# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Chuan-Feng Chen' _publ_contact_author_email cchen@iccas.ac.cn _publ_section_title ; Hg2+ recognition by triptycene-derived heterocalixarenes: selectivity tuned by bridging heteroatoms and macrocyclic cavity ; loop_ _publ_author_name 'Shu-Zhen Hu' 'Chuan-Feng Chen' # Attachment '2b.cif' data_mx476 _database_code_depnum_ccdc_archive 'CCDC 819712' #TrackingRef '2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H34 N6 O2' _chemical_formula_sum 'C56 H34 N6 O2' _chemical_formula_weight 822.89 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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 11.543(4) _cell_length_b 19.853(7) _cell_length_c 12.183(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.935(4) _cell_angle_gamma 90.00 _cell_volume 2765.2(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 526 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18120 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.30 _reflns_number_total 5175 _reflns_number_gt 3952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 200)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0676P)^2^+4.2072P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5175 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1157 _refine_ls_R_factor_gt 0.0948 _refine_ls_wR_factor_ref 0.2254 _refine_ls_wR_factor_gt 0.2137 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 O1 O -0.0090(2) 0.03605(13) 0.3903(2) 0.0415(6) Uani 1 1 d . . . N1 N 0.1047(3) 0.03294(15) 0.2452(2) 0.0356(7) Uani 1 1 d . . . N2 N 0.2126(2) 0.02819(14) 0.0999(2) 0.0322(7) Uani 1 1 d . . . N3 N 0.3188(3) 0.02537(16) -0.0504(3) 0.0390(7) Uani 1 1 d . . . H3B H 0.3291 0.0021 -0.1098 0.047 Uiso 1 1 calc R . . C1 C 0.0207(3) 0.00718(17) 0.2957(3) 0.0317(8) Uani 1 1 d . . . C2 C -0.0488(3) -0.04858(17) 0.2606(3) 0.0314(8) Uani 1 1 d . . . H2A H -0.1076 -0.0642 0.3018 0.038 Uiso 1 1 calc R . . C3 C -0.0291(3) -0.07975(18) 0.1644(3) 0.0353(8) Uani 1 1 d . . . H3A H -0.0753 -0.1172 0.1367 0.042 Uiso 1 1 calc R . . C4 C 0.0598(3) -0.05579(16) 0.1078(3) 0.0320(8) Uani 1 1 d . . . C5 C 0.0872(3) -0.08357(18) 0.0079(3) 0.0369(9) Uani 1 1 d . . . H5A H 0.0444 -0.1212 -0.0241 0.044 Uiso 1 1 calc R . . C6 C 0.1739(3) -0.05707(17) -0.0424(3) 0.0357(8) Uani 1 1 d . . . H6A H 0.1941 -0.0765 -0.1085 0.043 Uiso 1 1 calc