# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Pilar Souza' _publ_contact_author_address ; Departamento de Quimica Inorganica Facultad de Ciencias Universidad Autonoma de Madrid Cantoblanco Madrid 28049 ; _publ_contact_author_email PILAR.SOUZA@UAM.ES loop_ _publ_author_name 'Pilar Souza' 'Celine Joie' 'Ana I. Matesanz' # Attachment 'Pt-complex.cif' data_datos_0m_Pt _database_code_depnum_ccdc_archive 'CCDC 741353' #TrackingRef 'Pt-complex.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H38 N18 O Pt2 S4' _chemical_formula_weight 1113.14 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.1428(7) _cell_length_b 12.4059(10) _cell_length_c 19.2779(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.615(4) _cell_angle_gamma 90.00 _cell_volume 1934.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9955 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 30.38 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 7.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3159 _exptl_absorpt_correction_T_max 0.4669 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54344 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5654 _reflns_number_gt 4369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0503P)^2^+6.2079P] 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 5654 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.221 _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 Pt1 Pt 0.37292(2) 0.178191(18) 0.175737(12) 0.03431(9) Uani 1 1 d . . . S1 S 0.2702(2) 0.31808(14) 0.10993(11) 0.0521(4) Uani 1 1 d . . . S2 S 0.24134(18) 0.05629(14) 0.09934(9) 0.0428(4) Uani 1 1 d . . . C1 C 0.3643(7) 0.4207(6) 0.1685(3) 0.0425(14) Uani 1 1 d . . . C2 C 0.5816(7) 0.2626(5) 0.2917(3) 0.0392(13) Uani 1 1 d . . . C3 C 0.5951(7) 0.1458(5) 0.2980(3) 0.0329(11) Uani 1 1 d . . . C4 C 0.6473(6) -0.0161(5) 0.3203(3) 0.0314(11) Uani 1 1 d . . . C5 C 0.7246(7) -0.1165(5) 0.3476(3) 0.0342(11) Uani 1 1 d . . . C6 C 0.6326(8) -0.2199(6) 0.3303(4) 0.0502(17) Uani 1 1 d . . . H6A H 0.6976 -0.2796 0.3497 0.075 Uiso 1 1 calc R . . H6B H 0.6123 -0.2278 0.2805 0.075 Uiso 1 1 calc R . . H6C H 0.5292 -0.2183 0.3497 0.075 Uiso 1 1 calc R . . C7 C 0.4181(17) 0.6094(8) 0.1902(7) 0.109(4) Uani 1 1 d . . . H7A H 0.3924 0.6055 0.2375 0.164 Uiso 1 1 calc R . . H7B H 0.3838 0.6780 0.1706 0.164 Uiso 1 1 calc R . . H7C H 0.5352 0.6012 0.1896 0.164 Uiso 1 1 calc R . . C8 C 0.2196(15) 0.5536(9) 0.0897(7) 0.111(4) Uani 1 1 d . . . H8A H 0.2540 0.5212 0.0486 0.166 Uiso 1 1 calc R . . H8B H 0.2195 0.6306 0.0849 0.166 Uiso 1 1 