# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ognjen Miljanic' _publ_contact_author_email miljanic@uh.edu loop_ _publ_author_name 'Jaebum Lim' K.Osowska J.Armitage B.Martin O.Miljanic data_k1215 _database_code_depnum_ccdc_archive 'CCDC 874198' #TrackingRef '- Compounds_1_6_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 N2 O10, 2 (C2 H3 N)' _chemical_formula_sum 'C40 H34 N4 O10' _chemical_formula_weight 730.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5375(11) _cell_length_b 8.5549(12) _cell_length_c 14.7035(21) _cell_angle_alpha 101.088(2) _cell_angle_beta 98.465(2) _cell_angle_gamma 92.660(2) _cell_volume 917.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1455 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 23.54 _exptl_crystal_description 'thin plate' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6590 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'SAINT v7.12A' _publ_section_experimental ; All measurements were made with a Siemens SMART platform diffractometer equipped with a 4K CCD APEX II detector. A hemisphere of data (1271 frames at 6 cm detector distance) was collected using a narrow-frame algorithm with scan widths of 0.30\% in omega and an exposure time of 40 s/frame. The data were integrated using the Bruker-Nonius SAINT program, with the intensities corrected for Lorentz factor, polarization, air absorption, and absorption due to variation in the path length through the detector faceplate. A psi scan absorption correction was applied based on the entire data set. Redundant reflections were averaged. Final cell constants were refined using 1455 reflections having I>10\s(I), and these, along with other information pertinent to data collection and refinement, are listed in Table 1. The Laue symmetry was determined to be -1, and the space group was shown to be either P1 or P-1. The asymmetric unit consists of one-half molecule situated about an inversion center, and one molecule of acetonitrile solvent. The solvent molecule is disordered approximately 2/3:1/3 over two slightly different orientations, and this was treated by use of rigid body models with occupancies determined by comparison of the isotropic displacement parameters involved. ; _publ_section_figure_captions ; Fig. 1 -- View of the molecule showing the atom numbering scheme. Thermal ellipsoids are 40% equiprobability envelopes, with hydrogens as spheres of arbitrary diameter. Fig. 2 -- Isotropic view of the molecule. Fig. 3 -- Packing of the molecules in the unit cell. Only one orientation of the disordered solvent is shown at each site. ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 4K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 4097 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 23.54 _reflns_number_total 2699 _reflns_number_gt 1515 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'APEX2 v1.0-27 (Bruker-Nonius, 2005)' _computing_cell_refinement 'SAINT v7.12A (Bruker-Nonius, 2004)' _computing_data_reduction 'SAINT v7.12A (Bruker-Nonius, 2004)' _computing_structure_solution 'SHELXS v6.12 (G.M. Sheldrick, 2001)' _computing_structure_refinement 'SHELXL v6.12 (G.M. Sheldrick, 2001)' _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^ > 4sigma(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^)+(0.0610P)^2^+0.6643P] 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 none _refine_ls_number_reflns 2699 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.369 _refine_ls_shift/su_mean 0.017 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2909(3) 0.5905(2) 0.35639(16) 0.0486(6) Uani 1 1 d . . . O2 O 0.0974(4) 0.5476(3) 0.17789(19) 0.0727(8) Uani 1 1 d . . . O3 O 0.2252(4) 0.3178(3) 0.13967(19) 0.0714(8) Uani 1 1 d . . . O4 O 0.0459(3) 1.6548(2) 0.65005(17) 0.0529(7) Uani 1 1 d . . . O5 O 0.2504(3) 1.6591(2) 0.77700(18) 0.0543(6) Uani 1 1 d . . . N1 N 0.3861(3) 0.3450(3) 0.32006(18) 0.0351(6) Uani 1 1 d . . . C1 C 0.4364(4) 0.6623(3) 0.5232(2) 0.0366(8) Uani 1 1 d . . . C2 C 0.3937(4) 0.5606(3) 0.4358(2) 0.0363(7) Uani 1 1 d . . . C3 C 0.2940(4) 0.4560(4) 0.2915(2) 0.0460(8) Uani 1 1 d . . . C4 C 0.4529(4) 0.4074(3) 0.4131(2) 0.0374(8) Uani 1 1 d . . . C5 C 0.1946(4) 0.4493(4) 0.1973(3) 0.0504(9) Uani 1 1 d . . . C6 C 0.1361(7) 0.2941(6) 0.0428(3) 0.0869(14) Uani 1 1 d . . . H6A H 0.0175 0.3368 0.0407 0.104 Uiso 1 1 calc R . . H6B H 0.1191 0.1796 0.0151 0.104 Uiso 1 1 calc R . . C7 C 0.2470(8) 0.3764(7) -0.0110(4) 0.126(2) Uani 1 1 d . . . H7A H 0.1876 0.3609 -0.0756 0.189 Uiso 1 1 calc R . . H7B H 0.3637 0.3328 -0.0093 0.189 Uiso 1 1 calc R . . H7C H 0.2626 0.4897 0.0165 0.189 Uiso 1 1 calc R . . C8 C 0.3781(4) 0.8184(3) 0.5471(2) 0.0413(8) Uani 1 1 d . . . C9 C 0.3328(4) 0.9502(4) 0.5708(2) 0.0411(8) Uani 1 1 d . . . C10 C 0.2844(4) 1.1095(3) 0.6029(2) 0.0391(8) Uani 1 1 d . . . C11 C 0.1669(4) 1.1833(3) 0.5453(2) 0.0406(8) Uani 1 1 d . . . H11 H 0.1162 1.1282 0.4847 0.049 Uiso 1 1 