# Electronic Supplementary Material (ESI) for RSC Advances # 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_ortho _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Fe N2 O' _chemical_formula_weight 320.17 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' _symmetry_space_group_name_Hall 'P 2c -2n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 20.791(11) _cell_length_b 5.874(3) _cell_length_c 11.646(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1422.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7972 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 25.92 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7851 _exptl_absorpt_correction_T_max 0.9107 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13592 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.95 _reflns_number_total 2766 _reflns_number_gt 2636 _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^)+(0.0307P)^2^+0.3526P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 2766 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.184926(14) 0.20754(6) 0.66467(5) 0.03389(11) Uani 1 1 d . . . N1 N 0.00171(12) 0.3000(4) 0.5525(2) 0.0389(6) Uani 1 1 d . . . C1 C -0.08992(15) -0.1931(5) 0.6540(5) 0.0522(8) Uani 1 1 d . . . H1 H -0.1056 -0.3286 0.6237 0.063 Uiso 1 1 calc R . . C2 C 0.20633(17) 0.1877(6) 0.4947(3) 0.0521(8) Uani 1 1 d . . . H2 H 0.1800 0.2327 0.4343 0.063 Uiso 1 1 calc R . . C3 C -0.03273(14) 0.1486(5) 0.6253(2) 0.0326(7) Uani 1 1 d . . . C4 C 0.09460(12) 0.3345(4) 0.6806(3) 0.0341(7) Uani 1 1 d . . . O1 O 0.07258(10) 0.5823(4) 0.5275(2) 0.0552(6) Uani 1 1 d . . . N2 N -0.10328(14) -0.1478(5) 0.7624(3) 0.0577(8) Uani 1 1 d . . . C6 C 0.13962(14) 0.4765(5) 0.7383(3) 0.0411(7) Uani 1 1 d . . . H6 H 0.1474 0.6292 0.7226 0.049 Uiso 1 1 calc R . . C7 C -0.04700(16) 0.2046(6) 0.7363(3) 0.0401(8) Uani 1 1 d . . . H7 H -0.0338 0.3427 0.7674 0.048 Uiso 1 1 calc R . . C8 C 0.28063(15) 0.1912(7) 0.6357(4) 0.0650(13) Uani 1 1 d . . . H8 H 0.3126 0.2395 0.6860 0.078 Uiso 1 1 calc R . . C9 C 0.17011(16) 0.3459(7) 0.8229(3) 0.0505(8) Uani 1 1 d . . . H9 H 0.2014 0.3980 0.8736 0.061 Uiso 1 1 calc R . . C10 C 0.05608(13) 0.4178(4) 0.5823(3) 0.0368(6) Uani 1 1 d . . . C11 C 0.25381(15) -0.0278(6) 0.6317(3) 0.0584(11) Uani 1 1 d . . . H11 H 0.2647 -0.1501 0.6786 0.070 Uiso 1 1 calc R . . C12 C -0.02903(17) 0.3580(6) 0.4438(3) 0.0527(8) Uani 1 1 d . . . H12A H -0.0254 0.5189 0.4307 0.079 Uiso 1 1 calc R . . H12B H -0.0736 0.3160 0.4466 0.079 Uiso 1 