# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Leslie D. Field' _publ_contact_author_address ; School of Chemistry University of New South Wales High Street, Kensington Sydney New South Wales 2052 AUSTRALIA ; _publ_contact_author_email L.FIELD@UNSW.EDU.AU _publ_section_title ; The First Side-on-bound Metal Complex of Diazene, HN=NH ; loop_ _publ_author_name 'Leslie D. Field' 'Scott Dalgarno' 'Hsiu Li' 'Peter Turner' data_ldf139 _database_code_depnum_ccdc_archive 'CCDC 676768' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H36 Cl F6 Fe N2 P5' _chemical_formula_weight 568.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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 10.030(5) _cell_length_b 16.000(5) _cell_length_c 15.012(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.687(5) _cell_angle_gamma 90.00 _cell_volume 2404.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 947 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 26.05 _exptl_crystal_description columnar _exptl_crystal_colour orange _exptl_crystal_size_max 0.304 _exptl_crystal_size_mid 0.097 _exptl_crystal_size_min 0.091 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 173 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 23374 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5752 _reflns_number_gt 4283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _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^)+(0.03P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5752 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.331 _refine_ls_restrained_S_all 1.331 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.33670(3) 0.20389(2) 0.42062(2) 0.01436(10) Uani 1 1 d . . . P1 P 0.12925(6) 0.15720(4) 0.44340(5) 0.01908(15) Uani 1 1 d . . . P2 P 0.26993(6) 0.31599(4) 0.49158(4) 0.01876(15) Uani 1 1 d . . . P3 P 0.53036(6) 0.26625(4) 0.38933(4) 0.01779(15) Uani 1 1 d . . . P4 P 0.28301(6) 0.22630(4) 0.27854(5) 0.01981(16) Uani 1 1 d . . . N1 N 0.4159(2) 0.09041(14) 0.42542(16) 0.0213(5) Uani 1 1 d . . . H1NA H 0.494(3) 0.0804(17) 0.4126(19) 0.025(8) Uiso 1 1 d . . . H1NB H 0.369(3) 0.0416(19) 0.4251(19) 0.032(8) Uiso 1 1 d . . . N2 N 0.4220(2) 0.12743(15) 0.51329(16) 0.0220(5) Uani 1 1 d . . . H2NA H 0.510(3) 0.1284(19) 0.536(2) 0.041(9) Uiso 1 1 d . . . H2NB H 0.374(3) 0.0983(17) 0.5461(18) 0.022(8) Uiso 1 1 d . . . C1 C 0.1145(3) 0.10341(18) 0.54942(19) 0.0273(6) Uani 1 1 d . . . H1A H 0.0199 0.0959 0.5600 0.041 Uiso 1 1 calc R . . H1B H 0.1578 0.1368 0.5978 0.041 Uiso 1 1 calc R . . H1C H 0.1580 0.0486 0.5474 0.041 Uiso 1 1 calc R . . C2 C 0.0320(3) 0.08843(17) 0.3674(2) 0.0284(7) Uani 1 1 d . . . H2A H 0.0808 0.0360 0.3603 0.043 Uiso 1 1 calc R . . H2B H 0.0171 0.1158 0.3092 0.043 Uiso 1 1 calc R . . H2C H -0.0543 0.0765 0.3918 0.043 Uiso 1 1 calc R . . C3 C 0.0180(2) 0.24656(16) 0.45495(19) 0.0244(6) Uani 1 1 d . . . H3A H -0.0064 0.2712 0.3956 0.029 Uiso 1 1 calc R . . H3B H -0.0649 0.2284 0.4817 0.029 Uiso 1 1 calc R . . C4 C 0.0907(3) 0.31115(17) 0.51486(19) 0.0271(6) Uani 1 1 d . . . H4A H 0.0823 0.2961 0.5782 0.032 Uiso 1 1 calc R . . H4B H 0.0492 0.3667 0.5043 0.032 Uiso 1 1 calc R . . C5 C 0.3474(3) 0.3227(2) 0.60445(19) 0.0338(7) Uani 1 1 d . . . H5A H 0.4436 0.3323 0.6018 0.051 Uiso 1 1 calc R . . H5B H 0.3327 0.2703 0.6362 0.051 Uiso 1 1 calc R . . H5C H 0.3078 0.3691 0.6361 0.051 Uiso 1 1 calc R . . C6 C 0.2842(3) 0.42398(16) 0.4536(2) 0.0333(7) Uani 1 1 d . . . H6A H 0.2462 0.4617 0.4968 0.050 Uiso 1 1 calc R . . H6B H 0.2354 0.4304 0.3953 0.050 Uiso 1 1 calc R . . H6C H 0.3785 0.4378 0.4483 0.050 Uiso 1 1 calc R . . C7 C 0.6588(3) 0.20054(17) 0.34471(18) 0.0256(6) Uani 1 1 d . . . H7A H 0.6186 0.1656 0.2965 0.038 Uiso 1 1 calc R . . H7B H 0.6985 0.1647 0.3923 0.038 Uiso 1 1 calc R . . H7C H 0.7282 0.2359 0.3213 0.038 Uiso 1 1 calc R . . C8 C 0.6335(3) 0.32473(18) 0.4714(2) 0.0320(7) Uani 1 1 d . . . H8A H 0.7112 0.3475 0.4434 0.048 Uiso 1 1 calc R . . H8B H 0.6636 0.2876 0.5206 0.048 Uiso 1 1 calc R . . H8C H 0.5812 0.3707 0.4946 0.048 Uiso 1 1 calc R . . C9 C 0.4944(3) 0.33767(18) 0.29542(19) 0.0294(7) Uani 1 1 d . . . H9A H 0.4433 0.3867 0.3146 0.035 Uiso 1 1 calc R . . H9B H 0.5784 0.3575 0.2714 0.035 Uiso 1 1 calc R . . C10 C 0.4120(3) 0.2875(2) 0.22496(19) 0.0349(8) Uani 1 1 d . . . H10A H 0.4713 0.2494 0.1938 0.042 Uiso 1 1 calc R . . H10B H 0.3689 0.3260 0.1802 0.042 Uiso 1 1 calc R . . C11 C 0.2788(3) 0.1301(2) 0.2123(2) 0.0353(7) Uani 1 1 d . . . H11A