# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_H2L2Ph4 _database_code_depnum_ccdc_archive 'CCDC 881378' #TrackingRef 'web_deposit_cif_file_0_JustinWilson_1339011645.CCDC 881378.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H40 Cl4 N2 O8' _chemical_formula_weight 1130.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9567(16) _cell_length_b 13.8268(19) _cell_length_c 16.050(2) _cell_angle_alpha 85.563(2) _cell_angle_beta 80.664(2) _cell_angle_gamma 84.676(2) _cell_volume 2601.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6700 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; 77 Massachusetts Ave, 18-498 Cambridge, MA 02139 ; _diffrn_ambient_temperature 100(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_reflns_number 41574 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.13 _reflns_number_total 9300 _reflns_number_gt 6576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. Hydrogen atoms of the carboxylic acid were located on the difference map. They were placed and their thermal displacement parameters were constrained to 1.5 times that of the oxygen to which they were attached ; _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^)+(0.0848P)^2^+2.6679P] 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 9300 _refine_ls_number_parameters 727 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 O6 O 0.71932(18) 0.66807(15) -0.12929(14) 0.0207(5) Uani 1 1 d . . . O8 O 0.7987(2) 0.33220(16) 0.09625(15) 0.0269(6) Uani 1 1 d . . . O5 O 0.56425(17) 0.78223(15) 0.05495(14) 0.0187(5) Uani 1 1 d . . . O2 O 0.35560(18) 0.46049(15) 0.47285(14) 0.0199(5) Uani 1 1 d . . . O3 O 0.7432(2) 0.42509(17) 0.28871(15) 0.0266(6) Uani 1 1 d . . . O4 O 0.7005(2) 0.27933(17) 0.25728(16) 0.0293(6) Uani 1 1 d . . . H4O H 0.738(4) 0.290(3) 0.203(3) 0.044 Uiso 1 1 d . . . O1 O 0.38601(17) 0.67334(15) 0.33029(13) 0.0178(5) Uani 1 1 d . . . O7 O 0.8102(2) 0.48518(17) 0.12731(16) 0.0265(6) Uani 1 1 d . . . H7O H 0.797(3) 0.460(3) 0.182(3) 0.040 Uiso 1 1 d . . . N1 N 0.4941(2) 0.48667(19) 0.36176(17) 0.0202(6) Uani 1 1 d . . . C46 C 0.7843(3) 0.5795(2) -0.1247(2) 0.0192(7) Uani 1 1 d . . . C12 C 0.1962(3) 0.7237(2) 0.3558(2) 0.0220(7) Uani 1 1 d . . . C10 C 0.1198(3) 0.8758(2) 0.2990(2) 0.0221(7) Uani 1 1 d . . . H10 H 0.0567 0.9209 0.2918 0.026 Uiso 1 1 calc R . . C62 C 1.0700(3) 0.1211(3) -0.0661(2) 0.0265(8) Uani 1 1 d . . . H62 H 1.1118 0.0593 -0.0653 0.032 Uiso 1 1 calc R . . C45 C 0.6729(3) 0.6807(2) -0.0464(2) 0.0195(7) Uani 1 1 d . . . N2 N 0.7023(2) 0.61382(19) 0.00834(17) 0.0207(6) Uani 1 1 d . . . C48 C 0.8987(3) 0.4408(2) -0.1652(2) 0.0215(7) Uani 1 1 d . . . H48 H 0.9434 0.4033 -0.2075 0.026 Uiso 1 1 calc R . . C13 C 0.3045(3) 0.7469(2) 0.3157(2) 0.0178(7) Uani 1 1 d . . . C43 C 0.5246(3) 0.8190(2) -0.0781(2) 0.0203(7) Uani 1 1 d . . . H43 H 0.5282 0.8186 -0.1376 0.024 Uiso 1 1 calc R . . C17 C 0.3969(3) 0.5170(2) 0.4029(2) 0.0189(7) Uani 1 1 d . . . C51 C 0.7740(3) 0.5461(2) -0.0405(2) 0.0192(7) Uani 1 1 d . . . C52 C 0.8107(3) 0.4171(2) 0.0739(2) 0.0213(7) Uani 1 1 d . . . C42 C 0.4167(3) 0.8908(2) 0.1316(2) 0.0177(7) Uani 1 1 d . . . C23 C 0.5243(3) 0.4016(2) 0.4072(2) 0.0184(7) Uani 1 1 d . . . C25 C 0.3429(3) 0.2813(2) 0.5982(2) 0.0208(7) Uani 1 1 d . . . C59 C 0.9477(3) 0.3025(2) -0.0689(2) 0.0213(7) Uani 1 1 d . . . C19 C 0.4385(3) 0.3023(2) 0.5301(2) 0.0206(7) Uani 1 1 d . . . C6 C 0.5366(3) 0.9943(2) 0.2881(2) 0.0266(8) Uani 1 1 d . . . H6 H 0.6028 0.9511 0.2902 0.032 Uiso 1 1 calc R . . C22 C 0.6195(3) 0.3341(2) 0.3901(2) 0.0215(7) Uani 1 1 d . . . C14 C 0.3242(3) 0.8327(2) 0.2682(2) 0.0180(7) Uani 1 1 d . . . C18 C 0.4399(3) 0.3848(2) 0.4750(2) 0.0189(7) Uani 1 1 d . . . C37 C 0.3241(3) 0.9577(2) 0.1223(2) 0.0188(7) Uani 1 1 d . . . C1 C 0.2601(3) 0.9899(2) 0.2079(2) 0.0205(7) Uani 1 1 d . . . H1 H 0.1927 1.0372 0.2024 0.025 Uiso 1 1 calc R . . C44 C 0.5906(3) 0.7632(2) -0.0301(2) 0.0205(7) Uani 1 1 d . . . C9 C 0.2294(3) 0.8970(2) 0.2606(2) 0.0196(7) Uani 1 1 d . . . C2 C 0.3488(3) 1.0305(2) 0.2511(2) 0.0216(7) Uani 1 1 d . . . C41 C 0.4756(3) 0.8524(2) 0.0586(2) 0.0180(7) Uani 1 1 d . . . C60 C 1.0587(3) 0.2935(2) -0.0535(2) 0.0257(8) Uani 1 1 d . . . H60 H 1.0936 0.3498 -0.0438 0.031 Uiso 1 1 calc R . . C21 C 0.6276(3) 0.2530(2) 0.4483(2) 0.0219(7) Uani 1 1 d . . . C40 C 0.4476(3) 0.8793(2) -0.0219(2) 0.0189(7) Uani 1 1 d . . . C50 C 0.8259(3) 0.4556(2) -0.0163(2) 0.0199(7) Uani 1 1 d . . . C16 C 0.3275(3) 0.6036(2) 0.3814(2) 0.0204(7) Uani 1 1 d . . . C20 C 0.5374(3) 0.2388(2) 0.5151(2) 0.0230(7) Uani 1 1 d . . . H20 H 0.5438 0.1826 0.5525 0.028 Uiso 1 1 calc R . . C39 C 0.3572(3) 0.9500(2) -0.0297(2) 0.0206(7) Uani 1 1 d . . . H39 H 0.3376 0.9709 -0.0837 0.025 Uiso 1 1 calc R . . C49 C 0.8874(3) 0.4014(2) -0.0817(2) 0.0205(7) Uani 1 1 d . . . C26 C 0.2951(3) 0.1921(2) 0.6035(2) 0.0252(8) Uani 1 1 d . . . H26 H 0.3247 0.1453 0.5636 0.030 Uiso 1 1 calc R . . C15 C 0.2148(3) 0.6299(2) 0.3976(2) 0.0215(7) Uani 1 1 d . . . H15 H 0.1584 0.5930 0.4306 0.026 Uiso 1 1 calc R . . C30 C 0.2978(3) 0.3491(3) 0.6568(2) 0.0297(8) Uani 1 1 d . . . H30 H 0.3278 0.4108 0.6533 0.036 Uiso 1 1 calc R . . C63 C 0.9596(3) 0.1294(3) -0.0813(2) 0.0303(8) Uani 1 1 d . . . H63 H 0.9251 0.0728 -0.0906 0.036 Uiso 1 1 calc R . . C11 C 0.1031(3) 0.7901(3) 0.3473(2) 0.0253(8) Uani 1 1 d . . . H11 H 0.0290 0.7764 0.3744 0.030 Uiso 1 1 calc R . . C38 C 0.2972(3) 0.9885(2) 0.0429(2) 0.0207(7) Uani 1 1 d . . . H38 H 0.2364 1.0370 0.0384 0.025 Uiso 1 1 calc R . . C61 C 1.1199(3) 0.2033(2) -0.0519(2) 0.0277(8) Uani 1 1 d . . . H61 H 1.1961 0.1980 -0.0411 0.033 Uiso 1 1 calc R . . C64 C 0.8979(3) 0.2198(3) -0.0831(2) 0.0283(8) Uani 1 1 d . . . H64 H 0.8218 0.2248 -0.0940 0.034 Uiso 1 1 calc R . . C58 C 0.7853(3) 0.6284(2) -0.3165(2) 0.0249(8) Uani 1 1 d . . . H58 H 0.7139 0.6451 -0.2831 0.030 Uiso 1 1 calc R . . C28 C 0.1621(3) 0.2387(3) 0.7250(2) 0.0320(9) Uani 1 1 d . . . H28 H 0.1005 0.2245 0.7682 0.038 Uiso 1 1 calc R . . C24 C 0.6958(3) 0.3505(2) 0.3080(2) 0.0236(8) Uani 1 1 d . . . C7 C 0.4451(3) 0.9662(2) 0.2565(2) 0.0198(7) Uani 1 1 d . . . C5 C 0.5301(3) 1.0881(3) 0.3170(2) 0.0333(9) Uani 1 1 d . . . H5 H 0.5931 1.1087 0.3382 0.040 Uiso 1 1 calc R . . C3 C 0.3414(3) 1.1225(2) 0.2818(2) 0.0250(8) Uani 1 1 d . . . H3 H 0.2748 1.1653 0.2803 0.030 Uiso 1 1 calc R . . C32 C 0.7293(3) 0.0864(3) 0.4672(3) 0.0357(9) Uani 1 1 d . . . H32 H 0.6585 0.0606 0.4883 0.043 Uiso 1 1 calc R . . C54 C 0.9719(3) 0.5448(3) -0.3304(2) 0.0328(9) Uani 1 1 d . . . H54 H 1.0300 0.5057 -0.3068 0.039 Uiso 1 1 calc R . . C31 C 0.7320(3) 0.1852(3) 0.4427(2) 0.0271(8) Uani 1 1 d . . . C27 C 0.2053(3) 0.1712(3) 0.6663(2) 0.0306(9) Uani 1 1 d . . . H27 H 0.1732 0.1105 0.6691 0.037 Uiso 1 1 calc R . . C47 C 0.8494(3) 0.5310(2) -0.1908(2) 0.0214(7) Uani 1 1 d . . . C34 C 0.9314(4) 0.0620(4) 0.4310(3) 0.0490(12) Uani 1 1 d . . . H34 H 0.9987 0.0192 0.4255 0.059 Uiso 1 1 calc R . . C4 C 0.4333(3) 1.1511(3) 0.3150(2) 0.0291(8) Uani 1 1 d . . . H4 H 0.4295 1.2138 0.3363 0.035 Uiso 1 1 calc R . . C53 C 0.8675(3) 0.5693(2) -0.2800(2) 0.0234(8) Uani 1 1 d . . . C35 C 0.9373(3) 0.1592(3) 0.4087(3) 0.0417(10) Uani 1 1 d . . . H35 H 1.0088 0.1844 0.3890 0.050 Uiso 1 1 calc R . . C33 C 0.8272(4) 0.0260(3) 0.4614(3) 0.0471(11) Uani 1 1 d . . . H33 H 0.8237 -0.0411 0.4784 0.056 Uiso 1 1 calc R . . C56 C 0.9069(4) 0.6371(3) -0.4497(3) 0.0431(11) Uani 1 1 d . . . H56 H 0.9200 0.6598 -0.5076 0.052 Uiso 1 1 calc R . . C57 C 0.8050(3) 0.6627(3) -0.3992(2) 0.0329(9) Uani 1 1 d . . . H57 H 0.7484 0.7043 -0.4222 0.039 Uiso 1 1 calc R . . C36 C 0.8380(3) 0.2206(3) 0.4152(2) 0.0335(9) Uani 1 1 d . . . H36 H 0.8425 0.2882 0.4005 0.040 Uiso 1 1 calc R . . C29 C 0.2091(3) 0.3266(3) 0.7203(3) 0.0363(9) Uani 1 1 d . . . H29 H 0.1803 0.3725 0.7612 0.044 Uiso 1 1 calc R . . C55 C 0.9900(4) 0.5779(3) -0.4148(3) 0.0445(11) Uani 1 1 d . . . H55 H 1.0601 0.5599 -0.4492 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.61702(8) 0.37992(7) -0.12938(6) 0.0347(2) Uani 1 1 d . . . Cl2 Cl 0.47983(8) 0.56548(7) -0.13753(8) 0.0456(3) Uani 1 1 d . . . Cl3 Cl 1.12989(10) 0.92379(8) -0.21237(7) 0.0507(3) Uani 1 1 d . . . Cl4 Cl 0.97132(11) 0.77224(10) -0.19101(8) 0.0629(4) Uani 1 1 d . . . C66 C 0.4919(3) 0.4410(2) -0.1598(2) 0.0256(8) Uani 1 1 d . . . H66A H 0.4248 0.4095 -0.1290 0.031 Uiso 1 1 calc R . . H66B H 0.4933 0.4358 -0.2211 0.031 Uiso 1 1 calc R . . C67 C 1.0412(4) 0.8518(3) -0.1418(3) 0.0502(12) Uani 1 1 d . . . H67A H 0.9838 0.8946 -0.1075 0.060 Uiso 1 1 calc R . . H67B H 1.0871 0.8133 -0.1029 0.060 Uiso 1 1 calc R . . C8 C 0.4357(3) 0.8673(2) 0.2223(2) 0.0188(7) Uani 1 1 d . . . H8 H 0.5027 0.8196 0.2280 0.023 