# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Mallayan Palaniandavar' _publ_contact_author_email palanim51@yahoo.com _publ_section_title ; Biomimetic Iron(III) Complexes of N3O and N3O2 Donor Ligands: Protonation of Coordinated Ethanolate Donor Enhances Dioxygenase Activity ; _publ_author_name M.Palaniandavar # Attachment '- Revised Cif 1.cif' data_20mpks2m _database_code_depnum_ccdc_archive 'CCDC 819033' #TrackingRef '- Revised Cif 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Cl4 Fe2 N6 O5' _chemical_formula_weight 786.10 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0402(6) _cell_length_b 15.9083(14) _cell_length_c 17.0698(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.596(2) _cell_angle_gamma 90.00 _cell_volume 1905.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3486 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.65 _exptl_crystal_description block _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.082 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_Process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.7302 _exptl_absorpt_correction_T_max 0.8811 _exptl_special_details ; The crystals of the compund was very unstable on exposure to atmosphere and hence a crystal of suitable size was selected from the mother liquor, immersed immediately in paratone oil and mounted on the tip of a glass. The structure was solved by direct methods. Two molecules of Fe-complex was present in the asymmetric unit, three water molecules located in the lattice were refined anisotropically till convergence is reached.In addition to three water molecules located for the complex from difference Fourier map, number of diffused scattered peaks with electron density ranging from 2.9 -3 to 2.5 -3 were observed, which can be attributed to disordered solvent molecules (water) , present in the crystal lattice. Attempts to model these peaks were unsuccessful as the residual electron density of the peaks obtained was diffused and there were no obvious major site occupations for the solvent molecules. PLATON/SQUEEZE was used to correct the data for the presence of the disordered solvent molecules. A potential solvent volume of 228.7 3 was found with 91 electrons counts per unit cell worth of scattering was located in the void. This electron counts corresponds to tentatively five more water molecules molecules present in the unit cell. Thus, the structure of the compound revealed two molecules of Fe-complex, three located water molecules in the asymmetric unit along with tentatively 5 more molecules of disordered water molecule in the lattice, whose contribution is removed by PLATON/SQUEEZ program. With the modified data set using SQUEEZ program, the final cycles of least-squares refinements improved both the R-values and Goodness of Fit significantly. Hydrogen atoms attached to the ligand moiety were stereochemically fixed while the lattice water hydrogens could not be located from the differece Fourier map. Due to poor quality of the crystal and presence of disordered water molecules present in the lattice diffraction from high angle reflections were rather weak resulting the data completenss low. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11498 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7510 _reflns_number_gt 7028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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 'calc w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+2.9560P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.18(2) _refine_ls_number_reflns 7510 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.058 0.159 0.705 114.2 45.6 2 -0.085 0.659 0.295 114.2 45.7 _platon_squeeze_details ; ; 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 0.13357(10) 0.32008(5) 0.34180(4) 0.01599(17) Uani 1 d . . . Cl1 Cl -0.0110(2) 0.20051(10) 0.36961(9) 0.0280(3) Uani 1 d . . . Cl2 Cl -0.10330(19) 0.38590(10) 0.26720(8) 0.0259(3) Uani 1 d . . . O1 O 0.3839(6) 0.2742(3) 0.4008(2) 0.0267(10) Uani 1 d . . . N1 N 0.2791(6) 0.2934(3) 0.2406(3) 0.0201(10) Uani 1 d . . . N2 N 0.3266(7) 0.4295(3) 0.3359(3) 0.0245(11) Uani 1 d . . . N3 N 0.0853(6) 0.3928(3) 0.4425(3) 0.0208(10) Uani 