# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hiroyuki Furuta' _publ_contact_author_address ; Chemistry and Biochemistry Kyushu University 744 Motooka Nishi-ku Fukuoka 819-0395 JAPAN ; _publ_contact_author_email HFURUTA@CSTF.KYUSHU-U.AC.JP _publ_section_title ; Endocyclic extension of porphyrin ?-system in etheno-bridged N-confused tetraphenylporphyrin ; loop_ _publ_author_name 'Hiroyuki Furuta' 'Tomoyuki Kimura' 'Motoki Toganoh' # Attachment 'EtO-ethenoNCP.CIF' data_etheno _database_code_depnum_ccdc_archive 'CCDC 636924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H34 N4 O' _chemical_formula_sum 'C48 H34 N4 O' _chemical_formula_weight 682.79 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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.648(3) _cell_length_b 13.477(4) _cell_length_c 15.109(4) _cell_angle_alpha 82.536(6) _cell_angle_beta 74.261(6) _cell_angle_gamma 82.981(6) _cell_volume 1867.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10215 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.1977 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6532 _reflns_number_gt 2480 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0983P)^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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0045(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6532 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2142 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.2415 _refine_ls_wR_factor_gt 0.1854 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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 0.7314(6) 0.1328(4) 0.4784(3) 0.0426(14) Uani 1 1 d . . . C2 C 0.7855(5) 0.0781(4) 0.3959(3) 0.0400(13) Uani 1 1 d . . . C3 C 0.8115(5) 0.1548(4) 0.3225(3) 0.0369(13) Uani 1 1 d . . . C4 C 0.7640(5) 0.2479(4) 0.3610(3) 0.0413(14) Uani 1 1 d . . . C5 C 0.7531(5) 0.3464(4) 0.3170(3) 0.0396(13) Uani 1 1 d . . . C6 C 0.7520(6) 0.3700(4) 0.2228(3) 0.0398(13) Uani 1 1 d . . . C7 C 0.7711(6) 0.4665(4) 0.1698(4) 0.0486(15) Uani 1 1 d . . . H1 H 0.7867 0.5251 0.1920 0.058 Uiso 1 1 calc R . . C8 C 0.7630(6) 0.4593(4) 0.0828(4) 0.0466(14) Uani 1 1 d . . . H2 H 0.7712 0.5116 0.0345 0.056 Uiso 1 1 calc R . . C9 C 0.7395(6) 0.3566(4) 0.0776(3) 0.0395(13) Uani 1 1 d . . . C10 C 0.7371(6) 