Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Dario Braga' 'Lucia Maini' 'Marco Polito' 'Laurent Mirolo' 'Fabrizia Grepioni' _publ_contact_author_name 'Prof Dario Braga' _publ_contact_author_address ; Dipartimento di Chimica G. Ciamician University of Bologna Via Selmi 2 Bologna 40126 ITALY ; _publ_contact_author_email 'DBRAGA@CIAM.UNIBO.IT' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Mechanochemical Assembly of Hydrogen Bonded Organic-Organometallic Solid Compounds ; data_compound_3 _database_code_CSD 191507 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[Fe(C5H4COOH)(C5H4COO)][HDABCO]' _chemical_formula_sum 'C18 H22 Fe N2 O4' _chemical_formula_weight 386.23 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' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 '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 7.452(2) _cell_length_b 10.804(2) _cell_length_c 11.319(2) _cell_angle_alpha 104.83(2) _cell_angle_beta 98.96(2) _cell_angle_gamma 105.33(2) _cell_volume 824.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour Orange-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _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 ? _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 3052 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.1667 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2894 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0714P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2894 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1818 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 0.18050(14) 0.25441(11) 0.43178(9) 0.0254(3) Uani 1 1 d . . . C1 C 0.2406(6) 0.2655(4) 0.6165(4) 0.0232(14) Uiso 1 1 d G . . C2 C 0.3774(6) 0.3727(3) 0.5962(4) 0.0333(17) Uiso 1 1 d G . . H2 H 0.4023 0.4694 0.6362 0.10(3) Uiso 1 1 calc R . . C3 C 0.4700(5) 0.3150(4) 0.5065(4) 0.0366(17) Uiso 1 1 d G . . H3 H 0.5699 0.3650 0.4736 0.07(2) Uiso 1 1 calc R . . C4 C 0.3905(6) 0.1723(4) 0.4713(4) 0.0345(16) Uiso 1 1 d G . . H4 H 0.4265 0.1065 0.4105 0.15(4) Uiso 1 1 calc R . . C5 C 0.2487(6) 0.1417(3) 0.5393(4) 0.0287(15) Uiso 1 1 d G . . H5 H 0.1703 0.0511 0.5340 0.029(16) Uiso 1 1 calc R . . C6 C 0.1210(6) 0.2386(4) 0.2455(4) 0.0250(14) Uiso 1 1 d G . . C7 C -0.0077(6) 0.1290(3) 0.2680(4) 0.0330(16) Uiso 1 1 d G . . H7 H -0.0245 0.0331 0.2304 0.043(18) Uiso 1 1 calc R . . C8 C -0.1084(5) 0.1828(4) 0.3540(4) 0.0338(16) Uiso 1 1 d G . . H8 H -0.2062 0.1305 0.3867 0.07(2) Uiso 1 1 calc R . . C9 C -0.0420(6) 0.3257(4) 0.3846(4) 0.0318(16) Uiso 1 1 d G . . H9 H -0.0851 0.3893 0.4428 0.06(2) Uiso 1 1 calc R . . C10 C 0.0998(6) 0.3602(3) 0.3176(4) 0.0290(15) Uiso 1 1 d G . . H10 H 0.1713 0.4518 0.3211 0.030(16) Uiso 1 1 calc R . . C11 C 0.1094(9) 0.2833(7) 0.7008(6) 0.0299(15) Uiso 1 1 d . . . C12 C 0.2596(9) 0.2257(7) 0.1649(6) 0.0279(15) Uiso 1 1 d . . . C13 C 0.7272(8) 0.2665(7) 0.0611(6) 0.0302(15) Uiso 1 1 d . . . H13A H 0.6898 0.1941 0.0974 0.026(16) Uiso 1 1 calc R . . H13B H 0.7963 0.3494 0.1293 0.05(2) Uiso 1 1 calc R . . C14 C 0.8580(9) 0.2342(7) -0.0278(6) 0.0336(16) Uiso 1 1 d . . . H14A H 0.9818 0.3042 0.0015 0.030(16) Uiso 1 1 calc R . . H14B H 0.8776 0.1488 -0.0285 0.032(16) Uiso 1 1 calc R . . C15 C 0.6165(8) 0.3922(6) -0.0641(6) 0.0294(15) Uiso 1 1 d . . . H15A H 0.6897 0.4751 0.0029 0.06(2) Uiso 1 1 calc R . . H15B H 0.5049 0.4065 -0.1080 0.017(14) Uiso 1 1 calc R . . C16 C 0.7392(9) 0.3573(7) -0.1555(6) 0.0318(15) Uiso 1 1 d . . . H16A H 0.6770 0.3519 -0.2394 0.036(17) Uiso 1 1 calc R . . H16B H 0.8629 0.4273 -0.1298 0.028(16) Uiso 1 1 calc R . . C17 C 0.4481(8) 0.1555(7) -0.1134(6) 0.0299(15) Uiso 1 1 d . . . H17A H 0.3373 0.1669 -0.1614 0.06(2) Uiso 1 1 calc R . . H17B H 0.4032 0.0827 -0.0789 0.08(3) Uiso 1 1 calc R . . C18 C 0.5781(8) 0.1193(6) -0.2000(6) 0.0300(15) Uiso 1 1 d . . . H18A H 0.5951 0.0337 -0.1986 0.045(19) Uiso 1 1 calc R . . H18B H 0.5196 0.1104 -0.2858 0.017(14) Uiso 1 1 calc R . . N1 N 0.5546(7) 0.2816(5) -0.0100(4) 0.0241(12) Uani 1 1 d . . . N2 N 0.7656(7) 0.2266(5) -0.1563(5) 0.0250(12) Uani 1 1 d . . . O1 O 0.1349(7) 0.3953(5) 0.7732(5) 0.0566(15) Uani 1 1 d . . . O2 O -0.0200(6) 0.1758(5) 0.6946(4) 0.0401(12) Uani 1 1 d . . . O3 O 0.3458(6) 0.3349(4) 0.1449(4) 0.0344(11) Uani 1 1 d . . . O4 O 0.2780(8) 0.1148(5) 0.1201(5) 0.0495(14) Uani 1 1 d . . . H100 H 0.4216 0.3041 0.0832 0.05 Uiso 1 1 d . . . H200 H 0.8603 0.2154 -0.2186 0.05 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0236(4) 0.0281(6) 0.0235(5) 0.0084(4) 0.0044(3) 0.0072(4) N1 0.025(3) 0.023(3) 0.022(3) 0.006(2) 0.004(2) 0.008(2) N2 0.029(3) 0.021(3) 0.031(3) 0.011(2) 0.009(2) 0.014(2) O1 0.052(3) 0.038(4) 0.061(3) -0.012(3) 0.027(3) 0.001(3) O2 0.047(3) 0.030(3) 0.050(3) 0.012(2) 0.029(2) 0.013(2) O3 0.040(3) 0.025(3) 0.045(3) 0.013(2) 0.023(2) 0.012(2) O4 0.086(4) 0.026(3) 0.054(3) 0.018(2) 