Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'J. Reedijk' _publ_contact_author_address ; Leiden Institute of Chemistry Gorlaeus Laboratories Leiden University Leiden P O Box 9502 Leiden 2300 RA NETHERLANDS ; _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_section_title ; Versatility in the binding of 2-pyrazinecarboxylate with iron. Synthesis, structure and magnetic properties of iron(II) and iron(III) complexes ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garcia-Granda, S., Gould, R. O., Israel, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. Beurskens, P. T., Beurskens, G., Strumpel, M. & Nordman, C. E. (1987). In Patterson and Pattersons, pp. 356--367. Glusker, J. P., Patterson, B. K. & Rossi, M., Eds. Oxford, England: Clarendon Press. Duisenberg, A.J.M. (1998). Reflections on area detectors, PhD Thesis, Utrecht University, Utrecht, The Netherlands. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Nonius B.V. (1999). COLLECT, data collection software. Delft, The Netherlands. Sheldrick, G.M. (1996). SADABS. Program for Emperical Absorption Correction. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of Gottingen, Germany. Spek, A. L. (2003). PLATON. A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _publ_section_experimental ; Crystal colour: transparent red, crystal shape: rather regular fragment. Special remarks: CCD. Special experimental condition: measurements were performed at -65 degrees C. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+2.5372P] where P=(Fo^2^+2Fc^2^)/3 ; loop_ _publ_author_name 'J. Reedijk' 'Elisabeth Bouwman' 'R.de Gelder' 'Patrica Gallego' 'Fernande Grandjean' ; G.L.Long ; 'Ilpo Mutikainen' 'Leila Rebbouh' 'Stefania Tanase' 'Urho Turpeinen' #============================================================================== data_LEID21 _database_code_depnum_ccdc_archive 'CCDC 264661' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2005-02-24 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 Fe2 N14 Na2 O15' _chemical_formula_weight 1030.38 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' Na Na 0.0362 0.0249 '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 11.3333(9) _cell_length_b 11.6011(9) _cell_length_c 18.2472(10) _cell_angle_alpha 80.490(6) _cell_angle_beta 89.466(5) _cell_angle_gamma 64.006(5) _cell_volume 2121.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 232 _cell_measurement_theta_min 3.130 _cell_measurement_theta_max 27.500 _exptl_crystal_description 'rather regular fragment' _exptl_crystal_colour 'transparent red' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.21 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 33929 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9564 _reflns_number_gt 7117 _reflns_number_observed 7117 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+2.5372P] 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 9564 _refine_ls_number_parameters 622 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0465 _refine_ls_R_factor_obs 0.0465 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_all 0.1024 _refine_ls_wR_factor_gt 0.0941 _refine_ls_wR_factor_obs 0.0941 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_goodness_of_fit_all 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.16384(4) 0.24078(4) 0.33194(2) 0.01815(10) Uani 1 d . . . Fe2 Fe 0.22078(4) 0.14363(4) 0.15752(2) 0.01782(10) Uani 1 d . . . Na1 Na 0.43897(11) 0.19786(11) 0.25099(7) 0.0302(3) Uani 1 d . . . Na2 Na 0.70549(13) -0.06758(15) 0.25702(8) 0.0515(4) Uani 1 d . . . O1 O 0.21920(18) 0.18685(19) 0.24674(10) 0.0268(4) Uani 1 d . . . O2 O 0.6580(3) 0.0749(3) 0.34688(17) 0.0550(7) Uani 1 d . . . H2A H 0.705(3) 0.030(3) 0.3978(17) 0.019(7) Uiso 1 d . . . H2B H 0.695(5) 0.130(6) 0.349(3) 0.11(2) Uiso 1 d . . . O3 O 0.6183(3) 0.1736(3) 0.17979(17) 0.0639(8) Uani 1 d . . . H3A H 0.695(8) 0.206(8) 0.174(4) 0.19(3) Uiso 1 d . . . H3B H 0.570(2) 0.284(3) 0.1578(12) 0.003(6) Uiso 1 d . . . O11 O 0.11752(18) 0.42977(18) 0.30483(11) 0.0268(4) Uani 1 d . . . O12 O 0.3023(2) 0.4156(2) 0.25205(12) 0.0362(5) Uani 1 d . . . C10 C 0.1921(3) 0.4766(3) 0.27184(15) 0.0244(6) Uani 1 d . . . C11 C 0.1306(3) 0.6231(3) 0.25907(14) 0.0222(6) Uani 1 d . . . C12 C -0.0043(3) 0.6949(3) 0.25641(15) 0.0258(6) Uani 1 d . . . H12 H -0.0570 0.6505 0.2622 0.031 Uiso 1 calc R . . N13 N -0.0631(2) 0.8254(2) 0.24582(13) 0.0300(6) Uani 1 d . . . C14 C 0.0164(3) 0.8817(3) 0.23817(18) 0.0354(7) Uani 1 d . . . H14 H -0.0198 0.9731 0.2309 0.043 Uiso 1 calc R . . C15 C 0.1512(3) 0.8100(3) 0.2406(2) 0.0487(9) Uani 1 d . . . H15 H 0.2038 0.8546 0.2350 0.058 Uiso 1 calc R . . N16 N 0.2099(3) 0.6809(3) 0.25059(17) 0.0407(7) Uani 1 d . . . O21 O -0.02833(18) 0.27818(18) 0.32608(11) 0.0260(4) Uani 1 d . . . O22 O -0.1772(2) 0.2013(2) 0.34128(15) 0.0485(6) Uani 1 d . . . C20 C -0.0645(3) 0.1889(3) 0.34738(16) 0.0272(6) Uani 1 d . . . C21 C 0.0441(3) 0.0594(3) 0.38315(15) 0.0255(6) Uani 1 d . . . C22 C 