1 calc R . . H12C H -0.0083 0.2772 0.3825 0.079 Uiso 1 1 calc R . . C13 C 0.25136(17) 0.3240(6) 0.5516(3) 0.0598(10) Uani 1 1 d . . . H13 H 0.2602 0.4762 0.5360 0.072 Uiso 1 1 calc R . . C14 C 0.20811(15) -0.0284(6) 0.5450(3) 0.0504(8) Uani 1 1 d . . . H14 H 0.1828 -0.1521 0.5238 0.060 Uiso 1 1 calc R . . C15 C -0.08163(16) 0.0495(6) 0.8010(3) 0.0515(8) Uani 1 1 d . . . H15 H -0.0903 0.0868 0.8771 0.062 Uiso 1 1 calc R . . C16 C -0.05464(14) -0.0554(5) 0.5826(3) 0.0420(7) Uani 1 1 d . . . H16 H -0.0458 -0.0989 0.5075 0.050 Uiso 1 1 calc R . . C17 C 0.09915(13) 0.1126(5) 0.7309(3) 0.0391(7) Uani 1 1 d . . . H17 H 0.0756 -0.0152 0.7096 0.047 Uiso 1 1 calc R . . C18 C 0.14562(14) 0.1232(6) 0.8184(3) 0.0468(8) Uani 1 1 d . . . H18 H 0.1581 0.0030 0.8654 0.056 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 0.02354(17) 0.0395(2) 0.0387(2) -0.0055(3) 0.0010(2) -0.00081(14) N1 0.0378(14) 0.0434(14) 0.0356(13) 0.0063(11) -0.0031(11) -0.0022(10) C1 0.0488(16) 0.0397(15) 0.068(2) -0.0057(19) 0.004(2) -0.0081(12) C2 0.0513(19) 0.063(2) 0.0422(18) -0.0037(16) 0.0133(16) 0.0065(16) C3 0.0244(14) 0.0332(14) 0.0402(16) 0.0057(11) -0.0046(11) 0.0017(11) C4 0.0236(11) 0.0356(13) 0.0433(19) 0.0000(14) 0.0042(14) 0.0008(9) O1 0.0494(13) 0.0443(13) 0.0719(16) 0.0234(12) -0.0061(11) -0.0079(10) N2 0.0509(17) 0.060(2) 0.062(2) 0.0086(16) 0.0078(15) -0.0085(15) C6 0.0359(16) 0.0395(17) 0.0480(17) -0.0165(13) 0.0049(13) 0.0015(13) C7 0.0315(16) 0.0443(19) 0.0444(19) -0.0084(14) 0.0001(14) 0.0008(13) C8 0.0227(14) 0.088(3) 0.084(4) -0.026(2) 0.0114(16) -0.0020(15) C9 0.0393(17) 0.075(2) 0.0368(17) -0.0203(16) -0.0039(14) 0.0017(17) C10 0.0346(15) 0.0288(14) 0.0472(17) 0.0031(13) 0.0032(13) 0.0030(11) C11 0.0418(17) 0.054(2) 0.079(3) -0.0046(17) 0.0072(16) 0.0188(15) C12 0.059(2) 0.056(2) 0.0428(18) 0.0075(16) -0.0122(16) -0.0042(16) C13 0.054(2) 0.050(2) 0.075(3) -0.0008(19) 0.038(2) -0.0082(16) C14 0.0446(18) 0.0503(19) 0.056(2) -0.0213(16) 0.0122(15) 0.0018(15) C15 0.0407(17) 0.071(2) 0.0426(18) 0.0030(17) 0.0079(15) -0.0045(16) C16 0.0417(17) 0.0460(17) 0.0384(16) -0.0081(14) 0.0004(13) -0.0017(13) C17 0.0269(14) 0.0464(17) 0.0439(17) 0.0039(14) 0.0048(12) -0.0004(13) C18 0.0340(16) 0.070(2) 0.0365(16) 0.0115(15) 0.0023(13) 0.0056(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C8 2.021(3) . ? Fe1 C17 2.021(3) . ? Fe1 C14 2.024(3) . ? Fe1 C11 2.027(3) . ? Fe1 C13 2.027(3) . ? Fe1 C18 2.029(3) . ? Fe1 C4 2.029(3) . ? Fe1 C6 2.029(3) . ? Fe1 C2 2.032(4) . ? Fe1 