# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Qiang Xu' _publ_contact_author_address ; National Institute of Advanced Industrial Science and Technology (AIST) Ikeda, Osaka 563-8577 JAPAN ; _publ_contact_author_email Q.XU@AIST.GO.JP loop_ _publ_author_name 'Hai-Long Jiang' 'Qiang Xu' # Attachment '3.CIF' data_3 _database_code_depnum_ccdc_archive 'CCDC 734403' #TrackingRef '3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H26 Co2 F18 O12' _chemical_formula_weight 1290.58 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 19.030(4) _cell_length_b 7.2300(14) _cell_length_c 23.644(9) _cell_angle_alpha 90.00 _cell_angle_beta 123.76(2) _cell_angle_gamma 90.00 _cell_volume 2704.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.735 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8415 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35901 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6177 _reflns_number_gt 4962 _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^)+(0.0440P)^2^+1.3622P] 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 6177 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0906 _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 Co1 Co -0.449356(16) -0.33170(4) -0.475575(12) 0.02983(9) Uani 1 1 d . . . F1 F -0.07984(9) -1.2342(3) -0.56459(7) 0.0643(5) Uani 1 1 d . . . F2 F -0.17985(10) -1.2998(2) -0.55138(7) 0.0607(4) Uani 1 1 d . . . F3 F -0.09578(9) -1.0744(3) -0.49622(7) 0.0665(5) Uani 1 1 d . . . F4 F -0.19120(10) -0.7487(2) -0.66586(8) 0.0604(4) Uani 1 1 d . . . F5 F -0.08110(9) -0.8147(2) -0.56804(8) 0.0667(5) Uani 1 1 d . . . F6 F -0.11089(10) -0.9716(2) -0.65555(9) 0.0683(5) Uani 1 1 d . . . F7 F 0.06948(12) 0.5879(2) -0.26071(12) 0.0895(6) Uani 1 1 d . . . F8 F -0.05665(11) 0.5265(3) -0.34559(11) 0.0929(7) Uani 1 1 d . . . F9 F 0.04599(11) 0.3538(3) -0.32493(9) 0.0717(5) Uani 1 1 d . . . O1 O -0.38610(10) -0.5253(2) -0.50396(8) 0.0474(4) Uani 1 1 d . . . O2 O -0.46858(10) -0.7742(2) -0.54361(9) 0.0474(4) Uani 1 1 d . . . O3 O -0.48131(10) -1.2653(3) -0.92697(7) 0.0488(4) Uani 1 1 d . . . O4 O -0.39717(11) -1.5137(3) -0.89190(8) 0.0513(4) Uani 1 1 d . . . O5 O -0.34934(9) -0.1525(2) -0.43597(7) 0.0372(3) Uani 1 1 d . . . O6 O -0.25728(11) -0.3162(3) -0.44428(12) 0.0703(6) Uani 1 1 d . . . H6 H -0.2402 -0.3978 -0.4154 0.084 Uiso 1 1 d R . . C1 C -0.40519(13) -0.6847(3) -0.53098(10) 0.0372(5) Uani 1 1 d . . . C2 C -0.34982(13) -0.7702(3) -0.55043(10) 0.0360(5) Uani 1 1 d . . . C3 C -0.28125(17) -0.6773(4) -0.54212(15) 0.0560(7) Uani 1 1 d . . . H3A H -0.2679 -0.5600 -0.5227 0.067 Uiso 1 1 calc R . . C4 C -0.23200(16) -0.7557(4) -0.56226(14) 0.0542(7) Uani 1 1 d . . . H4A H -0.1860 -0.6909 -0.5561 0.065 Uiso 1 1 calc R . . C5 C -0.36770(13) -0.9470(3) -0.57804(11) 0.0375(5) Uani 1 1 d . . . H5A H -0.4125 -1.0135 -0.5827 0.045 Uiso 1 1 calc R . . C6 C -0.31895(13) -1.0242(3) -0.59854(11) 0.0386(5) Uani 1 1 d . . . H6A H -0.3319 -1.1420 -0.6176 0.046 Uiso 1 1 calc R . . C7 C -0.25090(12) -0.9295(3) -0.59137(10) 0.0347(4) Uani 1 1 d . . . C8 C -0.19860(12) -1.0260(3) -0.61452(10) 0.0347(5) Uani 1 1 d . . . C9 C -0.13766(14) -1.1601(4) -0.55654(11) 0.0485(6) Uani 1 1 d . . . C10 C -0.14488(14) -0.8887(4) -0.62554(13) 0.0477(6) Uani 1 1 d . . . C11 C -0.25761(12) -1.1245(3) -0.68324(10) 0.0334(4) Uani 1 1 d . . . C12 C -0.24422(13) -1.3034(3) -0.69667(10) 0.0380(5) Uani 1 1 d . . . H12A H -0.1991 -1.3723 -0.6627 0.046 Uiso 1 1 calc R . . C13 C -0.29799(14) -1.3794(3) -0.76063(10) 0.0393(5) Uani 1 1 d . . . H13A H -0.2890 -1.4998 -0.7690 0.047 Uiso 1 1 calc R . . C14 C -0.32568(13) -1.0243(3) -0.73530(11) 0.0421(5) Uani 1 1 d . . . H14A H -0.3357 -0.9048 -0.7268 0.050 Uiso 1 1 calc R . . C15 C -0.37852(13) -1.0997(4) -0.79935(10) 0.0414(5) Uani 1 1 d . . . H15A H -0.4231 -1.0305 -0.8338 0.050 Uiso 1 1 calc R . . C16 C -0.36493(13) -1.2789(3) -0.81221(10) 0.0349(4) Uani 1 1 d . . . C17 C -0.41918(13) -1.3594(3) -0.88246(10) 0.0390(5) Uani 1 1 d . . . C21 C -0.27841(13) -0.1728(3) -0.42372(10) 0.0371(5) Uani 1 1 d . . . C22 C -0.20988(13) -0.0376(3) -0.38413(11) 