# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1684 data_sa1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 B2 Fe2 O8' _chemical_formula_weight 513.62 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4542(3) _cell_length_b 12.2543(4) _cell_length_c 12.4180(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.604(3) _cell_angle_gamma 90.00 _cell_volume 980.22(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 1.528 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.6570 _exptl_absorpt_correction_T_max 0.8032 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method '2o phi+omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6704 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2243 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _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^)+(0.0147P)^2^+0.6970P] 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 SHELXL _refine_ls_extinction_coef 0.0030(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2243 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.12514(4) 0.789984(19) 0.674843(18) 0.01364(10) Uani 1 1 d . . . O1 O 0.47936(17) 0.88863(10) 0.81029(9) 0.0157(3) Uani 1 1 d . . . C1 C 0.5110(3) 0.94734(13) 0.90562(12) 0.0137(3) Uani 1 1 d . . . B1 B 0.2668(3) 0.86281(15) 0.80039(15) 0.0148(4) Uani 1 1 d . . . O2 O 0.17062(17) 0.90341(10) 0.89064(9) 0.0159(3) Uani 1 1 d . . . C2 C 0.3244(2) 0.95675(13) 0.95408(13) 0.0135(3) Uani 1 1 d . . . O3 O -0.0629(2) 0.64397(12) 0.82532(11) 0.0342(4) Uani 1 1 d . . . C3 C 0.3033(3) 1.01020(14) 1.05074(13) 0.0160(3) Uani 1 1 d . . . H3 H 0.180(4) 1.0161(18) 1.0830(17) 0.033(6) Uiso 1 1 d . . . O4 O 0.4961(2) 0.65821(11) 0.66435(11) 0.0293(3) Uani 1 1 d . . . C4 C 0.0596(3) 0.95285(15) 0.63459(14) 0.0211(4) Uani 1 1 d . . . H4 H 0.093(3) 1.0136(18) 0.6782(16) 0.023(5) Uiso 1 1 d . . . C5 C 0.1828(3) 0.90545(15) 0.55668(14) 0.0204(4) Uani 1 1 d . . . H5 H 0.315(3) 0.9279(17) 0.5412(16) 0.023(5) Uiso 1 1 d . . . C6 C 0.0694(3) 0.81685(15) 0.50733(13) 0.0206(4) Uani 1 1 d . . . H6 H 0.114(3) 0.7676(19) 0.4538(18) 0.032(6) Uiso 1 1 d . . . C7 C -0.1216(3) 0.80913(16) 0.55588(14) 0.0211(4) Uani 1 1 d . . . H7 H -0.223(3) 0.7594(18) 0.5403(16) 0.023(5) Uiso 1 1 d . . . C8 C -0.1272(3) 0.89296(16) 0.63539(14) 0.0219(4) Uani 1 1 d . . . H8 H -0.234(3) 0.9043(17) 0.6791(18) 0.029(6) Uiso 1 1 d . . . C9 C 0.0089(3) 0.70169(15) 0.76492(14) 0.0212(4) Uani 1 1 d . . . C10 C 0.3478(3) 0.70937(14) 0.66775(14) 0.0190(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 0.01480(15) 0.01382(15) 0.01247(14) -0.00021(9) 0.00221(9) -0.00051(9) O1 0.0136(6) 0.0201(6) 0.0138(5) -0.0045(5) 0.0034(4) -0.0010(5) C1 0.0159(8) 0.0142(8) 0.0113(7) -0.0008(6) 0.0028(6) 0.0018(6) B1 0.0152(9) 0.0139(9) 0.0154(9) 0.0023(7) 0.0023(7) 0.0010(7) O2 0.0121(6) 0.0203(6) 0.0153(6) -0.0034(5) 0.0014(4) -0.0012(5) C2 0.0116(8) 0.0142(8) 0.0146(7) 0.0006(6) 0.0012(6) -0.0006(6) O3 0.0380(9) 0.0363(8) 0.0293(8) 0.0101(6) 0.0097(6) -0.0105(7) C3 0.0131(8) 0.0197(9) 0.0156(8) -0.0004(7) 0.0045(6) 0.0008(7) O4 0.0241(7) 0.0242(7) 0.0400(8) -0.0029(6) 0.0057(6) 0.0073(6) C4 0.0322(11) 0.0143(9) 0.0161(8) -0.0004(7) -0.0038(7) 0.0024(7) C5 0.0233(10) 0.0197(9) 0.0182(8) 0.0052(7) 0.0023(7) -0.0025(7) C6 0.0295(10) 0.0204(9) 0.0119(8) -0.0008(7) 0.0017(7) 0.0014(8) C7 0.0200(9) 0.0240(9) 0.0186(9) 0.0021(7) -0.0045(7) -0.0028(8) C8 0.0204(9) 0.0282(10) 0.0172(8) 0.0022(7) 0.0014(7) 0.0076(8) C9 0.0214(9) 0.0223(10) 0.0200(9) -0.0012(7) 0.0015(7) -0.0012(7) C10 0.0247(10) 0.0154(8) 0.0172(8) -0.0019(7) 0.0038(7) -0.0048(7) _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 C10 1.7507(19) . ? Fe1 C9 1.7580(19) . ? Fe1 B1 1.9708(19) . ? Fe1 C5 2.0887(18) . ? Fe1 C8 2.0938(18) . ? Fe1 C4 2.0942(18) . ? Fe1 C6 2.1145(17) . ? Fe1 C7 2.1160(18) . ? O1 C1 1.3894(19) . ? O1 B1 1.406(2) . ? C1 C2 1.385(2) . ? C1 C3 1.385(2) 3_677 ? B1 O2 1.406(2) . ? O2 C2 1.3909(19) . ? C2 C3 1.382(2) . ? O3 C9 1.149(2) . ? C3 C1 1.385(2) 3_677 ? O4 C10 1.147(2) . ? C4 C8 1.412(3) . ? C4 C5 1.415(3) . ? C5 C6 1.426(3) . ? C6 C7 1.409(3) . ? C7 C8 1.427(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Fe1 C9 93.97(8) . . ? C10 Fe1 B1 87.35(8) . . ? C9 Fe1 B1 88.32(8) . . ? C10 Fe1 C5 99.43(8) . . ? C9 Fe1 C5 165.02(8) . . ? B1 Fe1 C5 98.90(7) . . ? C10 Fe1 C8 163.17(8) . . ? C9 Fe1 C8 99.38(8) . . ? B1 Fe1 C8 103.15(8) . . ? C5 Fe1 C8 66.28(8) . . ? C10 Fe1 C4 132.84(8) . . ? C9 Fe1 C4 130.58(8) . . ? B1 Fe1 C4 80.44(7) . . ? C5 Fe1 C4 39.55(7) . . ? C8 Fe1 C4 39.40(8) . . ? C10 Fe1 C6 97.34(8) . . ? C9 Fe1 C6 131.97(8) . . ? B1 Fe1 C6 138.55(8) . . ? C5 Fe1 C6 39.66(7) . . ? C8 Fe1 C6 66.06(7) . . ? C4 Fe1 C6 66.26(7) . . ? C10 Fe1 C7 127.70(8) . . ? C9 Fe1 C7 100.36(8) . . ? B1 Fe1 C7 142.51(8) . . ? C5 Fe1 C7 66.05(7) . . ? C8 Fe1 C7 39.62(7) . . ? C4 Fe1 C7 66.16(7) . . ? C6 Fe1 C7 38.91(7) . . ? C1 O1 B1 106.35(13) . . ? C2 C1 C3 123.61(15) . 