# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/242 data_global # Concomitant ferro- and antiferromagnetic interactions in a H-bonded # molecular ribbon duplex # PROCESSING SUMMARY _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? # SUBMISSION DETAILS loop_ _publ_contact_author_name _publ_contact_author_address 'Sutter, Jean-Pascal' ; Laboratoire des Sciences Moleclaires Institut de Chimie de la Matiere Condensee de Bordeaux UPR CNRS No. 9048, F-33608 Pessac France ; _publ_contact_author_email 'jpsutter@icmcb.u-bordeaux.fr' _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_letter ; ; _publ_requested_journal 'Perkin Transaction 2' #TITLE AND AUTHOR LIST _publ_section_title ; Concomitant ferro- and antiferromagnetic interactions in a H-bonded molecular ribbon duplex ; loop_ _publ_author_name _publ_author_address 'Daro, Nathalie' ; Laboratoire des Sciences Moleclaires Institut de Chimie de la Matiere Condensee de Bordeaux UPR CNRS No. 9048, F-33608 Pessac France ; 'Sutter, Jean-Pascal' ; Laboratoire des Sciences Moleclaires Institut de Chimie de la Matiere Condensee de Bordeaux UPR CNRS No. 9048, F-33608 Pessac France ; 'Pink, Maren' ; Department of Chemistry University of Minnesota 207 Pleasant St. S.E. Minneapolis Minnesota 55455 USA ; 'Kahn, Olivier' ; Laboratoire des Sciences Moleclaires Institut de Chimie de la Matiere Condensee de Bordeaux UPR CNRS No. 9048, F-33608 Pessac France ; data_00023 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 00023 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 N6 O2' _chemical_formula_weight 239.27 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6167(4) _cell_length_b 14.6927(6) _cell_length_c 16.5683(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.110(1) _cell_angle_gamma 90.00 _cell_volume 2335.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8087 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type 'multi-scans' _exptl_absorpt_correction_T_min 0.620730 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART Platform CCD, Siemen' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 16551 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4097 _reflns_number_gt 2934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Siemens' _computing_cell_refinement 'SMART, Siemens' _computing_data_reduction 'SAINT, Siemens' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL, Siemens' _computing_publication_material ? _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^)+(0.0471P)^2^+2.1533P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4097 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 O1 O 0.7868(2) 0.41728(15) 0.22749(13) 0.0361(6) Uani 1 1 d . . . O2 O 0.32724(19) 0.42487(14) 0.29846(12) 0.0306(5) Uani 1 1 d . . . N1 N 0.7365(2) 0.58478(16) 0.42290(14) 0.0243(5) Uani 1 1 d . . . N2 N 0.7425(2) 0.52635(16) 0.35930(14) 0.0252(6) Uani 1 1 d . . . N3 N 0.5196(2) 0.54050(15) 0.39600(14) 0.0225(5) Uani 1 1 d . . . N4 N 0.6544(2) 0.40630(16) 0.22676(14) 0.0252(6) Uani 1 1 d . . . N5 N 0.4376(2) 0.40911(15) 0.26023(13) 0.0227(5) Uani 1 1 d . . . N6 N 0.5658(3) 0.64784(17) 0.50396(16) 0.0263(6) Uani 1 1 d . . . C1 C 0.6101(3) 0.50197(18) 0.34553(16) 0.0207(6) Uani 1 1 d . . . C2 C 0.6045(3) 0.59207(18) 0.44439(16) 0.0211(6) Uani 1 1 d . . . C3 C 0.5677(3) 0.44022(18) 0.28040(17) 0.0222(6) Uani 1 1 d . . . C4 C 0.5731(3) 0.36522(19) 0.15475(17) 0.0257(7) Uani 1 1 d . . . C5 C 0.4371(3) 0.33855(19) 0.19373(16) 0.0224(6) Uani 1 1 d . . . C6 C 0.5529(4) 0.4426(2) 0.0923(2) 0.0347(8) Uani 1 1 d . . . C7 C 0.6537(4) 0.2880(2) 0.1197(2) 0.0353(8) Uani 1 1 d . . . C8 C 0.3041(3) 0.3464(2) 0.1378(2) 0.0315(7) Uani 1 1 d . . . C9 C 0.4440(4) 0.2462(2) 0.2366(2) 0.0307(7) Uani 1 1 d . . . H6A H 0.496(3) 0.492(2) 0.1137(17) 0.026(8) Uiso 1 1 d . . . H6B H 0.508(3) 0.418(2) 0.043(2) 0.042(9) Uiso 1 1 d . . . H6C H 0.649(3) 0.4623(19) 0.0817(16) 0.024(7) Uiso 1 1 d . . . H7A H 0.668(3) 0.236(2) 0.155(2) 0.042(9) Uiso 1 1 d . . . H7B H 0.748(4) 0.313(2) 0.103(2) 0.049(10) Uiso 1 1 d . . . H7C H 0.601(4) 0.262(3) 0.074(2) 0.061(12) Uiso 1 1 d . . . H8A H 0.289(3) 0.407(2) 0.1159(19) 0.043(9) Uiso 1 1 d . . . H8B H 0.223(4) 0.336(2) 0.171(2) 0.059(11) Uiso 1 1 d . . . H8C H 0.313(3) 0.301(2) 0.0905(19) 0.036(8) Uiso 1 1 d . . . H9A H 0.533(3) 0.2441(19) 0.2753(18) 0.028(8) Uiso 1 1 d . . . H9B H 0.440(3) 0.196(2) 0.1962(19) 0.039(9) Uiso 1 1 d . . . H9C H 0.359(4) 0.240(2) 0.269(2) 0.048(10) Uiso 1 1 d . . . H1N H 0.824(4) 0.607(2) 0.4453(19) 0.042(9) Uiso 1 1 d . . . H6N H 0.472(4) 0.645(2) 0.5135(19) 0.040(9) Uiso 1 1 d . . . H6O H 0.632(4) 0.665(2) 0.539(2) 0.039(10) Uiso 1 1 d . . . O3 O -0.1452(2) 0.70492(15) 0.54488(14) 0.0397(6) Uani 1 1 d . . . O4 O 0.3297(2) 0.75693(14) 0.59025(13) 0.0339(5) Uani 1 1 d . . . N7 N 0.2340(2) 0.54840(15) 0.42332(14) 0.0222(5) Uani 1 1 d . . . N8 N 0.2567(2) 