0.039(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C5 2.028(4) . ? Fe1 C7 2.034(4) . ? Fe1 C1 2.034(4) . ? Fe1 C6 2.038(4) . ? Fe1 C4 2.038(4) . ? Fe1 C2 2.047(4) . ? Fe1 C8 2.047(4) . ? Fe1 C10 2.053(4) . ? Fe1 C3 2.049(4) . ? Fe1 C9 2.058(4) . ? C1 C2 1.4200 . ? C1 C5 1.4200 . ? C1 C11 1.484(7) . ? C2 C3 1.4200 . ? C3 C4 1.4200 . ? C4 C5 1.4200 . ? C6 C7 1.4200 . ? C6 C10 1.4200 . ? C6 C12 1.491(7) . ? C7 C8 1.4200 . ? C8 C9 1.4200 . ? C9 C10 1.4200 . ? C11 O1 1.222(8) . ? C11 O2 1.276(7) . ? C12 O4 1.228(7) . ? C12 O3 1.279(7) . ? C13 N1 1.478(7) . ? C13 C14 1.546(8) . ? C14 N2 1.481(7) . ? C15 N1 1.480(7) . ? C15 C16 1.524(8) . ? C16 N2 1.474(7) . ? C17 N1 1.476(7) . ? C17 C18 1.533(8) . ? C18 N2 1.475(7) . ? 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 C5 Fe1 C7 108.83(18) . . ? C5 Fe1 C1 40.92(8) . . ? C7 Fe1 C1 138.4(2) . . ? C5 Fe1 C6 137.7(2) . . ? C7 Fe1 C6 40.81(8) . . ? C1 Fe1 C6 178.6(2) . . ? C5 Fe1 C4 40.88(8) . . ? C7 Fe1 C4 108.37(18) . . ? C1 Fe1 C4 68.70(10) . . ? C6 Fe1 C4 110.20(17) . . ? C5 Fe1 C2 68.64(9) . . ? C7 Fe1 C2 176.81(18) . . ? C1 Fe1 C2 40.73(7) . . ? C6 Fe1 C2 140.0(2) . . ? C4 Fe1 C2 68.46(10) . . ? C5 Fe1 C8 109.25(18) . . ? C7 Fe1 C8 40.72(8) . . ? C1 Fe1 C8 111.64(18) . . ? C6 Fe1 C8 68.45(10) . . ? C4 Fe1 C8 136.1(2) . . ? C2 Fe1 C8 141.5(2) . . ? C5 Fe1 C10 177.11(19) . . ? C7 Fe1 C10 68.40(10) . . ? C1 Fe1 C10 140.8(2) . . ? C6 Fe1 C10 40.62(8) . . ? C4 Fe1 C10 140.2(2) . . ? C2 Fe1 C10 114.15(18) . . ? C8 Fe1 C10 68.17(10) . . ? C5 Fe1 C3 68.59(10) . . ? C7 Fe1 C3 137.1(2) . . ? C1 Fe1 C3 68.49(10) . . ? C6 Fe1 C3 111.34(18) . . ? C4 Fe1 C3 40.66(8) . . ? C2 Fe1 C3 40.57(8) . . ? C8 Fe1 C3 176.7(2) . . ? C10 Fe1 C3 113.93(18) . . ? C5 Fe1 C9 138.3(2) . . ? C7 Fe1 C9 68.30(10) . . ? C1 Fe1 C9 112.81(17) . . ? C6 Fe1 C9 68.23(10) . . ? C4 Fe1 C9 176.5(2) . . ? C2 Fe1 C9 114.86(18) . . ? C8 Fe1 C9 40.47(8) . . ? C10 Fe1 C9 40.41(7) . . ? C3 Fe1 C9 142.7(2) . . ? C2 C1 C5 108.0 . . ? C2 C1 C11 124.9(4) . . ? C5 C1 C11 127.1(4) . . ? C2 C1 Fe1 70.13(17) . . ? C5 C1 Fe1 69.34(16) . . ? C11 C1 Fe1 124.5(3) . . ? C1 C2 C3 108.0 . . ? C1 C2 Fe1 69.14(16) . . ? C3 C2 Fe1 69.82(16) . . ? C4 C3 C2 108.0 . . ? C4 C3 Fe1 69.25(17) . . ? C2 C3 Fe1 69.61(16) . . ? C5 C4 C3 108.0 . . ? C5 C4 Fe1 69.19(16) . . ? C3 C4 Fe1 70.10(17) . . ? C4 C5 C1 108.0 . . ? C4 C5 Fe1 69.93(16) . . ? C1 C5 Fe1 69.74(16) . . ? C7 C6 C10 108.0 . . ? C7 C6 C12 125.0(4) . . ? C10 