# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound1S _database_code_depnum_ccdc_archive 'CCDC 925610' #TrackingRef 'compound1S.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 F6 Fe N6 O6 P2 S2' _chemical_formula_weight 768.41 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.52730(10) _cell_length_b 7.21510(10) _cell_length_c 16.4648(3) _cell_angle_alpha 97.988(2) _cell_angle_beta 90.106(2) _cell_angle_gamma 96.513(2) _cell_volume 762.81(2) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details 'Sortav, Blessing 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _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 14897 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4351 _reflns_number_gt 3393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 positional and isotropic displacement parameters of H1 were freely refined. ; _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^)+(0.0469P)^2^+0.1250P] 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 4351 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.5000 0.5000 0.01546(10) Uani 1 2 d S . . S1 S -0.23723(7) 0.73667(7) 0.23242(3) 0.01974(12) Uani 1 1 d . . . P1 P 0.47701(8) 0.21833(7) 0.22958(3) 0.01722(12) Uani 1 1 d . . . F1 F 0.1351(2) 0.8678(2) 0.28675(10) 0.0416(4) Uani 1 1 d . . . O1 O -0.1790(2) 0.5539(2) 0.24517(10) 0.0289(3) Uani 1 1 d . . . N1 N 0.3919(2) 0.3194(2) 0.32114(9) 0.0158(3) Uani 1 1 d . . . C1 C 0.4817(3) 0.3056(3) 0.39942(11) 0.0177(4) Uani 1 1 d . . . F2 F -0.0920(2) 0.8686(2) 0.38021(8) 0.0459(4) Uani 1 1 d . . . O2 O -0.1851(3) 0.7877(3) 0.15388(10) 0.0417(4) Uani 1 1 d . . . N2 N 0.2309(2) 0.4141(2) 0.32086(9) 0.0177(3) Uani 1 1 d . . . C2 C 0.6921(3) 0.3617(3) 0.42043(11) 0.0203(4) Uani 1 1 d . . . H2 H 0.7941 0.4175 0.3874 0.024 Uiso 1 1 calc R . . F3 F -0.0781(2) 1.07419(19) 0.29748(10) 0.0430(4) Uani 1 1 d . . . O3 O -0.4372(2) 0.7689(2) 0.26254(10) 0.0304(4) Uani 1 1 d . . . N3 N 0.1738(3) 0.4060(2) 0.24386(9) 0.0173(3) Uani 1 1 d . . . C3 C 0.7200(3) 0.3175(3) 0.50092(12) 0.0250(4) Uani 1 1 d . . . H3 H 0.8462 0.3391 0.5314 0.030 Uiso 1 1 calc R . . C4 C 0.5306(4) 0.2368(3) 0.52818(12) 0.0249(4) Uani 1 1 d . . . H4 H 0.5076 0.1957 0.5801 0.030 Uiso 1 1 calc R . . C5 C 0.3789(3) 0.2269(3) 0.46485(12) 0.0217(4) Uani 1 1 d . . . H5 H 0.2378 0.1777 0.4661 0.026 Uiso 1 1 calc R . . C6 C 0.2818(3) 0.3117(3) 0.18557(11) 0.0154(3) Uani 1 1 d . . . C7 C 0.2252(3) 0.3016(3) 0.09587(11) 0.0173(4) Uani 1 1 d . . . C8 C 0.2610(3) 0.5005(3) 0.07185(13) 0.0258(4) Uani 1 1 d . . . H8A H 0.1689 0.5810 0.1031 0.039 Uiso 1 1 calc R . . H8B H 0.2324 0.4946 0.0130 0.039 Uiso 1 1 calc R . . H8C H 0.4046 0.5530 0.0841 0.039 Uiso 1 1 calc R . . C9 C -0.0010(3) 0.2210(3) 0.08113(12) 0.0237(4) Uani 1 1 d . . . H9A H -0.0230 0.0959 0.0986 0.036 Uiso 1 1 calc R . . H9B H -0.0356 0.2108 0.0226 0.036 Uiso 1 1 calc R . . H9C H -0.0892 0.3047 0.1128 0.036 Uiso 1 1 calc R . . C10 C 0.3637(3) 0.1729(3) 0.04576(12) 0.0251(4) Uani 1 1 d . . . H10A H 0.5083 0.2258 0.0548 0.038 Uiso 1 1 calc R . . H10B H 0.3277 0.1628 -0.0126 0.038 Uiso 1 1 calc R . . H10C H 0.3439 0.0475 0.0630 0.038 Uiso 1 1 calc R . . C11 C -0.0589(3) 0.8943(3) 0.30263(14) 0.0248(4) Uani 1 1 d . . . H1 H 0.067(4) 0.468(4) 0.2373(15) 0.035(7) 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 Fe1 0.0207(2) 0.01416(19) 0.01186(18) 0.00096(14) -0.00107(14) 0.00444(15) S1 0.0181(2) 0.0205(2) 