calc R . . C12 C 0.1249(4) 1.3368(3) 0.5771(2) 0.0409(8) Uani 1 1 d . . . H12 H 0.0446 1.3857 0.5381 0.049 Uiso 1 1 calc R . . C13 C 0.1995(4) 1.4207(3) 0.6660(2) 0.0364(8) Uani 1 1 d . . . C14 C 0.3143(4) 1.3463(3) 0.7241(2) 0.0408(8) Uani 1 1 d . . . H14 H 0.3639 1.4015 0.7849 0.049 Uiso 1 1 calc R . . C15 C 0.3559(4) 1.1925(3) 0.6932(2) 0.0421(8) Uani 1 1 d . . . H15 H 0.4330 1.1427 0.7332 0.051 Uiso 1 1 calc R . . C16 C 0.1538(4) 1.5893(4) 0.6951(3) 0.0427(8) Uani 1 1 d . . . C17 C 0.2267(5) 1.8280(4) 0.8089(3) 0.0635(11) Uani 1 1 d . . . H17A H 0.2417 1.8868 0.7592 0.076 Uiso 1 1 calc R . . H17B H 0.1058 1.8412 0.8247 0.076 Uiso 1 1 calc R . . C18 C 0.3614(6) 1.8889(5) 0.8913(3) 0.0895(14) Uani 1 1 d . . . H18A H 0.3490 2.0016 0.9135 0.134 Uiso 1 1 calc R . . H18B H 0.4806 1.8748 0.8750 0.134 Uiso 1 1 calc R . . H18C H 0.3444 1.8310 0.9403 0.134 Uiso 1 1 calc R . . C19 C 0.1614(12) 0.9526(10) 0.2929(4) 0.059(3) Uiso 0.65 1 d PG A 1 H19A H 0.2793 0.9700 0.3299 0.071 Uiso 0.65 1 d PG A 1 H19B H 0.0943 1.0435 0.3100 0.071 Uiso 0.65 1 d PG A 1 H19C H 0.1003 0.8590 0.3043 0.071 Uiso 0.65 1 d PG A 1 C20 C 0.1763(6) 0.9311(5) 0.1968(4) 0.0612(18) Uiso 0.65 1 d PG A 1 N2 N 0.1893(8) 0.9148(7) 0.1195(4) 0.098(2) Uiso 0.65 1 d PG A 1 C21 C 0.135(3) 0.929(2) 0.2779(9) 0.079(7) Uiso 0.35 1 d PG B 2 H21A H 0.0061 0.9160 0.2635 0.094 Uiso 0.35 1 d PG B 2 H21B H 0.1769 0.8576 0.3179 0.094 Uiso 0.35 1 d PG B 2 H21C H 0.1720 1.0372 0.3094 0.094 Uiso 0.35 1 d PG B 2 C22 C 0.2103(14) 0.8936(11) 0.1918(7) 0.085(5) Uiso 0.35 1 d PG B 2 N3 N 0.2622(15) 0.8628(13) 0.1217(8) 0.095(4) Uiso 0.35 1 d PG B 2 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 0.0460(13) 0.0446(13) 0.0590(16) 0.0126(12) 0.0161(12) 0.0086(10) O2 0.0813(18) 0.0681(17) 0.070(2) 0.0139(15) 0.0074(15) 0.0291(15) O3 0.0818(18) 0.0703(18) 0.0570(18) 0.0014(14) 0.0035(15) 0.0265(15) O4 0.0552(14) 0.0358(13) 0.0693(17) 0.0097(12) 0.0126(13) 0.0162(11) O5 0.0581(14) 0.0346(13) 0.0654(18) -0.0042(12) 0.0113(14) 0.0108(11) N1 0.0352(13) 0.0300(13) 0.0427(17) 0.0061(12) 0.0151(13) 0.0058(11) C1 0.0374(16) 0.0257(16) 0.051(2) 0.0077(15) 0.0211(16) 0.0066(13) C2 0.0360(16) 0.0318(17) 0.047(2) 0.0118(16) 0.0172(16) 0.0078(13) C3 0.0418(18) 0.050(2) 0.047(2) 0.0065(18) 0.0153(17) 0.0007(16) C4 0.0375(16) 0.0316(17) 0.047(2) 0.0083(15) 0.0183(16) 0.0026(13) C5 0.048(2) 0.046(2) 0.060(3) 0.0112(19) 0.0163(19) 0.0100(17) C6 0.102(3) 0.095(3) 0.056(3) 0.001(3) 0.000(3) 0.026(3) C7 0.132(5) 0.172(6) 0.086(4) 0.048(4) 0.019(4) 0.043(4) C8 0.0426(17) 0.0305(18) 0.055(2) 0.0095(15) 0.0186(17) 0.0069(14) C9 0.0422(17) 0.0320(18) 0.052(2) 0.0086(15) 0.0177(16) 0.0057(14) C10 0.0436(17) 0.0266(16) 0.052(2) 0.0085(16) 0.0228(17) 0.0078(14) C11 0.0464(18) 0.0300(17) 0.046(2) 0.0045(15) 0.0126(16) 0.0053(14) C12 0.0424(17) 0.0338(17) 0.051(2) 0.0114(16) 0.0143(17) 0.0097(14) C13 0.0365(16) 0.0273(16) 0.048(2) 0.0065(15) 0.0174(16) 0.0046(13) C14 0.0425(17) 0.0348(17) 0.045(2) 0.0039(15) 0.0124(16) 0.0044(14) C15 0.0433(18) 0.0357(18) 0.051(2) 0.0130(17) 0.0115(17) 0.0121(14) C16 0.0423(18) 0.0321(17) 0.054(2) 0.0032(17) 0.0177(18) 0.0009(15) C17 0.071(2) 0.0339(19) 0.080(3) -0.0102(19) 0.019(2) 0.0108(18) C18 0.091(3) 0.058(3) 0.097(4) -0.026(3) 0.000(3) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.350(4) . ? O1 C2 1.377(4) . ? O2 C5 1.189(4) . ? O3 C5 1.324(4) . ? O3 C6 1.454(5) . ? O4 C16 1.200(4) . ? O5 C16 1.328(4) . ? O5 C17 1.458(4) . ? N1 C3 1.300(4) . ? N1 C4 1.379(4) . ? C1 C2 1.391(4) . ? C1 C4 1.399(4) 2_666 ? C1 C8 1.421(4) . ? C2 C4 1.399(4) . ? C3 C5 1.463(5) . ? C4 C1 1.399(4) 2_666 ? C6 C7 1.475(6) . ? C8 C9 1.195(4) . ? C9 C10 1.436(4) . ? C10 C11 1.392(4) . ? C10 C15 1.397(4) . ? C11 C12 1.375(4) . ? C12 C13 1.388(4) . ? C13 C14 1.388(4) . ? C13 C16 1.495(4) . ? C14 C15 1.374(4) . ? C17 C18 1.454(6) . ? C19 C20 1.4120 . ? C20 N2 1.1369 . ? C21 C22 1.4478 . ? C22 N3 1.1446 . ? 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 C3 O1 C2 103.8(2) . . ? C5 O3 C6 116.9(3) . . ? C16 O5 C17 115.9(3) . . ? C3 N1 C4 104.8(3) . . ? C2 C1 C4 111.6(2) . 2_666 ? C2 C1 C8 125.5(3) . . ? C4 C1 C8 122.9(3) 2_666 . ? O1 C2 C1 127.5(2) . . ? O1 C2 C4 107.6(3) . . ? C1 C2 C4 124.9(3) . . ? N1 C3 O1 115.7(3) . . ? N1 C3 C5 126.8(3) . . ? O1 C3 C5 117.5(3) . . ? N1 C4 C2 108.0(3) . . ? N1 C4 C1 128.4(3) . 2_666 ? C2 C4 C1 123.5(3) . 2_666 ? O2 C5 O3 126.1(4) . . ? O2 C5 C3 123.6(3) . . ? O3 C5 C3 110.3(3) . . ? O3 C6 C7 109.4(4) . . ? C9 C8 C1 177.4(4) . . ? C8 C9 C10 177.5(4) . . ? C11 C10 C15 119.1(3) . . ? C11 C10 C9 121.1(3) . . ? C15 C10 C9 119.8(3) . . ? C12 C11 C10 119.9(3) . . ? C11 C12 C13 120.9(3) . . ? C12 C13 C14 119.2(3) . . ? C12 C13 C16 118.3(3) . . ? C14 C13 C16 122.5(3) . . ? C15 C14 C13 120.3(3) . . ? C14 C15 C10 120.5(3) . . ? O4 C16 O5 124.0(3) . . ? O4 C16 C13 124.8(3) . . ? O5 C16 C13 111.2(3) . . ? C18 C17 O5 108.0(3) . . ? N2 C20 C19 179.4 . . ? N3 C22 C21 176.