# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Trevor Hambley' 'Antonia J. Clarke' 'Paul Jensen' 'Natsuho Yamamoto' _publ_contact_author_name 'Trevor Hambley' _publ_contact_author_email T.HAMBLEY@CHEM.USYD.EDU.AU _publ_section_title ; Iron(III) Complexes of Fluorescent Hydroxamate Ligands: Preparation, Properties, and Cellular Processing ; # Attachment '[Fe_C3haH__salen_].CIF' data_twh07pj2 _database_code_depnum_ccdc_archive 'CCDC 740748' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Fe N3 O6' _chemical_formula_sum 'C26 H20 Fe N3 O6' _chemical_formula_weight 526.30 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' Fe Fe 0.3463 0.8444 '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 10.9767(6) _cell_length_b 16.7965(9) _cell_length_c 18.7119(12) _cell_angle_alpha 84.418(2) _cell_angle_beta 85.093(3) _cell_angle_gamma 86.652(2) _cell_volume 3416.6(3) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5777 _cell_measurement_theta_min 2.9921 _cell_measurement_theta_max 25.1846 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1626 _exptl_absorpt_coefficient_mu 0.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; SADABS Ver. 2.10 (Bruker-AXS, 2004) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(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-Nonius FR591 Kappa APEX II' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55683 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.36 _reflns_number_total 12363 _reflns_number_gt 8802 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 Ver. 2.1-3 (Bruker-AXS, 2006)' _computing_cell_refinement 'SAINT Ver. 7.23A (Bruker-AXS, 2005)' _computing_data_reduction 'SAINT Ver. 7.23A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-Seed (Barbour, 2001), SHELXTL Ver. 6.14 (Bruker-AXS, 2003) ; _computing_publication_material 'modiCIFer-12162005 (Guzei, 2005)' _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^)+(0.0258P)^2^+3.3479P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12363 _refine_ls_number_parameters 982 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.27474(4) 0.09876(2) 0.04784(2) 0.02190(10) Uani 1 1 d . . . Fe2 Fe 0.38222(3) 0.21567(2) 0.33691(2) 0.01863(10) Uani 1 1 d . . . Fe3 Fe 0.79245(4) 0.47823(2) 0.40971(2) 0.02367(10) Uani 1 1 d . . . O1 O 0.17362(18) 0.01243(11) 0.03785(11) 0.0297(5) Uani 1 1 d . . . O2 O 0.30177(18) 0.12624(11) -0.05557(10) 0.0271(5) Uani 1 1 d . . . O3 O 0.23199(17) 0.10651(10) 0.15365(10) 0.0259(4) Uani 1 1 d . . . O4 O 0.16914(17) 0.20466(10) 0.04712(10) 0.0242(4) Uani 1 1 d . . . O5 O 0.00014(16) 0.28060(11) 0.23328(10) 0.0242(4) Uani 1 1 d . . . O6 O -0.01130(17) 0.40694(10) 0.18897(10) 0.0244(4) Uani 1 1 d . . . O7 O 0.44142(16) 0.11482(11) 0.30296(10) 0.0236(4) Uani 1 1 d . . . O8 O 0.43734(16) 0.27459(11) 0.24771(10) 0.0241(4) Uani 1 1 d . . . O9 O 0.21495(16) 0.23182(11) 0.30118(10) 0.0219(4) Uani 1 1 d . . . O10 O 0.26294(16) 0.16721(10) 0.42583(10) 0.0222(4) Uani 1 1 d . . . O11 O -0.11431(18) 0.17702(13) 0.39558(11) 0.0357(5) Uani 1 1 d . . . O12 O -0.15664(16) 0.11294(12) 0.50238(10) 0.0279(5) Uani 1 1 d . . . O13 O 0.67524(18) 0.46323(11) 0.49120(10) 0.0294(5) Uani 1 1 d . . . O14 O 0.81269(17) 0.58906(11) 0.42400(10) 0.0268(5) Uani 1 1 d . . . O15 O 0.71155(17) 0.52688(11) 0.32181(10) 0.0283(5) Uani 1 1 d . . . O16 O 0.75204(17) 0.37758(11) 0.36056(10) 0.0253(4) Uani 1 1 d . . . O17 O 0.71603(19) 0.42715(12) 0.13901(11) 0.0322(5) Uani 1 1 d . . . O18 O 0.76860(19) 0.30125(12) 0.12209(10) 0.0318(5) Uani 1 1 d . . . N1 N 0.4089(2) 0.00923(13) 0.08593(12) 0.0240(5) Uani 1 1 d . . . N2 N 0.4347(2) 0.16231(13) 0.05316(13) 0.0256(5) Uani 1 1 d . . . N3 N 0.1855(2) 0.18140(13) 0.16531(13) 0.0229(5) Uani 1 1 d D . . H3N H 0.188(3) 0.1962(17) 0.2073(12) 0.027 Uiso 1 1 d D . . N4 N 0.51291(19) 0.19182(13) 0.41684(12) 0.0211(5) Uani 1 1 d . . . N5 N 0.3900(2) 0.32530(13) 0.38230(12) 0.0240(5) Uani 1 1 d . . . N6 N 0.1227(2) 0.20416(13) 0.34876(12) 0.0200(5) Uani 1 1 d D . . H6N H 0.053(2) 0.2090(16) 0.3332(15) 0.024 Uiso 1 1 d D . . N7 N 0.9090(2) 0.39243(14) 0.47201(13) 0.0284(6) Uani 1 1 d . . . N8 N 0.9695(2) 0.48201(14) 0.35439(13) 0.0269(6) Uani 1 1 d . . . N9 N 0.7007(2) 0.47143(14) 0.27463(13) 0.0251(5) Uani 1 1 d D . . H9N H 0.687(3) 0.4853(17) 0.2310(12) 0.030 Uiso 1 1 d D . . C1 C 0.1727(3) -0.06192(16) 0.06696(15) 0.0265(7) Uani 1 1 d . . . C2 C 0.0658(3) -0.10437(17) 0.06571(16) 0.0312(7) Uani 1 1 d . . . H2 H -0.0053 -0.0774 0.0477 0.037 Uiso 1 1 calc R . . C3 C 0.0630(3) -0.18419(18) 0.09009(17) 0.0363(8) Uani 1 1 d . . . H3 H -0.0096 -0.2118 0.0883 0.044 Uiso 1 1 calc R . . C4 C 0.1666(3) -0.22539(18) 0.11763(18) 0.0396(8) Uani 1 1 d . . . H4 H 0.1652 -0.2810 0.1328 0.047 Uiso 1 1 calc R . . C5 C 0.2698(3) -0.18432(17) 0.12234(17) 0.0339(8) Uani 1 1 d . . . H5 H 0.3386 -0.2117 0.1427 0.041 Uiso 1 1 calc R . . C6 C 0.2761(3) -0.10273(16) 0.09778(15) 0.0261(7) Uani 1 1 d . . . C7 C 0.3876(3) -0.06438(17) 0.10512(15) 0.0281(7) Uani 1 1 d . . . H7 H 0.4515 -0.0966 0.1262 0.034 Uiso 1 1 calc R . . C8 C 0.5283(3) 0.03902(17) 0.09852(16) 0.0288(7) Uani 1 1 d . . . H8A H 0.5873 0.0327 0.0562 0.035 Uiso 1 1 calc R . . H8B H 0.5615 0.0084 0.1411 0.035 Uiso 1 1 calc R . . C9 C 0.5079(3) 0.12726(17) 0.11124(16) 0.0297(7) Uani 1 1 d . . . H9A H 0.4636 0.1334 0.1589 0.036 Uiso 1 1 calc R . . H9B H 0.5870 0.1532 0.1090 0.036 Uiso 1 1 calc R . . C10 C 0.4717(3) 0.21948(16) 0.00790(16) 0.0276(7) Uani 1 1 d . . . H10 H 0.5428 0.2454 0.0168 0.033 Uiso 1 1 calc R . . C11 C 0.4106(3) 0.24674(16) -0.05641(16) 0.0273(7) Uani 1 1 d . . . C12 C 0.4394(3) 0.32093(18) -0.09366(19) 0.0384(8) Uani 1 1 d . . . H12 H 0.4938 0.3534 -0.0741 0.046 Uiso 1 1 calc R . . C13 C 0.3911(3) 0.3478(2) -0.1574(2) 0.0459(9) Uani 1 1 d . . . H13 H 0.4114 0.3982 -0.1816 0.055 Uiso 1 1 calc R . . C14 C 0.3119(3) 0.2999(2) -0.18612(19) 0.0417(8) Uani 1 1 d . . . H14 H 0.2770 0.3183 -0.2299 0.050 Uiso 1 1 calc R . . C15 C 0.2835(3) 0.22646(18) -0.15204(17) 0.0335(7) Uani 1 1 d . . . H15 H 0.2308 0.1944 -0.1734 0.040 Uiso 1 1 calc R . . C16 C 0.3306(3) 0.19741(16) -0.08618(15) 0.0251(7) Uani 1 1 d . . . C17 C 0.1550(2) 0.22919(15) 0.10994(15) 0.0203(6) Uani 1 1 d . . . C18 C 0.1109(2) 0.31262(16) 0.11995(15) 0.0211(6) Uani 1 1 d . . . C19 C 0.0329(2) 0.32891(16) 0.18460(15) 0.0195(6) Uani 1 1 d . . . C20 C 0.0205(3) 0.46826(16) 0.13760(15) 0.0248(6) Uani 1 1 d . . . C21 C -0.0331(3) 0.54352(17) 0.14765(17) 0.0320(7) Uani 1 1 d . . . H21 H -0.0902 0.5515 0.1877 0.038 Uiso 1 1 calc R . . C22 C -0.0015(3) 0.60633(18) 0.09822(18) 0.0379(8) Uani 1 1 d . . . H22 H -0.0383 0.6582 0.1039 0.046 Uiso 1 1 calc R . . C23 C 0.0833(3) 0.59520(18) 0.03997(18) 0.0375(8) Uani 1 1 d . . . H23 