# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_1.HClO4 _database_code_CSD 184182 _journal_coden_Cambridge 182 loop_ _publ_author_name 'R.J.H.Davies' 'J.F.Malone' _publ_contact_author_name 'Prof R J H Davies' _publ_contact_author_address ; School of Biology & Biochemistry Queen's University BELFAST BT9 7BL NORTHERN IRELAND ; _publ_contact_author_email j.davies@qub.ac.uk _publ_requested_journal 'Chemical Communications' _publ_section_title ; Novel oxidation products from guanine nucleosides reacted with dimethyldioxirane ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-amidiniumcarbamoyl-5-hydroxyimidazole perchlorate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Cl N5 O6' _chemical_formula_weight 269.61 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.825(3) _cell_length_b 9.812(5) _cell_length_c 10.052(5) _cell_angle_alpha 100.444(7) _cell_angle_beta 94.615(7) _cell_angle_gamma 91.416(7) _cell_volume 466.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thin plates' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 0.8915 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5488 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.82 _reflns_number_total 2123 _reflns_number_gt 1359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0603P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refined _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2123 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 N1 N 0.2318(6) 1.1369(3) 0.9706(3) 0.0187(6) Uani 1 1 d . . . H1 H 0.127(9) 1.135(4) 1.032(4) 0.042(13) Uiso 1 1 d . . . C2 C 0.4048(7) 1.2429(4) 0.9634(4) 0.0201(7) Uani 1 1 d . . . H2 H 0.423(6) 1.327(3) 1.015(3) 0.009(8) Uiso 1 1 d . . . N3 N 0.5642(6) 1.2061(3) 0.8650(3) 0.0188(6) Uani 1 1 d . . . H3 H 0.667(9) 1.257(5) 0.838(4) 0.049(14) Uiso 1 1 d . . . C4 C 0.4977(6) 1.0690(3) 0.8035(3) 0.0169(7) Uani 1 1 d . . . C5 C 0.2822(7) 1.0230(3) 0.8722(3) 0.0186(7) Uani 1 1 d . . . O5 O 0.1565(5) 0.9069(2) 0.8541(2) 0.0214(5) Uani 1 1 d . . . C1' C 0.6221(7) 0.9972(3) 0.6891(3) 0.0185(7) Uani 1 1 d . . . O1' O 0.8043(5) 1.0471(2) 0.6310(2) 0.0226(6) Uani 1 1 d . . . N2' N 0.5100(7) 0.8629(3) 0.6462(3) 0.0198(7) Uani 1 1 d . . . H2' H 0.415(9) 0.843(5) 0.676(4) 0.032(15) Uiso 1 1 d . . . C3' C 0.5686(7) 0.7727(3) 0.5351(3) 0.0184(7) Uani 1 1 d . . . N4' N 0.4180(6) 0.6569(3) 0.4987(3) 0.0208(7) Uani 1 1 d . . . H4'A H 0.285(9) 0.645(4) 0.545(4) 0.040(13) Uiso 1 1 d . . . H4'B H 0.428(7) 0.604(3) 0.430(3) 0.008(9) Uiso 1 1 d . . . N5' N 0.7775(6) 0.8013(3) 0.4661(3) 0.0202(6) Uani 1 1 d . . . H5'A H 0.868(8) 0.885(4) 0.501(4) 0.035(11) Uiso 1 1 d . . . H5'B H 0.819(7) 0.744(4) 0.396(4) 0.023(10) Uiso 1 1 d . . . Cl1 Cl 0.10368(16) 0.51630(8) 0.77766(8) 0.0190(2) Uani 1 1 d . . . O1 O -0.0086(5) 0.3764(2) 0.7658(2) 0.0236(6) Uani 1 1 d . . . O2 O 0.4010(4) 0.5099(3) 0.7697(2) 0.0264(6) Uani 1 1 d . . . O3 O 0.0452(5) 0.5987(2) 0.9028(2) 0.0263(6) Uani 1 1 d . . . O4 O -0.0161(5) 0.5737(3) 0.6645(2) 0.0280(6) 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 