Supplementary Material (ESI) for New Journal of Chemistry This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Roger Guilard' _publ_contact_author_address ; Faculte des Sciences Universite de Bourgogne LIMSAG - UMR 5633 6, boulevard Gabriel Dijon 21100 FRANCE ; _publ_contact_author_email ROGER.GUILARD@U-BOURGOGNE.FR _publ_section_title ; Synthesis, Characterization and X-Ray Crystal Structures of Cyclam Derivatives. 7. Hydrogen-Bond Induced Allosteric Effects and Protonation Cooperativity in a Macrotricyclic Bisdioxocyclam Receptor ; loop_ _publ_author_name 'R. Guilard' 'Stephane Brandes' 'Enrique Espinosa' 'Laurent Fremond' 'Michel Meyer' 'Guy Yves Vollmer' #======================================================================== data_lf110a _database_code_depnum_ccdc_archive 'CCDC 233399' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H52 N8 O4, 4(H2 O)' _chemical_formula_sum 'C36 H60 N8 O8' _chemical_formula_weight 732.92 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 12.9970(2) _cell_length_b 18.4860(2) _cell_length_c 16.1270(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3874.71(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 10778 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 30.02 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.090 _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 110(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10778 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0949 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5657 _reflns_number_gt 3056 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0511P)^2^+0.7542P] 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 SHELXL _refine_ls_extinction_coef 0.0058(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5657 _refine_ls_number_parameters 255 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1415 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.003 _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 0.75620(12) 0.20335(8) 0.70815(9) 0.0308(4) Uani 1 1 d . . . HN1 H 0.7256(15) 0.1620(11) 0.7142(11) 0.037 Uiso 1 1 d . . . N2 N 0.73233(10) 0.05104(7) 0.69555(8) 0.0233(3) Uani 1 1 d . . . N3 N 0.74517(10) 0.08548(7) 0.87687(8) 0.0242(3) Uani 1 1 d . . . HN3 H 0.7088(14) 0.1231(9) 0.8618(10) 0.029 Uiso 1 1 d . . . N4 N 0.67836(10) 0.22988(7) 0.87937(8) 0.0255(3) Uani 1 1 d . . . C1 C 0.85236(14) 0.19804(10) 0.67886(10) 0.0334(4) Uani 1 1 d . . . O1 O 0.90845(10) 0.25120(8) 0.66880(8) 0.0512(4) Uani 1 1 d . . . C2 C 0.88969(13) 0.12285(10) 0.65896(11) 0.0359(4) Uani 1 1 d . . . H2A H 0.9236 0.1038 0.7079 0.043 Uiso 1 1 calc R . . H2B H 0.9414 0.1267 0.6158 0.043 Uiso 1 1 calc R . . C3 C 0.80985(12) 0.06752(9) 0.63089(10) 0.0290(4) Uani 1 1 d . . . H3A H 0.7749 0.0858 0.5821 0.035 Uiso 1 1 calc R . . H3B H 0.8447 0.0231 0.6154 0.035 Uiso 1 1 calc R . . C4 C 0.77577(13) 0.00289(9) 0.75930(10) 0.0282(4) Uani 1 1 d . . . H4A H 0.8490 0.0120 0.7641 0.034 Uiso 1 1 calc R . . H4B H 0.7667 -0.0470 0.7421 0.034 Uiso 1 1 calc R . . C5 C 0.72553(13) 0.01363(8) 0.84355(9) 0.0249(4) Uani 1 1 d . . . H5A H 0.6519 0.0065 0.8384 0.030 Uiso 