calc R . . H8C H 0.1103 0.5294 0.0959 0.166 Uiso 1 1 calc R . . C9 C 0.6732(10) 0.3380(6) 0.3422(4) 0.0528(17) Uani 1 1 d . . . H9A H 0.7135 0.3977 0.3173 0.079 Uiso 1 1 calc R . . H9B H 0.7647 0.3010 0.3675 0.079 Uiso 1 1 calc R . . H9C H 0.6005 0.3641 0.3743 0.079 Uiso 1 1 calc R . . C10 C 0.3758(6) -0.0439(5) 0.0808(3) 0.0347(11) Uani 1 1 d . . . C11 C 0.4213(10) -0.1914(6) -0.0008(6) 0.063(2) Uani 1 1 d . . . H11A H 0.5255 -0.1563 -0.0033 0.094 Uiso 1 1 calc R . . H11B H 0.3649 -0.1997 -0.0470 0.094 Uiso 1 1 calc R . . H11C H 0.4399 -0.2611 0.0204 0.094 Uiso 1 1 calc R . . C12 C 0.1425(9) -0.1402(7) 0.0225(4) 0.0559(18) Uani 1 1 d . . . H12A H 0.0842 -0.1197 0.0610 0.084 Uiso 1 1 calc R . . H12B H 0.1201 -0.2145 0.0111 0.084 Uiso 1 1 calc R . . H12C H 0.1065 -0.0960 -0.0173 0.084 Uiso 1 1 calc R . . O1 O 0.2500 0.8349(7) 0.2500 0.143(7) Uani 1 2 d S . . N1 N 0.3315(10) 0.5233(6) 0.1492(5) 0.075(2) Uani 1 1 d . . . N2 N 0.4566(7) 0.4007(4) 0.2249(4) 0.0503(14) Uani 1 1 d . . . N3 N 0.4820(6) 0.2933(4) 0.2390(3) 0.0338(10) Uani 1 1 d . . . N4 N 0.4984(5) 0.0838(4) 0.2512(2) 0.0311(9) Uani 1 1 d . . . N5 N 0.5298(5) -0.0192(4) 0.2653(3) 0.0331(10) Uani 1 1 d . . . N6 N 0.6911(6) 0.0850(4) 0.3426(3) 0.0344(10) Uani 1 1 d . . . N7 N 0.5380(6) -0.0347(4) 0.1045(3) 0.0365(10) Uani 1 1 d . . . H7 H 0.5823 0.0279 0.1111 0.044 Uiso 1 1 calc R . . N8 N 0.6319(6) -0.1263(4) 0.1181(3) 0.0385(11) Uani 1 1 d . . . N9 N 0.3192(6) -0.1256(4) 0.0416(3) 0.0395(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 Pt1 0.02565(12) 0.03651(13) 0.04064(14) 0.00129(9) 0.00325(8) 0.00522(8) S1 0.0494(10) 0.0477(9) 0.0582(11) 0.0142(8) 0.0026(8) 0.0148(7) S2 0.0267(6) 0.0525(9) 0.0470(9) -0.0059(7) -0.0049(6) 0.0054(6) C1 0.040(3) 0.046(3) 0.042(3) 0.014(3) 0.011(3) 0.013(3) C2 0.031(3) 0.044(3) 0.043(3) -0.002(3) 0.006(2) 0.003(2) C3 0.026(2) 0.038(3) 0.035(3) -0.002(2) 0.005(2) 0.002(2) C4 0.027(2) 0.036(3) 0.032(3) 0.001(2) 0.005(2) -0.003(2) C5 0.029(3) 0.037(3) 0.036(3) 0.000(2) 0.002(2) -0.002(2) C6 0.044(4) 0.040(3) 0.065(5) -0.001(3) -0.001(3) -0.006(3) C7 0.147(11) 0.035(4) 0.148(11) -0.005(6) 0.024(9) -0.001(6) C8 0.114(9) 0.062(6) 0.144(11) 0.038(7) -0.034(8) 0.013(6) C9 0.053(4) 0.046(4) 0.058(4) -0.011(3) 0.004(3) -0.005(3) C10 0.027(2) 0.040(3) 0.036(3) 0.006(2) -0.002(2) -0.001(2) C11 0.057(5) 0.040(4) 0.097(7) -0.027(4) 0.033(5) -0.009(3) C12 0.041(4) 0.065(5) 0.058(5) -0.004(4) -0.008(3) -0.013(3) O1 0.044(5) 0.039(5) 0.33(2) 0.000 -0.052(8) 0.000 N1 0.076(5) 0.046(4) 0.102(6) 0.012(4) 0.004(4) 0.011(3) N2 0.049(3) 