3_677 ? C2 C1 O1 109.15(14) . . ? C3 C1 O1 127.23(15) 3_677 . ? O2 B1 O1 109.15(14) . . ? O2 B1 Fe1 125.79(13) . . ? O1 B1 Fe1 124.94(12) . . ? C2 O2 B1 106.42(13) . . ? C3 C2 C1 123.57(15) . . ? C3 C2 O2 127.52(15) . . ? C1 C2 O2 108.90(14) . . ? C2 C3 C1 112.81(15) . 3_677 ? C8 C4 C5 107.95(16) . . ? C8 C4 Fe1 70.28(10) . . ? C5 C4 Fe1 70.01(10) . . ? C4 C5 C6 108.11(17) . . ? C4 C5 Fe1 70.43(10) . . ? C6 C5 Fe1 71.14(10) . . ? C7 C6 C5 107.85(16) . . ? C7 C6 Fe1 70.60(10) . . ? C5 C6 Fe1 69.19(10) . . ? C6 C7 C8 107.97(17) . . ? C6 C7 Fe1 70.49(10) . . ? C8 C7 Fe1 69.35(10) . . ? C4 C8 C7 108.10(16) . . ? C4 C8 Fe1 70.31(10) . . ? C7 C8 Fe1 71.03(11) . . ? O3 C9 Fe1 178.40(17) . . ? O4 C10 Fe1 178.52(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 O1 C1 C2 0.60(18) . . . . ? B1 O1 C1 C3 179.70(17) . . . 3_677 ? C1 O1 B1 O2 -1.39(18) . . . . ? C1 O1 B1 Fe1 174.84(12) . . . . ? C10 Fe1 B1 O2 -146.00(16) . . . . ? C9 Fe1 B1 O2 -51.95(16) . . . . ? C5 Fe1 B1 O2 114.87(15) . . . . ? C8 Fe1 B1 O2 47.29(16) . . . . ? C4 Fe1 B1 O2 79.73(15) . . . . ? C6 Fe1 B1 O2 115.89(15) . . . . ? C7 Fe1 B1 O2 53.0(2) . . . . ? C10 Fe1 B1 O1 38.39(15) . . . . ? C9 Fe1 B1 O1 132.44(16) . . . . ? C5 Fe1 B1 O1 -60.75(16) . . . . ? C8 Fe1 B1 O1 -128.32(15) . . . . ? C4 Fe1 B1 O1 -95.88(15) . . . . ? C6 Fe1 B1 O1 -59.7(2) . . . . ? C7 Fe1 B1 O1 -122.64(16) . . . . ? O1 B1 O2 C2 1.63(17) . . . . ? Fe1 B1 O2 C2 -174.56(13) . . . . ? C3 C1 C2 C3 0.5(3) 3_677 . . . ? O1 C1 C2 C3 179.63(15) . . . . ? C3 C1 C2 O2 -178.73(15) 3_677 . . . ? O1 C1 C2 O2 0.41(18) . . . . ? B1 O2 C2 C3 179.57(17) . . . . ? B1 O2 C2 C1 -1.25(17) . . . . ? C1 C2 C3 C1 -0.4(3) . . . 3_677 ? O2 C2 C3 C1 178.63(15) . . . 3_677 ? C10 Fe1 C4 C8 158.07(11) . . . . ? C9 Fe1 C4 C8 -45.20(14) . . . . ? B1 Fe1 C4 C8 -124.64(11) . . . . ? C5 Fe1 C4 C8 118.60(15) . . . . ? C6 Fe1 C4 C8 80.62(11) . . . . ? C7 Fe1 C4 C8 37.93(10) . . . . ? C10 Fe1 C4 C5 39.46(15) . . . . ? C9 Fe1 C4 C5 -163.81(12) . . . . ? B1 Fe1 C4 C5 116.76(12) . . . . ? C8 Fe1 C4 C5 -118.60(15) . . . . ? C6 Fe1 C4 C5 -37.99(11) . . . . ? C7 Fe1 C4 C5 -80.68(12) . . . . ? C8 C4 C5 C6 1.2(2) . . . . ? Fe1 C4 C5 C6 61.50(12) . . . . ? C8 C4 C5 Fe1 -60.32(12) . . . . ? C10 Fe1 C5 C4 -151.81(11) . . . . ? C9 Fe1 C5 C4 55.0(3) . . . . ? B1 Fe1 C5 C4 -63.03(12) . . . . ? C8 Fe1 C5 C4 37.50(11) . . . . ? C6 Fe1 C5 C4 