0.0211(2) 0.00409(19) -0.00031(18) 0.00288(18) P1 0.0187(2) 0.0194(2) 0.0139(2) 0.00100(18) -0.00075(17) 0.00523(19) F1 0.0169(6) 0.0388(8) 0.0661(10) 0.0000(7) -0.0001(6) -0.0004(6) O1 0.0216(8) 0.0187(7) 0.0469(10) 0.0038(7) 0.0001(7) 0.0047(6) N1 0.0186(8) 0.0142(7) 0.0141(7) 0.0007(6) -0.0019(6) 0.0018(6) C1 0.0259(10) 0.0166(9) 0.0107(8) -0.0001(7) -0.0019(7) 0.0055(8) F2 0.0472(9) 0.0630(11) 0.0229(7) 0.0028(7) -0.0072(6) -0.0096(8) O2 0.0515(11) 0.0509(11) 0.0225(8) 0.0121(8) 0.0005(8) -0.0037(9) N2 0.0199(8) 0.0182(8) 0.0148(7) 0.0010(6) -0.0022(6) 0.0036(6) C2 0.0232(10) 0.0219(10) 0.0164(9) -0.0001(8) -0.0009(7) 0.0093(8) F3 0.0425(8) 0.0189(7) 0.0649(11) -0.0021(7) -0.0025(7) 0.0013(6) O3 0.0176(7) 0.0337(9) 0.0408(9) 0.0048(7) -0.0003(6) 0.0072(6) N3 0.0179(8) 0.0194(8) 0.0144(7) 0.0006(6) -0.0027(6) 0.0035(6) C3 0.0336(12) 0.0254(11) 0.0178(9) -0.0012(8) -0.0060(8) 0.0164(9) C4 0.0432(13) 0.0175(10) 0.0160(9) 0.0034(8) -0.0019(8) 0.0108(9) C5 0.0325(11) 0.0137(9) 0.0186(9) 0.0023(7) 0.0007(8) 0.0010(8) C6 0.0152(9) 0.0143(8) 0.0158(8) 0.0008(7) 0.0003(7) -0.0003(7) C7 0.0185(9) 0.0201(9) 0.0137(8) 0.0030(7) -0.0012(7) 0.0036(7) C8 0.0304(12) 0.0274(11) 0.0205(10) 0.0081(9) 0.0004(8) 0.0016(9) C9 0.0205(10) 0.0296(11) 0.0194(9) 0.0014(8) -0.0044(8) -0.0017(8) C10 0.0270(11) 0.0314(12) 0.0165(9) -0.0011(8) 0.0000(8) 0.0071(9) C11 0.0204(10) 0.0233(10) 0.0306(11) 0.0048(9) 0.0011(8) 0.0012(8) _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 C1 2.0100(18) 2_666 ? Fe1 C1 2.0100(18) . ? Fe1 C5 2.042(2) 2_666 ? Fe1 C5 2.042(2) . ? Fe1 C4 2.047(2) 2_666 ? Fe1 C4 2.047(2) . ? Fe1 C2 2.0522(19) 2_666 ? Fe1 C2 2.0522(19) . ? Fe1 C3 2.0567(19) 2_666 ? Fe1 C3 2.0567(19) . ? S1 O2 1.4245(16) . ? S1 O3 1.4293(15) . ? S1 O1 1.4550(15) . ? S1 C11 1.820(2) . ? P1 N1 1.7036(16) . ? P1 C6 1.7114(19) . ? F1 C11 1.323(2) . ? N1 N2 1.317(2) . ? N1 C1 1.436(2) . ? C1 C2 1.415(3) . ? C1 C5 1.421(3) . ? F2 C11 1.330(2) . ? N2 N3 1.312(2) . ? C2 C3 1.421(3) . ? C2 H2 0.9500 . ? F3 C11 1.332(2) . ? N3 C6 1.346(2) . ? N3 H1 0.89(3) . ? C3 C4 1.408(3) . ? C3 H3 0.9500 . ? C4 C5 1.426(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.511(2) . ? C7 C10 1.530(3) . ? C7 C9 1.530(3) . ? C7 C8 1.534(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C1 Fe1 C1 180.0 2_666 . ? C1 Fe1 C5 41.05(8) 2_666 2_666 ? C1 Fe1 C5 138.95(8) . 2_666 ? C1 Fe1 C5 138.95(8) 2_666 . ? C1 Fe1 C5 41.05(8) . . ? C5 Fe1 C5 180.000(1) 2_666 . ? C1 Fe1 C4 68.15(8) 2_666 2_666 ? C1 Fe1 C4 111.85(8) . 2_666 ? C5 Fe1 C4 40.80(8) 2_666 2_666 ? C5 Fe1 C4 139.20(8) . 2_666 ? C1 Fe1 C4 111.85(8) 2_666 . ? C1 Fe1 C4 68.15(8) . . ? C5 Fe1 C4 139.20(8) 2_666 . ? C5 Fe1 C4 40.80(8) . . ? C4 Fe1 C4 180.00(10) 2_666 . ? C1 Fe1 C2 40.77(8) 2_666 2_666 ? C1 Fe1 C2 139.23(8) . 2_666 ? C5 Fe1 C2 69.25(8) 2_666 2_666 ? C5 Fe1 C2 110.75(8) . 2_666 ? C4 Fe1 C2 68.37(8) 2_666 2_666 ? C4 Fe1 C2 111.63(8) . 2_666 ? C1 Fe1 C2 139.23(8) 2_666 . ? C1 Fe1 C2 40.77(8) . . ? C5 Fe1 C2 110.75(8) 2_666 . ? C5 Fe1 C2 69.25(8) . . ? C4 Fe1 C2 111.63(8) 2_666 . ? C4 Fe1 C2 68.37(8) . . ? C2 Fe1 C2 180.00(9) 2_666 . ? C1 Fe1 C3 67.76(8) 2_666 2_666 ? C1 Fe1 C3 112.24(8) . 2_666 ? C5 Fe1 C3 68.31(9) 2_666 2_666 ? C5 Fe1 C3 111.69(9) . 2_666 ? C4 Fe1 C3 40.11(9) 2_666 2_666 ? C4 Fe1 C3 139.89(9) . 2_666 ? C2 Fe1 C3 40.47(7) 2_666 2_666 ? C2 Fe1 C3 139.53(7) . 