0.032(3) 0.072(4) 0.000(3) 0.018(3) 0.004(2) N3 0.029(2) 0.032(2) 0.043(3) -0.003(2) 0.009(2) 0.0010(18) N4 0.023(2) 0.039(2) 0.031(2) -0.0027(19) 0.0043(17) -0.0012(17) N5 0.027(2) 0.036(2) 0.036(2) -0.0007(19) 0.0035(18) 0.0000(18) N6 0.029(2) 0.038(3) 0.036(2) -0.005(2) 0.0019(19) -0.0042(19) N7 0.027(2) 0.039(3) 0.041(3) -0.002(2) -0.0032(19) 0.0013(19) N8 0.034(2) 0.037(3) 0.042(3) -0.002(2) -0.002(2) 0.002(2) N9 0.038(3) 0.044(3) 0.036(3) -0.002(2) 0.000(2) -0.003(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 Pt1 N3 2.016(5) . ? Pt1 N4 2.047(5) . ? Pt1 S1 2.2532(17) . ? Pt1 S2 2.2892(16) . ? S1 C1 1.813(8) . ? S2 C10 1.721(6) . ? C1 N2 1.271(9) . ? C1 N1 1.345(9) . ? C2 N3 1.283(8) . ? C2 C3 1.457(9) . ? C2 C9 1.487(10) . ? C3 N6 1.329(8) . ? C3 N4 1.364(7) . ? C4 N5 1.343(7) . ? C4 N6 1.361(7) . ? C4 C5 1.466(8) . ? C5 N8 1.281(7) 2_655 ? C5 C6 1.503(9) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N1 1.461(14) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.430(13) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N9 1.315(8) . ? C10 N7 1.352(7) . ? C11 N9 1.478(9) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N9 1.456(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N2 N3 1.371(7) . ? N4 N5 1.325(7) . ? N7 N8 1.377(7) . ? N7 H7 0.8600 . ? N8 C5 1.281(7) 2_655 ? 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 N3 Pt1 N4 80.0(2) . . ? N3 Pt1 S1 84.50(16) . . ? N4 Pt1 S1 164.48(14) . . ? N3 Pt1 S2 176.26(15) . . ? N4 Pt1 S2 103.74(14) . . ? S1 Pt1 S2 91.76(7) . . ? C1 S1 Pt1 95.0(2) . . ? C10 S2 Pt1 110.4(2) . . ? N2 C1 N1 120.0(7) . . ? N2 C1 S1 124.2(5) . . ? N1 C1 S1 115.8(6) . . ? N3 C2 C3 113.3(6) . . ? N3 C2 C9 123.7(6) . . ? C3 C2 C9 123.0(6) . . ? N6 C3 N4 111.1(5) . . ? N6 C3 C2 130.6(6) . . ? N4 C3 C2 118.3(5) . . ? N5 C4 N6 114.4(5) . . ? N5 C4 C5 119.8(5) . . ? N6 C4 C5 125.7(5) . . ? N8 C5 C4 126.5(5) 2_655 . ? N8 C5 C6 115.8(5) 2_655 . ? C4 C5 C6 117.6(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N9 C10 N7 121.5(5) . . ? N9 C10 S2 119.1(4) . . ? N7 C10 S2 119.3(5) . . ? N9 C11 H11A 109.5 . . ? N9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N9 C12 H12A 109.5 . . ? N9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 N1 C8 124.0(8) . . ? C1 N1 C7 118.2(9) . . ? C8 N1 C7 117.8(8) . . ? C1 N2 N3 114.8(6) . . ? C2 N3 N2 120.9(6) . . ? C2 N3 Pt1 117.6(4) . . ? N2 N3 Pt1 121.5(4) . . ? N5 N4 C3 109.0(5) . . ? N5 N4 Pt1 140.0(4) . . ? C3 N4 Pt1 110.5(4) . . ? N4 N5 C4 103.7(5) . . ? C3 N6 C4 101.8(5) . . ? C10 N7 N8 119.6(5) . . ? C10 