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 O6 0.0231(12) 0.0164(12) 0.0211(13) -0.0014(9) 0.0015(10) -0.0026(9) O8 0.0365(14) 0.0178(13) 0.0235(13) -0.0008(10) 0.0031(11) -0.0005(10) O5 0.0201(11) 0.0137(11) 0.0219(12) -0.0020(9) -0.0016(9) -0.0009(9) O2 0.0238(12) 0.0151(11) 0.0194(12) 0.0003(9) 0.0002(10) -0.0021(9) O3 0.0303(13) 0.0239(13) 0.0251(13) -0.0052(10) 0.0008(11) -0.0060(11) O4 0.0388(15) 0.0220(13) 0.0254(14) -0.0075(11) 0.0038(12) -0.0036(11) O1 0.0214(11) 0.0124(11) 0.0188(12) 0.0003(9) -0.0009(9) -0.0026(9) O7 0.0374(14) 0.0215(13) 0.0212(13) -0.0041(10) -0.0022(11) -0.0083(11) N1 0.0264(15) 0.0150(14) 0.0190(15) -0.0023(11) -0.0014(12) -0.0029(11) C46 0.0185(16) 0.0151(17) 0.0232(19) -0.0015(14) -0.0003(14) -0.0020(13) C12 0.0236(17) 0.0224(18) 0.0187(18) -0.0021(14) 0.0008(14) -0.0014(14) C10 0.0197(16) 0.0229(18) 0.0212(18) -0.0017(14) -0.0004(14) 0.0059(14) C62 0.0316(19) 0.0204(18) 0.027(2) 0.0003(15) -0.0061(16) 0.0011(15) C45 0.0217(16) 0.0170(17) 0.0197(18) -0.0039(14) 0.0001(14) -0.0039(13) N2 0.0222(14) 0.0165(14) 0.0230(16) -0.0026(12) -0.0011(12) -0.0027(11) C48 0.0185(16) 0.0202(18) 0.0250(19) -0.0057(14) 0.0021(14) -0.0029(13) C13 0.0212(16) 0.0150(16) 0.0166(17) -0.0037(13) -0.0019(13) 0.0023(13) C43 0.0223(17) 0.0183(17) 0.0209(18) -0.0025(14) -0.0027(14) -0.0037(13) C17 0.0258(17) 0.0146(16) 0.0161(17) -0.0015(13) -0.0005(14) -0.0057(13) C51 0.0182(16) 0.0182(17) 0.0214(18) -0.0055(14) -0.0004(13) -0.0033(13) C52 0.0201(17) 0.0199(19) 0.0233(19) -0.0061(14) 0.0005(14) -0.0010(13) C42 0.0207(16) 0.0140(16) 0.0192(17) 0.0005(13) -0.0035(13) -0.0061(13) C23 0.0277(17) 0.0102(16) 0.0184(17) -0.0018(13) -0.0029(14) -0.0073(13) C25 0.0235(17) 0.0192(17) 0.0199(18) 0.0039(14) -0.0053(14) -0.0037(14) C59 0.0252(17) 0.0187(17) 0.0182(18) -0.0019(14) 0.0024(14) -0.0018(14) C19 0.0266(17) 0.0162(17) 0.0194(18) -0.0046(14) -0.0023(14) -0.0039(14) C6 0.0324(19) 0.0199(18) 0.030(2) 0.0012(15) -0.0114(16) -0.0032(15) C22 0.0224(17) 0.0197(17) 0.0230(19) -0.0069(14) -0.0027(14) -0.0022(14) C14 0.0242(17) 0.0140(16) 0.0160(17) -0.0030(13) -0.0021(13) -0.0016(13) C18 0.0232(17) 0.0153(16) 0.0194(17) -0.0048(13) -0.0048(14) -0.0016(13) C37 0.0229(17) 0.0128(16) 0.0213(18) -0.0021(13) -0.0032(14) -0.0040(13) C1 0.0217(17) 0.0152(16) 0.0246(19) -0.0014(14) -0.0056(14) 0.0022(13) C44 0.0227(17) 0.0184(17) 0.0203(18) -0.0042(14) 0.0013(14) -0.0066(14) C9 0.0268(17) 0.0127(16) 0.0193(18) -0.0041(13) -0.0040(14) 0.0016(13) C2 0.0300(18) 0.0166(17) 0.0174(17) 0.0007(14) -0.0022(14) -0.0021(14) C41 0.0177(16) 0.0107(16) 0.0255(18) -0.0015(13) -0.0021(14) -0.0020(12) C60 0.0257(18) 0.0212(18) 0.032(2) -0.0029(15) -0.0082(16) -0.0047(14) C21 0.0277(18) 0.0148(17) 0.0251(19) -0.0060(14) -0.0067(15) -0.0026(14) C40 0.0197(16) 0.0164(16) 0.0208(18) -0.0004(13) -0.0015(13) -0.0059(13) C50 0.0200(16) 0.0185(17) 0.0219(18) -0.0042(14) -0.0022(14) -0.0043(13) C16 0.0306(18) 0.0140(17) 0.0164(17) 0.0008(13) -0.0015(14) -0.0050(14) C20 0.0308(19) 0.0190(18) 0.0213(18) -0.0028(14) -0.0085(15) -0.0039(14) C39 0.0234(17) 0.0172(17) 0.0228(18) 0.0020(14) -0.0077(14) -0.0048(13) C49 0.0173(16) 0.0206(17) 0.0240(19) -0.0029(14) -0.0022(14) -0.0048(13) C26 0.0324(19) 0.0168(17) 0.0249(19) -0.0011(14) -0.0012(15) 0.0000(14) C15 0.0222(17) 0.0217(18) 0.0184(18) 0.0010(14) 0.0049(14) -0.0059(14) C30 0.037(2) 0.0202(19) 0.030(2) -0.0043(16) 0.0040(17) -0.0093(16) C63 0.0297(19) 0.0205(19) 0.042(2) -0.0063(16) -0.0068(17) -0.0036(15) C11 0.0209(17) 0.029(2) 0.0231(19) -0.0007(15) 0.0045(14) -0.0027(15) C38 0.0202(16) 0.0132(16) 0.029(2) 0.0021(14) -0.0064(14) -0.0023(13) C61 0.0251(18) 0.0244(19) 0.035(2) 0.0010(16) -0.0114(16) -0.0010(15) C64 0.0221(18) 0.0240(19) 0.040(2) -0.0066(16) -0.0059(16) -0.0035(15) C58 0.035(2) 0.0164(17) 0.025(2) -0.0041(14) -0.0043(16) -0.0074(15) C28 0.030(2) 0.034(2) 0.030(2) 0.0017(17) 0.0027(16) -0.0080(16) C24 0.0257(18) 0.0171(18) 0.028(2) -0.0036(15) -0.0028(15) 0.0002(14) C7 0.0308(18) 0.0140(16) 0.0155(17) 0.0003(13) -0.0055(14) -0.0041(14) C5 0.045(2) 0.025(2) 0.034(2) -0.0010(17) -0.0169(18) -0.0111(17) C3 0.037(2) 0.0145(17) 0.0229(19) 0.0002(14) -0.0050(16) -0.0005(14) C32 0.042(2) 0.026(2) 0.042(2) -0.0079(18) -0.0152(19) 0.0022(17) C54 0.031(2) 0.034(2) 0.032(2) -0.0030(17) 0.0056(17) -0.0104(16) C31 0.036(2) 0.0235(19) 0.0242(19) -0.0091(15) -0.0116(16) 0.0036(15) C27 0.033(2) 0.0193(19) 0.039(2) 0.0040(16) -0.0014(17) -0.0083(15) C47 0.0210(17) 0.0215(18) 0.0222(18) -0.0033(14) -0.0008(14) -0.0078(14) C34 0.047(3) 0.058(3) 0.044(3) -0.023(2) -0.016(2) 0.021(2) C4 0.047(2) 0.0197(18) 0.024(2) -0.0051(15) -0.0118(17) -0.0033(16) C53 0.0278(18) 0.0187(18) 0.0240(19) -0.0050(14) 0.0017(15) -0.0098(14) C35 0.034(2) 0.059(3) 0.033(2) -0.013(2) -0.0085(18) 0.007(2) C33 0.066(3) 0.024(2) 0.057(3) -0.009(2) -0.031(2) 0.008(2) C56 0.066(3) 0.041(2) 0.021(2) 0.0065(18) 0.002(2) -0.022(2) C57 0.047(2) 0.024(2) 0.030(2) -0.0018(16) -0.0082(18) -0.0111(17) C36 0.032(2) 0.039(2) 0.029(2) -0.0094(17) -0.0057(17) 0.0047(17) C29 0.038(2) 0.034(2) 0.035(2) -0.0139(18) 0.0093(18) -0.0071(17) C55 0.050(3) 0.049(3) 0.030(2) -0.004(2) 0.015(2) -0.014(2) Cl1 0.0298(5) 0.0275(5) 0.0490(6) -0.0045(4) -0.0107(4) -0.0039(4) Cl2 0.0354(5) 0.0271(5) 0.0779(8) -0.0179(5) -0.0145(5) -0.0001(4) Cl3 0.0695(8) 0.0367(6) 0.0466(7) -0.0065(5) -0.0063(6) -0.0093(5) Cl4 0.0655(8) 0.0645(8) 0.0624(8) 0.0161(6) -0.0191(6) -0.0259(6) C66 0.0259(18) 0.0272(19) 0.0239(19) -0.0040(15) -0.0003(15) -0.0077(15) C67 0.057(3) 0.041(3) 0.048(3) 0.002(2) -0.006(2) 0.009(2) C8 0.0208(16) 0.0139(16) 0.0214(18) -0.0009(13) -0.0040(14) 0.0004(13) _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 O6 C45 1.374(4) . ? O6 C46 1.392(4) . ? O8 C52 1.215(4) . ? O5 C41 1.366(4) . ? O5 C44 1.390(4) . ? O2 C17 1.369(4) . ? O2 C18 1.386(4) . ? O3 C24 1.217(4) . ? O4 C24 1.317(4) . ? O4 H4O 0.92(4) . ? O1 C13 1.376(4) . ? O1 C16 1.382(4) . ? O7 C52 1.321(4) . ? O7 H7O 0.91(4) . ? N1 C17 1.291(4) . ? N1 C23 1.386(4) . ? C46 C51 1.384(5) . ? C46 C47 1.388(5) . ? C12 C11 1.393(5) . ? C12 C13 1.404(4) . ? C12 C15 1.428(5) . ? C10 C11 1.377(5) . ? C10 C9 1.401(5) . ? C10 H10 0.9500 . ? C62 C63 1.373(5) . ? C62 C61 1.381(5) . ? C62 H62 0.9500 . ? C45 N2 1.290(4) . ? C45 C44 1.447(5) . ? N2 C51 1.405(4) . ? C48 C47 1.391(5) . ? C48 C49 1.397(5) . ? C48 H48 0.9500 . ? C13 C14 1.377(4) . ? C43 C44 1.343(5) . ? C43 C40 1.436(4) . ? C43 H43 0.9500 . ? C17 C16 1.444(5) . ? C51 C50 1.400(5) . ? C52 C50 1.491(5) . ? C42 C41 1.382(4) . ? C42 C37 1.395(4) . ? C42 C8 1.516(4) . ? C23 C18 1.380(5) . ? C23 C22 1.408(5) . ? C25 C30 1.389(5) . ? C25 C26 1.398(5) . ? C25 C19 1.481(5) . ? C59 C60 1.382(5) . ? C59 C64 1.388(5) . ? C59 C49 1.500(5) . ? C19 C18 1.388(5) . ? C19 C20 1.405(5) . ? C6 C7 1.376(5) . ? C6 C5 1.401(5) . ? C6 H6 0.9500 . ? C22 C21 1.409(5) . ? C22 C24 1.491(5) . ? C14 C9 1.391(4) . ? C14 C8 1.514(4) . ? C37 C38 1.391(5) . ? C37 C1 1.536(5) . ? C1 C9 1.523(5) . ? C1 C2 1.526(5) . ? C1 H1 1.0000 . ? C2 C3 1.391(5) . ? C2 C7 1.397(5) . ? C41 C40 1.402(5) . ? C60 C61 1.387(5) . ? C60 H60 0.9500 . ? C21 C20 1.408(5) . ? C21 C31 1.485(5) . ? C40 C39 1.403(4) . ? C50 C49 1.405(5) . ? C16 C15 1.352(5) . ? C20 H20 0.9500 . ? C39 C38 1.381(5) . ? C39 H39 0.9500 . ? C26 C27 1.383(5) . ? C26 H26 0.9500 . ? C15 H15 0.9500 . ? C30 C29 1.386(5) . ? C30 H30 0.9500 . ? C63 C64 1.392(5) . ? C63 H63 0.9500 . ? C11 H11 0.9500 . ? C38 H38 0.9500 . ? C61 H61 0.9500 . ? C64 H64 0.9500 . ? C58 C57 1.366(5) . ? C58 C53 1.393(5) . ? C58 H58 0.9500 . ? C28 C29 1.377(5) . ? C28 C27 1.384(5) . ? C28 H28 0.9500 . ? C7 C8 1.533(4) . ? C5 C4 1.386(5) . ? C5 H5 0.9500 . ? C3 C4 1.397(5) . ? C3 H3 0.9500 . ? C32 C33 1.368(6) . ? C32 C31 1.393(5) . ? C32 H32 0.9500 . ? C54 C55 1.385(6) . ? C54 C53 1.401(5) . ? C54 H54 0.9500 . ? C31 C36 1.394(5) . ? C27 H27 0.9500 . ? C47 C53 1.476(5) . ? C34 C35 1.368(6) . ? C34 C33 1.385(7) . ? C34 H34 0.9500 . ? C4 H4 0.9500 . ? C35 C36 1.388(5) . ? C35 H35 0.9500 . ? C33 H33 0.9500 . ? C56 C57 1.382(6) . ? C56 C55 1.389(6) . ? C56 H56 0.9500 . ? C57 H57 0.9500 . ? C36 H36 0.9500 . ? C29 H29 0.9500 . ? C55 H55 0.9500 . ? Cl1 C66 1.768(4) . ? Cl2 C66 1.773(3) . ? Cl3 C67 1.740(5) . ? Cl4 C67 1.746(5) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? C67 H67A 0.9900 . ? C67 H67B 0.9900 . ? C8 H8 1.0000 . ? 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 C45 O6 C46 103.1(2) . . ? C41 O5 C44 104.7(2) . . ? C17 O2 C18 102.9(2) . . ? C24 O4 H4O 116(3) . . ? C13 O1 C16 105.0(2) . . ? C52 O7 H7O 110(3) . . ? C17 N1 C23 103.8(3) . . ? C51 C46 C47 124.5(3) . . ? C51 C46 O6 107.8(3) . . ? C47 C46 O6 127.7(3) . . ? C11 C12 C13 118.8(3) . . ? C11 C12 C15 136.4(3) . . ? C13 C12 C15 104.8(3) . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C63 C62 C61 119.6(3) . . ? C63 C62 H62 120.2 . . ? C61 C62 H62 120.2 . . ? N2 C45 O6 116.1(3) . . ? N2 C45 C44 126.7(3) . . ? O6 C45 C44 117.0(3) . . ? C45 N2 C51 104.2(3) . . ? C47 C48 C49 124.9(3) . . ? C47 C48 H48 117.6 . . ? C49 C48 H48 117.6 . . ? O1 C13 C14 125.5(3) . . ? O1 C13 C12 111.1(3) . . ? C14 C13 C12 123.4(3) . . ? C44 C43 C40 106.6(3) . . ? C44 C43 H43 126.7 . . ? C40 C43 H43 126.7 . . ? N1 C17 O2 116.4(3) . . ? N1 C17 C16 126.4(3) . . ? O2 C17 C16 117.3(3) . . ? C46 C51 C50 121.0(3) . . ? C46 C51 N2 108.7(3) . . ? C50 C51 N2 130.2(3) . . ? O8 C52 O7 123.2(3) . . ? O8 C52 C50 123.8(3) . . ? O7 C52 C50 113.0(3) . . ? C41 C42 C37 116.7(3) . . ? C41 C42 C8 128.8(3) . . ? C37 C42 C8 114.4(3) . . ? C18 C23 N1 109.4(3) . . ? C18 C23 C22 120.9(3) . . ? N1 C23 C22 129.6(3) . . ? C30 C25 C26 118.7(3) . . ? C30 C25 C19 121.5(3) . . ? C26 C25 C19 119.7(3) . . ? C60 C59 C64 119.0(3) . . ? C60 C59 C49 120.3(3) . . ? C64 C59 C49 120.1(3) . . ? C18 C19 C20 113.5(3) . . ? C18 C19 C25 124.2(3) . . ? C20 C19 C25 122.3(3) . . ? C7 C6 C5 118.6(3) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C23 C22 C21 116.9(3) . . ? C23 C22 C24 116.6(3) . . ? C21 C22 C24 126.2(3) . . ? C13 C14 C9 116.3(3) . . ? C13 C14 C8 129.0(3) . . ? C9 C14 C8 114.8(3) . . ? C23 C18 O2 107.6(3) . . ? C23 C18 C19 124.7(3) . . ? O2 C18 C19 127.6(3) . . ? C38 C37 C42 121.3(3) . . ? C38 C37 C1 126.6(3) . . ? C42 C37 C1 112.1(3) . . ? C9 C1 C2 104.9(3) . . ? C9 C1 C37 106.2(3) . . ? C2 C1 C37 105.5(3) . . ? C9 C1 H1 113.2 . . ? C2 C1 H1 113.2 . . ? C37 C1 H1 113.2 . . ? C43 C44 O5 112.4(3) . . ? C43 C44 C45 133.5(3) . . ? O5 C44 C45 113.6(3) . . ? C14 C9 C10 121.9(3) . . ? C14 C9 C1 112.3(3) . . ? C10 C9 C1 125.8(3) . . ? C3 C2 C7 120.3(3) . . ? C3 C2 C1 126.0(3) . . ? C7 C2 C1 113.7(3) . . ? O5 C41 C42 125.5(3) . . ? O5 C41 C40 111.4(3) . . ? C42 C41 C40 123.0(3) . . ? C59 C60 C61 120.8(3) . . ? C59 C60 H60 119.6 . . ? C61 C60 H60 119.6 . . ? C20 C21 C22 119.4(3) . . ? C20 C21 C31 119.5(3) . . ? C22 C21 C31 121.0(3) . . ? C41 C40 C39 119.0(3) . . ? C41 C40 C43 104.9(3) . . ? C39 C40 C43 136.1(3) . . ? C51 C50 C49 116.5(3) . . ? C51 C50 C52 121.3(3) . . ? C49 C50 C52 122.2(3) . . ? C15 C16 O1 111.9(3) . . ? C15 C16 C17 133.5(3) . . ? O1 C16 C17 114.6(3) . . ? C19 C20 C21 124.3(3) . . ? C19 C20 H20 117.8 . . ? C21 C20 H20 117.8 . . ? C38 C39 C40 118.5(3) . . ? C38 C39 H39 120.8 . . ? C40 C39 H39 120.8 . . ? C48 C49 C50 119.8(3) . . ? C48 C49 C59 115.6(3) . . ? C50 C49 C59 124.5(3) . . ? C27 C26 C25 120.7(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C16 C15 C12 107.3(3) . . ? C16 C15 H15 126.4 . . ? C12 C15 H15 126.4 . . ? C29 C30 C25 120.0(3) . . ? C29 C30 H30 120.0 . . ? C25 C30 H30 120.0 . . ? C62 C63 C64 120.6(3) . . ? C62 C63 H63 119.7 . . ? C64 C63 H63 119.7 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C39 C38 C37 121.4(3) . . ? C39 C38 H38 119.3 . . ? C37 C38 H38 119.3 . . ? C62 C61 C60 120.0(3) . . ? C62 C61 H61 120.0 . . ? C60 C61 H61 120.0 . . ? C59 C64 C63 119.9(3) . . ? C59 C64 H64 120.0 . . ? C63 C64 H64 120.0 . . ? C57 C58 C53 121.4(3) . . ? C57 C58 H58 119.3 . . ? C53 C58 H58 119.3 . . ? C29 C28 C27 119.5(3) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? O3 C24 O4 123.9(3) . . ? O3 C24 C22 122.7(3) . . ? O4 C24 C22 113.2(3) . . ? C6 C7 C2 120.9(3) . . ? C6 C7 C8 126.4(3) . . ? C2 C7 C8 112.6(3) . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C33 C32 C31 121.0(4) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C55 C54 C53 119.7(4) . . ? C55 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? C32 C31 C36 117.6(3) . . ? C32 C31 C21 122.5(3) . . ? C36 C31 C21 119.8(3) . . ? C26 C27 C28 120.1(3) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C46 C47 C48 113.2(3) . . ? C46 C47 C53 124.9(3) . . ? C48 C47 C53 121.9(3) . . ? C35 C34 C33 120.0(4) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C58 C53 C54 118.4(3) . . ? C58 C53 C47 122.9(3) . . ? C54 C53 C47 118.6(3) . . ? C34 C35 C36 119.5(4) . . ? C34 C35 H35 120.3 . . ? C36 C35 H35 120.3 . . ? C32 C33 C34 120.5(4) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C57 C56 C55 119.2(4) . . ? C57 C56 H56 120.4 . . ? C55 C56 H56 120.4 . . ? C58 C57 C56 120.4(4) . . ? C58 C57 H57 119.8 . . ? C56 C57 H57 119.8 . . ? C35 C36 C31 121.4(4) . . ? C35 C36 H36 119.3 . . ? C31 C36 H36 119.3 . . ? C28 C29 C30 120.9(3) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C54 C55 C56 120.8(4) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? Cl1 C66 Cl2 111.11(18) . . ? Cl1 C66 H66A 109.4 . . ? Cl2 C66 H66A 109.4 . . ? Cl1 C66 H66B 109.4 . . ? Cl2 C66 H66B 109.4 . . ? H66A C66 H66B 108.0 . . ? Cl3 C67 Cl4 113.6(3) . . ? Cl3 C67 H67A 108.8 . . ? Cl4 C67 H67A 108.8 . . ? Cl3 C67 H67B 108.8 . . ? Cl4 C67 H67B 108.8 . . ? H67A C67 H67B 107.7 . . ? C14 C8 C42 105.0(2) . . ? C14 C8 C7 105.5(3) . . ? C42 C8 C7 104.8(2) . . ? C14 C8 H8 113.5 . . ? C42 C8 H8 113.5 . . ? C7 C8 H8 113.5 . . ? 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 O7 H7O O3 0.91(4) 1.78(4) 2.676(3) 168(4) . O4 H4O O8 0.92(4) 1.82(5) 2.734(3) 170(4) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.251 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.085 data_[NaFe3(L2Ph4)2(mu3-O)(mu-O2CPh3)2(H2O)3](OTf)2 _database_code_depnum_ccdc_archive 'CCDC 881379' #TrackingRef 'web_deposit_cif_file_1_JustinWilson_1339011645.CCDC 881379.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C216 H158 F6 Fe3 N4 Na O30 S2' _chemical_formula_weight 3658.12 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.025(2) _cell_length_b 37.392(3) _cell_length_c 17.9887(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.5390(10) _cell_angle_gamma 90.00 _cell_volume 17472(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9022 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 19.29 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7588 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6504 _exptl_absorpt_correction_T_max 0.7446 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 78354 _diffrn_reflns_av_R_equivalents 0.0960 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 20.88 _reflns_number_total 9198 _reflns_number_gt 5715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. The diffraction intensity of the crystal was extremely low. The data was truncated at 1 angstrom resolution since no reflection were observed past that point. As a result the 2theta value is only 20 degrees, lower than the recommended 2theta value of 25 degrees. Hence, precise bond metrics should be intepreted with caution. Atomic connectivity (aside from the disordered solvent) is more or less unambiguous though. Because of the low resolution, there is a low data to parameter ratio. To help with the low data to parameter ratio, restraints on the direction and size of thermal displacement ellipsoids were applied on all atoms in the structure (SIMU and DELU) commands. A large Q peak within the core iron structure was assigned as a 50% occupancy sodium ion. This formulation is consistent with bulk elemental analysis of the sample. Two benzene molecules were located and assigned at full occupancy. Restraints on the 11, 12, and 13 bond distances were applied. Also restraints to keep the benezene molecule flat were also applied. Two additional benzene molecules were located near crystallographic special positions. These were refined at 50 percent occupancy with the same restraints using the PART-1 command. A molecule of pentane (or what was modeled as pentane) was located as well. Chemically equivalent bond distances were restrained to be similar. Several impossible close contacts are present in the lattice, giving rise to level A CheckCIF alerts. We postulate that these close contacts arise due to disorder and imperfect modeling of it. ; _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^)+(0.1782P)^2^+163.4933P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9198 _refine_ls_number_parameters 1240 _refine_ls_number_restraints 1411 _refine_ls_R_factor_all 0.1526 _refine_ls_R_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.3192 _refine_ls_wR_factor_gt 0.2645 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.007 _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 0.05761(5) 0.26254(4) 0.21750(6) 0.0476(5) Uani 1 1 d U . . Fe2 Fe 0.0000 0.18680(5) 0.2500 0.0501(6) Uani 1 2 d SU . . O2 O 0.1208(3) 0.41735(16) 0.3862(3) 0.0567(17) Uani 1 1 d U . . O1 O 0.1506(3) 0.40536(17) 0.1957(3) 