H 0.1067 0.6398 0.0075 0.045 Uiso 1 1 calc R . . C24 C 0.1337(3) 0.51959(17) 0.02916(17) 0.0324(7) Uani 1 1 d . . . H24 H 0.1902 0.5120 -0.0113 0.039 Uiso 1 1 calc R . . C25 C 0.1012(3) 0.45398(16) 0.07804(16) 0.0253(7) Uani 1 1 d . . . C26 C 0.1426(3) 0.37246(16) 0.06949(15) 0.0245(6) Uani 1 1 d . . . H26 H 0.1930 0.3605 0.0277 0.029 Uiso 1 1 calc R . . C27 C 0.4979(2) 0.05112(16) 0.33395(15) 0.0227(6) Uani 1 1 d . . . C28 C 0.5042(3) -0.02143(17) 0.30034(17) 0.0282(7) Uani 1 1 d . . . H28 H 0.4713 -0.0223 0.2551 0.034 Uiso 1 1 calc R . . C29 C 0.5574(3) -0.09063(17) 0.33249(18) 0.0333(8) Uani 1 1 d . . . H29 H 0.5596 -0.1387 0.3095 0.040 Uiso 1 1 calc R . . C30 C 0.6080(3) -0.09101(18) 0.39805(18) 0.0344(8) Uani 1 1 d . . . H30 H 0.6427 -0.1392 0.4204 0.041 Uiso 1 1 calc R . . C31 C 0.6071(3) -0.02092(17) 0.43009(17) 0.0295(7) Uani 1 1 d . . . H31 H 0.6436 -0.0211 0.4744 0.035 Uiso 1 1 calc R . . C32 C 0.5541(2) 0.05088(16) 0.39946(15) 0.0229(6) Uani 1 1 d . . . C33 C 0.5615(2) 0.12256(17) 0.43587(15) 0.0247(6) Uani 1 1 d . . . H33 H 0.6062 0.1178 0.4775 0.030 Uiso 1 1 calc R . . C34 C 0.5308(3) 0.25879(17) 0.45997(16) 0.0270(7) Uani 1 1 d . . . H34A H 0.6034 0.2881 0.4396 0.032 Uiso 1 1 calc R . . H34B H 0.5437 0.2382 0.5103 0.032 Uiso 1 1 calc R . . C35 C 0.4161(3) 0.31426(17) 0.45783(15) 0.0287(7) Uani 1 1 d . . . H35A H 0.3470 0.2897 0.4879 0.034 Uiso 1 1 calc R . . H35B H 0.4307 0.3662 0.4757 0.034 Uiso 1 1 calc R . . C36 C 0.3889(2) 0.39561(17) 0.34840(17) 0.0278(7) Uani 1 1 d . . . H36 H 0.3913 0.4402 0.3758 0.033 Uiso 1 1 calc R . . C37 C 0.3844(2) 0.41109(16) 0.27184(17) 0.0272(7) Uani 1 1 d . . . C38 C 0.3630(3) 0.49091(18) 0.24251(19) 0.0374(8) Uani 1 1 d . . . H38 H 0.3471 0.5320 0.2740 0.045 Uiso 1 1 calc R . . C39 C 0.3646(3) 0.5103(2) 0.1698(2) 0.0455(9) Uani 1 1 d . . . H39 H 0.3464 0.5639 0.1510 0.055 Uiso 1 1 calc R . . C40 C 0.3931(3) 0.4507(2) 0.1238(2) 0.0434(9) Uani 1 1 d . . . H40 H 0.3966 0.4641 0.0732 0.052 Uiso 1 1 calc R . . C41 C 0.4165(3) 0.37236(19) 0.15037(17) 0.0342(7) Uani 1 1 d . . . H41 H 0.4363 0.3329 0.1176 0.041 Uiso 1 1 calc R . . C42 C 0.4116(2) 0.34968(17) 0.22468(16) 0.0256(7) Uani 1 1 d . . . C43 C 0.1517(2) 0.17102(15) 0.41162(15) 0.0185(6) Uani 1 1 d . . . C44 C 0.0554(2) 0.13812(15) 0.46523(14) 0.0178(6) Uani 1 1 d . . . C45 C -0.0734(2) 0.14575(16) 0.44966(16) 0.0237(6) Uani 1 1 d . . . C46 C -0.1222(2) 0.07365(15) 0.56647(15) 0.0222(6) Uani 1 1 d . . . C47 C -0.2144(3) 0.04189(17) 0.61439(16) 0.0307(7) Uani 1 1 d . . . H47 H -0.2975 0.0480 0.6034 0.037 Uiso 1 1 calc R . . C48 C -0.1825(3) 0.00116(17) 0.67835(17) 0.0320(7) Uani 1 1 d . . . H48 H -0.2445 -0.0209 0.7118 0.038 Uiso 1 1 calc R . . C49 C -0.0613(3) -0.00800(17) 0.69446(17) 0.0326(7) Uani 1 1 d . . . H49 H -0.0405 -0.0360 0.7387 0.039 Uiso 1 1 calc R . . C50 C 0.0292(3) 0.02364(16) 0.64598(16) 0.0285(7) Uani 1 1 d . . . H50 H 0.1123 0.0169 0.6569 0.034 Uiso 1 1 calc R . . C51 C -0.0002(2) 0.06537(15) 0.58104(15) 0.0206(6) Uani 1 1 d . . . C52 C 0.0878(2) 0.10039(15) 0.52822(15) 0.0198(6) Uani 1 1 d . . . H52 H 0.1717 0.0970 0.5378 0.024 Uiso 1 1 calc R . . C53 C 0.6597(3) 0.40743(16) 0.54550(15) 0.0242(6) Uani 1 1 d . . . C54 C 0.5478(3) 0.40655(16) 0.58791(16) 0.0268(7) Uani 1 1 d . . . H54 H 0.4853 0.4463 0.5770 0.032 Uiso 1 1 calc R . . C55 C 0.5263(3) 0.34952(18) 0.64488(17) 0.0335(7) Uani 1 1 d . . . H55 H 0.4495 0.3505 0.6725 0.040 Uiso 1 1 calc R . . C56 C 0.6157(3) 0.29044(19) 0.66251(18) 0.0404(8) Uani 1 1 d . . . H56 H 0.6002 0.2508 0.7015 0.048 Uiso 1 1 calc R . . C57 C 0.7267(3) 0.29019(18) 0.62267(18) 0.0362(8) Uani 1 1 d . . . H57 H 0.7880 0.2500 0.6348 0.043 Uiso 1 1 calc R . . C58 C 0.7522(3) 0.34802(16) 0.56427(16) 0.0272(7) Uani 1 1 d . . . C59 C 0.8722(3) 0.34481(17) 0.52639(16) 0.0290(7) Uani 1 1 d . . . H59 H 0.9291 0.3038 0.5432 0.035 Uiso 1 1 calc R . . C60 C 1.0365(3) 0.38146(19) 0.44132(17) 0.0335(8) Uani 1 1 d . . . H60A H 1.0661 0.3249 0.4508 0.040 Uiso 1 1 calc R . . H60B H 1.0903 0.4157 0.4636 0.040 Uiso 1 1 calc R . . C61 C 1.0391(3) 0.40460(17) 0.36107(16) 0.0311(7) Uani 1 1 d . . . H61A H 1.1242 0.4099 0.3397 0.037 Uiso 1 1 calc R . . H61B H 1.0001 0.3641 0.3367 0.037 Uiso 1 1 calc R . . C62 C 1.0207(3) 0.54510(19) 0.32611(16) 0.0310(7) Uani 1 1 d . . . H62 H 1.1008 0.5392 0.3030 0.037 Uiso 1 1 calc R . . C63 C 0.9641(3) 0.62518(17) 0.32712(16) 0.0268(7) Uani 1 1 d . . . C64 C 1.0173(3) 0.68717(19) 0.28196(17) 0.0354(8) Uani 1 1 d . . . H64 H 1.0881 0.6750 0.2513 0.043 Uiso 1 1 calc R . . C65 C 0.9710(3) 0.76515(19) 0.28035(18) 0.0374(8) Uani 1 1 d . . . H65 H 1.0082 0.8062 0.2489 0.045 Uiso 1 1 calc R . . C66 C 0.8677(3) 0.78216(19) 0.32637(17) 0.0357(8) Uani 1 1 d . . . H66 H 0.8331 0.8354 0.3256 0.043 Uiso 1 1 calc R . . C67 C 0.8154(3) 0.72288(17) 0.37281(16) 0.0317(7) Uani 1 1 d . . . H67 H 0.7457 0.7365 0.4038 0.038 Uiso 1 1 calc R . . C68 C 0.8615(3) 0.64268(16) 0.37604(15) 0.0242(6) Uani 1 1 d . . . C69 C 0.7242(2) 0.39595(16) 0.29604(15) 0.0212(6) Uani 1 1 d . . . C70 C 0.7252(2) 0.33489(16) 0.24419(14) 0.0200(6) Uani 1 1 d . . . C71 C 0.7334(3) 0.35983(18) 0.16743(16) 0.0265(7) Uani 1 1 d . . . C72 C 0.7838(3) 0.22110(17) 0.14720(16) 0.0282(7) Uani 1 1 d . . . C73 C 0.8260(3) 0.16858(19) 0.09712(17) 0.0371(8) Uani 1 1 d . . . H73 H 0.8461 0.1875 0.0483 0.045 Uiso 1 1 calc R . . C74 C 0.8380(3) 0.0880(2) 0.11966(18) 0.0407(8) Uani 1 1 d . . . H74 H 0.8675 0.0510 0.0861 0.049 Uiso 1 1 calc R . . C75 C 0.8075(3) 0.06025(19) 0.19119(18) 0.0355(8) Uani 1 1 d . . . H75 H 0.8128 0.0045 0.2057 0.043 Uiso 1 1 calc R . . C76 C 0.7696(3) 0.11385(17) 0.24084(16) 0.0288(7) Uani 1 1 d . . . H76 H 0.7513 0.0949 0.2899 0.035 Uiso 1 1 calc R . . C77 C 0.7577(2) 0.19610(16) 0.21961(15) 0.0239(6) Uani 1 1 d . . . C78 C 0.7324(2) 0.25639(16) 0.26827(15) 0.0217(6) Uani 1 1 d . . . H78 H 0.7205 0.2411 0.3185 0.026 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 Fe1 0.0272(2) 0.0192(2) 0.0198(2) -0.00343(17) -0.00299(17) -0.00067(16) Fe2 0.0158(2) 0.0232(2) 0.0176(2) -0.00413(16) -0.00230(16) -0.00210(15) Fe3 0.0232(2) 0.0272(2) 0.0208(2) -0.00556(18) -0.00325(17) 0.00527(16) O1 0.0388(12) 0.0189(11) 0.0327(12) -0.0008(9) -0.0104(10) -0.0032(8) O2 0.0377(12) 0.0232(11) 0.0203(11) -0.0040(8) -0.0003(9) -0.0003(8) O3 0.0350(12) 0.0183(10) 0.0235(11) -0.0010(8) -0.0011(9) 0.0030(8) O4 0.0293(11) 0.0242(10) 0.0194(11) -0.0041(8) -0.0037(8) 0.0017(8) O5 0.0186(10) 0.0293(11) 0.0235(11) 0.0019(9) -0.0015(8) 0.0019(8) O6 0.0255(11) 0.0237(10) 0.0233(11) -0.0025(8) -0.0002(8) 0.0018(8) O7 0.0239(11) 0.0259(11) 0.0221(11) -0.0052(8) -0.0063(8) 0.0005(8) O8 0.0192(10) 0.0301(11) 0.0226(11) -0.0021(9) 0.0003(8) -0.0024(8) O9 0.0172(10) 0.0308(11) 