# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1698 data_global #======================================================================= # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Michael W. Day Beckman Institute California Institute of Technology Pasadena, CA 91125 USA ; _publ_contact_author_phone '(818) 395 2734' _publ_contact_author_fax '(818) 449 4159' _publ_contact_author_email mike@xray.caltech.edu _publ_requested_journal ? _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for deposition in the Cambridge Structural Database. ; #======================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Day, Michael W.' #<--'Last name, first name' ; Beckman Institute California Institute of Technology Pasadena, CA 91125 USA ; 'Louie, Janis' ; Division of Chemistry and Chemical Engineering California Institute of Technology Pasadena, CA 91125 USA ; 'Grubbs, Robert H.' ; Division of Chemistry and Chemical Engineering California Institute of Technology Pasadena, CA 91125 USA ; #======================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #======================================================================= # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the '?' in the data_? line below # by a unique identifier. #======================================================================= # 5. CHEMICAL DATA data_jal6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H40 Cl2 Fe N4' _chemical_formula_weight 487.33 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' '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 P2(1)/n 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 11.2022(8) _cell_length_b 14.7746(10) _cell_length_c 15.1190(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.1550(10) _cell_angle_gamma 90.00 _cell_volume 2502.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93 _cell_measurement_reflns_used 6227 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.36 _exptl_crystal_description Blades _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans at 3 f settings' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23927 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.40 _reflns_number_total 5862 _reflns_number_gt 4783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT v. 6.2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type 'Full matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details 'w=1/s^2^(Fo^2^)' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Direct methods' _atom_sites_solution_hydrogens 'Difference Fourier map' _refine_ls_hydrogen_treatment Unrestrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5862 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.547 _refine_ls_restrained_S_all 1.547 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe Fe 0.13898(2) 0.783043(13) 0.311884(14) 0.01370(7) Uani 1 1 d . . . Cl1 Cl -0.00580(4) 0.89372(2) 0.31439(3) 0.02003(10) Uani 1 1 d . . . Cl2 