# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Song Gao' _publ_contact_author_email GAOSONG@PKU.EDU.CN _publ_section_title ; Abrupt spin transition around room temperature and light induced properties in FeII complexes with N4O2 coordination sphere ; loop_ _publ_author_name 'Song Gao.' 'Zhe-Ming Wang.' 'Guan-Cheng Xu.' 'Hong-Bin Xu.' 'Teng Zhang.' ; Li Zhang ; # Attachment '1 CH3OH.cif' data_CH3OH _database_code_depnum_ccdc_archive 'CCDC 756166' #TrackingRef '1 CH3OH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 Fe N6 O5' _chemical_formula_sum 'C27 H24 Fe N6 O5' _chemical_formula_weight 568.37 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 20.676(4) _cell_length_b 10.389(2) _cell_length_c 12.566(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.90(3) _cell_angle_gamma 90.00 _cell_volume 2631.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 20473 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21612 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2313 _reflns_number_gt 1765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0526P)^2^+0.3107P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2313 _refine_ls_number_parameters 188 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.003 _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 1.0000 1.00512(4) 0.2500 0.04060(18) Uani 1 2 d S . . C1 C 1.09702(11) 1.2023(2) 0.3589(2) 0.0584(6) Uani 1 1 d . . . H1 H 1.1228 1.1822 0.3093 0.070 Uiso 1 1 calc R . . C2 C 1.11847(13) 1.2987(3) 0.4345(2) 0.0691(7) Uani 1 1 d . . . H2 H 1.1581 1.3418 0.4359 0.083 Uiso 1 1 calc R . . C3 C 1.08048(13) 1.3297(3) 0.5074(2) 0.0692(7) Uani 1 1 d . . . H3 H 1.0935 1.3957 0.5577 0.083 Uiso 1 1 calc R . . C4 C 1.02276(13) 1.2621(2) 0.5054(2) 0.0611(6) Uani 1 1 d . . . H4 H 0.9970 1.2809 0.5553 0.073 Uiso 1 1 calc R . . C5 C 1.00369(10) 1.1663(2) 0.42857(18) 0.0470(5) Uani 1 1 d . . . C6 C 0.94511(10) 1.0871(2) 0.41769(19) 0.0486(5) Uani 1 1 d . . . H6 H 0.9158 1.0932 0.4638 0.058 Uiso 1 1 calc R . . C7 C 0.89032(9) 0.85406(19) 0.22521(17) 0.0422(5) Uani 1 1 d . . . C8 C 0.84022(10) 0.7541(2) 0.18371(18) 0.0437(5) Uani 1 1 d . . . C9 C 0.79528(11) 0.7115(2) 0.2435(2) 0.0571(6) Uani 1 1 d . . . H9 H 0.7954 0.7488 0.3108 0.069 Uiso 1 1 calc R . . C10 C 0.75059(11) 0.6147(2) 0.2043(2) 0.0582(6) Uani 1 1 d . . . H10 H 0.7214 0.5865 0.2460 0.070 Uiso 1 1 calc R . . C11 C 0.74890(10) 0.5591(2) 0.10346(19) 0.0483(5) Uani 1 1 d . . . C12 C 0.79304(10) 0.6014(2) 0.04258(18) 0.0482(6) Uani 1 1 d . . . H12 H 0.7922 0.5655 -0.0255 0.058 Uiso 1 1 calc R . . C13 C 0.83818(10) 0.6966(2) 0.08290(18) 0.0469(5) Uani 1 1 d . . . H13 H 0.8680 0.7232 0.0418 0.056 Uiso 1 1 calc R . . C14 C 0.9469(12) 0.5172(12) 0.7840(11) 0.312(14) Uani 0.50 1 d PDU . . H14A H 0.9574 0.5248 0.8621 0.468 Uiso 0.50 1 calc PR . . H14B H 0.9075 0.4662 0.7612 0.468 Uiso 0.50 1 calc PR . . H14C H 0.9396 0.6013 0.7519 0.468 Uiso 0.50 1 calc PR . . N1 N 1.04077(8) 1.13696(16) 0.35398(14) 0.0455(4) Uani 1 1 d . . . N2 N 0.93773(8) 1.00657(15) 0.33678(14) 0.0400(4) Uani 1 1 d . . . N3 N 0.88424(8) 0.92365(17) 0.31189(15) 0.0443(4) Uani 1 1 d . . . O1 O 0.93851(6) 0.86937(13) 0.17655(11) 0.0448(4) Uani 1 1 d . . . O2 O 0.70647(8) 0.46420(16) 0.06094(14) 0.0620(5) Uani 1 1 d . . . H2A H 0.6828 0.4469 0.1033 0.093 Uiso 1 1 calc R . . O3 O 1.0000 0.457(3) 0.7500 0.386(10) Uani 1 2 d SDU . . H3A H 1.006(5) 0.41(3) 0.699(19) 0.464 Uiso 0.50 1 d PD . . 