C2 C1 111.11(11) . . ? C2 C3 C4 117.78(13) . . ? C2 C3 H23A 121.1 . . ? C4 C3 H23A 121.1 . . ? C5 C4 C3 120.94(13) . . ? C5 C4 H22A 119.5 . . ? C3 C4 H22A 119.5 . . ? C4 C5 C6 121.51(13) . . ? C4 C5 H21A 119.2 . . ? C6 C5 H21A 119.2 . . ? C7 C6 C5 116.58(13) . . ? C7 C6 H20A 121.7 . . ? C5 C6 H20A 121.7 . . ? C6 C7 C2 122.64(13) . . ? C6 C7 S1 130.77(11) . . ? C2 C7 S1 106.43(9) . . ? C9 C8 N2 119.26(12) . . ? C9 C8 C18 125.48(12) . . ? N2 C8 C18 115.13(11) . . ? C8 C9 C10 116.53(12) . . ? C8 C9 C12 122.43(12) . . ? C10 C9 C12 120.99(11) . . ? N5 C10 N4 116.58(12) . . ? N5 C10 C9 120.50(12) . . ? N4 C10 C9 122.92(12) . . ? N3 C11 N4 120.21(12) . . ? N3 C11 N2 117.82(12) . . ? N4 C11 N2 121.97(12) . . ? C13 C12 C17 118.83(13) . . ? C13 C12 C9 120.76(13) . . ? C17 C12 C9 120.40(13) . . ? C14 C13 C12 120.88(14) . . ? C14 C13 H8A 119.6 . . ? C12 C13 H8A 119.6 . . ? C15 C14 C13 118.91(14) . . ? C15 C14 H7A 120.5 . . ? C13 C14 H7A 120.5 . . ? C14 C15 C16 121.78(13) . . ? C14 C15 Cl1 119.44(12) . . ? C16 C15 Cl1 118.78(12) . . ? C15 C16 C17 118.90(15) . . ? C15 C16 H3A 120.5 . . ? C17 C16 H3A 120.5 . . ? C16 C17 C12 120.69(14) . . ? C16 C17 H6A 119.7 . . ? C12 C17 H6A 119.7 . . ? C8 C18 C19 110.77(12) . . ? C8 C18 H9A 109.5 . . ? C19 C18 H9A 109.5 . . ? C8 C18 H9B 109.5 . . ? C19 C18 H9B 109.5 . . ? H9A C18 H9B 108.1 . . ? C18 C19 H4A 109.5 . . ? C18 C19 H4B 109.5 . . ? H4A C19 H4B 109.5 . . ? C18 C19 H4C 109.5 . . ? H4A C19 H4C 109.5 . . ? H4B C19 H4C 109.5 . . ? O4 C20 H1A 109.5 . . ? O4 C20 H1B 109.5 . . ? H1A C20 H1B 109.5 . . ? O4 C20 H1C 109.5 . . ? H1A C20 H1C 109.5 . . ? H1B C20 H1C 109.5 . . ? C1 N1 S1 110.79(9) . . ? C11 N2 C8 121.20(11) . . ? C11 N2 H18 119.4 . . ? C8 N2 H18 119.4 . . ? C11 N3 H15A 120.0 . . ? C11 N3 H15B 120.0 . . ? H15A N3 H15B 120.0 . . ? C11 N4 C10 117.68(11) . . ? C10 N5 H10A 120.0 . . ? C10 N5 H10B 120.0 . . ? H10A N5 H10B 120.0 . . ? C20 O4 H2 107.7(17) . . ? O2 S1 O3 113.91(7) . . ? O2 S1 N1 111.63(7) . . ? O3 S1 N1 111.28(6) . . ? O2 S1 C7 108.99(6) . . ? O3 S1 C7 112.59(7) . . ? N1 S1 C7 97.25(6) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -1.5(2) . . . . ? N1 C1 C2 C3 178.80(13) . . . . ? O1 C1 C2 C7 179.12(13) . . . . ? N1 C1 C2 C7 -0.54(17) . . . . ? C7 C2 C3 C4 -1.2(2) . . . . ? C1 C2 C3 C4 179.54(13) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C3 C4 C5 C6 1.0(2) . . . . ? C4 C5 C6 C7 -0.7(2) . . . . ? C5 C6 C7 C2 -0.5(2) . . . . ? C5 C6 C7 S1 174.27(11) . . . . ? C3 C2 C7 C6 1.5(2) . . . . ? C1 C2 C7 C6 -179.10(13) . . . . ? C3 C2 C7 S1 -174.38(11) . . . . ? C1 C2 C7 S1 5.02(14) . . . . ? N2 C8 C9 C10 4.4(2) . . . . ? C18 C8 C9 C10 -171.33(13) . . . . ? N2 C8 C9 C12 -178.04(13) . . . . ? C18 C8 C9 C12 6.2(2) . . . . ? C8 C9 C10 N5 174.78(13) . . . . ? C12 C9 C10 N5 -2.8(2) . . . . ? C8 C9 C10 N4 -5.3(2) . . . . ? C12 C9 C10 N4 177.06(13) . . . . ? C8 C9 C12 C13 -106.71(16) . . . . ? C10 C9 C12 C13 70.77(18) . . . . ? C8 C9 C12 C17 74.41(19) . . . . ? C10 C9 C12 C17 -108.12(16) . . . . ? C17 C12 C13 C14 0.9(2) . . . . ? C9 C12 C13 C14 -177.98(13) . . . . ? C12 C13 C14 C15 -0.4(2) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C13 C14 C15 Cl1 178.81(11) . . . . ? C14 C15 C16 C17 1.1(2) . . . . ? Cl1 C15 C16 C17 -178.36(12) . . . . ? C15 C16 C17 C12 -0.5(2) . . . . ? C13 C12 C17 C16 -0.5(2) . . . . ? C9 C12 C17 C16 178.46(14) . . . . ? C9 C8 C18 C19 93.35(17) . . . . ? N2 C8 C18 C19 -82.51(15) . . . . ? O1 C1 N1 S1 175.55(12) . . . . ? C2 C1 N1 S1 -4.80(15) . . . . ? N3 C11 N2 C8 173.23(13) . . . . ? N4 C11 N2 C8 -6.3(2) . . . . ? C9 C8 N2 C11 1.0(2) . . . . ? C18 C8 N2 C11 177.15(13) . . . . ? N3 C11 N4 C10 -174.18(13) . . . . ? N2 C11 N4 C10 5.3(2) . . . . ? N5 C10 N4 C11 -179.61(13) . . . . ? C9 C10 N4 C11 0.5(2) . . . . ? C1 N1 S1 O2 -106.98(11) . . . . ? C1 N1 S1 O3 124.53(10) . . . . ? C1 N1 S1 C7 6.81(11) . . . . ? C6 C7 S1 O2 -66.47(15) . . . . ? C2 C7 S1 O2 108.94(10) . . . . ? C6 C7 S1 O3 60.94(15) . . . . ? C2 C7 S1 O3 -123.65(10) . . . . ? C6 C7 S1 N1 177.63(14) . . . . ? C2 C7 S1 N1 -6.96(11) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.332 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.053 data_wj1150 _database_code_depnum_ccdc_archive 'CCDC 885648' #TrackingRef 'pyrimethaminium+alpha-ketoglutarate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethaminium+alpha-ketoglutarate _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 Cl N4 1+, C5 H5 O5 1-' _chemical_formula_sum 'C17 H19 Cl N4 O5' _chemical_formula_weight 394.