# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global #TrackingRef '- CC-COM-06-2010-001687.cif' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Zhanxian Li' ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; 'Mingming Yu' ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; 'Lifeng Zhang' ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; 'Ming Yu' ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; 'Jinxia Liu' ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; ; Liuhe Wei ; ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; 'Hongyan Zhang' ; Key Laboratory of Photochemical Conversion and Optoelectronic Materials Technical Institute of Physics and Chemistry Chinese Academy of Sciences Beijing China ; _publ_contact_author_name 'Mingming Yu' _publ_contact_author_email yumm@zzu.edu.cn _publ_section_title ; A "switching on" fluorescent chemodosimeter of selectivity to Zn2+ and its application to MCF-4 cells ; loop_ _publ_contact_author_address ; Department of Chemistry Zhengzhou University Zhengzhou 450001 China ; loop_ _publ_contact_author_fax '+86 371 67781205' loop_ _publ_contact_author_phone '+86 371 67781205' data_compound _database_code_depnum_ccdc_archive 'CCDC 783331' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;(E)-2-(4-Hydroxyphenylimino)-4-methyl-7-acetamidyl-1,8- naphthyridine ; _chemical_melting_point ? _chemical_formula_moiety '2(C18 H15 N4 O2), H2 O' _chemical_formula_sum 'C36 H32 N8 O5' _chemical_formula_weight 656.70 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 orthorhombic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5496(15) _cell_length_b 13.657(3) _cell_length_c 30.427(6) _cell_angle_alpha 90.00(3) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 3137.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11967 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.82 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32427 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 14403 _reflns_number_gt 8981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+1.9333P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13839 _refine_ls_number_parameters 912 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.2247 _refine_ls_wR_factor_gt 0.1995 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _refine_ls_shift/su_max 0.093 _refine_ls_shift/su_mean 0.001 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 O1W O 0.1997(4) 0.9999(2) 0.24999(10) 0.0460(7) Uani 1 1 d D . . O2W O 0.6997(4) 0.5003(2) 0.25003(10) 0.0451(7) Uani 1 1 d D . . N7 N 0.3313(4) 0.7863(2) 0.08932(9) 0.0281(6) Uani 1 1 d . . . N6 N 0.1919(4) 0.7871(2) 0.15632(9) 0.0291(6) Uani 1 1 d . . . N5 N 0.0495(4) 0.8022(2) 0.22231(10) 0.0346(7) Uani 1 1 d . . . O4 O 0.7508(3) 1.00208(17) -0.15389(8) 0.0368(6) Uani 1 1 d . . . H4 H 0.7628 1.0592 -0.1461 0.055 Uiso 1 1 calc R . . C30 C 0.4654(5) 0.7991(2) 0.01963(11) 0.0309(7) Uani 1 1 d . . . H30 H 0.4626 0.8668 0.0227 0.037 Uiso 1 1 calc R . . C24 C 0.2535(4) 0.6291(2) 0.12194(11) 0.0272(7) Uani 1 1 d . . . C26 C 0.3286(4) 0.5782(2) 0.08551(11) 0.0274(7) Uani 1 1 d . . . N8 N 0.5275(4) 0.7623(2) -0.01579(9) 0.0306(6) Uani 1 1 d . . . C23 C 0.1700(4) 0.5832(2) 0.15764(11) 0.0307(7) Uani 1 1 d . . . H23 H 0.1621 0.5152 0.1584 0.037 Uiso 1 1 calc R . . C25 C 0.2598(4) 0.7329(2) 0.12283(11) 0.0279(7) Uani 1 1 d . . . C22 C 0.1006(5) 0.6365(2) 0.19105(11) 0.0327(8) Uani 1 1 d . . . H22 H 0.0448 0.6059 0.2146 0.039 Uiso 1 1 calc R . . C28 C 0.3977(4) 0.7374(2) 0.05594(11) 0.0285(7) Uani 1 1 d . . . C27 C 0.4014(4) 0.6343(2) 0.05321(11) 0.0286(7) Uani 1 1 d . . . H27 H 0.4542 0.6043 0.0291 0.034 Uiso 1 1 calc R . . C21 C 0.1151(4) 0.7400(2) 0.18930(11) 0.0302(7) Uani 1 1 d . . . C31 C 0.5870(4) 0.8263(2) -0.04944(11) 0.0279(7) Uani 1 1 d . . . O3 O -0.0801(4) 0.6912(2) 0.26847(9) 0.0532(8) Uani 1 1 d . . . C34 C 0.6974(5) 0.9463(2) -0.11850(11) 0.0313(8) Uani 1 1 d . . . C35 C 0.7131(4) 0.9784(2) -0.07575(11) 0.0287(7) Uani 1 1 d . . . H35 H 0.7609 1.0399 -0.0701 0.034 Uiso 1 1 calc R . . C32 C 0.5764(5) 0.7950(3) -0.09244(11) 0.0354(8) Uani 1 1 d . . . H32 H 0.5329 0.7326 -0.0984 0.042 Uiso 1 1 calc R . . C36 C 0.6582(4) 0.9198(2) -0.04119(11) 0.0310(7) Uani 1 1 d . . . H36 H 0.6683 0.9423 -0.0124 0.037 Uiso 1 