# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_Cambridge 0182 #======================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr Arno Kraft Department of Chemistry Heriot-Watt University Edinburgh EH14 4AS ; _publ_contact_author_phone '0131 451-30' _publ_contact_author_fax '0131 451 3180' _publ_contact_author_email A.Kraft@hw.ac.uk _publ_requested_coeditor_name ? _publ_contact_letter ; Here is the CIF file for the structure in a manuscript entitled,"Supramolecular binding of protonated amines to a microgel in aqueous medium" Thank you Georgina Rosair (G.M.Rosair@hw.ac.uk) ; _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ;Unusually weak binding interactions between tetrazole and amidines ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address A.Kraft ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; A.F.Tominey ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; G.M.Rosair ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; D.Andrew ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; J.Dupre ; School of Engineering & Physical Sciences Heriot-Watt University Edinburgh EH14 4AS UK ; _publ_contact_author_name 'Dr Arno Kraft' #====================================================== data_organic _database_code_depnum_ccdc_archive 'CCDC 603033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H30 N4, 4(C5 H6 N5 O)' _chemical_formula_sum 'C30 H54 N24 O4' _chemical_formula_weight 814.97 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 11.1364(14) _cell_length_b 13.482(2) _cell_length_c 14.299(2) _cell_angle_alpha 90.000(12) _cell_angle_beta 110.275(12) _cell_angle_gamma 90.000(11) _cell_volume 2013.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 22.32 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 Xcalibur-2 _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10445 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.1181 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 22.32 _reflns_number_total 1959 _reflns_number_gt 1513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis CCD' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2002)' _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^)+(0.0388P)^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 SHELXL _refine_ls_extinction_coef 0.0032(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1959 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1479 _refine_ls_R_factor_gt 0.1043 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _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 1.0108(6) 0.9450(4) 0.4971(5) 0.0190(18) Uani 1 1 d . . . H1A H 1.1017 0.9333 0.5056 0.023 Uiso 1 1 calc R . . H1B H 0.9933 0.9114 0.5526 0.023 Uiso 1 1 calc R . . C2 C 0.9274(5) 0.9002(5) 0.3999(5) 0.0177(18) Uani 1 1 d . . . H2A H 0.8364 0.9107 0.3917 0.021 Uiso 1 1 calc R . . H2B H 0.9440 0.9341 0.3441 0.021 Uiso 1 1 calc R . . N3 N 0.9518(4) 0.7927(4) 0.3955(4) 0.0175(15) Uani 1 1 d . . . H3A H 0.9265 0.7604 0.4422 0.021 Uiso 1 1 calc R . . H3B H 1.0384 0.7826 0.4117 0.021 Uiso 1 1 calc R . . C4 C 0.8833(6) 0.7490(5) 0.2955(5) 0.0189(19) Uani 1 1 d . . . H4A H 0.8960 0.7924 0.2439 0.023 Uiso 1 1 calc R . . H4B H 0.7905 0.7472 0.2843 0.023 