0.0237(3) -0.0468(3) 0.41365(19) 0.0417(8) Uani 1 d . . . H22 H -0.0619 -0.0400 0.4111 0.050 Uiso 1 calc R . . N23 N 0.1222(3) -0.1592(3) 0.44680(19) 0.0575(9) Uani 1 d . . . C24 C 0.2405(4) -0.1628(3) 0.4478(2) 0.0540(10) Uani 1 d . . . H24 H 0.3121 -0.2401 0.4709 0.065 Uiso 1 calc R . . C25 C 0.2639(3) -0.0586(3) 0.41666(18) 0.0362(7) Uani 1 d . . . H25 H 0.3502 -0.0669 0.4178 0.043 Uiso 1 calc R . . N26 N 0.1648(2) 0.0532(2) 0.38513(12) 0.0234(5) Uani 1 d . . . O31 O 0.35280(18) 0.17378(19) 0.37498(10) 0.0248(4) Uani 1 d . . . O32 O 0.49051(19) 0.1487(2) 0.46892(11) 0.0358(5) Uani 1 d . . . C30 C 0.3800(3) 0.1807(3) 0.44127(15) 0.0241(6) Uani 1 d . . . C31 C 0.2621(3) 0.2335(3) 0.48665(15) 0.0251(6) Uani 1 d . . . C32 C 0.2688(3) 0.2418(4) 0.56084(17) 0.0491(10) Uani 1 d . . . H32 H 0.3518 0.2116 0.5858 0.059 Uiso 1 calc R . . N33 N 0.1621(3) 0.2908(4) 0.59831(16) 0.0677(11) Uani 1 d . . . C34 C 0.0470(4) 0.3343(4) 0.56011(19) 0.0486(10) Uani 1 d . . . H34 H -0.0308 0.3721 0.5844 0.058 Uiso 1 calc R . . C35 C 0.0379(3) 0.3260(3) 0.48625(16) 0.0298(7) Uani 1 d . . . H35 H -0.0455 0.3570 0.4614 0.036 Uiso 1 calc R . . N36 N 0.1452(2) 0.2746(2) 0.44965(12) 0.0222(5) Uani 1 d . . . O41 O 0.34398(18) -0.04730(18) 0.18196(10) 0.0248(4) Uani 1 d . . . O42 O 0.4929(2) -0.0230(2) 0.24982(12) 0.0354(5) Uani 1 d . . . C40 C 0.4514(3) -0.0893(3) 0.22171(15) 0.0252(6) Uani 1 d . . . C41 C 0.5348(3) -0.2347(3) 0.23217(15) 0.0267(6) Uani 1 d . . . C42 C 0.4952(3) -0.3136(3) 0.20048(18) 0.0353(7) Uani 1 d . . . H42 H 0.4140 -0.2751 0.1724 0.042 Uiso 1 calc R . . N43 N 0.5679(3) -0.4424(3) 0.20826(17) 0.0439(7) Uani 1 d . . . C44 C 0.6819(3) -0.4901(3) 0.25009(19) 0.0409(8) Uani 1 d . . . H44 H 0.7360 -0.5804 0.2585 0.049 Uiso 1 calc R . . C45 C 0.7220(3) -0.4130(3) 0.28072(18) 0.0377(8) Uani 1 d . . . H45 H 0.8027 -0.4519 0.3094 0.045 Uiso 1 calc R . . N46 N 0.6502(2) -0.2831(3) 0.27134(15) 0.0353(6) Uani 1 d . . . O51 O 0.05904(18) 0.11455(18) 0.15309(10) 0.0252(4) Uani 1 d . . . O52 O -0.1596(2) 0.2037(3) 0.14116(15) 0.0511(6) Uani 1 d . . . C50 C -0.0551(3) 0.2106(3) 0.13823(15) 0.0278(6) Uani 1 d . . . C51 C -0.0553(3) 0.3416(3) 0.11532(15) 0.0269(6) Uani 1 d . . . C52 C -0.1689(3) 0.4580(3) 0.09801(19) 0.0440(9) Uani 1 d . . . H52 H -0.2509 0.4559 0.0976 0.053 Uiso 1 calc R . . N53 N -0.1652(3) 0.5720(3) 0.08207(18) 0.0571(9) Uani 1 d . . . C54 C -0.0476(4) 0.5693(3) 0.08452(19) 0.0494(10) Uani 1 d . . . H54 H -0.0418 0.6487 0.0750 0.059 Uiso 1 calc R . . C55 C 0.0678(3) 0.4542(3) 0.10053(16) 0.0342(7) Uani 1 d . . . H55 H 0.1495 0.4568 0.1009 0.041 Uiso 1 calc R . . N56 N 0.0628(2) 0.3399(2) 0.11540(12) 0.0244(5) Uani 1 d . . . O61 O 0.35217(18) 0.20953(19) 0.11827(10) 0.0257(4) Uani 1 d . . . O62 O 0.4814(2) 0.2259(2) 0.02872(12) 0.0437(6) Uani 1 d . . . C60 C 0.3946(3) 0.1975(3) 0.05326(15) 0.0258(6) Uani 1 d . . . C61 C 0.3311(3) 0.1413(3) 0.00647(15) 0.0233(6) Uani 1 d . . . C62 C 0.3587(3) 0.1265(3) -0.06624(16) 0.0338(7) Uani 1 d . . . H62 H 0.4212 0.1515 -0.0882 0.041 Uiso 1 calc R . . N63 N 0.2999(3) 0.0781(3) -0.10629(14) 0.0401(7) Uani 1 d . . . C64 C 0.2162(3) 0.0400(3) -0.07104(18) 0.0389(8) Uani 1 d . . . H64 H 0.1754 0.0017 -0.0967 0.047 Uiso 1 calc R . . C65 C 0.1864(3) 0.0540(3) 0.00169(16) 0.0294(6) Uani 1 d . . . H65 H 0.1260 0.0263 0.0241 0.035 Uiso 1 calc R . . N66 N 0.2434(2) 0.1069(2) 0.04013(12) 0.0222(5) Uani 1 d . . . N70 N 0.1316(5) 0.7443(5) 0.0528(3) 0.0990(15) Uani 1 d . . . C70 C 0.2333(5) 0.6688(5) 0.0584(2) 0.0645(12) Uani 1 d . . . C71 C 0.3681(5) 0.5643(6) 0.0705(3) 0.0985(19) Uani 1 d . . . H71A H 0.3924 0.5359 0.1235 0.148 Uiso 1 calc R . . H71B H 0.4279 0.5964 0.0471 0.148 Uiso 1 calc R . . H71C H 0.3734 0.4915 0.0487 0.148 Uiso 1 calc R . . N80 N 0.3064(5) 0.5014(5) 0.4764(3) 0.1067(17) Uani 1 d . . . C80 C 0.3844(5) 0.4812(4) 0.4350(3) 0.0663(12) Uani 1 d . . . C81 C 0.4839(5) 0.4558(5) 0.3821(3) 0.0777(14) Uani 1 d . . . H81A H 0.4433 0.5036 0.3330 0.117 Uiso 1 calc R . . H81B H 0.5274 0.3632 0.3809 0.117 Uiso 1 calc R . . H81C H 0.5480 0.4837 0.3967 0.117 Uiso 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 0.0178(2) 0.0197(2) 0.01806(19) -0.00142(15) 0.00062(14) -0.01003(16) Fe2 0.0174(2) 0.0187(2) 0.01795(19) -0.00187(14) 0.00037(14) -0.00899(16) Na1 0.0250(6) 0.0246(6) 0.0433(7) -0.0108(5) 0.0044(5) -0.0115(5) Na2 0.0279(7) 0.0632(10) 0.0702(10) -0.0352(8) 0.0076(6) -0.0184(7) O1 0.0295(11) 0.0331(11) 0.0200(9) -0.0069(8) 0.0028(8) -0.0152(10) O2 0.0509(16) 0.0664(19) 0.070(2) -0.0314(16) 0.0179(14) -0.0399(16) O3 0.0528(17) 0.090(2) 0.076(2) -0.0380(17) 0.0266(15) -0.0486(18) O11 0.0257(11) 0.0215(10) 0.0339(11) -0.0003(8) 0.0074(8) -0.0127(9) O12 0.0281(12) 0.0248(11) 0.0557(14) -0.0112(10) 0.0179(10) -0.0108(10) C10 0.0265(15) 0.0225(15) 0.0260(14) -0.0030(11) 0.0027(11) -0.0129(13) C11 0.0232(14) 0.0233(14) 0.0224(14) -0.0039(11) 0.0066(11) -0.0123(12) C12 0.0260(15) 0.0247(15) 0.0297(15) -0.0051(12) 0.0067(12) -0.0140(13) N13 0.0288(14) 