# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/316 data_compound_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-Amino-5,6-dichloro-pyrimidin-2-yl)-4-(pyridin-4-yl)- pyridinium chloride ; _chemical_name_common ? _chemical_formula_moiety '(C14 H10 Cl2 N5) (Cl) - 2 H2 O' _chemical_formula_sum 'C14 H14 Cl3 N5 O2' _chemical_formula_weight 390.65 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 monoclinic _symmetry_space_group_name_H-M 'P2(1)/n (no.14)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8039(3) _cell_length_b 16.9741(4) _cell_length_c 12.6159(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.222(2) _cell_angle_gamma 90.00 _cell_volume 1649.55(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 23342 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min '0.7823 (theor.)' _exptl_absorpt_correction_T_max '0.8939 (theor.)' _exptl_special_details ; dx = 28.87(1) mm; mos.= 0.822(2); scan 120 sec, 200 frames, 2 deg. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method 'rotation in phi, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22923 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 26.43 _reflns_number_total 3159 _reflns_number_gt 2801 _reflns_threshold_expression >2sigma(I) _computing_data_collection Kappa-CCD _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _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 w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+1.9801P] 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 3159 _refine_ls_number_parameters 234 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.065 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.77878(11) 0.57408(4) 0.36114(6) 0.0291(2) Uiso 0.8917(19) d P A 1 Cl1' Cl 0.7159(9) 0.5579(4) 0.3816(5) 0.0291(2) Uiso 0.1083(19) d P A 2 N1 N 0.5328(2) 0.93741(11) 0.35842(14) 0.0211(4) Uani 1 d . . . C2 C 0.3887(3) 0.95178(13) 0.40049(17) 0.0211(4) Uani 1 d . . . Cl2 Cl 0.29130(7) 1.04162(3) 0.36811(5) 0.02618(16) Uani 1 d . . . C3 C 0.3183(3) 0.89953(13) 0.46447(17) 0.0204(4) Uani 1 d . . . Cl3 Cl 0.13706(7) 0.92025(3) 0.52070(4) 0.02534(16) Uani 1 d . . . C4 C 0.3979(3) 0.82414(13) 0.48062(17) 0.0202(4) Uani 1 d . . . N4 N 0.3352(2) 0.76593(12) 0.53266(16) 0.0242(4) Uani 1 d D . . H4A H 0.379(4) 0.7199(12) 0.526(2) 0.036 Uiso 1 d D . . H4B H 0.243(3) 0.7717(17) 0.561(2) 0.036 Uiso 1 d D . . N5 N 0.5449(2) 0.80989(11) 0.43968(14) 0.0202(4) Uani 1 d . . . C6 C 0.5987(3) 0.86716(13) 0.38340(17) 0.0191(4) Uani 1 d . . . N7 N 0.7568(2) 0.84852(11) 0.33993(14) 0.0189(4) Uani 1 d . . . C8 C 0.8287(3) 0.90325(13) 0.28215(17) 0.0215(4) Uani 1 d . . . H8 H 0.7771 0.9538 0.2704 0.026 Uiso 1 calc R . . C9 C 0.9762(3) 0.88540(13) 0.24061(17) 0.0217(5) Uani 1 d . . . H9 H 1.0255 0.9238 0.1998 0.026 Uiso 1 calc R . . C10 C 1.0551(3) 0.81144(13) 0.25751(16) 0.0200(4) Uani 1 d . . . C11 C 0.9742(3) 0.75622(14) 0.31564(19) 0.0239(5) Uani 1 d . . . H11 H 1.0219 0.7049 0.3273 0.029 Uiso 1 calc R . . C12 C 0.8271(3) 0.77579(13) 0.35569(18) 0.0230(5) Uani 1 d . . . H12 H 0.7735 0.7378 0.3951 0.028 Uiso 1 calc R . . C13 C 1.2170(3) 0.79074(13) 0.21524(16) 0.0203(4) Uani 1 d . . . C14 C 1.2913(3) 0.84261(14) 0.14921(19) 0.0254(5) Uani 1 d . . . H14 H 1.2386 0.8921 0.1300 0.030 Uiso 1 calc R . . C15 C 