0.61163(15) 0.48411(13) 0.0232(5) Uani 1 1 d . . . N9 N 0.0249(2) 0.59786(15) 0.44644(14) 0.0244(6) Uani 1 1 d . . . N10 N -0.0276(2) 0.73839(16) 0.57023(14) 0.0257(6) Uani 1 1 d . . . N11 N 0.1973(2) 0.76455(16) 0.59070(14) 0.0261(6) Uani 1 1 d . . . N12 N 0.0426(3) 0.48600(19) 0.34262(17) 0.0319(7) Uani 1 1 d . . . C10 C 0.1281(3) 0.63828(18) 0.49523(17) 0.0217(6) Uani 1 1 d . . . C11 C 0.0970(3) 0.54118(19) 0.40210(17) 0.0231(6) Uani 1 1 d . . . C12 C 0.0997(3) 0.70987(18) 0.55179(16) 0.0223(6) Uani 1 1 d . . . C13 C -0.0179(3) 0.81099(19) 0.63535(18) 0.0257(7) Uani 1 1 d . . . C14 C 0.1300(3) 0.84823(19) 0.62390(18) 0.0265(7) Uani 1 1 d . . . C15 C -0.1363(4) 0.8795(2) 0.6193(2) 0.0359(8) Uani 1 1 d . . . C16 C -0.0327(4) 0.7615(2) 0.7151(2) 0.0370(8) Uani 1 1 d . . . C17 C 0.1336(4) 0.9203(2) 0.5574(2) 0.0379(8) Uani 1 1 d . . . C18 C 0.2099(4) 0.8805(3) 0.7006(2) 0.0384(8) Uani 1 1 d . . . H15A H -0.135(3) 0.904(2) 0.566(2) 0.046(10) Uiso 1 1 d . . . H15B H -0.124(3) 0.927(2) 0.659(2) 0.041(9) Uiso 1 1 d . . . H15C H -0.228(4) 0.848(2) 0.629(2) 0.058(11) Uiso 1 1 d . . . H16A H 0.048(3) 0.721(2) 0.7277(18) 0.032(8) Uiso 1 1 d . . . H16B H -0.126(3) 0.727(2) 0.7120(19) 0.042(9) Uiso 1 1 d . . . H16C H -0.033(3) 0.808(2) 0.762(2) 0.044(9) Uiso 1 1 d . . . H17A H 0.083(4) 0.900(3) 0.504(3) 0.073(13) Uiso 1 1 d . . . H17B H 0.230(4) 0.933(2) 0.5455(19) 0.043(9) Uiso 1 1 d . . . H17C H 0.093(4) 0.981(3) 0.574(2) 0.067(12) Uiso 1 1 d . . . H18A H 0.215(4) 0.836(3) 0.741(2) 0.058(12) Uiso 1 1 d . . . H18B H 0.158(4) 0.933(3) 0.724(2) 0.054(10) Uiso 1 1 d . . . H18C H 0.306(4) 0.893(2) 0.693(2) 0.055(11) Uiso 1 1 d . . . H7N H 0.316(4) 0.526(2) 0.398(2) 0.048(10) Uiso 1 1 d . . . H12N H 0.099(3) 0.452(2) 0.3228(18) 0.025(9) Uiso 1 1 d . . . H12O H -0.050(3) 0.485(2) 0.3347(17) 0.028(8) 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 O1 0.0199(11) 0.0472(14) 0.0417(14) -0.0115(11) 0.0067(9) -0.0022(10) O2 0.0178(10) 0.0411(12) 0.0337(12) -0.0106(10) 0.0069(9) 0.0008(9) N1 0.0185(13) 0.0299(13) 0.0245(14) -0.0044(11) 0.0011(10) -0.0011(10) N2 0.0220(13) 0.0298(13) 0.0239(14) -0.0046(11) 0.0013(10) 0.0003(10) N3 0.0212(12) 0.0238(12) 0.0224(13) -0.0016(10) 0.0014(10) 0.0000(10) N4 0.0199(13) 0.0316(13) 0.0240(13) -0.0046(11) 0.0019(10) 0.0008(10) N5 0.0196(13) 0.0255(12) 0.0229(13) -0.0001(10) 0.0012(10) 0.0009(10) N6 0.0186(14) 0.0333(14) 0.0268(15) -0.0075(11) -0.0006(12) -0.0014(11) C1 