1 calc R . . C20 C -0.0397(5) 0.7751(3) 0.25945(12) 0.0378(9) Uani 1 1 d . . . C29 C 0.3251(5) 0.4688(2) 0.08318(12) 0.0343(8) Uani 1 1 d . . . H29A H 0.3840 0.4475 0.0569 0.051 Uiso 1 1 calc R . . H29B H 0.2045 0.4465 0.0828 0.051 Uiso 1 1 calc R . . H29C H 0.3846 0.4421 0.1084 0.051 Uiso 1 1 calc R . . C33 C 0.6287(5) 0.8540(2) -0.12694(12) 0.0354(8) Uani 1 1 d . . . H33 H 0.6179 0.8319 -0.1557 0.043 Uiso 1 1 calc R . . C19 C -0.0900(6) 0.8584(3) 0.28966(13) 0.0483(10) Uani 1 1 d . . . H19A H -0.1943 0.8410 0.3059 0.072 Uiso 1 1 calc R . . H19B H -0.1131 0.9161 0.2725 0.072 Uiso 1 1 calc R . . H19C H 0.0055 0.8710 0.3097 0.072 Uiso 1 1 calc R . . N14 N 0.1918(4) 0.2130(2) 0.34374(9) 0.0290(6) Uani 1 1 d . . . N15 N 0.3312(4) 0.2136(2) 0.41060(9) 0.0280(6) Uani 1 1 d . . . O8 O 0.7509(3) -0.00192(17) 0.65386(8) 0.0364(6) Uani 1 1 d . . . H8 H 0.7688 -0.0583 0.6458 0.055 Uiso 1 1 calc R . . N13 N 0.0497(4) 0.1980(2) 0.27755(10) 0.0345(7) Uani 1 1 d . . . C66 C 0.4654(4) 0.2007(2) 0.48055(11) 0.0308(7) Uani 1 1 d . . . H66 H 0.4633 0.1330 0.4776 0.037 Uiso 1 1 calc R . . N16 N 0.5268(4) 0.2380(2) 0.51599(9) 0.0306(6) Uani 1 1 d . . . C62 C 0.3288(4) 0.4216(2) 0.41457(11) 0.0281(7) Uani 1 1 d . . . C60 C 0.2537(4) 0.3711(2) 0.37796(11) 0.0267(7) Uani 1 1 d . . . C58 C 0.1008(5) 0.3633(2) 0.30925(12) 0.0326(8) Uani 1 1 d . . . H58 H 0.0443 0.3938 0.2858 0.039 Uiso 1 1 calc R . . C63 C 0.4021(4) 0.3659(2) 0.44713(11) 0.0283(7) Uani 1 1 d . . . H63 H 0.4550 0.3960 0.4712 0.034 Uiso 1 1 calc R . . C59 C 0.1700(5) 0.4170(2) 0.34233(11) 0.0310(7) Uani 1 1 d . . . H59 H 0.1621 0.4849 0.3415 0.037 Uiso 1 1 calc R . . C67 C 0.5872(4) 0.1735(2) 0.54936(11) 0.0281(7) Uani 1 1 d . . . C61 C 0.2599(4) 0.2676(2) 0.37726(11) 0.0271(7) Uani 1 1 d . . . C64 C 0.3978(4) 0.2619(2) 0.44431(11) 0.0291(7) Uani 1 1 d . . . C57 C 0.1154(4) 0.2597(2) 0.31077(11) 0.0299(7) Uani 1 1 d . . . O7 O -0.0799(4) 0.3091(2) 0.23158(9) 0.0539(8) Uani 1 1 d . . . C69 C 0.7139(5) 0.0212(2) 0.57547(11) 0.0303(7) Uani 1 1 d . . . H69 H 0.7620 -0.0401 0.5696 0.036 Uiso 1 1 calc R . . C70 C 0.6977(5) 0.0536(2) 0.61864(11) 0.0319(8) Uani 1 1 d . . . C68 C 0.6582(4) 0.0807(2) 0.54134(11) 0.0299(7) Uani 1 1 d . . . H68 H 0.6681 0.0585 0.5125 0.036 Uiso 1 1 calc R . . C72 C 0.5765(5) 0.2050(2) 0.59244(11) 0.0341(8) Uani 1 1 d . . . H72 H 0.5330 0.2674 0.5983 0.041 Uiso 1 1 calc R . . C56 C -0.0401(5) 0.2248(3) 0.24039(12) 0.0377(9) Uani 1 1 d . . . C71 C 0.6288(5) 0.1460(2) 0.62699(12) 0.0369(8) Uani 1 1 d . . . H71 H 0.6178 0.1682 0.6558 0.044 Uiso 1 1 calc R . . C65 C 0.3259(5) 0.5310(2) 0.41677(12) 0.0352(8) Uani 1 1 d . . . H65A H 0.3829 0.5523 0.4433 0.053 Uiso 1 1 calc R . . H65B H 0.2054 0.5535 0.4166 0.053 Uiso 1 1 calc R . . H65C H 0.3875 0.5575 0.3918 0.053 Uiso 1 1 calc R . . N11 N 0.8313(4) 0.2865(2) 0.41064(9) 0.0290(6) Uani 1 1 d . . . N10 N 0.6915(4) 0.2870(2) 0.34377(9) 0.0290(6) Uani 1 1 d . . . O6 O 1.2506(3) 0.50214(17) 0.65390(8) 0.0360(6) Uani 1 1 d . . . H6 H 1.2658 0.5589 0.6460 0.054 Uiso 1 1 calc R . . N9 N 0.5497(4) 0.3018(2) 0.27775(10) 0.0351(7) Uani 1 1 d . . . C48 C 0.9650(4) 0.2993(2) 0.48039(11) 0.0303(7) Uani 1 1 d . . . H48 H 0.9621 0.3670 0.4773 0.036 Uiso 1 1 calc R . . N12 N 1.0271(4) 0.2622(2) 0.51594(9) 0.0303(6) Uani 1 1 d . . . C41 C 0.6695(5) 0.0830(2) 0.34239(11) 0.0304(7) Uani 1 1 d . . . H41 H 0.6611 0.0150 0.3417 0.037 Uiso 1 1 calc R . . C42 C 0.7538(4) 0.1292(2) 0.37808(11) 0.0278(7) Uani 1 1 d . . . C45 C 0.9017(4) 0.1344(2) 0.44713(11) 0.0286(7) Uani 1 1 d . . . H45 H 0.9539 0.1043 0.4713 0.034 Uiso 1 1 calc R . . C49 C 1.0867(4) 0.3263(2) 0.54935(11) 0.0282(7) Uani 1 1 d . . . C52 C 1.1977(5) 0.4466(2) 0.61858(11) 0.0305(7) Uani 1 1 d . . . O5 O 0.4199(4) 0.1908(2) 0.23174(9) 0.0535(8) Uani 1 1 d . . . C43 C 0.7594(4) 0.2326(2) 0.37739(11) 0.0273(7) Uani 1 1 d . . . C44 C 0.8288(4) 0.0783(2) 0.41444(11) 0.0296(7) Uani 1 1 d . . . C40 C 0.6007(5) 0.1363(3) 0.30907(12) 0.0334(8) Uani 1 1 d . . . H40 H 0.5448 0.1059 0.2855 0.040 Uiso 1 1 calc R . . C39 C 0.6156(4) 0.2399(2) 0.31084(11) 0.0298(7) Uani 1 1 d . . . C46 C 0.8980(4) 0.2375(2) 0.44426(11) 0.0284(7) Uani 1 1 d . . . C54 C 1.1581(5) 0.4195(2) 0.54126(11) 0.0320(8) Uani 1 1 d . . . H54 H 1.1683 0.4419 0.5125 0.038 Uiso 1 1 calc R . . C50 