# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1a _database_code_depnum_ccdc_archive 'CCDC 884404' #TrackingRef '11589_web_deposit_cif_file_0_IvanNemec_1338292662.[Fe(4OH-saltet)]X.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-Bis(4-hydroxysalicylaldiminato)-3,6-diazaoctane) -iron(iii) chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 Fe N4 O4, Cl' _chemical_formula_sum 'C20 H24 Cl Fe N4 O4' _chemical_formula_weight 475.73 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' Fe Fe 0.3463 0.8444 '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' 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' 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.660(9) _cell_length_b 9.651(9) _cell_length_c 13.590(12) _cell_angle_alpha 90.00 _cell_angle_beta 128.17(5) _cell_angle_gamma 90.00 _cell_volume 996.1(16) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 494 _exptl_absorpt_coefficient_mu 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details ;CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm ; _exptl_special_details ; face-indexed (CrysAlis RED; Oxford Diffraction, 2006) ; _diffrn_ambient_temperature 298(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 'Goniometer KM4/Xcalibur detector: Sapphire2 (large Be window)' _diffrn_measurement_method ; Rotation method data acquisition using omega and phi scans ; _diffrn_detector_area_resol_mean 8.4012 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5705 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1763 _reflns_number_gt 1254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material ' enCIFer (Allen et al., 2004)' _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^)+(0.0336P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1763 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0657 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 C1 C 0.7374(3) 0.5008(2) 0.37866(19) 0.0232(5) Uani 1 1 d . . . C2 C 0.8271(3) 0.6123(2) 0.3767(2) 0.0251(5) Uani 1 1 d . . . H2 H 0.8361 0.6188 0.3126 0.030 Uiso 1 1 calc R . . C3 C 0.9029(3) 0.7132(2) 0.46793(19) 0.0257(5) Uani 1 1 d . . . C4 C 0.8886(3) 0.7075(3) 0.5642(2) 0.0329(6) Uani 1 1 d . . . H4 H 0.9347 0.7778 0.6235 0.039 Uiso 1 1 calc R . . C5 C 0.8058(3) 0.5969(3) 0.5692(2) 0.0342(6) Uani 1 1 d . . . H5 H 0.8013 0.5907 0.6354 0.041 Uiso 1 1 calc R . . C6 C 0.7268(3) 0.4917(2) 0.4782(2) 0.0252(5) Uani 1 1 d . . . C7 C 0.6509(3) 0.3762(3) 0.4944(2) 0.0290(6) Uani 1 1 d . . . H7 H 0.6617 0.3731 0.5673 0.035 Uiso 1 1 calc R . . C8 C 0.4956(3) 0.1635(2) 0.4438(2) 0.0352(6) Uani 1 1 d . . . H8A H 0.4805 0.1931 0.5048 0.042 Uiso 1 1 calc R . . H8B H 0.5731 0.0836 0.4768 0.042 Uiso 1 1 calc R . . C9 C 0.3186(3) 0.1279(2) 0.3200(2) 0.0348(6) Uani 1 1 d . . . H9A H 0.2769 0.0399 0.3271 0.042 Uiso 1 1 calc R . . H9B H 0.2328 0.1986 0.2989 0.042 Uiso 1 1 calc R . . C10 C 0.4004(3) -0.0170(2) 0.2108(2) 0.0399(7) Uani 1 1 d . . . H10A H 0.3478 -0.0354 0.1240 0.048 Uiso 1 1 calc R . . H10B H 0.3638 -0.0895 