# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Patra, Malay' 'Merz, Klaus' 'Metzler-Nolte, Nils' _publ_contact_author_name 'Metzler-Nolte, Nils' _publ_contact_author_email nils.metzler-nolte@rub.de _publ_section_title ; Planar Chiral (e6-arene)Cr(CO)3 Containing Carboxylic Acid Derivatives: Synthesis and Use in the Preparation of Organometallic Analogues of the Antibiotic Platensimycin ; # Attachment '- compound_7.cif' data_shelx _database_code_depnum_ccdc_archive 'CCDC 826249' #TrackingRef '- compound_7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Cl3 Cr N0 O6' _chemical_formula_weight 487.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cr Cr 0.3209 0.6236 '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' _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 6.544(11) _cell_length_b 10.621(19) _cell_length_c 14.77(3) _cell_angle_alpha 88.23(5) _cell_angle_beta 82.95(3) _cell_angle_gamma 87.18(5) _cell_volume 1017(3) _cell_formula_units_Z 2 _cell_measurement_temperature 446(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.989 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9076 _exptl_absorpt_correction_T_max 0.9076 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 446(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4650 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3556 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0545P)^2^+1.5758P] 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 3556 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Cr1 Cr 0.41838(10) 0.22675(7) 0.57628(5) 0.0276(2) Uani 1 1 d . . . O4 O 0.2602(5) 0.3470(3) 0.9050(2) 0.0392(8) Uani 1 1 d . . . O3 O 0.6960(5) 0.0391(3) 0.6633(2) 0.0426(8) Uani 1 1 d . . . C3 C 0.1427(6) 0.3450(4) 0.6343(3) 0.0303(10) Uani 1 1 d . . . O2 O 0.6752(5) 0.4408(3) 0.6151(3) 0.0524(10) Uani 1 1 d . . . O1 O 0.7058(5) 0.1995(4) 0.4016(2) 0.0536(10) Uani 1 1 d . . . C13 C -0.2065(7) 0.2619(4) 0.9191(3) 0.0341(11) Uani 1 1 d . . . H13A H -0.3404 0.2256 0.9323 0.041 Uiso 1 1 calc R . . H13B H -0.1139 0.2173 0.9569 0.041 Uiso 1 1 calc R . . O5 O -0.2972(6) 0.4129(3) 1.0325(2) 0.0462(9) Uani 1 1 d . . . C14 C -0.2267(7) 0.3988(4) 0.9450(3) 0.0324(10) Uani 1 1 d . . . C10 C 0.1153(7) 0.2335(4) 0.7918(3) 0.0283(9) Uani 1 1 d . . . O6 O -0.1867(6) 0.4857(3) 0.8926(2) 0.0522(10) Uani 1 1 d . . . C4 C 0.1441(6) 0.2322(4) 0.6871(3) 0.0278(9) Uani 1 1 d . . . C7 C 0.1261(8) 