0.0211(15) 0.0232(14) 0.0178(15) 0.0006(12) 0.0013(12) 0.0009(12) C2 0.0183(15) 0.0224(14) 0.0221(15) 0.0030(12) -0.0013(12) 0.0002(11) C3 0.0192(15) 0.0235(14) 0.0238(16) -0.0002(12) 0.0021(12) 0.0028(11) C4 0.0249(16) 0.0303(16) 0.0220(16) -0.0047(13) 0.0021(12) 0.0009(12) C5 0.0199(14) 0.0260(14) 0.0214(16) -0.0050(12) 0.0023(12) 0.0002(12) C6 0.038(2) 0.042(2) 0.0255(19) 0.0017(16) 0.0047(15) -0.0027(16) C7 0.037(2) 0.0370(19) 0.032(2) -0.0099(16) 0.0057(16) 0.0018(16) C8 0.0293(18) 0.0369(19) 0.0277(19) -0.0049(15) -0.0018(14) 0.0021(14) C9 0.0323(19) 0.0280(17) 0.0316(19) -0.0015(14) 0.0010(15) -0.0019(14) O3 0.0175(11) 0.0463(13) 0.0556(15) -0.0222(12) 0.0043(10) -0.0044(10) O4 0.0182(11) 0.0449(13) 0.0384(13) -0.0136(10) -0.0002(9) -0.0023(9) N7 0.0182(13) 0.0248(12) 0.0240(14) -0.0044(11) 0.0043(10) 0.0014(10) N8 0.0219(13) 0.0270(12) 0.0209(13) -0.0031(10) 0.0029(10) 0.0009(10) N9 0.0206(13) 0.0259(13) 0.0271(14) -0.0072(11) 0.0037(11) 0.0005(10) N10 0.0188(13) 0.0278(13) 0.0303(14) -0.0057(11) 0.0021(10) -0.0005(10) N11 0.0209(13) 0.0317(13) 0.0257(14) -0.0050(11) 0.0006(10) 0.0002(10) N12 0.0190(15) 0.0380(16) 0.0388(17) -0.0175(13) 0.0028(12) 0.0017(12) C10 0.0187(15) 0.0218(14) 0.0246(16) 0.0009(12) 0.0005(12) -0.0005(11) C11 0.0210(15) 0.0258(15) 0.0227(16) -0.0008(12) 0.0026(12) -0.0025(12) C12 0.0188(15) 0.0241(15) 0.0243(16) 0.0015(12) 0.0037(12) -0.0022(12) C13 0.0241(16) 0.0261(15) 0.0274(17) -0.0096(13) 0.0045(13) -0.0001(12) C14 0.0268(16) 0.0252(15) 0.0277(17) -0.0065(13) 0.0035(13) -0.0015(12) C15 0.032(2) 0.0341(18) 0.042(2) -0.0080(17) 0.0061(16) 0.0055(15) C16 0.040(2) 0.0407(19) 0.032(2) -0.0013(16) 0.0132(16) 0.0012(17) C17 0.040(2) 0.0294(18) 0.046(2) 0.0002(16) 0.0100(17) -0.0046(15) C18 0.034(2) 0.045(2) 0.036(2) -0.0159(18) -0.0008(16) -0.0019(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 O1 N4 1.282(3) . ? O2 N5 1.295(3) . ? N1 C2 1.347(3) . ? N1 N2 1.364(3) . ? N1 H1N 0.95(3) . ? N2 C1 1.327(3) . ? N3 C2 1.338(3) . ? N3 C1 1.372(3) . ? N4 C3 1.356(3) . ? N4 C4 1.505(4) . ? N5 C3 1.352(3) . ? N5 C5 1.513(3) . ? N6 C2 1.355(4) . ? N6 H6N 0.93(4) . ? N6 H6O 0.87(3) . ? C1 C3 1.446(4) . ? C4 C7 1.513(4) . ? C4 C6 1.541(4) . ? C4 C5 1.551(4) . ? C5 C8 1.528(4) . ? C5 C9 1.530(4) . ? C6 H6A 0.99(3) . ? C6 H6B 0.97(3) . ? C6 H6C 0.99(3) . ? C7 H7A 0.97(3) . ? C7 H7B 1.04(4) . ? C7 H7C 0.96(4) . ? C8 H8A 0.97(3) . ? C8 H8B 1.00(4) . ? C8 H8C 1.04(3) . ? C9 