0.0243(13) 0.0325(13) -0.0029(10) 0.0051(10) -0.0085(11) C14 0.0383(19) 0.0214(16) 0.0445(18) 0.0002(13) 0.0089(14) -0.0135(14) C15 0.039(2) 0.0267(19) 0.086(3) -0.0059(17) 0.0153(19) -0.0216(16) N16 0.0294(15) 0.0278(15) 0.070(2) -0.0063(13) 0.0132(13) -0.0178(13) O21 0.0181(10) 0.0210(10) 0.0368(11) 0.0032(8) -0.0026(8) -0.0095(8) O22 0.0251(12) 0.0401(14) 0.0805(18) 0.0072(12) -0.0053(11) -0.0206(11) C20 0.0213(15) 0.0279(16) 0.0328(16) -0.0013(12) -0.0007(12) -0.0125(13) C21 0.0292(16) 0.0244(15) 0.0256(14) -0.0012(11) -0.0011(12) -0.0153(13) C22 0.0406(19) 0.0333(18) 0.054(2) 0.0049(15) -0.0019(15) -0.0232(16) N23 0.057(2) 0.0338(18) 0.080(2) 0.0173(16) -0.0154(17) -0.0280(16) C24 0.054(2) 0.0261(19) 0.072(3) 0.0166(17) -0.025(2) -0.0164(17) C25 0.0317(17) 0.0256(17) 0.0455(19) 0.0004(14) -0.0116(14) -0.0096(14) N26 0.0261(13) 0.0218(12) 0.0227(12) -0.0009(9) -0.0034(9) -0.0119(10) O31 0.0199(10) 0.0327(11) 0.0223(10) -0.0068(8) 0.0021(8) -0.0116(9) O32 0.0237(11) 0.0524(14) 0.0327(11) -0.0065(10) -0.0046(9) -0.0183(10) C30 0.0240(15) 0.0234(15) 0.0261(15) -0.0002(11) -0.0012(11) -0.0131(12) C31 0.0282(15) 0.0322(16) 0.0218(14) -0.0040(11) 0.0012(11) -0.0198(13) C32 0.042(2) 0.096(3) 0.0262(17) -0.0164(18) 0.0049(14) -0.044(2) N33 0.053(2) 0.145(4) 0.0332(16) -0.042(2) 0.0189(14) -0.061(2) C34 0.041(2) 0.083(3) 0.0393(19) -0.0326(19) 0.0208(16) -0.037(2) C35 0.0293(16) 0.0345(17) 0.0300(16) -0.0089(13) 0.0089(12) -0.0172(14) N36 0.0245(12) 0.0243(13) 0.0221(12) -0.0049(9) 0.0049(9) -0.0147(10) O41 0.0203(10) 0.0218(10) 0.0302(10) -0.0021(8) -0.0044(8) -0.0080(8) O42 0.0291(12) 0.0302(12) 0.0502(13) -0.0138(10) -0.0001(10) -0.0140(10) C40 0.0224(15) 0.0255(15) 0.0288(15) -0.0063(12) 0.0058(12) -0.0111(12) C41 0.0242(15) 0.0265(16) 0.0292(15) -0.0046(12) 0.0036(12) -0.0111(13) C42 0.0275(16) 0.0272(17) 0.0489(19) -0.0087(14) -0.0043(14) -0.0093(14) N43 0.0347(16) 0.0262(15) 0.066(2) -0.0123(13) -0.0018(14) -0.0076(13) C44 0.0294(18) 0.0241(17) 0.056(2) 0.0028(15) 0.0011(15) -0.0031(14) C45 0.0287(17) 0.0272(17) 0.0463(19) 0.0019(14) -0.0069(14) -0.0052(14) N46 0.0278(14) 0.0306(15) 0.0411(15) -0.0031(11) -0.0080(11) -0.0082(12) O51 0.0213(10) 0.0225(10) 0.0337(11) -0.0012(8) 0.0001(8) -0.0127(9) O52 0.0231(12) 0.0561(16) 0.0769(18) -0.0072(13) 0.0058(11) -0.0218(12) C50 0.0215(15) 0.0351(17) 0.0273(15) -0.0063(12) 0.0020(11) -0.0126(13) C51 0.0254(15) 0.0269(16) 0.0234(14) -0.0052(11) -0.0006(11) -0.0069(13) C52 0.0307(18) 0.035(2) 0.047(2) -0.0064(15) -0.0063(15) 0.0025(15) N53 0.054(2) 0.0291(17) 0.065(2) -0.0049(15) -0.0124(16) 0.0025(15) C54 0.071(3) 0.0201(18) 0.045(2) 0.0005(15) -0.0090(19) -0.0115(18) C55 0.049(2) 0.0254(16) 0.0296(16) -0.0014(12) -0.0028(14) -0.0188(15) N56 0.0296(13) 0.0221(12) 0.0195(11) -0.0019(9) -0.0013(9) -0.0102(11) O61 0.0255(10) 0.0316(11) 0.0267(10) -0.0065(8) 0.0049(8) -0.0182(9) O62 0.0389(13) 0.0639(17) 0.0442(13) -0.0128(12) 0.0176(10) -0.0364(13) C60 0.0222(15) 0.0233(15) 0.0287(15) -0.0014(11) 0.0025(11) -0.0084(12) C61 0.0189(14) 0.0199(14) 0.0230(14) -0.0005(11) 0.0027(11) -0.0025(11) C62 0.0314(17) 0.0333(17) 0.0293(16) -0.0046(13) 0.0097(13) -0.0080(14) N63 0.0463(17) 0.0442(17) 0.0282(14) -0.0145(12) 0.0061(12) -0.0157(14) C64 0.0411(19) 0.042(2) 0.0348(18) -0.0162(15) -0.0005(14) -0.0166(16) C65 0.0298(16) 0.0298(16) 0.0291(15) -0.0070(12) -0.0003(12) -0.0129(14) N66 0.0202(12) 0.0211(12) 0.0223(12) -0.0022(9) -0.0004(9) -0.0068(10) N70 0.076(3) 0.105(4) 0.104(4) -0.014(3) -0.012(3) -0.030(3) C70 0.063(3) 0.083(4) 0.060(3) -0.026(2) 0.000(2) -0.039(3) C71 0.068(4) 0.114(5) 0.129(5) -0.059(4) 0.001(3) -0.042(3) N80 0.103(4) 0.072(3) 0.152(5) -0.035(3) 0.053(4) -0.040(3) C80 0.070(3) 0.049(3) 0.086(3) -0.016(2) 0.009(3) -0.030(2) C81 0.077(3) 0.096(4) 0.064(3) -0.005(3) 0.002(2) -0.045(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 Fe1 O1 1.7779(18) . Y Fe1 O11 1.9912(19) . Y Fe1 O21 2.0258(18) . Y Fe1 O31 2.0439(18) . Y Fe1 N26 2.227(2) . Y Fe1 N36 2.238(2) . Y Fe1 Na1 3.3090(12) . Y Fe2 O1 1.7787(18) . Y Fe2 O41 2.0072(19) . Y Fe2 O51 2.0086(18) . Y Fe2 O61 2.0277(18) . Y Fe2 N56 2.204(2) . Y Fe2 N66 2.243(2) . Y Fe2 Na1 3.3491(12) . Y Na1 O12 2.316(2) . Y Na1 O3 2.339(3) . Y Na1 O42 2.363(2) . Y Na1 O31 2.478(2) . Y Na1 O1 2.552(2) . Y Na1 O61 2.583(2) . Y Na1 O2 2.723(3) . Y Na1 Na2 3.2186(18) . Y Na2 O42 2.232(2) . Y Na2 N13 2.384(3) 1_645 Y Na2 O2 2.411(3) . Y Na2 O3 2.663(4) . Y Na2 N63 2.776(3) 2_655 Y Na2 N46 2.804(3) . Y Na2 C40 3.082(3) . Y O11 C10 1.287(3) . Y O12 C10 1.221(3) . Y C10 C11 1.504(4) . Y C11 N16 1.332(4) . Y C11 C12 1.380(4) . Y C12 N13 1.341(4) . Y N13 C14 1.318(4) . Y N13 Na2 2.384(3) 1_465 Y C14 C15 1.380(5) . Y C15 N16 1.326(4) . Y O21 C20 1.276(3) . Y O22 C20 1.225(3) . Y C20 C21 1.506(4) . Y C21 N26 1.339(4) . Y C21 C22 1.379(4) . Y C22 N23 1.337(4) . Y N23 C24 1.322(5) . Y C24 C25 1.380(5) . Y C25 N26 1.328(4) . Y O31 C30 1.275(3) . Y O32 C30 1.226(3) . Y C30 C31 1.509(4) . Y C31 N36 1.340(3) . Y