# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mochida, Tomoyuki' _publ_contact_author_email tmochida@platinum.kobe-u.ac.jp loop_ _publ_author_name T.Mochida Y.Funasako H.Azumi data_DecaCl2NQ _database_code_depnum_ccdc_archive 'CCDC 766109' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; decamethylferrocene-dichloroonaphthoquinone complex ; _chemical_name_common 'decamethylferrocene-dichloroonaphthoquinone complex' _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 Fe, 2(C10 H4 Cl2 O2)' _chemical_formula_sum 'C40 H38 Cl4 Fe O4' _chemical_formula_weight 780.35 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.8780(10) _cell_length_b 8.3613(6) _cell_length_c 15.0171(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.092(2) _cell_angle_gamma 90.00 _cell_volume 1738.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 4204 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.22 _exptl_crystal_description plate _exptl_crystal_colour prange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.784 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8589 _exptl_absorpt_correction_T_max 0.9618 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 8.366 _diffrn_reflns_number 12597 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4307 _reflns_number_gt 3622 _reflns_threshold_expression >2\s _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^ > 2\s(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^)+(0.0491P)^2^+1.1474P] 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 4307 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.0000 1.0000 0.01772(12) Uani 1 2 d S . . Cl2 Cl 0.15611(5) 0.41105(7) 1.10108(4) 0.03170(16) Uani 1 1 d . . . Cl1 Cl 0.18727(5) 0.10503(7) 1.22351(4) 0.03060(15) Uani 1 1 d . . . O1 O 0.15523(13) -0.1893(2) 1.12415(11) 0.0312(4) Uani 1 1 d . . . C11 C 0.14516(17) -0.0748(3) 1.07540(15) 0.0223(5) Uani 1 1 d . . . C13 C 0.14454(17) 0.2212(3) 1.05953(15) 0.0231(5) Uani 1 1 d . . . O2 O 0.10340(15) 0.3289(2) 0.91723(12) 0.0364(5) Uani 1 1 d . . . C15 C 0.10487(16) 0.0459(3) 0.92411(15) 0.0205(4) Uani 1 1 d . . . C16 C 0.07959(17) 0.0292(3) 0.83331(16) 0.0247(5) Uani 1 1 d . . . C2 C 0.61864(16) -0.1415(3) 1.03148(15) 0.0212(4) Uani 1 1 d . . . C14 C 0.11657(17) 0.2089(3) 0.96236(15) 0.0237(5) Uani 1 1 d . . . C20 C 0.11824(16) -0.0895(3) 0.97817(15) 0.0211(4) Uani 1 1 d . . . C12 C 0.15808(17) 0.0913(3) 1.11140(14) 0.0216(4) Uani 1 1 d . . . C1 C 0.59988(17) -0.1302(3) 0.93718(15) 0.0234(5) Uani 1 1 d . . . C19 C 0.10572(18) -0.2411(3) 0.94049(17) 0.0262(5) Uani 1 1 d . . . C3 C 0.63443(16) 0.0161(3) 1.06618(17) 0.0250(5) Uani 1 1 d . . . C18 C 0.08175(18) -0.2568(3) 0.84980(17) 0.0284(5) Uani 1 1 d . . . C6 C 0.5820(2) -0.2691(4) 0.87460(19) 0.0413(7) Uani 1 1 d . . . H6A H 0.5462 -0.3501 0.9032 0.062 Uiso 1 1 calc R . . H6B H 0.6427 -0.3124 0.8592 0.062 Uiso 1 1 calc R . . H6C H 0.5458 -0.2334 0.8214 0.062 Uiso 1 1 calc R . . C17 C 0.06827(18) -0.1224(3) 0.79628(17) 0.0283(5) Uani 1 1 d . . . C4 C 0.37363(17) -0.1241(3) 1.00729(19) 0.0302(6) Uani 1 1 d . . . C7 C 0.6254(2) -0.2932(3) 1.08515(19) 0.0350(6) Uani 1 1 d . . . H7A H 0.6879 -0.3405 1.0808 0.052 Uiso 1 1 calc R . . H7B H 0.5763 -0.3665 1.0624 0.052 Uiso 1 1 calc R . . H7C H 0.6161 -0.2695 1.1465 0.052 Uiso 1 1 calc R . . C5 C 0.39476(17) -0.0342(3) 1.08693(17) 0.0289(5) Uani 1 1 d . . . C8 C 0.6587(2) 0.0583(4) 1.1624(2) 0.0452(8) Uani 1 1 d . . . H8A H 0.6392 0.1664 1.1729 0.068 Uiso 1 1 calc R . . H8B H 0.7271 0.0483 1.1759 0.068 Uiso 1 1 calc R . . H8C H 0.6253 -0.0129 1.1998 0.068 Uiso 1 1 calc R . . C9 C 0.3584(2) -0.3022(3) 1.0019(3) 0.0583(10) Uani 1 1 d . . . H9A H 0.2938 -0.3272 1.0162 0.088 Uiso 1 1 calc R . . H9B H 0.4037 -0.3546 1.0435 0.088 Uiso 1 1 calc R . . H9C H 0.3681 -0.3384 0.9425 0.088 Uiso 1 1 calc R . . C10 C 0.4066(2) -0.1026(5) 1.1796(2) 0.0563(10) Uani 1 1 d . . . H10A H 0.4413 -0.2018 1.1785 0.084 Uiso 1 1 calc R . . H10B H 0.3441 -0.1210 1.2013 0.084 Uiso 1 1 calc R . . H10C H 0.4420 -0.0285 1.2184 0.084 Uiso 1 1 calc R . . H19 H 0.1120(19) -0.330(3) 0.9753(18) 0.030(7) Uiso 1 1 d . . . H17 H 0.0539(19) -0.134(3) 0.7361(19) 0.027(7) Uiso 1 1 d . . . H16 H 0.072(2) 0.128(3) 0.7947(19) 0.033(8) Uiso 1 1 d . . . H18 H 0.075(2) -0.361(4) 0.8264(19) 0.032(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0181(2) 0.0141(2) 0.0210(2) 0.00147(16) 0.00117(16) 0.00120(17) Cl2 0.0455(4) 0.0208(3) 0.0287(3) -0.0043(2) 0.0023(3) -0.0042(2) Cl1 0.0381(3) 0.0353(3) 0.0179(3) -0.0005(2) -0.0016(2) 0.0008(3) O1 0.0412(11) 0.0261(9) 0.0261(9) 0.0077(7) 0.0013(8) 0.0016(8) C11 0.0222(11) 0.0231(11) 0.0218(11) 0.0021(9) 0.0032(9) 0.0003(9) C13 0.0251(12) 0.0205(10) 0.0241(11) -0.0043(9) 0.0044(9) -0.0012(9) O2 0.0626(13) 0.0217(9) 0.0247(9) 0.0052(7) 0.0018(9) 0.0010(8) C15 0.0189(11) 0.0220(10) 0.0211(11) -0.0005(8) 0.0044(8) 0.0014(8) C16 0.0251(12) 0.0283(12) 0.0211(11) 0.0015(9) 0.0028(9) 0.0021(9) C2 0.0201(11) 0.0196(10) 0.0238(11) 0.0019(8) 0.0013(9) 0.0021(8) C14 0.0269(12) 0.0245(11) 0.0200(11) 0.0011(9) 0.0041(9) 0.0005(9) C20 0.0213(11) 0.0215(10) 0.0206(11) -0.0004(8) 0.0024(8) 0.0002(9) C12 0.0234(11) 0.0266(11) 0.0148(10) -0.0016(8) 0.0012(8) -0.0019(9) C1 0.0209(11) 0.0269(11) 0.0223(11) -0.0012(9) 0.0010(9) 0.0037(9) C19 0.0245(12) 0.0225(11) 0.0314(13) 0.0003(10) 0.0017(10) 0.0019(9) C3 0.0191(11) 0.0235(11) 0.0320(12) -0.0068(9) -0.0003(9) 0.0014(9) C18 0.0264(13) 