0.3148(4) -0.0017(3) 0.0406(14) Uani 1 1 d . . . C11 C 0.7388(5) 0.2101(4) -0.0076(3) 0.0400(13) Uani 1 1 d . . . C12 C 0.7545(6) 0.1652(4) -0.0925(4) 0.0503(15) Uani 1 1 d . . . H3 H 0.7571 0.1997 -0.1510 0.060 Uiso 1 1 calc R . . C13 C 0.7646(6) 0.0649(4) -0.0716(4) 0.0474(14) Uani 1 1 d . . . H4 H 0.7757 0.0165 -0.1131 0.057 Uiso 1 1 calc R . . C14 C 0.7552(6) 0.0450(4) 0.0267(3) 0.0417(13) Uani 1 1 d . . . C15 C 0.7673(6) -0.0532(4) 0.0727(3) 0.0401(13) Uani 1 1 d . . . C16 C 0.7786(6) -0.0800(4) 0.1637(4) 0.0455(14) Uani 1 1 d . . . C17 C 0.7545(6) -0.1742(4) 0.2175(4) 0.0534(16) Uani 1 1 d . . . H5 H 0.7327 -0.2314 0.1963 0.064 Uiso 1 1 calc R . . C18 C 0.7677(6) -0.1692(4) 0.3048(4) 0.0537(16) Uani 1 1 d . . . H6 H 0.7583 -0.2223 0.3523 0.064 Uiso 1 1 calc R . . C19 C 0.7982(6) -0.0689(4) 0.3112(3) 0.0418(14) Uani 1 1 d . . . C20 C 0.7910(5) -0.0272(4) 0.3927(3) 0.0385(13) Uani 1 1 d . . . N1 N 0.7168(5) 0.2301(3) 0.4603(3) 0.0459(12) Uani 1 1 d . . . N2 N 0.7327(5) 0.3063(3) 0.1637(3) 0.0447(12) Uani 1 1 d . . . H7 H 0.7183 0.2432 0.1787 0.054 Uiso 1 1 calc R . . N3 N 0.7357(4) 0.1361(3) 0.0641(3) 0.0435(12) Uani 1 1 d . . . N4 N 0.8083(5) -0.0169(3) 0.2221(3) 0.0411(11) Uani 1 1 d . . . C21 C 0.9014(6) 0.1410(4) 0.2306(3) 0.0420(14) Uani 1 1 d . . . H8 H 0.9637 0.1906 0.2007 0.050 Uiso 1 1 calc R . . C22 C 0.9014(5) 0.0619(4) 0.1856(3) 0.0402(13) Uani 1 1 d . . . H9 H 0.9660 0.0578 0.1269 0.048 Uiso 1 1 calc R . . C23 C 0.7326(6) 0.4337(4) 0.3732(4) 0.0468(15) Uani 1 1 d . . . C24 C 0.8231(7) 0.4374(4) 0.4310(4) 0.0587(17) Uani 1 1 d . . . H10 H 0.8968 0.3857 0.4344 0.070 Uiso 1 1 calc R . . C25 C 0.8030(9) 0.5186(6) 0.4834(4) 0.080(2) Uani 1 1 d . . . H11 H 0.8650 0.5221 0.5211 0.096 Uiso 1 1 calc R . . C26 C 0.6940(11) 0.5930(5) 0.4804(5) 0.091(3) Uani 1 1 d . . . H12 H 0.6814 0.6470 0.5163 0.109 Uiso 1 1 calc R . . C27 C 0.6042(9) 0.5898(5) 0.4262(5) 0.084(2) Uani 1 1 d . . . H13 H 0.5299 0.6415 0.4243 0.100 Uiso 1 1 calc R . . C28 C 0.6222(7) 0.5086(4) 0.3722(4) 0.0644(18) Uani 1 1 d . . . H14 H 0.5584 0.5057 0.3355 0.077 Uiso 1 1 calc R . . C29 C 0.7438(6) 0.3833(4) -0.0886(3) 0.0441(14) Uani 1 1 d . . . C30 C 0.8750(7) 0.3960(5) -0.1541(4) 0.079(2) Uani 1 1 d . . . H15 H 0.9603 0.3612 -0.1431 0.095 Uiso 1 1 calc R . . C31 C 0.8823(9) 0.4589(6) -0.2352(5) 