118.03(16) . . . . ? C7 Fe1 C5 C4 80.99(12) . . . . ? C10 Fe1 C5 C6 90.16(12) . . . . ? C9 Fe1 C5 C6 -63.0(3) . . . . ? B1 Fe1 C5 C6 178.93(11) . . . . ? C8 Fe1 C5 C6 -80.54(12) . . . . ? C4 Fe1 C5 C6 -118.03(16) . . . . ? C7 Fe1 C5 C6 -37.04(11) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? Fe1 C5 C6 C7 60.29(12) . . . . ? C4 C5 C6 Fe1 -61.05(12) . . . . ? C10 Fe1 C6 C7 145.29(12) . . . . ? C9 Fe1 C6 C7 43.18(15) . . . . ? B1 Fe1 C6 C7 -120.37(13) . . . . ? C5 Fe1 C6 C7 -118.78(16) . . . . ? C8 Fe1 C6 C7 -37.65(11) . . . . ? C4 Fe1 C6 C7 -80.90(12) . . . . ? C10 Fe1 C6 C5 -95.93(12) . . . . ? C9 Fe1 C6 C5 161.96(12) . . . . ? B1 Fe1 C6 C5 -1.59(17) . . . . ? C8 Fe1 C6 C5 81.13(12) . . . . ? C4 Fe1 C6 C5 37.88(11) . . . . ? C7 Fe1 C6 C5 118.78(16) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? Fe1 C6 C7 C8 59.45(12) . . . . ? C5 C6 C7 Fe1 -59.40(12) . . . . ? C10 Fe1 C7 C6 -45.54(14) . . . . ? C9 Fe1 C7 C6 -148.86(12) . . . . ? B1 Fe1 C7 C6 110.22(14) . . . . ? C5 Fe1 C7 C6 37.75(11) . . . . ? C8 Fe1 C7 C6 118.91(16) . . . . ? C4 Fe1 C7 C6 81.18(12) . . . . ? C10 Fe1 C7 C8 -164.45(11) . . . . ? C9 Fe1 C7 C8 92.23(12) . . . . ? B1 Fe1 C7 C8 -8.68(18) . . . . ? C5 Fe1 C7 C8 -81.16(12) . . . . ? C4 Fe1 C7 C8 -37.72(11) . . . . ? C6 Fe1 C7 C8 -118.91(16) . . . . ? C5 C4 C8 C7 -1.2(2) . . . . ? Fe1 C4 C8 C7 -61.30(12) . . . . ? C5 C4 C8 Fe1 60.15(12) . . . . ? C6 C7 C8 C4 0.7(2) . . . . ? Fe1 C7 C8 C4 60.85(12) . . . . ? C6 C7 C8 Fe1 -60.16(13) . . . . ? C10 Fe1 C8 C4 -71.1(3) . . . . ? C9 Fe1 C8 C4 146.89(11) . . . . ? B1 Fe1 C8 C4 56.43(12) . . . . ? C5 Fe1 C8 C4 -37.64(10) . . . . ? C6 Fe1 C8 C4 -81.17(11) . . . . ? C7 Fe1 C8 C4 -118.16(15) . . . . ? C10 Fe1 C8 C7 47.1(3) . . . . ? C9 Fe1 C8 C7 -94.95(12) . . . . ? B1 Fe1 C8 C7 174.58(11) . . . . ? C5 Fe1 C8 C7 80.52(12) . . . . ? C4 Fe1 C8 C7 118.16(15) . . . . ? C6 Fe1 C8 C7 36.98(11) . . . . ? C10 Fe1 C9 O3 50(6) . . . . ? B1 Fe1 C9 O3 -37(6) . . . . ? C5 Fe1 C9 O3 -156(6) . . . . ? C8 Fe1 C9 O3 -140(6) . . . . ? C4 Fe1 C9 O3 -113(6) . . . . ? C6 Fe1 C9 O3 154(6) . . . . ? C7 Fe1 C9 O3 180(100) . . . . ? C9 Fe1 C10 O4 -109(7) . . . . ? B1 Fe1 C10 O4 -21(7) . . . . ? C5 Fe1 C10 O4 78(7) . . . . ? C8 Fe1 C10 O4 108(7) . . . . ? C4 Fe1 C10 O4 53(7) . . . . ? C6 Fe1 C10 O4 118(7) . . . . ? C7 Fe1 C10 O4 144(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.331 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.060