0.0253(12) 0.0333(13) -0.0076(10) 0.0018(10) 0.0000(10) C6 0.0344(15) 0.0516(17) 0.0372(15) -0.0229(13) -0.0009(12) 0.0054(13) C17 0.0275(13) 0.0355(13) 0.0217(12) -0.0059(10) 0.0015(10) -0.0002(10) C4 0.0190(12) 0.0184(11) 0.0539(17) 0.0036(10) 0.0066(11) 0.0010(9) C7 0.0308(14) 0.0299(13) 0.0442(16) 0.0141(11) 0.0026(11) 0.0072(11) C5 0.0209(11) 0.0369(13) 0.0293(13) 0.0139(10) 0.0056(9) 0.0067(10) C8 0.0296(15) 0.064(2) 0.0411(17) -0.0256(15) -0.0065(12) 0.0018(14) C9 0.0338(16) 0.0186(13) 0.124(3) 0.0073(16) 0.0135(19) -0.0023(11) C10 0.0406(17) 0.086(3) 0.0449(18) 0.0404(18) 0.0177(14) 0.0244(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl2 C13 1.709(2) . ? Cl1 C12 1.707(2) . ? O1 C11 1.207(3) . ? C11 C20 1.486(3) . ? C11 C12 1.497(3) . ? C13 C12 1.342(3) . ? C13 C14 1.486(3) . ? O2 C14 1.217(3) . ? C15 C16 1.390(3) . ? C15 C20 1.398(3) . ? C15 C14 1.484(3) . ? C16 C17 1.389(3) . ? C16 H16 1.01(3) . ? C2 C1 1.425(3) . ? C2 C3 1.428(3) . ? C2 C7 1.503(3) . ? C20 C19 1.393(3) . ? C1 C5 1.425(3) 3_657 ? C1 C6 1.503(3) . ? C19 C18 1.385(4) . ? C19 H19 0.91(3) . ? C3 C4 1.424(4) 3_657 ? C3 C8 1.502(4) . ? C18 C17 1.387(4) . ? C18 H18 0.94(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C17 H17 0.92(3) . ? C4 C3 1.424(4) 3_657 ? C4 C5 1.425(4) . ? C4 C9 1.505(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C5 C1 1.425(3) 3_657 ? C5 C10 1.503(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 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 . ? 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 C11 C20 122.7(2) . . ? O1 C11 C12 120.7(2) . . ? C20 C11 C12 116.54(19) . . ? C12 C13 C14 122.0(2) . . ? C12 C13 Cl2 122.28(18) . . ? C14 C13 Cl2 115.70(17) . . ? C16 C15 C20 120.1(2) . . ? C16 C15 C14 119.0(2) . . ? C20 C15 C14 120.9(2) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.8(16) . . ? C15 C16 H16 119.4(17) . . ? C1 C2 C3 108.3(2) . . ? C1 C2 C7 126.1(2) . . ? C3 C2 C7 125.5(2) . . ? O2 C14 C15 122.3(2) . . ? O2 C14 C13 120.5(2) . . ? C15 C14 C13 117.2(2) . . ? C19 C20 C15 119.5(2) . . ? C19 C20 C11 119.3(2) . . ? C15 C20 C11 121.14(19) . . ? C13 C12 C11 122.2(2) . . ? C13 C12 Cl1 122.14(18) . . ? C11 C12 Cl1 115.61(16) . . ? C2 C1 C5 107.9(2) . 3_657 ? C2 C1 C6 125.5(2) . . ? C5 C1 C6 126.6(2) 3_657 . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 119.7(18) . . ? C20 C19 H19 120.3(18) . . ? C4 C3 C2 107.5(2) 3_657 . ? C4 C3 C8 126.6(2) 3_657 . ? C2 C3 C8 125.9(2) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18 117.7(18) . . ? C17 C18 H18 121.9(18) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C18 C17 C16 120.1(2) . . ? C18 C17 H17 119.6(17) . . ? C16 C17 H17 120.3(17) . . ? C3 C4 C5 108.4(2) 3_657 . ? C3 C4 C9 125.6(3) 3_657 . ? C5 C4 C9 125.9(3) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C5 C4 107.9(2) 3_657 . ? C1 C5 C10 126.7(3) 3_657 . ? C4 C5 C10 125.4(3) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.538 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.079 # Attachment '- 2.cif' data_DecaBr2NQ _database_code_depnum_ccdc_archive 'CCDC 766110' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; decamethylferrocene-dibromonaphthoquinone complex ; _chemical_name_common 'decamethylferrocene-dibromonaphthoquinone complex' _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 Fe, 2(C10 H4 Br2 O2)' _chemical_formula_sum 'C40 H38 Br4 Fe O4' _chemical_formula_weight 958.19 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.0046(12) _cell_length_b 8.4462(7) _cell_length_c 15.2741(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.6160(10) _cell_angle_gamma 90.00 _cell_volume 1798.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 5079 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.32 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 4.906 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2162 _exptl_absorpt_correction_T_max 0.3028 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _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 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9336 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3285 _reflns_number_gt 2915 _reflns_threshold_expression >2\s(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^ > 2\s(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^)+(0.0276P)^2^+0.6884P] 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 3285 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0536 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.003 _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 0.0000 1.0000 0.01874(10) Uani 1 2 d S . . C6 C 0.35799(19) -0.2982(3) 0.9907(3) 0.0585(9) Uani 1 1 d . . . H6A H 0.2939 -0.3245 1.0029 0.088 Uiso 1 1 calc R . . H6B H 0.4032 -0.3543 1.0307 0.088 Uiso 1 1 calc R . . H6C H 0.3669 -0.3278 0.9314 0.088 Uiso 1 1 calc R . . C1 C 0.37361(15) -0.1227(3) 1.00199(17) 0.0311(5) Uani 1 1 d . . . C5 C 0.39683(15) -0.0430(3) 1.08326(16) 0.0313(5) Uani 1 1 d . . . Br2 Br 0.193501(17) 0.09522(3) 1.233853(14) 0.02988(8) Uani 1 1 d . . . Br1 Br 0.162866(18) 0.42009(3) 1.106048(15) 0.03074(8) Uani 1 1 d . . . C12 C 0.14803(15) 0.2138(2) 1.06154(14) 0.0229(5) Uani 1 1 d . . . C14 C 0.14566(15) -0.0790(2) 1.07554(14) 0.0230(5) Uani 1 1 d . . . C15 C 0.10202(15) -0.2407(3) 0.94176(15) 0.0267(5) Uani 1 1 d . . . H15 H 0.1085 -0.3309 0.9768 0.032 Uiso 1 1 calc R . . C18 C 0.07842(16) 0.0276(3) 0.83706(14) 0.0271(5) Uani 