R . . C7 C 0.2346(3) 0.00066(18) 0.0056(3) 0.0345(8) Uani 1 1 d . . . C8 C 0.1257(3) 0.00069(16) 0.1496(3) 0.0320(8) Uani 1 1 d . . . C9 C 0.3933(3) 0.08226(18) -0.0304(3) 0.0357(8) Uani 1 1 d . . . C10 C 0.4890(3) 0.08332(19) -0.0884(3) 0.0368(8) Uani 1 1 d . . . H10A H 0.5004 0.0468 -0.1362 0.044 Uiso 1 1 calc R . . C11 C 0.5678(3) 0.1361(2) -0.0785(3) 0.0405(9) Uani 1 1 d . . . H11A H 0.6319 0.1364 -0.1197 0.049 Uiso 1 1 calc R . . C12 C 0.5516(3) 0.18844(18) -0.0073(3) 0.0338(8) Uani 1 1 d . . . C13 C 0.6293(4) 0.2500 0.0171(4) 0.0369(12) Uani 1 2 d S . . H13A H 0.6986 0.2500 -0.0239 0.044 Uiso 1 2 calc SR . . C14 C 0.6623(5) 0.2500 0.1419(5) 0.0403(13) Uani 1 2 d S . . C15 C 0.7772(5) 0.2500 0.1988(5) 0.0472(14) Uani 1 2 d S . . H15A H 0.8427 0.2500 0.1594 0.057 Uiso 1 2 calc SR . . C16 C 0.7922(6) 0.2500 0.3135(5) 0.0596(17) Uani 1 2 d S . . H16A H 0.8692 0.2500 0.3529 0.072 Uiso 1 2 calc SR . . C17 C 0.6970(6) 0.2500 0.3723(6) 0.0593(17) Uani 1 2 d S . . H17A H 0.7086 0.2500 0.4510 0.071 Uiso 1 2 calc SR . . C18 C 0.5848(5) 0.2500 0.3137(5) 0.0461(14) Uani 1 2 d S . . H18A H 0.5191 0.2500 0.3529 0.055 Uiso 1 2 calc SR . . C19 C 0.5680(5) 0.2500 0.2009(4) 0.0373(12) Uani 1 2 d S . . C20 C 0.4498(4) 0.2500 0.1234(4) 0.0296(10) Uani 1 2 d S . . H20A H 0.3808 0.2500 0.1647 0.035 Uiso 1 2 calc SR . . C21 C 0.4541(3) 0.18852(18) 0.0499(3) 0.0332(8) Uani 1 1 d . . . C22 C 0.3751(3) 0.13608(17) 0.0390(3) 0.0322(8) Uani 1 1 d . . . H22A H 0.3093 0.1366 0.0781 0.039 Uiso 1 1 calc R . . C23 C 0.0554(3) 0.08742(18) 0.4481(3) 0.0361(8) Uani 1 1 d . . . C24 C 0.1748(3) 0.0852(2) 0.4779(3) 0.0380(9) Uani 1 1 d . . . H24A H 0.2191 0.0492 0.4536 0.046 Uiso 1 1 calc R . . C25 C 0.2304(3) 0.13647(18) 0.5443(3) 0.0373(8) Uani 1 1 d . . . H25A H 0.3127 0.1354 0.5658 0.045 Uiso 1 1 calc R . . C26 C 0.1647(3) 0.18854(17) 0.5781(3) 0.0302(8) Uani 1 1 d . . . C27 C 0.2097(4) 0.2500 0.6470(4) 0.0303(11) Uani 1 2 d S . . H27A H 0.2966 0.2500 0.6674 0.036 Uiso 1 2 calc SR . . C28 C 0.1447(4) 0.2500 0.7481(4) 0.0319(11) Uani 1 2 d S . . C29 C 0.1942(5) 0.2500 0.8594(4) 0.0378(12) Uani 1 2 d S . . H29A H 0.2767 0.2500 0.8792 0.045 Uiso 1 2 calc SR . . C30 C 0.1211(5) 0.2500 0.9406(4) 0.0393(13) Uani 1 2 d S . . H30A H 0.1538 0.2500 1.0166 0.047 Uiso 1 2 calc SR . . C31 C 0.0019(5) 0.2500 0.9121(4) 0.0405(13) Uani 1 2 d S . . H31A H -0.0468 0.2500 0.9689 0.049 Uiso 1 2 calc SR . . C32 C -0.0489(5) 0.2500 0.8020(4) 0.0348(12) Uani 1 2 d S . . H32A H -0.1316 0.2500 0.7834 0.042 Uiso 1 2 calc SR . . C33 C 0.0231(5) 0.2500 0.7193(4) 0.0353(12) Uani 1 2 d S . . C34 C -0.0146(4) 0.2500 0.5954(4) 0.0317(11) Uani 1 2 d S . . H34A H -0.1015 0.2500 0.5751 0.038 Uiso 1 2 calc SR . . C35 C 0.0434(3) 0.18916(17) 0.5498(3) 0.0317(8) Uani 1 1 d . . . C36 C -0.0118(3) 0.13870(17) 0.4844(3) 0.0318(8) Uani 1 1 d . . . H36A H -0.0943 0.1391 0.4645 0.038 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 O1 0.0430(15) 0.0429(15) 0.0387(14) -0.0117(12) 0.0062(12) -0.0105(12) N1 0.0435(18) 0.0307(16) 0.0312(16) -0.0045(13) -0.0003(13) -0.0004(13) N2 0.0331(15) 0.0353(16) 0.0274(15) 0.0001(13) 0.0019(12) -0.0024(13) N3 0.0417(18) 0.0400(18) 0.0358(17) -0.0081(14) 0.0068(14) 0.0000(14) C1 0.0369(19) 0.0292(18) 0.0281(18) -0.0022(14) 0.0009(15) 0.0018(15) C2 0.040(2) 0.0257(17) 0.0283(18) 0.0006(14) 0.0033(15) -0.0037(14) C3 0.045(2) 0.0267(18) 0.0335(19) 0.0045(15) 0.0011(16) -0.0036(15) C4 0.042(2) 0.0241(17) 0.0272(18) 0.0021(14) -0.0039(15) 0.0031(15) C5 0.048(2) 0.0304(19) 0.0294(19) -0.0032(15) -0.0054(16) -0.0024(16) C6 0.045(2) 0.0275(18) 0.0340(19) -0.0076(15) 0.0031(16) 0.0039(15) C7 0.038(2) 0.034(2) 0.0292(18) 0.0006(15) -0.0018(15) 0.0049(16) C8 0.044(2) 0.0230(18) 0.0276(18) -0.0026(14) -0.0006(15) 0.0024(15) C9 0.0353(19) 0.033(2) 0.0358(19) -0.0058(16) -0.0046(15) 0.0021(15) C10 0.0349(19) 0.040(2) 0.037(2) -0.0015(16) 0.0096(16) 0.0042(16) C11 0.041(2) 0.047(2) 0.034(2) 0.0059(17) 0.0049(16) 0.0010(17) C12 0.0318(18) 0.033(2) 0.0347(19) 0.0021(15) -0.0033(15) 0.0029(15) C13 0.034(3) 0.042(3) 0.035(3) 0.000 0.008(2) 0.000 C14 0.035(3) 0.041(3) 0.042(3) 0.000 -0.004(2) 0.000 C15 0.038(3) 0.052(4) 0.049(3) 0.000 -0.003(3) 0.000 C16 0.051(4) 0.072(4) 0.050(4) 0.000 -0.017(3) 0.000 C17 0.054(4) 0.071(5) 0.050(4) 0.000 -0.003(3) 0.000 C18 0.048(3) 0.056(4) 0.033(3) 0.000 0.000(2) 0.000 C19 0.037(3) 0.038(3) 0.034(3) 0.000 -0.002(2) 0.000 C20 0.024(2) 0.037(3) 0.027(2) 0.000 0.0026(19) 0.000 C21 0.0302(18) 0.037(2) 0.0310(19) 0.0049(15) -0.0010(14) 0.0028(15) C22 0.0311(18) 0.0348(19) 0.0306(18) 0.0009(15) 0.0041(14) 0.0010(15) C23 0.046(2) 0.036(2) 0.0250(18) -0.0033(15) 0.0018(15) -0.0053(16) C24 0.042(2) 0.044(2) 0.0286(19) -0.0076(16) 0.0063(16) 