N7 H7 120.2 . . ? N8 N7 H7 120.2 . . ? C5 N8 N7 118.3(5) 2_655 . ? C10 N9 C12 120.8(6) . . ? C10 N9 C11 124.2(5) . . ? C12 N9 C11 113.2(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 N3 Pt1 S1 C1 -1.5(2) . . . . ? N4 Pt1 S1 C1 -5.1(5) . . . . ? S2 Pt1 S1 C1 178.4(2) . . . . ? N3 Pt1 S2 C10 134(2) . . . . ? N4 Pt1 S2 C10 -46.6(2) . . . . ? S1 Pt1 S2 C10 132.4(2) . . . . ? Pt1 S1 C1 N2 1.2(6) . . . . ? Pt1 S1 C1 N1 -178.9(5) . . . . ? N3 C2 C3 N6 175.8(6) . . . . ? C9 C2 C3 N6 -4.9(10) . . . . ? N3 C2 C3 N4 -3.2(8) . . . . ? C9 C2 C3 N4 176.2(6) . . . . ? N5 C4 C5 N8 155.2(6) . . . 2_655 ? N6 C4 C5 N8 -20.1(9) . . . 2_655 ? N5 C4 C5 C6 -20.5(8) . . . . ? N6 C4 C5 C6 164.2(6) . . . . ? Pt1 S2 C10 N9 175.1(4) . . . . ? Pt1 S2 C10 N7 -7.3(5) . . . . ? N2 C1 N1 C8 -175.1(9) . . . . ? S1 C1 N1 C8 5.0(12) . . . . ? N2 C1 N1 C7 6.5(12) . . . . ? S1 C1 N1 C7 -173.4(8) . . . . ? N1 C1 N2 N3 -179.7(6) . . . . ? S1 C1 N2 N3 0.2(8) . . . . ? C3 C2 N3 N2 -179.1(5) . . . . ? C9 C2 N3 N2 1.6(9) . . . . ? C3 C2 N3 Pt1 -1.8(7) . . . . ? C9 C2 N3 Pt1 178.9(5) . . . . ? C1 N2 N3 C2 175.2(6) . . . . ? C1 N2 N3 Pt1 -2.0(7) . . . . ? N4 Pt1 N3 C2 4.0(4) . . . . ? S1 Pt1 N3 C2 -175.1(4) . . . . ? S2 Pt1 N3 C2 -176.6(18) . . . . ? N4 Pt1 N3 N2 -178.7(4) . . . . ? S1 Pt1 N3 N2 2.2(4) . . . . ? S2 Pt1 N3 N2 1(2) . . . . ? N6 C3 N4 N5 0.4(6) . . . . ? C2 C3 N4 N5 179.5(5) . . . . ? N6 C3 N4 Pt1 -173.0(4) . . . . ? C2 C3 N4 Pt1 6.1(6) . . . . ? N3 Pt1 N4 N5 -175.4(6) . . . . ? S1 Pt1 N4 N5 -171.8(4) . . . . ? S2 Pt1 N4 N5 4.6(6) . . . . ? N3 Pt1 N4 C3 -5.2(4) . . . . ? S1 Pt1 N4 C3 -1.6(7) . . . . ? S2 Pt1 N4 C3 174.8(3) . . . . ? C3 N4 N5 C4 -0.7(6) . . . . ? Pt1 N4 N5 C4 169.6(4) . . . . ? N6 C4 N5 N4 0.8(6) . . . . ? C5 C4 N5 N4 -175.0(5) . . . . ? N4 C3 N6 C4 0.1(6) . . . . ? C2 C3 N6 C4 -178.9(6) . . . . ? N5 C4 N6 C3 -0.6(6) . . . . ? C5 C4 N6 C3 174.9(5) . . . . ? N9 C10 N7 N8 -30.9(8) . . . . ? S2 C10 N7 N8 151.6(4) . . . . ? C10 N7 N8 C5 -167.3(5) . . . 2_655 ? N7 C10 N9 C12 173.6(6) . . . . ? S2 C10 N9 C12 -8.9(8) . . . . ? N7 C10 N9 C11 -22.9(10) . . . . ? S2 C10 N9 C11 154.6(6) . . . . ? 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 N7 H7 N6 0.86 2.08 2.755(7) 135.1 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.256 _refine_diff_density_min -1.687 _refine_diff_density_rms 0.271 data_datos_0m _database_code_depnum_ccdc_archive 'CCDC 763617' #TrackingRef 'Ligand.