# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jonathan Hill' _publ_contact_author_address ; International Center for Young Scientists National Institure for Materials Science Namiki 1-1 Tsukuba Ibaraki 305-0044 JAPAN ; _publ_contact_author_email jonathan.hill@nims.go.jp _publ_contact_author_phone '+81 29 860 4706' loop_ _publ_author_name _publ_author_address 'Jonathan P. Hill' ; International Center for Young Scientists, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; 'Yutaka Wakayama' ; Nanomaterials Assembly Group, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; 'Wolfgang Schmitt' ; International Center for Young Scientists, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; 'Tohru Tsuruoka' ; Atomic Electronics Group, Advanced Materials Laboratory, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; 'Takashi Nakanishi' ; Supermolecules Group, Advanced Materials Laboratory, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; ; M.L.Zandler ; ; Department of Chemistry, Wichita State University, 1845 N. Fairmount, Wichita, Kansas 67260-0051, USA. ; 'Amy L. McCarty' ; Department of Chemistry, Wichita State University, 1845 N. Fairmount, Wichita, Kansas 67260-0051, USA. ; "Francis D'Souza" ; Department of Chemistry, Wichita State University, 1845 N. Fairmount, Wichita, Kansas 67260-0051, USA. ; 'Lionel R. Milgrom' ; Department of Chemistry, Imperial Coll. Sci. Tech Med., Exhibition Rd., South Kensington, London, UK. ; 'Katsuhiko Ariga' ; Supermolecules Group, Advanced Materials Laboratory, National Institute for Materials Science, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan. ; _publ_section_title ; Regulating the stability of 2D crystal structures using an oxidation state?dependent molecular conformation ; data_sad2 _database_code_depnum_ccdc_archive 'CCDC 280476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,10,15,20-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl)porphyrin ; _chemical_name_common 5,10,15,20-tetrakis(3,5-di-t-butyl-4-hydroxyphenyl)porphyrin _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C94 H122 N4 O4' _chemical_formula_weight 1371.96 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.643(2) _cell_length_b 14.476(3) _cell_length_c 15.377(3) _cell_angle_alpha 97.08(3) _cell_angle_beta 102.40(3) _cell_angle_gamma 110.63(3) _cell_volume 2113.5(7) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 522 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 30.86 _exptl_crystal_description 'rhombic block' _exptl_crystal_colour purple-red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker SMART