# 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_test _database_code_depnum_ccdc_archive 'CCDC 847490' #TrackingRef '847490.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H42 Fe O3 P4' _chemical_formula_sum 'C20 H42 Fe O3 P4' _chemical_formula_weight 510.27 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.094(3) _cell_length_b 18.751(6) _cell_length_c 14.086(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.510(6) _cell_angle_gamma 90.00 _cell_volume 2621.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3528 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 24.12 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 1.293 _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088.0 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6200 _exptl_absorpt_correction_T_max 0.7658 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14531 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5153 _reflns_number_gt 3524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5153 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.006 _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 0.88828(3) 0.852455(17) 0.73318(3) 0.03047(12) Uani 1 1 d . . . P1 P 1.00018(8) 0.82964(4) 0.61099(6) 0.0436(2) Uani 1 1 d . . . P2 P 0.83181(7) 0.73926(4) 0.74607(6) 0.0434(2) Uani 1 1 d . . . P3 P 0.69588(7) 0.89493(4) 0.62894(6) 0.0438(2) Uani 1 1 d . . . P4 P 0.81573(8) 0.89141(4) 0.86799(6) 0.0438(2) Uani 1 1 d . . . O1 O 0.95524(17) 0.95246(8) 0.72435(13) 0.0370(4) Uani 1 1 d . . . O2 O 1.1057(2) 0.78420(11) 0.86683(16) 0.0578(6) Uani 1 1 d . . . O3 O 1.0706(2) 1.08152(11) 0.72523(17) 0.0651(6) Uani 1 1 d . . . C1 C 1.0765(3) 0.96077(14) 0.7748(2) 0.0369(6) Uani 1 1 d . . . C2 C 1.1444(3) 1.02741(15) 0.7771(2) 0.0454(7) Uani 1 1 d . . . C3 C 1.2729(3) 1.03340(18) 0.8287(3) 0.0591(9) Uani 1 1 d . . . H3 H 1.3184 1.0765 0.8289 0.071 Uiso 1 1 calc R . . C4 C 1.3365(3) 0.97595(19) 0.8811(3) 0.0620(10) Uani 1 1 d . . . H4 H 1.4233 0.9812 0.9163 0.074 Uiso 1 1 calc R . . C5 C 1.2718(3) 0.91217(17) 0.8806(2) 0.0537(8) Uani 1 1 d . . . H5 H 1.3142 0.8739 0.9157 0.064 Uiso 1 1 calc R . . C6 C 1.1412(3) 0.90419(14) 0.8273(2) 0.0406(7) Uani 1 1 d . . . C7 C 1.1274(4) 1.14968(16) 0.7331(3) 0.0737(11) Uani 1 1 d . . . H7A H 1.1446 1.1641 0.7996 0.111 Uiso 1 1 calc R . . H7B H 1.0661 1.1827 0.6961 0.111 Uiso 1 1 calc R . . H7C H 1.2105 1.1491 0.7091 0.111 Uiso 1 1 calc R . . C8 C 1.0587(3) 0.83753(14) 0.8192(2) 0.0392(7) Uani 1 1 d . . . C9 C 1.0315(4) 0.90793(17) 0.5411(3) 0.0766(12) Uani 1 1 d . . . H9A H 1.0837 0.9420 0.5831 0.115 Uiso 1 1 calc R . . H9B H 0.9471 0.9290 0.5121 0.115 Uiso 1 1 calc R . . H9C H 1.0801 0.8939 0.4916 0.115 Uiso 1 1 calc R . . C10 C 1.1734(3) 0.79717(19) 0.6435(3) 0.0731(11) Uani 1 1 d . . . H10A H 1.1749 0.7545 0.6814 0.110 Uiso 1 1 calc R . . H10B H 1.2283 0.8330 0.6803 0.110 Uiso 1 1 calc R . . H10C H 1.2080 0.7869 0.5858 0.110 Uiso 1 1 calc R . . C11 C 0.9389(3) 0.76630(16) 0.5136(2) 0.0658(10) Uani 1 1 d . . . H11A H 0.9967 0.7677 0.4666 0.099 Uiso 1 1 calc R . . H11B H 0.8489 0.7790 0.4835 0.099 Uiso 1 1 calc R . . H11C H 0.9390 0.7190 0.5398 0.099 Uiso 1 1 calc R . . C12 C 0.9543(3) 0.66967(15) 0.7329(3) 0.0690(11) Uani 1 1 d . . . H12A H 1.0345 0.6765 0.7804 0.104 Uiso 1 1 calc R . . H12B H 0.9762 0.6722 0.6695 0.104 Uiso 1 1 calc R . . H12C H 0.9164 0.6237 0.7420 0.104 Uiso 1 1 calc R . . C13 C 0.6859(4) 0.70389(17) 0.6626(3) 0.0840(13) Uani 1 1 d . . . H13A H 0.6751 0.6542 0.6758 0.126 Uiso 1 1 calc R . . H13B H 0.6997 0.7095 0.5974 0.126 Uiso 1 1 calc R . . H13C H 0.6063 0.7294 0.6710 0.126 Uiso 1 1 calc R . . C14 C 0.7928(4) 0.70550(17) 0.8593(3) 0.0803(12) Uani 1 1 d . . . H14A H 0.7148 0.7297 0.8734 0.120 Uiso 1 1 calc R . . H14B H 0.8680 0.7138 0.9105 0.120 Uiso 1 1 calc R . . H14C H 0.7750 0.6552 0.8535 0.120 Uiso 1 1 calc R . . C15 C 0.6555(4) 0.8706(2) 0.5014(3) 0.1020(16) Uani 1 1 d . . . H15A H 0.5715 0.8922 0.4725 0.153 Uiso 1 1 calc R . . H15B H 0.6483 0.8197 0.4954 0.153 Uiso 1 1 calc R . . H15C H 0.7256 0.8873 0.4691 0.153 Uiso 1 1 calc R . . C16 C 0.5241(3) 0.8843(3) 0.6538(4) 0.1164(18) Uani 1 1 d . . . H16A H 0.4609 0.9062 0.6031 0.175 Uiso 1 1 calc R . . H16B H 0.5183 0.9066 0.7142 0.175 Uiso 1 1 calc R . . H16C H 0.5037 0.8344 0.6571 0.175 Uiso 1 1 calc R . . C17 C 0.6974(4) 0.99132(17) 0.6140(3) 0.0901(14) Uani 1 1 d . . . H17A H 0.7832 1.0059 0.6004 0.135 Uiso 1 1 calc R . . H17B H 0.6825 1.0139 0.6723 0.135 Uiso 1 1 calc R . . H17C H 0.6274 1.0050 0.5615 0.135 Uiso 1 1 calc R . . C18 C 0.9185(4) 0.8710(3) 0.9844(3) 0.1066(16) Uani 1 1 d . . . H18A H 0.8829 0.8953 1.0343 0.160 Uiso 1 1 calc R . . H18B H 1.0094 0.8865 0.9852 0.160 Uiso 1 1 calc R . . H18C H 0.9177 0.8205 0.9954 0.160 Uiso 1 1 calc R . . C19 C 0.8087(5) 0.98736(18) 0.8793(3) 0.1050(17) Uani 1 1 d . . . H19A H 0.7866 0.9994 0.9408 0.158 Uiso 1 1 calc R . . H19B H 0.7411 1.0061 0.8287 0.158 Uiso 1 1 calc R . . H19C H 0.8947 1.0074 0.8745 0.158 Uiso 1 1 calc R . . C20 C 0.6521(4) 0.8694(2) 0.8975(3) 0.0945(15) Uani 1 1 d . . . H20A H 0.6255 0.8227 0.8733 0.142 Uiso 1 1 calc R . . H20B H 0.5866 0.9037 0.8683 0.142 Uiso 1 1 calc R . . H20C H 0.6582 0.8702 0.9663 0.142 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 0.0275(2) 0.02455(19) 0.0387(2) 0.00100(17) 0.00446(16) 0.00014(15) P1 0.0479(5) 0.0385(4) 0.0472(5) -0.0002(4) 0.0160(4) 0.0013(4) P2 0.0396(4) 0.0281(4) 0.0628(6) 0.0041(4) 0.0102(4) -0.0010(3) P3 0.0356(4) 0.0360(4) 0.0546(6) -0.0027(4) -0.0060(4) 0.0030(3) P4 0.0444(5) 0.0427(4) 0.0463(5) -0.0012(4) 0.0137(4) 0.0001(3) O1 0.0326(10) 0.0291(9) 0.0458(12) 0.0027(8) -0.0023(8) -0.0048(8) O2 0.0492(13) 0.0485(12) 0.0697(16) 0.0184(11) -0.0050(11) 0.0080(10) O3 0.0719(15) 0.0394(12) 0.0776(18) 0.0049(11) -0.0030(13) -0.0208(11) C1 0.0353(16) 0.0386(15) 0.0364(17) -0.0051(13) 0.0054(13) -0.0062(12) C2 0.0439(18) 0.0443(17) 0.047(2) -0.0073(15) 0.0063(15) -0.0119(14) C3 0.046(2) 0.059(2) 0.072(3) -0.0155(18) 0.0104(18) -0.0207(17) C4 0.0304(17) 0.077(3) 0.073(3) -0.022(2) -0.0049(16) -0.0097(17) C5 0.0360(17) 0.062(2) 0.059(2) -0.0036(17) -0.0023(15) 0.0055(15) C6 0.0312(15) 0.0449(17) 0.0445(19) -0.0027(14) 0.0034(13) 0.0007(13) C7 0.093(3) 0.052(2) 0.078(3) -0.0008(19) 0.021(2) -0.0279(19) C8 0.0338(15) 0.0421(17) 0.0418(18) 0.0023(13) 0.0073(13) 0.0051(12) C9 0.112(3) 0.058(2) 0.071(3) 0.0097(19) 0.047(2) -0.008(2) C10 0.048(2) 0.092(3) 0.086(3) -0.002(2) 0.030(2) 0.0165(19) C11 0.081(3) 0.059(2) 0.060(2) -0.0128(18) 0.020(2) 0.0020(19) C12 0.076(2) 0.0317(16) 0.105(3) 0.0065(18) 0.030(2) 0.0117(16) C13 0.073(3) 0.046(2) 0.121(4) 0.000(2) -0.016(2) -0.0225(18) C14 0.109(3) 0.0433(19) 0.099(3) 0.021(2) 0.048(3) 0.001(2) C15 0.104(3) 0.113(3) 0.069(3) -0.024(3) -0.036(2) 0.046(3) C16 0.037(2) 0.161(5) 0.148(5) 0.051(4) 0.007(3) 0.008(2) C17 0.084(3) 0.0386(19) 0.127(4) 0.008(2) -0.036(2) 0.0132(18) C18 0.087(3) 0.189(5) 0.043(3) -0.009(3) 0.009(2) 0.035(3) C19 0.186(5) 0.046(2) 0.106(4) -0.029(2) 0.086(3) -0.015(3) C20 0.068(3) 0.106(3) 0.124(4) -0.029(3) 0.058(3) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C8 1.935(3) . ? Fe1 O1 2.0048(17) . ? Fe1 P2 2.2137(10) . ? Fe1 P1 2.2651(10) . ? Fe1 P4 2.2766(10) . ? Fe1 P3 2.3498(10) . ? P1 C9 1.827(3) . ? P1 C10 1.829(3) . ? P1 C11 1.834(3) . ? P2 C14 1.824(3) . ? P2 C12 1.830(3) . ? P2 C13 1.833(3) . ? P3 C17 1.820(3) . ? P3 C15 1.826(4) . ? P3 C16 1.841(4) . ? P4 C19 1.809(3) . ? P4 C18 