0.2397 0.048 Uiso 1 1 calc R . . Fe1 Fe 0.5000 0.27462(5) 0.2500 0.02423(16) Uani 1 2 d S . . Cl1 Cl 1.0000 0.84842(10) 0.2500 0.0500(3) Uani 1 2 d S . . N1 N 0.5686(2) 0.27579(19) 0.41625(15) 0.0246(4) Uani 1 1 d . . . N2 N 0.3395(2) 0.11958(18) 0.22120(16) 0.0282(5) Uani 1 1 d . . . H1N2 H 0.2321 0.1362 0.1468 0.034 Uiso 1 1 calc R . . O1 O 0.67018(18) 0.40664(15) 0.28949(13) 0.0277(4) Uani 1 1 d . . . O2 O 0.9936(2) 0.82292(16) 0.47023(14) 0.0354(4) Uani 1 1 d . . . H2A H 0.9885 0.8211 0.4077 0.053 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 C1 0.0200(12) 0.0222(12) 0.0224(13) 0.0008(11) 0.0106(11) 0.0024(11) C2 0.0274(13) 0.0265(13) 0.0240(12) 0.0008(11) 0.0171(11) 0.0005(11) C3 0.0213(11) 0.0238(13) 0.0282(13) -0.0017(12) 0.0134(10) -0.0026(11) C4 0.0346(13) 0.0354(15) 0.0292(13) -0.0143(12) 0.0200(12) -0.0112(13) C5 0.0360(15) 0.0410(16) 0.0306(14) -0.0071(12) 0.0230(13) -0.0071(13) C6 0.0271(13) 0.0238(13) 0.0233(13) -0.0006(11) 0.0149(11) -0.0009(11) C7 0.0292(13) 0.0349(15) 0.0230(13) 0.0044(12) 0.0163(11) 0.0029(12) C8 0.0402(15) 0.0321(14) 0.0321(14) 0.0066(12) 0.0217(13) -0.0046(13) C9 0.0344(14) 0.0331(15) 0.0370(15) 0.0033(12) 0.0221(13) -0.0061(12) C10 0.0386(13) 0.0231(14) 0.0504(17) -0.0036(12) 0.0237(13) -0.0047(12) Fe1 0.0253(3) 0.0204(3) 0.0236(3) 0.000 0.0135(2) 0.000 Cl1 0.0592(6) 0.0542(7) 0.0492(6) 0.000 0.0399(5) 0.000 N1 0.0249(10) 0.0207(10) 0.0232(10) 0.0044(9) 0.0124(9) -0.0004(9) N2 0.0230(11) 0.0262(12) 0.0252(11) 0.0024(9) 0.0098(9) 0.0015(9) O1 0.0328(9) 0.0250(9) 0.0276(9) -0.0074(7) 0.0198(8) -0.0073(8) O2 0.0394(10) 0.0343(10) 0.0333(10) -0.0087(8) 0.0228(9) -0.0141(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 C1 O1 1.320(3) . ? C1 C2 1.392(3) . ? C1 C6 1.421(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 O2 1.362(3) . ? C3 C4 1.398(3) . ? C4 C5 1.360(3) . ? C4 H4 0.9300 . ? C5 C6 1.406(3) . ? C5 H5 0.9300 . ? C6 C7 1.424(3) . ? C7 N1 1.287(3) . ? C7 H7 0.9300 . ? C8 N1 1.462(3) . ? C8 C9 1.521(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.479(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.485(3) . ? C10 C10 1.518(5) 2_655 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Fe1 O1 1.877(2) . ? Fe1 O1 1.877(2) 2_655 ? Fe1 N1 1.922(3) 2_655 ? Fe1 N1 1.922(3) . ? Fe1 N2 2.011(2) . ? Fe1 N2 2.011(2) 2_655 ? N2 H1N2 0.9100 . ? 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 C1 C2 118.3(2) . . ? O1 C1 C6 123.2(2) . . ? C2 C1 C6 118.6(2) . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? O2 C3 C2 123.1(2) . . ? O2 C3 C4 116.3(2) . . ? C2 C3 C4 120.6(2) . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 122.6(2) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 118.7(2) . . ? C1 C6 C7 122.9(2) . . ? N1 C7 C6 125.2(2) . . ? N1 C7 H7 117.4 . . ? C6 C7 H7 117.4 . . ? N1 C8 C9 105.93(19) . . ? N1 C8 H8A 110.6 . . ? C9 C8 H8A 110.6 . . ? N1 C8 H8B 110.6 . . ? C9 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? N2 C9 C8 109.0(2) . . ? N2 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? N2 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C10 109.76(14) . 