# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/409 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Chambers, Richard D.' 'Diter, Patrick' 'Dunn, Stephen N.' 'Farren, Christopher' 'Sandford, Graham' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' _journal_name_full 'Journal of the Chemical Society, Perkin Transaction 1' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2000' _ccdc_journal_depnumber '?' _publ_section_title ; Free radical chemistry. Part 11. Additions of cyclic and acyclic alcohols and diols to hexafluoropropene. ; #====================================================================END data_19 _audit_creation_method SHELXL _chemical_name_systematic ; trans-cyclohexane-1,4-diol ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H12 O2' _chemical_formula_weight 116.16 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '19' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; none ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.374(1) _cell_length_b 21.313(5) _cell_length_c 7.328(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.864(10) _cell_angle_gamma 90.00 _cell_volume 990.25(15) _cell_formula_units_Z 6 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 276 _cell_measurement_theta_min 10 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method ? _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Full hemisphere of reciprocal space was scanned by \w in 0.3 deg. frames, 10 s/frame. ; _diffrn_ambient_temperature 295(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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5886 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1752 _reflns_number_observed 1191 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 39 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0193P)^2^+0.3977P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.042(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1713 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_obs 0.0478 _refine_ls_wR_factor_all 0.1127 _refine_ls_wR_factor_obs 0.0876 _refine_ls_goodness_of_fit_all 1.119 _refine_ls_goodness_of_fit_obs 1.179 _refine_ls_restrained_S_all 1.218 _refine_ls_restrained_S_obs 1.179 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.4100(2) 0.16933(8) 0.0619(2) 0.0510(5) Uani 1 d . . H01 H 0.5079(40) 0.1700(11) -0.0145(35) 0.067(9) Uiso 1 d . . C1 C 0.5032(3) 0.18417(11) 0.2438(3) 0.0387(5) Uani 1 d . . H1 H 0.5428(30) 0.2296(10) 0.2477(26) 0.043(6) Uiso 1 d . . O2 O 0.7010(3) 0.16568(8) 0.8119(2) 0.0503(5) Uani 1 d . . H02 H 0.8226(46) 0.1446(13) 0.8422(37) 0.083(10) Uiso 1 d . . C2 C 0.3374(3) 0.17403(13) 0.3747(3) 0.0434(6) Uani 1 d . . H21 H 0.2182(34) 0.2007(10) 0.3413(27) 0.044(6) Uiso 1 d . . H22 H 0.2878(31) 0.1292(10) 0.3669(26) 0.042(6) Uiso 1 d . . O3 O 1.0662(3) 0.10176(8) 0.9269(2) 0.0553(5) Uani 1 d . . H03 H 1.1761(47) 0.1239(13) 0.9815(38) 0.087(10) Uiso 1 d . . C3 C 0.4263(4) 0.18789(13) 0.5729(3) 0.0464(6) Uani 1 d . . H31 H 0.3206(34) 0.1799(10) 0.6622(30) 0.050(6) Uiso 1 d . . H32 H 0.4677(36) 0.2318(12) 0.5848(32) 0.062(8) Uiso 1 d . . C4 C 0.6222(3) 0.14933(11) 0.6270(3) 0.0394(6) Uani 1 d . . H4 H 0.5819(30) 0.1047(10) 0.6267(26) 0.042(6) Uiso 1 d . . C5 C 0.7874(3) 0.15971(13) 0.4951(3) 0.0422(6) Uani 1 d . . H51 H 0.8336(34) 0.2046(11) 0.5109(29) 0.052(7) Uiso 1 d . . H52 H 0.9109(35) 0.1346(10) 0.5302(28) 0.051(6) Uiso 1 d . . C6 C 0.6975(4) 0.14505(12) 0.2983(3) 0.0424(6) Uani 1 d . . H61 H 0.8032(35) 0.1523(9) 0.2143(30) 0.050(6) Uiso 1 d . . H62 H 0.6532(35) 0.0997(12) 0.2891(31) 0.060(7) Uiso 1 d . . C7 C 1.1358(4) 0.03888(11) 0.8923(3) 0.0497(6) Uani 1 d . . H7 H 1.2488(37) 0.0398(10) 0.8106(32) 0.064(7) Uiso 1 d . . C8 C 1.2223(4) 0.00688(12) 1.0691(4) 0.0502(6) Uani 1 d . . H81 H 1.2829(32) -0.0335(10) 1.0437(27) 0.045(6) Uiso 1 d . . H82 H 1.3402(35) 0.0321(10) 1.1322(29) 0.051(6) Uiso 1 d . . C9 C 1.0531(4) -0.00300(13) 1.1983(3) 0.0517(7) Uani 1 d . . H91 H 1.0063(32) 0.0375(11) 1.2401(28) 0.048(6) Uiso 1 d . . H92 H 1.1056(35) -0.0250(11) 1.3091(33) 0.057(7) Uiso 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 O1 0.0431(10) 0.0818(13) 0.0276(8) -0.0029(8) 0.0009(8) -0.0106(8) C1 0.0381(12) 0.0481(14) 0.0293(12) -0.0024(10) 0.0007(9) -0.0027(10) O2 0.0491(11) 0.0737(12) 0.0277(9) -0.0015(7) 0.0009(7) 0.0117(9) C2 0.0338(13) 0.060(2) 0.0363(13) 0.0009(11) 0.0015(10) 0.0049(12) O3 0.0426(10) 0.0473(10) 0.0726(12) 0.0026(8) -0.0106(8) 0.0003(8) C3 0.0415(13) 0.067(2) 0.0310(12) -0.0005(12) 0.0069(10) 0.0113(12) C4 0.0397(13) 0.051(2) 0.0273(12) 0.0004(10) 0.0042(9) 0.0023(11) C5 0.0349(13) 0.057(2) 0.0343(13) -0.0010(11) 0.0010(10) 0.0035(11) C6 0.0367(13) 0.061(2) 0.0304(12) -0.0039(11) 0.0088(10) 0.0004(11) C7 0.0399(14) 0.053(2) 0.057(2) 0.0000(12) 0.0066(12) 0.0033(11) C8 0.0347(13) 0.048(2) 0.066(2) -0.0051(12) -0.0068(12) 0.0034(11) C9 0.057(2) 0.050(2) 0.046(2) -0.0017(13) -0.0049(12) 0.0056(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.438(2) . ? O1 H01 0.88(3) . ? C1 C6 1.513(3) . ? C1 C2 1.513(3) . ? C1 H1 1.00(2) . ? O2 C4 1.439(2) . ? O2 H02 0.90(3) . ? C2 C3 1.533(3) . ? C2 H21 0.96(2) . ? C2 H22 1.01(2) . ? O3 C7 1.442(3) . ? O3 H03 0.90(3) . ? C3 C4 1.514(3) . ? C3 H31 1.00(2) . ? C3 H32 0.97(2) . ? C4 C5 1.516(3) . ? C4 H4 0.99(2) . ? C5 C6 1.529(3) . ? C5 H51 1.00(2) . ? C5 H52 0.97(2) . ? C6 H61 0.97(2) . ? C6 H62 1.01(2) . ? C7 C8 1.517(3) . ? C7 C9 1.521(3) 3_757 ? C7 H7 0.98(2) . ? C8 C9 1.520(3) . ? C8 H81 0.97(2) . ? C8 H82 1.00(2) . ? C9 C7 1.521(3) 3_757 ? C9 H91 0.97(2) . ? C9 H92 0.97(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H01 109.5(16) . . ? O1 C1 C6 111.9(2) . . ? O1 C1 C2 107.9(2) . . ? C6 C1 C2 111.1(2) . . ? O1 C1 H1 108.6(11) . . ? C6 C1 H1 109.2(11) . . ? C2 C1 H1 108.1(11) . . ? C4 O2 H02 108.6(17) . . ? C1 C2 C3 111.0(2) . . ? C1 C2 H21 109.8(12) . . ? C3 C2 H21 109.5(12) . . ? C1 C2 H22 109.6(12) . . ? C3 C2 H22 108.7(11) . . ? H21 C2 H22 108.2(17) . . ? C7 O3 H03 109.0(18) . . ? C4 C3 C2 111.1(2) . . ? C4 C3 H31 109.2(12) . . ? C2 C3 H31 112.2(12) . . ? C4 C3 H32 106.8(14) . . ? C2 C3 H32 109.9(14) . . ? H31 C3 H32 107.4(18) . . ? O2 C4 C3 108.3(2) . . ? O2 C4 C5 111.5(2) . . ? C3 C4 C5 111.2(2) . . ? O2 C4 H4 107.6(11) . . ? C3 C4 H4 108.4(11) . . ? C5 C4 H4 109.7(12) . . ? C4 C5 C6 110.8(2) . . ? C4 C5 H51 106.3(12) . . ? C6 C5 H51 112.4(12) . . ? C4 C5 H52 110.5(13) . . ? C6 C5 H52 110.8(13) . . ? H51 C5 H52 106.0(18) . . ? C1 C6 C5 110.7(2) . . ? C1 C6 H61 110.3(12) . . ? C5 C6 H61 110.4(12) . . ? C1 C6 H62 107.1(13) . . ? C5 C6 H62 109.5(13) . . ? H61 C6 H62 108.6(17) . . ? O3 C7 C8 111.1(2) . . ? O3 C7 C9 107.4(2) . 3_757 ? C8 C7 C9 110.4(2) . 3_757 ? O3 C7 H7 110.2(13) . . ? C8 C7 H7 107.8(14) . . ? C9 C7 H7 109.9(14) 3_757 . ? C7 C8 C9 112.0(2) . . ? C7 C8 H81 110.6(12) . . ? C9 C8 H81 108.6(12) . . ? C7 C8 H82 110.1(12) . . ? C9 C8 H82 109.5(12) . . ? H81 C8 H82 105.7(17) . . ? C8 C9 C7 112.2(2) . 