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 0.0348(3) 0.0394(3) 0.0522(3) 0.000 0.01960(19) 0.000 C1 0.0504(14) 0.0567(15) 0.0722(16) -0.0056(13) 0.0220(12) -0.0097(12) C2 0.0656(16) 0.0635(17) 0.0801(19) -0.0088(14) 0.0203(15) -0.0221(13) C3 0.0756(18) 0.0608(16) 0.0722(18) -0.0146(14) 0.0185(14) -0.0140(14) C4 0.0690(16) 0.0589(15) 0.0601(15) -0.0080(12) 0.0246(13) -0.0042(13) C5 0.0479(12) 0.0434(12) 0.0521(14) 0.0002(10) 0.0160(11) 0.0018(10) C6 0.0480(13) 0.0479(12) 0.0558(14) -0.0006(11) 0.0242(11) 0.0034(10) C7 0.0353(11) 0.0407(11) 0.0536(13) 0.0036(10) 0.0162(10) 0.0037(9) C8 0.0353(10) 0.0422(12) 0.0574(14) 0.0039(10) 0.0183(10) 0.0012(9) C9 0.0486(13) 0.0652(15) 0.0644(15) -0.0109(12) 0.0272(12) -0.0112(12) C10 0.0494(13) 0.0625(15) 0.0726(17) -0.0056(13) 0.0345(12) -0.0126(11) C11 0.0388(11) 0.0437(12) 0.0657(15) -0.0003(11) 0.0188(11) -0.0029(10) C12 0.0453(12) 0.0477(13) 0.0558(14) -0.0046(11) 0.0199(11) -0.0017(10) C13 0.0415(11) 0.0450(12) 0.0590(14) 0.0062(11) 0.0213(11) -0.0008(10) C14 0.59(4) 0.134(10) 0.123(11) 0.048(8) -0.111(16) -0.126(16) N1 0.0416(10) 0.0430(10) 0.0543(11) 0.0008(8) 0.0157(9) -0.0011(8) N2 0.0361(9) 0.0391(9) 0.0481(10) 0.0011(9) 0.0161(8) 0.0017(8) N3 0.0356(9) 0.0439(10) 0.0579(11) -0.0005(9) 0.0203(8) -0.0007(8) O1 0.0377(7) 0.0456(8) 0.0573(9) -0.0030(7) 0.0236(7) -0.0026(6) O2 0.0560(10) 0.0615(11) 0.0772(12) -0.0136(9) 0.0330(9) -0.0199(8) O3 0.377(16) 0.46(3) 0.333(19) 0.000 0.104(12) 0.000 _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 N2 1.8637(16) . ? Fe1 N2 1.8637(16) 2_755 ? Fe1 N1 1.9499(18) . ? Fe1 N1 1.9499(17) 2_755 ? Fe1 O1 1.9833(14) . ? Fe1 O1 1.9833(14) 2_755 ? C1 N1 1.336(3) . ? C1 C2 1.384(3) . ? C1 H1 0.9300 . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 N1 1.371(3) . ? C5 C6 1.445(3) . ? C6 N2 1.299(3) . ? C6 H6 0.9300 . ? C7 O1 1.290(2) . ? C7 N3 1.336(3) . ? C7 C8 1.477(3) . ? C8 C9 1.391(3) . ? C8 C13 1.392(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 O2 1.348(3) . ? C11 C12 1.387(3) . ? C12 C13 1.376(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O3 1.41(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N2 N3 1.382(2) . ? O2 H2A 0.8200 . ? O3 C14 1.41(2) 2_756 ? O3 H3A 0.84(3) . ? 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 N2 Fe1 N2 179.07(10) . 2_755 ? N2 Fe1 N1 81.60(7) . . ? N2 Fe1 N1 97.74(7) 2_755 . ? N2 Fe1 N1 97.74(7) . 2_755 ? N2 Fe1 N1 81.60(7) 2_755 2_755 ? N1 Fe1 N1 90.75(10) . 2_755 ? N2 Fe1 O1 79.82(6) . . ? N2 Fe1 O1 100.85(6) 2_755 . ? N1 Fe1 O1 161.38(6) . . ? N1 Fe1 O1 92.94(7) 2_755 . ? N2 Fe1 O1 100.85(6) . 2_755 ? N2 Fe1 O1 79.82(6) 2_755 2_755 ? N1 Fe1 O1 92.94(7) . 2_755 ? N1 Fe1 O1 161.38(6) 2_755 2_755 ? O1 Fe1 O1 89.35(8) . 2_755 ? N1 C1 C2 122.8(2) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.5(2) . . ? N1 C5 C6 113.19(19) . . ? C4 C5 C6 125.3(2) . . ? N2 C6 C5 112.96(18) . . ? N2 C6 H6 123.5 . . ? C5 C6 H6 123.5 . . ? O1 C7 N3 122.87(18) . . ? O1 C7 C8 118.31(18) . . ? N3 C7 C8 118.82(17) . . ? C9 C8 C13 117.8(2) . . ? C9 C8 C7 122.2(2) . . ? C13 C8 C7 119.94(18) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? O2 C11 C10 123.24(19) . . ? O2 C11 C12 117.6(2) . . ? C10 C11 C12 119.2(2) . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 121.56(19) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 N1 C5 118.00(19) . . ? C1 N1 Fe1 129.00(16) . . ? C5 N1 Fe1 112.96(13) . . ? C6 N2 N3 121.81(16) . . ? C6 N2 Fe1 119.16(14) . . ? N3 N2 Fe1 119.02(12) . . ? C7 N3 N2 107.80(15) . . ? C7 O1 Fe1 110.48(13) . . ? C11 O2 H2A 109.5 . . ? C14 O3 C14 128(3) . 2_756 ? C14 O3 H3A 139(6) . . ? C14 O3 H3A 76(10) 2_756 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.5(4) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? C3 C4 C5 N1 -0.1(4) . . . . ? C3 C4 C5 C6 179.3(2) . . . . ? N1 C5 C6 N2 -2.3(3) . . . . ? C4 C5 C6 N2 178.2(2) . . . . ? O1 C7 C8 C9 165.8(2) . . . . ? N3 C7 C8 C9 -13.5(3) . . . . ? O1 C7 C8 C13 -12.4(3) . . . . ? N3 C7 C8 C13 168.32(19) . . . . ? C13 C8 C9 C10 0.6(3) . . . . ? C7 C8 C9 C10 -177.7(2) . . . . ? C8 C9 C10 C11 -1.0(4) . . . . ? C9 C10 C11 O2 179.9(2) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? O2 C11 C12 C13 -178.9(2) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C8 -1.1(3) . . . . ? C9 C8 C13 C12 0.5(3) . . . . ? C7 C8 C13 C12 178.75(19) . . . . ? C2 C1 N1 C5 -1.0(3) . . . . ? C2 C1 N1 Fe1 176.59(19) . . . . ? C4 C5 N1 C1 1.3(3) . . . . ? C6 C5 N1 C1 -178.24(19) . . . . ? C4 C5 N1 Fe1 -176.67(18) . . . . ? C6 C5 N1 Fe1 3.8(2) . . . . ? N2 Fe1 N1 C1 179.1(2) . . . . ? N2 Fe1 N1 C1 -1.5(2) 2_755 . . . ? N1 Fe1 N1 C1 -83.1(2) 2_755 . . . ? O1 Fe1 N1 C1 175.33(19) . . . . ? O1 Fe1 N1 C1 78.6(2) 2_755 . . . ? N2 Fe1 N1 C5 -3.17(14) . . . . ? N2 Fe1 N1 C5 176.17(14) 2_755 . . . ? N1 Fe1 N1 C5 94.54(15) 2_755 . . . ? O1 Fe1 N1 C5 -7.0(3) . . . . ? O1 Fe1 N1 C5 -103.71(14) 2_755 . . . ? C5 C6 N2 N3 -179.09(16) . . . . ? C5 C6 N2 Fe1 -0.4(2) . . . . ? N2 Fe1 N2 C6 -42.85(17) 2_755 . . . ? N1 Fe1 N2 C6 2.00(16) . . . . ? N1 Fe1 N2 C6 -87.62(17) 2_755 . . . ? O1 Fe1 N2 C6 -179.24(17) . . . . ? O1 Fe1 N2 C6 93.41(16) 2_755 . . . ? N2 Fe1 N2 N3 135.86(14) 2_755 . . . ? N1 Fe1 N2 N3 -179.29(15) . . . . ? N1 Fe1 N2 N3 91.09(14) 2_755 . . . ? O1 Fe1 N2 N3 -0.52(13) . . . . ? O1 Fe1 N2 N3 -87.88(14) 2_755 . . . ? O1 C7 N3 N2 -1.3(3) . . . . ? C8 C7 N3 N2 178.01(16) . . . . ? C6 N2 N3 C7 179.74(18) . . . . ? Fe1 N2 N3 C7 1.1(2) . . . . ? N3 C7 O1 Fe1 0.9(2) . . . . ? C8 C7 O1 Fe1 -178.38(14) . . . . ? N2 Fe1 O1 C7 -0.17(13) . . . . ? N2 Fe1 O1 C7 -179.52(13) 2_755 . . . ? N1 Fe1 O1 C7 3.7(3) . . . . ? N1 Fe1 O1 C7 -97.51(13) 2_755 . . . ? O1 Fe1 O1 C7 100.98(13) 2_755 . . . ? 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 O2 H2A N3 0.82 1.94 2.754(2) 170.5 4_645 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.188 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.039 # Attachment '2 EtOH H2O.cif' data_EtOH _database_code_depnum_ccdc_archive 'CCDC 756167' #TrackingRef '2 EtOH H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 Fe N6 O6, C2 H6 O, Cl O4, H2O' _chemical_formula_sum 'C32 H36 Cl Fe N6 O12' _chemical_formula_weight 787.97 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' Fe Fe 0.3463 0.8444 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.716(3) _cell_length_b 23.544(5) _cell_length_c 12.907(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.41(3) _cell_angle_gamma 90.00 _cell_volume 3666.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 25332 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.373 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1628 _exptl_absorpt_coefficient_mu 0.553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 45225 _diffrn_reflns_av_R_equivalents 0.0893 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6408 _reflns_number_gt 3492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1004P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0004(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6408 _refine_ls_number_parameters 486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1679 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 Fe1 Fe 0.26123(4) 0.06015(2) 0.50219(4) 0.0455(2) Uani 1 1 d . . . C1 C 0.2420(4) 0.1885(2) 0.4366(4) 0.0623(12) Uani 1 1 d . . . H1 H 0.2018 0.1918 0.4853 0.075 Uiso 1 1 calc R . . C2 C 0.2597(4) 0.2361(2) 0.3845(4) 0.0736(14) Uani 1 1 d . . . H2 H 0.2322 0.2711 0.3974 0.088 Uiso 1 1 calc R . . C3 C 0.3185(4) 0.2316(2) 0.3131(4) 0.0725(14) Uani 1 1 d . . . H3 H 0.3311 0.2635 0.2760 0.087 Uiso 1 1 calc R . . C4 C 0.3594(3) 0.17884(19) 0.2963(4) 0.0581(12) Uani 1 1 d . . . H4 H 0.4007 0.1752 0.2487 0.070 Uiso 1 1 calc R . . C5 C 0.3388(3) 0.13249(18) 0.3500(3) 0.0446(10) Uani 1 1 d . . . C6 C 0.3756(3) 0.07441(17) 0.3394(3) 0.0405(10) Uani 1 1 d . . . C7 C 0.4681(4) 0.01685(19) 0.2334(4) 0.0617(12) Uani 1 1 d . . . H7A H 0.4070 -0.0093 0.2034 0.074 Uiso 1 1 calc R . . H7B H 0.5214 -0.0008 0.2960 0.074 Uiso 1 1 calc R . . C8 C 0.5205(5) 0.0320(2) 0.1504(4) 0.103(2) Uani 1 1 d . . . H8A H 0.4713 0.0559 0.0961 0.155 Uiso 1 