N1 0.0147(15) 0.0224(15) 0.0195(16) 0.0022(12) 0.0082(12) -0.0016(12) C2 0.0153(18) 0.0211(18) 0.0227(19) 0.0002(15) 0.0031(14) 0.0001(14) N3 0.0128(15) 0.0203(15) 0.0241(16) 0.0040(12) 0.0067(12) 0.0004(12) C4 0.0105(16) 0.0191(17) 0.0209(18) 0.0024(14) 0.0042(13) -0.0007(13) C5 0.0140(17) 0.0238(18) 0.0183(17) 0.0034(14) 0.0034(13) 0.0005(14) O5 0.0164(12) 0.0205(12) 0.0274(14) 0.0024(10) 0.0085(10) -0.0028(10) C1' 0.0129(17) 0.0250(18) 0.0190(18) 0.0066(14) 0.0045(13) -0.0001(14) O1' 0.0174(13) 0.0252(13) 0.0262(13) 0.0046(10) 0.0099(10) -0.0027(10) N2' 0.0151(16) 0.0206(16) 0.0229(17) -0.0013(13) 0.0099(13) -0.0033(13) C3' 0.0153(17) 0.0214(18) 0.0191(18) 0.0044(14) 0.0026(13) 0.0005(14) N4' 0.0173(16) 0.0216(16) 0.0221(18) -0.0019(14) 0.0085(13) -0.0027(12) N5' 0.0165(15) 0.0214(16) 0.0230(17) 0.0003(13) 0.0129(12) -0.0034(12) Cl1 0.0119(4) 0.0234(4) 0.0213(5) 0.0018(3) 0.0060(3) -0.0020(3) O1 0.0205(13) 0.0220(12) 0.0276(14) 0.0005(10) 0.0089(10) -0.0043(10) O2 0.0064(12) 0.0390(15) 0.0321(14) 0.0008(12) 0.0059(10) -0.0021(10) O3 0.0264(14) 0.0265(13) 0.0239(14) -0.0045(11) 0.0109(11) -0.0011(11) O4 0.0207(13) 0.0402(15) 0.0254(14) 0.0128(11) 0.0015(11) -0.0031(11) _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 C2 1.333(4) . ? N1 C5 1.392(4) . ? C2 N3 1.307(4) . ? N3 C4 1.393(4) . ? C4 C5 1.402(4) . ? C4 C1' 1.420(5) . ? C5 O5 1.254(4) . ? C1' O1' 1.233(4) . ? C1' N2' 1.392(4) . ? N2' C3' 1.347(4) . ? C3' N4' 1.311(4) . ? C3' N5' 1.321(4) . ? Cl1 O3 1.420(2) . ? Cl1 O1 1.444(2) . ? Cl1 O4 1.445(2) . ? Cl1 O2 1.445(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 C2 N1 C5 109.8(3) . . ? N3 C2 N1 109.4(3) . . ? C2 N3 C4 109.4(3) . . ? N3 C4 C5 106.6(3) . . ? N3 C4 C1' 124.5(3) . . ? C5 C4 C1' 128.8(3) . . ? O5 C5 N1 125.3(3) . . ? O5 C5 C4 129.9(3) . . ? N1 C5 C4 104.7(3) . . ? O1' C1' N2' 122.8(3) . . ? O1' C1' C4 124.8(3) . . ? N2' C1' C4 112.4(3) . . ? C3' N2' C1' 126.6(3) . . ? N4' C3' N5' 121.3(3) . . ? N4' C3' N2' 119.0(3) . . ? N5' C3' N2' 119.7(3) . . ? O3 Cl1 O1 110.63(14) . . ? O3 Cl1 O4 110.73(16) . . ? O1 Cl1 O4 108.54(15) . . ? O3 Cl1 O2 110.13(15) . . ? O1 Cl1 O2 107.99(14) . . ? O4 Cl1 O2 108.76(14) . . ? 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 C5 N1 C2 N3 0.7(4) . . . . ? N1 C2 N3 C4 -0.4(4) . . . . ? C2 N3 C4 C5 0.0(4) . . . . ? C2 N3 C4 C1' 177.2(3) . . . . ? C2 N1 C5 O5 179.0(3) . . . . ? C2 N1 C5 C4 -0.7(4) . . . . ? N3 C4 C5 O5 -179.2(3) . . . . ? C1' C4 C5 O5 3.7(6) . . . . ? N3 C4 C5 N1 0.4(3) . . . . ? C1' C4 C5 N1 -176.6(3) . . . . ? N3 C4 C1' O1' 0.4(5) . . . . ? C5 C4 C1' O1' 177.0(3) . . . . ? N3 C4 C1' N2' -178.1(3) . . . . ? C5 C4 C1' N2' -1.5(5) . . . . ? O1' C1' N2' C3' -3.8(5) . . . . ? C4 C1' N2' C3' 174.7(3) . . . . ? C1' N2' C3' N4' -170.9(3) . . . . ? C1' N2' C3' N5' 9.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.868 _diffrn_reflns_theta_full 28.82 _diffrn_measured_fraction_theta_full 0.868 _refine_diff_density_max 0.389 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.089