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H29 N9 O2 S4' _chemical_formula_weight 483.70 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.5254(7) _cell_length_b 11.4690(6) _cell_length_c 17.0475(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.249(2) _cell_angle_gamma 90.00 _cell_volume 2325.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9831 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.74 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.438 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8797 _exptl_absorpt_correction_T_max 0.9575 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 85578 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.80 _reflns_number_total 6025 _reflns_number_gt 5072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0648P)^2^+3.3279P] 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 6025 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 S1 S 0.26069(5) 0.38455(5) 0.09844(3) 0.02485(14) Uani 1 1 d . . . S2 S 0.22080(5) 0.37053(6) 0.71021(4) 0.03006(15) Uani 1 1 d . . . S3 S -0.00816(5) 0.66344(5) 0.16129(3) 0.02578(14) Uani 1 1 d . . . S4 S 0.97162(4) 0.26580(5) 0.50676(3) 0.02176(13) Uani 1 1 d . . . C1 C 0.2975(3) 0.5494(2) -0.03654(14) 0.0373(6) Uani 1 1 d . . . H1A H 0.3363 0.4791 -0.0457 0.056 Uiso 1 1 calc R . . H1B H 0.3119 0.6135 -0.0699 0.056 Uiso 1 1 calc R . . H1C H 0.2164 0.5344 -0.0526 0.056 Uiso 1 1 calc R . . C2 C 0.32610(17) 0.51468(18) 0.11046(13) 0.0186(4) Uani 1 1 d . . . C3 C 0.46111(17) 0.70858(18) 0.27149(12) 0.0181(4) Uani 1 1 d . . . C4 C 0.5253(2) 0.8205(2) 0.27869(14) 0.0272(5) Uani 1 1 d . . . H4A H 0.5272 0.8444 0.2239 0.041 Uiso 1 1 calc R . . H4B H 0.6023 0.8091 0.3154 0.041 Uiso 1 1 calc R . . H4C H 0.4884 0.8812 0.3014 0.041 Uiso 1 1 calc R . . C5 C 0.44106(16) 0.66324(17) 0.34625(12) 0.0156(4) Uani 1 1 d . . . C6 C 0.38002(15) 0.56305(17) 0.42685(11) 0.0146(3) Uani 1 1 d . . . C7 C 0.32305(15) 0.47715(17) 0.46333(12) 0.0151(4) Uani 1 1 d . . . C8 C 0.26230(19) 0.37785(19) 0.41183(13) 0.0224(4) Uani 1 1 d . . . H8A H 0.2838 0.3048 0.4426 0.034 Uiso 1 1 calc R . . H8B H 0.2822 0.3740 0.3607 0.034 Uiso 1 1 calc R . . H8C H 0.1810 0.3896 0.3984 0.034 Uiso 1 1 calc R . . C9 C 0.29324(17) 0.44904(19) 0.66101(12) 0.0187(4) Uani 1 1 d . . . C10 C 0.3873(2) 0.5681(2) 0.78106(13) 0.0263(5) Uani 1 1 d . . . H10A H 0.3195 0.6045 0.7870 0.039 Uiso 1 1 calc R . . H10B H 0.4493 0.6243 0.7960 0.039 Uiso 1 1 calc R . . H10C H 0.4074 0.5001 0.8175 0.039 Uiso 1 1 calc R . . C11 C 0.0163(2) 0.5831(2) 0.08003(15) 0.0314(5) Uani 1 1 d . . . H11A H -0.0520 0.5828 0.0322 0.047 Uiso 1 1 calc R . . H11B H 0.0367 0.5028 0.0982 0.047 Uiso 1 1 calc R . . H11C H 