2_666 ? C1 Fe1 C3 112.24(8) 2_666 . ? C1 Fe1 C3 67.76(8) . . ? C5 Fe1 C3 111.69(9) 2_666 . ? C5 Fe1 C3 68.31(9) . . ? C4 Fe1 C3 139.89(9) 2_666 . ? C4 Fe1 C3 40.11(9) . . ? C2 Fe1 C3 139.53(7) 2_666 . ? C2 Fe1 C3 40.47(7) . . ? C3 Fe1 C3 180.000(1) 2_666 . ? O2 S1 O3 117.54(11) . . ? O2 S1 O1 113.88(11) . . ? O3 S1 O1 113.21(9) . . ? O2 S1 C11 103.95(11) . . ? O3 S1 C11 104.64(10) . . ? O1 S1 C11 101.15(9) . . ? N1 P1 C6 86.27(8) . . ? N2 N1 C1 117.29(15) . . ? N2 N1 P1 118.35(12) . . ? C1 N1 P1 124.35(13) . . ? C2 C1 C5 110.21(17) . . ? C2 C1 N1 123.72(17) . . ? C5 C1 N1 125.99(18) . . ? C2 C1 Fe1 71.22(11) . . ? C5 C1 Fe1 70.69(11) . . ? N1 C1 Fe1 127.16(13) . . ? N3 N2 N1 106.71(15) . . ? C1 C2 C3 106.12(18) . . ? C1 C2 Fe1 68.01(10) . . ? C3 C2 Fe1 69.93(11) . . ? C1 C2 H2 126.9 . . ? C3 C2 H2 126.9 . . ? Fe1 C2 H2 126.7 . . ? N2 N3 C6 118.51(16) . . ? N2 N3 H1 113.4(17) . . ? C6 N3 H1 128.1(17) . . ? C4 C3 C2 109.03(19) . . ? C4 C3 Fe1 69.59(12) . . ? C2 C3 Fe1 69.59(11) . . ? C4 C3 H3 125.5 . . ? C2 C3 H3 125.5 . . ? Fe1 C3 H3 126.9 . . ? C3 C4 C5 108.64(18) . . ? C3 C4 Fe1 70.30(12) . . ? C5 C4 Fe1 69.40(11) . . ? C3 C4 H4 125.7 . . ? C5 C4 H4 125.7 . . ? Fe1 C4 H4 126.2 . . ? C1 C5 C4 106.00(19) . . ? C1 C5 Fe1 68.26(11) . . ? C4 C5 Fe1 69.79(12) . . ? C1 C5 H5 127.0 . . ? C4 C5 H5 127.0 . . ? Fe1 C5 H5 126.5 . . ? N3 C6 C7 120.61(16) . . ? N3 C6 P1 110.15(13) . . ? C7 C6 P1 129.24(14) . . ? C6 C7 C10 108.25(15) . . ? C6 C7 C9 109.81(15) . . ? C10 C7 C9 109.74(17) . . ? C6 C7 C8 108.77(16) . . ? C10 C7 C8 110.01(16) . . ? C9 C7 C8 110.23(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? F1 C11 F2 107.38(18) . . ? F1 C11 F3 107.44(17) . . ? F2 C11 F3 107.22(19) . . ? F1 C11 S1 111.59(15) . . ? F2 C11 S1 111.63(15) . . ? F3 C11 S1 111.34(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.443 _refine_diff_density_min -1.051 _refine_diff_density_rms 0.079 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 925611' #TrackingRef 'compound3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Fe N6 P2' _chemical_formula_weight 468.26 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 P(2)1/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 17.573(4) _cell_length_b 10.129(2) _cell_length_c 12.835(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.64(3) _cell_angle_gamma 90.00 _cell_volume 2280.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.735 _exptl_absorpt_correction_T_max 0.922 _exptl_absorpt_process_details 'Sortav, Blessing 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _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 9466 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4970 _reflns_number_gt 4094 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.0334P)^2^+1.1781P] 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 4970 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Fe1 Fe 0.419856(14) 0.71565(2) 0.922319(17) 0.01685(8) Uani 1 1 d . . . P1 P 0.16393(3) 0.67859(6) 0.93129(4) 0.02901(13) Uani 1 1 d . . . N1 N 0.25430(8) 0.66212(15) 0.98334(11) 0.0202(3) Uani 1 1 d . . . C1 C 0.31870(10) 0.62138(17) 0.92888(13) 0.0195(4) Uani 1 1 d . . . P2 P 0.29043(3) 1.04489(6) 0.85869(4) 0.02979(13) Uani 1 1 d . . . N2 N 0.26480(9) 0.68289(17) 1.08695(11) 0.0275(4) Uani 1 1 d . . . C2 C 0.37819(10) 0.53780(17) 0.96923(13) 0.0196(4) Uani 1 1 d . . . H2 H 0.3834 0.5011 1.0374 0.024 Uiso 1 1 calc R . . N3 N 0.20029(9) 0.71294(17) 1.12656(12) 0.0291(4) Uani 1 1 d . . . C3 C 0.42870(10) 0.51937(17) 0.88790(13) 0.0211(4) Uani 1 1 d . . . H3 H 0.4741 0.4682 0.8925 0.025 Uiso 1 1 calc R . . N4 N 0.38151(8) 0.99853(14) 0.84154(11) 0.0192(3) Uani 1 1 d . . . C4 C 0.39959(10) 0.59053(18) 0.79885(13) 0.0211(4) Uani 1 1 d . . . H4 H 0.4222 0.5943 0.7336 0.025 Uiso 1 1 calc R . . N5 N 0.41266(8) 1.04798(16) 0.75661(11) 0.0245(3) Uani 1 1 d . . . C5 C 0.33114(10) 0.65531(18) 0.82302(13) 0.0207(4) Uani 1 1 d . . . H5 H 0.2999 0.7101 0.7780 0.025 Uiso 1 1 calc R . . N6 N 0.36439(8) 1.12501(16) 0.70435(11) 0.0247(3) Uani 1 1 d . . . C6 C 0.42879(10) 0.91457(17) 0.90685(13) 0.0191(4) Uani 1 1 d . . . C7 C 0.41502(10) 0.88134(17) 1.01183(13) 0.0210(4) Uani 1 1 d . . . H7 H 0.3729 0.9087 1.0493 0.025 Uiso 1 1 calc R . . C8 C 0.47635(11) 0.79940(17) 1.04986(14) 0.0230(4) Uani 1 1 d . . . H8 H 0.4825 0.7625 1.1179 0.028 Uiso 1 1 calc R . . C9 C 0.52701(10) 0.78196(18) 0.96856(14) 0.0226(4) Uani 1 1 d . . . H9 H 0.5727 0.7316 0.9731 0.027 Uiso 1 1 calc R . . C10 C 0.49726(10) 0.85312(17) 0.87923(14) 0.0210(4) Uani 1 1 d . . . H10 H 0.5192 0.8584 0.8136 0.025 Uiso 1 1 calc R . . C11 C 0.13994(10) 0.71619(19) 1.05544(14) 0.0246(4) Uani 1 1 d . . . C12 C 0.06207(11) 0.7506(2) 1.09278(16) 0.0329(5) Uani 1 1 d . . . C13 C 0.00189(13) 0.7430(3) 1.0010(2) 0.0514(7) Uani 1 1 d . . . H13A H 0.0007 0.6534 0.9722 0.077 Uiso 1 1 calc R . . H13B H 0.0148 0.8057 0.9468 0.077 Uiso 1 1 calc R . . H13C H -0.0483 0.7651 1.0254 0.077 Uiso 1 1 calc R . . C14 C 0.04271(13) 0.6522(3) 1.17764(18) 0.0456(6) Uani 1 1 d . . . H14A H 0.0819 0.6565 1.2354 0.068 Uiso 1 1 calc R . . H14B H 0.0409 0.5628 1.1485 0.068 Uiso 1 1 calc R . . H14C H -0.0070 0.6745 1.2033 0.068 Uiso 1 1 calc R . . C15 C 0.06453(13) 0.8906(2) 1.13781(18) 0.0445(6) Uani 1 1 d . . . H15A H 0.0148 0.9124 1.1638 0.067 Uiso 1 1 calc R . . H15B H 0.0765 0.9534 1.0831 0.067 Uiso 1 1 calc R . . H15C H 0.1038 0.8955 1.1953 0.067 Uiso 1 1 calc R . . C16 C 0.29583(10) 1.13594(18) 0.74681(13) 0.0213(4) Uani 1 1 d . . . C17 C 0.23591(11) 1.22362(19) 0.69225(14) 0.0247(4) Uani 1 1 d . . . C18 C 0.21884(13) 1.1746(2) 0.58020(16) 0.0410(6) Uani 1 1 d . . . H18A H 0.2661 1.1732 0.5436 0.062 Uiso 1 1 calc R . . H18B H 0.1821 1.2340 0.5437 0.062 Uiso 1 1 calc R . . H18C H 0.1975 1.0853 0.5816 0.062 Uiso 1 1 calc R . . C19 C 0.16267(13) 1.2207(3) 0.74986(19) 0.0494(6) Uani 1 1 d . . . H19A H 0.1439 1.1297 0.7528 0.074 Uiso 1 1 calc R . . H19B H 0.1241 1.2761 0.7128 0.074 Uiso 1 1 calc R . . H19C H 0.1730 1.2543 0.8209 0.074 Uiso 1 1 calc R . . C20 C 0.26677(14) 1.3648(2) 0.6894(2) 0.0480(6) Uani 1 1 d . . . H20A H 0.2783 1.3962 0.7609 0.072 Uiso 1 1 calc R . . H20B H 0.2284 1.4224 0.6542 0.072 Uiso 1 1 calc R . . H20C H 0.3133 1.3661 0.6513 0.072 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 0.01912(14) 0.01644(13) 0.01504(12) -0.00063(9) 0.00137(9) -0.00051(10) P1 0.0200(2) 0.0447(3) 0.0219(2) -0.0039(2) -0.00197(19) 0.0042(2) N1 0.0183(7) 0.0242(8) 0.0180(7) -0.0010(6) 0.0000(6) 0.0003(6) C1 0.0187(8) 0.0213(9) 0.0188(8) -0.0011(7) 0.0020(7) -0.0012(7) P2 0.0242(3) 0.0353(3) 0.0309(3) 0.0108(2) 0.0102(2) 0.0079(2) N2 0.0209(8) 0.0419(10) 0.0196(7) -0.0053(7) 0.0020(6) 0.0012(7) C2 0.0233(9) 0.0169(9) 0.0187(8) 0.0019(7) 0.0021(7) -0.0020(7) N3 0.0202(8) 0.0423(10) 0.0249(8) -0.0059(7) 0.0026(6) 0.0014(7) C3 0.0234(9) 0.0159(9) 0.0240(8) -0.0034(7) 0.0026(7) -0.0011(7) N4 0.0202(7) 0.0173(7) 