0.089(2) Uani 1 1 d . . . H16 H 0.9719 0.4670 -0.2784 0.107 Uiso 1 1 calc R . . C32 C 0.7587(9) 0.5090(5) -0.2521(4) 0.0686(19) Uani 1 1 d . . . H17 H 0.7631 0.5512 -0.3073 0.082 Uiso 1 1 calc R . . C33 C 0.6300(8) 0.4981(4) -0.1893(4) 0.0646(18) Uani 1 1 d . . . H18 H 0.5451 0.5326 -0.2012 0.078 Uiso 1 1 calc R . . C34 C 0.6228(7) 0.4360(4) -0.1076(4) 0.0591(17) Uani 1 1 d . . . H19 H 0.5328 0.4301 -0.0642 0.071 Uiso 1 1 calc R . . C35 C 0.7635(6) -0.1401(4) 0.0202(3) 0.0421(14) Uani 1 1 d . . . C36 C 0.8777(6) -0.2144(4) 0.0066(3) 0.0410(13) Uani 1 1 d . . . H20 H 0.9569 -0.2107 0.0307 0.049 Uiso 1 1 calc R . . C37 C 0.8760(6) -0.2944(4) -0.0426(3) 0.0502(15) Uani 1 1 d . . . H21 H 0.9533 -0.3450 -0.0510 0.060 Uiso 1 1 calc R . . C38 C 0.7613(7) -0.2996(4) -0.0791(4) 0.0516(15) Uani 1 1 d . . . H22 H 0.7616 -0.3536 -0.1128 0.062 Uiso 1 1 calc R . . C39 C 0.6462(7) -0.2271(5) -0.0670(4) 0.0576(16) Uani 1 1 d . . . H23 H 0.5682 -0.2308 -0.0922 0.069 Uiso 1 1 calc R . . C40 C 0.6481(6) -0.1471(4) -0.0159(4) 0.0528(15) Uani 1 1 d . . . H24 H 0.5695 -0.0977 -0.0061 0.063 Uiso 1 1 calc R . . C41 C 0.7704(6) -0.0953(4) 0.4802(3) 0.0415(13) Uani 1 1 d . . . C42 C 0.6326(6) -0.1223(4) 0.5275(3) 0.0491(15) Uani 1 1 d . . . H25 H 0.5549 -0.1027 0.5007 0.059 Uiso 1 1 calc R . . C43 C 0.6087(7) -0.1778(4) 0.6138(4) 0.0582(17) Uani 1 1 d . . . H26 H 0.5149 -0.1937 0.6459 0.070 Uiso 1 1 calc R . . C44 C 0.7224(8) -0.2093(4) 0.6519(4) 0.0622(18) Uani 1 1 d . . . H27 H 0.7065 -0.2471 0.7100 0.075 Uiso 1 1 calc R . . C45 C 0.8603(8) -0.1856(5) 0.6050(4) 0.0664(18) Uani 1 1 d . . . H28 H 0.9386 -0.2077 0.6306 0.080 Uiso 1 1 calc R . . C46 C 0.8820(7) -0.1292(5) 0.5199(4) 0.0616(17) Uani 1 1 d . . . H29 H 0.9762 -0.1135 0.4882 0.074 Uiso 1 1 calc R . . O1 O 0.6990(4) 0.0842(3) 0.5631(2) 0.0587(11) Uani 1 1 d . . . C47 C 0.6441(8) 0.1458(5) 0.6405(4) 0.076(2) Uani 1 1 d . . . H30 H 0.5539 0.1856 0.6357 0.091 Uiso 1 1 calc R . . H31 H 0.7152 0.1916 0.6414 0.091 Uiso 1 1 calc R . . C48 C 0.6179(9) 0.0715(5) 0.7279(4) 0.101(3) Uani 1 1 d . . . H32 H 0.5513 0.0246 0.7243 0.152 Uiso 1 1 calc R . . H33 H 0.5770 0.1079 0.7817 0.152 Uiso 1 1 calc R . . H34 H 0.7089 0.0348 0.7329 0.152 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 0.051(4) 0.048(4) 0.032(3) -0.001(3) -0.012(3) -0.016(3) C2 