0.4692(4) 0.6831(3) 0.0386(11) Uani 1 1 d . . . H7A H 0.1831 0.5342 0.6412 0.046 Uiso 1 1 calc R . . H7B H -0.0183 0.4922 0.7005 0.046 Uiso 1 1 calc R . . C5 C 0.1580(6) 0.1158(4) 0.6404(3) 0.0319(10) Uani 1 1 d . . . H5A H 0.1889 0.0377 0.6742 0.038 Uiso 1 1 calc R . . C11 C 0.2084(8) 0.1153(4) 0.8368(3) 0.0395(11) Uani 1 1 d . . . H11A H 0.3552 0.1112 0.8207 0.059 Uiso 1 1 calc R . . H11B H 0.1513 0.0416 0.8158 0.059 Uiso 1 1 calc R . . H11C H 0.1770 0.1194 0.9019 0.059 Uiso 1 1 calc R . . C16 C 0.5767(7) 0.3569(5) 0.6004(3) 0.0360(11) Uani 1 1 d . . . C12 C -0.1257(7) 0.2412(4) 0.8186(3) 0.0339(10) Uani 1 1 d . . . H12A H -0.1826 0.3093 0.7827 0.041 Uiso 1 1 calc R . . H12B H -0.1798 0.1636 0.8006 0.041 Uiso 1 1 calc R . . C9 C 0.2076(6) 0.3501(4) 0.8275(3) 0.0304(10) Uani 1 1 d . . . C17 C 0.5901(7) 0.1128(4) 0.6305(3) 0.0321(10) Uani 1 1 d . . . C2 C 0.1481(7) 0.3408(5) 0.5378(3) 0.0386(11) Uani 1 1 d . . . H2A H 0.1711 0.4185 0.5012 0.046 Uiso 1 1 calc R . . C15 C 0.5925(7) 0.2093(5) 0.4692(3) 0.0380(11) Uani 1 1 d . . . C8 C 0.2367(7) 0.4656(4) 0.7674(3) 0.0360(11) Uani 1 1 d . . . H8A H 0.3830 0.4726 0.7483 0.043 Uiso 1 1 calc R . . H8B H 0.1897 0.5388 0.8032 0.043 Uiso 1 1 calc R . . C1 C 0.1586(7) 0.2252(6) 0.4930(3) 0.0468(14) Uani 1 1 d . . . H1A H 0.1860 0.2235 0.4263 0.056 Uiso 1 1 calc R . . C6 C 0.1619(7) 0.1115(5) 0.5452(3) 0.0415(12) Uani 1 1 d . . . H6A H 0.1931 0.0312 0.5144 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.3603(3) 0.09239(14) 0.08755(10) 0.0678(5) Uani 1 1 d . . . Cl2 Cl 0.0306(3) 0.21516(15) 0.20401(19) 0.1041(9) Uani 1 1 d . . . Cl3 Cl 0.4472(3) 0.24822(19) 0.23278(12) 0.0890(7) Uani 1 1 d . . . C18 C 0.2830(8) 0.2289(5) 0.1502(4) 0.0449(12) Uani 1 1 d . . . H15A H 0.2877 0.3026 0.1085 0.054 Uiso 1 1 calc R . . H1 H -0.326(11) 0.485(7) 1.056(5) 0.09(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 Cr1 0.0186(4) 0.0374(4) 0.0268(4) -0.0051(3) -0.0021(3) -0.0005(3) O4 0.045(2) 0.0411(18) 0.0349(18) -0.0093(15) -0.0145(15) -0.0014(16) O3 0.0309(18) 0.048(2) 0.049(2) 0.0013(17) -0.0095(16) 0.0036(17) C3 0.016(2) 0.036(2) 0.037(2) -0.005(2) 0.0005(18) 0.0056(18) O2 0.037(2) 0.049(2) 0.074(3) -0.0009(19) -0.0090(18) -0.0160(18) O1 0.040(2) 0.082(3) 0.0360(19) -0.0053(19) 0.0078(17) 0.0031(19) C13 0.034(3) 0.034(2) 0.032(2) -0.004(2) 0.007(2) -0.010(2) O5 0.064(3) 0.042(2) 0.0319(19) -0.0130(16) 0.0011(17) -0.0036(19) C14 0.026(2) 