H 0.2018 0.0963 0.2270 0.053 Uiso 1 1 calc R . . H11B H 0.3612 0.0984 0.2258 0.053 Uiso 1 1 calc R . . H11C H 0.2711 0.1443 0.1487 0.053 Uiso 1 1 calc R . . C12 C 0.1314(3) 0.27902(17) 0.23671(18) 0.0253(6) Uani 1 1 d . . . H12A H 0.1330 0.2866 0.1720 0.038 Uiso 1 1 calc R . . H12B H 0.1257 0.3337 0.2656 0.038 Uiso 1 1 calc R . . H12C H 0.0536 0.2452 0.2499 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.72733(6) 0.08391(4) 0.54693(4) 0.02334(15) Uani 1 1 d G . . P5A P 0.62584(19) -0.03135(13) 0.22403(7) 0.036(2) Uiso 0.35 1 d PG A 1 F1A F 0.6021(3) 0.06063(14) 0.18718(6) 0.039(7) Uiso 0.35 1 d PG A 1 F2A F 0.6509(3) -0.12453(11) 0.26203(11) 0.043(3) Uiso 0.35 1 d PG A 1 F3A F 0.47049(18) -0.0421(2) 0.23748(11) 0.0385(12) Uiso 0.35 1 d PG A 1 F4A F 0.64915(13) 0.00479(9) 0.32254(5) 0.0329(11) Uiso 0.35 1 d PG A 1 F5A F 0.7826(2) -0.0231(2) 0.21126(9) 0.0285(10) Uiso 0.35 1 d PG A 1 F6A F 0.6028(2) -0.06949(17) 0.12586(8) 0.0477(14) Uiso 0.35 1 d PG A 1 P5B P 0.62958(10) -0.03261(7) 0.22477(8) 0.009(2) Uiso 0.25 1 d PG B 2 F1B F 0.5914(2) 0.05656(8) 0.18374(11) 0.023(4) Uiso 0.25 1 d PG B 2 F2B F 0.6705(2) -0.12221(8) 0.26486(14) 0.033(3) Uiso 0.25 1 d PG B 2 F3B F 0.50376(19) -0.02848(13) 0.28330(14) 0.0190(13) Uiso 0.25 1 d PG B 2 F4B F 0.7211(2) 0.01050(12) 0.30237(12) 0.0338(16) Uiso 0.25 1 d PG B 2 F5B F 0.75669(16) -0.03648(13) 0.16463(16) 0.0276(14) Uiso 0.25 1 d PG B 2 F6B F 0.5410(2) -0.07628(12) 0.14528(12) 0.0192(13) Uiso 0.25 1 d PG B 2 P5C P 0.63029(10) -0.03188(7) 0.21527(8) 0.0183(10) Uiso 0.40 1 d PG B 3 F1C F 0.5990(2) 0.06227(8) 0.18694(12) 0.026(5) Uiso 0.40 1 d PG B 3 F2C F 0.6603(2) -0.12614(7) 0.24552(15) 0.0322(15) Uiso 0.40 1 d PG B 3 F3C F 0.5653(2) -0.01565(12) 0.30904(10) 0.0343(10) Uiso 0.40 1 d PG B 3 F4C F 0.77222(15) -0.00312(13) 0.25993(16) 0.0376(10) Uiso 0.40 1 d PG B 3 F5C F 0.6948(2) -0.04712(13) 0.12302(12) 0.0456(12) Uiso 0.40 1 d PG B 3 F6C F 0.48746(14) -0.06031(14) 0.17337(15) 0.0376(11) Uiso 0.40 1 d PG B 3 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 0.01248(18) 0.01441(19) 0.01623(19) 0.00134(14) 0.00117(14) 0.00078(14) P1 0.0138(3) 0.0187(3) 0.0249(4) 0.0036(3) 0.0026(3) 0.0004(3) P2 0.0180(3) 0.0183(3) 0.0199(4) -0.0017(3) 0.0007(3) 0.0030(3) P3 0.0149(3) 0.0190(3) 0.0195(4) 0.0006(3) 0.0014(3) -0.0018(3) P4 0.0162(3) 0.0259(4) 0.0172(3) 0.0012(3) 0.0003(3) 0.0025(3) N1 0.0157(12) 0.0189(12) 0.0295(13) -0.0009(10) 0.0027(10) 0.0005(10) N2 0.0178(12) 0.0240(13) 0.0242(13) 0.0061(10) 0.0009(10) 0.0015(10) C1 0.0226(14) 0.0278(15) 0.0323(16) 0.0098(13) 0.0077(12) 0.0014(12) C2 0.0223(14) 0.0224(15) 0.0399(18) 0.0013(13) -0.0022(12) -0.0044(12) C3 0.0151(13) 0.0263(15) 0.0322(16) 0.0031(12) 0.0047(11) 0.0043(11) C4 0.0211(14) 0.0280(15) 0.0329(16) -0.0020(13) 0.0083(12) 0.0051(12) C5 0.0316(16) 0.0430(19) 0.0262(16) -0.0113(14) -0.0027(13) 0.0121(14) C6 0.0358(17) 0.0194(15) 0.0450(19) -0.0011(14) 0.0051(14) 0.0040(13) C7 0.0193(14) 0.0296(15) 0.0283(16) 0.0010(12) 0.0060(12) -0.0001(11) C8 0.0241(15) 0.0344(17) 0.0373(18) -0.0082(14) 0.0006(13) -0.0092(13) C9 0.0222(14) 0.0305(16) 0.0362(17) 0.0149(13) 0.0073(12) -0.0015(12) C10 0.0239(15) 0.058(2) 0.0229(16) 0.0183(15) 0.0056(12) -0.0008(14) C11 0.0356(17) 0.0433(19) 0.0261(16) -0.0116(14) -0.0050(13) 0.0135(14) C12 0.0198(14) 0.0300(16) 0.0256(15) 0.0040(12) -0.0027(11) 0.0052(11) Cl1 0.0187(3) 0.0217(3) 0.0293(4) -0.0005(3) -0.0007(3) 0.0000(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 1.981(2) . ? Fe1 N2 2.003(2) . ? Fe1 P4 2.1955(10) . ? Fe1 P2 2.2117(9) . ? Fe1 P1 2.2574(12) . ? Fe1 P3 2.2598(11) . ? P1 C2 1.823(3) . ? P1 C1 1.824(3) . ? P1 C3 1.829(3) . ? P2 C5 1.822(3) . ? P2 C6 1.828(3) . ? P2 C4 1.855(3) . ? P3 C8 1.817(3) . ? P3 C7 1.823(3) . ? P3 C9 1.832(3) . ? P4 C12 1.816(3) . ? P4 C11 1.831(3) . ? P4 C10 1.848(3) . ? N1 N2 1.444(3) . ? N1 H1NA 0.83(3) . ? N1 H1NB 0.91(3) . ? N2 H2NA 0.92(3) . ? N2 H2NB 0.85(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.524(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.527(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? P5A F1A 1.5847 . ? P5A F4A 1.5910 . ? P5A F3A 1.5934 . ? P5A F6A 1.5981 . ? P5A F5A 1.6016 . ? P5A F2A 1.6102 . ? P5B F3B 1.5848 . ? P5B F1B 1.5911 . ? P5B F4B 1.5934 . ? P5B F2B 1.5981 . ? P5B F6B 1.6016 . ? P5B F5B 1.6102 . ? P5C F5C 1.5848 . ? P5C F1C 1.5911 . ? P5C F6C 1.5934 . ? P5C F2C 1.5981 . ? P5C F4C 1.6015 . ? P5C F3C 1.6102 . ? 