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8393(2) _cell_length_b 11.0472(3) _cell_length_c 12.1060(4) _cell_angle_alpha 82.881(2) _cell_angle_beta 71.670(2) _cell_angle_gamma 69.719(2) _cell_volume 933.38(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12793 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13606 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5418 _reflns_number_gt 4203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.3028P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5418 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.03017(19) 0.29418(13) 0.59623(12) 0.0287(3) Uani 1 1 d . . . C2 C 0.1269(2) 0.33462(14) 0.56313(13) 0.0343(3) Uani 1 1 d . . . H2 H 0.1480 0.3887 0.4963 0.041 Uiso 1 1 calc R . . C3 C 0.2541(2) 0.29484(14) 0.62928(13) 0.0319(3) Uani 1 1 d . . . H3 H 0.3609 0.3240 0.6084 0.038 Uiso 1 1 calc R . . C4 C 0.22707(18) 0.21316(12) 0.72527(11) 0.0244(2) Uani 1 1 d . . . C5 C 0.0670(2) 0.17525(15) 0.75679(13) 0.0357(3) Uani 1 1 d . . . H5 H 0.0459 0.1205 0.8230 0.043 Uiso 1 1 calc R . . C6 C -0.0631(2) 0.21624(16) 0.69291(13) 0.0365(3) Uani 1 1 d . . . H6 H -0.1734 0.1907 0.7157 0.044 Uiso 1 1 calc R . . C7 C 0.36709(18) 0.16656(12) 0.79368(11) 0.0246(2) Uani 1 1 d . . . C8 C 0.51737(18) 0.05541(12) 0.76844(11) 0.0259(3) Uani 1 1 d . . . C9 C 0.61681(18) 0.09216(12) 0.92370(11) 0.0245(2) Uani 1 1 d . . . C10 C 0.34482(18) 0.23641(12) 0.89288(11) 0.0244(2) Uani 1 1 d . . . C11 C 0.5670(2) -0.03097(14) 0.66868(14) 0.0362(3) Uani 1 1 d . . . H11A H 0.4515 -0.0181 0.6454 0.043 Uiso 1 1 calc R . . H11B H 0.6132 -0.1222 0.6939 0.043 Uiso 1 1 calc R . . C12 C 0.7188(3) -0.0033(2) 0.56484(16) 0.0557(5) Uani 1 1 d . . . H12A H 0.7435 -0.0582 0.5001 0.084 Uiso 1 1 calc R . . H12B H 0.8360 -0.0216 0.5862 0.084 Uiso 1 1 calc R . . H12C H 0.6749 0.0876 0.5412 0.084 Uiso 1 1 calc R . . C13 C 0.74934(18) 0.53689(13) 0.81462(12) 0.0291(3) Uani 1 1 d . . . C14 C 0.57660(19) 0.51484(13) 0.80387(14) 0.0334(3) Uani 1 1 d . . . H14A H 0.5525 0.4415 0.8547 0.040 Uiso 1 1 calc R . . H14B H 0.5968 0.4942 0.7225 0.040 Uiso 1 1 calc R . . C15 C 0.40727(19) 0.63768(14) 0.84016(14) 0.0330(3) Uani 1 1 d . . . H15A H 0.3654 0.6424 0.9261 0.040 Uiso 1 1 calc R . . H15B H 0.4493 0.7131 0.8088 0.040 Uiso 1 1 calc R . . C16 C 0.24105(19) 0.64693(13) 0.80009(12) 0.0285(3) Uani 1 1 d . . . C17 C 0.07246(19) 0.77465(13) 0.82782(13) 0.0300(3) Uani 1 1 d . . . Cl1 Cl -0.18727(6) 0.34090(4) 0.51239(3) 0.04210(11) Uani 1 1 d . . . N1 N 0.19520(17) 0.34063(11) 0.92847(10) 0.0318(3) Uani 1 1 d . . . H1A H 0.1828 0.3826 0.9893 0.038 Uiso 1 1 calc R . . H1B H 0.1083 0.3678 0.8913 0.038 Uiso 1 1 calc R . . N2 N 0.47191(15) 0.20053(10) 0.95394(9) 0.0258(2) Uani 1 1 d . . . N3 N 0.74630(16) 0.05101(11) 0.98148(10) 0.0292(2) Uani 1 1 d . . . H3A H 0.7360 0.0957 1.0400 0.035 Uiso 1 1 calc R . . H3B H 0.8422 -0.0209 0.9612 0.035 Uiso 1 1 calc R . . N4 N 0.64007(15) 0.01814(10) 0.83510(10) 0.0262(2) Uani 1 1 d . . . H4N H 0.7354 -0.0548 0.8203 0.031 Uiso 1 1 calc R . . O1 O 0.82129(14) 0.49177(10) 0.89250(9) 0.0354(2) Uani 1 1 d . . . O2 O 0.80822(15) 0.61641(11) 0.73302(9) 0.0398(3) Uani 1 1 d . . . H2X H 0.8948 0.6346 0.7470 0.048 Uiso 1 1 calc R . . O3 O 0.23362(17) 0.56326(10) 0.74832(11) 0.0445(3) Uani 1 1 d . . . O4 O -0.06974(14) 0.78409(10) 0.79626(10) 0.0354(2) Uani 1 1 d . . . O5 O 0.09200(15) 0.85855(10) 0.87849(11) 0.0433(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0291(6) 0.0292(6) 0.0294(6) -0.0039(5) -0.0158(5) -0.0037(5) C2 0.0407(8) 