0.0601(17) Uani 1 1 d U . . O5 O 0.1777(2) 0.31486(18) -0.0015(3) 0.0564(16) Uani 1 1 d U . . O9 O 0.0656(2) 0.18291(16) 0.3155(3) 0.0524(15) Uani 1 1 d U . . O3 O 0.0662(2) 0.29580(16) 0.3056(3) 0.0495(15) Uani 1 1 d U . . O10 O 0.1084(2) 0.22839(18) 0.2680(3) 0.0554(16) Uani 1 1 d U . . O6 O 0.1786(2) 0.22424(18) -0.0645(3) 0.0576(16) Uani 1 1 d U . . O8 O 0.0580(2) 0.23326(18) 0.1239(3) 0.0513(16) Uani 1 1 d U . . N2 N 0.1387(3) 0.2439(2) 0.0348(4) 0.0545(19) Uani 1 1 d U . . O7 O 0.0421(2) 0.17809(17) 0.1621(3) 0.0560(16) Uani 1 1 d U . . C46 C 0.1230(4) 0.2086(3) 0.0198(5) 0.051(2) Uani 1 1 d U . . C20 C 0.0466(4) 0.3379(3) 0.3982(5) 0.050(2) Uani 1 1 d U . . N1 N 0.1003(3) 0.3716(2) 0.3079(4) 0.056(2) Uani 1 1 d U . . C42 C 0.2092(4) 0.3425(3) -0.0260(5) 0.058(2) Uani 1 1 d U . . C23 C 0.0733(4) 0.3979(3) 0.4937(5) 0.052(2) Uani 1 1 d U . . C18 C 0.0893(4) 0.3945(2) 0.4221(5) 0.053(2) Uani 1 1 d U . . C30 C 0.0000(4) 0.3106(3) 0.5069(5) 0.053(2) Uani 1 1 d U . . C16 C 0.1562(4) 0.4191(3) 0.2674(5) 0.059(2) Uani 1 1 d U . . C9 C 0.1905(4) 0.4218(3) 0.0806(5) 0.068(3) Uani 1 1 d U . . C43 C 0.2370(4) 0.2905(3) -0.0726(5) 0.065(2) Uani 1 1 d U . . H43 H 0.2558 0.2733 -0.0985 0.078 Uiso 1 1 calc R . . C79 C 0.1994(4) 0.2140(3) 0.3355(5) 0.061(2) Uani 1 1 d U . . C17 C 0.1250(4) 0.4012(3) 0.3176(5) 0.055(2) Uani 1 1 d U . . C21 C 0.0291(3) 0.3397(2) 0.4694(4) 0.048(2) Uani 1 1 d U . . C8 C 0.1608(4) 0.3968(3) 0.0253(5) 0.067(2) Uani 1 1 d U . . H8 H 0.1361 0.3806 0.0490 0.080 Uiso 1 1 calc R . . C50 C 0.0820(4) 0.1513(3) 0.0247(5) 0.059(2) Uani 1 1 d U . . C22 C 0.0427(4) 0.3698(3) 0.5142(5) 0.052(2) Uani 1 1 d U . . H22 H 0.0297 0.3707 0.5624 0.062 Uiso 1 1 calc R . . C73 C 0.1708(4) 0.1504(3) 0.3120(5) 0.064(2) Uani 1 1 d U . . C31 C -0.0402(4) 0.3189(3) 0.5500(5) 0.061(2) Uani 1 1 d U . . H31 H -0.0526 0.3428 0.5508 0.073 Uiso 1 1 calc R . . C34 C -0.0066(4) 0.2494(3) 0.5446(5) 0.066(3) Uani 1 1 d U . . H34 H 0.0047 0.2253 0.5421 0.079 Uiso 1 1 calc R . . C11 C 0.2110(5) 0.4500(3) 0.2006(5) 0.074(3) Uani 1 1 d U . . C24 C 0.0890(4) 0.4269(3) 0.5439(5) 0.066(3) Uani 1 1 d U . . C19 C 0.0773(4) 0.3658(3) 0.3761(5) 0.052(2) Uani 1 1 d U . . C51 C 0.0878(4) 0.1866(3) 0.0534(5) 0.050(2) Uani 1 1 d U . . C45 C 0.1700(4) 0.2513(3) -0.0168(5) 0.056(2) Uani 1 1 d U . . C58 C 0.0451(4) 0.1249(3) 0.0554(5) 0.063(2) Uani 1 1 d U . . C41 C 0.2463(4) 0.3277(3) -0.0704(5) 0.065(2) Uani 1 1 d U . . C72 C 0.1588(4) 0.1513(3) 0.4661(6) 0.075(3) Uani 1 1 d U . . H72 H 0.1740 0.1319 0.4413 0.090 Uiso 1 1 calc R . . C1 C 0.2264(5) 0.4389(3) -0.0341(5) 0.082(3) Uani 1 1 d U . . H1 H 0.2511 0.4552 -0.0575 0.098 Uiso 1 1 calc R . . C77 C 0.2376(5) 0.1071(3) 0.2905(6) 0.079(3) Uani 1 1 d U . . H77 H 0.2731 0.1010 0.2927 0.095 Uiso 1 1 calc R . . C68 C 0.1226(4) 0.2093(3) 0.4642(5) 0.066(3) Uani 1 1 d U . . H68 H 0.1123 0.2306 0.4386 0.079 Uiso 1 1 calc R . . C15 C 0.1919(5) 0.4451(3) 0.2732(5) 0.068(3) Uani 1 1 d U . . H15 H 0.2026 0.4579 0.3171 0.081 Uiso 1 1 calc R . . C29 C 0.0980(5) 0.4204(3) 0.6199(5) 0.077(3) Uani 1 1 d U . . H29 H 0.0930 0.3971 0.6390 0.093 Uiso 1 1 calc R . . C38 C 0.2374(5) 0.3997(3) -0.0471(5) 0.072(3) Uani 1 1 d U . . C33 C -0.0451(4) 0.2585(3) 0.5893(5) 0.068(3) Uani 1 1 d U . . H33 H -0.0600 0.2408 0.6190 0.081 Uiso 1 1 calc R . . C25 C 0.0956(6) 0.4612(3) 0.5186(6) 0.097(4) Uani 1 1 d U . . H25 H 0.0885 0.4668 0.4675 0.117 Uiso 1 1 calc R . . C37 C 0.2020(4) 0.3772(3) -0.0148(5) 0.063(2) Uani 1 1 d U . . C52 C 0.1706(5) 0.1505(3) -0.1367(6) 0.078(3) Uani 1 1 d U . . C67 C 0.1457(4) 0.1823(3) 0.4272(5) 0.061(2) Uani 1 1 d U . . C69 C 0.1143(4) 0.2055(3) 0.5398(6) 0.071(3) Uani 1 1 d U . . H69 H 0.0997 0.2250 0.5648 0.085 Uiso 1 1 calc R . . C49 C 0.1089(4) 0.1407(3) -0.0362(5) 0.069(3) Uani 1 1 d U . . H49 H 0.1035 0.1172 -0.0552 0.083 Uiso 1 1 calc R . . C36 C 0.0314(4) 0.3087(3) 0.3434(5) 0.052(2) Uani 1 1 d U . . C65 C 0.1064(4) 0.2003(3) 0.3064(5) 0.050(2) Uani 1 1 d U . . C35 C 0.0158(4) 0.2758(3) 0.5028(5) 0.061(2) Uani 1 1 d U . . H35 H 0.0423 0.2697 0.4712 0.074 Uiso 1 1 calc R . . C80 C 0.2102(4) 0.2278(3) 0.2662(6) 0.066(3) Uani 1 1 d U . . H80 H 0.1906 0.2200 0.2230 0.079 Uiso 1 1 calc R . . C66 C 0.1575(4) 0.1868(3) 0.3442(5) 0.054(2) Uani 1 1 d U . . C32 C -0.0626(4) 0.2935(3) 0.5916(5) 0.064(3) Uani 1 1 d U . . H32 H -0.0898 0.2996 0.6219 0.077 Uiso 1 1 calc R . . C12 C 0.2469(6) 0.4717(3) 0.1683(6) 0.096(4) Uani 1 1 d U . . H12 H 0.2662 0.4887 0.1975 0.115 Uiso 1 1 calc R . . C78 C 0.2228(4) 0.1414(3) 0.3122(6) 0.074(3) Uani 1 1 d U . . H78 H 0.2483 0.1585 0.3272 0.088 Uiso 1 1 calc R . . C40 C 0.2814(4) 0.3511(4) -0.1006(6) 0.079(3) Uani 1 1 d U . . H40 H 0.3082 0.3423 -0.1291 0.094 Uiso 1 1 calc R . . C10 C 0.1844(4) 0.4254(3) 0.1562(5) 0.066(3) Uani 1 1 d U . . C64 C 0.0604(4) 0.2002(3) 0.1177(5) 0.053(2) Uani 1 1 d U . . C44 C 0.1961(4) 0.2838(3) -0.0310(5) 0.057(2) Uani 1 1 d U . . C71 C 0.1498(5) 0.1484(3) 0.5424(6) 0.082(3) Uani 1 1 d U . . H71 H 0.1601 0.1275 0.5693 0.099 Uiso 1 1 calc R . . C47 C 0.1479(4) 0.1960(3) -0.0418(5) 0.060(2) Uani 1 1 d U . . C84 C 0.2304(4) 0.2252(3) 0.3966(6) 0.071(3) Uani 1 1 d U . . H84 H 0.2251 0.2155 0.4443 0.085 Uiso 1 1 calc R . . C14 C 0.2247(5) 0.4444(3) 0.0506(5) 0.076(3) Uani 1 1 d U . . C2 C 0.1711(5) 0.4446(3) -0.0629(5) 0.076(3) Uani 1 1 d U . . C7 C 0.1355(5) 0.4220(3) -0.0315(5) 0.069(2) Uani 1 1 d U . . C70 C 0.1257(4) 0.1762(3) 0.5782(6) 0.076(3) Uani 1 1 d U . . H70 H 0.1178 0.1741 0.6289 0.091 Uiso 1 1 calc R . . C13 C 0.2539(6) 0.4682(3) 0.0938(6) 0.095(4) Uani 1 1 d U . . H13 H 0.2791 0.4824 0.0717 0.114 Uiso 1 1 calc R . . C6 C 0.0848(5) 0.4251(3) -0.0504(5) 0.074(3) Uani 1 1 d U . . H6 H 0.0610 0.4099 -0.0278 0.089 Uiso 1 1 calc R . . C59 C 0.0654(5) 0.0944(3) 0.0900(6) 0.080(3) Uani 1 1 d U . . H59 H 0.1016 0.0912 0.0952 0.095 Uiso 1 1 calc R . . C62 C -0.0391(5) 0.1031(4) 0.0745(7) 0.088(3) Uani 1 1 d U . . H62 H -0.0754 0.1063 0.0696 0.106 Uiso 1 1 calc R . . C39 C 0.2763(5) 0.3865(4) -0.0886(5) 0.078(3) Uani 1 1 d U . . H39 H 0.2999 0.4026 -0.1090 0.093 Uiso 1 1 calc R . . C75 C 0.1513(5) 0.0912(3) 0.2634(7) 0.091(3) Uani 1 1 d U . . H75 H 0.1261 0.0740 0.2473 0.109 Uiso 1 1 calc R . . C3 C 0.1532(6) 0.4695(3) -0.1156(6) 0.090(3) Uani 1 1 d U . . H3 H 0.1770 0.4848 -0.1381 0.108 Uiso 1 1 calc R . . C53 C 0.1458(7) 0.1279(4) -0.1877(7) 0.123(5) Uani 1 1 d U . . H53 H 0.1118 0.1202 -0.1800 0.148 Uiso 1 1 calc R . . C82 C 0.2777(5) 0.2648(3) 0.3189(7) 0.083(3) Uani 1 1 d U . . H82 H 0.3031 0.2828 0.3138 0.099 Uiso 1 1 calc R . . C4 C 0.1028(6) 0.4722(3) -0.1353(6) 0.092(4) Uani 1 1 d U . . H4 H 0.0915 0.4892 -0.1721 0.110 Uiso 1 1 calc R . . C76 C 0.2027(5) 0.0827(3) 0.2668(6) 0.085(3) Uani 1 1 d U . . H76 H 0.2134 0.0596 0.2523 0.102 Uiso 1 1 calc R . . C57 C 0.2181(5) 0.1620(3) -0.1510(7) 0.091(3) Uani 1 1 d U . . H57 H 0.2356 0.1786 -0.1184 0.110 Uiso 1 1 calc R . . C81 C 0.2490(4) 0.2528(3) 0.2592(6) 0.074(3) Uani 1 1 d U . . H81 H 0.2556 0.2615 0.2112 0.089 Uiso 1 1 calc R . . C28 C 0.1143(6) 0.4477(4) 0.6677(6) 0.108(5) Uani 1 1 d U . . H28 H 0.1211 0.4430 0.7192 0.129 Uiso 1 1 calc R . . C48 C 0.1432(4) 0.1630(3) -0.0703(5) 0.064(2) Uani 1 1 d U . . C56 C 0.2414(6) 0.1496(4) -0.2130(8) 0.108(4) Uani 1 1 d U . . H56 H 0.2747 0.1581 -0.2230 0.130 Uiso 1 1 calc R . . C63 C -0.0065(4) 0.1290(3) 0.0471(6) 0.075(3) Uani 1 1 d U . . H63 H -0.0207 0.1495 0.0225 0.090 Uiso 1 1 calc R . . C83 C 0.2689(4) 0.2501(3) 0.3890(6) 0.077(3) Uani 1 1 d U . . H83 H 0.2897 0.2575 0.4315 0.093 Uiso 1 1 calc R . . C26 C 0.1125(7) 0.4871(4) 0.5670(7) 0.126(5) Uani 1 1 d U . . H26 H 0.1188 0.5104 0.5485 0.152 Uiso 1 1 calc R . . C74 C 0.1375(5) 0.1242(3) 0.2833(6) 0.078(3) Uani 1 1 d U . . H74 H 0.1019 0.1302 0.2773 0.094 Uiso 1 1 calc R . . C27 C 0.1206(7) 0.4806(4) 0.6413(7) 0.126(5) Uani 1 1 d U . . H27 H 0.1306 0.4996 0.6743 0.151 Uiso 1 1 calc R . . C61 C -0.0181(5) 0.0727(4) 0.1092(7) 0.090(3) Uani 1 1 d U . . H61 H -0.0401 0.0548 0.1273 0.108 Uiso 1 1 calc R . . C60 C 0.0335(5) 0.0687(4) 0.1170(8) 0.093(3) Uani 1 1 d U . . H60 H 0.0478 0.0480 0.1411 0.111 Uiso 1 1 calc R . . C55 C 0.2176(7) 0.1258(4) -0.2594(8) 0.112(5) Uani 1 1 d U . . H55 H 0.2357 0.1159 -0.2989 0.134 Uiso 1 1 calc R . . C5 C 0.0668(6) 0.4506(3) -0.1031(6) 0.089(3) Uani 1 1 d U . . H5 H 0.0310 0.4530 -0.1163 0.107 Uiso 1 1 calc R . . C54 C 0.1702(8) 0.1159(5) -0.2513(8) 0.139(6) Uani 1 1 d U . . H54 H 0.1525 0.1010 -0.2872 0.167 Uiso 1 1 calc R . . O12 O 0.0000 0.2371(2) 0.2500 0.0491(19) Uani 1 2 d SU . . O4 O -0.0148(3) 0.30044(16) 0.3375(3) 0.0515(16) Uani 1 1 d U . . O13 O 0.0000 0.1294(2) 0.2500 0.066(2) Uani 1 2 d SU . . O11 