1.4422(3) 0.82100(15) 0.11227(19) 0.0272(5) Uani 1 d . . . H15 H 1.4900 0.8568 0.0669 0.033 Uiso 1 calc R . . N16 N 1.5247(2) 0.75285(12) 0.13659(16) 0.0249(4) Uani 1 d . . . C17 C 1.4555(3) 0.70340(14) 0.20133(18) 0.0251(5) Uani 1 d . . . H17 H 1.5131 0.6550 0.2207 0.030 Uiso 1 calc R . . C18 C 1.3039(3) 0.71987(13) 0.24115(17) 0.0223(5) Uani 1 d . . . H18 H 1.2591 0.6828 0.2861 0.027 Uiso 1 calc R . . O1W O 0.4577(3) 0.61675(12) 0.48282(17) 0.0424(5) Uani 1 d D . . H1W1 H 0.364(3) 0.5867(19) 0.468(3) 0.064 Uiso 1 d D . . H1W2 H 0.532(3) 0.598(2) 0.447(3) 0.064 Uiso 1 d D . . O2W O 0.1748(3) 0.52588(14) 0.42498(19) 0.0490(5) Uani 1 d D . . H2W1 H 0.064(3) 0.539(2) 0.403(3) 0.074 Uiso 1 d D . . H2W2 H 0.167(5) 0.503(2) 0.488(2) 0.074 Uiso 1 d 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 N1 0.0164(9) 0.0261(10) 0.0210(9) -0.0005(7) 0.0035(7) 0.0013(7) C2 0.0165(10) 0.0239(11) 0.0216(10) -0.0029(8) -0.0005(9) 0.0022(8) Cl2 0.0233(3) 0.0259(3) 0.0294(3) 0.0010(2) 0.0044(2) 0.0067(2) C3 0.0129(9) 0.0286(11) 0.0200(10) -0.0031(9) 0.0037(8) 0.0022(8) Cl3 0.0178(3) 0.0319(3) 0.0282(3) -0.0023(2) 0.0094(2) 0.0049(2) C4 0.0145(10) 0.0286(11) 0.0178(10) -0.0022(8) 0.0031(8) 0.0005(8) N4 0.0189(9) 0.0266(10) 0.0292(10) 0.0028(8) 0.0103(8) 0.0039(8) N5 0.0156(8) 0.0252(9) 0.0201(9) -0.0007(7) 0.0035(7) 0.0016(7) C6 0.0138(10) 0.0258(11) 0.0178(10) -0.0030(8) 0.0025(8) 0.0010(8) N7 0.0142(8) 0.0248(10) 0.0180(8) -0.0005(7) 0.0034(7) 0.0011(7) C8 0.0209(11) 0.0233(11) 0.0204(10) 0.0013(8) 0.0033(9) 0.0013(9) C9 0.0191(10) 0.0269(11) 0.0196(10) 0.0013(8) 0.0042(9) -0.0015(8) C10 0.0171(10) 0.0264(11) 0.0158(10) -0.0014(8) 0.0006(8) 0.0007(8) C11 0.0186(11) 0.0269(11) 0.0271(11) 0.0032(9) 0.0059(9) 0.0039(9) C12 0.0205(11) 0.0241(11) 0.0254(11) 0.0033(9) 0.0069(9) 0.0015(9) C13 0.0163(10) 0.0291(12) 0.0154(9) -0.0024(8) 0.0026(8) -0.0009(8) C14 0.0211(11) 0.0297(12) 0.0264(11) 0.0037(9) 0.0070(9) 0.0029(9) C15 0.0227(11) 0.0357(13) 0.0248(11) 0.0017(10) 0.0086(10) -0.0019(10) N16 0.0179(9) 0.0333(11) 0.0245(10) -0.0017(8) 0.0062(8) -0.0006(8) C17 0.0213(11) 0.0304(12) 0.0240(11) -0.0019(9) 0.0053(9) 0.0031(9) C18 0.0199(10) 0.0271(11) 0.0212(10) 0.0007(9) 0.0066(9) 0.0002(9) O1W 0.0447(12) 0.0397(11) 0.0446(12) -0.0030(9) 0.0127(10) 0.0056(9) O2W 0.0414(11) 0.0535(13) 0.0512(12) 0.0075(10) 0.0042(10) -0.0040(10) _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 N1 C6 1.317(3) . ? N1 C2 1.340(3) . ? C2 C3 1.372(3) . ? C2 Cl2 1.724(2) . ? C3 C4 1.423(3) . ? C3 Cl3 1.717(2) . ? C4 N4 1.323(3) . ? C4 N5 1.354(3) . ? N4 H4A 0.862(17) . ? N4 H4B 0.857(18) . ? N5 C6 1.312(3) . ? C6 N7 1.463(3) . ? N7 C12 1.352(3) . ? N7 C8 1.357(3) . ? C8 C9 1.373(3) . ? C8 H8 0.9500 . ? C9 C10 1.399(3) . ? C9 H9 0.9500 . ? C10 C11 1.401(3) . ? C10 C13 1.490(3) . ? C11 C12 1.368(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.394(3) . ? C13 C14 1.400(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 N16 1.335(3) . ? C15 H15 0.9500 . ? N16 C17 1.343(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O1W H1W1 0.890(18) . ? O1W H1W2 0.857(18) . ? O2W H2W1 0.898(18) . ? O2W H2W2 0.892(18) . ? 