0.036(3) 0.034(2) -0.008(2) 0.0026(19) -0.003(2) C10 0.028(2) 0.027(2) 0.030(2) -0.0044(18) -0.0010(18) -0.0026(19) O6 0.067(3) 0.0316(18) 0.052(2) 0.0023(17) 0.0131(19) 0.0016(18) C4 0.016(2) 0.038(2) 0.029(2) -0.0085(19) 0.0009(17) -0.0022(18) C7 0.038(3) 0.035(2) 0.042(3) 0.004(2) -0.003(2) 0.002(2) C5 0.019(2) 0.035(2) 0.040(3) -0.008(2) 0.0054(18) -0.0035(19) C11 0.051(3) 0.031(2) 0.036(3) -0.004(2) -0.008(2) 0.005(2) C16 0.020(2) 0.043(3) 0.043(3) 0.001(2) -0.002(2) 0.004(2) C12 0.027(2) 0.040(3) 0.034(2) -0.008(2) 0.0007(19) -0.006(2) C9 0.021(2) 0.033(2) 0.037(3) -0.010(2) -0.0008(19) 0.0028(19) C17 0.022(2) 0.040(3) 0.034(2) -0.009(2) 0.0010(19) -0.005(2) C2 0.022(2) 0.057(3) 0.036(3) 0.009(2) -0.0037(19) 0.005(2) C15 0.026(2) 0.052(3) 0.036(3) -0.007(2) -0.005(2) 0.000(2) C8 0.036(3) 0.028(2) 0.043(3) -0.010(2) -0.001(2) -0.002(2) C1 0.017(2) 0.095(4) 0.030(3) -0.017(3) -0.0064(19) 0.001(3) C6 0.022(2) 0.057(3) 0.047(3) -0.027(3) 0.001(2) -0.008(2) Cl1 0.1024(13) 0.0486(8) 0.0479(8) -0.0028(7) 0.0028(8) 0.0146(8) Cl2 0.0458(9) 0.0433(8) 0.212(3) -0.0090(12) 0.0272(12) 0.0006(7) Cl3 0.1118(15) 0.1010(14) 0.0628(10) 0.0115(10) -0.0259(10) -0.0624(13) C18 0.049(3) 0.034(3) 0.050(3) 0.000(2) -0.002(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cr1 C16 1.837(6) . ? Cr1 C15 1.840(5) . ? Cr1 C17 1.843(5) . ? Cr1 C2 2.216(5) . ? Cr1 C1 2.218(5) . ? Cr1 C5 2.218(5) . ? Cr1 C6 2.225(5) . ? Cr1 C3 2.243(5) . ? Cr1 C4 2.275(5) . ? O4 C9 1.233(6) . ? O3 C17 1.155(6) . ? C3 C4 1.410(6) . ? C3 C2 1.423(7) . ? C3 C7 1.515(7) . ? O2 C16 1.165(6) . ? O1 C15 1.173(6) . ? C13 C14 1.510(7) . ? C13 C12 1.533(6) . ? O5 C14 1.328(6) . ? C14 O6 1.204(6) . ? C10 C4 1.535(6) . ? C10 C11 1.536(6) . ? C10 C9 1.539(6) . ? C10 C12 1.577(6) . ? C4 C5 1.428(6) . ? C7 C8 1.514(7) . ? C5 C6 1.405(7) . ? C9 C8 1.498(7) . ? C2 C1 1.407(8) . ? C1 C6 1.412(8) . ? Cl1 C18 1.763(6) . ? Cl2 C18 1.754(6) . ? Cl3 C18 1.745(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 Cr1 C15 86.5(2) . . ? C16 Cr1 C17 90.6(2) . . ? C15 Cr1 C17 88.2(2) . . ? C16 Cr1 C2 98.2(2) . . ? C15 Cr1 C2 104.9(2) . . ? C17 Cr1 C2 164.59(18) . . ? C16 Cr1 C1 130.1(2) . . ? C15 Cr1 C1 87.3(2) . . ? C17 Cr1 C1 138.6(2) . . ? C2 Cr1 C1 37.0(2) . . ? C16 Cr1 C5 140.8(2) . . ? C15 Cr1 C5 132.4(2) . . ? C17 Cr1 C5 87.1(2) . . ? C2 Cr1 C5 78.1(2) . . ? C1 Cr1 C5 66.6(2) . . ? C16 Cr1 C6 164.4(2) . . ? C15 Cr1 C6 99.7(2) . . ? C17 