0.0361(4) Uani 1 1 d . . . C23 C -0.22388(14) 0.1167(3) -0.35699(13) 0.0473(6) Uani 1 1 d . . . H23A H -0.2777 0.1397 -0.3669 0.057 Uiso 1 1 calc R . . C24 C -0.15860(14) 0.2368(4) -0.31531(14) 0.0500(6) Uani 1 1 d . . . H24A H -0.1690 0.3410 -0.2980 0.060 Uiso 1 1 calc R . . C25 C -0.12994(13) -0.0657(3) -0.37119(12) 0.0423(5) Uani 1 1 d . . . H25A H -0.1205 -0.1648 -0.3912 0.051 Uiso 1 1 calc R . . C26 C -0.06458(13) 0.0530(3) -0.32872(12) 0.0436(5) Uani 1 1 d . . . H26A H -0.0112 0.0318 -0.3199 0.052 Uiso 1 1 calc R . . C27 C -0.07725(13) 0.2033(3) -0.29902(12) 0.0388(5) Uani 1 1 d . . . C28 C 0.0000 0.3254(5) -0.2500 0.0438(7) Uani 1 2 d S . . C29 C 0.01540(17) 0.4497(4) -0.29531(17) 0.0637(8) 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 Co1 0.02873(14) 0.03438(15) 0.02647(14) 0.00284(11) 0.01539(11) 0.00232(11) F1 0.0411(7) 0.0875(12) 0.0496(8) -0.0106(8) 0.0160(6) 0.0280(8) F2 0.0677(10) 0.0601(10) 0.0489(8) 0.0089(7) 0.0290(8) 0.0153(8) F3 0.0517(8) 0.0919(13) 0.0313(7) -0.0189(7) 0.0076(6) 0.0141(8) F4 0.0603(9) 0.0530(9) 0.0736(10) -0.0019(8) 0.0408(8) -0.0053(8) F5 0.0364(7) 0.0852(13) 0.0729(10) -0.0346(9) 0.0270(7) -0.0208(8) F6 0.0667(10) 0.0779(12) 0.0917(12) -0.0264(9) 0.0636(9) -0.0106(9) F7 0.0721(11) 0.0401(10) 0.1518(19) 0.0177(11) 0.0594(12) -0.0106(9) F8 0.0608(10) 0.0699(13) 0.1314(17) 0.0564(12) 0.0432(11) 0.0250(9) F9 0.0677(10) 0.0712(12) 0.0896(12) 0.0320(10) 0.0521(10) 0.0133(9) O1 0.0419(8) 0.0500(10) 0.0537(9) -0.0178(8) 0.0287(8) 0.0039(8) O2 0.0489(9) 0.0463(10) 0.0638(10) -0.0038(8) 0.0417(9) 0.0027(8) O3 0.0442(9) 0.0626(11) 0.0283(7) -0.0081(7) 0.0131(7) -0.0033(8) O4 0.0545(10) 0.0567(11) 0.0354(8) -0.0170(8) 0.0204(7) -0.0068(9) O5 0.0325(7) 0.0358(8) 0.0434(8) -0.0029(6) 0.0211(6) 0.0010(6) O6 0.0478(10) 0.0630(13) 0.0987(15) -0.0391(11) 0.0399(11) -0.0028(9) C1 0.0370(10) 0.0431(13) 0.0340(10) -0.0016(9) 0.0212(9) 0.0070(10) C2 0.0358(10) 0.0393(12) 0.0367(10) -0.0055(9) 0.0225(9) 0.0033(9) C3 0.0569(14) 0.0495(15) 0.0797(18) -0.0335(13) 0.0492(14) -0.0152(12) C4 0.0466(13) 0.0551(16) 0.0775(18) -0.0339(14) 0.0449(13) -0.0194(12) C5 0.0342(10) 0.0395(12) 0.0410(11) -0.0072(9) 0.0223(9) -0.0032(9) C6 0.0381(10) 0.0357(12) 0.0429(11) -0.0138(9) 0.0230(9) -0.0040(9) C7 0.0293(9) 0.0407(12) 0.0327(10) -0.0095(9) 0.0163(8) 0.0022(9) C8 0.0288(9) 0.0402(12) 0.0335(10) -0.0116(9) 0.0164(8) 0.0018(9) C9 0.0372(11) 0.0632(17) 0.0330(11) -0.0106(11) 0.0119(9) 0.0111(12) C10 0.0375(11) 0.0589(16) 0.0529(14) -0.0197(12) 0.0289(11) -0.0059(11) C11 0.0297(9) 0.0405(12) 0.0299(10) -0.0074(8) 0.0164(8) 0.0015(8) C12 0.0376(10) 0.0394(13) 0.0311(10) -0.0035(9) 0.0153(9) 0.0056(9) C13 0.0451(12) 0.0360(12) 0.0343(11) -0.0077(9) 0.0205(9) -0.0002(10) C14 0.0392(11) 0.0422(13) 0.0370(11) -0.0087(9) 0.0163(9) 0.0064(10) C15 0.0347(10) 0.0497(14) 0.0297(10) -0.0035(9) 0.0116(9) 0.0066(10) C16 0.0344(10) 0.0425(12) 0.0282(9) -0.0080(8) 0.0177(8) -0.0064(9) C17 0.0370(10) 0.0527(14) 0.0309(10) -0.0101(10) 0.0212(9) -0.0122(10) C21 0.0339(10) 0.0398(12) 0.0373(11) -0.0016(9) 0.0195(9) 0.0049(9) C22 0.0318(10) 0.0362(11) 0.0399(11) -0.0006(9) 0.0195(9) 0.0046(9) C23 0.0318(10) 0.0465(14) 0.0660(15) -0.0130(11) 0.0287(11) 0.0025(10) C24 0.0380(11) 0.0390(13) 0.0750(17) -0.0160(12) 0.0328(12) 0.0017(10) C25 0.0355(11) 0.0428(13) 0.0502(13) -0.0059(10) 0.0249(10) 0.0069(10) C26 0.0302(10) 0.0433(13) 0.0596(14) -0.0026(11) 0.0263(10) 0.0064(10) C27 0.0309(10) 0.0311(12) 0.0530(13) 0.0019(9) 0.0225(9) 0.0040(8) C28 0.0326(14) 0.0299(16) 0.068(2) 0.000 0.0272(15) 0.000 C29 0.0455(14) 0.0399(15) 0.097(2) 0.0207(14) 0.0338(15) 0.0051(12) _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 Co1 O3 1.9752(17) 2_463 ? Co1 O4 1.9913(16) 4_536 ? Co1 O2 2.0044(15) 3_444 ? Co1 O5 2.0488(15) . ? Co1 O1 2.1809(15) . ? Co1 Co1 2.9150(7) 3_444 ? F1 C9 1.329(3) . ? F2 C9 1.338(3) . ? F3 C9 1.338(3) . ? F4 C10 1.333(3) . ? F5 C10 1.332(3) . ? F6 C10 1.339(3) . ? F7 C29 1.338(3) . ? F8 C29 1.338(3) . ? F9 C29 1.328(4) . ? O1 C1 1.269(3) . ? O2 C1 1.250(3) . ? O2 Co1 2.0044(15) 3_444 ? O3 C17 1.259(3) . ? O3 Co1 1.9752(17) 2_443 ? O4 C17 1.255(3) . ? O4 Co1 1.9913(16) 4_535 ? O5 C21 1.222(2) . ? O6 C21 1.300(3) . ? O6 H6 0.8200 . ? C1 C2 1.498(3) . ? C2 C3 1.381(3) . ? C2 C5 1.389(3) . ? C3 C4 1.387(3) . ? C3 H3A 0.9300 . ? C4 C7 1.381(3) . ? C4 H4A 0.9300 . ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 C7 1.389(3) . ? C6 H6A 0.9300 . ? C7 C8 1.543(3) . ? C8 C11 1.543(3) . ? C8 C10 1.547(3) . ? C8 C9 1.548(3) . ? C11 C12 1.389(3) . ? C11 C14 1.395(3) . ? C12 C13 1.384(3) . ? C12 H12A 0.9300 . ? C13 C16 1.382(3) . ? C13 H13A 0.9300 . ? C14 C15 1.382(3) . ? C14 H14A 0.9300 . ? C15 C16 1.388(3) . ? C15 H15A 0.9300 . ? C16 C17 1.502(3) . ? C21 C22 1.475(3) . ? C22 C23 1.385(3) . ? C22 C25 1.390(3) . ? C23 C24 1.381(3) . ? C23 H23A 0.9300 . ? C24 C27 1.393(3) . ? C24 H24A 0.9300 . ? C25 C26 1.380(3) . ? C25 H25A 0.9300 . ? C26 C27 1.386(3) . ? C26 H26A 0.9300 . ? C27 C28 1.546(3) . ? C28 C29 1.546(3) . ? C28 C29 1.546(3) 2_554 ? C28 C27 1.546(3) 2_554 ? 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 O3 Co1 O4 159.45(8) 2_463 4_536 ? O3 Co1 O2 94.12(8) 2_463 3_444 ? O4 Co1 O2 90.61(8) 4_536 3_444 ? O3 Co1 O5 103.19(7) 2_463 . ? O4 Co1 O5 94.42(7) 4_536 . ? O2 Co1 O5 107.32(7) 3_444 . ? O3 Co1 O1 85.53(7) 2_463 . ? O4 Co1 O1 83.67(7) 4_536 . ? O2 Co1 O1 161.34(7) 3_444 . ? O5 Co1 O1 90.86(6) . . ? O3 Co1 Co1 82.80(6) 2_463 3_444 ? O4 Co1 Co1 77.29(6) 4_536 3_444 ? O2 Co1 Co1 88.95(5) 3_444 3_444 ? O5 Co1 Co1 161.97(4) . 3_444 ? O1 Co1 Co1 72.47(5) . 3_444 ? C1 O1 Co1 133.25(14) . . ? C1 O2 Co1 121.20(15) . 3_444 ? C17 O3 Co1 123.52(16) . 2_443 ? C17 O4 Co1 130.12(15) . 4_535 ? C21 O5 Co1 130.97(15) . . ? C21 O6 H6 109.0 . . ? O2 C1 O1 123.96(19) . . ? O2 C1 C2 117.6(2) . . ? O1 C1 C2 118.4(2) . . ? C3 C2 C5 118.68(19) . . ? C3 C2 C1 121.7(2) . . ? C5 C2 C1 119.6(2) . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C7 C4 C3 120.3(2) . . ? C7 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C6 C5 C2 120.0(2) . . ? C6 C5 H5A 120.0 . . ? C2 C5 H5A 120.0 . . ? C5 C6 C7 121.4(2) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C4 C7 C6 118.43(19) . . ? C4 C7 C8 123.19(19) . . ? C6 C7 C8 118.36(19) . . ? C11 C8 C7 110.29(16) . . ? C11 C8 C10 106.33(17) . . ? C7 C8 C10 112.72(18) . . ? C11 C8 C9 113.10(19) . . ? C7 C8 C9 106.40(17) . . ? C10 C8 C9 108.10(19) . . ? F1 C9 F3 106.81(18) . . ? F1 C9 F2 107.2(2) . . ? F3 C9 F2 106.5(2) . . ? F1 C9 C8 113.5(2) . . ? F3 C9 C8 111.3(2) . . ? F2 C9 C8 111.18(18) . . ? F5 C10 F4 106.9(2) . . ? F5 C10 F6 106.65(18) . . ? F4 C10 F6 106.5(2) . . ? F5 C10 C8 113.5(2) . . ? F4 C10 C8 111.81(18) . . ? F6 C10 C8 111.2(2) . . ? C12 C11 C14 118.72(19) . . ? C12 C11 C8 123.51(18) . . ? C14 C11 C8 117.71(19) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C16 C13 C12 121.0(2) . . ? C16 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C11 121.0(2) . . ? C15 C14 H14A 119.5 . . ? C11 C14 H14A 119.5 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C13 C16 C15 119.33(19) . . ? C13 C16 C17 120.1(2) . . ? C15 C16 C17 120.4(2) . . ? O4 C17 O3 125.7(2) . . ? O4 C17 C16 116.7(2) . . ? O3 C17 C16 117.7(2) . . ? O5 C21 O6 122.5(2) . . ? O5 C21 C22 122.79(19) . . ? O6 C21 C22 114.69(18) . . ? C23 C22 C25 119.0(2) . . ? C23 C22 C21 119.87(19) . . ? C25 C22 C21 121.1(2) . . ? C24 C23 C22 120.6(2) . . ? C24 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C23 C24 C27 120.6(2) . . ? C23 C24 H24A 119.7 . . ? C27 C24 H24A 119.7 . . ? C26 C25 C22 120.2(2) . . ? C26 C25 H25A 119.9 . . ? C22 C25 H25A 119.9 . . ? C25 C26 C27 121.08(19) . . ? C25 C26 H26A 119.5 . . ? C27 C26 H26A 119.5 . . ? C26 C27 C24 118.4(2) . . ? C26 C27 C28 117.84(18) . . ? C24 C27 C28 123.7(2) . . ? C29 C28 C29 108.9(3) . 2_554 ? C29 C28 C27 106.26(15) . . ? C29 C28 C27 112.58(13) 2_554 . ? C29 C28 C27 112.58(13) . 2_554 ? C29 C28 C27 106.26(15) 2_554 2_554 ? C27 C28 C27 110.3(3) . 2_554 ? F9 C29 F8 106.3(3) . . ? F9 C29 F7 107.4(2) . . ? F8 C29 F7 107.1(2) . . ? F9 C29 C28 111.7(2) . . ? F8 C29 C28 111.2(2) . . ? F7 C29 C28 112.8(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.420 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.057 # Attachment '1.