1 1 d . . . H18 H 0.0696 0.1175 0.8020 0.032 Uiso 1 1 calc R . . C3 C 0.38247(14) 0.1436(3) 0.97337(14) 0.0230(4) Uani 1 1 d . . . C17 C 0.06552(16) -0.1210(3) 0.79956(15) 0.0287(5) Uani 1 1 d . . . H17 H 0.0490 -0.1311 0.7394 0.034 Uiso 1 1 calc R . . C20 C 0.11722(15) -0.0918(2) 0.97976(14) 0.0214(4) Uani 1 1 d . . . C19 C 0.10448(14) 0.0432(3) 0.92680(14) 0.0218(4) Uani 1 1 d . . . C11 C 0.11893(16) 0.2039(3) 0.96530(14) 0.0247(5) Uani 1 1 d . . . C4 C 0.40259(15) 0.1224(3) 1.06563(15) 0.0263(5) Uani 1 1 d . . . C2 C 0.36469(15) -0.0081(3) 0.93363(15) 0.0257(5) Uani 1 1 d . . . C16 C 0.07734(16) -0.2550(3) 0.85222(15) 0.0294(5) Uani 1 1 d . . . H16 H 0.0686 -0.3549 0.8271 0.035 Uiso 1 1 calc R . . C7 C 0.33822(19) -0.0388(4) 0.83723(18) 0.0470(7) Uani 1 1 d . . . H7A H 0.3591 -0.1430 0.8227 0.071 Uiso 1 1 calc R . . H7B H 0.3688 0.0382 0.8031 0.071 Uiso 1 1 calc R . . H7C H 0.2699 -0.0313 0.8244 0.071 Uiso 1 1 calc R . . C9 C 0.42313(19) 0.2514(4) 1.13200(18) 0.0480(7) Uani 1 1 d . . . H9A H 0.4583 0.3346 1.1068 0.072 Uiso 1 1 calc R . . H9B H 0.4605 0.2095 1.1828 0.072 Uiso 1 1 calc R . . H9C H 0.3638 0.2927 1.1490 0.072 Uiso 1 1 calc R . . C8 C 0.37643(17) 0.2992(3) 0.92573(18) 0.0378(6) Uani 1 1 d . . . H8A H 0.3867 0.2827 0.8652 0.057 Uiso 1 1 calc R . . H8B H 0.4246 0.3697 0.9524 0.057 Uiso 1 1 calc R . . H8C H 0.3141 0.3448 0.9292 0.057 Uiso 1 1 calc R . . C13 C 0.16094(15) 0.0849(3) 1.11243(14) 0.0220(5) Uani 1 1 d . . . C10 C 0.4102(2) -0.1219(4) 1.1723(2) 0.0619(10) Uani 1 1 d . . . H10A H 0.3486 -0.1443 1.1920 0.093 Uiso 1 1 calc R . . H10B H 0.4454 -0.0527 1.2136 0.093 Uiso 1 1 calc R . . H10C H 0.4451 -0.2189 1.1679 0.093 Uiso 1 1 calc R . . O2 O 0.15571(12) -0.19408(19) 1.12309(10) 0.0331(4) Uani 1 1 d . . . O1 O 0.10683(14) 0.32309(19) 0.92101(11) 0.0400(4) 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 Fe1 0.0178(2) 0.0169(2) 0.0212(2) 0.00211(16) 0.00005(16) 0.00195(16) C6 0.0314(15) 0.0251(14) 0.120(3) 0.0044(16) 0.0121(16) -0.0034(11) C1 0.0178(11) 0.0221(11) 0.0537(16) 0.0035(10) 0.0058(10) 0.0005(9) C5 0.0196(11) 0.0425(14) 0.0327(13) 0.0156(11) 0.0073(9) 0.0078(10) Br2 0.03743(14) 0.03357(14) 0.01781(12) -0.00019(9) -0.00157(9) -0.00130(10) Br1 0.04365(15) 0.02077(12) 0.02775(14) -0.00361(9) 0.00323(10) -0.00458(9) C12 0.0261(11) 0.0208(11) 0.0223(11) -0.0020(9) 0.0045(9) -0.0016(9) C14 0.0238(11) 0.0221(11) 0.0232(12) 0.0032(9) 0.0026(9) 0.0000(9) C15 0.0261(11) 0.0212(11) 0.0325(13) 0.0009(9) 0.0010(9) 0.0022(9) C18 0.0273(12) 0.0327(12) 0.0213(12) 0.0019(10) 0.0030(9) -0.0003(10) C3 0.0179(10) 0.0212(11) 0.0296(12) 0.0021(9) 0.0011(9) 0.0034(9) C17 0.0256(12) 0.0391(14) 0.0214(12) -0.0055(10) 0.0015(9) -0.0016(10) C20 0.0178(10) 0.0235(11) 0.0226(11) -0.0006(9) 0.0015(8) 0.0015(8) C19 0.0199(10) 0.0244(11) 0.0218(11) 0.0000(9) 0.0050(8) 0.0013(9) C11 0.0289(11) 0.0244(12) 0.0213(11) 0.0009(9) 0.0052(9) -0.0001(9) C4 0.0200(11) 0.0344(13) 0.0242(12) -0.0047(10) 0.0007(9) 0.0059(9) C2 0.0188(11) 0.0284(12) 0.0295(12) -0.0060(10) -0.0006(9) 0.0009(9) C16 0.0266(12) 0.0284(12) 0.0328(13) -0.0106(10) 0.0010(9) 0.0003(10) C7 0.0308(14) 0.0672(19) 0.0412(16) -0.0209(14) -0.0059(11) 0.0056(13) C9 0.0350(14) 0.066(2) 0.0416(16) -0.0279(14) -0.0014(12) 0.0079(13) C8 0.0308(13) 0.0287(13) 0.0535(17) 0.0135(12) 0.0026(11) 0.0084(11) C13 0.0236(11) 0.0253(12) 0.0171(11) -0.0007(8) 0.0023(8) -0.0007(9) C10 0.0437(17) 0.095(3) 0.0497(19) 0.0436(18) 0.0168(14) 0.0254(17) O2 0.0477(10) 0.0240(9) 0.0263(9) 0.0060(7) -0.0025(7) -0.0012(7) O1 0.0711(13) 0.0241(9) 0.0242(9) 0.0059(7) 0.0018(8) -0.0002(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 C1 1.507(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C1 C2 1.420(3) . ? C1 C5 1.422(4) . ? C5 C4 1.426(3) . ? C5 C10 1.509(3) . ? Br2 C13 1.868(2) . ? Br1 C12 1.874(2) . ? C12 C13 1.340(3) . ? C12 C11 1.489(3) . ? C14 O2 1.213(3) . ? C14 C20 1.482(3) . ? C14 C13 1.502(3) . ? C15 C16 1.383(3) . ? C15 C20 1.393(3) . ? C15 H15 0.9300 . ? C18 C17 1.384(3) . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C3 C4 1.421(3) . ? C3 C2 1.429(3) . ? C3 C8 1.501(3) . ? C17 C16 1.389(3) . ? C17 H17 0.9300 . ? C20 C19 1.399(3) . ? C19 C11 1.485(3) . ? C11 O1 1.215(3) . ? C4 C9 1.496(3) . ? C2 C7 1.505(3) . ? C16 H16 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C1 C5 108.4(2) . . ? C2 C1 C6 125.8(3) . . ? C5 C1 C6 125.8(3) . . ? C1 C5 C4 108.1(2) . . ? C1 C5 C10 125.1(3) . . ? C4 C5 C10 126.8(3) . . ? C13 C12 C11 122.38(19) . . ? C13 C12 Br1 122.76(16) . . ? C11 C12 Br1 114.85(15) . . ? O2 C14 C20 122.5(2) . . ? O2 C14 C13 120.7(2) . . ? C20 C14 C13 116.87(18) . . ? C16 C15 C20 120.3(2) . . ? C16 C15 H15 119.9 . . ? C20 C15 H15 119.9 . . ? C17 C18 C19 120.3(2) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C4 C3 C2 108.54(19) . . ? C4 C3 C8 126.0(2) . . ? C2 C3 C8 125.5(2) . . ? C18 C17 C16 119.7(2) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C15 C20 C19 119.3(2) . . ? C15 C20 C14 119.50(19) . . ? C19 C20 C14 121.21(19) . . ? C18 C19 C20 120.0(2) . . ? C18 C19 C11 119.3(2) . . ? C20 C19 C11 120.73(19) . . ? O1 C11 C19 122.0(2) . . ? O1 C11 C12 120.8(2) . . ? C19 C11 C12 117.11(18) . . ? C3 C4 C5 107.5(2) . . ? C3 C4 C9 125.9(2) . . ? C5 C4 C9 126.5(2) . . ? C1 C2 C3 107.4(2) . . ? C1 C2 C7 126.7(2) . . ? C3 C2 C7 125.9(2) . . ? C15 C16 C17 120.4(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C13 C14 121.69(19) . . ? C12 C13 Br2 122.95(16) . . ? C14 C13 Br2 115.30(15) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.479 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.059 #==END data_me8cl2nqp2c _database_code_depnum_ccdc_archive 'CCDC 766111' #TrackingRef '- azumi.