1 d . . . C1 C 0.2803(8) 0.2168(4) 0.2065(3) 0.0201(12) Uani 1 d . . . H1 H 0.2148 0.1729 0.2282 0.024 Uiso 1 calc R . . C2 C 0.3747(9) 0.2019(5) 0.1412(3) 0.0280(14) Uani 1 d . . . H2 H 0.3701 0.1493 0.1175 0.034 Uiso 1 calc R . . C3 C 0.4782(8) 0.2673(5) 0.1108(4) 0.0317(15) Uani 1 d . . . H3 H 0.5457 0.2586 0.0668 0.038 Uiso 1 calc R . . C4 C 0.4794(8) 0.3456(5) 0.1469(4) 0.0274(14) Uani 1 d . . . H4 H 0.5479 0.3899 0.1275 0.033 Uiso 1 calc R . . C5 C 0.3768(8) 0.3569(4) 0.2126(4) 0.0248(13) Uani 1 d . . . C6 C 0.3664(9) 0.4389(4) 0.2522(4) 0.0294(14) Uani 1 d . . . H6A H 0.2667 0.4726 0.2251 0.035 Uiso 1 calc R . . H6B H 0.4862 0.4685 0.2494 0.035 Uiso 1 calc R . . C7 C 0.2217(9) 0.5023(4) 0.3672(4) 0.0280(13) Uani 1 d . . . H7A H 0.1267 0.5227 0.3275 0.034 Uiso 1 calc R . . H7B H 0.3098 0.5478 0.3812 0.034 Uiso 1 calc R . . C8 C 0.1261(8) 0.4739(4) 0.4390(3) 0.0249(13) Uani 1 d . . . C9 C 0.0842(9) 0.5300(5) 0.4985(4) 0.0297(14) Uani 1 d . . . H9 H 0.1147 0.5867 0.4958 0.036 Uiso 1 calc R . . C10 C -0.0035(8) 0.4979(5) 0.5606(4) 0.0317(15) Uani 1 d . . . H10 H -0.0350 0.5336 0.6008 0.038 Uiso 1 calc R . . C11 C -0.0454(8) 0.4144(5) 0.5646(3) 0.0288(15) Uani 1 d . . . H11 H -0.1054 0.3932 0.6070 0.035 Uiso 1 calc R . . C12 C 0.0013(8) 0.3623(4) 0.5060(3) 0.0247(13) Uani 1 d . . . H12 H -0.0243 0.3051 0.5092 0.030 Uiso 1 calc R . . C13 C 0.5037(8) 0.4135(4) 0.3895(4) 0.0274(13) Uani 1 d . . . H13A H 0.6088 0.4461 0.3720 0.033 Uiso 1 calc R . . H13B H 0.4825 0.4311 0.4425 0.033 Uiso 1 calc R . . C14 C 0.5535(8) 0.3213(5) 0.3893(4) 0.0312(14) Uani 1 d . . . H14A H 0.6018 0.3061 0.3396 0.037 Uiso 1 calc R . . H14B H 0.6512 0.3092 0.4311 0.037 Uiso 1 calc R . . Fe2 Fe 0.83170(11) 0.98742(5) 0.15840(4) 0.01996(19) Uani 1 d . . . Cl3 Cl 1.1182(2) 0.96606(11) 0.22734(8) 0.0284(3) Uani 1 d . . . Cl4 Cl 0.8626(2) 1.12208(10) 0.12298(8) 0.0273(3) Uani 1 d . . . O2 O 0.5630(6) 0.9886(3) 0.0917(2) 0.0289(9) Uani 1 d . . . N4 N 0.9217(7) 0.9221(4) 0.0603(3) 0.0267(11) Uani 1 d . . . N5 N 0.7286(8) 0.8587(4) 0.1766(3) 0.0313(13) Uani 1 d . . . N6 N 0.6844(7) 0.9964(4) 0.2604(3) 0.0209(10) Uani 1 d . . . C15 C 0.9738(9) 0.9607(5) -0.0052(4) 0.0300(14) Uani 1 d . . . H15 H 0.9721 1.0191 -0.0081 0.036 Uiso 1 calc R . . C16 C 1.0302(8) 0.9139(5) -0.0688(3) 0.0279(14) Uani 1 d . . . H16 H 1.0662 0.9411 -0.1136 0.034 Uiso 1 calc R . . C17 C 1.0319(8) 0.8291(5) -0.0649(4) 0.0367(18) Uani 1 d . . . H17 H 1.0692 0.7979 -0.1071 0.044 Uiso 1 calc R . . C18 C 0.9771(9) 0.7872(5) 0.0034(4) 0.0336(15) Uani 1 d . . . H18 H 0.9792 0.7289 0.0070 0.040 Uiso 1 calc R . . C19 C 0.9202(9) 0.8367(5) 0.0651(4) 0.0312(15) Uani 1 d . . . C20 C 0.8597(10) 0.8000(5) 0.1391(4) 0.0358(16) Uani 1 d . . . H20A H 0.9709 0.7892 0.1750 0.043 Uiso 1 calc R . . H20B H 0.7954 0.7469 0.1278 0.043 Uiso 1 calc R . . C21 C 0.7292(10) 0.8468(4) 0.2625(4) 0.0280(14) Uani 1 d . . . H21A H 0.8581 0.8368 0.2850 0.034 Uiso 1 calc R . . H21B H 0.6517 0.7986 0.2738 0.034 Uiso 1 calc R . . C22 C 0.6509(8) 0.9242(4) 0.2973(3) 0.0237(13) Uani 1 d . . . C23 C 0.5492(8) 0.9230(5) 0.3643(3) 0.0269(14) Uani 1 d . . . H23 H 0.5243 0.8724 0.3889 0.032 Uiso 1 calc R . . C24 C 0.4864(8) 0.9982(5) 0.3933(3) 0.0274(13) Uani 1 d . . . H24 H 0.4180 0.9988 0.4377 0.033 Uiso 1 calc R . . C25 C 0.5255(9) 1.0726(4) 0.3560(3) 0.0261(13) Uani 1 d . . . H25 H 0.4863 1.1239 0.3753 0.031 Uiso 1 calc R . . C26 C 0.6236(8) 1.0690(4) 0.2899(3) 0.0209(12) Uani 1 d . . . H26 H 0.6492 1.1189 0.2643 0.025 Uiso 1 calc R . . C28 C 0.4918(10) 0.9076(5) 0.0703(4) 0.0357(16) Uani 1 d . . . H28A H 0.5566 0.8859 0.0265 0.043 Uiso 1 calc R . . H28B H 0.3565 0.9107 0.0545 0.043 Uiso 1 calc R . . C27 C 0.5268(10) 0.8506(5) 0.1410(4) 0.0347(15) Uani 1 d . . . H27A H 0.4393 0.8651 0.1800 0.042 Uiso 1 calc R . . H27B H 0.5026 0.7927 0.1252 0.042 Uiso 1 calc R . . O3 O 0.4889(12) 0.1987(4) 0.5466(3) 0.073(2) Uani 1 d . . . O4 O 0.4794(10) 0.0914(4) 0.9588(3) 0.0583(17) Uani 1 d . . . O5 O 0.8030(8) 0.1368(4) 0.8533(4) 0.0554(16) Uani 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 0.0154(3) 0.0170(4) 0.0158(3) -0.0007(3) 0.0023(3) 0.0015(3) Cl1 0.0334(8) 0.0202(8) 0.0310(7) -0.0016(6) 0.0064(6) -0.0041(6) Cl2 