1 1 calc R . . H5B H 0.7517 -0.0224 0.8819 0.030 Uiso 1 1 calc R . . C6 C 0.82049(12) 0.10161(9) 0.92958(10) 0.0260(4) Uani 1 1 d . . . O6 O 0.87967(10) 0.05547(7) 0.95874(8) 0.0403(3) Uani 1 1 d . . . C7 C 0.83337(13) 0.18044(9) 0.95202(10) 0.0297(4) Uani 1 1 d . . . H7A H 0.8769 0.2030 0.9106 0.036 Uiso 1 1 calc R . . H7B H 0.8693 0.1832 1.0047 0.036 Uiso 1 1 calc R . . C8 C 0.73457(13) 0.22417(9) 0.95885(10) 0.0281(4) Uani 1 1 d . . . H8A H 0.6901 0.2017 0.9997 0.034 Uiso 1 1 calc R . . H8B H 0.7511 0.2724 0.9784 0.034 Uiso 1 1 calc R . . C9 C 0.72503(14) 0.28592(9) 0.82598(11) 0.0319(4) Uani 1 1 d . . . H9A H 0.7983 0.2885 0.8372 0.038 Uiso 1 1 calc R . . H9B H 0.6952 0.3326 0.8395 0.038 Uiso 1 1 calc R . . C10 C 0.70850(15) 0.27047(9) 0.73441(11) 0.0346(4) Uani 1 1 d . . . H10A H 0.6352 0.2681 0.7233 0.042 Uiso 1 1 calc R . . H10B H 0.7367 0.3100 0.7021 0.042 Uiso 1 1 calc R . . C11 C 0.63931(12) 0.01798(8) 0.65893(10) 0.0249(4) Uani 1 1 d . . . H11A H 0.5921 0.0047 0.7029 0.030 Uiso 1 1 calc R . . H11B H 0.6585 -0.0258 0.6296 0.030 Uiso 1 1 calc R . . C12 C 0.58588(12) 0.06901(8) 0.59973(9) 0.0222(4) Uani 1 1 d . . . C13 C 0.59341(12) 0.05831(9) 0.51447(10) 0.0260(4) Uani 1 1 d . . . H13 H 0.6263 0.0172 0.4943 0.031 Uiso 1 1 calc R . . C14 C 0.55256(13) 0.10795(9) 0.45938(10) 0.0281(4) Uani 1 1 d . . . H14 H 0.5586 0.1004 0.4026 0.034 Uiso 1 1 calc R . . C15 C 0.50279(12) 0.16874(9) 0.48883(10) 0.0261(4) Uani 1 1 d . . . H15 H 0.4771 0.2025 0.4515 0.031 Uiso 1 1 calc R . . C16 C 0.49043(12) 0.18026(8) 0.57391(10) 0.0239(4) Uani 1 1 d . . . C17 C 0.53319(12) 0.12985(8) 0.62775(10) 0.0225(4) Uani 1 1 d . . . H17 H 0.5264 0.1370 0.6846 0.027 Uiso 1 1 calc R . . C18 C 0.43239(13) 0.24534(8) 0.60607(11) 0.0285(4) Uani 1 1 d . . . H18A H 0.4635 0.2612 0.6576 0.034 Uiso 1 1 calc R . . H18B H 0.4385 0.2845 0.5663 0.034 Uiso 1 1 calc R . . OW1 O 1.02102(11) -0.06808(7) 0.59189(8) 0.0461(4) Uani 1 1 d D . . HW11 H 0.9698(12) -0.0710(11) 0.5501(10) 0.055 Uiso 1 1 d D . . HW12 H 1.0595(14) -0.0260(8) 0.5789(12) 0.055 Uiso 1 1 d D . . OW2 O 0.5000 -0.12841(9) 0.7500 0.0397(5) Uani 1 2 d SD . . HW21 H 0.4590(13) -0.1622(8) 0.7799(10) 0.048 Uiso 1 1 d D . . OW3 O 0.5000 0.37003(9) 0.7500 0.0498(5) Uani 1 2 d SD . . HW31 H 0.5004(16) 0.4004(9) 0.7027(9) 0.060 Uiso 1 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 0.0345(9) 0.0264(8) 0.0314(8) 0.0037(6) 0.0006(7) -0.0087(7) N2 0.0232(7) 0.0266(7) 0.0199(7) 0.0031(5) -0.0005(6) 0.0025(6) N3 0.0270(8) 0.0217(7) 0.0240(7) 0.0015(6) -0.0058(6) 0.0017(6) N4 0.0264(8) 0.0236(7) 0.0264(7) 0.0017(6) -0.0057(6) -0.0034(6) C1 0.0353(11) 0.0475(11) 0.0174(9) 0.0043(7) -0.0023(8) -0.0167(9) O1 0.0570(9) 0.0619(9) 0.0346(7) -0.0012(6) 0.0073(6) -0.0366(8) C2 0.0245(9) 0.0559(12) 0.0271(10) 0.0030(8) 0.0019(7) -0.0046(9) C3 0.0257(9) 0.0394(10) 0.0221(9) 0.0003(7) 0.0041(7) 0.0026(8) C4 0.0304(9) 0.0286(9) 0.0254(9) 0.0017(7) -0.0013(7) 0.0077(7) C5 0.0293(9) 0.0228(8) 0.0225(8) 0.0031(7) -0.0034(7) 0.0005(7) C6 0.0235(9) 0.0323(9) 0.0221(8) 0.0008(7) 0.0000(7) 0.0019(8) O6 0.0402(8) 0.0391(7) 0.0417(8) -0.0051(6) -0.0177(6) 0.0135(6) C7 