0.0172(10) -0.0006(8) 0.0001(8) -0.0036(8) O10 0.0170(10) 0.0282(11) 0.0216(11) -0.0001(8) -0.0042(8) -0.0036(8) O11 0.0196(11) 0.0581(14) 0.0267(13) 0.0125(11) -0.0066(9) -0.0004(9) O12 0.0148(10) 0.0440(12) 0.0231(12) 0.0076(9) -0.0022(8) -0.0029(8) O13 0.0318(12) 0.0308(11) 0.0231(12) 0.0005(9) 0.0012(9) 0.0085(9) O14 0.0309(11) 0.0280(11) 0.0213(11) -0.0064(9) 0.0017(9) 0.0029(8) O15 0.0315(12) 0.0279(11) 0.0263(12) -0.0061(9) -0.0067(9) 0.0039(8) O16 0.0291(11) 0.0289(11) 0.0184(11) -0.0014(8) -0.0064(9) -0.0002(8) O17 0.0388(13) 0.0333(13) 0.0239(12) 0.0030(10) -0.0061(9) -0.0012(9) O18 0.0398(13) 0.0343(12) 0.0210(12) -0.0029(9) 0.0008(9) -0.0032(9) N1 0.0295(14) 0.0219(13) 0.0205(13) -0.0042(10) -0.0023(10) 0.0022(10) N2 0.0297(14) 0.0239(13) 0.0240(14) -0.0070(11) -0.0021(11) 0.0000(10) N3 0.0266(13) 0.0243(13) 0.0177(14) -0.0029(11) -0.0013(11) 0.0008(10) N4 0.0159(12) 0.0269(13) 0.0213(13) -0.0047(10) -0.0030(10) -0.0024(9) N5 0.0223(13) 0.0267(14) 0.0240(14) -0.0062(11) -0.0029(10) -0.0011(10) N6 0.0138(12) 0.0271(13) 0.0191(14) -0.0022(10) -0.0016(10) -0.0012(10) N7 0.0279(14) 0.0356(14) 0.0233(15) -0.0118(12) -0.0076(11) 0.0084(11) N8 0.0262(14) 0.0317(14) 0.0241(14) -0.0116(11) -0.0044(11) 0.0056(11) N9 0.0228(13) 0.0321(15) 0.0210(14) -0.0039(12) -0.0055(11) 0.0024(10) C1 0.0374(18) 0.0206(15) 0.0216(17) -0.0057(12) 0.0030(13) -0.0029(12) C2 0.0369(18) 0.0259(17) 0.0303(18) -0.0054(13) 0.0034(14) -0.0014(13) C3 0.040(2) 0.0307(18) 0.037(2) -0.0056(15) 0.0096(15) -0.0099(14) C4 0.051(2) 0.0232(16) 0.041(2) 0.0021(14) 0.0126(17) -0.0029(15) C5 0.042(2) 0.0275(17) 0.0292(18) 0.0026(14) 0.0053(15) 0.0039(14) C6 0.0344(17) 0.0221(15) 0.0213(16) -0.0039(12) 0.0030(13) 0.0003(12) C7 0.0368(18) 0.0265(17) 0.0200(17) -0.0031(13) -0.0015(13) 0.0076(13) C8 0.0300(17) 0.0315(17) 0.0244(17) -0.0017(13) -0.0043(13) 0.0033(13) C9 0.0315(17) 0.0341(17) 0.0250(18) -0.0056(13) -0.0075(13) -0.0030(13) C10 0.0257(16) 0.0251(16) 0.0327(18) -0.0064(14) 0.0004(13) -0.0033(12) C11 0.0251(16) 0.0261(16) 0.0292(18) -0.0019(13) 0.0029(13) 0.0021(12) C12 0.0306(18) 0.0316(18) 0.051(2) 0.0061(16) 0.0012(16) -0.0044(13) C13 0.044(2) 0.038(2) 0.051(2) 0.0218(17) -0.0024(18) -0.0022(16) C14 0.0342(19) 0.049(2) 0.037(2) 0.0147(17) -0.0004(16) 0.0042(15) C15 0.0301(18) 0.0403(19) 0.0280(18) -0.0001(15) 0.0027(14) 0.0032(14) C16 0.0254(16) 0.0247(16) 0.0226(17) -0.0013(13) 0.0066(13) 0.0055(12) C17 0.0189(15) 0.0232(15) 0.0185(16) -0.0017(12) 0.0010(12) -0.0030(11) C18 0.0168(14) 0.0247(15) 0.0220(16) -0.0043(12) -0.0016(12) -0.0006(11) C19 0.0125(14) 0.0236(15) 0.0237(16) -0.0041(13) -0.0064(11) -0.0002(11) C20 0.0268(16) 0.0234(15) 0.0250(17) -0.0016(13) -0.0055(13) -0.0037(12) C21 0.0330(18) 0.0283(17) 0.0357(19) -0.0079(14) -0.0061(14) 0.0016(13) C22 0.049(2) 0.0210(16) 0.046(2) -0.0060(15) -0.0121(17) -0.0011(14) C23 0.045(2) 0.0273(17) 0.041(2) 0.0046(15) -0.0108(16) -0.0118(14) C24 0.0336(18) 0.0324(18) 0.0316(19) 0.0018(14) -0.0060(14) -0.0082(13) C25 0.0237(16) 0.0245(15) 0.0282(17) -0.0007(13) -0.0053(13) -0.0039(12) C26 0.0233(15) 0.0292(16) 0.0209(16) -0.0032(13) -0.0012(12) -0.0003(12) C27 0.0150(14) 0.0276(16) 0.0249(17) -0.0034(13) 0.0029(12) -0.0004(11) C28 0.0250(16) 0.0315(17) 0.0285(18) -0.0075(13) 0.0034(13) -0.0055(12) C29 0.0265(17) 0.0247(16) 0.048(2) -0.0078(15) 0.0051(15) -0.0014(13) C30 0.0260(17) 0.0277(17) 0.047(2) 0.0006(15) 0.0014(15) 0.0056(13) C31 0.0202(16) 0.0361(18) 0.0304(18) 0.0022(14) -0.0024(13) 0.0054(12) C32 0.0139(14) 0.0305(16) 0.0232(17) -0.0024(13) 0.0030(12) 0.0007(11) C33 0.0155(14) 0.0395(18) 0.0198(16) -0.0036(13) -0.0037(12) -0.0013(12) C34 0.0278(16) 0.0326(16) 0.0229(17) -0.0057(13) -0.0083(13) -0.0064(12) C35 0.0320(17) 0.0329(17) 0.0235(17) -0.0120(13) -0.0045(13) -0.0025(13) C36 0.0215(16) 0.0242(16) 0.040(2) -0.0093(14) -0.0057(13) -0.0030(12) C37 0.0184(15) 0.0267(16) 0.0370(19) 0.0021(14) -0.0068(13) -0.0074(12) C38 0.0268(18) 0.0322(18) 0.054(2) 0.0028(16) -0.0097(16) -0.0088(13) C39 0.035(2) 0.037(2) 0.062(3) 0.0204(19) -0.0144(18) -0.0105(15) C40 0.0319(19) 0.057(2) 0.039(2) 0.0186(18) -0.0082(16) -0.0136(16) C41 0.0276(17) 0.043(2) 0.0314(19) 0.0042(15) -0.0033(14) -0.0065(14) C42 0.0130(14) 0.0337(17) 0.0295(18) 0.0036(14) -0.0017(12) -0.0071(12) C43 0.0177(15) 0.0177(14) 0.0211(16) -0.0050(12) -0.0033(12) 0.0000(10) C44 0.0170(14) 0.0173(13) 0.0194(15) -0.0034(11) -0.0013(11) -0.0012(10) C45 0.0182(15) 0.0283(16) 0.0239(17) -0.0003(13) 0.0004(13) -0.0018(12) C46 0.0226(15) 0.0210(14) 0.0226(16) 0.0009(12) -0.0032(12) -0.0005(11) C47 0.0199(16) 0.0400(18) 0.0307(19) 0.0037(14) 0.0000(13) -0.0026(13) C48 0.0265(17) 0.0347(18) 0.0332(19) 0.0037(14) 0.0030(14) -0.0077(13) C49 0.0349(19) 0.0331(17) 0.0285(18) 0.0095(14) -0.0061(14) -0.0060(13) C50 0.0224(16) 0.0288(16) 0.0336(19) 0.0068(14) -0.0089(13) -0.0037(12) C51 0.0214(15) 0.0160(14) 0.0246(16) -0.0009(12) -0.0037(12) -0.0020(11) C52 0.0146(14) 0.0189(14) 0.0259(17) -0.0011(12) -0.0039(12) -0.0001(10) C53 0.0347(17) 0.0206(15) 0.0189(16) -0.0063(12) -0.0073(13) -0.0010(12) C54 0.0310(17) 0.0240(15) 0.0270(17) -0.0075(13) -0.0050(13) -0.0011(12) C55 0.0364(19) 0.0357(18) 0.0294(19) -0.0019(14) -0.0055(14) -0.0091(14) C56 0.046(2) 0.0389(19) 0.036(2) 0.0114(15) -0.0122(16) -0.0135(15) C57 0.046(2) 0.0259(17) 0.039(2) 0.0018(14) -0.0215(16) -0.0010(14) C58 0.0343(18) 0.0240(15) 0.0255(17) -0.0077(13) -0.0126(13) 0.0027(12) C59 0.0352(18) 0.0264(16) 0.0283(18) -0.0098(14) -0.0180(14) 0.0094(13) C60 0.0271(17) 0.0409(18) 0.0336(19) -0.0130(15) -0.0097(14) 0.0146(13) C61 0.0252(16) 0.0374(18) 0.0314(19) -0.0129(14) -0.0028(13) 0.0103(13) C62 0.0219(16) 0.048(2) 0.0249(18) -0.0145(15) -0.0012(13) 0.0033(14) C63 0.0250(16) 0.0338(17) 0.0231(17) -0.0104(13) -0.0016(13) -0.0021(12) C64 0.0304(18) 0.043(2) 0.0333(19) -0.0122(15) 0.0046(14) -0.0054(14) C65 0.040(2) 0.0372(19) 0.036(2) -0.0054(15) 0.0023(15) -0.0132(15) C66 0.044(2) 0.0321(18) 0.0319(19) -0.0099(15) -0.0020(15) -0.0008(14) C67 0.0361(18) 0.0317(17) 0.0277(18) -0.0087(14) 0.0022(14) -0.0010(13) C68 0.0244(16) 0.0299(16) 0.0207(16) -0.0093(13) -0.0065(12) -0.0020(12) C69 0.0141(14) 0.0270(16) 0.0217(17) -0.0001(12) -0.0001(12) -0.0006(11) C70 0.0115(14) 0.0308(16) 0.0179(15) -0.0017(12) -0.0016(11) -0.0036(11) C71 0.0218(16) 0.0349(18) 0.0240(17) -0.0042(14) -0.0046(13) -0.0066(12) C72 0.0232(16) 0.0355(18) 0.0268(18) -0.0037(14) -0.0033(13) -0.0044(12) C73 0.041(2) 0.047(2) 0.0234(18) -0.0085(15) 0.0015(15) 0.0012(15) C74 0.043(2) 0.043(2) 0.037(2) -0.0152(16) -0.0050(16) 0.0072(15) C75 0.0344(18) 0.0358(18) 0.037(2) -0.0060(15) -0.0091(15) 0.0040(14) C76 0.0258(16) 0.0360(18) 0.0249(17) -0.0024(14) -0.0049(13) -0.0011(13) C77 