C9 2.037(3) . ? N1 C10 1.370(4) . ? N1 C3 1.421(4) . ? N1 C12 1.459(4) . ? C1 N2 1.319(6) . ? C1 C16 1.372(5) . ? C2 C13 1.399(5) . ? C2 C14 1.399(5) . ? C3 C7 1.366(4) . ? C3 C16 1.375(4) . ? C4 C6 1.422(4) . ? C4 C17 1.432(4) . ? C4 C10 1.480(5) . ? O1 C10 1.208(3) . ? N2 C15 1.322(5) . ? C6 C9 1.400(5) . ? C7 C15 1.384(5) . ? C8 C13 1.393(6) . ? C8 C11 1.403(5) . ? C9 C18 1.405(5) . ? C11 C14 1.387(5) . ? C17 C18 1.405(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 C8 Fe1 C17 156.84(15) . . ? C8 Fe1 C14 67.54(14) . . ? C17 Fe1 C14 106.51(13) . . ? C8 Fe1 C11 40.55(15) . . ? C17 Fe1 C11 120.50(14) . . ? C14 Fe1 C11 40.03(14) . . ? C8 Fe1 C13 40.24(16) . . ? C17 Fe1 C13 160.39(16) . . ? C14 Fe1 C13 67.76(14) . . ? C11 Fe1 C13 68.02(15) . . ? C8 Fe1 C18 122.16(15) . . ? C17 Fe1 C18 40.59(12) . . ? C14 Fe1 C18 122.43(15) . . ? C11 Fe1 C18 106.58(15) . . ? C13 Fe1 C18 158.40(16) . . ? C8 Fe1 C4 160.77(14) . . ? C17 Fe1 C4 41.40(12) . . ? C14 Fe1 C4 122.35(13) . . ? C11 Fe1 C4 157.19(13) . . ? C13 Fe1 C4 124.47(16) . . ? C18 Fe1 C4 68.67(13) . . ? C8 Fe1 C6 124.39(14) . . ? C17 Fe1 C6 69.13(13) . . ? C14 Fe1 C6 159.18(13) . . ? C11 Fe1 C6 159.85(14) . . ? C13 Fe1 C6 109.16(14) . . ? C18 Fe1 C6 68.29(14) . . ? C4 Fe1 C6 41.03(11) . . ? C8 Fe1 C2 67.60(16) . . ? C17 Fe1 C2 123.31(14) . . ? C14 Fe1 C2 40.35(14) . . ? C11 Fe1 C2 67.77(15) . . ? C13 Fe1 C2 40.31(15) . . ? C18 Fe1 C2 158.99(15) . . ? C4 Fe1 C2 108.23(15) . . ? C6 Fe1 C2 123.91(14) . . ? C8 Fe1 C9 108.59(14) . . ? C17 Fe1 C9 68.37(13) . . ? C14 Fe1 C9 158.76(16) . . ? C11 Fe1 C9 123.38(14) . . ? C13 Fe1 C9 123.77(16) . . ? C18 Fe1 C9 40.41(15) . . ? C4 Fe1 C9 68.33(13) . . ? C6 Fe1 C9 40.27(14) . . ? C2 Fe1 C9 159.54(16) . . ? C10 N1 C3 125.5(2) . . ? C10 N1 C12 117.6(2) . . ? C3 N1 C12 116.3(2) . . ? N2 C1 C16 125.0(3) . . ? C13 C2 C14 107.7(3) . . ? C13 C2 Fe1 69.7(2) . . ? C14 C2 Fe1 69.51(18) . . ? C7 C3 C16 118.6(3) . . ? C7 C3 N1 121.5(3) . . ? C16 C3 N1 119.8(3) . . ? C6 C4 C17 107.3(3) . . ? C6 C4 C10 121.9(3) . . ? C17 C4 C10 130.8(3) . . ? C6 C4 Fe1 69.49(15) . . ? C17 C4 Fe1 69.01(15) . . ? C10 C4 Fe1 123.5(2) . . ? C1 N2 C15 115.5(3) . . ? C9 C6 C4 108.0(3) . . ? C9 C6 Fe1 70.18(18) . . ? C4 C6 Fe1 69.48(16) . . ? C3 C7 C15 118.0(3) . . ? C13 C8 C11 108.5(3) . . ? C13 C8 Fe1 70.14(18) . . ? C11 C8 Fe1 69.97(18) . . ? C6 C9 C18 108.6(3) . . ? C6 C9 Fe1 69.55(18) . . ? C18 C9 Fe1 69.47(18) . . ? O1 C10 N1 120.3(3) . . ? O1 C10 C4 121.3(3) . . ? N1 C10 C4 118.4(2) . . ? C14 