Uiso 1 1 calc R . . C5 C 0.9275(5) 0.6458(5) 0.2833(5) 0.0169(18) Uani 1 1 d . . . H5A H 1.0213 0.6466 0.2988 0.020 Uiso 1 1 calc R . . H5B H 0.8869 0.6251 0.2129 0.020 Uiso 1 1 calc R . . C6 C 0.8952(6) 0.5700(5) 0.3504(5) 0.0224(19) Uani 1 1 d . . . H6A H 0.9403 0.5879 0.4211 0.027 Uiso 1 1 calc R . . H6B H 0.8021 0.5716 0.3379 0.027 Uiso 1 1 calc R . . N7 N 0.9335(4) 0.4668(4) 0.3320(4) 0.0196(16) Uani 1 1 d . . . H7A H 0.8901 0.4494 0.2676 0.029 Uiso 1 1 calc R . . H7B H 0.9143 0.4235 0.3735 0.029 Uiso 1 1 calc R . . H7C H 1.0191 0.4651 0.3436 0.029 Uiso 1 1 calc R . . C11 C 0.6850(7) 0.2843(6) 0.4996(5) 0.0177(18) Uani 1 1 d . . . N12 N 0.6175(5) 0.3560(5) 0.4412(4) 0.0223(15) Uani 1 1 d . . . N13 N 0.7042(5) 0.4045(4) 0.4114(4) 0.0259(17) Uani 1 1 d . . . N14 N 0.8168(5) 0.3611(5) 0.4508(4) 0.0225(15) Uani 1 1 d . . . N15 N 0.8073(5) 0.2823(4) 0.5081(4) 0.0200(15) Uani 1 1 d . . . N16 N 0.6254(5) 0.2146(4) 0.5417(4) 0.0217(16) Uani 1 1 d . . . H16 H 0.5420 0.2198 0.5266 0.026 Uiso 1 1 calc R . . C17 C 0.6851(7) 0.1396(6) 0.6038(5) 0.0221(19) Uani 1 1 d . . . O17 O 0.8022(4) 0.1267(3) 0.6351(3) 0.0248(13) Uani 1 1 d . . . C18 C 0.5987(6) 0.0681(6) 0.6306(5) 0.0211(19) Uani 1 1 d . . . C19 C 0.6214(6) -0.0281(6) 0.6262(5) 0.037(2) Uani 1 1 d . . . H19B H 0.5688 -0.0754 0.6429 0.045 Uiso 1 1 calc R . . H19A H 0.6902 -0.0497 0.6064 0.045 Uiso 1 1 calc R . . C20 C 0.4927(6) 0.1083(5) 0.6609(5) 0.033(2) Uani 1 1 d . . . H20C H 0.4435 0.0532 0.6743 0.049 Uiso 1 1 calc R . . H20A H 0.4363 0.1495 0.6071 0.049 Uiso 1 1 calc R . . H20B H 0.5287 0.1485 0.7213 0.049 Uiso 1 1 calc R . . C21 C 0.7088(6) -0.1432(6) 0.0781(5) 0.0142(18) Uani 1 1 d . . . N22 N 0.6551(5) -0.2311(4) 0.0484(4) 0.0187(15) Uani 1 1 d . . . N23 N 0.7426(5) -0.2788(4) 0.0175(4) 0.0238(16) Uani 1 1 d . . . N24 N 0.8409(5) -0.2200(5) 0.0303(4) 0.0210(15) Uani 1 1 d . . . N25 N 0.8226(5) -0.1318(5) 0.0688(4) 0.0202(15) Uani 1 1 d . . . N26 N 0.6465(5) -0.0715(4) 0.1155(4) 0.0199(15) Uani 1 1 d . . . H26 H 0.5648 -0.0805 0.1060 0.024 Uiso 1 1 calc R . . C27 C 0.7042(7) 0.0110(5) 0.1657(5) 0.0208(19) Uani 1 1 d . . . O27 O 0.8201(4) 0.0257(3) 0.1898(3) 0.0250(13) Uani 1 1 d . . . C28 C 0.6217(6) 0.0831(5) 0.1954(5) 0.0190(18) Uani 1 1 d . . . C29 C 0.4970(6) 0.0896(5) 0.1496(5) 0.0240(19) Uani 1 1 d . . . H29B H 0.4552 0.0473 0.0948 0.029 Uiso 1 1 calc R . . H29A H 0.4487 0.1367 0.1713 0.029 Uiso 1 1 calc R . . C30 C 0.6928(6) 0.1519(6) 0.2785(6) 0.042(2) Uani 1 1 d . . . H30C H 0.6326 0.1989 0.2905 0.063 Uiso 1 1 calc R . . H30B H 0.7574 0.1884 0.2600 0.063 Uiso 1 1 calc R . . H30A H 0.7350 0.1134 0.3391 0.063 Uiso 1 1 calc R . . 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 0.022(4) 0.011(4) 0.023(5) 0.006(4) 0.007(3) -0.004(3) C2 0.011(4) 0.020(5) 0.020(5) 0.007(4) 0.003(3) 0.001(3) N3 0.016(3) 0.015(4) 0.024(4) 0.006(3) 0.009(3) 0.005(3) C4 0.015(4) 0.023(5) 0.012(5) -0.002(4) -0.004(3) -0.003(3) C5 0.017(4) 0.018(5) 0.013(5) 0.000(4) 0.001(3) -0.001(3) C6 0.029(4) 0.013(5) 0.026(5) -0.008(4) 0.011(3) 0.004(3) N7 0.015(3) 0.023(4) 0.019(4) 0.000(3) 0.004(3) -0.002(3) C11 0.020(5) 0.024(5) 0.011(5) 0.002(4) 0.009(4) 0.004(4) N12 0.021(3) 0.025(4) 0.020(4) 0.013(4) 0.006(3) 