0.0203(7) 0.0003(6) 0.0031(6) -0.0006(6) C4 0.0251(9) 0.0211(9) 0.0175(8) -0.0033(7) 0.0039(7) -0.0044(7) N5 0.0220(8) 0.0293(9) 0.0225(7) 0.0059(6) 0.0044(6) 0.0022(7) C5 0.0237(9) 0.0211(9) 0.0170(8) -0.0006(7) -0.0012(7) -0.0017(7) N6 0.0217(8) 0.0294(9) 0.0230(7) 0.0054(7) 0.0017(6) 0.0026(7) C6 0.0213(9) 0.0164(8) 0.0193(8) -0.0020(7) -0.0011(7) -0.0003(7) C7 0.0268(9) 0.0192(9) 0.0173(8) -0.0053(7) 0.0019(7) 0.0001(7) C8 0.0291(10) 0.0200(9) 0.0193(8) -0.0031(7) -0.0034(7) -0.0001(8) C9 0.0226(9) 0.0185(9) 0.0263(9) -0.0029(7) -0.0017(7) -0.0006(7) C10 0.0197(9) 0.0184(9) 0.0250(9) -0.0014(7) 0.0011(7) -0.0021(7) C11 0.0199(9) 0.0284(10) 0.0257(9) -0.0024(8) 0.0023(7) 0.0008(8) C12 0.0189(9) 0.0473(13) 0.0328(10) -0.0067(9) 0.0026(8) 0.0041(9) C13 0.0209(11) 0.086(2) 0.0468(13) -0.0141(13) -0.0031(10) 0.0113(12) C14 0.0288(11) 0.0589(16) 0.0510(13) -0.0011(12) 0.0160(10) -0.0010(11) C15 0.0367(12) 0.0489(15) 0.0483(13) -0.0100(11) 0.0056(10) 0.0127(11) C16 0.0213(9) 0.0204(9) 0.0224(8) -0.0030(7) 0.0023(7) -0.0004(7) C17 0.0222(9) 0.0252(10) 0.0266(9) 0.0000(8) 0.0008(7) 0.0036(8) C18 0.0375(12) 0.0497(14) 0.0343(11) -0.0044(10) -0.0105(10) 0.0135(11) C19 0.0307(12) 0.0712(18) 0.0473(14) 0.0138(13) 0.0098(10) 0.0200(12) C20 0.0456(14) 0.0237(11) 0.0722(16) 0.0045(11) -0.0157(12) 0.0056(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 2.0243(18) . ? Fe1 C6 2.0317(18) . ? Fe1 C7 2.0387(17) . ? Fe1 C4 2.0428(17) . ? Fe1 C5 2.0435(18) . ? Fe1 C8 2.0442(18) . ? Fe1 C3 2.0448(18) . ? Fe1 C10 2.0471(18) . ? Fe1 C2 2.0495(18) . ? Fe1 C9 2.0511(19) . ? P1 N1 1.6914(15) . ? P1 C11 1.7168(19) . ? N1 N2 1.348(2) . ? N1 C1 1.428(2) . ? C1 C2 1.417(2) . ? C1 C5 1.432(2) . ? P2 N4 1.6956(15) . ? P2 C16 1.7144(18) . ? N2 N3 1.307(2) . ? C2 C3 1.425(2) . ? N3 C11 1.355(2) . ? C3 C4 1.419(2) . ? N4 N5 1.347(2) . ? N4 C6 1.424(2) . ? C4 C5 1.422(2) . ? N5 N6 1.306(2) . ? N6 C16 1.358(2) . ? C6 C10 1.420(2) . ? C6 C7 1.424(2) . ? C7 C8 1.422(3) . ? C8 C9 1.425(3) . ? C9 C10 1.425(2) . ? C11 C12 1.519(3) . ? C12 C14 1.530(3) . ? C12 C15 1.531(3) . ? C12 C13 1.534(3) . ? C16 C17 1.515(3) . ? C17 C19 1.525(3) . ? C17 C20 1.531(3) . ? C17 C18 1.533(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe1 C6 123.05(7) . . ? C1 Fe1 C7 107.26(7) . . ? C6 Fe1 C7 40.97(7) . . ? C1 Fe1 C4 68.24(7) . . ? C6 Fe1 C4 123.38(7) . . ? C7 Fe1 C4 159.47(7) . . ? C1 Fe1 C5 41.21(7) . . ? C6 Fe1 C5 107.23(7) . . ? C7 Fe1 C5 122.70(7) . . ? C4 Fe1 C5 40.72(7) . . ? C1 Fe1 C8 123.06(7) . . ? C6 Fe1 C8 68.29(7) . . ? C7 Fe1 C8 40.76(7) . . ? C4 Fe1 C8 158.53(7) . . ? C5 Fe1 C8 159.40(7) . . ? C1 Fe1 C3 68.24(7) . . ? C6 Fe1 C3 159.35(7) . . ? C7 Fe1 C3 158.23(7) . . ? C4 Fe1 C3 40.63(7) . . ? C5 Fe1 C3 68.89(7) . . ? C8 Fe1 C3 122.47(7) . . ? C1 Fe1 C10 158.82(7) . . ? C6 Fe1 C10 40.73(7) . . ? C7 Fe1 C10 69.18(7) . . ? C4 Fe1 C10 107.37(7) . . ? C5 Fe1 C10 121.91(7) . . ? C8 Fe1 C10 68.70(7) . . ? C3 Fe1 C10 122.83(7) . . ? C1 Fe1 C2 40.71(7) . . ? C6 Fe1 C2 158.71(7) . . ? C7 Fe1 C2 121.98(7) . . ? C4 Fe1 C2 68.57(7) . . ? C5 Fe1 C2 69.37(7) . . ? C8 Fe1 C2 107.09(7) . . ? C3 Fe1 C2 40.73(7) . . ? C10 Fe1 C2 158.94(7) . . ? C1 Fe1 C9 159.20(7) . . ? C6 Fe1 C9 68.18(7) . . ? C7 Fe1 C9 68.76(7) . . ? C4 Fe1 C9 122.63(7) . . ? C5 Fe1 C9 158.19(7) . . ? C8 Fe1 C9 40.72(7) . . ? C3 Fe1 C9 107.45(7) . . ? C10 Fe1 C9 40.70(7) . . ? C2 Fe1 C9 122.78(7) . . ? N1 P1 C11 86.28(8) . . ? N2 