0.0779 0.6192 0.0647 0.047 Uiso 1 1 calc R . . C12 C 0.1300(2) 0.6556(2) 0.23258(16) 0.0365(6) Uani 1 1 d . . . H12A H 0.1847 0.6762 0.2045 0.055 Uiso 1 1 calc R . . H12B H 0.1447 0.5762 0.2544 0.055 Uiso 1 1 calc R . . H12C H 0.1368 0.7102 0.2781 0.055 Uiso 1 1 calc R . . C13 C 0.8536(2) 0.2789(2) 0.41585(15) 0.0321(5) Uani 1 1 d . . . H13A H 0.8519 0.3574 0.3928 0.048 Uiso 1 1 calc R . . H13B H 0.7843 0.2653 0.4297 0.048 Uiso 1 1 calc R . . H13C H 0.8595 0.2211 0.3751 0.048 Uiso 1 1 calc R . . C14 C 0.9356(2) 0.3811(2) 0.56376(16) 0.0300(5) Uani 1 1 d . . . H14A H 0.9963 0.3921 0.6159 0.045 Uiso 1 1 calc R . . H14B H 0.8660 0.3614 0.5754 0.045 Uiso 1 1 calc R . . H14C H 0.9248 0.4532 0.5314 0.045 Uiso 1 1 calc R . . N1 N 0.33853(17) 0.58105(18) 0.05033(11) 0.0224(4) Uani 1 1 d . . . N2 N 0.36923(15) 0.55907(16) 0.18858(11) 0.0198(3) Uani 1 1 d . . . N3 N 0.42598(15) 0.66232(15) 0.19907(11) 0.0196(3) Uani 1 1 d . . . N4 N 0.37935(14) 0.56547(14) 0.34893(10) 0.0153(3) Uani 1 1 d . . . N5 N 0.48000(14) 0.71897(15) 0.41818(10) 0.0174(3) Uani 1 1 d . . . N6 N 0.43924(14) 0.65333(15) 0.46841(10) 0.0160(3) Uani 1 1 d . . . N7 N 0.33182(13) 0.49843(15) 0.53942(10) 0.0155(3) Uani 1 1 d . . . N8 N 0.27891(15) 0.42666(16) 0.57903(11) 0.0184(3) Uani 1 1 d . . . N9 N 0.36609(16) 0.53143(17) 0.69611(11) 0.0193(3) Uani 1 1 d . . . O1 O -0.02050(17) 0.78899(15) 0.13116(10) 0.0315(4) Uani 1 1 d . . . O2 O 1.07120(13) 0.30854(15) 0.48220(10) 0.0243(3) Uani 1 1 d . . . H1 H 0.370(2) 0.639(3) 0.0646(18) 0.022(7) Uiso 1 1 d . . . H2 H 0.363(3) 0.517(3) 0.232(2) 0.036(8) Uiso 1 1 d . . . H6 H 0.450(3) 0.671(3) 0.515(2) 0.035(8) Uiso 1 1 d . . . H8 H 0.231(2) 0.387(3) 0.5581(18) 0.023(7) Uiso 1 1 d . . . H9 H 0.393(2) 0.563(3) 0.6735(18) 0.023(7) Uiso 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 S1 0.0289(3) 0.0226(3) 0.0211(3) 0.00164(19) 0.0050(2) -0.0061(2) S2 0.0258(3) 0.0434(4) 0.0221(3) 0.0124(2) 0.0091(2) -0.0056(2) S3 0.0287(3) 0.0293(3) 0.0218(3) 0.0066(2) 0.0115(2) 0.0060(2) S4 0.0201(2) 0.0219(3) 0.0247(3) 0.0000(2) 0.0091(2) 0.00174(18) C1 0.0582(17) 0.0377(14) 0.0139(10) 0.0001(9) 0.0082(10) -0.0159(12) C2 0.0186(9) 0.0189(9) 0.0192(9) 0.0009(7) 0.0075(7) 0.0013(7) C3 0.0227(9) 0.0170(9) 0.0161(9) 0.0013(7) 0.0082(7) 0.0018(7) C4 0.0411(13) 0.0207(10) 0.0221(10) -0.0009(8) 0.0135(9) -0.0078(9) C5 0.0177(8) 0.0168(9) 0.0131(8) 0.0005(7) 0.0058(7) 0.0025(7) C6 0.0124(8) 0.0173(9) 0.0136(8) -0.0005(7) 0.0035(6) 0.0029(7) C7 0.0138(8) 0.0161(9) 0.0155(8) 0.0003(7) 0.0047(7) 0.0019(7) C8 0.0261(10) 0.0232(10) 