O 0.1198(2) 0.28488(18) 0.1666(3) 0.0588(16) Uani 1 1 d U . . Na1 Na 0.0893(5) 0.3517(3) 0.1408(6) 0.106(3) Uani 0.50 1 d PU . . S1 S 0.3321(3) 0.4994(2) 0.8768(5) 0.200(3) Uani 1 1 d DU . . O14 O 0.2790(6) 0.5006(6) 0.8438(11) 0.246(7) Uani 1 1 d DU . . O15 O 0.3454(8) 0.4721(5) 0.9371(13) 0.308(10) Uani 1 1 d DU . . O16 O 0.3693(9) 0.5059(9) 0.8180(15) 0.388(14) Uani 1 1 d DU . . C85 C 0.3269(7) 0.5338(7) 0.9232(13) 0.207(6) Uani 1 1 d DU . . F1 F 0.3200(10) 0.5651(4) 0.8848(11) 0.328(9) Uani 1 1 d DU . . F2 F 0.2834(9) 0.5363(4) 0.9670(11) 0.301(9) Uani 1 1 d DU . . F3 F 0.3678(10) 0.5416(4) 0.9745(13) 0.378(12) Uani 1 1 d DU . . C86 C 0.2153(4) 0.3671(3) 0.4493(6) 0.099(4) Uani 1 1 d DU . . H86 H 0.2354 0.3851 0.4275 0.119 Uiso 1 1 calc R . . C87 C 0.1991(4) 0.3714(3) 0.5201(6) 0.108(4) Uani 1 1 d DU . . H87 H 0.2082 0.3925 0.5474 0.130 Uiso 1 1 calc R . . C88 C 0.1701(5) 0.3456(4) 0.5516(6) 0.115(4) Uani 1 1 d DU . . H88 H 0.1599 0.3484 0.6011 0.138 Uiso 1 1 calc R . . C89 C 0.1555(5) 0.3153(4) 0.5110(7) 0.115(4) Uani 1 1 d DU . . H89 H 0.1337 0.2981 0.5314 0.138 Uiso 1 1 calc R . . C90 C 0.1728(5) 0.3105(3) 0.4412(7) 0.107(4) Uani 1 1 d DU . . H90 H 0.1645 0.2892 0.4143 0.129 Uiso 1 1 calc R . . C91 C 0.2021(5) 0.3365(3) 0.4105(6) 0.101(4) Uani 1 1 d DU . . H91 H 0.2134 0.3333 0.3617 0.122 Uiso 1 1 calc R . . C805 C 0.511(4) 0.9152(9) 0.233(5) 0.36(3) Uani 0.50 1 d PDU A -1 H805 H 0.5148 0.8902 0.2275 0.436 Uiso 0.50 1 calc PR A -1 C802 C 0.508(3) 0.9833(9) 0.254(4) 0.35(3) Uani 0.50 1 d PDU A -1 H802 H 0.5091 1.0083 0.2627 0.423 Uiso 0.50 1 calc PR A -1 C803 C 0.520(3) 0.9707(15) 0.191(4) 0.35(3) Uani 0.50 1 d PDU A -1 H803 H 0.5293 0.9866 0.1524 0.420 Uiso 0.50 1 calc PR A -1 C804 C 0.520(3) 0.9368(16) 0.179(4) 0.36(3) Uani 0.50 1 d PDU A -1 H804 H 0.5264 0.9276 0.1313 0.428 Uiso 0.50 1 calc PR A -1 C801 C 0.496(3) 0.9619(15) 0.307(4) 0.34(3) Uani 0.50 1 d PDU A -1 H801 H 0.4862 0.9712 0.3530 0.414 Uiso 0.50 1 calc PR A -1 C800 C 0.495(3) 0.9278(14) 0.295(4) 0.35(3) Uani 0.50 1 d PDU A -1 H800 H 0.4841 0.9120 0.3323 0.418 Uiso 0.50 1 calc PR A -1 C903 C 0.488(2) 0.3315(11) 0.317(3) 0.186(13) Uani 0.50 1 d PDU B -1 H903 H 0.4848 0.3183 0.3621 0.223 Uiso 0.50 1 calc PR B -1 C902 C 0.488(2) 0.3145(7) 0.252(3) 0.201(14) Uani 0.50 1 d PDU B -1 H902 H 0.4753 0.2906 0.2475 0.241 Uiso 0.50 1 calc PR B -1 C904 C 0.494(2) 0.3672(11) 0.320(3) 0.203(14) Uani 0.50 1 d PDU B -1 H904 H 0.4842 0.3803 0.3623 0.244 Uiso 0.50 1 calc PR B -1 C905 C 0.512(2) 0.3839(8) 0.262(3) 0.216(16) Uani 0.50 1 d PDU B -1 H905 H 0.5225 0.4083 0.2655 0.259 Uiso 0.50 1 calc PR B -1 C901 C 0.5043(19) 0.3315(10) 0.193(3) 0.187(15) Uani 0.50 1 d PDU B -1 H901 H 0.5072 0.3190 0.1474 0.224 Uiso 0.50 1 calc PR B -1 C900 C 0.517(2) 0.3662(10) 0.198(3) 0.219(16) Uani 0.50 1 d PDU B -1 H900 H 0.5292 0.3782 0.1557 0.263 Uiso 0.50 1 calc PR B -1 C400 C 0.4960(16) 0.4691(12) 0.112(3) 0.41(3) Uani 1 1 d DU . . H40A H 0.5203 0.4706 0.0730 0.617 Uiso 1 1 calc R . . H40B H 0.5071 0.4503 0.1477 0.617 Uiso 1 1 calc R . . H40C H 0.4950 0.4921 0.1385 0.617 Uiso 1 1 calc R . . C401 C 0.4529(19) 0.4620(12) 0.0847(19) 0.41(2) Uani 1 1 d DU . . H40D H 0.4565 0.4394 0.0570 0.491 Uiso 1 1 calc R . . H40E H 0.4448 0.4807 0.0468 0.491 Uiso 1 1 calc R . . C402 C 0.4136(16) 0.4587(14) 0.120(3) 0.41(2) Uani 1 1 d DU . . H40F H 0.3840 0.4630 0.0842 0.498 Uiso 1 1 calc R . . H40G H 0.4120 0.4331 0.1344 0.498 Uiso 1 1 calc R . . C403 C 0.4049(12) 0.4758(12) 0.177(2) 0.41(2) Uani 1 1 d DU . . H40H H 0.3809 0.4610 0.2042 0.497 Uiso 1 1 calc R . . H40I H 0.3851 0.4971 0.1591 0.497 Uiso 1 1 calc R . . C404 C 0.438(2) 0.4869(7) 0.2242(19) 0.39(2) Uani 1 1 d DU . . H40J H 0.4211 0.4959 0.2676 0.584 Uiso 1 1 calc R . . H40K H 0.4578 0.5063 0.2028 0.584 Uiso 1 1 calc R . . H40L H 0.4614 0.4673 0.2395 0.584 Uiso 1 1 calc R . . C704 C 0.6455(6) 0.1496(4) 0.2862(7) 0.114(5) Uani 1 1 d DU . . H704 H 0.6735 0.1383 0.3133 0.137 Uiso 1 1 calc R . . C702 C 0.5595(5) 0.1499(5) 0.2420(10) 0.157(7) Uani 1 1 d DU . . H702 H 0.5266 0.1387 0.2385 0.188 Uiso 1 1 calc R . . C705 C 0.6523(5) 0.1812(4) 0.2527(9) 0.125(5) Uani 1 1 d DU . . H705 H 0.6850 0.1926 0.2566 0.150 Uiso 1 1 calc R . . C703 C 0.5987(7) 0.1343(4) 0.2811(8) 0.135(5) Uani 1 1 d DU . . H703 H 0.5934 0.1121 0.3054 0.162 Uiso 1 1 calc R . . C701 C 0.5662(6) 0.1812(5) 0.2078(7) 0.153(7) Uani 1 1 d DU . . H701 H 0.5383 0.1922 0.1799 0.183 Uiso 1 1 calc R . . C700 C 0.6124(7) 0.1970(4) 0.2132(7) 0.137(6) Uani 1 1 d DU . . H700 H 0.6173 0.2193 0.1894 0.164 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 0.0584(9) 0.0607(9) 0.0243(7) 0.0013(6) 0.0077(6) 0.0001(7) Fe2 0.0579(13) 0.0636(13) 0.0295(10) 0.000 0.0085(9) 0.000 O2 0.087(5) 0.060(4) 0.024(3) 0.000(3) 0.004(3) -0.003(3) O1 0.088(5) 0.066(4) 0.027(3) 0.002(3) 0.010(3) -0.006(3) O5 0.069(4) 0.072(4) 0.030(3) 0.003(3) 0.011(3) -0.004(3) O9 0.061(4) 0.063(4) 0.034(3) 0.002(3) 0.007(3) 0.001(3) O3 0.061(4) 0.059(4) 0.029(3) -0.002(3) 0.003(3) -0.005(3) O10 0.062(4) 0.066(4) 0.038(3) 0.005(3) 0.007(3) 0.001(3) O6 0.069(4) 0.073(4) 0.032(3) -0.001(3) 0.014(3) 0.014(3) O8 0.063(4) 0.067(4) 0.025(3) -0.004(3) 0.008(3) 0.002(3) N2 0.060(5) 0.073(5) 0.032(4) 0.003(4) 0.010(3) 0.004(4) O7 0.067(4) 0.066(4) 0.036(3) -0.006(3) 0.011(3) 0.000(3) C46 0.056(6) 0.068(5) 0.030(5) -0.003(4) 0.006(4) 0.006(4) C20 0.058(6) 0.066(6) 0.027(4) -0.005(4) 0.003(4) -0.005(4) N1 0.082(6) 0.060(5) 0.026(4) 0.002(3) 0.008(4) 0.003(4) C42 0.071(6) 0.079(5) 0.023(5) 0.008(5) 0.010(4) -0.005(5) C23 0.073(6) 0.056(5) 0.027(4) -0.001(4) 0.005(4) -0.001(4) C18 0.078(7) 0.051(5) 0.029(4) -0.001(4) 0.004(4) -0.002(5) C30 0.058(6) 0.072(5) 0.028(5) -0.007(4) -0.001(4) -0.012(4) C16 0.089(7) 0.067(6) 0.023(4) 0.003(4) 0.007(4) 0.002(5) C9 0.102(8) 0.068(6) 0.036(4) 0.003(4) 0.016(4) -0.014(5) C43 0.068(6) 0.093(6) 0.036(5) 0.012(5) 0.013(4) 0.012(5) C79 0.061(5) 0.078(6) 0.045(5) -0.009(5) 0.011(4) 0.001(4) C17 0.083(7) 0.055(6) 0.028(4) 0.003(4) 0.008(4) 0.012(5) C21 0.059(6) 0.061(5) 0.025(4) 0.001(4) -0.002(4) -0.003(4) C8 0.097(7) 0.071(6) 0.033(5) 0.005(4) 0.011(4) -0.011(4) C50 0.060(6) 0.073(5) 0.044(5) -0.009(4) 0.004(4) 0.005(5) C22 0.066(6) 0.066(6) 0.025(4) -0.001(4) 0.007(4) 0.001(4) C73 0.069(6) 0.077(6) 0.047(6) -0.006(5) 0.003(5) 0.017(4) C31 0.071(6) 0.079(6) 0.032(5) -0.005(5) 0.009(4) -0.012(5) C34 0.083(7) 0.070(6) 0.044(6) 0.002(5) 0.001(5) -0.006(5) C11 0.120(9) 0.066(7) 0.037(5) 0.007(5) 0.008(5) -0.023(5) C24 0.095(8) 0.070(6) 0.035(4) -0.010(4) 0.017(5) -0.013(6) C19 0.067(6) 0.064(6) 0.025(4) -0.004(4) 0.002(4) -0.001(4) C51 0.051(6) 0.068(5) 0.032(5) -0.001(4) 0.004(4) 0.005(4) C45 0.064(6) 0.073(5) 0.033(5) -0.003(4) 0.011(4) 0.012(5) C58 0.065(5) 0.074(6) 0.048(6) -0.015(5) 0.006(5) -0.007(5) C41 0.064(6) 0.096(6) 0.035(5) 0.007(5) 0.009(4) -0.002(5) C72 0.085(8) 0.093(7) 0.048(5) 0.014(5) 0.010(5) 0.018(6) C1 0.125(7) 0.083(6) 0.039(5) 0.016(5) 0.019(5) -0.028(6) C77 0.095(7) 0.082(7) 0.063(7) -0.007(6) 0.026(6) 0.017(5) C68 0.063(7) 0.095(7) 0.040(5) -0.006(5) 0.008(5) 0.009(5) C15 0.105(8) 0.062(7) 0.036(5) 0.003(4) 0.002(5) -0.004(5) C29 0.119(9) 0.082(7) 0.031(5) -0.012(4) 0.008(6) -0.017(7) C38 0.101(7) 0.089(6) 0.026(5) 0.013(5) 0.012(5) -0.018(5) C33 0.078(7) 0.096(6) 0.029(5) 0.010(5) 0.001(4) -0.017(6) C25 0.181(12) 0.072(6) 0.040(5) -0.010(5) 0.023(7) -0.023(8) C37 0.087(7) 0.075(5) 0.027(5) 0.007(4) 0.008(4) -0.012(5) C52 0.093(7) 0.088(8) 0.055(6) -0.003(5) 0.024(5) 0.029(6) C67 0.065(6) 0.079(7) 0.040(4) 0.001(4) 0.008(4) 0.014(5) C69 0.070(7) 0.094(7) 0.050(5) 0.001(5) 0.015(5) 0.011(6) C49 0.081(7) 0.082(7) 0.045(6) -0.018(5) 0.014(5) 0.005(5) C36 0.069(6) 0.068(6) 0.020(4) 0.004(4) 0.007(5) -0.005(5) C65 0.062(5) 0.060(6) 0.029(5) 0.000(4) 0.010(4) 0.005(4) C35 0.085(7) 0.067(5) 0.032(5) 0.000(5) 0.006(5) -0.009(5) C80 0.060(6) 0.087(8) 0.052(5) -0.004(5) 0.014(5) 0.002(5) C66 0.057(5) 0.073(5) 0.033(4) 0.000(4) 0.010(4) 0.007(4) C32 0.073(7) 0.090(7) 0.030(5) 0.000(5) 0.006(4) -0.015(5) C12 0.152(11) 0.090(8) 0.045(5) 0.005(6) 0.008(6) -0.053(7) C78 0.074(6) 0.083(7) 0.064(7) -0.007(6) 0.006(6) 0.015(5) C40 0.077(7) 0.118(7) 0.043(6) 0.012(6) 0.017(5) -0.009(6) C10 0.103(8) 0.063(6) 0.034(4) 0.005(4) 0.014(5) -0.013(5) C64 0.062(6) 0.069(6) 0.027(5) -0.006(4) 0.005(4) -0.001(5) C44 0.072(6) 0.074(5) 0.026(5) 0.010(4) 0.009(4) 0.010(5) C71 0.091(8) 0.101(8) 0.057(6) 0.020(6) 0.013(6) 0.017(7) C47 0.067(6) 0.077(5) 0.038(5) -0.001(4) 0.011(4) 0.009(5) C84 0.061(7) 0.102(8) 0.051(5) -0.012(5) 0.012(5) 0.000(5) C14 0.121(9) 0.071(7) 0.037(4) 0.011(4) 0.011(5) -0.025(6) C2 0.133(7) 0.065(6) 0.030(5) 0.003(4) 0.013(5) -0.010(5) C7 