Apex' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17899 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.56 _reflns_number_total 7878 _reflns_number_gt 3903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART Apex' _computing_cell_refinement 'Bruker SMART Apex' _computing_data_reduction 'Bruker SMART Apex' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 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^)+(0.1352P)^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 7878 _refine_ls_number_parameters 606 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1343 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2284 _refine_ls_wR_factor_gt 0.1697 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 0.1366(2) 0.08202(16) 0.01190(15) 0.0524(6) Uani 1 1 d . . . H1 H 0.1087 0.0266 -0.0225 0.079 Uiso 1 1 calc R . . O2 O 1.3317(3) 0.6084(2) 0.61517(14) 0.0728(8) Uani 1 1 d . . . H2 H 1.3290 0.5571 0.6336 0.109 Uiso 1 1 calc R . . N1 N 0.8161(2) 0.41384(17) -0.09530(15) 0.0341(6) Uani 1 1 d . . . N2 N 0.9169(2) 0.43725(18) 0.10060(16) 0.0327(6) Uani 1 1 d . . . C1 C 0.7839(3) 0.4170(2) -0.18614(19) 0.0334(7) Uani 1 1 d . . . C2 C 0.6373(3) 0.3574(2) -0.2274(2) 0.0383(7) Uani 1 1 d . . . H2A H 0.5889 0.3473 -0.2881 0.046 Uiso 1 1 calc R . . C3 C 0.5834(3) 0.3193(2) -0.16252(19) 0.0380(7) Uani 1 1 d . . . H3 H 0.4905 0.2781 -0.1700 0.046 Uiso 1 1 calc R . . C4 C 0.6939(3) 0.3530(2) -0.07936(18) 0.0333(7) Uani 1 1 d . . . C5 C 0.6788(3) 0.3294(2) 0.00444(18) 0.0312(7) Uani 1 1 d . . . C6 C 0.7837(3) 0.3687(2) 0.08711(18) 0.0326(7) Uani 1 1 d . . . C7 C 0.7708(3) 0.3462(2) 0.1735(2) 0.0367(7) Uani 1 1 d . . . H7 H 0.6921 0.2999 0.1839 0.044 Uiso 1 1 calc R . . C8 C 0.8910(3) 0.4029(2) 0.2368(2) 0.0354(7) Uani 1 1 d . . . C9 C 0.9856(3) 0.4608(2) 0.19150(18) 0.0334(7) Uani 1 1 d . . . C10 C 1.1243(3) 0.5291(2) 0.23250(18) 0.0330(7) Uani 1 1 d . . . C11 C 0.5366(3) 0.2615(2) 0.00693(19) 0.0356(7) Uani 1 1 d . . . C12 C 0.4700(3) 0.1628(2) -0.04475(19) 0.0365(7) Uani 1 1 d . . . H12 H 0.5162 0.1384 -0.0808 0.044 Uiso 1 1 calc R . . C13 C 0.3372(3) 0.0995(2) -0.04442(19) 0.0363(7) Uani 1 1 d . . . C14 C 0.2710(3) 0.1392(2) 0.0111(2) 0.0383(7) Uani 1 1 d . . . C15 C 0.3346(3) 0.2370(2) 0.06685(19) 0.0351(7) Uani 1 1 d . . . C16 C 0.4667(3) 0.2956(2) 0.0617(2) 0.0373(7) Uani 1 1 d . . . H16 H 0.5109 0.3612 0.0968 0.045 Uiso 1 1 calc R . . C17 C 1.1786(3) 0.5461(2) 0.33314(18) 0.0352(7) Uani 1 1 d . . . C18 C 1.1820(3) 0.4687(2) 0.3768(2) 0.0376(7) Uani 1 1 d . . . C19 C 1.2312(3) 0.4843(2) 0.47135(19) 0.0419(8) Uani 1 1 d . . . C20 C 1.2809(3) 0.5846(3) 0.52146(19) 0.0463(8) Uani 1 