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 C1 178.9(3) . . . . ? C3 O1 C2 C4 -0.1(3) . . . . ? C4 C1 C2 O1 -178.8(2) 2_666 . . . ? C8 C1 C2 O1 0.9(5) . . . . ? C4 C1 C2 C4 0.0(4) 2_666 . . . ? C8 C1 C2 C4 179.7(3) . . . . ? C4 N1 C3 O1 0.1(3) . . . . ? C4 N1 C3 C5 -179.7(3) . . . . ? C2 O1 C3 N1 0.0(3) . . . . ? C2 O1 C3 C5 179.8(2) . . . . ? C3 N1 C4 C2 -0.1(3) . . . . ? C3 N1 C4 C1 -178.9(3) . . . 2_666 ? O1 C2 C4 N1 0.1(3) . . . . ? C1 C2 C4 N1 -178.9(2) . . . . ? O1 C2 C4 C1 179.0(2) . . . 2_666 ? C1 C2 C4 C1 0.0(5) . . . 2_666 ? C6 O3 C5 O2 2.1(5) . . . . ? C6 O3 C5 C3 -179.7(3) . . . . ? N1 C3 C5 O2 171.7(3) . . . . ? O1 C3 C5 O2 -8.1(5) . . . . ? N1 C3 C5 O3 -6.5(4) . . . . ? O1 C3 C5 O3 173.7(3) . . . . ? C5 O3 C6 C7 86.1(4) . . . . ? C15 C10 C11 C12 1.0(4) . . . . ? C9 C10 C11 C12 -178.9(3) . . . . ? C10 C11 C12 C13 0.6(4) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? C11 C12 C13 C16 177.7(3) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? C16 C13 C14 C15 -178.2(3) . . . . ? C13 C14 C15 C10 0.5(4) . . . . ? C11 C10 C15 C14 -1.6(4) . . . . ? C9 C10 C15 C14 178.4(3) . . . . ? C17 O5 C16 O4 -3.5(4) . . . . ? C17 O5 C16 C13 175.6(3) . . . . ? C12 C13 C16 O4 6.1(4) . . . . ? C14 C13 C16 O4 -174.5(3) . . . . ? C12 C13 C16 O5 -172.9(2) . . . . ? C14 C13 C16 O5 6.4(4) . . . . ? C16 O5 C17 C18 -171.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 23.54 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.327 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.044 #===END data_shelxl _database_code_depnum_ccdc_archive 'CCDC 874199' #TrackingRef '- Compounds_1_6_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H34 Cl4 N4 O4' _chemical_formula_weight 824.55 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' Cl Cl 0.1484 0.1585 '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 9.0410(18) _cell_length_b 10.560(2) _cell_length_c 11.850(2) _cell_angle_alpha 65.99(3) _cell_angle_beta 79.99(3) _cell_angle_gamma 88.69(3) _cell_volume 1016.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description Platelet _exptl_crystal_colour Red _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.695 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'ABSCOR (Higashi, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCX mini' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 6.849 _diffrn_standards_number 0 _diffrn_reflns_number 10511 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4619 _reflns_number_gt 1969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SCXmini (Rigaku, 2006)' _computing_cell_refinement 'Process-Auto (Rigaku, 2006)' _computing_data_reduction 'Process-Auto (Rigaku, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1326P)^2^+0.4427P] 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 4619 _refine_ls_number_parameters 251 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1831 _refine_ls_R_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.2945 _refine_ls_wR_factor_gt 0.2320 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0425(3) 0.1792(3) 0.1116(2) 0.0688(8) Uani 1 1 d . . . O2 O 0.4143(6) -0.0773(6) 0.7991(4) 0.1411(19) Uani 1 1 d . . . N1 N -0.1507(4) 0.2422(4) -0.0602(3) 0.0678(10) Uani 1 1 d . . . N2 N -0.3216(5) 0.7309(5) 0.1421(4) 0.0863(12) Uani 1 1 d . . . C2 C -0.2836(6) 0.7435(6) 0.2516(5) 0.1012(17) Uani 1 1 d . . . H2C H -0.3189 0.6608 0.3253 0.152 Uiso 1 1 calc R . . H2B H -0.3305 0.8221 0.2607 0.152 Uiso 1 1 calc R . . H2A H -0.1765 0.7559 0.2411 0.152 Uiso 1 1 calc R . . C3 C -0.4183(7) 0.8301(6) 0.0690(5) 0.1052(18) Uani 1 1 d . . . H3C H -0.3810 0.8562 -0.0188 0.158 Uiso 1 1 calc R . . H3B H -0.4197 0.9110 0.0870 0.158 Uiso 1 1 calc R . . H3A H -0.5185 0.7890 0.0904 0.158 Uiso 1 1 calc R . . C4 C -0.2746(5) 0.6192(5) 0.1155(4) 0.0726(12) Uani 1 1 d . . . C5 C -0.1817(5) 0.5197(5) 0.1877(4) 0.0744(13) Uani 1 1 d . . . H5 H -0.1521 0.5295 0.2552 0.089 Uiso 1 1 calc R . . C6 C -0.3181(5) 0.5967(6) 0.0166(4) 0.0797(13) Uani 1 1 d . . . H6 H -0.3804 0.6583 -0.0321 0.096 Uiso 1 1 calc R . . C7 C -0.1348(5) 0.4103(5) 0.1600(4) 0.0716(12) Uani 1 1 d . . . H7 H -0.0734 0.3478 0.2091 0.086 Uiso 1 1 calc R . . C8 C -0.2705(5) 0.4855(6) -0.0096(4) 0.0818(14) Uani 1 1 d . . . H8 H -0.3014 0.4737 -0.0757 0.098 Uiso 1 1 calc R . . C9 C -0.1757(5) 0.3890(5) 0.0611(4) 0.0659(11) Uani 1 1 d . . . C10 C -0.1263(5) 0.2729(5) 0.0318(4) 0.0682(12) Uani 1 1 d . . . C11 C -0.0811(4) 0.1193(5) -0.0427(4) 0.0651(11) Uani 1 1 d . . . C12 C -0.0122(5) 0.0791(5) 0.0643(4) 0.0664(11) Uani 1 1 d . . . C13 C 0.0686(5) -0.0375(5) 0.1128(4) 0.0639(11) Uani 1 1 d . . . C14 C 0.1341(5) -0.0672(5) 0.2222(4) 0.0688(11) Uani 1 1 d . . . C15 C 0.1853(5) -0.0815(5) 0.3127(4) 0.0694(12) Uani 1 1 d . . . C16 C 0.2479(5) -0.0983(5) 0.4216(4) 0.0628(11) Uani 1 1 d . . . C17 C 0.3511(6) -0.1972(5) 0.4646(5) 0.0811(13) Uani 1 1 d . . . H17 H 0.3791 -0.2555 0.4241 0.097 Uiso 1 1 calc R . . C18 C 