0.110(6) 0.067(6) 0.030(5) 0.000(4) 0.015(5) -0.001(5) C70 0.072(7) 0.105(8) 0.051(6) 0.013(5) 0.008(5) 0.013(6) C13 0.144(11) 0.095(9) 0.047(5) 0.009(6) 0.020(6) -0.046(7) C6 0.117(7) 0.073(7) 0.032(5) -0.010(4) 0.005(5) 0.001(6) C59 0.064(6) 0.093(8) 0.082(8) 0.005(6) 0.010(6) -0.002(5) C62 0.062(7) 0.110(9) 0.094(9) -0.022(7) 0.015(6) -0.011(6) C39 0.091(8) 0.107(7) 0.036(6) 0.013(6) 0.017(5) -0.025(6) C75 0.095(7) 0.080(7) 0.098(9) -0.012(7) 0.004(7) 0.024(6) C3 0.153(9) 0.074(7) 0.043(6) 0.006(5) 0.018(7) -0.008(8) C53 0.156(11) 0.141(12) 0.078(8) -0.043(7) 0.051(8) 0.000(9) C82 0.085(8) 0.087(8) 0.076(7) -0.006(6) 0.007(6) -0.010(6) C4 0.163(10) 0.081(8) 0.031(6) 0.004(5) 0.007(7) 0.016(8) C76 0.107(8) 0.075(7) 0.074(8) -0.009(6) 0.006(7) 0.023(6) C57 0.112(8) 0.096(9) 0.072(7) 0.012(6) 0.045(6) 0.031(7) C81 0.084(8) 0.089(8) 0.052(5) 0.002(6) 0.020(5) -0.007(6) C28 0.188(13) 0.097(8) 0.038(6) -0.018(5) 0.009(7) -0.053(9) C48 0.070(7) 0.077(6) 0.047(6) -0.009(5) 0.010(4) 0.012(5) C56 0.133(10) 0.117(11) 0.080(9) 0.014(7) 0.056(8) 0.036(8) C63 0.064(5) 0.096(8) 0.065(7) -0.013(6) 0.005(5) -0.001(5) C83 0.076(7) 0.098(9) 0.057(5) -0.017(6) 0.004(6) -0.013(6) C26 0.234(15) 0.086(8) 0.062(6) -0.012(6) 0.033(9) -0.068(10) C74 0.074(7) 0.079(7) 0.081(8) -0.014(6) 0.003(6) 0.011(5) C27 0.223(15) 0.104(8) 0.054(6) -0.026(6) 0.031(9) -0.084(10) C61 0.083(7) 0.090(8) 0.098(9) -0.022(6) 0.028(7) -0.025(7) C60 0.087(7) 0.085(8) 0.107(9) 0.005(7) 0.014(7) -0.010(6) C55 0.147(11) 0.118(11) 0.076(9) 0.004(7) 0.049(9) 0.049(9) C5 0.132(9) 0.089(9) 0.047(7) -0.009(5) 0.005(6) 0.015(7) C54 0.178(13) 0.162(14) 0.084(9) -0.040(8) 0.060(10) 0.004(11) O12 0.060(5) 0.067(4) 0.020(4) 0.000 0.001(3) 0.000 O4 0.070(4) 0.061(4) 0.024(3) -0.006(3) 0.004(3) -0.003(3) O13 0.070(6) 0.067(5) 0.061(6) 0.000 0.007(5) 0.000 O11 0.062(4) 0.082(4) 0.033(3) 0.003(3) 0.009(3) -0.006(3) Na1 0.144(9) 0.095(6) 0.081(6) 0.002(5) 0.004(6) -0.029(5) S1 0.170(6) 0.202(6) 0.229(8) 0.000(5) 0.022(5) 0.017(5) O14 0.174(10) 0.32(2) 0.240(17) 0.029(14) -0.034(10) 0.038(13) O15 0.249(18) 0.212(14) 0.45(3) 0.077(16) -0.088(16) 0.102(15) O16 0.273(18) 0.51(4) 0.40(3) -0.081(19) 0.20(2) -0.01(2) C85 0.295(19) 0.141(10) 0.191(18) 0.023(8) 0.059(11) -0.026(16) F1 0.54(3) 0.187(9) 0.263(18) 0.070(11) 0.072(16) -0.029(16) F2 0.385(18) 0.182(12) 0.36(2) 0.041(12) 0.172(16) 0.014(14) F3 0.396(19) 0.168(13) 0.55(3) -0.019(13) -0.16(2) -0.077(15) C86 0.072(8) 0.153(10) 0.074(7) 0.002(7) 0.013(6) 0.011(8) C87 0.089(9) 0.171(12) 0.065(7) 0.007(7) 0.000(6) 0.015(8) C88 0.099(10) 0.179(13) 0.068(8) 0.027(7) 0.008(7) 0.020(9) C89 0.094(10) 0.153(11) 0.098(9) 0.038(8) 0.011(8) 0.030(8) C90 0.101(10) 0.112(9) 0.112(9) 0.023(7) 0.023(8) 0.037(7) C91 0.094(10) 0.129(11) 0.083(8) 0.008(6) 0.016(7) 0.015(8) C805 0.21(4) 0.27(3) 0.57(6) 0.22(4) -0.23(4) -0.08(4) C802 0.22(5) 0.26(3) 0.55(6) 0.26(4) -0.18(5) -0.07(4) C803 0.19(4) 0.29(3) 0.55(6) 0.25(5) -0.18(4) -0.08(4) C804 0.18(4) 0.30(4) 0.57(6) 0.22(5) -0.21(4) -0.07(4) C801 0.22(5) 0.25(3) 0.53(6) 0.27(4) -0.21(4) -0.05(4) C800 0.20(4) 0.26(3) 0.55(6) 0.25(5) -0.24(4) -0.07(4) C903 0.18(3) 0.25(3) 0.13(2) -0.07(3) 0.02(2) -0.03(3) C902 0.21(3) 0.25(2) 0.15(2) -0.10(3) 0.04(3) 0.01(3) C904 0.20(3) 0.26(3) 0.15(2) -0.10(3) 0.02(2) -0.05(3) C905 0.24(3) 0.23(2) 0.18(3) -0.12(3) 0.04(3) -0.09(3) C901 0.18(3) 0.24(3) 0.14(2) -0.13(3) 0.06(2) -0.01(3) C900 0.21(3) 0.26(3) 0.20(3) -0.13(3) 0.08(3) -0.04(3) C400 0.44(5) 0.28(4) 0.53(6) -0.03(4) 0.14(4) -0.13(4) C401 0.49(5) 0.28(3) 0.48(4) -0.18(3) 0.17(4) -0.23(4) C402 0.47(4) 0.31(3) 0.49(5) -0.17(3) 0.17(4) -0.19(3) C403 0.46(4) 0.31(4) 0.48(5) -0.17(3) 0.16(3) -0.21(3) C404 0.69(7) 0.101(18) 0.36(4) 0.06(2) -0.05(4) -0.08(3) C704 0.137(10) 0.153(12) 0.049(8) -0.034(8) -0.021(8) 0.035(9) C702 0.130(11) 0.189(17) 0.149(17) -0.091(11) -0.010(10) -0.045(11) C705 0.122(10) 0.164(13) 0.095(12) -0.034(9) 0.044(8) -0.007(10) C703 0.198(15) 0.142(12) 0.066(9) -0.026(8) 0.023(10) -0.033(11) C701 0.168(13) 0.219(18) 0.066(10) -0.048(11) -0.028(11) 0.043(12) C700 0.201(15) 0.161(13) 0.053(9) 0.014(8) 0.048(10) 0.018(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 O12 1.898(4) . ? Fe1 O8 2.009(6) . ? Fe1 O10 2.013(6) . ? Fe1 O3 2.016(6) . ? Fe1 O4 2.023(6) 2 ? Fe1 O11 2.083(6) . ? Fe2 O12 1.882(9) . ? Fe2 O7 2.006(6) . ? Fe2 O7 2.006(6) 2 ? Fe2 O9 2.019(6) 2 ? Fe2 O9 2.019(6) . ? Fe2 O13 2.146(10) . ? O2 C18 1.373(11) . ? O2 C17 1.385(10) . ? O1 C10 1.385(11) . ? O1 C16 1.388(11) . ? O1 Na1 2.711(12) . ? O5 C44 1.376(11) . ? O5 C42 1.406(11) . ? O9 C65 1.265(11) . ? O3 C36 1.262(11) . ? O10 C65 1.258(11) . ? O6 C45 1.353(11) . ? O6 C47 1.398(12) . ? O8 C64 1.243(11) . ? N2 C45 1.302(11) . ? N2 C46 1.402(12) . ? O7 C64 1.261(11) . ? C46 C51 1.395(13) . ? C46 C47 1.401(13) . ? C20 C21 1.387(12) . ? C20 C19 1.388(13) . ? C20 C36 1.507(13) . ? N1 C17 1.286(12) . ? N1 C19 1.414(11) . ? C42 C37 1.328(14) . ? C42 C41 1.405(14) . ? C23 C22 1.382(12) . ? C23 C18 1.384(12) . ? C23 C24 1.453(13) . ? C18 C19 1.378(12) . ? C30 C35 1.367(13) . ? C30 C31 1.376(13) . ? C30 C21 1.508(13) . ? C16 C15 1.344(14) . ? C16 C17 1.421(14) . ? C9 C14 1.364(14) . ? C9 C10 1.384(13) . ? C9 C8 1.537(14) . ? C43 C44 1.362(13) . ? C43 C41 1.413(15) . ? C43 H43 0.9500 . ? C79 C84 1.386(14) . ? C79 C80 1.394(13) . ? C79 C66 1.508(14) . ? C21 C22 1.415(12) . ? C8 C7 1.511(15) . ? C8 C37 1.516(15) . ? C8 H8 1.0000 . ? C50 C49 1.394(13) . ? C50 C51 1.422(13) . ? C50 C58 1.505(14) . ? C22 H22 0.9500 . ? C73 C74 1.386(15) . ? C73 C78 1.394(14) . ? C73 C66 1.529(14) . ? C31 C32 1.364(13) . ? C31 H31 0.9500 . ? C34 C33 1.365(14) . ? C34 C35 1.393(13) . ? C34 H34 0.9500 . ? C11 C10 1.378(14) . ? C11 C12 1.390(15) . ? C11 C15 1.437(14) . ? C24 C25 1.378(15) . ? C24 C29 1.393(14) . ? C51 C64 1.487(13) . ? C45 C44 1.423(14) . ? C58 C63 1.351(14) . ? C58 C59 1.389(15) . ? C41 C40 1.398(15) . ? C72 C67 1.386(14) . ? C72 C71 1.410(14) . ? C72 H72 0.9500 . ? C1 C2 1.513(17) . ? C1 C38 1.514(16) . ? C1 C14 1.540(14) . ? C1 H1 1.0000 . ? C77 C76 1.338(16) . ? C77 C78 1.402(15) . ? C77 H77 0.9500 . ? C68 C67 1.368(13) . ? C68 C69 1.396(14) . ? C68 H68 0.9500 . ? C15 H15 0.9500 . ? C29 C28 1.384(15) . ? C29 H29 0.9500 . ? C38 C39 1.387(16) . ? C38 C37 1.400(14) . ? C33 C32 1.385(15) . ? C33 H33 0.9500 . ? C25 C26 1.355(16) . ? C25 H25 0.9500 . ? C52 C57 1.350(16) . ? C52 C53 1.380(18) . ? C52 C48 1.503(14) . ? C67 C66 1.551(13) . ? C69 C70 1.320(14) . ? C69 H69 0.9500 . ? C49 C48 1.391(14) . ? C49 H49 0.9500 . ? C36 O4 1.239(11) . ? C65 C66 1.541(13) . ? C35 H35 0.9500 . ? C80 C81 1.386(14) . ? C80 H80 0.9500 . ? C32 H32 0.9500 . ? C12 C13 1.369(15) . ? C12 H12 0.9500 . ? C78 H78 0.9500 . ? C40 C39 1.346(16) . ? C40 H40 0.9500 . ? C71 C70 1.391(15) . ? C71 H71 0.9500 . ? C47 C48 1.342(14) . ? C84 C83 1.383(15) . ? C84 H84 0.9500 . ? C14 C13 1.379(15) . ? C2 C3 1.387(16) . ? C2 C7 1.399(15) . ? C7 C6 1.347(15) . ? C70 H70 0.9500 . ? C13 H13 0.9500 . ? C6 C5 1.404(15) . ? C6 H6 0.9500 . ? C59 C60 1.378(16) . ? C59 H59 0.9500 . ? C62 C61 1.392(17) . ? C62 C63 1.398(16) . ? C62 H62 0.9500 . ? C39 H39 0.9500 . ? C75 C74 1.342(15) . ? C75 C76 1.371(16) . ? C75 H75 0.9500 . ? C3 C4 1.343(18) . ? C3 H3 0.9500 . ? C53 C54 1.414(18) . ? C53 H53 0.9500 . ? C82 C81 1.346(15) . ? C82 C83 1.407(15) . ? C82 H82 0.9500 . ? C4 C5 1.390(18) . ? C4 H4 0.9500 . ? C76 H76 0.9500 . ? C57 C56 1.381(16) . ? C57 H57 0.9500 . ? C81 H81 0.9500 . ? C28 C27 1.333(17) . ? C28 H28 0.9500 . ? C56 C55 1.35(2) . ? C56 H56 0.9500 . ? C63 H63 0.9500 . ? C83 H83 0.9500 . ? C26 C27 1.363(18) . ? C26 H26 0.9500 . ? C74 H74 0.9500 . ? C27 H27 0.9500 . ? C61 C60 1.350(17) . ? C61 H61 0.9500 . ? C60 H60 0.9500 . ? C55 C54 1.30(2) . ? C55 H55 0.9500 . ? C5 H5 0.9500 . ? C54 H54 0.9500 . ? O12 Fe1 1.897(4) 2 ? O4 Fe1 2.023(6) 2 ? O4 Na1 2.771(12) 2 ? O11 Na1 2.654(13) . ? Na1 O4 2.771(12) 2 ? S1 O14 1.470(13) . ? S1 O16 1.498(15) . ? S1 O15 1.514(15) . ? S1 C85 1.54(3) . ? C85 F1 1.366(18) . ? C85 F3 1.397(18) . ? C85 F2 1.420(19) . ? C86 C91 1.373(12) . ? C86 C87 1.375(11) . ? C86 H86 0.9500 . ? C87 C88 1.370(12) . ? C87 H87 0.9500 . ? C88 C89 1.387(17) . ? C88 H88 0.9500 . ? C89 C90 1.371(12) . ? C89 H89 0.9500 . ? C90 C91 1.374(12) . ? C90 H90 0.9500 . ? C91 H91 0.9500 . ? C805 C800 1.29(2) . ? C805 C804 1.30(2) . ? C805 H805 0.9500 . ? C802 C803 1.29(2) . ? C802 C801 1.29(2) . ? C802 H802 0.9500 . ? C803 C804 1.28(2) . ? C803 H803 0.9500 . ? C804 H804 0.9500 . ? C801 C800 1.29(2) . ? C801 H801 0.9500 . ? C800 H800 0.9500 . ? C903 C902 1.338(17) . ? C903 C904 1.343(17) . ? C903 H903 0.9500 . ? C902 C901 1.335(17) . ? C902 H902 0.9500 . ? C904 C905 1.344(17) . ? C904 H904 0.9500 . ? C905 C900 1.337(17) . ? C905 H905 0.9500 . ? C901 C900 1.340(17) . ? C901 H901 0.9500 . ? C900 H900 0.9500 . ? C400 C401 1.23(3) . ? C400 H40A 0.9800 . ? C400 H40B 0.9800 . ? C400 H40C 0.9800 . ? C401 C402 1.25(3) . ? C401 H40D 0.9900 . ? C401 H40E 0.9900 . ? C402 C403 1.23(3) . ? C402 H40F 0.9900 . ? C402 H40G 0.9900 . ? C403 C404 1.25(3) . ? C403 H40H 0.9900 . ? C403 H40I 0.9900 . ? C404 H40J 0.9800 . ? C404 H40K 0.9800 . ? C404 H40L 0.9800 . ? C704 C705 1.343(12) . ? C704 C703 1.347(12) . ? C704 H704 0.9500 . ? C702 C703 1.336(12) . ? C702 C701 1.341(12) . ? C702 H702 0.9500 . ? C705 C700 1.355(12) . ? C705 H705 0.9500 . ? C703 H703 0.9500 . ? C701 C700 1.336(12) . ? C701 H701 0.9500 . ? C700 H700 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 O12 Fe1 O8 91.7(2) . . ? O12 Fe1 O10 93.0(2) . . ? O8 Fe1 O10 89.7(2) . . ? O12 Fe1 O3 96.8(2) . . ? O8 Fe1 O3 171.5(2) . . ? O10 Fe1 O3 89.9(2) . . ? O12 Fe1 O4 94.6(3) . 