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 734404' #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 Cu F6 O5' _chemical_formula_weight 471.79 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.710(3) _cell_length_b 6.9800(14) _cell_length_c 23.624(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.50(2) _cell_angle_gamma 90.00 _cell_volume 1841.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7330 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15560 _diffrn_reflns_av_R_equivalents 0.1333 _diffrn_reflns_av_sigmaI/netI 0.1443 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4093 _reflns_number_gt 3000 _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4093 _refine_ls_number_parameters 276 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.002 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 Cu1 Cu 0.43216(3) 0.15176(6) -0.018740(19) 0.01780(15) Uani 1 1 d . . . F1 F -0.0719(2) -0.5864(3) -0.31852(12) 0.0348(6) Uani 1 1 d . . . F2 F 0.0553(2) -0.8097(3) -0.30261(12) 0.0360(6) Uani 1 1 d . . . F3 F -0.09131(19) -0.7620(3) -0.39726(11) 0.0330(5) Uani 1 1 d . . . F4 F -0.0693(2) -0.4860(3) -0.46709(10) 0.0349(6) Uani 1 1 d . . . F5 F -0.10162(19) -0.3139(3) -0.40214(11) 0.0335(6) Uani 1 1 d . . . F6 F 0.0462(2) -0.2485(3) -0.41889(12) 0.0367(6) Uani 1 1 d . . . O1 O 0.3384(2) 0.0126(4) -0.09995(13) 0.0327(7) Uani 1 1 d . . . O1W O 0.3352(2) 0.4170(4) -0.04116(15) 0.0335(7) Uani 1 1 d D . . O2 O 0.4515(3) -0.2502(4) -0.06685(13) 0.0352(7) Uani 1 1 d . . . O3 O 0.3457(2) -1.0249(4) -0.47972(15) 0.0340(7) Uani 1 1 d . . . O4 O 0.4588(3) -0.7603(4) -0.44947(16) 0.0369(7) Uani 1 1 d . . . C1 C 0.3653(3) -0.1545(5) -0.10819(18) 0.0240(8) Uani 1 1 d . . . C2 C 0.2883(3) -0.2491(5) -0.17191(16) 0.0215(7) Uani 1 1 d . . . C3 C 0.1866(3) -0.1580(5) -0.21825(18) 0.0278(8) Uani 1 1 d . . . H3A H 0.1656 -0.0381 -0.2096 0.038(12) Uiso 1 1 d R . . C4 C 0.1158(3) -0.2441(5) -0.27744(18) 0.0269(8) Uani 1 1 d . . . H4A H 0.0477 -0.1816 -0.3080 0.040(13) Uiso 1 1 d R . . C5 C 0.3168(3) -0.4302(6) -0.18519(18) 0.0260(8) Uani 1 1 d . . . H5A H 0.3833 -0.4945 -0.1540 0.037(12) Uiso 1 1 d R . . C6 C 0.2469(3) -0.5162(5) -0.24447(18) 0.0267(8) Uani 1 1 d . . . H6A H 0.2676 -0.6365 -0.2530 0.034(12) Uiso 1 1 d R . . C7 C 0.1458(3) -0.4230(5) -0.29153(17) 0.0193(7) Uani 1 1 d . . . C8 C 0.0695(3) -0.5279(5) -0.35612(16) 0.0186(7) Uani 1 1 d . . . C9 C -0.0105(3) -0.6727(5) -0.34370(18) 0.0251(8) Uani 1 1 d . . . C10 C -0.0144(3) -0.3943(5) -0.41101(18) 0.0247(8) Uani 1 1 d . . . C11 C 0.1499(3) -0.6263(5) -0.37995(17) 0.0195(7) Uani 1 1 d . . . C12 C 0.1296(3) -0.8100(5) -0.4064(2) 0.0266(8) Uani 1 1 d . . . H12A H 0.0665 -0.8824 -0.4083 0.049(14) Uiso 1 1 d R . . C13 C 0.2019(4) -0.8859(6) -0.4297(2) 0.0292(9) Uani 1 1 d . . . H13A H 0.1865 -1.0081 -0.4476 0.067(17) Uiso 1 1 d R . . C14 C 0.2462(3) -0.5230(5) -0.37718(19) 0.0266(8) Uani 1 1 d . . . H14A H 0.2617 -0.4006 -0.3594 0.060(16) Uiso 1 1 d R . . C15 C 0.3190(3) -0.5980(6) -0.40013(19) 0.0277(8) Uani 1 1 d . . . H15A H 0.3827 -0.5261 -0.3977 0.031(11) Uiso 1 1 d R . . C16 C 0.2981(3) -0.7801(5) -0.42673(17) 0.0218(7) Uani 1 1 d . . . C17 C 0.3725(3) -0.8617(5) -0.45433(18) 0.0235(8) Uani 1 1 d . . . H1WA H 0.378(3) 0.516(3) -0.0300(18) 0.028 Uiso 1 1 d D . . H1WB H 0.301(3) 0.411(5) -0.0188(16) 0.028 Uiso 1 1 d 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 Cu1 0.0195(2) 0.0167(2) 0.0181(2) -0.00076(16) 0.0097(2) -0.00323(19) F1 0.0364(12) 0.0416(14) 0.0415(14) -0.0053(11) 0.0307(11) -0.0014(11) F2 0.0411(13) 0.0299(12) 0.0383(14) 0.0114(11) 0.0200(12) 0.0058(11) F3 0.0280(11) 0.0370(13) 0.0361(13) -0.0096(11) 0.0170(10) -0.0110(11) F4 0.0408(13) 0.0398(13) 0.0166(11) -0.0030(10) 0.0077(10) 0.0051(12) F5 0.0289(11) 0.0385(13) 0.0318(13) 0.0015(11) 0.0135(10) 0.0141(11) F6 0.0411(13) 0.0313(12) 0.0399(14) 0.0089(11) 0.0210(12) -0.0015(11) O1 0.0316(14) 0.0293(14) 0.0230(14) -0.0086(12) 0.0014(12) 0.0007(13) O1W 0.0297(14) 0.0242(13) 0.0463(18) 0.0034(14) 0.0179(14) 0.0001(13) O2 0.0350(15) 0.0264(14) 