0.2078(5) -0.0129(5) 0.4839(4) 0.0769(13) Uani 1 1 d . . . H18 H 0.1392 0.0549 0.4559 0.092 Uiso 1 1 calc R . . C19 C 0.4130(6) -0.2103(5) 0.5670(5) 0.0845(14) Uani 1 1 d . . . H19 H 0.4831 -0.2766 0.5943 0.101 Uiso 1 1 calc R . . C20 C 0.2692(5) -0.0278(5) 0.5871(4) 0.0796(13) Uani 1 1 d . . . H20 H 0.2407 0.0293 0.6289 0.096 Uiso 1 1 calc R . . C21 C 0.3720(5) -0.1263(5) 0.6288(4) 0.0738(13) Uani 1 1 d . . . C22 C 0.4402(7) -0.1429(6) 0.7376(5) 0.0996(18) Uani 1 1 d . . . H22 H 0.5098 -0.2108 0.7603 0.120 Uiso 1 1 calc R . . Cl1A Cl 0.3672(2) 0.5273(2) 0.3201(3) 0.1045(12) Uiso 0.766(10) 1 d PD A 1 C1A C 0.1717(7) 0.5204(7) 0.3417(10) 0.116(4) Uiso 0.766(10) 1 d PD A 1 H1A1 H 0.1347 0.5885 0.3738 0.139 Uiso 0.766(10) 1 calc PR A 1 H1A2 H 0.1419 0.5463 0.2607 0.139 Uiso 0.766(10) 1 calc PR A 1 Cl2A Cl 0.0865(3) 0.3596(3) 0.4432(3) 0.1125(11) Uiso 0.766(10) 1 d PD A 1 Cl1B Cl 0.3701(14) 0.5133(15) 0.395(2) 0.210(7) Uiso 0.234(10) 1 d PD A 2 C1B C 0.1852(16) 0.5281(14) 0.370(2) 0.063(6) Uiso 0.234(10) 1 d PD A 2 H1B1 H 0.1831 0.5916 0.2834 0.075 Uiso 0.234(10) 1 calc PR A 2 H1B2 H 0.1266 0.5656 0.4245 0.075 Uiso 0.234(10) 1 calc PR A 2 Cl2B Cl 0.1053(19) 0.3647(17) 0.399(2) 0.212(8) Uiso 0.234(10) 1 d PD A 2 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 0.0676(18) 0.087(2) 0.0541(16) -0.0295(15) -0.0143(14) -0.0047(15) O2 0.160(4) 0.182(5) 0.083(3) -0.050(3) -0.027(3) -0.061(4) N1 0.064(2) 0.087(3) 0.0507(19) -0.0254(18) -0.0106(16) -0.0093(19) N2 0.093(3) 0.092(3) 0.082(3) -0.041(2) -0.026(2) 0.005(2) C2 0.099(4) 0.119(5) 0.104(4) -0.062(4) -0.023(3) 0.006(3) C3 0.121(5) 0.097(4) 0.100(4) -0.037(3) -0.033(4) 0.006(3) C4 0.067(3) 0.082(3) 0.063(3) -0.025(2) -0.006(2) -0.015(2) C5 0.068(3) 0.094(3) 0.062(3) -0.031(3) -0.014(2) -0.013(3) C6 0.081(3) 0.091(3) 0.071(3) -0.032(3) -0.029(2) 0.014(3) C7 0.064(3) 0.082(3) 0.065(3) -0.024(2) -0.015(2) -0.008(2) C8 0.075(3) 0.112(4) 0.061(3) -0.035(3) -0.021(2) -0.004(3) C9 0.060(2) 0.083(3) 0.054(2) -0.028(2) -0.008(2) -0.011(2) C10 0.060(3) 0.083(3) 0.055(2) -0.022(2) -0.005(2) -0.016(2) C11 0.057(2) 0.082(3) 0.050(2) -0.019(2) -0.0114(19) -0.008(2) C12 0.062(3) 0.086(3) 0.050(2) -0.026(2) -0.008(2) -0.014(2) C13 0.061(2) 0.084(3) 0.046(2) -0.024(2) -0.0124(19) -0.007(2) C14 0.068(3) 0.081(3) 0.056(2) -0.025(2) -0.014(2) -0.006(2) C15 0.072(3) 0.075(3) 0.059(3) -0.023(2) -0.016(2) -0.003(2) C16 0.063(2) 0.072(3) 0.054(2) -0.026(2) -0.010(2) -0.005(2) C17 0.095(3) 0.079(3) 0.080(3) -0.039(3) -0.027(3) 0.011(3) C18 0.071(3) 0.094(3) 0.077(3) -0.043(3) -0.021(2) 0.005(2) C19 0.090(3) 0.081(3) 0.080(3) -0.025(3) -0.033(3) 0.014(3) C20 0.078(3) 0.099(4) 0.075(3) -0.050(3) -0.008(3) -0.006(3) C21 0.073(3) 0.082(3) 0.054(2) -0.014(2) -0.014(2) -0.013(3) C22 0.116(4) 0.115(4) 0.059(3) -0.022(3) -0.024(3) -0.034(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.379(5) . ? O1 C12 1.387(5) . ? O2 C22 1.187(7) . ? N1 C10 1.310(5) . ? N1 C11 1.383(6) . ? N2 C4 1.380(6) . ? N2 C3 1.448(7) . ? N2 C2 1.455(6) . ? C4 C6 1.405(6) . ? C4 C5 1.422(7) . ? C5 C7 1.364(6) . ? C6 C8 1.373(7) . ? C7 C9 1.389(6) . ? C8 C9 1.411(7) . ? C9 C10 1.446(6) . ? C11 C13 1.413(6) 2 ? C11 C12 1.414(6) . ? C12 C13 1.382(6) . ? C13 C11 1.413(6) 2 ? C13 C14 1.434(6) . ? C14 C15 1.193(6) . ? C15 C16 1.443(6) . ? C16 C17 1.381(6) . ? C16 C18 1.388(6) . ? C17 C19 1.378(7) . ? C18 C20 1.380(6) . ? C19 C21 1.371(7) . ? C20 C21 1.374(7) . ? C21 C22 1.470(7) . ? Cl1A C1A 1.741(6) . ? C1A Cl2A 1.732(6) . ? Cl1B C1B 1.742(8) . ? C1B Cl2B 1.760(8) . ? 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 C10 O1 C12 104.8(3) . . ? C10 N1 C11 105.3(4) . . ? C4 N2 C3 121.2(4) . . ? C4 N2 C2 119.6(4) . . ? C3 N2 C2 119.0(4) . . ? N2 C4 C6 121.7(4) . . ? N2 C4 C5 121.8(4) . . ? C6 C4 C5 116.4(5) . . ? C7 C5 C4 121.4(4) . . ? C8 C6 C4 121.4(4) . . ? C5 C7 C9 122.3(4) . . ? C6 C8 C9 121.7(4) . . ? C7 C9 C8 116.8(5) . . ? C7 C9 C10 122.3(4) . . ? C8 C9 C10 120.9(4) . . ? N1 C10 O1 114.3(4) . . ? N1 C10 C9 129.2(4) . . ? O1 C10 C9 116.4(4) . . ? N1 C11 C13 131.0(4) . 2 ? N1 C11 C12 109.0(4) . . ? C13 C11 C12 119.9(4) 2 . ? C13 C12 O1 126.6(4) . . ? C13 C12 C11 126.8(4) . . ? O1 C12 C11 106.5(4) . . ? C12 C13 C11 113.2(4) . 2 ? C12 C13 C14 121.8(4) . . ? C11 C13 C14 125.0(4) 2 . ? C15 C14 C13 174.7(5) . . ? C14 C15 C16 179.7(5) . . ? C17 C16 C18 118.5(4) . . ? C17 C16 C15 121.1(4) . . ? C18 C16 C15 120.4(4) . . ? C19 C17 C16 120.7(5) . . ? C20 C18 C16 120.4(5) . . ? C21 C19 C17 120.6(5) . . ? C21 C20 C18 120.5(4) . . ? C19 C21 C20 119.3(4) . . ? C19 C21 C22 119.2(5) . . ? C20 C21 C22 121.4(5) . . ? O2 C22 C21 125.9(7) . . ? Cl2A C1A Cl1A 114.4(4) . . ? Cl1B C1B Cl2B 110.3(7) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.357 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.052 #===END data_uhouston01 _database_code_depnum_ccdc_archive 'CCDC 874200' #TrackingRef '- Compounds_1_6_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; uhouston01 ; _chemical_name_common uhouston01 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H34 N4 O6' _chemical_formula_weight 906.