0.0017(17) C25 0.041(2) 0.0337(19) 0.038(2) -0.0061(16) 0.0060(16) 0.0034(16) C26 0.0292(17) 0.0316(19) 0.0281(17) 0.0003(14) -0.0020(14) -0.0022(14) C27 0.026(2) 0.034(3) 0.027(2) 0.000 -0.0086(19) 0.000 C28 0.037(3) 0.021(2) 0.035(3) 0.000 -0.007(2) 0.000 C29 0.056(3) 0.031(3) 0.024(2) 0.000 -0.004(2) 0.000 C30 0.056(3) 0.031(3) 0.028(3) 0.000 -0.008(2) 0.000 C31 0.063(4) 0.030(3) 0.030(3) 0.000 0.012(3) 0.000 C32 0.053(3) 0.022(2) 0.031(3) 0.000 0.015(2) 0.000 C33 0.054(3) 0.028(3) 0.026(3) 0.000 0.010(2) 0.000 C34 0.030(3) 0.035(3) 0.027(3) 0.000 -0.003(2) 0.000 C35 0.043(2) 0.0327(19) 0.0190(16) 0.0015(14) 0.0026(14) 0.0012(15) C36 0.0352(18) 0.0352(19) 0.0245(17) -0.0001(15) 0.0021(14) -0.0021(15) _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 C1 1.373(4) . ? O1 C23 1.394(4) . ? N1 C1 1.321(5) . ? N1 C8 1.380(4) . ? N2 C7 1.328(4) . ? N2 C8 1.356(4) . ? N3 C7 1.354(5) . ? N3 C9 1.420(5) . ? N3 H3B 0.8800 . ? C1 C2 1.399(5) . ? C2 C3 1.371(5) . ? C2 H2A 0.9500 . ? C3 C4 1.397(5) . ? C3 H3A 0.9500 . ? C4 C8 1.411(5) . ? C4 C5 1.411(5) . ? C5 C6 1.351(5) . ? C5 H5A 0.9500 . ? C6 C7 1.426(5) . ? C6 H6A 0.9500 . ? C9 C10 1.391(5) . ? C9 C22 1.396(5) . ? C10 C11 1.382(5) . ? C10 H10A 0.9500 . ? C11 C12 1.383(5) . ? C11 H11A 0.9500 . ? C12 C21 1.403(5) . ? C12 C13 1.521(5) . ? C13 C14 1.516(7) . ? C13 C12 1.521(5) 4_565 ? C13 H13A 1.0000 . ? C14 C19 1.385(8) . ? C14 C15 1.409(7) . ? C15 C16 1.384(8) . ? C15 H15A 0.9500 . ? C16 C17 1.392(9) . ? C16 H16A 0.9500 . ? C17 C18 1.390(8) . ? C17 H17A 0.9500 . ? C18 C19 1.362(7) . ? C18 H18A 0.9500 . ? C19 C20 1.548(7) . ? C20 C21 1.518(4) . ? C20 C21 1.518(5) 4_565 ? C20 H20A 1.0000 . ? C21 C22 1.379(5) . ? C22 H22A 0.9500 . ? C23 C24 1.377(5) . ? C23 C36 1.389(5) . ? C24 C25 1.399(5) . ? C24 H24A 0.9500 . ? C25 C26 1.379(5) . ? C25 H25A 0.9500 . ? C26 C35 1.395(5) . ? C26 C27 1.531(4) . ? C27 C28 1.527(7) . ? C27 C26 1.531(4) 4_565 ? C27 H27A 1.0000 . ? C28 C29 1.398(7) . ? C28 C33 1.399(7) . ? C29 C30 1.386(8) . ? C29 H29A 0.9500 . ? C30 C31 1.372(8) . ? C30 H30A 0.9500 . ? C31 C32 1.387(7) . ? C31 H31A 0.9500 . ? C32 C33 1.392(7) . ? C32 H32A 0.9500 . ? C33 C34 1.512(7) . ? C34 C35 1.523(4) 4_565 ? C34 C35 1.523(4) . ? C34 H34A 1.0000 . ? C35 C36 1.381(5) . ? C36 H36A 0.9500 . ? 