1.815(4) . ? P4 C20 1.822(3) . ? O1 C1 1.308(3) . ? O2 C8 1.249(3) . ? O3 C2 1.385(3) . ? O3 C7 1.397(3) . ? C1 C6 1.386(4) . ? C1 C2 1.423(4) . ? C2 C3 1.371(4) . ? C3 C4 1.394(4) . ? C3 H3 0.9300 . ? C4 C5 1.362(4) . ? C4 H4 0.9300 . ? C5 C6 1.401(4) . ? C5 H5 0.9300 . ? C6 C8 1.494(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C8 Fe1 O1 84.42(10) . . ? C8 Fe1 P2 91.31(8) . . ? O1 Fe1 P2 175.30(6) . . ? C8 Fe1 P1 86.49(9) . . ? O1 Fe1 P1 84.78(6) . . ? P2 Fe1 P1 93.03(3) . . ? C8 Fe1 P4 84.76(9) . . ? O1 Fe1 P4 85.13(6) . . ? P2 Fe1 P4 96.46(3) . . ? P1 Fe1 P4 167.23(3) . . ? C8 Fe1 P3 168.29(8) . . ? O1 Fe1 P3 83.90(6) . . ? P2 Fe1 P3 100.39(3) . . ? P1 Fe1 P3 93.38(4) . . ? P4 Fe1 P3 93.30(4) . . ? C9 P1 C10 98.68(17) . . ? C9 P1 C11 100.69(17) . . ? C10 P1 C11 98.52(16) . . ? C9 P1 Fe1 114.63(12) . . ? C10 P1 Fe1 117.33(12) . . ? C11 P1 Fe1 122.93(11) . . ? C14 P2 C12 95.65(16) . . ? C14 P2 C13 99.12(19) . . ? C12 P2 C13 98.96(17) . . ? C14 P2 Fe1 120.28(12) . . ? C12 P2 Fe1 119.12(11) . . ? C13 P2 Fe1 118.90(12) . . ? C17 P3 C15 98.0(2) . . ? C17 P3 C16 99.1(2) . . ? C15 P3 C16 96.4(2) . . ? C17 P3 Fe1 112.66(12) . . ? C15 P3 Fe1 122.75(13) . . ? C16 P3 Fe1 122.94(15) . . ? C19 P4 C18 98.9(2) . . ? C19 P4 C20 98.85(19) . . ? C18 P4 C20 98.0(2) . . ? C19 P4 Fe1 114.61(13) . . ? C18 P4 Fe1 117.94(13) . . ? C20 P4 Fe1 124.05(14) . . ? C1 O1 Fe1 111.74(16) . . ? C2 O3 C7 117.1(3) . . ? O1 C1 C6 120.1(2) . . ? O1 C1 C2 121.1(3) . . ? C6 C1 C2 118.8(3) . . ? C3 C2 O3 125.8(3) . . ? C3 C2 C1 119.3(3) . . ? O3 C2 C1 114.9(3) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.6(3) . . ? C1 C6 C8 113.4(2) . . ? C5 C6 C8 125.9(3) . . ? O3 C7 H7A 109.5 . . ? O3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C6 118.5(3) . . ? O2 C8 Fe1 131.3(2) . . ? C6 C8 Fe1 110.25(19) . . ? P1 C9 H9A 109.5 . . ? P1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? P1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? P1 C10 H10A 109.5 . . ? P1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? P1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? P1 C11 H11A 109.5 . . ? P1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? P1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P2 C12 H12A 109.5 . . ? P2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? P2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? P2 C13 H13A 109.5 . . ? P2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? P2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? P2 C14 H14A 109.5 . . ? P2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? P2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? P3 C15 H15A 109.5 . . ? P3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? P3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? P3 C16 H16A 109.5 . . ? P3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? P3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? P3 C17 H17A 109.5 . . ? P3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? P3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? P4 C18 H18A 109.5 . . ? P4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? P4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? P4 C19 H19A 109.5 . . ? P4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? P4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? P4 C20 H20A 109.5 . . ? P4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? P4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.433 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.069 data_1 _database_code_depnum_ccdc_archive 'CCDC 847491' #TrackingRef '847491.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H44 F2 Fe N P3 Si' _chemical_formula_sum 'C27 H44 F2 Fe N P3 Si' _chemical_formula_weight 597.48 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.661(2) _cell_length_b 21.657(5) _cell_length_c 15.892(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.072(4) _cell_angle_gamma 90.00 _cell_volume 3251.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3318 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.02 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 1.220 _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264.0 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18087 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6383 _reflns_number_gt 4055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.3118P] 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 6383 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5999(3) 0.10406(13) -0.06619(19) 0.0503(7) Uani 1 1 d . . . C2 C 0.6692(4) 0.11750(16) -0.1305(2) 0.0699(9) Uani 1 1 d . . . C3 C 0.6279(5) 0.09874(19) -0.2145(2) 0.0878(11) Uani 1 1 d . . . H3 H 0.6801 0.1091 -0.2554 0.105 Uiso 1 1 calc R . . C4 C 0.5061(5) 0.06395(18) -0.2360(2) 0.0882(12) Uani 1 1 d . . . H4 H 0.4753 0.0506 -0.2924 0.106 Uiso 1 1 calc R . . C5 C 0.4299(4) 0.04883(16) -0.1754(3) 0.0806(11) Uani 1 1 d . . . H5 H 0.3478 0.0253 -0.1894 0.097 Uiso 1 1 calc R . . C6 C 0.4800(3) 0.07000(15) -0.0928(2) 0.0647(9) Uani 1 1 d . . . C7 C 0.6519(3) 0.12411(13) 0.02593(18) 0.0489(7) Uani 1 1 d . . . C8 C 0.7717(3) 0.08933(13) 0.07852(19) 0.0502(7) Uani 1 1 d . . . C9 C 0.8277(3) 0.03752(14) 0.0473(2) 0.0628(9) Uani 1 1 d . . . H9 H 0.7914 0.0244 -0.0087 0.075 Uiso 1 1 calc R . . C10 C 0.9374(4) 0.00491(17) 0.0985(2) 0.0780(10) Uani 1 1 d . . . H10 H 0.9726 -0.0304 0.0771 0.094 Uiso 1 1 calc R . . C11 C 0.9938(4) 0.02437(19) 0.1802(3) 0.0833(11) Uani 1 1 d . . . H11 H 1.0684 0.0028 0.2141 0.100 Uiso 1 1 calc R . . C12 C 0.9400(4) 0.07589(19) 0.2119(2) 0.0822(11) Uani 1 1 d . . . H12 H 0.9787 0.0893 0.2674 0.099 Uiso 1 1 calc R . . C13 C 0.8294(3) 0.10786(16) 0.1624(2) 0.0671(9) Uani 1 1 d . . . H13 H 0.7926 0.1422 0.1852 0.081 Uiso 1 1 calc R . . C14 C 0.2177(3) 0.17070(16) 0.0293(2) 0.0787(10) Uani 1 1 d . . . H14A H 0.1397 0.1474 0.0415 0.118 Uiso 1 1 calc R . . H14B H 0.2610 0.1481 -0.0104 0.118 Uiso 1 1 calc R . . H14C H 0.1841 0.2097 0.0044 0.118 Uiso 1 1 calc R . . C15 C 0.3746(4) 0.10545(15) 0.1718(2) 0.0813(11) Uani 1 1 d . . . H15A H 0.4259 0.1073 0.2304 0.122 Uiso 1 1 calc R . . H15B H 0.4277 0.0820 0.1382 0.122 Uiso 1 1 calc R . . H15C H 0.2846 0.0860 0.1696 0.122 Uiso 1 1 calc R . . C16 C 0.2334(4) 0.21885(18) 0.1937(2) 0.0880(11) Uani 1 1 d . . . H16A H 0.2047 0.2592 0.1717 0.132 Uiso 1 1 calc R . . H16B H 0.2847 0.2223 0.2522 0.132 Uiso 1 1 calc R . . H16C H 0.1513 0.1935 0.1916 0.132 Uiso 1 1 calc R . . C17 C 0.6080(4) 0.29469(17) -0.0751(2) 0.0800(10) Uani 1 1 d . . . H17A H 0.5161 0.3137 -0.0867 0.120 Uiso 1 1 calc R . . H17B H 0.6008 0.2537 -0.0985 0.120 Uiso 1 1 calc R . . H17C H 0.6714 0.3186 -0.1012 0.120 Uiso 1 1 calc R . . C18 C 0.8566(3) 0.26397(16) 0.0455(3) 0.0788(10) Uani 1 1 d . . . H18A H 0.8554 0.2205 0.0334 0.118 Uiso 1 1 calc R . . H18B H 0.9124 0.2714 0.1020 0.118 Uiso 1 1 calc R . . H18C H 0.8970 0.2858 0.0038 0.118 Uiso 1 1 calc R . . C19 C 0.7006(3) 0.37286(14) 0.0663(2) 0.0763(10) Uani 1 1 d . . . H19A H 0.7482 0.3922 0.0259 0.114 Uiso 1 1 calc R . . H19B H 0.7569 0.3772 0.1234 0.114 Uiso 1 1 calc R . . H19C H 0.6103 0.3922 0.0633 0.114 Uiso 1 1 calc R . . C20 C 0.5494(4) 0.33953(17) 0.2688(2) 0.0930(13) Uani 1 1 d . . . H20A H 0.4490 0.3367 0.2642 0.139 Uiso 1 1 calc R . . H20B H 0.5700 0.3728 0.2335 0.139 Uiso 1 1 calc R . . H20C H 0.5948 0.3471 0.3276 0.139 Uiso 1 1 calc R . . C21 C 0.5971(5) 0.21435(18) 0.3198(2) 