Cr1 C6 103.8(2) . . ? C2 Cr1 C6 66.4(2) . . ? C1 Cr1 C6 37.1(2) . . ? C5 Cr1 C6 36.87(19) . . ? C16 Cr1 C3 87.3(2) . . ? C15 Cr1 C3 139.8(2) . . ? C17 Cr1 C3 131.6(2) . . ? C2 Cr1 C3 37.21(18) . . ? C1 Cr1 C3 67.1(2) . . ? C5 Cr1 C3 66.1(2) . . ? C6 Cr1 C3 78.7(2) . . ? C16 Cr1 C4 105.5(2) . . ? C15 Cr1 C4 165.73(18) . . ? C17 Cr1 C4 99.3(2) . . ? C2 Cr1 C4 66.23(19) . . ? C1 Cr1 C4 79.0(2) . . ? C5 Cr1 C4 37.03(16) . . ? C6 Cr1 C4 66.80(19) . . ? C3 Cr1 C4 36.35(17) . . ? C4 C3 C2 120.1(4) . . ? C4 C3 C7 118.4(4) . . ? C2 C3 C7 121.4(4) . . ? C4 C3 Cr1 73.1(3) . . ? C2 C3 Cr1 70.4(3) . . ? C7 C3 Cr1 131.2(3) . . ? C14 C13 C12 113.9(4) . . ? O6 C14 O5 123.5(4) . . ? O6 C14 C13 124.3(4) . . ? O5 C14 C13 112.2(4) . . ? C4 C10 C11 113.7(4) . . ? C4 C10 C9 111.6(4) . . ? C11 C10 C9 108.3(4) . . ? C4 C10 C12 104.4(3) . . ? C11 C10 C12 109.7(4) . . ? C9 C10 C12 109.1(3) . . ? C3 C4 C5 117.9(4) . . ? C3 C4 C10 121.3(4) . . ? C5 C4 C10 120.6(4) . . ? C3 C4 Cr1 70.6(2) . . ? C5 C4 Cr1 69.3(2) . . ? C10 C4 Cr1 135.5(3) . . ? C8 C7 C3 113.4(4) . . ? C6 C5 C4 122.0(5) . . ? C6 C5 Cr1 71.8(3) . . ? C4 C5 Cr1 73.6(3) . . ? O2 C16 Cr1 178.9(4) . . ? C13 C12 C10 117.4(4) . . ? O4 C9 C8 120.4(4) . . ? O4 C9 C10 119.7(4) . . ? C8 C9 C10 119.8(4) . . ? O3 C17 Cr1 178.3(4) . . ? C1 C2 C3 121.2(5) . . ? C1 C2 Cr1 71.5(3) . . ? C3 C2 Cr1 72.4(3) . . ? O1 C15 Cr1 178.9(4) . . ? C9 C8 C7 115.4(4) . . ? C2 C1 C6 119.2(4) . . ? C2 C1 Cr1 71.4(3) . . ? C6 C1 Cr1 71.8(3) . . ? C5 C6 C1 119.5(4) . . ? C5 C6 Cr1 71.3(3) . . ? C1 C6 Cr1 71.2(3) . . ? Cl3 C18 Cl2 109.1(3) . . ? Cl3 C18 Cl1 110.2(3) . . ? Cl2 C18 Cl1 109.6(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.074 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.082 # Attachment '- compound_8.cif' data_x101125-ii _database_code_depnum_ccdc_archive 'CCDC 826250' #TrackingRef '- compound_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Cr N0 O6' _chemical_formula_weight 368.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cr Cr 0.3209 0.6236 '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 8.523(19) _cell_length_b 12.07(2) _cell_length_c 15.87(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.22(2) _cell_angle_gamma 90.00 _cell_volume 1607(6) _cell_formula_units_Z 4 _cell_measurement_temperature 446(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9295 _exptl_absorpt_correction_T_max 0.9295 