C6 C12 127.0(4) . . ? C7 C6 Fe1 69.45(17) . . ? C10 C6 Fe1 70.25(16) . . ? C12 C6 Fe1 123.6(3) . . ? C8 C7 C6 108.0 . . ? C8 C7 Fe1 70.11(16) . . ? C6 C7 Fe1 69.74(16) . . ? C7 C8 C9 108.0 . . ? C7 C8 Fe1 69.17(16) . . ? C9 C8 Fe1 70.20(17) . . ? C10 C9 C8 108.0 . . ? C10 C9 Fe1 69.60(16) . . ? C8 C9 Fe1 69.33(17) . . ? C9 C10 C6 108.0 . . ? C9 C10 Fe1 69.99(16) . . ? C6 C10 Fe1 69.13(16) . . ? O1 C11 O2 124.8(6) . . ? O1 C11 C1 119.5(6) . . ? O2 C11 C1 115.7(6) . . ? O4 C12 O3 125.4(6) . . ? O4 C12 C6 119.7(6) . . ? O3 C12 C6 114.9(5) . . ? N1 C13 C14 109.7(5) . . ? N2 C14 C13 108.9(5) . . ? N1 C15 C16 110.3(5) . . ? N2 C16 C15 109.2(5) . . ? N1 C17 C18 110.0(5) . . ? N2 C18 C17 109.2(5) . . ? C17 N1 C15 108.9(5) . . ? C17 N1 C13 110.0(5) . . ? C15 N1 C13 108.4(5) . . ? C16 N2 C18 109.8(5) . . ? C16 N2 C14 109.8(5) . . ? C18 N2 C14 109.3(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.673 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.104 #===END data_compound_5 _database_code_CSD 191508 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[Fe(C5H4COOH)(C5H4COO)][C6H4(NH2)(NH3)]' _chemical_formula_sum 'C18 H18 Fe N2 O4' _chemical_formula_weight 382.19 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' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 '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 7.228(7) _cell_length_b 10.216(4) _cell_length_c 11.803(3) _cell_angle_alpha 103.74(3) _cell_angle_beta 105.57(4) _cell_angle_gamma 96.88(5) _cell_volume 799.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.970 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _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 ? _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 4852 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.2557 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 29.95 _reflns_number_total 4646 _reflns_number_gt 1597 _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^)+(0.0673P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4646 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2473 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.919 _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 -0.20605(12) 0.28833(9) -0.41305(8) 0.0283(3) Uani 1 1 d . . . C1 C -0.1993(5) 0.1058(4) -0.3731(4) 0.0383(15) Uani 1 1 d G . . H1 H -0.2990 0.0540 -0.3569 0.046 Uiso 1 1 calc R . . C2 C -0.0461(6) 0.2103(4) -0.2851(3) 0.0300(13) Uani 