1 calc R . . H8B H 0.5357 -0.0020 0.1165 0.155 Uiso 1 1 calc R . . H8C H 0.5885 0.0519 0.1845 0.155 Uiso 1 1 calc R . . C9 C 0.3440(3) -0.04634(17) 0.4720(3) 0.0440(10) Uani 1 1 d . . . C10 C 0.3610(3) -0.10806(17) 0.4877(3) 0.0421(10) Uani 1 1 d . . . C11 C 0.3986(4) -0.14075(19) 0.4177(4) 0.0600(12) Uani 1 1 d . . . H11 H 0.4137 -0.1234 0.3592 0.072 Uiso 1 1 calc R . . C12 C 0.4141(4) -0.1986(2) 0.4327(4) 0.0670(13) Uani 1 1 d . . . H12 H 0.4397 -0.2198 0.3848 0.080 Uiso 1 1 calc R . . C13 C 0.3914(4) -0.2250(2) 0.5200(4) 0.0609(12) Uani 1 1 d . . . C14 C 0.3536(4) -0.1920(2) 0.5894(4) 0.0632(12) Uani 1 1 d . . . H14 H 0.3381 -0.2089 0.6480 0.076 Uiso 1 1 calc R . . C15 C 0.3389(3) -0.13508(19) 0.5731(3) 0.0544(11) Uani 1 1 d . . . H15 H 0.3131 -0.1139 0.6209 0.065 Uiso 1 1 calc R . . C16 C 0.0802(4) 0.01860(19) 0.2850(3) 0.0598(12) Uani 1 1 d . . . H16 H 0.1403 0.0082 0.2628 0.072 Uiso 1 1 calc R . . C17 C -0.0246(4) 0.0083(2) 0.2153(4) 0.0658(13) Uani 1 1 d . . . H17 H -0.0353 -0.0080 0.1472 0.079 Uiso 1 1 calc R . . C18 C -0.1125(4) 0.0227(2) 0.2486(4) 0.0658(13) Uani 1 1 d . . . H18 H -0.1845 0.0164 0.2030 0.079 Uiso 1 1 calc R . . C19 C -0.0947(3) 0.04643(19) 0.3495(4) 0.0554(12) Uani 1 1 d . . . H19 H -0.1543 0.0551 0.3739 0.066 Uiso 1 1 calc R . . C20 C 0.0114(3) 0.05721(17) 0.4141(3) 0.0444(10) Uani 1 1 d . . . C21 C 0.0407(3) 0.08407(18) 0.5232(3) 0.0505(11) Uani 1 1 d . . . C22 C -0.0429(5) 0.1254(3) 0.6559(6) 0.108(2) Uani 1 1 d . . . H22A H -0.1100 0.1186 0.6745 0.130 Uiso 1 1 calc R . . H22B H 0.0207 0.1130 0.7157 0.130 Uiso 1 1 calc R . . C23 C -0.0340(6) 0.1792(4) 0.6318(7) 0.143(3) Uani 1 1 d . . . H23A H 0.0270 0.1836 0.6037 0.214 Uiso 1 1 calc R . . H23B H -0.0212 0.2019 0.6964 0.214 Uiso 1 1 calc R . . H23C H -0.1012 0.1913 0.5777 0.214 Uiso 1 1 calc R . . C24 C 0.2949(3) 0.11105(16) 0.7057(3) 0.0443(10) Uani 1 1 d . . . C25 C 0.3594(3) 0.13316(16) 0.8139(3) 0.0449(10) Uani 1 1 d . . . C26 C 0.3074(4) 0.15871(19) 0.8823(3) 0.0600(12) Uani 1 1 d . . . H26 H 0.2307 0.1625 0.8586 0.072 Uiso 1 1 calc R . . C27 C 0.3671(4) 0.1782(2) 0.9831(4) 0.0659(13) Uani 1 1 d . . . H27 H 0.3308 0.1948 1.0277 0.079 Uiso 1 1 calc R . . C28 C 0.4810(4) 0.1734(2) 1.0193(4) 0.0624(12) Uani 1 1 d . . . C29 C 0.5361(3) 0.14916(19) 0.9523(3) 0.0567(11) Uani 1 1 d . . . H29 H 0.6130 0.1462 0.9757 0.068 Uiso 1 1 calc R . . C30 C 0.4741(3) 0.12958(17) 0.8507(3) 0.0521(11) Uani 1 1 d . . . H30 H 0.5103 0.1135 0.8055 0.062 Uiso 1 1 calc R . . C31 C 0.9320(6) 0.2047(3) 0.2913(6) 0.140(3) Uani 1 1 d . . . H31A H 0.9178 0.1895 0.3546 0.210 Uiso 1 1 calc R . . H31B H 0.9759 0.2385 0.3110 0.210 Uiso 1 1 calc R . . H31C H 0.9713 0.1771 0.2630 0.210 Uiso 1 1 calc R . . C32 C 0.8316(6) 0.2177(3) 0.2118(6) 0.122(2) Uani 1 1 d . . . H32A H 0.7941 0.2463 0.2413 0.146 Uiso 1 1 calc R . . H32B H 0.8478 0.2345 0.1499 0.146 Uiso 1 1 calc R . . Cl1 Cl 0.81591(13) 0.08686(8) 0.93787(13) 0.0999(5) Uani 1 1 d . . . N1 N 0.2795(3) 0.13738(14) 0.4212(3) 0.0484(8) Uani 1 1 d . . . N2 N 0.3520(2) 0.03738(15) 0.4000(2) 0.0434(8) Uani 1 1 d . . . N3 N 0.3790(2) -0.02026(14) 0.3994(3) 0.0464(8) Uani 1 1 d . . . N4 N 0.1002(3) 0.04296(14) 0.3836(3) 0.0485(8) Uani 1 1 d . . . N5 N 0.1451(3) 0.09006(14) 0.5730(2) 0.0460(8) Uani 1 1 d . . . N6 N 0.1865(3) 0.11388(14) 0.6756(3) 0.0511(9) Uani 1 1 d . . . O1 O 0.2939(2) -0.01975(11) 0.5331(2) 0.0494(7) Uani 1 1 d . . . O2 O 0.4038(3) -0.28067(14) 0.5412(3) 0.0889(11) Uani 1 1 d . . . H2A H 0.4473 -0.2939 0.5124 0.133 Uiso 1 1 calc R . . O3 O 0.4279(2) 0.07069(11) 0.2649(2) 0.0570(8) Uani 1 1 d . . . O4 O 0.3491(2) 0.08920(12) 0.6446(2) 0.0530(7) Uani 1 1 d . . . O5 O 0.5376(3) 0.19178(18) 1.1220(2) 0.0872(11) Uani 1 1 d . . . H5 H 0.6041 0.1861 1.1345 0.131 Uiso 1 1 calc R . . O6 O -0.0471(2) 0.09705(16) 0.5519(3) 0.0827(11) Uani 1 1 d . . . O7 O 0.7597(3) 