# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,5,6,7-tetrafluoro-1,2,3-tris(pentafluorophenyl)-1-boraindene' ; _chemical_name_common Perfluoroarylbenzoborole _chemical_melting_point Unknown _chemical_formula_moiety 'C26 B F19' _chemical_formula_sum 'C26 B F19' _chemical_formula_weight 684.07 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.0400(4) _cell_length_b 8.8720(3) _cell_length_c 23.9650(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.6140(10) _cell_angle_gamma 90.00 _cell_volume 2299.24(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5343 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.976 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5561 _exptl_absorpt_correction_T_max 0.8514 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; 'None' ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 9564 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.37 _reflns_number_total 5161 _reflns_number_gt 4054 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0750P)^2^+5.5591P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5161 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1727 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 F17 F 0.9993(2) -0.2859(3) 0.10664(11) 0.0343(5) Uani 1 1 d . . . F1 F 0.5087(2) -0.4021(3) 0.05574(11) 0.0365(6) Uani 1 1 d . . . F5 F 0.1080(2) -0.0177(3) 0.14624(11) 0.0344(5) Uani 1 1 d . . . F11 F 0.6450(2) 0.3497(3) 0.29238(10) 0.0404(6) Uani 1 1 d . . . F15 F 0.7006(2) -0.1319(3) 0.20787(10) 0.0362(6) Uani 1 1 d . . . F4 F 0.0863(2) -0.0769(3) 0.03620(10) 0.0341(5) Uani 1 1 d . . . F19 F 0.6092(2) -0.1407(3) 0.00717(9) 0.0337(5) Uani 1 1 d . . . F7 F 0.0287(2) 0.4769(3) 0.19224(12) 0.0438(6) Uani 1 1 d . . . F16 F 0.9314(2) -0.2239(3) 0.20674(10) 0.0372(6) Uani 1 1 d . . . F18 F 0.8405(2) -0.2311(3) 0.00697(10) 0.0336(5) Uani 1 1 d . . . F3 F 0.0839(2) -0.3493(3) -0.01226(12) 0.0434(6) Uani 1 1 d . . . F9 F 0.3781(2) 0.3741(3) 0.11817(12) 0.0378(6) Uani 1 1 d . . . F2 F 0.2944(2) -0.5110(3) -0.00066(11) 0.0414(6) Uani 1 1 d . . . F14 F 0.6428(2) 0.2066(3) 0.07308(10) 0.0417(6) Uani 1 1 d . . . F6 F -0.0380(2) 0.1822(3) 0.18219(12) 0.0409(6) Uani 1 1 d . . . F12 F 0.7827(3) 0.5111(3) 0.23212(12) 0.0467(7) Uani 1 1 d . . . F10 F 0.5001(2) 0.1245(3) 0.24273(11) 0.0393(6) Uani 1 1 d . . . F8 F 0.2367(2) 0.5709(3) 0.15906(12) 0.0436(6) Uani 1 1 d . . . F13 F 0.7832(3) 0.4349(3) 0.12244(12) 0.0489(7) Uani 1 1 d . . . C25 C 0.8057(3) -0.2078(4) 0.05629(16) 0.0263(8) Uani 1 1 d . . . C24 C 0.8879(3) -0.2318(4) 0.10687(17) 0.0274(8) Uani 1 1 d . . . C1 C 0.4810(3) 0.0428(4) 0.12671(15) 0.0240(7) Uani 1 1 d . . . C2 C 0.5182(3) -0.0870(4) 0.10568(15) 0.0239(7) Uani 1 1 d . . . C7 C 0.1926(3) -0.1537(4) 0.04388(16) 0.0275(8) Uani 1 1 d . . . C10 C 0.2772(3) 0.3223(4) 0.13484(17) 0.0282(8) Uani 1 1 d . . . C17 C 0.6434(4) 0.3157(4) 0.23818(16) 0.0293(8) Uani 1 1 d . . . C21 C 0.6470(3) -0.1341(4) 0.10734(16) 0.0236(7) Uani 1 1 d . . . C26 C 0.6878(3) -0.1606(4) 0.05713(16) 0.0258(8) Uani 1 1 d . . . C4 C 0.4072(3) -0.3169(4) 0.05289(16) 0.0260(8) Uani 1 1 d . . . C20 C 0.6423(4) 0.2403(5) 0.12755(17) 0.0288(8) Uani 1 1 d . . . C9 C 0.2497(3) 0.1686(4) 0.13049(16) 0.0260(8) Uani 1 1 d . . . C15 C 0.5667(3) 0.1589(4) 0.15636(16) 0.0253(7) Uani 1 1 d . . . C8 C 0.3002(3) -0.0951(4) 0.07470(15) 0.0242(7) Uani 1 1 d . . . C6 C 0.1890(3) -0.2945(5) 0.01815(16) 0.0300(8) Uani 1 1 d . . . C11 C 0.2048(4) 0.4253(4) 0.15478(18) 0.0320(9) Uani 1 1 d . . . B1 B 0.3356(4) 0.0496(5) 0.11077(18) 0.0263(9) Uani 1 1 d . . . C13 C 0.0652(4) 0.2287(5) 0.16667(17) 0.0306(8) Uani 1 1 d . . . C18 C 0.7143(4) 0.3961(5) 0.20787(18) 0.0335(9) Uani 1 1 d . . . C3 C 0.4108(3) -0.1772(4) 0.07657(15) 0.0236(7) Uani 1 1 d . . . C16 C 0.5701(3) 0.2000(4) 0.21239(16) 0.0274(8) Uani 1 1 d . . . C5 C 0.2948(4) -0.3756(5) 0.02346(17) 0.0309(8) Uani 1 1 d . . . C14 C 0.1401(3) 0.1279(4) 0.14696(17) 0.0280(8) Uani 1 1 d . . . C23 C 0.8514(3) -0.2032(4) 0.15760(16) 0.0279(8) Uani 1 1 d . . . C12 C 0.0980(4) 0.3782(5) 0.17133(18) 0.0325(9) Uani 1 1 d . . . C19 C 0.7140(4) 0.3575(5) 0.15224(18) 0.0340(9) Uani 1 1 d . . . C22 C 0.7336(4) -0.1546(4) 0.15767(16) 0.0271(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 F17 0.0257(11) 0.0359(13) 0.0415(14) 0.0002(11) 0.0076(10) 0.0038(9) F1 0.0309(12) 0.0310(12) 0.0494(15) -0.0090(11) 0.0121(11) 0.0022(10) F5 0.0344(12) 0.0310(12) 0.0395(14) -0.0035(10) 0.0117(10) -0.0059(10) F11 0.0550(15) 0.0407(14) 0.0258(12) -0.0125(10) 0.0087(11) -0.0034(12) F15 0.0372(13) 0.0496(15) 0.0215(11) -0.0021(10) 0.0047(9) 0.0079(11) F4 0.0228(10) 0.0405(13) 0.0357(13) 0.0005(11) -0.0015(9) 0.0013(10) F19 0.0295(11) 0.0504(15) 0.0194(11) 0.0026(10) 0.0010(9) -0.0016(10) F7 0.0486(15) 0.0384(14) 0.0479(16) -0.0029(12) 0.0179(12) 0.0136(12) F16 0.0337(12) 0.0462(14) 0.0275(12) 0.0031(11) -0.0035(9) 0.0062(11) F18 0.0343(12) 0.0428(13) 0.0265(12) -0.0039(10) 0.0129(9) -0.0038(10) F3 0.0308(12) 0.0537(16) 0.0433(15) -0.0167(13) 0.0017(11) -0.0116(11) F9 0.0322(12) 0.0301(12) 0.0524(16) 0.0070(11) 0.0118(11) -0.0025(10) F2 0.0449(14) 0.0360(13) 0.0449(15) -0.0185(12) 0.0130(12) -0.0083(11) F14 0.0501(15) 0.0525(16) 0.0240(12) -0.0025(11) 0.0113(10) -0.0191(12) F6 0.0325(12) 0.0464(15) 0.0473(15) -0.0014(12) 0.0162(11) 0.0004(11) F12 0.0565(16) 0.0402(14) 0.0404(15) -0.0113(12) 0.0024(12) -0.0206(12) F10 0.0463(13) 0.0450(14) 0.0309(13) -0.0049(11) 0.0181(11) -0.0122(12) F8 0.0475(15) 0.0245(12) 0.0592(18) -0.0010(12) 0.0119(13) 0.0016(11) F13 0.0535(16) 0.0540(17) 0.0399(15) 0.0037(13) 0.0114(12) -0.0277(13) C25 0.0297(18) 0.0253(18) 0.0259(18) -0.0024(15) 0.0099(15) -0.0052(15) C24 0.0202(17) 0.0263(18) 0.035(2) -0.0004(16) 0.0031(15) -0.0012(14) C1 0.0248(17) 0.0280(18) 0.0189(16) 0.0013(14) 0.0035(13) -0.0030(14) C2 0.0251(17) 0.0271(18) 0.0188(16) 0.0016(14) 0.0030(13) -0.0005(14) C7 0.0266(18) 0.033(2) 0.0227(18) 0.0047(15) 0.0042(14) 0.0007(16) C10 0.0262(18) 0.0290(19) 0.0292(19) 0.0033(16) 0.0047(15) 0.0015(15) C17 0.036(2) 0.0279(19) 0.0229(18) -0.0063(15) 0.0031(15) 0.0008(16) C21 0.0233(17) 0.0233(17) 0.0243(18) -0.0025(14) 0.0048(14) -0.0030(14) C26 0.0249(17) 0.0303(19) 0.0209(17) 0.0000(15) 0.0013(14) -0.0040(15) C4 0.0290(18) 0.0285(18) 0.0222(18) -0.0021(15) 0.0088(14) -0.0012(15) C20 0.0295(19) 0.035(2) 0.0226(18) -0.0028(16) 0.0060(14) -0.0049(16) C9 0.0241(17) 0.0303(19) 0.0216(17) -0.0006(15) -0.0001(14) 0.0016(15) C15 0.0225(16) 0.0279(18) 0.0242(18) -0.0012(15) 0.0017(14) 0.0018(14) C8 0.0267(17) 0.0269(18) 0.0196(17) 0.0021(14) 0.0058(13) -0.0016(15) C6 0.0265(18) 0.038(2) 0.0249(19) -0.0034(16) 0.0037(15) -0.0117(16) C11 0.035(2) 0.0248(18) 0.033(2) 0.0025(16) 0.0005(16) 0.0023(16) B1 0.029(2) 0.029(2) 0.0213(19) 0.0028(17) 0.0048(16) -0.0027(17) C13 0.0266(18) 0.038(2) 0.028(2) 0.0027(17) 0.0055(15) 0.0028(16) C18 0.032(2) 0.029(2) 0.036(2) -0.0033(17) -0.0032(17) -0.0041(16) C3 0.0261(17) 0.0268(17) 0.0184(16) -0.0003(14) 0.0052(13) -0.0043(15) C16 0.0288(18) 0.0292(19) 0.0252(18) 0.0015(15) 0.0080(14) 0.0012(15) C5 0.034(2) 0.0299(19) 0.031(2) -0.0082(16) 0.0108(16) -0.0093(16) C14 0.0281(18) 0.0265(18) 0.0273(19) 0.0017(15) 0.0007(15) -0.0020(15) C23 0.0287(18) 0.0272(18) 0.0243(18) 0.0038(15) -0.0030(14) -0.0007(15) C12 0.034(2) 0.033(2) 0.029(2) -0.0001(16) 0.0034(16) 0.0124(17) C19 0.032(2) 0.039(2) 0.030(2) 0.0040(18) 0.0042(16) -0.0089(18) C22 0.0318(19) 0.0287(19) 0.0212(17) -0.0026(15) 0.0067(14) -0.0007(15) _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 F17 C24 1.321(4) . ? F1 C4 1.342(4) . ? F5 C14 1.339(4) . ? F11 C17 1.330(4) . ? F15 C22 1.340(4) . ? F4 C7 1.337(4) . ? F19 C26 1.341(4) . ? F7 C12 1.326(5) . ? F16 C23 1.335(4) . ? F18 C25 1.330(4) . ? F3 C6 1.332(4) . ? F9 C10 1.338(4) . ? F2 C5 1.333(5) . ? F14 C20 1.340(4) . ? F6 C13 1.333(5) . ? F12 C18 1.331(5) . ? F10 C16 1.342(4) . ? F8 C11 1.337(5) . ? F13 C19 1.336(5) . ? C25 C26 1.372(5) . ? C25 C24 1.377(5) . ? C24 C23 1.379(6) . ? C1 C2 1.353(5) . ? C1 C15 1.480(5) . ? C1 B1 1.575(5) . ? C2 C21 1.476(5) . ? C2 C3 1.483(5) . ? C7 C8 1.369(5) . ? C7 C6 1.390(6) . ? C10 