0.0214(6) 0.0355(9) 0.0211(6) 0.0073(6) 0.0049(5) 0.0074(6) O1 0.0191(19) 0.034(3) 0.026(2) 0.0026(18) -0.0032(16) 0.0013(18) N1 0.018(2) 0.021(3) 0.022(2) -0.0058(19) 0.0002(17) 0.0049(19) N2 0.024(2) 0.022(3) 0.028(3) -0.003(2) 0.008(2) -0.002(2) N3 0.016(2) 0.023(3) 0.023(2) -0.001(2) 0.0004(17) 0.004(2) C1 0.020(3) 0.024(3) 0.015(2) -0.003(2) -0.005(2) 0.009(2) C2 0.036(3) 0.030(4) 0.018(3) -0.012(2) 0.000(2) 0.013(3) C3 0.018(3) 0.052(5) 0.026(3) -0.002(3) 0.002(2) 0.010(3) C4 0.016(3) 0.042(4) 0.024(3) 0.005(3) 0.000(2) 0.006(2) C5 0.020(3) 0.033(4) 0.021(3) 0.005(2) 0.001(2) 0.007(2) C6 0.028(3) 0.033(4) 0.029(3) 0.007(3) 0.009(2) -0.003(3) C7 0.034(3) 0.011(3) 0.040(3) 0.002(3) 0.011(3) 0.003(2) C8 0.017(3) 0.028(4) 0.029(3) -0.005(3) 0.000(2) 0.005(2) C9 0.027(3) 0.026(4) 0.037(4) -0.010(3) 0.005(3) 0.002(3) C10 0.018(3) 0.041(4) 0.036(3) -0.023(3) 0.007(2) 0.000(3) C11 0.022(3) 0.046(4) 0.018(3) -0.007(3) 0.006(2) -0.004(3) C12 0.023(3) 0.026(3) 0.023(3) 0.003(2) -0.006(2) 0.002(2) C13 0.020(3) 0.030(4) 0.034(3) -0.002(3) 0.006(2) 0.000(3) C14 0.023(3) 0.035(4) 0.036(3) -0.008(3) 0.003(2) -0.001(3) Fe2 0.0218(4) 0.0211(5) 0.0173(4) -0.0027(3) 0.0030(3) 0.0038(3) Cl3 0.0246(7) 0.0371(9) 0.0235(7) 0.0027(6) 0.0027(5) 0.0076(6) Cl4 0.0340(8) 0.0231(8) 0.0253(7) 0.0026(6) 0.0068(6) 0.0007(6) O2 0.024(2) 0.036(3) 0.027(2) -0.010(2) -0.0023(16) 0.007(2) N4 0.027(3) 0.035(3) 0.018(2) -0.006(2) 0.0027(19) 0.003(2) N5 0.033(3) 0.034(3) 0.028(3) 0.001(2) 0.005(2) 0.013(2) N6 0.025(2) 0.025(3) 0.013(2) -0.002(2) 0.0033(17) 0.003(2) C15 0.025(3) 0.034(4) 0.031(3) -0.008(3) 0.000(2) 0.010(3) C16 0.024(3) 0.047(4) 0.013(3) -0.008(3) -0.002(2) 0.004(3) C17 0.022(3) 0.055(5) 0.032(3) -0.030(3) -0.002(2) 0.014(3) C18 0.029(3) 0.031(4) 0.041(4) -0.018(3) 0.004(3) 0.004(3) C19 0.025(3) 0.031(4) 0.039(4) -0.008(3) 0.007(3) 0.006(3) C20 0.043(4) 0.031(4) 0.035(3) -0.001(3) 0.011(3) 0.009(3) C21 0.038(3) 0.019(3) 0.028(3) -0.001(2) 0.012(3) -0.002(3) C22 0.022(3) 0.027(3) 0.021(3) 0.003(2) -0.005(2) 0.002(3) C23 0.023(3) 0.041(4) 0.018(3) 0.007(3) 0.005(2) 0.005(3) C24 0.023(3) 0.037(4) 0.023(3) 0.002(3) 0.007(2) 0.001(3) C25 0.028(3) 0.030(4) 0.019(3) -0.010(2) -0.003(2) 0.014(3) C26 0.020(3) 0.024(3) 0.018(3) -0.003(2) -0.006(2) 0.002(2) C28 0.030(3) 0.047(5) 0.029(3) -0.013(3) -0.003(3) 0.005(3) C27 0.037(4) 0.034(4) 0.033(3) -0.009(3) 0.000(3) -0.001(3) O3 0.155(7) 0.041(4) 0.027(3) 0.026(2) 0.036(3) 0.063(4) O4 0.091(5) 0.046(4) 0.038(3) 0.002(3) 0.004(3) 0.017(3) O5 0.036(3) 0.039(4) 0.092(4) 0.002(3) 0.010(3) -0.023(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 2.090(4) . ? Fe1 N1 2.121(5) . ? Fe1 N3 2.122(5) . ? Fe1 N2 2.216(5) . ? Fe1 Cl1 2.2264(17) . ? Fe1 Cl2 2.2712(15) . ? O1 C14 1.437(8) . ? N1 C5 1.331(8) . ? N1 C1 1.351(8) . ? N2 C6 1.484(7) . ? N2 C7 1.496(8) . ? N2 C13 1.508(8) . ? N3 C8 1.323(8) . ? N3 C12 1.366(8) . ? C1 C2 1.363(8) . ? C1 H1 0.9300 . ? C2 C3 1.393(11) . ? C2 H2 0.9300 . ? C3 C4 1.390(10) . ? C3 H3 0.9300 . ? C4 C5 1.393(8) . ? C4 H4 0.9300 . ? C5 C6 1.475(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.514(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.401(9) . ? C9 C10 1.368(10) . ? C9 H9 0.9300 . ? C10 C11 1.364(11) . ? C10 H10 0.9300 . ? C11 C12 1.359(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.508(11) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? Fe2 N6 2.102(4) . ? Fe2 N4 2.111(5) . ? Fe2 O2 2.128(4) . ? Fe2 N5 2.202(6) . ? Fe2 Cl4 2.2413(18) . ? Fe2 Cl3 2.2779(16) . ? O2 C28 1.420(9) . ? N4 C15 1.351(9) . ? N4 C19 1.362(9) . ? N5 C21 1.478(8) . ? N5 C20 1.493(8) . ? N5 C27 1.505(9) . ? N6 C22 1.340(8) . ? N6 C26 1.343(8) . ? C15 C16 1.400(9) . ? C15 H15 0.9300 . ? C16 C17 1.350(11) . ? C16 H16 0.9300 . ? C17 C18 1.423(11) . ? C17 H17 0.9300 . ? C18 C19 1.398(9) . ? C18 H18 0.9300 . ? C19 C20 1.485(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.491(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.397(8) . ? C23 C24 1.382(10) . ? C23 H23 0.9300 . ? C24 C25 1.382(10) . ? C24 H24 0.9300 . ? C25 C26 1.370(8) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C28 C27 1.515(10) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? 