C11 C8 107.4(3) . . ? C14 C11 Fe1 69.86(18) . . ? C8 C11 Fe1 69.48(19) . . ? C8 C13 C2 107.8(3) . . ? C8 C13 Fe1 69.6(2) . . ? C2 C13 Fe1 70.03(19) . . ? C11 C14 C2 108.7(3) . . ? C11 C14 Fe1 70.11(19) . . ? C2 C14 Fe1 70.14(19) . . ? N2 C15 C7 124.6(3) . . ? C1 C16 C3 118.1(3) . . ? C18 C17 C4 107.6(3) . . ? C18 C17 Fe1 69.99(18) . . ? C4 C17 Fe1 69.59(15) . . ? C9 C18 C17 108.5(3) . . ? C9 C18 Fe1 70.12(18) . . ? C17 C18 Fe1 69.41(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.410 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 941950' ####################################################################### # # 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_mono #TrackingRef '12876_web_deposit_cif_file_0_Dr.ProdeepPhukan_1343305789.Fer-Dipyridin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Fe N4 O2' _chemical_formula_weight 454.31 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.447(9) _cell_length_b 6.2758(19) _cell_length_c 12.914(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.647(7) _cell_angle_gamma 90.00 _cell_volume 2060.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7042 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 25.91 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7711 _exptl_absorpt_correction_T_max 0.9142 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _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_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10015 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.93 _reflns_number_total 1994 _reflns_number_gt 1878 _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^)+(0.0535P)^2^+1.1147P] 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 1994 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 0.24115(5) 0.7500 0.03213(15) Uani 1 2 d S . . O1 O 0.40250(6) -0.1365(2) 0.68917(17) 0.0675(5) Uani 1 1 d . . . C6 C 0.39984(8) 0.0369(3) 0.72924(19) 0.0472(5) Uani 1 1 d . . . C7 C 0.34201(8) 0.2893(3) 0.7630(2) 0.0455(5) Uani 1 1 d . . . N2 N 0.35193(6) 0.1344(3) 0.69603(15) 0.0486(4) Uani 1 1 d . . . C2 C 0.44757(7) 0.1530(3) 0.80804(16) 0.0414(4) Uani 1 1 d . . . C4 C 0.48900(8) 0.4090(4) 0.60497(17) 0.0511(5) Uani 1 1 d . . . H4 H 0.4723 0.5400 0.5811 0.061 Uiso 1 1 calc R . . C1 C 0.49697(8) 0.0499(4) 0.87228(17) 0.0477(5) Uani 1 1 d . . . H1 H 0.5027 -0.0965 0.8779 0.057 Uiso 1 1 calc R . . C3 C 0.45701(8) 0.3784(3) 0.82232(17) 0.0454(5) Uani 1 1 d . . . H3 H 0.4320 0.4850 0.7894 0.055 Uiso 1 1 calc