# 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 _publ_contact_author_name 'Liu, Shi-Xia' _publ_contact_author_email liu@iac.unibe.ch _publ_section_title ; Synthesis, Structures, Redox and Photophysical Properties of Benzodifuran-functionalised Pyrene and Anthracene Fluorophores ; loop_ _publ_author_name S.Keller C.Yi C.Li S.-X.Liu C.Blum G.Frei O.Sereda A.Neels ; T.Wandlowski ; S.Decurtins # Attachment 'compound1.CIF' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 783323' #TrackingRef 'compound1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H70 N4 O2' _chemical_formula_weight 1023.32 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.8530(13) _cell_length_b 15.5929(15) _cell_length_c 25.462(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.951(6) _cell_angle_gamma 90.00 _cell_volume 5659.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4147 _cell_measurement_theta_min 1.43 _cell_measurement_theta_max 22.03 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.072 _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 173(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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38921 _diffrn_reflns_av_R_equivalents 0.3199 _diffrn_reflns_av_sigmaI/netI 0.4024 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.16 _reflns_number_total 10102 _reflns_number_gt 1782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _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^)+(0.0001P)^2^] 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 10102 _refine_ls_number_parameters 647 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3205 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1745 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.668 _refine_ls_restrained_S_all 0.668 _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 0.3853(5) 0.3819(4) 0.1310(3) 0.048(2) Uani 1 1 d . . . C2 C 0.5402(5) 0.3096(5) 0.1687(4) 0.069(3) Uani 1 1 d . . . H2A H 0.5917 0.3203 0.2079 0.083 Uiso 1 1 calc R . . H2B H 0.5492 0.3482 0.1407 0.083 Uiso 1 1 calc R . . C3 C 0.5443(5) 0.2162(5) 0.1513(3) 0.060(2) Uani 1 1 d . . . H3A H 0.5037 0.2085 0.1090 0.071 Uiso 1 1 calc R . . H3B H 0.5214 0.1778 0.1732 0.071 Uiso 1 1 calc R . . C4 C 0.6464(4) 0.1939(5) 0.1652(3) 0.062(2) Uani 1 1 d . . . H4A H 0.6682 0.2329 0.1430 0.074 Uiso 1 1 calc R . . H4B H 0.6863 0.2037 0.2073 0.074 Uiso 1 1 calc R . . C5 C 0.6585(4) 0.1020(5) 0.1504(4) 0.064(2) Uani 1 1 d . . . H5A H 0.6189 0.0924 0.1082 0.077 Uiso 1 1 calc R . . H5B H 0.6359 0.0631 0.1722 0.077 Uiso 1 1 calc R . . C6 C 0.7601(5) 0.0787(5) 0.1647(4) 0.069(3) Uani 1 1 d . . . H6A H 0.7815 0.1155 0.1412 0.082 Uiso 1 1 calc R . . H6B H 0.8002 0.0914 0.2064 0.082 Uiso 1 1 calc R . . C7 C 0.7732(5) -0.0144(5) 0.1530(3) 0.077(3) Uani 1 1 d . . . H7A H 0.7614 -0.0510 0.1803 0.115 Uiso 1 1 calc R . . H7B H 0.8376 -0.0233 0.1582 0.115 Uiso 1 1 calc R . . H7C H 0.7291 -0.0291 0.1128 0.115 Uiso 1 1 calc R . . C8 C 0.4453(4) 0.3119(5) 0.2248(3) 0.054(2) Uani 1 1 d . . . H8A H 0.4757 0.2559 0.2398 0.065 Uiso 1 1 calc R . . H8B H 0.3792 0.3075 0.2184 0.065 Uiso 1 1 calc R . . C9 C 0.4941(5) 0.3799(5) 0.2705(3) 0.062(2) Uani 1 1 d . . . H9A H 0.5614 0.3799 0.2792 0.075 Uiso 1 1 calc R . . H9B H 0.4681 0.4365 0.2533 0.075 Uiso 1 1 calc R . . C10 C 0.4869(5) 0.3715(5) 0.3271(3) 0.068(3) Uani 1 1 d . . . H10A H 0.5029 0.3119 0.3414 0.081 Uiso 1 1 calc R . . H10B H 0.4211 0.3819 0.3197 0.081 Uiso 1 1 calc R . . C11 C 0.5503(5) 0.4326(5) 0.3752(3) 0.067(2) Uani 1 1 d . . . H11A H 0.6166 0.4192 0.3853 0.080 Uiso 1 1 calc R . . H11B H 0.5380 0.4922 0.3603 0.080 Uiso 1 1 calc R . . C12 C 0.5352(5) 0.4266(5) 0.4291(3) 0.061(2) Uani 1 1 d . . . H12A H 0.5471 0.3671 0.4442 0.073 Uiso 1 1 calc R . . H12B H 0.4692 0.4409 0.4194 0.073 Uiso 1 1 calc R . . C13 C 0.5999(5) 0.4875(6) 0.4758(4) 0.092(3) Uani 1 1 d . . . H13A H 0.6648 0.4775 0.4823 0.138 Uiso 1 1 calc R . . H13B H 0.5946 0.4774 0.5123 0.138 Uiso 1 1 calc R . . H13C H 0.5822 0.5468 0.4631 0.138 Uiso 1 1 calc R . . C14 C 0.3054(5) 0.4255(5) 0.1284(3) 0.048(2) Uani 1 1 d . . . C15 C 0.2768(5) 0.4316(5) 0.1732(4) 0.061(2) Uani 1 1 d . . . C16 C 0.2666(4) 0.4666(5) 0.0733(3) 0.044(2) Uani 1 1 d . . . C17 C 0.3245(5) 0.4468(5) 0.0460(3) 0.048(2) Uani 1 1 d . . . C18 C 0.3128(5) 0.4744(5) -0.0072(4) 0.052(2) Uani 1 1 d . . . C19 C 0.2357(5) 0.5280(5) -0.0383(3) 0.051(2) Uani 1 1 d . . . C20 C 0.1763(5) 0.5452(5) -0.0111(3) 0.046(2) Uani 1 1 d . . . C21 C 0.1173(5) 0.6143(5) -0.0958(3) 0.050(2) Uani 1 1 d . . . C22 C 0.0756(6) 0.7023(6) -0.1837(4) 0.0916(13) Uani 1 1 d . . . H22A H 0.1444 0.7078 -0.1691 0.110 Uiso 1 1 calc R . . H22B H 0.0485 0.7607 -0.1924 0.110 Uiso 1 1 calc R . . C23 C 0.0379(6) 0.6516(6) -0.2395(4) 0.0916(13) Uani 1 1 d . . . H23A H -0.0315 0.6528 -0.2572 0.110 Uiso 1 1 calc R . . H23B H 0.0579 0.5911 -0.2302 0.110 Uiso 1 1 calc R . . C24 C 0.0700(6) 0.6845(6) -0.2846(4) 0.0916(13) Uani 1 1 d . . . H24A H 0.1344 0.6635 -0.2737 0.110 Uiso 1 1 calc R . . H24B H 0.0725 0.7479 -0.2827 0.110 Uiso 1 1 calc R . . C25 C 0.0009(6) 0.6546(6) -0.3540(4) 0.0916(13) Uani 1 1 d . . . H25A H -0.0665 0.6586 -0.3632 0.110 Uiso 1 1 calc R . . H25B H 0.0134 0.6892 -0.3824 0.110 Uiso 1 1 calc R . . C26 C 0.0289(6) 0.5708(6) -0.3528(4) 0.0916(13) Uani 1 1 d . . . H26A H 0.0172 0.5358 -0.3241 0.110 Uiso 1 1 calc R . . H26B H 0.0957 0.5663 -0.3449 0.110 Uiso 1 1 calc R . . C27 C -0.0430(5) 0.5452(6) -0.4213(4) 0.0916(13) Uani 1 1 d . . . H27A H -0.1079 0.5566 -0.4284 0.137 Uiso 1 1 calc R . . H27B H -0.0359 0.4842 -0.4277 0.137 Uiso 1 1 calc R . . H27C H -0.0276 0.5797 -0.4480 0.137 Uiso 1 1 calc R . . C28 C -0.0392(5) 0.6802(5) -0.1407(4) 0.065(2) Uani 1 1 d . . . H28A H -0.0535 0.6335 -0.1195 0.078 Uiso 1 1 calc R . . H28B H -0.0864 0.6778 -0.1820 0.078 Uiso 1 1 calc R . . C29 C -0.0476(5) 0.7656(5) -0.1149(4) 0.071(3) Uani 1 1 d . . . H29A H -0.0203 0.8114 -0.1297 0.085 Uiso 1 1 calc R . . H29B H -0.0116 0.7635 -0.0719 0.085 Uiso 1 1 calc R . . C30 C -0.1506(5) 0.7868(5) -0.1311(3) 0.064(2) Uani 1 1 d . . . H30A H -0.1854 0.7929 -0.1740 0.077 Uiso 1 1 calc R . . H30B H -0.1790 0.7389 -0.1189 0.077 Uiso 1 1 calc R . . C31 C -0.1597(6) 0.8689(6) -0.1021(4) 0.088(3) Uani 1 1 d . . . H31A H -0.1276 0.9158 -0.1123 0.105 Uiso 1 1 calc R . . H31B H -0.1278 0.8614 -0.0591 0.105 Uiso 1 1 calc R . . C32 C -0.2617(6) 0.8948(7) -0.1200(4) 0.103(4) Uani 1 1 d . . . H32A H -0.2634 0.9413 -0.0940 0.124 Uiso 1 1 calc R . . H32B H -0.2963 0.8452 -0.1149 0.124 Uiso 1 1 calc R . . C33 C -0.3110(6) 0.9256(7) -0.1838(4) 0.135(5) Uani 1 1 d . . . H33A H -0.2699 0.9654 -0.1915 0.203 Uiso 1 1 calc R . . H33B H -0.3696 0.9547 -0.1905 0.203 Uiso 1 1 calc R . . H33C H -0.3248 0.8761 -0.2101 0.203 Uiso 1 1 calc R . . C34 C 0.1967(5) 0.5727(5) -0.0920(3) 0.052(2) Uani 1 1 d . . . C35 C 0.2340(5) 0.5702(5) -0.1346(4) 0.061(3) Uani 1 1 d . . . C36 C 0.1865(5) 0.5197(5) 0.0422(3) 0.049(2) Uani 1 1 d . . . C37 C 0.1229(5) 0.5416(5) 0.0677(3) 0.051(2) Uani 1 1 d . . . C38 C 0.0753(5) 0.5598(5) 0.0913(3) 0.052(2) Uani 1 1 d . . . C39 C 0.0196(5) 0.5806(5) 0.1230(4) 0.047(2) Uani 1 1 d . . . C40 C -0.0622(5) 0.6327(5) 0.0929(3) 0.047(2) Uani 1 1 d . . . C41 C -0.1152(5) 0.6503(5) 0.1254(3) 0.051(2) Uani 1 1 d . . . C42 C -0.0860(5) 0.6221(5) 0.1834(3) 0.051(2) Uani 1 1 d . . . C43 C -0.0041(5) 0.5724(5) 0.2091(3) 0.059(2) Uani 1 1 d . . . H43A H 0.0159 0.5523 0.2479 0.070 Uiso 1 1 calc R . . C44 C 0.0488(5) 0.5518(5) 0.1792(4) 0.058(2) Uani 1 1 d . . . H44A H 0.1042 0.5183 0.1974 0.070 Uiso 1 1 calc R . . C45 C -0.1412(6) 0.6419(5) 0.2148(4) 0.067(3) Uani 1 1 d . . . H45A H -0.1217 0.6228 0.2538 0.081 Uiso 1 1 calc R . . C46 C -0.2216(5) 0.6886(5) 0.1871(4) 0.069(3) Uani 1 1 d . . . H46A H -0.2589 0.7000 0.2070 0.082 Uiso 1 1 calc R . . C47 C -0.2513(5) 0.7205(5) 0.1297(4) 0.055(2) Uani 1 1 d . . . C48 C -0.1987(5) 0.7012(5) 0.0977(3) 0.048(2) Uani 1 1 d . . . C49 C -0.2272(5) 0.7303(5) 0.0431(4) 0.050(2) Uani 1 1 d . . . C50 C -0.1716(5) 0.7102(5) 0.0107(3) 0.049(2) Uani 1 1 d . . . H50A H -0.1917 0.7308 -0.0280 0.059 Uiso 1 1 calc R . . C51 C -0.0909(5) 0.6617(5) 0.0364(3) 0.054(2) Uani 1 1 d . . . H51A H -0.0554 0.6485 0.0155 0.065 Uiso 1 1 calc R . . C52 C -0.3112(5) 0.7798(5) 0.0152(4) 0.071(3) Uani 1 1 d . . . H52A H -0.3308 0.8010 -0.0233 0.085 Uiso 1 1 calc R . . C53 C -0.3628(5) 0.7959(5) 0.0458(4) 0.069(3) Uani 1 1 d . . . H53A H -0.4205 0.8261 0.0274 0.083 Uiso 1 1 calc R . . C54 C -0.3325(5) 0.7696(5) 0.1010(4) 0.068(3) Uani 1 1 d . . . H54A H -0.3678 0.7849 0.1216 0.082 Uiso 1 1 calc R . . C55 C 0.3748(6) 0.4505(6) -0.0325(3) 0.061(2) Uani 1 1 d . . . C56 C 0.4241(5) 0.4290(5) -0.0558(4) 0.057(2) Uani 1 1 d . . . C57 C 0.4806(5) 0.4063(5) -0.0849(3) 0.048(2) Uani 1 1 d . . . C58 C 0.5590(5) 0.3513(5) -0.0604(4) 0.051(2) Uani 1 1 d . . . C59 C 0.6127(5) 0.3306(5) -0.0918(4) 0.050(2) Uani 1 1 d . . . C60 C 0.5851(5) 0.3698(5) -0.1466(3) 0.049(2) Uani 1 1 d . . . C61 C 0.5074(5) 0.4213(5) -0.1714(3) 0.058(2) Uani 1 1 d . . . H61A H 0.4888 0.4449 -0.2093 0.069 Uiso 1 1 calc R . . C62 C 0.4561(5) 0.4383(5) -0.1397(4) 0.061(2) Uani 1 1 d . . . H62A H 0.4020 0.4736 -0.1569 0.073 Uiso 1 1 calc R . . C63 C 0.6417(6) 0.3502(5) -0.1786(4) 0.061(2) Uani 1 1 d . . . H63A H 0.6263 0.3751 -0.2157 0.073 Uiso 1 1 calc R . . C64 C 0.7173(6) 0.2951(6) -0.1534(4) 0.074(3) Uani 1 1 d . . . H64A H 0.7530 0.2827 -0.1743 0.088 Uiso 1 1 calc R . . C65 C 0.7439(6) 0.2563(6) -0.0984(4) 0.062(3) Uani 1 1 d . . . C66 C 0.6901(5) 0.2747(5) -0.0660(4) 0.054(2) Uani 1 1 d . . . C67 C 0.7173(5) 0.2389(5) -0.0105(4) 0.057(2) Uani 1 1 d . . . C68 C 0.6628(5) 0.2598(5) 0.0205(3) 0.061(2) Uani 1 1 d . . . H68A H 0.6785 0.2357 0.0580 0.073 Uiso 1 1 calc R . . C69 C 0.5879(5) 0.3148(5) -0.0043(4) 0.062(2) Uani 1 1 d . . . H69A H 0.5537 0.3289 0.0172 0.074 Uiso 1 1 calc R . . C70 C 0.7921(6) 0.1820(6) 0.0125(4) 0.084(3) Uani 1 1 d . . . H70A H 0.8102 0.1559 0.0496 0.101 Uiso 1 1 calc R . . C71 C 0.8404(6) 0.1648(7) -0.0221(5) 0.094(3) Uani 1 1 d . . . H71A H 0.8916 0.1258 -0.0073 0.113 Uiso 1 1 calc R . . C72 C 0.8174(6) 0.2008(7) -0.0747(4) 0.091(4) Uani 1 1 d . . . H72A H 0.8528 0.1873 -0.0955 0.109 Uiso 1 1 calc R . . N1 N 0.4472(4) 0.3292(4) 0.1693(3) 0.0550(17) Uiso 1 1 d . . . N2 N 0.2549(5) 0.4394(5) 0.2103(3) 0.075(2) Uiso 1 1 d . . . N3 N 0.0559(4) 0.6653(4) -0.1377(3) 0.0575(18) Uiso 1 1 d . . . N4 N 0.2634(5) 0.5718(5) -0.1689(3) 0.076(2) Uiso 1 1 d . . . O1 O 0.3953(3) 0.3921(3) 0.0818(2) 0.0463(13) Uiso 1 1 d . . . O2 O 0.1026(3) 0.5984(3) -0.0482(2) 0.0519(14) 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 0.044(4) 0.033(4) 0.050(5) 0.005(4) 0.004(4) 0.001(4) C2 0.047(5) 0.091(7) 0.075(6) 0.012(5) 0.031(5) 0.011(5) C3 0.051(5) 0.056(6) 0.066(5) -0.015(5) 0.020(4) 0.012(4) C4 0.033(4) 0.070(6) 0.079(6) 0.001(5) 0.021(4) 0.011(4) C5 0.048(5) 0.057(6) 0.087(6) 0.003(5) 0.029(4) 0.000(4) C6 0.046(5) 0.073(7) 0.086(7) -0.004(5) 0.028(5) 0.009(4) C7 0.062(5) 0.073(7) 0.091(7) -0.014(5) 0.031(5) 0.020(5) C8 0.029(4) 0.062(5) 0.044(5) -0.012(4) -0.009(3) 0.012(4) C9 0.051(4) 0.084(7) 0.063(5) 0.011(5) 0.034(4) 0.008(5) C10 0.063(5) 0.053(6) 0.092(7) 0.036(5) 0.039(5) 0.030(4) C11 0.058(5) 0.085(7) 0.049(5) -0.020(5) 0.015(4) -0.009(5) C12 0.057(5) 0.067(6) 0.047(5) 0.002(4) 0.012(4) 0.001(4) C13 0.069(6) 0.122(9) 0.083(7) -0.001(6) 0.032(5) -0.008(6) C14 0.034(4) 0.063(6) 0.032(5) 0.000(4) 0.002(4) 0.010(4) C15 0.055(5) 0.059(6) 0.060(6) -0.003(5) 0.017(5) 0.005(4) C16 0.027(4) 0.045(5) 0.045(5) -0.005(4) 0.000(4) -0.007(4) C17 0.037(4) 0.049(5) 0.051(5) 0.006(4) 0.012(4) 0.009(4) C18 0.045(5) 0.051(6) 0.058(6) -0.002(5) 0.022(5) 0.000(4) C19 0.041(5) 0.063(6) 0.049(6) -0.013(5) 0.019(4) -0.005(4) C20 0.028(4) 0.039(5) 0.052(5) -0.009(4) 0.000(4) 0.002(4) C21 0.042(4) 0.052(5) 0.041(5) 0.000(4) 0.005(4) 0.008(4) C22 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C23 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C24 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C25 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C26 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C27 0.088(3) 0.098(3) 0.100(3) 0.025(3) 0.052(3) 0.026(3) C28 0.039(4) 0.063(6) 0.092(7) 0.019(5) 0.027(4) 0.007(4) C29 0.054(5) 0.067(6) 0.077(6) -0.005(5) 0.014(5) 0.006(4) C30 0.046(5) 0.090(7) 0.048(5) -0.005(5) 0.013(4) 0.009(5) C31 0.069(6) 0.091(7) 0.088(7) -0.013(6) 0.020(5) 0.008(5) C32 0.077(6) 0.128(9) 0.081(7) -0.012(7) 0.014(5) 0.031(6) C33 0.093(8) 0.162(12) 0.114(9) 0.013(9) 0.012(7) 0.064(8) C34 0.056(5) 0.057(6) 0.044(5) -0.007(5) 0.023(5) -0.021(5) C35 0.042(5) 0.056(6) 0.054(6) 0.009(5) -0.009(4) 0.017(4) C36 0.040(5) 0.037(5) 0.057(6) -0.011(4) 0.010(4) -0.002(4) C37 0.043(5) 0.048(5) 0.045(5) -0.014(4) 0.003(4) -0.004(4) C38 0.047(5) 0.047(5) 0.047(5) -0.004(4) 0.006(4) 0.006(4) C39 0.043(5) 0.038(5) 0.064(6) -0.008(4) 0.029(5) 0.001(4) C40 0.041(4) 0.066(6) 0.037(5) -0.005(4) 0.020(4) -0.012(4) C41 0.040(5) 0.054(6) 0.047(5) -0.011(4) 0.008(4) -0.012(4) C42 0.054(5) 0.055(5) 0.051(5) -0.010(5) 0.029(4) -0.002(4) C43 0.067(5) 0.059(6) 0.050(5) 0.000(5) 0.025(5) -0.007(5) C44 0.046(5) 0.058(6) 0.063(6) 0.003(5) 0.017(5) 0.001(4) C45 0.075(6) 0.066(6) 0.074(6) -0.005(5) 0.045(5) -0.011(5) C46 0.044(5) 0.083(7) 0.085(7) -0.005(6) 0.034(5) 0.008(5) C47 0.055(5) 0.060(6) 0.054(6) -0.017(5) 0.026(5) -0.007(4) C48 0.052(5) 0.059(6) 0.030(5) -0.017(4) 0.014(4) -0.018(4) C49 0.040(5) 0.055(6) 0.054(6) -0.017(4) 0.020(4) -0.014(4) C50 0.058(5) 0.044(5) 0.047(5) -0.006(4) 0.024(4) -0.005(4) C51 0.048(5) 0.056(6) 0.049(6) -0.006(4) 0.012(4) 0.005(4) C52 0.056(5) 0.063(6) 0.101(7) 0.015(6) 0.041(6) 0.013(5) C53 0.034(4) 0.077(7) 0.082(7) -0.002(6) 0.012(5) 0.023(4) C54 0.043(5) 0.061(6) 0.091(7) -0.011(6) 0.020(5) -0.005(4) C55 0.053(5) 0.067(6) 0.046(5) -0.003(5) 0.004(5) -0.014(5) C56 0.045(5) 0.066(6) 0.060(6) -0.008(5) 0.023(5) -0.018(4) C57 0.048(5) 0.049(5) 0.035(5) -0.001(4) 0.005(4) -0.012(4) C58 0.039(5) 0.042(5) 0.055(6) -0.005(4) 0.003(4) -0.008(4) C59 0.051(5) 0.054(5) 0.052(6) -0.008(4) 0.029(5) -0.004(4) C60 0.048(5) 0.052(6) 0.046(5) -0.010(4) 0.019(4) -0.008(4) C61 0.056(5) 0.062(6) 0.052(5) 0.011(5) 0.021(5) -0.002(5) C62 0.056(5) 0.056(6) 0.069(6) 0.000(5) 0.025(5) 0.004(4) C63 0.059(5) 0.057(6) 0.060(6) -0.004(5) 0.021(5) -0.009(5) C64 0.074(6) 0.107(8) 0.061(6) -0.017(6) 0.048(6) -0.021(6) C65 0.050(5) 0.084(7) 0.058(6) -0.022(5) 0.029(5) -0.010(5) C66 0.041(5) 0.053(6) 0.064(6) -0.024(5) 0.020(5) -0.013(4) C67 0.053(5) 0.060(6) 0.055(6) -0.002(5) 0.021(5) -0.012(4) C68 0.060(5) 0.049(5) 0.051(5) -0.008(4) 0.004(5) -0.004(4) C69 0.032(4) 0.074(6) 0.075(7) -0.009(5) 0.020(4) -0.004(4) C70 0.058(6) 0.105(8) 0.077(7) -0.001(6) 0.019(5) 0.029(6) C71 0.046(5) 0.103(9) 0.123(9) 0.002(8) 0.026(6) 0.016(5) C72 0.060(6) 0.136(10) 0.076(7) -0.008(7) 0.030(6) 0.033(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 1.324(8) . ? C1 O1 1.342(8) . ? C1 C14 1.412(9) . ? C2 N1 1.511(8) . ? C2 C3 1.530(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.538(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.531(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.515(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N1 1.453(8) . ? C8 C9 1.513(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.500(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.529(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.496(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.517(9) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.403(11) . ? C14 C16 1.415(9) . ? C15 N2 1.147(9) . ? C16 C17 1.409(10) . ? C16 C36 1.429(9) . ? C17 C18 1.353(10) . ? C17 O1 1.387(8) . ? C18 C19 1.405(10) . ? C18 C55 1.440(12) . ? C19 C34 1.415(10) . ? C19 C20 1.416(10) . ? C20 C36 1.356(10) . ? C20 O2 1.407(7) . ? C21 N3 1.345(8) . ? C21 O2 1.352(8) . ? C21 C34 1.382(9) . ? C22 N3 1.458(9) . ? C22 C23 1.502(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.531(11) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.688(11) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.376(10) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.661(11) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 N3 1.494(8) . ? C28 C29 1.516(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.535(9) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.517(10) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.529(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.539(11) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.444(12) . ? C35 N4 1.156(10) . ? C36 C37 1.459(11) . ? C37 C38 1.184(10) . ? C38 C39 1.470(11) . ? C39 C44 1.373(9) . ? C39 C40 1.434(9) . ? C40 C51 1.383(9) . ? C40 C41 1.440(10) . ? C41 C42 1.410(9) . ? C41 C48 1.435(10) . ? C42 C43 1.404(9) . ? C42 C45 1.453(10) . ? C43 C44 1.393(10) . ? C43 