0.0207(10) -0.0059(8) 0.0114(8) -0.0069(8) C9 0.0178(9) 0.0237(10) 0.0154(9) 0.0062(7) 0.0064(7) 0.0045(7) C10 0.0342(12) 0.0322(12) 0.0132(9) -0.0009(8) 0.0084(8) 0.0052(9) C11 0.0457(14) 0.0234(11) 0.0227(11) -0.0012(9) 0.0073(10) 0.0035(10) C12 0.0424(14) 0.0346(13) 0.0229(11) 0.0010(10) -0.0037(10) 0.0064(11) C13 0.0240(11) 0.0435(14) 0.0259(11) -0.0071(10) 0.0034(9) -0.0007(10) C14 0.0233(10) 0.0353(13) 0.0323(12) -0.0087(10) 0.0101(9) 0.0032(9) N1 0.0298(10) 0.0227(9) 0.0154(8) 0.0007(7) 0.0079(7) -0.0045(8) N2 0.0264(9) 0.0196(8) 0.0147(8) 0.0006(7) 0.0084(7) -0.0031(7) N3 0.0244(8) 0.0181(8) 0.0168(8) 0.0000(6) 0.0073(7) 0.0011(7) N4 0.0177(7) 0.0165(8) 0.0123(7) 0.0004(6) 0.0053(6) 0.0016(6) N5 0.0204(8) 0.0177(8) 0.0154(8) 0.0010(6) 0.0077(6) 0.0003(6) N6 0.0187(8) 0.0183(8) 0.0115(7) -0.0007(6) 0.0056(6) -0.0001(6) N7 0.0150(7) 0.0182(8) 0.0139(7) 0.0034(6) 0.0055(6) 0.0008(6) N8 0.0183(8) 0.0216(8) 0.0159(8) 0.0005(7) 0.0063(7) -0.0045(7) N9 0.0239(9) 0.0239(9) 0.0116(8) 0.0021(7) 0.0078(7) -0.0002(7) O1 0.0527(11) 0.0248(8) 0.0187(7) 0.0063(6) 0.0137(7) 0.0172(8) O2 0.0215(7) 0.0271(8) 0.0269(8) -0.0050(6) 0.0113(6) -0.0022(6) _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 S1 C2 1.684(2) . ? S2 C9 1.678(2) . ? S3 O1 1.5203(17) . ? S3 C11 1.769(2) . ? S3 C12 1.778(3) . ? S4 O2 1.5160(16) . ? S4 C14 1.781(2) . ? S4 C13 1.782(2) . ? C1 N1 1.453(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.325(3) . ? C2 N2 1.369(3) . ? C3 N3 1.288(3) . ? C3 C5 1.469(3) . ? C3 C4 1.499(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N5 1.332(3) . ? C5 N4 1.371(3) . ? C6 N4 1.326(2) . ? C6 N6 1.340(3) . ? C6 C7 1.464(3) . ? C7 N7 1.290(2) . ? C7 C8 1.493(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N9 1.320(3) . ? C9 N8 1.376(3) . ? C10 N9 1.450(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 H1 0.77(3) . ? N2 N3 1.364(2) . ? N2 H2 0.91(3) . ? N5 N6 1.355(2) . ? N6 H6 0.80(3) . ? N7 N8 1.361(2) . ? N8 H8 0.75(3) . ? N9 H9 0.69(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 S3 C11 104.66(11) . . ? O1 S3 C12 104.65(12) . . ? C11 S3 C12 97.97(13) . . ? O2 S4 C14 106.34(11) . . ? O2 S4 C13 105.25(11) . . ? C14 S4 C13 97.42(12) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 115.65(19) . . ? N1 C2 S1 125.86(17) . . ? N2 C2 S1 118.48(15) . . ? N3 C3 C5 125.86(19) . . ? N3 C3 C4 116.40(18) . . ? C5 C3 C4 117.71(18) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N5 C5 N4 114.18(17) . . ? N5 C5 C3 121.05(18) . . ? N4 C5 C3 124.73(17) . . ? N4 C6 N6 110.02(17) . . ? N4 C6 