C11 1.362(6) . ? C10 C9 1.396(5) . ? C17 C18 1.371(6) . ? C17 C16 1.374(5) . ? C21 C26 1.387(5) . ? C21 C22 1.392(5) . ? C4 C3 1.361(5) . ? C4 C5 1.398(5) . ? C20 C19 1.367(6) . ? C20 C15 1.388(5) . ? C9 C14 1.394(5) . ? C9 B1 1.555(6) . ? C15 C16 1.385(5) . ? C8 C3 1.415(5) . ? C8 B1 1.553(6) . ? C6 C5 1.356(6) . ? C11 C12 1.382(6) . ? C13 C14 1.365(6) . ? C13 C12 1.373(6) . ? C18 C19 1.376(6) . ? C23 C22 1.371(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 F18 C25 C26 120.3(3) . . ? F18 C25 C24 120.1(3) . . ? C26 C25 C24 119.6(3) . . ? F17 C24 C25 120.1(3) . . ? F17 C24 C23 120.5(3) . . ? C25 C24 C23 119.3(3) . . ? C2 C1 C15 123.9(3) . . ? C2 C1 B1 108.3(3) . . ? C15 C1 B1 127.7(3) . . ? C1 C2 C21 126.5(3) . . ? C1 C2 C3 111.1(3) . . ? C21 C2 C3 122.3(3) . . ? F4 C7 C8 121.5(4) . . ? F4 C7 C6 116.8(3) . . ? C8 C7 C6 121.6(4) . . ? F9 C10 C11 117.2(4) . . ? F9 C10 C9 119.7(3) . . ? C11 C10 C9 123.2(4) . . ? F11 C17 C18 120.1(4) . . ? F11 C17 C16 120.0(4) . . ? C18 C17 C16 119.8(4) . . ? C26 C21 C22 116.4(3) . . ? C26 C21 C2 120.2(3) . . ? C22 C21 C2 123.4(3) . . ? F19 C26 C25 118.2(3) . . ? F19 C26 C21 119.2(3) . . ? C25 C26 C21 122.6(3) . . ? F1 C4 C3 122.5(3) . . ? F1 C4 C5 117.6(3) . . ? C3 C4 C5 119.9(4) . . ? F14 C20 C19 118.4(4) . . ? F14 C20 C15 119.3(3) . . ? C19 C20 C15 122.3(4) . . ? C14 C9 C10 114.8(3) . . ? C14 C9 B1 121.8(3) . . ? C10 C9 B1 123.3(3) . . ? C16 C15 C20 116.3(3) . . ? C16 C15 C1 122.6(3) . . ? C20 C15 C1 120.9(3) . . ? C7 C8 C3 118.1(3) . . ? C7 C8 B1 135.1(4) . . ? C3 C8 B1 106.8(3) . . ? F3 C6 C5 119.8(4) . . ? F3 C6 C7 120.9(4) . . ? C5 C6 C7 119.3(3) . . ? F8 C11 C10 120.7(4) . . ? F8 C11 C12 119.8(4) . . ? C10 C11 C12 119.5(4) . . ? C8 B1 C9 129.1(3) . . ? C8 B1 C1 103.5(3) . . ? C9 B1 C1 127.3(3) . . ? F6 C13 C14 120.3(4) . . ? F6 C13 C12 120.1(4) . . ? C14 C13 C12 119.5(4) . . ? F12 C18 C17 120.1(4) . . ? F12 C18 C19 120.3(4) . . ? C17 C18 C19 119.6(4) . . ? C4 C3 C8 120.2(3) . . ? C4 C3 C2 129.9(3) . . ? C8 C3 C2 109.9(3) . . ? F10 C16 C17 118.7(4) . . ? F10 C16 C15 119.2(3) . . ? C17 C16 C15 122.1(4) . . ? F2 C5 C6 120.7(4) . . ? F2 C5 C4 118.7(4) . . ? C6 C5 C4 120.6(4) . . ? F5 C14 C13 117.3(3) . . ? F5 C14 C9 119.3(3) . . ? C13 C14 C9 123.3(4) . . ? F16 C23 C22 120.1(4) . . ? F16 C23 C24 119.6(3) . . ? C22 C23 C24 120.3(3) . . ? F7 C12 C13 120.4(4) . . ? F7 C12 C11 119.9(4) . . ? C13 C12 C11 119.7(4) . . ? F13 C19 C20 120.2(4) . . ? F13 C19 C18 120.0(4) . . ? C20 C19 C18 119.8(4) . . ? F15 C22 C23 118.5(3) . . ? F15 C22 C21 119.7(3) . . ? C23 C22 C21 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.366 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 956378' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1215 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'bis(2,3,4,5-tetrafluorophenyl) zirconocene' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F8 Zr' _chemical_formula_sum 'C22 H12 F8 Zr' _chemical_formula_weight 519.54 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.7831(3) _cell_length_b 13.7152(3) _cell_length_c 20.0961(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3798.82(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15940 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9490 _exptl_absorpt_correction_T_max 0.9614 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; None ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 15940 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4350 _reflns_number_gt 3209 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0428P)^2^+9.1888P] 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 4350 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.232 _refine_ls_restrained_S_all 1.232 _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 C13 C 0.3944(4) 0.8700(4) 0.3201(3) 0.0417(13) Uani 1 1 d . . . C11 C 0.2321(3) 0.8175(3) 0.3483(2) 0.0318(10) Uani 1 1 d . . . C12 C 0.3276(3) 0.8337(3) 0.3643(2) 0.0323(11) Uani 1 1 d . . . C16 C 0.2064(4) 0.8439(3) 0.2835(3) 0.0397(12) Uani 1 1 d . . . H16 H 0.1410 0.8367 0.2696 0.048 Uiso 1 1 calc R . . C15 C 0.2735(4) 0.8800(4) 0.2395(3) 0.0453(13) Uani 1 1 d . . . C14 C 0.3680(4) 0.8936(4) 0.2571(3) 0.0432(13) Uani 1 1 d . . . C7 C 0.1449(4) 0.9172(4) 0.4767(3) 0.0408(12) Uani 1 1 d . . . H7 H 0.2096 0.9405 0.4798 0.049 Uiso 1 1 calc R . . C8 C 0.0795(4) 0.9358(3) 0.4246(3) 0.0393(12) Uani 1 1 d . . . H8 H 0.0922 0.9739 0.3861 0.047 Uiso 1 1 calc R . . C9 C -0.0077(4) 0.8879(4) 0.4394(3) 0.0407(12) Uani 1 1 d . . . H9 H -0.0646 0.8884 0.4127 0.049 Uiso 1 1 calc R . . C10 C 0.0034(4) 0.8398(4) 0.4994(3) 0.0406(12) Uani 1 1 d . . . H10 H -0.0443 0.8009 0.5209 0.049 Uiso 1 1 calc R . . C6 C 0.0974(4) 0.8586(4) 0.5231(3) 0.0406(12) Uani 1 1 d . . . H6 H 0.1241 0.8353 0.5637 0.049 Uiso 1 1 calc R . . C2 C 0.2440(4) 0.6284(3) 0.4356(3) 0.0375(12) Uani 1 1 d . . . H2 H 0.3056 0.6384 0.4155 0.045 Uiso 1 1 calc R . . C3 C 0.2171(4) 0.6589(4) 0.4986(3) 0.0448(13) Uani 1 1 d . . . H3 H 0.2562 0.6945 0.5290 0.054 Uiso 1 1 calc R . . C4 C 0.1209(4) 0.6274(4) 0.5097(3) 0.0472(14) Uani 1 1 d . . . H4 H 0.0841 0.6375 0.5491 0.057 Uiso 1 1 calc R . . C5 C 0.0893(4) 0.5789(3) 0.4531(3) 0.0400(12) Uani 1 1 d . . . H5 H 0.0274 0.5499 0.4468 0.048 Uiso 1 1 calc R . . C1 C 0.1654(4) 0.5806(3) 0.4068(3) 0.0376(12) Uani 1 1 d . . . H1 H 0.1637 0.5538 0.3632 0.045 Uiso 1 1 calc R . . C17 C -0.0043(3) 0.7026(3) 0.3478(2) 0.0329(11) Uani 1 1 d . . . C22 C 0.0204(4) 0.6793(3) 0.2820(3) 0.0379(11) Uani 1 1 d . . . H22 H 0.0854 0.6884 0.2678 0.046 Uiso 1 1 calc R . . C18 C -0.0986(4) 0.6839(4) 0.3634(3) 0.0402(12) Uani 1 1 d . . . C19 C -0.1661(4) 0.6471(4) 0.3201(3) 0.0454(13) Uani 1 1 d . . . C21 C -0.0460(4) 0.6439(3) 0.2378(3) 0.0418(13) Uani 1 1 d . . . C20 C -0.1389(4) 0.6273(4) 0.2564(3) 0.0419(13) Uani 1 1 d . . . F1 F 0.3601(2) 0.8170(2) 0.42679(15) 0.0457(7) Uani 1 1 d . . . F2 F 0.4870(2) 0.8845(3) 0.33931(18) 0.0586(9) Uani 1 1 d . . . F3 F 0.4329(3) 0.9297(2) 0.21435(17) 0.0640(10) Uani 1 1 d . . . F4 F 0.2468(3) 0.9031(3) 0.17675(16) 0.0697(11) Uani 1 1 d . . . F8 F -0.0206(3) 0.6250(2) 0.17441(15) 0.0592(9) Uani 1 1 d . . . F7 F -0.2036(3) 0.5912(2) 0.21279(19) 0.0659(10) Uani 1 1 d . . . F6 F -0.2580(3) 0.6311(3) 0.33875(19) 0.0685(10) Uani 1 1 d . . . F5 F -0.1306(2) 0.6965(3) 0.42694(17) 0.0581(9) Uani 1 1 d . . . Zr1 Zr 0.11501(3) 0.75562(3) 0.42196(2) 0.02637(14) 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 C13 0.032(3) 0.031(3) 0.061(4) -0.010(2) 0.009(3) -0.004(2) C11 0.035(3) 0.023(2) 0.037(3) 0.0011(19) 0.008(2) 0.0017(18) C12 0.037(3) 0.024(2) 0.036(3) -0.0011(19) 0.002(2) 0.0025(19) C16 0.044(3) 0.030(2) 0.044(3) 0.002(2) 0.002(2) -0.006(2) C15 0.069(4) 0.038(3) 0.030(3) 0.005(2) 0.007(3) -0.001(3) C14 0.050(3) 0.034(3) 0.046(3) -0.003(2) 0.021(3) -0.007(2) C7 0.043(3) 0.031(2) 0.048(3) -0.012(2) 0.006(3) -0.003(2) C8 0.061(3) 0.022(2) 0.035(3) -0.001(2) 0.011(3) 0.006(2) C9 0.043(3) 0.036(3) 0.043(3) -0.009(2) -0.001(2) 0.010(2) C10 0.043(3) 0.037(3) 0.041(3) -0.010(2) 0.011(2) -0.004(2) C6 0.059(4) 0.035(3) 0.027(3) -0.005(2) 0.002(2) 0.005(2) C2 0.037(3) 0.027(2) 0.049(3) 0.007(2) -0.003(2) 0.006(2) C3 0.056(3) 0.032(3) 0.046(3) 0.005(2) -0.019(3) 0.001(2) C4 0.070(4) 0.037(3) 0.035(3) 0.011(2) 0.002(3) 0.005(3) C5 0.044(3) 0.028(2) 0.047(3) 0.010(2) 0.002(3) -0.006(2) C1 0.049(3) 0.021(2) 0.043(3) -0.001(2) -0.002(2) 0.005(2) C17 0.036(3) 0.030(2) 0.033(3) -0.0010(19) -0.002(2) 0.003(2) C22 0.042(3) 0.034(2) 0.038(3) 0.000(2) -0.002(2) 0.001(2) C18 0.042(3) 0.041(3) 0.038(3) -0.002(2) 0.001(2) 0.000(2) C19 0.039(3) 0.042(3) 0.055(4) 0.001(3) -0.003(3) -0.002(2) C21 0.065(4) 0.034(3) 0.027(2) -0.001(2) -0.003(3) -0.001(2) C20 0.052(3) 0.033(2) 0.040(3) 0.002(2) -0.021(3) -0.010(2) F1 0.0456(18) 0.0461(17) 0.0453(19) 0.0054(14) -0.0075(15) -0.0032(13) F2 0.0400(19) 0.063(2) 0.073(3) -0.0038(18) 0.0048(17) -0.0105(16) F3 0.080(3) 0.056(2) 0.056(2) -0.0028(16) 0.0323(19) -0.0202(18) F4 0.093(3) 0.074(3) 0.042(2) 0.0209(17) -0.003(2) -0.014(2) F8 0.087(3) 0.057(2) 0.0341(18) -0.0070(15) -0.0065(17) -0.0049(19) F7 0.074(2) 0.055(2) 