0.001(3) N13 0.020(4) 0.032(5) 0.027(4) 0.011(4) 0.010(3) 0.007(3) N14 0.031(4) 0.017(4) 0.020(4) -0.001(4) 0.011(3) -0.004(3) N15 0.024(4) 0.014(4) 0.023(4) 0.001(3) 0.009(3) 0.002(3) N16 0.014(3) 0.024(4) 0.028(4) 0.005(4) 0.008(3) 0.003(3) C17 0.029(5) 0.019(5) 0.015(5) 0.002(5) 0.003(4) 0.007(4) O17 0.025(3) 0.025(3) 0.022(3) 0.007(3) 0.005(2) 0.007(2) C18 0.019(4) 0.019(6) 0.020(5) 0.006(4) 0.000(3) 0.000(4) C19 0.040(5) 0.031(6) 0.040(6) 0.011(5) 0.014(4) 0.005(4) C20 0.028(5) 0.029(6) 0.044(6) 0.021(4) 0.015(4) 0.005(4) C21 0.015(5) 0.022(6) 0.007(5) 0.008(4) 0.005(3) 0.008(4) N22 0.018(3) 0.010(4) 0.027(4) -0.009(3) 0.007(3) -0.003(3) N23 0.019(4) 0.023(4) 0.029(4) -0.010(3) 0.007(3) -0.001(3) N24 0.022(4) 0.021(4) 0.022(4) -0.003(3) 0.009(3) -0.002(3) N25 0.022(4) 0.022(4) 0.020(4) -0.001(4) 0.011(3) 0.001(3) N26 0.016(3) 0.025(4) 0.018(4) -0.006(4) 0.005(3) -0.003(3) C27 0.023(5) 0.018(6) 0.021(5) 0.008(4) 0.008(4) -0.003(4) O27 0.024(3) 0.023(3) 0.025(3) 0.001(3) 0.006(2) -0.001(2) C28 0.022(5) 0.018(5) 0.013(5) 0.002(4) 0.001(4) 0.004(4) C29 0.036(5) 0.015(5) 0.025(5) 0.002(4) 0.017(4) -0.002(4) C30 0.045(5) 0.041(6) 0.035(6) 0.004(5) 0.007(4) 0.017(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 C2 1.505(9) . ? C1 C1 1.509(12) 3_776 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N3 1.480(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? N3 C4 1.489(8) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? C4 C5 1.505(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.528(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N7 1.505(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 H7A 0.9100 . ? N7 H7B 0.9100 . ? N7 H7C 0.9100 . ? C11 N15 1.326(7) . ? C11 N12 1.328(8) . ? C11 N16 1.401(8) . ? N12 N13 1.351(7) . ? N13 N14 1.320(7) . ? N14 N15 1.368(7) . ? N16 C17 1.358(8) . ? N16 H16 0.8800 . ? C17 O17 1.236(7) . ? C17 C18 1.503(9) . ? C18 C19 1.327(9) . ? C18 C20 1.493(8) . ? C19 H19B 0.9500 . ? C19 H19A 0.9500 . ? C20 H20C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C21 N25 1.328(7) . ? C21 N22 1.329(8) . ? C21 N26 1.400(8) . ? N22 N23 1.363(7) . ? N23 N24 1.312(7) . ? N24 N25 1.354(7) . ? N26 C27 1.359(8) . ? N26 H26 0.8800 . ? C27 O27 1.231(7) . ? C27 C28 1.497(9) . ? C28 C29 1.317(8) . ? C28 C30 1.499(9) . ? C29 H29B 0.9500 . ? C29 H29A 0.9500 . ? C30 H30C 0.9800 . ? C30 H30B 0.9800 . ? C30 H30A 0.9800 . ? 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 C1 C1 112.7(7) . 3_776 ? C2 C1 H1A 109.0 . . ? C1 C1 H1A 109.0 3_776 . ? C2 C1 H1B 109.0 . . ? C1 C1 H1B 109.0 3_776 . ? H1A C1 H1B 107.8 . . ? N3 C2 C1 111.6(5) . . ? N3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 N3 C4 112.8(5) . . ? C2 N3 H3A 109.0 . . ? C4 N3 H3A 109.0 . . ? C2 N3 H3B 109.0 . . ? C4 N3 H3B 109.0 . . ? H3A N3 H3B 107.8 . . ? N3 C4 C5 113.4(5) . . ? N3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 112.8(5) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N7 C6 C5 111.5(5) . . ? N7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C6 N7 H7A 109.5 . . ? C6 N7 H7B 109.5 . . ? H7A N7 H7B 109.5 . . ? C6 N7 H7C 109.5 . . ? H7A N7 H7C 109.5 . . ? H7B N7 H7C 109.5 . . ? N15 C11 N12 114.3(6) . . ? N15 C11 N16 