0.1021(14) Uani 1 1 d . . . H21A H 0.6562 0.2281 0.3727 0.153 Uiso 1 1 calc R . . H21B H 0.6255 0.1736 0.3065 0.153 Uiso 1 1 calc R . . H21C H 0.5002 0.2135 0.3257 0.153 Uiso 1 1 calc R . . C22 C 0.8058(3) 0.27968(17) 0.2653(2) 0.0874(12) Uani 1 1 d . . . H22A H 0.8334 0.3124 0.2316 0.131 Uiso 1 1 calc R . . H22B H 0.8546 0.2425 0.2562 0.131 Uiso 1 1 calc R . . H22C H 0.8296 0.2906 0.3252 0.131 Uiso 1 1 calc R . . C23 C 0.4057(3) 0.30186(13) 0.07143(18) 0.0495(7) Uani 1 1 d . . . C24 C 0.3287(3) 0.34581(14) 0.0473(2) 0.0594(8) Uani 1 1 d . . . C25 C 0.0486(3) 0.41043(17) -0.0084(3) 0.1011(14) Uani 1 1 d . . . H25A H 0.0196 0.3780 -0.0494 0.152 Uiso 1 1 calc R . . H25B H 0.0058 0.4486 -0.0311 0.152 Uiso 1 1 calc R . . H25C H 0.0192 0.4007 0.0442 0.152 Uiso 1 1 calc R . . C26 C 0.2965(4) 0.44558(18) -0.0861(2) 0.0997(13) Uani 1 1 d . . . H26A H 0.3978 0.4487 -0.0762 0.149 Uiso 1 1 calc R . . H26B H 0.2552 0.4854 -0.1017 0.149 Uiso 1 1 calc R . . H26C H 0.2638 0.4168 -0.1319 0.149 Uiso 1 1 calc R . . C27 C 0.2984(4) 0.47823(15) 0.0981(2) 0.0797(10) Uani 1 1 d . . . H27A H 0.2681 0.4661 0.1494 0.120 Uiso 1 1 calc R . . H27B H 0.2555 0.5170 0.0781 0.120 Uiso 1 1 calc R . . H27C H 0.3995 0.4825 0.1103 0.120 Uiso 1 1 calc R . . F1 F 0.7912(2) 0.15064(12) -0.10942(14) 0.1139(8) Uani 1 1 d . . . F2 F 0.4071(2) 0.05487(11) -0.03118(15) 0.1105(8) Uani 1 1 d . . . Fe1 Fe 0.53334(4) 0.234657(18) 0.10203(2) 0.04427(13) Uani 1 1 d . . . N1 N 0.5923(2) 0.17004(10) 0.05464(14) 0.0498(6) Uani 1 1 d . . . P1 P 0.34715(8) 0.18374(4) 0.12835(5) 0.0549(2) Uani 1 1 d . . . P2 P 0.67514(8) 0.29112(4) 0.04016(5) 0.0546(2) Uani 1 1 d . . . P3 P 0.61493(9) 0.26733(4) 0.23302(5) 0.0599(2) Uani 1 1 d . . . Si1 Si 0.24408(8) 0.41819(4) 0.01323(6) 0.0527(2) Uani 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 C1 0.0500(17) 0.0441(17) 0.0572(19) -0.0009(15) 0.0123(15) 0.0036(14) C2 0.070(2) 0.076(2) 0.067(2) -0.0122(19) 0.0229(19) -0.0048(19) C3 0.107(3) 0.094(3) 0.068(3) -0.007(2) 0.031(2) 0.008(3) C4 0.116(3) 0.081(3) 0.060(2) -0.012(2) 0.000(2) 0.023(3) C5 0.079(3) 0.067(2) 0.083(3) -0.014(2) -0.011(2) -0.0014(19) C6 0.067(2) 0.056(2) 0.073(2) 0.0020(18) 0.0203(19) 0.0049(17) C7 0.0465(17) 0.0447(18) 0.0577(19) -0.0008(14) 0.0161(14) -0.0016(14) C8 0.0468(17) 0.0486(18) 0.0575(19) 0.0050(15) 0.0160(14) 0.0008(14) C9 0.061(2) 0.062(2) 0.067(2) 0.0026(17) 0.0178(17) 0.0133(17) C10 0.076(2) 0.073(2) 0.091(3) 0.015(2) 0.030(2) 0.026(2) C11 0.070(2) 0.103(3) 0.077(3) 0.028(2) 0.015(2) 0.026(2) C12 0.087(3) 0.099(3) 0.056(2) 0.006(2) 0.0050(19) 0.015(2) C13 0.073(2) 0.069(2) 0.059(2) -0.0019(18) 0.0112(17) 0.0081(18) C14 0.062(2) 0.082(3) 0.085(3) 0.008(2) -0.0004(19) -0.0065(19) C15 0.084(2) 0.065(2) 0.095(3) 0.024(2) 0.020(2) -0.0058(19) C16 0.075(2) 0.101(3) 0.099(3) 0.011(2) 0.043(2) 0.012(2) C17 0.082(2) 0.096(3) 0.066(2) 0.018(2) 0.0250(19) 0.000(2) C18 0.0517(19) 0.068(2) 0.122(3) 0.006(2) 0.030(2) 0.0042(17) C19 0.063(2) 0.050(2) 0.117(3) 0.0079(19) 0.021(2) -0.0029(16) C20 0.114(3) 0.085(3) 0.073(2) -0.023(2) 0.004(2) 0.031(2) C21 0.142(4) 0.101(3) 0.054(2) 0.015(2) -0.003(2) -0.005(3) C22 0.074(2) 0.084(3) 0.088(3) -0.014(2) -0.019(2) 0.007(2) C23 0.0470(16) 0.0469(18) 0.0553(18) 0.0044(15) 0.0120(14) 0.0031(14) C24 0.0538(18) 0.0519(19) 0.072(2) 0.0131(17) 0.0125(16) 0.0086(16) C25 0.053(2) 0.065(2) 0.179(4) -0.011(3) 0.010(2) 0.0053(18) C26 0.143(4) 0.080(3) 0.078(3) 0.014(2) 0.028(3) -0.008(3) C27 0.092(3) 0.067(2) 0.077(2) 0.0013(19) 0.009(2) -0.004(2) F1 0.1074(17) 0.158(2) 0.0911(15) -0.0258(15) 0.0544(13) -0.0471(17) F2 0.1030(17) 0.1105(18) 0.1190(19) -0.0119(15) 0.0256(15) -0.0383(14) Fe1 0.0422(2) 0.0409(2) 0.0488(2) 0.00276(19) 0.00745(17) 0.00587(18) N1 0.0478(13) 0.0474(15) 0.0563(15) 0.0003(12) 0.0153(11) -0.0025(12) P1 0.0501(5) 0.0542(5) 0.0616(5) 0.0102(4) 0.0148(4) 0.0033(4) P2 0.0446(4) 0.0495(5) 0.0703(6) 0.0064(4) 0.0129(4) 0.0006(4) P3 0.0660(5) 0.0555(5) 0.0534(5) -0.0019(4) 0.0015(4) 0.0102(4) Si1 0.0458(5) 0.0431(5) 0.0676(6) 0.0099(4) 0.0084(4) 0.0044(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.364(4) . ? C1 C2 1.366(4) . ? C1 C7 1.509(4) . ? C2 F1 1.361(4) . ? C2 C3 1.372(5) . ? C3 C4 1.378(5) . ? C4 C5 1.368(5) . ? C5 C6 1.379(4) . ? C6 F2 1.361(4) . ? C7 N1 1.281(3) . ? C7 C8 1.483(4) . ? C8 C9 1.382(4) . ? C8 C13 1.392(4) . ? C9 C10 1.387(4) . ? C10 C11 1.366(5) . ? C11 C12 1.371(5) . ? C12 C13 1.374(4) . ? C14 P1 1.816(3) . ? C15 P1 1.829(3) . ? C16 P1 1.828(3) . ? C17 P2 1.813(3) . ? C18 P2 1.834(3) . ? C19 P2 1.823(3) . ? C20 P3 1.822(3) . ? C21 P3 1.829(4) . ? C22 P3 1.828(3) . ? C23 C24 1.219(4) . ? C23 Fe1 1.904(3) . ? C24 Si1 1.799(3) . ? C25 Si1 1.855(3) . ? C26 Si1 1.854(4) . ? C27 Si1 1.868(3) . ? Fe1 N1 1.740(2) . ? Fe1 P3 2.1838(10) . ? Fe1 P2 2.2140(9) . ? Fe1 P1 2.2229(9) . ? 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 C1 C2 113.6(3) . . ? C6 C1 C7 123.1(3) . . ? C2 C1 C7 123.3(3) . . ? F1 C2 C1 117.6(3) . . ? F1 C2 C3 117.2(3) . . ? C1 C2 C3 125.2(3) . . ? C2 C3 C4 117.5(4) . . ? C5 C4 C3 120.9(4) . . ? C4 C5 C6 117.2(4) . . ? F2 C6 C1 116.2(3) . . ? F2 C6 C5 118.3(3) . . ? C1 C6 C5 125.5(3) . . ? N1 C7 C8 123.4(3) . . ? N1 C7 C1 119.1(2) . . ? C8 C7 C1 117.6(2) . . ? C9 C8 C13 118.0(3) . . ? C9 C8 C7 121.8(3) . . ? C13 C8 C7 120.1(3) . . ? C8 C9 C10 120.7(3) . . ? C11 C10 C9 120.4(3) . . ? C10 C11 C12 119.6(3) . . ? C11 C12 C13 120.6(3) . . ? C12 C13 C8 120.7(3) . . ? C24 C23 Fe1 175.5(3) . . ? C23 C24 Si1 169.8(3) . . ? N1 Fe1 C23 139.22(12) . . ? N1 Fe1 P3 125.98(8) . . ? C23 Fe1 P3 94.65(9) . . ? N1 Fe1 P2 87.89(8) . . ? C23 Fe1 P2 83.82(9) . . ? P3 Fe1 P2 96.37(4) . . ? N1 Fe1 P1 91.91(8) . . ? C23 Fe1 P1 85.45(9) . . ? P3 Fe1 P1 97.26(4) . . ? P2 Fe1 P1 163.28(3) . . ? C7 N1 Fe1 172.3(2) . . ? C14 P1 C16 99.84(17) . . ? C14 P1 C15 101.67(16) . . ? C16 P1 C15 103.16(17) . . ? C14 P1 Fe1 110.58(12) . . ? C16 P1 Fe1 120.45(13) . . ? C15 P1 Fe1 118.15(12) . . ? C17 P2 C19 101.03(17) . . ? C17 P2 C18 101.36(17) . . ? C19 P2 C18 102.61(15) . . ? C17 P2 Fe1 110.39(11) . . ? C19 P2 Fe1 120.13(12) . . ? C18 P2 Fe1 118.47(12) . . ? C20 P3 C22 100.52(17) . . ? C20 P3 C21 102.09(19) . . ? C22 P3 C21 97.38(19) . . ? C20 P3 Fe1 119.73(12) . . ? C22 P3 Fe1 117.20(13) . . ? C21 P3 Fe1 116.31(13) . . ? C24 Si1 C26 110.34(17) . . ? C24 Si1 C25 110.97(16) . . ? C26 Si1 C25 108.7(2) . . ? C24 Si1 C27 110.35(15) . . ? C26 Si1 C27 107.85(16) . . ? C25 Si1 C27 108.56(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.046 data_d:\tmp\h_sun\2\sun2 _database_code_depnum_ccdc_archive 'CCDC 847492' #TrackingRef '847492.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 F2 Fe O2 P2' _chemical_formula_weight 606.38 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' 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' 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 9.6343(8) _cell_length_b 9.3988(8) _cell_length_c 33.449(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.814(2) _cell_angle_gamma 90.00 _cell_volume 3025.