0.068(2) -0.0011(17) -0.036(2) -0.0160(17) F6 0.0376(19) 0.088(3) 0.080(3) -0.005(2) 0.0001(18) -0.0159(18) F5 0.052(2) 0.073(2) 0.050(2) -0.0153(17) 0.0112(16) -0.0067(17) Zr1 0.0309(2) 0.0230(2) 0.0252(2) 0.00023(18) 0.00133(18) -0.00046(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 C13 F2 1.348(6) . ? C13 C14 1.356(8) . ? C13 C12 1.372(7) . ? C11 C12 1.373(7) . ? C11 C16 1.397(7) . ? C11 Zr1 2.348(5) . ? C12 F1 1.353(5) . ? C16 C15 1.372(7) . ? C16 H16 0.9500 . ? C15 F4 1.351(6) . ? C15 C14 1.363(8) . ? C14 F3 1.336(6) . ? C7 C6 1.395(7) . ? C7 C8 1.405(8) . ? C7 Zr1 2.509(5) . ? C7 H7 0.9500 . ? C8 C9 1.401(7) . ? C8 Zr1 2.519(4) . ? C8 H8 0.9500 . ? C9 C10 1.384(7) . ? C9 Zr1 2.505(5) . ? C9 H9 0.9500 . ? C10 C6 1.404(7) . ? C10 Zr1 2.475(5) . ? C10 H10 0.9500 . ? C6 Zr1 2.487(5) . ? C6 H6 0.9500 . ? C2 C3 1.385(7) . ? C2 C1 1.392(7) . ? C2 Zr1 2.506(5) . ? C2 H2 0.9500 . ? C3 C4 1.412(8) . ? C3 Zr1 2.473(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(8) . ? C4 Zr1 2.492(5) . ? C4 H4 0.9500 . ? C5 C1 1.402(7) . ? C5 Zr1 2.527(5) . ? C5 H5 0.9500 . ? C1 Zr1 2.517(4) . ? C1 H1 0.9500 . ? C17 C18 1.363(7) . ? C17 C22 1.401(7) . ? C17 Zr1 2.336(5) . ? C22 C21 1.364(7) . ? C22 H22 0.9500 . ? C18 F5 1.361(6) . ? C18 C19 1.371(7) . ? C19 F6 1.339(6) . ? C19 C20 1.360(8) . ? C21 F8 1.346(6) . ? C21 C20 1.353(8) . ? C20 F7 1.345(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 F2 C13 C14 119.1(5) . . ? F2 C13 C12 120.2(5) . . ? C14 C13 C12 120.7(5) . . ? C12 C11 C16 114.7(4) . . ? C12 C11 Zr1 124.8(4) . . ? C16 C11 Zr1 120.5(4) . . ? F1 C12 C13 116.1(5) . . ? F1 C12 C11 120.4(4) . . ? C13 C12 C11 123.4(5) . . ? C15 C16 C11 121.6(5) . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? F4 C15 C14 118.1(5) . . ? F4 C15 C16 120.2(5) . . ? C14 C15 C16 121.7(5) . . ? F3 C14 C13 120.6(5) . . ? F3 C14 C15 121.6(5) . . ? C13 C14 C15 117.8(5) . . ? C6 C7 C8 107.6(5) . . ? C6 C7 Zr1 72.9(3) . . ? C8 C7 Zr1 74.2(3) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? Zr1 C7 H7 118.7 . . ? C9 C8 C7 107.9(5) . . ? C9 C8 Zr1 73.2(3) . . ? C7 C8 Zr1 73.4(3) . . ? C9 C8 H8 126.1 . . ? C7 C8 H8 126.1 . . ? Zr1 C8 H8 119.2 . . ? C10 C9 C8 108.3(5) . . ? C10 C9 Zr1 72.7(3) . . ? C8 C9 Zr1 74.4(3) . . ? C10 C9 H9 125.9 . . ? C8 C9 H9 125.9 . . ? Zr1 C9 H9 119.0 . . ? C9 C10 C6 108.1(5) . . ? C9 C10 Zr1 75.1(3) . . ? C6 C10 Zr1 74.0(3) . . ? C9 C10 H10 126.0 . . ? C6 C10 H10 126.0 . . ? Zr1 C10 H10 117.0 . . ? C7 C6 C10 108.2(5) . . ? C7 C6 Zr1 74.7(3) . . ? C10 C6 Zr1 73.1(3) . . ? C7 C6 H6 125.9 . . ? C10 C6 H6 125.9 . . ? Zr1 C6 H6 118.3 . . ? C3 C2 C1 108.3(5) . . ? C3 C2 Zr1 72.5(3) . . ? C1 C2 Zr1 74.3(3) . . ? C3 C2 H2 125.9 . . ? C1 C2 H2 125.9 . . ? Zr1 C2 H2 119.1 . . ? C2 C3 C4 107.7(5) . . ? C2 C3 Zr1 75.2(3) . . ? C4 C3 Zr1 74.2(3) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? Zr1 C3 H3 116.5 . . ? C5 C4 C3 108.1(5) . . ? C5 C4 Zr1 75.3(3) . . ? C3 C4 Zr1 72.7(3) . . ? C5 C4 H4 125.9 . . ? C3 C4 H4 125.9 . . ? Zr1 C4 H4 117.9 . . ? C4 C5 C1 107.6(5) . . ? C4 C5 Zr1 72.6(3) . . ? C1 C5 Zr1 73.5(3) . . ? C4 C5 H5 126.2 . . ? C1 C5 H5 126.2 . . ? Zr1 C5 H5 119.6 . . ? C2 C1 C5 108.3(5) . . ? C2 C1 Zr1 73.5(3) . . ? C5 C1 Zr1 74.3(3) . . ? C2 C1 H1 125.9 . . ? C5 C1 H1 125.9 . . ? Zr1 C1 H1 118.3 . . ? C18 C17 C22 114.0(5) . . ? C18 C17 Zr1 125.7(4) . . ? C22 C17 Zr1 120.2(4) . . ? C21 C22 C17 122.2(5) . . ? C21 C22 H22 118.9 . . ? C17 C22 H22 118.9 . . ? F5 C18 C17 120.1(5) . . ? F5 C18 C19 115.0(5) . . ? C17 C18 C19 124.7(5) . . ? F6 C19 C20 119.5(5) . . ? F6 C19 C18 121.6(5) . . ? C20 C19 C18 118.9(5) . . ? F8 C21 C20 118.4(5) . . ? F8 C21 C22 120.7(5) . . ? C20 C21 C22 120.9(5) . . ? F7 C20 C21 120.6(5) . . ? F7 C20 C19 120.2(5) . . ? C21 C20 C19 119.2(5) . . ? C17 Zr1 C11 101.19(17) . . ? C17 Zr1 C3 129.14(17) . . ? C11 Zr1 C3 101.29(19) . . ? C17 Zr1 C10 96.28(17) . . ? C11 Zr1 C10 130.91(16) . . ? C3 Zr1 C10 102.2(2) . . ? C17 Zr1 C6 129.05(18) . . ? C11 Zr1 C6 112.13(17) . . ? C3 Zr1 C6 81.42(18) . . ? C10 Zr1 C6 32.88(17) . . ? C17 Zr1 C4 104.76(18) . . ? C11 Zr1 C4 132.76(18) . . ? C3 Zr1 C4 33.05(18) . . ? C10 Zr1 C4 84.51(19) . . ? C6 Zr1 C4 79.95(18) . . ? C17 Zr1 C9 80.76(17) . . ? C11 Zr1 C9 106.85(17) . . ? C3 Zr1 C9 133.30(19) . . ? C10 Zr1 C9 32.27(17) . . ? C6 Zr1 C9 53.76(18) . . ? C4 Zr1 C9 115.75(19) . . ? C17 Zr1 C2 110.64(16) . . ? C11 Zr1 C2 80.38(16) . . ? C3 Zr1 C2 32.29(17) . . ? C10 Zr1 C2 134.21(18) . . ? C6 Zr1 C2 112.03(17) . . ? C4 Zr1 C2 53.73(18) . . ? C9 Zr1 C2 165.48(17) . . ? C17 Zr1 C7 132.12(17) . . ? C11 Zr1 C7 81.03(17) . . ? C3 Zr1 C7 96.17(18) . . ? C10 Zr1 C7 54.11(17) . . ? C6 Zr1 C7 32.41(17) . . ? C4 Zr1 C7 107.93(19) . . ? C9 Zr1 C7 53.81(18) . . ? C2 Zr1 C7 116.78(17) . . ? C17 Zr1 C1 79.64(16) . . ? C11 Zr1 C1 94.51(16) . . ? C3 Zr1 C1 53.61(17) . . ? C10 Zr1 C1 133.86(17) . . ? C6 Zr1 C1 131.86(17) . . ? C4 Zr1 C1 53.41(18) . . ? C9 Zr1 C1 153.39(18) . . ? C2 Zr1 C1 32.18(16) . . ? C7 Zr1 C1 148.24(18) . . ? C17 Zr1 C8 100.48(17) . . ? C11 Zr1 C8 77.98(16) . . ? C3 Zr1 C8 128.60(18) . . ? C10 Zr1 C8 53.75(17) . . ? C6 Zr1 C8 53.65(17) . . ? C4 Zr1 C8 133.15(18) . . ? C9 Zr1 C8 32.39(17) . . ? C2 Zr1 C8 144.90(18) . . ? C7 Zr1 C8 32.46(17) . . ? C1 Zr1 C8 172.40(17) . . ? C17 Zr1 C5 76.18(17) . . ? C11 Zr1 C5 126.79(16) . . ? C3 Zr1 C5 53.90(18) . . ? C10 Zr1 C5 101.81(17) . . ? C6 Zr1 C5 109.17(18) . . ? C4 Zr1 C5 32.08(18) . . ? C9 Zr1 C5 124.44(18) . . ? C2 Zr1 C5 53.49(17) . . ? C7 Zr1 C5 139.59(19) . . ? C1 Zr1 C5 32.28(17) . . ? C8 Zr1 C5 155.23(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.540 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 956379' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1201 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H10 F14 Zr' _chemical_formula_sum 'C30 H10 F14 Zr' _chemical_formula_weight 727.60 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 '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/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 8.4551(3) _cell_length_b 16.9172(5) _cell_length_c 17.7991(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.924(2) _cell_angle_gamma 90.00 _cell_volume 2536.45(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11213 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.905 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9463 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; None ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 11213 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5779 _reflns_number_gt 4351 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0000P)^2^+7.5867P] 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 5779 _refine_ls_number_parameters 446 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 Zr1 Zr -0.14328(4) 0.12312(2) 0.73207(2) 0.02451(10) Uani 1 1 d . . . F1 F -0.2127(3) 0.19559(16) 0.91110(13) 0.0423(6) Uani 1 1 d . . . F2 F -0.0773(3) 0.31692(17) 0.99216(13) 0.0486(7) Uani 1 1 d . . . F3 F 0.1149(3) 0.41952(16) 0.92669(14) 0.0483(7) Uani 1 1 d . . . F4 F 0.1722(3) 0.40404(15) 0.78369(14) 0.0421(6) Uani 1 1 d . . . F5 F 0.1701(3) 0.08919(16) 0.58904(15) 0.0493(7) Uani 1 1 d . . . F6 F 0.1738(4) 0.06581(17) 0.44077(16) 0.0600(8) Uani 1 1 d . . . F7 F 0.0099(4) 0.16349(18) 0.34154(14) 0.0589(8) Uani 1 1 d . . . F8 F -0.1660(3) 0.28205(16) 0.39281(14) 0.0493(7) Uani 1 1 d . . . F9 F -0.1831(3) 0.30288(14) 0.54053(13) 0.0376(6) Uani 1 1 d . . . F10 F 0.3277(3) 0.25999(16) 0.62660(15) 0.0451(7) Uani 1 1 d . . . F11 F 0.4591(3) 0.37114(19) 0.54443(15) 0.0541(8) Uani 1 1 d . . . F12 F 0.3042(4) 0.51012(17) 0.51471(14) 0.0540(8) Uani 1 1 d . . . F13 F 0.0270(4) 0.53884(15) 0.57497(14) 0.0483(7) Uani 1 1 d . . . F14 F -0.1040(3) 0.42742(14) 0.65756(13) 0.0375(6) Uani 1 1 d . . . C1 C 0.0678(6) 0.0819(3) 0.8310(3) 0.0426(12) Uani 1 1 d . . . C2 C -0.0593(6) 0.0294(3) 0.8353(3) 0.0396(11) Uani 1 1 d . . . C3 C -0.0710(6) -0.0158(3) 0.7694(3) 0.0388(11) Uani 1 1 d . . . C4 C 0.0444(6) 0.0106(3) 0.7241(3) 0.0395(11) Uani 1 1 d . . . C5 C 0.1308(5) 0.0713(3) 0.7621(3) 0.0418(11) Uani 1 1 d . . . C6 C -0.4253(6) 0.1033(5) 0.7495(4) 0.064(2) Uani 1 1 d . . . C7 C -0.3943(7) 0.0537(4) 0.6927(4) 0.069(2) Uani 1 1 d . . . C8 C -0.3607(6) 0.0978(3) 0.6322(3) 0.0502(14) Uani 1 1 d . . . C9 C -0.3713(5) 0.1769(3) 0.6499(3) 0.0410(12) Uani 1 1 d . . . C10 C -0.4136(6) 0.1801(4) 0.7249(3) 0.0503(14) Uani 1 1 d . . . C11 C -0.0172(5) 0.2071(2) 0.6543(2) 0.0253(8) Uani 1 1 d . . . C12 C 0.0315(4) 0.2758(2) 0.6873(2) 0.0245(8) Uani 1 1 d . . . C13 C 0.0059(4) 0.2891(2) 0.7677(2) 0.0260(8) Uani 1 1 d . . . C14 C -0.0916(5) 0.2344(2) 0.8023(2) 0.0270(8) Uani 1 1 d . . . C15 C -0.1184(5) 0.2466(3) 0.8762(2) 0.0322(9) Uani 1 1 d . . . C16 C -0.0515(5) 0.3080(3) 0.9192(2) 0.0352(10) Uani 1 1 d . . . C17 C 0.0461(5) 0.3599(2) 0.8861(2) 0.0313(9) Uani 1 1 d . . . C18 C 0.0746(5) 0.3507(2) 0.8114(2) 0.0294(9) Uani 1 1 d . . . C19 C -0.0058(5) 0.1968(2) 0.5720(2) 0.0284(9) Uani 1 1 d . . . C20 C 0.0808(5) 0.1371(2) 0.5425(2) 0.0349(10) Uani 1 1 d . . . C21 C 0.0860(6) 0.1249(3) 0.4659(3) 0.0415(11) Uani 1 1 d . . . C22 C 0.0026(6) 0.1739(3) 0.4160(2) 0.0405(11) Uani 1 1 d . . . C23 C -0.0860(5) 0.2333(3) 0.4419(2) 0.0353(10) Uani 1 1 d . . . C24 C -0.0908(5) 0.2440(2) 0.5178(2) 0.0302(9) Uani 1 1 d . . . C25 C 0.1062(5) 0.3395(2) 0.6439(2) 0.0264(8) Uani 1 1 d . . . C26 C 0.2502(5) 0.3283(3) 0.6140(2) 0.0313(9) Uani 1 1 d . . . C27 C 0.3194(5) 0.3844(3) 0.5715(2) 0.0358(10) Uani 1 1 d . . . C28 C 0.2425(6) 0.4549(3) 0.5575(2) 0.0378(11) Uani 1 1 d . . . C29 C 0.1002(5) 0.4692(2) 0.5877(2) 0.0337(10) Uani 1 1 d . . . C30 C 0.0358(5) 0.4121(2) 0.6298(2) 0.0287(9) Uani 1 1 d . . . H5 H 0.214(5) 0.095(3) 0.743(2) 0.036(12) Uiso 1 1 d . . . H3 H -0.145(5) -0.054(3) 0.758(2) 0.041(13) Uiso 1 1 d . . . H4 H 0.057(5) -0.010(3) 0.677(3) 0.041(13) Uiso 1 1 d . . . H8 H -0.333(6) 0.073(3) 0.587(3) 0.052(15) Uiso 1 1 d . . . H9 H -0.358(5) 0.220(3) 0.624(3) 0.040(13) Uiso 1 1 d . . . H1 H 0.095(6) 0.114(3) 0.869(3) 0.053(16) Uiso 1 1 d . . . H2 H -0.120(6) 0.023(3) 0.873(3) 0.043(14) Uiso 1 1 d . . . H6 H -0.450(6) 0.089(3) 0.798(3) 0.057(16) Uiso 1 1 d . . . H10 H -0.419(7) 0.223(4) 0.743(3) 0.08(2) Uiso 1 1 d . . . H7 H -0.392(8) -0.005(4) 0.701(4) 0.10(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 Zr1 0.02299(18) 0.02546(19) 0.02487(18) 0.00219(17) 0.00090(13) 0.00086(17) F1 0.0474(15) 0.0514(16) 0.0296(12) 0.0048(12) 0.0111(11) -0.0113(13) F2 0.0599(17) 0.0637(19) 0.0224(12) -0.0089(12) 0.0051(12) -0.0054(15) F3 0.0623(18) 0.0455(16) 0.0356(14) -0.0111(12) -0.0042(13) -0.0099(14) F4 0.0482(15) 0.0401(15) 0.0379(14) -0.0009(11) 0.0027(12) -0.0160(12) F5 0.0614(18) 0.0454(16) 0.0428(15) 0.0032(13) 0.0147(13) 0.0233(14) F6 0.087(2) 0.0473(18) 0.0500(17) -0.0131(14) 0.0282(16) 0.0103(16) F7 0.096(2) 0.0542(18) 0.0277(14) -0.0071(13) 0.0124(15) -0.0139(17) F8 0.0649(18) 0.0482(17) 0.0328(14) 0.0091(12) -0.0065(13) -0.0051(14) F9 0.0412(14) 0.0361(14) 0.0352(13) 0.0033(11) 0.0013(11) 0.0061(11) F10 0.0321(13) 0.0527(17) 0.0516(16) 0.0037(13) 0.0107(12) 0.0175(12) F11 0.0361(14) 0.083(2) 0.0466(15) -0.0093(16) 0.0210(12) -0.0172(15) F12 0.079(2) 0.0550(18) 0.0292(13) 0.0045(13) 0.0108(13) -0.0351(16) F13 0.079(2) 0.0289(14) 0.0361(14) 0.0056(11) 0.0001(14) 0.0002(14) F14 0.0377(13) 0.0339(14) 0.0422(14) 0.0035(11) 0.0110(11) 0.0118(11) C1 0.041(3) 0.041(3) 0.043(3) 0.005(2) -0.015(2) 0.010(2) C2 0.044(3) 0.037(3) 0.039(3) 0.012(2) 0.004(2) 0.007(2) C3 0.037(2) 0.026(2) 0.054(3) 0.006(2) 0.003(2) 0.000(2) C4 0.041(3) 0.028(2) 0.050(3) 0.004(2) 0.006(2) 0.012(2) C5 0.027(2) 0.038(3) 0.060(3) 0.012(2) 0.002(2) 0.007(2) C6 0.025(2) 0.114(6) 0.054(3) 0.042(4) -0.002(2) -0.009(3) C7 0.050(3) 0.055(4) 0.096(5) 0.018(4) -0.033(4) -0.015(3) C8 0.039(3) 0.064(4) 0.044(3) -0.017(3) -0.015(2) 0.011(2) C9 0.024(2) 0.051(3) 0.046(3) 0.023(2) -0.0058(19) 0.004(2) C10 0.028(2) 0.069(4) 0.052(3) -0.021(3) -0.007(2) 0.014(3) C11 0.0269(19) 0.026(2) 0.0231(18) -0.0005(15) 0.0035(15) 0.0045(16) C12 0.0199(18) 0.027(2) 0.0264(19) 0.0053(16) 0.0024(15) 0.0019(15) C13 0.0234(19) 0.028(2) 0.0265(19) 0.0027(16) -0.0008(16) 0.0041(16) C14 0.0256(19) 0.031(2) 0.0246(19) 0.0023(16) 0.0011(16) 0.0050(16) C15 0.036(2) 0.037(2) 0.025(2) 0.0050(18) 0.0044(17) -0.0003(19) C16 0.046(3) 0.043(3) 0.0164(18) -0.0028(18) 0.0020(17) 0.005(2) C17 0.036(2) 0.030(2) 0.026(2) -0.0043(17) -0.0034(17) 0.0007(18) C18 0.029(2) 0.028(2) 0.031(2) 0.0033(17) -0.0004(17) 0.0006(17) C19 0.032(2) 0.027(2) 0.027(2) -0.0008(16) 0.0065(17) -0.0042(17) C20 0.045(2) 0.028(2) 0.033(2) 0.0007(18) 0.0086(19) -0.0006(19) C21 0.056(3) 0.030(2) 0.041(2) -0.008(2) 0.020(2) -0.008(2) C22 0.058(3) 0.039(3) 0.025(2) -0.0035(19) 0.008(2) -0.017(2) C23 0.041(2) 0.035(2) 0.030(2) 0.0058(19) 0.0019(19) -0.008(2) C24 0.031(2) 0.030(2) 0.030(2) 0.0017(17) 0.0031(17) -0.0028(17) C25 0.028(2) 0.027(2) 0.0245(19) -0.0004(16) 0.0010(16) 0.0007(16) C26 0.027(2) 0.039(2) 0.028(2) -0.0040(18) 0.0030(17) 0.0014(18) C27 0.030(2) 0.051(3) 0.028(2) -0.007(2) 0.0080(17) -0.012(2) C28 0.048(3) 0.042(3) 0.023(2) 0.0014(19) 0.0015(19) -0.021(2) C29 0.049(3) 0.026(2) 0.025(2) -0.0019(17) -0.0041(19) -0.0060(19) C30 0.030(2) 0.032(2) 0.0242(19) -0.0020(17) 0.0037(16) 0.0009(18) _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 Zr1 C14 2.282(4) . ? Zr1 C11 2.307(4) . ? Zr1 C6 2.454(5) . ? Zr1 C10 2.473(5) . ? Zr1 C7 2.474(6) . ? Zr1 C8 2.482(5) . ? Zr1 C2 2.484(4) . ? Zr1 C9 2.490(4) . ? Zr1 C4 2.490(4) . ? Zr1 C5 2.492(4) . ? Zr1 C1 2.496(4) . ? Zr1 C3 2.504(4) . ? F1 C15 1.361(5) . ? F2 C16 1.343(4) . ? F3 C17 1.344(4) . ? F4 C18 1.344(5) . ? F5 C20 1.344(5) . ? F6 C21 1.344(5) . ? F7 C22 1.343(5) . ? F8 C23 1.342(5) . ? F9 C24 1.349(5) . ? F10 C26 1.338(5) . ? F11 C27 1.333(5) . ? F12 C28 1.340(5) . ? F13 C29 1.341(5) . ? F14 C30 1.344(4) . ? C1 C5 1.390(7) . ? C1 C2 1.402(7) . ? C1 H1 0.88(5) . ? C2 C3 1.397(7) . ? C2 H2 0.89(5) . ? C3 C4 1.391(7) . ? C3 H3 0.91(5) . ? C4 C5 1.400(7) . ? C4 H4 0.92(4) . ? C5 H5 0.90(4) . ? C6 C7 1.357(9) . ? C6 C10 1.377(9) . ? C6 H6 0.94(5) . ? C7 C8 1.360(9) . ? C7 H7 1.00(7) . ? C8 C9 1.378(7) . ? C8 H8 0.96(5) . ? C9 C10 1.413(7) . ? C9 H9 0.88(5) . ? C10 H10 0.79(6) . ? C11 C12 1.350(5) . ? C11 C19 1.487(5) . ? C12 C13 1.483(5) . ? C12 C25 1.498(5) . ? C13 C18 1.397(5) . ? C13 C14 1.414(5) . ? C14 C15 1.368(5) . ? C15 C16 1.383(6) . ? C16 C17 1.373(6) . ? C17 C18 1.380(5) . ? C19 C20 1.377(6) . ? C19 C24 1.401(6) . ? C20 C21 1.384(6) . ? C21 C22 1.366(7) . ? C22 C23 1.358(6) . ? C23 C24 1.367(6) . ? C25 C30 1.378(5) . ? C25 C26 1.382(5) . ? C26 C27 1.375(6) . ? C27 C28 1.371(7) . ? C28 C29 1.380(6) . ? C29 C30 1.365(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 C14 Zr1 C11 75.14(14) . . ? C14 Zr1 C6 100.7(2) . . ? C11 Zr1 C6 131.60(16) . . ? C14 Zr1 C10 80.75(17) . . ? C11 Zr1 C10 101.63(18) . . ? C6 Zr1 C10 32.4(2) . . ? C14 Zr1 C7 131.8(2) . . ? C11 Zr1 C7 123.5(2) . . ? C6 Zr1 C7 32.0(2) . . ? C10 Zr1 C7 53.4(2) . . ? C14 Zr1 C8 129.04(16) . . ? C11 Zr1 C8 91.64(18) . . ? C6 Zr1 C8 53.1(2) . . ? C10 Zr1 C8 53.57(18) . . ? C7 Zr1 C8 31.9(2) . . ? C14 Zr1 C2 95.32(15) . . ? C11 Zr1 C2 135.98(15) . . ? C6 Zr1 C2 92.22(18) . . ? C10 Zr1 C2 119.4(2) . . ? C7 Zr1 C2 95.18(19) . . ? C8 Zr1 C2 124.53(19) . . ? C14 Zr1 C9 97.04(16) . . ? C11 Zr1 C9 78.30(14) . . ? C6 Zr1 C9 53.99(17) . . ? C10 Zr1 C9 33.07(17) . . ? C7 Zr1 C9 53.47(19) . . ? C8 Zr1 C9 32.19(17) . . ? C2 Zr1 C9 145.63(16) . . ? C14 Zr1 C4 124.71(15) . . ? C11 Zr1 C4 96.15(15) . . ? C6 Zr1 C4 122.3(2) . . ? C10 Zr1 C4 152.30(19) . . ? C7 Zr1 C4 99.0(2) . . ? C8 Zr1 C4 105.28(17) . . ? C2 Zr1 C4 53.92(17) . . ? C9 Zr1 C4 135.29(18) . . ? C14 Zr1 C5 92.43(15) . . ? C11 Zr1 C5 82.88(15) . . ? C6 Zr1 C5 145.16(19) . . ? C10 Zr1 C5 170.45(18) . . ? C7 Zr1 C5 130.8(2) . . ? C8 Zr1 C5 135.27(18) . . ? C2 Zr1 C5 54.23(17) . . ? C9 Zr1 C5 155.94(17) . . ? C4 Zr1 C5 32.64(16) . . ? C14 Zr1 C1 75.66(15) . . ? C11 Zr1 C1 104.80(16) . . ? C6 Zr1 C1 121.11(18) . . ? C10 Zr1 C1 138.30(18) . . ? C7 Zr1 C1 127.7(2) . . ? C8 Zr1 C1 153.86(18) . . ? C2 Zr1 C1 32.70(16) . . ? C9 Zr1 C1 170.75(18) . . ? C4 Zr1 C1 53.59(17) . . ? C5 Zr1 C1 32.37(16) . . ? C14 