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 N2 42.49(9) . . ? N1 Fe1 P4 104.93(7) . . ? N2 Fe1 P4 147.33(7) . . ? N1 Fe1 P2 149.17(7) . . ? N2 Fe1 P2 106.85(7) . . ? P4 Fe1 P2 105.81(3) . . ? N1 Fe1 P1 93.58(8) . . ? N2 Fe1 P1 92.83(8) . . ? P4 Fe1 P1 91.74(3) . . ? P2 Fe1 P1 83.38(3) . . ? N1 Fe1 P3 93.69(8) . . ? N2 Fe1 P3 94.57(8) . . ? P4 Fe1 P3 83.48(3) . . ? P2 Fe1 P3 91.89(3) . . ? P1 Fe1 P3 172.13(3) . . ? C2 P1 C1 101.03(14) . . ? C2 P1 C3 103.06(13) . . ? C1 P1 C3 101.66(13) . . ? C2 P1 Fe1 124.51(10) . . ? C1 P1 Fe1 114.56(9) . . ? C3 P1 Fe1 109.25(9) . . ? C5 P2 C6 101.38(15) . . ? C5 P2 C4 100.84(13) . . ? C6 P2 C4 101.21(13) . . ? C5 P2 Fe1 111.81(10) . . ? C6 P2 Fe1 125.73(10) . . ? C4 P2 Fe1 112.59(9) . . ? C8 P3 C7 99.30(13) . . ? C8 P3 C9 106.03(14) . . ? C7 P3 C9 100.70(13) . . ? C8 P3 Fe1 123.08(10) . . ? C7 P3 Fe1 117.30(9) . . ? C9 P3 Fe1 107.81(9) . . ? C12 P4 C11 102.30(13) . . ? C12 P4 C10 101.40(14) . . ? C11 P4 C10 101.64(15) . . ? C12 P4 Fe1 124.02(9) . . ? C11 P4 Fe1 112.70(11) . . ? C10 P4 Fe1 111.99(10) . . ? N2 N1 Fe1 69.54(13) . . ? N2 N1 H1NA 108(2) . . ? Fe1 N1 H1NA 123.3(19) . . ? N2 N1 H1NB 110.3(18) . . ? Fe1 N1 H1NB 125.4(18) . . ? H1NA N1 H1NB 109(3) . . ? N1 N2 Fe1 67.97(13) . . ? N1 N2 H2NA 108.7(19) . . ? Fe1 N2 H2NA 126.7(19) . . ? N1 N2 H2NB 108.2(19) . . ? Fe1 N2 H2NB 120.4(18) . . ? H2NA N2 H2NB 111(3) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? P1 C2 H2A 109.5 . . ? P1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? P1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 P1 108.32(18) . . ? C4 C3 H3A 110.0 . . ? P1 C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? P1 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C3 C4 P2 110.47(18) . . ? C3 C4 H4A 109.6 . . ? P2 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? P2 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? P2 C5 H5A 109.5 . . ? P2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? P2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? P2 C6 H6A 109.5 . . ? P2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? P2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? P3 C7 H7A 109.5 . . ? P3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? P3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? P3 C8 H8A 109.5 . . ? P3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? P3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 P3 106.05(19) . . ? C10 C9 H9A 110.5 . . ? P3 C9 H9A 110.5 . . ? C10 C9 H9B 110.5 . . ? P3 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C9 C10 P4 109.86(19) . . ? C9 C10 H10A 109.7 . . ? P4 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? P4 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? P4 C11 H11A 109.5 . . ? P4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? P4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P4 C12 H12A 109.5 . . ? P4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? P4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F1A P5A F4A 89.8 . . ? F1A P5A F3A 91.1 . . ? F4A P5A F3A 90.5 . . ? F1A P5A F6A 91.3 . . ? F4A P5A F6A 178.9 . . ? F3A P5A F6A 89.5 . . ? F1A P5A F5A 90.5 . . ? F4A P5A F5A 89.7 . . ? F3A P5A F5A 178.5 . . ? F6A P5A F5A 90.3 . . ? F1A P5A F2A 179.5 . . ? F4A P5A F2A 89.8 . . ? F3A P5A F2A 89.2 . . ? F6A P5A F2A 89.0 . . ? F5A P5A F2A 89.2 . . ? F3B P5B F1B 89.8 . . ? F3B P5B F4B 91.1 . . ? F1B P5B F4B 90.5 . . ? F3B P5B F2B 91.3 . . ? F1B P5B F2B 178.9 . . ? F4B P5B F2B 89.5 . . ? F3B P5B F6B 90.5 . . ? F1B P5B F6B 89.7 . . ? F4B P5B F6B 178.5 . . ? F2B P5B F6B 90.3 . . ? F3B P5B F5B 179.5 . . ? F1B P5B F5B 89.8 . . ? F4B P5B F5B 89.2 . . ? F2B P5B F5B 89.0 . . ? F6B P5B F5B 89.2 . . ? F5C P5C F1C 89.8 . . ? F5C P5C F6C 91.1 . . ? F1C P5C F6C 90.5 . . ? F5C P5C F2C 91.3 . . ? F1C P5C F2C 178.9 . . ? F6C P5C F2C 89.5 . . ? F5C P5C F4C 90.5 . . ? F1C P5C F4C 89.7 . . ? F6C P5C F4C 178.5 . . ? F2C P5C F4C 90.3 . . ? F5C P5C F3C 179.5 . . ? F1C P5C F3C 89.8 . . ? F6C P5C F3C 89.2 . . ? F2C P5C F3C 89.0 . . ? F4C P5C F3C 89.