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; octamethylferrocene-dibromonaphthoquinone complex ; _chemical_name_common 'octamethylferrocene-dibromonaphthoquinone complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H32 Cl4 Fe O4' _chemical_formula_weight 750.29 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' Cl Cl 0.1484 0.1585 '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 13.8088(10) _cell_length_b 8.1646(6) _cell_length_c 15.0981(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.989(2) _cell_angle_gamma 90.00 _cell_volume 1692.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.802 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6899 _exptl_absorpt_correction_T_max 0.9241 _exptl_absorpt_process_details 'SADABS;Sheldrick 1996' _exptl_special_details ; SADABS;Sheldrick,1996 ; _diffrn_ambient_temperature 173 _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 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12231 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4197 _reflns_number_gt 3278 _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^)+(0.0608P)^2^+0.5054P] 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 4197 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 0.39984(19) 0.1202(5) 1.0662(2) 0.0795(11) Uani 1 1 d . . . C2 C 0.37989(18) 0.1469(5) 0.9733(2) 0.0761(10) Uani 1 1 d . . . C3 C 0.3636(2) -0.0049(6) 0.9307(3) 0.0882(12) Uani 1 1 d . . . C4 C 0.6268(2) 0.1255(6) 1.0014(4) 0.1023(15) Uani 1 1 d . . . C5 C 0.6043(2) 0.0512(6) 0.9178(3) 0.0942(14) Uani 1 1 d . . . C6 C 0.4195(3) 0.2461(10) 1.1305(4) 0.122(2) Uani 0.80 1 d P . . H6A H 0.4544 0.3332 1.1053 0.184 Uiso 0.80 1 calc PR . . H6B H 0.4582 0.2026 1.1817 0.184 Uiso 0.80 1 calc PR . . H6C H 0.3593 0.2874 1.1480 0.184 Uiso 0.80 1 calc PR . . C7 C 0.3737(3) 0.3060(7) 0.9270(3) 0.1010(18) Uani 0.80 1 d P . . H7A H 0.3912 0.2924 0.8676 0.152 Uiso 0.80 1 calc PR . . H7B H 0.4175 0.3823 0.9586 0.152 Uiso 0.80 1 calc PR . . H7C H 0.3083 0.3471 0.9247 0.152 Uiso 0.80 1 calc PR . . C8 C 0.3402(3) -0.0309(9) 0.8337(3) 0.112(2) Uani 0.80 1 d P . . H8A H 0.2712 -0.0212 0.8185 0.168 Uiso 0.80 1 calc PR . . H8B H 0.3611 -0.1383 0.8181 0.168 Uiso 0.80 1 calc PR . . H8C H 0.3732 0.0498 0.8017 0.168 Uiso 0.80 1 calc PR . . C9 C 0.6393(4) 0.2947(9) 1.0134(7) 0.181(4) Uani 0.80 1 d P . . H9A H 0.7062 0.3229 1.0093 0.272 Uiso 0.80 1 calc PR . . H9B H 0.6216 0.3251 1.0711 0.272 Uiso 0.80 1 calc PR . . H9C H 0.5985 0.3520 0.9682 0.272 Uiso 0.80 1 calc PR . . C10 C 0.5927(3) 0.1444(8) 0.8319(4) 0.124(2) Uani 0.80 1 d P . . H10A H 0.5728 0.2546 0.8429 0.187 Uiso 0.80 1 calc PR . . H10B H 0.5442 0.0922 0.7912 0.187 Uiso 0.80 1 calc PR . . H10C H 0.6536 0.1460 0.8066 0.187 Uiso 0.80 1 calc PR . . C11 C 0.14608(13) -0.0823(2) 1.07905(11) 0.0264(4) Uani 1 1 d . . . C12 C 0.16195(13) 0.0857(2) 1.11666(11) 0.0258(3) Uani 1 1 d . . . C13 C 0.14944(13) 0.2202(2) 1.06619(11) 0.0271(4) Uani 1 1 d . . . C14 C 0.11978(13) 0.2118(2) 0.96820(11) 0.0277(4) Uani 1 1 d . . . C15 C 0.10534(12) 0.0461(2) 0.92887(11) 0.0247(3) Uani 1 1 d . . . C16 C 0.07970(14) 0.0312(2) 0.83762(12) 0.0288(4) Uani 1 1 d . . . H16 H 0.0711 0.1244 0.8023 0.035 Uiso 1 1 calc R . . C17 C 0.06692(14) -0.1227(2) 0.79946(12) 0.0322(4) Uani 1 1 d . . . H17 H 0.0502 -0.1325 0.7384 0.039 Uiso 1 1 calc R . . C18 C 0.07894(14) -0.2619(2) 0.85165(13) 0.0327(4) Uani 1 1 d . . . H18 H 0.0703 -0.3648 0.8256 0.039 Uiso 1 1 calc R . . C19 C 0.10394(13) -0.2483(2) 0.94287(12) 0.0297(4) Uani 1 1 d . . . H19 H 0.1113 -0.3419 0.9780 0.036 Uiso 1 1 calc R . . C20 C 0.11786(12) -0.0945(2) 0.98149(11) 0.0245(3) Uani 1 1 d . . . Cl1 Cl 0.19419(4) 0.09588(6) 1.22876(3) 0.03740(14) Uani 1 1 d . . . Cl2 Cl 0.16462(4) 0.41342(6) 1.10881(3) 0.03906(14) Uani 1 1 d . . . Fe1 Fe 0.5000 0.0000 1.0000 0.0732(2) Uani 1 2 d S . . O1 O 0.15545(10) -0.20150(16) 1.12693(8) 0.0359(3) Uani 1 1 d . . . O2 O 0.10702(12) 0.33548(17) 0.92432(9) 0.0418(4) 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 0.0330(13) 0.133(3) 0.074(2) 0.030(2) 0.0133(13) 0.0220(16) C2 0.0294(12) 0.118(3) 0.082(2) 0.045(2) 0.0132(13) 0.0144(15) C3 0.0277(13) 0.135(4) 0.103(3) 0.031(3) 0.0125(15) 0.0130(17) C4 0.0287(14) 0.105(3) 0.178(5) 0.043(3) 0.030(2) 0.0103(16) C5 0.0356(14) 0.147(4) 0.104(3) 0.071(3) 0.0249(17) 0.0255(18) C6 0.060(3) 0.205(7) 0.103(4) 0.009(5) 0.017(3) 0.033(3) C7 0.0411(19) 0.137(4) 0.127(4) 0.070(3) 0.016(2) 0.024(2) C8 0.0363(19) 0.210(6) 0.089(3) -0.009(4) 0.001(2) 0.017(3) C9 0.058(3) 0.124(6) 0.368(13) 0.040(7) 0.056(5) 0.010(3) C10 0.051(2) 0.195(6) 0.133(4) 0.112(4) 0.039(2) 0.045(3) C11 0.0295(9) 0.0247(8) 0.0255(8) 0.0004(7) 0.0049(7) 0.0004(7) C12 0.0306(9) 0.0265(9) 0.0203(8) -0.0003(6) 0.0028(6) -0.0007(7) C13 0.0336(9) 0.0209(8) 0.0271(8) -0.0021(6) 0.0051(7) -0.0024(7) C14 0.0348(9) 0.0230(8) 0.0257(8) 0.0007(7) 0.0058(7) -0.0010(7) C15 0.0270(8) 0.0230(8) 0.0246(8) -0.0003(6) 0.0056(7) 0.0001(6) C16 0.0357(9) 0.0276(9) 0.0233(8) 0.0006(7) 0.0045(7) 0.0010(7) C17 0.0361(10) 0.0354(10) 0.0249(8) -0.0045(7) 0.0025(7) -0.0006(8) C18 0.0360(10) 0.0271(9) 0.0347(9) -0.0074(8) 0.0029(8) -0.0004(7) C19 0.0345(9) 