C 1.0763(5) 0.2948(2) 0.59242(11) 0.0331(8) Uani 1 1 d . . . H50 H 1.0332 0.2324 0.5983 0.040 Uiso 1 1 calc R . . C53 C 1.2134(4) 0.4786(2) 0.57558(11) 0.0294(7) Uani 1 1 d . . . H53 H 1.2613 0.5399 0.5697 0.035 Uiso 1 1 calc R . . C38 C 0.4602(5) 0.2750(3) 0.24039(12) 0.0375(9) Uani 1 1 d . . . C51 C 1.1287(5) 0.3542(2) 0.62713(12) 0.0359(8) Uani 1 1 d . . . H51 H 1.1175 0.3323 0.6559 0.043 Uiso 1 1 calc R . . C47 C 0.8252(5) -0.0309(2) 0.41685(12) 0.0343(8) Uani 1 1 d . . . H47A H 0.8824 -0.0520 0.4434 0.051 Uiso 1 1 calc R . . H47B H 0.8863 -0.0577 0.3919 0.051 Uiso 1 1 calc R . . H47C H 0.7046 -0.0531 0.4168 0.051 Uiso 1 1 calc R . . C37 C 0.4096(6) 0.3585(3) 0.21054(13) 0.0471(10) Uani 1 1 d . . . H37A H 0.5040 0.3708 0.1901 0.071 Uiso 1 1 calc R . . H37B H 0.3885 0.4162 0.2278 0.071 Uiso 1 1 calc R . . H37C H 0.3040 0.3417 0.1947 0.071 Uiso 1 1 calc R . . N3 N 0.8317(4) 0.71381(19) 0.08948(9) 0.0283(6) Uani 1 1 d . . . N2 N 0.6917(4) 0.7130(2) 0.15624(9) 0.0296(6) Uani 1 1 d . . . O2 O 1.2506(3) 0.49809(17) -0.15383(8) 0.0366(6) Uani 1 1 d . . . H2 H 1.2626 0.4410 -0.1461 0.055 Uiso 1 1 calc R . . C12 C 0.9653(4) 0.7007(2) 0.01951(11) 0.0293(7) Uani 1 1 d . . . H12 H 0.9626 0.6330 0.0224 0.035 Uiso 1 1 calc R . . N1 N 0.5500(4) 0.6979(2) 0.22227(10) 0.0347(7) Uani 1 1 d . . . N4 N 1.0267(4) 0.7378(2) -0.01582(9) 0.0307(6) Uani 1 1 d . . . C6 C 0.7536(4) 0.8706(2) 0.12201(11) 0.0269(7) Uani 1 1 d . . . C9 C 0.9020(4) 0.8659(2) 0.05295(11) 0.0279(7) Uani 1 1 d . . . H9 H 0.9543 0.8961 0.0288 0.033 Uiso 1 1 calc R . . C5 C 0.6698(5) 0.9170(2) 0.15765(11) 0.0320(8) Uani 1 1 d . . . H5 H 0.6617 0.9849 0.1584 0.038 Uiso 1 1 calc R . . C8 C 0.8293(4) 0.9214(2) 0.08549(11) 0.0275(7) Uani 1 1 d . . . C4 C 0.6011(5) 0.8632(2) 0.19072(11) 0.0321(8) Uani 1 1 d . . . H4A H 0.5448 0.8937 0.2142 0.039 Uiso 1 1 calc R . . C13 C 1.0875(4) 0.6736(2) -0.04945(11) 0.0286(7) Uani 1 1 d . . . C16 C 1.1978(5) 0.5538(2) -0.11857(11) 0.0310(8) Uani 1 1 d . . . C18 C 1.1583(4) 0.5806(2) -0.04127(11) 0.0305(7) Uani 1 1 d . . . H18 H 1.1684 0.5584 -0.0125 0.037 Uiso 1 1 calc R . . C10 C 0.8983(4) 0.7619(2) 0.05579(11) 0.0283(7) Uani 1 1 d . . . C3 C 0.6155(4) 0.7598(2) 0.18925(11) 0.0297(7) Uani 1 1 d . . . C7 C 0.7602(4) 0.7672(2) 0.12282(11) 0.0277(7) Uani 1 1 d . . . O1 O 0.4199(4) 0.8089(2) 0.26841(9) 0.0546(8) Uani 1 1 d . . . C14 C 1.0768(5) 0.7052(2) -0.09253(11) 0.0332(8) Uani 1 1 d . . . H14 H 1.0333 0.7675 -0.0984 0.040 Uiso 1 1 calc R . . C17 C 1.2134(4) 0.5215(3) -0.07561(11) 0.0298(7) Uani 1 1 d . . . H17 H 1.2609 0.4601 -0.0698 0.036 Uiso 1 1 calc R . . C2 C 0.4601(5) 0.7251(3) 0.25961(12) 0.0372(8) Uani 1 1 d . . . C15 C 1.1293(5) 0.6461(2) -0.12721(11) 0.0358(8) Uani 1 1 d . . . H15 H 1.1186 0.6681 -0.1560 0.043 Uiso 1 1 calc R . . C11 C 0.8254(5) 1.0314(2) 0.08313(12) 0.0361(8) Uani 1 1 d . . . H11A H 0.8811 1.0527 0.0564 0.054 Uiso 1 1 calc R . . H11B H 0.8879 1.0582 0.1078 0.054 Uiso 1 1 calc R . . H11C H 0.7048 1.0537 0.0836 0.054 Uiso 1 1 calc R . . C1 C 0.4106(6) 0.6416(3) 0.28934(13) 0.0480(10) Uani 1 1 d . . . H1A H 0.5061 0.6288 0.3094 0.072 Uiso 1 1 calc R . . H1B H 0.3880 0.5842 0.2720 0.072 Uiso 1 1 calc R . . H1C H 0.3061 0.6584 0.3056 0.072 Uiso 1 1 calc R . . H2W1 H 0.770(19) 0.522(13) 0.268(5) 0.43(10) Uiso 1 1 d D . . H1W2 H 0.273(13) 0.971(8) 0.266(4) 0.25(6) Uiso 1 1 d D . . H1W1 H 0.28(2) 1.027(17) 0.237(7) 0.53(14) Uiso 1 1 d D . . H2W2 H 0.759(7) 0.472(4) 0.2308(16) 0.11(2) Uiso 1 1 d D . . C55 C -0.0903(6) 0.1418(3) 0.21063(13) 0.0472(10) Uani 1 1 d . . . H55A H -0.1926 0.1599 0.1937 0.071 Uiso 1 1 calc R . . H55B H -0.1170 0.0849 0.2279 0.071 Uiso 1 1 calc R . . H55C H 0.0064 0.1276 0.1912 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1W 0.0578(19) 0.0373(15) 0.0427(16) 0.0028(12) -0.0004(13) 0.0019(13) O2W 0.061(2) 0.0344(15) 0.0402(15) -0.0051(12) 0.0023(13) 0.0021(13) N7 0.0225(15) 0.0255(15) 0.0363(15) 0.0013(11) -0.0024(11) -0.0026(11) N6 0.0267(16) 0.0247(14) 0.0358(15) 0.0002(11) -0.0040(12) -0.0006(11) N5 0.0322(17) 0.0325(16) 0.0392(17) -0.0027(13) 0.0036(12) -0.0010(13) O4 0.0499(17) 0.0269(13) 0.0338(13) 0.0033(10) 0.0078(11) 0.0014(12) C30 0.031(2) 0.0244(17) 0.0374(19) 0.0033(14) -0.0018(14) -0.0022(14) C24 0.0225(17) 0.0243(17) 0.0349(18) 