2 ? O8 Fe1 O4 90.2(2) . 2 ? O10 Fe1 O4 172.4(3) . 2 ? O3 Fe1 O4 89.0(2) . 2 ? O12 Fe1 O11 170.5(2) . . ? O8 Fe1 O11 78.8(2) . . ? O10 Fe1 O11 86.9(3) . . ? O3 Fe1 O11 92.7(2) . . ? O4 Fe1 O11 85.6(3) 2 . ? O12 Fe2 O7 99.34(19) . . ? O12 Fe2 O7 99.35(19) . 2 ? O7 Fe2 O7 161.3(4) . 2 ? O12 Fe2 O9 94.12(18) . 2 ? O7 Fe2 O9 90.7(2) . 2 ? O7 Fe2 O9 88.0(2) 2 2 ? O12 Fe2 O9 94.13(18) . . ? O7 Fe2 O9 88.0(2) . . ? O7 Fe2 O9 90.7(2) 2 . ? O9 Fe2 O9 171.7(4) 2 . ? O12 Fe2 O13 180.000(1) . . ? O7 Fe2 O13 80.66(19) . . ? O7 Fe2 O13 80.65(19) 2 . ? O9 Fe2 O13 85.88(18) 2 . ? O9 Fe2 O13 85.87(18) . . ? C18 O2 C17 103.3(7) . . ? C10 O1 C16 104.0(7) . . ? C10 O1 Na1 126.3(6) . . ? C16 O1 Na1 129.7(6) . . ? C44 O5 C42 106.2(7) . . ? C65 O9 Fe2 125.0(6) . . ? C36 O3 Fe1 127.7(6) . . ? C65 O10 Fe1 136.7(6) . . ? C45 O6 C47 105.0(7) . . ? C64 O8 Fe1 128.3(6) . . ? C45 N2 C46 104.5(8) . . ? C64 O7 Fe2 129.6(6) . . ? C51 C46 C47 119.6(9) . . ? C51 C46 N2 131.5(8) . . ? C47 C46 N2 108.9(8) . . ? C21 C20 C19 117.1(8) . . ? C21 C20 C36 123.5(8) . . ? C19 C20 C36 119.3(8) . . ? C17 N1 C19 104.4(7) . . ? C37 C42 C41 125.4(10) . . ? C37 C42 O5 125.5(9) . . ? C41 C42 O5 108.8(9) . . ? C22 C23 C18 113.0(8) . . ? C22 C23 C24 123.1(8) . . ? C18 C23 C24 123.8(9) . . ? O2 C18 C19 108.7(7) . . ? O2 C18 C23 127.2(8) . . ? C19 C18 C23 124.0(9) . . ? C35 C30 C31 119.1(9) . . ? C35 C30 C21 120.1(9) . . ? C31 C30 C21 120.6(9) . . ? C15 C16 O1 111.9(8) . . ? C15 C16 C17 135.5(9) . . ? O1 C16 C17 112.6(9) . . ? C14 C9 C10 116.4(10) . . ? C14 C9 C8 115.7(8) . . ? C10 C9 C8 127.8(9) . . ? C44 C43 C41 107.8(10) . . ? C44 C43 H43 126.1 . . ? C41 C43 H43 126.1 . . ? C84 C79 C80 117.3(10) . . ? C84 C79 C66 120.7(9) . . ? C80 C79 C66 122.0(9) . . ? N1 C17 O2 115.5(8) . . ? N1 C17 C16 128.5(9) . . ? O2 C17 C16 116.0(9) . . ? C20 C21 C22 118.7(8) . . ? C20 C21 C30 125.4(8) . . ? C22 C21 C30 115.6(7) . . ? C7 C8 C37 105.7(8) . . ? C7 C8 C9 103.9(9) . . ? C37 C8 C9 105.1(9) . . ? C7 C8 H8 113.7 . . ? C37 C8 H8 113.7 . . ? C9 C8 H8 113.7 . . ? C49 C50 C51 120.2(10) . . ? C49 C50 C58 117.6(9) . . ? C51 C50 C58 122.1(8) . . ? C23 C22 C21 125.4(8) . . ? C23 C22 H22 117.3 . . ? C21 C22 H22 117.3 . . ? C74 C73 C78 114.6(10) . . ? C74 C73 C66 128.1(10) . . ? C78 C73 C66 117.3(10) . . ? C32 C31 C30 121.1(11) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C33 C34 C35 119.1(11) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C10 C11 C12 118.2(9) . . ? C10 C11 C15 104.6(9) . . ? C12 C11 C15 137.2(11) . . ? C25 C24 C29 117.9(10) . . ? C25 C24 C23 121.8(9) . . ? C29 C24 C23 120.3(10) . . ? C18 C19 C20 121.8(8) . . ? C18 C19 N1 108.1(8) . . ? C20 C19 N1 130.1(8) . . ? C46 C51 C50 116.6(8) . . ? C46 C51 C64 119.7(9) . . ? C50 C51 C64 123.6(9) . . ? N2 C45 O6 115.4(9) . . ? N2 C45 C44 129.5(9) . . ? O6 C45 C44 115.1(8) . . ? C63 C58 C59 119.2(11) . . ? C63 C58 C50 122.5(11) . . ? C59 C58 C50 118.2(10) . . ? C40 C41 C42 117.6(11) . . ? C40 C41 C43 136.1(11) . . ? C42 C41 C43 106.3(9) . . ? C67 C72 C71 120.4(11) . . ? C67 C72 H72 119.8 . . ? C71 C72 H72 119.8 . . ? C2 C1 C38 105.6(10) . . ? C2 C1 C14 103.7(10) . . ? C38 C1 C14 107.4(9) . . ? C2 C1 H1 113.1 . . ? C38 C1 H1 113.1 . . ? C14 C1 H1 113.1 . . ? C76 C77 C78 121.3(12) . . ? C76 C77 H77 119.4 . . ? C78 C77 H77 119.4 . . ? C67 C68 C69 119.9(11) . . ? C67 C68 H68 120.1 . . ? C69 C68 H68 120.1 . . ? C16 C15 C11 107.3(9) . . ? C16 C15 H15 126.3 . . ? C11 C15 H15 126.3 . . ? C28 C29 C24 120.6(11) . . ? C28 C29 H29 119.7 . . ? C24 C29 H29 119.7 . . ? C39 C38 C37 122.1(11) . . ? C39 C38 C1 125.5(10) . . ? C37 C38 C1 112.4(10) . . ? C34 C33 C32 120.5(10) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C26 C25 C24 119.7(11) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C42 C37 C38 114.9(10) . . ? C42 C37 C8 130.9(10) . . ? C38 C37 C8 114.2(10) . . ? C57 C52 C53 117.7(11) . . ? C57 C52 C48 122.7(12) . . ? C53 C52 C48 119.6(12) . . ? C68 C67 C72 118.2(9) . . ? C68 C67 C66 120.5(9) . . ? C72 C67 C66 121.4(9) . . ? C70 C69 C68 123.4(11) . . ? C70 C69 H69 118.3 . . ? C68 C69 H69 118.3 . . ? C48 C49 C50 122.8(10) . . ? C48 C49 H49 118.6 . . ? C50 C49 H49 118.6 . . ? O4 C36 O3 125.7(9) . . ? O4 C36 C20 116.9(9) . . ? O3 C36 C20 117.4(9) . . ? O10 C65 O9 124.3(9) . . ? O10 C65 C66 116.9(9) . . ? O9 C65 C66 118.8(8) . . ? C30 C35 C34 120.7(10) . . ? C30 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C81 C80 C79 121.2(10) . . ? C81 C80 H80 119.4 . . ? C79 C80 H80 119.4 . . ? C79 C66 C73 112.2(8) . . ? C79 C66 C65 110.1(8) . . ? C73 C66 C65 109.6(8) . . ? C79 C66 C67 111.2(8) . . ? C73 C66 C67 109.3(8) . . ? C65 C66 C67 104.1(7) . . ? C31 C32 C33 119.4(10) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C13 C12 C11 119.2(11) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C73 C78 C77 120.3(11) . . ? C73 C78 H78 119.9 . . ? C77 C78 H78 119.9 . . ? C39 C40 C41 118.6(11) . . ? C39 C40 H40 120.7 . . ? C41 C40 H40 120.7 . . ? C11 C10 C9 123.5(10) . . ? C11 C10 O1 112.1(8) . . ? C9 C10 O1 124.4(9) . . ? O8 C64 O7 124.9(8) . . ? O8 C64 C51 116.0(9) . . ? O7 C64 C51 119.1(9) . . ? C43 C44 O5 110.9(9) . . ? C43 C44 C45 130.9(10) . . ? O5 C44 C45 118.2(8) . . ? C70 C71 C72 120.0(11) . . ? C70 C71 H71 120.0 . . ? C72 C71 H71 120.0 . . ? C48 C47 O6 128.7(9) . . ? C48 C47 C46 125.1(10) . . ? O6 C47 C46 106.2(9) . . ? C83 C84 C79 121.0(10) . . ? C83 C84 H84 119.5 . . ? C79 C84 H84 119.5 . . ? C9 C14 C13 121.8(9) . . ? C9 C14 C1 111.6(10) . . ? C13 C14 C1 126.6(10) . . ? C3 C2 C7 118.6(13) . . ? C3 C2 C1 126.9(11) . . ? C7 C2 C1 114.5(10) . . ? C6 C7 C2 120.7(11) . . ? C6 C7 C8 127.1(11) . . ? C2 C7 C8 112.2(11) . . ? C69 C70 C71 118.0(11) . . ? C69 C70 H70 121.0 . . ? C71 C70 H70 121.0 . . ? C12 C13 C14 120.8(11) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C7 C6 C5 120.6(12) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C60 C59 C58 120.8(11) . . ? C60 C59 H59 119.6 . . ? C58 C59 H59 119.6 . . ? C61 C62 C63 119.6(12) . . ? C61 C62 H62 120.2 . . ? C63 C62 H62 120.2 . . ? C40 C39 C38 121.2(11) . . ? C40 C39 H39 119.4 . . ? C38 C39 H39 119.4 . . ? C74 C75 C76 118.6(13) . . ? C74 C75 H75 120.7 . . ? C76 C75 H75 120.7 . . ? C4 C3 C2 120.8(13) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C52 C53 C54 121.2(16) . . ? C52 C53 H53 119.4 . . ? C54 C53 H53 119.4 . . ? C81 C82 C83 118.1(11) . . ? C81 C82 H82 120.9 . . ? C83 C82 H82 120.9 . . ? C3 C4 C5 121.3(12) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C77 C76 C75 119.8(12) . . ? C77 C76 H76 120.1 . . ? C75 C76 H76 120.1 . . ? C52 C57 C56 120.1(14) . . ? C52 C57 H57 120.0 . . ? C56 C57 H57 120.0 . . ? C82 C81 C80 121.6(11) . . ? C82 C81 H81 119.2 . . ? C80 C81 H81 119.2 . . ? C27 C28 C29 119.9(11) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C47 C48 C49 115.5(9) . . ? C47 C48 C52 123.5(10) . . ? C49 C48 C52 121.0(10) . . ? C55 C56 C57 120.9(16) . . ? C55 C56 H56 119.5 . . ? C57 C56 H56 119.5 . . ? C58 C63 C62 120.3(12) . . ? C58 C63 H63 119.8 . . ? C62 C63 H63 119.8 . . ? C84 C83 C82 120.7(11) . . ? C84 C83 H83 119.7 . . ? C82 C83 H83 119.7 . . ? C25 C26 C27 121.9(12) . . ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C75 C74 C73 125.1(12) . . ? C75 C74 H74 117.4 . . ? C73 C74 H74 117.4 . . ? C28 C27 C26 119.9(12) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C60 C61 C62 119.8(12) . . ? C60 C61 H61 120.1 . . ? C62 C61 H61 120.1 . . ? C61 C60 C59 120.2(13) . . ? C61 C60 H60 119.9 . . ? C59 C60 H60 119.9 . . ? C54 C55 C56 121.3(15) . . ? C54 C55 H55 119.3 . . ? C56 C55 H55 119.3 . . ? C4 C5 C6 118.1(13) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C55 C54 C53 118.4(17) . . ? C55 C54 H54 120.8 . . ? C53 C54 H54 120.8 . . ? Fe2 O12 Fe1 120.0(2) . 