3_757 ? C8 C9 H91 109.4(13) . . ? C7 C9 H91 109.2(13) 3_757 . ? C8 C9 H92 112.5(13) . . ? C7 C9 H92 108.2(14) 3_757 . ? H91 C9 H92 104.9(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 C3 56.1(3) . . . . ? C1 C2 C3 C4 -55.3(3) . . . . ? C2 C3 C4 O2 178.5(2) . . . . ? C2 C3 C4 C5 55.6(3) . . . . ? O2 C4 C5 C6 -177.3(2) . . . . ? C3 C4 C5 C6 -56.3(3) . . . . ? O1 C1 C6 C5 -177.5(2) . . . . ? C2 C1 C6 C5 -56.8(3) . . . . ? C4 C5 C6 C1 56.7(3) . . . . ? O3 C7 C8 C9 65.0(3) . . . . ? C9 C7 C8 C9 -54.1(3) 3_757 . . . ? C7 C8 C9 C7 55.1(3) . . . 3_757 ? _refine_diff_density_max 0.121 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.033 #================================================================END data_23 _audit_creation_method SHELXL _chemical_name_systematic ; trans-1,3-di(1,1,2,3,3,3-hexafluoropropyl)-cyclopentane-1,3-diol ; _chemical_name_common 'trans-1,3-di-(2H-hexafluoropropyl)-cyclopentane-1,3-diol' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H10 F12 O2' _chemical_formula_weight 402.19 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id '23' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; C(6A), C(7A), F(1A), F(2A), F(3A) are disordered over two positions each, with occupancies 75(2)% (unprimed) and 25(2)% (primed); F(3A') coincides with F(1A). F(9A) is disordered over two positions, with occupancies 92(1)% (primed)and 8(1)% (unprimed). ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P2(1)/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 12.651(1) _cell_length_b 10.436(1) _cell_length_c 22.301(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.69(1) _cell_angle_gamma 90.00 _cell_volume 2860.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 386 _cell_measurement_theta_min 10 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method ? _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0200 0.00 0.00 -1.00 0.0200 0.00 -1.00 0.00 0.1500 0.00 1.00 0.00 0.1500 -1.00 0.00 0.00 0.2250 1.00 0.00 0.00 0.2250 -1.00 -2.00 1.00 0.1600 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (10 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 92 duplicate reflections. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 150(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.6 _diffrn_reflns_number 16913 _diffrn_reflns_av_R_equivalents 0.1069 _diffrn_reflns_av_sigmaI/netI 0.0937 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5038 _reflns_number_observed 2747 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 193 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+16.4106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4845 _refine_ls_number_parameters 473 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1832 _refine_ls_R_factor_obs 0.0944 _refine_ls_wR_factor_all 0.2028 _refine_ls_wR_factor_obs 0.1500 _refine_ls_goodness_of_fit_all 1.123 _refine_ls_goodness_of_fit_obs 1.293 _refine_ls_restrained_S_all 1.245 _refine_ls_restrained_S_obs 1.297 _refine_ls_shift/esd_max 0.005 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1A O 0.2405(4) 0.2566(4) 0.2191(2) 0.0422(13) Uani 1 d . . H01A H 0.2505(4) 0.2160(4) 0.1883(2) 0.055 Uiso 1 d R . O3A O 0.5439(3) 0.4617(4) 0.1979(2) 0.0278(10) Uani 1 d . . H03A H 0.5908(3) 0.4314(4) 0.2279(2) 0.036 Uiso 1 d R . C1A C 0.3316(6) 0.3390(7) 0.2422(3) 0.039(2) Uani 1 d D . C2A C 0.4380(5) 0.2857(7) 0.2294(3) 0.035(2) Uani 1 d . . H2A1 H 0.4285(5) 0.1946(7) 0.2170(3) 0.045 Uiso 1 d R . H2A2 H 0.4990(5) 0.2922(7) 0.2665(3) 0.045 Uiso 1 d R . C3A C 0.4609(5) 0.3684(6) 0.1756(3) 0.028(2) Uani 1 d . . C4A C 0.3548(5) 0.4398(6) 0.1497(3) 0.035(2) Uani 1 d . . H4A1 H 0.3033(5) 0.3870(6) 0.1192(3) 0.045 Uiso 1 d R . H4A2 H 0.3685(5) 0.5211(6) 0.1299(3) 0.045 Uiso 1 d R . C5A C 0.3122(6) 0.4649(7) 0.2078(3) 0.043(2) Uani 1 d . . H5A1 H 0.2336(6) 0.4858(7) 0.1965(3) 0.056 Uiso 1 d R . H5A2 H 0.3521(6) 0.5361(7) 0.2326(3) 0.056 Uiso 1 d R . C6A C 0.3522(8) 0.3382(10) 0.3146(5) 0.037(3) Uani 0.746(15) d P 1 C7A C 0.2514(8) 0.3700(9) 0.3388(4) 0.037(3) Uani 0.746(15) d P 1 H7A H 0.1925(8) 0.3096(9) 0.3183(4) 0.048 Uiso 0.746(15) d PR 1 C6A' C 0.3066(18) 0.3950(21) 0.2991(10) 0.021(7) Uiso 0.254(15) d PD 2 C7A' C 0.2943(18) 0.2844(22) 0.3439(9) 0.026(8) Uiso 0.254(15) d PD 2 H7A' H 0.2284(18) 0.2341(22) 0.3232(9) 0.033 Uiso 0.254(15) d PR 2 F1A' F 0.3936(17) 0.4701(19) 0.3249(9) 0.034(5) Uiso 0.254(15) d PD 2 F2A' F 0.2174(18) 0.4754(21) 0.2928(11) 0.044(7) Uiso 0.254(15) d PD 2 C8A C 0.2682(9) 0.3510(11) 0.4072(4) 0.070(3) Uani 1 d D . C9A C 0.5018(5) 0.2820(6) 0.1301(3) 0.031(2) Uani 1 d . . C10A C 0.5342(7) 0.3490(8) 0.0777(4) 0.048(2) Uani 1 d D . H10A H 0.5857(7) 0.4198(8) 0.0951(4) 0.062 Uiso 0.923(10) d PR 1 C11A C 0.5850(6) 0.2673(8) 0.0348(4) 0.046(2) Uani 1 d . . F1A F 0.3842(3) 0.2129(4) 0.3399(2) 0.0417(10) Uani 1 d D . F2A F 0.4345(6) 0.4221(8) 0.3394(3) 0.039(2) Uani 0.746(15) d P 1 F3A F 0.2255(5) 0.4953(6) 0.3221(5) 0.047(2) Uani 0.746(15) d P 1 F4A F 0.2742(5) 0.2286(6) 0.4278(2) 0.085(2) Uani 1 d . . F5A F 0.1820(5) 0.4039(6) 0.4204(3) 0.087(2) Uani 1 d . . F6A F 0.3585(5) 0.4051(6) 0.4397(2) 0.094(2) Uani 1 d . . F7A F 0.5933(3) 0.2160(3) 0.1613(2) 0.0341(9) Uani 1 d . . F8A F 0.4248(3) 0.1913(3) 0.1070(2) 0.0406(10) Uani 1 d . . F9A F 0.4423(4) 0.4028(5) 0.0407(2) 0.067(2) Uani 0.923(10) d P 1 F9A' F 0.5754(35) 0.4607(30) 0.0869(20) 0.031(17) Uiso 0.077(10) d PD 2 F10A F 0.5243(4) 0.1624(5) 0.0148(2) 0.0678(15) Uani 1 d . . F11A F 0.6806(4) 0.2200(5) 0.0632(2) 0.0664(14) Uani 1 d . . F12A F 0.5943(5) 0.3297(5) -0.0137(2) 0.090(2) Uani 1 d . . O1B O 1.0050(3) 0.2225(4) 0.2940(2) 0.0297(11) Uani 1 d . . H01B H 0.9998(3) 0.1417(4) 0.2972(2) 0.039 Uiso 1 d R . O3B O 0.6952(3) 0.4100(4) 0.3080(2) 0.0342(11) Uani 1 d . . H03B H 0.6825(3) 0.4658(4) 0.3333(2) 0.044 Uiso 1 d R . C1B C 0.9104(5) 0.2987(6) 0.2712(3) 0.0261(15) Uani 1 d . . C2B C 0.8070(5) 0.2403(6) 0.2871(3) 0.030(2) Uani 1 d . . H2B1 H 0.7451(5) 0.2403(6) 0.2504(3) 0.039 Uiso 1 d R . H2B2 H 0.8208(5) 0.1513(6) 0.3023(3) 0.039 Uiso 1 d R . C3B C 0.7826(5) 0.3261(6) 0.3379(3) 0.0256(15) Uani 1 d . . C4B C 0.8868(5) 0.4015(6) 0.3631(3) 0.031(2) Uani 1 d . . H4B1 H 0.9400(5) 0.3503(6) 0.3934(3) 0.040 Uiso 1 d R . H4B2 H 0.8718(5) 0.4824(6) 0.3828(3) 0.040 Uiso 1 d R . C5B C 0.9265(5) 0.4279(6) 0.3047(3) 0.028(2) Uani 1 d . . H5B1 H 1.0043(5) 0.4526(6) 0.3153(3) 0.037 Uiso 1 d R . H5B2 H 0.8836(5) 0.4964(6) 0.2793(3) 0.037 Uiso 1 d R . C6B C 0.8918(6) 0.3064(6) 0.2009(3) 0.036(2) Uani 1 d . . C7B C 0.9871(6) 0.3490(8) 0.1773(4) 0.049(2) Uani 1 d . . H7B H 1.0507(6) 0.2939(8) 0.1966(4) 0.064 Uiso 1 d R . C8B C 0.9728(8) 0.3475(10) 0.1067(4) 0.059(2) Uani 1 d . . C9B C 0.7429(5) 0.2468(7) 0.3874(3) 0.033(2) Uani 1 d . . C10B C 0.7344(7) 0.3206(8) 0.4453(3) 0.050(2) Uani 1 d . . H10B H 0.8095(7) 0.3354(8) 0.4712(3) 0.066 Uiso 1 d R . C11B C 0.6674(7) 0.2521(10) 0.4850(4) 0.058(2) Uani 1 d . . F1B F 0.8639(3) 0.1808(4) 0.1754(2) 0.0401(10) Uani 1 d . . F2B F 0.8038(3) 0.3821(4) 0.1774(2) 0.0437(11) Uani 1 d . . F3B F 1.0106(4) 0.4718(4) 0.1971(2) 0.0569(13) Uani 1 d . . F4B F 0.9639(5) 0.2286(6) 0.0853(2) 0.090(2) Uani 1 d . . F5B F 1.0569(4) 0.3991(6) 0.0927(2) 0.080(2) Uani 1 d . . F6B F 0.8822(5) 0.4051(7) 0.0766(2) 0.098(2) Uani 1 d . . F7B F 0.8185(3) 0.1526(4) 0.4083(2) 0.0483(11) Uani 1 d . . F8B F 0.6489(3) 0.1855(4) 0.3598(2) 0.0471(11) Uani 1 d . . F9B F 0.6864(5) 0.4358(5) 0.4293(2) 0.074(2) Uani 1 d . . F10B F 0.5648(4) 0.2436(6) 0.4594(2) 0.093(2) Uani 1 d . . F11B F 0.7062(4) 0.1346(6) 0.4990(2) 0.075(2) Uani 1 d . . F12B F 0.6796(5) 0.3144(6) 0.5383(2) 0.086(2) Uani 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 O1A 0.036(3) 0.039(3) 0.059(3) -0.027(3) 0.026(3) -0.021(2) O3A 0.024(2) 0.023(2) 0.035(3) -0.002(2) 0.004(2) -0.004(2) C1A 0.034(4) 0.042(5) 0.046(5) -0.014(4) 0.019(4) -0.021(4) C2A 0.038(4) 0.034(4) 0.035(4) 0.001(3) 0.012(4) -0.008(3) C3A 0.030(4) 0.020(4) 0.036(4) -0.008(3) 0.012(3) -0.005(3) C4A 0.024(4) 0.026(4) 0.052(5) -0.003(3) 0.005(4) -0.001(3) C5A 0.026(4) 0.039(5) 0.069(6) -0.022(4) 0.018(4) -0.006(3) C6A 0.025(6) 0.035(7) 0.048(7) -0.002(5) 0.005(5) -0.003(5) C7A 0.041(6) 0.026(6) 0.048(7) 0.007(5) 0.017(5) 0.006(5) C8A 0.081(8) 0.097(9) 0.035(5) -0.001(5) 0.019(5) -0.052(7) C9A 0.027(4) 0.021(4) 0.043(4) -0.003(3) 0.000(3) -0.006(3) C10A 0.053(5) 0.047(5) 0.051(5) 0.004(4) 0.026(4) 0.004(4) C11A 0.046(5) 0.052(5) 0.046(5) -0.015(4) 0.022(4) -0.004(4) F1A 0.041(2) 0.040(2) 0.046(2) 0.008(2) 0.015(2) 0.016(2) F2A 0.030(4) 0.049(4) 0.036(4) -0.008(3) 0.005(3) -0.016(4) F3A 0.049(4) 0.034(4) 0.066(6) 0.021(4) 0.027(4) 0.016(3) F4A 0.112(5) 0.086(4) 0.075(4) 0.006(3) 0.056(4) 0.003(4) F5A 0.089(4) 0.089(4) 0.084(4) 0.024(3) 0.022(4) -0.005(4) F6A 0.094(4) 0.135(5) 0.048(3) -0.004(3) 0.005(3) -0.042(4) F7A 0.026(2) 0.026(2) 0.050(2) 0.005(2) 0.007(2) 0.006(2) F8A 0.037(2) 0.034(2) 0.051(3) -0.014(2) 0.012(2) -0.010(2) F9A 0.064(4) 0.085(4) 0.059(4) 0.032(3) 0.029(3) 0.036(3) F10A 0.067(3) 0.084(4) 0.056(3) -0.037(3) 0.022(3) -0.009(3) F11A 0.044(3) 0.098(4) 0.061(3) -0.015(3) 0.019(3) 0.015(3) F12A 0.138(5) 0.089(4) 0.064(3) 0.021(3) 0.066(4) 0.035(4) O1B 0.024(2) 0.024(2) 0.041(3) 0.008(2) 0.007(2) 0.006(2) O3B 0.035(3) 0.031(3) 0.036(3) 0.001(2) 0.007(2) 0.011(2) C1B 0.023(4) 0.020(4) 0.034(4) 0.000(3) 0.005(3) 0.001(3) C2B 0.028(4) 0.022(4) 0.037(4) -0.002(3) 0.003(3) 0.002(3) C3B 0.027(4) 0.025(4) 0.025(4) 0.002(3) 0.006(3) 0.003(3) C4B 0.031(4) 0.027(4) 0.035(4) -0.002(3) 0.011(3) -0.001(3) C5B 0.026(4) 0.023(4) 0.037(4) 0.003(3) 0.009(3) 0.004(3) C6B 0.039(4) 0.027(4) 0.039(4) 0.008(3) 0.004(4) 0.010(3) C7B 0.039(5) 0.050(5) 0.059(5) 0.006(4) 0.012(4) 0.001(4) C8B 0.080(7) 0.068(7) 0.037(5) -0.008(5) 0.028(5) -0.007(6) C9B 0.032(4) 0.035(4) 0.029(4) 0.010(3) 0.003(3) 0.004(3) C10B 0.058(6) 0.056(6) 0.045(5) 0.016(4) 0.027(4) 0.013(4) C11B 0.042(5) 0.088(8) 0.045(5) 0.003(5) 0.011(4) -0.004(5) F1B 0.046(3) 0.032(2) 0.043(2) -0.002(2) 0.010(2) -0.014(2) F2B 0.046(3) 0.043(3) 0.040(2) 0.011(2) 0.007(2) 0.016(2) F3B 0.063(3) 0.051(3) 0.066(3) -0.018(2) 0.032(3) -0.031(2) F4B 0.115(5) 0.097(5) 0.074(4) -0.013(3) 0.056(4) -0.033(4) F5B 0.077(4) 0.117(5) 0.059(3) 0.002(3) 0.042(3) -0.021(3) F6B 0.076(4) 0.174(6) 0.044(3) 0.039(4) 0.015(3) 0.020(4) F7B 0.042(3) 0.047(3) 0.056(3) 0.021(2) 0.011(2) 0.008(2) F8B 0.033(2) 0.045(3) 0.063(3) 0.006(2) 0.009(2) -0.008(2) F9B 0.109(4) 0.064(3) 0.064(3) 0.004(3) 0.048(3) 0.020(3) F10B 0.035(3) 0.178(6) 0.070(4) 0.034(4) 0.020(3) -0.002(4) F11B 0.071(4) 0.093(4) 0.065(3) 0.031(3) 0.022(3) -0.001(3) F12B 0.097(4) 0.115(5) 0.058(3) 0.004(3) 0.040(3) -0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.433(7) . ? O3A C3A 1.432(7) . ? C1A C6A' 1.50(2) . ? C1A C5A 1.512(10) . ? C1A C2A 1.544(9) . ? C1A C6A 1.574(12) . ? C2A C3A 1.561(9) . ? C3A C4A 1.524(9) . ? C3A C9A 1.535(9) . ? C4A C5A 1.540(9) . ? C6A F2A 1.372(10) . ? C6A F1A 1.443(11) . ? C6A C7A 1.534(13) . ? C7A F3A 1.378(10) . ? C7A C8A 1.501(12) . ? C6A' F1A' 1.36(2) . ? C6A' F2A' 1.39(2) . ? C6A' C7A' 1.56(2) . ? C7A' F1A 1.38(2) . ? C7A' C8A 1.67(2) . ? C8A F5A 1.317(11) . ? C8A F6A 1.326(10) . ? C8A F4A 1.353(11) . ? C9A F8A 1.368(7) . ? C9A F7A 1.384(7) . ? C9A C10A 1.499(9) . ? C10A F9A' 1.27(3) . ? C10A F9A 1.377(9) . ? C10A C11A 1.532(10) . ? C11A F12A 1.291(9) . ? C11A F11A 1.321(9) . ? C11A F10A 1.351(9) . ? O1B C1B 1.427(7) . ? O3B C3B 1.444(7) . ? C1B C5B 1.531(8) . ? C1B C6B 1.531(9) . ? C1B C2B 1.558(8) . ? C2B C3B 1.532(8) . ? C3B C4B 1.524(9) . ? C3B C9B 1.554(9) . ? C4B C5B 1.529(8) . ? C6B F2B 1.364(7) . ? C6B F1B 1.439(8) . ? C6B C7B 1.493(10) . ? C7B F3B 1.366(8) . ? C7B C8B 1.541(11) . ? C8B F5B 1.297(9) . ? C8B F4B 1.325(10) . ? C8B F6B 1.328(10) . ? C9B F8B 1.362(7) . ? C9B F7B 1.374(7) . ? C9B C10B 1.531(10) . ? C10B F9B 1.355(8) . ? C10B C11B 1.538(11) . ? C11B F10B 1.292(9) . ? C11B F12B 1.332(9) . ? C11B F11B 1.330(10) . ? 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 O1A C1A C6A' 103.0(9) . . ? O1A C1A C5A 108.6(6) . . ? C6A' C1A C5A 92.8(10) . . ? O1A C1A C2A 112.3(6) . . ? C6A' C1A C2A 131.8(11) . . ? C5A C1A C2A 105.3(5) . . ? O1A C1A C6A 106.8(6) . . ? C5A C1A C6A 119.5(7) . . ? C2A C1A C6A 104.4(6) . . ? C1A C2A C3A 105.8(5) . . ? O3A C3A C4A 107.9(5) . . ? O3A C3A C9A 107.1(5) . . ? C4A C3A C9A 116.1(6) . . ? O3A C3A C2A 111.3(5) . . ? C4A C3A C2A 104.8(5) . . ? C9A C3A C2A 109.7(5) . . ? C3A C4A C5A 102.5(6) . . ? C1A C5A C4A 103.4(5) . . ? F2A C6A F1A 107.8(8) . . ? F2A C6A C7A 109.6(8) . . ? F1A C6A C7A 103.8(7) . . ? F2A C6A C1A 109.6(7) . . ? F1A C6A C1A 111.6(7) . . ? C7A C6A C1A 114.2(8) . . ? F3A C7A C8A 111.5(9) . . ? F3A C7A C6A 105.9(8) . . ? C8A C7A C6A 113.5(9) . . ? F1A' C6A' F2A' 104.6(19) . . ? F1A' C6A' C1A 105.7(15) . . ? F2A' C6A' C1A 118.8(18) . . ? F1A' C6A' C7A' 110.4(19) . . ? F2A' C6A' C7A' 108.1(18) . . ? C1A C6A' C7A' 109.1(15) . . ? F1A C7A' C6A' 98.6(15) . . ? F1A C7A' C8A 127.5(16) . . ? C6A' C7A' C8A 107.6(15) . . ? F5A C8A F6A 110.5(8) . . ? F5A C8A F4A 107.6(7) . . ? F6A C8A F4A 104.2(9) . . ? F5A C8A C7A 104.3(9) . . ? F6A C8A C7A 113.4(7) . . ? F4A C8A C7A 116.9(8) . . ? F5A C8A C7A' 134.6(11) . . ? F6A C8A C7A' 108.8(11) . . ? F4A C8A C7A' 83.6(10) . . ? F8A C9A F7A 106.3(5) . . ? F8A C9A C10A 109.4(6) . . ? F7A C9A C10A 105.9(5) . . ? F8A C9A C3A 109.5(5) . . ? F7A C9A C3A 109.4(5) . . ? C10A C9A C3A 116.0(6) . . ? F9A' C10A C9A 118.6(21) . . ? F9A C10A C9A 108.0(6) . . ? F9A' C10A C11A 113.2(21) . . ? F9A C10A C11A 105.8(6) . . ? C9A C10A C11A 117.4(7) . . ? F12A C11A F11A 109.6(6) . . ? F12A C11A F10A 106.8(7) . . ? F11A C11A F10A 103.9(7) . . ? F12A C11A C10A 112.2(7) . . ? F11A C11A C10A 112.3(7) . . ? F10A C11A C10A 111.5(6) . . ? O1B C1B C5B 108.2(5) . . ? O1B C1B C6B 107.8(5) . . ? C5B C1B C6B 115.1(5) . . ? O1B C1B C2B 112.3(5) . . ? C5B C1B C2B 104.8(5) . . ? C6B C1B C2B 108.7(5) . . ? C3B C2B C1B 105.5(5) . . ? O3B C3B C4B 