H43A 0.9500 . ? C44 H44A 0.9500 . ? C45 C46 1.366(10) . ? C45 H45A 0.9500 . ? C46 C47 1.414(10) . ? C46 H46A 0.9500 . ? C47 C54 1.398(10) . ? C47 C48 1.432(10) . ? C48 C49 1.339(10) . ? C49 C52 1.430(10) . ? C49 C50 1.479(10) . ? C50 C51 1.380(9) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? C52 C53 1.376(11) . ? C52 H52A 0.9500 . ? C53 C54 1.336(10) . ? C53 H53A 0.9500 . ? C54 H54A 0.9500 . ? C55 C56 1.218(11) . ? C56 C57 1.434(11) . ? C57 C62 1.369(9) . ? C57 C58 1.412(9) . ? C58 C69 1.414(10) . ? C58 C59 1.437(10) . ? C59 C60 1.405(9) . ? C59 C66 1.410(10) . ? C60 C61 1.371(9) . ? C60 C63 1.484(10) . ? C61 C62 1.400(10) . ? C61 H61A 0.9500 . ? C62 H62A 0.9500 . ? C63 C64 1.383(10) . ? C63 H63A 0.9500 . ? C64 C65 1.411(11) . ? C64 H64A 0.9500 . ? C65 C72 1.362(11) . ? C65 C66 1.451(11) . ? C66 C67 1.401(10) . ? C67 C70 1.388(10) . ? C67 C68 1.440(10) . ? C68 C69 1.374(9) . ? C68 H68A 0.9500 . ? C69 H69A 0.9500 . ? C70 C71 1.422(12) . ? C70 H70A 0.9500 . ? C71 C72 1.347(12) . ? C71 H71A 0.9500 . ? C72 H72A 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 N1 C1 O1 114.0(7) . . ? N1 C1 C14 134.1(8) . . ? O1 C1 C14 111.7(6) . . ? N1 C2 C3 111.1(6) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 108.8(6) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 113.1(6) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 113.6(6) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 113.6(6) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 113.4(6) . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 116.7(7) . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C9 C10 C11 114.5(7) . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 112.5(7) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 110.8(7) . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C1 126.6(7) . . ? C15 C14 C16 128.3(8) . . ? C1 C14 C16 105.0(7) . . ? N2 C15 C14 177.5(10) . . ? C17 C16 C14 107.2(7) . . ? C17 C16 C36 117.8(7) . . ? C14 C16 C36 135.0(8) . . ? C18 C17 O1 124.8(7) . . ? C18 C17 C16 126.2(7) . . ? O1 C17 C16 109.0(7) . . ? C17 C18 C19 117.2(8) . . ? C17 C18 C55 122.9(7) . . ? C19 C18 C55 119.9(8) . . ? C18 C19 C34 137.9(8) . . ? C18 C19 C20 116.0(8) . . ? C34 C19 C20 106.1(7) . . ? C36 C20 O2 123.1(7) . . ? C36 C20 C19 128.3(7) . . ? O2 C20 C19 108.6(7) . . ? N3 C21 O2 118.1(7) . . ? N3 C21 C34 130.7(8) . . ? O2 C21 C34 111.2(6) . . ? N3 C22 C23 114.6(8) . . ? N3 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? N3 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C24 114.0(8) . . ? C22 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? C22 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C23 C24 C25 114.6(7) . . ? C23 C24 H24A 108.6 . . ? C25 C24 H24A 108.6 . . ? C23 C24 H24B 108.6 . . ? C25 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 100.6(7) . . ? C26 C25 H25A 111.7 . . ? C24 C25 H25A 111.7 . . ? C26 C25 H25B 111.7 . . ? C24 C25 H25B 111.7 . . ? H25A C25 H25B 109.4 . . ? C25 C26 C27 97.9(7) . . ? C25 C26 H26A 112.2 . . ? C27 C26 H26A 112.2 . . ? C25 C26 H26B 112.2 . . ? C27 C26 H26B 112.2 . . ? H26A C26 H26B 109.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C28 C29 113.1(6) . . ? N3 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? N3 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C28 C29 C30 110.9(6) . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 108.0 . . ? C31 C30 C29 111.6(7) . . ? C31 C30 H30A 109.3 . . ? C29 C30 H30A 109.3 . . ? C31 C30 H30B 109.3 . . ? C29 C30 H30B 109.3 . . ? H30A C30 H30B 108.0 . . ? C30 C31 C32 113.0(7) . . ? C30 C31 H31A 109.0 . . ? C32 C31 H31A 109.0 . . ? C30 C31 H31B 109.0 . . ? C32 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? C31 C32 C33 112.4(8) . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32B 109.1 . . ? C33 C32 H32B 109.1 . . ? H32A C32 H32B 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C21 C34 C19 107.2(7) . . ? C21 C34 C35 128.4(8) . . ? C19 C34 C35 124.4(8) . . ? N4 C35 C34 177.3(10) . . ? C20 C36 C16 114.4(8) . . ? C20 C36 C37 125.1(7) . . ? C16 C36 C37 120.6(8) . . ? C38 C37 C36 176.5(8) . . ? C37 C38 C39 177.4(9) . . ? C44 C39 C40 123.7(8) . . ? C44 C39 C38 119.4(7) . . ? C40 C39 C38 116.9(7) . . ? C51 C40 C39 123.3(7) . . ? C51 C40 C41 121.8(8) . . ? C39 C40 C41 114.9(7) . . ? C42 C41 C48 119.8(8) . . ? C42 C41 C40 122.3(7) . . ? C48 C41 C40 117.8(8) . . ? C43 C42 C41 118.2(7) . . ? C43 C42 C45 121.2(8) . . ? C41 C42 C45 120.5(8) . . ? C44 C43 C42 121.8(8) . . ? C44 C43 H43A 119.1 . . ? C42 C43 H43A 119.1 . . ? C39 C44 C43 119.0(7) . . ? C39 C44 H44A 120.5 . . ? C43 C44 H44A 120.5 . . ? C46 C45 C42 118.7(8) . . ? C46 C45 H45A 120.7 . . ? C42 C45 H45A 120.7 . . ? C45 C46 C47 122.3(8) . . ? C45 C46 H46A 118.8 . . ? C47 C46 H46A 118.8 . . ? C54 C47 C46 123.2(8) . . ? C54 C47 C48 116.7(8) . . ? C46 C47 C48 120.1(8) . . ? C49 C48 C47 120.3(8) . . ? C49 C48 C41 121.2(8) . . ? C47 C48 C41 118.5(8) . . ? C48 C49 C52 121.1(8) . . ? C48 C49 C50 119.5(8) . . ? C52 C49 C50 119.4(8) . . ? C51 C50 C49 120.6(7) . . ? C51 C50 H50A 119.7 . . ? C49 C50 H50A 119.7 . . ? C50 C51 C40 119.1(8) . . ? C50 C51 H51A 120.5 . . ? C40 C51 H51A 120.5 . . ? C53 C52 C49 118.2(8) . . ? C53 C52 H52A 120.9 . . ? C49 C52 H52A 120.9 . . ? C54 C53 C52 120.7(8) . . ? C54 C53 H53A 119.7 . . ? C52 C53 H53A 119.7 . . ? C53 C54 C47 122.9(9) . . ? C53 C54 H54A 118.5 . . ? C47 C54 H54A 118.5 . . ? C56 C55 C18 177.3(9) . . ? C55 C56 C57 177.8(10) . . ? C62 C57 C58 118.3(8) . . ? C62 C57 C56 118.3(8) . . ? C58 C57 C56 123.4(8) . . ? C57 C58 C69 121.6(8) . . ? C57 C58 C59 120.9(8) . . ? C69 C58 C59 117.6(7) . . ? C60 C59 C66 124.1(8) . . ? C60 C59 C58 116.8(8) . . ? C66 C59 C58 119.0(8) . . ? C61 C60 C59 122.7(8) . . ? C61 C60 C63 120.2(8) . . ? C59 C60 C63 117.0(8) . . ? C60 C61 C62 118.4(8) . . ? C60 C61 H61A 120.8 . . ? C62 C61 H61A 120.8 . . ? C57 C62 C61 122.9(8) . . ? C57 C62 H62A 118.6 . . ? C61 C62 H62A 118.6 . . ? C64 C63 C60 118.9(8) . . ? C64 C63 H63A 120.5 . . ? C60 C63 H63A 120.5 . . ? C63 C64 C65 123.2(8) . . ? C63 C64 H64A 118.4 . . ? C65 C64 H64A 118.4 . . ? C72 C65 C64 122.5(9) . . ? C72 C65 C66 118.4(9) . . ? C64 C65 C66 119.1(9) . . ? C67 C66 C59 122.5(8) . . ? C67 C66 C65 119.8(8) . . ? C59 C66 C65 117.7(9) . . ? C70 C67 C66 120.6(9) . . ? C70 C67 C68 121.4(8) . . ? C66 C67 C68 118.0(8) . . ? C69 C68 C67 119.6(8) . . ? C69 C68 H68A 120.2 . . ? C67 C68 H68A 120.2 . . ? C68 C69 C58 123.3(8) . . ? C68 C69 H69A 118.4 . . ? C58 C69 H69A 118.4 . . ? C67 C70 C71 116.9(9) . . ? C67 C70 H70A 121.6 . . ? C71 C70 H70A 121.6 . . ? C72 C71 C70 123.5(9) . . ? C72 C71 H71A 118.3 . . ? C70 C71 H71A 118.3 . . ? C71 C72 C65 120.8(10) . . ? C71 C72 H72A 119.6 . . ? C65 C72 H72A 119.6 . . ? C1 N1 C8 120.3(6) . . ? C1 N1 C2 122.1(7) . . ? C8 N1 C2 114.1(6) . . ? C21 N3 C22 122.5(7) . . ? C21 N3 C28 119.7(7) . . ? C22 N3 C28 117.6(6) . . ? C1 O1 C17 107.1(6) . . ? C21 O2 C20 106.9(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 N1 C2 C3 C4 -166.8(6) . . . . ? C2 C3 C4 C5 179.1(7) . . . . ? C3 C4 C5 C6 -179.4(7) . . . . ? C4 C5 C6 C7 176.9(7) . . . . ? N1 C8 C9 C10 174.1(6) . . . . ? C8 C9 C10 C11 170.4(6) . . . . ? C9 C10 C11 C12 175.5(6) . . . . ? C10 C11 C12 C13 179.4(6) . . . . ? N1 C1 C14 C15 9.0(14) . . . . ? O1 C1 C14 C15 -176.8(7) . . . . ? N1 C1 C14 C16 -175.8(8) . . . . ? O1 C1 C14 C16 -1.6(8) . . . . ? C1 C14 C15 N2 98(21) . . . . ? C16 C14 C15 N2 -76(21) . . . . ? C15 C14 C16 C17 174.7(8) . . . . ? C1 C14 C16 C17 -0.5(8) . . . . ? C15 C14 C16 C36 -5.7(14) . . . . ? C1 C14 C16 C36 179.2(8) . . . . ? C14 C16 C17 C18 -179.1(8) . . . . ? C36 C16 C17 C18 1.2(12) . . . . ? C14 C16 C17 O1 2.3(8) . . . . ? C36 C16 C17 O1 -177.4(6) . . . . ? O1 C17 C18 C19 178.4(7) . . . . ? C16 C17 C18 C19 0.1(12) . . . . ? O1 C17 C18 C55 -1.1(13) . . . . ? C16 C17 C18 C55 -179.4(7) . . . . ? C17 C18 C19 C34 178.2(9) . . . . ? C55 C18 C19 C34 -2.3(14) . . . . ? C17 C18 C19 C20 -2.0(11) . . . . ? C55 C18 C19 C20 177.5(7) . . . . ? C18 C19 C20 C36 3.2(12) . . . . ? C34 C19 C20 C36 -176.9(7) . . . . ? C18 C19 C20 O2 -179.2(6) . . . . ? C34 C19 C20 O2 0.6(8) . . . . ? N3 C22 C23 C24 -172.3(6) . . . . ? C22 C23 C24 C25 -158.7(7) . . . . ? C23 C24 C25 C26 -77.0(10) . . . . ? C24 C25 C26 C27 178.7(6) . . . . ? N3 C28 C29 C30 167.3(7) . . . . ? C28 C29 C30 C31 175.9(7) . . . . ? C29 C30 C31 C32 176.6(8) . . . . ? C30 C31 C32 C33 -70.3(11) . . . . ? N3 C21 C34 C19 