1 1 d G . . C3 C 0.0742(5) 0.2633(4) -0.3476(3) 0.0328(14) Uani 1 1 d G . . H3 H 0.1852 0.3328 -0.3119 0.039 Uiso 1 1 calc R . . C4 C -0.0046(6) 0.1916(4) -0.4742(3) 0.0412(16) Uani 1 1 d G . . H4 H 0.0457 0.2059 -0.5359 0.049 Uiso 1 1 calc R . . C5 C -0.1736(6) 0.0943(4) -0.4899(3) 0.0409(15) Uani 1 1 d G . . H5 H -0.2535 0.0336 -0.5638 0.049 Uiso 1 1 calc R . . C6 C -0.4773(5) 0.3283(4) -0.4210(4) 0.0398(16) Uani 1 1 d G . . H6 H -0.5768 0.2738 -0.4070 0.048 Uiso 1 1 calc R . . C7 C -0.3310(6) 0.4357(4) -0.3310(3) 0.0303(13) Uani 1 1 d G . . C8 C -0.2083(6) 0.4924(4) -0.3904(4) 0.0398(16) Uani 1 1 d G . . H8 H -0.1007 0.5644 -0.3530 0.048 Uiso 1 1 calc R . . C9 C -0.2789(7) 0.4200(5) -0.5171(3) 0.0526(19) Uani 1 1 d G . . H9 H -0.2256 0.4362 -0.5771 0.063 Uiso 1 1 calc R . . C10 C -0.4451(6) 0.3186(4) -0.5359(3) 0.0482(18) Uani 1 1 d G . . H10 H -0.5198 0.2567 -0.6105 0.058 Uiso 1 1 calc R . . C11 C -0.0248(8) 0.2596(6) -0.1542(5) 0.0315(13) Uani 1 1 d . . . C12 C -0.3084(7) 0.4797(5) -0.1983(5) 0.0262(12) Uani 1 1 d . . . C13 C -0.3267(5) 0.2580(3) 0.1189(4) 0.0331(13) Uani 1 1 d G . . C14 C -0.5137(5) 0.2025(4) 0.1159(4) 0.0341(14) Uani 1 1 d G . . H14 H -0.6166 0.2474 0.0941 0.041 Uiso 1 1 calc R . . C15 C -0.5471(4) 0.0797(4) 0.1454(4) 0.0349(14) Uani 1 1 d G . . H15 H -0.6723 0.0426 0.1434 0.042 Uiso 1 1 calc R . . C16 C -0.3934(5) 0.0125(3) 0.1780(3) 0.0288(13) Uani 1 1 d G . . C17 C -0.2064(4) 0.0680(4) 0.1810(4) 0.0379(15) Uani 1 1 d G . . H17 H -0.1035 0.0231 0.2028 0.045 Uiso 1 1 calc R . . C18 C -0.1730(4) 0.1908(4) 0.1514(4) 0.0385(15) Uani 1 1 d G . . H18 H -0.0478 0.2279 0.1535 0.046 Uiso 1 1 calc R . . N1 N -0.2898(10) 0.3848(6) 0.0840(6) 0.0397(13) Uani 1 1 d . . . N2 N -0.4272(9) -0.1088(6) 0.2093(5) 0.0423(14) Uani 1 1 d . . . O1 O 0.1414(5) 0.3449(4) -0.0883(4) 0.0356(10) Uani 1 1 d . . . O2 O -0.1508(6) 0.2251(4) -0.1102(4) 0.0439(11) Uani 1 1 d . . . O3 O -0.1470(5) 0.5591(4) -0.1295(4) 0.0359(10) Uani 1 1 d . . . O4 O -0.4472(5) 0.4407(4) -0.1613(4) 0.0399(11) Uani 1 1 d . . . H200 H -0.550(10) -0.144(6) 0.190(6) 0.046(19) Uiso 1 1 d . . . H201 H -0.342(10) -0.164(7) 0.207(6) 0.06(2) Uiso 1 1 d . . . H100 H -0.375(9) 0.437(6) 0.099(5) 0.041(19) Uiso 1 1 d . . . H101 H -0.331(10) 0.366(7) -0.004(7) 0.07(2) Uiso 1 1 d . . . H102 H -0.152(12) 0.420(8) 0.128(7) 0.10(3) Uiso 1 1 d . . . H111 H 0.144(10) 0.385(7) 0.011(7) 0.08(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0289(4) 