# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Lee, Chang-Hee' _publ_contact_author_name 'Lee, Chang-Hee' _publ_contact_author_email chhlee@kangwon.ac.kr _publ_section_title ; Anion-Modulated, Highly Sensitive Supramolecular Fluorescence Chemosensor for C70 ; # Attachment '- C1P3P-cif.cif' data_yk861p21n _database_code_depnum_ccdc_archive 'CCDC 771695' #TrackingRef '- C1P3P-cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H41 N3' _chemical_formula_weight 563.76 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' _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 10.0878(11) _cell_length_b 32.621(4) _cell_length_c 10.2902(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.273(2) _cell_angle_gamma 90.00 _cell_volume 3196.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2358 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 20.79 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.068 _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 293(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17811 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.1171 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6284 _reflns_number_gt 2647 _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^)+(0.0235P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6284 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0648 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _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 0.94789(15) 0.13244(6) 0.21150(15) 0.0448(5) Uani 1 1 d . . . C2 C 1.06660(15) 0.11945(6) 0.15645(15) 0.0672(6) Uani 1 1 d . . . H2A H 1.1553 0.1283 0.2195 0.101 Uiso 1 1 calc R . . H2B H 1.0516 0.1318 0.0681 0.101 Uiso 1 1 calc R . . H2C H 1.0666 0.0902 0.1475 0.101 Uiso 1 1 calc R . . C3 C 0.95543(16) 0.17940(6) 0.22523(16) 0.0639(6) Uani 1 1 d . . . H3A H 0.8869 0.1887 0.2648 0.096 Uiso 1 1 calc R . . H3B H 0.9366 0.1915 0.1359 0.096 Uiso 1 1 calc R . . H3C H 1.0475 0.1873 0.2836 0.096 Uiso 1 1 calc R . . C4 C 0.97077(16) 0.11568(5) 0.35394(16) 0.0450(5) Uani 1 1 d . . . C5 C 1.08554(17) 0.10310(6) 0.45843(17) 0.0657(6) Uani 1 1 d . . . H5 H 1.1749 0.0990 0.4534 0.079 Uiso 1 1 calc R . . C6 C 1.04495(18) 0.09741(6) 0.57656(17) 0.0675(6) Uani 1 1 d . . . H6 H 1.1036 0.0891 0.6629 0.081 Uiso 1 1 calc R . . C7 C 0.90640(17) 0.10611(5) 0.54254(16) 0.0478(5) Uani 1 1 d . . . C8 C 0.80597(17) 0.10477(6) 0.62385(16) 0.0508(5) Uani 1 1 d . . . C9 C 0.87560(17) 0.12489(6) 0.76581(15) 0.0796(7) Uani 1 1 d . . . H9A H 0.8999 0.1527 0.7535 0.119 Uiso 1 1 calc R . . H9B H 0.9589 0.1099 0.8155 0.119 Uiso 1 1 calc R . . H9C H 0.8113 0.1245 0.8168 0.119 Uiso 1 1 calc R . . C10 C 0.77261(18) 0.05991(6) 0.64579(18) 0.0774(6) Uani 1 1 d . . . H10A H 0.7070 0.0589 0.6953 0.116 Uiso 1 1 calc R . . H10B H 0.8575 0.0460 0.6977 0.116 Uiso 1 1 calc R . . H10C H 0.7325 0.0467 0.5581 0.116 Uiso 1 1 calc R . . C11 C 0.67221(18) 0.12699(6) 0.54765(15) 0.0452(5) Uani 1 1 d . . . C12 C 0.53672(18) 0.11443(6) 0.49813(16) 0.0552(5) Uani 1 1 d . . . H12 H 0.5045 0.0881 0.5050 0.066 Uiso 1 1 calc R . . C13 C 0.45273(17) 0.14825(6) 0.43427(16) 0.0537(5) Uani 1 1 d . . . H13 H 0.3558 0.1478 0.3922 0.064 Uiso 1 1 calc R . . C14 C 0.53711(17) 0.18148(6) 0.44452(15) 0.0416(4) Uani 1 1 d . . . C15 C 0.50481(16) 0.22423(5) 0.38885(15) 0.0442(5) Uani 1 1 d . . . C16 C 0.60515(16) 0.25534(5) 0.48439(15) 0.0598(5) Uani 1 1 d . . . H16A H 0.6993 0.2502 0.4857 0.090 Uiso 1 1 calc R . . H16B H 0.6010 0.2526 0.5759 0.090 Uiso 1 1 calc R . . H16C H 0.5778 0.2826 0.4513 0.090 Uiso 1 1 calc R . . C17 C 0.35316(16) 0.23543(5) 0.37998(16) 0.0669(6) Uani 1 1 d . . . H17A H 0.3320 0.2628 0.3446 0.100 Uiso 1 1 calc R . . H17B H 0.3446 0.2339 0.4701 0.100 Uiso 1 1 calc R . . H17C H 0.2886 0.2165 0.3197 0.100 Uiso 1 1 calc R . . C18 C 0.51649(16) 0.22684(6) 0.24622(16) 0.0418(4) Uani 1 1 d . . . C19 C 0.54557(16) 0.25822(6) 0.17312(17) 0.0547(5) Uani 1 1 d . . . H19 H 0.5713 0.2846 0.2055 0.066 Uiso 1 1 calc R . . C20 C 0.52998(16) 0.24378(6) 0.03909(17) 0.0526(5) Uani 1 1 d . . . H20 H 0.5442 0.2591 -0.0314 0.063 Uiso 1 1 calc R . . C21 C 0.49078(15) 0.20377(5) 0.03094(16) 0.0407(4) Uani 1 1 d . . . C22 C 0.45889(16) 0.17203(5) -0.08245(15) 0.0433(4) Uani 1 1 d . . . C23 C 0.30770(15) 0.15684(5) -0.10252(16) 0.0651(6) Uani 1 1 d . . . H23A H 0.3099 0.1377 -0.0311 0.098 Uiso 1 1 calc R . . H23B H 0.2701 0.1437 -0.1906 0.098 Uiso 1 1 calc R . . H23C H 0.2496 0.1798 -0.0983 0.098 Uiso 1 1 calc R . . C24 C 0.46413(19) 0.19294(5) -0.21489(15) 0.0711(6) Uani 1 1 d . . . H24A H 0.3951 0.2144 -0.2407 0.107 Uiso 1 1 calc R . . H24B H 0.4448 0.1731 -0.2876 0.107 Uiso 1 1 calc R . . H24C H 0.5558 0.2044 -0.1989 0.107 Uiso 1 1 calc R . . C25 C 0.56881(15) 0.13726(5) -0.04168(14) 0.0378(4) Uani 1 1 d . . . C26 C 0.69831(16) 0.14628(5) 0.05548(14) 0.0407(4) Uani 1 1 d . . . H26 H 0.7152 0.1733 0.0848 0.049 Uiso 1 1 calc R . . C27 C 0.80472(15) 0.11788(5) 0.11223(14) 0.0390(4) Uani 1 1 d . . . C28 C 0.77554(16) 0.07644(5) 0.07519(15) 0.0395(4) Uani 1 1 d . . . C29 C 0.86624(17) 0.04331(6) 0.14216(17) 0.0547(5) Uani 1 1 d . . . H29 H 0.9459 0.0490 0.2170 0.066 Uiso 1 1 calc R . . C30 C 0.83912(19) 0.00450(6) 0.09977(19) 0.0639(6) Uani 1 1 d . . . H30 H 0.9008 -0.0160 0.1461 0.077 Uiso 1 1 calc R . . C31 C 0.72000(19) -0.00650(6) -0.01302(18) 0.0519(5) Uani 1 1 d . . . C32 C 0.6929(2) -0.04653(6) -0.0585(2) 0.0677(6) Uani 1 1 d . . . H32 H 0.7553 -0.0671 -0.0143 