2 ? Fe2 O12 Fe1 120.0(2) . . ? Fe1 O12 Fe1 119.9(4) 2 . ? C36 O4 Fe1 135.9(6) . 2 ? C36 O4 Na1 119.9(7) . 2 ? Fe1 O4 Na1 100.6(4) 2 2 ? Fe1 O11 Na1 102.8(3) . . ? O11 Na1 O1 118.0(5) . . ? O11 Na1 O4 61.9(3) . 2 ? O1 Na1 O4 149.5(4) . 2 ? O14 S1 O16 110.0(16) . . ? O14 S1 O15 118.6(13) . . ? O16 S1 O15 119.1(17) . . ? O14 S1 C85 94.7(11) . . ? O16 S1 C85 109.2(15) . . ? O15 S1 C85 101.5(12) . . ? F1 C85 F3 103(2) . . ? F1 C85 F2 98(2) . . ? F3 C85 F2 103(2) . . ? F1 C85 S1 116.9(17) . . ? F3 C85 S1 116.2(17) . . ? F2 C85 S1 116.9(16) . . ? C91 C86 C87 119.2(8) . . ? C91 C86 H86 120.4 . . ? C87 C86 H86 120.4 . . ? C88 C87 C86 120.6(9) . . ? C88 C87 H87 119.7 . . ? C86 C87 H87 119.7 . . ? C87 C88 C89 119.8(8) . . ? C87 C88 H88 120.1 . . ? C89 C88 H88 120.1 . . ? C90 C89 C88 119.8(8) . . ? C90 C89 H89 120.1 . . ? C88 C89 H89 120.1 . . ? C89 C90 C91 119.7(9) . . ? C89 C90 H90 120.1 . . ? C91 C90 H90 120.1 . . ? C86 C91 C90 120.9(8) . . ? C86 C91 H91 119.6 . . ? C90 C91 H91 119.6 . . ? C800 C805 C804 120.1(12) . . ? C800 C805 H805 119.9 . . ? C804 C805 H805 120.0 . . ? C803 C802 C801 120.4(11) . . ? C803 C802 H802 119.8 . . ? C801 C802 H802 119.8 . . ? C804 C803 C802 120.2(11) . . ? C804 C803 H803 119.9 . . ? C802 C803 H803 119.9 . . ? C803 C804 C805 119.3(12) . . ? C803 C804 H804 120.4 . . ? C805 C804 H804 120.3 . . ? C800 C801 C802 119.6(11) . . ? C800 C801 H801 120.2 . . ? C802 C801 H801 120.2 . . ? C801 C800 C805 119.8(12) . . ? C801 C800 H800 120.1 . . ? C805 C800 H800 120.1 . . ? C902 C903 C904 119.8(12) . . ? C902 C903 H903 120.1 . . ? C904 C903 H903 120.1 . . ? C901 C902 C903 119.2(11) . . ? C901 C902 H902 120.4 . . ? C903 C902 H902 120.4 . . ? C903 C904 C905 118.7(12) . . ? C903 C904 H904 120.7 . . ? C905 C904 H904 120.7 . . ? C900 C905 C904 119.8(11) . . ? C900 C905 H905 120.1 . . ? C904 C905 H905 120.1 . . ? C902 C901 C900 120.2(11) . . ? C902 C901 H901 119.9 . . ? C900 C901 H901 119.9 . . ? C905 C900 C901 120.0(11) . . ? C905 C900 H900 120.0 . . ? C901 C900 H900 120.0 . . ? C401 C400 H40A 109.5 . . ? C401 C400 H40B 109.5 . . ? H40A C400 H40B 109.5 . . ? C401 C400 H40C 109.5 . . ? H40A C400 H40C 109.5 . . ? H40B C400 H40C 109.5 . . ? C400 C401 C402 125(3) . . ? C400 C401 H40D 106.1 . . ? C402 C401 H40D 106.1 . . ? C400 C401 H40E 106.1 . . ? C402 C401 H40E 106.1 . . ? H40D C401 H40E 106.3 . . ? C403 C402 C401 125(2) . . ? C403 C402 H40F 106.1 . . ? C401 C402 H40F 106.1 . . ? C403 C402 H40G 106.1 . . ? C401 C402 H40G 106.1 . . ? H40F C402 H40G 106.3 . . ? C402 C403 C404 126(3) . . ? C402 C403 H40H 105.9 . . ? C404 C403 H40H 105.9 . . ? C402 C403 H40I 105.9 . . ? C404 C403 H40I 105.9 . . ? H40H C403 H40I 106.3 . . ? C403 C404 H40J 109.5 . . ? C403 C404 H40K 109.5 . . ? H40J C404 H40K 109.5 . . ? C403 C404 H40L 109.5 . . ? H40J C404 H40L 109.5 . . ? H40K C404 H40L 109.5 . . ? C705 C704 C703 119.2(9) . . ? C705 C704 H704 120.4 . . ? C703 C704 H704 120.4 . . ? C703 C702 C701 120.4(9) . . ? C703 C702 H702 119.8 . . ? C701 C702 H702 119.8 . . ? C704 C705 C700 120.0(9) . . ? C704 C705 H705 120.0 . . ? C700 C705 H705 120.0 . . ? C702 C703 C704 120.6(9) . . ? C702 C703 H703 119.7 . . ? C704 C703 H703 119.7 . . ? C700 C701 C702 119.7(9) . . ? C700 C701 H701 120.1 . . ? C702 C701 H701 120.1 . . ? C701 C700 C705 120.1(9) . . ? C701 C700 H700 119.9 . . ? C705 C700 H700 119.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.88 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.539 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.113 data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 881380' #TrackingRef 'web_deposit_cif_file_2_JustinWilson_1339011645.CCDC 881380.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4,6-dibromo-3-hydroxy-2-nitrobenzoic acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H3 Br2 N O5' _chemical_formula_weight 340.92 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7083(4) _cell_length_b 15.0200(9) _cell_length_c 8.5232(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.8300(10) _cell_angle_gamma 90.00 _cell_volume 922.31(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9904 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 30.14 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 8.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1595 _exptl_absorpt_correction_T_max 0.2371 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19654 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 30.15 _reflns_number_total 2692 _reflns_number_gt 2508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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. The hydrogen atoms attached to the oxygens were located on the difference map. The O-H bond distances were constrained to 0.84 angstroms and the thermal displacement parameters of the hydrogen atoms were constrained to 1.5 times those of the oxygen atoms to which they were attached. ; _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^)+(0.0197P)^2^+1.1691P] 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 2692 _refine_ls_number_parameters 142 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0491 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 Br1 Br 0.42142(3) 0.139906(13) 0.04669(2) 0.01861(6) Uani 1 1 d . . . C1 C 0.5874(2) 0.10928(12) 0.2614(2) 0.0113(3) Uani 1 1 d . . . C2 C 0.6054(2) 0.02147(12) 0.3103(2) 0.0116(3) Uani 1 1 d . . . H1 H 0.5400 -0.0235 0.2338 0.014 Uiso 1 1 calc R . . C6 C 0.6870(2) 0.17732(11) 0.3686(2) 0.0108(3) Uani 1 1 d . . . C4 C 0.8158(2) 0.06319(11) 0.5869(2) 0.0098(3) Uani 1 1 d . . . C5 C 0.8033(2) 0.15191(11) 0.5303(2) 0.0103(3) Uani 1 1 d . . . C3 C 0.7202(2) -0.00134(11) 0.4732(2) 0.0105(3) Uani 1 1 d . . . Br2 Br 0.73760(3) -0.123004(11) 0.53233(2) 0.01505(5) Uani 1 1 d . . . O1 O 0.82511(18) 0.05483(9) 0.86728(16) 0.0131(2) Uani 1 1 d . . . O2 O 1.06200(18) -0.00443(9) 0.80760(17) 0.0144(3) Uani 1 1 d D . . H2 H 1.103(4) -0.0170(18) 0.908(2) 0.022 Uiso 1 1 d D . . O5 O 0.66443(19) 0.26030(9) 0.30853(17) 0.0146(3) Uani 1 1 d D . . H3 H 0.718(3) 0.2934(16) 0.386(3) 0.022 Uiso 1 1 d D . . O3 O 1.0391(2) 0.19240(9) 0.77341(17) 0.0185(3) Uani 1 1 d . . . O4 O 0.9005(2) 0.29728(9) 0.60072(18) 0.0195(3) Uani 1 1 d . . . N1 N 0.9219(2) 0.21794(10) 0.64241(19) 0.0127(3) Uani 1 1 d . . . C7 C 0.9053(2) 0.03889(11) 0.7699(2) 0.0103(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02153(10) 0.01810(10) 0.00952(9) 0.00086(6) -0.00271(7) -0.00056(7) C1 0.0105(7) 0.0147(8) 0.0069(7) -0.0007(6) 0.0006(6) 0.0003(6) C2 0.0114(7) 0.0131(8) 0.0098(8) -0.0037(6) 0.0032(6) -0.0017(6) C6 0.0122(7) 0.0106(7) 0.0094(8) 0.0000(6) 0.0037(6) 0.0002(6) C4 0.0101(7) 0.0114(7) 0.0076(7) 0.0016(6) 0.0026(6) 0.0011(6) C5 0.0119(7) 0.0100(7) 0.0079(7) -0.0006(6) 0.0021(6) -0.0016(6) C3 0.0121(7) 0.0085(7) 0.0107(8) 0.0004(6) 0.0039(6) 0.0005(6) Br2 0.01999(10) 0.00852(8) 0.01734(10) 0.00056(6) 0.00750(7) 0.00018(6) O1 0.0141(6) 0.0151(6) 0.0092(6) 0.0013(5) 0.0032(5) 0.0028(5) O2 0.0131(6) 0.0194(6) 0.0095(6) 0.0038(5) 0.0026(5) 0.0058(5) O5 0.0205(7) 0.0101(6) 0.0098(6) 0.0014(5) 0.0013(5) -0.0013(5) O3 0.0182(6) 0.0174(6) 0.0121(6) 0.0012(5) -0.0041(5) -0.0029(5) O4 0.0285(8) 0.0102(6) 0.0144(6) 0.0012(5) 0.0007(6) -0.0052(5) N1 0.0155(7) 0.0123(7) 0.0094(7) 0.0011(5) 0.0035(6) -0.0014(5) C7 0.0116(7) 0.0082(7) 0.0091(7) 0.0002(6) 0.0011(6) -0.0010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.8795(17) . ? C1 C2 1.375(2) . ? C1 C6 1.403(2) . ? C2 C3 1.398(2) . ? C2 H1 0.9500 . ? C6 O5 1.335(2) . ? C6 C5 1.404(2) . ? C4 C3 1.383(2) . ? C4 C5 1.409(2) . ? C4 C7 1.509(2) . ? C5 N1 1.453(2) . ? C3 Br2 1.8877(17) . ? O1 C7 1.221(2) . ? O2 C7 1.308(2) . ? O2 H2 0.819(17) . ? O5 H3 0.812(17) . ? O3 N1 1.222(2) . ? O4 N1 1.238(2) . ? 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 C2 C1 C6 121.88(16) . . ? C2 C1 Br1 119.36(13) . . ? C6 C1 Br1 118.75(13) . . ? C1 C2 C3 119.74(16) . . ? C1 C2 H1 120.1 . . ? C3 C2 H1 120.1 . . ? O5 C6 C1 117.63(16) . . ? O5 C6 C5 125.51(16) . . ? C1 C6 C5 116.86(16) . . ? C3 C4 C5 117.93(16) . . ? C3 C4 C7 119.24(15) . . ? C5 C4 C7 122.22(15) . . ? C6 C5 C4 122.36(16) . . ? C6 C5 N1 119.54(15) . . ? C4 C5 N1 118.05(15) . . ? C4 C3 C2 121.03(16) . . ? C4 C3 Br2 121.45(13) . . ? C2 C3 Br2 117.52(13) . . ? C7 O2 H2 110.5(19) . . ? C6 O5 H3 107(2) . . ? O3 N1 O4 122.99(16) . . ? O3 N1 C5 118.33(15) . . ? O4 N1 C5 118.68(15) . . ? O1 C7 O2 125.25(16) . . ? O1 C7 C4 119.95(15) . . ? O2 C7 C4 114.62(15) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.15 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.625 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.093