0.0028(13) -0.0054(13) -0.0030(13) C26 0.0234(18) 0.0253(17) 0.0334(17) 0.0036(13) -0.0044(13) -0.0001(13) N8 0.0291(16) 0.0280(15) 0.0347(16) 0.0037(12) -0.0030(12) -0.0019(12) C23 0.0307(19) 0.0229(17) 0.0385(19) 0.0066(13) -0.0063(14) -0.0052(14) C25 0.0255(18) 0.0245(17) 0.0339(17) 0.0041(13) -0.0064(13) 0.0002(13) C22 0.034(2) 0.0304(18) 0.0339(18) 0.0045(14) -0.0012(14) -0.0066(15) C28 0.0266(18) 0.0223(16) 0.0366(18) 0.0034(13) -0.0050(13) -0.0044(13) C27 0.0237(18) 0.0280(17) 0.0340(18) 0.0006(13) -0.0062(13) -0.0008(13) C21 0.0286(19) 0.0290(18) 0.0331(18) 0.0021(14) -0.0029(14) -0.0041(14) C31 0.0273(18) 0.0223(16) 0.0339(17) 0.0047(13) 0.0011(13) 0.0020(13) O3 0.080(2) 0.0447(17) 0.0350(15) -0.0010(12) 0.0105(14) -0.0144(15) C34 0.032(2) 0.0254(17) 0.0364(18) 0.0028(14) 0.0059(14) 0.0071(14) C35 0.0292(19) 0.0252(17) 0.0316(17) -0.0002(13) 0.0005(13) -0.0006(14) C32 0.050(2) 0.0225(17) 0.0334(18) -0.0009(13) -0.0016(15) 0.0042(15) C36 0.031(2) 0.0325(19) 0.0297(17) 0.0030(14) -0.0050(14) -0.0017(14) C20 0.040(2) 0.043(2) 0.0299(18) -0.0011(15) -0.0054(15) -0.0130(17) C29 0.038(2) 0.0271(18) 0.0379(19) 0.0018(14) 0.0004(15) -0.0026(15) C33 0.048(2) 0.0268(18) 0.0318(18) -0.0019(14) 0.0012(15) 0.0050(16) C19 0.055(3) 0.046(2) 0.044(2) -0.0103(18) 0.0056(19) -0.0066(19) N14 0.0258(16) 0.0260(15) 0.0352(15) 0.0011(11) 0.0034(11) -0.0005(11) N15 0.0221(15) 0.0273(15) 0.0345(15) 0.0056(11) 0.0024(11) 0.0013(11) O8 0.0505(17) 0.0280(13) 0.0307(13) 0.0031(10) -0.0075(11) -0.0039(12) N13 0.0332(17) 0.0335(16) 0.0369(16) -0.0022(12) -0.0024(12) 0.0007(13) C66 0.0302(19) 0.0237(17) 0.0385(19) 0.0023(14) 0.0013(14) 0.0008(14) N16 0.0307(17) 0.0271(15) 0.0338(15) 0.0070(12) 0.0031(12) 0.0012(12) C62 0.0268(19) 0.0244(17) 0.0330(17) 0.0020(13) 0.0061(13) -0.0005(13) C60 0.0226(17) 0.0250(17) 0.0325(17) 0.0011(13) 0.0065(13) 0.0016(13) C58 0.032(2) 0.0292(18) 0.0371(19) 0.0059(14) -0.0022(14) 0.0026(14) C63 0.0257(18) 0.0283(17) 0.0308(17) -0.0008(13) 0.0031(13) -0.0009(14) C59 0.035(2) 0.0217(17) 0.0363(18) 0.0049(13) 0.0051(14) 0.0021(14) C67 0.0261(18) 0.0268(17) 0.0315(17) 0.0020(13) 0.0013(13) -0.0043(13) C61 0.0220(17) 0.0282(17) 0.0312(17) 0.0046(13) 0.0052(13) 0.0001(13) C64 0.0240(18) 0.0284(18) 0.0347(18) 0.0043(14) 0.0050(13) 0.0007(14) C57 0.0260(19) 0.0298(18) 0.0339(18) 0.0025(14) 0.0043(13) 0.0005(14) O7 0.083(2) 0.0404(17) 0.0381(16) 0.0002(12) -0.0102(14) 0.0123(15) C69 0.0313(19) 0.0242(17) 0.0356(18) -0.0017(13) 0.0002(14) -0.0015(14) C70 0.037(2) 0.0262(17) 0.0325(18) 0.0052(13) -0.0054(14) -0.0103(15) C68 0.033(2) 0.0274(17) 0.0294(17) 0.0035(13) 0.0039(13) 0.0005(14) C72 0.048(2) 0.0175(16) 0.0365(19) -0.0013(13) -0.0006(15) -0.0028(15) C56 0.042(2) 0.038(2) 0.0330(19) -0.0008(15) 0.0043(15) 0.0058(17) C71 0.053(2) 0.0255(18) 0.0326(18) -0.0033(14) 0.0000(16) -0.0079(16) C65 0.039(2) 0.0257(18) 0.041(2) 0.0026(14) 0.0021(15) -0.0005(15) N11 0.0269(16) 0.0248(15) 0.0353(15) -0.0054(11) 0.0015(11) -0.0018(11) N10 0.0269(16) 0.0259(15) 0.0343(15) -0.0036(11) 0.0022(11) -0.0017(11) O6 0.0495(16) 0.0265(13) 0.0321(13) -0.0046(10) -0.0079(11) 0.0012(11) N9 0.0323(17) 0.0351(17) 0.0380(17) 0.0015(13) -0.0024(12) -0.0021(13) C48 0.0291(19) 0.0240(17) 0.0378(19) -0.0059(14) -0.0006(14) -0.0042(14) N12 0.0319(17) 0.0256(15) 0.0335(15) -0.0065(11) 0.0030(12) -0.0009(12) C41 0.0308(19) 0.0211(16) 0.0394(19) -0.0044(13) 0.0031(14) -0.0056(14) C42 0.0266(18) 0.0225(16) 0.0341(18) -0.0039(13) 0.0059(13) -0.0052(13) C45 0.0235(18) 0.0290(18) 0.0333(17) -0.0017(13) 0.0048(13) -0.0020(14) C49 0.0272(18) 0.0249(17) 0.0325(17) -0.0069(13) 0.0007(13) 0.0014(13) C52 0.0310(19) 0.0271(18) 0.0332(18) -0.0069(13) -0.0052(14) 0.0065(14) O5 0.082(2) 0.0425(17) 0.0363(15) -0.0012(12) -0.0106(14) -0.0168(15) C43 0.0238(18) 0.0257(17) 0.0324(17) -0.0060(13) 0.0059(13) -0.0016(13) C44 0.0252(18) 0.0243(17) 0.0394(19) -0.0035(13) 0.0051(14) -0.0004(13) C40 0.033(2) 0.0296(18) 0.0370(19) -0.0065(14) -0.0010(14) -0.0035(15) C39 0.0275(19) 0.0284(18) 0.0334(18) -0.0036(13) 0.0041(13) -0.0023(14) C46 0.0268(18) 0.0247(17) 0.0338(18) -0.0064(13) 0.0051(13) -0.0006(13) C54 0.032(2) 0.0330(19) 0.0315(18) -0.0062(14) 0.0049(14) -0.0036(15) C50 0.043(2) 0.0221(17) 0.0341(18) 0.0020(13) 0.0012(15) 0.0030(15) C53 0.0273(19) 