0.0237(14) -0.0074(13) -0.0026(12) 0.0011(14) O3 0.0375(15) 0.0287(14) 0.0519(19) -0.0105(14) 0.0344(15) -0.0018(13) O4 0.0387(15) 0.0321(15) 0.060(2) -0.0158(15) 0.0394(16) -0.0053(14) C1 0.0279(18) 0.0283(19) 0.0186(18) 0.0010(15) 0.0133(16) -0.0052(17) C2 0.0220(16) 0.0241(18) 0.0159(17) -0.0020(15) 0.0069(14) -0.0036(16) C3 0.0309(19) 0.0222(18) 0.0236(19) -0.0072(15) 0.0075(17) 0.0010(17) C4 0.0289(18) 0.0251(18) 0.0191(18) -0.0037(16) 0.0053(16) 0.0062(18) C5 0.0198(16) 0.0309(19) 0.0210(18) -0.0031(17) 0.0047(15) 0.0045(17) C6 0.0288(18) 0.0267(19) 0.0217(19) -0.0060(16) 0.0097(16) 0.0034(18) C7 0.0192(15) 0.0243(17) 0.0154(16) -0.0019(15) 0.0090(13) 0.0028(16) C8 0.0204(16) 0.0228(17) 0.0148(17) -0.0011(14) 0.0103(14) 0.0017(15) C9 0.0292(19) 0.0264(18) 0.025(2) -0.0047(16) 0.0175(17) -0.0008(17) C10 0.0260(17) 0.0280(19) 0.0194(18) -0.0015(16) 0.0102(16) 0.0038(17) C11 0.0201(16) 0.0221(17) 0.0193(17) -0.0015(14) 0.0119(14) 0.0027(15) C12 0.0308(19) 0.0211(18) 0.038(2) -0.0040(17) 0.0247(19) -0.0017(17) C13 0.036(2) 0.0251(19) 0.036(2) -0.0062(18) 0.0250(19) -0.0009(18) C14 0.0289(18) 0.0255(19) 0.029(2) -0.0076(17) 0.0165(17) -0.0017(17) C15 0.0244(18) 0.031(2) 0.034(2) -0.0093(18) 0.0186(17) -0.0049(17) C16 0.0229(16) 0.0240(18) 0.0213(17) -0.0026(15) 0.0127(15) 0.0017(16) C17 0.0268(18) 0.0255(18) 0.0221(18) 0.0033(15) 0.0148(16) 0.0090(16) _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 Cu1 O3 1.952(3) 4_546 ? Cu1 O4 1.964(3) 2_664 ? Cu1 O1 1.965(3) . ? Cu1 O2 1.973(3) 3_655 ? Cu1 O1W 2.146(3) . ? Cu1 Cu1 2.6056(9) 3_655 ? F1 C9 1.330(4) . ? F2 C9 1.335(4) . ? F3 C9 1.343(4) . ? F4 C10 1.330(4) . ? F5 C10 1.345(4) . ? F6 C10 1.342(4) . ? O1 C1 1.256(4) . ? O1W H1WA 0.842(10) . ? O1W H1WB 0.835(10) . ? O2 C1 1.257(5) . ? O2 Cu1 1.973(3) 3_655 ? O3 C17 1.256(4) . ? O3 Cu1 1.952(3) 4_545 ? O4 C17 1.263(4) . ? O4 Cu1 1.964(3) 2_644 ? C1 C2 1.501(5) . ? C2 C3 1.387(5) . ? C2 C5 1.391(5) . ? C3 C4 1.387(5) . ? C3 H3A 0.9301 . ? C4 C7 1.392(5) . ? C4 H4A 0.9300 . ? C5 C6 1.387(5) . ? C5 H5A 0.9300 . ? C6 C7 1.395(5) . ? C6 H6A 0.9302 . ? C7 C8 1.547(5) . ? C8 C10 1.539(5) . ? C8 C11 1.544(4) . ? C8 C9 1.557(5) . ? C11 C14 1.394(5) . ? C11 C12 1.396(5) . ? C12 C13 1.384(5) . ? C12 H12A 0.9303 . ? C13 C16 1.400(5) . ? C13 H13A 0.9299 . ? C14 C15 1.380(5) . ? C14 H14A 0.9299 . ? C15 C16 1.386(5) . ? C15 H15A 0.9301 . ? C16 C17 1.495(5) . ? 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 O3 Cu1 O4 169.10(11) 4_546 2_664 ? O3 Cu1 O1 91.20(13) 4_546 . ? O4 Cu1 O1 89.50(13) 2_664 . ? O3 Cu1 O2 89.41(13) 4_546 3_655 ? O4 Cu1 O2 87.84(14) 2_664 3_655 ? O1 Cu1 O2 168.89(11) . 3_655 ? O3 Cu1 O1W 96.98(11) 4_546 . ? O4 Cu1 O1W 93.60(11) 2_664 . ? O1 Cu1 O1W 100.15(11) . . ? O2 Cu1 O1W 90.78(11) 3_655 . ? O3 Cu1 Cu1 84.33(8) 4_546 3_655 ? O4 Cu1 Cu1 84.88(9) 2_664 3_655 ? O1 Cu1 Cu1 85.68(8) . 3_655 ? O2 Cu1 Cu1 83.35(8) 3_655 3_655 ? O1W Cu1 Cu1 173.98(8) . 3_655 ? C1 O1 Cu1 121.8(2) . . ? Cu1 O1W H1WA 115(3) . . ? Cu1 O1W H1WB 102(3) . . ? H1WA O1W H1WB 107.6(16) . . ? C1 O2 Cu1 124.1(3) . 3_655 ? C17 O3 Cu1 123.4(2) . 4_545 ? C17 O4 Cu1 122.0(2) . 2_644 ? O1 C1 O2 125.0(4) . . ? O1 C1 C2 117.9(3) . . ? O2 C1 C2 117.0(3) . . ? C3 C2 C5 118.9(3) . . ? C3 C2 C1 120.4(3) . . ? C5 C2 C1 120.7(3) . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.6 . . ? C3 C4 C7 120.6(3) . . ? C3 C4 H4A 119.7 . . ? C7 C4 H4A 119.6 . . ? C6 C5 C2 120.7(3) . . ? C6 C5 H5A 119.6 . . ? C2 C5 H5A 119.7 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.8 . . ? C4 C7 C6 118.7(3) . . ? C4 C7 C8 123.1(3) . . ? C6 C7 C8 118.1(3) . . ? C10 C8 C11 106.0(3) . . ? C10 C8 C7 113.6(3) . . ? C11 C8 C7 110.9(3) . . ? C10 C8 C9 107.5(3) . . ? C11 C8 C9 112.7(3) . . ? C7 C8 C9 106.2(3) . . ? F1 C9 F2 107.3(3) . . ? F1 C9 F3 106.4(3) . . ? F2 C9 F3 106.6(3) . . ? F1 C9 C8 111.4(3) . . ? F2 C9 C8 111.3(3) . . ? F3 C9 C8 113.5(3) . . ? F4 C10 F6 106.8(3) . . ? F4 C10 F5 106.1(3) . . ? F6 C10 F5 106.0(3) . . ? F4 C10 C8 111.8(3) . . ? F6 C10 C8 111.3(3) . . ? F5 C10 C8 114.4(3) . . ? C14 C11 C12 117.9(3) . . ? C14 C11 C8 118.2(3) . . ? C12 C11 C8 