Cl 0.28531(4) 0.81040(3) 0.20910(3) 0.02168(10) Uani 1 1 d . . . N1 N -0.04595(12) 0.62969(8) 0.34560(8) 0.0148(3) Uani 1 1 d . . . N2 N 0.05187(12) 0.59495(8) 0.22854(8) 0.0151(3) Uani 1 1 d . . . N3 N 0.21237(11) 0.79398(8) 0.51665(8) 0.0144(3) Uani 1 1 d . . . N4 N 0.30794(12) 0.69024(8) 0.44703(8) 0.0145(3) Uani 1 1 d . . . C1 C 0.04301(14) 0.65977(9) 0.29175(10) 0.0147(3) Uani 1 1 d . . . C2 C -0.07679(15) 0.67753(10) 0.42839(11) 0.0172(3) Uani 1 1 d . . . C3 C -0.03112(18) 0.62612(12) 0.50855(12) 0.0225(4) Uani 1 1 d . . . C4 C -0.20816(17) 0.70174(13) 0.43442(14) 0.0262(4) Uani 1 1 d . . . C5 C -0.09184(14) 0.54700(10) 0.31573(10) 0.0163(3) Uani 1 1 d . . . C6 C -0.19471(18) 0.49773(12) 0.35581(13) 0.0239(4) Uani 1 1 d . . . C7 C -0.02971(14) 0.52505(10) 0.24231(11) 0.0168(3) Uani 1 1 d . . . C8 C -0.04044(17) 0.44093(11) 0.18784(13) 0.0210(4) Uani 1 1 d . . . C9 C 0.13515(15) 0.60435(11) 0.15305(11) 0.0191(4) Uani 1 1 d . . . C10 C 0.06884(17) 0.62380(12) 0.06766(12) 0.0231(4) Uani 1 1 d . . . C11 C 0.22042(18) 0.52494(14) 0.14575(13) 0.0281(4) Uani 1 1 d . . . C12 C 0.22700(14) 0.75819(9) 0.43454(10) 0.0141(3) Uani 1 1 d . . . C13 C 0.14113(15) 0.87768(10) 0.53122(11) 0.0171(3) Uani 1 1 d . . . C14 C 0.02749(17) 0.86085(13) 0.58360(13) 0.0246(4) Uani 1 1 d . . . C15 C 0.21670(17) 0.95224(11) 0.57245(12) 0.0204(4) Uani 1 1 d . . . C16 C 0.28116(14) 0.74854(10) 0.57959(10) 0.0158(3) Uani 1 1 d . . . C17 C 0.28297(18) 0.76756(12) 0.67629(11) 0.0216(4) Uani 1 1 d . . . C18 C 0.34307(14) 0.68390(10) 0.53499(10) 0.0151(3) Uani 1 1 d . . . C19 C 0.43890(16) 0.62348(11) 0.57065(12) 0.0196(4) Uani 1 1 d . . . C20 C 0.34387(15) 0.62922(10) 0.37378(11) 0.0165(3) Uani 1 1 d . . . C21 C 0.47709(17) 0.63430(13) 0.35522(13) 0.0253(4) Uani 1 1 d . . . C22 C 0.29877(18) 0.53322(11) 0.38939(12) 0.0217(4) Uani 1 1 d . . . H2 H -0.0315(13) 0.7349(9) 0.4253(9) 0.004(4) Uiso 1 1 d . . . H3A H -0.0676(16) 0.5660(12) 0.5150(11) 0.027(5) Uiso 1 1 d . . . H3B H -0.0504(18) 0.6581(12) 0.5610(13) 0.035(5) Uiso 1 1 d . . . H3C H 0.0524(18) 0.6175(11) 0.5056(12) 0.025(5) Uiso 1 1 d . . . H4A H -0.2367(18) 0.7287(12) 0.3834(14) 0.035(6) Uiso 1 1 d . . . H4B H -0.2160(18) 0.7382(12) 0.4861(14) 0.038(6) Uiso 1 1 d . . . H4C H -0.2586(18) 0.6487(12) 0.4409(12) 0.035(5) Uiso 1 1 d . . . H6A H -0.2710(18) 0.5260(12) 0.3425(12) 0.035(5) Uiso 1 1 d . . . H6B H -0.1901(17) 0.4985(11) 0.4194(13) 0.034(5) Uiso 1 1 d . . . H6C H -0.1962(19) 0.4366(14) 0.3373(14) 0.047(6) Uiso 1 1 d . . . H8A H 0.0222(18) 0.3993(11) 0.2041(12) 0.030(5) Uiso 1 1 d . . . H8B H -0.0406(15) 0.4504(10) 0.1272(12) 0.017(4) Uiso 1 1 d . . . H8C H -0.1165(17) 0.4123(11) 0.1993(12) 0.025(5) Uiso 1 1 d . . . H9 H 0.1806(14) 0.6555(10) 0.1668(10) 0.011(4) Uiso 1 1 d . . . H10A H 0.0218(17) 0.5722(11) 0.0461(12) 0.026(5) Uiso 1 1 d . . . H10B H 0.1281(16) 0.6354(10) 0.0199(12) 0.023(5) Uiso 1 1 d . . . H10C H 0.0173(18) 0.6771(12) 0.0746(12) 0.037(5) Uiso 1 1 d . . . H11A H 0.2593(19) 0.5129(13) 0.1990(15) 0.043(6) Uiso 1 1 d . . . H11B H 0.2829(17) 0.5421(11) 0.1025(13) 0.035(5) Uiso 1 1 d . . . H11C H 0.1815(18) 0.4720(12) 0.1243(13) 0.037(6) Uiso 1 1 d . . . H13 H 0.1209(14) 0.8960(9) 0.4733(11) 0.008(4) Uiso 1 1 d . . . H14A H -0.0259(18) 0.8253(12) 0.5538(13) 0.033(5) Uiso 1 1 d . . . H14B H -0.0103(16) 0.9169(12) 0.5947(12) 0.025(5) Uiso 1 1 d . . . H14C H 0.0468(17) 0.8328(12) 0.6407(13) 0.034(5) Uiso 1 1 d . . . H15A H 0.2310(15) 0.9425(10) 0.6348(13) 0.024(5) Uiso 1 1 d . . . H15B H 0.1794(16) 1.0072(11) 0.5638(11) 0.024(5) Uiso 1 1 d . . . H15C H 0.2935(17) 0.9547(10) 0.5461(12) 0.021(5) Uiso 1 1 d . . . H17A H 0.3268(18) 0.7231(12) 0.7056(12) 0.031(5) Uiso 1 1 d . . . H17B H 0.205(2) 0.7712(13) 0.7027(14) 0.043(6) Uiso 1 1 d . . . H17C H 0.3262(17) 0.8249(12) 0.6892(11) 0.027(5) Uiso 1 1 d . . . H19A H 0.5207(18) 0.6447(11) 0.5549(12) 0.031(5) Uiso 1 1 d . . . H19B H 0.4280(16) 0.5592(12) 0.5492(12) 0.028(5) Uiso 1 1 d . . . H19C H 0.4359(16) 0.6238(10) 0.6349(12) 0.024(5) Uiso 1 1 d . . . H20 H 0.3045(13) 0.6505(9) 0.3241(10) 0.003(4) Uiso 1 1 d . . . H21A H 0.5006(16) 0.6961(12) 0.3444(12) 0.030(5) Uiso 1 1 d . . . H21B H 0.4915(17) 0.5987(12) 0.3038(13) 0.035(5) Uiso 1 1 d . . . H21C H 0.5276(17) 0.6106(11) 0.4035(13) 0.027(5) Uiso 1 1 d . . . H22A H 0.3285(16) 0.5081(11) 0.4458(12) 0.027(5) Uiso 1 1 d . . . H22B H 0.3198(16) 0.4957(10) 0.3433(12) 0.019(4) Uiso 1 1 d . . . H22C H 0.2108(16) 0.5318(10) 0.3917(11) 0.021(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.01280(12) 0.01460(11) 0.01370(12) -0.00049(9) 0.00166(9) 0.00041(9) Cl1 0.0205(2) 0.01864(19) 0.0209(2) -0.00261(15) -0.00169(16) 0.00549(16) Cl2 0.0242(2) 0.02028(19) 0.0206(2) 0.00011(15) 0.00877(17) -0.00366(16) N1 0.0142(7) 0.0162(6) 0.0141(7) -0.0009(5) 0.0021(5) 0.0002(5) N2 0.0137(7) 0.0164(6) 0.0153(7) -0.0012(5) 0.0030(5) -0.0003(5) N3 0.0132(7) 0.0148(6) 0.0150(7) -0.0012(5) 0.0013(5) 0.0001(5) N4 0.0143(7) 0.0142(6) 0.0151(7) -0.0005(5) 0.0025(5) -0.0004(5) C1 0.0132(8) 0.0156(7) 0.0154(8) -0.0002(6) -0.0003(6) 0.0021(6) C2 0.0172(9) 0.0178(8) 0.0166(8) -0.0024(6) 0.0046(7) -0.0001(7) C3 0.0271(11) 0.0234(9) 0.0169(9) -0.0003(7) 0.0049(8) 0.0002(8) C4 0.0202(10) 0.0335(10) 0.0250(10) -0.0041(8) 0.0044(8) 0.0039(8) C5 0.0168(9) 0.0148(7) 0.0174(8) 0.0023(6) -0.0006(7) -0.0018(6) C6 0.0236(10) 0.0246(9) 0.0237(10) 0.0002(7) 0.0046(8) -0.0068(8) C7 0.0165(9) 0.0151(7) 0.0188(9) 0.0016(6) -0.0023(7) -0.0011(6) C8 0.0232(10) 0.0190(8) 0.0210(10) -0.0015(7) -0.0010(8) -0.0010(7) C9 0.0174(9) 0.0216(8) 0.0185(9) -0.0046(7) 0.0064(7) -0.0031(7) C10 0.0247(10) 0.0235(9) 0.0213(9) 0.0022(7) 0.0061(8) 0.0021(8) C11 0.0227(11) 0.0407(11) 0.0208(10) -0.0047(9) 0.0022(8) 0.0096(9) C12 0.0114(8) 0.0140(7) 0.0170(8) -0.0012(6) 0.0032(6) -0.0019(6) C13 0.0182(9) 0.0177(8) 0.0153(9) -0.0017(6) 0.0004(7) 0.0047(7) C14 0.0195(10) 0.0249(9) 0.0295(11) -0.0092(8) 0.0056(8) 0.0011(8) C15 