0.0346(7) 0.0335(7) 0.0106(6) -0.0198(6) -0.0152(6) C3 0.0326(7) 0.0336(7) 0.0358(7) 0.0075(6) -0.0168(6) -0.0152(6) C4 0.0246(6) 0.0235(6) 0.0244(6) -0.0015(5) -0.0105(5) -0.0036(5) C5 0.0342(7) 0.0465(8) 0.0312(7) 0.0127(6) -0.0151(6) -0.0184(6) C6 0.0303(7) 0.0489(9) 0.0367(7) 0.0080(6) -0.0153(6) -0.0185(6) C7 0.0246(6) 0.0254(6) 0.0250(6) 0.0021(5) -0.0112(5) -0.0069(5) C8 0.0265(6) 0.0260(6) 0.0282(6) 0.0007(5) -0.0126(5) -0.0084(5) C9 0.0227(6) 0.0272(6) 0.0249(6) 0.0032(5) -0.0089(5) -0.0091(5) C10 0.0238(6) 0.0254(6) 0.0241(6) 0.0032(5) -0.0096(5) -0.0068(5) C11 0.0371(7) 0.0294(7) 0.0443(8) -0.0098(6) -0.0218(7) -0.0016(6) C12 0.0642(12) 0.0561(11) 0.0381(9) -0.0186(8) -0.0070(9) -0.0101(9) C13 0.0239(6) 0.0275(6) 0.0352(7) -0.0080(5) -0.0126(5) -0.0013(5) C14 0.0265(6) 0.0279(6) 0.0484(8) -0.0070(6) -0.0179(6) -0.0034(5) C15 0.0258(6) 0.0319(7) 0.0429(8) -0.0081(6) -0.0161(6) -0.0035(5) C16 0.0271(6) 0.0269(6) 0.0333(7) 0.0014(5) -0.0134(5) -0.0075(5) C17 0.0264(6) 0.0284(6) 0.0367(7) -0.0002(5) -0.0147(5) -0.0060(5) Cl1 0.0425(2) 0.0492(2) 0.0432(2) 0.00312(16) -0.02904(17) -0.01188(17) N1 0.0300(6) 0.0328(6) 0.0300(6) -0.0065(5) -0.0154(5) 0.0009(5) N2 0.0238(5) 0.0282(5) 0.0257(5) -0.0004(4) -0.0112(4) -0.0053(4) N3 0.0247(5) 0.0327(6) 0.0307(6) -0.0016(5) -0.0139(5) -0.0043(4) N4 0.0230(5) 0.0240(5) 0.0311(5) -0.0015(4) -0.0126(4) -0.0027(4) O1 0.0322(5) 0.0361(5) 0.0386(5) -0.0030(4) -0.0194(4) -0.0029(4) O2 0.0389(6) 0.0540(7) 0.0387(6) 0.0055(5) -0.0216(5) -0.0227(5) O3 0.0443(6) 0.0330(5) 0.0647(8) -0.0101(5) -0.0330(6) -0.0047(5) O4 0.0275(5) 0.0343(5) 0.0477(6) -0.0050(4) -0.0207(5) -0.0040(4) O5 0.0329(6) 0.0336(5) 0.0682(8) -0.0153(5) -0.0277(6) -0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.375(2) . ? C1 C2 1.380(2) . ? C1 Cl1 1.7405(13) . ? C2 C3 1.3926(19) . ? C2 H2 0.9500 . ? C3 C4 1.3882(18) . ? C3 H3 0.9500 . ? C4 C5 1.3852(19) . ? C4 C7 1.4935(17) . ? C5 C6 1.3902(19) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.3612(18) . ? C7 C10 1.4396(18) . ? C8 N4 1.3701(16) . ? C8 C11 1.5011(19) . ? C9 N2 1.3274(16) . ? C9 N3 1.3320(16) . ? C9 N4 1.3577(17) . ? C10 N1 1.3251(17) . ? C10 N2 1.3464(16) . ? C11 C12 1.519(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O1 1.2160(16) . ? C13 O2 1.3190(18) . ? C13 C14 1.5024(19) . ? C14 C15 1.5260(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.4955(18) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O3 1.2059(17) . ? C16 C17 1.5478(19) . ? C17 O5 1.2480(17) . ? C17 O4 1.2558(16) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4N 0.8800 . ? O2 H2X 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.29(12) . . ? C6 C1 Cl1 119.55(11) . . ? C2 C1 Cl1 119.15(11) . . ? C1 C2 C3 118.88(13) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 120.96(13) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 118.70(12) . . ? C5 C4 C7 120.29(12) . . ? C3 C4 C7 121.01(12) . . ? C4 C5 C6 120.95(13) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 119.18(13) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C10 116.72(11) . . ? C8 C7 C4 122.42(11) . . ? C10 C7 C4 120.84(11) . . ? C7 C8 N4 119.34(12) . . ? C7 C8 C11 125.23(12) . . ? N4 C8 C11 115.39(11) . . ? N2 C9 N3 120.25(12) . . ? N2 C9 N4 122.69(11) . . ? N3 C9 N4 117.06(11) . . ? N1 C10 N2 116.68(12) . . ? N1 C10 C7 120.67(11) . . ? N2 C10 C7 122.65(11) . . ? C8 C11 C12 111.47(13) . . ? C8 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C8 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 O2 123.77(13) . . ? O1 C13 C14 124.08(14) . . ? O2 C13 C14 112.06(12) . . ? C13 C14 C15 108.23(11) . . ? C13 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? C13 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C16 C15 C14 114.38(12) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? O3 C16 C15 124.22(13) . . ? O3 C16 C17 120.11(12) . . ? C15 C16 C17 115.67(11) . . ? O5 C17 O4 126.43(13) . . ? O5 C17 C16 116.72(11) . . ? O4 C17 C16 116.85(12) . . ? C10 N1 H1A 120.0 . . ? C10 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C9 N2 C10 117.45(11) . . ? C9 N3 H3A 120.0 . . ? C9 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C9 N4 C8 120.97(11) . . ? C9 N4 H4N 119.5 . . ? C8 N4 H4N 119.5 . . ? C13 O2 H2X 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.263 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.046 data_wj10106 _database_code_depnum_ccdc_archive 'CCDC 885649' #TrackingRef 'pyrimethaminium+aspirinate+acetonitrile.