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 446(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 3461 _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_sigmaI/netI 0.1790 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2080 _reflns_number_gt 1166 _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^)+(0.0234P)^2^+5.9646P] 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 2080 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1668 _refine_ls_R_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1396 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cr52 Cr 0.9538(2) 0.17876(14) 0.40012(9) 0.0327(5) Uani 1 1 d . . . C13 C 0.4645(12) 0.2048(8) 0.1464(6) 0.037(3) Uani 1 1 d . . . H13A H 0.3638 0.1964 0.1661 0.045 Uiso 1 1 calc R . . H13B H 0.4637 0.2762 0.1182 0.045 Uiso 1 1 calc R . . O5 O 0.3586(9) 0.0655(6) 0.0445(4) 0.047(2) Uani 1 1 d . . . O2 O 1.0685(8) 0.2024(6) 0.2330(4) 0.042(2) Uani 1 1 d . . . C11 C 0.4340(11) 0.3126(9) 0.3152(6) 0.042(3) Uani 1 1 d . . . H11A H 0.4347 0.3737 0.3539 0.062 Uiso 1 1 calc R . . H11B H 0.4096 0.2455 0.3427 0.062 Uiso 1 1 calc R . . H11C H 0.3548 0.3252 0.2650 0.062 Uiso 1 1 calc R . . O3 O 0.8726(9) -0.0543(7) 0.3454(5) 0.048(2) Uani 1 1 d . . . O6 O 0.6230(9) 0.0930(6) 0.0709(4) 0.049(2) Uani 1 1 d . . . H6A H 0.6200 0.0439 0.0350 0.073 Uiso 1 1 calc R . . O1 O 0.5293(9) 0.4637(6) 0.2035(5) 0.052(2) Uani 1 1 d . . . C12 C 0.6024(12) 0.2023(8) 0.2245(5) 0.034(3) Uani 1 1 d . . . H12A H 0.7030 0.2037 0.2040 0.041 Uiso 1 1 calc R . . H12B H 0.5972 0.1332 0.2550 0.041 Uiso 1 1 calc R . . O4 O 1.2902(10) 0.1083(7) 0.4742(5) 0.058(2) Uani 1 1 d . . . C15 C 1.0244(11) 0.1950(8) 0.2982(6) 0.029(2) Uani 1 1 d . . . C10 C 0.5994(12) 0.3019(8) 0.2892(5) 0.029(3) Uani 1 1 d . . . C2 C 0.9696(13) 0.3370(9) 0.4717(6) 0.040(3) Uani 1 1 d . . . H2A H 1.0709 0.3774 0.4832 0.048 Uiso 1 1 calc R . . C4 C 0.8088(14) 0.1816(10) 0.5064(5) 0.043(3) Uani 1 1 d . . . H4A H 0.8027 0.1150 0.5408 0.052 Uiso 1 1 calc R . . C8 C 0.8077(12) 0.4296(8) 0.2416(6) 0.037(3) Uani 1 1 d . . . H8A H 0.8193 0.4959 0.2087 0.044 Uiso 1 1 calc R . . H8B H 0.8542 0.3681 0.2153 0.044 Uiso 1 1 calc R . . C16 C 0.9019(13) 0.0366(10) 0.3696(6) 0.036(3) Uani 1 1 d . . . C14 C 0.4801(14) 0.1145(9) 0.0828(6) 0.031(3) Uani 1 1 d . . . C5 C 0.7014(13) 0.1945(9) 0.4263(5) 0.039(3) Uani 1 1 d . . . H5A H 0.6224 0.1369 0.4064 0.047 Uiso 1 1 calc R . . C6 C 0.7301(12) 0.2824(8) 