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2256 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 21.17 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9384 _exptl_absorpt_correction_T_max 0.9685 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17439 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6858 _reflns_number_gt 3898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6858 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 Fe Fe 0.16920(5) 0.35205(5) 0.113282(13) 0.03662(15) Uani 1 1 d . A . F1 F 0.5788(3) 0.7038(3) 0.09594(9) 0.1010(9) Uani 1 1 d . A . F2 F -0.2154(2) -0.0298(2) 0.12102(7) 0.0716(7) Uani 1 1 d . A . O1 O 0.3017(2) 0.4310(2) 0.15231(6) 0.0404(5) Uani 1 1 d . A . O2 O 0.0973(2) 0.2488(2) 0.15898(6) 0.0396(5) Uani 1 1 d . A . P1 P 0.31459(10) 0.17981(11) 0.09688(3) 0.0521(3) Uani 1 1 d . . . P2 P 0.01403(10) 0.52786(10) 0.11639(3) 0.0453(2) Uani 1 1 d . . . C1 C 0.2692(4) 0.4763(4) 0.07758(11) 0.0465(9) Uani 1 1 d . . . C2 C 0.2528(4) 0.5014(4) 0.03597(11) 0.0608(11) Uani 1 1 d . A . H2A H 0.1812 0.4559 0.0214 0.073 Uiso 1 1 calc R . . C3 C 0.3400(5) 0.5915(5) 0.01638(13) 0.0726(13) Uani 1 1 d . . . H3A H 0.3254 0.6061 -0.0110 0.087 Uiso 1 1 calc R A . C4 C 0.4487(5) 0.6603(5) 0.03678(15) 0.0780(14) Uani 1 1 d . A . H4A H 0.5079 0.7199 0.0234 0.094 Uiso 1 1 calc R . . C5 C 0.4668(4) 0.6388(4) 0.07656(14) 0.0635(11) Uani 1 1 d . . . C6 C 0.3801(4) 0.5529(4) 0.09879(11) 0.0477(9) Uani 1 1 d . A . C7 C 0.3893(3) 0.5200(4) 0.14113(11) 0.0430(8) Uani 1 1 d . . . C8 C 0.4883(3) 0.5739(4) 0.17310(11) 0.0470(9) Uani 1 1 d . A . C9 C 0.5268(4) 0.7153(5) 0.17685(14) 0.0722(13) Uani 1 1 d . . . H9A H 0.4959 0.7810 0.1576 0.087 Uiso 1 1 calc R A . C10 C 0.6110(5) 0.7591(5) 0.20912(17) 0.0931(17) Uani 1 1 d . A . H10A H 0.6331 0.8550 0.2120 0.112 Uiso 1 1 calc R . . C11 C 0.6618(5) 0.6649(6) 0.23660(15) 0.0824(15) Uani 1 1 d . . . H11A H 0.7219 0.6948 0.2575 0.099 Uiso 1 1 calc R A . C12 C 0.6237(4) 0.5247(5) 0.23325(13) 0.0679(12) Uani 1 1 d . A . H12A H 0.6574 0.4594 0.2523 0.081 Uiso 1 1 calc R . . C13 C 0.5369(4) 0.4799(4) 0.20232(11) 0.0530(10) Uani 1 1 d . . . H13A H 0.5102 0.3849 0.2009 0.064 Uiso 1 1 calc R A . C14 C 0.0237(3) 0.2424(4) 0.08404(10) 0.0429(8) Uani 1 1 d . . . C15 C -0.0181(4) 0.2279(4) 0.04351(11) 0.0592(10) Uani 1 1 d . A . H15A H 0.0244 0.2850 0.0250 0.071 Uiso 1 1 calc R . . C16 C -0.1186(5) 0.1340(5) 0.02974(13) 0.0701(12) Uani 1 1 d . . . H16A H -0.1425 0.1296 0.0025 0.084 Uiso 1 1 calc R A . C17 C -0.1850(4) 0.0454(5) 0.05606(13) 0.0674(12) Uani 1 1 d . A . H17A H -0.2505 -0.0208 0.0467 0.081 Uiso 1 1 calc R . . C18 C -0.1518(4) 0.0582(4) 0.09536(11) 0.0497(9) Uani 1 1 d . . . C19 C -0.0506(3) 0.1530(3) 0.11052(10) 0.0400(8) Uani 1 1 d . A . C20 C -0.0048(3) 0.1684(3) 0.15214(10) 0.0365(7) Uani 1 1 d . . . C21 C -0.0652(3) 0.1024(4) 0.18774(10) 0.0413(8) Uani 1 1 d . A . C22 C 0.0104(4) 0.0057(4) 0.21068(12) 0.0617(11) Uani 1 1 d . . . H22A H 0.0962 -0.0254 0.2025 0.074 Uiso 1 1 calc R A . C23 C -0.0411(5) -0.0462(5) 0.24625(13) 0.0789(14) Uani 1 1 d . A . H23A H 0.0099 -0.1132 0.2612 0.095 Uiso 1 1 calc R . . C24 C -0.1632(6) -0.0004(6) 0.25907(13) 0.0788(15) Uani 1 1 d . . . H24A H -0.1963 -0.0351 0.2828 0.095 Uiso 1 1 calc R A . C25 C -0.2387(5) 0.0976(5) 0.23698(15) 0.0784(14) Uani 1 1 d . A . H25A H -0.3215 0.1319 0.2464 0.094 Uiso 1 1 calc R . . C26 C -0.1936(4) 0.1470(4) 0.20052(13) 0.0645(11) Uani 1 1 d . . . H26A H -0.2486 0.2089 0.1849 0.077 Uiso 1 1 calc R A . C27A C 0.4997(9) 0.2243(11) 0.1021(3) 0.079(3) Uiso 0.50 1 d P A 1 H27A H 0.5229 0.2527 0.1292 0.094 Uiso 0.50 1 calc PR A 1 H27B H 0.5193 0.3010 0.0843 0.094 Uiso 0.50 1 calc PR A 1 H27C H 0.5538 0.1426 0.0955 0.094 Uiso 0.50 1 calc PR A 1 C28A C 0.3078(11) 0.1256(11) 0.0439(3) 0.073(3) Uiso 0.50 1 d P A 1 H28A H 0.3121 0.2085 0.0273 0.087 Uiso 0.50 1 calc PR A 1 H28B H 0.2226 0.0755 0.0377 0.087 Uiso 0.50 1 calc PR A 1 H28C H 0.3852 0.0645 0.0392 0.087 Uiso 0.50 1 calc PR A 1 C29A C 0.3091(11) 0.0200(11) 0.1232(3) 0.090(3) Uiso 0.50 1 d P A 1 H29A H 0.2162 -0.0172 0.1214 0.108 Uiso 0.50 1 calc PR A 1 H29B H 0.3368 0.0363 0.1508 0.108 Uiso 0.50 1 calc PR A 1 H29C H 0.3713 -0.0471 0.1119 0.108 Uiso 0.50 1 calc PR A 1 C27B C 0.4849(10) 0.1732(10) 0.1230(3) 0.075(3) Uiso 0.50 1 d P A 2 H27D H 0.4744 0.1501 0.1506 0.091 Uiso 0.50 1 calc PR A 2 H27E H 0.5295 0.2642 0.1211 0.091 Uiso 0.50 1 calc PR A 2 H27F H 0.5408 0.1019 0.1110 0.091 Uiso 0.50 1 calc PR A 2 C28B C 0.3639(12) 0.1600(12) 0.0466(3) 0.087(4) Uiso 0.50 1 d P A 2 H28D H 0.4315 0.2312 0.0408 0.104 Uiso 0.50 1 calc PR A 2 H28E H 0.2836 0.1709 0.0288 0.104 Uiso 0.50 1 calc PR A 2 H28F H 0.4032 0.0672 0.0432 0.104 Uiso 0.50 1 calc PR A 2 C29B C 0.2558(9) -0.0083(8) 0.1059(3) 0.062(2) Uiso 0.50 1 d P A 2 H29D H 0.1721 -0.0270 0.0899 0.074 Uiso 0.50 1 calc PR A 2 H29E H 0.2382 -0.0204 0.1337 0.074 Uiso 0.50 1 calc PR A 2 H29F H 0.3270 -0.0735 0.0986 0.074 Uiso 0.50 1 calc PR A 2 C30 C -0.0601(5) 0.5982(5) 0.06935(13) 0.0772(13) Uani 1 1 d . A . H30A H -0.1247 0.6727 0.0747 0.116 Uiso 1 1 calc R . . H30B H -0.1075 0.5235 0.0547 0.116 Uiso 1 1 calc R . . H30C H 0.0129 0.6355 0.0538 0.116 Uiso 1 1 calc R . . C31 C 0.0749(5) 0.6889(4) 0.14189(14) 0.0770(14) Uani 1 1 d . A . H31A H 0.0010 0.7575 0.1416 0.116 Uiso 1 1 calc R . . H31B H 0.1521 0.7275 0.1284 0.116 Uiso 1 1 calc R . . H31C H 0.1035 0.6666 0.1691 0.116 Uiso 1 1 calc R . . C32 C -0.1428(4) 0.4914(4) 0.14308(14) 0.0706(12) Uani 1 1 d . A . H32A H -0.2011 0.5743 0.1424 0.106 Uiso 1 1 calc R . . H32B H -0.1177 0.4673 0.1704 0.106 Uiso 1 1 calc R . . H32C H -0.1922 0.4134 0.1305 0.106 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 Fe 0.0391(3) 0.0409(3) 0.0301(3) 0.0002(2) 0.00418(19) -0.0035(2) F1 0.0787(18) 0.119(2) 0.107(2) 0.0181(18) 0.0160(16) -0.0473(17) F2 0.0725(15) 0.0703(16) 0.0717(16) -0.0057(12) 0.0002(13) -0.0314(13) O1 0.0383(12) 0.0466(14) 0.0363(13) -0.0018(10) 0.0036(10) -0.0088(11) O2 0.0382(12) 0.0463(14) 0.0342(13) 0.0024(10) -0.0002(10) -0.0057(11) P1 0.0518(6) 0.0524(6) 0.0530(6) -0.0036(5) 0.0122(5) 0.0048(5) P2 0.0488(6) 0.0444(6) 0.0430(6) 0.0038(4) 0.0037(4) 0.0024(4) C1 0.049(2) 0.046(2) 0.046(2) 0.0063(16) 0.0124(17) 0.0049(17) C2 0.068(3) 0.074(3) 0.041(2) 0.0088(19) 0.0118(19) -0.004(2) C3 0.095(3) 0.078(3) 0.047(3) 0.017(2) 0.020(2) 0.001(3) C4 0.090(3) 0.077(3) 0.070(3) 0.027(2) 0.038(3) -0.013(3) C5 0.053(2) 0.065(3) 0.075(3) 0.004(2) 0.018(2) -0.015(2) C6 0.045(2) 0.047(2) 0.053(2) 0.0046(17) 0.0140(17) -0.0018(17) C7 0.0380(18) 0.041(2) 0.051(2) -0.0046(16) 0.0057(16) 0.0000(16) C8 0.0343(18) 0.051(2) 0.056(2) -0.0060(18) 0.0028(17) -0.0075(17) C9 0.073(3) 0.053(3) 0.088(3) -0.003(2) -0.015(3) -0.012(2) C10 0.096(4) 0.055(3) 0.125(5) -0.022(3) -0.035(3) -0.015(3) C11 0.069(3) 0.087(4) 0.088(4) -0.014(3) -0.027(3) -0.011(3) C12 0.062(3) 0.074(3) 0.067(3) -0.006(2) -0.013(2) -0.005(2) C13 0.047(2) 0.054(2) 0.058(2) -0.0048(19) 0.0014(19) -0.0055(18) C14 0.050(2) 0.042(2) 0.036(2) -0.0021(15) 0.0000(16) 0.0032(16) C15 0.071(3) 0.067(3) 0.039(2) -0.0027(18) -0.0023(19) -0.013(2) C16 0.084(3) 0.080(3) 0.044(2) -0.011(2) -0.019(2) -0.005(3) C17 0.070(3) 0.066(3) 0.065(3) -0.016(2) -0.015(2) -0.015(2) C18 0.049(2) 0.049(2) 0.051(2) -0.0062(18) 0.0005(18) -0.0099(18) C19 0.0411(19) 0.042(2) 0.0363(19) -0.0035(15) -0.0005(15) 0.0009(16) C20 0.0364(18) 0.0336(19) 0.0394(19) 0.0001(14) 0.0014(14) -0.0026(14) C21 0.045(2) 0.043(2) 0.0356(19) -0.0004(15) 0.0022(16) -0.0112(16) C22 0.057(2) 0.075(3) 0.053(3) 0.010(2) -0.001(2) -0.007(2) C23 0.079(3) 0.106(4) 0.051(3) 0.026(3) -0.005(2) -0.019(3) C24 0.105(4) 0.093(4) 0.039(2) -0.001(2) 0.007(3) -0.049(3) C25 0.081(3) 0.075(3) 0.083(4) -0.015(3) 0.044(3) -0.029(3) C26 0.059(3) 0.061(3) 0.075(3) 0.006(2) 0.025(2) -0.005(2) C30 0.083(3) 0.088(3) 0.059(3) 0.016(2) -0.006(2) 0.024(3) C31 