123.9(3) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C16 120.5(3) . . ? C12 C13 H13A 119.8 . . ? C16 C13 H13A 119.7 . . ? C15 C14 C11 121.6(3) . . ? C15 C14 H14A 119.2 . . ? C11 C14 H14A 119.2 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C15 C16 C13 118.8(3) . . ? C15 C16 C17 121.5(3) . . ? C13 C16 C17 119.7(3) . . ? O3 C17 O4 125.3(3) . . ? O3 C17 C16 118.0(3) . . ? O4 C17 C16 116.7(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.728 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.120 # Attachment '2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 734405' #TrackingRef '2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H26 Cu2 F18 O12' _chemical_formula_weight 1299.80 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.760(4) _cell_length_b 7.2800(15) _cell_length_c 23.402(9) _cell_angle_alpha 90.00 _cell_angle_beta 123.12(2) _cell_angle_gamma 90.00 _cell_volume 2676.8(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7711 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23981 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6073 _reflns_number_gt 3630 _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^)+(0.0389P)^2^+3.4162P] 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 6073 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_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 Cu1 Cu -0.45015(3) -0.35343(6) -0.47806(2) 0.03082(13) Uani 1 1 d . . . F1 F -0.08142(15) -1.2339(4) -0.56590(12) 0.0624(7) Uani 1 1 d . . . F2 F -0.18220(17) -1.2954(4) -0.55113(12) 0.0597(7) Uani 1 1 d . . . F3 F -0.09719(15) -1.0711(4) -0.49736(11) 0.0658(8) Uani 1 1 d . . . F4 F -0.19252(17) -0.7527(3) -0.66843(14) 0.0604(7) Uani 1 1 d . . . F5 F -0.08150(15) -0.8188(4) -0.57108(14) 0.0664(8) Uani 1 1 d . . . F6 F -0.11284(16) -0.9764(4) -0.65904(14) 0.0684(8) Uani 1 1 d . . . F7 F 0.07147(19) 0.6031(4) -0.25999(18) 0.0868(10) Uani 1 1 d . . . F8 F -0.05398(19) 0.5419(4) -0.34545(18) 0.0889(10) Uani 1 1 d . . . F9 F 0.04988(18) 0.3704(4) -0.32376(15) 0.0703(8) Uani 1 1 d . . . O1 O -0.38488(16) -0.5142(4) -0.50339(13) 0.0438(7) Uani 1 1 d . . . O2 O -0.47101(17) -0.7579(4) -0.54157(14) 0.0428(6) Uani 1 1 d . . . O3 O -0.48179(16) -1.2701(4) -0.92809(12) 0.0431(6) Uani 1 1 d . . . O4 O -0.39656(17) -1.5175(4) -0.89159(12) 0.0451(7) Uani 1 1 d . . . O5 O -0.34837(15) -0.1437(4) -0.43603(13) 0.0411(6) Uani 1 1 d . . . O6 O -0.2523(2) -0.3012(5) -0.44329(19) 0.0743(11) Uani 1 1 d . . . H6 H -0.2352 -0.3829 -0.4146 0.089 Uiso 1 1 d R . . C1 C -0.4066(2) -0.6741(5) -0.53013(17) 0.0357(8) Uani 1 1 d . . . C2 C -0.3514(2) -0.7636(5) -0.55011(18) 0.0351(8) Uani 1 1 d . . . C3 C -0.2820(3) -0.6739(6) -0.5424(2) 0.0540(11) Uani 1 1 d . . . H3A H -0.2679 -0.5571 -0.5232 0.065 Uiso 1 1 calc R . . C4 C -0.2328(3) -0.7553(6) -0.5629(2) 0.0525(11) Uani 1 1 d . . . H4A H -0.1859 -0.6932 -0.5569 0.063 Uiso 1 1 calc R . . C5 C -0.3706(2) -0.9393(5) -0.57735(18) 0.0387(9) Uani 1 1 d . . . H5A H -0.4160 -1.0033 -0.5813 0.046 Uiso 1 1 calc R . . C6 C -0.3219(2) -1.0193(5) -0.59863(19) 0.0401(9) Uani 1 1 d . . . H6A H -0.3357 -1.1364 -0.6176 0.048 Uiso 1 1 calc R . . C7 C -0.2529(2) -0.9278(5) -0.59225(18) 0.0343(8) Uani 1 1 d . . . C8 C -0.2004(2) -1.0264(5) -0.61562(18) 0.0360(8) Uani 1 1 d . . . C9 C -0.1395(2) -1.1568(6) -0.55716(19) 0.0466(10) Uani 1 1 d . . . C10 C -0.1463(3) -0.8918(6) -0.6283(2) 0.0480(11) Uani 1 1 d . . . C11 C -0.2599(2) -1.1258(5) -0.68415(17) 0.0347(8) Uani 1 1 d . . . C12 C -0.2476(2) -1.3055(5) -0.69696(18) 0.0394(9) Uani 1 1 d . . . H12A H -0.2032 -1.3747 -0.6624 0.047 Uiso 1 1 calc R . . C13 C -0.3008(2) -1.3817(5) -0.76068(18) 0.0400(9) Uani 1 1 d . . . H13A H -0.2922 -1.5024 -0.7685 0.048 Uiso 1 1 calc R . . C14 C -0.3270(2) -1.0261(6) -0.73665(18) 0.0424(9) Uani 1 1 d . . . H14A H -0.3366 -0.9063 -0.7287 0.051 Uiso 1 1 calc R . . C15 C -0.3796(2) -1.1028(5) -0.80068(19) 0.0416(9) Uani 1 1 d . . . H15A H -0.4237 -1.0338 -0.8356 0.050 Uiso 1 1 calc R . . C16 C -0.3667(2) -1.2818(5) -0.81297(17) 0.0359(8) Uani 1 1 d . . . C17 C -0.4196(2) -1.3632(6) -0.88323(18) 