1 d . . . C21 C 1.2837(3) 0.6660(2) 0.4801(2) 0.0418(8) Uani 1 1 d . . . C22 C 1.2296(3) 0.6441(2) 0.3868(2) 0.0388(7) Uani 1 1 d . . . C23 C 0.2665(3) -0.0099(2) -0.1033(2) 0.0443(8) Uani 1 1 d . . . C24 C 0.3653(5) -0.0368(3) -0.1513(3) 0.0587(11) Uani 1 1 d . . . C25 C 0.1388(4) -0.0201(3) -0.1779(3) 0.0595(10) Uani 1 1 d . . . C26 C 0.2264(5) -0.0875(3) -0.0442(3) 0.0583(10) Uani 1 1 d . . . C27 C 0.2646(3) 0.2783(2) 0.1308(2) 0.0458(8) Uani 1 1 d . . . C28 C 0.3632(4) 0.3839(3) 0.1899(3) 0.0624(11) Uani 1 1 d . . . C29 C 0.1353(4) 0.2902(4) 0.0761(3) 0.0651(11) Uani 1 1 d . . . C30 C 0.2272(5) 0.2101(4) 0.1975(3) 0.0681(12) Uani 1 1 d . . . C31 C 1.3464(4) 0.7756(3) 0.5353(2) 0.0584(10) Uani 1 1 d . . . C32 C 1.2693(7) 0.7908(4) 0.6063(4) 0.0889(16) Uani 1 1 d . . . C33 C 1.3372(6) 0.8494(3) 0.4735(3) 0.0733(13) Uani 1 1 d . . . C34 C 1.5031(5) 0.8039(3) 0.5804(3) 0.0973(16) Uani 1 1 d . . . H34A H 1.5134 0.7590 0.6198 0.146 Uiso 1 1 calc R . . H34B H 1.5442 0.8722 0.6154 0.146 Uiso 1 1 calc R . . H34C H 1.5492 0.7982 0.5339 0.146 Uiso 1 1 calc R . . C35 C 1.2302(4) 0.3960(3) 0.5177(2) 0.0515(9) Uani 1 1 d . . . C36 C 1.1739(6) 0.2967(3) 0.4469(3) 0.0671(12) Uani 1 1 d . . . C37 C 1.3772(6) 0.4107(5) 0.5710(4) 0.0780(14) Uani 1 1 d . . . C38 C 1.1315(6) 0.3818(4) 0.5793(3) 0.0756(13) Uani 1 1 d . . . C39 C -0.3075(5) 0.5847(3) 0.1362(4) 0.0986(16) Uani 1 1 d . . . H39A H -0.4013 0.5804 0.1295 0.148 Uiso 1 1 calc R . . H39B H -0.2855 0.5470 0.1801 0.148 Uiso 1 1 calc R . . H39C H -0.2995 0.5572 0.0785 0.148 Uiso 1 1 calc R . . C40 C -0.2089(5) 0.6919(4) 0.1677(4) 0.0933(15) Uani 1 1 d . . . H40A H -0.2348 0.7297 0.1241 0.112 Uiso 1 1 calc R . . H40B H -0.2187 0.7190 0.2256 0.112 Uiso 1 1 calc R . . C41 C -0.0614(5) 0.7081(4) 0.1790(3) 0.0842(13) Uani 1 1 d . . . H41A H -0.0539 0.6735 0.1233 0.101 Uiso 1 1 calc R . . H41B H -0.0329 0.6768 0.2277 0.101 Uiso 1 1 calc R . . C42 C 0.0405(5) 0.8179(4) 0.2005(4) 0.0958(15) Uani 1 1 d . . . H42A H 0.0038 0.8515 0.1568 0.115 Uiso 1 1 calc R . . H42B H 0.0424 0.8497 0.2603 0.115 Uiso 1 1 calc R . . C43 C 0.1868(5) 0.8371(3) 0.1997(3) 0.0897(14) Uani 1 1 d . . . H43A H 0.2220 0.8000 0.2402 0.108 Uiso 1 1 calc R . . H43B H 0.1863 0.8101 0.1386 0.108 Uiso 1 1 calc R . . C44 C 0.2839(6) 0.9438(4) 0.2270(4) 0.119(2) Uani 1 1 d . . . H44A H 0.3753 0.9489 0.2243 0.178 Uiso 1 1 calc R . . H44B H 0.2880 0.9710 0.2882 0.178 Uiso 1 1 calc R . . H44C H 0.2518 0.9812 0.1865 0.178 Uiso 1 1 calc R . . C45 C 1.2896(17) 0.1192(12) 0.6293(11) 0.097(5) Uiso 0.50 1 d P . . C47 C 1.0486(14) 0.0281(10) 0.5417(9) 0.107(4) Uiso 0.50 1 d P . . C46A C 1.1914(16) 