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 N1 83.08(17) . . ? O1 Fe1 N3 89.05(17) . . ? N1 Fe1 N3 152.6(2) . . ? O1 Fe1 N2 78.45(19) . . ? N1 Fe1 N2 77.39(19) . . ? N3 Fe1 N2 75.35(19) . . ? O1 Fe1 Cl1 88.92(13) . . ? N1 Fe1 Cl1 105.18(15) . . ? N3 Fe1 Cl1 100.82(15) . . ? N2 Fe1 Cl1 166.79(15) . . ? O1 Fe1 Cl2 169.75(13) . . ? N1 Fe1 Cl2 90.93(13) . . ? N3 Fe1 Cl2 92.55(14) . . ? N2 Fe1 Cl2 92.16(15) . . ? Cl1 Fe1 Cl2 100.70(6) . . ? C14 O1 Fe1 115.5(4) . . ? C5 N1 C1 120.5(5) . . ? C5 N1 Fe1 116.0(4) . . ? C1 N1 Fe1 123.4(4) . . ? C6 N2 C7 113.7(5) . . ? C6 N2 C13 113.0(5) . . ? C7 N2 C13 108.7(5) . . ? C6 N2 Fe1 106.7(4) . . ? C7 N2 Fe1 105.6(4) . . ? C13 N2 Fe1 108.7(4) . . ? C8 N3 C12 119.4(5) . . ? C8 N3 Fe1 116.5(4) . . ? C12 N3 Fe1 123.8(4) . . ? N1 C1 C2 121.9(6) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 118.7(6) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.2(6) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 120.5(6) . . ? N1 C5 C6 117.4(5) . . ? C4 C5 C6 122.1(6) . . ? C5 C6 N2 111.8(5) . . ? C5 C6 H6A 109.2 . . ? N2 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? N2 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 108.8(5) . . ? N2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C9 122.0(6) . . ? N3 C8 C7 116.1(5) . . ? C9 C8 C7 121.9(6) . . ? C10 C9 C8 117.3(7) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? C11 C10 C9 120.9(6) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 119.5(6) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 N3 120.8(6) . . ? C11 C12 H12 119.6 . . ? N3 C12 H12 119.6 . . ? C14 C13 N2 110.1(5) . . ? C14 C13 H13A 109.6 . . ? N2 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? N2 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? O1 C14 C13 108.1(5) . . ? O1 C14 H14A 110.1 . . ? C13 C14 H14A 110.1 . . ? O1 C14 H14B 110.1 . . ? C13 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? N6 Fe2 N4 152.9(2) . . ? N6 Fe2 O2 88.05(17) . . ? N4 Fe2 O2 83.73(18) . . ? N6 Fe2 N5 75.9(2) . . ? N4 Fe2 N5 77.2(2) . . ? O2 Fe2 N5 78.2(2) . . ? N6 Fe2 Cl4 102.91(16) . . ? N4 Fe2 Cl4 102.37(17) . . ? O2 Fe2 Cl4 87.05(15) . . ? N5 Fe2 Cl4 165.18(15) . . ? N6 Fe2 Cl3 93.29(13) . . ? N4 Fe2 Cl3 91.54(14) . . ? O2 Fe2 Cl3 171.90(15) . . ? N5 Fe2 Cl3 94.40(15) . . ? Cl4 Fe2 Cl3 100.42(7) . . ? C28 O2 Fe2 114.2(4) . . ? C15 N4 C19 120.4(6) . . ? C15 N4 Fe2 123.5(5) . . ? C19 N4 Fe2 116.0(4) . . ? C21 N5 C20 113.1(5) . . ? C21 N5 C27 108.5(5) . . ? C20 N5 C27 111.6(6) . . ? C21 N5 Fe2 106.5(4) . . ? C20 N5 Fe2 107.4(4) . . ? C27 N5 Fe2 109.5(4) . . ? C22 N6 C26 119.2(5) . . ? C22 N6 Fe2 116.6(4) . . ? C26 N6 Fe2 124.2(4) . . ? N4 C15 C16 120.9(7) . . ? N4 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 119.6(6) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.5(6) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 117.8(7) . . ? C19 C18 H18 121.1 . . ? C17 C18 H18 121.1 . . ? N4 C19 C18 120.8(7) . . ? N4 C19 C20 116.6(6) . . ? C18 C19 C20 122.6(7) . . ? C19 C20 N5 110.4(6) . . ? C19 C20 H20A 109.6 . . ? N5 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? N5 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? N5 C21 C22 108.5(5) . . ? N5 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? N5 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? N6 C22 C23 121.2(6) . . ? N6 C22 C21 115.9(5) . . ? C23 C22 C21 123.0(6) . . ? C24 C23 C22 118.7(6) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C25 C24 C23 119.7(5) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 118.4(6) . . ? C26 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? N6 C26 C25 122.7(6) . . ? N6 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? O2 C28 C27 107.8(5) . . ? O2 C28 H28A 110.1 . . ? C27 C28 H28A 110.1 . . ? O2 C28 H28B 110.1 . . ? C27 C28 H28B 110.1 . . ? H28A C28 H28B 108.5 . . ? N5 C27 C28 111.0(6) . . ? N5 C27 H27A 109.4 . . ? C28 C27 H27A 109.4 . . ? N5 C27 H27B 109.4 . . ? C28 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.319 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.121 # Attachment '- 3.cif' data_mpksfa9m _database_code_depnum_ccdc_archive 'CCDC 819034' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 Cl3 Fe N3 