2_655 ? N2 C10 H10A 109.7 . . ? C10 C10 H10A 109.7 2_655 . ? N2 C10 H10B 109.7 . . ? C10 C10 H10B 109.7 2_655 . ? H10A C10 H10B 108.2 . . ? O1 Fe1 O1 94.50(12) . 2_655 ? O1 Fe1 N1 86.38(8) . 2_655 ? O1 Fe1 N1 93.16(8) 2_655 2_655 ? O1 Fe1 N1 93.16(8) . . ? O1 Fe1 N1 86.38(8) 2_655 . ? N1 Fe1 N1 179.32(11) 2_655 . ? O1 Fe1 N2 173.78(7) . . ? O1 Fe1 N2 90.91(11) 2_655 . ? N1 Fe1 N2 96.39(8) 2_655 . ? N1 Fe1 N2 84.11(8) . . ? O1 Fe1 N2 90.91(11) . 2_655 ? O1 Fe1 N2 173.78(7) 2_655 2_655 ? N1 Fe1 N2 84.11(8) 2_655 2_655 ? N1 Fe1 N2 96.39(8) . 2_655 ? N2 Fe1 N2 83.86(13) . 2_655 ? C7 N1 C8 119.8(2) . . ? C7 N1 Fe1 124.27(16) . . ? C8 N1 Fe1 115.21(15) . . ? C9 N2 C10 114.77(18) . . ? C9 N2 Fe1 107.71(14) . . ? C10 N2 Fe1 112.09(16) . . ? C9 N2 H1N2 107.3 . . ? C10 N2 H1N2 107.3 . . ? Fe1 N2 H1N2 107.3 . . ? C1 O1 Fe1 125.23(14) . . ? C3 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.00(18) . . . . ? C6 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 O2 179.18(19) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? O2 C3 C4 C5 -177.3(2) . . . . ? C2 C3 C4 C5 3.1(3) . . . . ? C3 C4 C5 C6 -3.1(4) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C4 C5 C6 C7 176.8(2) . . . . ? O1 C1 C6 C5 178.94(19) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? O1 C1 C6 C7 3.5(3) . . . . ? C2 C1 C6 C7 -174.65(19) . . . . ? C5 C6 C7 N1 177.1(2) . . . . ? C1 C6 C7 N1 -7.5(4) . . . . ? N1 C8 C9 N2 45.3(2) . . . . ? C6 C7 N1 C8 -179.6(2) . . . . ? C6 C7 N1 Fe1 -9.9(3) . . . . ? C9 C8 N1 C7 140.6(2) . . . . ? C9 C8 N1 Fe1 -30.1(2) . . . . ? O1 Fe1 N1 C7 22.29(18) . . . . ? O1 Fe1 N1 C7 -72.03(19) 2_655 . . . ? N1 Fe1 N1 C7 -24.86(19) 2_655 . . . ? N2 Fe1 N1 C7 -163.32(18) . . . . ? N2 Fe1 N1 C7 113.56(19) 2_655 . . . ? O1 Fe1 N1 C8 -167.54(15) . . . . ? O1 Fe1 N1 C8 98.15(18) 2_655 . . . ? N1 Fe1 N1 C8 145.32(15) 2_655 . . . ? N2 Fe1 N1 C8 6.86(15) . . . . ? N2 Fe1 N1 C8 -76.26(18) 2_655 . . . ? C8 C9 N2 C10 85.2(2) . . . . ? C8 C9 N2 Fe1 -40.4(2) . . . . ? C10 C10 N2 C9 -93.1(3) 2_655 . . . ? C10 C10 N2 Fe1 30.2(3) 2_655 . . . ? O1 Fe1 N2 C9 83.3(7) . . . . ? O1 Fe1 N2 C9 -67.19(14) 2_655 . . . ? N1 Fe1 N2 C9 -160.47(14) 2_655 . . . ? N1 Fe1 N2 C9 19.07(14) . . . . ? N2 Fe1 N2 C9 116.18(16) 2_655 . . . ? O1 Fe1 N2 C10 -43.8(7) . . . . ? O1 Fe1 N2 C10 165.64(15) 2_655 . . . ? N1 Fe1 N2 C10 72.35(16) 2_655 . . . ? N1 Fe1 N2 C10 -108.10(16) . . . . ? N2 Fe1 N2 C10 -11.00(11) 2_655 . . . ? C2 C1 O1 Fe1 -164.00(14) . . . . ? C6 C1 O1 Fe1 17.8(3) . . . . ? O1 Fe1 O1 C1 60.35(15) 2_655 . . . ? N1 Fe1 O1 C1 153.24(17) 2_655 . . . ? N1 Fe1 O1 C1 -26.26(17) . . . . ? N2 Fe1 O1 C1 -90.1(7) . . . . ? N2 Fe1 O1 C1 -122.72(17) 2_655 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.055 data_1b _database_code_depnum_ccdc_archive 'CCDC 884405' #TrackingRef '11589_web_deposit_cif_file_0_IvanNemec_1338292662.[Fe(4OH-saltet)]X.