179.6(8) . . . . ? O2 C21 C34 C19 -0.5(9) . . . . ? N3 C21 C34 C35 -2.8(14) . . . . ? O2 C21 C34 C35 177.1(7) . . . . ? C18 C19 C34 C21 179.7(9) . . . . ? C20 C19 C34 C21 -0.1(9) . . . . ? C18 C19 C34 C35 2.0(15) . . . . ? C20 C19 C34 C35 -177.8(7) . . . . ? C21 C34 C35 N4 48(18) . . . . ? C19 C34 C35 N4 -135(17) . . . . ? O2 C20 C36 C16 -179.3(6) . . . . ? C19 C20 C36 C16 -2.0(11) . . . . ? O2 C20 C36 C37 1.4(11) . . . . ? C19 C20 C36 C37 178.7(7) . . . . ? C17 C16 C36 C20 -0.2(9) . . . . ? C14 C16 C36 C20 -179.9(8) . . . . ? C17 C16 C36 C37 179.1(7) . . . . ? C14 C16 C36 C37 -0.5(13) . . . . ? C20 C36 C37 C38 -143(15) . . . . ? C16 C36 C37 C38 38(16) . . . . ? C36 C37 C38 C39 -27(33) . . . . ? C37 C38 C39 C44 -7(21) . . . . ? C37 C38 C39 C40 171(20) . . . . ? C44 C39 C40 C51 179.7(8) . . . . ? C38 C39 C40 C51 1.3(11) . . . . ? C44 C39 C40 C41 -2.5(11) . . . . ? C38 C39 C40 C41 179.1(7) . . . . ? C51 C40 C41 C42 -179.1(7) . . . . ? C39 C40 C41 C42 3.1(11) . . . . ? C51 C40 C41 C48 -1.5(11) . . . . ? C39 C40 C41 C48 -179.3(6) . . . . ? C48 C41 C42 C43 -180.0(7) . . . . ? C40 C41 C42 C43 -2.4(11) . . . . ? C48 C41 C42 C45 1.9(11) . . . . ? C40 C41 C42 C45 179.4(7) . . . . ? C41 C42 C43 C44 0.9(11) . . . . ? C45 C42 C43 C44 179.1(8) . . . . ? C40 C39 C44 C43 1.2(12) . . . . ? C38 C39 C44 C43 179.5(7) . . . . ? C42 C43 C44 C39 -0.3(12) . . . . ? C43 C42 C45 C46 -178.3(7) . . . . ? C41 C42 C45 C46 -0.2(12) . . . . ? C42 C45 C46 C47 -2.1(13) . . . . ? C45 C46 C47 C54 -178.9(8) . . . . ? C45 C46 C47 C48 2.6(13) . . . . ? C54 C47 C48 C49 0.5(11) . . . . ? C46 C47 C48 C49 179.1(8) . . . . ? C54 C47 C48 C41 -179.4(7) . . . . ? C46 C47 C48 C41 -0.8(11) . . . . ? C42 C41 C48 C49 178.7(7) . . . . ? C40 C41 C48 C49 1.1(11) . . . . ? C42 C41 C48 C47 -1.3(10) . . . . ? C40 C41 C48 C47 -179.0(7) . . . . ? C47 C48 C49 C52 -1.0(11) . . . . ? C41 C48 C49 C52 178.9(7) . . . . ? C47 C48 C49 C50 179.7(7) . . . . ? C41 C48 C49 C50 -0.4(11) . . . . ? C48 C49 C50 C51 0.0(11) . . . . ? C52 C49 C50 C51 -179.3(7) . . . . ? C49 C50 C51 C40 -0.4(11) . . . . ? C39 C40 C51 C50 178.7(7) . . . . ? C41 C40 C51 C50 1.1(11) . . . . ? C48 C49 C52 C53 -0.8(12) . . . . ? C50 C49 C52 C53 178.5(7) . . . . ? C49 C52 C53 C54 3.3(13) . . . . ? C52 C53 C54 C47 -3.9(14) . . . . ? C46 C47 C54 C53 -176.6(8) . . . . ? C48 C47 C54 C53 2.0(12) . . . . ? C17 C18 C55 C56 122(21) . . . . ? C19 C18 C55 C56 -58(22) . . . . ? C18 C55 C56 C57 74(36) . . . . ? C55 C56 C57 C62 -17(24) . . . . ? C55 C56 C57 C58 165(23) . . . . ? C62 C57 C58 C69 -179.1(7) . . . . ? C56 C57 C58 C69 -0.4(11) . . . . ? C62 C57 C58 C59 1.0(10) . . . . ? C56 C57 C58 C59 179.7(7) . . . . ? C57 C58 C59 C60 2.0(11) . . . . ? C69 C58 C59 C60 -177.9(7) . . . . ? C57 C58 C59 C66 -179.4(7) . . . . ? C69 C58 C59 C66 0.7(11) . . . . ? C66 C59 C60 C61 177.5(7) . . . . ? C58 C59 C60 C61 -4.0(11) . . . . ? C66 C59 C60 C63 0.1(11) . . . . ? C58 C59 C60 C63 178.6(7) . . . . ? C59 C60 C61 C62 2.8(12) . . . . ? C63 C60 C61 C62 -179.8(7) . . . . ? C58 C57 C62 C61 -2.3(12) . . . . ? C56 C57 C62 C61 178.9(8) . . . . ? C60 C61 C62 C57 0.5(12) . . . . ? C61 C60 C63 C64 -177.2(7) . . . . ? C59 C60 C63 C64 0.3(11) . . . . ? C60 C63 C64 C65 -0.3(12) . . . . ? C63 C64 C65 C72 178.6(9) . . . . ? C63 C64 C65 C66 -0.1(13) . . . . ? C60 C59 C66 C67 178.0(8) . . . . ? C58 C59 C66 C67 -0.5(11) . . . . ? C60 C59 C66 C65 -0.4(12) . . . . ? C58 C59 C66 C65 -178.9(7) . . . . ? C72 C65 C66 C67 3.1(12) . . . . ? C64 C65 C66 C67 -178.0(7) . . . . ? C72 C65 C66 C59 -178.4(8) . . . . ? C64 C65 C66 C59 0.5(12) . . . . ? C59 C66 C67 C70 177.9(8) . . . . ? C65 C66 C67 C70 -3.7(12) . . . . ? C59 C66 C67 C68 0.7(12) . . . . ? C65 C66 C67 C68 179.1(7) . . . . ? C70 C67 C68 C69 -178.4(7) . . . . ? C66 C67 C68 C69 -1.3(11) . . . . ? C67 C68 C69 C58 1.6(11) . . . . ? C57 C58 C69 C68 178.8(7) . . . . ? C59 C58 C69 C68 -1.3(11) . . . . ? C66 C67 C70 C71 1.9(13) . . . . ? C68 C67 C70 C71 179.0(8) . . . . ? C67 C70 C71 C72 0.3(15) . . . . ? C70 C71 C72 C65 -0.8(17) . . . . ? C64 C65 C72 C71 -179.7(10) . . . . ? C66 C65 C72 C71 -0.9(15) . . . . ? O1 C1 N1 C8 179.9(6) . . . . ? C14 C1 N1 C8 -6.0(12) . . . . ? O1 C1 N1 C2 22.0(10) . . . . ? C14 C1 N1 C2 -163.9(8) . . . . ? C9 C8 N1 C1 -82.3(8) . . . . ? C9 C8 N1 C2 77.2(8) . . . . ? C3 C2 N1 C1 -112.2(8) . . . . ? C3 C2 N1 C8 88.7(8) . . . . ? O2 C21 N3 C22 165.7(7) . . . . ? C34 C21 N3 C22 -14.4(13) . . . . ? O2 C21 N3 C28 -19.0(10) . . . . ? C34 C21 N3 C28 160.9(8) . . . . ? C23 C22 N3 C21 94.9(9) . . . . ? C23 C22 N3 C28 -80.5(9) . . . . ? C29 C28 N3 C21 100.9(8) . . . . ? C29 C28 N3 C22 -83.6(9) . . . . ? N1 C1 O1 C17 178.5(6) . . . . ? C14 C1 O1 C17 3.0(8) . . . . ? C18 C17 O1 C1 178.1(7) . . . . ? C16 C17 O1 C1 -3.3(8) . . . . ? N3 C21 O2 C20 -179.2(6) . . . . ? C34 C21 O2 C20 0.9(8) . . . . ? C36 C20 O2 C21 176.8(7) . . . . ? C19 C20 O2 C21 -0.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.16 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.239 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.041 # start Validation Reply Form _vrf_RINTA01_complex1 ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: The compound crystallises in form of very thin needles. Attempts to grow bigger crystals with a higher quality failed. Nevertheless, the structure shows reasonable standard uncertainties in atomic positions, bond lengths and angles. ; _vrf_PLAT026_complex1 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 18 Perc. RESPONSE: The compound crystallises in form of very thin needles. Attempts to grow bigger crystals with a higher quality failed. As result, teh number of observed reflections is low. Nevertheless, the structure could be solved and shows reasonable standard uncertainties in atomic positions, bond lengths and angles. ; # end Validation Reply Form # Attachment 'compound2a.CIF' data_complex2a _database_code_depnum_ccdc_archive 'CCDC 783324' #TrackingRef 'compound2a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C68 H70 N4 O2' _chemical_formula_sum 'C68 H70 N4 O2' _chemical_formula_weight 975.28 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 13.7947(9) _cell_length_b 9.0999(6) _cell_length_c 22.2042(16) _cell_angle_alpha 90.00 _cell_angle_beta 105.631(5) _cell_angle_gamma 90.00 _cell_volume 2684.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4223 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 29.47 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.072 _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 173(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 'STOE IPDS-2' _diffrn_measurement_method 'phi & omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15649 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1344 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.64 _reflns_number_total 4982 _reflns_number_gt 2294 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-Area V1.35 (Stoe & Cie, 2006)' _computing_cell_refinement 'X-Area V1.35' _computing_data_reduction 'X-RED32 V1.31 (Stoe & Cie, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL-97 _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^)+(0.0795P)^2^] 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 4982 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1494 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1723 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 0.860 _refine_ls_restrained_S_all 0.860 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.53709(18) 0.2680(2) 0.07911(10) 1.000 0.0239(8) . . N1 N Uani 0.6505(2) 0.2163(3) 0.17266(13) 1.000 0.0314(10) . . N2 N Uani 0.7956(3) 0.5993(4) 0.18240(17) 1.000 0.0541(14) . . C1 C Uani 0.6176(3) 0.3139(4) 0.12636(15) 1.000 0.0250(11) . . C2 C Uani 0.5932(3) 0.0810(4) 0.17473(17) 1.000 0.0326(11) . . C3 C Uani 0.5098(3) 0.0963(4) 0.20804(18) 1.000 0.0388(14) . . C4 C Uani 0.4289(3) 0.2119(4) 0.18012(18) 1.000 0.0392(14) . . C5 C Uani 0.3488(3) 0.2260(5) 0.21486(19) 1.000 0.0454(14) . . C6 C Uani 0.2667(4) 0.3360(5) 0.1874(2) 1.000 0.0512(17) . . C7 C Uani 0.2014(4) 0.2965(5) 0.1226(2) 1.000 0.0559(17) . . C8 C Uani 0.7410(4) 0.2438(6) 0.2241(2) 1.000 0.0567(7) . . C9 C Uani 0.7142(4) 0.3089(5) 0.2790(2) 1.000 0.0567(7) . . C10 C Uani 0.8066(4) 0.3616(5) 0.3317(2) 1.000 0.0567(7) . . C11 C Uani 0.8843(4) 0.2486(5) 0.3607(2) 1.000 0.0567(7) . . C12 C Uani 0.9601(4) 0.3052(5) 0.4200(2) 1.000 0.0567(7) . . C13 C Uani 1.0408(4) 0.1902(5) 