O2' _chemical_formula_weight 449.56 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.358(8) _cell_length_b 19.495(19) _cell_length_c 13.953(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.352(17) _cell_angle_gamma 90.00 _cell_volume 1947(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1952 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 24.76 _exptl_crystal_description PLATES _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.201 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6857 _exptl_absorpt_correction_T_max 0.9101 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9901 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3817 _reflns_number_gt 3044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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 'calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+3.2117P] 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 3817 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.1837 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 0.24763(11) 0.43640(5) 0.26090(6) 0.0115(3) Uani 1 d . . . Cl3 Cl 0.16812(19) 0.46508(8) 0.40754(10) 0.0167(4) Uani 1 d . . . Cl1 Cl 0.1582(2) 0.32074(8) 0.25974(11) 0.0183(4) Uani 1 d . . . Cl2 Cl -0.01958(19) 0.47336(8) 0.15088(11) 0.0192(4) Uani 1 d . . . O1 O 0.8058(5) 0.2931(2) 0.4688(3) 0.0186(10) Uani 1 d . . . O2 O 1.0221(7) 0.1957(3) 0.3789(3) 0.0297(12) Uani 1 d . . . H2 H 1.0742 0.2266 0.3555 0.045 Uiso 1 calc R . . N1 N 0.3858(6) 0.5345(3) 0.2681(3) 0.0133(11) Uani 1 d . . . N2 N 0.5533(6) 0.4085(3) 0.3369(3) 0.0137(11) Uani 1 d . . . N3 N 0.3913(6) 0.4133(3) 0.1421(3) 0.0121(11) Uani 1 d . . . C1 C 0.2945(8) 0.5952(3) 0.2413(4) 0.0153(13) Uani 1 d . . . H1 H 0.1667 0.5943 0.2140 0.018 Uiso 1 calc R . . C2 C 0.3856(10) 0.6579(4) 0.2534(5) 0.0240(16) Uani 1 d . . . H2A H 0.3211 0.6984 0.2334 0.029 Uiso 1 calc R . . C3 C 0.5783(10) 0.6587(4) 0.2967(5) 0.0289(17) Uani 1 d . . . H3 H 0.6428 0.7001 0.3057 0.035 Uiso 1 calc R . . C4 C 0.6712(8) 0.5983(4) 0.3257(5) 0.0223(15) Uani 1 d . . . H4 H 0.7977 0.5984 0.3562 0.027 Uiso 1 calc R . . C5 C 0.5723(8) 0.5367(3) 0.3085(4) 0.0136(13) Uani 1 d . . . C6 C 0.6754(8) 0.4699(3) 0.3333(4) 0.0157(14) Uani 1 d . . . H6A H 0.7482 0.4613 0.2847 0.019 Uiso 1 calc R . . H6B H 0.7622 0.4746 0.3968 0.019 Uiso 1 calc R . . C7 C 0.6049(8) 0.3524(3) 0.2756(4) 0.0152(13) Uani 1 d . . . H7A H 0.5491 0.3097 0.2898 0.018 Uiso 1 calc R . . H7B H 0.7395 0.3466 0.2915 0.018 Uiso 1 calc R . . C8 C 0.5374(8) 0.3693(3) 0.1666(4) 0.0140(13) Uani 1 d . . . C9 C 0.6237(9) 0.3408(4) 0.0959(5) 0.0220(15) Uani 1 d . . . H9 H 0.7224 0.3101 0.1141 0.026 Uiso 1 calc R . . C10 C 0.5568(9) 0.3600(4) -0.0029(4) 0.0225(15) Uani 1 d . . . H10 H 0.6101 0.3411 -0.0512 0.027 Uiso 1 calc R . . C11 C 0.4112(8) 0.4069(4) -0.0292(4) 0.0212(15) Uani 1 d . . . H11 H 0.3680 0.4210 -0.0941 0.025 Uiso 1 calc R . . C12 C 0.3328(8) 0.4320(3) 0.0456(4) 0.0197(14) Uani 1 d . . . H12 H 0.2350 0.4632 0.0289 0.024 Uiso 1 calc R . . C13 C 0.5713(8) 0.3847(3) 0.4413(4) 0.0143(13) Uani 1 d . . . H13A H 0.4851 0.3469 0.4403 0.017 Uiso 1 calc R . . H13B H 0.5312 0.4218 0.4778 0.017 Uiso 1 calc R . . C14 C 0.7652(9) 0.3613(4) 0.4982(4) 0.0214(15) Uani 1 d . . . H14A H 0.8589 0.3930 0.4858 0.026 Uiso 1 calc R . . H14B H 0.7702 0.3618 0.5683 0.026 Uiso 1 calc R . . C15 C 1.0000(8) 0.2771(3) 0.5117(5) 0.0204(15) Uani 1 d . . . H15A H 1.0232 0.2802 0.5829 0.025 Uiso 1 calc R . . H15B H 1.0795 0.3103 0.4895 0.025 Uiso 1 calc R . . C16 C 1.0473(9) 0.2065(4) 0.4831(5) 0.0229(15) Uani 1 d . . . H16A H 1.1765 0.1969 0.5149 0.028 Uiso 1 calc R . . H16B H 0.9703 0.1737 0.5081 0.028 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 0.0087(4) 0.0132(5) 0.0118(4) -0.0008(3) 0.0010(3) -0.0001(4) Cl3 0.0117(7) 0.0222(9) 0.0161(7) -0.0026(6) 0.0027(5) 0.0009(6) Cl1 0.0196(7) 0.0150(9) 0.0201(7) -0.0005(6) 0.0040(6) -0.0045(7) Cl2 0.0120(7) 0.0248(10) 0.0181(7) 0.0018(6) -0.0019(5) 0.0007(6) O1 0.011(2) 0.016(3) 0.026(2) 0.0045(19) -0.0006(17) 0.0075(18) O2 0.031(3) 0.027(3) 0.032(3) 0.000(2) 0.009(2) -0.006(2) N1 0.012(2) 0.014(3) 0.014(2) 0.001(2) 0.0029(19) 0.001(2) N2 0.012(2) 0.017(3) 0.011(2) -0.003(2) 0.0011(18) 0.001(2) N3 