Zr1 C3 126.77(15) . . ? C11 Zr1 C3 128.48(15) . . ? C6 Zr1 C3 93.2(2) . . ? C10 Zr1 C3 125.7(2) . . ? C7 Zr1 C3 79.25(19) . . ? C8 Zr1 C3 100.20(18) . . ? C2 Zr1 C3 32.52(15) . . ? C9 Zr1 C3 131.12(17) . . ? C4 Zr1 C3 32.35(15) . . ? C5 Zr1 C3 53.95(16) . . ? C1 Zr1 C3 53.66(17) . . ? C5 C1 C2 108.6(5) . . ? C5 C1 Zr1 73.7(3) . . ? C2 C1 Zr1 73.2(3) . . ? C5 C1 H1 131(3) . . ? C2 C1 H1 120(3) . . ? Zr1 C1 H1 120(3) . . ? C3 C2 C1 107.5(5) . . ? C3 C2 Zr1 74.5(3) . . ? C1 C2 Zr1 74.1(3) . . ? C3 C2 H2 125(3) . . ? C1 C2 H2 128(3) . . ? Zr1 C2 H2 120(3) . . ? C4 C3 C2 108.0(4) . . ? C4 C3 Zr1 73.3(3) . . ? C2 C3 Zr1 73.0(3) . . ? C4 C3 H3 127(3) . . ? C2 C3 H3 125(3) . . ? Zr1 C3 H3 117(3) . . ? C3 C4 C5 108.5(5) . . ? C3 C4 Zr1 74.4(3) . . ? C5 C4 Zr1 73.7(3) . . ? C3 C4 H4 123(3) . . ? C5 C4 H4 128(3) . . ? Zr1 C4 H4 118(3) . . ? C1 C5 C4 107.3(5) . . ? C1 C5 Zr1 74.0(3) . . ? C4 C5 Zr1 73.6(3) . . ? C1 C5 H5 130(3) . . ? C4 C5 H5 122(3) . . ? Zr1 C5 H5 120(3) . . ? C7 C6 C10 108.9(5) . . ? C7 C6 Zr1 74.9(4) . . ? C10 C6 Zr1 74.6(3) . . ? C7 C6 H6 127(3) . . ? C10 C6 H6 124(3) . . ? Zr1 C6 H6 117(3) . . ? C6 C7 C8 108.4(6) . . ? C6 C7 Zr1 73.2(3) . . ? C8 C7 Zr1 74.4(3) . . ? C6 C7 H7 120(4) . . ? C8 C7 H7 131(4) . . ? Zr1 C7 H7 115(4) . . ? C7 C8 C9 109.3(6) . . ? C7 C8 Zr1 73.8(3) . . ? C9 C8 Zr1 74.2(3) . . ? C7 C8 H8 121(3) . . ? C9 C8 H8 130(3) . . ? Zr1 C8 H8 117(3) . . ? C8 C9 C10 106.3(5) . . ? C8 C9 Zr1 73.6(3) . . ? C10 C9 Zr1 72.8(3) . . ? C8 C9 H9 132(3) . . ? C10 C9 H9 121(3) . . ? Zr1 C9 H9 119(3) . . ? C6 C10 C9 107.1(5) . . ? C6 C10 Zr1 73.0(3) . . ? C9 C10 Zr1 74.1(3) . . ? C6 C10 H10 136(5) . . ? C9 C10 H10 117(5) . . ? Zr1 C10 H10 115(5) . . ? C12 C11 C19 119.1(4) . . ? C12 C11 Zr1 114.1(3) . . ? C19 C11 Zr1 126.2(3) . . ? C11 C12 C13 119.1(3) . . ? C11 C12 C25 121.4(3) . . ? C13 C12 C25 119.5(3) . . ? C18 C13 C14 118.4(4) . . ? C18 C13 C12 124.2(4) . . ? C14 C13 C12 117.4(3) . . ? C15 C14 C13 118.1(4) . . ? C15 C14 Zr1 127.6(3) . . ? C13 C14 Zr1 113.1(3) . . ? F1 C15 C14 119.7(4) . . ? F1 C15 C16 116.8(4) . . ? C14 C15 C16 123.5(4) . . ? F2 C16 C17 119.8(4) . . ? F2 C16 C15 121.9(4) . . ? C17 C16 C15 118.3(4) . . ? F3 C17 C16 119.8(4) . . ? F3 C17 C18 120.0(4) . . ? C16 C17 C18 120.2(4) . . ? F4 C18 C17 116.2(4) . . ? F4 C18 C13 122.4(4) . . ? C17 C18 C13 121.4(4) . . ? C20 C19 C24 114.4(4) . . ? C20 C19 C11 122.9(4) . . ? C24 C19 C11 122.6(4) . . ? F5 C20 C19 119.8(4) . . ? F5 C20 C21 117.0(4) . . ? C19 C20 C21 123.2(4) . . ? F6 C21 C22 120.3(4) . . ? F6 C21 C20 120.2(4) . . ? C22 C21 C20 119.5(4) . . ? F7 C22 C23 120.4(4) . . ? F7 C22 C21 119.8(4) . . ? C23 C22 C21 119.8(4) . . ? F8 C23 C22 119.7(4) . . ? F8 C23 C24 120.5(4) . . ? C22 C23 C24 119.8(4) . . ? F9 C24 C23 117.4(4) . . ? F9 C24 C19 119.4(4) . . ? C23 C24 C19 123.3(4) . . ? C30 C25 C26 115.7(4) . . ? C30 C25 C12 122.7(4) . . ? C26 C25 C12 121.6(4) . . ? F10 C26 C27 117.5(4) . . ? F10 C26 C25 119.3(4) . . ? C27 C26 C25 123.2(4) . . ? F11 C27 C28 120.1(4) . . ? F11 C27 C26 121.1(4) . . ? C28 C27 C26 118.8(4) . . ? F12 C28 C27 120.5(4) . . ? F12 C28 C29 119.6(4) . . ? C27 C28 C29 119.9(4) . . ? F13 C29 C30 120.9(4) . . ? F13 C29 C28 119.6(4) . . ? C30 C29 C28 119.4(4) . . ? F14 C30 C29 118.1(4) . . ? F14 C30 C25 119.0(4) . . ? C29 C30 C25 122.9(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.446 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 956380' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1203 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H6 F14 Sn' _chemical_formula_sum 'C22 H6 F14 Sn' _chemical_formula_weight 654.96 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8081(4) _cell_length_b 14.4792(9) _cell_length_c 9.4551(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.521(3) _cell_angle_gamma 90.00 _cell_volume 1068.90(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3452 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 1.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8788 _exptl_absorpt_correction_T_max 0.9247 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 3452 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3452 _reflns_number_gt 3397 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0294P)^2^+0.9492P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.006(19) _refine_ls_number_reflns 3452 _refine_ls_number_parameters 336 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Sn1 Sn 0.46544(2) 1.32358(2) -0.417152(19) 0.02724(7) Uani 1 1 d . . . F5 F 0.2386(3) 1.20823(19) 0.0607(3) 0.0438(6) Uani 1 1 d . . . F11 F 0.4626(4) 1.57256(19) 0.1690(2) 0.0468(6) Uani 1 1 d . . . F1 F 0.3656(3) 1.1223(2) -0.5907(2) 0.0445(6) Uani 1 1 d . . . F4 F -0.0464(3) 1.16639(18) -0.1376(3) 0.0363(6) Uani 1 1 d . . . F2 F 0.1097(4) 1.00189(19) -0.5378(3) 0.0487(6) Uani 1 1 d . . . F12 F 0.3996(3) 1.72496(18) 0.0120(3) 0.0481(6) Uani 1 1 d . . . F13 F 0.3167(4) 1.70805(18) -0.2661(3) 0.0485(6) Uani 1 1 d . . . F7 F -0.1719(4) 1.3847(2) 0.2954(3) 0.0514(7) Uani 1 1 d . . . F14 F 0.2787(3) 1.54024(18) -0.3816(2) 0.0414(6) Uani 1 1 d . . . F8 F -0.2154(3) 1.49032(19) 0.0614(3) 0.0498(7) Uani 1 1 d . . . F10 F 0.4365(3) 1.40399(17) 0.0523(2) 0.0383(5) Uani 1 1 d . . . F9 F -0.0364(4) 1.45414(18) -0.1728(3) 0.0385(6) Uani 1 1 d . . . F6 F 0.0565(4) 1.2436(2) 0.2943(3) 0.0528(7) Uani 1 1 d . . . F3 F -0.0936(3) 1.02772(17) -0.3103(3) 0.0429(6) Uani 1 1 d . . . C3 C 0.3282(5) 1.3751(3) -0.2359(3) 0.0269(7) Uani 1 1 d . . . C4 C 0.2145(4) 1.3129(3) -0.1914(3) 0.0267(8) Uani 1 1 d . . . C6 C 0.2924(5) 1.2105(3) -0.3915(4) 0.0290(7) Uani 1 1 d . . . C5 C 0.1886(4) 1.2259(3) -0.2734(4) 0.0259(7) Uani 1 1 d . . . C12 C 0.1269(5) 1.2781(3) 0.0584(4) 0.0330(8) Uani 1 1 d . . . C11 C 0.1080(4) 1.3297(4) -0.0631(3) 0.0268(6) Uani 1 1 d . . . C9 C 0.0339(5) 1.0866(3) -0.3367(4) 0.0328(8) Uani 1 1 d . . . C14 C -0.0830(5) 1.3662(3) 0.1785(4) 0.0358(9) Uani 1 1 d . . . C18 C 0.4003(5) 1.4779(3) -0.0285(4) 0.0297(7) Uani 1 1 d . . . C17 C 0.3520(5) 1.4657(3) -0.1686(4) 0.0278(7) Uani 1 1 d . . . C19 C 0.4167(5) 1.5636(3) 0.0329(4) 0.0336(8) Uani 1 1 d . . . C1 C 0.4234(6) 1.3944(4) -0.6089(4) 0.0444(11) Uani 1 1 d . . . H1A H 0.4534 1.3542 -0.6883 0.067 Uiso 1 1 calc R . . H1B H 0.4947 1.4501 -0.6110 0.067 Uiso 1 1 calc R . . H1C H 0.3024 1.4119 -0.6167 0.067 Uiso 1 1 calc R . . C13 C 0.0337(5) 1.2956(3) 0.1786(4) 0.0363(9) Uani 1 1 d . . . C16 C -0.0105(5) 1.4016(3) -0.0596(4) 0.0299(8) Uani 1 1 d . . . C20 C 0.3868(5) 1.6412(3) -0.0464(5) 0.0356(8) Uani 1 1 d . . . C21 C 0.3433(5) 1.6324(3) -0.1876(4) 0.0335(8) Uani 1 1 d . . . C22 C 0.3251(5) 1.5464(3) -0.2459(4) 0.0317(8) Uani 1 1 d . . . C7 C 0.2661(5) 1.1363(3) -0.4763(4) 0.0333(8) Uani 1 1 d . . . C2 C 0.7223(5) 1.2881(4) -0.3689(5) 0.0432(10) Uani 1 1 d . . . H2A H 0.7910 1.3445 -0.3599 0.065 Uiso 1 1 calc R . . H2B H 0.7683 1.2496 -0.4449 0.065 Uiso 1 1 calc R . . H2C H 0.7265 1.2538 -0.2796 0.065 Uiso 1 1 calc R . . C8 C 0.1366(5) 1.0736(3) -0.4525(4) 0.0345(8) Uani 1 1 d . . . C15 C -0.1044(5) 1.4194(3) 0.0609(4) 0.0336(8) Uani 1 1 d . . . C10 C 0.0613(5) 1.1612(3) -0.2483(4) 0.0294(7) 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 Sn1 0.02869(10) 0.02996(11) 0.02314(10) 0.00254(13) 0.00450(7) 0.00215(13) F5 0.0415(12) 0.0458(15) 0.0443(13) 0.0138(12) 0.0104(10) 0.0139(11) F11 0.0605(15) 0.0443(15) 0.0358(13) -0.0123(12) 0.0013(11) -0.0066(13) F1 0.0508(14) 0.0483(15) 0.0346(12) -0.0105(11) 0.0154(10) 0.0015(12) F4 0.0365(12) 0.0374(14) 0.0351(12) 0.0004(11) 0.0111(9) -0.0036(11) F2 0.0639(17) 0.0365(14) 0.0457(14) -0.0139(12) -0.0003(12) -0.0072(13) F12 0.0519(14) 0.0289(13) 0.0637(16) -0.0150(12) 0.0146(12) -0.0056(11) F13 0.0591(15) 0.0261(12) 0.0604(16) 0.0117(12) 0.0087(12) 0.0076(11) F7 0.0580(15) 0.0530(16) 0.0438(13) -0.0149(13) 0.0314(12) -0.0126(13) F14 0.0522(14) 0.0381(14) 0.0338(12) 0.0081(11) -0.0024(10) 0.0004(12) F8 0.0414(13) 0.0382(14) 0.0700(17) -0.0100(13) 0.0164(12) 0.0091(12) F10 0.0529(14) 0.0330(13) 0.0290(10) 0.0046(10) -0.0020(10) -0.0013(11) F9 0.0397(13) 0.0362(14) 0.0396(13) 0.0063(11) -0.0017(11) 0.0065(11) F6 