0.0279(10) 0.0320(9) 0.0291(9) -0.0006(7) -0.0067(7) -0.0042(8) C8 0.0298(10) 0.0270(9) 0.0276(9) -0.0019(7) -0.0061(7) -0.0021(8) C9 0.0367(10) 0.0219(8) 0.0371(10) 0.0033(7) -0.0046(8) -0.0078(8) C10 0.0465(11) 0.0238(9) 0.0335(10) 0.0082(7) -0.0056(8) -0.0063(8) C11 0.0289(9) 0.0230(8) 0.0229(8) 0.0006(6) 0.0000(7) -0.0001(7) C12 0.0204(8) 0.0239(8) 0.0223(8) 0.0012(6) -0.0004(7) -0.0054(7) C13 0.0268(9) 0.0271(9) 0.0241(9) -0.0032(7) 0.0001(7) -0.0010(7) C14 0.0292(10) 0.0356(10) 0.0195(8) 0.0011(7) -0.0007(7) -0.0037(8) C15 0.0247(9) 0.0278(9) 0.0259(9) 0.0061(7) -0.0044(7) -0.0054(7) C16 0.0226(9) 0.0228(8) 0.0264(9) 0.0007(7) -0.0032(7) -0.0056(7) C17 0.0239(9) 0.0254(8) 0.0180(8) -0.0002(6) -0.0007(6) -0.0044(7) C18 0.0293(10) 0.0234(8) 0.0328(9) 0.0006(7) -0.0072(7) -0.0012(7) OW1 0.0572(9) 0.0364(8) 0.0448(9) 0.0127(6) -0.0214(7) -0.0112(7) OW2 0.0582(13) 0.0332(10) 0.0278(10) 0.000 0.0039(9) 0.000 OW3 0.0861(15) 0.0257(10) 0.0375(12) 0.000 -0.0204(11) 0.000 _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 C1 1.340(2) . ? N1 C10 1.450(2) . ? N1 HN1 0.87(2) . ? N2 C4 1.472(2) . ? N2 C11 1.478(2) . ? N2 C3 1.482(2) . ? N3 C6 1.330(2) . ? N3 C5 1.455(2) . ? N3 HN3 0.876(18) . ? N4 C9 1.477(2) . ? N4 C8 1.479(2) . ? N4 C18 1.486(2) 4_656 ? C1 O1 1.234(2) . ? C1 C2 1.507(3) . ? C2 C3 1.526(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.521(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O6 1.2411(19) . ? C6 C7 1.511(2) . ? C7 C8 1.521(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.519(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.511(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.392(2) . ? C12 C13 1.393(2) . ? C13 C14 1.383(2) . ? C13 H13 0.9300 . ? C14 C15 1.381(2) . ? C14 H14 0.9300 . ? C15 C16 1.398(2) . ? C15 H15 0.9300 . ? C16 C17 1.390(2) . ? C16 C18 1.512(2) . ? C17 H17 0.9300 . ? C18 N4 1.486(2) 4_656 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? OW1 HW11 0.949(9) . ? OW1 HW12 0.949(9) . ? OW2 HW21 0.952(5) . ? OW3 HW31 0.948(9) . ? 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 C1 N1 C10 124.37(15) . . ? C1 N1 HN1 113.7(12) . . ? C10 N1 HN1 121.7(12) . . ? C4 N2 C11 110.04(12) . . ? C4 N2 C3 110.80(12) . . ? C11 N2 C3 111.10(12) . . ? C6 N3 C5 124.72(14) . . ? C6 N3 HN3 113.3(11) . . ? C5 N3 HN3 121.9(11) . . ? C9 N4 C8 110.62(13) . . ? C9 N4 C18 110.79(13) . 4_656 ? C8 N4 C18 110.80(13) . 4_656 ? O1 C1 N1 122.61(18) . . ? O1 C1 C2 121.09(17) . . ? N1 C1 C2 116.31(15) . . ? C1 C2 C3 117.55(15) . . ? C1 C2 H2A 107.9 . . ? C3 C2 H2A 107.9 . . ? C1 C2 H2B 107.9 . . ? C3 C2 H2B 107.9 . . ? H2A C2 H2B 107.2 . . ? N2 C3 C2 113.05(13) . . ? N2 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? N2 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? N2 C4 C5 112.35(13) . . ? N2 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? N2 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? N3 C5 C4 111.95(13) . . ? N3 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? N3 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? O6 C6 N3 122.96(16) . . ? O6 C6 C7 120.23(15) . . ? N3 C6 C7 116.80(14) . . ? C6 