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 N1 C2 112.98(19) . . ? N1 C2 C3 123.8(2) . . ? N1 C2 Cl2 115.68(17) . . ? C3 C2 Cl2 120.55(17) . . ? C2 C3 C4 117.32(19) . . ? C2 C3 Cl3 123.01(17) . . ? C4 C3 Cl3 119.63(17) . . ? N4 C4 N5 117.4(2) . . ? N4 C4 C3 123.73(19) . . ? N5 C4 C3 118.9(2) . . ? C4 N4 H4A 116(2) . . ? C4 N4 H4B 122(2) . . ? H4A N4 H4B 121(3) . . ? C6 N5 C4 116.01(19) . . ? N5 C6 N1 130.8(2) . . ? N5 C6 N7 113.88(18) . . ? N1 C6 N7 115.27(19) . . ? C12 N7 C8 120.74(18) . . ? C12 N7 C6 119.25(18) . . ? C8 N7 C6 119.98(18) . . ? N7 C8 C9 119.9(2) . . ? N7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 121.0(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 117.1(2) . . ? C9 C10 C13 122.3(2) . . ? C11 C10 C13 120.6(2) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? N7 C12 C11 120.8(2) . . ? N7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C18 C13 C14 116.7(2) . . ? C18 C13 C10 121.9(2) . . ? C14 C13 C10 121.4(2) . . ? C15 C14 C13 119.3(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N16 C15 C14 123.9(2) . . ? N16 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? C15 N16 C17 117.08(19) . . ? N16 C17 C18 123.0(2) . . ? N16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C17 C18 C13 120.0(2) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? H1W1 O1W H1W2 106(2) . . ? H2W1 O2W H2W2 100(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 C6 N1 C2 C3 1.1(3) . . . . ? C6 N1 C2 Cl2 -178.22(15) . . . . ? N1 C2 C3 C4 -4.2(3) . . . . ? Cl2 C2 C3 C4 175.05(16) . . . . ? N1 C2 C3 Cl3 178.07(16) . . . . ? Cl2 C2 C3 Cl3 -2.7(3) . . . . ? C2 C3 C4 N4 -174.1(2) . . . . ? Cl3 C3 C4 N4 3.7(3) . . . . ? C2 C3 C4 N5 5.0(3) . . . . ? Cl3 C3 C4 N5 -177.16(15) . . . . ? N4 C4 N5 C6 176.33(19) . . . . ? C3 C4 N5 C6 -2.8(3) . . . . ? C4 N5 C6 N1 -0.6(3) . . . . ? C4 N5 C6 N7 -179.32(17) . . . . ? C2 N1 C6 N5 1.6(3) . . . . ? C2 N1 C6 N7 -179.72(17) . . . . ? N5 C6 N7 C12 3.2(3) . . . . ? N1 C6 N7 C12 -175.74(19) . . . . ? N5 C6 N7 C8 -178.51(19) . . . . ? N1 C6 N7 C8 2.6(3) . . . . ? C12 N7 C8 C9 -1.2(3) . . . . ? C6 N7 C8 C9 -179.42(19) . . . . ? N7 C8 C9 C10 -0.5(3) . . . . ? C8 C9 C10 C11 1.8(3) . . . . ? C8 C9 C10 C13 -178.86(19) . . . . ? C9 C10 C11 C12 -1.6(3) . . . . ? C13 C10 C11 C12 179.0(2) . . . . ? C8 N7 C12 C11 1.3(3) . . . . ? C6 N7 C12 C11 179.6(2) . . . . ? C10 C11 C12 N7 0.1(3) . . . . ? C9 C10 C13 C18 173.7(2) . . . . ? C11 C10 C13 C18 -7.0(3) . . . . ? C9 C10 C13 C14 -4.9(3) . . . . ? C11 C10 C13 C14 174.4(2) . . . . ? C18 C13 C14 C15 1.0(3) . . . . ? C10 C13 C14 C15 179.7(2) . . . . ? C13 C14 C15 N16 -0.6(4) . . . . ? C14 C15 N16 C17 -0.4(3) . . . . ? C15 N16 C17 C18 1.1(3) . . . . ? N16 C17 C18 C13 -0.7(3) . . . . ? C14 C13 C18 C17 -0.4(3) . . . . ? C10 C13 C18 C17 -179.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O1W 0.862(17) 1.961(19) 2.813(3) 169(3) . N4 H4B N16 0.857(18) 2.12(2) 2.951(3) 162(3) 4_476 O1W H1W1 O2W 0.890(18) 1.808(19) 2.696(3) 175(3) . O1W H1W2 Cl1 0.857(18) 2.386(18) 3.224(2) 166(3) . O1W H1W2 Cl1' 0.857(18) 1.887(19) 2.740(7) 173(3) . O2W H2W1 Cl1 0.898(18) 2.278(19) 3.174(2) 176(3) 1_455 O2W H2W1 Cl1' 0.898(18) 2.70(2) 3.577(7) 165(3) 1_455 O2W H2W2 Cl1 0.892(18) 2.297(19) 3.159(2) 162(3) 3_666 O2W H2W2 Cl1' 0.892(18) 2.04(2) 2.835(6) 148(3) 3_666 _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 0.615 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.067