0.0221(8) 0.0324(9) -0.0005(7) 0.0029(7) 0.0018(7) C20 0.0250(8) 0.0237(8) 0.0252(8) 0.0004(6) 0.0045(6) 0.0016(6) Cl1 0.0528(3) 0.0361(3) 0.0222(2) -0.00056(17) -0.00138(19) -0.0027(2) Cl2 0.0620(3) 0.0227(2) 0.0321(2) -0.00513(17) 0.0033(2) -0.0051(2) Fe1 0.0262(2) 0.1110(6) 0.0845(4) 0.0445(4) 0.0153(2) 0.0147(3) O1 0.0533(8) 0.0245(7) 0.0295(7) 0.0063(5) 0.0021(6) 0.0006(6) O2 0.0714(10) 0.0230(7) 0.0302(7) 0.0039(6) 0.0020(7) 0.0003(6) _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 C2 1.417(4) . ? C1 C6 1.420(7) . ? C1 C5 1.423(6) 3_657 ? C1 Fe1 2.040(3) . ? C2 C3 1.403(6) . ? C2 C7 1.474(5) . ? C2 Fe1 2.052(3) . ? C3 C4 1.418(6) 3_657 ? C3 C8 1.482(6) . ? C3 Fe1 2.057(3) . ? C4 C9 1.402(8) . ? C4 C5 1.405(6) . ? C4 C3 1.418(6) 3_657 ? C4 Fe1 2.027(3) . ? C5 C1 1.423(6) 3_657 ? C5 C10 1.498(5) . ? C5 Fe1 2.040(3) . ? C11 O1 1.211(2) . ? C11 C20 1.487(2) . ? C11 C12 1.492(2) . ? C12 C13 1.338(2) . ? C12 Cl1 1.7066(17) . ? C13 C14 1.495(2) . ? C13 Cl2 1.7088(18) . ? C14 O2 1.211(2) . ? C14 C15 1.482(2) . ? C15 C16 1.392(2) . ? C15 C20 1.397(2) . ? C16 C17 1.386(3) . ? C17 C18 1.383(3) . ? C18 C19 1.389(3) . ? C19 C20 1.389(2) . ? Fe1 C4 2.027(3) 3_657 ? Fe1 C5 2.040(3) 3_657 ? Fe1 C1 2.040(3) 3_657 ? Fe1 C2 2.052(3) 3_657 ? Fe1 C3 2.057(3) 3_657 ? 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 C1 C6 124.7(4) . . ? C2 C1 C5 108.2(4) . 3_657 ? C6 C1 C5 127.2(4) . 3_657 ? C2 C1 Fe1 70.20(19) . . ? C6 C1 Fe1 126.3(3) . . ? C5 C1 Fe1 69.6(2) 3_657 . ? C3 C2 C1 108.9(3) . . ? C3 C2 C7 124.2(4) . . ? C1 C2 C7 126.9(5) . . ? C3 C2 Fe1 70.21(19) . . ? C1 C2 Fe1 69.29(17) . . ? C7 C2 Fe1 127.9(2) . . ? C2 C3 C4 106.5(4) . 3_657 ? C2 C3 C8 126.0(4) . . ? C4 C3 C8 127.5(5) 3_657 . ? C2 C3 Fe1 69.85(19) . . ? C4 C3 Fe1 68.6(2) 3_657 . ? C8 C3 Fe1 126.8(2) . . ? C9 C4 C5 123.7(6) . . ? C9 C4 C3 126.1(7) . 3_657 ? C5 C4 C3 110.2(4) . 3_657 ? C9 C4 Fe1 126.4(3) . . ? C5 C4 Fe1 70.3(2) . . ? C3 C4 Fe1 70.8(2) 3_657 . ? C4 C5 C1 106.3(3) . 3_657 ? C4 C5 C10 123.5(5) . . ? C1 C5 C10 130.1(5) 3_657 . ? C4 C5 Fe1 69.3(2) . . ? C1 C5 Fe1 69.60(18) 3_657 . ? C10 C5 Fe1 127.7(2) . . ? O1 C11 C20 122.53(16) . . ? O1 C11 C12 120.60(15) . . ? C20 C11 C12 116.86(14) . . ? C13 C12 C11 122.19(15) . . ? C13 C12 Cl1 121.98(14) . . ? C11 C12 Cl1 115.81(12) . . ? C12 C13 C14 122.14(16) . . ? C12 C13 Cl2 122.69(14) . . ? C14 C13 Cl2 115.16(13) . . ? O2 C14 C15 122.42(16) . . ? O2 C14 C13 120.83(16) . . ? C15 C14 C13 116.73(14) . . ? C16 C15 C20 119.65(16) . . ? C16 C15 C14 119.09(15) . . ? C20 C15 C14 121.25(15) . . ? C17 C16 C15 119.94(17) . . ? C18 C17 C16 120.37(17) . . ? C17 C18 C19 120.13(17) . . ? C20 C19 C18 119.85(17) . . ? C19 C20 C15 120.05(16) . . ? C19 C20 C11 119.14(15) . . ? C15 C20 C11 120.81(15) . . ? C4 Fe1 C4 180.0 3_657 . ? C4 Fe1 C5 40.40(18) 3_657 3_657 ? C4 Fe1 C5 139.60(18) . 3_657 ? C4 Fe1 C5 139.60(18) 3_657 . ? C4 Fe1 C5 40.40(18) . . ? C5 Fe1 C5 179.999(1) 3_657 . ? C4 Fe1 C1 67.61(19) 3_657 . ? C4 Fe1 C1 112.39(19) . . ? C5 Fe1 C1 40.81(17) 3_657 . ? C5 Fe1 C1 139.19(17) . . ? C4 Fe1 C1 112.39(19) 3_657 3_657 ? C4 Fe1 C1 67.61(18) . 3_657 ? C5 Fe1 C1 139.19(17) 3_657 3_657 ? C5 Fe1 C1 40.81(17) . 3_657 ? C1 Fe1 C1 180.00(10) . 3_657 ? C4 Fe1 C2 67.27(15) 3_657 . ? C4 Fe1 C2 112.73(15) . . ? C5 Fe1 C2 68.38(12) 3_657 . ? C5 Fe1 C2 111.62(12) . . ? C1 Fe1 C2 40.51(13) . . ? C1 Fe1 C2 139.49(13) 3_657 . ? C4 Fe1 C2 112.73(15) 3_657 3_657 ? C4 Fe1 C2 67.27(15) . 3_657 ? C5 Fe1 C2 111.62(12) 3_657 3_657 ? C5 Fe1 C2 68.38(12) . 3_657 ? C1 Fe1 C2 139.49(13) . 3_657 ? C1 Fe1 C2 40.51(13) 3_657 3_657 ? C2 Fe1 C2 180.00(19) . 3_657 ? C4 Fe1 C3 40.61(16) 3_657 . ? C4 Fe1 C3 139.38(16) . . ? C5 Fe1 C3 68.78(15) 3_657 . ? C5 Fe1 C3 111.22(15) . . ? C1 Fe1 C3 68.09(16) . . ? C1 Fe1 C3 111.91(16) 3_657 . ? C2 Fe1 C3 39.94(15) . . ? C2 Fe1 C3 140.06(16) 3_657 . ? C4 Fe1 C3 139.39(16) 3_657 3_657 ? C4 Fe1 C3 40.61(16) . 3_657 ? C5 Fe1 C3 111.22(15) 3_657 3_657 ? C5 Fe1 C3 68.78(15) . 3_657 ? C1 Fe1 C3 111.91(16) . 3_657 ? C1 Fe1 C3 68.09(16) 3_657 3_657 ? C2 Fe1 C3 140.06(16) . 3_657 ? C2 Fe1 C3 39.94(15) 3_657 3_657 ? C3 Fe1 C3 180.0(3) . 3_657 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.644 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.063 #==END data_octmeclnqp2c _database_code_depnum_ccdc_archive 'CCDC 766112' #TrackingRef '- azumi.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; octamethylferrocene-dibromonaphthoquinone complex ; _chemical_name_common 'octamethylferrocene-dibromonaphthoquinone complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H32 Cl4 Fe O4' _chemical_formula_weight 750.29 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' Cl Cl 0.1484 0.1585 '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 13.7023(7) _cell_length_b 8.1596(4) _cell_length_c 15.0503(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.1850(10) _cell_angle_gamma 90.00 _cell_volume 1672.91(15) _cell_formula_units_Z 2 _cell_measurement_temperature 90 _cell_measurement_reflns_used 3661 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.88 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7115 _exptl_absorpt_correction_T_max 0.9053 _exptl_absorpt_process_details 'SADABS;Sheldrick 1996' _exptl_special_details ; SADABS;Sheldrick,1996 ; _diffrn_ambient_temperature 90 _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 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10518 