0.008(2) 0.013(3) 0.013(2) -0.003(2) -0.0021(18) -0.006(2) C1 0.017(3) 0.017(4) 0.011(3) -0.001(2) 0.002(2) 0.001(3) C2 0.033(4) 0.014(4) 0.022(3) 0.009(3) 0.001(3) 0.004(3) C3 0.036(4) 0.020(4) 0.028(4) -0.001(3) 0.002(3) -0.016(3) C4 0.011(3) 0.023(4) 0.027(3) 0.001(3) -0.008(3) -0.009(3) C5 0.015(3) 0.022(4) 0.003(2) -0.002(2) 0.002(2) -0.002(3) C6 0.013(3) 0.022(4) 0.012(3) -0.007(3) 0.002(2) -0.003(3) C7 0.014(3) 0.017(4) 0.015(3) 0.009(3) 0.006(2) 0.002(3) C8 0.013(3) 0.009(3) 0.019(3) -0.003(3) 0.002(2) -0.004(3) C9 0.019(3) 0.021(4) 0.026(3) 0.001(3) 0.005(3) 0.009(3) C10 0.022(3) 0.031(4) 0.015(3) -0.004(3) 0.005(3) -0.001(3) C11 0.019(3) 0.032(4) 0.011(3) 0.005(3) 0.001(2) -0.003(3) C12 0.014(3) 0.022(4) 0.020(3) 0.001(3) -0.001(2) -0.005(3) C13 0.017(3) 0.019(4) 0.007(3) 0.004(2) 0.004(2) 0.004(3) C14 0.024(3) 0.026(4) 0.012(3) -0.001(3) 0.001(2) 0.010(3) C15 0.013(3) 0.027(4) 0.019(3) 0.000(3) -0.002(2) 0.006(3) C16 0.021(3) 0.025(4) 0.022(3) 0.003(3) 0.003(3) 0.004(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 N1 2.157(5) . ? Fe1 N3 2.209(5) . ? Fe1 Cl2 2.312(2) . ? Fe1 N2 2.319(5) . ? Fe1 Cl3 2.323(3) . ? Fe1 Cl1 2.348(3) . ? O1 C14 1.442(8) . ? O1 C15 1.451(7) . ? O2 C16 1.438(8) . ? O2 H2 0.8200 . ? N1 C5 1.358(7) . ? N1 C1 1.370(8) . ? N2 C7 1.490(8) . ? N2 C6 1.505(8) . ? N2 C13 1.505(7) . ? N3 C8 1.356(8) . ? N3 C12 1.364(8) . ? C1 C2 1.384(9) . ? C1 H1 0.9300 . ? C2 C3 1.407(10) . ? C2 H2A 0.9300 . ? C3 C4 1.375(10) . ? C3 H3 0.9300 . ? C4 C5 1.395(9) . ? C4 H4 0.9300 . ? C5 C6 1.508(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.522(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.405(8) . ? C9 C10 1.403(9) . ? C9 H9 0.9300 . ? C10 C11 1.392(9) . ? C10 H10 0.9300 . ? C11 C12 1.392(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.533(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.497(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N3 85.02(18) . . ? N1 Fe1 Cl2 94.25(14) . . ? N3 Fe1 Cl2 92.64(15) . . ? N1 Fe1 N2 77.88(19) . . ? N3 Fe1 N2 73.36(18) . . ? Cl2 Fe1 N2 164.34(13) . . ? N1 Fe1 Cl3 87.56(14) . . ? N3 Fe1 Cl3 166.39(13) . . ? Cl2 Fe1 Cl3 99.28(9) . . ? N2 Fe1 Cl3 93.94(13) . . ? N1 Fe1 Cl1 168.51(14) . . ? N3 Fe1 Cl1 88.92(14) . . ? Cl2 Fe1 Cl4 95.78(7) . . ? N2 Fe1 Cl1 91.04(14) . . ? Cl3 Fe1 Cl1 96.32(7) . . ? C14 O1 C15 109.3(5) . . ? C16 O2 H2 109.5 . . ? C5 N1 C1 118.0(5) . . ? C5 N1 Fe1 117.9(4) . . ? C1 N1 Fe1 123.9(4) . . ? C7 N2 C6 109.3(4) . . ? C7 N2 C13 110.7(5) . . ? C6 N2 C13 111.0(4) . . ? C7 N2 Fe1 105.0(3) . . ? C6 N2 Fe1 108.7(4) . . ? C13 N2 Fe1 112.0(3) . . ? C8 N3 C12 118.0(5) . . ? C8 N3 Fe1 115.4(4) . . ? C12 N3 Fe1 126.1(4) . . ? N1 C1 C2 122.4(6) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.3(6) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C4 C3 C2 120.0(6) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.4(6) . . ? N1 C5 C6 118.3(5) . . ? C4 C5 C6 119.3(5) . . ? N2 C6 C5 115.0(5) . . ? N2 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? N2 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N2 C7 C8 110.3(5) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 122.2(5) . . ? N3 C8 C7 116.5(5) . . ? C9 C8 C7 121.3(5) . . ? C10 C9 C8 118.1(6) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C11 C10 C9 120.5(6) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 117.4(6) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? N3 C12 C11 123.7(6) . . ? N3 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? N2 C13 C14 117.1(5) . . ? N2 C13 H13A 108.0 . . ? C14 C13 H13A 108.0 . . ? N2 C13 H13B 108.0 . . ? C14 C13 H13B 108.0 . . ? H13A C13 H13B 107.3 . . ? O1 C14 C13 110.8(5) . . ? O1 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? O1 C15 C16 110.8(5) . . ? O1 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O2 C16 C15 114.9(5) . . ? O2 C16 H16A 108.6 . . ? C15 C16 H16A 108.6 . . ? O2 C16 H16B 108.6 . . ? C15 C16 H16B 108.6 . . ? H16A C16 H16B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.846 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.152 # Attachment '- Revised Cif 5.cif' data_8mpksm _database_code_depnum_ccdc_archive 'CCDC 819035' #TrackingRef '- Revised Cif 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 Cl4 Fe2 N10 O10' _chemical_formula_weight 878.13 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 P21/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 8.1513(7) _cell_length_b 12.0527(10) _cell_length_c 17.3786(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.6750(10) _cell_angle_gamma 90.00 _cell_volume 1707.