C31 C32 1.378(4) . Y C32 N33 1.328(4) . Y N33 C34 1.329(5) . Y C34 C35 1.375(4) . Y C35 N36 1.327(4) . Y O41 C40 1.275(3) . Y O42 C40 1.236(3) . Y C40 C41 1.508(4) . Y C41 N46 1.333(4) . Y C41 C42 1.384(4) . Y C42 N43 1.336(4) . Y N43 C44 1.345(4) . Y C44 C45 1.358(5) . Y C45 N46 1.344(4) . Y O51 C50 1.278(3) . Y O52 C50 1.222(3) . Y C50 C51 1.506(4) . Y C51 N56 1.330(4) . Y C51 C52 1.387(4) . Y C52 N53 1.325(5) . Y N53 C54 1.321(5) . Y C54 C55 1.388(5) . Y C55 N56 1.335(4) . Y O61 C60 1.282(3) . Y O62 C60 1.226(3) . Y C60 C61 1.510(4) . Y C61 N66 1.333(3) . Y C61 C62 1.381(4) . Y C62 N63 1.328(4) . Y N63 C64 1.331(4) . Y N63 Na2 2.776(3) 2_655 Y C64 C65 1.384(4) . Y C65 N66 1.336(3) . Y N70 C70 1.093(6) . Y C70 C71 1.465(7) . Y N80 C80 1.127(6) . Y C80 C81 1.440(7) . Y 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 O11 101.28(8) . . Y O1 Fe1 O21 103.23(8) . . Y O11 Fe1 O21 91.54(8) . . Y O1 Fe1 O31 91.58(8) . . Y O11 Fe1 O31 99.13(8) . . Y O21 Fe1 O31 159.74(8) . . Y O1 Fe1 N26 94.02(9) . . Y O11 Fe1 N26 162.18(8) . . Y O21 Fe1 N26 75.95(8) . . Y O31 Fe1 N26 89.45(8) . . Y O1 Fe1 N36 165.86(9) . . Y O11 Fe1 N36 85.46(8) . . Y O21 Fe1 N36 88.87(8) . . Y O31 Fe1 N36 74.98(8) . . Y N26 Fe1 N36 81.70(8) . . Y O1 Fe1 Na1 49.78(6) . . Y O11 Fe1 Na1 84.67(6) . . Y O21 Fe1 Na1 150.79(6) . . Y O31 Fe1 Na1 48.36(5) . . Y N26 Fe1 Na1 112.44(6) . . Y N36 Fe1 Na1 119.54(6) . . Y O1 Fe2 O41 100.05(8) . . Y O1 Fe2 O51 102.83(8) . . Y O41 Fe2 O51 93.97(8) . . Y O1 Fe2 O61 95.08(8) . . Y O41 Fe2 O61 98.42(8) . . Y O51 Fe2 O61 156.08(8) . . Y O1 Fe2 N56 89.51(9) . . Y O41 Fe2 N56 167.82(8) . . Y O51 Fe2 N56 76.43(8) . . Y O61 Fe2 N56 88.13(8) . . Y O1 Fe2 N66 170.38(9) . . Y O41 Fe2 N66 82.83(8) . . Y O51 Fe2 N66 86.04(8) . . Y O61 Fe2 N66 75.38(8) . . Y N56 Fe2 N66 88.96(8) . . Y O1 Fe2 Na1 48.67(6) . . Y O41 Fe2 Na1 87.80(6) . . Y O51 Fe2 Na1 151.09(6) . . Y O61 Fe2 Na1 50.40(6) . . Y N56 Fe2 Na1 104.25(6) . . Y N66 Fe2 Na1 122.75(6) . . Y O12 Na1 O3 111.29(11) . . Y O12 Na1 O42 156.48(9) . . Y O3 Na1 O42 88.18(10) . . Y O12 Na1 O31 81.28(8) . . Y O3 Na1 O31 148.96(10) . . Y O42 Na1 O31 88.54(8) . . Y O12 Na1 O1 81.90(8) . . Y O3 Na1 O1 141.55(9) . . Y O42 Na1 O1 74.59(7) . . Y O31 Na1 O1 66.15(6) . . Y O12 Na1 O61 93.23(8) . . Y O3 Na1 O61 76.60(9) . . Y O42 Na1 O61 78.13(7) . . Y O31 Na1 O61 132.58(7) . . Y O1 Na1 O61 66.44(6) . . Y O12 Na1 O2 118.38(9) . . Y O3 Na1 O2 73.34(10) . . Y O42 Na1 O2 78.90(8) . . Y O31 Na1 O2 75.74(8) . . Y O1 Na1 O2 133.47(9) . . Y O61 Na1 O2 142.43(8) . . Y O12 Na1 Na2 159.55(7) . . Y O3 Na1 Na2 54.53(9) . . Y O42 Na1 Na2 43.89(6) . . Y O31 Na1 Na2 104.42(6) . . Y O1 Na1 Na2 118.46(6) . . Y O61 Na1 Na2 96.79(6) . . Y O2 Na1 Na2 46.96(6) . . Y O12 Na1 Fe1 67.58(6) . . Y O3 Na1 Fe1 172.91(9) . . Y O42 Na1 Fe1 91.44(6) . . Y O31 Na1 Fe1 38.06(4) . . Y O1 Na1 Fe1 32.14(4) . . Y O61 Na1 Fe1 96.39(5) . . Y O2 Na1 Fe1 113.53(7) . . Y Na2 Na1 Fe1 128.47(5) . . Y O12 Na1 Fe2 95.85(7) . . Y O3 Na1 Fe2 109.99(8) . . Y O42 Na1 Fe2 64.07(6) . . Y O31 Na1 Fe2 96.15(5) . . Y O1 Na1 Fe2 31.56(4) . . Y O61 Na1 Fe2 37.22(4) . . Y O2 Na1 Fe2 142.41(7) . . Y Na2 Na1 Fe2 102.92(4) . . Y Fe1 Na1 Fe2 63.64(2) . . Y O42 Na2 N13 160.62(10) . 1_645 Y O42 Na2 O2 88.56(9) . . Y N13 Na2 O2 109.90(10) 1_645 . Y O42 Na2 O3 83.38(9) . . Y N13 Na2 O3 107.03(10) 1_645 . Y O2 Na2 O3 73.38(11) . . Y O42 Na2 N63 86.38(9) . 2_655 Y N13 Na2 N63 81.77(9) 1_645 2_655 Y O2 Na2 N63 144.78(12) . 2_655 Y O3 Na2 N63 71.42(9) . 2_655 Y O42 Na2 N46 63.91(8) . . Y N13 Na2 N46 99.38(9) 1_645 . Y O2 Na2 N46 124.71(11) . . Y O3 Na2 N46 140.01(9) . . Y N63 Na2 N46 83.56(9) 2_655 . Y O42 Na2 C40 19.71(7) . . Y N13 Na2 C40 140.92(9) 1_645 . Y O2 Na2 C40 107.52(9) . . Y O3 Na2 C40 93.98(9) . . Y N63 Na2 C40 74.10(9) 2_655 . Y N46 Na2 C40 48.36(7) . . Y O42 Na2 Na1 47.23(6) . . Y N13 Na2 Na1 149.59(9) 1_645 . Y O2 Na2 Na1 55.64(8) . . Y O3 Na2 Na1 45.65(7) . . Y N63 Na2 Na1 97.26(8) 2_655 . Y N46 Na2 Na1 110.76(7) . . Y C40 Na2 Na1 65.34(6) . . Y Fe1 O1 Fe2 161.59(12) . . Y Fe1 O1 Na1 98.08(8) . . Y Fe2 O1 Na1 99.77(8) . . Y Na2 O2 Na1 77.40(9) . . Y Na1 O3 Na2 79.82(10) . . Y C10 O11 Fe1 124.96(18) . . Y C10 O12 Na1 135.40(19) . . Y O12 C10 O11 127.2(3) . . Y O12 C10 C11 120.0(2) . . Y O11 C10 C11 112.8(2) . . Y N16 C11 C12 121.3(3) . . Y N16 C11 C10 118.1(2) . . Y C12 C11 C10 120.6(2) . . Y N13 C12 C11 122.5(3) . . Y C14 N13 C12 115.7(3) . . Y C14 N13 Na2 125.9(2) . 1_465 Y C12 N13 Na2 117.94(19) . 