0.081 Uiso 1 1 calc R . . C33 C 0.5758(2) -0.05654(6) -0.1675(2) 0.0723(6) Uani 1 1 d . . . H33 H 0.5599 -0.0836 -0.1969 0.087 Uiso 1 1 calc R . . C34 C 0.4819(2) -0.02636(7) -0.23350(19) 0.0649(6) Uani 1 1 d . . . H34 H 0.4029 -0.0332 -0.3075 0.078 Uiso 1 1 calc R . . C35 C 0.50381(18) 0.01413(6) -0.19077(17) 0.0471(5) Uani 1 1 d . . . C36 C 0.62468(17) 0.02495(6) -0.07873(16) 0.0420(4) Uani 1 1 d . . . C37 C 0.64984(15) 0.06628(5) -0.03335(15) 0.0378(4) Uani 1 1 d . . . C38 C 0.54912(15) 0.09739(5) -0.09694(15) 0.0379(4) Uani 1 1 d . . . C39 C 0.43297(16) 0.08519(6) -0.21559(15) 0.0465(5) Uani 1 1 d . . . H39 H 0.3701 0.1052 -0.2637 0.056 Uiso 1 1 calc R . . C40 C 0.41163(17) 0.04629(6) -0.25964(16) 0.0512(5) Uani 1 1 d . . . H40 H 0.3349 0.0401 -0.3369 0.061 Uiso 1 1 calc R . . N1 N 0.86305(15) 0.11711(5) 0.40637(14) 0.0481(4) Uani 1 1 d . . . H1N H 0.7779(16) 0.1247(5) 0.3649(16) 0.077(7) Uiso 1 1 d . . . N2 N 0.67122(16) 0.16786(5) 0.51384(14) 0.0480(4) Uani 1 1 d . . . H2N H 0.7424(16) 0.1834(5) 0.5342(16) 0.067(7) Uiso 1 1 d . . . N3 N 0.48173(14) 0.19392(5) 0.15783(14) 0.0437(4) Uani 1 1 d . . . H3N H 0.4657(15) 0.1692(5) 0.1850(15) 0.063(6) 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 C1 0.0315(10) 0.0678(14) 0.0339(10) -0.0058(9) 0.0094(8) -0.0101(9) C2 0.0385(10) 0.1170(19) 0.0488(11) -0.0077(11) 0.0180(9) -0.0072(11) C3 0.0549(12) 0.0786(17) 0.0520(11) -0.0073(11) 0.0092(10) -0.0276(11) C4 0.0303(10) 0.0697(14) 0.0349(10) -0.0013(9) 0.0105(9) -0.0038(9) C5 0.0352(11) 0.1131(19) 0.0478(12) 0.0116(12) 0.0123(10) 0.0059(11) C6 0.0425(12) 0.1128(19) 0.0389(11) 0.0160(11) 0.0023(10) 0.0040(11) C7 0.0403(11) 0.0697(14) 0.0298(10) 0.0056(9) 0.0070(9) 0.0006(9) C8 0.0517(12) 0.0645(15) 0.0369(10) 0.0078(10) 0.0153(9) -0.0001(10) C9 0.0712(14) 0.131(2) 0.0340(11) -0.0036(12) 0.0138(10) 0.0105(13) C10 0.0725(14) 0.0874(18) 0.0766(14) 0.0315(12) 0.0305(11) 0.0093(12) C11 0.0484(12) 0.0557(14) 0.0341(10) 0.0055(9) 0.0172(9) -0.0040(10) C12 0.0534(12) 0.0616(15) 0.0487(11) 0.0025(10) 0.0143(10) -0.0136(11) C13 0.0396(11) 0.0671(15) 0.0485(11) -0.0019(10) 0.0063(9) -0.0093(11) C14 0.0348(11) 0.0585(14) 0.0318(10) -0.0059(9) 0.0113(9) -0.0042(10) C15 0.0393(11) 0.0546(14) 0.0396(11) -0.0080(9) 0.0143(9) -0.0034(9) C16 0.0644(12) 0.0613(14) 0.0532(11) -0.0174(10) 0.0186(10) -0.0063(10) C17 0.0498(12) 0.0874(17) 0.0669(13) -0.0013(11) 0.0240(10) 0.0097(10) C18 0.0419(10) 0.0426(12) 0.0396(10) -0.0070(10) 0.0119(9) -0.0036(9) C19 0.0676(13) 0.0447(13) 0.0523(12) -0.0089(10) 0.0206(10) -0.0137(10) C20 0.0658(12) 0.0480(14) 0.0460(12) 0.0062(10) 0.0209(10) -0.0040(10) C21 0.0468(11) 0.0415(13) 0.0337(11) 0.0056(9) 0.0130(8) 0.0052(9) C22 0.0481(11) 0.0450(12) 0.0309(10) 