R . . C11 C 0.31000(9) 0.4614(4) 0.7108(2) 0.0576(6) Uani 1 1 d . . . H11 H 0.2957 0.4808 0.6310 0.069 Uiso 1 1 calc R . . N1 N 0.31855(9) 0.5897(4) 0.8929(2) 0.0754(6) Uani 1 1 d . . . C12 C 0.30732(9) 0.0520(4) 0.5920(2) 0.0631(6) Uani 1 1 d . . . H12A H 0.3070 0.1171 0.5245 0.095 Uiso 1 1 calc R . . H12B H 0.2751 0.0846 0.5956 0.095 Uiso 1 1 calc R . . H12C H 0.3106 -0.0996 0.5880 0.095 Uiso 1 1 calc R . . C5 C 0.46443(9) 0.2080(4) 0.57430(18) 0.0520(5) Uani 1 1 d . . . H5 H 0.4289 0.1839 0.5270 0.062 Uiso 1 1 calc R . . C8 C 0.36142(10) 0.2694(4) 0.8818(2) 0.0562(6) Uani 1 1 d . . . H8 H 0.3825 0.1541 0.9206 0.067 Uiso 1 1 calc R . . C9 C 0.34909(9) 0.4226(5) 0.9417(2) 0.0679(7) Uani 1 1 d . . . H9 H 0.3631 0.4081 1.0217 0.082 Uiso 1 1 calc R . . C10 C 0.29974(10) 0.6031(4) 0.7784(3) 0.0745(8) Uani 1 1 d . . . H10 H 0.2779 0.7177 0.7416 0.089 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 0.0359(2) 0.0325(2) 0.0315(2) 0.000 0.01833(17) 0.000 O1 0.0624(10) 0.0445(9) 0.1043(14) -0.0108(9) 0.0451(10) -0.0050(7) C6 0.0500(11) 0.0424(11) 0.0623(12) 0.0080(9) 0.0368(10) 0.0021(9) C7 0.0385(10) 0.0514(11) 0.0565(13) 0.0105(9) 0.0302(10) 0.0044(8) N2 0.0441(9) 0.0536(10) 0.0534(10) 0.0034(8) 0.0267(8) 0.0029(8) C2 0.0460(10) 0.0446(11) 0.0466(10) 0.0065(9) 0.0324(9) 0.0066(9) C4 0.0534(12) 0.0585(13) 0.0425(10) 0.0149(9) 0.0223(9) -0.0018(10) C1 0.0552(12) 0.0517(12) 0.0467(11) 0.0188(9) 0.0324(10) 0.0137(9) C3 0.0484(11) 0.0462(11) 0.0484(11) -0.0043(9) 0.0277(9) 0.0084(9) C11 0.0507(12) 0.0660(14) 0.0603(13) 0.0156(11) 0.0287(11) 0.0147(10) N1 0.0750(14) 0.0812(15) 0.0869(16) -0.0021(13) 0.0512(13) 0.0179(12) C12 0.0543(13) 0.0691(15) 0.0656(14) -0.0016(12) 0.0266(11) -0.0056(11) C5 0.0497(12) 0.0733(14) 0.0324(10) -0.0052(9) 0.0177(9) -0.0114(10) C8 0.0547(13) 0.0675(15) 0.0590(14) 0.0179(10) 0.0367(12) 0.0183(10) C9 0.0598(14) 0.096(2) 0.0611(14) 0.0038(13) 0.0388(12) 0.0112(13) C10 0.0697(16) 0.0691(16) 0.096(2) 0.0154(15) 0.0472(16) 0.0275(13) _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 2.0160(19) . ? Fe1 C1 2.0160(19) 2_656 ? Fe1 C2 2.0235(18) . ? Fe1 C2 2.0236(18) 2_656 ? Fe1 C3 2.0332(19) 2_656 ? Fe1 C3 2.0332(19) . ? Fe1 C5 2.039(2) . ? Fe1 C5 2.039(2) 2_656 ? Fe1 C4 2.047(2) . ? Fe1 C4 2.047(2) 2_656 ? O1 C6 1.221(3) . ? C6 N2 1.375(3) . ? C6 C2 1.474(3) . ? C7 C11 1.378(3) . ? C7 C8 1.384(3) . ? C7 N2 1.411(3) . ? N2 C12 1.467(3) . ? C2 C1 1.427(3) . ? C2 C3 1.436(3) . ? C4 C3 1.409(3) 2_656 ? C4 C5 1.410(3) . ? C1 C5 1.410(3) 2_656 ? C3 C4 1.409(3) 2_656 ? C11 C10 1.367(4) . ? N1 C9 1.327(3) . ? N1 C10 1.331(4) . ? C5 C1 1.410(3) 2_656 ? C8 C9 1.374(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 C1 106.91(13) . 