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3980 _reflns_number_gt 3289 _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^)+(0.0100P)^2^+11.0000P] 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 3980 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.69616(7) 1.09628(11) 1.22986(5) 0.0238(2) Uani 1 1 d . . . Cl1 Cl 0.66515(8) 1.41440(11) 1.10937(6) 0.0263(2) Uani 1 1 d . . . Fe1 Fe 1.0000 0.0000 1.0000 0.0717(5) Uani 1 2 d S . . O2 O 0.65512(19) 0.7981(3) 1.12792(16) 0.0217(5) Uani 1 1 d . . . O1 O 0.6043(2) 1.3364(3) 0.92437(17) 0.0265(6) Uani 1 1 d . . . C14 C 0.6459(2) 0.9173(4) 1.0795(2) 0.0158(6) Uani 1 1 d . . . C20 C 0.6175(2) 0.9051(4) 0.9816(2) 0.0154(6) Uani 1 1 d . . . C18 C 0.5791(2) 1.0309(4) 0.8367(2) 0.0185(7) Uani 1 1 d . . . H18 H 0.5698 1.1262 0.8006 0.022 Uiso 1 1 calc R . . C15 C 0.6043(2) 0.7502(4) 0.9429(2) 0.0179(7) Uani 1 1 d . . . H15 H 0.6120 0.6545 0.9790 0.022 Uiso 1 1 calc R . . C11 C 0.6177(2) 1.2117(4) 0.9681(2) 0.0171(6) Uani 1 1 d . . . C12 C 0.6492(3) 1.2210(4) 1.0667(2) 0.0180(7) Uani 1 1 d . . . C13 C 0.6623(2) 1.0863(4) 1.1172(2) 0.0171(6) Uani 1 1 d . . . C19 C 0.6046(2) 1.0456(4) 0.9286(2) 0.0149(6) Uani 1 1 d . . . C16 C 0.5799(3) 0.7371(4) 0.8509(2) 0.0216(7) Uani 1 1 d . . . H16 H 0.5718 0.6319 0.8241 0.026 Uiso 1 1 calc R . . C17 C 0.5672(3) 0.8764(4) 0.7982(2) 0.0209(7) Uani 1 1 d . . . H17 H 0.5504 0.8663 0.7355 0.025 Uiso 1 1 calc R . . C2 C 0.8782(3) 0.1465(10) 0.9747(5) 0.076(3) Uani 1 1 d . . . C4 C 1.1256(5) 0.1211(12) 0.9939(10) 0.124(5) Uani 1 1 d . . . C1 C 0.9033(4) 0.1267(12) 1.0706(6) 0.092(3) Uani 1 1 d . . . C3 C 0.8619(4) -0.0060(13) 0.9365(8) 0.106(4) Uani 1 1 d . . . C5 C 1.1016(6) 0.0482(16) 0.9133(8) 0.135(6) Uani 1 1 d . . . C7 C 0.8698(5) 0.3037(10) 0.9258(6) 0.080(3) Uani 0.80 1 d P . . H7A H 0.8910 0.2888 0.8662 0.120 Uiso 0.80 1 calc PR . . H7B H 0.9116 0.3859 0.9587 0.120 Uiso 0.80 1 calc PR . . H7C H 0.8014 0.3408 0.9202 0.120 Uiso 0.80 1 calc PR . . C10 C 1.0895(7) 0.1424(17) 0.8280(8) 0.152(7) Uani 0.80 1 d P . . H10A H 1.0652 0.2526 0.8392 0.228 Uiso 0.80 1 calc PR . . H10B H 1.0424 0.0860 0.7848 0.228 Uiso 0.80 1 calc PR . . H10C H 1.1530 0.1504 0.8039 0.228 Uiso 0.80 1 calc PR . . C6 C 0.9260(10) 0.253(2) 1.1254(7) 0.171(9) Uani 0.80 1 d P . . H6A H 0.8656 0.3016 1.1433 0.257 Uiso 0.80 1 calc PR . . H6B H 0.9617 0.3360 1.0944 0.257 Uiso 0.80 1 calc PR . . H6C H 0.9673 0.2151 1.1785 0.257 Uiso 0.80 1 calc PR . . C9 C 1.1383(7) 0.2899(13) 0.9984(13) 0.174(9) Uani 0.80 1 d P . . H9A H 1.2081 0.3161 0.9988 0.261 Uiso 0.80 1 calc PR . . H9B H 1.1145 0.3316 1.0532 0.261 Uiso 0.80 1 calc PR . . H9C H 1.1012 0.3413 0.9464 0.261 Uiso 0.80 1 calc PR . . C8 C 0.8409(6) -0.0208(17) 0.8303(9) 0.128(5) Uani 0.80 1 d P . . H8A H 0.7708 -0.0037 0.8122 0.193 Uiso 0.80 1 calc PR . . H8B H 0.8600 -0.1302 0.8115 0.193 Uiso 0.80 1 calc PR . . H8C H 0.8791 0.0623 0.8022 0.193 Uiso 0.80 1 calc PR . . 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 Cl2 0.0370(5) 0.0212(4) 0.0129(4) -0.0005(3) 0.0009(3) -0.0006(4) Cl1 0.0473(6) 0.0135(4) 0.0182(4) -0.0027(3) 0.0045(4) -0.0024(4) Fe1 0.0159(4) 0.0882(9) 0.1137(11) 0.0776(9) 0.0196(5) 0.0146(5) O2 0.0302(13) 0.0157(12) 0.0190(12) 0.0030(9) 0.0025(10) 0.0003(10) O1 0.0450(16) 0.0138(12) 0.0205(13) 0.0028(10) 0.0031(11) 0.0012(11) C14 0.0171(15) 0.0154(15) 0.0153(15) -0.0002(12) 0.0039(12) -0.0003(12) C20 0.0160(15) 0.0143(15) 0.0165(15) 0.0003(12) 0.0045(12) 0.0006(12) C18 0.0219(16) 0.0177(16) 0.0164(16) 0.0020(13) 0.0045(13) 0.0007(13) C15 0.0225(16) 0.0135(15) 0.0177(16) 0.0009(12) 0.0018(13) 0.0009(13) C11 0.0209(16) 0.0164(16) 0.0145(15) 0.0013(12) 0.0048(12) -0.0004(13) C12 0.0254(17) 0.0123(15) 0.0169(16) -0.0026(12) 0.0052(13) -0.0024(13) C13 0.0215(16) 0.0188(16) 0.0109(14) -0.0003(12) 0.0020(12) 0.0003(13) C19 0.0156(15) 0.0148(15) 0.0150(15) -0.0008(12) 0.0049(12) 0.0008(12) C16 0.0255(17) 0.0165(16) 0.0228(17) -0.0048(14) 0.0021(14) 0.0007(14) C17 0.0244(17) 0.0238(18) 0.0146(15) -0.0027(13) 0.0029(13) 0.0005(14) C2 0.017(2) 0.104(6) 0.110(5) 0.080(5) 0.020(3) 0.018(3) C4 0.022(3) 0.087(6) 0.270(14) 0.104(9) 0.050(6) 0.016(3) C1 0.031(3) 0.121(7) 0.127(7) 0.082(6) 0.026(4) 0.035(4) C3 0.022(3) 0.114(7) 0.182(10) 0.063(7) 0.005(4) 0.019(4) C5 0.051(5) 0.181(12) 0.184(10) 0.153(10) 0.067(6) 0.066(6) C7 0.028(3) 0.093(6) 0.123(7) 0.088(6) 0.029(4) 0.029(3) C10 0.081(6) 0.206(14) 0.183(12) 0.169(11) 0.079(7) 0.090(8) C6 0.137(11) 0.31(2) 0.061(6) -0.014(10) -0.007(7) 0.158(14) C9 0.036(5) 0.058(6) 0.43(3) -0.042(11) 0.044(9) -0.001(4) C8 0.029(4) 0.181(13) 0.176(12) 0.077(11) 0.013(6) 0.024(6) _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 Cl2 C13 1.711(3) . ? Cl1 C12 1.709(3) . ? Fe1 C4 1.995(7) . ? Fe1 C4 1.995(7) 3_757 ? Fe1 C3 2.027(7) . ? Fe1 C3 2.027(7) 3_757 ? Fe1 C5 2.046(7) . ? Fe1 C5 2.046(7) 3_757 ? Fe1 C2 2.055(5) . ? Fe1 C2 2.055(5) 3_757 ? Fe1 C1 2.063(9) 3_757 ? Fe1 C1 2.063(9) . ? O2 C14 1.214(4) . ? O1 C11 1.216(4) . ? C14 C20 1.486(4) . ? C14 C13 1.499(5) . ? C20 C15 1.395(5) . ? C20 C19 1.397(4) . ? C18 C17 1.390(5) . ? C18 C19 1.395(5) . ? C18 H18 0.9500 . ? C15 C16 1.394(5) . ? C15 H15 0.9500 . ? C11 C19 1.482(5) . ? C11 C12 1.501(5) . ? C12 C13 1.338(5) . ? C16 C17 1.386(5) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C2 C3 1.379(13) . ? C2 C1 1.456(11) . ? C2 C7 1.477(8) . ? C4 C5 1.360(17) . ? C4 C9 1.389(13) . ? C4 C3 1.403(12) 3_757 ? C1 C6 1.338(17) . ? C1 C5 1.451(14) 3_757 ? C3 C4 1.403(12) 3_757 ? C3 C8 1.597(15) . ? C5 C1 1.451(14) 3_757 ? C5 C10 1.490(11) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 Fe1 C4 179.999(1) . 