0.0004(9) 0.0053(8) 0.0054(9) C23 0.0444(11) 0.0722(15) 0.0667(12) -0.0180(10) 0.0019(10) 0.0106(10) C24 0.1078(16) 0.0648(15) 0.0376(11) 0.0071(10) 0.0199(11) 0.0150(12) C25 0.0401(10) 0.0452(13) 0.0276(9) 0.0005(9) 0.0104(8) -0.0005(9) C26 0.0443(11) 0.0442(12) 0.0340(10) -0.0044(8) 0.0133(9) -0.0045(9) C27 0.0336(10) 0.0555(14) 0.0292(9) -0.0015(9) 0.0119(8) -0.0036(9) C28 0.0331(10) 0.0516(13) 0.0341(10) 0.0017(9) 0.0115(8) 0.0042(9) C29 0.0426(11) 0.0619(15) 0.0541(12) -0.0013(11) 0.0084(9) 0.0072(11) C30 0.0560(13) 0.0630(16) 0.0679(14) 0.0049(12) 0.0139(11) 0.0194(11) C31 0.0570(13) 0.0489(15) 0.0550(13) -0.0035(11) 0.0256(11) 0.0039(11) C32 0.0802(15) 0.0548(16) 0.0728(15) -0.0017(12) 0.0318(13) 0.0103(12) C33 0.1016(18) 0.0456(16) 0.0762(16) -0.0109(12) 0.0379(14) -0.0044(13) C34 0.0765(15) 0.0606(16) 0.0587(13) -0.0154(12) 0.0239(11) -0.0145(13) C35 0.0515(12) 0.0490(14) 0.0439(12) -0.0099(10) 0.0201(10) -0.0096(11) C36 0.0461(11) 0.0460(13) 0.0383(11) -0.0023(10) 0.0196(9) 0.0007(10) C37 0.0347(10) 0.0466(13) 0.0329(10) -0.0022(9) 0.0124(8) 0.0029(9) C38 0.0356(10) 0.0486(13) 0.0290(9) -0.0030(9) 0.0100(8) -0.0047(9) C39 0.0426(11) 0.0556(14) 0.0382(10) -0.0054(9) 0.0092(9) 0.0025(9) C40 0.0464(11) 0.0629(15) 0.0399(11) -0.0134(11) 0.0083(9) -0.0070(11) N1 0.0341(9) 0.0762(12) 0.0332(9) 0.0053(8) 0.0102(8) 0.0033(8) N2 0.0380(10) 0.0630(13) 0.0435(9) -0.0009(9) 0.0142(8) -0.0093(9) N3 0.0555(10) 0.0372(11) 0.0389(9) 0.0014(8) 0.0162(8) -0.0054(8) _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 C4 1.509(2) . ? C1 C3 1.538(2) . ? C1 C27 1.5430(18) . ? C1 C2 1.543(2) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.3576(18) . ? C4 N1 1.3642(18) . ? C5 C6 1.417(2) . ? C5 H5 0.9300 . ? C6 C7 1.3541(19) . ? C6 H6 0.9300 . ? C7 N1 1.3708(18) . ? C7 C8 1.513(2) . ? C8 C11 1.504(2) . ? C8 C10 1.535(2) . ? C8 C9 1.543(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.355(2) . ? C11 N2 1.377(2) . ? C12 C13 1.414(2) . ? C12 H12 0.9300 . ? C13 C14 1.361(2) . ? C13 H13 0.9300 . ? C14 N2 1.3783(19) . ? C14 C15 1.502(2) . ? C15 C18 1.513(2) . ? C15 C16 1.5376(19) . ? C15 C17 1.5460(19) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.358(2) . ? C18 N3 1.3757(19) . ? C19 C20 1.416(2) . ? C19 H19 0.9300 . ? C20 C21 1.358(2) . ? C20 H20 0.9300 . ? C21 N3 1.3766(18) . ? C21 C22 1.513(2) . ? C22 C24 1.5404(19) . ? C22 C25 1.544(2) . ? C22 C23 1.5513(19) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.3894(17) . ? C25 C38 1.407(2) . ? C26 C27 1.3921(19) . ? C26 H26 0.9300 . ? C27 C28 1.409(2) . ? C28 C37 1.4248(18) . ? C28 C29 1.437(2) . ? C29 C30 1.338(2) . ? C29 H29 0.9300 . ? C30 C31 1.414(2) . ? C30 H30 0.9300 . ? C31 C32 1.384(2) . ? C31 C36 1.416(2) . ? C32 C33 1.373(2) . ? C32 H32 0.9300 . ? C33 C34 1.380(2) . ? C33 H33 0.9300 . ? C34 C35 1.387(2) . ? C34 H34 0.9300 . ? C35 C36 1.4186(19) . ? C35 C40 1.426(2) . ? C36 C37 1.422(2) . ? C37 C38 1.4321(19) . ? C38 C39 1.4414(18) . ? C39 C40 1.341(2) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? N1 H1N 0.860(14) . ? N2 H2N 0.848(15) . ? N3 H3N 0.885(15) . ? 