0.4469(2) 1.000 0.0567(7) . . C14 C Uani 0.6465(3) 0.4546(4) 0.11435(15) 1.000 0.0242(11) . . C15 C Uani 0.7285(3) 0.5347(4) 0.15147(16) 1.000 0.0308(13) . . C16 C Uani 0.5786(3) 0.4992(3) 0.05558(14) 1.000 0.0210(10) . . C17 C Uani 0.5128(3) 0.3815(4) 0.03597(14) 1.000 0.0221(11) . . C18 C Uani 0.4330(3) 0.3724(4) -0.01783(15) 1.000 0.0226(11) . . C19 C Uani 0.3712(3) 0.2410(4) -0.03236(14) 1.000 0.0219(11) . . C20 C Uani 0.3277(3) 0.1310(4) -0.03943(15) 1.000 0.0243(11) . . C21 C Uani 0.2743(3) -0.0095(4) -0.04616(16) 1.000 0.0255(11) . . C22 C Uani 0.1910(3) -0.0359(4) -0.09849(16) 1.000 0.0281(11) . . C23 C Uani 0.1375(3) -0.1725(4) -0.10333(17) 1.000 0.0302(12) . . C24 C Uani 0.1700(3) -0.2781(4) -0.05694(18) 1.000 0.0352(14) . . C25 C Uani 0.2529(3) -0.2576(4) -0.00631(16) 1.000 0.0291(11) . . C26 C Uani 0.3069(3) -0.1207(4) -0.00019(16) 1.000 0.0261(11) . . C27 C Uani 0.3922(3) -0.1027(4) 0.05167(16) 1.000 0.0307(11) . . C28 C Uani 0.4237(3) -0.2121(4) 0.09415(17) 1.000 0.0355(14) . . C29 C Uani 0.3711(3) -0.3469(4) 0.08872(18) 1.000 0.0378(14) . . C30 C Uani 0.2878(3) -0.3686(4) 0.03967(18) 1.000 0.0369(14) . . C31 C Uani 0.0517(3) -0.1960(4) -0.15566(18) 1.000 0.0349(12) . . C32 C Uani 0.0230(3) -0.0926(5) -0.20133(19) 1.000 0.0403(16) . . C33 C Uani 0.0776(3) 0.0415(4) -0.19705(18) 1.000 0.0385(14) . . C34 C Uani 0.1583(3) 0.0677(4) -0.14778(17) 1.000 0.0330(12) . . H2A H Uiso 0.64060 0.00370 0.19610 1.000 0.0490 calc R H2B H Uiso 0.56250 0.04770 0.13130 1.000 0.0490 calc R H3A H Uiso 0.54120 0.12180 0.25240 1.000 0.0580 calc R H3B H Uiso 0.47640 -0.00020 0.20730 1.000 0.0580 calc R H4A H Uiso 0.46200 0.30850 0.18020 1.000 0.0590 calc R H4B H Uiso 0.39620 0.18570 0.13610 1.000 0.0590 calc R H5A H Uiso 0.31740 0.12850 0.21580 1.000 0.0680 calc R H5B H Uiso 0.38170 0.25440 0.25860 1.000 0.0680 calc R H6A H Uiso 0.29810 0.43300 0.18520 1.000 0.0770 calc R H6B H Uiso 0.22300 0.34570 0.21600 1.000 0.0770 calc R H7A H Uiso 0.16740 0.20270 0.12460 1.000 0.0840 calc R H7B H Uiso 0.24360 0.28770 0.09370 1.000 0.0840 calc R H7C H Uiso 0.15100 0.37360 0.10790 1.000 0.0840 calc R H8A H Uiso 0.78620 0.31170 0.20980 1.000 0.0850 calc R H8B H Uiso 0.77750 0.15030 0.23660 1.000 0.0850 calc R H9A H Uiso 0.67680 0.23480 0.29650 1.000 0.0850 calc R H9B H Uiso 0.66870 0.39350 0.26460 1.000 0.0850 calc R H10A H Uiso 0.84040 0.44080 0.31440 1.000 0.0850 calc R H10B H Uiso 0.78140 0.40560 0.36540 1.000 0.0850 calc R H11A H Uiso 0.92090 0.21920 0.32990 1.000 0.0850 calc R H11B H Uiso 0.85010 0.16030 0.37110 1.000 0.0850 calc R H12A H Uiso 0.99240 0.39580 0.41010 1.000 0.0850 calc R H12B H Uiso 0.92410 0.33020 0.45170 1.000 0.0850 calc R H13A H Uiso 1.07700 0.16640 0.41570 1.000 0.0850 calc R H13B H Uiso 1.00890 0.10120 0.45750 1.000 0.0850 calc R H13C H Uiso 1.08820 0.22920 0.48460 1.000 0.0850 calc R H24 H Uiso 0.13380 -0.36790 -0.06020 1.000 0.0530 calc R H27 H Uiso 0.42820 -0.01250 0.05680 1.000 0.0460 calc R H28 H Uiso 0.48190 -0.19760 0.12800 1.000 0.0530 calc R H29 H Uiso 0.39350 -0.42210 0.11900 1.000 0.0570 calc R H30 H Uiso 0.25260 -0.45930 0.03620 1.000 0.0560 calc R H31 H Uiso 0.01440 -0.28470 -0.15850 1.000 0.0530 calc R H32 H Uiso -0.03340 -0.10990 -0.23610 1.000 0.0610 calc R H33 H Uiso 0.05720 0.11330 -0.22900 1.000 0.0580 calc R H34 H Uiso 0.19400 0.15760 -0.14610 1.000 0.0490 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 0.0238(14) 0.0255(13) 0.0197(12) 0.0038(10) 0.0012(11) -0.0052(11) N1 0.0243(18) 0.0369(18) 0.0262(16) 0.0071(14) -0.0050(15) -0.0094(15) N2 0.052(3) 0.044(2) 0.048(2) 0.0158(18) -0.018(2) -0.018(2) C1 0.023(2) 0.0292(19) 0.0225(17) 0.0035(15) 0.0055(17) 0.0008(16) C2 0.035(2) 0.029(2) 0.0320(19) 0.0110(16) 0.0061(19) -0.0033(17) C3 0.043(3) 0.039(2) 0.032(2) 0.0080(17) 0.006(2) -0.013(2) C4 0.047(3) 0.034(2) 0.039(2) 0.0004(17) 0.016(2) -0.0022(19) C5 0.055(3) 0.042(2) 0.042(2) -0.0032(19) 0.018(2) -0.011(2) C6 0.056(3) 0.048(3) 0.056(3) 0.002(2) 0.026(3) 0.003(2) C7 0.049(3) 0.047(3) 0.071(3) 0.009(2) 0.015(3) 0.002(2) C8 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C9 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C10 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C11 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C12 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C13 0.0526(14) 0.0618(13) 0.0544(11) 0.0063(9) 0.0121(10) -0.0061(10) C14 0.023(2) 0.0267(19) 0.0206(17) 0.0001(14) 0.0020(16) -0.0013(16) C15 0.035(3) 0.0274(19) 0.0247(19) 0.0057(16) -0.0009(19) -0.0002(19) C16 0.021(2) 0.0223(18) 0.0184(16) -0.0017(13) 0.0029(16) -0.0017(15) C17 0.024(2) 0.0235(18) 0.0172(17) 0.0048(14) 0.0029(16) 0.0029(16) C18 0.021(2) 0.0239(18) 0.0216(17) 0.0017(14) 0.0036(16) -0.0026(15) C19 0.025(2) 0.0232(19) 0.0155(16) 0.0061(14) 0.0019(15) 0.0089(17) C20 0.019(2) 0.033(2) 0.0193(17) 0.0006(15) 0.0023(16) 0.0016(17) C21 0.025(2) 0.0249(18) 0.0268(18) -0.0041(15) 0.0072(17) -0.0030(16) C22 0.025(2) 0.0287(19) 0.0307(19) -0.0050(16) 0.0077(18) -0.0010(16) C23 0.028(2) 0.032(2) 0.033(2) -0.0065(17) 0.0122(19) -0.0051(17) C24 0.038(3) 0.027(2) 0.044(2) -0.0061(17) 0.017(2) -0.0109(18) C25 0.033(2) 0.027(2) 0.0315(19) -0.0020(16) 0.0157(19) -0.0038(17) C26 0.025(2) 0.0262(19) 0.0285(19) -0.0034(15) 0.0096(18) 0.0005(16) C27 0.035(2) 0.028(2) 0.0276(19) 0.0000(16) 0.0061(19) -0.0033(17) C28 0.044(3) 0.036(2) 0.0262(19) -0.0011(17) 0.0090(19) 0.0050(19) C29 0.051(3) 0.036(2) 0.032(2) 0.0070(17) 0.021(2) 0.006(2) C30 0.051(3) 0.026(2) 0.040(2) -0.0012(17) 0.023(2) -0.0037(19) C31 0.023(2) 0.042(2) 0.039(2) -0.0165(19) 0.007(2) -0.0046(18) C32 0.027(3) 0.048(3) 0.039(2) -0.013(2) -0.003(2) 0.006(2) C33 0.039(3) 0.033(2) 0.039(2) -0.0009(18) 0.003(2) 0.0046(19) C34 0.029(2) 0.030(2) 0.036(2) -0.0004(17) 0.002(2) -0.0025(17) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.371(4) . . yes O1 C17 1.387(4) . . yes N1 C1 1.342(4) . . yes N1 C2 1.471(5) . . yes N1 C8 1.469(6) . . yes N2 C15 1.154(5) . . yes C1 C14 1.388(5) . . no C2 C3 1.533(6) . . no C3 C4 1.537(6) . . no C4 C5 1.514(6) . . no C5 C6 1.511(7) . . no C6 C7 1.521(6) . . no C8 C9 1.489(7) . . no C9 C10 1.556(7) . . no C10 C11 1.500(7) . . no C11 C12 1.533(7) . . no C12 C13 1.527(7) . . no C14 C15 1.410(5) . . no C14 C16 1.444(5) . . no C16 C17 1.396(5) . . no C16 C18 1.422(5) . 3_665 no C17 C18 1.392(5) . . no C18 C19 1.453(5) . . no C19 C20 1.156(5) . . no C20 C21 1.463(5) . . no C21 C22 1.417(5) . . no C21 C26 1.422(5) . . no C22 C23 1.435(5) . . no C22 C34 1.423(5) . . no C23 C24 1.392(5) . . no C23 C31 1.434(6) . . no C24 C25 1.383(5) . . no C25 C26 1.439(5) . . no C25 C30 1.425(5) . . no C26 C27 1.417(5) . . no C27 C28 1.360(5) . . no C28 C29 1.414(5) . . no C29 C30 1.368(6) . . no C31 C32 1.362(6) . . no C32 C33 1.424(6) . . no C33 C34 1.355(6) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C4 H4A 0.9900 . . no C4 H4B 0.9900 . . no C5 H5A 0.9900 . . no C5 H5B 0.9900 . . no C6 H6A 0.9900 . . no C6 H6B 0.9900 . . no C7 H7A 0.9800 . . no C7 H7B 0.9800 . . no C7 H7C 0.9800 . . no C8 H8A 0.9900 . . no C8 H8B 0.9900 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C11 H11A 0.9900 . . no C11 H11B 0.9900 . . no C12 H12A 0.9900 . . no C12 H12B 0.9900 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C24 H24 0.9500 . . no C27 H27 0.9500 . . no C28 H28 0.9500 . . no C29 H29 0.9500 . . no C30 H30 0.9500 . . no C31 H31 0.9500 . . no C32 H32 0.9500 . . no C33 H33 0.9500 . . no C34 H34 0.9500 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C17 107.3(3) . . . yes C1 N1 C2 120.3(3) . . . yes C1 N1 C8 121.6(3) . . . yes C2 N1 C8 118.0(3) . . . yes O1 C1 N1 114.9(3) . . . yes O1 C1 C14 110.4(3) . . . yes N1 C1 C14 134.6(3) . . . yes N1 C2 C3 114.8(3) . . . yes C2 C3 C4 115.2(3) . . . no C3 C4 C5 113.8(3) . . . no C4 C5 C6 114.9(4) . . . no C5 C6 C7 114.4(4) . . . no N1 C8 C9 111.0(4) . . . yes C8 C9 C10 113.9(5) . . . no C9 C10 C11 117.2(4) . . . no C10 C11 C12 112.4(4) . . . no C11 C12 C13 111.2(4) . . . no C1 C14 C15 126.3(3) . . . no C1 C14 C16 106.4(3) . . . no C15 C14 C16 127.3(3) . . . no N2 C15 C14 179.3(4) . . . yes C14 C16 C17 106.0(3) . . . no C14 C16 C18 134.9(3) . . 3_665 no C17 C16 C18 119.1(3) . . 