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethaminium+aspirinate+acetonitrile _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 Cl N4 1+, C9 H7 O4 1-, C2 H3 N' _chemical_formula_sum 'C23 H24 Cl N5 O4' _chemical_formula_weight 469.92 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0012(3) _cell_length_b 11.5494(4) _cell_length_c 11.7171(4) _cell_angle_alpha 107.432(2) _cell_angle_beta 106.355(2) _cell_angle_gamma 99.557(2) _cell_volume 1191.76(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6934 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description Blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'multi-scan from symmetry-related measurements Sortav (Blessing 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11821 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.84 _reflns_number_total 5574 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5574 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9816(2) 0.6200(2) 0.7837(2) 0.0599(6) Uani 1 1 d . . . C2 C 0.9904(3) 0.5607(2) 0.8775(2) 0.0741(7) Uani 1 1 d . . . H52A H 0.8951 0.5391 0.8851 0.089 Uiso 1 1 calc R . . H52B H 1.0609 0.6191 0.9604 0.089 Uiso 1 1 calc R . . H52C H 1.0211 0.4838 0.8503 0.089 Uiso 1 1 calc R . . C3 C 0.58906(16) 0.16531(14) 0.17628(15) 0.0330(4) Uani 1 1 d . . . C4 C 0.60352(16) 0.29711(14) 0.06460(15) 0.0337(4) Uani 1 1 d . . . C5 C 0.69335(18) 0.38632(15) 0.29093(16) 0.0380(4) Uani 1 1 d . . . C6 C 0.65733(17) 0.26903(14) 0.29652(15) 0.0341(4) Uani 1 1 d . . . C7 C 0.69108(18) 0.24593(14) 0.41885(15) 0.0355(4) Uani 1 1 d . . . C8 C 0.5819(2) 0.20123(17) 0.45869(18) 0.0461(4) Uani 1 1 d . . . H55A H 0.4837 0.1881 0.4088 0.055 Uiso 1 1 calc R . . C9 C 0.6133(2) 0.17532(19) 0.57013(18) 0.0518(5) Uani 1 1 d . . . H2A H 0.5377 0.1452 0.5969 0.062 Uiso 1 1 calc R . . C10 C 0.7561(2) 0.19416(17) 0.64107(16) 0.0448(4) Uani 1 1 d . . . C11 C 0.8669(2) 0.23856(17) 0.60475(17) 0.0454(4) Uani 1 1 d . . . H4A H 0.9648 0.2518 0.6553 0.055 Uiso 1 1 calc R . . C12 C 0.83391(19) 0.26391(15) 0.49287(16) 0.0412(4) Uani 1 1 d . . . H7A H 0.9100 0.2940 0.4666 0.049 Uiso 1 1 calc R . . C13 C 0.7543(3) 0.50729(16) 0.40492(18) 0.0598(6) Uani 1 1 d . . . H53A H 0.8095 0.4916 0.4807 0.072 Uiso 1 1 calc R . . H53B H 0.8214 0.5689 0.3891 0.072 Uiso 1 1 calc R . . C14 C 0.6343(4) 0.5600(2) 0.4297(4) 0.1391(17) Uani 1 1 d . . . H51A H 0.6726 0.6304 0.5123 0.209 Uiso 1 1 calc R . . H51B H 0.5600 0.4941 0.4313 0.209 Uiso 1 1 calc R . . H51C H 0.5914 0.5901 0.3618 0.209 Uiso 1 1 calc R . . C15 C 0.25635(19) 0.35244(16) 0.91864(18) 0.0410(4) Uani 1 1 d . . . C16 C 0.21966(17) 0.22297(15) 0.92583(16) 0.0370(4) Uani 1 1 d . . . C17 C 0.16616(17) 0.10861(15) 0.82097(16) 0.0363(4) Uani 1 1 d . . . C18 C 0.13353(19) -0.00598(16) 0.83429(19) 0.0441(4) Uani 1 1 d . . . H9A H 0.0969 -0.0817 0.7611 0.053 Uiso 1 1 calc R . . C19 C 0.1541(2) -0.01088(17) 0.95389(19) 0.0494(5) Uani 1 1 d . . . H1A H 0.1320 -0.0899 0.9634 0.059 Uiso 1 1 calc R . . C20 C 0.20691(19) 0.09966(18) 1.06002(19) 0.0493(5) Uani 1 1 d . . . H3A H 0.2210 0.0968 1.1427 0.059 Uiso 1 1 calc R . . C21 C 0.23920(18) 0.21447(16) 1.04563(17) 0.0417(4) Uani 1 1 d . . . H5A H 0.2757 0.2898 1.1194 0.050 Uiso 1 1 calc R . . C22 C 0.23831(19) 0.11957(14) 0.64714(16) 0.0373(4) Uani 1 1 d . . . C23 C 0.18244(19) 0.12163(17) 0.51582(16) 0.0453(4) Uani 1 1 d . . . H6A H 0.2622 0.1305 0.4832 0.068 Uiso 1 1 calc R . . H6B H 0.1407 0.1930 0.5185 0.068 Uiso 1 1 calc R . . H6C H 0.1077 0.0427 0.4595 0.068 Uiso 1 1 calc R . . N1 N 0.66578(14) 0.39934(12) 