H9A 1.03(3) . ? C9 H9B 1.00(3) . ? C9 H9C 1.01(3) . ? O3 N10 1.276(3) . ? O4 N11 1.279(3) . ? N7 C11 1.343(3) . ? N7 N8 1.376(3) . ? N7 H7N 0.98(3) . ? N8 C10 1.322(3) . ? N9 C11 1.337(3) . ? N9 C10 1.370(3) . ? N10 C12 1.350(3) . ? N10 C13 1.515(4) . ? N11 C12 1.362(3) . ? N11 C14 1.511(4) . ? N12 C11 1.352(4) . ? N12 H12N 0.82(3) . ? N12 H12O 0.89(3) . ? C10 C12 1.448(4) . ? C13 C16 1.524(4) . ? C13 C15 1.528(4) . ? C13 C14 1.549(4) . ? C14 C18 1.513(4) . ? C14 C17 1.530(4) . ? C15 H15A 0.96(4) . ? C15 H15B 0.96(3) . ? C15 H15C 1.02(4) . ? C16 H16A 0.99(3) . ? C16 H16B 1.03(3) . ? C16 H16C 1.03(3) . ? C17 H17A 1.02(4) . ? C17 H17B 0.98(3) . ? C17 H17C 1.01(4) . ? C18 H18A 0.93(4) . ? C18 H18B 1.01(4) . ? C18 H18C 0.96(4) . ? 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 N2 110.3(2) . . ? C2 N1 H1N 133.8(19) . . ? N2 N1 H1N 115.6(19) . . ? C1 N2 N1 102.1(2) . . ? C2 N3 C1 102.2(2) . . ? O1 N4 C3 127.2(2) . . ? O1 N4 C4 121.1(2) . . ? C3 N4 C4 111.0(2) . . ? O2 N5 C3 126.5(2) . . ? O2 N5 C5 121.3(2) . . ? C3 N5 C5 111.5(2) . . ? C2 N6 H6N 114(2) . . ? C2 N6 H6O 116(2) . . ? H6N N6 H6O 125(3) . . ? N2 C1 N3 115.3(2) . . ? N2 C1 C3 120.9(2) . . ? N3 C1 C3 123.8(2) . . ? N3 C2 N1 110.0(2) . . ? N3 C2 N6 126.2(3) . . ? N1 C2 N6 123.6(3) . . ? N5 C3 N4 108.4(2) . . ? N5 C3 C1 127.1(2) . . ? N4 C3 C1 124.5(2) . . ? N4 C4 C7 110.7(2) . . ? N4 C4 C6 105.7(2) . . ? C7 C4 C6 109.8(3) . . ? N4 C4 C5 100.2(2) . . ? C7 C4 C5 116.2(3) . . ? C6 C4 C5 113.4(2) . . ? N5 C5 C8 110.4(2) . . ? N5 C5 C9 105.8(2) . . ? C8 C5 C9 110.8(2) . . ? N5 C5 C4 99.9(2) . . ? C8 C5 C4 115.0(2) . . ? C9 C5 C4 114.0(2) . . ? C4 C6 H6A 110.5(17) . . ? C4 C6 H6B 109.0(19) . . ? H6A C6 H6B 111(3) . . ? C4 C6 H6C 105.0(16) . . ? H6A C6 H6C 113(2) . . ? H6B C6 H6C 108(2) . . ? C4 C7 H7A 114.1(19) . . ? C4 C7 H7B 109.0(19) . . ? H7A C7 H7B 111(3) . . ? C4 C7 H7C 110(2) . . ? H7A C7 H7C 102(3) . . ? H7B C7 H7C 110(3) . . ? C5 C8 H8A 113.2(19) . . ? C5 C8 H8B 108(2) . . ? H8A C8 H8B 104(3) . . ? C5 C8 H8C 107.6(17) . . ? H8A C8 H8C 109(3) . . ? H8B C8 H8C 116(3) . . ? C5 C9 H9A 108.7(16) . . ? C5 C9 H9B 110.4(18) . . ? H9A C9 H9B 113(2) . . ? C5 C9 H9C 108.3(19) . . ? H9A C9 H9C 109(2) . . ? H9B C9 H9C 107(3) . . ? C11 N7 N8 110.2(2) . . ? C11 N7 H7N 132(2) . . ? N8 N7 H7N 117(2) . . ? C10 N8 N7 101.6(2) . . ? C11 N9 C10 102.2(2) . . ? O3 N10 C12 127.1(2) . . ? O3 N10 C13 120.9(2) . . ? C12 N10 C13 111.7(2) . . ? O4 