1_465 Y N13 C14 C15 121.8(3) . . Y N16 C15 C14 122.8(3) . . Y C15 N16 C11 115.9(3) . . Y C20 O21 Fe1 121.52(17) . . Y O22 C20 O21 125.6(3) . . Y O22 C20 C21 119.5(3) . . Y O21 C20 C21 115.0(2) . . Y N26 C21 C22 120.8(3) . . Y N26 C21 C20 115.5(2) . . Y C22 C21 C20 123.7(3) . . Y N23 C22 C21 122.0(3) . . Y C24 N23 C22 116.0(3) . . Y N23 C24 C25 123.2(3) . . Y N26 C25 C24 120.2(3) . . Y C25 N26 C21 117.8(2) . . Y C25 N26 Fe1 130.3(2) . . Y C21 N26 Fe1 111.87(17) . . Y C30 O31 Fe1 122.49(17) . . Y C30 O31 Na1 137.01(17) . . Y Fe1 O31 Na1 93.58(7) . . Y O32 C30 O31 125.5(3) . . Y O32 C30 C31 120.0(2) . . Y O31 C30 C31 114.4(2) . . Y N36 C31 C32 120.2(3) . . Y N36 C31 C30 115.3(2) . . Y C32 C31 C30 124.5(3) . . Y N33 C32 C31 122.4(3) . . Y C32 N33 C34 116.4(3) . . Y N33 C34 C35 122.2(3) . . Y N36 C35 C34 120.9(3) . . Y C35 N36 C31 117.8(2) . . Y C35 N36 Fe1 129.52(19) . . Y C31 N36 Fe1 112.64(17) . . Y C40 O41 Fe2 121.46(17) . . Y C40 O42 Na2 122.79(19) . . Y C40 O42 Na1 139.86(19) . . Y Na2 O42 Na1 88.88(8) . . Y O42 C40 O41 126.6(3) . . Y O42 C40 C41 118.7(2) . . Y O41 C40 C41 114.6(2) . . Y O42 C40 Na2 37.50(14) . . Y O41 C40 Na2 149.2(2) . . Y C41 C40 Na2 87.08(16) . . Y N46 C41 C42 121.5(3) . . Y N46 C41 C40 117.0(3) . . Y C42 C41 C40 121.4(3) . . Y N43 C42 C41 122.6(3) . . Y C42 N43 C44 115.0(3) . . Y N43 C44 C45 122.7(3) . . Y N46 C45 C44 122.2(3) . . Y C41 N46 C45 115.9(3) . . Y C41 N46 Na2 102.80(19) . . Y C45 N46 Na2 135.5(2) . . Y C50 O51 Fe2 120.91(18) . . Y O52 C50 O51 125.7(3) . . Y O52 C50 C51 119.5(3) . . Y O51 C50 C51 114.8(2) . . Y N56 C51 C52 121.0(3) . . Y N56 C51 C50 115.3(2) . . Y C52 C51 C50 123.7(3) . . Y N53 C52 C51 121.9(3) . . Y C54 N53 C52 116.5(3) . . Y N53 C54 C55 122.8(3) . . Y N56 C55 C54 120.1(3) . . Y C51 N56 C55 117.7(3) . . Y C51 N56 Fe2 111.98(18) . . Y C55 N56 Fe2 129.6(2) . . Y C60 O61 Fe2 121.99(17) . . Y C60 O61 Na1 138.99(17) . . Y Fe2 O61 Na1 92.38(7) . . Y O62 C60 O61 125.0(3) . . Y O62 C60 C61 120.1(3) . . Y O61 C60 C61 114.9(2) . . Y N66 C61 C62 121.2(3) . . Y N66 C61 C60 115.1(2) . . Y C62 C61 C60 123.7(3) . . Y N63 C62 C61 122.3(3) . . Y C62 N63 C64 115.8(3) . . Y C62 N63 Na2 131.8(2) . 2_655 Y C64 N63 Na2 112.0(2) . 2_655 Y N63 C64 C65 123.1(3) . . Y N66 C65 C64 120.1(3) . . Y C61 N66 C65 117.5(2) . . Y C61 N66 Fe2 112.45(17) . . Y C65 N66 Fe2 130.02(19) . . Y N70 C70 C71 176.5(6) . . Y N80 C80 C81 179.8(5) . . Y _diffrn_reflns_theta_full 27.50 _refine_diff_density_max 0.762 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.068 # Attachment '281052.cif' data_leid24 _database_code_depnum_ccdc_archive 'CCDC 281052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Fe N4 O6' _chemical_formula_weight 338.07 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4301(2) _cell_length_b 11.0425(4) _cell_length_c 12.1683(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.185(2) _cell_angle_gamma 90.00 _cell_volume 1266.84(6) _cell_formula_units_Z 4 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.227 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22883 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2903 _reflns_number_gt 2006 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0160P)^2^+1.4842P] 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 2903 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.03745(4) 0.14277(4) 0.32674(3) 0.01977(12) Uani 1 d . . . O1 O -0.1427(3) 0.0348(2) 0.3415(2) 0.0348(6) Uani 1 d . . . H1A H -0.227(4) 0.056(3) 0.338(3) 0.055(13) Uiso 1 d . . . H1B H -0.144(4) -0.022(4) 0.368(3) 0.059(15) Uiso 1 d . . . C10 C 0.0476(3) 0.2662(3) 0.1162(2) 0.0280(7) Uani 1 d . . . C11 C 0.1683(3) 0.3245(2) 0.1808(2) 0.0207(6) Uani 1 d . . . O11 O -0.0175(2) 0.18303(17) 0.16669(16) 0.0265(5) Uani 1 d . . . O12 O 0.0216(3) 0.3009(2) 0.02248(18) 0.0540(7) Uani 1 d . . . C12 C 0.2388(3) 0.4275(3) 0.1484(2) 0.0228(7) Uani 1 d . . . H12 H 0.214(3) 0.464(2) 0.092(2) 0.015(8) Uiso 1 d . . . N13 N 0.3445(2) 0.4761(2) 0.20800(19) 0.0208(5) Uani 1 d . . . C14 C 0.3803(3) 0.4179(3) 0.3003(2) 0.0229(7) Uani 1 d . . . H14 H 0.453(3) 0.452(2) 0.340(2) 0.015(7) Uiso 1 d . . . C15 C 0.3092(3) 0.3157(3) 0.3354(2) 0.0214(6) Uani 1 d . . . H15 H 0.334(3) 0.276(3) 0.405(2) 0.030(8) Uiso 1 d . . . N16 N 0.2022(2) 0.2700(2) 0.27701(18) 0.0187(5) Uani 1 d . . . C20 C 0.0559(3) 0.2245(3) 0.5532(3) 0.0265(7) Uani 1 d . . . C21 C -0.0495(3) 0.3113(3) 0.5031(2) 0.0214(6) Uani 1 d . . . O21 O 0.1056(2) 0.14553(18) 0.48840(16) 0.0268(5) Uani 1 d . . . O22 O 0.0855(2) 0.2321(2) 0.65224(17) 0.0399(6) Uani 1 d . . . C22 C -0.1140(4) 0.4022(3) 0.5616(3) 0.0316(8) Uani 1 d . . . H22 H -0.094(3) 0.411(3) 0.633(2) 0.026(8) Uiso 1 d . . . N23 N -0.2036(3) 0.4817(2) 0.5145(2) 0.0361(7) Uani 1 d . . . C24 C -0.2300(3) 0.4661(3) 0.4078(3) 0.0312(8) Uani 1 d . . . H24 H -0.291(3) 0.523(3) 0.374(2) 0.036(9) Uiso 1 d . . . C25 C -0.1694(3) 0.3738(3) 0.3488(3) 0.0260(7) Uani 1 d . . . H25 H -0.192(3) 0.363(3) 0.275(2) 0.028(8) Uiso 1 d . . . N26 N -0.0789(2) 0.2966(2) 0.39585(19) 0.0206(5) Uani 1 d . . . O99 O 0.0867(3) 0.3994(3) 0.8235(3) 0.0394(6) Uani 1 d . . . H99A H 0.072(3) 0.373(3) 0.883(3) 0.039(11) Uiso 1 d . . . H99B H 0.082(4) 0.347(4) 0.784(3) 0.049(15) Uiso 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 Fe1 0.0215(2) 0.01543(19) 0.0224(2) 0.0015(2) -0.00027(15) 0.0002(2) O1 0.0226(14) 0.0228(13) 0.0590(17) 0.0146(12) -0.0007(12) -0.0009(11) C10 0.0334(18) 0.0299(17) 0.0204(16) -0.0011(14) -0.0040(13) -0.0090(15) C11 0.0212(15) 