0.086(3) 0.045(2) 0.099(4) -0.011(2) -0.006(3) 0.008(2) C32 0.055(3) 0.069(3) 0.089(3) 0.007(2) 0.023(2) 0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe O1 1.929(2) . ? Fe C1 1.957(3) . ? Fe C14 1.962(3) . ? Fe O2 1.965(2) . ? Fe P1 2.2269(11) . ? Fe P2 2.2341(10) . ? F1 C5 1.374(5) . ? F2 C18 1.360(4) . ? O1 C7 1.258(4) . ? O2 C20 1.253(3) . ? P1 C29A 1.743(10) . ? P1 C28B 1.778(11) . ? P1 C27B 1.822(9) . ? P1 C27A 1.832(9) . ? P1 C28A 1.841(10) . ? P1 C29B 1.886(8) . ? P2 C31 1.820(4) . ? P2 C30 1.820(4) . ? P2 C32 1.825(4) . ? C1 C2 1.413(5) . ? C1 C6 1.446(5) . ? C2 C3 1.381(5) . ? C3 C4 1.382(6) . ? C4 C5 1.349(6) . ? C5 C6 1.401(5) . ? C6 C7 1.448(5) . ? C7 C8 1.487(5) . ? C8 C13 1.382(5) . ? C8 C9 1.384(5) . ? C9 C10 1.380(6) . ? C10 C11 1.350(6) . ? C11 C12 1.371(6) . ? C12 C13 1.364(5) . ? C14 C15 1.402(5) . ? C14 C19 1.437(4) . ? C15 C16 1.373(5) . ? C16 C17 1.390(6) . ? C17 C18 1.343(5) . ? C18 C19 1.397(4) . ? C19 C20 1.447(4) . ? C20 C21 1.486(4) . ? C21 C22 1.375(5) . ? C21 C26 1.394(5) . ? C22 C23 1.399(5) . ? C23 C24 1.343(7) . ? C24 C25 1.368(6) . ? C25 C26 1.394(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe C1 81.63(13) . . ? O1 Fe C14 166.51(12) . . ? C1 Fe C14 111.71(15) . . ? O1 Fe O2 84.86(9) . . ? C1 Fe O2 166.43(13) . . ? C14 Fe O2 81.84(12) . . ? O1 Fe P1 92.48(7) . . ? C1 Fe P1 87.08(10) . . ? C14 Fe P1 86.45(10) . . ? O2 Fe P1 94.72(7) . . ? O1 Fe P2 96.08(7) . . ? C1 Fe P2 86.43(10) . . ? C14 Fe P2 87.04(10) . . ? O2 Fe P2 93.85(7) . . ? P1 Fe P2 168.39(4) . . ? C7 O1 Fe 119.1(2) . . ? C20 O2 Fe 117.4(2) . . ? C29A P1 C27A 101.7(5) . . ? C29A P1 C28A 104.3(5) . . ? C27A P1 C28A 98.2(5) . . ? C28B P1 C29B 98.6(5) . . ? C27B P1 C29B 99.4(4) . . ? C28B P1 C27B 100.0(5) . . ? C29A P1 Fe 117.9(4) . . ? C28B P1 Fe 120.6(4) . . ? C27B P1 Fe 118.0(3) . . ? C27A P1 Fe 115.6(3) . . ? C28A P1 Fe 116.4(3) . . ? C29B P1 Fe 116.4(3) . . ? C31 P2 C30 101.9(2) . . ? C31 P2 C32 100.5(2) . . ? C30 P2 C32 101.1(2) . . ? C31 P2 Fe 115.85(15) . . ? C30 P2 Fe 117.60(15) . . ? C32 P2 Fe 117.13(14) . . ? C2 C1 C6 116.4(3) . . ? C2 C1 Fe 131.8(3) . . ? C6 C1 Fe 111.8(2) . . ? C3 C2 C1 121.9(4) . . ? C2 C3 C4 121.1(4) . . ? C5 C4 C3 118.4(4) . . ? C4 C5 F1 117.3(4) . . ? C4 C5 C6 124.0(4) . . ? F1 C5 C6 118.7(4) . . ? C5 C6 C1 118.2(4) . . ? C5 C6 C7 129.3(4) . . ? C1 C6 C7 112.4(3) . . ? O1 C7 C6 115.0(3) . . ? O1 C7 C8 115.4(3) . . ? C6 C7 C8 129.6(3) . . ? C13 C8 C9 118.0(3) . . ? C13 C8 C7 118.3(3) . . ? C9 C8 C7 123.5(4) . . ? C10 C9 C8 120.1(4) . . ? C11 C10 C9 121.1(4) . . ? C10 C11 C12 119.2(4) . . ? C13 C12 C11 120.7(4) . . ? C12 C13 C8 120.9(4) . . ? C15 C14 C19 114.2(3) . . ? C15 C14 Fe 134.3(3) . . ? C19 C14 Fe 111.4(2) . . ? C16 C15 C14 123.5(4) . . ? C15 C16 C17 120.8(4) . . ? C18 C17 C16 118.1(4) . . ? C17 C18 F2 118.1(3) . . ? C17 C18 C19 122.7(4) . . ? F2 C18 C19 119.1(3) . . ? C18 C19 C14 120.6(3) . . ? C18 C19 C20 126.0(3) . . ? C14 C19 C20 113.4(3) . . ? O2 C20 C19 115.8(3) . . ? O2 C20 C21 116.1(3) . . ? C19 C20 C21 128.1(3) . . ? C22 C21 C26 118.8(3) . . ? C22 C21 C20 120.4(3) . . ? C26 C21 C20 120.6(3) . . ? C21 C22 C23 120.3(4) . . ? C24 C23 C22 120.9(5) . . ? C23 C24 C25 119.6(4) . . ? C24 C25 C26 121.1(4) . . ? C21 C26 C25 119.2(4) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.394 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.067 data_test2 _database_code_depnum_ccdc_archive 'CCDC 847494' #TrackingRef '847494.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H36 F2 Fe N P3' _chemical_formula_sum 'C22 H36 F2 Fe N P3' _chemical_formula_weight 501.28 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' 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' 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 9.300(7) _cell_length_b 11.375(9) _cell_length_c 13.620(10) _cell_angle_alpha 66.927(11) _cell_angle_beta 79.162(13) _cell_angle_gamma 74.851(13) _cell_volume 1273.5(17) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3400 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.19 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8558 _exptl_absorpt_correction_T_max 0.9027 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6552 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4435 _reflns_number_gt 3568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens constr _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4435 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5469(3) 0.4381(3) 0.3202(2) 0.0374(7) Uani 1 1 d . . . C2 C 0.4432(4) 0.3937(3) 0.4064(3) 0.0505(8) Uani 1 1 d . . . C3 C 0.3324(5) 0.4732(4) 0.4466(4) 0.0683(11) Uani 1 1 d . . . H3 H 0.2661 0.4379 0.5048 0.082 Uiso 1 1 calc R . . C4 C 0.3205(5) 0.6059(4) 0.3998(4) 0.0691(11) Uani 1 1 d . . . H4 H 0.2467 0.6615 0.4266 0.083 Uiso 1 1 calc R . . C5 C 0.4181(5) 0.6560(4) 0.3133(3) 0.0706(12) Uani 1 1 d . . . H5 H 0.4099 0.7458 0.2802 0.085 Uiso 1 1 calc R . . C6 C 0.5284(4) 0.5721(3) 0.2759(3) 0.0527(9) Uani 1 1 d . . . C7 C 0.6673(3) 0.3481(3) 0.2804(2) 0.0336(6) Uani 1 1 d . . . C8 C 0.8239(3) 0.3383(3) 0.2796(2) 0.0373(7) Uani 1 1 d . . . C9 C 0.8853(4) 0.4101(3) 0.3184(3) 0.0490(8) Uani 1 1 d . . . H9 H 0.8226 0.4709 0.3456 0.059 Uiso 1 1 calc R . . C10 C 1.0370(4) 0.3910(4) 0.3162(3) 0.0561(9) Uani 1 1 d . . . H10 H 1.0780 0.4383 0.3420 0.067 Uiso 1 1 calc R . . C11 C 1.1296(4) 0.2999(3) 0.2750(3) 0.0510(9) Uani 1 1 d . . . H11 H 1.2329 0.2872 0.2728 0.061 Uiso 1 1 calc R . . C12 C 1.0706(3) 0.2287(3) 0.2375(3) 0.0452(8) Uani 1 1 d . . . H12 H 1.1364 0.1685 0.2109 0.054 Uiso 1 1 calc R . . C13 C 0.9147(3) 0.2416(3) 0.2370(2) 0.0351(6) Uani 1 1 d . . . C14 C 0.4874(4) 0.0111(3) 0.2654(3) 0.0566(9) Uani 1 1 d . . . H14A H 0.4113 -0.0076 0.2382 0.085 Uiso 1 1 calc R . . H14B H 0.4423 0.0731 0.2996 0.085 Uiso 1 1 calc R . . H14C H 0.5373 -0.0680 0.3165 0.085 Uiso 1 1 calc R . . C15 C 0.6730(5) -0.0451(4) 0.0927(3) 0.0668(11) Uani 1 1 d . . . H15A H 0.7358 -0.1218 0.1372 0.100 Uiso 1 1 calc R . . H15B H 0.7253 -0.0121 0.0231 0.100 Uiso 1 1 calc R . . H15C H 0.5832 -0.0669 0.0860 0.100 Uiso 1 1 calc R . . C16 C 0.4852(4) 0.2033(3) 0.0655(3) 0.0571(9) Uani 1 1 d . . . H16A H 0.5339 0.2414 -0.0047 0.086 Uiso 1 1 calc R . . H16B H 0.4396 0.2703 0.0946 0.086 Uiso 1 1 calc R . . H16C H 0.4098 0.1626 0.0607 0.086 Uiso 1 1 calc R . . C17 C 0.7366(4) -0.0165(4) 0.4592(3) 0.0559(9) Uani 1 1 d . . . H17A H 0.7731 -0.0934 0.5182 0.084 Uiso 1 1 calc R . . H17B H 0.6351 -0.0145 0.4523 0.084 Uiso 1 1 calc R . . H17C H 0.7406 0.0597 0.4721 0.084 Uiso 1 1 calc R . . C18 C 0.8532(5) -0.1835(3) 0.3413(3) 0.0590(10) Uani 1 1 d . . . H18A H 0.9216 -0.2018 0.2844 0.089 Uiso 1 1 calc R . . H18B H 0.7543 -0.1875 0.3335 0.089 Uiso 1 1 calc R . . H18C H 0.8836 -0.2470 0.4090 0.089 Uiso 1 1 calc R . . C19 C 1.0388(4) -0.0599(3) 0.3807(3) 0.0602(10) Uani 1 1 d . . . H19A H 1.0562 0.0132 0.3919 0.090 Uiso 1 1 calc R . . H19B H 1.1130 -0.0805 0.3273 0.090 Uiso 1 1 calc R . . H19C H 1.0447 -0.1340 0.4467 0.090 Uiso 1 1 calc R . . C20 C 1.0363(4) 0.3230(4) -0.0109(3) 0.0589(10) Uani 1 1 d . . . H20A H 1.0449 0.3763 -0.0857 0.088 Uiso 1 1 calc R . . H20B H 1.1128 0.2448 0.0023 0.088 Uiso 1 1 calc R . . H20C H 1.0479 0.3706 0.0308 0.088 Uiso 1 1 calc R . . C21 C 0.8529(5) 0.2279(4) -0.0854(3) 0.0679(11) Uani 1 1 d . . . H21A H 0.7536 0.2209 -0.0892 0.102 Uiso 1 1 calc R . . H21B H 0.9196 0.1446 -0.0743 0.102 Uiso 1 1 calc R . . H21C H 0.8858 0.2911 -0.1513 0.102 Uiso 