N11 C12 126.8(2) . . ? O4 N11 C14 121.7(2) . . ? C12 N11 C14 110.7(2) . . ? C11 N12 H12N 115(2) . . ? C11 N12 H12O 116.6(19) . . ? H12N N12 H12O 128(3) . . ? N8 C10 N9 115.8(2) . . ? N8 C10 C12 121.8(2) . . ? N9 C10 C12 122.3(2) . . ? N9 C11 N7 110.2(2) . . ? N9 C11 N12 125.8(3) . . ? N7 C11 N12 124.0(3) . . ? N10 C12 N11 108.4(2) . . ? N10 C12 C10 126.1(2) . . ? N11 C12 C10 125.4(2) . . ? N10 C13 C16 106.1(2) . . ? N10 C13 C15 109.4(2) . . ? C16 C13 C15 110.5(3) . . ? N10 C13 C14 99.9(2) . . ? C16 C13 C14 114.7(3) . . ? C15 C13 C14 115.2(3) . . ? N11 C14 C18 110.8(3) . . ? N11 C14 C17 105.6(2) . . ? C18 C14 C17 110.6(3) . . ? N11 C14 C13 100.3(2) . . ? C18 C14 C13 115.1(3) . . ? C17 C14 C13 113.6(3) . . ? C13 C15 H15A 110(2) . . ? C13 C15 H15B 108(2) . . ? H15A C15 H15B 111(3) . . ? C13 C15 H15C 108(2) . . ? H15A C15 H15C 113(3) . . ? H15B C15 H15C 107(3) . . ? C13 C16 H16A 110.5(17) . . ? C13 C16 H16B 109.1(18) . . ? H16A C16 H16B 112(3) . . ? C13 C16 H16C 110.1(18) . . ? H16A C16 H16C 106(3) . . ? H16B C16 H16C 108(2) . . ? C14 C17 H17A 113(2) . . ? C14 C17 H17B 110.2(19) . . ? H17A C17 H17B 106(3) . . ? C14 C17 H17C 113(2) . . ? H17A C17 H17C 109(3) . . ? H17B C17 H17C 106(3) . . ? C14 C18 H18A 112(2) . . ? C14 C18 H18B 109(2) . . ? H18A C18 H18B 105(3) . . ? C14 C18 H18C 113(2) . . ? H18A C18 H18C 103(3) . . ? H18B C18 H18C 114(3) . . ? 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 C2 N1 N2 C1 0.5(3) . . . . ? N1 N2 C1 N3 -0.2(3) . . . . ? N1 N2 C1 C3 178.8(2) . . . . ? C2 N3 C1 N2 -0.3(3) . . . . ? C2 N3 C1 C3 -179.2(3) . . . . ? C1 N3 C2 N1 0.6(3) . . . . ? C1 N3 C2 N6 177.3(3) . . . . ? N2 N1 C2 N3 -0.8(3) . . . . ? N2 N1 C2 N6 -177.6(2) . . . . ? O2 N5 C3 N4 178.1(2) . . . . ? C5 N5 C3 N4 7.8(3) . . . . ? O2 N5 C3 C1 -4.2(4) . . . . ? C5 N5 C3 C1 -174.5(3) . . . . ? O1 N4 C3 N5 -177.0(3) . . . . ? C4 N4 C3 N5 12.9(3) . . . . ? O1 N4 C3 C1 5.2(4) . . . . ? C4 N4 C3 C1 -164.9(2) . . . . ? N2 C1 C3 N5 179.2(3) . . . . ? N3 C1 C3 N5 -1.9(4) . . . . ? N2 C1 C3 N4 -3.4(4) . . . . ? N3 C1 C3 N4 175.5(3) . . . . ? O1 N4 C4 C7 39.2(4) . . . . ? C3 N4 C4 C7 -150.0(3) . . . . ? O1 N4 C4 C6 -79.6(3) . . . . ? C3 N4 C4 C6 91.2(3) . . . . ? O1 N4 C4 C5 162.4(2) . . . . ? C3 N4 C4 C5 -26.8(3) . . . . ? O2 N5 C5 C8 43.9(3) . . . . ? C3 N5 C5 C8 -145.2(3) . . . . ? O2 N5 C5 C9 -76.0(3) . . . . ? C3 N5 C5 C9 94.9(3) . . . . ? O2 N5 C5 C4 165.4(2) . . . . ? C3 N5 C5 C4 -23.7(3) . . . . ? N4 