0.0224(10) 0.0183(8) 0.0205(10) -0.0025(7) 0.0011(8) 0.0017(7) C16 0.0155(8) 0.0164(7) 0.0156(8) 0.0010(6) -0.0007(7) -0.0031(6) C17 0.0246(10) 0.0247(9) 0.0156(9) -0.0013(7) -0.0018(8) 0.0026(8) C18 0.0134(8) 0.0158(7) 0.0161(8) 0.0011(6) 0.0000(6) -0.0027(6) C19 0.0194(10) 0.0201(8) 0.0193(9) 0.0005(7) -0.0013(7) 0.0019(7) C20 0.0183(9) 0.0182(8) 0.0131(8) -0.0008(6) 0.0015(7) 0.0047(7) C21 0.0212(10) 0.0294(10) 0.0252(10) 0.0010(8) 0.0073(8) 0.0048(8) C22 0.0265(11) 0.0179(8) 0.0207(10) -0.0032(7) 0.0008(8) 0.0011(7) _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 Fe C12 2.1298(16) . yes Fe C1 2.1363(15) . yes Fe Cl2 2.2976(4) . yes Fe Cl1 2.3035(4) . yes N1 C1 1.3630(19) . ? N1 C5 1.3998(19) . ? N1 C2 1.4792(19) . ? N2 C1 1.3569(19) . ? N2 C7 1.3950(19) . ? N2 C9 1.483(2) . ? N3 C12 1.3597(19) . ? N3 C16 1.395(2) . ? N3 C13 1.4884(19) . ? N4 C12 1.3656(19) . ? N4 C18 1.389(2) . ? N4 C20 1.4844(19) . ? C2 C3 1.518(2) . ? C2 C4 1.518(2) . ? C2 H2 0.989(14) . ? C3 H3A 0.983(17) . ? C3 H3B 0.948(19) . ? C3 H3C 0.946(19) . ? C4 H4A 0.93(2) . ? C4 H4B 0.95(2) . ? C4 H4C 0.971(19) . ? C5 C7 1.351(2) . ? C5 C6 1.493(2) . ? C6 H6A 0.97(2) . ? C6 H6B 0.963(19) . ? C6 H6C 0.95(2) . ? C7 C8 1.496(2) . ? C8 H8A 0.964(19) . ? C8 H8B 0.928(17) . ? C8 H8C 0.968(18) . ? C9 C10 1.515(3) . ? C9 C11 1.517(2) . ? C9 H9 0.935(15) . ? C10 H10A 0.981(18) . ? C10 H10B 0.997(18) . ? C10 H10C 0.983(19) . ? C11 H11A 0.93(2) . ? C11 H11B 0.992(19) . ? C11 H11C 0.95(2) . ? C13 C14 1.522(2) . ? C13 C15 1.522(2) . ? C13 H13 0.943(16) . ? C14 H14A 0.91(2) . ? C14 H14B 0.946(17) . ? C14 H14C 0.98(2) . ? C15 H15A 0.966(19) . ? C15 H15B 0.922(17) . ? C15 H15C 0.950(18) . ? C16 C18 1.360(2) . ? C16 C17 1.489(2) . ? C17 H17A 0.932(19) . ? C17 H17B 0.96(2) . ? C17 H17C 0.995(18) . ? C18 C19 1.496(2) . ? C19 H19A 0.998(19) . ? C19 H19B 1.011(17) . ? C19 H19C 0.972(18) . ? C20 C22 1.524(2) . ? C20 C21 1.521(2) . ? C20 H20 0.925(15) . ? C21 H21A 0.964(18) . ? C21 H21B 0.953(19) . ? C21 H21C 0.986(19) . ? C22 H22A 0.987(19) . ? C22 H22B 0.922(17) . ? C22 H22C 0.987(18) . ? 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 C12 Fe C1 102.05(6) . . yes C12 Fe Cl2 106.85(4) . . yes C1 Fe Cl2 114.41(4) . . yes C12 Fe Cl1 115.62(4) . . yes C1 Fe Cl1 104.68(4) . . yes Cl2 Fe Cl1 112.947(17) . . yes C1 N1 C5 111.12(12) . . ? C1 N1 C2 121.49(12) . . ? C5 N1 C2 127.13(12) . . ? C1 N2 C7 111.60(12) . . ? C1 N2 C9 121.56(13) . . ? C7 N2 C9 126.74(13) . . ? C12 N3 C16 111.59(12) . . ? C12 N3 C13 121.61(13) . . ? C16 N3 C13 126.46(13) . . ? C12 N4 C18 111.60(12) . . ? C12 N4 C20 121.65(13) . . ? C18 N4 C20 126.63(13) . . ? N2 C1 N1 104.21(12) . . ? N2 C1 Fe 131.64(11) . . ? N1 C1 Fe 124.15(10) . . ? N1 C2 C3 110.95(13) . . ? N1 C2 C4 113.09(14) . . ? C3 C2 C4 113.25(15) . . ? N1 C2 H2 104.4(8) . . ? C3 C2 H2 107.1(9) . . ? C4 C2 H2 107.4(8) . . ? C2 C3 H3A 113.1(11) . . ? C2 C3 H3B 109.9(11) . . ? H3A C3 H3B 105.8(15) . . ? C2 C3 H3C 