C7 C8 115.87(14) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? N4 C8 C7 113.08(13) . . ? N4 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? N4 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N4 C9 C10 112.12(13) . . ? N4 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N4 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N1 C10 C9 112.59(14) . . ? N1 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? N1 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N2 C11 C12 111.73(12) . . ? N2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N2 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C17 C12 C13 118.02(14) . . ? C17 C12 C11 121.69(14) . . ? C13 C12 C11 120.19(14) . . ? C14 C13 C12 120.86(15) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 119.92(15) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 121.03(15) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 117.72(14) . . ? C17 C16 C18 121.25(14) . . ? C15 C16 C18 121.02(14) . . ? C16 C17 C12 122.38(14) . . ? C16 C17 H17 118.8 . . ? C12 C17 H17 118.8 . . ? N4 C18 C16 112.61(12) 4_656 . ? N4 C18 H18A 109.1 4_656 . ? C16 C18 H18A 109.1 . . ? N4 C18 H18B 109.1 4_656 . ? C16 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? HW11 OW1 HW12 105.0(17) . . ? 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 C10 N1 C1 O1 -2.6(3) . . . . ? C10 N1 C1 C2 176.96(15) . . . . ? O1 C1 C2 C3 -150.01(16) . . . . ? N1 C1 C2 C3 30.4(2) . . . . ? C4 N2 C3 C2 -76.43(17) . . . . ? C11 N2 C3 C2 160.91(13) . . . . ? C1 C2 C3 N2 -63.8(2) . . . . ? C11 N2 C4 C5 -85.34(16) . . . . ? C3 N2 C4 C5 151.39(14) . . . . ? C6 N3 C5 C4 -95.37(17) . . . . ? N2 C4 C5 N3 -64.53(18) . . . . ? C5 N3 C6 O6 -3.3(3) . . . . ? C5 N3 C6 C7 175.47(14) . . . . ? O6 C6 C7 C8 -145.56(16) . . . . ? N3 C6 C7 C8 35.7(2) . . . . ? C9 N4 C8 C7 -79.68(17) . . . . ? C18 N4 C8 C7 157.05(13) 4_656 . . . ? C6 C7 C8 N4 -63.86(19) . . . . ? C8 N4 C9 C10 152.08(15) . . . . ? C18 N4 C9 C10 -84.64(17) 4_656 . . . ? C1 N1 C10 C9 -90.6(2) . . . . ? N4 C9 C10 N1 -62.2(2) . . . . ? C4 N2 C11 C12 173.95(12) . . . . ? C3 N2 C11 C12 -62.97(16) . . . . ? N2 C11 C12 C17 -71.11(18) . . . . ? N2 C11 C12 C13 105.14(16) . . . . ? C17 C12 C13 C14 2.1(2) . . . . ? C11 C12 C13 C14 -174.34(15) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C16 -1.7(2) . . . . ? C14 C15 C16 C17 2.3(2) . . . . ? C14 C15 C16 C18 -177.63(15) . . . . ? C15 C16 C17 C12 -0.7(2) . . . . ? C18 C16 C17 C12 179.19(14) . . . . ? C13 C12 C17 C16 -1.4(2) . . . . ? C11 C12 C17 C16 174.94(14) . . . . ? C17 C16 C18 N4 -87.10(18) . . . 4_656 ? C15 C16 C18 N4 92.83(18) . . . 4_656 ? 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 HN1 N2 0.87(2) 2.074(19) 2.8401(19) 146.7(17) . N3 HN3 N4 0.876(18) 2.032(18) 2.8072(19) 147.0(15) . OW1 HW11 O6 0.949(9) 1.904(10) 2.8356(17) 166.6(18) 8 OW1 HW12 O6 0.949(9) 1.806(10) 2.7477(18) 171.6(19) 4_756 OW2 HW21 O1 0.952(5) 1.918(7) 2.8431(19) 163.3(17) 6_557 OW3 HW31 OW1 0.948(9) 1.900(11) 2.8081(15) 159.8(18) 7_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.210 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.051