0.0233(16) 0.0175(15) -0.0026(12) 0.0012(12) 0.0001(12) O11 0.0296(12) 0.0240(11) 0.0257(11) -0.0001(9) -0.0049(9) -0.0097(9) O12 0.0686(18) 0.0712(18) 0.0214(13) 0.0157(12) -0.0178(12) -0.0390(15) C12 0.0268(17) 0.0231(17) 0.0185(16) 0.0032(14) 0.0017(13) 0.0023(14) N13 0.0195(13) 0.0171(12) 0.0258(14) -0.0013(11) 0.0030(11) -0.0005(10) C14 0.0178(15) 0.0215(16) 0.0294(17) -0.0025(14) -0.0034(13) -0.0006(13) C15 0.0205(15) 0.0205(15) 0.0232(17) 0.0007(13) 0.0001(13) 0.0051(13) N16 0.0194(13) 0.0180(12) 0.0187(13) -0.0021(10) 0.0007(10) 0.0005(10) C20 0.0255(17) 0.0260(17) 0.0280(18) 0.0088(14) -0.0002(14) -0.0088(14) C21 0.0237(16) 0.0213(15) 0.0191(15) 0.0028(12) 0.0033(12) -0.0040(13) O21 0.0321(12) 0.0215(10) 0.0265(11) 0.0039(10) -0.0065(9) 0.0031(10) O22 0.0492(15) 0.0501(15) 0.0201(12) 0.0088(11) -0.0066(10) -0.0005(12) C22 0.042(2) 0.0314(18) 0.0214(18) -0.0009(15) 0.0084(15) -0.0013(15) N23 0.0409(17) 0.0317(16) 0.0359(17) -0.0033(13) 0.0078(13) 0.0076(13) C24 0.0279(18) 0.0254(17) 0.040(2) 0.0017(15) 0.0005(15) 0.0072(15) C25 0.0271(17) 0.0261(18) 0.0246(17) 0.0028(14) -0.0010(13) 0.0038(14) N26 0.0226(13) 0.0184(12) 0.0208(13) 0.0037(10) -0.0001(10) 0.0005(11) O99 0.0388(15) 0.0501(17) 0.0294(15) 0.0053(15) -0.0002(12) -0.0129(12) _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 O11 2.054(2) . ? Fe1 O21 2.0570(19) . ? Fe1 O1 2.087(2) . ? Fe1 N16 2.189(2) . ? Fe1 N13 2.196(2) 2_545 ? Fe1 N26 2.199(2) . ? C10 O12 1.223(3) . ? C10 O11 1.270(3) . ? C10 C11 1.513(4) . ? C11 N16 1.349(3) . ? C11 C12 1.380(4) . ? C12 N13 1.333(4) . ? N13 C14 1.332(4) . ? N13 Fe1 2.196(2) 2 ? C14 C15 1.385(4) . ? C15 N16 1.322(4) . ? C20 O22 1.235(3) . ? C20 O21 1.272(4) . ? C20 C21 1.501(4) . ? C21 N26 1.339(3) . ? C21 C22 1.379(4) . ? C22 N23 1.339(4) . ? N23 C24 1.328(4) . ? C24 C25 1.378(4) . ? C25 N26 1.327(4) . ? 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 O11 Fe1 O21 166.27(8) . . ? O11 Fe1 O1 90.87(9) . . ? O21 Fe1 O1 99.51(9) . . ? O11 Fe1 N16 76.44(8) . . ? O21 Fe1 N16 92.60(8) . . ? O1 Fe1 N16 166.98(10) . . ? O11 Fe1 N13 96.77(8) . 2_545 ? O21 Fe1 N13 92.68(8) . 2_545 ? O1 Fe1 N13 87.42(10) . 2_545 ? N16 Fe1 N13 96.83(8) . 2_545 ? O11 Fe1 N26 94.43(8) . . ? O21 Fe1 N26 76.79(8) . . ? O1 Fe1 N26 89.70(10) . . ? N16 Fe1 N26 88.43(8) . . ? N13 Fe1 N26 168.47(9) 2_545 . ? O12 C10 O11 126.0(3) . . ? O12 C10 C11 119.0(3) . . ? O11 C10 C11 115.0(3) . . ? N16 C11 C12 120.6(3) . . ? N16 C11 C10 115.1(2) . . ? C12 C11 C10 124.3(3) . . ? C10 O11 Fe1 120.02(18) . . ? N13 C12 C11 122.4(3) . . ? C14 N13 C12 116.0(3) . . ? C14 N13 Fe1 116.49(19) . 2 ? C12 N13 Fe1 127.5(2) . 2 ? N13 C14 C15 122.5(3) . . ? N16 C15 C14 121.0(3) . . ? C15 N16 C11 117.5(2) . . ? C15 N16 Fe1 129.4(2) . . ? C11 N16 Fe1 111.66(17) . . ? O22 C20 O21 125.0(3) . . ? O22 C20 C21 119.2(3) . . ? O21 C20 C21 115.9(3) . . ? N26 C21 C22 120.4(3) . . ? N26 C21 C20 116.1(3) . . ? C22 C21 C20 123.4(3) . . ? C20 O21 Fe1 119.40(18) . . ? N23 C22 C21 122.5(3) . . ? C24 N23 C22 115.9(3) . . ? N23 C24 C25 122.3(3) . . ? N26 C25 C24 121.4(3) . . ? C25 N26 C21 117.5(3) . . ? C25 N26 Fe1 130.7(2) . . ? C21 N26 Fe1 111.81(18) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.361 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.079 # Attachment '415624.CIF' data_pm15 _database_code_depnum_ccdc_archive 'CCDC 289254' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H21 Fe N7 O4' _chemical_formula_weight 539.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Fe Fe 0.3463 0.8444 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.239(2) _cell_length_b 28.497(2) _cell_length_c 10.402(4) _cell_angle_alpha 90.00 _cell_angle_beta 118.93(2) _cell_angle_gamma 90.00 _cell_volume 2396.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 35346 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.53 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8765 _exptl_absorpt_correction_T_max 0.9478 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35346 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5486 _reflns_number_gt 4072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002)' _computing_cell_refinement 'COLLECT (Nonius, 2002)' _computing_data_reduction 'COLLECT (Nonius, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXTL (Sheldrick, 1990)' _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^)+(0.0376P)^2^+1.2197P] 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 5486 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.33229(4) 0.109197(10) 0.65612(3) 0.01867(9) Uani 1 d . . . N11 N 0.5466(2) 0.07631(6) 0.65234(19) 0.0211(4) Uani 1 d . . . C12 C 0.5091(3) 0.06362(7) 0.5149(2) 0.0206(4) Uani 1 d . . . C13 C 0.6313(3) 0.04876(8) 0.4832(3) 0.0272(5) Uani 1 d . . . H13A H 0.6009 0.0412 0.3843 0.033 Uiso 1 calc R . . N14 N 0.7904(3) 0.04459(7) 0.5859(2) 0.0316(5) Uani 1 d . . . C15 C 0.8231(3) 0.05527(8) 0.7221(3) 0.0309(5) Uani 1 d . . . H15A H 0.9332 0.0516 0.7997 0.037 Uiso 1 calc R . . C16 C 