111.1(11) . . ? H3A C3 H3C 107.2(14) . . ? H3B C3 H3C 109.5(16) . . ? C2 C4 H4A 112.6(13) . . ? C2 C4 H4B 105.9(12) . . ? H4A C4 H4B 114.1(17) . . ? C2 C4 H4C 112.4(11) . . ? H4A C4 H4C 103.4(16) . . ? H4B C4 H4C 108.5(16) . . ? C7 C5 N1 106.56(13) . . ? C7 C5 C6 128.05(14) . . ? N1 C5 C6 125.29(14) . . ? C5 C6 H6A 112.7(11) . . ? C5 C6 H6B 111.1(11) . . ? H6A C6 H6B 104.2(15) . . ? C5 C6 H6C 111.0(13) . . ? H6A C6 H6C 109.5(17) . . ? H6B C6 H6C 107.9(16) . . ? C5 C7 N2 106.50(13) . . ? C5 C7 C8 127.66(15) . . ? N2 C7 C8 125.78(14) . . ? C7 C8 H8A 109.4(11) . . ? C7 C8 H8B 114.8(10) . . ? H8A C8 H8B 110.3(15) . . ? C7 C8 H8C 109.5(10) . . ? H8A C8 H8C 108.4(14) . . ? H8B C8 H8C 104.2(15) . . ? N2 C9 C10 111.45(14) . . ? N2 C9 C11 112.41(14) . . ? C10 C9 C11 113.08(15) . . ? N2 C9 H9 104.4(9) . . ? C10 C9 H9 107.6(9) . . ? C11 C9 H9 107.4(10) . . ? C9 C10 H10A 113.4(10) . . ? C9 C10 H10B 108.9(10) . . ? H10A C10 H10B 104.5(14) . . ? C9 C10 H10C 110.3(11) . . ? H10A C10 H10C 110.0(15) . . ? H10B C10 H10C 109.5(14) . . ? C9 C11 H11A 112.2(12) . . ? C9 C11 H11B 107.2(10) . . ? H11A C11 H11B 106.9(17) . . ? C9 C11 H11C 111.9(12) . . ? H11A C11 H11C 110.5(17) . . ? H11B C11 H11C 107.9(16) . . ? N3 C12 N4 103.96(13) . . ? N3 C12 Fe 132.17(11) . . ? N4 C12 Fe 123.56(11) . . ? N3 C13 C14 113.01(13) . . ? N3 C13 C15 111.35(14) . . ? C14 C13 C15 111.74(14) . . ? N3 C13 H13 103.2(9) . . ? C14 C13 H13 109.3(10) . . ? C15 C13 H13 107.7(9) . . ? C13 C14 H14A 112.6(12) . . ? C13 C14 H14B 108.9(10) . . ? H14A C14 H14B 107.3(16) . . ? C13 C14 H14C 110.1(12) . . ? H14A C14 H14C 109.4(16) . . ? H14B C14 H14C 108.2(15) . . ? C13 C15 H15A 112.5(10) . . ? C13 C15 H15B 109.1(11) . . ? H15A C15 H15B 110.1(14) . . ? C13 C15 H15C 111.1(10) . . ? H15A C15 H15C 105.5(15) . . ? H15B C15 H15C 108.5(14) . . ? C18 C16 N3 106.32(14) . . ? C18 C16 C17 127.86(15) . . ? N3 C16 C17 125.81(14) . . ? C16 C17 H17A 109.9(11) . . ? C16 C17 H17B 114.1(13) . . ? H17A C17 H17B 108.6(17) . . ? C16 C17 H17C 111.0(10) . . ? H17A C17 H17C 104.6(15) . . ? H17B C17 H17C 108.2(15) . . ? C16 C18 N4 106.49(13) . . ? C16 C18 C19 127.35(15) . . ? N4 C18 C19 125.91(14) . . ? C18 C19 H19A 112.7(10) . . ? C18 C19 H19B 111.0(10) . . ? H19A C19 H19B 109.2(14) . . ? C18 C19 H19C 109.3(10) . . ? H19A C19 H19C 105.7(15) . . ? H19B C19 H19C 108.7(13) . . ? N4 C20 C22 111.04(13) . . ? N4 C20 C21 112.07(14) . . ? C22 C20 C21 113.59(14) . . ? N4 C20 H20 105.6(9) . . ? C22 C20 H20 106.5(9) . . ? C21 C20 H20 107.4(9) . . ? C20 C21 H21A 110.2(11) . . ? C20 C21 H21B 107.0(12) . . ? H21A C21 H21B 109.7(15) . . ? C20 C21 H21C 114.1(11) . . ? H21A C21 H21C 107.7(15) . . ? H21B C21 H21C 108.1(15) . . ? C20 C22 H22A 111.9(10) . . ? C20 C22 H22B 111.0(10) . . ? H22A C22 H22B 109.9(14) . . ? C20 C22 H22C 110.9(9) . . ? H22A C22 H22C 107.2(14) . . ? H22B C22 H22C 105.8(15) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.588 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.061