0.3689(6) 0.034(3) Uani 1 1 d . . . C1 C 0.8658(12) 0.3510(8) 0.3920(6) 0.035(3) Uani 1 1 d . . . C17 C 1.1590(13) 0.1359(8) 0.4475(6) 0.032(3) Uani 1 1 d . . . C3 C 0.9406(14) 0.2527(9) 0.5265(6) 0.044(3) Uani 1 1 d . . . H3A H 1.0239 0.2341 0.5754 0.053 Uiso 1 1 calc R . . C9 C 0.6350(12) 0.4075(8) 0.2404(6) 0.029(3) Uani 1 1 d . . . C7 C 0.8963(13) 0.4451(8) 0.3346(6) 0.039(3) Uani 1 1 d . . . H7A H 1.0099 0.4504 0.3347 0.047 Uiso 1 1 calc R . . H7B H 0.8622 0.5140 0.3571 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cr52 0.0457(11) 0.0309(9) 0.0184(8) -0.0017(9) -0.0025(7) 0.0051(10) C13 0.040(7) 0.037(7) 0.034(6) -0.004(5) 0.007(5) 0.002(6) O5 0.042(5) 0.052(5) 0.045(5) -0.022(4) 0.004(4) -0.011(4) O2 0.060(5) 0.033(5) 0.032(4) 0.006(4) 0.004(4) 0.005(4) C11 0.026(6) 0.054(8) 0.048(7) -0.009(6) 0.014(5) 0.009(7) O3 0.048(6) 0.045(5) 0.049(5) -0.003(4) 0.002(4) 0.004(5) O6 0.044(5) 0.056(5) 0.049(5) -0.029(4) 0.013(4) -0.008(5) O1 0.047(5) 0.031(5) 0.070(6) 0.011(4) -0.010(4) 0.000(4) C12 0.043(7) 0.032(7) 0.023(5) -0.005(5) -0.005(5) 0.014(6) O4 0.041(5) 0.075(6) 0.051(5) -0.001(5) -0.012(4) 0.011(5) C15 0.032(6) 0.030(6) 0.024(6) 0.011(5) 0.002(5) -0.002(6) C10 0.044(7) 0.015(6) 0.025(5) -0.003(4) -0.002(5) -0.002(6) C2 0.043(7) 0.035(7) 0.035(6) -0.016(6) -0.014(5) 0.008(6) C4 0.075(9) 0.040(7) 0.019(6) 0.008(5) 0.018(6) 0.024(8) C8 0.047(8) 0.029(6) 0.033(6) 0.001(5) 0.005(6) 0.005(6) C16 0.046(8) 0.041(7) 0.020(6) -0.001(5) 0.002(5) 0.002(7) C14 0.039(7) 0.035(7) 0.018(6) 0.001(5) 0.002(5) 0.006(6) C5 0.059(8) 0.040(7) 0.021(6) -0.009(5) 0.011(5) -0.001(7) C6 0.045(7) 0.034(7) 0.019(5) -0.009(5) -0.006(5) -0.009(6) C1 0.038(7) 0.035(7) 0.029(6) -0.007(5) 0.000(5) 0.005(6) C17 0.044(8) 0.036(7) 0.015(5) -0.015(5) -0.001(5) 0.003(6) C3 0.064(9) 0.046(8) 0.023(6) -0.003(6) 0.009(6) 0.007(7) C9 0.024(7) 0.030(6) 0.033(6) -0.017(5) 0.002(5) 0.009(6) C7 0.044(8) 0.038(7) 0.032(6) -0.004(5) 0.001(5) 0.002(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 Cr52 C16 1.817(12) . ? Cr52 C15 1.833(10) . ? Cr52 C17 1.851(11) . ? Cr52 C1 2.207(11) . ? Cr52 C2 2.215(10) . ? Cr52 C3 2.216(10) . ? Cr52 C6 2.261(11) . ? Cr52 C4 2.261(10) . ? Cr52 C5 2.270(11) . ? C13 C14 1.508(13) . ? C13 C12 1.550(12) . ? O5 C14 1.252(11) . ? O2 C15 1.166(9) . ? C11 C10 1.542(12) . ? O3 C16 1.174(12) . ? O6 C14 1.292(11) . ? O1 C9 1.195(11) . ? C12 C10 1.585(12) . ? O4 C17 1.172(12) . ? C10 C6 1.549(12) . ? C10 C9 1.549(13) . ? C2 C3 1.390(13) . ? C2 C1 1.419(13) . ? C4 C3 1.404(14) . ? C4 C5 1.437(13) . ? C8 C9 1.492(13) . ? C8 C7 1.546(13) . ? C5 C6 1.447(13) . ? C6 C1 1.417(13) . ? C1 C7 1.507(13) . ? 