0.7041(3) 0.07156(8) 0.7558(2) 0.0261(5) Uani 1 d . . . H16A H 0.7352 0.0795 0.8546 0.031 Uiso 1 calc R . . C17 C 0.3290(3) 0.06500(7) 0.4017(2) 0.0222(5) Uani 1 d . . . O18 O 0.23295(18) 0.08295(5) 0.44736(15) 0.0239(3) Uani 1 d . . . O19 O 0.2854(2) 0.04922(6) 0.27899(17) 0.0314(4) Uani 1 d . . . N21 N 0.2818(2) 0.04899(6) 0.75945(18) 0.0189(4) Uani 1 d . . . C22 C 0.3447(3) 0.05443(7) 0.9054(2) 0.0193(4) Uani 1 d . . . C23 C 0.3105(3) 0.02197(8) 0.9869(2) 0.0250(5) Uani 1 d . . . H23A H 0.3568 0.0267 1.0897 0.030 Uiso 1 calc R . . N24 N 0.2144(3) -0.01578(7) 0.9258(2) 0.0305(5) Uani 1 d . . . C25 C 0.1538(3) -0.02051(8) 0.7808(3) 0.0292(5) Uani 1 d . . . H25A H 0.0851 -0.0467 0.7327 0.035 Uiso 1 calc R . . C26 C 0.1874(3) 0.01138(7) 0.6979(2) 0.0232(5) Uani 1 d . . . H26A H 0.1424 0.0063 0.5953 0.028 Uiso 1 calc R . . C27 C 0.4506(3) 0.09770(7) 0.9709(2) 0.0224(5) Uani 1 d . . . O28 O 0.45563(19) 0.12588(5) 0.87580(16) 0.0238(3) Uani 1 d . . . O29 O 0.5208(2) 0.10352(6) 1.10416(16) 0.0350(4) Uani 1 d . . . N31 N 0.4052(2) 0.17809(6) 0.60746(19) 0.0219(4) Uani 1 d . . . C32 C 0.5292(3) 0.20283(8) 0.7120(2) 0.0264(5) Uani 1 d . . . H32A H 0.5864 0.1900 0.8081 0.032 Uiso 1 calc R . . C33 C 0.5786(3) 0.24621(8) 0.6875(3) 0.0313(5) Uani 1 d . . . H33A H 0.6674 0.2625 0.7653 0.038 Uiso 1 calc R . . C34 C 0.4971(3) 0.26545(8) 0.5485(3) 0.0351(6) Uani 1 d . . . H34A H 0.5275 0.2953 0.5288 0.042 Uiso 1 calc R . . C35 C 0.3702(3) 0.24011(9) 0.4390(3) 0.0366(6) Uani 1 d . . . H35A H 0.3128 0.2522 0.3418 0.044 Uiso 1 calc R . . C36 C 0.3268(3) 0.19682(8) 0.4717(3) 0.0290(5) Uani 1 d . . . H36A H 0.2386 0.1798 0.3955 0.035 Uiso 1 calc R . . N41 N 0.0872(2) 0.13759(6) 0.60123(19) 0.0215(4) Uani 1 d . . . C42 C 0.0566(3) 0.15556(8) 0.7051(3) 0.0261(5) Uani 1 d . . . H42A H 0.1454 0.1579 0.8028 0.031 Uiso 1 calc R . . C43 C -0.0981(3) 0.17086(9) 0.6764(3) 0.0317(5) Uani 1 d . . . H43A H -0.1147 0.1835 0.7528 0.038 Uiso 1 calc R . . C44 C -0.2281(3) 0.16744(8) 0.5353(3) 0.0314(5) Uani 1 d . . . H44A H -0.3358 0.1775 0.5130 0.038 Uiso 1 calc R . . C45 C -0.1991(3) 0.14913(8) 0.4269(3) 0.0287(5) Uani 1 d . . . H45A H -0.2862 0.1464 0.3287 0.034 Uiso 1 calc R . . C46 C -0.0409(3) 0.13497(8) 0.4646(2) 0.0246(5) Uani 1 d . . . H46A H -0.0215 0.1226 0.3894 0.030 Uiso 1 calc R . . N51 N 0.1456(3) 0.19388(11) 1.0735(3) 0.0611(7) Uani 1 d . . . C52 C 0.0120(4) 0.21986(10) 1.0562(3) 0.0495(8) Uani 1 d . . . H52A H 0.0131 0.2527 1.0413 0.059 Uiso 1 calc R . . C53 C -0.1182(3) 0.20157(9) 1.0590(3) 0.0394(6) Uani 1 d . . . H53A H -0.2081 0.2208 1.0465 0.047 Uiso 1 calc R . . C54 C -0.1201(3) 0.15518(10) 1.0801(3) 0.0419(7) Uani 1 d . . . H54A H -0.2128 0.1417 1.0826 0.050 Uiso 1 calc R . . C55 C 0.0087(3) 0.12653(10) 1.0982(3) 0.0366(6) Uani 1 d . . . H55A H 0.0046 0.0937 1.1118 0.044 Uiso 1 calc R . . C56 C 0.1432(3) 0.14641(10) 1.0962(3) 0.0377(6) Uani 1 d . . . H56A H 0.2342 0.1274 1.1105 0.045 Uiso 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 0.01879(16) 0.02184(16) 0.01704(15) -0.00212(13) 0.00997(13) -0.00145(13) N11 0.0231(10) 0.0192(9) 0.0237(10) -0.0003(7) 0.0134(8) 0.0003(7) C12 0.0224(12) 0.0186(10) 0.0227(11) -0.0016(9) 0.0126(10) -0.0014(8) C13 0.0315(14) 0.0270(12) 0.0291(12) -0.0039(10) 0.0196(11) 0.0011(10) N14 0.0277(12) 0.0325(11) 0.0369(12) -0.0026(9) 0.0174(10) 0.0043(9) C15 0.0243(13) 0.0304(13) 0.0331(14) 0.0005(10) 0.0100(11) 0.0046(10) C16 0.0264(13) 0.0271(12) 0.0228(12) 0.0002(9) 0.0103(10) 0.0014(9) C17 0.0298(13) 0.0198(11) 0.0208(11) -0.0004(9) 0.0153(10) 0.0010(9) O18 0.0224(9) 0.0300(8) 0.0200(8) -0.0040(6) 0.0109(7) -0.0001(6) O19 0.0351(10) 0.0386(9) 0.0220(8) -0.0063(7) 0.0150(8) 0.0022(7) N21 0.0175(9) 0.0226(9) 0.0179(9) -0.0007(7) 0.0096(8) 0.0018(7) C22 0.0179(11) 0.0227(11) 0.0185(11) -0.0002(8) 0.0097(9) 0.0033(8) C23 0.0274(13) 0.0287(12) 0.0205(11) 0.0008(9) 0.0129(10) 0.0011(9) N24 0.0392(13) 0.0269(10) 0.0298(11) 0.0003(9) 0.0202(10) -0.0032(9) C25 0.0343(14) 0.0232(11) 0.0321(13) -0.0048(10) 0.0175(11) -0.0060(10) C26 0.0229(12) 0.0253(11) 0.0216(11) -0.0050(9) 0.0109(10) -0.0002(9) C27 0.0196(11) 0.0282(11) 0.0208(11) -0.0027(9) 0.0109(10) 0.0000(9) O28 0.0255(9) 0.0265(8) 0.0201(8) -0.0029(6) 0.0115(7) -0.0046(6) O29 0.0384(10) 0.0461(11) 0.0163(8) -0.0067(7) 0.0099(8) -0.0122(8) N31 0.0226(10) 0.0236(9) 0.0228(10) -0.0006(8) 0.0138(8) -0.0005(8) C32 0.0266(13) 0.0297(12) 0.0240(12) -0.0021(10) 0.0131(10) -0.0017(10) C33 0.0310(14) 0.0292(13) 0.0361(14) -0.0082(11) 0.0181(12) -0.0097(10) C34 0.0390(15) 0.0248(12) 0.0474(16) 0.0047(11) 0.0256(14) -0.0022(11) C35 0.0361(15) 0.0367(14) 0.0363(15) 0.0107(12) 0.0170(13) 0.0014(11) C36 0.0261(13) 0.0304(12) 0.0291(13) 0.0018(10) 0.0123(11) -0.0022(10) N41 0.0222(10) 0.0212(9) 0.0233(10) 0.0010(7) 0.0126(8) 0.0007(7) C42 0.0245(13) 0.0296(12) 0.0235(12) -0.0029(10) 0.0112(10) 0.0010(9) C43 0.0299(14) 0.0386(13) 0.0312(13) -0.0029(11) 0.0183(12) 0.0069(11) C44 0.0214(13) 0.0342(13) 0.0397(14) 0.0029(11) 0.0157(12) 