111.0(5) . . ? O3B C3B C2B 106.2(5) . . ? C4B C3B C2B 105.4(5) . . ? O3B C3B C9B 108.0(5) . . ? C4B C3B C9B 114.2(5) . . ? C2B C3B C9B 111.7(5) . . ? C3B C4B C5B 102.1(5) . . ? C4B C5B C1B 103.0(5) . . ? F2B C6B F1B 106.0(5) . . ? F2B C6B C7B 110.2(6) . . ? F1B C6B C7B 105.9(6) . . ? F2B C6B C1B 109.7(5) . . ? F1B C6B C1B 108.8(5) . . ? C7B C6B C1B 115.8(6) . . ? F3B C7B C6B 107.3(6) . . ? F3B C7B C8B 107.7(7) . . ? C6B C7B C8B 116.6(7) . . ? F5B C8B F4B 107.8(7) . . ? F5B C8B F6B 110.5(8) . . ? F4B C8B F6B 104.6(8) . . ? F5B C8B C7B 109.8(7) . . ? F4B C8B C7B 110.9(8) . . ? F6B C8B C7B 113.1(7) . . ? F8B C9B F7B 106.3(5) . . ? F8B C9B C10B 113.0(6) . . ? F7B C9B C10B 104.8(5) . . ? F8B C9B C3B 108.9(5) . . ? F7B C9B C3B 107.8(5) . . ? C10B C9B C3B 115.5(6) . . ? F9B C10B C9B 109.9(6) . . ? F9B C10B C11B 106.9(7) . . ? C9B C10B C11B 114.2(7) . . ? F10B C11B F12B 108.7(8) . . ? F10B C11B F11B 108.4(8) . . ? F12B C11B F11B 106.3(7) . . ? F10B C11B C10B 114.3(7) . . ? F12B C11B C10B 108.9(7) . . ? F11B C11B C10B 110.0(7) . . ? _refine_diff_density_max 0.554 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.080 #==============================================================END data_24 _audit_creation_method SHELXL _chemical_name_systematic ; cis-1,3-di(1,1,2,3,3,3-hexafluoropropyl)-cyclohexane-1,3-diol ; _chemical_name_common 'cis-1,3-di(2H-hexafluoropropyl)-cyclohexane-1,3-diol' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H12 F12 O2' _chemical_formula_weight 416.22 _chemical_melting_point '84-86 deg.C' _chemical_compound_source ? _ccdc_compound_id '24' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; ? ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P2(1)/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 10.590(2) _cell_length_b 39.347(3) _cell_length_c 15.135(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.60(1) _cell_angle_gamma 90.00 _cell_volume 6286(3) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 369 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method ? _exptl_crystal_F_000 3328 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.6017 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1996)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.0300 0.00 1.00 0.00 0.0300 1.00 1.00 0.00 0.1250 -1.00 -1.00 0.00 0.1250 0.00 1.00 -1.00 0.2250 0.00 -1.00 1.00 0.2250 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (30 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 287 duplicate reflections. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 150(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 'Siemens CCD area detector' _diffrn_measurement_method '\w scan' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 37884 _diffrn_reflns_av_R_equivalents 0.1290 _diffrn_reflns_av_sigmaI/netI 0.0976 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 51 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11064 _reflns_number_observed 6678 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 388 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+56.8599P] 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 10675 _refine_ls_number_parameters 858 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2140 _refine_ls_R_factor_obs 0.1416 _refine_ls_wR_factor_all 0.3780 _refine_ls_wR_factor_obs 0.3052 _refine_ls_goodness_of_fit_all 1.170 _refine_ls_goodness_of_fit_obs 1.346 _refine_ls_restrained_S_all 1.290 _refine_ls_restrained_S_obs 1.346 _refine_ls_shift/esd_max -0.008 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1A C 0.4581(9) 0.0712(2) 0.3602(6) 0.037(2) Uiso 1 d . . C2A C 0.4005(8) 0.1024(2) 0.4009(6) 0.031(2) Uiso 1 d . . H2A1 H 0.3139(8) 0.0966(2) 0.4163(6) 0.041 Uiso 1 d R . H2A2 H 0.3936(8) 0.1210(2) 0.3570(6) 0.041 Uiso 1 d R . C3A C 0.4806(8) 0.1141(2) 0.4849(6) 0.028(2) Uiso 1 d . . C4A C 0.5015(10) 0.0855(3) 0.5518(7) 0.047(3) Uiso 1 d . . H4A1 H 0.5568(10) 0.0932(3) 0.6038(7) 0.061 Uiso 1 d R . H4A2 H 0.4185(10) 0.0791(3) 0.5727(7) 0.061 Uiso 1 d R . C5A C 0.5571(10) 0.0545(3) 0.5124(7) 0.049(3) Uiso 1 d . . H5A1 H 0.6425(10) 0.0605(3) 0.4953(7) 0.064 Uiso 1 d R . H5A2 H 0.5667(10) 0.0361(3) 0.5573(7) 0.064 Uiso 1 d R . C6A C 0.4775(10) 0.0417(3) 0.4286(7) 0.047(3) Uiso 1 d . . H6A1 H 0.3940(10) 0.0340(3) 0.4459(7) 0.060 Uiso 1 d R . H6A2 H 0.5202(10) 0.0221(3) 0.4026(7) 0.060 Uiso 1 d R . C7A C 0.3736(9) 0.0583(3) 0.2777(6) 0.041(2) Uani 1 d . . C8A C 0.3577(10) 0.0847(3) 0.2051(6) 0.047(3) Uani 1 d . . H8A H 0.4372(10) 0.0983(3) 0.2031(6) 0.061 Uiso 1 d R . C9A C 0.3214(12) 0.0672(4) 0.1106(7) 0.063(3) Uani 1 d . . C10A C 0.4247(8) 0.1461(2) 0.5282(6) 0.034(2) Uani 1 d . . C11A C 0.4057(9) 0.1779(3) 0.4679(6) 0.038(2) Uani 1 d . . C12A C 0.3787(12) 0.2104(3) 0.5129(8) 0.064(3) Uani 1 d . . O1A O 0.5771(6) 0.0795(2) 0.3250(4) 0.039(2) Uani 1 d . . H01A H 0.6124(49) 0.0954(19) 0.3548(45) 0.058 Uiso 1 d R . O3A O 0.5992(5) 0.1257(2) 0.4537(4) 0.0323(14) Uani 1 d . . H03A H 0.6585(14) 0.1219(23) 0.4927(27) 0.048 Uiso 1 d R . F1A F 0.2589(6) 0.0488(2) 0.3021(4) 0.060(2) Uani 1 d . . F2A F 0.4306(6) 0.0296(2) 0.2455(4) 0.061(2) Uani 1 d . . F3A F 0.2605(7) 0.1051(2) 0.2198(4) 0.071(2) Uani 1 d . . F4A F 0.2860(7) 0.0922(2) 0.0536(4) 0.081(2) Uani 1 d . . F5A F 0.2272(7) 0.0454(2) 0.1109(4) 0.071(2) Uani 1 d . . F6A F 0.4197(7) 0.0525(2) 0.0803(4) 0.093(3) Uani 1 d . . F7A F 0.3122(5) 0.13765(15) 0.5617(3) 0.0473(14) Uani 1 d . . F8A F 0.5074(5) 0.15494(14) 0.5992(3) 0.0440(14) Uani 1 d . . F9A F 0.2983(7) 0.1725(2) 0.4098(5) 0.056(3) Uani 0.815(14) d P 1 F9A' F 0.5242(30) 0.1901(8) 0.4640(21) 0.053(11) Uiso 0.185(14) d P 2 F10A F 0.3509(6) 0.2349(2) 0.4579(4) 0.063(2) Uani 1 d . . F11A F 0.2950(12) 0.2093(2) 0.5693(6) 0.134(5) Uani 1 d . . F12A F 0.4899(9) 0.2208(2) 0.5591(6) 0.102(3) Uani 1 d . . C1B C 0.9078(8) 0.1439(2) 0.5534(6) 0.029(2) Uiso 1 d . . C2B C 0.9971(8) 0.1553(2) 0.6321(6) 0.031(2) Uiso 1 d . . H2B1 H 1.0804(8) 0.1614(2) 0.6112(6) 0.040 Uiso 1 d R . H2B2 H 1.0105(8) 0.1361(2) 0.6741(6) 0.040 Uiso 1 d R . C3B C 0.9448(8) 0.1856(2) 0.6815(6) 0.035(2) Uiso 1 d . . C4B C 0.9121(9) 0.2152(2) 0.6164(6) 0.037(2) Uiso 1 d . . H4B1 H 0.8739(9) 0.2340(2) 0.6484(6) 0.048 Uiso 1 d R . H4B2 H 0.9908(9) 0.2237(2) 0.5930(6) 0.048 Uiso 1 d R . C5B C 0.8211(9) 0.2036(3) 0.5395(7) 0.043(2) Uiso 1 d . . H5B1 H 0.8034(9) 0.2229(3) 0.4984(7) 0.056 Uiso 1 d R . H5B2 H 0.7402(9) 0.1967(3) 0.5627(7) 0.056 Uiso 1 d R . C6B C 0.8753(9) 0.1743(2) 0.4900(6) 0.040(2) Uiso 1 d . . H6B1 H 0.9519(9) 0.1817(2) 0.4619(6) 0.052 Uiso 1 d R . H6B2 H 0.8116(9) 0.1667(2) 0.4427(6) 0.052 Uiso 1 d R . C7B C 0.9647(9) 0.1143(3) 0.5020(6) 0.039(2) Uani 1 d . . C8B C 0.9970(10) 0.0825(3) 0.5572(6) 0.044(2) Uani 1 d . . C9B C 1.0132(18) 0.0511(4) 0.5059(11) 0.049(4) Uiso 0.727(12) d P 1 C9B' C 1.0859(36) 0.0537(8) 0.5235(22) 0.028(8) Uiso 0.273(12) d P 2 C10B C 1.0368(8) 0.1964(2) 0.7592(6) 0.037(2) Uani 1 d . . C11B C 1.0690(10) 0.1692(3) 0.8283(6) 