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Fe1 P1 C2 -63.37(13) . . . . ? N2 Fe1 P1 C2 -105.92(13) . . . . ? P4 Fe1 P1 C2 41.72(12) . . . . ? P2 Fe1 P1 C2 147.44(12) . . . . ? P3 Fe1 P1 C2 94.1(2) . . . . ? N1 Fe1 P1 C1 61.34(13) . . . . ? N2 Fe1 P1 C1 18.78(13) . . . . ? P4 Fe1 P1 C1 166.42(11) . . . . ? P2 Fe1 P1 C1 -87.86(11) . . . . ? P3 Fe1 P1 C1 -141.2(2) . . . . ? N1 Fe1 P1 C3 174.59(12) . . . . ? N2 Fe1 P1 C3 132.04(12) . . . . ? P4 Fe1 P1 C3 -80.33(10) . . . . ? P2 Fe1 P1 C3 25.39(10) . . . . ? P3 Fe1 P1 C3 -28.0(3) . . . . ? N1 Fe1 P2 C5 20.74(19) . . . . ? N2 Fe1 P2 C5 15.67(14) . . . . ? P4 Fe1 P2 C5 -163.44(11) . . . . ? P1 Fe1 P2 C5 106.63(12) . . . . ? P3 Fe1 P2 C5 -79.68(12) . . . . ? N1 Fe1 P2 C6 144.08(19) . . . . ? N2 Fe1 P2 C6 139.02(15) . . . . ? P4 Fe1 P2 C6 -40.09(13) . . . . ? P1 Fe1 P2 C6 -130.03(13) . . . . ? P3 Fe1 P2 C6 43.66(13) . . . . ? N1 Fe1 P2 C4 -91.96(18) . . . . ? N2 Fe1 P2 C4 -97.03(13) . . . . ? P4 Fe1 P2 C4 83.87(11) . . . . ? P1 Fe1 P2 C4 -6.07(10) . . . . ? P3 Fe1 P2 C4 167.62(10) . . . . ? N1 Fe1 P3 C8 -104.04(14) . . . . ? N2 Fe1 P3 C8 -61.44(14) . . . . ? P4 Fe1 P3 C8 151.33(12) . . . . ? P2 Fe1 P3 C8 45.63(12) . . . . ? P1 Fe1 P3 C8 98.5(3) . . . . ? N1 Fe1 P3 C7 19.55(13) . . . . ? N2 Fe1 P3 C7 62.15(13) . . . . ? P4 Fe1 P3 C7 -85.08(11) . . . . ? P2 Fe1 P3 C7 169.22(11) . . . . ? P1 Fe1 P3 C7 -137.9(2) . . . . ? N1 Fe1 P3 C9 132.22(13) . . . . ? N2 Fe1 P3 C9 174.81(12) . . . . ? P4 Fe1 P3 C9 27.59(11) . . . . ? P2 Fe1 P3 C9 -78.12(11) . . . . ? P1 Fe1 P3 C9 -25.2(3) . . . . ? N1 Fe1 P4 C12 140.64(13) . . . . ? N2 Fe1 P4 C12 144.44(17) . . . . ? P2 Fe1 P4 C12 -37.15(12) . . . . ? P1 Fe1 P4 C12 46.46(12) . . . . ? P3 Fe1 P4 C12 -127.27(12) . . . . ? N1 Fe1 P4 C11 16.50(13) . . . . ? N2 Fe1 P4 C11 20.30(18) . . . . ? P2 Fe1 P4 C11 -161.28(11) . . . . ? P1 Fe1 P4 C11 -77.67(11) . . . . ? P3 Fe1 P4 C11 108.59(11) . . . . ? N1 Fe1 P4 C10 -97.37(14) . . . . ? N2 Fe1 P4 C10 -93.57(18) . . . . ? P2 Fe1 P4 C10 84.84(12) . . . . ? P1 Fe1 P4 C10 168.46(12) . . . . ? P3 Fe1 P4 C10 -5.28(12) . . . . ? P4 Fe1 N1 N2 176.96(12) . . . . ? P2 Fe1 N1 N2 -7.2(2) . . . . ? P1 Fe1 N1 N2 -90.28(13) . . . . ? P3 Fe1 N1 N2 92.74(13) . . . . ? P4 Fe1 N2 N1 -5.4(2) . . . . ? P2 Fe1 N2 N1 176.16(12) . . . . ? P1 Fe1 N2 N1 92.22(13) . . . . ? P3 Fe1 N2 N1 -90.47(13) . . . . ? C2 P1 C3 C4 -177.78(19) . . . . ? C1 P1 C3 C4 77.8(2) . . . . ? Fe1 P1 C3 C4 -43.6(2) . . . . ? P1 C3 C4 P2 38.1(2) . . . . ? C5 P2 C4 C3 -137.9(2) . . . . ? C6 P2 C4 C3 118.1(2) . . . . ? Fe1 P2 C4 C3 -18.6(2) . . . . ? C8 P3 C9 C10 177.97(19) . . . . ? C7 P3 C9 C10 74.9(2) . . . . ? Fe1 P3 C9 C10 -48.5(2) . . . . ? P3 C9 C10 P4 44.0(2) . . . . ? C12 P4 C10 C9 111.1(2) . . . . ? C11 P4 C10 C9 -143.6(2) . . . . ? Fe1 P4 C10 C9 -23.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1NA F3C 0.83(3) 2.33(3) 2.918(3) 128(2) . N1 H1NA F4A 0.83(3) 2.45(3) 3.194(3) 150(3) . N1 H1NA F3B 0.83(3) 2.61(3) 3.031(3) 112(2) . N1 H1NB Cl1 0.91(3) 2.28(3) 3.177(3) 168(3) 3_656 N2 H2NA Cl1 0.92(3) 2.29(3) 3.150(3) 155(3) . N2 H2NB F3C 0.85(3) 2.58(3) 3.207(6) 131(2) 3_656 N2 H2NB F4A 0.85(3) 2.59(3) 3.359(6) 151(2) 3_656 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 1.207 _refine_diff_density_min -0.907 _refine_diff_density_rms 0.089 #===END data_lhl1442a _database_code_depnum_ccdc_archive 'CCDC 676769' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H34 Fe1 N2 P4' _chemical_formula_weight 386.16 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' P P 0.1023 0.0942 '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 Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 18.053(2) _cell_length_b 14.6836(17) _cell_length_c 14.5977(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3869.7(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Red _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 1.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9170 _exptl_absorpt_correction_T_max 0.9470 _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 Nonius X8Apex2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25282 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 23.29 _reflns_number_total 5088 _reflns_number_gt 4078 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystals were weakly diffracting, resulting in a lower than normal theta full value. Restraints were applied in order to place and refine hydrogen atoms of the diazenes. ; _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^)+(0.0352P)^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 mixed _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 0.01(3) _refine_ls_number_reflns 5088 _refine_ls_number_parameters 371 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.69742(5) 0.49281(5) 0.36384(7) 0.0119(3) Uani 1 1 d . . . P1 P 0.61894(9) 0.39402(11) 0.42165(13) 0.0157(4) Uani 1 1 d . . . N1 N 0.7214(4) 0.5124(4) 0.4984(5) 