0.044(3) 0.041(3) 0.036(3) 0.000(3) -0.013(3) -0.007(3) C3 0.043(3) 0.033(3) 0.032(3) 0.002(2) -0.005(3) -0.006(2) C4 0.043(3) 0.044(4) 0.037(3) 0.002(3) -0.010(3) -0.013(3) C5 0.047(3) 0.031(3) 0.038(3) -0.001(3) -0.007(3) -0.006(3) C6 0.049(4) 0.029(3) 0.042(3) 0.002(3) -0.013(3) -0.009(3) C7 0.060(4) 0.033(3) 0.053(4) 0.002(3) -0.014(3) -0.009(3) C8 0.061(4) 0.036(3) 0.043(3) 0.013(3) -0.019(3) -0.010(3) C9 0.047(3) 0.031(3) 0.041(3) 0.003(3) -0.013(3) -0.006(3) C10 0.046(3) 0.044(3) 0.033(3) 0.006(3) -0.013(3) -0.011(3) C11 0.037(3) 0.046(4) 0.038(3) 0.000(3) -0.013(3) -0.003(3) C12 0.061(4) 0.056(4) 0.037(3) -0.001(3) -0.019(3) -0.006(3) C13 0.055(4) 0.042(4) 0.046(3) -0.006(3) -0.015(3) -0.003(3) C14 0.046(3) 0.038(3) 0.039(3) -0.001(3) -0.009(3) -0.004(3) C15 0.047(3) 0.034(3) 0.039(3) -0.002(3) -0.009(3) -0.008(3) C16 0.050(4) 0.038(3) 0.050(3) -0.005(3) -0.015(3) -0.005(3) C17 0.079(5) 0.035(3) 0.049(4) -0.003(3) -0.016(3) -0.014(3) C18 0.070(4) 0.037(4) 0.050(4) 0.003(3) -0.012(3) -0.004(3) C19 0.054(4) 0.029(3) 0.039(3) 0.007(3) -0.009(3) -0.007(3) C20 0.041(3) 0.038(3) 0.040(3) 0.002(3) -0.016(3) -0.010(3) N1 0.059(3) 0.036(3) 0.043(3) -0.001(2) -0.013(2) -0.010(2) N2 0.061(3) 0.028(2) 0.046(3) 0.004(2) -0.014(2) -0.014(2) N3 0.052(3) 0.037(3) 0.039(3) 0.002(2) -0.010(2) -0.007(2) N4 0.055(3) 0.031(2) 0.039(3) -0.002(2) -0.013(2) -0.009(2) C21 0.048(4) 0.036(3) 0.042(3) 0.003(3) -0.012(3) -0.013(3) C22 0.041(3) 0.045(3) 0.034(3) 0.001(3) -0.006(3) -0.011(3) C23 0.057(4) 0.038(3) 0.043(3) -0.001(3) -0.007(3) -0.013(3) C24 0.071(4) 0.060(4) 0.047(4) -0.004(3) -0.017(3) -0.013(3) C25 0.125(7) 0.063(5) 0.063(5) -0.023(4) -0.021(4) -0.040(5) C26 0.165(9) 0.042(5) 0.055(5) -0.015(4) 0.000(5) -0.023(5) C27 0.140(7) 0.034(4) 0.067(5) -0.003(4) -0.017(5) 0.002(4) C28 0.088(5) 0.038(4) 0.061(4) -0.001(3) -0.012(4) -0.004(4) C29 0.052(4) 0.040(3) 0.044(3) -0.001(3) -0.017(3) -0.007(3) C30 0.063(5) 0.092(6) 0.065(4) 0.027(4) -0.009(4) -0.001(4) C31 0.085(6) 0.095(6) 0.068(5) 0.036(4) -0.004(4) -0.015(5) C32 0.109(6) 0.049(4) 0.049(4) 0.010(3) -0.026(4) -0.015(4) C33 0.081(5) 0.062(4) 0.058(4) 0.011(4) -0.035(4) -0.009(4) C34 0.065(4) 0.063(4) 0.049(4) 0.007(3) -0.019(3) -0.007(3) C35 0.047(4) 0.037(3) 0.041(3) -0.002(3) -0.010(3) -0.006(3) C36 0.043(3) 