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 O1 C23 123.5(3) . . ? C1 N1 C8 116.1(3) . . ? C7 N2 C8 117.5(3) . . ? C7 N3 C9 131.4(3) . . ? C7 N3 H3B 114.3 . . ? C9 N3 H3B 114.3 . . ? N1 C1 O1 120.9(3) . . ? N1 C1 C2 126.3(3) . . ? O1 C1 C2 112.8(3) . . ? C3 C2 C1 117.5(3) . . ? C3 C2 H2A 121.2 . . ? C1 C2 H2A 121.2 . . ? C2 C3 C4 119.2(3) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C8 119.3(3) . . ? C3 C4 C5 124.1(3) . . ? C8 C4 C5 116.6(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? N2 C7 N3 121.6(3) . . ? N2 C7 C6 123.0(3) . . ? N3 C7 C6 115.5(3) . . ? N2 C8 N1 114.7(3) . . ? N2 C8 C4 123.7(3) . . ? N1 C8 C4 121.7(3) . . ? C10 C9 C22 119.5(3) . . ? C10 C9 N3 115.4(3) . . ? C22 C9 N3 125.1(3) . . ? C11 C10 C9 121.7(3) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 C12 118.7(3) . . ? C10 C11 H11A 120.6 . . ? C12 C11 H11A 120.6 . . ? C11 C12 C21 120.0(3) . . ? C11 C12 C13 126.8(3) . . ? C21 C12 C13 113.2(3) . . ? C14 C13 C12 104.8(3) . . ? C14 C13 C12 104.8(3) . 4_565 ? C12 C13 C12 107.0(4) . 4_565 ? C14 C13 H13A 113.2 . . ? C12 C13 H13A 113.2 . . ? C12 C13 H13A 113.2 4_565 . ? C19 C14 C15 119.9(5) . . ? C19 C14 C13 114.5(5) . . ? C15 C14 C13 125.6(5) . . ? C16 C15 C14 118.4(6) . . ? C16 C15 H15A 120.8 . . ? C14 C15 H15A 120.8 . . ? C15 C16 C17 121.5(6) . . ? C15 C16 H16A 119.3 . . ? C17 C16 H16A 119.3 . . ? C18 C17 C16 118.8(6) . . ? C18 C17 H17A 120.6 . . ? C16 C17 H17A 120.6 . . ? C19 C18 C17 120.7(6) . . ? C19 C18 H18A 119.6 . . ? C17 C18 H18A 119.6 . . ? C18 C19 C14 120.8(5) . . ? C18 C19 C20 127.3(5) . . ? C14 C19 C20 111.9(4) . . ? C21 C20 C21 107.0(4) . 4_565 ? C21 C20 C19 105.2(3) . . ? C21 C20 C19 105.2(3) 4_565 . ? C21 C20 H20A 112.9 . . ? C21 C20 H20A 112.9 4_565 . ? C19 C20 H20A 112.9 . . ? C22 C21 C12 121.1(3) . . ? C22 C21 C20 126.1(3) . . ? C12 C21 C20 112.8(3) . . ? C21 C22 C9 118.9(3) . . ? C21 C22 H22A 120.6 . . ? C9 C22 H22A 120.6 . . ? C24 C23 C36 121.5(3) . . ? C24 C23 O1 123.7(3) . . ? C36 C23 O1 114.5(3) . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24A 120.2 . . ? C25 C24 H24A 120.2 . . ? C26 C25 C24 119.4(3) . . ? C26 C25 H25A 120.3 . . ? C24 C25 H25A 120.3 . . ? C25 C26 C35 120.5(3) . . ? C25 C26 C27 127.1(3) . . ? C35 C26 C27 112.4(3) . . ? C28 C27 C26 106.0(3) . . ? C28 C27 C26 106.0(3) . 4_565 ? C26 C27 C26 105.7(4) . 