0.17583(12) 0.0365(3) Uani 1 1 d . . . H24N H 0.6885 0.4751 0.1730 0.044 Uiso 1 1 calc R . . N2 N 0.56465(14) 0.18030(11) 0.06388(12) 0.0351(3) Uani 1 1 d . . . N3 N 0.58281(15) 0.31653(12) -0.04336(13) 0.0419(4) Uani 1 1 d . . . H21A H 0.5431 0.2524 -0.1168 0.050 Uiso 1 1 calc R . . H21B H 0.6087 0.3937 -0.0422 0.050 Uiso 1 1 calc R . . N4 N 0.54682(15) 0.04854(12) 0.17309(14) 0.0410(4) Uani 1 1 d . . . H11A H 0.5048 -0.0148 0.0992 0.049 Uiso 1 1 calc R . . H11B H 0.5609 0.0346 0.2448 0.049 Uiso 1 1 calc R . . N5 N 0.9765(3) 0.6676(2) 0.7118(2) 0.0819(6) Uani 1 1 d . . . O1 O 0.24513(13) 0.36216(10) 0.81276(11) 0.0467(3) Uani 1 1 d . . . O2 O 0.29562(18) 0.44388(12) 1.02223(13) 0.0650(4) Uani 1 1 d . . . O3 O 0.36242(12) 0.12605(10) 0.70400(11) 0.0419(3) Uani 1 1 d . . . O4 O 0.13145(11) 0.10598(10) 0.69491(11) 0.0394(3) Uani 1 1 d . . . Cl1 Cl 0.79554(7) 0.15710(6) 0.77866(5) 0.0691(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0705(14) 0.0535(12) 0.0534(13) 0.0132(11) 0.0305(11) 0.0078(10) C2 0.0916(17) 0.0764(16) 0.0734(15) 0.0359(13) 0.0440(14) 0.0298(13) C3 0.0313(8) 0.0322(8) 0.0367(9) 0.0161(7) 0.0099(7) 0.0087(7) C4 0.0331(8) 0.0326(8) 0.0344(9) 0.0145(7) 0.0090(7) 0.0075(7) C5 0.0472(9) 0.0324(8) 0.0353(9) 0.0139(7) 0.0146(8) 0.0102(7) C6 0.0366(8) 0.0337(8) 0.0346(9) 0.0155(7) 0.0128(7) 0.0106(7) C7 0.0454(10) 0.0294(8) 0.0354(9) 0.0149(7) 0.0155(8) 0.0119(7) C8 0.0434(10) 0.0571(11) 0.0480(10) 0.0285(9) 0.0193(8) 0.0165(8) C9 0.0564(12) 0.0646(12) 0.0519(11) 0.0330(10) 0.0297(10) 0.0211(9) C10 0.0635(12) 0.0496(10) 0.0360(9) 0.0236(8) 0.0247(9) 0.0254(9) C11 0.0476(10) 0.0532(11) 0.0408(10) 0.0217(8) 0.0150(8) 0.0200(8) C12 0.0453(10) 0.0407(9) 0.0413(9) 0.0192(8) 0.0167(8) 0.0106(7) C13 0.1043(16) 0.0318(9) 0.0384(10) 0.0136(8) 0.0223(11) 0.0098(10) C14 0.175(3) 0.0485(14) 0.202(4) -0.0067(18) 0.152(3) 0.0012(17) C15 0.0473(10) 0.0361(9) 0.0453(10) 0.0201(8) 0.0196(8) 0.0106(8) C16 0.0363(8) 0.0371(9) 0.0434(10) 0.0220(8) 0.0150(7) 0.0097(7) C17 0.0329(8) 0.0383(9) 0.0415(9) 0.0206(8) 0.0127(7) 0.0086(7) C18 0.0442(10) 0.0354(9) 0.0559(11) 0.0216(8) 0.0182(9) 0.0089(7) C19 0.0525(11) 0.0419(10) 0.0689(13) 0.0341(10) 0.0281(10) 0.0138(8) C20 0.0497(10) 0.0612(12) 0.0543(12) 0.0377(10) 0.0243(9) 0.0183(9) C21 0.0420(9) 0.0445(10) 0.0445(10) 0.0223(8) 0.0177(8) 0.0116(8) C22 0.0456(10) 0.0255(8) 0.0400(9) 0.0136(7) 0.0145(8) 0.0059(7) C23 0.0494(10) 0.0441(10) 0.0390(10) 0.0171(8) 0.0100(8) 0.0099(8) N1 0.0478(8) 0.0269(7) 0.0356(8) 0.0150(6) 0.0130(6) 0.0084(6) N2 0.0395(7) 0.0302(7) 0.0338(7) 0.0155(6) 0.0079(6) 0.0060(6) N3 0.0558(9) 0.0311(7) 0.0335(8) 0.0142(6) 0.0095(7) 0.0049(6) N4 0.0523(8) 0.0301(7) 0.0369(8) 0.0162(6) 0.0095(7) 0.0052(6) N5 0.1090(16) 0.0706(13) 0.0620(13) 0.0242(11) 0.0354(12) 0.0047(11) O1 0.0651(8) 0.0355(6) 0.0420(7) 0.0224(5) 0.0159(6) 0.0100(6) O2 0.1081(11) 0.0366(7) 0.0499(8) 0.0153(6) 0.0374(8) 0.0033(7) O3 0.0401(7) 0.0467(7) 0.0432(7) 0.0240(6) 0.0129(6) 0.0113(5) O4 0.0381(6) 0.0403(6) 0.0391(6) 0.0180(5) 0.0107(5) 0.0076(5) Cl1 0.0920(4) 0.0927(4) 0.0521(3) 0.0485(3) 0.0341(3) 0.0441(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.131(3) . ? C1 C2 1.449(3) . ? C2 H52A 0.9800 . ? C2 H52B 0.9800 . ? C2 H52C 0.9800 . ? C3 N4 1.330(2) . ? C3 N2 1.339(2) . ? C3 C6 1.436(2) . ? C4 N3 1.316(2) . ? C4 N2 1.337(2) . ? C4 N1 1.3628(19) . ? C5 N1 1.358(2) . ? C5 C6 1.369(2) . ? C5 C13 1.499(2) . ? C6 C7 1.492(2) . ? C7 C8 1.386(2) . ? C7 C12 1.390(2) . ? C8 C9 1.388(3) . ? C8 H55A 0.9500 . ? C9 C10 1.378(3) . ? C9 H2A 0.9500 . ? C10 C11 1.371(3) . ? C10 Cl1 1.7462(18) . ? C11 C12 1.390(2) . ? C11 H4A 0.9500 . ? C12 H7A 0.9500 . ? C13 C14 1.493(4) . ? C13 H53A 0.9900 . ? C13 H53B 0.9900 . ? C14 H51A 0.9800 . ? C14 H51B 0.9800 . ? C14 H51C 0.9800 . ? C15 O2 1.252(2) . ? C15 O1 1.254(2) . ? C15 C16 1.513(2) . ? C16 C21 1.397(2) . ? C16 C17 1.401(2) . ? C17 C18 1.375(2) . ? C17 O4 1.409(2) . ? C18 C19 1.378(3) . ? C18 H9A 0.9500 . ? C19 C20 1.382(3) . ? C19 H1A 0.9500 . ? C20 C21 