0.0155(14) 0.0329(17) 0.0237(17) -0.0030(13) -0.0017(12) -0.0051(11) C78 0.0129(14) 0.0318(17) 0.0202(16) -0.0017(12) 0.0002(11) -0.0025(11) _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 Fe1 O1 1.9094(19) . ? Fe1 O2 1.9467(19) . ? Fe1 O3 2.0102(19) . ? Fe1 O4 2.0652(18) . ? Fe1 N2 2.122(2) . ? Fe1 N1 2.157(2) . ? Fe2 O7 1.9248(17) . ? Fe2 O8 1.9254(19) . ? Fe2 O9 2.0021(18) . ? Fe2 O10 2.1527(18) . ? Fe2 N4 2.154(2) . ? Fe2 N5 2.111(2) . ? Fe3 O13 1.9161(19) . ? Fe3 O14 1.9343(19) . ? Fe3 O15 2.016(2) . ? Fe3 O16 2.0882(18) . ? Fe3 N8 2.123(2) . ? Fe3 N7 2.188(2) . ? O1 C1 1.313(3) . ? O2 C16 1.318(3) . ? O3 N3 1.360(3) . ? O4 C17 1.277(3) . ? O5 C19 1.205(3) . ? O6 C19 1.378(3) . ? O6 C20 1.378(3) . ? O7 C27 1.315(3) . ? O8 C42 1.315(3) . ? O9 N6 1.362(3) . ? O10 C43 1.268(3) . ? O11 C45 1.203(3) . ? O12 C45 1.382(3) . ? O12 C46 1.382(3) . ? O13 C53 1.320(3) . ? O14 C68 1.312(3) . ? O15 N9 1.361(3) . ? O16 C69 1.275(3) . ? O17 C71 1.214(3) . ? O18 C71 1.378(3) . ? O18 C72 1.388(3) . ? N1 C7 1.283(3) . ? N1 C8 1.474(4) . ? N2 C10 1.278(4) . ? N2 C9 1.464(4) . ? N3 C17 1.302(4) . ? N3 H3N 0.85(2) . ? N4 C33 1.282(3) . ? N4 C34 1.478(3) . ? N5 C36 1.285(4) . ? N5 C35 1.458(4) . ? N6 C43 1.308(3) . ? N6 H6N 0.84(2) . ? N7 C59 1.284(4) . ? N7 C60 1.475(4) . ? N8 C62 1.276(4) . ? N8 C61 1.469(3) . ? N9 C69 1.310(4) . ? N9 H9N 0.85(2) . ? C1 C2 1.411(4) . ? C1 C6 1.426(4) . ? C2 C3 1.375(4) . ? C2 H2 0.9500 . ? C3 C4 1.406(5) . ? C3 H3 0.9500 . ? C4 C5 1.374(4) . ? C4 H4 0.9500 . ? C5 C6 1.406(4) . ? C5 H5 0.9500 . ? C6 C7 1.439(4) . ? C7 H7 0.9500 . ? C8 C9 1.525(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.450(4) . ? C10 H10 0.9500 . ? C11 C12 1.406(4) . ? C11 C16 1.423(4) . ? C12 C13 1.373(5) . ? C12 H12 0.9500 . ? C13 C14 1.391(5) . ? C13 H13 0.9500 . ? C14 C15 1.373(4) . ? C14 H14 0.9500 . ? C15 C16 1.410(4) . ? C15 H15 0.9500 . ? C17 C18 1.480(4) . ? C18 C26 1.350(4) . ? C18 C19 1.460(4) . ? C20 C21 1.386(4) . ? C20 C25 1.393(4) . ? C21 C22 1.373(4) . ? C21 H21 0.9500 . ? C22 C23 1.391(5) . ? C22 H22 0.9500 . ? C23 C24 1.381(4) . ? C23 H23 0.9500 . ? C24 C25 1.404(4) . ? C24 H24 0.9500 . ? C25 C26 1.437(4) . ? C26 H26 0.9500 . ? C27 C32 1.418(4) . ? C27 C28 1.420(4) . ? C28 C29 1.378(4) . ? C28 H28 0.9500 . ? C29 C30 1.388(5) . ? C29 H29 0.9500 . ? C30 C31 1.371(4) . ? C30 H30 0.9500 . ? C31 C32 1.401(4) . ? C31 H31 0.9500 . ? C32 C33 1.449(4) . ? C33 H33 0.9500 . ? C34 C35 1.523(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.435(4) . ? C36 H36 0.9500 . ? C37 C38 1.413(4) . ? C37 C42 1.424(4) . ? C38 C39 1.367(5) . ? C38 H38 0.9500 . ? C39 C40 1.387(5) . ? C39 H39 0.9500 . ? C40 C41 1.378(4) . ? C40 H40 0.9500 . ? C41 C42 1.403(4) . ? C41 H41 0.9500 . ? C43 C44 1.486(4) . ? C44 C52 1.348(4) . ? C44 C45 1.464(4) . ? C46 C51 1.386(4) . ? C46 C47 1.388(4) . ? C47 C48 1.381(4) . ? C47 H47 0.9500 . ? C48 C49 1.386(4) . ? C48 H48 0.9500 . ? C49 C50 1.381(4) . ? C49 H49 0.9500 . ? C50 C51 1.395(4) . ? C50 H50 0.9500 . ? C51 C52 1.431(4) . ? C52 H52 0.9500 . ? C53 C54 1.405(4) . ? C53 C58 1.423(4) . ? C54 C55 1.376(4) . ? C54 H54 0.9500 . ? C55 C56 1.391(4) . ? C55 H55 0.9500 . ? C56 C57 1.373(5) . ? C56 H56 0.9500 . ? C57 C58 1.410(4) . ? C57 H57 0.9500 . ? C58 C59 1.442(4) . ? C59 H59 0.9500 . ? C60 C61 1.512(4) . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C62 C63 1.449(4) . ? C62 H62 0.9500 . ? C63 C64 1.398(4) . ? C63 C68 1.425(4) . ? C64 C65 1.376(4) . ? C64 H64 0.9500 . ? C65 C66 1.397(4) . ? C65 H65 0.9500 . ? C66 C67 1.374(4) . ? C66 H66 0.9500 . ? C67 C68 1.409(4) . ? C67 H67 0.9500 . ? C69 C70 1.478(4) . ? C70 C78 1.351(4) . ? C70 C71 1.453(4) . ? C72 C73 1.382(4) . ? C72 C77 1.390(4) . ? C73 C74 1.381(4) . ? C73 H73 0.9500 . ? C74 C75 1.393(5) . ? C74 H74 0.9500 . ? C75 C76 1.378(4) . ? C75 H75 0.9500 . ? C76 C77 1.402(4) . ? C76 H76 0.9500 . ? C77 C78 1.427(4) . ? C78 H78 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe1 O2 93.83(8) . . ? O1 Fe1 O3 97.02(8) . . ? O2 Fe1 O3 162.31(7) . . ? O1 Fe1 O4 109.53(8) . . ? O2 Fe1 O4 84.88(8) . . ? O3 Fe1 O4 78.35(7) . . ? O1 Fe1 N2 159.89(9) . . ? O2 Fe1 N2 84.41(9) . . ? O3 Fe1 N2 90.05(8) . . ? O4 Fe1 N2 90.30(8) . . ? O1 Fe1 N1 86.93(8) . . ? O2 Fe1 N1 111.42(8) . . ? O3 Fe1 N1 83.16(8) . . ? O4 Fe1 N1 156.49(8) . . ? N2 Fe1 N1 75.21(9) . . ? O7 Fe2 O8 92.43(8) . . ? O7 Fe2 O9 103.20(7) . . ? O8 Fe2 O9 85.59(8) . . ? O7 Fe2 N5 157.48(8) . . ? O8 Fe2 N5 85.19(8) . . ? O9 Fe2 N5 98.94(8) . . ? O7 Fe2 O10 96.80(7) . . ? O8 Fe2 O10 160.79(7) . . ? O9 Fe2 O10 75.93(7) . . ? N5 Fe2 O10 92.45(8) . . ? O7 Fe2 N4 86.03(8) . . ? O8 Fe2 N4 116.88(8) . . ? O9 Fe2 N4 155.64(8) . . ? N5 Fe2 N4 75.25(9) . . ? O10 Fe2 N4 80.66(8) . . ? O13 Fe3 O14 93.42(8) . . ? O13 Fe3 O15 111.13(8) . . ? O14 Fe3 O15 83.08(8) . . ? O13 Fe3 O16 96.56(8) . . ? O14 Fe3 O16 160.18(8) . . ? O15 Fe3 O16 77.36(7) . . ? O13 Fe3 N8 156.31(9) . . ? O14 Fe3 N8 85.48(8) . . ? O15 Fe3 N8 92.26(9) . . ? O16 Fe3 N8 92.06(8) . . ? O13 Fe3 N7 84.80(9) . . ? O14 Fe3 N7 114.30(9) . . ? O15 Fe3 N7 156.35(8) . . ? O16 Fe3 N7 83.72(8) . . ? N8 Fe3 N7 74.23(9) . . ? C1 O1 Fe1 132.58(19) . . ? C16 O2 Fe1 124.83(17) . . ? N3 O3 Fe1 110.26(15) . . ? C17 O4 Fe1 110.86(17) . . ? C19 O6 C20 122.8(2) . . ? C27 O7 Fe2 132.63(17) . . ? C42 O8 Fe2 129.10(17) . . ? N6 O9 Fe2 114.80(15) . . ? C43 O10 Fe2 112.50(17) . . ? C45 O12 C46 122.8(2) . . ? C53 O13 Fe3 134.70(17) . . ? C68 O14 Fe3 125.73(16) . . ? N9 O15 Fe3 111.43(15) . . ? C69 O16 Fe3 111.76(16) . . ? C71 O18 C72 122.2(2) . . ? C7 N1 C8 119.0(2) . . ? C7 N1 Fe1 124.8(2) . . ? C8 N1 Fe1 115.77(16) . . ? C10 N2 C9 122.2(2) . . ? C10 N2 Fe1 125.5(2) . . ? C9 N2 Fe1 111.89(18) . . ? C17 N3 O3 118.1(2) . . ? C17 N3 H3N 124(2) . . ? O3 N3 H3N 117(2) . . ? C33 N4 C34 118.5(2) . . ? C33 N4 Fe2 124.96(19) . . ? C34 N4 Fe2 115.77(17) . . ? C36 N5 C35 120.2(2) . . ? C36 N5 Fe2 126.6(2) . . ? C35 N5 Fe2 112.59(17) . . ? C43 N6 O9 117.7(2) . . ? C43 N6 H6N 127(2) . . ? O9 N6 H6N 115(2) . . ? C59 N7 C60 118.2(3) . . ? C59 N7 Fe3 125.6(2) . . ? C60 N7 Fe3 115.55(19) . . ? C62 N8 C61 120.7(3) . . ? C62 N8 Fe3 125.7(2) . . ? C61 N8 Fe3 112.88(19) . . ? C69 N9 O15 118.1(2) . . ? C69 N9 H9N 120(2) . . ? O15 N9 H9N 121(2) . . ? O1 C1 C2 118.6(3) . . ? O1 C1 C6 123.1(3) . . ? C2 C1 C6 118.3(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 119.0(3) . . ? C5 C6 C7 117.9(3) . . ? C1 C6 C7 123.1(3) . . ? N1 C7 C6 126.2(3) . . ? N1 C7 H7 116.9 . . ? C6 C7 H7 116.9 . . ? N1 C8 C9 107.6(2) . . ? N1 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? N1 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N2 C9 C8 105.0(2) . . ? N2 C9 H9A 110.7 . . ? C8 C9 H9A 110.7 . . ? N2 C9 H9B 