3_665 no O1 C17 C16 109.9(3) . . . yes O1 C17 C18 122.5(3) . . . yes C16 C17 C18 127.7(3) . . . no C17 C18 C19 121.4(3) . . . no C16 C18 C17 113.2(3) 3_665 . . no C16 C18 C19 125.4(3) 3_665 . . no C18 C19 C20 174.1(4) . . . no C19 C20 C21 178.1(4) . . . no C20 C21 C22 120.4(3) . . . no C20 C21 C26 119.7(3) . . . no C22 C21 C26 119.9(3) . . . no C21 C22 C23 119.7(3) . . . no C21 C22 C34 122.5(3) . . . no C23 C22 C34 117.8(3) . . . no C22 C23 C24 119.1(3) . . . no C22 C23 C31 119.1(3) . . . no C24 C23 C31 121.9(3) . . . no C23 C24 C25 122.6(4) . . . no C24 C25 C26 119.2(3) . . . no C24 C25 C30 122.2(3) . . . no C26 C25 C30 118.7(3) . . . no C21 C26 C25 119.5(3) . . . no C21 C26 C27 122.3(3) . . . no C25 C26 C27 118.2(3) . . . no C26 C27 C28 121.3(4) . . . no C27 C28 C29 121.0(4) . . . no C28 C29 C30 119.7(3) . . . no C25 C30 C29 121.2(3) . . . no C23 C31 C32 120.8(4) . . . no C31 C32 C33 120.0(4) . . . no C32 C33 C34 120.6(4) . . . no C22 C34 C33 121.7(4) . . . no N1 C2 H2A 109.00 . . . no N1 C2 H2B 109.00 . . . no C3 C2 H2A 109.00 . . . no C3 C2 H2B 109.00 . . . no H2A C2 H2B 108.00 . . . no C2 C3 H3A 108.00 . . . no C2 C3 H3B 109.00 . . . no C4 C3 H3A 108.00 . . . no C4 C3 H3B 108.00 . . . no H3A C3 H3B 108.00 . . . no C3 C4 H4A 109.00 . . . no C3 C4 H4B 109.00 . . . no C5 C4 H4A 109.00 . . . no C5 C4 H4B 109.00 . . . no H4A C4 H4B 108.00 . . . no C4 C5 H5A 109.00 . . . no C4 C5 H5B 109.00 . . . no C6 C5 H5A 109.00 . . . no C6 C5 H5B 109.00 . . . no H5A C5 H5B 108.00 . . . no C5 C6 H6A 109.00 . . . no C5 C6 H6B 109.00 . . . no C7 C6 H6A 109.00 . . . no C7 C6 H6B 109.00 . . . no H6A C6 H6B 108.00 . . . no C6 C7 H7A 109.00 . . . no C6 C7 H7B 110.00 . . . no C6 C7 H7C 109.00 . . . no H7A C7 H7B 110.00 . . . no H7A C7 H7C 109.00 . . . no H7B C7 H7C 110.00 . . . no N1 C8 H8A 110.00 . . . no N1 C8 H8B 109.00 . . . no C9 C8 H8A 109.00 . . . no C9 C8 H8B 109.00 . . . no H8A C8 H8B 108.00 . . . no C8 C9 H9A 109.00 . . . no C8 C9 H9B 109.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C9 C10 H10A 108.00 . . . no C9 C10 H10B 108.00 . . . no C11 C10 H10A 108.00 . . . no C11 C10 H10B 108.00 . . . no H10A C10 H10B 107.00 . . . no C10 C11 H11A 109.00 . . . no C10 C11 H11B 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no C11 C12 H12A 109.00 . . . no C11 C12 H12B 109.00 . . . no C13 C12 H12A 109.00 . . . no C13 C12 H12B 109.00 . . . no H12A C12 H12B 108.00 . . . no C12 C13 H13A 109.00 . . . no C12 C13 H13B 109.00 . . . no C12 C13 H13C 110.00 . . . no H13A C13 H13B 110.00 . . . no H13A C13 H13C 110.00 . . . no H13B C13 H13C 109.00 . . . no C23 C24 H24 119.00 . . . no C25 C24 H24 119.00 . . . no C26 C27 H27 119.00 . . . no C28 C27 H27 119.00 . . . no C27 C28 H28 119.00 . . . no C29 C28 H28 120.00 . . . no C28 C29 H29 120.00 . . . no C30 C29 H29 120.00 . . . no C25 C30 H30 119.00 . . . no C29 C30 H30 119.00 . . . no C23 C31 H31 120.00 . . . no C32 C31 H31 120.00 . . . no C31 C32 H32 120.00 . . . no C33 C32 H32 120.00 . . . no C32 C33 H33 120.00 . . . no C34 C33 H33 120.00 . . . no C22 C34 H34 119.00 . . . no C33 C34 H34 119.00 . . . no 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 C17 O1 C1 N1 179.6(3) . . . . no C17 O1 C1 C14 -0.5(4) . . . . no C1 O1 C17 C16 0.5(4) . . . . no C1 O1 C17 C18 -179.1(4) . . . . no C2 N1 C1 O1 -8.1(5) . . . . no C2 N1 C1 C14 172.0(4) . . . . no C8 N1 C1 O1 175.0(3) . . . . no C8 N1 C1 C14 -4.9(7) . . . . no C1 N1 C2 C3 -86.7(4) . . . . no C8 N1 C2 C3 90.3(4) . . . . no C1 N1 C8 C9 95.0(5) . . . . no C2 N1 C8 C9 -82.0(5) . . . . no O1 C1 C14 C15 -177.6(4) . . . . no O1 C1 C14 C16 0.3(4) . . . . no N1 C1 C14 C15 2.3(7) . . . . no N1 C1 C14 C16 -179.8(4) . . . . no N1 C2 C3 C4 58.8(4) . . . . no C2 C3 C4 C5 -179.0(3) . . . . no C3 C4 C5 C6 -178.4(3) . . . . no C4 C5 C6 C7 65.0(5) . . . . no N1 C8 C9 C10 -171.8(4) . . . . no C8 C9 C10 C11 -59.5(6) . . . . no C9 C10 C11 C12 -168.7(4) . . . . no C10 C11 C12 C13 -177.6(4) . . . . no C1 C14 C16 C17 0.0(4) . . . . no C1 C14 C16 C18 179.8(4) . . . 3_665 no C15 C14 C16 C17 177.9(4) . . . . no C15 C14 C16 C18 -2.4(7) . . . 3_665 no C14 C16 C17 O1 -0.4(4) . . . . no C14 C16 C17 C18 179.2(4) . . . . no C18 C16 C17 O1 179.9(3) 3_665 . . . no C18 C16 C17 C18 -0.6(6) 3_665 . . . no C14 C16 C18 C17 -179.2(4) . . 3_665 3_665 no C14 C16 C18 C19 -0.4(7) . . 3_665 3_665 no C17 C16 C18 C17 0.5(5) . . 3_665 3_665 no C17 C16 C18 C19 179.3(4) . . 3_665 3_665 no O1 C17 C18 C19 -1.1(6) . . . . no O1 C17 C18 C16 -180.0(3) . . . 3_665 no C16 C17 C18 C19 179.4(4) . . . . no C16 C17 C18 C16 0.5(6) . . . 3_665 no C20 C21 C22 C23 -178.0(4) . . . . no C20 C21 C22 C34 3.0(6) . . . . no C26 C21 C22 C23 2.6(6) . . . . no C26 C21 C22 C34 -176.4(4) . . . . no C20 C21 C26 C25 178.7(4) . . . . no C20 C21 C26 C27 -2.1(6) . . . . no C22 C21 C26 C25 -1.9(6) . . . . no C22 C21 C26 C27 177.3(4) . . . . no C21 C22 C23 C24 -1.4(6) . . . . no C21 C22 C23 C31 178.3(4) . . . . no C34 C22 C23 C24 177.7(4) . . . . no C34 C22 C23 C31 -2.6(6) . . . . no C21 C22 C34 C33 -179.1(4) . . . . no C23 C22 C34 C33 1.9(6) . . . . no C22 C23 C24 C25 -0.7(6) . . . . no C31 C23 C24 C25 179.7(4) . . . . no C22 C23 C31 C32 2.2(6) . . . . no C24 C23 C31 C32 -178.2(4) . . . . no C23 C24 C25 C26 1.4(6) . . . . no C23 C24 C25 C30 -177.6(4) . . . . no C24 C25 C26 C21 -0.1(6) . . . . no C24 C25 C26 C27 -179.3(4) . . . . no C30 C25 C26 C21 178.9(4) . . . . no C30 C25 C26 C27 -0.3(6) . . . . no C24 C25 C30 C29 178.8(4) . . . . no C26 C25 C30 C29 -0.2(6) . . . . no C21 C26 C27 C28 -178.1(4) . . . . no C25 C26 C27 C28 1.1(6) . . . . no C26 C27 C28 C29 -1.3(6) . . . . no C27 C28 C29 C30 0.7(6) . . . . no C28 C29 C30 C25 0.1(6) . . . . no C23 C31 C32 C33 -0.8(6) . . . . no C31 C32 C33 C34 0.0(6) . . . . no C32 C33 C34 C22 -0.6(6) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C3 3.370(4) . . no O1 C4 3.053(5) . . no O1 C26 3.396(5) . 3_655 no O1 H4A 2.7400 . . no O1 H4B 2.7000 . . no O1 H2B 2.2900 . . no N2 C34 3.231(5) . 3_665 no N1 H4A 2.7800 . . no N2 H8A 2.7000 . . no N2 H34 2.3700 . 3_665 no N2 H32 2.5600 . 4_655 no C1 C4 3.277(6) . . no C3 C9 3.432(6) . . no C3 O1 3.370(4) . . no C4 O1 3.053(5) . . no C4 C1 3.277(6) . . no C8 C15 3.080(6) . . no C8 C23 3.584(6) . 3_655 no C9 C15 3.547(6) . . no C9 C3 3.432(6) . . no C14 C24 3.514(6) . 3_655 no C14 C25 3.562(5) . 3_655 no C15 C9 3.547(6) . . no C15 C19 3.331(5) . 3_665 no C15 C8 3.080(6) . . no C16 C25 3.578(5) . 3_655 no C16 C29 3.440(6) . 1_565 no C16 C30 3.374(5) . 3_655 no C17 C30 3.590(6) . 3_655 no C17 C29 3.541(5) . 1_565 no C17 C28 3.585(5) . 3_655 no C17 C29 3.566(5) . 3_655 no C18 C28 3.273(6) . 3_655 no C18 C30 3.546(6) . 1_565 no C18 C29 3.482(6) . 3_655 no C19 C28 3.471(6) . 3_655 no C19 C15 3.331(5) . 3_665 no C23 C8 3.584(6) . 3_655 no C24 C14 3.514(6) . 3_655 no C25 C16 3.578(5) . 3_655 no C25 C14 3.562(5) . 3_655 no C26 O1 3.396(5) . 3_655 no C28 C19 3.471(6) . 3_655 no C28 C17 3.585(5) . 3_655 no C28 C18 3.273(6) . 3_655 no C29 C17 3.541(5) . 1_545 no C29 C17 3.566(5) . 3_655 no C29 C18 3.482(6) . 3_655 no C29 C16 3.440(6) . 1_545 no C30 C18 3.546(6) . 1_545 no C30 C17 3.590(6) . 3_655 no C30 C16 3.374(5) . 3_655 no C34 N2 3.231(5) . 3_665 no C1 H4A 2.7200 . . no C1 H9B 3.0500 . . no C2 H28 3.0000 . . no C2 H27 3.0900 . . no C2 H9A 2.9900 . . no C3 H9A 2.8800 . . no C4 H7B 2.8400 . . no C5 H9B 3.0800 . 2_645 no C6 H2A 2.9800 . 2_655 no C7 H13C 3.0500 . 4_454 no C7 H4B 2.8100 . . no C8 H11A 2.9300 . . no C9 H3A 2.8600 . . no C9 H5A 2.9500 . 2_655 no C10 H5A 2.9900 . 2_655 no C11 H8B 2.8900 . . no C14 H8A 2.7700 . . no C15 H34 3.0100 . 3_665 no C15 H8A 2.4200 . . no C19 H34 3.1000 . . no C19 H27 3.0000 . . no C20 H34 2.5900 . . no C20 H27 2.5700 . . no C22 H12A 3.0700 . 4_454 no C27 H2B 2.8800 . . no C28 H2B 3.0100 . . no C28 H3B 3.0900 . . no C29 H9A 2.9000 . 2_645 no C31 H8A 3.0000 . 3_655 no C32 H10A 2.9700 . 4_454 no C33 H8B 2.9600 . 3_655 no C33 H12A 2.9800 . 4_454 no C34 H8B 3.0900 . 3_655 no C34 H12A 2.9300 . 4_454 no H2A H8B 2.2900 . . no H2A C6 2.9800 . 2_645 no H2A H5B 2.5300 . 2_645 no H2B O1 2.2900 . . no H2B C27 2.8800 . . no H2B C28 3.0100 . . no H2B H27 2.1900 . . no H2B H28 2.4900 . . no H3A C9 2.8600 . . no H3A H5B 2.5500 . . no H3A H9A 2.1300 . . no H3B C28 3.0900 . . no H3B H5A 2.5400 . . no H3B H28 2.5300 . . no H3B H9B 2.4500 . 2_645 no H4A O1 2.7400 . . no H4A N1 2.7800 . . no H4A C1 2.7200 . . no H4A H6A 2.5600 . . no H4B O1 2.7000 . . no H4B C7 2.8100 . . no H4B H7B 2.2600 . . no H5A H3B 2.5400 . . no H5A H7A 2.5700 . . no H5A C9 2.9500 . 2_645 no H5A C10 2.9900 . 2_645 no H5A H9B 2.1800 . 2_645 no H5B H3A 2.5500 . . no H5B H2A 2.5300 . 