0.044(2) Uani 1 d . . H11B H 0.9952(10) 0.1536(3) 0.8317(6) 0.057 Uiso 1 d R . C12B C 1.1089(10) 0.1835(3) 0.9210(7) 0.052(3) Uani 1 d . . O1B O 0.7938(5) 0.1291(2) 0.5841(4) 0.0324(14) Uani 1 d . . H01B H 0.7441(41) 0.1447(2) 0.5968(64) 0.049 Uiso 1 d R . O3B O 0.8322(5) 0.1729(2) 0.7196(4) 0.0335(14) Uani 1 d . . H03B H 0.7895(51) 0.1893(2) 0.7364(63) 0.050 Uiso 1 d R . F1B F 1.0684(5) 0.1252(2) 0.4636(4) 0.052(2) Uani 1 d . . F2B F 0.8776(5) 0.1053(2) 0.4340(3) 0.0480(14) Uani 1 d . . F3B F 1.1188(8) 0.0899(2) 0.6011(5) 0.058(3) Uani 0.727(12) d P 1 F3B' F 0.8659(27) 0.0610(7) 0.5491(20) 0.085(10) Uiso 0.273(12) d P 2 F4B F 1.0677(8) 0.0267(2) 0.5608(5) 0.079(2) Uani 1 d . . F5B F 1.0801(8) 0.0528(2) 0.4373(5) 0.092(3) Uani 1 d . . F6B F 0.9005(10) 0.0402(2) 0.4750(7) 0.077(3) Uani 0.727(12) d P 1 F6B' F 1.1948(26) 0.0661(7) 0.5419(18) 0.078(9) Uiso 0.273(12) d P 2 F7B F 1.1459(5) 0.20889(15) 0.7286(3) 0.0471(14) Uani 1 d . . F8B F 0.9829(5) 0.22424(14) 0.8000(4) 0.0481(14) Uani 1 d . . F9B F 1.1730(6) 0.1512(2) 0.8036(4) 0.059(2) Uani 1 d . . F10B F 1.1557(6) 0.1582(2) 0.9725(4) 0.069(2) Uani 1 d . . F11B F 1.1957(7) 0.2074(2) 0.9230(4) 0.070(2) Uani 1 d . . F12B F 1.0045(7) 0.1948(2) 0.9583(4) 0.089(3) Uani 1 d . . C1C C 0.5801(8) 0.2137(2) -0.1420(5) 0.027(2) Uiso 1 d . . C2C C 0.5549(8) 0.2093(2) -0.0444(6) 0.030(2) Uiso 1 d . . H2C1 H 0.6123(8) 0.2243(2) -0.0073(6) 0.039 Uiso 1 d R . H2C2 H 0.4667(8) 0.2162(2) -0.0363(6) 0.039 Uiso 1 d R . C3C C 0.5733(8) 0.1729(2) -0.0127(5) 0.027(2) Uiso 1 d . . C4C C 0.4947(9) 0.1476(2) -0.0713(6) 0.038(2) Uiso 1 d . . H4C1 H 0.4035(9) 0.1511(2) -0.0640(6) 0.050 Uiso 1 d R . H4C2 H 0.5171(9) 0.1241(2) -0.0528(6) 0.050 Uiso 1 d R . C5C C 0.5221(9) 0.1528(2) -0.1709(6) 0.040(2) Uiso 1 d . . H5C1 H 0.6109(9) 0.1466(2) -0.1792(6) 0.053 Uiso 1 d R . H5C2 H 0.4660(9) 0.1378(2) -0.2089(6) 0.053 Uiso 1 d R . C6C C 0.4996(9) 0.1891(2) -0.1998(6) 0.039(2) Uiso 1 d . . H6C1 H 0.5187(9) 0.1919(2) -0.2624(6) 0.051 Uiso 1 d R . H6C2 H 0.4092(9) 0.1948(2) -0.1957(6) 0.051 Uiso 1 d R . C7C C 0.5490(10) 0.2510(3) -0.1667(6) 0.042(2) Uani 1 d . . C8C C 0.6246(17) 0.2660(3) -0.2423(8) 0.079(4) Uani 1 d . . C9C C 0.5776(20) 0.3005(4) -0.2783(10) 0.100(6) Uani 1 d . . C10C C 0.5404(9) 0.1694(2) 0.0851(6) 0.037(2) Uani 1 d . . C11C C 0.6225(11) 0.1896(2) 0.1532(6) 0.037(2) Uani 1 d . . C12C C 0.6111(13) 0.1799(3) 0.2505(6) 0.059(3) Uani 1 d . . O1C O 0.7099(6) 0.2094(2) -0.1533(4) 0.038(2) Uani 1 d . . H01C H 0.7426(23) 0.1968(22) -0.1130(42) 0.056 Uiso 1 d R . O3C O 0.7067(6) 0.1656(2) -0.0111(4) 0.0366(15) Uani 1 d . . H03C H 0.7179(9) 0.1444(2) -0.0091(73) 0.055 Uiso 1 d R . F1C F 0.5872(7) 0.27258(15) -0.0986(4) 0.060(2) Uani 1 d . . F2C F 0.4242(6) 0.2559(2) -0.1821(5) 0.068(2) Uani 1 d . . F3C F 0.6334(8) 0.2444(2) -0.3074(4) 0.063(3) Uani 0.82(2) d P 1 F3C' F 0.7391(41) 0.2709(10) -0.2351(26) 0.071(14) Uiso 0.18(2) d P 2 F4C F 0.5511(14) 0.3218(2) -0.2208(6) 0.147(5) Uani 1 d . . F5C F 0.4675(12) 0.2964(3) -0.3293(7) 0.136(4) Uani 1 d . . F6C F 0.6561(13) 0.3115(3) -0.3341(7) 0.144(4) Uani 1 d . . F7C F 0.4165(5) 0.1781(2) 0.0912(4) 0.059(2) Uani 1 d . . F8C F 0.5497(6) 0.13588(14) 0.1102(4) 0.054(2) Uani 1 d . . F9C F 0.5944(10) 0.2226(2) 0.1478(4) 0.087(4) Uani 0.88(2) d P 1 F9C' F 0.7222(66) 0.1905(16) 0.1501(42) 0.080(23) Uiso 0.12(2) d P 2 F10C F 0.6667(8) 0.2022(2) 0.3049(4) 0.075(2) Uani 1 d . . F11C F 0.4974(8) 0.1741(3) 0.2698(4) 0.116(4) Uani 1 d . . F12C F 0.6758(9) 0.1501(2) 0.2673(4) 0.094(3) Uani 1 d . . C1D C 0.8555(9) 0.0782(2) 0.0397(6) 0.039(2) Uiso 1 d . . C2D C 0.8388(9) 0.0425(2) 0.0756(6) 0.037(2) Uiso 1 d . . H2D1 H 0.9184(9) 0.0295(2) 0.0721(6) 0.049 Uiso 1 d R . H2D2 H 0.7713(9) 0.0306(2) 0.0384(6) 0.049 Uiso 1 d R . C3D C 0.8056(8) 0.0430(2) 0.1740(6) 0.034(2) Uiso 1 d . . C4D C 0.9056(9) 0.0629(2) 0.2309(7) 0.043(2) Uiso 1 d . . H4D1 H 0.9873(9) 0.0506(2) 0.2325(7) 0.056 Uiso 1 d R . H4D2 H 0.8798(9) 0.0644(2) 0.2922(7) 0.056 Uiso 1 d R . C5D C 0.9220(11) 0.0985(3) 0.1947(8) 0.057(3) Uiso 1 d . . H5D1 H 0.8430(11) 0.1116(3) 0.1999(8) 0.075 Uiso 1 d R . H5D2 H 0.9911(11) 0.1102(3) 0.2307(8) 0.075 Uiso 1 d R . C6D C 0.9548(11) 0.0987(3) 0.0975(7) 0.057(3) Uiso 1 d . . H6D1 H 1.0401(11) 0.0889(3) 0.0934(7) 0.073 Uiso 1 d R . H6D2 H 0.9563(11) 0.1224(3) 0.0753(7) 0.073 Uiso 1 d R . C7D C 0.8958(10) 0.0766(3) -0.0574(7) 0.049(3) Uani 1 d . . C8D C 0.8025(14) 0.0574(3) -0.1218(7) 0.064(3) Uani 1 d . . C9D C 0.8085(17) 0.0655(4) -0.2193(9) 0.084(5) Uani 1 d . . C10D C 0.7923(10) 0.0071(3) 0.2095(6) 0.045(3) Uani 1 d . . C11D C 0.6901(15) -0.0146(3) 0.1606(7) 0.069(4) Uani 1 d . . C12D C 0.6514(21) -0.0468(4) 0.2066(11) 0.103(6) Uani 1 d . . O1D O 0.7368(6) 0.0958(2) 0.0308(4) 0.045(2) Uani 1 d . . H01D H 0.6847(33) 0.0858(17) 0.0609(63) 0.067 Uiso 1 d R . O3D O 0.6831(6) 0.0590(2) 0.1722(4) 0.037(2) Uani 1 d . . H03D H 0.6709(42) 0.0661(24) 0.2231(15) 0.056 Uiso 1 d R . F1D F 1.0118(7) 0.0639(2) -0.0586(5) 0.089(3) Uani 1 d . . F2D F 0.8985(8) 0.1095(2) -0.0875(5) 0.080(2) Uani 1 d . . F3D F 0.8419(12) 0.0229(2) -0.1130(5) 0.091(5) Uani 0.76(2) d P 1 F3D' F 0.6819(40) 0.0558(10) -0.1079(27) 0.104(15) Uiso 0.24(2) d P 2 F4D F 0.7538(12) 0.0421(2) -0.2708(5) 0.127(4) Uani 1 d . . F5D F 0.9273(9) 0.0694(2) -0.2417(5) 0.106(3) Uani 1 d . . F6D F 0.7481(10) 0.0943(2) -0.2370(5) 0.108(3) Uani 1 d . . F7D F 0.9035(7) -0.0092(2) 0.2150(4) 0.071(2) Uani 1 d . . F8D F 0.7541(7) 0.0094(2) 0.2947(3) 0.062(2) Uani 1 d . . F9D F 0.7314(10) -0.0259(2) 0.0837(4) 0.075(4) Uani 0.78(2) d P 1 F9D' F 0.6114(35) -0.0060(9) 0.1159(26) 0.080(13) Uiso 0.22(2) d P 2 F10D F 0.5739(14) -0.0664(2) 0.1525(7) 0.158(6) Uani 1 d . . F11D F 0.7443(13) -0.0656(2) 0.2379(7) 0.130(4) Uani 1 d . . F12D F 0.5829(12) -0.0388(2) 0.2759(6) 0.125(4) Uani 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 C7A 0.046(6) 0.042(6) 0.035(5) -0.011(5) 0.005(4) -0.007(5) C8A 0.043(6) 0.073(8) 0.024(5) 0.004(5) -0.005(4) -0.010(6) C9A 0.065(8) 0.091(10) 0.032(6) -0.014(6) -0.010(6) 0.004(8) C10A 0.029(5) 0.054(6) 0.021(5) -0.005(4) 0.003(4) -0.005(4) C11A 0.044(6) 0.047(6) 0.023(5) -0.003(4) -0.002(4) 0.001(5) C12A 0.071(8) 0.072(9) 0.044(7) -0.010(6) -0.014(6) 0.013(7) O1A 0.043(4) 0.047(4) 0.027(3) -0.009(3) 0.012(3) -0.004(3) O3A 0.032(3) 0.048(4) 0.017(3) 0.001(3) 0.001(2) -0.002(3) F1A 0.054(4) 0.087(5) 0.040(3) -0.019(3) 0.015(3) -0.030(3) F2A 0.074(4) 0.064(4) 0.046(4) -0.022(3) 0.010(3) 0.000(3) F3A 0.097(5) 0.074(5) 0.038(4) -0.012(3) -0.016(3) 0.010(4) F4A 0.079(5) 0.127(7) 0.036(4) -0.004(4) -0.010(3) -0.016(5) F5A 0.072(5) 0.086(5) 0.050(4) -0.025(4) -0.017(3) -0.014(4) F6A 0.071(5) 0.181(9) 0.028(3) -0.038(4) -0.003(3) 0.029(5) F7A 0.047(3) 0.062(4) 0.035(3) -0.005(3) 0.022(3) -0.008(3) F8A 0.054(3) 0.059(4) 0.019(3) -0.011(2) 0.005(2) 0.003(3) F9A 0.069(5) 0.057(5) 0.038(4) -0.006(3) -0.016(4) 0.008(4) F10A 0.076(5) 0.051(4) 0.062(4) 0.003(3) -0.005(3) 0.010(3) F11A 0.225(12) 0.085(6) 