1.383(3) . ? C20 H3A 0.9500 . ? C21 H5A 0.9500 . ? C22 O3 1.210(2) . ? C22 O4 1.347(2) . ? C22 C23 1.491(2) . ? C23 H6A 0.9800 . ? C23 H6B 0.9800 . ? C23 H6C 0.9800 . ? N1 H24N 0.8800 . ? N3 H21A 0.8800 . ? N3 H21B 0.8800 . ? N4 H11A 0.8800 . ? N4 H11B 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 C1 C2 179.0(3) . . ? C1 C2 H52A 109.5 . . ? C1 C2 H52B 109.5 . . ? H52A C2 H52B 109.5 . . ? C1 C2 H52C 109.5 . . ? H52A C2 H52C 109.5 . . ? H52B C2 H52C 109.5 . . ? N4 C3 N2 117.14(13) . . ? N4 C3 C6 120.25(15) . . ? N2 C3 C6 122.61(14) . . ? N3 C4 N2 120.50(14) . . ? N3 C4 N1 117.85(14) . . ? N2 C4 N1 121.66(15) . . ? N1 C5 C6 119.95(14) . . ? N1 C5 C13 115.33(14) . . ? C6 C5 C13 124.59(16) . . ? C5 C6 C3 116.36(15) . . ? C5 C6 C7 123.25(14) . . ? C3 C6 C7 120.34(14) . . ? C8 C7 C12 118.47(16) . . ? C8 C7 C6 121.29(15) . . ? C12 C7 C6 120.19(15) . . ? C7 C8 C9 121.24(17) . . ? C7 C8 H55A 119.4 . . ? C9 C8 H55A 119.4 . . ? C10 C9 C8 118.71(17) . . ? C10 C9 H2A 120.6 . . ? C8 C9 H2A 120.6 . . ? C11 C10 C9 121.65(17) . . ? C11 C10 Cl1 119.55(15) . . ? C9 C10 Cl1 118.79(15) . . ? C10 C11 C12 119.02(17) . . ? C10 C11 H4A 120.5 . . ? C12 C11 H4A 120.5 . . ? C11 C12 C7 120.92(16) . . ? C11 C12 H7A 119.5 . . ? C7 C12 H7A 119.5 . . ? C14 C13 C5 109.9(2) . . ? C14 C13 H53A 109.7 . . ? C5 C13 H53A 109.7 . . ? C14 C13 H53B 109.7 . . ? C5 C13 H53B 109.7 . . ? H53A C13 H53B 108.2 . . ? C13 C14 H51A 109.5 . . ? C13 C14 H51B 109.5 . . ? H51A C14 H51B 109.5 . . ? C13 C14 H51C 109.5 . . ? H51A C14 H51C 109.5 . . ? H51B C14 H51C 109.5 . . ? O2 C15 O1 124.58(16) . . ? O2 C15 C16 115.85(16) . . ? O1 C15 C16 119.57(15) . . ? C21 C16 C17 116.29(15) . . ? C21 C16 C15 118.46(15) . . ? C17 C16 C15 125.25(16) . . ? C18 C17 C16 122.21(17) . . ? C18 C17 O4 116.34(15) . . ? C16 C17 O4 121.24(15) . . ? C17 C18 C19 119.97(17) . . ? C17 C18 H9A 120.0 . . ? C19 C18 H9A 120.0 . . ? C18 C19 C20 119.75(17) . . ? C18 C19 H1A 120.1 . . ? C20 C19 H1A 120.1 . . ? C19 C20 C21 119.86(18) . . ? C19 C20 H3A 120.1 . . ? C21 C20 H3A 120.1 . . ? C20 C21 C16 121.93(17) . . ? C20 C21 H5A 119.0 . . ? C16 C21 H5A 119.0 . . ? O3 C22 O4 123.36(16) . . ? O3 C22 C23 125.31(16) . . ? O4 C22 C23 111.30(15) . . ? C22 C23 H6A 109.5 . . ? C22 C23 H6B 109.5 . . ? H6A C23 H6B 109.5 . . ? C22 C23 H6C 109.5 . . ? H6A C23 H6C 109.5 . . ? H6B C23 H6C 109.5 . . ? C5 N1 C4 121.16(14) . . ? C5 N1 H24N 119.4 . . ? C4 N1 H24N 119.4 . . ? C4 N2 C3 118.24(13) . . ? C4 N3 H21A 120.0 . . ? C4 N3 H21B 120.0 . . ? H21A N3 H21B 120.0 . . ? C3 N4 H11A 120.0 . . ? C3 N4 H11B 120.0 . . ? H11A N4 H11B 120.0 . . ? C22 O4 C17 119.00(12) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.370 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.044 data_wj1147 _database_code_depnum_ccdc_archive 'CCDC 885650' #TrackingRef 'pyrimethaminium+p-coumarate+water.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic Pyrimethaminium+p-coumarate+water _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 Cl N4 1+, C9 H7 O3 1-, H2 O' _chemical_formula_sum 'C21 H23 Cl N4 O4' _chemical_formula_weight 430.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.60860(10) _cell_length_b 9.9450(2) _cell_length_c 14.6138(3) _cell_angle_alpha 80.9630(10) _cell_angle_beta 87.2240(10) _cell_angle_gamma 72.8160(10) _cell_volume 1043.31(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9187 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.843 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 18083 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 33.65 _reflns_number_total 8180 _reflns_number_gt 5728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8180 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.35017(14) 0.22191(10) 1.02731(7) 0.02889(19) Uani 1 1 d . . . H1 H 0.4015 0.2311 1.0832 0.035 Uiso 1 1 calc R . . C2 C 0.35358(13) 0.31614(9) 0.94694(6) 0.02622(18) Uani 1 1 d . . . H2 H 0.4101 0.3892 0.9480 0.031 Uiso 1 1 calc R . . C3 C 0.27610(12) 0.30628(8) 0.86453(6) 0.02127(16) Uani 1 1 d . . . C4 C 0.19732(13) 0.19562(9) 