N1 C1 117.71(14) . . ? N2 N1 P1 116.14(12) . . ? C1 N1 P1 126.04(11) . . ? C2 C1 N1 125.63(15) . . ? C2 C1 C5 109.68(15) . . ? N1 C1 C5 124.65(15) . . ? C2 C1 Fe1 70.60(10) . . ? N1 C1 Fe1 127.53(12) . . ? C5 C1 Fe1 70.11(10) . . ? N4 P2 C16 86.41(8) . . ? N3 N2 N1 110.63(14) . . ? C1 C2 C3 106.85(15) . . ? C1 C2 Fe1 68.69(10) . . ? C3 C2 Fe1 69.46(10) . . ? N2 N3 C11 113.86(15) . . ? C4 C3 C2 108.31(15) . . ? C4 C3 Fe1 69.61(10) . . ? C2 C3 Fe1 69.81(10) . . ? N5 N4 C6 116.52(14) . . ? N5 N4 P2 115.95(11) . . ? C6 N4 P2 127.53(12) . . ? C3 C4 C5 108.99(15) . . ? C3 C4 Fe1 69.76(10) . . ? C5 C4 Fe1 69.67(10) . . ? N6 N5 N4 110.71(14) . . ? C4 C5 C1 106.18(15) . . ? C4 C5 Fe1 69.62(10) . . ? C1 C5 Fe1 68.68(10) . . ? N5 N6 C16 113.98(15) . . ? C10 C6 N4 125.95(15) . . ? C10 C6 C7 109.28(15) . . ? N4 C6 C7 124.76(15) . . ? C10 C6 Fe1 70.22(10) . . ? N4 C6 Fe1 127.16(12) . . ? C7 C6 Fe1 69.78(10) . . ? C8 C7 C6 106.98(16) . . ? C8 C7 Fe1 69.82(10) . . ? C6 C7 Fe1 69.25(10) . . ? C7 C8 C9 108.43(15) . . ? C7 C8 Fe1 69.41(10) . . ? C9 C8 Fe1 69.90(10) . . ? C8 C9 C10 108.19(16) . . ? C8 C9 Fe1 69.38(10) . . ? C10 C9 Fe1 69.50(10) . . ? C6 C10 C9 107.11(15) . . ? C6 C10 Fe1 69.05(10) . . ? C9 C10 Fe1 69.80(10) . . ? N3 C11 C12 118.38(16) . . ? N3 C11 P1 113.08(14) . . ? C12 C11 P1 128.54(14) . . ? C11 C12 C14 108.70(18) . . ? C11 C12 C15 109.11(17) . . ? C14 C12 C15 109.66(18) . . ? C11 C12 C13 109.71(17) . . ? C14 C12 C13 109.9(2) . . ? C15 C12 C13 109.8(2) . . ? N6 C16 C17 118.08(16) . . ? N6 C16 P2 112.95(13) . . ? C17 C16 P2 128.97(14) . . ? C16 C17 C19 110.35(16) . . ? C16 C17 C20 108.79(16) . . ? C19 C17 C20 109.95(19) . . ? C16 C17 C18 109.44(16) . . ? C19 C17 C18 109.13(18) . . ? C20 C17 C18 109.16(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.371 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.057 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 925612' #TrackingRef 'compound4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Fe N6 P2' _chemical_formula_weight 384.10 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' 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 P2(1)/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 9.1840(18) _cell_length_b 13.517(3) _cell_length_c 12.433(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.27(3) _cell_angle_gamma 90.00 _cell_volume 1543.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'Sortav, Blessing 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _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 5131 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2722 _reflns_number_gt 2117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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. ; _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^)+(0.0334P)^2^+0.5946P] 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 2722 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Fe1 Fe 0.73845(4) 0.12733(3) 0.08438(3) 0.02020(14) Uani 1 1 d . . . P1 P 1.01134(9) 0.06516(6) 0.37894(6) 0.0287(2) Uani 1 1 d . . . N1 N 0.9801(2) 0.04612(16) 0.24620(18) 0.0209(5) Uani 1 1 d . . . C1 C 0.8410(3) 0.03681(19) 0.1934(2) 0.0201(6) Uani 1 1 d . . . P2 P 1.06639(8) 0.29045(6) 0.21650(6) 0.0273(2) Uani 1 1 d . . . N2 N 1.0980(2) 0.02665(17) 0.18642(19) 0.0268(6) Uani 1 1 d . . . C2 C 0.7071(3) 0.0719(2) 0.2356(2) 0.0240(7) Uani 1 1 d . . . H2 H 0.6955 0.1096 0.2993 0.029 