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 C4 C1 C3 106.53(13) . . ? C4 C1 C27 109.95(13) . . ? C3 C1 C27 111.99(13) . . ? C4 C1 C2 111.63(13) . . ? C3 C1 C2 106.64(14) . . ? C27 C1 C2 110.04(12) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 N1 106.23(14) . . ? C5 C4 C1 134.09(15) . . ? N1 C4 C1 119.04(14) . . ? C4 C5 C6 107.85(15) . . ? C4 C5 H5 126.1 . . ? C6 C5 H5 126.1 . . ? C7 C6 C5 108.46(14) . . ? C7 C6 H6 125.8 . . ? C5 C6 H6 125.8 . . ? C6 C7 N1 105.84(15) . . ? C6 C7 C8 132.35(16) . . ? N1 C7 C8 121.81(14) . . ? C11 C8 C7 110.32(14) . . ? C11 C8 C10 109.48(14) . . ? C7 C8 C10 109.17(15) . . ? C11 C8 C9 109.77(15) . . ? C7 C8 C9 109.43(13) . . ? C10 C8 C9 108.64(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N2 105.99(16) . . ? C12 C11 C8 132.10(18) . . ? N2 C11 C8 121.91(16) . . ? C11 C12 C13 108.31(17) . . ? C11 C12 H12 125.8 . . ? C13 C12 H12 125.8 . . ? C14 C13 C12 108.79(16) . . ? C14 C13 H13 125.6 . . ? C12 C13 H13 125.6 . . ? C13 C14 N2 105.38(17) . . ? C13 C14 C15 131.21(16) . . ? N2 C14 C15 123.30(15) . . ? C14 C15 C18 110.22(14) . . ? C14 C15 C16 110.78(13) . . ? C18 C15 C16 109.73(14) . . ? C14 C15 C17 109.13(14) . . ? C18 C15 C17 108.77(13) . . ? C16 C15 C17 108.16(14) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 N3 106.05(14) . . ? C19 C18 C15 132.81(17) . . ? N3 C18 C15 120.87(16) . . ? C18 C19 C20 108.29(15) . . ? C18 C19 H19 125.9 . . ? C20 C19 H19 125.9 . . ? C21 C20 C19 108.43(15) . . ? C21 C20 H20 125.8 . . ? C19 C20 H20 125.8 . . ? C20 C21 N3 105.95(15) . . ? C20 C21 C22 133.52(16) . . ? N3 C21 C22 120.52(16) . . ? C21 C22 C24 108.57(14) . . ? C21 C22 C25 110.01(13) . . ? C24 C22 C25 109.53(13) . . ? C21 C22 C23 105.71(13) . . ? C24 C22 C23 110.07(13) . . ? C25 C22 C23 112.81(14) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C38 117.41(14) . . ? C26 C25 C22 117.40(15) . . ? C38 C25 C22 125.18(14) . . ? C25 C26 C27 124.93(15) . . ? C25 C26 H26 117.5 . . ? C27 C26 H26 117.5 . . ? C26 C27 C28 117.51(14) . . ? C26 C27 C1 119.77(16) . . ? C28 C27 C1 122.73(15) . . ? C27 C28 C37 119.17(15) . . ? C27 C28 C29 123.29(15) . . ? C37 C28 C29 117.54(16) . . ? C30 C29 C28 121.75(17) . . ? C30 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? C29 C30 C31 122.33(17) . . ? C29 C30 H30 118.8 . . ? C31 C30 H30 118.8 . . ? C32 C31 C30 122.46(19) . . ? C32 C31 