0.0573(15) 0.071(2) 0.0304(12) 0.0139(13) 0.0078(11) -0.0030(14) F3 0.0428(13) 0.0345(13) 0.0515(14) -0.0033(11) -0.0003(11) -0.0122(11) C3 0.0325(17) 0.0266(19) 0.0215(14) 0.0018(14) 0.0038(12) 0.0020(15) C4 0.0279(13) 0.028(2) 0.0241(13) 0.0044(17) 0.0036(10) 0.0008(17) C6 0.0293(16) 0.0287(18) 0.0290(16) -0.0001(15) -0.0003(13) 0.0019(15) C5 0.0258(15) 0.0268(18) 0.0250(15) 0.0016(14) 0.0009(12) 0.0043(14) C12 0.0316(17) 0.033(2) 0.0342(18) 0.0026(16) 0.0041(14) 0.0015(16) C11 0.0276(13) 0.0272(18) 0.0256(12) 0.005(2) 0.0028(10) 0.0000(19) C9 0.0312(17) 0.031(2) 0.0362(19) 0.0054(16) -0.0032(14) -0.0035(16) C14 0.0335(19) 0.040(2) 0.0336(19) -0.0107(17) 0.0135(15) -0.0103(17) C18 0.0301(16) 0.0307(19) 0.0284(16) 0.0029(15) 0.0048(13) -0.0009(15) C17 0.0296(16) 0.0244(17) 0.0295(16) -0.0009(14) 0.0048(13) -0.0007(14) C19 0.0348(19) 0.033(2) 0.0328(18) -0.0052(16) 0.0038(15) -0.0021(16) C1 0.052(2) 0.051(3) 0.0295(18) 0.0138(19) 0.0043(17) 0.014(2) C13 0.0395(19) 0.047(3) 0.0222(15) 0.0022(15) 0.0049(13) -0.0067(17) C16 0.0321(17) 0.028(2) 0.0298(16) -0.0031(15) 0.0027(14) -0.0004(15) C20 0.0348(18) 0.0255(18) 0.047(2) -0.0072(17) 0.0117(16) -0.0016(16) C21 0.0338(18) 0.0246(18) 0.042(2) 0.0069(16) 0.0109(16) 0.0042(15) C22 0.0296(17) 0.0313(19) 0.0344(18) 0.0031(16) 0.0055(14) 0.0006(16) C7 0.0365(18) 0.035(2) 0.0285(17) -0.0022(16) 0.0025(14) 0.0042(17) C2 0.0322(18) 0.054(3) 0.044(2) 0.007(2) -0.0006(16) 0.0035(18) C8 0.044(2) 0.0279(19) 0.0314(18) -0.0051(16) -0.0065(16) -0.0016(17) C15 0.0279(17) 0.031(2) 0.042(2) -0.0077(17) 0.0069(15) -0.0015(15) C10 0.0312(17) 0.0288(19) 0.0283(17) 0.0023(15) 0.0026(13) 0.0045(15) _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 Sn1 C1 2.106(4) . ? Sn1 C2 2.116(4) . ? Sn1 C6 2.138(4) . ? Sn1 C3 2.162(3) . ? F5 C12 1.336(5) . ? F11 C19 1.339(5) . ? F1 C7 1.353(4) . ? F4 C10 1.351(4) . ? F2 C8 1.330(5) . ? F12 C20 1.336(5) . ? F13 C21 1.338(5) . ? F7 C14 1.338(4) . ? F14 C22 1.333(4) . ? F8 C15 1.344(5) . ? F10 C18 1.343(4) . ? F9 C16 1.326(5) . ? F6 C13 1.338(5) . ? F3 C9 1.336(4) . ? C3 C4 1.335(5) . ? C3 C17 1.469(5) . ? C4 C5 1.493(6) . ? C4 C11 1.496(4) . ? C6 C7 1.355(6) . ? C6 C5 1.403(5) . ? C5 C10 1.388(5) . ? C12 C11 1.377(5) . ? C12 C13 1.379(5) . ? C11 C16 1.394(6) . ? C9 C8 1.376(6) . ? C9 C10 1.381(5) . ? C14 C15 1.362(6) . ? C14 C13 1.370(6) . ? C18 C19 1.376(6) . ? C18 C17 1.385(5) . ? C17 C22 1.394(5) . ? C19 C20 1.369(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C16 C15 1.385(5) . ? C20 C21 1.381(6) . ? C21 C22 1.369(6) . ? C7 C8 1.379(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 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 C1 Sn1 C2 116.35(18) . . ? C1 Sn1 C6 112.14(17) . . ? C2 Sn1 C6 112.85(16) . . ? C1 Sn1 C3 116.09(16) . . ? C2 Sn1 C3 112.86(15) . . ? C6 Sn1 C3 81.71(14) . . ? C4 C3 C17 123.1(3) . . ? C4 C3 Sn1 110.7(3) . . ? C17 C3 Sn1 126.2(2) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C11 121.5(4) . . ? C5 C4 C11 119.0(4) . . ? C7 C6 C5 120.7(4) . . ? C7 C6 Sn1 129.2(3) . . ? C5 C6 Sn1 109.8(3) . . ? C10 C5 C6 116.7(3) . . ? C10 C5 C4 125.1(3) . . ? C6 C5 C4 118.1(3) . . ? F5 C12 C11 119.3(3) . . ? F5 C12 C13 118.4(3) . . ? C11 C12 C13 122.3(4) . . ? C12 C11 C16 116.9(3) . . ? C12 C11 C4 122.1(4) . . ? C16 C11 C4 121.0(4) . . ? F3 C9 C8 120.1(4) . . ? F3 C9 C10 119.8(3) . . ? C8 C9 C10 120.0(4) . . ? F7 C14 C15 120.1(4) . . ? F7 C14 C13 119.9(4) . . ? C15 C14 C13 119.9(3) . . ? F10 C18 C19 117.4(3) . . ? F10 C18 C17 119.7(3) . . ? C19 C18 C17 122.8(4) . . ? C18 C17 C22 115.6(3) . . ? C18 C17 C3 124.1(3) . . ? C22 C17 C3 120.2(3) . . ? F11 C19 C20 119.3(4) . . ? F11 C19 C18 121.0(4) . . ? C20 C19 C18 119.6(4) . . ? Sn1 C1 H1A 109.5 . . ? Sn1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Sn1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? F6 C13 C14 120.2(3) . . ? F6 C13 C12 120.2(4) . . ? C14 C13 C12 119.5(4) . . ? F9 C16 C15 118.6(4) . . ? F9 C16 C11 120.4(3) . . ? C15 C16 C11 121.0(3) . . ? F12 C20 C19 120.4(4) . . ? F12 C20 C21 120.0(4) . . ? C19 C20 C21 119.6(4) . . ? F13 C21 C22 120.4(3) . . ? F13 C21 C20 119.8(4) . . ? C22 C21 C20 119.8(4) . . ? F14 C22 C21 118.4(3) . . ? F14 C22 C17 119.1(4) . . ? C21 C22 C17 122.5(3) . . ? F1 C7 C6 120.5(4) . . ? F1 C7 C8 117.3(3) . . ? C6 C7 C8 122.2(4) . . ? Sn1 C2 H2A 109.5 . . ? Sn1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Sn1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? F2 C8 C9 119.9(4) . . ? F2 C8 C7 121.8(4) . . ? C9 C8 C7 118.2(4) . . ? F8 C15 C14 120.2(4) . . ? F8 C15 C16 119.4(4) . . ? C14 C15 C16 120.3(4) . . ? F4 C10 C9 114.7(3) . . ? F4 C10 C5 123.1(3) . . ? C9 C10 C5 122.1(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.770 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 956381' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1204 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-bora-1-bromo-4,5,6,7-tetrafluoro-2,3-bis(pentafluorophenyl)indene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 B Br F14' _chemical_formula_sum 'C20 B Br F14' _chemical_formula_weight 596.92 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 9.0742(3) _cell_length_b 10.2272(4) _cell_length_c 10.9121(3) _cell_angle_alpha 71.095(2) _cell_angle_beta 79.247(2) _cell_angle_gamma 84.755(2) _cell_volume 940.71(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7922 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 2.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8004 _exptl_absorpt_correction_T_max 0.8729 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; None ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 7922 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.58 _reflns_number_total 4291 _reflns_number_gt 3859 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0299P)^2^+1.2986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4291 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Br1 Br 0.90424(3) 0.14248(3) 1.06958(3) 0.03558(9) Uani 1 1 d . . . F9 F 0.38320(17) 0.10147(16) 0.85143(15) 0.0315(3) Uani 1 1 d . . . F4 F 0.17745(17) 0.25876(18) 1.20136(15) 0.0359(4) Uani 1 1 d . . . F5 F 0.28860(19) 0.49302(16) 0.99533(16) 0.0353(4) Uani 1 1 d . . . F14 F 0.76571(18) 0.01949(16) 0.86220(15) 0.0351(4) Uani 1 1 d . . . F13 F 0.8887(2) 0.0635(2) 0.60918(18) 0.0470(4) Uani 1 1 d . . . F8 F 0.1551(2) 0.18303(18) 0.71465(16) 0.0396(4) Uani 1 1 d . . . F1 F 0.70854(19) 0.12029(19) 1.37828(16) 0.0410(4) Uani 1 1 d . . . F7 F -0.00487(19) 0.41864(19) 0.71612(17) 0.0429(4) Uani 1 1 d . . . F6 F 0.06209(19) 0.57303(17) 0.85730(17) 0.0417(4) Uani 1 1 d . . . F3 F 0.1926(2) 0.2149(2) 1.45182(16) 0.0453(4) Uani 1 1 d . . . F10 F 0.5778(2) 0.48022(16) 0.75725(17) 0.0398(4) Uani 1 1 d . . . F2 F 0.4579(2) 0.1511(2) 1.54165(15) 0.0435(4) Uani 1 1 d . . . C3 C 0.4405(3) 0.2246(2) 1.1516(2) 0.0241(5) Uani 1 1 d . . . B15 B 0.6974(3) 0.1829(3) 1.0764(3) 0.0262(6) Uani 1 1 d . . . C12 C 0.1082(3) 0.3788(3) 0.7841(2) 0.0307(6) Uani 1 1 d . . . C2 C 0.4638(3) 0.2488(2) 1.0071(2) 0.0233(5) Uani 1 1 d . . . C9 C 0.3407(3) 0.2935(2) 0.9300(2) 0.0227(5) Uani 1 1 d . . . C13 C 0.1898(3) 0.2595(3) 0.7829(2) 0.0289(5) Uani 1 1 d . . . F12 F 0.8572(2) 0.3162(2) 0.42928(17) 0.0523(5) Uani 1 1 d . . . C10 C 0.2562(3) 0.4139(3) 0.9274(2) 0.0266(5) Uani 1 1 d . . . C14 C 0.3052(3) 0.2187(3) 0.8540(2) 0.0250(5) Uani 1 1 d . . . F11 F 0.6956(2) 0.52109(19) 0.50486(17) 0.0523(5) Uani 1 1 d . . . C5 C 0.5820(3) 0.1605(3) 1.3283(3) 0.0301(5) Uani 1 1 d . . . C19 C 0.8125(3) 0.1655(3) 0.6460(3) 0.0335(6) Uani 1 1 d . . . C4 C 0.5793(3) 0.1869(3) 1.1976(2) 0.0258(5) Uani 1 1 d . . . C16 C 0.6522(3) 0.3743(3) 0.7238(3) 0.0302(5) Uani 1 1 d . . . C15 C 0.6687(3) 0.2482(3) 0.8190(2) 0.0259(5) Uani 1 1 d . . . C20 C 0.7500(3) 0.1456(3) 0.7755(3) 0.0285(5) Uani 1 1 d . . . C1 C 0.6087(3) 0.2255(2) 0.9590(2) 0.0244(5) Uani 1 1 d . . . C8 C 0.3122(3) 0.2295(3) 1.2377(2) 0.0272(5) Uani 1 1 d . . . C11 C 0.1412(3) 0.4572(3) 0.8563(3) 0.0289(5) Uani 1 1 d . . . C6 C 0.4521(3) 0.1725(3) 1.4145(2) 0.0322(6) Uani 1 1 d . . . C7 C 0.3182(3) 0.2051(3) 1.3701(3) 