0.0265(17) 0.0345(18) -0.0014(13) -0.0001(13) -0.0023(14) C38 0.038(2) 0.044(2) 0.0302(18) -0.0001(15) 0.0030(15) -0.0097(17) C51 0.048(2) 0.0250(18) 0.0351(19) -0.0012(14) 0.0006(15) 0.0069(16) C47 0.036(2) 0.0234(17) 0.044(2) -0.0029(14) -0.0014(15) -0.0024(14) C37 0.053(3) 0.046(2) 0.042(2) 0.0075(18) -0.0056(18) -0.0055(19) N3 0.0253(16) 0.0249(14) 0.0348(15) -0.0039(11) -0.0002(11) -0.0003(11) N2 0.0277(16) 0.0261(15) 0.0349(15) -0.0031(11) -0.0033(12) -0.0019(11) O2 0.0495(17) 0.0268(13) 0.0336(13) -0.0044(10) 0.0083(11) -0.0051(12) C12 0.0290(19) 0.0262(17) 0.0325(17) -0.0063(13) 0.0003(13) 0.0022(14) N1 0.0333(17) 0.0342(17) 0.0368(16) 0.0015(12) 0.0003(12) 0.0021(13) N4 0.0298(16) 0.0303(16) 0.0321(15) -0.0062(12) -0.0019(12) 0.0002(12) C6 0.0237(17) 0.0239(16) 0.0330(17) -0.0042(13) -0.0067(13) 0.0039(13) C9 0.0274(18) 0.0260(17) 0.0302(17) -0.0048(13) -0.0046(13) -0.0012(13) C5 0.034(2) 0.0226(17) 0.0392(19) -0.0090(14) -0.0045(15) 0.0032(14) C8 0.0242(18) 0.0230(16) 0.0352(18) -0.0030(13) -0.0064(13) -0.0007(13) C4 0.031(2) 0.0286(18) 0.0368(19) -0.0087(14) 0.0017(14) 0.0031(14) C13 0.0288(19) 0.0248(17) 0.0322(17) -0.0053(13) -0.0007(13) -0.0040(13) C16 0.034(2) 0.0251(17) 0.0335(18) -0.0076(13) 0.0042(14) -0.0071(14) C18 0.0300(19) 0.0324(19) 0.0291(17) -0.0061(13) -0.0037(13) -0.0015(14) C10 0.0218(17) 0.0294(18) 0.0336(18) -0.0059(13) -0.0041(13) 0.0001(13) C3 0.0251(18) 0.0301(18) 0.0339(18) -0.0039(14) -0.0032(13) 0.0011(14) C7 0.0250(18) 0.0243(17) 0.0337(17) -0.0075(13) -0.0036(13) 0.0009(13) O1 0.084(2) 0.0416(17) 0.0380(16) -0.0012(12) 0.0102(14) 0.0127(15) C14 0.042(2) 0.0210(17) 0.0370(19) -0.0022(13) -0.0015(15) -0.0054(14) C17 0.0297(19) 0.0270(17) 0.0328(18) -0.0027(13) 0.0003(13) -0.0021(14) C2 0.043(2) 0.036(2) 0.0322(19) 0.0007(15) -0.0048(15) 0.0047(17) C15 0.054(2) 0.0233(18) 0.0306(18) 0.0026(13) -0.0001(15) -0.0069(16) C11 0.041(2) 0.0261(18) 0.041(2) -0.0026(15) 0.0032(16) -0.0002(15) C1 0.055(3) 0.048(2) 0.041(2) 0.0058(18) 0.0040(18) 0.004(2) C55 0.053(3) 0.046(2) 0.042(2) -0.0078(18) -0.0064(18) 0.0049(19) _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 O1W H1W2 0.84(11) . ? O1W H1W1 0.81(19) . ? O2W H2W1 0.82(17) . ? O2W H2W2 0.83(5) . ? N7 C28 1.315(4) . ? N7 C25 1.364(4) . ? N6 C21 1.325(4) . ? N6 C25 1.359(4) . ? N5 C20 1.366(5) . ? N5 C21 1.405(4) . ? O4 C34 1.379(4) . ? O4 H4 0.8200 . ? C30 N8 1.278(5) . ? C30 C28 1.480(5) . ? C30 H30 0.9300 . ? C24 C23 1.404(5) . ? C24 C25 1.419(4) . ? C24 C26 1.425(5) . ? C26 C27 1.362(5) . ? C26 C29 1.497(5) . ? N8 C31 1.420(4) . ? C23 C22 1.355(5) . ? C23 H23 0.9300 . ? C22 C21 1.419(5) . ? C22 H22 0.9300 . ? C28 C27 1.410(4) . ? C27 H27 0.9300 . ? C31 C32 1.379(5) . ? C31 C36 1.407(5) . ? O3 C20 1.216(4) . ? C34 C35 1.378(5) . ? C34 C33 1.387(5) . ? C35 C36 1.385(5) . ? C35 H35 0.9300 . ? C32 C33 1.381(5) . ? C32 H32 0.9300 . ? C36 H36 0.9300 . ? C20 C19 1.511(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C33 H33 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N14 C57 1.321(4) . ? N14 C61 1.364(4) . ? N15 C64 1.319(4) . ? N15 C61 1.365(4) . ? O8 C70 1.373(4) . ? O8 H8 0.8200 . ? N13 C56 1.368(5) . ? N13 C57 1.407(4) . ? C66 N16 1.279(5) . ? C66 C64 1.474(5) . ? C66 H66 0.9300 . ? N16 C67 1.420(4) . ? C62 C63 1.366(5) . ? C62 C60 1.427(5) . ? C62 C65 1.496(5) . ? C60 C59 1.403(5) . ? C60 C61 1.414(4) . ? C58 C59 1.351(5) . ? C58 C57 1.420(5) . ? C58 H58 0.9300 . ? C63 C64 1.424(5) . ? C63 H63 0.9300 . ? C59 H59 0.9300 . ? C67 C72 1.382(5) . ? C67 C68 1.397(5) . ? O7 C56 1.220(4) . ? C69 C68 1.384(5) . ? C69 C70 1.392(5) . ? C69 H69 0.9300 . ? C70 C71 1.389(5) . ? C68 H68 0.9300 . ? C72 C71 1.382(5) . ? C72 H72 0.9300 . ? C56 C55 1.499(5) . ? C71 H71 0.9300 . ? C65 H65A 0.9600 . ? C65 H65B 0.9600 . ? C65 H65C 0.9600 . ? N11 C46 1.322(4) . ? N11 C43 1.364(4) . ? N10 C39 1.321(4) . ? N10 C43 1.364(4) . ? O6 C52 1.375(4) . ? O6 H6 0.8200 . ? N9 C38 1.372(5) . ? N9 C39 1.406(4) . ? C48 N12 1.283(5) . ? C48 C46 1.476(4) . ? C48 H48 0.9300 . ? N12 C49 1.415(4) . ? C41 C40 1.353(5) . ? C41 C42 1.408(5) . ? C41 H41 0.9300 . ? C42 C43 1.413(4) . ? C42 C44 1.424(5) . ? C45 C44 1.371(5) . ? C45 C46 1.411(5) . ? C45 H45 0.9300 . ? C49 C50 1.381(5) . ? C49 C54 1.405(5) . ? C52 C53 1.384(5) . ? C52 C51 1.389(5) . ? O5 C38 1.218(4) . ? C44 C47 1.493(5) . ? C40 C39 1.420(5) . ? C40 H40 0.9300 . ? C54 C53 1.384(5) . ? C54 H54 0.9300 . ? C50 C51 1.389(5) . ? C50 H50 0.9300 . ? C53 H53 0.9300 . ? C38 C37 1.507(5) . ? C51 H51 0.9300 . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? N3 C10 1.317(4) . ? N3 C7 1.361(4) . ? N2 C3 1.322(4) . ? N2 C7 1.360(4) . ? O2 C16 1.374(4) . ? O2 H2 0.8200 . ? C12 N4 1.276(4) . ? C12 C10 1.473(4) . ? C12 H12 0.9300 . ? N1 C2 1.375(5) . ? N1 C3 1.403(4) . ? N4 C13 1.424(4) . ? C6 C5 1.406(5) . ? C6 C7 1.414(4) . ? C6 C8 1.429(5) . ? C9 C8 1.362(4) . ? C9 C10 1.424(5) . ? C9 H9 0.9300 . ? C5 C4 1.349(5) . ? C5 H5 0.9300 . ? C8 C11 1.505(5) . ? C4 C3 1.418(5) . ? C4 H4A 0.9300 . ? C13 C14 1.382(5) . ? C13 C18 1.400(5) . ? C16 C17 1.384(5) . ? C16 C15 1.388(5) . ? C18 C17 1.384(4) . ? C18 H18 0.9300 . ? O1 C2 1.213(4) . ? C14 C15 1.386(5) . ? C14 H14 0.9300 . ? C17 H17 0.9300 . ? C2 C1 1.503(5) . ? C15 H15 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? 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 H1W2 O1W H1W1 89(10) . . ? H2W1 O2W H2W2 107(10) . . ? C28 N7 C25 117.2(3) . . ? C21 N6 C25 118.0(3) . . ? C20 N5 C21 126.9(3) . . ? C34 O4 H4 109.5 . . ? N8 C30 C28 122.2(3) . . ? N8 C30 H30 118.9 . . ? C28 C30 H30 118.9 . . ? C23 C24 C25 116.5(3) . . ? C23 C24 C26 124.3(3) . . ? C25 C24 C26 119.2(3) . . ? C27 C26 C24 116.6(3) . . ? C27 C26 C29 122.3(3) . . ? C24 C26 C29 121.1(3) . . ? C30 N8 C31 118.8(3) . . ? C22 C23 C24 120.9(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? N6 C25 N7 114.7(3) . . ? N6 C25 C24 123.0(3) . . ? N7 C25 C24 122.2(3) . . ? C23 C22 C21 118.5(3) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.8 . . ? N7 C28 C27 124.0(3) . . ? N7 C28 C30 114.8(3) . . ? C27 C28 C30 121.1(3) . . ? C26 C27 C28 120.7(3) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? N6 C21 N5 113.7(3) . . ? N6 C21 C22 123.0(3) . . ? N5 C21 C22 123.2(3) . . ? C32 C31 C36 118.2(3) . . ? C32 C31 N8 118.3(3) . . ? C36 C31 N8 123.4(3) . . ? C35 C34 O4 122.4(3) . . ? C35 C34 C33 119.8(3) . . ? O4 C34 C33 117.8(3) . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C32 C33 121.5(3) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C35 C36 C31 120.2(3) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? O3 C20 N5 124.4(4) . . ? O3 C20 C19 120.6(3) . . ? N5 C20 C19 115.0(3) . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C33 C34 119.8(3) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C57 N14 C61 118.0(3) . . ? C64 N15 C61 117.3(3) . . ? C70 O8 H8 109.5 . . ? C56 N13 C57 127.5(3) . . ? N16 C66 C64 122.0(3) . . ? N16 C66 H66 119.0 . . ? C64 C66 H66 119.0 . . ? C66 N16 C67 118.2(3) . . ? C63 C62 C60 117.3(3) . . ? C63 C62 C65 122.0(3) . . ? C60 C62 C65 120.8(3) . . ? C59 C60 C61 116.7(3) . . ? C59 C60 C62 124.5(3) . . ? C61 C60 C62 118.8(3) . . ? C59 C58 C57 119.1(3) . . ? C59 C58 H58 120.4 . . ? C57 C58 H58 120.4 . . ? C62 C63 C64 120.2(3) . . ? C62 C63 H63 119.9 . . ? C64 C63 H63 119.9 . . ? C58 C59 C60 120.5(3) . . ? C58 C59 H59 119.8 . . ? C60 C59 H59 119.8 . . ? C72 C67 C68 118.1(3) . . ? C72 C67 N16 117.8(3) . . ? C68 C67 N16 124.2(3) . . ? N14 C61 N15 114.2(3) . . ? N14 C61 C60 123.0(3) . . ? N15 C61 C60 122.8(3) . . ? N15 C64 C63 123.7(3) . . ? N15 C64 C66 115.5(3) . . ? C63 C64 C66 120.8(3) . . ? N14 C57 N13 114.2(3) . . ? N14 C57 C58 122.6(3) . . ? N13 C57 C58 123.1(3) . . ? C68 C69 C70 119.7(3) . . ? C68 C69 H69 120.2 . . ? C70 C69 H69 120.2 . . ? O8 C70 C71 118.0(3) . . ? O8 C70 C69 122.4(3) . . ? C71 C70 C69 119.6(3) . . ? C69 C68 C67 121.2(3) . . ? C69 C68 H68 119.4 . . ? C67 C68 H68 119.4 . . ? C71 C72 C67 121.6(3) . . ? C71 C72 H72 119.2 . . ? C67 C72 H72 119.2 . . ? O7 C56 N13 123.8(4) . . ? O7 C56 C55 121.2(4) . . ? N13 C56 C55 115.0(3) . . ? C72 C71 C70 119.8(3) . . ? C72 C71 H71 120.1 . . ? C70 C71 H71 120.1 . . ? C62 C65 H65A 109.5 . . ? C62 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C62 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C46 N11 C43 116.9(3) . . ? C39 N10 C43 117.8(3) . . ? C52 O6 H6 109.5 . . ? C38 N9 C39 127.4(3) . . ? N12 C48 C46 121.8(3) . . ? N12 C48 H48 119.1 . . ? C46 C48 H48 119.1 . . ? C48 N12 C49 118.6(3) . . ? C40 C41 C42 120.7(3) . . ? C40 C41 H41 119.7 . . ? C42 C41 H41 119.7 . . ? C41 