0.111(7) 0.018(5) 0.127(8) 0.061(7) F12A 0.132(8) 0.069(5) 0.094(6) -0.021(4) -0.057(6) 0.004(5) C7B 0.034(5) 0.055(6) 0.027(5) -0.015(4) -0.001(4) -0.010(5) C8B 0.062(7) 0.045(6) 0.023(5) 0.003(4) -0.002(5) 0.009(5) C10B 0.024(5) 0.051(6) 0.036(5) -0.014(5) 0.002(4) -0.007(4) C11B 0.044(6) 0.067(7) 0.021(5) 0.002(5) 0.002(4) -0.005(5) C12B 0.040(6) 0.084(9) 0.028(6) -0.008(6) -0.011(5) -0.004(6) O1B 0.030(3) 0.042(4) 0.024(3) -0.002(3) -0.002(3) 0.001(3) O3B 0.029(3) 0.042(4) 0.030(3) -0.006(3) 0.009(3) -0.006(3) F1B 0.045(3) 0.075(4) 0.037(3) -0.008(3) 0.019(3) -0.004(3) F2B 0.052(3) 0.070(4) 0.021(3) -0.011(3) -0.004(2) 0.003(3) F3B 0.067(6) 0.059(6) 0.043(5) -0.011(4) -0.023(4) 0.002(4) F4B 0.116(6) 0.055(4) 0.063(5) -0.007(4) -0.013(4) 0.015(4) F5B 0.124(7) 0.101(6) 0.053(4) -0.020(4) 0.028(4) 0.048(5) F6B 0.088(8) 0.055(6) 0.083(7) -0.009(5) -0.015(6) -0.008(5) F7B 0.043(3) 0.065(4) 0.034(3) -0.004(3) 0.003(2) -0.017(3) F8B 0.053(4) 0.055(4) 0.037(3) -0.011(3) 0.006(3) -0.001(3) F9B 0.082(5) 0.062(4) 0.033(3) -0.003(3) 0.004(3) 0.016(4) F10B 0.069(4) 0.106(6) 0.029(3) 0.010(3) -0.008(3) 0.004(4) F11B 0.080(5) 0.091(5) 0.035(3) -0.022(3) -0.011(3) -0.021(4) F12B 0.076(5) 0.151(8) 0.043(4) -0.003(4) 0.020(4) 0.026(5) C7C 0.047(6) 0.051(6) 0.028(5) -0.001(4) -0.001(4) 0.002(5) C8C 0.130(14) 0.066(9) 0.046(8) 0.015(6) 0.037(8) 0.014(9) C9C 0.166(17) 0.091(12) 0.050(9) 0.049(9) 0.049(10) 0.063(12) C10C 0.039(5) 0.047(6) 0.025(5) 0.002(4) 0.010(4) 0.006(5) C11C 0.055(7) 0.040(6) 0.018(5) 0.006(4) 0.005(4) 0.007(5) C12C 0.085(9) 0.082(9) 0.012(5) 0.000(5) 0.013(5) 0.007(7) O1C 0.035(3) 0.052(4) 0.027(3) -0.002(3) 0.009(3) 0.012(3) O3C 0.047(4) 0.041(4) 0.023(3) -0.002(3) 0.011(3) 0.005(3) F1C 0.095(5) 0.051(4) 0.032(3) -0.011(3) -0.010(3) 0.005(3) F2C 0.050(4) 0.066(4) 0.087(5) 0.018(4) -0.010(3) 0.008(3) F3C 0.085(6) 0.080(6) 0.026(4) -0.007(4) 0.019(4) 0.008(5) F4C 0.294(16) 0.074(6) 0.078(6) 0.028(5) 0.059(8) 0.062(8) F5C 0.157(10) 0.152(10) 0.094(7) 0.028(7) -0.021(7) 0.069(8) F6C 0.205(13) 0.124(8) 0.111(8) 0.051(7) 0.060(8) -0.002(8) F7C 0.048(4) 0.103(5) 0.028(3) 0.003(3) 0.012(3) 0.014(3) F8C 0.086(5) 0.049(4) 0.031(3) 0.004(3) 0.024(3) -0.006(3) F9C 0.192(10) 0.043(5) 0.021(4) -0.003(3) -0.023(5) 0.022(5) F10C 0.122(6) 0.081(5) 0.021(3) -0.004(3) -0.002(3) 0.004(4) F11C 0.094(6) 0.234(11) 0.022(3) 0.002(5) 0.027(4) -0.025(7) F12C 0.168(8) 0.079(5) 0.033(4) 0.015(4) 0.001(4) 0.024(5) C7D 0.056(7) 0.041(6) 0.052(7) 0.020(5) 0.027(5) 0.014(5) C8D 0.107(11) 0.057(8) 0.031(6) 0.007(5) 0.018(6) -0.003(7) C9D 0.119(13) 0.086(11) 0.054(9) 0.014(8) 0.043(9) 0.038(10) C10D 0.063(7) 0.054(6) 0.016(5) -0.003(4) 0.001(4) 0.016(6) C11D 0.115(11) 0.061(8) 0.029(6) 0.014(6) 0.002(7) -0.011(8) C12D 0.193(20) 0.054(9) 0.061(10) 0.015(8) 0.007(11) 0.021(11) O1D 0.051(4) 0.046(4) 0.038(4) 0.010(3) 0.013(3) 0.008(3) O3D 0.043(4) 0.049(4) 0.020(3) -0.001(3) 0.008(3) 0.009(3) F1D 0.076(5) 0.133(7) 0.065(5) 0.025(5) 0.045(4) 0.038(5) F2D 0.111(6) 0.071(5) 0.062(4) 0.019(4) 0.039(4) -0.024(4) F3D 0.194(13) 0.053(6) 0.028(5) 0.008(4) 0.025(6) 0.015(6) F4D 0.252(13) 0.108(7) 0.023(4) -0.005(4) 0.019(5) -0.002(8) F5D 0.142(8) 0.139(8) 0.043(4) 0.034(4) 0.050(5) 0.061(6) F6D 0.167(9) 0.106(7) 0.054(5) 0.033(4) 0.033(5) 0.054(6) F7D 0.101(6) 0.069(4) 0.043(4) 0.011(3) 0.005(3) 0.042(4) F8D 0.109(5) 0.069(4) 0.009(3) 0.007(3) 0.013(3) 0.014(4) F9D 0.160(10) 0.051(5) 0.015(4) -0.007(3) 0.018(5) -0.019(6) F10D 0.302(17) 0.089(7) 0.081(7) 0.011(5) 0.002(8) -0.098(9) F11D 0.238(13) 0.049(5) 0.102(7) 0.029(5) 0.008(8) 0.007(7) F12D 0.213(12) 0.094(6) 0.078(6) 0.018(5) 0.068(7) -0.032(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A O1A 1.444(11) . ? C1A C2A 1.522(12) . ? C1A C6A 1.559(14) . ? C1A C7A 1.561(13) . ? C2A C3A 1.542(12) . ? C3A O3A 1.450(10) . ? C3A C4A 1.518(13) . ? C3A C10A 1.558(12) . ? C4A C5A 1.501(14) . ? C5A C6A 1.549(14) . ? C7A F1A 1.350(11) . ? C7A F2A 1.388(11) . ? C7A C8A 1.512(14) . ? C8A F3A 1.338(12) . ? C8A C9A 1.607(14) . ? C9A F6A 1.305(14) . ? C9A F5A 1.315(14) . ? C9A F4A 1.342(14) . ? C10A F7A 1.372(10) . ? C10A F8A 1.375(10) . ? C10A C11A 1.552(13) . ? C11A F9A' 1.35(3) . ? C11A F9A 1.397(11) . ? C11A C12A 1.486(15) . ? C12A F11A 1.280(15) . ? C12A F10A 1.293(13) . ? C12A F12A 1.383(14) . ? C1B O1B 1.449(10) . ? C1B C2B 1.528(12) . ? C1B C7B 1.547(13) . ? C1B C6B 1.557(12) . ? C2B C3B 1.536(12) . ? C3B O3B 1.454(10) . ? C3B C10B 1.526(12) . ? C3B C4B 1.547(13) . ? C4B C5B 1.519(13) . ? C5B C6B 1.512(13) . ? C7B F1B 1.352(10) . ? C7B F2B 1.373(10) . ? C7B C8B 1.531(14) . ? C8B F3B 1.433(13) . ? C8B C9B 1.48(2) . ? C8B C9B' 1.58(3) . ? C8B F3B' 1.62(3) . ? C9B F5B 1.31(2) . ? C9B F6B 1.32(2) . ? C9B F4B 1.37(2) . ? C9B' F4B 1.23(3) . ? C9B' F6B' 1.26(4) . ? C9B' F5B 1.30(3) . ? C10B F7B 1.371(10) . ? C10B F8B 1.401(10) . ? C10B C11B 1.514(14) . ? C11B F9B 1.388(11) . ? C11B C12B 1.540(13) . ? C12B F11B 1.313(12) . ? C12B F10B 1.337(13) . ? C12B F12B 1.355(12) . ? C1C O1C 1.408(10) . ? C1C C6C 1.520(12) . ? C1C C2C 1.532(12) . ? C1C C7C 1.545(13) . ? C2C C3C 1.519(12) . ? C3C O3C 1.440(10) . ? C3C C4C 1.533(12) . ? C3C C10C 1.553(11) . ? C4C C5C 1.571(13) . ? C5C C6C 1.508(13) . ? C7C F2C 1.338(11) . ? C7C F1C 1.371(11) . ? C7C C8C 1.56(2) . ? C8C F3C' 1.22(4) . ? C8C F3C 1.312(15) . ? C8C C9C 1.53(2) . ? C9C F4C 1.26(2) . ? C9C F6C 1.31(2) . ? C9C F5C 1.36(2) . ? C10C F7C 1.367(10) . ? C10C F8C 1.374(11) . ? C10C C11C 1.519(14) . ? C11C F9C' 1.06(7) . ? C11C F9C 1.332(11) . ? C11C C12C 1.535(12) . ? C12C F11C 1.282(14) . ? C12C F10C 1.311(13) . ? C12C F12C 1.371(14) . ? C1D O1D 1.430(11) . ? C1D C2D 1.524(13) . ? C1D C6D 1.541(14) . ? C1D C7D 1.564(14) . ? C2D C3D 1.558(13) . ? C3D O3D 1.440(11) . ? C3D C10D 1.522(14) . ? C3D C4D 1.527(13) . ? C4D C5D 1.520(15) . ? C5D C6D 1.54(2) . ? C7D F1D 1.328(12) . ? C7D F2D 1.373(12) . ? C7D C8D 1.53(2) . ? C8D F3D' 1.31(4) . ? C8D F3D 1.419(15) . ? C8D C9D 1.52(2) . ? C9D F4D 1.31(2) . ? C9D F6D 1.32(2) . ? C9D F5D 1.34(2) . ? C10D F7D 1.339(12) . ? C10D F8D 1.385(10) . ? C10D C11D 1.52(2) . ? C11D F9D' 1.08(4) . ? C11D F9D 1.353(14) . ? C11D C12D 1.52(2) . ? C12D F11D 1.29(2) . ? C12D F10D 1.35(2) . ? C12D F12D 1.36(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A C1A C2A 110.9(7) . . ? O1A C1A C6A 110.0(8) . . ? C2A C1A C6A 111.5(8) . . ? O1A C1A C7A 103.9(7) . . ? C2A C1A C7A 111.3(8) . . ? C6A C1A C7A 109.0(8) . . ? C1A C2A C3A 111.3(7) . . ? O3A C3A C4A 111.5(7) . . ? O3A C3A C2A 105.0(6) . . ? C4A C3A C2A 111.6(7) . . ? O3A C3A C10A 104.7(7) . . ? C4A C3A C10A 111.0(7) . . ? C2A C3A C10A 112.8(7) . . ? C5A C4A C3A 112.3(9) . . ? C4A C5A C6A 112.6(9) . . ? C5A C6A C1A 109.6(8) . . ? F1A C7A F2A 107.2(8) . . ? F1A C7A C8A 109.9(8) . . ? F2A C7A C8A 109.2(8) . . ? F1A C7A C1A 110.0(7) . . ? F2A C7A C1A 107.9(8) . . ? C8A C7A C1A 112.4(8) . . ? F3A C8A C7A 109.4(8) . . ? F3A C8A C9A 105.9(8) . . ? C7A C8A C9A 110.9(9) . . ? F6A C9A F5A 