0.0054(10) C45 0.0240(13) 0.0283(12) 0.0279(13) 0.0013(10) 0.0079(11) 0.0025(10) C46 0.0257(13) 0.0251(11) 0.0220(12) -0.0013(9) 0.0106(10) 0.0008(9) N51 0.0552(18) 0.078(2) 0.0488(16) 0.0013(14) 0.0241(15) -0.0145(15) C52 0.063(2) 0.0324(15) 0.0456(18) -0.0021(13) 0.0201(17) -0.0007(14) C53 0.0330(15) 0.0405(15) 0.0450(16) -0.0041(13) 0.0191(13) 0.0093(12) C54 0.0244(14) 0.0648(19) 0.0335(15) -0.0027(13) 0.0116(12) -0.0071(13) C55 0.0411(16) 0.0397(14) 0.0252(13) 0.0027(11) 0.0130(12) -0.0042(12) C56 0.0332(15) 0.0497(16) 0.0320(14) 0.0045(12) 0.0172(13) 0.0075(12) _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 O18 2.0468(16) . ? Fe1 O28 2.0559(17) . ? Fe1 N21 2.1914(17) . ? Fe1 N41 2.2038(19) . ? Fe1 N11 2.2081(18) . ? Fe1 N31 2.2122(17) . ? N11 C16 1.334(3) . ? N11 C12 1.347(3) . ? C12 C13 1.387(3) . ? C12 C17 1.504(3) . ? C13 N14 1.341(3) . ? C13 H13A 0.9500 . ? N14 C15 1.333(3) . ? C15 C16 1.387(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O19 1.224(2) . ? C17 O18 1.297(2) . ? N21 C26 1.333(3) . ? N21 C22 1.347(3) . ? C22 C23 1.391(3) . ? C22 C27 1.515(3) . ? C23 N24 1.343(3) . ? C23 H23A 0.9500 . ? N24 C25 1.338(3) . ? C25 C26 1.387(3) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 O29 1.225(3) . ? C27 O28 1.292(3) . ? N31 C32 1.336(3) . ? N31 C36 1.347(3) . ? C32 C33 1.383(3) . ? C32 H32A 0.9500 . ? C33 C34 1.380(3) . ? C33 H33A 0.9500 . ? C34 C35 1.379(4) . ? C34 H34A 0.9500 . ? C35 C36 1.390(3) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? N41 C46 1.341(3) . ? N41 C42 1.344(3) . ? C42 C43 1.382(3) . ? C42 H42A 0.9500 . ? C43 C44 1.379(3) . ? C43 H43A 0.9500 . ? C44 C45 1.381(3) . ? C44 H44A 0.9500 . ? C45 C46 1.378(3) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? N51 C52 1.374(4) . ? N51 C56 1.375(4) . ? C52 C53 1.325(4) . ? C52 H52A 0.9500 . ? C53 C54 1.341(4) . ? C53 H53A 0.9500 . ? C54 C55 1.379(4) . ? C54 H54A 0.9500 . ? C55 C56 1.375(4) . ? C55 H55A 0.9500 . ? C56 H56A 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 O18 Fe1 O28 170.65(6) . . ? O18 Fe1 N21 98.15(6) . . ? O28 Fe1 N21 76.76(6) . . ? O18 Fe1 N41 88.97(7) . . ? O28 Fe1 N41 98.66(7) . . ? N21 Fe1 N41 88.78(6) . . ? O18 Fe1 N11 76.81(7) . . ? O28 Fe1 N11 95.64(7) . . ? N21 Fe1 N11 94.70(6) . . ? N41 Fe1 N11 165.69(7) . . ? O18 Fe1 N31 96.39(6) . . ? O28 Fe1 N31 89.01(6) . . ? N21 Fe1 N31 165.40(6) . . ? N41 Fe1 N31 90.19(6) . . ? N11 Fe1 N31 89.86(6) . . ? C16 N11 C12 116.70(18) . . ? C16 N11 Fe1 131.76(14) . . ? C12 N11 Fe1 111.13(14) . . ? N11 C12 C13 120.9(2) . . ? N11 C12 C17 116.27(18) . . ? C13 C12 C17 122.8(2) . . ? N14 C13 C12 122.9(2) . . ? N14 C13 H13A 118.6 . . ? C12 C13 H13A 118.6 . . ? C15 N14 C13 115.1(2) . . ? N14 C15 C16 123.1(2) . . ? N14 C15 H15A 118.5 . . ? C16 C15 H15A 118.5 . . ? N11 C16 C15 121.2(2) . . ? N11 C16 H16A 119.4 . . ? C15 C16 H16A 119.4 . . ? O19 C17 O18 126.1(2) . . ? O19 C17 C12 119.23(19) . . ? O18 C17 C12 114.70(18) . . ? C17 O18 Fe1 119.83(14) . . ? C26 N21 C22 117.34(18) . . ? C26 N21 Fe1 129.69(14) . . ? C22 N21 Fe1 112.62(13) . . ? N21 C22 C23 120.6(2) . . ? N21 C22 C27 115.68(17) . . ? C23 C22 C27 123.71(19) . . ? N24 C23 C22 122.5(2) . . ? N24 C23 H23A 118.7 . . ? C22 C23 H23A 118.7 . . ? C25 N24 C23 115.77(19) . . ? N24 C25 C26 122.5(2) . . ? N24 C25 H25A 118.8 . . ? C26 C25 H25A 118.8 . . ? N21 C26 C25 121.3(2) . . ? N21 C26 H26A 119.4 . . ? C25 C26 H26A 119.4 . . ? O29 C27 O28 125.9(2) . . ? O29 C27 C22 119.50(19) . . ? O28 C27 C22 114.57(18) . . ? C27 O28 Fe1 120.09(13) . . ? C32 N31 C36 117.29(19) . . ? C32 N31 Fe1 121.20(14) . . ? C36 N31 Fe1 121.51(15) . . ? N31 C32 C33 123.4(2) . . ? N31 C32 H32A 118.3 . . ? C33 C32 H32A 118.3 . . ? C34 C33 C32 119.1(2) . . ? C34 C33 H33A 120.4 . . ? C32 C33 H33A 120.4 . . ? C35 C34 C33 118.2(2) . . ? C35 C34 H34A 120.9 . . ? C33 C34 H34A 120.9 . . ? C34 C35 C36 119.6(2) . . ? C34 C35 H35A 120.2 . . ? C36 C35 H35A 120.2 . . ? N31 C36 C35 122.4(2) . . ? N31 C36 H36A 118.8 . . ? C35 C36 H36A 118.8 . . ? C46 N41 C42 116.89(19) . . ? C46 N41 Fe1 121.57(14) . . ? C42 N41 Fe1 121.41(15) . . ? N41 C42 C43 123.0(2) . . ? N41 C42 H42A 118.5 . . ? C43 C42 H42A 118.5 . . ? C44 C43 C42 119.0(2) . . ? C44 C43 H43A 120.5 . . ? C42 C43 H43A 120.5 . . ? C43 C44 C45 118.9(2) . . ? C43 C44 H44A 120.6 . . ? C45 C44 H44A 120.6 . . ? C46 C45 C44 118.5(2) . . ? C46 C45 H45A 120.8 . . ? C44 C45 H45A 120.8 . . ? N41 C46 C45 123.8(2) . . ? N41 C46 H46A 118.1 . . ? C45 C46 H46A 118.1 . . ? C52 N51 C56 117.7(3) . . ? C53 C52 N51 123.6(3) . . ? C53 C52 H52A 118.2 . . ? N51 C52 H52A 118.2 . . ? C52 C53 C54 118.4(3) . . ? C52 C53 H53A 120.8 . . ? C54 C53 H53A 120.8 . . ? C53 C54 C55 121.8(3) . . ? C53 C54 H54A 119.1 . . ? C55 C54 H54A 119.1 . . ? C56 C55 C54 118.7(3) . . ? C56 C55 H55A 120.6 . . ? C54 C55 H55A 120.6 . . ? N51 C56 C55 119.9(3) . . ? N51 C56 H56A 120.1 . . ? C55 C56 H56A 120.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.417 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.061