4_565 ? C28 C27 H27A 112.9 . . ? C26 C27 H27A 112.9 . . ? C26 C27 H27A 112.9 4_565 . ? C29 C28 C33 120.3(5) . . ? C29 C28 C27 127.0(5) . . ? C33 C28 C27 112.7(4) . . ? C30 C29 C28 119.0(5) . . ? C30 C29 H29A 120.5 . . ? C28 C29 H29A 120.5 . . ? C31 C30 C29 120.5(5) . . ? C31 C30 H30A 119.8 . . ? C29 C30 H30A 119.8 . . ? C30 C31 C32 121.4(5) . . ? C30 C31 H31A 119.3 . . ? C32 C31 H31A 119.3 . . ? C31 C32 C33 119.0(5) . . ? C31 C32 H32A 120.5 . . ? C33 C32 H32A 120.5 . . ? C32 C33 C28 119.8(5) . . ? C32 C33 C34 127.2(5) . . ? C28 C33 C34 113.0(4) . . ? C33 C34 C35 106.5(3) . 4_565 ? C33 C34 C35 106.5(3) . . ? C35 C34 C35 105.0(4) 4_565 . ? C33 C34 H34A 112.8 . . ? C35 C34 H34A 112.8 4_565 . ? C35 C34 H34A 112.8 . . ? C36 C35 C26 120.3(3) . . ? C36 C35 C34 126.5(3) . . ? C26 C35 C34 113.2(3) . . ? C35 C36 C23 118.8(3) . . ? C35 C36 H36A 120.6 . . ? C23 C36 H36A 120.6 . . ? 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 C8 N1 C1 O1 -178.8(3) . . . . ? C8 N1 C1 C2 -0.9(5) . . . . ? C23 O1 C1 N1 -9.1(5) . . . . ? C23 O1 C1 C2 172.7(3) . . . . ? N1 C1 C2 C3 -0.3(5) . . . . ? O1 C1 C2 C3 177.8(3) . . . . ? C1 C2 C3 C4 1.3(5) . . . . ? C2 C3 C4 C8 -1.2(5) . . . . ? C2 C3 C4 C5 -179.5(3) . . . . ? C3 C4 C5 C6 179.4(3) . . . . ? C8 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 C7 -1.8(5) . . . . ? C8 N2 C7 N3 179.1(3) . . . . ? C8 N2 C7 C6 -2.1(5) . . . . ? C9 N3 C7 N2 -3.4(6) . . . . ? C9 N3 C7 C6 177.8(3) . . . . ? C5 C6 C7 N2 2.5(5) . . . . ? C5 C6 C7 N3 -178.7(3) . . . . ? C7 N2 C8 N1 -178.0(3) . . . . ? C7 N2 C8 C4 1.2(5) . . . . ? C1 N1 C8 N2 -179.8(3) . . . . ? C1 N1 C8 C4 1.0(5) . . . . ? C3 C4 C8 N2 -179.1(3) . . . . ? C5 C4 C8 N2 -0.6(5) . . . . ? C3 C4 C8 N1 0.0(5) . . . . ? C5 C4 C8 N1 178.5(3) . . . . ? C7 N3 C9 C10 164.5(4) . . . . ? C7 N3 C9 C22 -17.4(6) . . . . ? C22 C9 C10 C11 0.8(5) . . . . ? N3 C9 C10 C11 178.9(3) . . . . ? C9 C10 C11 C12 1.1(5) . . . . ? C10 C11 C12 C21 -2.4(5) . . . . ? C10 C11 C12 C13 178.7(4) . . . . ? C11 C12 C13 C14 -124.6(4) . . . . ? C21 C12 C13 C14 56.5(4) . . . . ? C11 C12 C13 C12 124.5(4) . . . 4_565 ? C21 C12 C13 C12 -54.4(5) . . . 4_565 ? C12 C13 C14 C19 -56.2(3) . . . . ? C12 C13 C14 C19 56.2(3) 4_565 . . . ? C12 C13 C14 C15 123.8(3) . . . . ? C12 C13 C14 C15 -123.8(3) 4_565 . . . ? C19 C14 C15 C16 0.0 . . . . ? C13 C14 C15 C16 180.