0.86483(6) 0.02578(18) Uani 1 1 d . . . H4 H 0.1442 0.1863 0.8095 0.031 Uiso 1 1 calc R . . C5 C 0.19525(13) 0.09941(10) 0.94414(7) 0.02786(19) Uani 1 1 d . . . H5 H 0.1426 0.0241 0.9432 0.033 Uiso 1 1 calc R . . C6 C 0.27056(13) 0.11440(9) 1.02450(6) 0.02569(18) Uani 1 1 d . . . C7 C 0.28316(11) 0.40559(8) 0.77820(6) 0.02063(16) Uani 1 1 d . . . C8 C 0.20599(11) 0.55018(9) 0.76960(6) 0.02071(16) Uani 1 1 d . . . C9 C 0.32419(12) 0.57704(9) 0.61648(6) 0.02194(16) Uani 1 1 d . . . C10 C 0.37826(12) 0.35192(9) 0.69737(6) 0.02123(16) Uani 1 1 d . . . C11 C 0.09559(12) 0.62954(9) 0.84299(6) 0.02491(18) Uani 1 1 d . . . H11A H 0.0599 0.5610 0.8915 0.030 Uiso 1 1 calc R . . H11B H -0.0186 0.6974 0.8149 0.030 Uiso 1 1 calc R . . C12 C 0.20145(15) 0.71151(11) 0.88809(8) 0.0345(2) Uani 1 1 d . . . H12A H 0.1221 0.7640 0.9335 0.052 Uiso 1 1 calc R . . H12B H 0.2389 0.7785 0.8403 0.052 Uiso 1 1 calc R . . H12C H 0.3109 0.6443 0.9193 0.052 Uiso 1 1 calc R . . C13 C 0.68515(13) 0.63470(9) 0.72160(7) 0.02549(18) Uani 1 1 d . . . C14 C 0.68168(13) 0.52070(9) 0.78893(7) 0.02742(19) Uani 1 1 d . . . H14 H 0.6239 0.5375 0.8468 0.033 Uiso 1 1 calc R . . C15 C 0.76205(13) 0.38215(9) 0.77230(7) 0.02568(18) Uani 1 1 d . . . H15 H 0.7569 0.3050 0.8188 0.031 Uiso 1 1 calc R . . C16 C 0.85064(12) 0.35399(9) 0.68809(6) 0.02339(17) Uani 1 1 d . . . C17 C 0.85512(14) 0.46982(9) 0.62168(7) 0.02811(19) Uani 1 1 d . . . H17 H 0.9154 0.4531 0.5643 0.034 Uiso 1 1 calc R . . C18 C 0.77390(14) 0.60901(9) 0.63703(7) 0.0295(2) Uani 1 1 d . . . H18 H 0.7784 0.6863 0.5906 0.035 Uiso 1 1 calc R . . C19 C 0.93292(13) 0.20527(9) 0.67500(6) 0.02491(17) Uani 1 1 d . . . H19 H 0.8951 0.1366 0.7177 0.030 Uiso 1 1 calc R . . C20 C 1.05399(14) 0.15395(9) 0.61089(7) 0.02888(19) Uani 1 1 d . . . H20 H 1.0913 0.2183 0.5645 0.035 Uiso 1 1 calc R . . C21 C 1.13235(14) -0.00237(9) 0.61032(7) 0.02771(19) Uani 1 1 d . . . Cl1 Cl 0.26312(4) -0.00380(3) 1.124792(18) 0.03838(8) Uani 1 1 d . . . H1W H 0.813(2) 0.9539(14) 0.6436(10) 0.046 Uiso 1 1 d . . . H2W H 0.688(2) 0.9776(14) 0.5657(11) 0.046 Uiso 1 1 d . . . N1 N 0.22805(10) 0.63380(7) 0.68910(5) 0.02229(15) Uani 1 1 d . . . H1N H 0.1789 0.7266 0.6840 0.027 Uiso 1 1 calc R . . N2 N 0.34333(12) 0.66559(8) 0.54167(5) 0.03005(18) Uani 1 1 d . . . H2A H 0.4034 0.6321 0.4932 0.036 Uiso 1 1 calc R . . H2B H 0.2959 0.7580 0.5404 0.036 Uiso 1 1 calc R . . N3 N 0.39609(10) 0.43602(7) 0.61894(5) 0.02316(15) Uani 1 1 d . . . N4 N 0.45650(11) 0.21239(8) 0.70003(6) 0.02744(17) Uani 1 1 d . . . H4A H 0.5166 0.1795 0.6514 0.033 Uiso 1 1 calc R . . H4B H 0.4480 0.1532 0.7504 0.033 Uiso 1 1 calc R . . O1 O 0.60022(11) 0.76756(7) 0.74080(5) 0.03633(17) Uani 1 1 d . . . H1X H 0.6160 0.8278 0.6965 0.044 Uiso 1 1 calc R . . O2 O 1.26491(11) -0.04384(7) 0.55700(5) 0.03913(19) Uani 1 1 d . . . O3 O 1.06280(10) -0.08573(7) 0.66474(5) 0.03356(16) Uani 1 1 d . . . O1W O 0.69379(12) 0.96846(8) 0.62618(6) 0.03519(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0370(5) 0.0288(4) 0.0211(4) -0.0010(3) -0.0018(4) -0.0111(4) C2 0.0342(5) 0.0237(4) 0.0224(4) -0.0026(3) -0.0009(3) -0.0111(3) C3 0.0227(4) 0.0190(3) 0.0199(4) -0.0019(3) 0.0022(3) -0.0036(3) C4 0.0282(4) 0.0257(4) 0.0239(4) -0.0010(3) -0.0024(3) -0.0095(3) C5 0.0303(5) 0.0234(4) 0.0302(5) 0.0003(3) 0.0002(4) -0.0105(3) C6 0.0277(4) 0.0204(4) 0.0242(4) 0.0021(3) 0.0039(3) -0.0033(3) C7 0.0225(4) 0.0193(4) 0.0187(4) -0.0023(3) 0.0000(3) -0.0043(3) C8 0.0213(4) 0.0208(4) 0.0187(4) -0.0022(3) 0.0002(3) -0.0045(3) C9 0.0239(4) 0.0205(4) 0.0185(4) -0.0018(3) -0.0005(3) -0.0026(3) C10 0.0223(4) 0.0195(3) 0.0203(4) -0.0029(3) -0.0004(3) -0.0037(3) C11 0.0256(4) 0.0221(4) 0.0243(4) -0.0049(3) 0.0056(3) -0.0030(3) C12 0.0372(5) 0.0335(5) 0.0347(5) -0.0162(4) 0.0056(4) -0.0083(4) C13 0.0289(4) 0.0202(4) 0.0276(5) -0.0054(3) 0.0011(3) -0.0067(3) C14 0.0316(5) 0.0250(4) 0.0267(5) -0.0058(3) 0.0049(4) -0.0096(3) C15 0.0287(4) 0.0224(4) 0.0255(4) -0.0009(3) 0.0021(3) -0.0086(3) C16 0.0246(4) 0.0208(4) 