2_655 no H6A H4A 2.5600 . . no H6A H29 2.5800 . 1_565 no H7A H5A 2.5700 . . no H7B C4 2.8400 . . no H7B H4B 2.2600 . . no H8A N2 2.7000 . . no H8A C14 2.7700 . . no H8A C15 2.4200 . . no H8A H10A 2.5300 . . no H8A C31 3.0000 . 3_655 no H8B C11 2.8900 . . no H8B H2A 2.2900 . . no H8B H11A 2.5300 . . no H8B C33 2.9600 . 3_655 no H8B C34 3.0900 . 3_655 no H9A C2 2.9900 . . no H9A C3 2.8800 . . no H9A H3A 2.1300 . . no H9A C29 2.9000 . 2_655 no H9B C1 3.0500 . . no H9B C5 3.0800 . 2_655 no H9B H3B 2.4500 . 2_655 no H9B H5A 2.1800 . 2_655 no H10A H8A 2.5300 . . no H10A H12A 2.5800 . . no H10A C32 2.9700 . 4_655 no H10B H12B 2.4500 . . no H11A C8 2.9300 . . no H11A H8B 2.5300 . . no H11A H13A 2.5100 . . no H11B H13B 2.5500 . . no H12A H10A 2.5800 . . no H12A C22 3.0700 . 4_655 no H12A C33 2.9800 . 4_655 no H12A C34 2.9300 . 4_655 no H12B H10B 2.4500 . . no H13A H11A 2.5100 . . no H13B H11B 2.5500 . . no H13C C7 3.0500 . 4_655 no H24 H30 2.4600 . . no H24 H31 2.4700 . . no H27 C2 3.0900 . . no H27 C19 3.0000 . . no H27 C20 2.5700 . . no H27 H2B 2.1900 . . no H28 C2 3.0000 . . no H28 H2B 2.4900 . . no H28 H3B 2.5300 . . no H29 H6A 2.5800 . 1_545 no H30 H24 2.4600 . . no H31 H24 2.4700 . . no H31 H33 2.6000 . 2_544 no H32 N2 2.5600 . 4_454 no H33 H31 2.6000 . 2_554 no H34 C19 3.1000 . . no H34 C20 2.5900 . . no H34 N2 2.3700 . 3_665 no H34 C15 3.0100 . 3_665 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C2 H2B O1 0.9900 2.2900 2.668(4) 101.00 . yes C32 H32 N2 0.9500 2.5600 3.485(6) 165.00 4_454 yes C34 H34 N2 0.9500 2.3700 3.231(5) 150.00 3_665 yes _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.518 _refine_diff_density_min -1.017 _refine_diff_density_rms 0.051 # Attachment 'compound2b.CIF' data_c:complex2b _database_code_depnum_ccdc_archive 'CCDC 783325' #TrackingRef 'compound2b.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H70 N4 O2' _chemical_formula_weight 975.28 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' O O 0.0106 0.0060 '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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0856(10) _cell_length_b 17.2822(16) _cell_length_c 16.4631(16) _cell_angle_alpha 90.00 _cell_angle_beta 129.164(6) _cell_angle_gamma 90.00 _cell_volume 2666.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2893 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 25.17 _exptl_crystal_description cube _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.073 _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 173(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 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13637 _diffrn_reflns_av_R_equivalents 0.1203 _diffrn_reflns_av_sigmaI/netI 0.2328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.11 _reflns_number_total 4685 _reflns_number_gt 1598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _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^)+(0.0223P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4685 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1715 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 0.686 _refine_ls_restrained_S_all 0.686 _refine_ls_shift/su_max 0.001 _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 0.3036(4) 0.36953(19) 0.3125(3) 0.0308(9) Uani 1 1 d . . . C2 C 0.1803(5) 0.3582(2) 0.1232(3) 0.0480(12) Uani 1 1 d . . . H2A H 0.2050 0.3181 0.0940 0.058 Uiso 1 1 calc R . . H2B H 0.2365 0.4052 0.1365 0.058 Uiso 1 1 calc R . . C3 C 0.0238(5) 0.3768(2) 0.0438(3) 0.0493(12) Uani 1 1 d . . . H3A H -0.0012 0.4168 0.0728 0.059 Uiso 1 1 calc R . . H3B H -0.0326 0.3298 0.0301 0.059 Uiso 1 1 calc R . . C4 C -0.0157(4) 0.4060(2) -0.0601(3) 0.0446(11) Uani 1 1 d . . . H4A H -0.1143 0.4266 -0.1042 0.053 Uiso 1 1 calc R . . H4B H 0.0485 0.4495 -0.0444 0.053 Uiso 1 1 calc R . . C5 C -0.0068(5) 0.3460(2) -0.1224(3) 0.0726(16) Uani 1 1 d . . . H5A H -0.0556 0.2985 -0.1260 0.087 Uiso 1 1 calc R . . H5B H 0.0949 0.3329 -0.0839 0.087 Uiso 1 1 calc R . . C6 C -0.0709(7) 0.3693(3) -0.2331(4) 0.102(2) Uani 1 1 d . . . H6A H -0.0332 0.3329 -0.2568 0.122 Uiso 1 1 calc R . . H6B H -0.1749 0.3598 -0.2777 0.122 Uiso 1 1 calc R . . C7 C -0.0524(6) 0.4469(4) -0.2568(4) 0.100(2) Uani 1 1 d . . . H7A H -0.0853 0.4848 -0.2320 0.151 Uiso 1 1 calc R . . H7B H -0.1081 0.4524 -0.3327 0.151 Uiso 1 1 calc R . . H7C H 0.0488 0.4558 -0.2217 0.151 Uiso 1 1 calc R . . C8 C 0.1717(4) 0.25164(18) 0.2223(3) 0.0427(11) Uani 1 1 d . . . H8A H 0.0746 0.2425 0.1556 0.051 Uiso 1 1 calc R . . H8B H 0.1678 0.2466 0.2804 0.051 Uiso 1 1 calc R . . C9 C 0.2764(5) 0.1911(2) 0.2355(4) 0.0838(18) Uani 1 1 d . . . H9A H 0.3193 0.2131 0.2056 0.101 Uiso 1 1 calc R . . H9B H 0.3546 0.1836 0.3115 0.101 Uiso 1 1 calc R . . C10 C 0.2211(6) 0.1186(3) 0.1906(4) 0.098(2) Uani 1 1 d . . . H10A H 0.1899 0.0941 0.2276 0.117 Uiso 1 1 calc R . . H10B H 0.3005 0.0869 0.2059 0.117 Uiso 1 1 calc R . . C11 C 0.0963(5) 0.1123(3) 0.0722(4) 0.0741(16) Uani 1 1 d . . . H11A H 0.0508 0.0610 0.0581 0.089 Uiso 1 1 calc R . . H11B H 0.0243 0.1520 0.0530 0.089 Uiso 1 1 calc R . . C12 C 0.1339(5) 0.1216(3) 0.0034(4) 0.0692(15) Uani 1 1 d . . . H12A H 0.2066 0.0824 0.0228 0.083 Uiso 1 1 calc R . . H12B H 0.1777 0.1732 0.0161 0.083 Uiso 1 1 calc R . . C13 C 0.0081(5) 0.1138(3) -0.1137(4) 0.0787(16) Uani 1 1 d . . . H13A H -0.0281 0.0606 -0.1290 0.118 Uiso 1 1 calc R . . H13B H 0.0398 0.1262 -0.1542 0.118 Uiso 1 1 calc R . . H13C H -0.0680 0.1496 -0.1329 0.118 Uiso 1 1 calc R . . C14 C 0.3641(4) 0.35555(17) 0.4155(3) 0.0255(9) Uani 1 1 d . . . C15 C 0.3630(4) 0.2849(2) 0.4599(3) 0.0337(10) Uani 1 1 d . . . C16 C 0.4394(4) 0.42566(17) 0.4736(2) 0.0229(8) Uani 1 1 d . . . C17 C 0.4203(4) 0.47724(17) 0.4007(2) 0.0235(9) Uani 1 1 d . . . C18 C 0.4761(4) 0.55162(17) 0.4199(3) 0.0248(9) Uani 1 1 d . . . C19 C 0.4477(4) 0.59812(17) 0.3358(3) 0.0265(9) Uani 1 1 d . . . C20 C 0.4167(4) 0.63023(19) 0.2625(3) 0.0257(9) Uani 1 1 d . . . C21 C 0.3778(4) 0.66776(19) 0.1679(3) 0.0295(9) Uani 1 1 d . . . C22 C 0.3669(4) 0.7501(2) 0.1600(3) 0.0316(9) Uani 1 1 d . . . C23 C 0.3273(4) 0.7860(2) 0.0660(3) 0.0345(10) Uani 1 1 d . . . C24 C 0.3044(4) 0.7400(2) -0.0133(3) 0.0370(10) Uani 1 1 d . . . H24A H 0.2796 0.7640 -0.0747 0.044 Uiso 1 1 calc R . . C25 C 0.3171(4) 0.6598(2) -0.0044(3) 0.0348(10) Uani 1 1 d . . . C26 C 0.3531(4) 0.62329(19) 0.0865(3) 0.0313(9) Uani 1 1 d . . . C27 C 0.3658(4) 0.54028(19) 0.0928(3) 0.0366(10) Uani 1 1 d . . . H27A H 0.3886 0.5141 0.1525 0.044 Uiso 1 1 calc R . . C28 C 0.3453(4) 0.4993(2) 0.0140(3) 0.0445(11) Uani 1 1 d . . . H28A H 0.3538 0.4445 0.0194 0.053 Uiso 1 1 calc R . . C29 C 0.3117(5) 0.5358(2) -0.0755(3) 0.0513(12) Uani 1 1 d . . . H29A H 0.2987 0.5058 -0.1293 0.062 Uiso 1 1 calc R . . C30 C 0.2980(4) 0.6137(2) -0.0847(3) 0.0461(11) Uani 1 1 d . . . H30A H 0.2753 0.6381 -0.1453 0.055 Uiso 1 1 calc R . . C31 C 0.3167(4) 0.8691(2) 0.0588(3) 0.0426(11) Uani 1 1 d . . . H31A H 0.2887 0.8941 -0.0030 0.051 Uiso 1 1 calc R . . C32 C 0.3463(4) 0.9119(2) 0.1391(3) 0.0459(12) Uani 1 1 d . . . H32A H 0.3398 0.9667 0.1334 0.055 Uiso 1 1 calc R . . C33 C 0.3864(4) 0.8762(2) 0.2306(3) 0.0423(11) Uani 1 1 d . . . H33A H 0.4077 0.9074 0.2864 0.051 Uiso 1 1 calc R . . C34 C 0.3955(4) 0.79788(19) 0.2414(3) 0.0374(10) Uani 1 1 d . . . H34A H 0.4211 0.7751 0.3037 0.045 Uiso 1 1 calc R . . O1 O 0.3360(2) 0.44424(11) 0.30169(16) 0.0288(6) Uani 1 1 d . . . N1 N 0.2198(3) 0.33044(16) 0.2224(2) 0.0378(8) Uani 1 1 d . . . N2 N 0.3627(4) 0.22785(16) 0.4948(2) 0.0479(10) Uani 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 0.025(3) 0.035(2) 0.030(2) -0.0028(18) 0.017(2) 0.0010(18) C2 0.055(4) 0.045(2) 0.033(2) -0.0115(19) 0.023(2) -0.015(2) C3 0.061(3) 0.033(2) 0.048(3) 0.0040(19) 0.032(3) 0.003(2) C4 0.054(3) 0.040(2) 0.040(2) -0.0008(19) 0.030(2) 0.000(2) C5 0.068(4) 0.064(3) 0.051(3) -0.006(3) 0.021(3) 0.024(3) C6 0.151(7) 0.095(4) 0.083(4) -0.037(4) 0.086(5) -0.011(4) C7 0.073(5) 0.175(6) 0.055(3) -0.009(4) 0.042(4) 0.008(5) C8 0.043(3) 0.0251(18) 0.036(2) -0.0093(17) 0.013(2) -0.0066(19) C9 0.062(4) 0.044(3) 0.069(3) -0.010(2) 0.006(3) 0.015(2) C10 0.099(5) 0.074(4) 0.090(4) -0.021(3) 0.045(4) 0.023(3) C11 0.065(4) 0.082(3) 0.066(3) -0.032(3) 0.037(3) -0.008(3) C12 0.062(4) 0.064(3) 0.078(4) 0.024(3) 0.042(3) 0.013(3) C13 0.084(4) 0.081(3) 0.065(4) -0.006(3) 0.044(3) -0.006(3) C14 0.028(2) 0.0227(18) 0.026(2) -0.0026(16) 0.0175(19) -0.0040(16) C15 0.033(3) 0.028(2) 0.032(2) -0.0097(18) 