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C14 0.0 . . . . ? C17 C18 C19 C20 180.0 . . . . ? C15 C14 C19 C18 0.0 . . . . ? C13 C14 C19 C18 180.0 . . . . ? C15 C14 C19 C20 180.0 . . . . ? C13 C14 C19 C20 0.0 . . . . ? C18 C19 C20 C21 -123.6(2) . . . . ? C14 C19 C20 C21 56.4(2) . . . . ? C18 C19 C20 C21 123.6(2) . . . 4_565 ? C14 C19 C20 C21 -56.4(2) . . . 4_565 ? C11 C12 C21 C22 1.9(5) . . . . ? C13 C12 C21 C22 -179.0(3) . . . . ? C11 C12 C21 C20 -179.5(3) . . . . ? C13 C12 C21 C20 -0.4(4) . . . . ? C21 C20 C21 C22 -125.9(3) 4_565 . . . ? C19 C20 C21 C22 122.6(4) . . . . ? C21 C20 C21 C12 55.6(5) 4_565 . . . ? C19 C20 C21 C12 -56.0(4) . . . . ? C12 C21 C22 C9 0.0(5) . . . . ? C20 C21 C22 C9 -178.4(3) . . . . ? C10 C9 C22 C21 -1.3(5) . . . . ? N3 C9 C22 C21 -179.3(3) . . . . ? C1 O1 C23 C24 -49.1(5) . . . . ? C1 O1 C23 C36 137.6(3) . . . . ? C36 C23 C24 C25 -1.4(6) . . . . ? O1 C23 C24 C25 -174.3(3) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? C24 C25 C26 C35 2.2(5) . . . . ? C24 C25 C26 C27 -177.7(3) . . . . ? C25 C26 C27 C28 -123.8(4) . . . . ? C35 C26 C27 C28 56.2(4) . . . . ? C25 C26 C27 C26 124.0(3) . . . 4_565 ? C35 C26 C27 C26 -56.0(5) . . . 4_565 ? C26 C27 C28 C29 124.0(2) . . . . ? C26 C27 C28 C29 -124.0(2) 4_565 . . . ? C26 C27 C28 C33 -56.0(2) . . . . ? C26 C27 C28 C33 56.0(2) 4_565 . . . ? C33 C28 C29 C30 0.000(2) . . . . ? C27 C28 C29 C30 180.000(2) . . . . ? C28 C29 C30 C31 0.000(2) . . . . ? C29 C30 C31 C32 0.000(2) . . . . ? C30 C31 C32 C33 0.000(2) . . . . ? C31 C32 C33 C28 0.000(2) . . . . ? C31 C32 C33 C34 180.000(2) . . . . ? C29 C28 C33 C32 0.000(2) . . . . ? C27 C28 C33 C32 180.000(1) . . . . ? C29 C28 C33 C34 180.000(1) . . . . ? C27 C28 C33 C34 0.000(1) . . . . ? C32 C33 C34 C35 124.2(3) . . . 4_565 ? C28 C33 C34 C35 -55.8(3) . . . 4_565 ? C32 C33 C34 C35 -124.2(3) . . . . ? C28 C33 C34 C35 55.8(3) . . . . ? C25 C26 C35 C36 -2.2(5) . . . . ? C27 C26 C35 C36 177.7(3) . . . . ? C25 C26 C35 C34 179.3(3) . . . . ? C27 C26 C35 C34 -0.7(4) . . . . ? C33 C34 C35 C36 126.1(4) . . . . ? C35 C34 C35 C36 -121.2(3) 4_565 . . . ? C33 C34 C35 C26 -55.5(4) . . . . ? C35 C34 C35 C26 57.1(4) 4_565 . . . ? C26 C35 C36 C23 0.4(5) . . . . ? C34 C35 C36 C23 178.7(3) . . . . ? C24 C23 C36 C35 1.4(5) . . . . ? O1 C23 C36 C35 174.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.266 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.056 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.216 0.500 978 280 ' '