0.039(3) 0.044(3) 0.000(3) -0.015(3) -0.009(3) C37 0.059(4) 0.037(3) 0.050(3) -0.001(3) -0.006(3) -0.006(3) C38 0.063(4) 0.039(4) 0.052(4) -0.007(3) -0.009(3) -0.011(3) C39 0.053(4) 0.067(4) 0.061(4) -0.016(3) -0.020(3) -0.015(4) C40 0.046(4) 0.049(4) 0.064(4) -0.012(3) -0.014(3) 0.001(3) C41 0.053(4) 0.034(3) 0.040(3) 0.003(3) -0.016(3) -0.007(3) C42 0.047(4) 0.058(4) 0.043(3) 0.003(3) -0.015(3) -0.012(3) C43 0.069(5) 0.058(4) 0.045(4) 0.005(3) -0.007(3) -0.023(3) C44 0.103(6) 0.036(4) 0.048(4) 0.009(3) -0.023(4) -0.015(4) C45 0.074(5) 0.062(4) 0.068(4) 0.008(4) -0.036(4) 0.000(4) C46 0.056(4) 0.070(4) 0.062(4) 0.010(3) -0.023(3) -0.014(3) O1 0.089(3) 0.050(2) 0.037(2) -0.002(2) -0.011(2) -0.017(2) C47 0.100(6) 0.075(5) 0.054(4) -0.002(4) -0.020(4) -0.016(4) C48 0.158(8) 0.103(6) 0.045(4) -0.007(4) -0.023(4) -0.025(6) _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 N1 1.302(6) . ? C1 O1 1.334(6) . ? C1 C2 1.470(7) . ? C2 C3 1.405(6) . ? C2 C20 1.421(7) . ? C3 C4 1.423(7) . ? C3 C21 1.446(6) . ? C4 C5 1.411(7) . ? C4 N1 1.442(6) . ? C5 C6 1.420(6) . ? C5 C23 1.502(7) . ? C6 N2 1.377(6) . ? C6 C7 1.441(6) . ? C7 C8 1.354(6) . ? C7 H1 0.9400 . ? C8 C9 1.444(6) . ? C8 H2 0.9400 . ? C9 N2 1.375(6) . ? C9 C10 1.396(6) . ? C10 C11 1.422(7) . ? C10 C29 1.495(7) . ? C11 N3 1.371(6) . ? C11 C12 1.452(6) . ? C12 C13 1.345(7) . ? C12 H3 0.9400 . ? C13 C14 1.454(7) . ? C13 H4 0.9400 . ? C14 N3 1.389(6) . ? C14 C15 1.420(7) . ? C15 C16 1.406(7) . ? C15 C35 1.506(7) . ? C16 N4 1.407(6) . ? C16 C17 1.423(7) . ? C17 C18 1.369(7) . ? C17 H5 0.9400 . ? C18 C19 1.439(7) . ? C18 H6 0.9400 . ? C19 C20 1.401(6) . ? C19 N4 1.418(6) . ? C20 C41 1.489(6) . ? N2 H7 0.8700 . ? N4 C22 1.432(6) . ? C21 C22 1.337(6) . ? C21 H8 0.9400 . ? C22 H9 0.9400 . ? C23 C28 1.377(8) . ? C23 C24 1.400(7) . ? C24 C25 1.398(8) . ? C24 H10 0.9400 . ? C25 C26 1.368(10) . ? C25 H11 0.9400 . ? C26 C27 1.351(9) . ? C26 H12 0.9400 . ? C27 C28 1.415(8) . ? C27 H13 0.9400 . ? C28 H14 0.9400 . ? C29 C34 1.370(7) . ? C29 C30 1.393(7) . ? C30 C31 1.388(8) . ? C30 H15 0.9400 . ? C31 C32 1.366(9) . ? C31 H16 0.9400 . ? C32 C33 1.354(8) . ? C32 H17 0.9400 . ? C33 C34 1.389(7) . ? C33 H18 0.9400 . ? C34 H19 0.9400 . ? C35 C40 1.384(7) . ? C35 C36 1.386(7) . ? C36 C37 1.392(7) . ? C36 H20 0.9400 . ? C37 C38 