0.0465(11) 0.5575(11) 0.126(4) Uiso 0.50 1 d P . . C47A C 1.110(2) 0.0141(15) 0.4886(15) 0.188(7) Uiso 0.50 1 d P . . C46 C 1.112(3) 0.0647(16) 0.5892(15) 0.188(8) Uiso 0.50 1 d P . . C45A C 1.3238(18) 0.1089(13) 0.6313(11) 0.108(6) Uiso 0.50 1 d P . . H1A H 0.950(5) 0.468(3) 0.063(3) 0.101(16) Uiso 1 1 d . . . H8 H 0.912(3) 0.404(2) 0.302(2) 0.042(8) Uiso 1 1 d . . . H18 H 1.145(3) 0.397(2) 0.3391(19) 0.038(8) Uiso 1 1 d . . . H22 H 1.226(3) 0.695(2) 0.351(2) 0.044(9) Uiso 1 1 d . . . H24A H 0.448(4) -0.033(3) -0.112(3) 0.069(13) Uiso 1 1 d . . . H24C H 0.312(3) -0.104(3) -0.191(2) 0.055(10) Uiso 1 1 d . . . H24B H 0.390(3) 0.004(3) -0.198(2) 0.056(10) Uiso 1 1 d . . . H25A H 0.066(4) -0.006(3) -0.154(3) 0.086(14) Uiso 1 1 d . . . H25B H 0.167(4) 0.029(3) -0.218(3) 0.081(13) Uiso 1 1 d . . . H25C H 0.095(4) -0.098(3) -0.220(3) 0.078(11) Uiso 1 1 d . . . H26A H 0.155(4) -0.088(3) -0.011(2) 0.066(11) Uiso 1 1 d . . . H26B H 0.304(6) -0.093(4) 0.000(4) 0.122(19) Uiso 1 1 d . . . H26C H 0.190(4) -0.160(3) -0.080(3) 0.071(11) Uiso 1 1 d . . . H28A H 0.454(4) 0.382(3) 0.227(3) 0.074(12) Uiso 1 1 d . . . H28B H 0.400(4) 0.441(3) 0.148(3) 0.080(12) Uiso 1 1 d . . . H28C H 0.307(4) 0.406(3) 0.232(2) 0.070(11) Uiso 1 1 d . . . H29A H 0.062(4) 0.221(3) 0.032(3) 0.087(13) Uiso 1 1 d . . . H29B H 0.069(5) 0.303(3) 0.118(3) 0.099(14) Uiso 1 1 d . . . H29C H 0.156(5) 0.339(4) 0.042(3) 0.099(17) Uiso 1 1 d . . . H30A H 0.163(5) 0.139(4) 0.161(3) 0.108(17) Uiso 1 1 d . . . H30B H 0.173(5) 0.244(3) 0.244(3) 0.104(14) Uiso 1 1 d . . . H30C H 0.316(5) 0.207(3) 0.231(3) 0.093(15) Uiso 1 1 d . . . H32A H 1.145(9) 0.766(6) 0.589(6) 0.24(4) Uiso 1 1 d . . . H32B H 1.275(5) 0.751(3) 0.645(3) 0.086(16) Uiso 1 1 d . . . H32C H 1.315(5) 0.872(4) 0.641(3) 0.105(15) Uiso 1 1 d . . . H33A H 1.391(4) 0.845(3) 0.427(3) 0.070(12) Uiso 1 1 d . . . H33B H 1.374(4) 0.919(3) 0.508(2) 0.068(11) Uiso 1 1 d . . . H33C H 1.225(5) 0.833(3) 0.443(3) 0.105(16) Uiso 1 1 d . . . H36A H 1.172(4) 0.245(3) 0.477(3) 0.066(11) Uiso 1 1 d . . . H36B H 1.073(4) 0.280(3) 0.407(2) 0.063(11) Uiso 1 1 d . . . H36C H 1.229(4) 0.299(3) 0.403(3) 0.077(13) Uiso 1 1 d . . . H37A H 1.424(5) 0.402(4) 0.523(4) 0.115(19) Uiso 1 1 d . . . H37B H 1.368(5) 0.349(4) 0.598(3) 0.107(16) Uiso 1 1 d . . . H37C H 1.427(5) 0.468(4) 0.609(4) 0.11(2) Uiso 1 1 d . . . H38A H 1.028(6) 0.368(4) 0.541(4) 0.14(2) Uiso 1 1 d . . . H38B H 1.160(5) 0.429(3) 0.628(3) 0.085(15) Uiso 1 1 d . . . H38C H 1.120(4) 0.315(3) 0.601(3) 0.084(13) 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 0.0329(12) 0.0421(13) 0.0694(16) 0.0013(11) 0.0192(11) 0.0004(10) O2 0.103(2) 