2_656 ? C1 Fe1 C2 41.37(8) . . ? C1 Fe1 C2 115.15(8) 2_656 . ? C1 Fe1 C2 115.15(8) . 2_656 ? C1 Fe1 C2 41.38(8) 2_656 2_656 ? C2 Fe1 C2 148.28(12) . 2_656 ? C1 Fe1 C3 149.07(9) . 2_656 ? C1 Fe1 C3 69.30(9) 2_656 2_656 ? C2 Fe1 C3 168.81(8) . 2_656 ? C2 Fe1 C3 41.45(9) 2_656 2_656 ? C1 Fe1 C3 69.30(8) . . ? C1 Fe1 C3 149.07(9) 2_656 . ? C2 Fe1 C3 41.45(9) . . ? C2 Fe1 C3 168.81(8) 2_656 . ? C3 Fe1 C3 129.88(12) 2_656 . ? C1 Fe1 C5 129.55(10) . . ? C1 Fe1 C5 40.68(9) 2_656 . ? C2 Fe1 C5 107.70(9) . . ? C2 Fe1 C5 68.91(9) 2_656 . ? C3 Fe1 C5 68.44(9) 2_656 . ? C3 Fe1 C5 116.99(9) . . ? C1 Fe1 C5 40.68(9) . 2_656 ? C1 Fe1 C5 129.55(10) 2_656 2_656 ? C2 Fe1 C5 68.92(9) . 2_656 ? C2 Fe1 C5 107.69(9) 2_656 2_656 ? C3 Fe1 C5 116.99(9) 2_656 2_656 ? C3 Fe1 C5 68.45(9) . 2_656 ? C5 Fe1 C5 168.28(14) . 2_656 ? C1 Fe1 C4 168.66(9) . . ? C1 Fe1 C4 68.43(10) 2_656 . ? C2 Fe1 C4 130.09(8) . . ? C2 Fe1 C4 68.73(9) 2_656 . ? C3 Fe1 C4 40.39(8) 2_656 . ? C3 Fe1 C4 109.01(9) . . ? C5 Fe1 C4 40.38(9) . . ? C5 Fe1 C4 150.09(11) 2_656 . ? C1 Fe1 C4 68.43(10) . 2_656 ? C1 Fe1 C4 168.66(9) 2_656 2_656 ? C2 Fe1 C4 68.73(9) . 2_656 ? C2 Fe1 C4 130.09(8) 2_656 2_656 ? C3 Fe1 C4 109.01(9) 2_656 2_656 ? C3 Fe1 C4 40.39(8) . 2_656 ? C5 Fe1 C4 150.09(10) . 2_656 ? C5 Fe1 C4 40.38(9) 2_656 2_656 ? C4 Fe1 C4 118.06(14) . 2_656 ? O1 C6 N2 120.3(2) . . ? O1 C6 C2 121.36(19) . . ? N2 C6 C2 118.19(18) . . ? C11 C7 C8 117.4(2) . . ? C11 C7 N2 120.6(2) . . ? C8 C7 N2 121.83(19) . . ? C6 N2 C7 123.92(18) . . ? C6 N2 C12 117.26(18) . . ? C7 N2 C12 118.36(18) . . ? C1 C2 C3 107.07(17) . . ? C1 C2 C6 122.62(19) . . ? C3 C2 C6 129.59(17) . . ? C1 C2 Fe1 69.03(10) . . ? C3 C2 Fe1 69.64(10) . . ? C6 C2 Fe1 118.90(13) . . ? C3 C4 C5 108.7(2) 2_656 . ? C3 C4 Fe1 69.29(11) 2_656 . ? C5 C4 Fe1 69.50(12) . . ? C5 C1 C2 108.24(19) 2_656 . ? C5 C1 Fe1 70.52(12) 2_656 . ? C2 C1 Fe1 69.60(10) . . ? C4 C3 C2 107.76(18) 2_656 . ? C4 C3 Fe1 70.33(11) 2_656 . ? C2 C3 Fe1 68.91(10) . . ? C10 C11 C7 118.7(2) . . ? C9 N1 C10 115.4(2) . . ? C1 C5 C4 108.2(2) 2_656 . ? C1 C5 Fe1 68.79(11) 2_656 . ? C4 C5 Fe1 70.12(12) . . ? C9 C8 C7 119.0(2) . . ? N1 C9 C8 124.3(2) . . ? N1 C10 C11 125.1(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.216 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 893849'