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-Bis(4-hydroxysalicylaldiminato)-3,6-diazaoctane) -iron(iii) chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 Fe1 N4 O4, Br' _chemical_formula_sum 'C20 H24 Br Fe N4 O4' _chemical_formula_weight 519.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.9131(4) _cell_length_b 9.6378(4) _cell_length_c 13.7350(7) _cell_angle_alpha 90.00 _cell_angle_beta 129.198(3) _cell_angle_gamma 90.00 _cell_volume 1016.95(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 2.742 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.494 _exptl_absorpt_correction_T_max 0.566 _exptl_absorpt_process_details ;CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET) (compiled Apr 18 2008,18:17:43) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm ; _exptl_special_details ; face-indexed (CrysAlis RED; Oxford Diffraction, 2006) ; _diffrn_ambient_temperature 298(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 'Goniometer KM4/Xcalibur detector: Sapphire2 (large Be window)' _diffrn_measurement_method ; Rotation method data acquisition using omega and phi scans ; _diffrn_detector_area_resol_mean 8.4012 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6595 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1800 _reflns_number_gt 1430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material ' enCIFer (Allen et al., 2004)' _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^)+(0.0496P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1800 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C 0.7364(3) 0.5019(3) 0.3819(2) 0.0293(6) Uani 1 1 d . . . C2 C 0.8253(3) 0.6135(3) 0.3802(2) 0.0314(6) Uani 1 1 d . . . H2 H 0.8332 0.6203 0.3164 0.038 Uiso 1 1 calc R . . C3 C 0.9016(3) 0.7141(3) 0.4735(2) 0.0345(6) Uani 1 1 d . . . C4 C 0.8879(4) 0.7076(3) 0.5685(2) 0.0419(7) Uani 1 1 d . . . H4 H 0.9344 0.7777 0.6283 0.050 Uiso 1 1 calc R . . C5 C 0.8057(4) 0.5976(3) 0.5725(2) 0.0421(7) Uani 1 1 d . . . H5 H 0.8011 0.5915 0.6379 0.050 Uiso 1 1 calc R . . C6 C 0.7272(3) 0.4924(3) 0.4804(2) 0.0323(6) Uani 1 1 d . . . C7 C 0.6511(3) 0.3773(3) 0.4948(2) 0.0365(7) Uani 1 1 d . . . H7 H 0.6617 0.3742 0.5671 0.044 Uiso 1 1 calc R . . C8 C 0.4968(4) 0.1654(3) 0.4422(3) 0.0479(8) Uani 1 1 d . . . H8A H 0.4823 0.1953 0.5026 0.057 Uiso 1 1 calc R . . H8B H 0.5732 0.0853 0.4761 0.057 Uiso 1 1 calc R . . C9 C 0.3224(4) 0.1299(3) 0.3181(3) 0.0490(8) Uani 1 1 d . . . H9A H 0.2815 0.0418 0.3247 0.059 Uiso 1 1 calc R . . H9B H 0.2377 0.2007 0.2961 0.059 Uiso 1 1 calc R . . C10 C 0.4020(4) -0.0147(3) 0.2099(3) 0.0574(9) Uani 1 1 d . . . H10A H 0.3660 -0.0880 0.2375 0.069 Uiso 1 1 calc R . . H10B H 0.3498 -0.0321 0.1230 0.069 Uiso 1 1 calc R . . Fe1 Fe 0.5000 0.27697(5) 0.2500 0.02992(17) Uani 1 2 d S . . Br1 Br 1.0000 0.85379(5) 0.2500 0.05369(18) Uani 1 2 d S . . N1 N 0.5691(3) 0.2776(2) 0.41614(19) 0.0331(5) Uani 1 1 d . . . N2 N 0.3415(3) 0.1216(2) 0.2202(2) 0.0387(6) Uani 1 1 d . . . H1N2 H 0.2349 0.1382 0.1452 0.046 Uiso 1 1 calc R . . O1 O 