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? N2 C10 C11 123.2(3) . . ? N2 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C12 C11 C16 119.1(3) . . ? C12 C11 C10 119.0(3) . . ? C16 C11 C10 121.7(3) . . ? C13 C12 C11 121.9(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 120.8(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? O2 C16 C15 119.7(3) . . ? O2 C16 C11 122.8(3) . . ? C15 C16 C11 117.5(3) . . ? O4 C17 N3 119.6(2) . . ? O4 C17 C18 120.7(2) . . ? N3 C17 C18 119.7(2) . . ? C26 C18 C19 120.9(2) . . ? C26 C18 C17 119.9(2) . . ? C19 C18 C17 119.2(2) . . ? O5 C19 O6 116.8(2) . . ? O5 C19 C18 126.5(2) . . ? O6 C19 C18 116.6(2) . . ? O6 C20 C21 116.8(3) . . ? O6 C20 C25 120.9(2) . . ? C21 C20 C25 122.3(3) . . ? C22 C21 C20 118.3(3) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? C21 C22 C23 121.1(3) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 120.2(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C20 C25 C24 118.1(3) . . ? C20 C25 C26 117.6(3) . . ? C24 C25 C26 124.3(3) . . ? C18 C26 C25 121.0(3) . . ? C18 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? O7 C27 C32 123.4(2) . . ? O7 C27 C28 118.8(3) . . ? C32 C27 C28 117.8(3) . . ? C29 C28 C27 120.9(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 120.9(3) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C31 C30 C29 119.2(3) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C30 C31 C32 121.9(3) . . ? C30 C31 H31 119.0 . . ? C32 C31 H31 119.0 . . ? C31 C32 C27 119.2(3) . . ? C31 C32 C33 118.0(3) . . ? C27 C32 C33 122.7(2) . . ? N4 C33 C32 125.7(3) . . ? N4 C33 H33 117.1 . . ? C32 C33 H33 117.1 . . ? N4 C34 C35 107.5(2) . . ? N4 C34 H34A 110.2 . . ? C35 C34 H34A 110.2 . . ? N4 C34 H34B 110.2 . . ? C35 C34 H34B 110.2 . . ? H34A C34 H34B 108.5 . . ? N5 C35 C34 105.3(2) . . ? N5 C35 H35A 110.7 . . ? C34 C35 H35A 110.7 . . ? N5 C35 H35B 110.7 . . ? C34 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? N5 C36 C37 124.2(3) . . ? N5 C36 H36 117.9 . . ? C37 C36 H36 117.9 . . ? C38 C37 C42 119.4(3) . . ? C38 C37 C36 118.6(3) . . ? C42 C37 C36 121.8(3) . . ? C39 C38 C37 121.5(3) . . ? C39 C38 H38 119.3 . . ? C37 C38 H38 119.3 . . ? C38 C39 C40 119.1(3) . . ? C38 C39 H39 120.5 . . ? C40 C39 H39 120.5 . . ? C41 C40 C39 121.1(3) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C40 C41 C42 121.4(3) . . ? C40 C41 H41 119.3 . . ? C42 C41 H41 119.3 . . ? O8 C42 C41 119.5(3) . . ? O8 C42 C37 123.0(3) . . ? C41 C42 C37 117.4(3) . . ? O10 C43 N6 119.0(2) . . ? O10 C43 C44 120.8(2) . . ? N6 C43 C44 120.2(2) . . ? C52 C44 C45 120.2(2) . . ? C52 C44 C43 119.3(2) . . ? C45 C44 C43 120.5(2) . . ? O11 C45 O12 116.6(2) . . ? O11 C45 C44 126.8(3) . . ? O12 C45 C44 116.5(2) . . ? O12 C46 C51 120.8(2) . . ? O12 C46 C47 117.2(2) . . ? C51 C46 C47 121.9(3) . . ? C48 C47 C46 118.5(3) . . ? C48 C47 H47 120.8 . . ? C46 C47 H47 120.8 . . ? C47 C48 C49 120.9(3) . . ? C47 C48 H48 119.5 . . ? C49 C48 H48 119.5 . . ? C50 C49 C48 119.8(3) . . ? C50 C49 H49 120.1 . . ? C48 C49 H49 120.1 . . ? C49 C50 C51 120.6(3) . . ? C49 C50 H50 119.7 . . ? C51 C50 H50 119.7 . . ? C46 C51 C50 118.3(2) . . ? C46 C51 C52 117.6(2) . . ? C50 C51 C52 124.1(3) . . ? C44 C52 C51 122.0(2) . . ? C44 C52 H52 119.0 . . ? C51 C52 H52 119.0 . . ? O13 C53 C54 119.2(2) . . ? O13 C53 C58 123.1(3) . . ? C54 C53 C58 117.7(3) . . ? C55 C54 C53 121.7(3) . . ? C55 C54 H54 119.2 . . ? C53 C54 H54 119.2 . . ? C54 C55 C56 120.7(3) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C57 C56 C55 119.0(3) . . ? C57 C56 H56 120.5 . . ? C55 C56 H56 120.5 . . ? C56 C57 C58 121.8(3) . . ? C56 C57 H57 119.1 . . ? C58 C57 H57 119.1 . . ? C57 C58 C53 119.0(3) . . ? C57 C58 C59 118.3(3) . . ? C53 C58 C59 122.7(3) . . ? N7 C59 C58 125.7(3) . . ? N7 C59 H59 117.1 . . ? C58 C59 H59 117.1 . . ? N7 C60 C61 107.9(2) . . ? N7 C60 H60A 110.1 . . ? C61 C60 H60A 110.1 . . ? N7 C60 H60B 110.1 . . ? C61 C60 H60B 110.1 . . ? H60A C60 H60B 108.4 . . ? N8 C61 C60 104.6(2) . . ? N8 C61 H61A 110.8 . . ? C60 C61 H61A 110.8 . . ? N8 C61 H61B 110.8 . . ? C60 C61 H61B 110.8 . . ? H61A C61 H61B 108.9 . . ? N8 C62 C63 124.0(3) . . ? N8 C62 H62 118.0 . . ? C63 C62 H62 118.0 . . ? C64 C63 C68 119.7(3) . . ? C64 C63 C62 118.5(3) . . ? C68 C63 C62 121.6(3) . . ? C65 C64 C63 122.4(3) . . ? C65 C64 H64 118.8 . . ? C63 C64 H64 118.8 . . ? C64 C65 C66 118.1(3) . . ? C64 C65 H65 121.0 . . ? C66 C65 H65 121.0 . . ? C67 C66 C65 120.9(3) . . ? C67 C66 H66 119.6 . . ? C65 C66 H66 119.6 . . ? C66 C67 C68 122.3(3) . . ? C66 C67 H67 118.9 . . ? C68 C67 H67 118.9 . . ? O14 C68 C67 120.0(2) . . ? O14 C68 C63 123.4(2) . . ? C67 C68 C63 116.6(3) . . ? O16 C69 N9 118.7(2) . . ? O16 C69 C70 121.6(2) . . ? N9 C69 C70 119.6(3) . . ? C78 C70 C71 120.6(2) . . ? C78 C70 C69 119.5(2) . . ? C71 C70 C69 119.4(2) . . ? O17 C71 O18 116.4(3) . . ? O17 C71 C70 127.0(3) . . ? O18 C71 C70 116.5(3) . . ? C73 C72 O18 116.9(3) . . ? C73 C72 C77 122.4(3) . . ? O18 C72 C77 120.7(2) . . ? C74 C73 C72 118.5(3) . . ? C74 C73 H73 120.7 . . ? C72 C73 H73 120.7 . . ? C73 C74 C75 120.7(3) . . ? C73 C74 H74 119.7 . . ? C75 C74 H74 119.7 . . ? C76 C75 C74 119.9(3) . . ? C76 C75 H75 120.0 . . ? C74 C75 H75 120.0 . . ? C75 C76 C77 120.6(3) . . ? C75 C76 H76 119.7 . . ? C77 C76 H76 119.7 . . ? C72 C77 C76 117.8(3) . . ? C72 C77 C78 117.6(3) . . ? C76 C77 C78 124.3(3) . . ? C70 C78 C77 121.2(3) . . ? C70 C78 H78 119.4 . . ? C77 C78 H78 119.4 . . ? 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 O2 Fe1 O1 C1 132.3(2) . . . . ? O3 Fe1 O1 C1 -61.7(2) . . . . ? O4 Fe1 O1 C1 -141.8(2) . . . . ? N2 Fe1 O1 C1 48.1(4) . . . . ? N1 Fe1 O1 C1 21.1(2) . . . . ? O1 Fe1 O2 C16 155.7(2) . . . . ? O3 Fe1 O2 C16 27.8(4) . . . . ? O4 Fe1 O2 C16 46.4(2) . . . . ? N2 Fe1 O2 C16 -44.4(2) . . . . ? N1 Fe1 O2 C16 -116.1(2) . . . . ? O1 Fe1 O3 N3 -122.34(16) . . . . ? O2 Fe1 O3 N3 5.1(4) . . . . ? O4 Fe1 O3 N3 -13.76(15) . . . . ? N2 Fe1 O3 N3 76.54(16) . . . . ? N1 Fe1 O3 N3 151.63(17) . . . . ? O1 Fe1 O4 C17 107.65(17) . . . . ? O2 Fe1 O4 C17 -160.09(17) . . . . ? O3 Fe1 O4 C17 14.25(17) . . . . ? N2 Fe1 O4 C17 -75.73(17) . . . . ? N1 Fe1 O4 C17 -24.6(3) . . . . ? O8 Fe2 O7 C27 139.3(2) . . . . ? O9 Fe2 O7 C27 -134.7(2) . . . . ? N5 Fe2 O7 C27 56.0(3) . . . . ? O10 Fe2 O7 C27 -57.6(2) . . . . ? N4 Fe2 O7 C27 22.5(2) . . . . ? O7 Fe2 O8 C42 167.7(2) . . . . ? O9 Fe2 O8 C42 64.7(2) . . . . ? N5 Fe2 O8 C42 -34.7(2) . . . . ? O10 Fe2 O8 C42 48.9(3) . . . . ? N4 Fe2 O8 C42 -105.5(2) . . . . ? O7 Fe2 O9 N6 92.88(15) . . . . ? O8 Fe2 O9 N6 -175.65(15) . . . . ? N5 Fe2 O9 N6 -91.23(16) . . . . ? O10 Fe2 O9 N6 -0.93(14) . . . . ? N4 Fe2 O9 N6 -17.3(3) . . . . ? O7 Fe2 O10 C43 -100.49(17) . . . . ? O8 Fe2 O10 C43 17.7(3) . . . . ? O9 Fe2 O10 C43 1.47(16) . . . . ? N5 Fe2 O10 C43 