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2346 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.43 _exptl_crystal_description BLOCKS _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.231 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5669 _exptl_absorpt_correction_T_max 0.9524 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRAVTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10085 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3939 _reflns_number_gt 3433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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 'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+6.2085P] 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 3939 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1600 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.52463(6) 0.45048(4) 0.58435(3) 0.01252(16) Uani 1 d . . . Cl1 Cl 0.74440(11) 0.45274(8) 0.66980(5) 0.0209(2) Uani 1 d . . . N1 N 0.5535(4) 0.2816(3) 0.56853(18) 0.0179(7) Uani 1 d . . . N2 N 0.5138(5) 0.1084(3) 0.6029(2) 0.0259(8) Uani 1 d . . . N3 N 0.2845(4) 0.3671(3) 0.63214(18) 0.0158(6) Uani 1 d . . . N4 N 0.2231(4) 0.6419(3) 0.7212(2) 0.0235(7) Uani 1 d . . . N5 N 0.4105(4) 0.5729(3) 0.64599(18) 0.0178(6) Uani 1 d . . . O1 O 0.3610(3) 0.4768(2) 0.49747(14) 0.0146(5) Uani 1 d . . . C1 C 0.6717(5) 0.2163(3) 0.5338(2) 0.0230(8) Uani 1 d . . . H1 H 0.7541 0.2417 0.5017 0.028 Uiso 1 calc R . . C2 C 0.6472(6) 0.1099(4) 0.5544(3) 0.0288(9) Uani 1 d . . . H2 H 0.7084 0.0489 0.5389 0.035 Uiso 1 calc R . . C3 C 0.4622(5) 0.2134(3) 0.6098(2) 0.0192(8) Uani 1 d . . . C4 C 0.3261(5) 0.2536(3) 0.6592(2) 0.0192(8) Uani 1 d . . . H4B H 0.2315 0.2051 0.6542 0.023 Uiso 1 calc R . . H4A H 0.3608 0.2552 0.7128 0.023 Uiso 1 calc R . . C5 C 0.2091(5) 0.4360(3) 0.6926(2) 0.0216(8) Uani 1 d . . . H5A H 0.2335 0.4050 0.7430 0.026 Uiso 1 calc R . . H5B H 0.0910 0.4379 0.6855 0.026 Uiso 1 calc R . . C6 C 0.2780(5) 0.5504(3) 0.6868(2) 0.0184(8) Uani 1 d . . . C7 C 0.3249(5) 0.7281(4) 0.7011(3) 0.0279(9) Uani 1 d . . . H7 H 0.3156 0.8018 0.7161 0.034 Uiso 1 calc R . . C8 C 0.4410(5) 0.6846(3) 0.6552(2) 0.0216(8) Uani 1 d . . . H8 H 0.5273 0.7236 0.6334 0.026 Uiso 1 calc R . . C9 C 0.1916(4) 0.4621(3) 0.5134(2) 0.0180(7) Uani 1 d . . . H9B H 0.1294 0.4534 0.4658 0.022 Uiso 1 calc R . . H9A H 0.1494 0.5261 0.5407 0.022 Uiso 1 calc R . . C10 C 0.1764(5) 0.3593(3) 0.5623(2) 0.0206(8) Uani 1 d . . . H10A H 0.0633 0.3503 0.5779 0.025 Uiso 1 calc R . . H10B H 0.2069 0.2947 0.5324 0.025 Uiso 1 calc R . . C11 C 0.4403(7) 0.0104(4) 0.6387(3) 0.0412(13) Uani 1 d . . . H11A H 0.4368 0.0208 0.6934 0.062 Uiso 1 calc R . . H11B H 0.5052 -0.0539 0.6273 0.062 Uiso 1 calc R . . H11C H 0.3309 0.0002 0.6189 0.062 Uiso 1 calc R . . C12 C 0.0752(6) 0.6514(4) 0.7680(3) 0.0316(10) Uani 1 d . . . H12A H -0.0173 0.6682 0.7353 0.047 Uiso 1 calc R . . H12B H 0.0897 0.7097 0.8051 0.047 Uiso 1 calc R . . H12C H 0.0562 0.5826 0.7942 0.047 Uiso 1 calc R . . Cl2 Cl 0.07310(16) 0.16467(11) 0.40273(8) 0.0417(3) Uani 1 d . . . O2 O -0.0049(5) 0.2693(3) 0.4142(2) 0.0465(9) Uani 1 d . . . O3 O 0.2170(6) 0.1727(4) 0.3726(3) 0.0762(16) Uani 1 d . . . O4 O -0.0273(6) 0.0938(5) 0.3559(4) 0.0853(19) Uani 1 d . . . O5 O 0.1024(10) 0.1154(5) 0.4782(3) 0.109(3) Uani 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 0.0099(3) 0.0145(3) 0.0132(3) 0.00115(19) 0.00324(18) 0.00054(18) Cl1 0.0167(4) 0.0271(5) 0.0188(5) 0.0046(4) -0.0018(3) -0.0006(3) N1 0.0163(15) 0.0194(16) 0.0182(16) 0.0004(12) 0.0048(12) 0.0026(12) N2 0.039(2) 0.0162(17) 0.0224(18) 0.0029(13) 0.0077(15) 0.0047(14) N3 0.0135(14) 0.0170(15) 0.0169(16) 0.0015(12) 0.0049(12) 0.0003(12) N4 0.0223(17) 0.0260(18) 0.0224(18) -0.0054(14) 0.0062(13) 0.0018(14) N5 0.0168(15) 0.0193(16) 0.0174(16) -0.0011(12) 0.0037(12) -0.0010(12) O1 0.0087(11) 0.0186(13) 