1 1 calc R . . C22 C 0.7337(4) 0.4440(3) -0.0178(3) 0.0640(11) Uani 1 1 d . . . H22A H 0.7306 0.4848 0.0326 0.096 Uiso 1 1 calc R . . H22B H 0.6343 0.4378 -0.0221 0.096 Uiso 1 1 calc R . . H22C H 0.7740 0.4953 -0.0871 0.096 Uiso 1 1 calc R . . F1 F 0.4555(3) 0.2632(2) 0.4553(2) 0.0920(9) Uani 1 1 d . . . F2 F 0.6229(3) 0.6239(2) 0.1901(2) 0.0942(9) Uani 1 1 d . . . Fe1 Fe 0.79777(4) 0.15269(4) 0.19157(3) 0.03090(15) Uani 1 1 d . . . H1 H 0.921(4) 0.078(3) 0.149(3) 0.059(10) Uiso 1 1 d . . . N1 N 0.6377(3) 0.2663(2) 0.24412(18) 0.0332(5) Uani 1 1 d . . . H2 H 0.5463 0.2634 0.2439 0.040 Uiso 1 1 calc R . . P1 P 0.62447(9) 0.07963(8) 0.15359(7) 0.0403(2) Uani 1 1 d . . . P2 P 0.85314(9) -0.01908(7) 0.33561(6) 0.0379(2) Uani 1 1 d . . . P3 P 0.85244(9) 0.27995(8) 0.02679(6) 0.0411(2) Uani 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 C1 0.0403(17) 0.0330(15) 0.0389(16) -0.0176(13) -0.0026(13) -0.0014(13) C2 0.053(2) 0.0383(17) 0.062(2) -0.0263(16) 0.0125(16) -0.0120(15) C3 0.063(3) 0.067(3) 0.080(3) -0.045(2) 0.022(2) -0.012(2) C4 0.065(3) 0.060(2) 0.087(3) -0.049(2) -0.002(2) 0.012(2) C5 0.093(3) 0.0377(19) 0.074(3) -0.022(2) -0.017(2) 0.009(2) C6 0.071(2) 0.0381(17) 0.0422(19) -0.0127(15) 0.0021(17) -0.0073(17) C7 0.0404(17) 0.0304(14) 0.0295(14) -0.0134(12) 0.0013(12) -0.0057(13) C8 0.0428(18) 0.0343(15) 0.0331(16) -0.0116(13) -0.0001(13) -0.0088(13) C9 0.058(2) 0.0522(19) 0.0426(19) -0.0216(16) -0.0022(16) -0.0165(17) C10 0.061(2) 0.064(2) 0.050(2) -0.0146(18) -0.0106(17) -0.031(2) C11 0.0403(19) 0.057(2) 0.050(2) -0.0054(17) -0.0074(15) -0.0191(17) C12 0.0336(17) 0.0450(17) 0.0501(19) -0.0118(15) -0.0028(14) -0.0065(14) C13 0.0356(16) 0.0331(15) 0.0318(15) -0.0081(12) 0.0003(12) -0.0077(13) C14 0.044(2) 0.051(2) 0.073(3) -0.0209(19) -0.0035(18) -0.0112(17) C15 0.082(3) 0.055(2) 0.081(3) -0.047(2) -0.020(2) 0.000(2) C16 0.052(2) 0.058(2) 0.064(2) -0.0269(19) -0.0169(18) -0.0002(18) C17 0.060(2) 0.059(2) 0.0355(18) -0.0107(16) 0.0010(16) -0.0043(18) C18 0.068(2) 0.0335(16) 0.064(2) -0.0110(16) -0.0025(19) -0.0040(17) C19 0.052(2) 0.049(2) 0.062(2) -0.0035(18) -0.0184(18) 0.0003(17) C20 0.053(2) 0.064(2) 0.046(2) -0.0115(18) 0.0109(16) -0.0124(18) C21 0.075(3) 0.085(3) 0.039(2) -0.028(2) 0.0027(18) -0.007(2) C22 0.061(2) 0.0436(19) 0.055(2) 0.0019(17) 0.0017(18) 0.0051(18) F1 0.106(2) 0.0489(13) 0.1016(19) -0.0293(13) 0.0522(16) -0.0252(13) F2 0.132(2) 0.0474(12) 0.0731(17) -0.0070(12) 0.0208(16) -0.0141(14) Fe1 0.0312(3) 0.0283(2) 0.0305(2) -0.01261(18) -0.00014(17) -0.00065(17) N1 0.0307(13) 0.0319(12) 0.0366(13) -0.0157(11) -0.0005(10) -0.0027(10) P1 0.0411(5) 0.0368(4) 0.0478(5) -0.0232(4) -0.0077(4) -0.0009(4) P2 0.0374(5) 0.0325(4) 0.0361(4) -0.0088(3) -0.0029(3) -0.0008(3) P3 0.0412(5) 0.0395(4) 0.0326(4) -0.0110(3) 0.0027(3) 0.0005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.377(4) . ? C1 C2 1.389(5) . ? C1 C7 1.484(4) . ? C2 F1 1.350(4) . ? C2 C3 1.367(5) . ? C3 C4 1.371(6) . ? C3 H3 0.9300 . ? C4 C5 1.371(6) . ? C4 H4 0.9300 . ? C5 C6 1.377(5) . ? C5 H5 0.9300 . ? C6 F2 1.352(4) . ? C7 N1 1.315(4) . ? C7 C8 1.430(4) . ? C8 C9 1.402(4) . ? C8 C13 1.446(4) . ? C9 C10 1.366(5) . ? C9 H9 0.9300 . ? C10 C11 1.392(5) . ? C10 H10 0.9300 . ? C11 C12 1.371(5) . ? C11 H11 0.9300 . ? C12 C13 1.420(4) . ? C12 H12 0.9300 . ? C13 Fe1 1.977(3) . ? C14 P1 1.847(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 P1 1.830(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 P1 1.846(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 P2 1.829(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 P2 1.841(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 P2 1.825(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 P3 1.827(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 P3 1.841(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 P3 1.832(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? Fe1 N1 1.928(2) . ? Fe1 P2 2.1866(14) . ? Fe1 P3 2.1908(16) . ? Fe1 P1 2.2150(15) . ? Fe1 H1 1.42(3) . ? N1 H2 0.8600 . ? 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 C1 C2 114.1(3) . . ? C6 C1 C7 123.4(3) . . ? C2 C1 C7 122.5(3) . . ? F1 C2 C3 118.1(3) . . ? F1 C2 C1 117.6(3) . . ? C3 C2 C1 124.3(3) . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? F2 C6 C5 118.3(3) . . ? F2 C6 C1 118.1(3) . . ? C5 C6 C1 123.6(3) . . ? N1 C7 C8 113.5(2) . . ? N1 C7 C1 122.0(3) . . ? C8 C7 C1 124.5(3) . . ? C9 C8 C7 124.9(3) . . ? C9 C8 C13 122.8(3) . . ? C7 C8 C13 112.2(3) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 123.6(3) . . ? C11 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C12 C13 C8 113.1(3) . . ? C12 C13 Fe1 132.9(2) . . ? C8 C13 Fe1 114.0(2) . . ? P1 C14 H14A 109.5 . . ? P1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? P1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? P1 C15 H15A 109.5 . . ? P1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? P1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? P1 C16 H16A 109.5 . . ? P1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? P1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? P2 C17 H17A 109.5 . . ? P2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? P2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? P2 C18 H18A 109.5 . . ? P2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? P2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? P2 C19 H19A 109.5 . . ? P2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? P2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? P3 C20 H20A 109.5 . . ? P3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? P3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? P3 C21 H21A 109.5 . . ? P3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? P3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? P3 C22 H22A 109.5 . . ? P3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? P3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 Fe1 C13 79.79(12) . . ? N1 Fe1 P2 103.54(9) . . ? C13 Fe1 P2 88.09(10) . . ? N1 Fe1 P3 102.56(8) . . ? C13 Fe1 P3 86.89(10) . . ? P2 Fe1 P3 152.07(4) . . ? N1 Fe1 P1 87.75(9) . . ? C13 Fe1 P1 167.54(9) . . ? P2 Fe1 P1 94.71(6) . . ? P3 Fe1 P1 96.08(6) . . ? N1 Fe1 H1 175.5(13) . . ? C13 Fe1 H1 97.0(13) . . ? P2 Fe1 H1 79.4(13) . . ? P3 Fe1 H1 74.0(13) . . ? P1 Fe1 H1 95.4(13) . . ? C7 N1 Fe1 120.5(2) . . ? C7 N1 H2 119.8 . . ? Fe1 N1 H2 119.8 . . ? C15 P1 C16 100.73(18) . . ? C15 P1 C14 100.48(19) . . ? C16 P1 C14 95.98(19) . . ? C15 P1 Fe1 121.95(15) . . ? C16 P1 Fe1 116.48(13) . . ? C14 P1 Fe1 116.82(13) . . ? C19 P2 C17 100.07(19) . . ? C19 P2 C18 96.25(18) . . ? C17 P2 C18 101.01(18) . . ? C19 P2 Fe1 118.88(12) . . ? C17 P2 Fe1 115.82(13) . . ? C18 P2 Fe1 120.85(13) . . ? C20 P3 C22 99.46(19) . . ? C20 P3 C21 97.29(19) . . ? C22 P3 C21 101.4(2) . . ? C20 P3 Fe1 119.16(12) . . ? C22 P3 Fe1 115.91(13) . . ? C21 P3 Fe1 119.79(15) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.751 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.077 data_sun7 _database_code_depnum_ccdc_archive 'CCDC 847495' #TrackingRef 'SUN7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H35 Br F2 Fe N P3' _chemical_formula_weight 580.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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' Br Br -0.2901 2.4595 '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 ? _symmetry_space_group_name_H-M ? 