109.9(11) . . ? F6A C9A F4A 106.8(11) . . ? F5A C9A F4A 107.9(10) . . ? F6A C9A C8A 111.2(9) . . ? F5A C9A C8A 113.8(10) . . ? F4A C9A C8A 107.0(10) . . ? F7A C10A F8A 106.9(7) . . ? F7A C10A C11A 109.7(7) . . ? F8A C10A C11A 107.5(7) . . ? F7A C10A C3A 109.2(7) . . ? F8A C10A C3A 107.0(7) . . ? C11A C10A C3A 116.1(7) . . ? F9A' C11A C12A 85.9(15) . . ? F9A C11A C12A 104.1(8) . . ? F9A' C11A C10A 103.5(15) . . ? F9A C11A C10A 107.9(8) . . ? C12A C11A C10A 116.4(8) . . ? F11A C12A F10A 108.7(11) . . ? F11A C12A F12A 106.3(11) . . ? F10A C12A F12A 104.2(11) . . ? F11A C12A C11A 116.6(12) . . ? F10A C12A C11A 112.9(9) . . ? F12A C12A C11A 107.4(10) . . ? O1B C1B C2B 110.3(7) . . ? O1B C1B C7B 103.2(7) . . ? C2B C1B C7B 111.8(7) . . ? O1B C1B C6B 110.9(7) . . ? C2B C1B C6B 110.3(7) . . ? C7B C1B C6B 110.1(7) . . ? C1B C2B C3B 112.5(7) . . ? O3B C3B C10B 106.5(7) . . ? O3B C3B C2B 105.4(7) . . ? C10B C3B C2B 111.0(7) . . ? O3B C3B C4B 111.3(7) . . ? C10B C3B C4B 112.2(8) . . ? C2B C3B C4B 110.2(7) . . ? C5B C4B C3B 111.0(8) . . ? C6B C5B C4B 111.4(8) . . ? C5B C6B C1B 110.8(8) . . ? F1B C7B F2B 106.2(7) . . ? F1B C7B C8B 109.9(8) . . ? F2B C7B C8B 107.7(8) . . ? F1B C7B C1B 110.0(8) . . ? F2B C7B C1B 107.8(7) . . ? C8B C7B C1B 114.8(7) . . ? F3B C8B C9B 106.1(11) . . ? F3B C8B C7B 103.8(8) . . ? C9B C8B C7B 115.4(9) . . ? C7B C8B C9B' 121.5(14) . . ? C7B C8B F3B' 103.5(12) . . ? C9B' C8B F3B' 97.5(18) . . ? F5B C9B F6B 105.5(13) . . ? F5B C9B F4B 106.9(13) . . ? F6B C9B F4B 108.3(13) . . ? F5B C9B C8B 117.9(13) . . ? F6B C9B C8B 108.6(13) . . ? F4B C9B C8B 109.2(12) . . ? F4B C9B' F6B' 114.0(31) . . ? F4B C9B' F5B 116.3(26) . . ? F6B' C9B' F5B 101.6(27) . . ? F4B C9B' C8B 110.6(24) . . ? F6B' C9B' C8B 102.1(25) . . ? F5B C9B' C8B 111.2(24) . . ? F7B C10B F8B 104.7(7) . . ? F7B C10B C11B 109.7(8) . . ? F8B C10B C11B 108.9(7) . . ? F7B C10B C3B 110.0(7) . . ? F8B C10B C3B 107.4(7) . . ? C11B C10B C3B 115.5(8) . . ? F9B C11B C10B 108.4(7) . . ? F9B C11B C12B 105.5(8) . . ? C10B C11B C12B 113.7(9) . . ? F11B C12B F10B 107.1(8) . . ? F11B C12B F12B 110.5(10) . . ? F10B C12B F12B 106.2(9) . . ? F11B C12B C11B 115.0(9) . . ? F10B C12B C11B 108.7(9) . . ? F12B C12B C11B 109.0(8) . . ? O1C C1C C6C 111.2(7) . . ? O1C C1C C2C 110.5(7) . . ? C6C C1C C2C 110.5(7) . . ? O1C C1C C7C 106.0(7) . . ? C6C C1C C7C 111.5(7) . . ? C2C C1C C7C 107.0(7) . . ? C3C C2C C1C 112.6(7) . . ? O3C C3C C2C 107.1(7) . . ? O3C C3C C4C 111.5(7) . . ? C2C C3C C4C 112.3(7) . . ? O3C C3C C10C 105.2(6) . . ? C2C C3C C10C 110.5(7) . . ? C4C C3C C10C 110.0(7) . . ? C3C C4C C5C 109.7(7) . . ? C6C C5C C4C 111.4(8) . . ? C5C C6C C1C 111.5(8) . . ? F2C C7C F1C 105.7(8) . . ? F2C C7C C1C 111.5(8) . . ? F1C C7C C1C 111.2(7) . . ? F2C C7C C8C 112.1(9) . . ? F1C C7C C8C 100.3(9) . . ? C1C C7C C8C 115.1(9) . . ? F3C' C8C C9C 100.7(23) . . ? F3C C8C C9C 110.4(11) . . ? F3C' C8C C7C 123.8(23) . . ? F3C C8C C7C 112.1(11) . . ? C9C C8C C7C 115.1(12) . . ? F4C C9C F6C 114.7(17) . . ? F4C C9C F5C 104.2(15) . . ? F6C C9C F5C 103.5(13) . . ? F4C C9C C8C 115.4(11) . . ? F6C C9C C8C 108.5(13) . . ? F5C C9C C8C 109.7(16) . . ? F7C C10C F8C 105.6(8) . . ? F7C C10C C11C 108.9(8) . . ? F8C C10C C11C 106.8(7) . . ? F7C C10C C3C 109.4(7) . . ? F8C C10C C3C 109.3(7) . . ? C11C C10C C3C 116.2(8) . . ? F9C' C11C C10C 120.3(35) . . ? F9C C11C C10C 110.7(8) . . ? F9C' C11C C12C 101.9(35) . . ? F9C C11C C12C 105.5(8) . . ? C10C C11C C12C 115.9(9) . . ? F11C C12C F10C 111.0(9) . . ? F11C C12C F12C 105.6(11) . . ? F10C C12C F12C 105.4(10) . . ? F11C C12C C11C 114.2(10) . . ? F10C C12C C11C 111.7(10) . . ? F12C C12C C11C 108.3(9) . . ? O1D C1D C2D 110.7(8) . . ? O1D C1D C6D 110.8(8) . . ? C2D C1D C6D 112.0(8) . . ? O1D C1D C7D 103.6(7) . . ? C2D C1D C7D 110.2(8) . . ? C6D C1D C7D 109.2(8) . . ? C1D C2D C3D 111.6(8) . . ? O3D C3D C10D 107.7(7) . . ? O3D C3D C4D 111.6(7) . . ? C10D C3D C4D 110.9(8) . . ? O3D C3D C2D 105.1(7) . . ? C10D C3D C2D 111.1(7) . . ? C4D C3D C2D 110.3(8) . . ? C5D C4D C3D 111.3(8) . . ? C4D C5D C6D 113.0(10) . . ? C5D C6D C1D 110.1(9) . . ? F1D C7D F2D 107.8(9) . . ? F1D C7D C8D 110.8(10) . . ? F2D C7D C8D 106.6(9) . . ? F1D C7D C1D 110.5(9) . . ? F2D C7D C1D 106.8(8) . . ? C8D C7D C1D 114.1(9) . . ? F3D' C8D C9D 106.4(21) . . ? F3D C8D C9D 105.0(10) . . ? F3D' C8D C7D 120.5(20) . . ? F3D C8D C7D 104.1(11) . . ? C9D C8D C7D 116.1(12) . . ? F4D C9D F6D 107.4(14) . . ? F4D C9D F5D 108.0(11) . . ? F6D C9D F5D 107.6(13) . . ? F4D C9D C8D 112.3(13) . . ? F6D C9D C8D 108.8(11) . . ? F5D C9D C8D 112.5(14) . . ? F7D C10D F8D 107.2(7) . . ? F7D C10D C11D 110.4(9) . . ? F8D C10D C11D 103.9(9) . . ? F7D C10D C3D 111.2(9) . . ? F8D C10D C3D 108.0(8) . . ? C11D C10D C3D 115.5(8) . . ? F9D' C11D C12D 108.8(24) . . ? F9D C11D C12D 103.6(11) . . ? F9D' C11D C10D 127.7(22) . . ? F9D C11D C10D 109.7(11) . . ? C12D C11D C10D 116.9(12) . . ? F11D C12D F10D 107.8(13) . . ? F11D C12D F12D 106.6(13) . . ? F10D C12D F12D 105.3(17) . . ? F11D C12D C11D 114.8(17) . . ? F10D C12D C11D 111.8(12) . . ? F12D C12D C11D 109.9(12) . . ? _refine_diff_density_max 0.853 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.117 #================================================END data_25 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1,4-di(1,1,2,3,3,3-hexafluoropropyl)-cyclohexane-1,4-diol ; _chemical_name_common ? _chemical_melting_point '378-380 K' _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 F12 O2' _chemical_formula_weight 416.22 _ccdc_compound_id '25' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Rotational disorder of CF3 groups in molecules A, C and D; molecule A is a superposition of two diastereomers with different configurations of C8A. Atoms F3A, F4A, F5A, F6A are disordered between two positions (primed and unprimed labels) with occupancies of 50%. F4C, F5C, F6C are disordered between 2 positions, with occupancies 67% (unprimed) and 33% (primed). F4D, F5D, F6D are disordered between 2 positions, with occupancies 70% (unprimed) and 30% (primed). ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 14.6732(16) _cell_length_b 10.8011(19) _cell_length_c 18.8818(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.904(8) _cell_angle_gamma 90.00 _cell_volume 2992.