0.0306(5) 0.0264(4) 0.0078(4) 0.0088(4) 0.0093(4) C1 0.038(3) 0.033(4) 0.039(4) 0.004(3) 0.009(3) 0.004(3) C2 0.030(3) 0.027(3) 0.034(3) 0.011(3) 0.008(3) 0.011(3) C3 0.030(3) 0.038(4) 0.038(3) 0.013(3) 0.017(3) 0.015(3) C4 0.037(3) 0.044(4) 0.047(4) 0.010(3) 0.019(3) 0.017(3) C5 0.046(4) 0.034(4) 0.040(4) 0.002(3) 0.012(3) 0.014(3) C6 0.030(3) 0.052(4) 0.033(3) 0.002(3) 0.007(3) 0.016(3) C7 0.029(3) 0.033(4) 0.032(3) 0.012(3) 0.011(3) 0.010(3) C8 0.049(4) 0.042(4) 0.042(4) 0.020(3) 0.024(3) 0.020(3) C9 0.073(5) 0.056(5) 0.048(4) 0.029(4) 0.025(4) 0.037(4) C10 0.049(4) 0.064(5) 0.028(3) 0.006(3) 0.001(3) 0.034(4) C11 0.035(3) 0.032(3) 0.029(3) 0.011(3) 0.010(3) 0.006(3) C12 0.027(3) 0.022(3) 0.029(3) 0.003(2) 0.009(2) 0.006(2) C13 0.050(4) 0.023(3) 0.029(3) 0.008(3) 0.020(3) 0.002(3) C14 0.031(3) 0.032(4) 0.039(4) 0.013(3) 0.009(3) 0.008(3) C15 0.030(3) 0.025(3) 0.045(4) 0.007(3) 0.012(3) -0.006(3) C16 0.034(3) 0.018(3) 0.030(3) 0.007(2) 0.005(3) -0.002(2) C17 0.028(3) 0.029(4) 0.053(4) 0.015(3) 0.007(3) -0.004(3) C18 0.027(3) 0.039(4) 0.047(4) 0.012(3) 0.010(3) -0.001(3) N1 0.052(4) 0.028(3) 0.046(4) 0.016(3) 0.021(3) 0.006(3) N2 0.035(3) 0.037(4) 0.058(4) 0.027(3) 0.010(3) 0.004(3) O1 0.027(2) 0.044(3) 0.027(2) 0.006(2) 0.0028(18) -0.0051(18) O2 0.042(2) 0.047(3) 0.038(3) 0.012(2) 0.014(2) -0.012(2) O3 0.032(2) 0.036(3) 0.031(2) 0.003(2) 0.0058(19) -0.0057(19) O4 0.039(2) 0.037(3) 0.044(3) 0.004(2) 0.024(2) -0.0020(19) _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 C2 2.027(4) . ? Fe1 C7 2.030(4) . ? Fe1 C6 2.033(4) . ? Fe1 C1 2.033(4) . ? Fe1 C3 2.036(4) . ? Fe1 C8 2.041(4) . ? Fe1 C10 2.045(4) . ? Fe1 C5 2.044(4) . ? Fe1 C4 2.046(4) . ? Fe1 C9 2.050(4) . ? C1 C2 1.4200 . ? C1 C5 1.4200 . ? C2 C3 1.4200 . ? C2 C11 1.465(6) . ? C3 C4 1.4200 . ? C4 C5 1.4200 . ? C6 C10 1.4200 . ? C6 C7 1.4200 . ? C7 C8 1.4200 . ? C7 C12 1.481(6) . ? C8 C9 1.4200 . ? C9 C10 1.4200 . ? C11 O2 1.220(6) . ? C11 O1 1.317(6) . ? C12 O4 1.257(6) . ? C12 O3 1.277(6) . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C13 N1 1.466(6) . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C16 N2 1.388(6) . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? 