0.1731(2) 0.1744(4) 0.1304(18) Uani 1 1 d . . . H7 H 0.7914 0.1476 0.1528 0.196 Uiso 1 1 calc R . . O8 O 0.4104(4) 0.6378(2) 0.3955(4) 0.059(2) Uani 0.618(8) 1 d P A 1 O9 O 0.8534(4) 0.1225(2) 1.0281(4) 0.1368(18) Uani 1 1 d . . . O10 O 0.9003(4) 0.0561(3) 0.9266(5) 0.187(3) Uani 1 1 d . . . O11 O 0.7465(5) 0.0439(3) 0.9735(6) 0.207(3) Uani 1 1 d . . . O12 O 0.7432(5) 0.1145(3) 0.8502(4) 0.170(2) Uani 1 1 d . . . O8A O 0.3467(6) 0.5951(3) 0.4295(6) 0.054(3) Uani 0.382(8) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0456(4) 0.0484(4) 0.0467(4) -0.0040(3) 0.0207(3) 0.0034(3) C1 0.063(3) 0.054(3) 0.077(3) -0.005(3) 0.030(2) 0.009(2) C2 0.083(3) 0.046(3) 0.100(4) 0.001(3) 0.040(3) 0.004(3) C3 0.081(3) 0.051(3) 0.092(4) 0.005(3) 0.037(3) -0.004(3) C4 0.059(3) 0.053(3) 0.066(3) 0.002(2) 0.025(2) -0.005(2) C5 0.040(2) 0.048(3) 0.047(2) -0.007(2) 0.0165(19) -0.0030(19) C6 0.037(2) 0.045(3) 0.039(2) -0.0076(19) 0.0115(19) -0.0042(18) C7 0.071(3) 0.062(3) 0.061(3) -0.001(2) 0.035(2) 0.010(2) C8 0.160(6) 0.080(4) 0.107(5) 0.006(3) 0.097(5) 0.023(4) C9 0.037(2) 0.049(3) 0.044(2) -0.008(2) 0.0100(19) -0.0010(19) C10 0.042(2) 0.044(3) 0.042(2) -0.003(2) 0.0152(19) -0.0018(19) C11 0.078(3) 0.047(3) 0.065(3) 0.000(2) 0.036(3) -0.001(2) C12 0.089(3) 0.052(3) 0.068(3) -0.008(3) 0.035(3) 0.008(3) C13 0.067(3) 0.044(3) 0.074(3) 0.004(3) 0.025(3) -0.002(2) C14 0.080(3) 0.051(3) 0.068(3) 0.007(3) 0.038(3) -0.001(2) C15 0.059(3) 0.054(3) 0.057(3) -0.004(2) 0.028(2) 0.000(2) C16 0.058(3) 0.072(3) 0.053(3) -0.009(2) 0.023(2) 0.004(2) C17 0.062(3) 0.077(4) 0.057(3) -0.016(3) 0.016(3) -0.004(3) C18 0.050(3) 0.079(4) 0.063(3) -0.006(3) 0.009(2) -0.007(2) C19 0.048(3) 0.060(3) 0.061(3) -0.004(2) 0.022(2) -0.001(2) C20 0.039(2) 0.045(3) 0.052(3) -0.002(2) 0.019(2) 0.0025(19) C21 0.045(3) 0.050(3) 0.061(3) -0.006(2) 0.023(2) 0.004(2) C22 0.069(4) 0.116(6) 0.146(6) -0.033(5) 0.042(4) 0.002(4) C23 0.108(5) 0.156(8) 0.164(7) 0.007(7) 0.043(5) 0.023(6) C24 0.049(3) 0.037(2) 0.048(3) -0.004(2) 0.017(2) -0.0026(19) C25 0.051(3) 0.038(2) 0.049(3) -0.002(2) 0.021(2) 0.0017(19) C26 0.053(3) 0.074(3) 0.054(3) -0.007(2) 0.018(2) 0.002(2) C27 0.058(3) 0.088(4) 0.053(3) -0.019(3) 0.020(2) 0.004(3) C28 0.070(3) 0.073(3) 0.045(3) -0.010(2) 0.018(2) -0.002(3) C29 0.051(2) 0.065(3) 0.053(3) -0.005(2) 0.014(2) 0.000(2) C30 0.057(3) 0.052(3) 0.052(3) -0.003(2) 0.025(2) 0.004(2) C31 0.124(6) 0.114(6) 0.149(7) -0.015(5) -0.004(5) 0.019(5) C32 0.097(5) 0.120(6) 0.133(6) -0.048(5) 0.015(5) 0.000(5) Cl1 0.0870(10) 0.1084(14) 0.0880(11) -0.0274(10) 0.0042(9) 0.0327(10) N1 0.0491(19) 0.045(2) 0.052(2) -0.0071(17) 0.0172(17) -0.0016(17) N2 0.0428(18) 0.044(2) 0.047(2) 0.0007(17) 0.0189(16) -0.0014(16) N3 0.054(2) 0.042(2) 0.051(2) 0.0021(17) 0.0272(17) 0.0028(16) N4 0.050(2) 0.049(2) 0.049(2) -0.0037(17) 0.0193(17) 0.0003(16) N5 0.044(2) 0.051(2) 0.043(2) -0.0055(17) 0.0137(16) 0.0023(16) N6 0.046(2) 0.060(2) 0.049(2) -0.0143(18) 0.0158(16) -0.0013(17) O1 0.0535(16) 0.0499(18) 0.0541(17) 0.0025(14) 0.0304(14) 0.0086(13) O2 0.110(3) 0.044(2) 0.131(3) 0.007(2) 0.066(2) 0.0046(19) O3 0.0678(18) 0.051(2) 0.0654(19) -0.0003(15) 0.0396(16) 0.0045(14) O4 0.0460(15) 0.067(2) 0.0481(16) -0.0118(15) 0.0181(13) 0.0089(14) O5 0.070(2) 0.133(3) 0.053(2) -0.029(2) 0.0117(17) 0.000(2) O6 0.0472(18) 0.125(3) 0.081(2) -0.048(2) 0.0283(16) -0.0025(18) O7 0.073(2) 0.179(5) 0.124(4) -0.088(3) 0.010(2) -0.003(3) O8 0.065(3) 0.052(4) 0.060(3) 0.009(2) 0.021(2) 0.031(3) O9 0.130(4) 0.158(5) 0.112(3) -0.062(3) 0.025(3) 0.018(3) O10 0.137(4) 0.214(6) 0.205(6) -0.089(4) 0.046(4) 0.080(4) O11 0.179(6) 0.173(6) 0.238(7) 0.029(5) 0.020(5) -0.040(5) O12 0.171(5) 0.216(6) 0.085(3) 0.018(3) -0.012(3) 0.053(4) O8A 0.054(5) 0.038(5) 0.063(5) 0.006(4) 0.006(4) 0.012(4) _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 1.941(3) . ? Fe1 O4 1.948(3) . ? Fe1 N2 2.079(3) . ? Fe1 N5 2.089(3) . ? Fe1 N1 2.146(3) . ? Fe1 N4 2.173(3) . ? C1 N1 1.331(5) . ? C1 C2 1.364(6) . ? C1 H1 0.9300 . ? C2 C3 1.361(6) . ? C2 H2 0.9300 . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 C5 1.362(5) . ? C4 H4 0.9300 . ? C5 N1 1.365(4) . ? C5 C6 1.466(5) . ? C6 N2 1.269(5) . ? C6 O3 1.334(4) . ? C7 O3 1.471(5) . ? C7 C8 1.473(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N3 1.310(5) . ? C9 O1 1.318(4) . ? C9 C10 1.474(5) . ? C10 C15 1.376(5) . ? C10 C11 1.381(5) . ? C11 C12 1.381(6) . ? C11 H11 0.9300 . ? C12 C13 1.395(6) . ? C12 H12 0.9300 . ? C13 O2 1.339(5) . ? C13 C14 1.381(6) . ? C14 C15 1.360(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N4 1.345(5) . ? C16 C17 1.373(6) . ? C16 H16 0.9300 . ? C17 C18 1.361(5) . ? C17 H17 0.9300 . ? C18 C19 1.369(6) . ? C18 H18 0.9300 . ? C19 C20 1.368(5) . ? C19 H19 0.9300 . ? C20 N4 1.350(4) . ? C20 C21 1.480(5) . ? C21 N5 1.287(5) . ? C21 O6 1.318(4) . ? C22 C23 1.317(8) . ? C22 O6 1.486(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O4 1.306(4) . ? C24 N6 1.311(5) . ? C24 C25 1.473(5) . ? C25 C30 1.387(5) . ? C25 C26 1.394(5) . ? C26 C27 1.362(6) . ? C26 H26 0.9300 . ? C27 C28 1.380(6) . ? C27 H27 0.9300 . ? C28 O5 1.363(5) . ? C28 C29 1.396(5) . ? C29 C30 1.379(5) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.396(8) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 O7 1.375(7) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? Cl1 O10 1.340(4) . ? Cl1 O12 1.377(5) . ? Cl1 O9 1.392(4) . ? Cl1 O11 1.506(7) . ? N2 N3 1.400(4) . ? N5 N6 1.381(4) . ? O2 H2A 0.8200 . ? O5 H5 0.8200 . ? O7 H7 0.8200 . ? 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 O4 97.16(12) . . ? O1 Fe1 N2 75.77(12) . . ? O4 Fe1 N2 114.90(11) . . ? O1 Fe1 N5 111.86(11) . . ? O4 Fe1 N5 75.12(11) . . ? N2 Fe1 N5 167.26(13) . . ? O1 Fe1 N1 150.71(11) . . ? O4 Fe1 N1 92.52(12) . . ? N2 Fe1 N1 75.07(13) . . ? N5 Fe1 N1 97.32(12) . . ? O1 Fe1 N4 93.29(12) . . ? O4 Fe1 N4 149.55(11) . . ? N2 Fe1 N4 95.37(12) . . ? N5 Fe1 N4 74.44(12) . . ? N1 Fe1 N4 92.15(12) . . ? N1 C1 C2 123.1(4) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.2(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 N1 120.7(4) . . ? C4 C5 C6 125.5(3) . . ? N1 C5 C6 113.7(3) . . ? N2 C6 O3 131.9(4) . . ? N2 C6 C5 116.0(3) . . ? O3 C6 C5 112.1(3) . . ? O3 C7 C8 105.6(4) . . ? O3 C7 H7A 110.6 . . ? C8 C7 H7A 110.6 . . ? O3 C7 H7B 110.6 . . ? C8 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 O1 122.9(4) . . ? N3 C9 C10 119.5(3) . . ? O1 C9 C10 117.6(3) . . ? C15 C10 C11 117.8(4) . . ? C15 C10 C9 120.5(3) . . ? C11 C10 C9 121.7(3) . . ? C12 C11 C10 121.5(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 119.7(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? O2 C13 C14 117.5(4) . . ? O2 C13 C12 124.1(4) . . ? C14 C13 C12 118.5(4) . . ? C15 C14 C13 120.9(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C10 121.7(4) . . ? C14 C15 H15 119.1 . . ? C10 C15 H15 119.1 . . ? N4 C16 C17 123.3(4) . . ? N4 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 118.3(4) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C17 C18 C19 119.8(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 119.4(4) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? N4 C20 C19 122.1(4) . . ? N4 C20 C21 113.7(3) . . ? C19 C20 C21 124.3(3) . . ? N5 C21 O6 131.8(4) . . ? N5 C21 C20 115.6(3) . . ? O6 C21 C20 112.6(3) . . ? C23 C22 O6 101.5(7) . . ? C23 C22 H22A 111.5 . . ? O6 C22 H22A 111.5 . . ? C23 C22 H22B 111.5 . . ? O6 C22 H22B 111.5 . . ? H22A C22 H22B 109.