# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 186/1239 data_p85c_fs _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H8 Fe N2 O4' _chemical_formula_weight 300.05 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 4.95440(10) _cell_length_b 13.2443(2) _cell_length_c 10.49830(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.5860(10) _cell_angle_gamma 90.00 _cell_volume 674.84(2) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method ? _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 1.127 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7105 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 28.27 _reflns_number_total 7105 _reflns_number_observed 5981 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0751P)^2^+1.7888P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7105 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_obs 0.0574 _refine_ls_wR_factor_all 0.1810 _refine_ls_wR_factor_obs 0.1628 _refine_ls_goodness_of_fit_all 1.190 _refine_ls_goodness_of_fit_obs 1.167 _refine_ls_restrained_S_all 1.190 _refine_ls_restrained_S_obs 1.167 _refine_ls_shift/esd_max -0.004 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe Fe 0.0000 0.0000 0.0000 0.01373(13) Uani 1 d S . O1 O 0.6264(3) -0.03749(12) -0.1331(2) 0.0238(4) Uani 1 d . . O2 O 0.2064(3) -0.08781(11) -0.1133(2) 0.0233(4) Uani 1 d . . N1 N 0.4757(3) -0.36360(13) -0.3835(2) 0.0195(4) Uani 1 d . . C1 C 0.4827(9) -0.2706(4) -0.4336(5) 0.0266(11) Uani 0.508(3) d P 1 H1 H 0.4941(9) -0.2641(4) -0.5225(5) 0.032 Uiso 0.508(3) calc PR 1 C2 C 0.4742(9) -0.1839(4) -0.3615(4) 0.0266(11) Uani 0.508(3) d P 1 H2 H 0.4867(9) -0.1196(4) -0.4001(4) 0.032 Uiso 0.508(3) calc PR 1 C3 C 0.4474(4) -0.1904(2) -0.2333(2) 0.0178(4) Uani 1 d . . C4 C 0.4426(11) -0.2864(4) -0.1793(5) 0.0315(12) Uani 0.508(3) d P 1 H4 H 0.4266(11) -0.2946(4) -0.0912(5) 0.038 Uiso 0.508(3) calc PR 1 C5 C 0.4619(10) -0.3700(3) -0.2577(5) 0.0276(11) Uani 0.508(3) d P 1 H5 H 0.4654(10) -0.4352(3) -0.2196(5) 0.033 Uiso 0.508(3) calc PR 1 C6 C 0.4286(4) -0.0973(2) -0.1518(2) 0.0160(4) Uani 1 d . . C7 C 0.6926(9) -0.3032(4) -0.3458(5) 0.0290(12) Uani 0.492(3) d P 2 H7 H 0.8607(9) -0.3205(4) -0.3708(5) 0.035 Uiso 0.492(3) calc PR 2 C8 C 0.6860(9) -0.2169(4) -0.2723(5) 0.0284(12) Uani 0.492(3) d P 2 H8 H 0.8460(9) -0.1761(4) -0.2490(5) 0.034 