C4 C5 N5 27.9(2) . . . . ? C7 C4 C5 N5 147.2(3) . . . . ? C6 C4 C5 N5 -84.2(3) . . . . ? N4 C4 C5 C8 146.1(2) . . . . ? C7 C4 C5 C8 -94.7(3) . . . . ? C6 C4 C5 C8 33.9(4) . . . . ? N4 C4 C5 C9 -84.4(3) . . . . ? C7 C4 C5 C9 34.9(4) . . . . ? C6 C4 C5 C9 163.4(3) . . . . ? C11 N7 N8 C10 0.1(3) . . . . ? N7 N8 C10 N9 -0.3(3) . . . . ? N7 N8 C10 C12 -176.5(2) . . . . ? C11 N9 C10 N8 0.4(3) . . . . ? C11 N9 C10 C12 176.6(2) . . . . ? C10 N9 C11 N7 -0.3(3) . . . . ? C10 N9 C11 N12 -178.5(3) . . . . ? N8 N7 C11 N9 0.2(3) . . . . ? N8 N7 C11 N12 178.4(3) . . . . ? O3 N10 C12 N11 179.3(3) . . . . ? C13 N10 C12 N11 -7.8(3) . . . . ? O3 N10 C12 C10 3.9(5) . . . . ? C13 N10 C12 C10 176.8(2) . . . . ? O4 N11 C12 N10 177.5(2) . . . . ? C14 N11 C12 N10 -12.8(3) . . . . ? O4 N11 C12 C10 -7.1(4) . . . . ? C14 N11 C12 C10 162.6(3) . . . . ? N8 C10 C12 N10 -176.4(3) . . . . ? N9 C10 C12 N10 7.7(4) . . . . ? N8 C10 C12 N11 9.0(4) . . . . ? N9 C10 C12 N11 -166.9(3) . . . . ? O3 N10 C13 C16 77.7(3) . . . . ? C12 N10 C13 C16 -95.7(3) . . . . ? O3 N10 C13 C15 -41.6(4) . . . . ? C12 N10 C13 C15 145.1(3) . . . . ? O3 N10 C13 C14 -162.8(2) . . . . ? C12 N10 C13 C14 23.8(3) . . . . ? O4 N11 C14 C18 -40.9(4) . . . . ? C12 N11 C14 C18 148.8(3) . . . . ? O4 N11 C14 C17 78.8(3) . . . . ? C12 N11 C14 C17 -91.4(3) . . . . ? O4 N11 C14 C13 -162.9(2) . . . . ? C12 N11 C14 C13 26.8(3) . . . . ? N10 C13 C14 N11 -27.9(2) . . . . ? C16 C13 C14 N11 85.0(3) . . . . ? C15 C13 C14 N11 -145.0(3) . . . . ? N10 C13 C14 C18 -146.9(3) . . . . ? C16 C13 C14 C18 -34.0(4) . . . . ? C15 C13 C14 C18 96.1(3) . . . . ? N10 C13 C14 C17 84.2(3) . . . . ? C16 C13 C14 C17 -162.9(3) . . . . ? C15 C13 C14 C17 -32.8(4) . . . . ? 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 N1 H1N N9 0.95(3) 1.93(3) 2.779(3) 146(3) 1_655 N1 H1N O3 0.95(3) 2.19(3) 2.857(3) 126(2) 1_655 N6 H6N N8 0.93(4) 2.15(4) 3.015(4) 155(3) . N6 H6N O4 0.93(4) 2.54(3) 3.199(3) 128(2) . N6 H6O O3 0.87(3) 2.21(3) 2.935(3) 140(3) 1_655 N7 H7N N3 0.98(3) 1.97(3) 2.818(3) 143(3) . N7 H7N O2 0.98(3) 2.22(3) 2.940(3) 129(3) . N12 H12N O2 0.82(3) 2.30(3) 3.020(3) 147(3) . N12 H12O N2 0.89(3) 2.15(3) 2.978(4) 154(3) 1_455 N12 H12O O1 0.89(3) 2.49(3) 3.168(3) 133(2) 1_455 C9 H9A O4 1.03(3) 2.51(3) 3.475(4) 156(2) 3_666 C16 H16A O1 0.99(3) 2.65(3) 3.616(4) 165(2) 3_666 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.232 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.056