0.0711(18) 0.0261(12) 0.0038(11) -0.0040(13) 0.0276(17) N1 0.0353(14) 0.0342(14) 0.0292(13) 0.0073(10) 0.0105(11) 0.0086(11) N2 0.0294(14) 0.0327(14) 0.0304(14) 0.0077(11) 0.0069(11) 0.0063(11) C1 0.0314(17) 0.0352(17) 0.0317(15) 0.0075(13) 0.0064(13) 0.0123(14) C2 0.0322(17) 0.0374(18) 0.0339(16) 0.0052(13) 0.0010(13) 0.0060(14) C3 0.0281(16) 0.0390(18) 0.0344(16) 0.0037(13) 0.0042(13) 0.0027(14) C4 0.0302(16) 0.0324(17) 0.0335(16) 0.0057(13) 0.0082(13) 0.0087(13) C5 0.0284(15) 0.0292(16) 0.0338(16) 0.0043(12) 0.0091(13) 0.0094(13) C6 0.0319(17) 0.0299(16) 0.0328(16) 0.0062(12) 0.0096(13) 0.0081(13) C7 0.0317(17) 0.0369(17) 0.0410(17) 0.0114(14) 0.0151(14) 0.0090(14) C8 0.0341(17) 0.0390(18) 0.0280(16) 0.0070(13) 0.0072(14) 0.0093(14) C9 0.0380(17) 0.0335(17) 0.0240(14) 0.0046(12) 0.0048(13) 0.0112(14) C10 0.0368(17) 0.0302(16) 0.0253(14) 0.0030(12) 0.0049(13) 0.0085(14) C11 0.0322(16) 0.0343(17) 0.0344(16) 0.0074(13) 0.0081(13) 0.0066(14) C12 0.0327(17) 0.0358(18) 0.0363(16) 0.0053(13) 0.0096(13) 0.0089(14) C13 0.0331(17) 0.0335(17) 0.0375(16) 0.0048(13) 0.0092(13) 0.0086(14) C14 0.0274(16) 0.0362(18) 0.0420(17) 0.0092(14) 0.0092(14) 0.0017(14) C15 0.0307(16) 0.0349(17) 0.0362(16) 0.0051(13) 0.0108(13) 0.0086(14) C16 0.0338(17) 0.0330(17) 0.0384(16) 0.0041(13) 0.0114(14) 0.0058(14) C17 0.0303(16) 0.0416(18) 0.0281(15) 0.0054(14) 0.0058(13) 0.0094(14) C18 0.0359(18) 0.042(2) 0.0320(16) 0.0075(14) 0.0077(13) 0.0132(15) C19 0.0429(19) 0.050(2) 0.0319(16) 0.0103(15) 0.0082(14) 0.0183(16) C20 0.052(2) 0.052(2) 0.0250(16) 0.0045(15) 0.0014(14) 0.0158(17) C21 0.0403(19) 0.0432(19) 0.0321(17) -0.0010(14) 0.0050(14) 0.0108(15) C22 0.0386(18) 0.0413(19) 0.0307(16) 0.0052(14) 0.0075(14) 0.0111(15) C23 0.0375(18) 0.0348(18) 0.0513(19) 0.0015(15) 0.0122(16) 0.0060(15) C24 0.049(3) 0.044(2) 0.070(3) -0.009(2) 0.021(2) 0.006(2) C25 0.045(2) 0.058(3) 0.053(2) -0.006(2) -0.0010(19) 0.010(2) C26 0.052(2) 0.039(2) 0.083(3) 0.014(2) 0.026(2) 0.0117(19) C27 0.0371(19) 0.0430(19) 0.0504(19) 0.0012(15) 0.0170(15) 0.0077(15) C28 0.046(2) 0.055(2) 0.070(3) -0.016(2) 0.023(2) 0.0066(19) C29 0.047(2) 0.066(3) 0.083(3) 0.005(3) 0.018(2) 0.027(2) C30 0.071(3) 0.073(3) 0.054(2) 0.010(2) 0.029(2) 0.014(3) C31 0.064(2) 0.048(2) 0.045(2) -0.0027(16) 0.0073(18) 0.0087(19) C32 0.142(5) 0.065(3) 0.064(3) 0.002(3) 0.052(3) 0.036(3) C33 0.106(4) 0.040(2) 0.058(3) 0.001(2) 0.019(3) 0.016(2) C34 0.077(3) 0.066(3) 0.093(3) -0.008(2) -0.021(3) -0.002(2) C35 0.063(2) 0.059(2) 0.0352(17) 0.0159(16) 0.0105(16) 0.0272(19) C36 0.096(4) 0.062(3) 0.050(2) 0.022(2) 0.017(3) 0.037(3) C37 0.083(3) 0.086(4) 0.065(3) 0.025(3) -0.002(3) 