0.016(2) -0.0074(18) C16 0.022(2) 0.0221(17) 0.024(2) -0.0024(15) 0.0137(18) -0.0019(15) C17 0.025(2) 0.0251(18) 0.0170(19) -0.0014(15) 0.0116(18) -0.0009(15) C18 0.028(2) 0.0248(18) 0.029(2) 0.0047(16) 0.0217(19) 0.0031(16) C19 0.025(3) 0.0224(18) 0.031(2) -0.0056(17) 0.0168(19) -0.0016(16) C20 0.021(2) 0.0298(19) 0.022(2) -0.0045(17) 0.0115(18) -0.0028(17) C21 0.027(3) 0.036(2) 0.026(2) 0.0041(17) 0.017(2) -0.0025(18) C22 0.027(3) 0.035(2) 0.031(2) 0.0040(17) 0.017(2) -0.0008(18) C23 0.026(3) 0.043(2) 0.033(2) 0.0145(19) 0.018(2) 0.0049(19) C24 0.043(3) 0.046(2) 0.025(2) 0.0075(18) 0.023(2) 0.000(2) C25 0.029(3) 0.046(2) 0.026(2) 0.0002(18) 0.016(2) -0.0055(19) C26 0.028(3) 0.035(2) 0.028(2) -0.0020(18) 0.017(2) -0.0058(18) C27 0.042(3) 0.040(2) 0.031(2) 0.0016(18) 0.025(2) -0.002(2) C28 0.054(3) 0.039(2) 0.048(3) -0.006(2) 0.036(3) -0.005(2) C29 0.054(3) 0.062(3) 0.037(3) -0.018(2) 0.029(2) -0.014(2) C30 0.047(3) 0.063(3) 0.033(2) -0.001(2) 0.028(2) -0.006(2) C31 0.035(3) 0.041(2) 0.045(3) 0.019(2) 0.022(2) 0.003(2) C32 0.054(3) 0.033(2) 0.062(3) 0.007(2) 0.042(3) 0.000(2) C33 0.051(3) 0.033(2) 0.050(3) -0.0044(19) 0.036(2) -0.005(2) C34 0.039(3) 0.037(2) 0.038(2) 0.0027(19) 0.024(2) -0.0008(19) O1 0.0374(18) 0.0233(12) 0.0208(14) -0.0032(10) 0.0160(13) -0.0056(11) N1 0.033(2) 0.0417(18) 0.0283(18) -0.0127(15) 0.0148(17) -0.0144(16) N2 0.057(3) 0.0284(18) 0.042(2) -0.0021(15) 0.023(2) -0.0111(16) _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 1.336(4) . ? C1 C14 1.380(4) . ? C1 O1 1.393(4) . ? C2 N1 1.464(4) . ? C2 C3 1.506(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.542(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.510(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.517(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.453(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N1 1.480(4) . ? C8 C9 1.549(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.392(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.541(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.472(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.531(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.427(4) . ? C14 C16 1.453(4) . ? C15 N2 1.143(4) . ? C16 C17 1.392(4) . ? C16 C18 1.418(4) 3_666 ? C17 O1 1.386(3) . ? C17 C18 1.392(4) . ? C18 C16 1.418(4) 3_666 ? C18 C19 1.442(4) . ? C19 C20 1.154(4) . ? C20 C21 1.465(5) . ? C21 C26 1.403(5) . ? C21 C22 1.427(5) . ? C22 C34 1.418(5) . ? C22 C23 1.440(5) . ? C23 C24 1.399(5) . ? C23 C31 1.441(5) . ? C24 C25 1.391(5) . ? C24 H24A 0.9500 . ? C25 C26 1.417(5) . ? C25 C30 1.432(5) . ? C26 C27 1.440(5) . ? C27 C28 1.356(5) . ? C27 H27A 0.9500 . ? C28 C29 1.407(5) . ? C28 H28A 0.9500 . ? C29 C30 1.354(5) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C32 1.350(5) . ? C31 H31A 0.9500 . ? C32 C33 1.401(5) . ? C32 H32A 0.9500 . ? C33 C34 1.360(5) . ? C33 H33A 0.9500 . ? C34 H34A 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 N1 C1 C14 135.9(3) . . ? N1 C1 O1 113.9(3) . . ? C14 C1 O1 110.2(3) . . ? N1 C2 C3 112.5(3) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 111.8(3) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 115.0(3) . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C4 C5 C6 115.6(4) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C6 C5 H5B 108.4 . . ? H5A C5 H5B 107.4 . . ? C7 C6 C5 121.3(5) . . ? C7 C6 H6A 107.0 . . ? C5 C6 H6A 107.0 . . ? C7 C6 H6B 107.0 . . ? C5 C6 H6B 107.0 . . ? H6A C6 H6B 106.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 109.6(3) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C8 117.2(4) . . ? C10 C9 H9A 108.0 . . ? C8 C9 H9A 108.0 . . ? C10 C9 H9B 108.0 . . ? C8 C9 H9B 108.0 . . ? H9A C9 H9B 107.2 . . ? C9 C10 C11 119.6(5) . . ? C9 C10 H10A 107.4 . . ? C11 C10 H10A 107.4 . . ? C9 C10 H10B 107.4 . . ? C11 C10 H10B 107.4 . . ? H10A C10 H10B 106.9 . . ? C12 C11 C10 115.8(5) . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? C10 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C11 C12 C13 114.6(4) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 C14 C15 127.6(3) . . ? C1 C14 C16 106.7(3) . . ? C15 C14 C16 125.5(3) . . ? N2 C15 C14 179.1(4) . . ? C17 C16 C18 119.1(3) . 3_666 ? C17 C16 C14 105.8(3) . . ? C18 C16 C14 135.0(3) 3_666 . ? O1 C17 C18 122.5(3) . . ? O1 C17 C16 110.4(3) . . ? C18 C17 C16 127.1(3) . . ? C17 C18 C16 113.8(3) . 3_666 ? C17 C18 C19 120.6(3) . . ? C16 C18 C19 125.6(3) 3_666 . ? C20 C19 C18 173.9(4) . . ? C19 C20 C21 177.5(4) . . ? C26 C21 C22 120.5(3) . . ? C26 C21 C20 120.3(3) . . ? C22 C21 C20 119.2(3) . . ? C34 C22 C21 122.8(3) . . ? C34 C22 C23 118.8(3) . . ? C21 C22 C23 118.4(3) . . ? C24 C23 C22 119.6(3) . . ? C24 C23 C31 122.4(3) . . ? C22 C23 C31 118.0(4) . . ? C25 C24 C23 121.7(3) . . ? C25 C24 H24A 119.2 . . ? C23 C24 H24A 119.2 . . ? C24 C25 C26 119.6(3) . . ? C24 C25 C30 121.0(3) . . ? C26 C25 C30 119.3(3) . . ? C21 C26 C25 120.2(3) . . ? C21 C26 C27 121.9(3) . . ? C25 C26 C27 117.9(3) . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C27 C28 C29 121.7(4) . . ? C27 C28 H28A 119.2 . . ? C29 C28 H28A 119.2 . . ? C30 C29 C28 119.8(4) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C29 C30 C25 120.9(4) . . ? C29 C30 H30A 119.5 . . ? C25 C30 H30A 119.5 . . ? C32 C31 C23 120.7(4) . . ? C32 C31 H31A 119.6 . . ? C23 C31 H31A 119.6 . . ? C31 C32 C33 120.6(4) . . ? C31 C32 H32A 119.7 . . ? C33 C32 H32A 119.7 . . ? C34 C33 C32 121.5(4) . . ? C34 C33 H33A 119.2 . . ? C32 C33 H33A 119.2 . . ? C33 C34 C22 120.3(3) . . ? C33 C34 H34A 119.9 . . ? C22 C34 H34A 119.9 . . ? C17 O1 C1 106.8(2) . . ? C1 N1 C2 123.9(3) . . ? C1 N1 C8 119.2(3) . . ? C2 N1 C8 116.7(3) . . ? 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 N1 C2 C3 C4 179.9(3) . . . . ? C2 C3 C4 C5 68.8(5) . . . . ? C3 C4 C5 C6 169.1(5) . . . . ? C4 C5 C6 C7 40.4(8) . . . . ? N1 C8 C9 C10 -150.8(4) . . . . ? C8 C9 C10 C11 57.5(7) . . . . ? C9 C10 C11 C12 76.5(6) . . . . ? C10 C11 C12 C13 179.1(4) . . . . ? N1 C1 C14 C15 6.6(7) . . . . ? O1 C1 C14 C15 -176.0(3) . . . . ? N1 C1 C14 C16 -177.3(4) . . . . ? O1 C1 C14 C16 0.0(4) . . . . ? C1 C14 C15 N2 51(31) . . . . ? C16 C14 C15 N2 -125(31) . . . . ? C1 C14 C16 C17 -0.8(4) . . . . ? C15 C14 C16 C17 175.4(3) . . . . ? C1 C14 C16 C18 -178.5(4) . . . 3_666 ? C15 C14 C16 C18 -2.4(6) . . . 3_666 ? C18 C16 C17 O1 179.5(3) 3_666 . . . ? C14 C16 C17 O1 1.3(4) . . . . ? C18 C16 C17 C18 0.1(6) 3_666 . . . ? C14 C16 C17 C18 -178.1(3) . . . . ? O1 C17 C18 C16 -179.4(3) . . . 3_666 ? C16 C17 C18 C16 -0.1(6) . . . 3_666 ? O1 C17 C18 C19 0.1(5) . . . . ? C16 C17 C18 C19 179.4(3) . . . . ? C17 C18 C19 C20 7(4) . . . . ? C16 C18 C19 C20 -173(3) 3_666 . . . ? C18 C19 C20 C21 -43(12) . . . . ? C19 C20 C21 C26 7(10) . . . . ? C19 C20 C21 C22 -173(9) . . . . ? C26 C21 C22 C34 -177.8(4) . . . . ? C20 C21 C22 C34 1.5(6) . . . . ? C26 C21 C22 C23 1.2(6) . . . . ? C20 C21 C22 C23 -179.5(3) . . . . ? C34 C22 C23 C24 177.4(4) . . . . ? C21 C22 C23 C24 -1.7(6) . . . . ? C34 C22 C23 C31 -0.9(5) . . . . ? C21 C22 C23 C31 -180.0(3) . . . . ? C22 C23 C24 C25 0.9(6) . . . . ? C31 C23 C24 C25 179.0(4) . . . . ? C23 C24 C25 C26 0.5(6) . . . . ? C23 C24 C25 C30 -177.9(4) . . . . ? C22 C21 C26 C25 0.1(6) . . . . ? C20 C21 C26 C25 -179.2(4) . . . . ? C22 C21 C26 C27 178.8(4) . . . . ? C20 C21 C26 C27 -0.5(6) . . . . ? C24 C25 C26 C21 -0.9(6) . . . . ? C30 C25 C26 C21 177.5(4) . . . . ? C24 C25 C26 C27 -179.7(4) . . . . ? C30 C25 C26 C27 -1.3(6) . . . . ? C21 C26 C27 C28 -178.0(4) . . . . ? C25 C26 C27 C28 0.8(6) . . . . ? C26 C27 C28 C29 0.2(6) . . . . ? C27 C28 C29 C30 -0.6(7) . . . . ? C28 C29 C30 C25 0.0(7) . . . . ? C24 C25 C30 C29 179.4(4) . . . . ? C26 C25 C30 C29 1.0(6) . . . . ? C24 C23 C31 C32 -176.8(4) . . . . ? C22 C23 C31 C32 1.4(6) . . . . ? C23 C31 C32 C33 -0.7(6) . . . . ? C31 C32 C33 C34 -0.7(6) . . . . ? C32 C33 C34 C22 1.3(6) . . . . ? C21 C22 C34 C33 178.6(4) . . . . ? C23 C22 C34 C33 -0.5(6) . . . . ? C18 C17 O1 C1 178.1(3) . . . . ? C16 C17 O1 C1 -1.3(4) . . . . ? N1 C1 O1 C17 178.8(3) . . . . ? C14 C1 O1 C17 0.8(4) . . . . ? C14 C1 N1 C2 -174.7(4) . . . . ? O1 C1 N1 C2 8.0(5) . . . . ? C14 C1 N1 C8 0.3(7) . . . . ? O1 C1 N1 C8 -177.0(3) . . . . ? C3 C2 N1 C1 -112.9(4) . . . . ? C3 C2 N1 C8 72.0(4) . . . . ? C9 C8 N1 C1 -92.9(4) . . . . ? C9 C8 N1 C2 82.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.315 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.036