0.6683(2) 0.40880(19) 0.29138(15) 0.0341(4) Uani 1 1 d . . . O2 O 0.9900(3) 0.8237(2) 0.47651(18) 0.0432(5) Uani 1 1 d . . . H2A H 0.9939 0.8169 0.4188 0.065 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 C1 0.0253(13) 0.0281(13) 0.0264(13) -0.0012(11) 0.0124(11) 0.0008(11) C2 0.0336(14) 0.0316(14) 0.0270(13) -0.0028(11) 0.0181(12) -0.0031(11) C3 0.0290(14) 0.0321(15) 0.0337(14) -0.0005(12) 0.0156(12) -0.0014(12) C4 0.0438(17) 0.0444(18) 0.0334(15) -0.0154(13) 0.0225(14) -0.0129(14) C5 0.0467(17) 0.0493(18) 0.0321(15) -0.0074(14) 0.0257(14) -0.0087(15) C6 0.0306(14) 0.0328(14) 0.0287(13) -0.0013(12) 0.0164(11) -0.0029(12) C7 0.0345(15) 0.0443(17) 0.0252(14) 0.0069(12) 0.0162(13) 0.0019(12) C8 0.0460(18) 0.0434(18) 0.0417(17) 0.0129(14) 0.0218(15) -0.0073(14) C9 0.0436(18) 0.0444(19) 0.0495(18) 0.0090(14) 0.0249(16) -0.0082(14) C10 0.0489(18) 0.0278(16) 0.073(2) -0.0035(16) 0.0277(17) -0.0030(14) Fe1 0.0277(3) 0.0241(3) 0.0284(3) 0.000 0.0132(2) 0.000 Br1 0.0560(3) 0.0605(3) 0.0533(3) 0.000 0.0387(3) 0.000 N1 0.0300(11) 0.0294(12) 0.0280(12) 0.0074(10) 0.0127(10) -0.0004(10) N2 0.0265(12) 0.0325(13) 0.0369(13) 0.0014(10) 0.0104(10) -0.0015(9) O1 0.0399(10) 0.0310(10) 0.0323(10) -0.0083(8) 0.0232(8) -0.0088(8) O2 0.0460(11) 0.0417(11) 0.0391(12) -0.0115(9) 0.0255(10) -0.0174(10) _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 C1 O1 1.321(3) . ? C1 C2 1.399(4) . ? C1 C6 1.416(4) . ? C2 C3 1.390(4) . ? C2 H2 0.9300 . ? C3 O2 1.356(3) . ? C3 C4 1.395(4) . ? C4 C5 1.360(4) . ? C4 H4 0.9300 . ? C5 C6 1.410(4) . ? C5 H5 0.9300 . ? C6 C7 1.425(4) . ? C7 N1 1.281(3) . ? C7 H7 0.9300 . ? C8 N1 1.462(4) . ? C8 C9 1.512(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.473(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.511(6) 2_655 ? C10 N2 1.487(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Fe1 O1 1.8771(18) . ? Fe1 O1 1.8771(18) 2_655 ? Fe1 N1 1.924(2) . ? Fe1 N1 1.924(2) 2_655 ? Fe1 N2 2.016(2) . ? Fe1 N2 2.016(2) 2_655 ? N2 H1N2 0.9100 . ? 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 C1 C2 117.3(2) . . ? O1 C1 C6 123.5(2) . . ? C2 C1 C6 119.1(2) . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? O2 C3 C4 116.7(2) . . ? O2 C3 C2 122.4(3) . . ? C4 C3 C2 120.9(3) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 122.0(3) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.6(2) . . ? C5 C6 C7 118.4(2) . . ? C1 C6 C7 122.9(2) . . ? N1 C7 C6 125.2(3) . . ? N1 C7 H7 117.4 . . ? C6 C7 H7 117.4 . . ? N1 C8 C9 106.2(2) . . ? N1 C8 H8A 110.5 . . ? C9 C8 H8A 110.5 . . ? N1 C8 H8B 110.5 . . ? C9 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? N2 C9 C8 109.1(3) . . ? N2 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? N2 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C10 C10 N2 109.92(18) 2_655 . ? C10 C10 H10A 109.7 2_655 . ? N2 C10 H10A 109.7 . . ? C10 C10 H10B 109.7 2_655 . ? N2 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O1 Fe1 O1 94.80(12) . 2_655 ? O1 Fe1 N1 93.24(8) . . ? O1 Fe1 N1 86.50(8) 2_655 . ? O1 Fe1 N1 86.50(8) . 