0.0360(8) Uani 1 1 d . . . C21 C -0.2766(2) -0.1594(5) -0.42315(18) 0.0387(8) Uani 1 1 d . . . C22 C -0.2084(2) -0.0226(5) -0.38409(19) 0.0373(8) Uani 1 1 d . . . C23 C -0.2240(2) 0.1324(6) -0.3579(2) 0.0479(10) Uani 1 1 d . . . H23A H -0.2787 0.1549 -0.3684 0.057 Uiso 1 1 calc R . . C24 C -0.1593(3) 0.2532(6) -0.3167(2) 0.0501(11) Uani 1 1 d . . . H24A H -0.1709 0.3577 -0.3004 0.060 Uiso 1 1 calc R . . C25 C -0.1273(2) -0.0493(6) -0.3704(2) 0.0441(9) Uani 1 1 d . . . H25A H -0.1165 -0.1484 -0.3897 0.053 Uiso 1 1 calc R . . C26 C -0.0630(2) 0.0697(5) -0.3286(2) 0.0436(9) Uani 1 1 d . . . H26A H -0.0088 0.0496 -0.3195 0.052 Uiso 1 1 calc R . . C27 C -0.0771(2) 0.2202(5) -0.2994(2) 0.0382(9) Uani 1 1 d . . . C28 C 0.0000 0.3419(7) -0.2500 0.0418(13) Uani 1 2 d S . . C29 C 0.0176(3) 0.4657(6) -0.2946(3) 0.0625(13) 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 Cu1 0.0296(2) 0.0371(2) 0.0288(2) 0.0031(2) 0.01798(18) 0.0052(2) F1 0.0392(14) 0.0842(18) 0.0506(14) -0.0098(13) 0.0160(12) 0.0256(13) F2 0.0662(17) 0.0599(16) 0.0498(14) 0.0081(12) 0.0296(14) 0.0154(13) F3 0.0505(15) 0.091(2) 0.0307(12) -0.0187(13) 0.0061(11) 0.0158(14) F4 0.0603(17) 0.0551(15) 0.0739(17) -0.0009(14) 0.0419(15) -0.0024(13) F5 0.0375(14) 0.0847(19) 0.0742(18) -0.0334(15) 0.0288(14) -0.0180(13) F6 0.0676(18) 0.0791(19) 0.0909(19) -0.0257(16) 0.0642(16) -0.0080(14) F7 0.076(2) 0.0423(15) 0.146(3) 0.0139(17) 0.063(2) -0.0110(14) F8 0.067(2) 0.0656(18) 0.126(3) 0.0482(19) 0.0478(19) 0.0212(16) F9 0.0707(18) 0.0696(18) 0.090(2) 0.0283(16) 0.0560(17) 0.0134(15) O1 0.0376(15) 0.0452(16) 0.0541(16) -0.0149(14) 0.0287(14) -0.0014(12) O2 0.0432(16) 0.0414(15) 0.0566(17) -0.0024(13) 0.0355(14) 0.0024(13) O3 0.0382(16) 0.0519(16) 0.0327(13) -0.0091(13) 0.0153(13) -0.0004(13) O4 0.0493(17) 0.0433(16) 0.0351(14) -0.0084(13) 0.0183(13) -0.0017(13) O5 0.0317(14) 0.0453(15) 0.0473(15) -0.0039(13) 0.0222(12) -0.0020(12) O6 0.0494(19) 0.066(2) 0.109(3) -0.039(2) 0.045(2) -0.0014(16) C1 0.033(2) 0.045(2) 0.0296(17) -0.0018(17) 0.0178(16) 0.0040(17) C2 0.035(2) 0.036(2) 0.0380(19) -0.0029(17) 0.0223(17) 0.0058(16) C3 0.054(3) 0.049(3) 0.076(3) -0.029(2) 0.046(3) -0.011(2) C4 0.045(3) 0.056(3) 0.073(3) -0.029(2) 0.042(2) -0.016(2) C5 0.036(2) 0.044(2) 0.043(2) -0.0040(18) 0.0256(18) 0.0001(17) C6 0.037(2) 0.040(2) 0.044(2) -0.0107(18) 0.0219(18) 0.0016(17) C7 0.0284(19) 0.043(2) 0.0324(18) -0.0102(17) 0.0172(16) 0.0000(16) C8 0.0273(19) 0.043(2) 0.0345(18) -0.0110(17) 0.0152(16) 0.0001(16) C9 0.035(2) 0.063(3) 0.034(2) -0.012(2) 0.0142(18) 0.009(2) C10 0.036(2) 0.061(3) 0.052(2) -0.022(2) 0.027(2) -0.005(2) C11 0.0299(19) 0.044(2) 0.0307(17) -0.0117(17) 0.0168(16) -0.0006(16) C12 0.040(2) 0.042(2) 0.0300(18) -0.0039(17) 0.0152(17) 0.0062(17) C13 0.043(2) 0.039(2) 0.0346(19) -0.0079(17) 0.0187(18) 0.0000(17) C14 0.040(2) 0.044(2) 0.0360(19) -0.0102(18) 0.0161(18) 0.0075(18) C15 0.034(2) 0.048(2) 0.034(2) -0.0065(18) 0.0133(17) 0.0068(17) C16 0.030(2) 0.049(2) 0.0298(18) -0.0072(17) 0.0168(16) -0.0053(16) C17 0.031(2) 0.049(2) 0.0308(18) -0.0072(19) 0.0189(17) -0.0092(18) C21 0.036(2) 0.042(2) 0.0380(19) -0.0050(19) 0.0206(17) -0.0013(18) C22 0.031(2) 0.040(2) 0.043(2) -0.0019(18) 0.0218(18) 0.0013(16) C23 0.034(2) 0.046(2) 0.067(3) -0.010(2) 0.029(2) 0.0046(19) C24 0.043(2) 0.040(2) 0.071(3) -0.010(2) 0.033(2) 0.0073(19) C25 0.036(2) 0.043(2) 0.054(2) -0.007(2) 0.025(2) 0.0062(18) C26 0.030(2) 0.046(2) 0.058(3) -0.001(2) 0.026(2) 0.0063(18) C27 0.033(2) 0.0288(18) 0.055(2) 0.0017(18) 0.0260(19) 0.0026(15) C28 0.038(3) 0.029(3) 0.065(4) 0.000 0.033(3) 0.000 C29 0.048(3) 0.041(2) 0.095(4) 0.018(3) 0.036(3) 0.007(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 Cu1 O3 1.938(3) 2_463 ? Cu1 O4 1.940(3) 4_536 ? Cu1 O2 1.949(2) 3_444 ? Cu1 O1 2.004(2) . ? Cu1 O5 2.212(3) . ? Cu1 Cu1 2.6473(10) 3_444 ? F1 C9 1.337(4) . ? F2 C9 1.343(5) . ? F3 C9 1.328(4) . ? F4 C10 1.330(5) . ? F5 C10 1.331(5) . ? F6 C10 1.337(4) . ? F7 C29 1.336(5) . ? F8 C29 1.334(5) . ? F9 C29 1.328(5) . ? O1 C1 1.278(4) . ? O2 C1 1.246(4) . ? O2 Cu1 1.949(2) 3_444 ? O3 C17 1.258(4) . ? O3 Cu1 1.938(3) 