0.0196(16) Uani 1 1 d D . . H100 H 0.7692(15) 0.528(4) 0.499(4) 0.024 Uiso 1 1 d D . . C1 C 0.5456(3) 0.3404(4) 0.3529(5) 0.0249(17) Uani 1 1 d . . . H1A H 0.5238 0.2807 0.3897 0.037 Uiso 1 1 calc R . . H1B H 0.5686 0.3186 0.2866 0.037 Uiso 1 1 calc R . . H1C H 0.5007 0.3896 0.3413 0.037 Uiso 1 1 calc R . . Fe2 Fe 0.04885(5) 0.01262(6) 0.55167(7) 0.0136(3) Uani 1 1 d . . . P2 P 0.76326(9) 0.37403(12) 0.33027(12) 0.0162(5) Uani 1 1 d . . . N2 N 0.6812(3) 0.5877(3) 0.4617(4) 0.0164(13) Uani 1 1 d D . . H101 H 0.6360(17) 0.580(4) 0.484(4) 0.020 Uiso 1 1 d D . . C2 C 0.5653(3) 0.4225(4) 0.5240(4) 0.0199(16) Uani 1 1 d . . . H2A H 0.5397 0.3604 0.5518 0.030 Uiso 1 1 calc R . . H2B H 0.5217 0.4717 0.5060 0.030 Uiso 1 1 calc R . . H2C H 0.6021 0.4526 0.5759 0.030 Uiso 1 1 calc R . . P3 P 0.77664(9) 0.59556(11) 0.31419(13) 0.0156(4) Uani 1 1 d . . . N3 N 0.0383(4) -0.0151(4) 0.4176(5) 0.0212(16) Uani 1 1 d D . . H102 H -0.0089(17) -0.029(4) 0.400(4) 0.025 Uiso 1 1 d D . . C3 C 0.6721(4) 0.2933(4) 0.4565(4) 0.0211(17) Uani 1 1 d . . . H3A H 0.7071 0.3091 0.5161 0.025 Uiso 1 1 calc R . . H3B H 0.6347 0.2371 0.4746 0.025 Uiso 1 1 calc R . . P4 P 0.62978(9) 0.53661(11) 0.24981(13) 0.0163(4) Uani 1 1 d . . . N4 N 0.0771(3) -0.0851(3) 0.4613(4) 0.0198(14) Uani 1 1 d D . . H103 H 0.1251(15) -0.075(4) 0.446(4) 0.024 Uiso 1 1 d D . . C4 C 0.7204(3) 0.2673(4) 0.3734(5) 0.0211(16) Uani 1 1 d . . . H4A H 0.6862 0.2358 0.3197 0.025 Uiso 1 1 calc R . . H4B H 0.7635 0.2185 0.3940 0.025 Uiso 1 1 calc R . . P5 P 0.12772(9) 0.11395(12) 0.50046(13) 0.0178(4) Uani 1 1 d . . . C5 C 0.7877(4) 0.3388(4) 0.2138(4) 0.0228(17) Uani 1 1 d . . . H5A H 0.8091 0.3977 0.1755 0.034 Uiso 1 1 calc R . . H5B H 0.7381 0.3120 0.1791 0.034 Uiso 1 1 calc R . . H5C H 0.8304 0.2854 0.2167 0.034 Uiso 1 1 calc R . . P6 P -0.02566(9) 0.12627(12) 0.56759(13) 0.0180(5) Uani 1 1 d . . . C6 C 0.8546(3) 0.3680(4) 0.3878(5) 0.0242(18) Uani 1 1 d . . . H6A H 0.8828 0.3045 0.3681 0.036 Uiso 1 1 calc R . . H6B H 0.8468 0.3693 0.4625 0.036 Uiso 1 1 calc R . . H6C H 0.8886 0.4266 0.3669 0.036 Uiso 1 1 calc R . . P7 P -0.02960(9) -0.09211(11) 0.59882(13) 0.0159(4) Uani 1 1 d . . . C7 C 0.8463(3) 0.5752(4) 0.2243(4) 0.0176(16) Uani 1 1 d . . . H7A H 0.8187 0.5494 0.1623 0.026 Uiso 1 1 calc R . . H7B H 0.8868 0.5247 0.2485 0.026 Uiso 1 1 calc R . . H7C H 0.8749 0.6394 0.2083 0.026 Uiso 1 1 calc R . . P8 P 0.11203(9) -0.02426(12) 0.67222(13) 0.0166(4) Uani 1 1 d . . . C8 C 0.8327(4) 0.6599(4) 0.3978(5) 0.0219(18) Uani 1 1 d . . . H8A H 0.8739 0.6142 0.4290 0.033 Uiso 1 1 calc R . . H8B H 0.7963 0.6876 0.4515 0.033 Uiso 1 1 calc R . . H8C H 0.8612 0.7161 0.3627 0.033 Uiso 1 1 calc R . . C9 C 0.7209(4) 0.6847(4) 0.2592(5) 0.0201(16) Uani 1 1 d . . . H9A H 0.6882 0.7218 0.3107 0.024 Uiso 1 1 calc R . . H9B H 0.7570 0.7335 0.2234 0.024 Uiso 1 1 calc R . . C10 C 0.6699(3) 0.6372(4) 0.1913(5) 0.0230(17) Uani 1 1 d . . . H10A H 0.7012 0.6158 0.1304 0.028 Uiso 1 1 calc R . . H10B H 0.6255 0.6838 0.1694 0.028 Uiso 1 1 calc R . . C11 C 0.6082(4) 0.4667(4) 0.1484(5) 0.0249(17) Uani 1 1 d . . . H11A H 0.5730 0.4090 0.1687 0.037 Uiso 1 1 calc R . . H11B H 0.6600 0.4409 0.1183 0.037 Uiso 1 1 calc R . . H11C H 0.5788 0.5085 0.0975 0.037 Uiso 1 1 calc R . . C12 C 0.5375(3) 0.5799(4) 0.2777(5) 0.0229(17) Uani 1 1 d . . . H12A H 0.5093 0.6012 0.2145 0.034 Uiso 1 1 calc R . . H12B H 0.5425 0.6385 0.3242 0.034 Uiso 1 1 calc R . . H12C H 0.5051 0.5259 0.3113 0.034 Uiso 1 1 calc R . . C13 C 0.1949(3) 0.0829(4) 0.4116(4) 0.0251(18) Uani 1 1 d . . . H13A H 0.1662 0.0476 0.3554 0.038 Uiso 1 1 calc R . . H13B H 0.2372 0.0376 0.4410 0.038 Uiso 1 1 calc R . . H13C H 0.2216 0.1449 0.3851 0.038 Uiso 1 1 calc R . . C14 C 0.1885(3) 0.1811(4) 0.5753(5) 0.0246(18) Uani 1 1 d . . . H14A H 0.2298 0.1360 0.6071 0.037 Uiso 1 1 calc R . . H14B H 0.1552 0.2139 0.6291 0.037 Uiso 1 1 calc R . . H14C H 0.2169 0.2336 0.5346 0.037 Uiso 1 1 calc R . . C15 C 0.0731(3) 0.2070(4) 0.4490(5) 0.0242(17) Uani 1 1 d . . . H15A H 0.1089 0.2657 0.4335 0.029 Uiso 1 1 calc R . . H15B H 0.0466 0.1841 0.3852 0.029 Uiso 1 1 calc R . . C16 C 0.0145(3) 0.2333(4) 0.5200(5) 0.0229(17) Uani 1 1 d . . . H16A H -0.0293 0.2743 0.4876 0.027 Uiso 1 1 calc R . . H16B H 0.0398 0.2737 0.5751 0.027 Uiso 1 1 calc R . . C17 C -0.1126(3) 0.1210(4) 0.5010(5) 0.0199(16) Uani 1 1 d . . . H17A H -0.1467 0.1812 0.5164 0.030 Uiso 1 1 calc R . . H17B H -0.1433 0.0589 0.5195 0.030 Uiso 1 1 calc R . . H17C H -0.0996 0.1197 0.4274 0.030 