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4382(9) _cell_length_b 17.0249(19) _cell_length_c 20.224(2) _cell_angle_alpha 96.374(9) _cell_angle_beta 97.194(9) _cell_angle_gamma 94.166(8) _cell_volume 2515.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5922 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 67.14 _exptl_crystal_description blade _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 0.631 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9282 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 10 _space_group.centring_type primitive _space_group.IT_number 2 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.073 0.324 0.356 38 2 ' ' 2 0.072 0.676 0.644 38 2 ' ' 3 0.500 1.000 0.000 296 127 'unknown diffuse solvent' _platon_squeeze_details ; ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 28025 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 68.08 _reflns_number_total 8696 _reflns_number_gt 5516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2008 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.1114P)^2^+1.5467P] 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 8696 _refine_ls_number_parameters 633 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2316 _refine_ls_wR_factor_gt 0.2156 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.1564(5) 0.0160(2) 0.63524(16) 0.0329(7) Uani 1 1 d . A . C2 C 0.1190(5) 0.0896(2) 0.61344(16) 0.0314(7) Uani 1 1 d . . . C3 C 0.1464(5) 0.1077(2) 0.54967(16) 0.0329(7) Uani 1 1 d . A . C4 C 0.2127(5) 0.0576(2) 0.50031(16) 0.0321(7) Uani 1 1 d . . . C5 C 0.2500(5) -0.0146(2) 0.52239(17) 0.0333(8) Uani 1 1 d . A . C6 C 0.2226(5) -0.0340(2) 0.58647(17) 0.0326(7) Uani 1 1 d . . . C7 C 0.0416(5) 0.2065(2) 0.60432(19) 0.0391(8) Uani 1 1 d . . . C8 C -0.0214(5) 0.2846(2) 0.61652(17) 0.0332(7) Uani 1 1 d . A . C9 C -0.0795(5) 0.3093(2) 0.67735(18) 0.0413(9) Uani 1 1 d . . . H9 H -0.0767 0.2748 0.7113 0.050 Uiso 1 1 calc R A . C10 C -0.1408(6) 0.3825(2) 0.68909(19) 0.0457(9) Uani 1 1 d . A . H10 H -0.1821 0.3989 0.7306 0.055 Uiso 1 1 calc R . . C11 C -0.1418(5) 0.4331(2) 0.63895(18) 0.0396(8) Uani 1 1 d . . . C12 C -0.0841(5) 0.4089(2) 0.57774(18) 0.0385(8) Uani 1 1 d . A . H12 H -0.0863 0.4433 0.5438 0.046 Uiso 1 1 calc R . . C13 C -0.0239(5) 0.3347(2) 0.56678(17) 0.0341(8) Uani 1 1 d . . . H13 H 0.0160 0.3177 0.5251 0.041 Uiso 1 1 calc R A . C14 C -0.1974(6) 0.5123(3) 0.6531(2) 0.0482(10) Uani 1 1 d . A . C15 C 0.3226(5) -0.1322(2) 0.52992(19) 0.0380(8) Uani 1 1 d . . . C16 C 0.3903(5) -0.2091(2) 0.51668(17) 0.0339(8) Uani 1 1 d . A . C17 C 0.4520(5) -0.2289(2) 0.45469(17) 0.0367(8) Uani 1 1 d . . . H17 H 0.4431 -0.1930 0.4218 0.044 Uiso 1 1 calc R A . C18 C 0.5254(5) -0.2998(2) 0.44121(17) 0.0359(8) Uani 1 1 d . A . H18 H 0.5672 -0.3129 0.3992 0.043 Uiso 1 1 calc R . . C19 C 0.5382(5) -0.3521(2) 0.48929(17) 0.0358(8) Uani 1 1 d . . . C20 C 0.4729(5) -0.3340(2) 0.55136(18) 0.0400(8) Uani 1 1 d . A . H20 H 0.4792 -0.3704 0.5837 0.048 Uiso 1 1 calc R . . C21 C 0.3997(5) -0.2624(2) 0.56424(17) 0.0355(8) Uani 1 1 d . . . H21 H 0.3554 -0.2495 0.6058 0.043 Uiso 1 1 calc R A . C22 C 0.6238(5) -0.4244(2) 0.47584(19) 0.0405(9) Uani 1 1 d . A . C23 C 0.1285(5) -0.0052(2) 0.69970(16) 0.0333(8) Uani 1 1 d . . . C24 C 0.1032(5) -0.0294(2) 0.75101(18) 0.0397(8) Uani 1 1 d . A . C25 C 0.0660(5) -0.0617(2) 0.81103(16) 0.0353(8) Uani 1 1 d . . . C26 C -0.0166(6) -0.0205(2) 0.86014(19) 0.0449(9) Uani 1 1 d . A . H26 H -0.0445 0.0324 0.8557 0.054 Uiso 1 1 calc R . . C27 C -0.0589(6) -0.0548(3) 0.91520(18) 0.0468(10) Uani 1 1 d . . . H27 H -0.1189 -0.0259 0.9475 0.056 Uiso 1 1 calc R A . C28 C -0.0153(5) -0.1310(2) 0.92420(18) 0.0429(9) Uani 1 1 d . A . C29 C 0.0729(5) -0.1727(2) 0.87560(19) 0.0441(9) Uani 1 1 d . . . H29 H 0.1059 -0.2247 0.8811 0.053 Uiso 1 1 calc R A . C30 C 0.1116(5) -0.1383(2) 0.81985(19) 0.0416(9) Uani 1 1 d . A . H30 H 0.1702 -0.1670 0.7870 0.050 Uiso 1 1 calc R . . C31 C -0.0623(5) -0.1691(3) 0.97987(19) 0.0464(10) Uani 1 1 d . . . C32 C -0.1027(6) -0.2022(3) 1.02601(19) 0.0474(10) Uani 1 1 d . A . C33 C -0.1567(5) -0.2442(3) 1.07854(19) 0.0467(10) Uani 1 1 d . . . C34 C -0.2048(7) -0.2033(3) 1.1371(2) 0.0563(11) Uani 1 1 d . A . H34 H -0.1989 -0.1470 1.1423 0.068 Uiso 1 1 calc R . . C35 C -0.2604(7) -0.2443(3) 1.1869(2) 0.0601(12) Uani 1 1 d . . . H35 H -0.2949 -0.2160 1.2258 0.072 Uiso 1 1 calc R A . C36 C -0.2667(6) -0.3254(3) 1.18104(19) 0.0507(10) Uani 1 1 d . A . C37 C -0.2170(6) -0.3667(3) 1.12347(19) 0.0463(9) Uani 1 1 d . . . H37 H -0.2207 -0.4230 1.1193 0.056 Uiso 1 1 calc R A . C38 C -0.1633(6) -0.3275(3) 1.07318(19) 0.0488(10) Uani 1 1 d . A . H38 H -0.1302 -0.3564 1.0343 0.059 Uiso 1 1 calc R . . C39 C -0.3242(6) -0.3653(3) 1.23766(19) 0.0515(11) Uani 1 1 d . . . C40 C -0.3489(7) -0.4842(3) 