2_443 ? O4 C17 1.257(4) . ? O4 Cu1 1.940(3) 4_535 ? O5 C21 1.213(4) . ? O6 C21 1.315(4) . ? O6 H6 0.8201 . ? C1 C2 1.498(5) . ? C2 C3 1.379(5) . ? C2 C5 1.387(5) . ? C3 C4 1.383(5) . ? C3 H3A 0.9300 . ? C4 C7 1.382(5) . ? C4 H4A 0.9300 . ? C5 C6 1.385(5) . ? C5 H5A 0.9300 . ? C6 C7 1.390(5) . ? C6 H6A 0.9300 . ? C7 C8 1.540(5) . ? C8 C9 1.539(5) . ? C8 C11 1.544(5) . ? C8 C10 1.551(5) . ? C11 C14 1.389(5) . ? C11 C12 1.390(5) . ? C12 C13 1.379(5) . ? C12 H12A 0.9300 . ? C13 C16 1.378(5) . ? C13 H13A 0.9300 . ? C14 C15 1.384(5) . ? C14 H14A 0.9300 . ? C15 C16 1.384(5) . ? C15 H15A 0.9300 . ? C16 C17 1.502(5) . ? C21 C22 1.479(5) . ? C22 C25 1.387(5) . ? C22 C23 1.389(5) . ? C23 C24 1.378(6) . ? C23 H23A 0.9300 . ? C24 C27 1.384(5) . ? C24 H24A 0.9300 . ? C25 C26 1.369(5) . ? C25 H25A 0.9300 . ? C26 C27 1.391(5) . ? C26 H26A 0.9300 . ? C27 C28 1.545(5) . ? C28 C29 1.545(6) 2_554 ? C28 C29 1.545(6) . ? C28 C27 1.545(5) 2_554 ? 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 O3 Cu1 O4 168.05(12) 2_463 4_536 ? O3 Cu1 O2 91.26(11) 2_463 3_444 ? O4 Cu1 O2 89.03(11) 4_536 3_444 ? O3 Cu1 O1 88.76(11) 2_463 . ? O4 Cu1 O1 88.48(11) 4_536 . ? O2 Cu1 O1 167.96(11) 3_444 . ? O3 Cu1 O5 99.32(11) 2_463 . ? O4 Cu1 O5 92.35(11) 4_536 . ? O2 Cu1 O5 100.95(10) 3_444 . ? O1 Cu1 O5 90.92(10) . . ? O3 Cu1 Cu1 85.66(9) 2_463 3_444 ? O4 Cu1 Cu1 82.41(9) 4_536 3_444 ? O2 Cu1 Cu1 87.74(8) 3_444 3_444 ? O1 Cu1 Cu1 80.25(8) . 3_444 ? O5 Cu1 Cu1 169.81(7) . 3_444 ? C1 O1 Cu1 126.5(2) . . ? C1 O2 Cu1 121.2(2) . 3_444 ? C17 O3 Cu1 120.9(2) . 2_443 ? C17 O4 Cu1 124.7(2) . 4_535 ? C21 O5 Cu1 128.1(3) . . ? C21 O6 H6 109.4 . . ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 118.3(3) . . ? O1 C1 C2 117.4(3) . . ? C3 C2 C5 119.1(3) . . ? C3 C2 C1 121.2(3) . . ? C5 C2 C1 119.6(3) . . ? C2 C3 C4 120.9(4) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C7 C4 C3 120.7(4) . . ? C7 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C6 C5 C2 119.7(4) . . ? C6 C5 H5A 120.1 . . ? C2 C5 H5A 120.1 . . ? C5 C6 C7 121.3(4) . . ? C5 C6 H6A 119.4 . . ? C7 C6 H6A 119.4 . . ? C4 C7 C6 118.3(3) . . ? C4 C7 C8 123.2(3) . . ? C6 C7 C8 118.5(3) . . ? C9 C8 C7 106.3(3) . . ? C9 C8 C11 113.5(3) . . ? C7 C8 C11 110.3(3) . . ? C9 C8 C10 108.3(3) . . ? C7 C8 C10 112.6(3) . . ? C11 C8 C10 106.0(3) . . ? F3 C9 F1 106.9(3) . . ? F3 C9 F2 106.9(3) . . ? F1 C9 F2 106.5(4) . . ? F3 C9 C8 111.9(3) . . ? F1 C9 C8 113.2(3) . . ? F2 C9 C8 111.2(3) . . ? F4 C10 F5 106.9(3) . . ? F4 C10 F6 106.6(3) . . ? F5 C10 F6 106.6(3) . . ? F4 C10 C8 112.0(3) . . ? F5 C10 C8 113.2(3) . . ? F6 C10 C8 111.1(3) . . ? C14 C11 C12 118.6(3) . . ? C14 C11 C8 117.7(3) . . ? C12 C11 C8 123.6(3) . . ? C13 C12 C11 120.3(4) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C16 C13 C12 121.1(4) . . ? C16 C13 H13A 119.4 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C11 120.8(4) . . ? C15 C14 H14A 119.6 . . ? C11 C14 H14A 119.6 . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C13 C16 C15 119.1(3) . . ? C13 C16 C17 120.0(3) . . ? C15 C16 C17 120.8(3) . . ? O4 C17 O3 126.3(3) . . ? O4 C17 C16 116.4(3) . . ? O3 C17 C16 117.3(3) . . ? O5 C21 O6 122.7(4) . . ? O5 C21 C22 123.9(3) . . ? O6 C21 C22 113.4(3) . . ? C25 C22 C23 118.7(4) . . ? C25 C22 C21 121.2(3) . . ? C23 C22 C21 120.0(3) . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C23 C24 C27 120.6(4) . . ? C23 C24 H24A 119.7 . . ? C27 C24 H24A 119.7 . . ? C26 C25 C22 120.2(4) . . ? C26 C25 H25A 119.9 . . ? C22 C25 H25A 119.9 . . ? C25 C26 C27 121.3(3) . . ? C25 C26 H26A 119.3 . . ? C27 C26 H26A 119.3 . . ? C24 C27 C26 118.2(4) . . ? C24 C27 C28 123.9(3) . . ? C26 C27 C28 117.9(3) . . ? C29 C28 C29 108.7(5) 2_554 . ? C29 C28 C27 112.4(2) 2_554 . ? C29 C28 C27 106.7(2) . . ? C29 C28 C27 106.7(2) 2_554 2_554 ? C29 C28 C27 112.4(2) . 2_554 ? C27 C28 C27 110.0(4) . 2_554 ? F9 C29 F8 106.2(4) . . ? F9 C29 F7 107.2(4) . . ? F8 C29 F7 106.8(4) . . ? F9 C29 C28 111.6(3) . . ? F8 C29 C28 111.3(3) . . ? F7 C29 C28 113.4(4) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.718 _refine_diff_density_min -1.110 _refine_diff_density_rms 0.108