C42 C43 116.8(3) . . ? C41 C42 C44 124.1(3) . . ? C43 C42 C44 119.2(3) . . ? C44 C45 C46 120.3(3) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C50 C49 C54 118.0(3) . . ? C50 C49 N12 118.1(3) . . ? C54 C49 N12 123.8(3) . . ? O6 C52 C53 122.6(3) . . ? O6 C52 C51 117.6(3) . . ? C53 C52 C51 119.7(3) . . ? N11 C43 N10 114.3(3) . . ? N11 C43 C42 122.7(3) . . ? N10 C43 C42 123.0(3) . . ? C45 C44 C42 116.8(3) . . ? C45 C44 C47 122.0(3) . . ? C42 C44 C47 121.2(3) . . ? C41 C40 C39 118.6(3) . . ? C41 C40 H40 120.7 . . ? C39 C40 H40 120.7 . . ? N10 C39 N9 113.8(3) . . ? N10 C39 C40 123.2(3) . . ? N9 C39 C40 123.0(3) . . ? N11 C46 C45 124.1(3) . . ? N11 C46 C48 114.6(3) . . ? C45 C46 C48 121.2(3) . . ? C53 C54 C49 120.8(3) . . ? C53 C54 H54 119.6 . . ? C49 C54 H54 119.6 . . ? C49 C50 C51 121.6(3) . . ? C49 C50 H50 119.2 . . ? C51 C50 H50 119.2 . . ? C54 C53 C52 120.2(3) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? O5 C38 N9 123.6(4) . . ? O5 C38 C37 121.4(3) . . ? N9 C38 C37 115.0(3) . . ? C50 C51 C52 119.6(3) . . ? C50 C51 H51 120.2 . . ? C52 C51 H51 120.2 . . ? C44 C47 H47A 109.5 . . ? C44 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C38 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C10 N3 C7 117.7(3) . . ? C3 N2 C7 118.1(3) . . ? C16 O2 H2 109.5 . . ? N4 C12 C10 122.1(3) . . ? N4 C12 H12 119.0 . . ? C10 C12 H12 119.0 . . ? C2 N1 C3 127.0(3) . . ? C12 N4 C13 118.6(3) . . ? C5 C6 C7 116.9(3) . . ? C5 C6 C8 124.1(3) . . ? C7 C6 C8 119.0(3) . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C9 C8 C6 117.2(3) . . ? C9 C8 C11 121.9(3) . . ? C6 C8 C11 120.9(3) . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C14 C13 C18 118.3(3) . . ? C14 C13 N4 118.1(3) . . ? C18 C13 N4 123.6(3) . . ? O2 C16 C17 122.5(3) . . ? O2 C16 C15 117.6(3) . . ? C17 C16 C15 120.0(3) . . ? C17 C18 C13 120.6(3) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? N3 C10 C9 123.5(3) . . ? N3 C10 C12 115.6(3) . . ? C9 C10 C12 120.9(3) . . ? N2 C3 N1 114.0(3) . . ? N2 C3 C4 122.6(3) . . ? N1 C3 C4 123.4(3) . . ? N2 C7 N3 114.6(3) . . ? N2 C7 C6 122.9(3) . . ? N3 C7 C6 122.4(3) . . ? C13 C14 C15 121.6(3) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? O1 C2 N1 124.2(4) . . ? O1 C2 C1 121.4(4) . . ? N1 C2 C1 114.5(3) . . ? C14 C15 C16 119.4(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C56 C55 H55A 109.5 . . ? C56 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C56 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? 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 C23 C24 C26 C27 178.7(3) . . . . ? C25 C24 C26 C27 -0.5(4) . . . . ? C23 C24 C26 C29 -0.9(5) . . . . ? C25 C24 C26 C29 179.9(3) . . . . ? C28 C30 N8 C31 178.9(3) . . . . ? C25 C24 C23 C22 -0.4(5) . . . . ? C26 C24 C23 C22 -179.6(3) . . . . ? C21 N6 C25 N7 177.8(3) . . . . ? C21 N6 C25 C24 -0.7(5) . . . . ? C28 N7 C25 N6 -179.5(3) . . . . ? C28 N7 C25 C24 -1.1(5) . . . . ? C23 C24 C25 N6 0.9(5) . . . . ? C26 C24 C25 N6 -179.8(3) . . . . ? C23 C24 C25 N7 -177.4(3) . . . . ? C26 C24 C25 N7 1.8(5) . . . . ? C24 C23 C22 C21 -0.3(5) . . . . ? C25 N7 C28 C27 -1.0(5) . . . . ? C25 N7 C28 C30 177.2(3) . . . . ? N8 C30 C28 N7 -177.2(3) . . . . ? N8 C30 C28 C27 1.0(5) . . . . ? C24 C26 C27 C28 -1.4(5) . . . . ? C29 C26 C27 C28 178.2(3) . . . . ? N7 C28 C27 C26 2.3(5) . . . . ? C30 C28 C27 C26 -175.7(3) . . . . ? C25 N6 C21 N5 179.9(3) . . . . ? C25 N6 C21 C22 -0.1(5) . . . . ? C20 N5 C21 N6 178.2(3) . . . . ? C20 N5 C21 C22 -1.9(6) . . . . ? C23 C22 C21 N6 0.6(5) . . . . ? C23 C22 C21 N5 -179.4(3) . . . . ? C30 N8 C31 C32 -150.6(3) . . . . ? C30 N8 C31 C36 30.1(5) . . . . ? O4 C34 C35 C36 -179.8(3) . . . . ? C33 C34 C35 C36 -1.0(5) . . . . ? C36 C31 C32 C33 -1.9(5) . . . . ? N8 C31 C32 C33 178.8(3) . . . . ? C34 C35 C36 C31 0.5(5) . . . . ? C32 C31 C36 C35 0.9(5) . . . . ? N8 C31 C36 C35 -179.8(3) . . . . ? C21 N5 C20 O3 -2.4(6) . . . . ? C21 N5 C20 C19 178.5(3) . . . . ? C31 C32 C33 C34 1.4(6) . . . . ? C35 C34 C33 C32 0.1(5) . . . . ? O4 C34 C33 C32 178.9(3) . . . . ? C64 C66 N16 C67 179.3(3) . . . . ? C63 C62 C60 C59 178.5(3) . . . . ? C65 C62 C60 C59 -1.4(5) . . . . ? C63 C62 C60 C61 -0.2(4) . . . . ? C65 C62 C60 C61 179.9(3) . . . . ? C60 C62 C63 C64 -1.6(5) . . . . ? C65 C62 C63 C64 178.3(3) . . . . ? C57 C58 C59 C60 -0.6(5) . . . . ? C61 C60 C59 C58 -0.4(5) . . . . ? C62 C60 C59 C58 -179.2(3) . . . . ? C66 N16 C67 C72 -151.0(3) . . . . ? C66 N16 C67 C68 29.6(5) . . . . ? C57 N14 C61 N15 178.0(3) . . . . ? C57 N14 C61 C60 -0.7(5) . . . . ? C64 N15 C61 N14 -179.3(3) . . . . ? C64 N15 C61 C60 -0.6(4) . . . . ? C59 C60 C61 N14 1.1(5) . . . . ? C62 C60 C61 N14 180.0(3) . . . . ? C59 C60 C61 N15 -177.4(3) . . . . ? C62 C60 C61 N15 1.5(5) . . . . ? C61 N15 C64 C63 -1.4(5) . . . . ? C61 N15 C64 C66 177.1(3) . . . . ? C62 C63 C64 N15 2.6(5) . . . . ? C62 C63 C64 C66 -175.8(3) . . . . ? N16 C66 C64 N15 -177.1(3) . . . . ? N16 C66 C64 C63 1.4(5) . . . . ? C61 N14 C57 N13 179.7(3) . . . . ? C61 N14 C57 C58 -0.5(5) . . . . ? C56 N13 C57 N14 177.8(3) . . . . ? C56 N13 C57 C58 -2.0(5) . . . . ? C59 C58 C57 N14 1.1(5) . . . . ? C59 C58 C57 N13 -179.1(3) . . . . ? C68 C69 C70 O8 -179.9(3) . . . . ? C68 C69 C70 C71 -1.2(5) . . . . ? C70 C69 C68 C67 0.6(5) . . . . ? C72 C67 C68 C69 0.9(5) . . . . ? N16 C67 C68 C69 -179.7(3) . . . . ? C68 C67 C72 C71 -2.0(5) . . . . ? N16 C67 C72 C71 178.6(3) . . . . ? C57 N13 C56 O7 -2.0(6) . . . . ? C57 N13 C56 C55 178.9(3) . . . . ? C67 C72 C71 C70 1.5(6) . . . . ? O8 C70 C71 C72 178.9(3) . . . . ? C69 C70 C71 C72 0.1(5) . . . . ? C46 C48 N12 C49 -179.2(3) . . . . ? C40 C41 C42 C43 1.0(5) . . . . ? C40 C41 C42 C44 179.7(3) . . . . ? C48 N12 C49 C50 150.8(3) . . . . ? C48 N12 C49 C54 -30.0(5) . . . . ? C46 N11 C43 N10 179.5(3) . . . . ? C46 N11 C43 C42 0.3(5) . . . . ? C39 N10 C43 N11 -178.4(3) . . . . ? C39 N10 C43 C42 0.9(5) . . . . ? C41 C42 C43 N11 177.6(3) . . . . ? C44 C42 C43 N11 -1.1(5) . . . . ? C41 C42 C43 N10 -1.6(5) . . . . ? C44 C42 C43 N10 179.7(3) . . . . ? C46 C45 C44 C42 1.0(5) . . . . ? C46 C45 C44 C47 -178.2(3) . . . . ? C41 C42 C44 C45 -178.2(3) . . . . ? C43 C42 C44 C45 0.4(5) . . . . ? C41 C42 C44 C47 1.0(5) . . . . ? C43 C42 C44 C47 179.6(3) . . . . ? C42 C41 C40 C39 0.1(5) . . . . ? C43 N10 C39 N9 -180.0(3) . . . . ? C43 N10 C39 C40 0.4(5) . . . . ? C38 N9 C39 N10 -177.9(3) . . . . ? C38 N9 C39 C40 1.7(5) . . . . ? C41 C40 C39 N10 -0.9(5) . . . . ? C41 C40 C39 N9 179.5(3) . . . . ? C43 N11 C46 C45 1.3(5) . . . . ? C43 N11 C46 C48 -176.7(3) . . . . ? C44 C45 C46 N11 -2.0(5) . . . . ? C44 C45 C46 C48 175.9(3) . . . . ? N12 C48 C46 N11 177.2(3) . . . . ? N12 C48 C46 C45 -0.9(5) . . . . ? C50 C49 C54 C53 -1.1(5) . . . . ? N12 C49 C54 C53 179.8(3) . . . . ? C54 C49 C50 C51 2.2(5) . . . . ? N12 C49 C50 C51 -178.6(3) . . . . ? C49 C54 C53 C52 -0.5(5) . . . . ? O6 C52 C53 C54 179.9(3) . . . . ? C51 C52 C53 C54 1.0(5) . . . . ? C39 N9 C38 O5 2.7(6) . . . . ? C39 N9 C38 C37 -178.8(3) . . . . ? C49 C50 C51 C52 -1.7(5) . . . . ? O6 C52 C51 C50 -178.9(3) . . . . ? C53 C52 C51 C50 0.1(5) . . . . ? C10 C12 N4 C13 -179.5(3) . . . . ? C7 C6 C5 C4 0.4(5) . . . . ? C8 C6 C5 C4 179.7(3) . . . . ? C10 C9 C8 C6 1.0(5) . . . . ? C10 C9 C8 C11 -178.1(3) . . . . ? C5 C6 C8 C9 -178.4(3) . . . . ? C7 C6 C8 C9 0.9(4) . . . . ? C5 C6 C8 C11 0.7(5) . . . . ? C7 C6 C8 C11 179.9(3) . . . . ? C6 C5 C4 C3 0.5(5) . . . . ? C12 N4 C13 C14 150.8(3) . . . . ? C12 N4 C13 C18 -29.5(5) . . . . ? C14 C13 C18 C17 -1.0(5) . . . . ? N4 C13 C18 C17 179.4(3) . . . . ? C7 N3 C10 C9 1.2(5) . . . . ? C7 N3 C10 C12 -176.8(3) . . . . ? C8 C9 C10 N3 -2.1(5) . . . . ? C8 C9 C10 C12 175.7(3) . . . . ? N4 C12 C10 N3 177.2(3) . . . . ? N4 C12 C10 C9 -0.8(5) . . . . ? C7 N2 C3 N1 -179.6(3) . . . . ? C7 N2 C3 C4 0.8(5) . . . . ? C2 N1 C3 N2 -177.8(3) . . . . ? C2 N1 C3 C4 1.8(5) . . . . ? C5 C4 C3 N2 -1.1(5) . . . . ? C5 C4 C3 N1 179.3(3) . . . . ? C3 N2 C7 N3 -178.2(3) . . . . ? C3 N2 C7 C6 0.2(5) . . . . ? C10 N3 C7 N2 179.2(3) . . . . ? C10 N3 C7 C6 0.8(5) . . . . ? C5 C6 C7 N2 -0.7(5) . . . . ? C8 C6 C7 N2 180.0(3) . . . . ? C5 C6 C7 N3 177.5(3) . . . . ? C8 C6 C7 N3 -1.8(5) . . . . ? C18 C13 C14 C15 1.9(5) . . . . ? N4 C13 C14 C15 -178.4(3) . . . . ? C13 C18 C17 C16 -0.4(5) . . . . ? O2 C16 C17 C18 179.9(3) . . . . ? C15 C16 C17 C18 0.9(5) . . . . ? C3 N1 C2 O1 2.4(6) . . . . ? C3 N1 C2 C1 -178.7(3) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? O2 C16 C15 C14 -179.1(3) . . . . ? C17 C16 C15 C14 0.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.616 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.061