0.0319(6) Uani 1 1 d . . . C17 C 0.7134(3) 0.3966(3) 0.5932(3) 0.0359(6) Uani 1 1 d . . . C18 C 0.7952(3) 0.2927(3) 0.5548(3) 0.0382(7) 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 Br1 0.02449(14) 0.03827(16) 0.04201(16) -0.00925(12) -0.00743(11) 0.00041(10) F9 0.0346(8) 0.0269(8) 0.0361(8) -0.0152(6) -0.0048(6) 0.0005(6) F4 0.0239(7) 0.0466(10) 0.0354(8) -0.0127(7) -0.0056(6) 0.0083(7) F5 0.0468(9) 0.0277(8) 0.0380(8) -0.0162(7) -0.0164(7) 0.0070(7) F14 0.0403(9) 0.0270(8) 0.0357(8) -0.0089(7) -0.0054(7) 0.0049(7) F13 0.0526(11) 0.0470(11) 0.0428(10) -0.0241(8) 0.0061(8) -0.0003(8) F8 0.0479(10) 0.0455(10) 0.0337(8) -0.0177(7) -0.0135(7) -0.0103(8) F1 0.0362(9) 0.0527(11) 0.0358(9) -0.0097(8) -0.0189(7) 0.0013(8) F7 0.0338(9) 0.0498(11) 0.0435(9) -0.0044(8) -0.0207(7) -0.0016(7) F6 0.0416(9) 0.0339(9) 0.0467(10) -0.0098(7) -0.0130(8) 0.0159(7) F3 0.0392(9) 0.0649(12) 0.0298(8) -0.0184(8) 0.0008(7) 0.0071(8) F10 0.0501(10) 0.0239(8) 0.0393(9) -0.0043(7) -0.0037(8) 0.0017(7) F2 0.0523(10) 0.0552(11) 0.0239(8) -0.0119(7) -0.0106(7) 0.0001(8) C3 0.0270(12) 0.0203(11) 0.0253(11) -0.0068(9) -0.0062(9) 0.0001(9) B15 0.0258(13) 0.0217(13) 0.0304(14) -0.0065(11) -0.0058(11) -0.0016(10) C12 0.0243(12) 0.0385(15) 0.0251(12) -0.0017(11) -0.0073(10) -0.0044(10) C2 0.0275(12) 0.0179(11) 0.0250(11) -0.0067(9) -0.0060(9) -0.0006(9) C9 0.0227(11) 0.0227(11) 0.0216(11) -0.0058(9) -0.0030(9) -0.0003(9) C13 0.0302(13) 0.0350(14) 0.0222(11) -0.0083(10) -0.0036(10) -0.0090(11) F12 0.0701(13) 0.0561(12) 0.0276(8) -0.0130(8) 0.0070(8) -0.0186(10) C10 0.0306(12) 0.0243(12) 0.0261(12) -0.0090(10) -0.0065(10) 0.0005(10) C14 0.0279(12) 0.0229(12) 0.0231(11) -0.0071(9) -0.0010(9) -0.0022(9) F11 0.0761(14) 0.0369(10) 0.0336(9) 0.0047(8) -0.0086(9) -0.0092(9) C5 0.0325(13) 0.0287(13) 0.0309(13) -0.0080(10) -0.0130(11) 0.0004(10) C19 0.0332(14) 0.0380(15) 0.0329(13) -0.0175(12) -0.0005(11) -0.0062(11) C4 0.0273(12) 0.0225(12) 0.0284(12) -0.0077(10) -0.0075(10) 0.0002(9) C16 0.0320(13) 0.0267(13) 0.0320(13) -0.0087(10) -0.0054(10) -0.0036(10) C15 0.0246(12) 0.0264(12) 0.0263(12) -0.0068(10) -0.0052(9) -0.0022(9) C20 0.0263(12) 0.0278(13) 0.0304(12) -0.0078(10) -0.0043(10) -0.0021(10) C1 0.0262(12) 0.0195(11) 0.0276(12) -0.0065(9) -0.0065(9) -0.0010(9) C8 0.0296(13) 0.0243(12) 0.0280(12) -0.0078(10) -0.0079(10) 0.0026(10) C11 0.0269(12) 0.0252(12) 0.0300(12) -0.0040(10) -0.0046(10) 0.0040(10) C6 0.0439(15) 0.0297(13) 0.0240(12) -0.0075(10) -0.0098(11) -0.0013(11) C7 0.0352(14) 0.0321(14) 0.0274(12) -0.0107(11) -0.0007(11) 0.0008(11) C17 0.0423(16) 0.0323(14) 0.0295(13) -0.0013(11) -0.0076(12) -0.0107(12) C18 0.0431(16) 0.0469(17) 0.0242(12) -0.0103(12) 0.0006(11) -0.0154(13) _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 Br1 B15 1.878(3) . ? F9 C14 1.341(3) . ? F4 C8 1.334(3) . ? F5 C10 1.343(3) . ? F14 C20 1.344(3) . ? F13 C19 1.328(3) . ? F8 C13 1.333(3) . ? F1 C5 1.337(3) . ? F7 C12 1.335(3) . ? F6 C11 1.330(3) . ? F3 C7 1.327(3) . ? F10 C16 1.340(3) . ? F2 C6 1.344(3) . ? C3 C8 1.361(4) . ? C3 C4 1.417(3) . ? C3 C2 1.492(3) . ? B15 C4 1.548(4) . ? B15 C1 1.562(4) . ? C12 C13 1.371(4) . ? C12 C11 1.377(4) . ? C2 C1 1.352(3) . ? C2 C9 1.474(3) . ? C9 C10 1.385(3) . ? C9 C14 1.389(3) . ? C13 C14 1.374(4) . ? F12 C18 1.332(3) . ? C10 C11 1.371(3) . ? F11 C17 1.342(3) . ? C5 C4 1.368(4) . ? C5 C6 1.387(4) . ? C19 C18 1.375(4) . ? C19 C20 1.377(4) . ? C16 C17 1.382(4) . ? C16 C15 1.385(4) . ? C15 C20 1.386(4) . ? C15 C1 1.472(3) . ? C8 C7 1.395(4) . ? C6 C7 1.365(4) . ? C17 C18 1.372(4) . ? 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 C8 C3 C4 120.0(2) . . ? C8 C3 C2 130.2(2) . . ? C4 C3 C2 109.7(2) . . ? C4 B15 C1 105.2(2) . . ? C4 B15 Br1 127.75(19) . . ? C1 B15 Br1 127.0(2) . . ? F7 C12 C13 119.9(2) . . ? F7 C12 C11 119.7(3) . . ? C13 C12 C11 120.3(2) . . ? C1 C2 C9 125.8(2) . . ? C1 C2 C3 111.7(2) . . ? C9 C2 C3 122.5(2) . . ? C10 C9 C14 116.5(2) . . ? C10 C9 C2 121.7(2) . . ? C14 C9 C2 121.8(2) . . ? F8 C13 C12 119.8(2) . . ? F8 C13 C14 120.6(2) . . ? C12 C13 C14 119.6(2) . . ? F5 C10 C11 118.3(2) . . ? F5 C10 C9 119.2(2) . . ? C11 C10 C9 122.6(2) . . ? F9 C14 C13 118.4(2) . . ? F9 C14 C9 119.6(2) . . ? C13 C14 C9 122.0(2) . . ? F1 C5 C4 121.6(2) . . ? F1 C5 C6 117.5(2) . . ? C4 C5 C6 120.9(2) . . ? F13 C19 C18 120.2(2) . . ? F13 C19 C20 120.7(3) . . ? C18 C19 C20 119.1(3) . . ? C5 C4 C3 118.8(2) . . ? C5 C4 B15 135.1(2) . . ? C3 C4 B15 106.1(2) . . ? F10 C16 C17 117.8(2) . . ? F10 C16 C15 120.2(2) . . ? C17 C16 C15 122.0(3) . . ? C16 C15 C20 116.1(2) . . ? C16 C15 C1 122.2(2) . . ? C20 C15 C1 121.7(2) . . ? F14 C20 C19 118.0(2) . . ? F14 C20 C15 119.0(2) . . ? C19 C20 C15 123.0(2) . . ? C2 C1 C15 124.6(2) . . ? C2 C1 B15 107.4(2) . . ? C15 C1 B15 127.9(2) . . ? F4 C8 C3 122.9(2) . . ? F4 C8 C7 117.0(2) . . ? C3 C8 C7 120.1(2) . . ? F6 C11 C10 120.6(2) . . ? F6 C11 C12 120.3(2) . . ? C10 C11 C12 119.1(2) . . ? F2 C6 C7 120.0(3) . . ? F2 C6 C5 120.0(2) . . ? C7 C6 C5 119.9(2) . . ? F3 C7 C6 120.6(2) . . ? F3 C7 C8 119.2(2) . . ? C6 C7 C8 120.1(2) . . ? F11 C17 C18 120.3(3) . . ? F11 C17 C16 119.7(3) . . ? C18 C17 C16 119.9(3) . . ? F12 C18 C17 119.6(3) . . ? F12 C18 C19 120.5(3) . . ? C17 C18 C19 119.9(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.575 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 956382' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ah1304 _audit_creation_method SHELXL-97 _chemical_melting_point Unknown _chemical_formula_moiety 'C26 H B Cl F19' _chemical_formula_sum 'C26 H B Cl F19' _chemical_formula_weight 720.53 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' Cl Cl 0.1484 0.1585 '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' B B 0.0013 0.0007 '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' 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 11.2301(3) _cell_length_b 17.6492(4) _cell_length_c 15.5641(5) _cell_angle_alpha 90.00 _cell_angle_beta 126.554(2) _cell_angle_gamma 90.00 _cell_volume 2478.04(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 21099 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.57 _exptl_crystal_description Rectangle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_special_details ; None ; _diffrn_ambient_temperature 173(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 'Nonius APEX CCD' _diffrn_measurement_method ' \w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 21099 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.57 _reflns_number_total 5731 _reflns_number_gt 3745 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0000P)^2^+3.5043P] 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 5731 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 C1 C 0.7527(4) 0.1528(2) 0.5727(3) 0.0458(9) Uani 1 1 d . . . C2 C 0.8998(4) 0.14588(19) 0.6069(3) 0.0421(8) Uani 1 1 d . . . C3 C 1.0246(4) 0.1717(2) 0.7155(3) 0.0410(8) Uani 1 1 d . . . C4 C 1.0148(4) 0.2365(2) 0.7548(3) 0.0425(8) Uani 1 1 d . . . H4 H 0.9313 0.2677 0.7074 0.051 Uiso 1 1 calc R . . C5 C 0.9243(4) 0.1160(2) 0.5371(3) 0.0516(9) Uani 1 1 d . . . C6 C 0.8121(5) 0.0925(2) 0.4367(3) 0.0602(11) Uani 1 1 d . . . C7 C 0.6686(5) 0.0990(2) 0.4032(3) 0.0622(11) Uani 1 1 d . . . C8 C 0.6415(4) 0.1295(2) 0.4699(3) 0.0570(10) Uani 1 1 d . . . C9 C 1.1602(4) 0.1247(2) 0.7750(3) 0.0439(8) Uani 1 1 d . . . C10 C 1.1547(5) 0.0487(2) 0.7904(3) 0.0571(10) Uani 1 1 d . . . C11 C 1.2756(7) 0.0026(3) 0.8381(3) 0.0767(15) Uani 1 1 d . . . C12 C 1.4076(6) 0.0325(4) 0.8704(3) 0.089(2) Uani 1 1 d . . . C13 C 1.4204(5) 0.1082(4) 0.8598(3) 0.0771(16) Uani 1 1 d . . . C14 C 1.2975(4) 0.1534(3) 0.8118(3) 0.0555(10) Uani 1 1 d . . . C15 C 1.1211(4) 0.2642(2) 0.8643(3) 0.0422(8) Uani 1 1 d . . . C16 C 1.1793(4) 0.2209(2) 0.9547(3) 0.0459(9) Uani 1 1 d . . . C17 C 1.2748(4) 0.2495(2) 1.0558(3) 0.0512(10) Uani 1 1 d . . . C18 C 1.3141(4) 0.3243(3) 1.0681(3) 0.0567(11) Uani 1 1 d . . . C19 C 1.2583(5) 0.3694(2) 0.9813(4) 0.0574(10) Uani 1 1 d . . . C20 C 1.1639(4) 0.3394(2) 0.8812(3) 0.0506(9) Uani 1 1 d . . . C21 C 0.7573(4) 0.1420(2) 0.7506(3) 0.0456(9) Uani 1 1 d . . . C22 C 0.8058(4) 