0.0244(4) -0.0032(3) -0.0002(3) -0.0062(3) C17 0.0364(5) 0.0225(4) 0.0247(4) -0.0040(3) 0.0054(4) -0.0081(3) C18 0.0401(5) 0.0207(4) 0.0264(5) -0.0011(3) 0.0040(4) -0.0087(4) C19 0.0285(4) 0.0202(4) 0.0250(4) -0.0011(3) -0.0013(3) -0.0064(3) C20 0.0359(5) 0.0190(4) 0.0282(5) -0.0001(3) 0.0041(4) -0.0051(3) C21 0.0314(5) 0.0214(4) 0.0258(5) -0.0017(3) 0.0007(4) -0.0019(3) Cl1 0.04763(16) 0.03294(13) 0.02927(13) 0.01007(9) 0.00243(10) -0.01162(10) N1 0.0256(4) 0.0163(3) 0.0212(4) -0.0020(3) 0.0023(3) -0.0012(3) N2 0.0416(5) 0.0202(3) 0.0208(4) -0.0002(3) 0.0064(3) 0.0000(3) N3 0.0274(4) 0.0194(3) 0.0191(3) -0.0026(3) 0.0009(3) -0.0017(3) N4 0.0349(4) 0.0179(3) 0.0252(4) -0.0031(3) 0.0056(3) -0.0020(3) O1 0.0513(5) 0.0204(3) 0.0352(4) -0.0068(3) 0.0112(3) -0.0077(3) O2 0.0460(4) 0.0269(3) 0.0375(4) -0.0040(3) 0.0156(3) -0.0029(3) O3 0.0366(4) 0.0192(3) 0.0380(4) 0.0009(3) 0.0086(3) -0.0017(3) O1W 0.0415(4) 0.0271(3) 0.0363(4) -0.0066(3) 0.0087(3) -0.0094(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3822(13) . ? C1 C2 1.3871(13) . ? C1 H1 0.9500 . ? C2 C3 1.3955(12) . ? C2 H2 0.9500 . ? C3 C4 1.3994(12) . ? C3 C7 1.4843(12) . ? C4 C5 1.3848(13) . ? C4 H4 0.9500 . ? C5 C6 1.3786(14) . ? C5 H5 0.9500 . ? C6 Cl1 1.7388(9) . ? C7 C8 1.3710(11) . ? C7 C10 1.4460(11) . ? C8 N1 1.3637(11) . ? C8 C11 1.5052(11) . ? C9 N2 1.3229(11) . ? C9 N3 1.3417(10) . ? C9 N1 1.3598(10) . ? C10 N4 1.3337(11) . ? C10 N3 1.3351(11) . ? C11 C12 1.5349(13) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O1 1.3552(10) . ? C13 C14 1.3853(13) . ? C13 C18 1.4019(13) . ? C14 C15 1.3873(12) . ? C14 H14 0.9500 . ? C15 C16 1.4012(13) . ? C15 H15 0.9500 . ? C16 C17 1.3924(12) . ? C16 C19 1.4649(12) . ? C17 C18 1.3881(12) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.3326(13) . ? C19 H19 0.9500 . ? C20 C21 1.4927(12) . ? C20 H20 0.9500 . ? C21 O2 1.2544(11) . ? C21 O3 1.2694(11) . ? N1 H1N 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? O1 H1X 0.8400 . ? O1W H1W 0.917(15) . ? O1W H2W 0.877(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.66(9) . . ? C6 C1 H1 120.7 . . ? C2 C1 H1 120.7 . . ? C1 C2 C3 121.67(8) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 117.70(8) . . ? C2 C3 C7 121.51(8) . . ? C4 C3 C7 120.74(8) . . ? C5 C4 C3 121.32(9) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 119.11(8) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.52(9) . . ? C5 C6 Cl1 119.13(7) . . ? C1 C6 Cl1 119.34(7) . . ? C8 C7 C10 116.06(8) . . ? C8 C7 C3 123.72(7) . . ? C10 C7 C3 120.20(7) . . ? N1 C8 C7 119.56(7) . . ? N1 C8 C11 114.86(7) . . ? C7 C8 C11 125.58(8) . . ? N2 C9 N3 120.31(7) . . ? N2 C9 N1 117.83(7) . . ? N3 C9 N1 121.86(8) . . ? N4 C10 N3 117.09(7) . . ? N4 C10 C7 119.73(8) . . ? N3 C10 C7 123.16(7) . . ? C8 C11 C12 112.75(8) . . ? C8 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C8 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 C14 117.80(8) . . ? O1 C13 C18 122.77(8) . . ? C14 C13 C18 119.43(8) . . ? C13 C14 C15 120.40(8) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 121.13(8) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 117.72(8) . . ? C17 C16 C19 123.89(8) . . ? C15 C16 C19 118.39(8) . . ? C18 C17 C16 121.80(8) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C13 119.52(8) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? C20 C19 C16 128.30(9) . . ? C20 C19 H19 115.9 . . ? C16 C19 H19 115.9 . . ? C19 C20 C21 121.50(9) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? O2 C21 O3 123.78(8) . . ? O2 C21 C20 118.07(9) . . ? O3 C21 C20 118.15(8) . . ? C9 N1 C8 121.50(7) . . ? C9 N1 H1N 119.2 . . ? C8 N1 H1N 119.2 . . ? C9 N2 H2A 120.0 . . ? C9 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C10 N3 C9 117.75(7) . . ? C10 N4 H4A 120.0 . . ? C10 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C13 O1 H1X 109.5 . . ? H1W O1W H2W 109.6(12) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 33.65 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.412 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.048