C7 126.05(18) . . ? N6 C6 C7 123.91(17) . . ? N7 C7 C6 113.60(17) . . ? N7 C7 C8 127.07(18) . . ? C6 C7 C8 119.33(17) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N9 C9 N8 116.47(18) . . ? N9 C9 S2 124.27(16) . . ? N8 C9 S2 119.25(16) . . ? N9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S3 C11 H11A 109.5 . . ? S3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S3 C12 H12A 109.5 . . ? S3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? S4 C13 H13A 109.5 . . ? S4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S4 C14 H14A 109.5 . . ? S4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C2 N1 C1 123.7(2) . . ? C2 N1 H1 115(2) . . ? C1 N1 H1 121(2) . . ? N3 N2 C2 118.77(17) . . ? N3 N2 H2 122(2) . . ? C2 N2 H2 119(2) . . ? C3 N3 N2 119.41(17) . . ? C6 N4 C5 102.93(16) . . ? C5 N5 N6 102.32(16) . . ? C6 N6 N5 110.55(16) . . ? C6 N6 H6 128(2) . . ? N5 N6 H6 121(2) . . ? C7 N7 N8 118.88(17) . . ? N7 N8 C9 117.52(18) . . ? N7 N8 H8 125(2) . . ? C9 N8 H8 115(2) . . ? C9 N9 C10 122.99(19) . . ? C9 N9 H9 121(2) . . ? C10 N9 H9 116(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 N3 C3 C5 N5 -179.0(2) . . . . ? C4 C3 C5 N5 -0.9(3) . . . . ? N3 C3 C5 N4 -1.5(3) . . . . ? C4 C3 C5 N4 176.67(19) . . . . ? N4 C6 C7 N7 -176.27(18) . . . . ? N6 C6 C7 N7 2.2(3) . . . . ? N4 C6 C7 C8 3.4(3) . . . . ? N6 C6 C7 C8 -178.13(18) . . . . ? N2 C2 N1 C1 -179.4(2) . . . . ? S1 C2 N1 C1 -0.7(3) . . . . ? N1 C2 N2 N3 -3.6(3) . . . . ? S1 C2 N2 N3 177.57(15) . . . . ? C5 C3 N3 N2 -3.3(3) . . . . ? C4 C3 N3 N2 178.51(19) . . . . ? C2 N2 N3 C3 175.84(19) . . . . ? N6 C6 N4 C5 -0.5(2) . . . . ? C7 C6 N4 C5 178.20(18) . . . . ? N5 C5 N4 C6 0.8(2) . . . . ? C3 C5 N4 C6 -176.92(18) . . . . ? N4 C5 N5 N6 -0.8(2) . . . . ? C3 C5 N5 N6 177.02(17) . . . . ? N4 C6 N6 N5 0.0(2) . . . . ? C7 C6 N6 N5 -178.69(17) . . . . ? C5 N5 N6 C6 0.5(2) . . . . ? C6 C7 N7 N8 177.76(16) . . . . ? C8 C7 N7 N8 -1.9(3) . . . . ? C7 N7 N8 C9 177.64(18) . . . . ? N9 C9 N8 N7 -6.4(3) . . . . ? S2 C9 N8 N7 174.64(14) . . . . ? N8 C9 N9 C10 177.59(19) . . . . ? S2 C9 N9 C10 -3.5(3) . . . . ? 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 N9 H9 O1 0.69(3) 2.25(3) 2.910(3) 161(3) 4_676 N8 H8 O2 0.75(3) 2.21(3) 2.939(2) 166(3) 1_455 N6 H6 O1 0.80(3) 1.95(3) 2.741(2) 178(3) 4_676 N2 H2 N4 0.91(3) 2.02(3) 2.698(2) 130(3) . N1 H1 O2 0.77(3) 2.31(3) 2.964(3) 143(3) 2_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.80 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.557 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.090