0.043(3) C38 0.105(4) 0.075(3) 0.054(3) 0.024(3) 0.036(3) 0.032(3) C39 0.071(3) 0.064(3) 0.160(5) 0.025(3) 0.034(3) 0.024(3) C40 0.087(4) 0.102(4) 0.098(4) 0.028(3) 0.025(3) 0.043(3) C41 0.074(3) 0.097(4) 0.085(3) 0.022(3) 0.012(2) 0.042(3) C42 0.095(4) 0.079(4) 0.106(4) 0.010(3) 0.015(3) 0.037(3) C43 0.092(4) 0.073(3) 0.097(3) 0.016(3) 0.020(3) 0.028(3) C44 0.116(5) 0.086(4) 0.123(5) 0.004(3) 0.038(4) 0.006(3) _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 C14 1.381(3) . ? O2 C20 1.378(4) . ? N1 C1 1.376(3) . ? N1 C4 1.382(3) . ? N2 C6 1.367(4) . ? N2 C9 1.368(4) . ? C1 C10 1.404(4) 2_765 ? C1 C2 1.440(4) . ? C2 C3 1.337(4) . ? C3 C4 1.433(4) . ? C4 C5 1.401(4) . ? C5 C6 1.397(4) . ? C5 C11 1.498(4) . ? C6 C7 1.430(4) . ? C7 C8 1.337(4) . ? C8 C9 1.432(4) . ? C9 C10 1.404(4) . ? C10 C1 1.404(4) 2_765 ? C10 C17 1.487(4) . ? C11 C16 1.391(4) . ? C11 C12 1.392(4) . ? C12 C13 1.388(4) . ? C13 C14 1.406(4) . ? C13 C23 1.552(4) . ? C14 C15 1.405(4) . ? C15 C16 1.388(4) . ? C15 C27 1.537(4) . ? C17 C18 1.383(4) . ? C17 C22 1.402(4) . ? C18 C19 1.395(4) . ? C19 C20 1.410(4) . ? C19 C35 1.536(5) . ? C20 C21 1.402(5) . ? C21 C22 1.376(4) . ? C21 C31 1.537(5) . ? C23 C25 1.527(5) . ? C23 C26 1.533(5) . ? C23 C24 1.535(5) . ? C27 C30 1.528(5) . ? C27 C29 1.529(5) . ? C27 C28 1.544(5) . ? C31 C33 1.529(6) . ? C31 C32 1.537(6) . ? C31 C34 1.543(6) . ? C35 C37 1.528(6) . ? C35 C36 1.529(5) . ? C35 C38 1.539(6) . ? C39 C40 1.481(6) . ? C40 C41 1.471(6) . ? C41 C42 1.521(6) . ? C42 C43 1.486(6) . ? C43 C44 1.470(6) . ? C45 C46A 1.37(2) . ? C45 C46 1.70(3) . ? C47 C46 0.84(2) . ? C47 C47A 1.19(2) . ? C47 C47 1.40(3) 2_756 ? C47 C46A 1.41(2) . ? C47 C47A 1.51(2) 2_756 ? C46A C47A 1.14(2) . ? C46A C46 1.15(2) . ? C46A C45A 1.50(2) . ? C47A C47 1.51(2) 2_756 ? C47A C46 1.62(3) . ? C46 C45A 2.04(3) . ? 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 C4 106.7(2) . . ? C6 N2 C9 108.7(2) . . ? N1 C1 C10 126.7(3) . 2_765 ? N1 C1 C2 109.0(2) . . ? C10 C1 C2 124.3(3) 2_765 . ? C3 C2 C1 107.5(3) . . ? C2 C3 C4 108.0(3) . . ? N1 C4 C5 126.0(3) . . ? N1 C4 C3 108.8(2) . . ? C5 C4 C3 125.1(3) . . ? C6 C5 C4 125.2(3) . . ? C6 C5 C11 117.2(2) . . ? C4 C5 C11 117.5(2) . . ? N2 C6 C5 126.3(2) . . ? N2 C6 C7 107.4(2) . . ? C5 C6 C7 126.3(3) . . ? C8 C7 C6 108.5(3) . . ? C7 C8 C9 107.6(3) . . ? N2 C9 C10 125.9(3) . . ? N2 C9 C8 107.8(2) . . ? C10 C9 C8 126.4(2) . . ? C1 C10 C9 125.3(3) 2_765 . ? C1 C10 C17 117.2(3) 2_765 . ? C9 C10 C17 117.5(2) . . ? C16 C11 C12 117.7(3) . . ? C16 C11 C5 120.5(3) . . ? C12 C11 C5 121.8(3) . . ? C13 C12 C11 122.4(3) . . ? C12 C13 C14 117.1(3) . . ? C12 C13 C23 