100.08(17) . . . . ? N4 Fe2 O10 C43 174.69(17) . . . . ? O14 Fe3 O13 C53 -134.0(2) . . . . ? O15 Fe3 O13 C53 142.1(2) . . . . ? O16 Fe3 O13 C53 63.1(3) . . . . ? N8 Fe3 O13 C53 -47.5(4) . . . . ? N7 Fe3 O13 C53 -19.9(2) . . . . ? O13 Fe3 O14 C68 -163.1(2) . . . . ? O15 Fe3 O14 C68 -52.2(2) . . . . ? O16 Fe3 O14 C68 -42.9(4) . . . . ? N8 Fe3 O14 C68 40.6(2) . . . . ? N7 Fe3 O14 C68 111.1(2) . . . . ? O13 Fe3 O15 N9 -104.77(16) . . . . ? O14 Fe3 O15 N9 164.23(17) . . . . ? O16 Fe3 O15 N9 -12.55(16) . . . . ? N8 Fe3 O15 N9 79.06(17) . . . . ? N7 Fe3 O15 N9 25.1(3) . . . . ? O13 Fe3 O16 C69 124.38(18) . . . . ? O14 Fe3 O16 C69 4.6(3) . . . . ? O15 Fe3 O16 C69 14.13(17) . . . . ? N8 Fe3 O16 C69 -77.73(18) . . . . ? N7 Fe3 O16 C69 -151.61(18) . . . . ? O1 Fe1 N1 C7 -13.7(2) . . . . ? O2 Fe1 N1 C7 -106.6(2) . . . . ? O3 Fe1 N1 C7 83.7(2) . . . . ? O4 Fe1 N1 C7 122.0(2) . . . . ? N2 Fe1 N1 C7 175.6(2) . . . . ? O1 Fe1 N1 C8 174.09(19) . . . . ? O2 Fe1 N1 C8 81.18(19) . . . . ? O3 Fe1 N1 C8 -88.45(19) . . . . ? O4 Fe1 N1 C8 -50.2(3) . . . . ? N2 Fe1 N1 C8 3.41(18) . . . . ? O1 Fe1 N2 C10 113.7(3) . . . . ? O2 Fe1 N2 C10 27.8(2) . . . . ? O3 Fe1 N2 C10 -135.4(2) . . . . ? O4 Fe1 N2 C10 -57.0(2) . . . . ? N1 Fe1 N2 C10 141.7(2) . . . . ? O1 Fe1 N2 C9 -59.8(3) . . . . ? O2 Fe1 N2 C9 -145.69(18) . . . . ? O3 Fe1 N2 C9 51.14(18) . . . . ? O4 Fe1 N2 C9 129.49(18) . . . . ? N1 Fe1 N2 C9 -31.77(17) . . . . ? Fe1 O3 N3 C17 12.4(3) . . . . ? O7 Fe2 N4 C33 -19.7(2) . . . . ? O8 Fe2 N4 C33 -110.4(2) . . . . ? O9 Fe2 N4 C33 94.0(3) . . . . ? N5 Fe2 N4 C33 172.9(2) . . . . ? O10 Fe2 N4 C33 77.9(2) . . . . ? O7 Fe2 N4 C34 170.53(19) . . . . ? O8 Fe2 N4 C34 79.82(19) . . . . ? O9 Fe2 N4 C34 -75.8(3) . . . . ? N5 Fe2 N4 C34 3.16(18) . . . . ? O10 Fe2 N4 C34 -91.90(18) . . . . ? O7 Fe2 N5 C36 105.2(3) . . . . ? O8 Fe2 N5 C36 20.5(2) . . . . ? O9 Fe2 N5 C36 -64.3(2) . . . . ? O10 Fe2 N5 C36 -140.4(2) . . . . ? N4 Fe2 N5 C36 139.9(2) . . . . ? O7 Fe2 N5 C35 -65.9(3) . . . . ? O8 Fe2 N5 C35 -150.64(19) . . . . ? O9 Fe2 N5 C35 124.60(18) . . . . ? O10 Fe2 N5 C35 48.46(18) . . . . ? N4 Fe2 N5 C35 -31.22(18) . . . . ? Fe2 O9 N6 C43 0.3(3) . . . . ? O13 Fe3 N7 C59 17.4(2) . . . . ? O14 Fe3 N7 C59 108.8(2) . . . . ? O15 Fe3 N7 C59 -116.6(3) . . . . ? O16 Fe3 N7 C59 -79.8(2) . . . . ? N8 Fe3 N7 C59 -173.8(2) . . . . ? O13 Fe3 N7 C60 -172.02(19) . . . . ? O14 Fe3 N7 C60 -80.6(2) . . . . ? O15 Fe3 N7 C60 54.0(3) . . . . ? O16 Fe3 N7 C60 90.78(19) . . . . ? N8 Fe3 N7 C60 -3.17(18) . . . . ? O13 Fe3 N8 C62 -110.3(3) . . . . ? O14 Fe3 N8 C62 -22.0(2) . . . . ? O15 Fe3 N8 C62 60.8(2) . . . . ? O16 Fe3 N8 C62 138.3(2) . . . . ? N7 Fe3 N8 C62 -138.9(3) . . . . ? O13 Fe3 N8 C61 60.5(3) . . . . ? O14 Fe3 N8 C61 148.67(19) . . . . ? O15 Fe3 N8 C61 -128.45(18) . . . . ? O16 Fe3 N8 C61 -51.03(19) . . . . ? N7 Fe3 N8 C61 31.85(18) . . . . ? Fe3 O15 N9 C69 10.3(3) . . . . ? Fe1 O1 C1 C2 161.4(2) . . . . ? Fe1 O1 C1 C6 -20.7(4) . . . . ? O1 C1 C2 C3 174.7(3) . . . . ? C6 C1 C2 C3 -3.3(4) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 2.3(5) . . . . ? C3 C4 C5 C6 -2.4(5) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? O1 C1 C6 C5 -174.8(3) . . . . ? C2 C1 C6 C5 3.1(4) . . . . ? O1 C1 C6 C7 5.2(4) . . . . ? C2 C1 C6 C7 -176.9(3) . . . . ? C8 N1 C7 C6 179.1(3) . . . . ? Fe1 N1 C7 C6 7.1(4) . . . . ? C5 C6 C7 N1 -179.8(3) . . . . ? C1 C6 C7 N1 0.2(4) . . . . ? C7 N1 C8 C9 -149.2(3) . . . . ? Fe1 N1 C8 C9 23.4(3) . . . . ? C10 N2 C9 C8 -120.6(3) . . . . ? Fe1 N2 C9 C8 53.2(2) . . . . ? N1 C8 C9 N2 -47.6(3) . . . . ? C9 N2 C10 C11 170.0(2) . . . . ? Fe1 N2 C10 C11 -2.9(4) . . . . ? N2 C10 C11 C12 165.1(3) . . . . ? N2 C10 C11 C16 -20.5(4) . . . . ? C16 C11 C12 C13 1.0(5) . . . . ? C10 C11 C12 C13 175.6(3) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 C15 -0.9(5) . . . . ? C13 C14 C15 C16 1.5(5) . . . . ? Fe1 O2 C16 C15 -143.9(2) . . . . ? Fe1 O2 C16 C11 37.5(3) . . . . ? C14 C15 C16 O2 -179.5(3) . . . . ? C14 C15 C16 C11 -0.8(4) . . . . ? C12 C11 C16 O2 178.2(2) . . . . ? C10 C11 C16 O2 3.8(4) . . . . ? C12 C11 C16 C15 -0.5(4) . . . . ? C10 C11 C16 C15 -174.8(3) . . . . ? Fe1 O4 C17 N3 -12.4(3) . . . . ? Fe1 O4 C17 C18 164.28(19) . . . . ? O3 N3 C17 O4 0.2(4) . . . . ? O3 N3 C17 C18 -176.5(2) . . . . ? O4 C17 C18 C26 -34.0(4) . . . . ? N3 C17 C18 C26 142.6(3) . . . . ? O4 C17 C18 C19 145.8(2) . . . . ? N3 C17 C18 C19 -37.6(4) . . . . ? C20 O6 C19 O5 178.9(2) . . . . ? C20 O6 C19 C18 -3.5(3) . . . . ? C26 C18 C19 O5 -179.1(3) . . . . ? C17 C18 C19 O5 1.1(4) . . . . ? C26 C18 C19 O6 3.5(4) . . . . ? C17 C18 C19 O6 -176.3(2) . . . . ? C19 O6 C20 C21 178.3(2) . . . . ? C19 O6 C20 C25 -0.5(4) . . . . ? O6 C20 C21 C22 178.7(3) . . . . ? C25 C20 C21 C22 -2.4(5) . . . . ? C20 C21 C22 C23 -0.9(5) . . . . ? C21 C22 C23 C24 2.8(5) . . . . ? C22 C23 C24 C25 -1.4(5) . . . . ? O6 C20 C25 C24 -177.5(2) . . . . ? C21 C20 C25 C24 3.7(4) . . . . ? O6 C20 C25 C26 4.5(4) . . . . ? C21 C20 C25 C26 -174.3(3) . . . . ? C23 C24 C25 C20 -1.7(4) . . . . ? C23 C24 C25 C26 176.2(3) . . . . ? C19 C18 C26 C25 0.4(4) . . . . ? C17 C18 C26 C25 -179.8(3) . . . . ? C20 C25 C26 C18 -4.3(4) . . . . ? C24 C25 C26 C18 177.8(3) . . . . ? Fe2 O7 C27 C32 -15.3(4) . . . . ? Fe2 O7 C27 C28 165.11(18) . . . . ? O7 C27 C28 C29 -177.0(2) . . . . ? C32 C27 C28 C29 3.4(4) . . . . ? C27 C28 C29 C30 -1.0(4) . . . . ? C28 C29 C30 C31 -1.6(4) . . . . ? C29 C30 C31 C32 1.6(4) . . . . ? C30 C31 C32 C27 1.0(4) . . . . ? C30 C31 C32 C33 -177.8(3) . . . . ? O7 C27 C32 C31 177.0(2) . . . . ? C28 C27 C32 C31 -3.4(4) . . . . ? O7 C27 C32 C33 -4.2(4) . . . . ? C28 C27 C32 C33 175.4(2) . . . . ? C34 N4 C33 C32 -179.3(2) . . . . ? Fe2 N4 C33 C32 11.1(4) . . . . ? C31 C32 C33 N4 -176.5(3) . . . . ? C27 C32 C33 N4 4.7(4) . . . . ? C33 N4 C34 C35 -147.3(2) . . . . ? Fe2 N4 C34 C35 23.1(3) . . . . ? C36 N5 C35 C34 -119.4(3) . . . . ? Fe2 N5 C35 C34 52.4(2) . . . . ? N4 C34 C35 N5 -46.7(3) . . . . ? C35 N5 C36 C37 169.3(3) . . . . ? Fe2 N5 C36 C37 -1.2(4) . . . . ? N5 C36 C37 C38 169.5(3) . . . . ? N5 C36 C37 C42 -16.2(4) . . . . ? C42 C37 C38 C39 1.8(4) . . . . ? C36 C37 C38 C39 176.2(3) . . . . ? C37 C38 C39 C40 -2.8(5) . . . . ? C38 C39 C40 C41 1.7(5) . . . . ? C39 C40 C41 C42 0.4(5) . . . . ? Fe2 O8 C42 C41 -153.5(2) . . . . ? Fe2 O8 C42 C37 29.7(4) . . . . ? C40 C41 C42 O8 -178.4(3) . . . . ? C40 C41 C42 C37 -1.5(4) . . . . ? C38 C37 C42 O8 177.3(2) . . . . ? C36 C37 C42 O8 3.0(4) . . . . ? C38 C37 C42 C41 0.4(4) . . . . ? C36 C37 C42 C41 -173.8(3) . . . . ? Fe2 O10 C43 N6 -1.8(3) . . . . ? Fe2 O10 C43 C44 177.93(17) . . . . ? O9 N6 C43 O10 1.1(3) . . . . ? O9 N6 C43 C44 -178.7(2) . . . . ? O10 C43 C44 C52 -3.2(4) . . . . ? N6 C43 C44 C52 176.5(2) . . . . ? O10 C43 C44 