Uiso 1 1 calc R . . N3 N 1.2164(3) 0.02597(17) 0.2473(2) 0.0301(6) Uani 1 1 d . . . C3 C 0.5944(3) 0.0394(2) 0.1637(2) 0.0269(7) Uani 1 1 d . . . H3 H 0.4933 0.0515 0.1712 0.032 Uiso 1 1 calc R . . N4 N 1.0194(2) 0.25410(16) 0.09035(18) 0.0227(5) Uani 1 1 d . . . C4 C 0.6586(3) -0.0142(2) 0.0789(2) 0.0261(7) Uani 1 1 d . . . H4 H 0.6077 -0.0444 0.0202 0.031 Uiso 1 1 calc R . . N5 N 1.1306(2) 0.22898(17) 0.02504(19) 0.0269(6) Uani 1 1 d . . . C5 C 0.8120(3) -0.0152(2) 0.0965(2) 0.0235(7) Uani 1 1 d . . . H5 H 0.8819 -0.0451 0.0517 0.028 Uiso 1 1 calc R . . N6 N 1.2552(2) 0.23908(18) 0.0765(2) 0.0296(6) Uani 1 1 d . . . C6 C 0.8751(3) 0.23999(19) 0.0472(2) 0.0216(6) Uani 1 1 d . . . C7 C 0.7457(3) 0.2788(2) 0.0917(2) 0.0241(7) Uani 1 1 d . . . H7 H 0.7392 0.3182 0.1547 0.029 Uiso 1 1 calc R . . C8 C 0.6277(3) 0.2474(2) 0.0239(2) 0.0291(7) Uani 1 1 d . . . H8 H 0.5278 0.2622 0.0336 0.035 Uiso 1 1 calc R . . C9 C 0.6855(3) 0.1898(2) -0.0609(2) 0.0298(7) Uani 1 1 d . . . H9 H 0.6306 0.1598 -0.1178 0.036 Uiso 1 1 calc R . . C10 C 0.8389(3) 0.1848(2) -0.0464(2) 0.0258(7) Uani 1 1 d . . . H10 H 0.9050 0.1508 -0.0911 0.031 Uiso 1 1 calc R . . C11 C 1.1918(3) 0.0449(2) 0.3531(2) 0.0287(7) Uani 1 1 d . . . C12 C 1.3192(3) 0.0463(2) 0.4307(3) 0.0405(9) Uani 1 1 d . . . H12A H 1.3916 -0.0024 0.4084 0.061 Uiso 1 1 calc R . . H12B H 1.2861 0.0298 0.5029 0.061 Uiso 1 1 calc R . . H12C H 1.3631 0.1124 0.4315 0.061 Uiso 1 1 calc R . . C13 C 1.2427(3) 0.2707(2) 0.1800(2) 0.0274(7) Uani 1 1 d . . . C14 C 1.3788(3) 0.2836(2) 0.2489(3) 0.0365(8) Uani 1 1 d . . . H14A H 1.4415 0.2255 0.2412 0.055 Uiso 1 1 calc R . . H14B H 1.3520 0.2908 0.3244 0.055 Uiso 1 1 calc R . . H14C H 1.4311 0.3428 0.2259 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 0.0153(2) 0.0249(2) 0.0203(2) 0.00204(18) -0.00124(16) 0.00084(17) P1 0.0290(5) 0.0364(5) 0.0205(4) -0.0013(3) -0.0054(4) 0.0020(4) N1 0.0184(13) 0.0226(12) 0.0217(13) 0.0025(10) 0.0002(10) 0.0005(10) C1 0.0177(15) 0.0211(15) 0.0214(15) 0.0041(12) -0.0001(12) -0.0017(12) P2 0.0217(4) 0.0304(4) 0.0299(4) -0.0062(4) 0.0008(3) 0.0008(3) N2 0.0175(13) 0.0350(15) 0.0276(14) -0.0054(12) -0.0027(11) 0.0015(11) C2 0.0236(16) 0.0267(16) 0.0219(16) 0.0041(13) 0.0023(13) -0.0005(13) N3 0.0247(14) 0.0303(14) 0.0350(15) -0.0036(12) -0.0048(12) 0.0017(11) C3 0.0181(16) 0.0319(17) 0.0306(17) 0.0087(14) -0.0003(13) -0.0039(13) N4 0.0159(13) 0.0249(13) 0.0274(14) 0.0027(11) 0.0057(10) 0.0014(10) C4 0.0256(17) 0.0243(16) 0.0281(16) 0.0011(13) -0.0061(13) -0.0044(13) N5 0.0164(13) 0.0347(14) 0.0297(14) -0.0004(11) 0.0046(11) 0.0002(11) C5 0.0230(16) 0.0230(15) 0.0244(16) 0.0002(13) -0.0019(13) 0.0026(13) N6 0.0172(14) 0.0356(15) 0.0361(16) -0.0037(12) -0.0005(12) -0.0011(11) C6 0.0174(15) 0.0213(15) 0.0261(16) 0.0074(13) 0.0014(13) 0.0007(12) C7 0.0228(16) 0.0205(15) 0.0291(17) 0.0031(13) 0.0026(13) 0.0041(12) C8 0.0180(16) 0.0320(17) 0.0374(18) 0.0139(15) 0.0020(14) 0.0076(13) C9 0.0250(17) 0.0392(18) 0.0248(16) 0.0103(14) -0.0067(13) -0.0008(14) C10 0.0239(16) 0.0348(17) 0.0186(15) 0.0043(14) 0.0030(12) -0.0027(13) C11 0.0288(18) 0.0260(16) 0.0310(18) -0.0025(14) -0.0089(14) 0.0024(13) C12 0.0345(19) 0.0428(19) 0.043(2) -0.0037(16) -0.0192(16) 0.0028(15) C13 0.0244(17) 0.0243(16) 0.0335(18) -0.0058(14) -0.0005(14) -0.0017(13) C14 0.0209(17) 0.0408(18) 0.048(2) -0.0127(16) -0.0056(15) 0.0007(14) _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 