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 C2 Fe1 C7 109.42(14) . . ? C2 Fe1 C6 124.22(15) . . ? C7 Fe1 C6 40.92(8) . . ? C2 Fe1 C1 40.95(8) . . ? C7 Fe1 C1 122.94(14) . . ? C6 Fe1 C1 106.57(15) . . ? C2 Fe1 C3 40.92(7) . . ? C7 Fe1 C3 125.77(15) . . ? C6 Fe1 C3 161.81(15) . . ? C1 Fe1 C3 68.77(10) . . ? C2 Fe1 C8 124.49(16) . . ? C7 Fe1 C8 40.83(8) . . ? C6 Fe1 C8 68.67(10) . . ? C1 Fe1 C8 159.93(15) . . ? C3 Fe1 C8 109.32(15) . . ? C2 Fe1 C10 159.31(17) . . ? C7 Fe1 C10 68.64(10) . . ? C6 Fe1 C10 40.76(8) . . ? C1 Fe1 C10 121.51(17) . . ? C3 Fe1 C10 156.81(16) . . ? C8 Fe1 C10 68.44(11) . . ? C2 Fe1 C5 68.71(10) . . ? C7 Fe1 C5 157.41(15) . . ? C6 Fe1 C5 120.17(15) . . ? C1 Fe1 C5 40.77(8) . . ? C3 Fe1 C5 68.55(10) . . ? C8 Fe1 C5 158.73(15) . . ? C10 Fe1 C5 104.79(15) . . ? C2 Fe1 C4 68.67(9) . . ? C7 Fe1 C4 161.43(15) . . ? C6 Fe1 C4 155.66(16) . . ? C1 Fe1 C4 68.57(10) . . ? C3 Fe1 C4 40.72(8) . . ? C8 Fe1 C4 123.90(15) . . ? C10 Fe1 C4 119.95(15) . . ? C5 Fe1 C4 40.62(8) . . ? C2 Fe1 C9 159.54(17) . . ? C7 Fe1 C9 68.54(10) . . ? C6 Fe1 C9 68.50(10) . . ? C1 Fe1 C9 157.60(16) . . ? C3 Fe1 C9 122.56(16) . . ? C8 Fe1 C9 40.62(8) . . ? C10 Fe1 C9 40.58(8) . . ? C5 Fe1 C9 121.33(15) . . ? C4 Fe1 C9 106.43(14) . . ? C2 C1 C5 108.0 . . ? C2 C1 Fe1 69.32(15) . . ? C5 C1 Fe1 70.06(15) . . ? C3 C2 C1 108.0 . . ? C3 C2 C11 126.4(3) . . ? C1 C2 C11 125.5(3) . . ? C3 C2 Fe1 69.86(16) . . ? C1 C2 Fe1 69.73(16) . . ? C11 C2 Fe1 123.1(3) . . ? C4 C3 C2 108.0 . . ? C4 C3 Fe1 70.05(15) . . ? C2 C3 Fe1 69.22(16) . . ? C5 C4 C3 108.0 . . ? C5 C4 Fe1 69.62(16) . . ? C3 C4 Fe1 69.24(15) . . ? C4 C5 C1 108.0 . . ? C4 C5 Fe1 69.76(16) . . ? C1 C5 Fe1 69.17(15) . . ? C10 C6 C7 108.0 . . ? C10 C6 Fe1 70.08(16) . . ? C7 C6 Fe1 69.45(16) . . ? C8 C7 C6 108.0 . . ? C8 C7 C12 126.0(3) . . ? C6 C7 C12 126.0(3) . . ? C8 C7 Fe1 69.99(16) . . ? C6 C7 Fe1 69.63(17) . . ? C12 C7 Fe1 125.3(3) . . ? C7 C8 C9 108.0 . . ? C7 C8 Fe1 69.18(15) . . ? C9 C8 Fe1 70.03(15) . . ? C10 C9 C8 108.0 . . ? C10 C9 Fe1 69.51(16) . . ? C8 C9 Fe1 69.35(15) . . ? C6 C10 C9 108.0 . . ? C6 C10 Fe1 69.16(16) . . ? C9 C10 Fe1 69.90(17) . . ? O2 C11 O1 122.8(5) . . ? O2 C11 C2 122.8(5) . . ? O1 C11 C2 114.3(5) . . ? O4 C12 O3 124.6(5) . . ? O4 C12 C7 119.2(5) . . ? O3 C12 C7 116.2(4) . . ? C14 C13 C18 120.0 . . ? C14 C13 N1 120.8(4) . . ? C18 C13 N1 119.2(4) . . ? C13 C14 C15 120.0 . . ? C14 C15 C16 120.0 . . ? N2 C16 C17 120.3(4) . . ? N2 C16 C15 119.7(4) . . ? C17 C16 C15 120.0 . . ? C16 C17 C18 120.0 . . ? C17 C18 C13 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.459 _refine_diff_density_min -0.742 _refine_diff_density_rms 0.110 #===END