Uiso 1 1 calc R . . C18 C -0.0629(4) 0.1689(4) 0.6770(5) 0.0292(18) Uani 1 1 d . . . H18A H -0.0170 0.1820 0.7247 0.044 Uiso 1 1 calc R . . H18B H -0.1003 0.1176 0.7067 0.044 Uiso 1 1 calc R . . H18C H -0.0937 0.2324 0.6649 0.044 Uiso 1 1 calc R . . C19 C -0.0775(4) -0.1616(4) 0.5150(5) 0.0260(19) Uani 1 1 d . . . H19A H -0.0389 -0.1806 0.4599 0.039 Uiso 1 1 calc R . . H104 H -0.1241 -0.1228 0.4859 0.039 Uiso 1 1 calc R . . H19C H -0.0987 -0.2236 0.5482 0.039 Uiso 1 1 calc R . . C20 C -0.1051(3) -0.0689(4) 0.6803(5) 0.0240(17) Uani 1 1 d . . . H20A H -0.1314 -0.1335 0.7005 0.036 Uiso 1 1 calc R . . H20B H -0.1465 -0.0245 0.6477 0.036 Uiso 1 1 calc R . . H20C H -0.0825 -0.0350 0.7414 0.036 Uiso 1 1 calc R . . C21 C 0.0231(4) -0.1762(4) 0.6664(5) 0.0216(16) Uani 1 1 d . . . H21A H -0.0146 -0.2230 0.7023 0.026 Uiso 1 1 calc R . . H21B H 0.0599 -0.2163 0.6218 0.026 Uiso 1 1 calc R . . C22 C 0.0686(4) -0.1198(4) 0.7355(5) 0.0193(16) Uani 1 1 d . . . H22A H 0.1115 -0.1625 0.7673 0.023 Uiso 1 1 calc R . . H22B H 0.0323 -0.0934 0.7898 0.023 Uiso 1 1 calc R . . C23 C 0.2043(3) -0.0745(4) 0.6488(5) 0.0259(18) Uani 1 1 d . . . H23A H 0.2394 -0.0238 0.6142 0.039 Uiso 1 1 calc R . . H23B H 0.1980 -0.1346 0.6044 0.039 Uiso 1 1 calc R . . H23C H 0.2304 -0.0949 0.7137 0.039 Uiso 1 1 calc R . . C24 C 0.1351(4) 0.0510(4) 0.7696(5) 0.0263(18) Uani 1 1 d . . . H24A H 0.1611 0.0107 0.8243 0.040 Uiso 1 1 calc R . . H24B H 0.0842 0.0829 0.7958 0.040 Uiso 1 1 calc R . . H24C H 0.1738 0.1042 0.7466 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0121(6) 0.0144(5) 0.0092(6) -0.0012(4) 0.0001(5) -0.0006(4) P1 0.0161(10) 0.0172(9) 0.0137(11) -0.0005(7) 0.0021(8) -0.0032(8) N1 0.017(3) 0.024(3) 0.017(4) -0.008(3) -0.005(3) 0.001(3) C1 0.020(4) 0.029(4) 0.026(4) -0.011(3) -0.007(4) -0.011(3) Fe2 0.0132(6) 0.0145(5) 0.0132(7) -0.0010(5) -0.0003(5) -0.0005(4) P2 0.0152(11) 0.0185(10) 0.0148(11) -0.0003(8) 0.0007(8) 0.0024(7) N2 0.019(3) 0.020(3) 0.010(3) -0.004(2) 0.002(3) 0.001(3) C2 0.025(4) 0.026(4) 0.009(4) -0.004(3) 0.005(3) -0.003(3) P3 0.0160(10) 0.0180(10) 0.0128(11) -0.0035(8) 0.0037(9) -0.0025(7) N3 0.020(3) 0.025(3) 0.018(4) -0.001(3) -0.002(3) 0.000(3) C3 0.031(4) 0.020(4) 0.013(4) 0.001(3) 0.004(3) 0.004(3) P4 0.0159(10) 0.0186(9) 0.0145(11) -0.0019(9) -0.0016(8) 0.0027(8) N4 0.017(3) 0.022(3) 0.020(4) -0.003(3) 0.000(3) 0.005(3) C4 0.026(4) 0.017(4) 0.020(4) 0.003(3) -0.002(4) 0.006(3) P5 0.0173(10) 0.0219(10) 0.0143(11) 0.0030(8) -0.0026(9) -0.0028(8) C5 0.026(4) 0.026(4) 0.017(4) -0.004(3) 0.003(3) 0.005(3) P6 0.0194(10) 0.0166(10) 0.0179(11) -0.0015(8) 0.0012(9) 0.0018(8) C6 0.015(4) 0.025(4) 0.033(5) -0.002(3) -0.005(3) 0.005(3) P7 0.0156(10) 0.0174(10) 0.0146(11) -0.0005(8) -0.0014(9) -0.0037(8) C7 0.021(4) 0.017(4) 0.015(4) -0.001(3) 0.006(3) -0.006(3) P8 0.0143(10) 0.0194(9) 0.0161(11) 0.0013(9) -0.0002(8) -0.0007(8) C8 0.015(4) 0.033(4) 0.018(4) -0.006(3) -0.001(3) -0.011(3) C9 0.029(4) 0.010(3) 0.021(4) 0.005(3) 0.008(4) 0.001(3) C10 0.026(4) 0.019(4) 0.024(4) 0.011(3) -0.005(4) 0.003(3) C11 0.036(4) 0.026(4) 0.012(4) -0.003(3) -0.012(4) 0.009(3) C12 0.023(4) 0.018(4) 0.028(5) -0.003(3) -0.003(3) 0.004(3) C13 0.026(4) 0.031(4) 0.018(4) 0.006(3) 0.002(3) -0.008(3) C14 0.027(4) 0.020(4) 0.027(5) 0.006(3) -0.005(3) -0.008(3) C15 0.026(4) 0.018(4) 0.029(5) 0.004(3) -0.001(4) -0.007(3) C16 0.022(4) 0.014(4) 0.033(4) 0.004(3) -0.008(4) 0.001(3) C17 0.017(4) 0.023(4) 0.020(4) 0.002(3) -0.001(3) 0.004(3) C18 0.037(5) 0.028(4) 0.023(4) -0.007(3) 0.003(4) 0.016(3) C19 0.027(4) 0.022(4) 0.029(5) 0.003(3) -0.006(4) -0.009(3) C20 0.016(4) 0.032(4) 0.024(4) 0.007(3) 0.007(3) -0.002(3) C21 0.024(4) 0.017(4) 0.024(4) 0.002(3) -0.001(4) -0.002(3) C22 0.023(4) 0.020(4) 0.015(4) 0.004(3) -0.002(3) 0.000(3) C23 0.014(4) 0.033(4) 0.031(5) 0.008(3) -0.012(3) 0.000(3) C24 0.031(4) 0.036(4) 0.012(4) 0.001(3) 0.000(3) -0.011(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 N2 2.016(5) . ? Fe1 N1 2.032(7) . ? Fe1 P4 2.162(2) . ? Fe1 P2 2.1667(19) . ? Fe1 P1 2.196(2) . ? Fe1 P3 2.2015(19) . ? P1 C2 1.829(6) . ? P1 C3 1.835(6) . ? P1 C1 1.838(6) . ? N1 N2 1.427(7) . ? Fe2 N3 2.009(7) . ? Fe2 N4 2.014(5) . ? Fe2 P6 2.1560(19) . ? Fe2 P8 2.166(2) . ? Fe2 P5 2.191(2) . ? Fe2 P7 2.201(2) . ? P2 C5 1.831(6) . ? P2 C6 1.853(6) . ? P2 C4 1.858(6) . ? P3 C9 1.836(6) . ? P3 C7 1.842(6) . ? P3 C8 1.845(6) . ? N3 N4 1.398(8) . ? C3 C4 1.542(9) . ? P4 C12 1.830(6) . ? P4 C11 1.843(6) . ? P4 C10 1.854(6) . ? P5 C13 