1.2852(2) 0.0605(12) Uani 1 1 d . . . H40A H -0.4795 -0.4823 1.2899 0.073 Uiso 1 1 calc R A . H40B H -0.2762 -0.4588 1.3275 0.073 Uiso 1 1 calc R . . C41 C -0.3057(9) -0.5687(3) 1.2709(2) 0.0750(16) Uani 1 1 d . A . H41A H -0.3898 -0.5954 1.2325 0.113 Uiso 1 1 calc R . . H41B H -0.3185 -0.5962 1.3104 0.113 Uiso 1 1 calc R . . H41C H -0.1805 -0.5698 1.2606 0.113 Uiso 1 1 calc R . . C42 C 0.2407(5) 0.0800(2) 0.43660(17) 0.0355(8) Uani 1 1 d . A . C43 C 0.2637(5) 0.1030(2) 0.38474(18) 0.0371(8) Uani 1 1 d . . . C44 C 0.3003(5) 0.1351(2) 0.32448(16) 0.0364(8) Uani 1 1 d . A . C45 C 0.3864(5) 0.0916(2) 0.27627(18) 0.0392(8) Uani 1 1 d . . . H45 H 0.4128 0.0387 0.2816 0.047 Uiso 1 1 calc R A . C46 C 0.4325(5) 0.1253(2) 0.22151(18) 0.0382(8) Uani 1 1 d . A . H46 H 0.4893 0.0951 0.1890 0.046 Uiso 1 1 calc R . . C47 C 0.3974(5) 0.2032(2) 0.21271(16) 0.0353(8) Uani 1 1 d . . . C48 C 0.3109(5) 0.2458(2) 0.26055(18) 0.0403(8) Uani 1 1 d . A . H48 H 0.2856 0.2988 0.2552 0.048 Uiso 1 1 calc R . . C49 C 0.2614(5) 0.2126(2) 0.31540(17) 0.0375(8) Uani 1 1 d . . . H49 H 0.2008 0.2424 0.3470 0.045 Uiso 1 1 calc R A . C50 C 0.4561(5) 0.2392(2) 0.15768(18) 0.0378(8) Uani 1 1 d . A . C51 C 0.5080(5) 0.2718(2) 0.11299(18) 0.0386(8) Uani 1 1 d . . . C52 C 0.5683(5) 0.3092(2) 0.05840(18) 0.0376(8) Uani 1 1 d . A . C53 C 0.6073(6) 0.2641(2) 0.00127(19) 0.0454(9) Uani 1 1 d . . . H53 H 0.5960 0.2078 -0.0012 0.054 Uiso 1 1 calc R A . C54 C 0.6617(6) 0.2991(2) -0.05157(19) 0.0450(9) Uani 1 1 d . A . H54 H 0.6830 0.2672 -0.0910 0.054 Uiso 1 1 calc R . . C55 C 0.6857(5) 0.3815(2) -0.04732(17) 0.0408(9) Uani 1 1 d . . . C56 C 0.6522(5) 0.4277(2) 0.01014(18) 0.0426(9) Uani 1 1 d . A . H56 H 0.6699 0.4839 0.0134 0.051 Uiso 1 1 calc R . . C57 C 0.5932(5) 0.3919(2) 0.06262(18) 0.0417(9) Uani 1 1 d . . . H57 H 0.5694 0.4237 0.1017 0.050 Uiso 1 1 calc R A . C58 C 0.7406(6) 0.4172(3) -0.10677(19) 0.0470(10) Uani 1 1 d . A . C59 C 0.8489(6) 0.5315(3) -0.1501(2) 0.0510(10) Uani 1 1 d . A . H59A H 0.7445 0.5284 -0.1862 0.061 Uiso 1 1 calc R . . H59B H 0.9489 0.5048 -0.1686 0.061 Uiso 1 1 calc R . . C60 C 0.9095(6) 0.6151(3) -0.1247(2) 0.0560(11) Uani 1 1 d . . . H60A H 0.8119 0.6399 -0.1041 0.084 Uiso 1 1 calc R . . H60B H 0.9394 0.6435 -0.1620 0.084 Uiso 1 1 calc R . . H60C H 1.0175 0.6174 -0.0911 0.084 Uiso 1 1 calc R . . N1 N 0.0533(4) 0.15395(16) 0.64727(13) 0.0381(6) Uani 0.50 1 d P A 1 O1A O 0.0533(4) 0.15395(16) 0.64727(13) 0.0381(6) Uani 0.50 1 d P A 2 N2 N 0.3142(4) -0.07948(17) 0.48817(13) 0.0386(6) Uani 0.50 1 d P A 1 O2A O 0.3142(4) -0.07948(17) 0.48817(13) 0.0386(6) Uani 0.50 1 d P A 2 N3 N -0.2401(6) 0.5747(2) 0.6641(2) 0.0652(11) Uani 1 1 d . . . N4 N 0.6962(5) -0.4798(2) 0.46346(18) 0.0482(8) Uani 1 1 d . . . O1 O 0.0942(3) 0.18264(14) 0.54433(12) 0.0298(5) Uani 0.50 1 d P A 1 N1A N 0.0942(3) 0.18264(14) 0.54433(12) 0.0298(5) Uani 0.50 1 d P A 2 O2 O 0.2684(4) -0.10942(15) 0.59024(12) 0.0334(6) Uani 0.50 1 d P A 1 N2A N 0.2684(4) -0.10942(15) 0.59024(12) 0.0334(6) Uani 0.50 1 d P A 2 O3 O -0.3818(5) -0.3318(2) 1.28510(14) 0.0621(9) Uani 1 1 d . A . O4 O -0.3055(4) -0.44354(19) 1.22986(13) 0.0557(8) Uani 1 1 d . A . O5 O 0.7395(5) 0.3788(2) -0.16134(14) 0.0630(9) Uani 1 1 d . . . O6 O 0.7955(4) 0.49364(17) -0.09322(13) 0.0493(7) 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 0.0376(19) 0.0353(18) 0.0274(16) 0.0078(13) 0.0083(13) 0.0005(15) C2 0.0350(18) 0.0307(18) 0.0300(16) 0.0078(13) 0.0073(13) 0.0013(15) C3 0.0400(19) 0.0322(18) 0.0278(16) 0.0086(13) 0.0056(13) 0.0019(15) C4 0.0342(18) 0.0372(18) 0.0260(15) 0.0071(13) 0.0079(13) -0.0015(15) C5 0.0352(18) 0.0336(18) 0.0325(17) 0.0064(14) 0.0094(14) -0.0001(15) C6 0.0380(19) 0.0294(17) 0.0327(17) 0.0115(13) 0.0086(14) 0.0011(15) C7 0.0331(19) 0.037(2) 0.048(2) 0.0114(16) 0.0045(15) -0.0017(16) C8 0.0328(18) 0.0347(18) 0.0332(17) 0.0062(14) 0.0051(13) 0.0057(15) C9 0.048(2) 0.045(2) 0.0349(18) 0.0158(16) 0.0079(16) 0.0109(18) C10 0.049(2) 0.050(2) 0.040(2) 0.0024(17) 0.0153(17) 0.0089(19) C11 0.042(2) 0.038(2) 0.0400(19) 0.0056(15) 0.0072(15) 0.0087(17) C12 0.0338(19) 0.045(2) 0.0395(19) 0.0140(16) 0.0065(15) 0.0047(17) C13 0.0333(18) 0.0385(19) 0.0320(16) 0.0076(14) 0.0088(13) -0.0003(15) C14 0.056(3) 0.043(2) 0.048(2) 0.0081(18) 0.0135(18) 0.012(2) C15 0.0322(18) 0.0340(19) 0.047(2) 0.0064(15) 0.0030(15) -0.0019(15) C16 0.0335(18) 0.0296(18) 0.0374(18) 0.0025(14) 0.0038(14) -0.0017(15) C17 0.0392(19) 0.039(2) 0.0332(17) 0.0106(15) 0.0068(14) 0.0011(16) C18 0.0383(19) 0.0363(19) 0.0335(17) 0.0012(14) 0.0110(14) -0.0003(16) C19 0.0396(19) 0.0296(18) 0.0384(18) 0.0072(14) 0.0060(15) -0.0010(16) C20 0.051(2) 0.037(2) 0.0354(18) 0.0112(15) 0.0097(15) 0.0032(17) C21 0.043(2) 0.0350(19) 0.0289(16) 0.0032(14) 0.0076(14) 0.0056(16) C22 0.045(2) 0.034(2) 0.045(2) 0.0113(16) 0.0141(16) -0.0017(19) C23 0.0416(19) 0.0333(17) 0.0280(16) 0.0152(13) 0.0080(14) 0.0011(15) C24 0.043(2) 0.044(2) 0.0327(18) 