C36 119.66(18) . . ? C30 C31 C36 117.86(18) . . ? C33 C32 C31 121.44(19) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C34 119.9(2) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C35 120.81(19) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C34 C35 C36 119.93(18) . . ? C34 C35 C40 122.26(18) . . ? C36 C35 C40 117.75(17) . . ? C31 C36 C35 118.30(17) . . ? C31 C36 C37 120.71(16) . . ? C35 C36 C37 121.00(16) . . ? C36 C37 C28 119.60(15) . . ? C36 C37 C38 119.93(15) . . ? C28 C37 C38 120.47(16) . . ? C25 C38 C37 119.08(14) . . ? C25 C38 C39 124.35(15) . . ? C37 C38 C39 116.57(15) . . ? C40 C39 C38 122.86(16) . . ? C40 C39 H39 118.6 . . ? C38 C39 H39 118.6 . . ? C39 C40 C35 121.52(16) . . ? C39 C40 H40 119.2 . . ? C35 C40 H40 119.2 . . ? C4 N1 C7 111.61(14) . . ? C4 N1 H1N 127.6(11) . . ? C7 N1 H1N 120.8(11) . . ? C11 N2 C14 111.53(15) . . ? C11 N2 H2N 125.7(12) . . ? C14 N2 H2N 122.7(12) . . ? C18 N3 C21 111.27(15) . . ? C18 N3 H3N 122.3(10) . . ? C21 N3 H3N 126.0(10) . . ? 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 C3 C1 C4 C5 -92.2(2) . . . . ? C27 C1 C4 C5 146.2(2) . . . . ? C2 C1 C4 C5 23.8(3) . . . . ? C3 C1 C4 N1 77.13(18) . . . . ? C27 C1 C4 N1 -44.4(2) . . . . ? C2 C1 C4 N1 -166.84(15) . . . . ? N1 C4 C5 C6 -0.7(2) . . . . ? C1 C4 C5 C6 169.59(19) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 N1 -0.3(2) . . . . ? C5 C6 C7 C8 178.67(18) . . . . ? C6 C7 C8 C11 166.4(2) . . . . ? N1 C7 C8 C11 -14.8(2) . . . . ? C6 C7 C8 C10 -73.2(2) . . . . ? N1 C7 C8 C10 105.56(18) . . . . ? C6 C7 C8 C9 45.5(3) . . . . ? N1 C7 C8 C9 -135.66(16) . . . . ? C7 C8 C11 C12 119.68(19) . . . . ? C10 C8 C11 C12 -0.5(2) . . . . ? C9 C8 C11 C12 -119.6(2) . . . . ? C7 C8 C11 N2 -59.8(2) . . . . ? C10 C8 C11 N2 -179.91(14) . . . . ? C9 C8 C11 N2 60.92(19) . . . . ? N2 C11 C12 C13 -0.35(19) . . . . ? C8 C11 C12 C13 -179.85(16) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 N2 0.11(19) . . . . ? C12 C13 C14 C15 176.35(15) . . . . ? C13 C14 C15 C18 -89.1(2) . . . . ? N2 C14 C15 C18 86.56(17) . . . . ? C13 C14 C15 C16 149.27(17) . . . . ? N2 C14 C15 C16 -35.1(2) . . . . ? C13 C14 C15 C17 30.3(2) . . . . ? N2 C14 C15 C17 -154.05(14) . . . . ? C14 C15 C18 C19 -153.62(18) . . . . ? C16 C15 C18 C19 -31.4(2) . . . . ? C17 C15 C18 C19 86.8(2) . . . . ? C14 C15 C18 N3 33.2(2) . . . . ? C16 C15 C18 N3 155.47(15) . . . . ? C17 C15 C18 N3 -86.40(18) . . . . ? N3 C18 C19 C20 -0.83(19) . . . . ? C15 C18 C19 C20 -174.73(16) . . . . ? C18 C19 C20 C21 0.3(2) . . . . ? C19 C20 C21 N3 0.33(18) . . . . ? C19 C20 C21 C22 -179.82(16) . . . . ? C20 C21 C22 C24 -5.1(2) . . . . ? N3 C21 C22 C24 174.71(13) . . . . ? C20 C21 C22 C25 114.7(2) . . . . ? N3 C21 C22 C25 -65.44(18) . . . . ? C20 