C45 177.4(2) . . . . ? N6 C43 C44 C45 -2.9(4) . . . . ? C46 O12 C45 O11 178.5(2) . . . . ? C46 O12 C45 C44 -0.9(4) . . . . ? C52 C44 C45 O11 -179.1(3) . . . . ? C43 C44 C45 O11 0.2(4) . . . . ? C52 C44 C45 O12 0.2(4) . . . . ? C43 C44 C45 O12 179.6(2) . . . . ? C45 O12 C46 C51 0.1(4) . . . . ? C45 O12 C46 C47 -178.7(2) . . . . ? O12 C46 C47 C48 178.9(3) . . . . ? C51 C46 C47 C48 0.2(4) . . . . ? C46 C47 C48 C49 -0.1(4) . . . . ? C47 C48 C49 C50 -0.2(5) . . . . ? C48 C49 C50 C51 0.5(4) . . . . ? O12 C46 C51 C50 -178.7(2) . . . . ? C47 C46 C51 C50 0.1(4) . . . . ? O12 C46 C51 C52 1.4(4) . . . . ? C47 C46 C51 C52 -179.9(2) . . . . ? C49 C50 C51 C46 -0.4(4) . . . . ? C49 C50 C51 C52 179.6(3) . . . . ? C45 C44 C52 C51 1.3(4) . . . . ? C43 C44 C52 C51 -178.1(2) . . . . ? C46 C51 C52 C44 -2.1(4) . . . . ? C50 C51 C52 C44 178.0(3) . . . . ? Fe3 O13 C53 C54 -166.13(19) . . . . ? Fe3 O13 C53 C58 14.9(4) . . . . ? O13 C53 C54 C55 179.6(3) . . . . ? C58 C53 C54 C55 -1.3(4) . . . . ? C53 C54 C55 C56 0.1(4) . . . . ? C54 C55 C56 C57 0.7(5) . . . . ? C55 C56 C57 C58 -0.2(5) . . . . ? C56 C57 C58 C53 -1.0(4) . . . . ? C56 C57 C58 C59 178.4(3) . . . . ? O13 C53 C58 C57 -179.2(2) . . . . ? C54 C53 C58 C57 1.7(4) . . . . ? O13 C53 C58 C59 1.4(4) . . . . ? C54 C53 C58 C59 -177.6(2) . . . . ? C60 N7 C59 C58 178.3(3) . . . . ? Fe3 N7 C59 C58 -11.3(4) . . . . ? C57 C58 C59 N7 179.3(3) . . . . ? C53 C58 C59 N7 -1.3(4) . . . . ? C59 N7 C60 C61 147.3(3) . . . . ? Fe3 N7 C60 C61 -24.1(3) . . . . ? C62 N8 C61 C60 117.5(3) . . . . ? Fe3 N8 C61 C60 -53.8(3) . . . . ? N7 C60 C61 N8 47.9(3) . . . . ? C61 N8 C62 C63 -170.5(3) . . . . ? Fe3 N8 C62 C63 -0.5(4) . . . . ? N8 C62 C63 C64 -166.7(3) . . . . ? N8 C62 C63 C68 17.5(5) . . . . ? C68 C63 C64 C65 -3.0(5) . . . . ? C62 C63 C64 C65 -178.8(3) . . . . ? C63 C64 C65 C66 0.6(5) . . . . ? C64 C65 C66 C67 1.2(5) . . . . ? C65 C66 C67 C68 -0.7(5) . . . . ? Fe3 O14 C68 C67 144.4(2) . . . . ? Fe3 O14 C68 C63 -38.0(4) . . . . ? C66 C67 C68 O14 176.2(3) . . . . ? C66 C67 C68 C63 -1.6(4) . . . . ? C64 C63 C68 O14 -174.4(3) . . . . ? C62 C63 C68 O14 1.4(4) . . . . ? C64 C63 C68 C67 3.3(4) . . . . ? C62 C63 C68 C67 179.1(3) . . . . ? Fe3 O16 C69 N9 -13.4(3) . . . . ? Fe3 O16 C69 C70 163.00(18) . . . . ? O15 N9 C69 O16 2.4(4) . . . . ? O15 N9 C69 C70 -174.1(2) . . . . ? O16 C69 C70 C78 12.9(4) . . . . ? N9 C69 C70 C78 -170.8(2) . . . . ? O16 C69 C70 C71 -159.7(2) . . . . ? N9 C69 C70 C71 16.7(4) . . . . ? C72 O18 C71 O17 -175.8(2) . . . . ? C72 O18 C71 C70 6.2(4) . . . . ? C78 C70 C71 O17 172.0(3) . . . . ? C69 C70 C71 O17 -15.6(4) . . . . ? C78 C70 C71 O18 -10.3(4) . . . . ? C69 C70 C71 O18 162.1(2) . . . . ? C71 O18 C72 C73 -176.5(3) . . . . ? C71 O18 C72 C77 3.4(4) . . . . ? O18 C72 C73 C74 -177.7(3) . . . . ? C77 C72 C73 C74 2.4(5) . . . . ? C72 C73 C74 C75 0.5(5) . . . . ? C73 C74 C75 C76 -2.7(5) . . . . ? C74 C75 C76 C77 2.0(4) . . . . ? C73 C72 C77 C76 -3.1(4) . . . . ? O18 C72 C77 C76 177.1(2) . . . . ? C73 C72 C77 C78 170.9(3) . . . . ? O18 C72 C77 C78 -9.0(4) . . . . ? C75 C76 C77 C72 0.8(4) . . . . ? C75 C76 C77 C78 -172.7(3) . . . . ? C71 C70 C78 C77 4.9(4) . . . . ? C69 C70 C78 C77 -167.5(2) . . . . ? C72 C77 C78 C70 4.8(4) . . . . ? C76 C77 C78 C70 178.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O9 0.85(2) 1.96(2) 2.807(3) 173(3) . N6 H6N O5 0.84(2) 2.22(3) 2.808(3) 127(2) . N6 H6N O11 0.84(2) 2.15(3) 2.723(3) 125(2) . N9 H9N O17 0.85(2) 2.05(3) 2.702(3) 133(3) . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.291 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.065 # Attachment 'c343haH.CIF' data_twh07pj1 _database_code_depnum_ccdc_archive 'CCDC 740749' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc ' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0319(4) _cell_length_b 8.4492(3) _cell_length_c 13.5644(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.452(2) _cell_angle_gamma 90.00 _cell_volume 1329.11(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7421 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 33.73 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; SADABS Ver. 2004/1 (Bruker-AXS, 2004) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius FR591 Kappa APEX II' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28088 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 33.78 _reflns_number_total 5315 _reflns_number_gt 3875 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 Ver. 2.1-3 (Bruker-AXS, 2007)' _computing_cell_refinement 'SAINT Ver. 7.23A (Bruker-AXS, 2005)' _computing_data_reduction 'SAINT Ver. 7.23A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-Seed (Barbour, 2001), SHELXTL Ver. 6.14 (Bruker-AXS, 2003) ; _computing_publication_material 'modiCIFer-12162005 (Guzei, 2005)' _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^)+(0.0743P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5315 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.10673(6) 0.40274(10) -0.04165(6) 0.02392(17) Uani 1 1 d . . . O2 O 0.02822(7) 0.70870(11) -0.06832(7) 0.02829(19) Uani 1 1 d . . . O3 O 0.35710(7) 0.75894(8) 0.06813(6) 0.01945(15) Uani 1 1 d . . . O4 O 0.49030(6) 0.57804(8) 0.12633(5) 0.01517(14) Uani 1 1 d . . . N1 N 0.14110(8) 0.66608(11) -0.01873(7) 0.02154(18) Uani 1 1 d D . . N2 N 0.80376(7) 0.22239(10) 0.24551(6) 0.01636(16) Uani 1 1 d . . . C1 C 0.17474(8) 0.51486(12) -0.01057(7) 0.01683(18) Uani 1 1 d . . . C2 C 0.29874(8) 0.48738(12) 0.04043(7) 0.01459(17) Uani 1 1 d . . . C3 C 0.37827(8) 0.61703(11) 0.07669(7) 0.01462(17) Uani 1 1 d . . . C4 C 0.33818(8) 0.33341(11) 0.05255(7) 0.01494(17) Uani 1 1 d . . . H4 H 0.2856 0.2495 0.0275 0.018 Uiso 1 1 calc R . . C5 C 0.45407(8) 0.29708(11) 0.10095(7) 0.01356(16) Uani 1 1 d . . . C6 C 0.52970(8) 0.42374(10) 0.13952(7) 0.01274(16) Uani 1 1 d . . . C7 C 0.64519(8) 0.40456(11) 0.19012(7) 0.01325(16) Uani 1 1 d . . . C8 C 0.68982(8) 0.24805(11) 0.19950(7) 0.01301(16) Uani 1 1 d . . . C9 C 0.61512(8) 0.11605(11) 0.16118(7) 0.01401(17) Uani 1 1 d . . . C10 C 0.50088(8) 0.14202(11) 0.11376(7) 0.01462(17) Uani 1 1 d . . . H10 H 0.4520 0.0543 0.0889 0.018 Uiso 1 1 calc R . . C11 C 0.72075(8) 0.54378(11) 0.23422(7) 0.01629(18) Uani 1 1 d . . . H11A H 0.6745 0.6247 0.2582 0.020 Uiso 1 1 calc R . . H11B H 0.7519 0.5921 0.1807 0.020 Uiso 1 1 calc R . . C12 C 0.81998(9) 0.48939(12) 0.32346(7) 0.01830(18) Uani 1 1 d . . . H12A H 0.8743 0.5781 0.3470 0.022 Uiso 1 1 calc R . . H12B H 0.7896 0.4561 0.3812 0.022 Uiso 1 1 calc R . . C13 C 0.88276(9) 0.35160(12) 0.28981(8) 0.01955(19) Uani 1 1 d . . . H13A H 0.9218 0.3895 0.2386 0.023 Uiso 1 1 calc R . . H13B H 0.9426 0.3112 0.3495 0.023 Uiso 1 1 calc R . . C14 C 0.86145(9) 0.07082(12) 0.23969(9) 