0.0058(15) 0.0081(15) 0.0005(17) C25 0.0396(19) 0.0422(19) 0.0246(15) 0.0111(14) 0.0034(13) -0.0010(16) C26 0.055(2) 0.045(2) 0.0373(19) 0.0114(16) 0.0096(17) 0.0055(19) C27 0.057(2) 0.056(2) 0.0311(18) 0.0147(17) 0.0119(16) 0.005(2) C28 0.044(2) 0.053(2) 0.0343(18) 0.0191(17) 0.0044(15) -0.0014(18) C29 0.048(2) 0.048(2) 0.0404(19) 0.0176(17) 0.0109(16) 0.0015(18) C30 0.047(2) 0.043(2) 0.0382(19) 0.0124(16) 0.0120(16) 0.0033(18) C31 0.045(2) 0.061(3) 0.0346(19) 0.0167(18) 0.0051(16) -0.0035(19) C32 0.052(2) 0.058(3) 0.0344(19) 0.0159(18) 0.0097(17) 0.001(2) C33 0.043(2) 0.065(3) 0.0358(19) 0.0208(18) 0.0106(16) 0.002(2) C34 0.080(3) 0.051(2) 0.040(2) 0.0172(18) 0.010(2) -0.002(2) C35 0.081(3) 0.066(3) 0.036(2) 0.0062(19) 0.021(2) -0.001(3) C36 0.055(2) 0.067(3) 0.0318(19) 0.0222(18) 0.0051(17) -0.004(2) C37 0.049(2) 0.055(2) 0.0373(19) 0.0163(17) 0.0089(16) -0.0005(19) C38 0.050(2) 0.067(3) 0.0350(19) 0.0207(18) 0.0115(16) 0.010(2) C39 0.055(2) 0.066(3) 0.033(2) 0.0132(19) 0.0051(17) -0.012(2) C40 0.066(3) 0.076(3) 0.041(2) 0.025(2) 0.0113(19) -0.020(2) C41 0.104(4) 0.071(3) 0.049(3) 0.023(2) 0.007(3) -0.020(3) C42 0.0395(19) 0.0383(19) 0.0313(17) 0.0134(14) 0.0080(14) 0.0015(16) C43 0.0351(19) 0.041(2) 0.0353(18) 0.0088(15) 0.0067(14) -0.0036(16) C44 0.0380(19) 0.046(2) 0.0263(16) 0.0104(14) 0.0059(13) -0.0044(16) C45 0.048(2) 0.0357(19) 0.0366(18) 0.0126(15) 0.0083(15) 0.0023(17) C46 0.048(2) 0.0348(19) 0.0352(17) 0.0099(14) 0.0140(15) 0.0015(17) C47 0.043(2) 0.0386(19) 0.0253(15) 0.0067(13) 0.0080(14) 0.0018(16) C48 0.045(2) 0.039(2) 0.0402(19) 0.0139(15) 0.0099(16) 0.0080(17) C49 0.043(2) 0.044(2) 0.0278(16) 0.0071(14) 0.0103(14) 0.0032(17) C50 0.045(2) 0.0342(19) 0.0379(18) 0.0104(15) 0.0115(15) 0.0076(16) C51 0.041(2) 0.042(2) 0.0357(18) 0.0123(15) 0.0079(15) 0.0048(17) C52 0.0393(19) 0.042(2) 0.0357(18) 0.0183(15) 0.0069(14) 0.0062(16) C53 0.059(2) 0.042(2) 0.0391(19) 0.0135(16) 0.0166(17) 0.0063(19) C54 0.060(2) 0.043(2) 0.0364(19) 0.0106(16) 0.0134(17) 0.0085(19) C55 0.045(2) 0.050(2) 0.0296(17) 0.0117(15) 0.0067(15) 0.0015(18) C56 0.053(2) 0.039(2) 0.0402(19) 0.0193(16) 0.0101(17) 0.0078(18) C57 0.048(2) 0.048(2) 0.0338(18) 0.0101(16) 0.0125(16) 0.0120(18) C58 0.051(2) 0.058(3) 0.037(2) 0.0211(18) 0.0085(16) 0.007(2) C59 0.058(3) 0.059(3) 0.042(2) 0.0246(19) 0.0160(18) 0.004(2) C60 0.062(3) 0.058(3) 0.057(2) 0.028(2) 0.019(2) 0.010(2) N1 0.0422(15) 0.0387(15) 0.0359(14) 0.0111(12) 0.0088(11) 0.0046(13) O1A 0.0422(15) 0.0387(15) 0.0359(14) 0.0111(12) 0.0088(11) 0.0046(13) N2 0.0413(15) 0.0375(15) 0.0377(14) 0.0040(11) 0.0095(11) 0.0025(12) O2A 0.0413(15) 0.0375(15) 0.0377(14) 0.0040(11) 0.0095(11) 0.0025(12) N3 0.079(3) 0.044(2) 0.076(3) 0.0037(19) 0.016(2) 0.022(2) N4 0.058(2) 0.0348(19) 0.057(2) 0.0093(15) 0.0243(17) 0.0061(17) O1 0.0323(13) 0.0284(13) 0.0308(12) 0.0088(10) 0.0076(10) 0.0034(11) N1A 0.0323(13) 0.0284(13) 0.0308(12) 0.0088(10) 0.0076(10) 0.0034(11) O2 0.0370(14) 0.0301(13) 0.0351(13) 0.0100(10) 0.0070(11) 0.0036(11) N2A 0.0370(14) 0.0301(13) 0.0351(13) 0.0100(10) 0.0070(11) 0.0036(11) O3 0.073(2) 0.081(2) 0.0341(15) 0.0141(14) 0.0181(14) -0.0083(17) O4 0.0663(19) 0.070(2) 0.0322(13) 0.0220(13) 0.0091(12) -0.0104(16) O5 0.086(2) 0.070(2) 0.0357(15) 0.0167(14) 0.0191(14) -0.0047(18) O6 0.0664(18) 0.0499(16) 0.0380(14) 0.0226(12) 0.0157(12) 0.0048(14) _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 C6 1.391(5) . ? C1 C2 1.408(5) . ? C1 C23 1.426(4) . ? C2 N1 1.380(5) . ? C2 C3 1.395(4) . ? C3 O1 1.372(4) . ? C3 C4 1.401(5) . ? C4 C5 1.388(5) . ? C4 C42 1.419(4) . ? C5 N2 1.385(5) . ? C5 C6 1.408(4) . ? C6 O2 1.360(4) . ? C7 N1 1.314(4) . ? C7 O1 1.350(4) . ? C7 C8 1.447(5) . ? C8 C9 1.386(5) . ? C8 C13 1.389(5) . ? C9 C10 1.365(6) . ? C9 H9 0.9500 . ? C10 C11 1.401(5) . ? C10 H10 0.9500 . ? C11 C12 1.390(5) . ? C11 C14 1.448(6) . ? C12 C13 1.375(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N3 1.137(6) . ? C15 N2 1.299(4) . ? C15 O2 1.357(5) . ? C15 C16 1.445(5) . ? C16 C21 1.393(5) . ? C16 C17 1.403(5) . ? C17 C18 1.375(5) . ? C17 H17 0.9500 . ? C18 C19 1.389(5) . ? C18 H18 0.9500 . ? C19 C20 1.413(5) . ? C19 C22 1.442(6) . ? C20 C21 1.383(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N4 1.138(5) . ? C23 C24 1.190(5) . ? C24 C25 1.436(5) . ? C25 C26 1.385(5) . ? C25 C30 1.395(5) . ? C26 C27 1.373(5) . ? C26 H26 0.9500 . ? C27 C28 1.387(6) . ? C27 H27 0.9500 . ? C28 C29 1.405(6) . ? C28 C31 1.428(5) . ? C29 C30 1.379(5) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.201(5) . ? C32 C33 1.426(5) . ? C33 C34 1.406(6) . ? C33 C38 1.406(6) . ? C34 C35 1.374(6) . ? C34 H34 0.9500 . ? C35 C36 1.370(6) . ? C35 H35 0.9500 . ? C36 C37 1.397(6) . ? C36 C39 1.486(5) . ? C37 C38 1.362(5) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 O3 1.203(5) . ? C39 O4 1.343(6) . ? C40 O4 1.438(4) . ? C40 C41 1.502(7) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.187(5) . ? C43 C44 1.438(5) . ? C44 C49 1.399(5) . ? C44 C45 1.405(5) . ? C45 C46 1.371(5) . ? C45 H45 0.9500 . ? C46 C47 1.396(5) . ? C46 H46 0.9500 . ? C47 C48 1.394(5) . ? C47 C50 1.428(5) . ? C48 C49 1.377(5) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.201(5) . ? C51 C52 1.436(5) . ? C52 C53 1.388(5) . ? C52 C57 1.400(5) . ? C53 C54 1.369(5) . ? C53 H53 0.9500 . ? C54 C55 1.393(5) . ? C54 H54 0.9500 . ? C55 C56 1.389(6) . ? C55 C58 1.494(5) . ? C56 C57 1.383(5) . ? C56 H56 0.9500 . ? C57 H57 0.9500 . ? C58 O5 1.217(5) . ? C58 O6 1.324(5) . ? C59 O6 1.463(4) . ? C59 C60 1.477(6) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? 