Uiso 0.492(3) calc PR 2 C10 C 0.2159(8) -0.2522(3) -0.2746(4) 0.0196(10) Uani 0.492(3) d P 2 H10 H 0.0448(8) -0.2354(3) -0.2522(4) 0.024 Uiso 0.492(3) calc PR 2 C11 C 0.2377(8) -0.3376(3) -0.3479(5) 0.0212(10) Uani 0.492(3) d P 2 H11 H 0.0802(8) -0.3792(3) -0.3741(5) 0.025 Uiso 0.492(3) calc PR 2 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 0.0146(2) 0.0114(2) 0.0169(2) -0.0012(2) 0.00713(15) -0.0006(2) O1 0.0180(8) 0.0248(8) 0.0286(9) -0.0074(7) 0.0052(6) -0.0047(6) O2 0.0218(8) 0.0211(8) 0.0306(9) -0.0096(7) 0.0138(6) -0.0032(6) N1 0.0169(9) 0.0192(10) 0.0234(10) -0.0043(7) 0.0064(7) 0.0001(7) C1 0.032(3) 0.025(2) 0.023(3) -0.003(2) 0.008(2) 0.003(2) C2 0.035(3) 0.021(2) 0.024(3) -0.001(2) 0.008(2) 0.001(2) C3 0.0151(10) 0.0166(10) 0.0226(11) -0.0029(8) 0.0056(8) 0.0004(8) C4 0.048(3) 0.022(2) 0.029(3) -0.003(2) 0.019(2) -0.001(2) C5 0.043(3) 0.016(2) 0.027(3) 0.000(2) 0.015(2) -0.004(2) C6 0.0171(10) 0.0154(10) 0.0152(10) 0.0001(8) 0.0027(7) 0.0022(7) C7 0.015(2) 0.034(3) 0.041(3) -0.018(2) 0.010(2) -0.004(2) C8 0.016(2) 0.028(3) 0.043(3) -0.018(2) 0.012(2) -0.008(2) C10 0.012(2) 0.019(2) 0.030(3) -0.008(2) 0.008(2) -0.003(2) C11 0.015(2) 0.021(2) 0.030(3) -0.009(2) 0.009(2) -0.003(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 O2 2.0740(14) . ? Fe O2 2.0740(14) 3 ? Fe O1 2.1415(15) 3_655 ? Fe O1 2.1415(15) 1_455 ? Fe N1 2.198(2) 4_556 ? Fe N1 2.198(2) 2_554 ? O1 C6 1.244(2) . ? O1 Fe 2.1415(15) 1_655 ? O2 C6 1.253(2) . ? N1 C7 1.334(5) . ? N1 C5 1.340(5) . ? N1 C1 1.343(5) . ? N1 C11 1.351(4) . ? N1 Fe 2.198(2) 2_544 ? C1 C2 1.380(6) . ? C2 C3 1.381(5) . ? C3 C8 1.372(5) . ? C3 C4 1.393(5) . ? C3 C10 1.404(4) . ? C3 C6 1.515(3) . ? C4 C5 1.395(6) . ? C7 C8 1.383(6) . ? C10 C11 1.385(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 O2 Fe O2 180.0 . 3 ? O2 Fe O1 92.47(6) . 3_655 ? O2 Fe O1 87.53(6) 3 3_655 ? O2 Fe O1 87.53(6) . 1_455 ? O2 Fe O1 92.47(6) 3 1_455 ? O1 Fe O1 180.0 3_655 1_455 ? O2 Fe N1 86.93(6) . 4_556 ? O2 Fe N1 93.07(6) 3 4_556 ? O1 Fe N1 87.96(6) 3_655 4_556 ? O1 Fe N1 92.04(6) 1_455 4_556 ? O2 Fe N1 93.07(6) . 2_554 ? O2 Fe N1 86.93(6) 3 2_554 ? O1 Fe N1 92.04(6) 3_655 2_554 ? O1 Fe N1 87.96(6) 1_455 2_554 ? N1 Fe N1 180.0 4_556 2_554 ? C6 O1 Fe 143.19(15) . 1_655 ? C6 O2 Fe 143.85(14) . . ? C5 N1 C1 117.1(3) . . ? C7 N1 C11 117.4(3) . . ? C7 N1 Fe 121.8(2) . 