3_757 ? C4 Fe1 C3 139.2(4) . . ? C4 Fe1 C3 40.8(4) 3_757 . ? C4 Fe1 C3 40.8(4) . 3_757 ? C4 Fe1 C3 139.2(4) 3_757 3_757 ? C3 Fe1 C3 179.997(2) . 3_757 ? C4 Fe1 C5 39.3(5) . . ? C4 Fe1 C5 140.7(5) 3_757 . ? C3 Fe1 C5 111.6(4) . . ? C3 Fe1 C5 68.4(4) 3_757 . ? C4 Fe1 C5 140.7(5) . 3_757 ? C4 Fe1 C5 39.3(5) 3_757 3_757 ? C3 Fe1 C5 68.4(4) . 3_757 ? C3 Fe1 C5 111.6(4) 3_757 3_757 ? C5 Fe1 C5 179.998(4) . 3_757 ? C4 Fe1 C2 113.0(3) . . ? C4 Fe1 C2 67.0(3) 3_757 . ? C3 Fe1 C2 39.5(3) . . ? C3 Fe1 C2 140.5(3) 3_757 . ? C5 Fe1 C2 111.4(3) . . ? C5 Fe1 C2 68.6(3) 3_757 . ? C4 Fe1 C2 67.0(3) . 3_757 ? C4 Fe1 C2 113.0(3) 3_757 3_757 ? C3 Fe1 C2 140.5(3) . 3_757 ? C3 Fe1 C2 39.5(3) 3_757 3_757 ? C5 Fe1 C2 68.6(3) . 3_757 ? C5 Fe1 C2 111.4(3) 3_757 3_757 ? C2 Fe1 C2 179.999(3) . 3_757 ? C4 Fe1 C1 67.6(4) . 3_757 ? C4 Fe1 C1 112.4(4) 3_757 3_757 ? C3 Fe1 C1 111.3(4) . 3_757 ? C3 Fe1 C1 68.7(4) 3_757 3_757 ? C5 Fe1 C1 41.3(4) . 3_757 ? C5 Fe1 C1 138.7(4) 3_757 3_757 ? C2 Fe1 C1 138.6(3) . 3_757 ? C2 Fe1 C1 41.4(3) 3_757 3_757 ? C4 Fe1 C1 112.4(4) . . ? C4 Fe1 C1 67.6(4) 3_757 . ? C3 Fe1 C1 68.7(4) . . ? C3 Fe1 C1 111.3(4) 3_757 . ? C5 Fe1 C1 138.7(4) . . ? C5 Fe1 C1 41.3(4) 3_757 . ? C2 Fe1 C1 41.4(3) . . ? C2 Fe1 C1 138.6(3) 3_757 . ? C1 Fe1 C1 180.0(4) 3_757 . ? O2 C14 C20 122.7(3) . . ? O2 C14 C13 120.6(3) . . ? C20 C14 C13 116.7(3) . . ? C15 C20 C19 120.2(3) . . ? C15 C20 C14 118.9(3) . . ? C19 C20 C14 120.9(3) . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C16 C15 C20 119.4(3) . . ? C16 C15 H15 120.3 . . ? C20 C15 H15 120.3 . . ? O1 C11 C19 122.9(3) . . ? O1 C11 C12 120.2(3) . . ? C19 C11 C12 116.9(3) . . ? C13 C12 C11 121.8(3) . . ? C13 C12 Cl1 122.7(3) . . ? C11 C12 Cl1 115.4(2) . . ? C12 C13 C14 122.3(3) . . ? C12 C13 Cl2 122.0(3) . . ? C14 C13 Cl2 115.6(2) . . ? C18 C19 C20 119.9(3) . . ? C18 C19 C11 118.9(3) . . ? C20 C19 C11 121.3(3) . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C3 C2 C1 108.9(7) . . ? C3 C2 C7 125.2(8) . . ? C1 C2 C7 125.9(9) . . ? C3 C2 Fe1 69.1(4) . . ? C1 C2 Fe1 69.6(3) . . ? C7 C2 Fe1 128.0(4) . . ? C5 C4 C9 119.6(14) . . ? C5 C4 C3 111.8(10) . 3_757 ? C9 C4 C3 128.5(16) . 3_757 ? C5 C4 Fe1 72.4(6) . . ? C9 C4 Fe1 126.4(6) . . ? C3 C4 Fe1 70.8(4) 3_757 . ? C6 C1 C5 131.9(11) . 3_757 ? C6 C1 C2 122.7(9) . . ? C5 C1 C2 105.4(10) 3_757 . ? C6 C1 Fe1 125.8(7) . . ? C5 C1 Fe1 68.7(5) 3_757 . ? C2 C1 Fe1 69.0(5) . . ? C2 C3 C4 106.9(10) . 3_757 ? C2 C3 C8 119.3(9) . . ? C4 C3 C8 133.7(12) 3_757 . ? C2 C3 Fe1 71.4(5) . . ? C4 C3 Fe1 68.4(5) 3_757 . ? C8 C3 Fe1 122.1(5) . . ? C4 C5 C1 107.0(8) . 3_757 ? C4 C5 C10 122.5(13) . . ? C1 C5 C10 130.5(14) 3_757 . ? C4 C5 Fe1 68.3(5) . . ? C1 C5 Fe1 70.0(4) 3_757 . ? C10 C5 Fe1 129.0(6) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.674 _refine_diff_density_min -2.016 _refine_diff_density_rms 0.117 #==END # Attachment '- 3.cif' data_OctaCl2NQ_173 _database_code_depnum_ccdc_archive 'CCDC 828944' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; octamethylferrocene-dichloronaphthoquinone complex ; _chemical_name_common 'octamethylferrocene-dichloronaphthoquinone complex' _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 Fe, 2(C10 H4 Cl2 O2)' _chemical_formula_sum 'C38 H34 Cl4 Fe O4' _chemical_formula_weight 750.29 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.846(3) _cell_length_b 8.1681(17) _cell_length_c 15.110(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.016(2) _cell_angle_gamma 90.00 _cell_volume 1699.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 4132 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.36 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6632 _exptl_absorpt_correction_T_max 0.7353 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 9312 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3821 _reflns_number_gt 3240 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^ > 2\s(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^)+(0.0523P)^2^+0.7295P] 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 3821 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6267(2) 0.1260(5) 1.0017(4) 0.1017(14) Uani 1 1 d . . . C2 C 0.6046(2) 0.0520(6) 0.9178(3) 0.0948(14) Uani 1 1 d . . . C3 C 0.6392(4) 0.2968(9) 1.0133(7) 0.181(4) Uani 0.80 1 d P . . H3A H 0.7081 0.3244 1.0133 0.272 Uiso 0.80 1 calc PR . . H3B H 0.6169 0.3297 1.0701 0.272 Uiso 0.80 1 calc PR . . H3C H 0.6013 0.3546 0.9646 0.272 Uiso 0.80 1 calc PR . . C4 C 0.5929(3) 0.1447(8) 0.8318(4) 0.127(2) Uani 0.80 1 d P . . H4A H 0.5694 0.2554 0.8423 0.191 Uiso 0.80 1 calc PR . . H4B H 0.5460 0.0880 0.7893 0.191 Uiso 0.80 1 calc PR . . H4C H 0.6557 0.1512 0.8075 0.191 Uiso 0.80 1 calc PR . . C5 C 0.40009(18) 0.1197(5) 1.0663(2) 0.0804(10) Uani 1 1 d . . . C6 C 0.38003(17) 0.1473(5) 0.9735(2) 0.0768(10) Uani 1 1 d . . . C7 C 0.36335(19) -0.0050(6) 0.9306(3) 0.0875(11) Uani 1 1 d . . . C8 C 0.4198(3) 0.2457(9) 1.1309(4) 0.122(2) Uani 0.80 1 d P . . H8A H 0.4542 0.3356 1.1049 0.183 Uiso 0.80 1 calc PR . . H8B H 0.4602 0.2018 1.1826 0.183 Uiso 0.80 1 calc PR . . H8C H 0.3585 0.2864 1.1496 0.183 Uiso 0.80 1 calc PR . . C9 C 0.3736(3) 0.3058(7) 0.9266(3) 0.1018(17) Uani 0.80 1 d P . . H9A H 0.3910 0.2911 0.8659 0.153 Uiso 0.80 