1.833(6) . ? P5 C14 1.836(6) . ? P5 C15 1.845(6) . ? P6 C18 1.843(7) . ? P6 C17 1.849(6) . ? P6 C16 1.864(6) . ? P7 C19 1.814(7) . ? P7 C20 1.840(6) . ? P7 C21 1.845(6) . ? P8 C24 1.848(6) . ? P8 C22 1.853(6) . ? P8 C23 1.854(6) . ? C9 C10 1.521(8) . ? C15 C16 1.530(9) . ? C21 C22 1.542(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N1 41.3(2) . . ? N2 Fe1 P4 104.93(16) . . ? N1 Fe1 P4 145.34(18) . . ? N2 Fe1 P2 142.75(17) . . ? N1 Fe1 P2 102.45(17) . . ? P4 Fe1 P2 112.03(9) . . ? N2 Fe1 P1 95.17(16) . . ? N1 Fe1 P1 81.91(19) . . ? P4 Fe1 P1 97.35(7) . . ? P2 Fe1 P1 84.79(7) . . ? N2 Fe1 P3 81.63(16) . . ? N1 Fe1 P3 94.75(18) . . ? P4 Fe1 P3 84.81(8) . . ? P2 Fe1 P3 96.94(8) . . ? P1 Fe1 P3 176.52(10) . . ? C2 P1 C3 103.6(3) . . ? C2 P1 C1 99.4(3) . . ? C3 P1 C1 100.5(3) . . ? C2 P1 Fe1 120.3(2) . . ? C3 P1 Fe1 107.5(2) . . ? C1 P1 Fe1 122.5(2) . . ? N2 N1 Fe1 68.8(3) . . ? N3 Fe2 N4 40.7(2) . . ? N3 Fe2 P6 101.71(19) . . ? N4 Fe2 P6 141.24(18) . . ? N3 Fe2 P8 142.3(2) . . ? N4 Fe2 P8 102.74(17) . . ? P6 Fe2 P8 115.75(9) . . ? N3 Fe2 P5 82.36(19) . . ? N4 Fe2 P5 95.49(17) . . ? P6 Fe2 P5 85.21(7) . . ? P8 Fe2 P5 96.01(8) . . ? N3 Fe2 P7 95.84(19) . . ? N4 Fe2 P7 82.53(16) . . ? P6 Fe2 P7 96.07(8) . . ? P8 Fe2 P7 84.84(8) . . ? P5 Fe2 P7 177.98(10) . . ? C5 P2 C6 101.1(3) . . ? C5 P2 C4 100.2(3) . . ? C6 P2 C4 100.2(3) . . ? C5 P2 Fe1 124.7(2) . . ? C6 P2 Fe1 115.1(2) . . ? C4 P2 Fe1 112.0(2) . . ? N1 N2 Fe1 69.9(3) . . ? C9 P3 C7 100.2(3) . . ? C9 P3 C8 103.0(3) . . ? C7 P3 C8 100.4(3) . . ? C9 P3 Fe1 106.0(2) . . ? C7 P3 Fe1 124.5(2) . . ? C8 P3 Fe1 119.3(2) . . ? N4 N3 Fe2 69.9(4) . . ? C4 C3 P1 106.1(4) . . ? C12 P4 C11 100.4(3) . . ? C12 P4 C10 100.5(3) . . ? C11 P4 C10 99.0(3) . . ? C12 P4 Fe1 116.5(2) . . ? C11 P4 Fe1 124.9(2) . . ? C10 P4 Fe1 111.8(2) . . ? N3 N4 Fe2 69.5(3) . . ? C3 C4 P2 107.0(4) . . ? C13 P5 C14 99.2(3) . . ? C13 P5 C15 104.5(3) . . ? C14 P5 C15 99.4(3) . . ? C13 P5 Fe2 120.2(2) . . ? C14 P5 Fe2 123.4(2) . . ? C15 P5 Fe2 107.1(2) . . ? C18 P6 C17 99.2(3) . . ? C18 P6 C16 100.3(3) . . ? C17 P6 C16 99.7(3) . . ? C18 P6 Fe2 125.7(2) . . ? C17 P6 Fe2 116.1(2) . . ? C16 P6 Fe2 111.7(2) . . ? C19 P7 C20 100.8(3) . . ? C19 P7 C21 103.3(3) . . ? C20 P7 C21 99.2(3) . . ? C19 P7 Fe2 119.3(3) . . ? C20 P7 Fe2 123.3(2) . . ? C21 P7 Fe2 107.6(2) . . ? C24 P8 C22 99.5(3) . . ? C24 P8 C23 100.2(3) . . ? C22 P8 C23 99.9(3) . . ? C24 P8 Fe2 126.5(2) . . ? C22 P8 Fe2 111.8(2) . . ? C23 P8 Fe2 115.0(2) . . ? C10 C9 P3 106.9(4) . . ? C9 C10 P4 107.5(4) . . ? C16 C15 P5 106.3(4) . . ? C15 C16 P6 108.0(4) . . ? C22 C21 P7 105.3(4) . . ? C21 C22 P8 107.8(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.379 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.083 #===END data_LHL1467 _database_code_depnum_ccdc_archive 'CCDC 676770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H42 Fe1 N2 P4' _chemical_formula_weight 538.35 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' P P 0.1023 0.0942 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.9761(13) _cell_length_b 16.911(3) _cell_length_c 17.931(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.899(7) _cell_angle_gamma 90.00 _cell_volume 2681.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7918 _exptl_absorpt_correction_T_max 0.9228 _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 Nonius X8Apex2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8539 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 23.72 _reflns_number_total 1999 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystals were weakly diffracting, resulting in a lower than normal theta full value. ; _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^)+(0.0171P)^2^+6.4767P] 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 1999 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.23491(3) 0.2500 0.01095(14) Uani 1 2 d S . . N1 N 0.5791(2) 0.12416(12) 0.26197(11) 0.0143(5) Uani 1 1 d . . . C1 C 0.5937(3) -0.01264(16) 0.42565(14) 0.0217(6) Uani 1 1 d . . . H1 H 0.5305 -0.0494 0.4453 0.026 Uiso 1 1 calc R . . P2 P 0.40801(7) 0.23647(4) 0.35813(3) 0.01567(17) Uani 1 1 d . . . C2 C 0.5390(3) 0.02724(15) 0.35888(14) 0.0167(6) Uani 1 1 d . . . H2 H 0.4397 0.0163 0.3330 0.020 Uiso 1 1 calc R . . P3 P 0.67774(7) 0.32224(4) 0.28587(4) 0.01622(17) Uani 1 1 d . . . C3 C 0.6273(3) 0.08322(15) 0.32909(13) 0.0142(6) Uani 1 1 d . . . C4 C 0.7782(3) 0.09218(15) 0.36600(14) 0.0193(6) Uani 1 1 d . . . H4 H 0.8443 0.1262 0.3449 