1.376(7) . ? C37 H21 0.9400 . ? C38 C39 1.375(8) . ? C38 H22 0.9400 . ? C39 C40 1.409(7) . ? C39 H23 0.9400 . ? C40 H24 0.9400 . ? C41 C46 1.373(7) . ? C41 C42 1.395(7) . ? C42 C43 1.393(7) . ? C42 H25 0.9400 . ? C43 C44 1.370(8) . ? C43 H26 0.9400 . ? C44 C45 1.381(8) . ? C44 H27 0.9400 . ? C45 C46 1.384(8) . ? C45 H28 0.9400 . ? C46 H29 0.9400 . ? O1 C47 1.465(6) . ? C47 C48 1.532(8) . ? C47 H30 0.9800 . ? C47 H31 0.9800 . ? C48 H32 0.9700 . ? C48 H33 0.9700 . ? C48 H34 0.9700 . ? 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 N1 C1 O1 124.7(5) . . ? N1 C1 C2 114.0(4) . . ? O1 C1 C2 121.3(5) . . ? C3 C2 C20 129.1(5) . . ? C3 C2 C1 103.8(4) . . ? C20 C2 C1 126.7(4) . . ? C2 C3 C4 107.2(4) . . ? C2 C3 C21 124.6(5) . . ? C4 C3 C21 126.6(4) . . ? C5 C4 C3 130.2(4) . . ? C5 C4 N1 120.1(5) . . ? C3 C4 N1 109.7(4) . . ? C4 C5 C6 124.4(5) . . ? C4 C5 C23 119.0(4) . . ? C6 C5 C23 116.5(5) . . ? N2 C6 C5 127.5(4) . . ? N2 C6 C7 106.0(4) . . ? C5 C6 C7 126.4(4) . . ? C8 C7 C6 109.0(4) . . ? C8 C7 H1 125.5 . . ? C6 C7 H1 125.5 . . ? C7 C8 C9 107.6(4) . . ? C7 C8 H2 126.2 . . ? C9 C8 H2 126.2 . . ? N2 C9 C10 126.6(4) . . ? N2 C9 C8 106.8(4) . . ? C10 C9 C8 126.4(5) . . ? C9 C10 C11 124.6(4) . . ? C9 C10 C29 118.1(4) . . ? C11 C10 C29 117.1(4) . . ? N3 C11 C10 125.4(4) . . ? N3 C11 C12 109.7(4) . . ? C10 C11 C12 124.7(5) . . ? C13 C12 C11 107.1(5) . . ? C13 C12 H3 126.4 . . ? C11 C12 H3 126.4 . . ? C12 C13 C14 107.7(5) . . ? C12 C13 H4 126.2 . . ? C14 C13 H4 126.2 . . ? N3 C14 C15 127.8(4) . . ? N3 C14 C13 108.7(4) . . ? C15 C14 C13 123.5(5) . . ? C16 C15 C14 127.7(4) . . ? C16 C15 C35 115.0(4) . . ? C14 C15 C35 117.4(4) . . ? C15 C16 N4 126.7(5) . . ? C15 C16 C17 127.5(5) . . ? N4 C16 C17 105.8(4) . . ? C18 C17 C16 110.2(5) . . ? C18 C17 H5 124.9 . . ? C16 C17 H5 124.9 . . ? C17 C18 C19 108.4(5) . . ? C17 C18 H6 125.8 . . ? C19 C18 H6 125.8 . . ? C20 C19 N4 127.1(4) . . ? C20 C19 C18 126.1(4) . . ? N4 C19 C18 105.7(4) . . ? C19 C20 C2 122.1(4) . . ? C19 C20 C41 118.0(4) . . ? C2 C20 C41 119.5(4) . . ? C1 N1 C4 105.1(4) . . ? C9 N2 C6 110.5(4) . . ? C9 N2 H7 124.8 . . ? C6 N2 H7 124.8 . . ? C11 N3 C14 106.7(4) . . ? C16 N4 C19 109.9(4) . . ? C16 N4 C22 121.0(4) . . ? C19 N4 C22 122.3(4) . . ? C22 C21 C3 123.9(5) . . ? C22 C21 H8 118.0 . . ? C3 C21 H8 118.0 . . ? C21 C22 