124.9(7) . . ? N12 C11 N16 120.7(6) . . ? C11 N12 N13 103.9(5) . . ? N14 N13 N12 109.2(5) . . ? N13 N14 N15 109.9(5) . . ? C11 N15 N14 102.7(5) . . ? C17 N16 C11 125.6(6) . . ? C17 N16 H16 117.2 . . ? C11 N16 H16 117.2 . . ? O17 C17 N16 123.9(6) . . ? O17 C17 C18 120.4(7) . . ? N16 C17 C18 115.6(6) . . ? C19 C18 C20 123.4(6) . . ? C19 C18 C17 117.7(6) . . ? C20 C18 C17 118.8(6) . . ? C18 C19 H19B 120.0 . . ? C18 C19 H19A 120.0 . . ? H19B C19 H19A 120.0 . . ? C18 C20 H20C 109.5 . . ? C18 C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20C C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N25 C21 N22 114.2(6) . . ? N25 C21 N26 125.1(7) . . ? N22 C21 N26 120.7(6) . . ? C21 N22 N23 103.4(5) . . ? N24 N23 N22 109.0(5) . . ? N23 N24 N25 110.6(5) . . ? C21 N25 N24 102.8(5) . . ? C27 N26 C21 124.1(6) . . ? C27 N26 H26 118.0 . . ? C21 N26 H26 118.0 . . ? O27 C27 N26 122.5(6) . . ? O27 C27 C28 120.2(7) . . ? N26 C27 C28 117.2(6) . . ? C29 C28 C27 123.2(7) . . ? C29 C28 C30 122.0(6) . . ? C27 C28 C30 114.8(6) . . ? C28 C29 H29B 120.0 . . ? C28 C29 H29A 120.0 . . ? H29B C29 H29A 120.0 . . ? C28 C30 H30C 109.5 . . ? C28 C30 H30B 109.5 . . ? H30C C30 H30B 109.5 . . ? C28 C30 H30A 109.5 . . ? H30C C30 H30A 109.5 . . ? H30B C30 H30A 109.5 . . ? 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 C1 C1 C2 N3 179.2(6) 3_776 . . . ? C1 C2 N3 C4 -172.5(5) . . . . ? C2 N3 C4 C5 168.1(5) . . . . ? N3 C4 C5 C6 66.4(7) . . . . ? C4 C5 C6 N7 176.6(5) . . . . ? N15 C11 N12 N13 -1.0(8) . . . . ? N16 C11 N12 N13 -177.1(6) . . . . ? C11 N12 N13 N14 0.6(7) . . . . ? N12 N13 N14 N15 0.0(7) . . . . ? N12 C11 N15 N14 1.0(8) . . . . ? N16 C11 N15 N14 176.8(6) . . . . ? N13 N14 N15 C11 -0.6(7) . . . . ? N15 C11 N16 C17 5.7(10) . . . . ? N12 C11 N16 C17 -178.7(7) . . . . ? C11 N16 C17 O17 3.9(10) . . . . ? C11 N16 C17 C18 -173.9(6) . . . . ? O17 C17 C18 C19 -43.9(10) . . . . ? N16 C17 C18 C19 133.9(7) . . . . ? O17 C17 C18 C20 135.9(7) . . . . ? N16 C17 C18 C20 -46.2(9) . . . . ? N25 C21 N22 N23 -0.2(7) . . . . ? N26 C21 N22 N23 179.9(5) . . . . ? C21 N22 N23 N24 0.5(6) . . . . ? N22 N23 N24 N25 -0.6(7) . . . . ? N22 C21 N25 N24 -0.2(7) . . . . ? N26 C21 N25 N24 179.8(6) . . . . ? N23 N24 N25 C21 0.5(7) . . . . ? N25 C21 N26 C27 -13.9(10) . . . . ? N22 C21 N26 C27 166.1(6) . . . . ? C21 N26 C27 O27 -6.3(10) . . . . ? C21 N26 C27 C28 176.5(6) . . . . ? O27 C27 C28 C29 159.2(6) . . . . ? N26 C27 C28 C29 -23.6(9) . . . . ? O27 C27 C28 C30 -17.7(9) . . . . ? N26 C27 C28 C30 159.6(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 N3 H3A N24 0.92 1.90 2.802(8) 165.0 4_566 N3 H3A N23 0.92 2.63 3.365(7) 136.8 4_566 N3 H3B N15 0.92 1.92 2.749(8) 149.6 3_766 N3 H3B O17 0.92 2.43 3.115(6) 131.1 3_766 N7 H7A O17 0.91 2.08 2.966(7) 165.4 4_565 N7 H7B N14 0.91 1.98 2.852(7) 159.0 . N7 H7B N13 0.91 2.59 3.245(7) 129.3 . N7 H7C O27 0.91 2.17 2.975(6) 147.6 2_755 N7 H7C N25 0.91 2.20 2.914(7) 134.4 2_755 N16 H16 N22 0.88 2.18 3.027(7) 160.0 2_655 N26 H26 N12 0.88 2.09 2.933(7) 160.6 2_645 _diffrn_measured_fraction_theta_max 0.761 _diffrn_reflns_theta_full 22.32 _diffrn_measured_fraction_theta_full 0.761 _refine_diff_density_max 0.175 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.041