2_655 ? O1 Fe1 N1 93.24(8) 2_655 2_655 ? N1 Fe1 N1 179.62(13) . 2_655 ? O1 Fe1 N2 173.59(8) . . ? O1 Fe1 N2 90.67(9) 2_655 . ? N1 Fe1 N2 83.73(9) . . ? N1 Fe1 N2 96.55(9) 2_655 . ? O1 Fe1 N2 90.67(9) . 2_655 ? O1 Fe1 N2 173.59(8) 2_655 2_655 ? N1 Fe1 N2 96.55(9) . 2_655 ? N1 Fe1 N2 83.73(9) 2_655 2_655 ? N2 Fe1 N2 84.08(13) . 2_655 ? C7 N1 C8 119.7(2) . . ? C7 N1 Fe1 124.32(19) . . ? C8 N1 Fe1 115.24(18) . . ? C9 N2 C10 115.3(2) . . ? C9 N2 Fe1 107.91(17) . . ? C10 N2 Fe1 111.48(19) . . ? C9 N2 H1N2 107.3 . . ? C10 N2 H1N2 107.3 . . ? Fe1 N2 H1N2 107.3 . . ? C1 O1 Fe1 124.94(16) . . ? C3 O2 H2A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.068 data_1c _database_code_depnum_ccdc_archive 'CCDC 884406' #TrackingRef '11589_web_deposit_cif_file_0_IvanNemec_1338292662.[Fe(4OH-saltet)]X.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,8-Bis(4-hydroxysalicylaldiminato)-3,6-diazaoctane) -iron(iii) iodide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 Fe N4 O4, I' _chemical_formula_sum 'C20 H24 Fe I N4 O4' _chemical_formula_weight 567.18 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.168(3) _cell_length_b 9.680(3) _cell_length_c 13.871(4) _cell_angle_alpha 90.00 _cell_angle_beta 130.17(2) _cell_angle_gamma 90.00 _cell_volume 1043.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 566 _exptl_absorpt_coefficient_mu 2.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5730 _exptl_absorpt_correction_T_max 0.6888 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; face-indexed (CrysAlis RED; Oxford Diffraction, 2006) ; _diffrn_ambient_temperature 160(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 'Goniometer KM4/Xcalibur detector: Sapphire2 (large Be window)' _diffrn_measurement_method ; Rotation method data acquisition using omega and phi scans ; _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8646 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1844 _reflns_number_gt 1464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material ' enCIFer (Allen et al., 2004)' _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^)+(0.1077P)^2^+0.3035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1844 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 C1 C 0.7347(7) 0.5019(6) 0.3848(5) 0.0193(13) Uani 1 1 d . . . C2 C 0.8245(8) 0.6132(6) 0.3859(6) 0.0225(14) Uani 1 1 d . . . H2 H 0.8352 0.6194 0.3229 0.027 Uiso 1 1 calc R . . C3 C 0.8978(8) 0.7143(6) 0.4789(6) 0.0233(14) Uani 1 1 d . . . C4 C 0.8848(8) 0.7076(7) 0.5729(6) 0.0296(16) Uani 1 1 d . . . H4 H 0.9332 0.7781 0.6350 0.035 Uiso 1 1 calc R . . C5 C 0.8012(8) 0.5980(7) 0.5741(6) 0.0258(14) Uani 1 1 d . . . H5 H 0.7940 0.5925 0.6389 0.031 Uiso 1 1 calc R . . C6 C 0.7259(8) 0.4939(6) 0.4830(6) 0.0221(13) Uani 1 1 d . . . C7 C 0.6496(8) 0.3779(7) 0.4964(6) 0.0248(15) Uani 1 1 d . . . H7 H 0.6610 0.3742 0.5699 0.030 Uiso 1 1 calc R . . C8 C 0.4965(9) 0.1672(7) 0.4421(7) 0.0339(17) Uani 1 1 d . . . H8A H 0.4805 0.1984 0.5019 