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O4 C24 N6 123.2(3) . . ? O4 C24 C25 118.1(3) . . ? N6 C24 C25 118.7(3) . . ? C30 C25 C26 117.9(4) . . ? C30 C25 C24 120.8(3) . . ? C26 C25 C24 121.3(4) . . ? C27 C26 C25 121.1(4) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 120.4(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? O5 C28 C27 118.6(4) . . ? O5 C28 C29 121.2(4) . . ? C27 C28 C29 120.1(4) . . ? C30 C29 C28 118.6(4) . . ? C30 C29 H29 120.7 . . ? C28 C29 H29 120.7 . . ? C29 C30 C25 121.9(4) . . ? C29 C30 H30 119.0 . . ? C25 C30 H30 119.0 . . ? C32 C31 H31A 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C32 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O7 C32 C31 116.3(7) . . ? O7 C32 H32A 108.2 . . ? C31 C32 H32A 108.2 . . ? O7 C32 H32B 108.2 . . ? C31 C32 H32B 108.2 . . ? H32A C32 H32B 107.4 . . ? O10 Cl1 O12 121.2(4) . . ? O10 Cl1 O9 110.0(3) . . ? O12 Cl1 O9 111.5(3) . . ? O10 Cl1 O11 103.7(5) . . ? O12 Cl1 O11 105.2(4) . . ? O9 Cl1 O11 103.2(4) . . ? C1 N1 C5 118.5(4) . . ? C1 N1 Fe1 126.4(3) . . ? C5 N1 Fe1 115.1(3) . . ? C6 N2 N3 123.8(3) . . ? C6 N2 Fe1 120.1(3) . . ? N3 N2 Fe1 116.1(2) . . ? C9 N3 N2 108.1(3) . . ? C16 N4 C20 117.1(3) . . ? C16 N4 Fe1 126.9(3) . . ? C20 N4 Fe1 115.9(2) . . ? C21 N5 N6 123.0(3) . . ? C21 N5 Fe1 120.3(3) . . ? N6 N5 Fe1 116.6(2) . . ? C24 N6 N5 108.1(3) . . ? C9 O1 Fe1 116.8(2) . . ? C13 O2 H2A 109.5 . . ? C6 O3 C7 123.5(3) . . ? C24 O4 Fe1 117.0(2) . . ? C28 O5 H5 109.5 . . ? C21 O6 C22 124.5(4) . . ? C32 O7 H7 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.575 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.068 # Attachment '1.cif' data_last _database_code_depnum_ccdc_archive 'CCDC 765793' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Fe N6 O4' _chemical_formula_sum 'C26 H20 Fe N6 O4' _chemical_formula_weight 536.33 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 Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 22.801(5) _cell_length_b 9.917(2) _cell_length_c 11.686(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.47(3) _cell_angle_gamma 90.00 _cell_volume 2533.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 61490 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21599 _diffrn_reflns_av_R_equivalents 0.0873 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2474 _reflns_number_gt 1674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0523P)^2^+0.6294P] 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 constru _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0005(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2474 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Fe1 Fe 0.0000 0.02100(5) 0.7500 0.0473(2) Uani 1 2 d S . . C1 C -0.08670(12) -0.2173(3) 0.6085(3) 0.0611(7) Uani 1 1 d . . . H1 H -0.1142 -0.1901 0.6494 0.073 Uiso 1 1 calc R . . C2 C -0.10069(13) -0.3287(3) 0.5358(3) 0.0695(8) Uani 1 1 d . . . H2 H -0.1362 -0.3774 0.5303 0.083 Uiso 1 1 calc R . . C3 C -0.06188(14) -0.3671(3) 0.4717(3) 0.0689(8) Uani 1 1 d . . . H3 H -0.0711 -0.4409 0.4206 0.083 Uiso 1 1 calc R . . C4 C -0.00901(12) -0.2952(3) 0.4838(2) 0.0588(7) Uani 1 1 d . . . H4 H 0.0181 -0.3194 0.4410 0.071 Uiso 1 1 calc R . . C5 C 0.00319(11) -0.1862(2) 0.5608(2) 0.0491(6) Uani 1 1 d . . . C6 C 0.05903(11) -0.1054(2) 0.5811(2) 0.0491(6) Uani 1 1 d . . . H6 H 0.0878 -0.1217 0.5401 0.059 Uiso 1 1 calc R . . C7 C 0.11388(10) 0.1570(2) 0.7695(2) 0.0446(6) Uani 1 1 d . . . C8 C 0.16475(10) 0.2549(2) 0.8131(2) 0.0453(6) Uani 1 1 d . . . C9 C 0.20825(11) 0.2794(3) 0.7527(2) 0.0526(6) Uani 1 1 d . . . H9 H 0.2057 0.2338 0.6819 0.063 Uiso 1 1 calc R . . C10 C 0.25524(11) 0.3706(3) 0.7964(2) 0.0548(7) Uani 1 1 d . . . H10 H 0.2835 0.3873 0.7543 0.066 Uiso 1 1 calc R . . C11 C 0.26015(10) 0.4370(2) 0.9033(2) 0.0470(6) Uani 1 1 d . . . C12 C 0.21753(10) 0.4130(2) 0.9649(2) 0.0482(6) Uani 1 1 d . . . H12 H 0.2208 0.4564 1.0370 0.058 Uiso 1 1 calc R . . C13 C 0.17004(10) 0.3241(2) 0.9184(2) 0.0479(6) Uani 1 1 d . . . H13 H 0.1409 0.3105 0.9590 0.057 Uiso 1 1 calc R . . N1 N -0.03538(9) -0.14645(19) 0.62304(18) 0.0500(5) Uani 1 1 d . . . N2 N 0.06579(8) -0.01127(19) 0.65823(18) 0.0437(5) Uani 1 1 d . . . N3 N 0.11719(8) 0.0699(2) 0.68424(18) 0.0466(5) Uani 1 1 d . . . O1 O 0.06939(7) 0.16054(17) 0.81638(15) 0.0513(4) Uani 1 1 d . . . O2 O 0.30609(8) 0.52467(18) 0.95277(16) 0.0564(5) Uani 1 1 d . . . H2A H 0.3257 0.5401 0.9052 0.085 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 0.0308(3) 0.0525(3) 0.0631(4) 0.000 0.0207(2) 0.000 C1 0.0416(16) 0.0711(19) 0.0715(19) 0.0032(15) 0.0172(13) -0.0105(13) C2 0.0531(17) 0.0705(19) 0.082(2) -0.0003(17) 0.0137(16) -0.0226(15) C3 0.069(2) 0.0536(17) 0.079(2) -0.0074(15) 0.0116(17) -0.0114(15) C4 0.0548(17) 0.0526(16) 0.0698(18) -0.0066(14) 0.0191(14) 0.0020(13) C5 0.0427(15) 0.0476(14) 0.0560(15) 0.0027(13) 0.0124(12) 0.0015(11) C6 0.0382(14) 0.0511(15) 0.0628(17) 0.0020(13) 0.0220(12) 0.0041(11) C7 0.0299(13) 0.0486(14) 0.0565(15) 0.0058(12) 0.0145(11) 0.0021(10) C8 0.0319(13) 0.0484(13) 0.0573(15) 0.0054(12) 0.0152(11) 0.0018(10) C9 0.0429(14) 0.0632(16) 0.0555(15) -0.0052(13) 0.0201(12) -0.0079(12) C10 0.0426(15) 0.0685(17) 0.0603(17) -0.0012(14) 0.0257(13) -0.0104(13) C11 0.0344(14) 0.0486(14) 0.0595(16) 0.0026(12) 0.0157(12) -0.0006(11) C12 0.0393(14) 0.0504(14) 0.0571(15) -0.0032(12) 0.0171(12) 0.0011(11) C13 0.0360(14) 0.0512(15) 0.0618(17) 0.0010(12) 0.0224(12) -0.0001(11) N1 0.0354(11) 0.0533(12) 0.0622(14) 0.0020(10) 0.0153(10) -0.0029(9) N2 0.0313(10) 0.0454(11) 0.0567(12) 0.0007(10) 0.0162(9) -0.0001(9) N3 0.0308(11) 0.0518(12) 0.0610(13) -0.0031(10) 0.0194(9) -0.0019(9) O1 0.0342(9) 0.0592(11) 0.0667(11) -0.0059(8) 0.0242(8) -0.0049(8) O2 0.0406(10) 0.0639(11) 0.0685(12) -0.0072(10) 0.0219(8) -0.0134(9) _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 2.0793(17) . ? Fe1 O1 2.0793(16) 2_556 ? Fe1 N2 2.101(2) 2_556 ? Fe1 N2 2.101(2) . ? Fe1 N1 2.221(2) . ? Fe1 N1 2.221(2) 2_556 ? C1 N1 1.334(3) . ? C1 C2 1.375(4) . ? C1 H1 0.9300 . ? C2 C3 1.366(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 N1 1.349(3) . ? C5 C6 1.466(3) . ? C6 N2 1.276(3) . ? C6 H6 0.9300 . ? C7 O1 1.283(3) . ? C7 N3 1.337(3) . ? C7 C8 1.488(3) . ? C8 C13 1.385(3) . ? C8 C9 1.392(3) . ? C9 C10 1.384(3) . ? C9 H9 0.9300 . ? C10 C11 1.388(3) . ? C10 H10 0.9300 . ? C11 O2 1.358(3) . ? C11 C12 1.384(3) . ? C12 C13 1.382(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N2 N3 1.383(3) . ? O2 H2A 0.8200 . ? 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 O1 96.56(10) . 2_556 ? O1 Fe1 N2 119.26(7) . 2_556 ? O1 Fe1 N2 73.38(7) 2_556 2_556 ? O1 Fe1 N2 73.38(7) . . ? O1 Fe1 N2 119.26(7) 2_556 . ? N2 Fe1 N2 162.48(11) 2_556 . ? O1 Fe1 N1 147.22(7) . . ? O1 Fe1 N1 98.89(7) 2_556 . ? N2 Fe1 N1 92.89(8) 2_556 . ? N2 Fe1 N1 73.85(7) . . ? O1 Fe1 N1 98.89(7) . 2_556 ? O1 Fe1 N1 147.22(7) 2_556 2_556 ? N2 Fe1 N1 73.85(7) 2_556 2_556 ? N2 Fe1 N1 92.89(7) . 2_556 ? N1 Fe1 N1 83.20(10) . 2_556 ? N1 C1 C2 122.9(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.0(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.5(2) . . ? N1 C5 C6 115.0(2) . . ? C4 C5 C6 122.5(2) . . ? N2 C6 C5 116.0(2) . . ? N2 C6 H6 122.0 . . ? C5 C6 H6 122.0 . . ? O1 C7 N3 123.7(2) . . ? O1 C7 C8 118.0(2) . . ? N3 C7 C8 118.3(2) . . ? C13 C8 C9 118.0(2) . . ? C13 C8 C7 119.4(2) . . ? C9 C8 C7 122.6(2) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? O2 C11 C12 117.3(2) . . ? O2 C11 C10 122.9(2) . . ? C12 C11 C10 119.8(2) . . ? C13 C12 C11 119.5(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 121.7(2) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? C1 N1 C5 117.4(2) . . ? C1 N1 Fe1 128.19(18) . . ? C5 N1 Fe1 114.19(15) . . ? C6 N2 N3 120.4(2) . . ? C6 N2 Fe1 120.76(16) . . ? N3 N2 Fe1 118.85(15) . . ? C7 N3 N2 108.45(19) . . ? C7 O1 Fe1 115.62(15) . . ? C11 O2 H2A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.222 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.057