120.8(3) . . ? C14 C13 C23 122.1(2) . . ? O1 C14 C15 116.7(3) . . ? O1 C14 C13 120.2(3) . . ? C15 C14 C13 123.1(3) . . ? C16 C15 C14 116.1(3) . . ? C16 C15 C27 121.0(3) . . ? C14 C15 C27 122.9(2) . . ? C15 C16 C11 123.5(3) . . ? C18 C17 C22 117.9(3) . . ? C18 C17 C10 122.6(3) . . ? C22 C17 C10 119.5(3) . . ? C17 C18 C19 122.7(3) . . ? C18 C19 C20 116.7(3) . . ? C18 C19 C35 121.2(3) . . ? C20 C19 C35 122.2(3) . . ? O2 C20 C21 115.8(3) . . ? O2 C20 C19 121.4(3) . . ? C21 C20 C19 122.8(3) . . ? C22 C21 C20 117.1(3) . . ? C22 C21 C31 120.9(3) . . ? C20 C21 C31 122.0(3) . . ? C21 C22 C17 122.8(3) . . ? C25 C23 C26 111.0(3) . . ? C25 C23 C24 106.9(3) . . ? C26 C23 C24 106.1(3) . . ? C25 C23 C13 110.0(3) . . ? C26 C23 C13 111.1(3) . . ? C24 C23 C13 111.5(3) . . ? C30 C27 C29 110.9(3) . . ? C30 C27 C15 110.7(3) . . ? C29 C27 C15 110.8(3) . . ? C30 C27 C28 106.0(3) . . ? C29 C27 C28 106.5(3) . . ? C15 C27 C28 111.7(3) . . ? C33 C31 C32 106.5(4) . . ? C33 C31 C21 111.3(3) . . ? C32 C31 C21 112.2(3) . . ? C33 C31 C34 106.9(4) . . ? C32 C31 C34 111.7(4) . . ? C21 C31 C34 108.2(3) . . ? C37 C35 C36 106.2(4) . . ? C37 C35 C19 111.9(3) . . ? C36 C35 C19 110.9(3) . . ? C37 C35 C38 111.3(4) . . ? C36 C35 C38 106.4(4) . . ? C19 C35 C38 109.9(3) . . ? C41 C40 C39 114.4(4) . . ? C40 C41 C42 115.6(4) . . ? C43 C42 C41 117.1(4) . . ? C44 C43 C42 115.3(5) . . ? C46A C45 C46 42.2(9) . . ? C46 C47 C47A 104(3) . . ? C46 C47 C47 175(3) . 2_756 ? C47A C47 C47 71.1(16) . 2_756 ? C46 C47 C46A 54.7(19) . . ? C47A C47 C46A 51.2(13) . . ? C47 C47 C46A 121.5(17) 2_756 . ? C46 C47 C47A 137(3) . 2_756 ? C47A C47 C47A 119.0(17) . 2_756 ? C47 C47 C47A 47.9(10) 2_756 2_756 ? C46A C47 C47A 166.9(16) . 2_756 ? C47A C46A C46 90.1(19) . . ? C47A C46A C45 157.3(19) . . ? C46 C46A C45 84.7(18) . . ? C47A C46A C47 54.3(12) . . ? C46 C46A C47 36.9(12) . . ? C45 C46A C47 121.1(15) . . ? C47A C46A C45A 162.3(19) . . ? C46 C46A C45A 99.7(19) . . ? C45 C46A C45A 16.6(10) . . ? C47 C46A C45A 136.5(16) . . ? C46A C47A C47 74.5(17) . . ? C46A C47A C47 134(2) . 2_756 ? C47 C47A C47 61.0(17) . 2_756 ? C46A C47A C46 45.2(12) . . ? C47 C47A C46 30.4(11) . . ? C47 C47A C46 91(2) 2_756 . ? C47 C46 C46A 88(2) . . ? C47 C46 C47A 45.3(18) . . ? C46A C46 C47A 44.7(12) . . ? C47 C46 C45 141(3) . . ? C46A C46 C45 53.0(14) . . ? C47A C46 C45 95.3(17) . . ? C47 C46 C45A 135(3) . . ? C46A C46 C45A 46.6(15) . . ? C47A C46 C45A 90.3(16) . . ? C45 C46 C45A 8.6(9) . . ? C46A C45A C46 33.7(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.56 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.495 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.075