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' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y, z-1/2' _cell_length_a 13.432(3) _cell_length_b 12.134(3) _cell_length_c 33.252(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5419(2) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 2.232 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6054 _exptl_absorpt_correction_T_max 0.6765 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _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 14857 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3201 _reflns_number_gt 2427 _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^)+(0.1124P)^2^+27.7177P] 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 3201 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1952 _refine_ls_wR_factor_gt 0.1763 _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 1.0000 0.31962(7) 0.15084(3) 0.0229(2) Uani 1 2 d S . . Br1 Br 1.0000 0.52822(6) 0.16529(2) 0.0443(3) Uani 1 2 d S . . P1 P 0.83177(9) 0.33667(11) 0.14852(4) 0.0335(3) Uani 1 1 d . . . P2 P 1.0000 0.26235(14) 0.21511(5) 0.0296(4) Uani 1 2 d S . . N1 N 1.0000 0.3560(5) 0.09364(16) 0.0297(12) Uani 1 2 d S . . H1 H 1.0000 0.4239 0.0863 0.036 Uiso 1 2 calc SR . . C1 C 1.0000 0.1704(5) 0.1277(2) 0.0280(13) Uani 1 2 d S . . C2 C 1.0000 0.0631(6) 0.1444(2) 0.0360(15) Uani 1 2 d S . . H2 H 1.0000 0.0567 0.1723 0.043 Uiso 1 2 calc SR . . C3 C 1.0000 -0.0330(6) 0.1219(3) 0.046(2) Uani 1 2 d S . . H3 H 1.0000 -0.1006 0.1351 0.055 Uiso 1 2 calc SR . . C4 C 1.0000 -0.0306(7) 0.0809(3) 0.053(2) Uani 1 2 d S . . H4 H 1.0000 -0.0955 0.0660 0.063 Uiso 1 2 calc SR . . C5 C 1.0000 0.0715(7) 0.0621(3) 0.053(2) Uani 1 2 d S . . H5 H 1.0000 0.0751 0.0342 0.064 Uiso 1 2 calc SR . . C6 C 1.0000 0.1689(6) 0.0845(2) 0.0374(16) Uani 1 2 d S . . C7 C 1.0000 0.2799(6) 0.0670(2) 0.0357(15) Uani 1 2 d S . . C8 C 0.7567(5) 0.2120(6) 0.1409(3) 0.0656(19) Uani 1 1 d . . . H8A H 0.7691 0.1610 0.1624 0.098 Uiso 1 1 calc R . . H8B H 0.7744 0.1785 0.1157 0.098 Uiso 1 1 calc R . . H8C H 0.6874 0.2312 0.1406 0.098 Uiso 1 1 calc R . . C9 C 0.7865(5) 0.4213(6) 0.10639(19) 0.0560(16) Uani 1 1 d . . . H9A H 0.7155 0.4288 0.1082 0.084 Uiso 1 1 calc R . . H9B H 0.8036 0.3865 0.0814 0.084 Uiso 1 1 calc R . . H9C H 0.8168 0.4929 0.1076 0.084 Uiso 1 1 calc R . . C10 C 0.7653(5) 0.4059(5) 0.18965(18) 0.0525(15) Uani 1 1 d . . . H10A H 0.7888 0.4803 0.1921 0.079 Uiso 1 1 calc R . . H10B H 0.7771 0.3671 0.2144 0.079 Uiso 1 1 calc R . . H10C H 0.6952 0.4063 0.1840 0.079 Uiso 1 1 calc R . . C11 C 0.8969(4) 0.1764(5) 0.23408(18) 0.0458(13) Uani 1 1 d . . . H11A H 0.9124 0.1509 0.2607 0.069 Uiso 1 1 calc R . . H11B H 0.8877 0.1142 0.2166 0.069 Uiso 1 1 calc R . . H11C H 0.8368 0.2192 0.2348 0.069 Uiso 1 1 calc R . . C12 C 1.0000 0.3687(8) 0.2540(2) 0.051(2) Uani 1 2 d S . . H12A H 0.9378 0.4076 0.2535 0.076 Uiso 0.50 1 calc PR . . H12B H 1.0535 0.4194 0.2491 0.076 Uiso 0.50 1 calc PR . . H12C H 1.0087 0.3350 0.2799 0.076 Uiso 0.50 1 calc PR . . C13 C 1.0135(10) 0.3016(7) 0.0235(2) 0.034(2) Uiso 0.50 1 d P . . C14 C 0.9330(13) 0.3376(15) -0.0004(5) 0.068(4) Uiso 0.50 1 d P . -1 C15 C 0.9331(15) 0.3539(16) -0.0410(6) 0.078(5) Uiso 0.50 1 d P . -1 H15A H 0.8759 0.3698 -0.0556 0.094 Uiso 0.50 1 calc PR . -1 C16 C 1.0256(9) 0.3447(10) -0.0581(4) 0.055(3) Uiso 0.50 1 d P . -1 H16A H 1.0332 0.3626 -0.0851 0.066 Uiso 0.50 1 calc PR . -1 C17 C 1.1075(15) 0.3098(16) -0.0368(6) 0.082(5) Uiso 0.50 1 d P . -1 H17A H 1.1697 0.3019 -0.0488 0.098 Uiso 0.50 1 calc PR . -1 C18 C 1.0928(12) 0.2885(14) 0.0013(5) 0.062(4) Uiso 0.50 1 d P . -1 F1 F 0.8446(16) 0.3558(19) 0.0159(6) 0.177(7) Uiso 0.50 1 d P A -1 F2 F 1.1718(11) 0.2577(13) 0.0211(5) 0.132(5) Uiso 0.50 1 d P B -1 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 0.0245(5) 0.0202(4) 0.0240(5) -0.0005(3) 0.000 0.000 Br1 0.0571(5) 0.0329(4) 0.0428(5) -0.0040(3) 0.000 0.000 P1 0.0257(7) 0.0329(7) 0.0418(7) 0.0016(5) 0.0003(5) 0.0016(5) P2 0.0338(9) 0.0275(8) 0.0276(8) 0.0029(6) 0.000 0.000 N1 0.036(3) 0.027(3) 0.026(3) 0.001(2) 0.000 0.000 C1 0.023(3) 0.026(3) 0.035(3) -0.002(3) 0.000 0.000 C2 0.040(4) 0.025(3) 0.043(4) 0.004(3) 0.000 0.000 C3 0.042(4) 0.024(4) 0.073(6) 0.001(3) 0.000 0.000 C4 0.065(6) 0.034(4) 0.060(6) -0.025(4) 0.000 0.000 C5 0.077(6) 0.039(4) 0.043(5) -0.019(3) 0.000 0.000 C6 0.049(4) 0.027(3) 0.037(4) -0.004(3) 0.000 0.000 C7 0.044(4) 0.035(4) 0.028(3) -0.002(3) 0.000 0.000 C8 0.039(3) 0.061(4) 0.097(5) -0.004(4) -0.011(3) -0.010(3) C9 0.041(3) 0.072(4) 0.055(4) 0.011(3) -0.006(3) 0.017(3) C10 0.042(3) 0.060(4) 0.055(3) 0.004(3) 0.013(3) 0.017(3) C11 0.045(3) 0.045(3) 0.047(3) 0.013(2) 0.009(2) -0.003(3) C12 0.070(6) 0.056(5) 0.026(4) -0.010(3) 0.000 0.000 _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 1.952(5) . ? Fe1 C1 1.967(6) . ? Fe1 P2 2.2474(19) . ? Fe1 P1 2.2704(14) . ? Fe1 P1 2.2704(14) 11_755 ? Fe1 Br1 2.5765(12) . ? P1 C8 1.836(7) . ? P1 C10 1.836(6) . ? P1 C9 1.841(6) . ? P2 C12 1.827(8) . ? P2 C11 1.845(5) 11_755 ? P2 C11 1.845(5) . ? N1 C7 1.279(9) . ? C1 C2 1.416(9) . ? C1 C6 1.438(10) . ? C2 C3 1.385(11) . ? C3 C4 1.364(14) . ? C4 C5 1.387(13) . ? C5 C6 1.397(10) . ? C6 C7 1.467(10) . ? C7 C13 1.483(11) . ? C7 C13 1.483(11) 11_755 ? C13 C13 0.36(3) 11_755 ? C13 C14 1.16(2) 11_755 ? C13 C18 1.30(2) . ? C13 C14 1.41(2) . ? C13 C18 1.61(2) 11_755 ? C14 C13 1.16(2) 11_755 ? C14 F1 1.32(3) . ? C14 C15 1.36(2) . ? C15 C16 1.37(2) . ? C16 C17 1.37(2) . ? C17 C18 1.31(2) . ? C18 F2 1.30(2) . ? C18 C13 1.61(2) 11_755 ? 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 C1 80.1(3) . . ? N1 Fe1 P2 175.05(18) . . ? C1 Fe1 P2 95.0(2) . . ? N1 Fe1 P1 86.92(4) . . ? C1 Fe1 P1 94.05(4) . . ? P2 Fe1 P1 93.47(4) . . ? N1 Fe1 P1 86.92(4) . 11_755 ? C1 Fe1 P1 94.05(4) . 11_755 ? P2 Fe1 P1 93.47(4) . 11_755 ? P1 Fe1 P1 168.84(8) . 11_755 ? N1 Fe1 Br1 87.69(17) . . ? C1 Fe1 Br1 167.7(2) . . ? P2 Fe1 Br1 97.26(6) . . ? P1 Fe1 Br1 85.23(4) . . ? P1 Fe1 Br1 85.23(4) 11_755 . ? C8 P1 C10 102.3(3) . . ? C8 P1 C9 100.0(4) . . ? C10 P1 C9 98.7(3) . . ? C8 P1 Fe1 118.4(2) . . ? C10 P1 Fe1 120.0(2) . . ? C9 P1 Fe1 113.9(2) . . ? C12 P2 C11 99.0(3) . 11_755 ? C12 P2 C11 99.0(3) . . ? C11 P2 C11 97.3(4) 11_755 . ? C12 P2 Fe1 117.1(3) . . ? C11 P2 Fe1 120.0(2) 11_755 . ? C11 P2 Fe1 120.0(2) . . ? C7 N1 Fe1 120.8(5) . . ? C2 C1 C6 112.4(6) . . ? C2 C1 Fe1 133.9(5) . . ? C6 C1 Fe1 113.7(5) . . ? C3 C2 C1 124.2(7) . . ? C4 C3 C2 121.5(7) . . ? C3 C4 C5 117.9(7) . . ? C4 C5 C6 121.1(8) . . ? C5 C6 C1 122.9(7) . . ? C5 C6 C7 124.5(7) . . ? C1 C6 C7 112.6(6) . . ? N1 C7 C6 112.8(6) . . ? N1 C7 C13 123.3(7) . . ? C6 C7 C13 123.3(6) . . ? N1 C7 C13 123.3(7) . 11_755 ? C6 C7 C13 123.3(6) . 11_755 ? C13 C7 C13 14.0(10) . 11_755 ? C13 C13 C14 128.4(11) 11_755 11_755 ? C13 C13 C18 144.8(8) 11_755 . ? C14 C13 C18 31.9(10) 11_755 . ? C13 C13 C14 40.0(8) 11_755 . ? C14 C13 C14 88.4(17) 11_755 . ? C18 C13 C14 110.3(11) . . ? C13 C13 C7 83.0(5) 11_755 . ? C14 C13 C7 144.4(13) 11_755 . ? C18 C13 C7 129.0(11) . . ? C14 C13 C7 120.7(11) . . ? C13 C13 C18 27.8(7) 11_755 11_755 ? C14 C13 C18 105.9(12) 11_755 11_755 ? C18 C13 C18 117.0(14) . 11_755 ? C14 C13 C18 25.3(8) . 11_755 ? C7 C13 C18 108.6(10) . 11_755 ? C13 C14 F1 109.8(17) 11_755 . ? C13 C14 C15 137.2(18) 11_755 . ? F1 C14 C15 112.4(18) . . ? C13 C14 C13 11.6(9) 11_755 . ? F1 C14 C13 120.6(16) . . ? C15 C14 C13 127.0(16) . . ? C14 C15 C16 113.6(18) . . ? C15 C16 C17 122.4(14) . . ? C18 C17 C16 116.0(18) . . ? F2 C18 C13 114.5(14) . . ? F2 C18 C17 115.1(17) . . ? C13 C18 C17 130.2(17) . . ? F2 C18 C13 121.2(13) . 