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 C6 C1 C2 112.2(3) . . ? C6 C1 C23 123.8(3) . . ? C2 C1 C23 124.0(3) . . ? N1 C2 C3 108.5(3) . . ? N1 C2 C1 129.2(3) . . ? C3 C2 C1 122.2(3) . . ? O1 C3 C2 107.4(3) . . ? O1 C3 C4 126.8(3) . . ? C2 C3 C4 125.8(3) . . ? C5 C4 C3 111.5(3) . . ? C5 C4 C42 125.2(3) . . ? C3 C4 C42 123.3(3) . . ? N2 C5 C4 128.8(3) . . ? N2 C5 C6 107.8(3) . . ? C4 C5 C6 123.4(3) . . ? O2 C6 C1 127.7(3) . . ? O2 C6 C5 107.5(3) . . ? C1 C6 C5 124.8(3) . . ? N1 C7 O1 114.6(3) . . ? N1 C7 C8 125.7(3) . . ? O1 C7 C8 119.7(3) . . ? C9 C8 C13 120.0(3) . . ? C9 C8 C7 120.4(3) . . ? C13 C8 C7 119.6(3) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.0(3) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C12 C11 C10 120.7(4) . . ? C12 C11 C14 120.6(3) . . ? C10 C11 C14 118.7(3) . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C8 120.1(3) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? N3 C14 C11 179.6(5) . . ? N2 C15 O2 115.0(3) . . ? N2 C15 C16 124.6(3) . . ? O2 C15 C16 120.4(3) . . ? C21 C16 C17 119.8(3) . . ? C21 C16 C15 121.7(3) . . ? C17 C16 C15 118.4(3) . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.7(3) . . ? C18 C19 C22 119.1(3) . . ? C20 C19 C22 120.2(3) . . ? C21 C20 C19 118.9(3) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C20 C21 C16 120.5(3) . . ? C20 C21 H21 119.8 . . ? C16 C21 H21 119.8 . . ? N4 C22 C19 176.8(4) . . ? C24 C23 C1 174.4(4) . . ? C23 C24 C25 177.1(4) . . ? C26 C25 C30 118.4(3) . . ? C26 C25 C24 122.7(3) . . ? C30 C25 C24 118.9(3) . . ? C27 C26 C25 121.1(4) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 120.9(4) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C29 118.5(3) . . ? C27 C28 C31 122.1(4) . . ? C29 C28 C31 119.3(4) . . ? C30 C29 C28 120.1(4) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C25 120.9(4) . . ? C29 C30 H30 119.5 . . ? C25 C30 H30 119.5 . . ? C32 C31 C28 178.9(5) . . ? C31 C32 C33 177.2(5) . . ? C34 C33 C38 118.2(3) . . ? C34 C33 C32 120.7(4) . . ? C38 C33 C32 121.0(4) . . ? C35 C34 C33 120.4(4) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C36 C35 C34 120.9(4) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C35 C36 C37 119.3(4) . . ? C35 C36 C39 117.7(4) . . ? C37 C36 C39 123.0(4) . . ? C38 C37 C36 120.9(4) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C33 120.3(4) . . ? C37 C38 H38 119.9 . . ? C33 C38 H38 119.9 . . ? O3 C39 O4 123.5(4) . . ? O3 C39 C36 124.1(4) . . ? O4 C39 C36 112.4(4) . . ? O4 C40 C41 107.6(4) . . ? O4 C40 H40A 110.2 . . ? C41 C40 H40A 110.2 . . ? O4 C40 H40B 110.2 . . ? C41 C40 H40B 110.2 . . ? H40A C40 H40B 108.5 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C4 176.3(4) . . ? C42 C43 C44 176.1(4) . . ? C49 C44 C45 119.0(3) . . ? C49 C44 C43 119.9(3) . . ? C45 C44 C43 120.9(3) . . ? C46 C45 C44 120.2(3) . . ? C46 C45 H45 119.9 . . ? C44 C45 H45 119.9 . . ? C45 C46 C47 121.2(3) . . ? C45 C46 H46 119.4 . . ? C47 C46 H46 119.4 . . ? C48 C47 C46 118.3(3) . . ? C48 C47 C50 121.0(3) . . ? C46 C47 C50 120.7(3) . . ? C49 C48 C47 121.4(3) . . ? C49 C48 H48 119.3 . . ? C47 C48 H48 119.3 . . ? C48 C49 C44 119.9(3) . . ? C48 C49 H49 120.0 . . ? C44 C49 H49 120.0 . . ? C51 C50 C47 177.7(4) . . ? C50 C51 C52 178.6(4) . . ? C53 C52 C57 118.7(3) . . ? C53 C52 C51 120.8(3) . . ? C57 C52 C51 120.4(3) . . ? C54 C53 C52 121.3(4) . . ? C54 C53 H53 119.4 . . ? C52 C53 H53 119.4 . . ? C53 C54 C55 119.8(4) . . ? C53 C54 H54 120.1 . . ? C55 C54 H54 120.1 . . ? C56 C55 C54 119.9(3) . . ? C56 C55 C58 122.1(4) . . ? C54 C55 C58 118.0(3) . . ? C57 C56 C55 120.0(4) . . ? C57 C56 H56 120.0 . . ? C55 C56 H56 120.0 . . ? C56 C57 C52 120.3(3) . . ? C56 C57 H57 119.9 . . ? C52 C57 H57 119.9 . . ? O5 C58 O6 124.0(3) . . ? O5 C58 C55 122.9(4) . . ? O6 C58 C55 113.1(3) . . ? O6 C59 C60 106.9(3) . . ? O6 C59 H59A 110.3 . . ? C60 C59 H59A 110.3 . . ? O6 C59 H59B 110.3 . . ? C60 C59 H59B 110.3 . . ? H59A C59 H59B 108.6 . . ? C59 C60 H60A 109.5 . . ? C59 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C59 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C7 N1 C2 104.7(3) . . ? C15 N2 C5 105.0(3) . . ? C7 O1 C3 104.8(3) . . ? C15 O2 C6 104.7(3) . . ? C39 O4 C40 114.6(3) . . ? C58 O6 C59 115.1(3) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.321 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.061