0.041 Uiso 1 1 calc R . . H8B H 0.5739 0.0860 0.4783 0.041 Uiso 1 1 calc R . . C9 C 0.3233(9) 0.1317(7) 0.3139(6) 0.0311(16) Uani 1 1 d . . . H9A H 0.2816 0.0419 0.3192 0.037 Uiso 1 1 calc R . . H9B H 0.2373 0.2033 0.2899 0.037 Uiso 1 1 calc R . . C10 C 0.4048(9) -0.0125(7) 0.2101(7) 0.0402(18) Uani 1 1 d . . . H10A H 0.3697 -0.0864 0.2388 0.048 Uiso 1 1 calc R . . H10B H 0.3512 -0.0318 0.1214 0.048 Uiso 1 1 calc R . . Fe1 Fe 0.5000 0.27780(12) 0.2500 0.0178(3) Uani 1 2 d S . . I1 I 1.0000 0.85385(7) 0.2500 0.0374(3) Uani 1 2 d S . . N1 N 0.5674(7) 0.2791(5) 0.4159(5) 0.0211(11) Uani 1 1 d . . . N2 N 0.3428(7) 0.1240(5) 0.2175(5) 0.0244(12) Uani 1 1 d . . . H1N2 H 0.2354 0.1405 0.1395 0.029 Uiso 1 1 calc R . . O1 O 0.6683(5) 0.4084(4) 0.2951(4) 0.0206(9) Uani 1 1 d . . . O2 O 0.9842(6) 0.8241(4) 0.4826(4) 0.0288(11) Uani 1 1 d . . . H2A H 0.9907 0.8160 0.4255 0.043 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 C1 0.017(3) 0.018(3) 0.021(3) -0.003(3) 0.011(3) -0.002(2) C2 0.025(3) 0.023(3) 0.021(3) -0.002(3) 0.016(3) -0.001(3) C3 0.020(3) 0.012(3) 0.033(4) 0.002(3) 0.015(3) 0.003(2) C4 0.034(4) 0.028(4) 0.021(3) -0.014(3) 0.015(3) -0.010(3) C5 0.027(3) 0.032(4) 0.020(3) -0.001(3) 0.016(3) -0.001(3) C6 0.026(3) 0.020(3) 0.024(3) 0.003(3) 0.018(3) 0.003(3) C7 0.023(3) 0.033(4) 0.021(3) 0.010(3) 0.015(3) 0.006(3) C8 0.036(4) 0.026(4) 0.040(4) 0.007(3) 0.024(4) -0.004(3) C9 0.028(4) 0.028(4) 0.033(4) 0.007(3) 0.018(3) -0.007(3) C10 0.046(4) 0.015(4) 0.056(5) 0.002(3) 0.032(4) 0.005(3) Fe1 0.0199(7) 0.0113(6) 0.0225(7) 0.000 0.0138(6) 0.000 I1 0.0431(5) 0.0365(5) 0.0461(5) 0.000 0.0349(4) 0.000 N1 0.026(3) 0.015(3) 0.023(3) 0.007(2) 0.016(2) 0.001(2) N2 0.020(3) 0.012(3) 0.034(3) 0.001(2) 0.015(2) -0.003(2) O1 0.031(2) 0.016(2) 0.028(2) -0.0077(18) 0.025(2) -0.0075(18) O2 0.030(3) 0.023(3) 0.032(3) -0.005(2) 0.019(2) -0.011(2) _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 C1 O1 1.319(7) . ? C1 C2 1.405(9) . ? C1 C6 1.424(8) . ? C2 C3 1.392(9) . ? C2 H2 0.9500 . ? C3 O2 1.359(7) . ? C3 C4 1.394(9) . ? C4 C5 1.366(10) . ? C4 H4 0.9500 . ? C5 C6 1.397(9) . ? C5 H5 0.9500 . ? C6 C7 1.443(9) . ? C7 N1 1.286(8) . ? C7 H7 0.9500 . ? C8 N1 1.470(8) . ? C8 C9 1.530(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.475(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C10 1.486(15) 2_655 ? C10 N2 1.496(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? Fe1 O1 1.881(4) . ? Fe1 O1 1.881(4) 2_655 ? Fe1 N1 1.932(5) 2_655 ? Fe1 N1 1.932(5) . ? Fe1 N2 2.011(5) . ? Fe1 N2 2.011(5) 2_655 ? N2 H1N2 0.9300 . ? O2 H2A 0.8400 . ? 