N4 123.5(5) . . ? C21 C22 H9 118.2 . . ? N4 C22 H9 118.2 . . ? C28 C23 C24 119.0(5) . . ? C28 C23 C5 121.2(5) . . ? C24 C23 C5 119.8(5) . . ? C25 C24 C23 119.5(6) . . ? C25 C24 H10 120.3 . . ? C23 C24 H10 120.3 . . ? C26 C25 C24 120.6(7) . . ? C26 C25 H11 119.7 . . ? C24 C25 H11 119.7 . . ? C27 C26 C25 120.7(7) . . ? C27 C26 H12 119.7 . . ? C25 C26 H12 119.7 . . ? C26 C27 C28 119.9(7) . . ? C26 C27 H13 120.0 . . ? C28 C27 H13 120.0 . . ? C23 C28 C27 120.3(6) . . ? C23 C28 H14 119.9 . . ? C27 C28 H14 119.9 . . ? C34 C29 C30 117.2(5) . . ? C34 C29 C10 122.0(5) . . ? C30 C29 C10 120.8(5) . . ? C31 C30 C29 121.3(7) . . ? C31 C30 H15 119.4 . . ? C29 C30 H15 119.4 . . ? C32 C31 C30 119.7(7) . . ? C32 C31 H16 120.2 . . ? C30 C31 H16 120.2 . . ? C33 C32 C31 120.1(6) . . ? C33 C32 H17 120.0 . . ? C31 C32 H17 120.0 . . ? C32 C33 C34 120.3(6) . . ? C32 C33 H18 119.9 . . ? C34 C33 H18 119.9 . . ? C29 C34 C33 121.5(6) . . ? C29 C34 H19 119.2 . . ? C33 C34 H19 119.2 . . ? C40 C35 C36 118.7(5) . . ? C40 C35 C15 121.3(5) . . ? C36 C35 C15 120.0(5) . . ? C35 C36 C37 120.5(5) . . ? C35 C36 H20 119.8 . . ? C37 C36 H20 119.8 . . ? C38 C37 C36 120.0(5) . . ? C38 C37 H21 120.0 . . ? C36 C37 H21 120.0 . . ? C39 C38 C37 121.1(5) . . ? C39 C38 H22 119.5 . . ? C37 C38 H22 119.5 . . ? C38 C39 C40 118.4(5) . . ? C38 C39 H23 120.8 . . ? C40 C39 H23 120.8 . . ? C35 C40 C39 121.3(5) . . ? C35 C40 H24 119.4 . . ? C39 C40 H24 119.4 . . ? C46 C41 C42 117.7(5) . . ? C46 C41 C20 122.3(5) . . ? C42 C41 C20 119.9(5) . . ? C43 C42 C41 120.8(5) . . ? C43 C42 H25 119.6 . . ? C41 C42 H25 119.6 . . ? C44 C43 C42 119.9(6) . . ? C44 C43 H26 120.0 . . ? C42 C43 H26 120.0 . . ? C43 C44 C45 120.1(6) . . ? C43 C44 H27 120.0 . . ? C45 C44 H27 120.0 . . ? C44 C45 C46 119.4(6) . . ? C44 C45 H28 120.3 . . ? C46 C45 H28 120.3 . . ? C41 C46 C45 122.1(6) . . ? C41 C46 H29 119.0 . . ? C45 C46 H29 119.0 . . ? C1 O1 C47 116.9(4) . . ? O1 C47 C48 105.7(5) . . ? O1 C47 H30 110.6 . . ? C48 C47 H30 110.6 . . ? O1 C47 H31 110.6 . . ? C48 C47 H31 110.6 . . ? H30 C47 H31 108.7 . . ? C47 C48 H32 109.5 . . ? C47 C48 H33 109.5 . . ? H32 C48 H33 109.5 . . ? C47 C48 H34 109.5 . . ? H32 C48 H34 109.5 . . ? H33 C48 H34 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.424 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.068