0.0167(13) 0.0027(10) 0.0033(9) -0.0003(9) C1 0.023(2) 0.025(2) 0.021(2) 0.0008(16) 0.0058(15) 0.0057(16) C2 0.037(2) 0.024(2) 0.026(2) -0.0002(17) 0.0099(18) 0.0095(18) C3 0.0229(19) 0.0164(18) 0.0183(19) 0.0008(14) -0.0008(15) 0.0004(14) C4 0.0227(19) 0.0178(18) 0.0171(18) 0.0036(14) 0.0061(14) -0.0022(15) C5 0.0202(19) 0.025(2) 0.0197(19) -0.0006(15) 0.0093(15) 0.0009(15) C6 0.0164(17) 0.023(2) 0.0156(18) -0.0017(14) 0.0042(14) 0.0013(14) C7 0.028(2) 0.022(2) 0.034(2) -0.0094(17) 0.0087(18) -0.0021(17) C8 0.0205(19) 0.021(2) 0.023(2) -0.0041(15) 0.0048(15) -0.0026(15) C9 0.0116(16) 0.0223(19) 0.0203(19) 0.0007(15) 0.0034(13) -0.0001(14) C10 0.0170(18) 0.027(2) 0.0176(19) 0.0031(15) 0.0033(14) -0.0057(15) C11 0.067(4) 0.016(2) 0.041(3) 0.0059(19) 0.019(3) -0.001(2) C12 0.030(2) 0.032(2) 0.033(2) -0.0109(19) 0.0179(19) 0.0013(18) Cl2 0.0399(7) 0.0387(7) 0.0467(7) -0.0165(5) 0.0077(5) -0.0032(5) O2 0.048(2) 0.042(2) 0.049(2) -0.0104(17) -0.0028(18) 0.0046(17) O3 0.046(3) 0.087(4) 0.096(4) -0.058(3) -0.004(2) -0.003(2) O4 0.047(3) 0.078(3) 0.131(5) -0.065(3) -0.001(3) -0.010(2) O5 0.204(8) 0.052(3) 0.070(4) -0.004(3) -0.004(4) 0.035(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 1.921(2) 3_666 ? Fe1 O1 2.028(3) . ? Fe1 N5 2.053(3) . ? Fe1 N1 2.067(3) . ? Fe1 Cl1 2.3135(10) . ? Fe1 N3 2.360(3) . ? N1 C3 1.326(5) . ? N1 C1 1.388(5) . ? N2 C3 1.340(5) . ? N2 C2 1.384(5) . ? N2 C11 1.466(6) . ? N3 C5 1.478(5) . ? N3 C4 1.485(5) . ? N3 C10 1.494(5) . ? N4 C6 1.335(5) . ? N4 C7 1.377(5) . ? N4 C12 1.466(5) . ? N5 C6 1.328(5) . ? N5 C8 1.377(5) . ? O1 C9 1.423(4) . ? O1 Fe1 1.921(2) 3_666 ? C1 C2 1.347(6) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.492(5) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C6 1.492(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 C8 1.350(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.509(5) . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? Cl2 O3 1.294(5) . ? Cl2 O2 1.427(4) . ? Cl2 O4 1.430(4) . ? Cl2 O5 1.457(6) . ? 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 72.41(11) 3_666 . ? O1 Fe1 N5 106.57(12) 3_666 . ? O1 Fe1 N5 88.73(12) . . ? O1 Fe1 N1 107.07(12) 3_666 . ? O1 Fe1 N1 97.48(12) . . ? N5 Fe1 N1 146.11(13) . . ? O1 Fe1 Cl1 95.22(8) 3_666 . ? O1 Fe1 Cl1 166.80(8) . . ? N5 Fe1 Cl1 90.50(10) . . ? N1 Fe1 Cl1 90.48(9) . . ? O1 Fe1 N3 150.04(11) 3_666 . ? O1 Fe1 N3 77.74(10) . . ? N5 Fe1 N3 74.91(12) . . ? N1 Fe1 N3 73.98(12) . . ? Cl1 Fe1 N3 114.74(8) . . ? C3 N1 C1 106.3(3) . . ? C3 N1 Fe1 118.3(3) . . ? C1 N1 Fe1 134.2(3) . . ? C3 N2 C2 107.0(3) . . ? C3 N2 C11 126.3(4) . . ? C2 N2 C11 126.7(4) . . ? C5 N3 C4 112.8(3) . . ? C5 N3 C10 111.5(3) . . ? C4 N3 C10 109.2(3) . . ? C5 N3 Fe1 111.4(2) . . ? C4 N3 Fe1 108.4(2) . . ? C10 N3 Fe1 103.0(2) . . ? C6 N4 C7 107.6(3) . . ? C6 N4 C12 126.5(4) . . ? C7 N4 C12 125.7(4) . . ? C6 N5 C8 106.5(3) . . ? C6 N5 Fe1 120.5(3) . . ? C8 N5 Fe1 132.9(3) . . ? C9 O1 Fe1 133.0(2) . 3_666 ? C9 O1 Fe1 117.8(2) . . ? Fe1 O1 Fe1 107.59(11) 3_666 . ? C2 C1 N1 108.6(4) . . ? C2 C1 H1 125.7 . . ? N1 C1 H1 125.7 . . ? C1 C2 N2 107.1(4) . . ? C1 C2 H2 126.4 . . ? N2 C2 H2 126.4 . . ? N1 C3 N2 111.0(3) . . ? N1 C3 C4 122.4(3) . . ? N2 C3 C4 126.5(4) . . ? N3 C4 C3 106.6(3) . . ? N3 C4 H4B 110.4 . . ? C3 C4 H4B 110.4 . . ? N3 C4 H4A 110.4 . . ? C3 C4 H4A 110.4 . . ? H4B C4 H4A 108.6 . . ? N3 C5 C6 108.1(3) . . ? N3 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? N3 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N5 C6 N4 110.5(4) . . ? N5 C6 C5 122.3(3) . . ? N4 C6 C5 127.2(3) . . ? C8 C7 N4 106.6(4) . . ? C8 C7 H7 126.7 . . ? N4 C7 H7 126.7 . . ? C7 C8 N5 108.7(4) . . ? C7 C8 H8 125.6 . . ? N5 C8 H8 125.6 . . ? O1 C9 C10 107.3(3) . . ? O1 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? O1 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? H9B C9 H9A 108.5 . . ? N3 C10 C9 110.7(3) . . ? N3 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 Cl2 O2 113.4(3) . . ? O3 Cl2 O4 109.3(3) . . ? O2 Cl2 O4 110.7(3) . . ? O3 Cl2 O5 104.8(4) . . ? O2 Cl2 O5 107.6(3) . . ? O4 Cl2 O5 110.8(4) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 1.367 _refine_diff_density_min -1.090 _refine_diff_density_rms 0.126