C6 2.033(3) . ? Fe1 C1 2.041(3) . ? Fe1 C10 2.041(3) . ? Fe1 C9 2.043(3) . ? Fe1 C5 2.046(3) . ? Fe1 C3 2.048(3) . ? Fe1 C8 2.049(3) . ? Fe1 C4 2.049(3) . ? Fe1 C2 2.050(3) . ? Fe1 C7 2.050(3) . ? P1 N1 1.688(2) . ? P1 C11 1.717(3) . ? N1 N2 1.352(3) . ? N1 C1 1.429(3) . ? C1 C5 1.415(4) . ? C1 C2 1.428(4) . ? P2 N4 1.691(2) . ? P2 C13 1.712(3) . ? N2 N3 1.311(3) . ? C2 C3 1.421(4) . ? N3 C11 1.364(4) . ? C3 C4 1.418(4) . ? N4 N5 1.362(3) . ? N4 C6 1.431(3) . ? C4 C5 1.420(4) . ? N5 N6 1.305(3) . ? N6 C13 1.363(4) . ? C6 C10 1.416(4) . ? C6 C7 1.423(4) . ? C7 C8 1.423(4) . ? C8 C9 1.423(4) . ? C9 C10 1.418(4) . ? C11 C12 1.500(4) . ? C13 C14 1.510(4) . ? 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 C6 Fe1 C1 108.79(10) . . ? C6 Fe1 C10 40.67(11) . . ? C1 Fe1 C10 123.18(11) . . ? C6 Fe1 C9 67.99(11) . . ? C1 Fe1 C9 158.82(12) . . ? C10 Fe1 C9 40.63(11) . . ? C6 Fe1 C5 121.18(11) . . ? C1 Fe1 C5 40.52(10) . . ? C10 Fe1 C5 105.23(12) . . ? C9 Fe1 C5 121.74(12) . . ? C6 Fe1 C3 162.35(12) . . ? C1 Fe1 C3 68.00(11) . . ? C10 Fe1 C3 155.91(11) . . ? C9 Fe1 C3 121.48(11) . . ? C5 Fe1 C3 68.50(12) . . ? C6 Fe1 C8 68.11(11) . . ? C1 Fe1 C8 159.47(12) . . ? C10 Fe1 C8 68.64(12) . . ? C9 Fe1 C8 40.69(12) . . ? C5 Fe1 C8 158.91(11) . . ? C3 Fe1 C8 108.41(12) . . ? C6 Fe1 C4 156.04(12) . . ? C1 Fe1 C4 67.78(10) . . ? C10 Fe1 C4 119.76(12) . . ? C9 Fe1 C4 106.18(12) . . ? C5 Fe1 C4 40.58(11) . . ? C3 Fe1 C4 40.51(11) . . ? C8 Fe1 C4 123.56(12) . . ? C6 Fe1 C2 125.63(11) . . ? C1 Fe1 C2 40.87(11) . . ? C10 Fe1 C2 160.91(11) . . ? C9 Fe1 C2 157.88(12) . . ? C5 Fe1 C2 68.95(11) . . ? C3 Fe1 C2 40.59(11) . . ? C8 Fe1 C2 123.19(12) . . ? C4 Fe1 C2 68.38(11) . . ? C6 Fe1 C7 40.77(11) . . ? C1 Fe1 C7 123.72(11) . . ? C10 Fe1 C7 68.95(12) . . ? C9 Fe1 C7 68.49(12) . . ? C5 Fe1 C7 157.93(11) . . ? C3 Fe1 C7 125.37(12) . . ? C8 Fe1 C7 40.62(11) . . ? C4 Fe1 C7 160.88(11) . . ? C2 Fe1 C7 109.24(11) . . ? N1 P1 C11 86.35(13) . . ? N2 N1 C1 116.7(2) . . ? N2 N1 P1 116.51(17) . . ? C1 N1 P1 126.36(19) . . ? C5 C1 C2 109.3(2) . . ? C5 C1 N1 125.8(3) . . ? C2 C1 N1 124.8(2) . . ? C5 C1 Fe1 69.93(15) . . ? C2 C1 Fe1 69.92(15) . . ? N1 C1 Fe1 130.31(18) . . ? N4 P2 C13 86.11(13) . . ? N3 N2 N1 110.4(2) . . ? C3 C2 C1 106.7(3) . . ? C3 C2 Fe1 69.63(16) . . ? C1 C2 Fe1 69.21(16) . . ? N2 N3 C11 113.7(2) . . ? C4 C3 C2 108.4(3) . . ? C4 C3 Fe1 69.80(16) . . ? C2 C3 Fe1 69.78(16) . . ? N5 N4 C6 116.3(2) . . ? N5 N4 P2 116.48(18) . . ? C6 N4 P2 127.01(19) . . ? C3 C4 C5 108.5(2) . . ? C3 C4 Fe1 69.69(16) . . ? C5 C4 Fe1 69.57(15) . . ? N6 N5 N4 110.0(2) . . ? C1 C5 C4 107.1(3) . . ? C1 C5 Fe1 69.55(15) . . ? C4 C5 Fe1 69.85(15) . . ? N5 N6 C13 113.8(2) . . ? C10 C6 C7 109.4(2) . . ? C10 C6 N4 125.2(3) . . ? C7 C6 N4 125.4(2) . . ? C10 C6 Fe1 69.96(16) . . ? C7 C6 Fe1 70.27(16) . . ? N4 C6 Fe1 125.84(18) . . ? C6 C7 C8 106.9(3) . . ? C6 C7 Fe1 68.96(15) . . ? C8 C7 Fe1 69.64(16) . . ? C7 C8 C9 108.1(3) . . ? C7 C8 Fe1 69.74(15) . . ? C9 C8 Fe1 69.44(16) . . ? C10 C9 C8 108.5(2) . . ? C10 C9 Fe1 69.59(16) . . ? C8 C9 Fe1 69.87(16) . . ? C6 C10 C9 107.1(3) . . ? C6 C10 Fe1 69.37(16) . . ? C9 C10 Fe1 69.78(16) . . ? N3 C11 C12 118.6(3) . . ? N3 C11 P1 113.1(2) . . ? C12 C11 P1 128.3(2) . . ? N6 C13 C14 119.1(3) . . ? N6 C13 P2 113.5(2) . . ? C14 C13 P2 127.4(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.437 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.070