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 C1 C2 118.0(5) . . ? O1 C1 C6 123.7(5) . . ? C2 C1 C6 118.2(5) . . ? C3 C2 C1 120.3(6) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? O2 C3 C2 122.1(6) . . ? O2 C3 C4 116.8(6) . . ? C2 C3 C4 121.1(6) . . ? C5 C4 C3 118.8(6) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 122.1(6) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 119.3(6) . . ? C5 C6 C7 118.1(6) . . ? C1 C6 C7 122.4(6) . . ? N1 C7 C6 124.7(6) . . ? N1 C7 H7 117.7 . . ? C6 C7 H7 117.7 . . ? N1 C8 C9 105.0(5) . . ? N1 C8 H8A 110.7 . . ? C9 C8 H8A 110.7 . . ? N1 C8 H8B 110.7 . . ? C9 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? N2 C9 C8 109.7(6) . . ? N2 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C10 C10 N2 110.6(4) 2_655 . ? C10 C10 H10A 109.5 2_655 . ? N2 C10 H10A 109.5 . . ? C10 C10 H10B 109.5 2_655 . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 Fe1 O1 95.5(3) . 2_655 ? O1 Fe1 N1 86.51(19) . 2_655 ? O1 Fe1 N1 92.98(19) 2_655 2_655 ? O1 Fe1 N1 92.98(19) . . ? O1 Fe1 N1 86.51(19) 2_655 . ? N1 Fe1 N1 179.2(3) 2_655 . ? O1 Fe1 N2 173.3(2) . . ? O1 Fe1 N2 90.12(19) 2_655 . ? N1 Fe1 N2 96.8(2) 2_655 . ? N1 Fe1 N2 83.8(2) . . ? O1 Fe1 N2 90.12(19) . 2_655 ? O1 Fe1 N2 173.3(2) 2_655 2_655 ? N1 Fe1 N2 83.8(2) 2_655 2_655 ? N1 Fe1 N2 96.8(2) . 2_655 ? N2 Fe1 N2 84.5(3) . 2_655 ? C7 N1 C8 118.8(6) . . ? C7 N1 Fe1 124.8(4) . . ? C8 N1 Fe1 115.8(4) . . ? C9 N2 C10 114.6(5) . . ? C9 N2 Fe1 108.2(4) . . ? C10 N2 Fe1 111.1(4) . . ? C9 N2 H1N2 107.6 . . ? C10 N2 H1N2 107.6 . . ? Fe1 N2 H1N2 107.6 . . ? C1 O1 Fe1 125.3(4) . . ? C3 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.7(5) . . . . ? C6 C1 C2 C3 -1.9(9) . . . . ? C1 C2 C3 O2 -179.4(5) . . . . ? C1 C2 C3 C4 0.2(9) . . . . ? O2 C3 C4 C5 -179.1(6) . . . . ? C2 C3 C4 C5 1.3(9) . . . . ? C3 C4 C5 C6 -1.1(10) . . . . ? C4 C5 C6 C1 -0.5(10) . . . . ? C4 C5 C6 C7 176.2(6) . . . . ? O1 C1 C6 C5 179.7(5) . . . . ? C2 C1 C6 C5 2.0(9) . . . . ? O1 C1 C6 C7 3.1(9) . . . . ? C2 C1 C6 C7 -174.6(6) . . . . ? C5 C6 C7 N1 175.7(6) . . . . ? C1 C6 C7 N1 -7.6(10) . . . . ? N1 C8 C9 N2 44.5(7) . . . . ? C6 C7 N1 C8 180.0(6) . . . . ? C6 C7 N1 Fe1 -9.3(9) . . . . ? C9 C8 N1 C7 142.0(6) . . . . ? C9 C8 N1 Fe1 -29.5(7) . . . . ? O1 Fe1 N1 C7 21.9(5) . . . . ? O1 Fe1 N1 C7 -73.4(5) 2_655 . . . ? N1 Fe1 N1 C7 -25.7(5) 2_655 . . . ? N2 Fe1 N1 C7 -163.9(5) . . . . ? N2 Fe1 N1 C7 112.4(5) 2_655 . . . ? O1 Fe1 N1 C8 -167.1(4) . . . . ? O1 Fe1 N1 C8 97.5(5) 2_655 . . . ? N1 Fe1 N1 C8 145.2(4) 2_655 . . . ? N2 Fe1 N1 C8 7.0(4) . . . . ? N2 Fe1 N1 C8 -76.6(5) 2_655 . . . ? C8 C9 N2 C10 84.5(7) . . . . ? C8 C9 N2 Fe1 -40.1(6) . . . . ? C10 C10 N2 C9 -93.4(9) 2_655 . . . ? C10 C10 N2 Fe1 29.6(9) 2_655 . . . ? O1 Fe1 N2 C9 80.0(18) . . . . ? O1 Fe1 N2 C9 -67.8(4) 2_655 . . . ? N1 Fe1 N2 C9 -160.8(4) 2_655 . . . ? N1 Fe1 N2 C9 18.7(4) . . . . ? N2 Fe1 N2 C9 116.1(5) 2_655 . . . ? O1 Fe1 N2 C10 -47(2) . . . . ? O1 Fe1 N2 C10 165.6(5) 2_655 . . . ? N1 Fe1 N2 C10 72.6(5) 2_655 . . . ? N1 Fe1 N2 C10 -107.9(5) . . . . ? N2 Fe1 N2 C10 -10.5(4) 2_655 . . . ? C2 C1 O1 Fe1 -164.0(4) . . . . ? C6 C1 O1 Fe1 18.4(8) . . . . ? O1 Fe1 O1 C1 60.4(4) 2_655 . . . ? N1 Fe1 O1 C1 153.1(5) 2_655 . . . ? N1 Fe1 O1 C1 -26.3(5) . . . . ? N2 Fe1 O1 C1 -87.2(18) . . . . ? N2 Fe1 O1 C1 -123.1(5) 2_655 . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.619 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.209