C21 C22 C23 -123.19(19) . . . . ? N3 C21 C22 C23 56.64(18) . . . . ? C21 C22 C25 C26 -23.07(19) . . . . ? C24 C22 C25 C26 96.19(16) . . . . ? C23 C22 C25 C26 -140.84(14) . . . . ? C21 C22 C25 C38 158.14(14) . . . . ? C24 C22 C25 C38 -82.60(19) . . . . ? C23 C22 C25 C38 40.4(2) . . . . ? C38 C25 C26 C27 -6.7(2) . . . . ? C22 C25 C26 C27 174.38(14) . . . . ? C25 C26 C27 C28 -4.4(2) . . . . ? C25 C26 C27 C1 175.55(13) . . . . ? C4 C1 C27 C26 113.76(16) . . . . ? C3 C1 C27 C26 -4.47(19) . . . . ? C2 C1 C27 C26 -122.89(16) . . . . ? C4 C1 C27 C28 -66.30(19) . . . . ? C3 C1 C27 C28 175.48(14) . . . . ? C2 C1 C27 C28 57.06(19) . . . . ? C26 C27 C28 C37 10.0(2) . . . . ? C1 C27 C28 C37 -169.96(13) . . . . ? C26 C27 C28 C29 -169.61(14) . . . . ? C1 C27 C28 C29 10.4(2) . . . . ? C27 C28 C29 C30 -176.46(16) . . . . ? C37 C28 C29 C30 3.9(2) . . . . ? C28 C29 C30 C31 -0.1(3) . . . . ? C29 C30 C31 C32 178.92(17) . . . . ? C29 C30 C31 C36 -2.4(3) . . . . ? C30 C31 C32 C33 179.41(17) . . . . ? C36 C31 C32 C33 0.7(3) . . . . ? C31 C32 C33 C34 -0.4(3) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? C33 C34 C35 C36 0.6(3) . . . . ? C33 C34 C35 C40 177.69(17) . . . . ? C32 C31 C36 C35 -0.4(2) . . . . ? C30 C31 C36 C35 -179.13(14) . . . . ? C32 C31 C36 C37 179.64(15) . . . . ? C30 C31 C36 C37 0.9(2) . . . . ? C34 C35 C36 C31 -0.2(2) . . . . ? C40 C35 C36 C31 -177.50(14) . . . . ? C34 C35 C36 C37 179.72(15) . . . . ? C40 C35 C36 C37 2.5(2) . . . . ? C31 C36 C37 C28 2.9(2) . . . . ? C35 C36 C37 C28 -177.02(13) . . . . ? C31 C36 C37 C38 -177.16(14) . . . . ? C35 C36 C37 C38 2.9(2) . . . . ? C27 C28 C37 C36 175.12(14) . . . . ? C29 C28 C37 C36 -5.3(2) . . . . ? C27 C28 C37 C38 -4.8(2) . . . . ? C29 C28 C37 C38 174.85(14) . . . . ? C26 C25 C38 C37 11.9(2) . . . . ? C22 C25 C38 C37 -169.31(14) . . . . ? C26 C25 C38 C39 -167.89(13) . . . . ? C22 C25 C38 C39 10.9(2) . . . . ? C36 C37 C38 C25 173.64(14) . . . . ? C28 C37 C38 C25 -6.5(2) . . . . ? C36 C37 C38 C39 -6.6(2) . . . . ? C28 C37 C38 C39 173.34(13) . . . . ? C25 C38 C39 C40 -174.95(15) . . . . ? C37 C38 C39 C40 5.3(2) . . . . ? C38 C39 C40 C35 0.0(2) . . . . ? C34 C35 C40 C39 178.84(16) . . . . ? C36 C35 C40 C39 -4.0(2) . . . . ? C5 C4 N1 C7 0.6(2) . . . . ? C1 C4 N1 C7 -171.48(15) . . . . ? C6 C7 N1 C4 -0.2(2) . . . . ? C8 C7 N1 C4 -179.27(16) . . . . ? C12 C11 N2 C14 0.44(18) . . . . ? C8 C11 N2 C14 180.00(14) . . . . ? C13 C14 N2 C11 -0.34(18) . . . . ? C15 C14 N2 C11 -176.95(14) . . . . ? C19 C18 N3 C21 1.07(18) . . . . ? C15 C18 N3 C21 175.86(13) . . . . ? C20 C21 N3 C18 -0.87(18) . . . . ? C22 C21 N3 C18 179.25(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.108 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.027