1 calc PR . . H9B H 0.4184 0.3839 0.9584 0.153 Uiso 0.80 1 calc PR . . H9C H 0.3071 0.3477 0.9244 0.153 Uiso 0.80 1 calc PR . . C10 C 0.3400(3) -0.0307(9) 0.8337(3) 0.1122(19) Uani 0.80 1 d P . . H10A H 0.3586 -0.1419 0.8181 0.168 Uiso 0.80 1 calc PR . . H10B H 0.3758 0.0488 0.8011 0.168 Uiso 0.80 1 calc PR . . H10C H 0.2701 -0.0158 0.8177 0.168 Uiso 0.80 1 calc PR . . C12 C 0.14610(12) -0.08253(19) 1.07903(10) 0.0260(3) Uani 1 1 d . . . C13 C 0.16197(12) 0.0859(2) 1.11670(10) 0.0259(3) Uani 1 1 d . . . C14 C 0.14969(12) 0.2201(2) 1.06624(10) 0.0267(3) Uani 1 1 d . . . C15 C 0.11965(12) 0.2113(2) 0.96817(10) 0.0272(3) Uani 1 1 d . . . C16 C 0.07970(13) 0.0312(2) 0.83743(11) 0.0286(3) Uani 1 1 d . . . H16 H 0.0708 0.1264 0.8014 0.034 Uiso 1 1 calc R . . C17 C 0.06701(13) -0.1225(2) 0.79933(11) 0.0317(4) Uani 1 1 d . . . H17 H 0.0499 -0.1325 0.7370 0.038 Uiso 1 1 calc R . . C18 C 0.07915(13) -0.2617(2) 0.85170(12) 0.0324(4) Uani 1 1 d . . . H18 H 0.0705 -0.3667 0.8250 0.039 Uiso 1 1 calc R . . C19 C 0.10386(13) -0.2487(2) 0.94296(11) 0.0294(3) Uani 1 1 d . . . H19 H 0.1112 -0.3444 0.9788 0.035 Uiso 1 1 calc R . . C20 C 0.11782(12) -0.09470(19) 0.98162(10) 0.0244(3) Uani 1 1 d . . . C21 C 0.10562(12) 0.04584(19) 0.92892(10) 0.0242(3) Uani 1 1 d . . . Cl1 Cl 0.19426(4) 0.09580(5) 1.22886(3) 0.03706(13) Uani 1 1 d . . . Cl2 Cl 0.16465(4) 0.41346(5) 1.10888(3) 0.03869(14) Uani 1 1 d . . . Fe1 Fe 0.5000 0.0000 1.0000 0.0734(2) Uani 1 2 d S . . O1 O 0.15546(10) -0.20147(15) 1.12707(8) 0.0363(3) Uani 1 1 d . . . O2 O 0.10700(11) 0.33534(15) 0.92429(8) 0.0422(3) 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 0.0307(14) 0.108(3) 0.171(4) 0.045(3) 0.031(2) 0.0117(15) C2 0.0374(14) 0.145(3) 0.106(3) 0.075(3) 0.0282(16) 0.0267(17) C3 0.061(3) 0.118(5) 0.372(13) 0.036(6) 0.056(5) 0.010(3) C4 0.054(2) 0.200(6) 0.134(4) 0.119(4) 0.042(2) 0.048(3) C5 0.0332(13) 0.137(3) 0.0728(19) 0.030(2) 0.0129(12) 0.0209(15) C6 0.0290(12) 0.121(3) 0.0821(19) 0.047(2) 0.0141(12) 0.0143(14) C7 0.0284(13) 0.133(3) 0.102(3) 0.031(2) 0.0127(14) 0.0129(16) C8 0.056(2) 0.206(7) 0.105(4) 0.007(4) 0.014(2) 0.030(3) C9 0.0439(19) 0.140(4) 0.124(4) 0.070(3) 0.020(2) 0.028(2) C10 0.0334(18) 0.213(6) 0.089(3) -0.009(4) 0.0006(18) 0.018(3) C12 0.0304(8) 0.0241(8) 0.0239(8) 0.0011(6) 0.0048(6) 0.0010(6) C13 0.0315(9) 0.0270(8) 0.0192(7) -0.0020(6) 0.0033(6) -0.0011(6) C14 0.0343(9) 0.0215(7) 0.0247(8) -0.0030(6) 0.0055(6) -0.0016(6) C15 0.0359(9) 0.0238(8) 0.0225(7) 0.0008(6) 0.0056(6) 0.0005(6) C16 0.0358(9) 0.0277(8) 0.0227(8) 0.0012(6) 0.0049(6) 0.0006(7) C17 0.0373(10) 0.0351(9) 0.0229(8) -0.0045(7) 0.0034(7) 0.0006(7) C18 0.0373(9) 0.0274(8) 0.0325(9) -0.0083(7) 0.0041(7) -0.0007(7) C19 0.0347(9) 0.0232(8) 0.0305(8) -0.0005(7) 0.0039(7) 0.0016(7) C20 0.0264(8) 0.0236(8) 0.0236(8) -0.0002(6) 0.0041(6) 0.0019(6) C21 0.0280(8) 0.0227(8) 0.0227(7) -0.0001(6) 0.0059(6) 0.0011(6) Cl1 0.0540(3) 0.0359(2) 0.0203(2) -0.00056(16) -0.00070(17) -0.00251(19) Cl2 0.0633(3) 0.0225(2) 0.0300(2) -0.00531(16) 0.0037(2) -0.00488(19) Fe1 0.0270(2) 0.1123(5) 0.0831(4) 0.0457(4) 0.0167(2) 0.0153(3) O1 0.0542(8) 0.0257(6) 0.0286(6) 0.0065(5) 0.0024(5) 0.0013(6) O2 0.0752(10) 0.0225(6) 0.0285(6) 0.0042(5) 0.0037(6) 0.0009(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.410(6) . ? C1 C3 1.414(8) . ? C1 C7 1.418(5) 3_657 ? C2 C5 1.425(6) 3_657 ? C2 C4 1.498(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.420(4) . ? C5 C8 1.425(7) . ? C5 C2 1.425(6) 3_657 ? C6 C7 1.410(5) . ? C6 C9 1.473(5) . ? C7 C1 1.418(5) 3_657 ? C7 C10 1.482(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 O1 1.211(2) . ? C12 C20 1.486(2) . ? C12 C13 1.496(2) . ? C13 C14 1.337(2) . ? C13 Cl1 1.7086(16) . ? C14 C15 1.498(2) . ? C14 Cl2 1.7098(16) . ? C15 O2 1.213(2) . ? C15 C21 1.481(2) . ? C16 C17 1.384(2) . ? C16 C21 1.396(2) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(2) . ? C18 H18 0.9500 . ? C19 C20 1.392(2) . ? C19 H19 0.9500 . ? C20 C21 1.397(2) . ? 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 C1 C3 123.2(6) . . ? C2 C1 C7 110.2(4) . 3_657 ? C3 C1 C7 126.7(6) . 3_657 ? C1 C2 C5 106.3(3) . 3_657 ? C1 C2 C4 123.9(5) . . ? C5 C2 C4 129.8(5) 3_657 . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C8 124.4(4) . . ? C6 C5 C2 108.4(4) . 3_657 ? C8 C5 C2 127.2(4) . 3_657 ? C7 C6 C5 108.6(3) . . ? C7 C6 C9 123.8(4) . . ? C5 C6 C9 127.6(4) . . ? C6 C7 C1 106.6(4) . 3_657 ? C6 C7 C10 125.9(4) . . ? C1 C7 C10 127.5(5) 3_657 . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C12 C20 122.70(15) . . ? O1 C12 C13 120.48(14) . . ? C20 C12 C13 116.82(13) . . ? C14 C13 C12 122.19(14) . . ? C14 C13 Cl1 122.09(13) . . ? C12 C13 Cl1 115.71(12) . . ? C13 C14 C15 122.03(14) . . ? C13 C14 Cl2 122.67(13) . . ? C15 C14 Cl2 115.29(12) . . ? O2 C15 C21 122.54(14) . . ? O2 C15 C14 120.63(15) . . ? C21 C15 C14 116.82(13) . . ? C17 C16 C21 119.84(15) . . ? C17 C16 H16 120.1 . . ? C21 C16 H16 120.1 . . ? C16 C17 C18 120.26(15) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C19 120.46(16) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 119.62(15) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C21 120.01(15) . . ? C19 C20 C12 119.12(14) . . ? C21 C20 C12 120.86(14) . . ? C16 C21 C20 119.80(15) . . ? C16 C21 C15 118.95(14) . . ? C20 C21 C15 121.25(14) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.382 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.058