0.1785(2) 0.8448(3) 0.0553(10) Uani 1 1 d . . . C23 C 0.8457(5) 0.1413(3) 0.9350(3) 0.0611(11) Uani 1 1 d . . . C25 C 0.7871(4) 0.0251(2) 0.8421(3) 0.0559(10) Uani 1 1 d . . . C26 C 0.7493(4) 0.0641(2) 0.7533(3) 0.0491(9) Uani 1 1 d . . . C24 C 0.8357(4) 0.0641(3) 0.9332(3) 0.0601(11) Uani 1 1 d . . . Cl1 Cl 0.60936(12) 0.26620(6) 0.60825(10) 0.0714(3) Uani 1 1 d . . . F10 F 1.1399(2) 0.14793(12) 0.94590(16) 0.0577(6) Uani 1 1 d . . . F1 F 1.0635(2) 0.11113(14) 0.56547(17) 0.0669(6) Uani 1 1 d . . . F9 F 1.3118(2) 0.22670(16) 0.79839(18) 0.0701(7) Uani 1 1 d . . . F14 F 1.1119(3) 0.38382(13) 0.7963(2) 0.0741(7) Uani 1 1 d . . . F34 F 0.6990(3) 0.02398(12) 0.66486(18) 0.0647(6) Uani 1 1 d . . . F11 F 1.3306(3) 0.20517(15) 1.14096(17) 0.0746(7) Uani 1 1 d . . . F12 F 1.4087(3) 0.35288(15) 1.16629(19) 0.0809(8) Uani 1 1 d . . . F5 F 1.0254(3) 0.01834(13) 0.75852(19) 0.0724(7) Uani 1 1 d . . . F4 F 0.4999(2) 0.13301(15) 0.43574(19) 0.0788(7) Uani 1 1 d . . . F17 F 0.8949(3) 0.17912(18) 1.0240(2) 0.0954(9) Uani 1 1 d . . . F19 F 0.7773(3) -0.05009(14) 0.8409(2) 0.0786(7) Uani 1 1 d . . . F13 F 1.2978(3) 0.44207(14) 0.9948(2) 0.0855(8) Uani 1 1 d . . . F16 F 0.8199(3) 0.25413(14) 0.8503(2) 0.0802(8) Uani 1 1 d . . . F8 F 1.5505(3) 0.1383(2) 0.8927(2) 0.1138(12) Uani 1 1 d . . . F2 F 0.8422(3) 0.06443(16) 0.37232(18) 0.0850(8) Uani 1 1 d . . . F6 F 1.2660(4) -0.07060(17) 0.8526(2) 0.1152(12) Uani 1 1 d . . . F18 F 0.8738(3) 0.02672(17) 1.02041(19) 0.0861(8) Uani 1 1 d . . . F3 F 0.5592(3) 0.07406(16) 0.30566(19) 0.0908(9) Uani 1 1 d . . . F7 F 1.5282(3) -0.0111(2) 0.9157(2) 0.1325(15) Uani 1 1 d . . . B1 B 0.7144(4) 0.1832(2) 0.6476(4) 0.0485(11) 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 0.041(2) 0.040(2) 0.047(2) 0.0077(17) 0.0212(18) -0.0014(16) C2 0.048(2) 0.040(2) 0.0356(19) 0.0042(15) 0.0233(17) -0.0051(16) C3 0.0443(19) 0.041(2) 0.044(2) 0.0029(16) 0.0295(18) -0.0043(16) C4 0.0353(18) 0.044(2) 0.043(2) 0.0076(17) 0.0208(16) 0.0000(16) C5 0.054(2) 0.055(2) 0.047(2) 0.0044(19) 0.031(2) -0.0080(19) C6 0.078(3) 0.061(3) 0.038(2) 0.000(2) 0.033(2) -0.008(2) C7 0.063(3) 0.063(3) 0.034(2) -0.001(2) 0.014(2) -0.013(2) C8 0.044(2) 0.054(2) 0.051(2) 0.008(2) 0.016(2) -0.0053(19) C9 0.044(2) 0.056(2) 0.0318(18) -0.0021(16) 0.0229(17) 0.0034(18) C10 0.068(3) 0.057(3) 0.040(2) -0.0022(19) 0.029(2) 0.004(2) C11 0.102(4) 0.077(4) 0.041(2) 0.009(2) 0.037(3) 0.041(3) C12 0.080(4) 0.137(5) 0.036(2) 0.012(3) 0.027(3) 0.065(4) C13 0.042(2) 0.151(5) 0.035(2) -0.009(3) 0.021(2) 0.017(3) C14 0.052(2) 0.077(3) 0.041(2) -0.003(2) 0.030(2) 0.002(2) C15 0.0401(18) 0.045(2) 0.043(2) -0.0013(17) 0.0252(17) -0.0006(16) C16 0.047(2) 0.048(2) 0.050(2) -0.0072(18) 0.0329(19) -0.0041(18) C17 0.049(2) 0.066(3) 0.044(2) -0.004(2) 0.0306(19) 0.003(2) C18 0.048(2) 0.077(3) 0.052(2) -0.026(2) 0.033(2) -0.012(2) C19 0.061(3) 0.049(2) 0.072(3) -0.017(2) 0.045(2) -0.010(2) C20 0.051(2) 0.046(2) 0.056(2) 0.0007(19) 0.033(2) 0.0032(19) C21 0.0401(19) 0.043(2) 0.058(2) -0.0009(18) 0.0317(19) 0.0005(16) C22 0.055(2) 0.054(3) 0.071(3) -0.015(2) 0.046(2) -0.004(2) C23 0.059(3) 0.079(3) 0.057(3) -0.013(2) 0.041(2) -0.003(2) C25 0.054(2) 0.055(3) 0.063(3) 0.010(2) 0.037(2) 0.005(2) C26 0.044(2) 0.051(2) 0.051(2) -0.0041(19) 0.0272(19) -0.0005(18) C24 0.048(2) 0.089(3) 0.050(2) 0.012(2) 0.032(2) 0.010(2) Cl1 0.0577(6) 0.0499(6) 0.1051(9) 0.0152(6) 0.0477(6) 0.0096(5) F10 0.0703(14) 0.0537(14) 0.0513(13) 0.0012(10) 0.0374(12) -0.0072(11) F1 0.0647(15) 0.0932(18) 0.0550(14) -0.0080(13) 0.0423(12) -0.0072(13) F9 0.0550(14) 0.097(2) 0.0675(16) -0.0119(14) 0.0414(13) -0.0228(14) F14 0.0903(18) 0.0447(13) 0.0739(17) 0.0052(12) 0.0417(15) -0.0031(13) F34 0.0852(17) 0.0460(13) 0.0601(14) -0.0042(11) 0.0417(13) -0.0104(12) F11 0.0818(17) 0.0933(19) 0.0440(13) 0.0004(13) 0.0349(13) -0.0049(14) F12 0.0781(16) 0.103(2) 0.0632(16) -0.0355(15) 0.0428(14) -0.0269(15) F5 0.0929(19) 0.0468(14) 0.0657(15) 0.0033(12) 0.0409(15) -0.0058(13) F4 0.0440(13) 0.0879(19) 0.0705(16) 0.0027(14) 0.0156(12) -0.0065(13) F17 0.104(2) 0.125(2) 0.0717(18) -0.0311(17) 0.0603(17) -0.0102(19) F19 0.0945(19) 0.0571(16) 0.0851(18) 0.0190(13) 0.0540(16) 0.0035(14) F13 0.108(2) 0.0552(16) 0.095(2) -0.0285(14) 0.0615(18) -0.0254(15) F16 0.103(2) 0.0569(16) 0.102(2) -0.0265(14) 0.0725(18) -0.0117(14) F8 0.0439(14) 0.230(4) 0.0615(17) -0.014(2) 0.0282(13) 0.0116(19) F2 0.108(2) 0.098(2) 0.0485(14) -0.0146(14) 0.0467(15) -0.0074(17) F6 0.180(3) 0.074(2) 0.0740(19) 0.0244(15) 0.066(2) 0.063(2) F18 0.0759(17) 0.128(2) 0.0611(16) 0.0231(16) 0.0443(15) 0.0154(16) F3 0.0812(18) 0.099(2) 0.0445(14) -0.0085(14) 0.0118(14) -0.0146(16) F7 0.114(2) 0.208(4) 0.0545(17) 0.022(2) 0.0389(17) 0.107(3) B1 0.033(2) 0.040(2) 0.064(3) -0.003(2) 0.024(2) -0.0059(18) _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 C8 1.381(5) . ? C1 C2 1.406(5) . ? C1 B1 1.559(6) . ? C2 C5 1.375(5) . ? C2 C3 1.486(5) . ? C3 C4 1.332(5) . ? C3 C9 1.478(5) . ? C4 C15 1.465(5) . ? C4 H4 0.9500 . ? C5 F1 1.351(4) . ? C5 C6 1.363(5) . ? C6 F2 1.329(4) . ? C6 C7 1.371(6) . ? C7 F3 1.336(4) . ? C7 C8 1.356(6) . ? C8 F4 1.345(4) . ? C9 C10 1.371(5) . ? C9 C14 1.382(5) . ? C10 F5 1.335(5) . ? C10 C11 1.363(6) . ? C11 F6 1.327(6) . ? C11 C12 1.357(8) . ? C12 F7 1.337(5) . ? C12 C13 1.363(8) . ? C13 F8 1.338(5) . ? C13 C14 1.368(6) . ? C14 F9 1.335(5) . ? C15 C16 1.376(5) . ? C15 C20 1.384(5) . ? C16 F10 1.341(4) . ? C16 C17 1.368(5) . ? C17 F11 1.331(4) . ? C17 C18 1.370(6) . ? C18 F12 1.336(4) . ? C18 C19 1.357(6) . ? C19 F13 1.333(4) . ? C19 C20 1.365(5) . ? C20 F14 1.334(4) . ? C21 C26 1.381(5) . ? C21 C22 1.383(5) . ? C21 B1 1.552(6) . ? C22 F16 1.341(4) . ? C22 C23 1.361(6) . ? C23 F17 1.326(4) . ? C23 C24 1.366(6) . ? C25 F19 1.330(4) . ? C25 C24 1.364(6) . ? C25 C26 1.366(5) . ? C26 F34 1.337(4) . ? C24 F18 1.330(4) . ? Cl1 B1 1.747(4) . ? 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 C8 C1 C2 117.5(4) . . ? C8 C1 B1 120.4(3) . . ? C2 C1 B1 122.1(3) . . ? C5 C2 C1 118.5(3) . . ? C5 C2 C3 121.3(3) . . ? C1 C2 C3 120.2(3) . . ? C4 C3 C9 122.0(3) . . ? C4 C3 C2 120.4(3) . . ? C9 C3 C2 117.5(3) . . ? C3 C4 C15 126.0(3) . . ? C3 C4 H4 117.0 . . ? C15 C4 H4 117.0 . . ? F1 C5 C6 117.1(4) . . ? F1 C5 C2 120.3(3) . . ? C6 C5 C2 122.6(4) . . ? F2 C6 C5 120.1(4) . . ? F2 C6 C7 120.9(4) . . ? C5 C6 C7 119.1(4) . . ? F3 C7 C8 121.8(4) . . ? F3 C7 C6 118.8(4) . . ? C8 C7 C6 119.4(4) . . ? F4 C8 C7 117.9(4) . . ? F4 C8 C1 119.0(4) . . ? C7 C8 C1 123.0(4) . . ? C10 C9 C14 116.2(4) . . ? C10 C9 C3 121.4(3) . . ? C14 C9 C3 122.3(4) . . ? F5 C10 C11 118.3(4) . . ? F5 C10 C9 118.7(4) . . ? C11 C10 C9 123.0(5) . . ? F6 C11 C12 119.9(5) . . ? F6 C11 C10 121.2(6) . . ? C12 C11 C10 118.9(5) . . ? F7 C12 C11 120.7(7) . . ? F7 C12 C13 118.8(6) . . ? C11 C12 C13 120.5(5) . . ? F8 C13 C12 120.9(5) . . ? F8 C13 C14 119.6(6) . . ? C12 C13 C14 119.5(5) . . ? F9 C14 C13 118.3(4) . . ? F9 C14 C9 119.9(4) . . ? C13 C14 C9 121.8(5) . . ? C16 C15 C20 116.1(3) . . ? C16 C15 C4 124.5(3) . . ? C20 C15 C4 119.4(3) . . ? F10 C16 C17 117.2(3) . . ? F10 C16 C15 120.1(3) . . ? C17 C16 C15 122.7(4) . . ? F11 C17 C16 120.7(4) . . ? F11 C17 C18 120.4(4) . . ? C16 C17 C18 118.9(4) . . ? F12 C18 C19 119.9(4) . . ? F12 C18 C17 119.7(4) . . ? C19 C18 C17 120.4(4) . . ? F13 C19 C18 119.6(4) . . ? F13 C19 C20 120.8(4) . . ? C18 C19 C20 119.6(4) . . ? F14 C20 C19 119.2(4) . . ? F14 C20 C15 118.6(3) . . ? C19 C20 C15 122.2(4) . . ? C26 C21 C22 115.0(4) . . ? C26 C21 B1 120.8(3) . . ? C22 C21 B1 124.2(3) . . ? F16 C22 C23 117.5(4) . . ? F16 C22 C21 119.2(4) . . ? C23 C22 C21 123.3(4) . . ? F17 C23 C22 120.7(4) . . ? F17 C23 C24 120.1(4) . . ? C22 C23 C24 119.2(4) . . ? F19 C25 C24 119.8(4) . . ? F19 C25 C26 121.0(4) . . ? C24 C25 C26 119.2(4) . . ? F34 C26 C25 117.4(4) . . ? F34 C26 C21 119.4(3) . . ? C25 C26 C21 123.1(4) . . ? F18 C24 C25 119.8(4) . . ? F18 C24 C23 120.1(4) . . ? C25 C24 C23 120.1(4) . . ? C21 B1 C1 123.9(3) . . ? C21 B1 Cl1 119.0(3) . . ? C1 B1 Cl1 117.1(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.243 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 956383'