0.0215(2) Uani 1 1 d . . . H14A H 0.8784 0.0180 0.3072 0.026 Uiso 1 1 calc R . . H14B H 0.9357 0.0912 0.2236 0.026 Uiso 1 1 calc R . . C15 C 0.78885(9) -0.03915(12) 0.15904(8) 0.0204(2) Uani 1 1 d . . . H15A H 0.8237 -0.1461 0.1663 0.024 Uiso 1 1 calc R . . H15B H 0.7862 0.0011 0.0899 0.024 Uiso 1 1 calc R . . C16 C 0.66664(9) -0.04802(11) 0.17229(8) 0.01752(18) Uani 1 1 d . . . H16A H 0.6187 -0.1191 0.1199 0.021 Uiso 1 1 calc R . . H16B H 0.6689 -0.0912 0.2407 0.021 Uiso 1 1 calc R . . H1 H 0.1906(10) 0.7424(14) 0.0002(10) 0.021 Uiso 1 1 d D . . H2 H -0.0164(12) 0.6636(16) -0.0271(10) 0.021 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0156(3) 0.0241(4) 0.0294(4) -0.0035(3) 0.0014(3) -0.0019(3) O2 0.0180(4) 0.0319(5) 0.0329(4) 0.0085(4) 0.0032(3) 0.0074(3) O3 0.0198(4) 0.0124(3) 0.0260(4) 0.0015(3) 0.0058(3) 0.0023(3) O4 0.0147(3) 0.0099(3) 0.0197(3) 0.0001(2) 0.0025(2) 0.0008(2) N1 0.0142(4) 0.0204(4) 0.0272(4) 0.0020(3) 0.0008(3) 0.0037(3) N2 0.0137(4) 0.0116(3) 0.0221(4) -0.0013(3) 0.0018(3) 0.0003(3) C1 0.0150(4) 0.0191(4) 0.0164(4) 0.0001(3) 0.0043(3) 0.0013(3) C2 0.0129(4) 0.0156(4) 0.0151(4) 0.0001(3) 0.0032(3) 0.0000(3) C3 0.0152(4) 0.0142(4) 0.0150(4) 0.0005(3) 0.0049(3) 0.0005(3) C4 0.0149(4) 0.0144(4) 0.0155(4) -0.0011(3) 0.0039(3) -0.0021(3) C5 0.0145(4) 0.0112(4) 0.0150(4) -0.0008(3) 0.0039(3) -0.0013(3) C6 0.0150(4) 0.0091(4) 0.0146(4) -0.0002(3) 0.0048(3) -0.0002(3) C7 0.0142(4) 0.0102(4) 0.0152(4) -0.0004(3) 0.0037(3) -0.0012(3) C8 0.0141(4) 0.0117(4) 0.0134(4) 0.0004(3) 0.0039(3) -0.0001(3) C9 0.0169(4) 0.0101(4) 0.0153(4) 0.0000(3) 0.0048(3) -0.0007(3) C10 0.0165(4) 0.0106(4) 0.0168(4) -0.0013(3) 0.0044(3) -0.0028(3) C11 0.0173(4) 0.0106(4) 0.0202(4) -0.0015(3) 0.0036(3) -0.0022(3) C12 0.0179(4) 0.0153(4) 0.0195(4) -0.0024(3) 0.0012(3) -0.0030(3) C13 0.0144(4) 0.0166(4) 0.0252(5) -0.0019(4) 0.0010(3) -0.0022(3) C14 0.0169(4) 0.0145(4) 0.0313(5) 0.0002(4) 0.0034(4) 0.0040(3) C15 0.0217(5) 0.0133(4) 0.0273(5) -0.0015(4) 0.0084(4) 0.0019(4) C16 0.0204(5) 0.0102(4) 0.0217(4) 0.0000(3) 0.0053(3) -0.0002(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 C1 1.2493(13) . ? O2 N1 1.3928(12) . ? O2 H2 0.952(14) . ? O3 C3 1.2249(12) . ? O4 C3 1.3766(12) . ? O4 C6 1.3825(11) . ? N1 C1 1.3359(14) . ? N1 H1 0.869(8) . ? N2 C8 1.3638(12) . ? N2 C13 1.4670(13) . ? N2 C14 1.4688(13) . ? C1 C2 1.4861(13) . ? C2 C4 1.3795(13) . ? C2 C3 1.4515(13) . ? C4 C5 1.4078(13) . ? C4 H4 0.9500 . ? C5 C6 1.4119(13) . ? C5 C10 1.4183(13) . ? C6 C7 1.3857(13) . ? C7 C8 1.4201(13) . ? C7 C11 1.5094(13) . ? C8 C9 1.4398(13) . ? C9 C10 1.3712(13) . ? C9 C16 1.5096(13) . ? C10 H10 0.9500 . ? C11 C12 1.5270(14) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5225(14) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5212(15) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5300(15) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O2 H2 104.0(8) . . ? C3 O4 C6 123.11(8) . . ? C1 N1 O2 121.48(9) . . ? C1 N1 H1 121.1(9) . . ? O2 N1 H1 117.0(9) . . ? C8 N2 C13 122.12(8) . . ? C8 N2 C14 123.09(8) . . ? C13 N2 C14 114.01(8) . . ? O1 C1 N1 122.72(9) . . ? O1 C1 C2 121.64(9) . . ? N1 C1 C2 115.62(9) . . ? C4 C2 C3 119.77(8) . . ? C4 C2 C1 118.27(9) . . ? C3 C2 C1 121.96(9) . . ? O3 C3 O4 115.63(9) . . ? O3 C3 C2 127.22(9) . . ? O4 C3 C2 117.15(8) . . ? C2 C4 C5 121.85(9) . . ? C2 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 117.91(8) . . ? C4 C5 C10 124.76(9) . . ? C6 C5 C10 117.33(8) . . ? O4 C6 C7 116.01(8) . . ? O4 C6 C5 120.13(8) . . ? C7 C6 C5 123.86(8) . . ? C6 C7 C8 117.30(8) . . ? C6 C7 C11 121.58(8) . . ? C8 C7 C11 121.11(8) . . ? N2 C8 C7 119.94(8) . . ? N2 C8 C9 119.78(8) . . ? C7 C8 C9 120.28(8) . . ? C10 C9 C8 119.78(8) . . ? C10 C9 C16 121.83(8) . . ? C8 C9 C16 118.36(8) . . ? C9 C10 C5 121.40(8) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? C7 C11 C12 109.92(8) . . ? C7 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? C7 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 109.76(8) . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C13 C12 111.89(8) . . ? N2 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? N2 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? N2 C14 C15 112.47(8) . . ? N2 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? N2 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 109.34(8) . . ? C14 C15 H15A 109.8 . . ? C16 C15 H15A 109.8 . . ? C14 C15 H15B 109.8 . . ? C16 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? C9 C16 C15 108.98(8) . . ? C9 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? C9 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 N1 C1 O1 -3.84(16) . . . . ? O2 N1 C1 C2 177.53(9) . . . . ? O1 C1 C2 C4 0.34(14) . . . . ? N1 C1 C2 C4 178.98(9) . . . . ? O1 C1 C2 C3 179.97(9) . . . . ? N1 C1 C2 C3 -1.39(13) . . . . ? C6 O4 C3 O3 -177.77(8) . . . . ? C6 O4 C3 C2 2.19(12) . . . . ? C4 C2 C3 O3 177.15(9) . . . . ? C1 C2 C3 O3 -2.47(15) . . . . ? C4 C2 C3 O4 -2.81(13) . . . . ? C1 C2 C3 O4 177.58(8) . . . . ? C3 C2 C4 C5 1.03(14) . . . . ? C1 C2 C4 C5 -179.34(8) . . . . ? C2 C4 C5 C6 1.43(13) . . . . ? C2 C4 C5 C10 -178.42(9) . . . . ? C3 O4 C6 C7 179.26(8) . . . . ? C3 O4 C6 C5 0.26(13) . . . . ? C4 C5 C6 O4 -2.10(13) . . . . ? C10 C5 C6 O4 177.76(8) . . . . ? C4 C5 C6 C7 178.97(8) . . . . ? C10 C5 C6 C7 -1.17(13) . . . . ? O4 C6 C7 C8 -176.37(8) . . . . ? C5 C6 C7 C8 2.60(13) . . . . ? O4 C6 C7 C11 4.01(13) . . . . ? C5 C6 C7 C11 -177.03(8) . . . . ? C13 N2 C8 C7 2.27(13) . . . . ? C14 N2 C8 C7 -167.01(9) . . . . ? C13 N2 C8 C9 -177.34(8) . . . . ? C14 N2 C8 C9 13.38(14) . . . . ? C6 C7 C8 N2 177.82(8) . . . . ? C11 C7 C8 N2 -2.56(13) . . . . ? C6 C7 C8 C9 -2.57(13) . . . . ? C11 C7 C8 C9 177.05(8) . . . . ? N2 C8 C9 C10 -179.17(8) . . . . ? C7 C8 C9 C10 1.22(13) . . . . ? N2 C8 C9 C16 -0.77(13) . . . . ? C7 C8 C9 C16 179.61(8) . . . . ? C8 C9 C10 C5 0.28(13) . . . . ? C16 C9 C10 C5 -178.06(9) . . . . ? C4 C5 C10 C9 179.51(9) . . . . ? C6 C5 C10 C9 -0.34(13) . . . . ? C6 C7 C11 C12 153.77(9) . . . . ? C8 C7 C11 C12 -25.83(12) . . . . ? C7 C11 C12 C13 52.76(11) . . . . ? C8 N2 C13 C12 26.85(13) . . . . ? C14 N2 C13 C12 -162.97(9) . . . . ? C11 C12 C13 N2 -54.17(11) . . . . ? C8 N2 C14 C15 12.74(14) . . . . ? C13 N2 C14 C15 -157.33(9) . . . . ? N2 C14 C15 C16 -48.93(12) . . . . ? C10 C9 C16 C15 142.82(9) . . . . ? C8 C9 C16 C15 -35.53(12) . . . . ? C14 C15 C16 C9 59.34(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.869(8) 1.974(11) 2.6694(12) 136.1(12) . O2 H2 O1 0.952(14) 1.704(14) 2.6531(12) 174.1(13) 3_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.78 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.586 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.062