11_755 ? C13 C18 C13 7.4(6) . 11_755 ? C17 C18 C13 123.7(15) . 11_755 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.871 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.136 data_d:\tmp\h_sun\9\sun9 _database_code_depnum_ccdc_archive 'CCDC 847496' #TrackingRef '847496.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H35 F2 Fe I N P3' _chemical_formula_weight 627.17 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' 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M cmca 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' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x, y, z' 'x, -y-1/2, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y, z-1/2' _cell_length_a 13.492(7) _cell_length_b 12.097(6) _cell_length_c 34.022(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5553(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1070 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 18.43 _exptl_crystal_description flake _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 1.851 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7687 _exptl_absorpt_correction_T_max 0.8660 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17416 _diffrn_reflns_av_R_equivalents 0.1621 _diffrn_reflns_av_sigmaI/netI 0.1821 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 28.50 _reflns_number_total 3628 _reflns_number_gt 1452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3628 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1667 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1639 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _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 1.0000 0.32244(12) 0.14983(4) 0.0330(4) Uani 1 2 d S . . I1 I 1.0000 0.54728(6) 0.16505(2) 0.0466(3) Uani 1 2 d S . . P1 P 0.83258(17) 0.33763(17) 0.14729(7) 0.0448(6) Uani 1 1 d . . . P2 P 1.0000 0.2643(2) 0.21226(9) 0.0434(8) Uani 1 2 d S . . N1 N 1.0000 0.3582(7) 0.0941(3) 0.036(2) Uani 1 2 d S . . H1 H 1.0000 0.4263 0.0869 0.043 Uiso 1 2 calc SR . . C1 C 1.0000 0.1732(8) 0.1265(3) 0.041(3) Uani 1 2 d S . . C2 C 1.0000 0.0677(9) 0.1426(4) 0.050(3) Uani 1 2 d S . . H2 H 1.0000 0.0605 0.1698 0.060 Uiso 1 2 calc SR . . C3 C 1.0000 -0.0283(9) 0.1196(5) 0.065(4) Uani 1 2 d S . . H3 H 1.0000 -0.0972 0.1317 0.078 Uiso 1 2 calc SR . . C4 C 1.0000 -0.0219(12) 0.0792(5) 0.070(4) Uani 1 2 d S . . H4 H 1.0000 -0.0860 0.0641 0.084 Uiso 1 2 calc SR . . C5 C 1.0000 0.0774(10) 0.0619(4) 0.074(5) Uani 1 2 d S . . H5 H 1.0000 0.0822 0.0346 0.089 Uiso 1 2 calc SR . . C6 C 1.0000 0.1735(10) 0.0843(3) 0.047(3) Uani 1 2 d S . . C7 C 1.0000 0.2817(10) 0.0678(4) 0.045(3) Uani 1 2 d S . . C8 C 0.7627(7) 0.2114(7) 0.1360(3) 0.085(4) Uani 1 1 d . . . H8A H 0.7771 0.1560 0.1554 0.128 Uiso 1 1 calc R . . H8B H 0.7816 0.1847 0.1105 0.128 Uiso 1 1 calc R . . H8C H 0.6931 0.2274 0.1362 0.128 Uiso 1 1 calc R . . C9 C 0.7863(6) 0.4203(7) 0.1061(2) 0.061(3) Uani 1 1 d . . . H9A H 0.7159 0.4296 0.1086 0.091 Uiso 1 1 calc R . . H9B H 0.8008 0.3832 0.0818 0.091 Uiso 1 1 calc R . . H9C H 0.8179 0.4914 0.1063 0.091 Uiso 1 1 calc R . . C10 C 0.7618(7) 0.4003(7) 0.1873(3) 0.069(3) Uani 1 1 d . . . H10A H 0.7887 0.4718 0.1932 0.103 Uiso 1 1 calc R . . H10B H 0.7656 0.3540 0.2102 0.103 Uiso 1 1 calc R . . H10C H 0.6938 0.4080 0.1794 0.103 Uiso 1 1 calc R . . C11 C 0.8958(6) 0.1759(7) 0.2295(3) 0.059(3) Uani 1 1 d . . . H11A H 0.9121 0.1445 0.2546 0.088 Uiso 1 1 calc R . . H11B H 0.8845 0.1177 0.2108 0.088 Uiso 1 1 calc R . . H11C H 0.8369 0.2200 0.2319 0.088 Uiso 1 1 calc R . . C12 C 1.0000 0.3673(11) 0.2514(3) 0.069(4) Uani 1 2 d S . . H12A H 0.9350 0.3989 0.2538 0.104 Uiso 0.50 1 calc PR . . H12B H 1.0468 0.4245 0.2452 0.104 Uiso 0.50 1 calc PR . . H12C H 1.0182 0.3329 0.2758 0.104 Uiso 0.50 1 calc PR . . C13 C 1.014(2) 0.3012(10) 0.0250(4) 0.049(5) Uiso 0.50 1 d P . . C14 C 0.9402(19) 0.338(2) 0.0031(7) 0.086(8) Uiso 0.50 1 d P . -1 C15 C 0.936(2) 0.358(3) -0.0374(9) 0.119(12) Uiso 0.50 1 d P . -1 H15A H 0.8810 0.3804 -0.0517 0.142 Uiso 0.50 1 calc PR . -1 C16 C 1.0310(13) 0.3375(14) -0.0523(5) 0.054(6) Uiso 0.50 1 d P . -1 H16A H 1.0377 0.3477 -0.0793 0.065 Uiso 0.50 1 calc PR . -1 C17 C 1.112(2) 0.306(2) -0.0342(8) 0.105(9) Uiso 0.50 1 d P . -1 H17A H 1.1725 0.2983 -0.0467 0.126 Uiso 0.50 1 calc PR . -1 C18 C 1.098(2) 0.285(2) 0.0054(7) 0.080(7) Uiso 0.50 1 d P . -1 F1 F 0.8449(14) 0.3591(16) 0.0185(5) 0.162(7) Uiso 0.50 1 d P A -1 F2 F 1.1754(12) 0.2479(14) 0.0255(5) 0.139(5) Uiso 0.50 1 d P B -1 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 0.0314(9) 0.0270(8) 0.0406(9) -0.0010(7) 0.000 0.000 I1 0.0559(5) 0.0326(4) 0.0514(5) -0.0054(4) 0.000 0.000 P1 0.0329(13) 0.0395(12) 0.0619(15) 0.0032(11) -0.0004(11) 0.0001(10) P2 0.044(2) 0.0390(17) 0.047(2) 0.0070(15) 0.000 0.000 N1 0.033(6) 0.028(5) 0.047(6) -0.002(4) 0.000 0.000 C1 0.043(7) 0.028(6) 0.051(8) -0.004(5) 0.000 0.000 C2 0.041(8) 0.040(7) 0.068(9) 0.004(6) 0.000 0.000 C3 0.047(8) 0.017(6) 0.130(14) -0.002(7) 0.000 0.000 C4 0.084(11) 0.057(10) 0.069(10) -0.034(8) 0.000 0.000 C5 0.116(14) 0.030(7) 0.076(11) -0.029(7) 0.000 0.000 C6 0.063(9) 0.043(7) 0.033(7) -0.012(6) 0.000 0.000 C7 0.044(8) 0.046(7) 0.047(8) 0.004(6) 0.000 0.000 C8 0.039(6) 0.057(6) 0.159(11) 0.007(7) -0.015(6) -0.015(5) C9 0.038(5) 0.068(6) 0.077(7) 0.015(5) -0.003(5) 0.014(5) C10 0.050(6) 0.069(6) 0.087(7) 0.009(6) 0.016(6) 0.013(5) C11 0.052(6) 0.051(5) 0.073(6) 0.023(5) 0.007(5) -0.007(5) C12 0.099(12) 0.080(10) 0.029(7) 0.010(7) 0.000 0.000 _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 1.945(9) . ? Fe1 C1 1.973(10) . ? Fe1 P2 2.238(3) . ? Fe1 P1 2.268(2) . ? Fe1 I1 2.769(2) . ? P1 C10 1.827(9) . ? P1 C9 1.831(8) . ? P1 C8 1.835(8) . ? P2 C12 1.824(13) . ? P2 C11 1.860(8) . ? N1 C7 1.287(13) . ? C1 C2 1.388(14) . ? C1 C6 1.436(14) . ? C2 C3 1.400(16) . ? C3 C4 1.376(19) . ? C4 C5 1.339(17) . ? C5 C6 1.389(14) . ? C6 C7 1.424(15) . ? C7 C13 1.487(16) . ? C13 C14 1.32(3) . ? C13 C18 1.34(4) . ? C14 C15 1.40(3) . ? C14 F1 1.41(3) . ? C15 C16 1.40(3) . ? C16 C17 1.31(3) . ? C17 C18 1.38(3) . ? C18 F2 1.32(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 N1 Fe1 C1 79.1(4) . . ? N1 Fe1 P2 174.5(3) . . ? C1 Fe1 P2 95.4(3) . . ? N1 Fe1 P1 86.84(7) . . ? C1 Fe1 P1 93.37(7) . . ? P2 Fe1 P1 93.54(7) . . ? N1 Fe1 I1 87.9(3) . . ? C1 Fe1 I1 167.1(3) . . ? P2 Fe1 I1 97.55(10) . . ? P1 Fe1 I1 85.85(6) . . ? C10 P1 C9 99.5(4) . . ? C10 P1 C8 103.4(5) . . ? C9 P1 C8 96.9(5) . . ? C10 P1 Fe1 121.7(3) . . ? C9 P1 Fe1 114.4(3) . . ? C8 P1 Fe1 116.9(3) . . ? C12 P2 C11 99.4(4) . . ? C12 P2 Fe1 118.5(4) . . ? C11 P2 Fe1 118.6(3) . . ? C7 N1 Fe1 121.2(8) . . ? C2 C1 C6 113.4(10) . . ? C2 C1 Fe1 133.1(9) . . ? C6 C1 Fe1 113.6(8) . . ? C1 C2 C3 122.9(13) . . ? C4 C3 C2 120.7(12) . . ? C5 C4 C3 119.3(12) . . ? C4 C5 C6 120.6(14) . . ? C5 C6 C7 123.5(12) . . ? C5 C6 C1 123.1(12) . . ? C7 C6 C1 113.4(10) . . ? N1 C7 C6 112.8(11) . . ? N1 C7 C13 124.5(11) . . ? C6 C7 C13 122.1(11) . . ? C14 C13 C18 114.3(19) . . ? C14 C13 C7 121(2) . . ? C18 C13 C7 125(2) . . ? C13 C14 C15 130(3) . . ? C13 C14 F1 123(2) . . ? C15 C14 F1 107(2) . . ? C16 C15 C14 107(3) . . ? C17 C16 C15 130(2) . . ? C16 C17 C18 114(3) . . ? F2 C18 C13 118(2) . . ? F2 C18 C17 118(3) . . ? C13 C18 C17 125(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.788 _refine_diff_density_min -0.669 _refine_diff_density_rms 0.120