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 C16 Cr52 C15 88.2(4) . . ? C16 Cr52 C17 90.7(5) . . ? C15 Cr52 C17 87.4(4) . . ? C16 Cr52 C1 144.2(4) . . ? C15 Cr52 C1 90.5(4) . . ? C17 Cr52 C1 125.0(4) . . ? C16 Cr52 C2 160.3(4) . . ? C15 Cr52 C2 111.2(4) . . ? C17 Cr52 C2 93.8(4) . . ? C1 Cr52 C2 37.4(3) . . ? C16 Cr52 C3 124.9(4) . . ? C15 Cr52 C3 146.4(5) . . ? C17 Cr52 C3 86.6(4) . . ? C1 Cr52 C3 66.6(4) . . ? C2 Cr52 C3 36.6(3) . . ? C16 Cr52 C6 108.0(5) . . ? C15 Cr52 C6 98.2(4) . . ? C17 Cr52 C6 160.6(4) . . ? C1 Cr52 C6 37.0(3) . . ? C2 Cr52 C6 66.9(4) . . ? C3 Cr52 C6 78.4(4) . . ? C16 Cr52 C4 94.2(5) . . ? C15 Cr52 C4 164.7(4) . . ? C17 Cr52 C4 107.7(4) . . ? C1 Cr52 C4 78.7(4) . . ? C2 Cr52 C4 66.2(4) . . ? C3 Cr52 C4 36.5(4) . . ? C6 Cr52 C4 66.6(4) . . ? C16 Cr52 C5 86.2(4) . . ? C15 Cr52 C5 128.5(4) . . ? C17 Cr52 C5 143.8(4) . . ? C1 Cr52 C5 67.0(4) . . ? C2 Cr52 C5 78.9(4) . . ? C3 Cr52 C5 66.4(4) . . ? C6 Cr52 C5 37.3(3) . . ? C4 Cr52 C5 37.0(3) . . ? C14 C13 C12 112.1(8) . . ? C13 C12 C10 114.0(8) . . ? O2 C15 Cr52 178.3(9) . . ? C11 C10 C6 110.7(8) . . ? C11 C10 C9 109.5(8) . . ? C6 C10 C9 110.9(8) . . ? C11 C10 C12 110.9(8) . . ? C6 C10 C12 108.8(8) . . ? C9 C10 C12 105.9(7) . . ? C3 C2 C1 119.6(10) . . ? C3 C2 Cr52 71.8(6) . . ? C1 C2 Cr52 71.0(6) . . ? C3 C4 C5 119.6(10) . . ? C3 C4 Cr52 70.0(6) . . ? C5 C4 Cr52 71.9(5) . . ? C9 C8 C7 110.3(8) . . ? O3 C16 Cr52 175.8(9) . . ? O5 C14 O6 123.7(9) . . ? O5 C14 C13 120.2(10) . . ? O6 C14 C13 116.1(10) . . ? C4 C5 C6 118.9(10) . . ? C4 C5 Cr52 71.2(6) . . ? C6 C5 Cr52 71.0(6) . . ? C1 C6 C5 119.2(9) . . ? C1 C6 C10 123.9(9) . . ? C5 C6 C10 116.6(9) . . ? C1 C6 Cr52 69.5(6) . . ? C5 C6 Cr52 71.7(6) . . ? C10 C6 Cr52 136.0(6) . . ? C6 C1 C2 120.8(9) . . ? C6 C1 C7 120.3(9) . . ? C2 C1 C7 118.8(10) . . ? C6 C1 Cr52 73.6(6) . . ? C2 C1 Cr52 71.6(6) . . ? C7 C1 Cr52 130.7(7) . . ? O4 C17 Cr52 177.3(9) . . ? C2 C3 C4 121.9(10) . . ? C2 C3 Cr52 71.7(5) . . ? C4 C3 Cr52 73.5(6) . . ? O1 C9 C8 124.1(10) . . ? O1 C9 C10 121.0(9) . . ? C8 C9 C10 114.9(9) . . ? C1 C7 C8 112.3(9) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.404 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.096