0.023 Uiso 1 1 calc R . . C5 C 0.8314(3) 0.05212(16) 0.43264(15) 0.0238(7) Uani 1 1 d . . . H5 H 0.9327 0.0601 0.4574 0.029 Uiso 1 1 calc R . . C6 C 0.7387(3) 0.00034(16) 0.46387(15) 0.0232(7) Uani 1 1 d . . . H10 H 0.7744 -0.0256 0.5105 0.028 Uiso 1 1 calc R . . C7 C 0.3190(3) 0.33194(16) 0.37124(14) 0.0207(6) Uani 1 1 d . . . H7A H 0.2375 0.3241 0.4013 0.025 Uiso 1 1 calc R . . H7B H 0.3951 0.3680 0.3998 0.025 Uiso 1 1 calc R . . C8 C 0.5246(3) 0.22197(18) 0.45151(14) 0.0255(7) Uani 1 1 d . . . H8A H 0.6058 0.2614 0.4593 0.038 Uiso 1 1 calc R . . H8B H 0.5686 0.1688 0.4544 0.038 Uiso 1 1 calc R . . H8C H 0.4617 0.2280 0.4907 0.038 Uiso 1 1 calc R . . C9 C 0.2518(3) 0.16861(16) 0.36495(15) 0.0225(6) Uani 1 1 d . . . H9A H 0.2072 0.1821 0.4095 0.034 Uiso 1 1 calc R . . H9B H 0.2899 0.1142 0.3697 0.034 Uiso 1 1 calc R . . H9C H 0.1746 0.1732 0.3193 0.034 Uiso 1 1 calc R . . C10 C 0.7470(3) 0.36966(17) 0.20477(15) 0.0267(7) Uani 1 1 d . . . H10A H 0.7202 0.4265 0.2033 0.032 Uiso 1 1 calc R . . H10B H 0.8587 0.3657 0.2126 0.032 Uiso 1 1 calc R . . C11 C 0.8581(3) 0.28909(18) 0.34034(16) 0.0290(7) Uani 1 1 d . . . H11A H 0.9255 0.3346 0.3524 0.044 Uiso 1 1 calc R . . H11B H 0.9049 0.2508 0.3104 0.044 Uiso 1 1 calc R . . H11C H 0.8405 0.2641 0.3874 0.044 Uiso 1 1 calc R . . C12 C 0.6519(3) 0.40952(18) 0.34315(18) 0.0369(8) Uani 1 1 d . . . H12A H 0.6413 0.3928 0.3943 0.055 Uiso 1 1 calc R . . H12B H 0.5606 0.4380 0.3198 0.055 Uiso 1 1 calc R . . H12C H 0.7398 0.4444 0.3459 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0097(3) 0.0118(3) 0.0117(3) 0.000 0.0028(2) 0.000 N1 0.0099(10) 0.0142(12) 0.0187(11) 0.0011(9) 0.0022(9) -0.0005(9) C1 0.0343(17) 0.0131(15) 0.0218(14) -0.0001(12) 0.0161(13) 0.0039(13) P2 0.0166(4) 0.0166(4) 0.0148(3) -0.0007(3) 0.0058(3) 0.0005(3) C2 0.0171(14) 0.0134(14) 0.0213(14) -0.0023(11) 0.0079(11) 0.0035(11) P3 0.0143(3) 0.0166(4) 0.0182(3) -0.0023(3) 0.0042(3) -0.0032(3) C3 0.0169(13) 0.0116(14) 0.0155(13) -0.0026(11) 0.0066(10) 0.0035(11) C4 0.0198(14) 0.0159(15) 0.0229(14) 0.0011(12) 0.0054(11) 0.0000(12) C5 0.0227(15) 0.0223(16) 0.0235(15) -0.0014(12) -0.0044(12) 0.0056(13) C6 0.0390(17) 0.0150(15) 0.0155(13) 0.0004(11) 0.0041(13) 0.0084(13) C7 0.0237(14) 0.0192(15) 0.0213(14) -0.0039(12) 0.0101(12) 0.0000(12) C8 0.0262(15) 0.0348(18) 0.0161(14) -0.0004(12) 0.0055(12) 0.0036(13) C9 0.0230(15) 0.0222(16) 0.0254(14) 0.0004(12) 0.0135(12) -0.0014(13) C10 0.0259(15) 0.0263(17) 0.0288(16) 0.0037(13) 0.0067(13) -0.0089(13) C11 0.0209(15) 0.0342(18) 0.0294(16) 0.0041(14) -0.0031(12) -0.0099(13) C12 0.0322(17) 0.0277(18) 0.056(2) -0.0225(16) 0.0218(15) -0.0160(15) _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 2.002(2) 2_655 ? Fe1 N1 2.002(2) . ? Fe1 P3 2.1880(8) . ? Fe1 P3 2.1880(8) 2_655 ? Fe1 P2 2.2342(7) 2_655 ? Fe1 P2 2.2342(7) . ? N1 C3 1.391(3) . ? N1 N1 1.412(4) 2_655 ? C1 C6 1.380(4) . ? C1 C2 1.388(4) . ? P2 C8 1.832(3) . ? P2 C9 1.832(3) . ? P2 C7 1.834(3) . ? C2 C3 1.399(4) . ? P3 C11 1.829(3) . ? P3 C12 1.836(3) . ? P3 C10 1.859(3) . ? C3 C4 1.410(3) . ? C4 C5 1.385(4) . ? C5 C6 1.391(4) . ? C7 C10 1.529(4) 2_655 ? C10 C7 1.529(4) 2_655 ? 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 N1 41.30(11) 2_655 . ? N1 Fe1 P3 152.94(6) 2_655 . ? N1 Fe1 P3 111.88(6) . . ? N1 Fe1 P3 111.88(6) 2_655 2_655 ? N1 Fe1 P3 152.94(6) . 2_655 ? P3 Fe1 P3 95.10(4) . 2_655 ? N1 Fe1 P2 95.46(6) 2_655 2_655 ? N1 Fe1 P2 85.81(6) . 2_655 ? P3 Fe1 P2 83.54(3) . 2_655 ? P3 Fe1 P2 95.54(3) 2_655 2_655 ? N1 Fe1 P2 85.81(6) 2_655 . ? N1 Fe1 P2 95.46(6) . . ? P3 Fe1 P2 95.54(3) . . ? P3 Fe1 P2 83.54(3) 2_655 . ? P2 Fe1 P2 178.65(5) 2_655 . ? C3 N1 N1 114.2(2) . 2_655 ? C3 N1 Fe1 127.61(16) . . ? N1 N1 Fe1 69.35(5) 2_655 . ? C6 C1 C2 121.0(3) . . ? C8 P2 C9 100.28(13) . . ? C8 P2 C7 101.16(13) . . ? C9 P2 C7 100.81(12) . . ? C8 P2 Fe1 123.60(9) . . ? C9 P2 Fe1 116.86(9) . . ? C7 P2 Fe1 110.83(9) . . ? C1 C2 C3 121.2(2) . . ? C11 P3 C12 97.66(14) . . ? C11 P3 C10 99.53(13) . . ? C12 P3 C10 100.50(14) . . ? C11 P3 Fe1 118.93(10) . . ? C12 P3 Fe1 123.45(10) . . ? C10 P3 Fe1 112.73(9) . . ? N1 C3 C2 123.7(2) . . ? N1 C3 C4 118.9(2) . . ? C2 C3 C4 117.1(2) . . ? C5 C4 C3 120.9(2) . . ? C4 C5 C6 120.9(2) . . ? C1 C6 C5 118.6(2) . . ? C10 C7 P2 111.33(18) 2_655 . ? C7 C10 P3 112.73(18) 2_655 . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 23.72 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.303 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.054