2_544 ? C5 N1 Fe 121.0(2) . 2_544 ? C1 N1 Fe 121.9(2) . 2_544 ? C11 N1 Fe 120.8(2) . 2_544 ? N1 C1 C2 122.9(4) . . ? C1 C2 C3 120.1(4) . . ? C2 C3 C4 117.8(3) . . ? C8 C3 C10 117.3(3) . . ? C8 C3 C6 122.1(2) . . ? C2 C3 C6 121.8(3) . . ? C4 C3 C6 120.3(3) . . ? C10 C3 C6 120.6(2) . . ? C3 C4 C5 118.4(4) . . ? N1 C5 C4 123.7(4) . . ? O1 C6 O2 126.9(2) . . ? O1 C6 C3 118.2(2) . . ? O2 C6 C3 114.9(2) . . ? N1 C7 C8 123.6(4) . . ? C3 C8 C7 119.7(4) . . ? C11 C10 C3 119.8(3) . . ? N1 C11 C10 122.1(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe O2 C6 71.3(37) 3 . . . ? O1 Fe O2 C6 -31.7(2) 3_655 . . . ? O1 Fe O2 C6 148.3(2) 1_455 . . . ? N1 Fe O2 C6 -119.5(2) 4_556 . . . ? N1 Fe O2 C6 60.5(2) 2_554 . . . ? C7 N1 C1 C2 -68.0(5) . . . . ? C5 N1 C1 C2 -0.5(6) . . . . ? C11 N1 C1 C2 55.9(5) . . . . ? Fe N1 C1 C2 -178.5(3) 2_544 . . . ? N1 C1 C2 C3 -2.4(7) . . . . ? C1 C2 C3 C8 71.5(5) . . . . ? C1 C2 C3 C4 2.9(6) . . . . ? C1 C2 C3 C10 -52.7(4) . . . . ? C1 C2 C3 C6 -178.2(3) . . . . ? C8 C3 C4 C5 -52.8(5) . . . . ? C2 C3 C4 C5 -0.7(6) . . . . ? C10 C3 C4 C5 69.8(5) . . . . ? C6 C3 C4 C5 -179.7(3) . . . . ? C7 N1 C5 C4 55.3(5) . . . . ? C1 N1 C5 C4 2.9(6) . . . . ? C11 N1 C5 C4 -68.5(5) . . . . ? Fe N1 C5 C4 -179.2(4) 2_544 . . . ? C3 C4 C5 N1 -2.3(7) . . . . ? Fe O1 C6 O2 88.3(3) 1_655 . . . ? Fe O1 C6 C3 -93.9(3) 1_655 . . . ? Fe O2 C6 O1 -6.2(4) . . . . ? Fe O2 C6 C3 176.0(2) . . . . ? C8 C3 C6 O1 8.4(4) . . . . ? C2 C3 C6 O1 -61.1(3) . . . . ? C4 C3 C6 O1 117.8(3) . . . . ? C10 C3 C6 O1 -170.1(3) . . . . ? C8 C3 C6 O2 -173.6(3) . . . . ? C2 C3 C6 O2 116.9(3) . . . . ? C4 C3 C6 O2 -64.2(3) . . . . ? C10 C3 C6 O2 7.9(4) . . . . ? C5 N1 C7 C8 -55.0(6) . . . . ? C1 N1 C7 C8 69.6(5) . . . . ? C11 N1 C7 C8 0.5(7) . . . . ? Fe N1 C7 C8 -179.9(4) 2_544 . . . ? C2 C3 C8 C7 -70.5(5) . . . . ? C4 C3 C8 C7 54.0(6) . . . . ? C10 C3 C8 C7 -2.0(7) . . . . ? C6 C3 C8 C7 179.5(4) . . . . ? N1 C7 C8 C3 0.8(8) . . . . ? C8 C3 C10 C11 2.1(6) . . . . ? C2 C3 C10 C11 54.1(5) . . . . ? C4 C3 C10 C11 -69.3(4) . . . . ? C6 C3 C10 C11 -179.4(3) . . . . ? C7 N1 C11 C10 -0.4(6) . . . . ? C5 N1 C11 C10 68.9(5) . . . . ? C1 N1 C11 C10 -53.5(5) . . . . ? Fe N1 C11 C10 180.0(3) 2_544 . . . ? C3 C10 C11 N1 -0.9(7) . . . . ? _refine_diff_density_max 1.381 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.162