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 21.1 _cell_measurement_theta_max 24.3 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 2.051 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.18 0.00 -1.00 0.00 0.18 1.00 0.00 -1.00 0.06 -1.00 0.00 1.00 0.06 1.00 0.00 1.00 0.03 -1.00 0.00 -1.00 0.03 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.2 _diffrn_reflns_number 5205 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 74.89 _reflns_number_total 4771 _reflns_number_gt 3201 _reflns_threshold_expression >2sigma(I) _computing_data_collection AFC/MSC _computing_cell_refinement AFC/MSC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. CF~3~ groups were restrained to regular geometry. ; _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^)+(0.1000P)^2^] 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; determination unreliable' _refine_ls_abs_structure_Flack 0.2(6) _refine_ls_number_reflns 4771 _refine_ls_number_parameters 666 _refine_ls_number_restraints 150 _refine_ls_R_factor_all 0.1844 _refine_ls_R_factor_gt 0.1370 _refine_ls_wR_factor_ref 0.3410 _refine_ls_wR_factor_gt 0.3101 _refine_ls_goodness_of_fit_ref 2.121 _refine_ls_restrained_S_all 2.158 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.006 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 O1A O 0.6902(9) 0.9065(12) 0.2292(7) 0.041(3) Uani 1 1 d . . . H01A H 0.6678 0.9012 0.1882 0.062 Uiso 1 1 d R . . O4A O 0.8796(9) 0.6195(12) 0.3270(7) 0.045(4) Uani 1 1 d . . . H04A H 0.9063 0.5634 0.3045 0.067 Uiso 1 1 d R . . C1A C 0.6870(15) 0.787(2) 0.2660(11) 0.042(5) Uiso 1 1 d . . . C2A C 0.7424(15) 0.701(2) 0.2172(11) 0.044(5) Uiso 1 1 d . . . H21A H 0.7183 0.7061 0.1697 0.052 Uiso 1 1 d R . . H22A H 0.7314 0.6187 0.2339 0.052 Uiso 1 1 d R . . C3A C 0.8451(13) 0.7160(19) 0.2155(10) 0.030(4) Uiso 1 1 d . . . H31A H 0.8725 0.6445 0.1943 0.036 Uiso 1 1 d R . . H32A H 0.8574 0.7858 0.1856 0.036 Uiso 1 1 d R . . C4A C 0.8855(15) 0.738(2) 0.2882(11) 0.046(5) Uiso 1 1 d . . . C5A C 0.8390(14) 0.8216(19) 0.3326(11) 0.038(5) Uiso 1 1 d . . . H51A H 0.8490 0.9050 0.3170 0.045 Uiso 1 1 d R . . H52A H 0.8628 0.8149 0.3801 0.045 Uiso 1 1 d R . . C6A C 0.7390(12) 0.8073(17) 0.3344(9) 0.024(4) Uiso 1 1 d . . . H61A H 0.7113 0.8733 0.3605 0.029 Uiso 1 1 d R . . H62A H 0.7298 0.7327 0.3610 0.029 Uiso 1 1 d R . . C7A C 0.5903(14) 0.756(2) 0.2685(11) 0.043(6) Uani 1 1 d . A . C8A C 0.5301(17) 0.824(3) 0.3079(14) 0.116(12) Uiso 1 1 d D . . C9A C 0.4314(17) 0.8052(14) 0.3072(7) 0.051(6) Uiso 1 1 d D A . C10A C 0.9921(13) 0.7571(18) 0.2818(10) 0.029(5) Uiso 1 1 d . . . C11A C 1.0462(13) 0.7749(16) 0.3450(8) 0.034(5) Uiso 1 1 d D . . H11A H 1.0302 0.7075 0.3789 0.040 Uiso 1 1 d R . . C12A C 1.1480(19) 0.7706(14) 0.3358(8) 0.060(7) Uiso 1 1 d D . . F1A F 0.5528(9) 0.7218(15) 0.2061(7) 0.068(4) Uani 1 1 d . . . F2A F 0.5816(9) 0.6494(16) 0.3084(9) 0.085(5) Uani 1 1 d . . . F3A F 0.5553(19) 0.826(2) 0.3825(14) 0.065(7) Uiso 0.50 1 d P A 1 F4A F 0.3926(15) 0.771(2) 0.2469(10) 0.060(7) Uiso 0.50 1 d PD A 1 F5A F 0.4036(19) 0.721(3) 0.3521(14) 0.117(13) Uiso 0.50 1 d PD A 1 F6A F 0.3828(19) 0.904(3) 0.3247(18) 0.156(18) Uiso 0.50 1 d PD A 1 F3A' F 0.5493(15) 0.934(2) 0.3348(11) 0.040(5) Uiso 0.50 1 d P A 2 F4A' F 0.4058(19) 0.692(2) 0.2882(16) 0.117(13) Uiso 0.50 1 d PD A 2 F5A' F 0.3912(14) 0.821(2) 0.3675(10) 0.051(6) Uiso 0.50 1 d PD A 2 F6A' F 0.3878(18) 0.877(3) 0.2619(14) 0.112(12) Uiso 0.50 1 d PD A 2 F7A F 1.0263(10) 0.6807(17) 0.2366(7) 0.095(7) Uani 1 1 d . . . F8A F 0.9958(10) 0.8717(11) 0.2433(6) 0.059(4) Uani 1 1 d . . . F9A F 1.0270(9) 0.8882(11) 0.3780(7) 0.062(4) Uani 1 1 d . . . F10A F 1.1749(10) 0.6562(14) 0.3219(8) 0.085(5) Uani 1 1 d D . . F11A F 1.1941(9) 0.8026(15) 0.3929(6) 0.083(5) Uani 1 1 d D . . F12A F 1.1767(10) 0.8402(16) 0.2849(7) 0.105(7) Uani 1 1 d D . . O1B O 0.1018(9) 0.8372(12) 0.0973(6) 0.039(3) Uani 1 1 d . . . H01B H 0.0730 0.8368 0.1354 0.059 Uiso 1 1 d R . . O4B O 0.3067(11) 1.1282(12) 0.0265(7) 0.053(4) Uani 1 1 d . . . H04B H 0.3088 1.1862 0.0562 0.079 Uiso 1 1 d R . . C1B C 0.1038(14) 0.9691(18) 0.0698(10) 0.035(5) Uiso 1 1 d . . . C2B C 0.1585(13) 0.9437(18) 0.0002(10) 0.033(5) Uiso 1 1 d . . . H21B H 0.1506 1.0142 -0.0303 0.040 Uiso 1 1 d R . . H22B H 0.1308 0.8739 -0.0230 0.040 Uiso 1 1 d R . . C3B C 0.2568(14) 0.9213(18) 0.0097(10) 0.034(5) Uiso 1 1 d . . . H31B H 0.2851 0.9265 -0.0357 0.041 Uiso 1 1 d R . . H32B H 0.2650 0.8383 0.0269 0.041 Uiso 1 1 d R . . C4B C 0.3054(13) 1.0072(18) 0.0632(10) 0.033(5) Uiso 1 1 d . . . C5B C 0.2550(14) 1.0195(19) 0.1316(10) 0.035(5) Uiso 1 1 d . . . H51B H 0.2820 1.0824 0.1612 0.042 Uiso 1 1 d R . . H52B H 0.2596 0.9420 0.1563 0.042 Uiso 1 1 d R . . C6B C 0.1591(16) 1.045(2) 0.1205(12) 0.049(6) Uiso 1 1 d . . . H61B H 0.1277 1.0394 0.1647 0.059 Uiso 1 1 d R . . H62B H 0.1553 1.1291 0.1048 0.059 Uiso 1 1 d R . . C7B C 0.0132(14) 0.9975(19) 0.0596(10) 0.030(5) Uiso 1 1 d . . . C8B C -0.0548(17) 0.9316(19) 0.0046(11) 0.054(6) Uiso 1 1 d D . . H8B H -0.0486 0.8421 0.0173 0.070 Uiso 1 1 calc R . . C9B C -0.1505(16) 0.9523(14) 0.0090(7) 0.046(6) Uiso 1 1 d D . . C10B C 0.4026(15) 0.971(2) 0.0794(11) 0.040(5) Uiso 1 1 d . . . C11B C 0.4701(14) 0.9603(16) 0.0180(9) 0.041(5) Uiso 1 1 d D . . H11B H 0.4595 1.0352 -0.0121 0.053 Uiso 1 1 calc R . . C12B C 0.5705(19) 0.9581(14) 0.0337(8) 0.064(7) Uiso 1 1 d D . . F1B F -0.0330(10) 1.0126(17) 0.1187(7) 0.088(6) Uani 1 1 d . . . F2B F 0.0058(9) 1.1237(13) 0.0336(7) 0.065(4) Uani 1 1 d . . . F3B F -0.0259(9) 0.9349(17) -0.0589(7) 0.088(5) Uani 1 1 d . . . F4B F -0.1943(9) 0.9073(16) -0.0466(8) 0.103(7) Uani 1 1 d D . . F5B F -0.1873(11) 0.8980(15) 0.0639(8) 0.094(6) Uani 1 1 d D . . F6B F -0.1729(8) 1.0694(13) 0.0128(7) 0.076(5) Uani 1 1 d D . . F7B F 0.4071(9) 0.8551(11) 0.1091(7) 0.057(3) Uani 1 1 d . . . F8B F 0.4418(8) 1.0468(12) 0.1289(5) 0.045(3) Uani 1 1 d . . . F9B F 0.4503(9) 0.8611(13) -0.0247(6) 0.064(4) Uani 1 1 d . . . F10B F 0.6144(7) 0.9372(14) -0.0232(6) 0.075(5) Uani 1 1 d D . . F11B F 0.5928(9) 0.8807(18) 0.0801(7) 0.117(8) Uani 1 1 d D . . F12B F 0.5983(10) 1.0643(15) 0.0558(10) 0.133(9) Uani 1 1 d D . . O1C O 0.7055(9) 0.1232(12) 0.3144(6) 0.039(3) Uani 1 1 d . . . H01C H 0.6790 0.0705 0.2886 0.059 Uiso 1 1 d R . . O4C O 0.9101(10) 0.4099(12) 0.2406(7) 0.046(4) Uani 1 1 d . . . H04C H 0.9385 0.4054 0.2024 0.068 Uiso 1 1 d R . . C1C C 0.7045(14) 0.2453(19) 0.2780(10) 0.037(5) Uiso 1 1 d . . . C2C C 0.7582(13) 0.2291(19) 0.2079(10) 0.034(5) Uiso 1 1 d . . . H21C H 0.7537 0.3029 0.1796 0.041 Uiso 1 1 d R . . H22C H 0.7296 0.1633 0.1816 0.041 Uiso 1 1 d R . . C3C C 0.8571(11) 0.1994(16) 0.2199(8) 0.021(4) Uiso 1 1 d . . . H31C H 0.8866 0.2008 0.1748 0.025 Uiso 1 1 d R . . H32C H 0.8621 0.1169 0.2385 0.025 Uiso 1 1 d R . . C4C C 0.9039(13) 0.2890(17) 0.2740(9) 0.031(4) Uiso 1 1 d . . . C5C C 0.8543(12) 0.2954(17) 0.3407(9) 0.027(4) Uiso 1 1 d . . . H51C H 0.8814 0.3567 0.3712 0.032 Uiso 1 1 d R . . H52C H 0.8597 0.2168 0.3642 0.032 Uiso 1 1 d R . . C6C C 0.7509(11) 0.3280(16) 0.3303(9) 0.021(4) Uiso 1 1 d . . . H61C H 0.7205 0.3166 0.3745 0.025 Uiso 1 1 d R . . H62C H 0.7446 0.4134 0.3170 0.025 Uiso 1 1 d R . . C7C C 0.6033(15) 0.268(2) 0.2636(11) 0.042(5) Uiso 1 1 d . . . C8C C 0.5414(15) 0.268(2) 0.3240(11) 0.046(5) Uiso 1 1 d . B . H8C H 0.5531 0.1949 0.3554 0.060 Uiso 1 1 d R . . C9C C 0.4397(6) 0.2836(9) 0.3077(4) 0.035(5) Uiso 1 1 d . . . F4C' F 0.4294(6) 0.3979(12) 0.2918(4) 0.061(3) Uiso 0.33 1 d PR B 1 F5C' F 0.3977(6) 0.2660(9) 0.3656(6) 0.061(3) Uiso 0.33 1 d PR B 1 F6C' F 0.4009(6) 0.2251(10) 0.2632(5) 0.061(3) Uiso 0.33 1 d PR B 1 F4C F 0.4265(6) 0.3632(10) 0.2585(6) 0.061(3) Uiso 0.67 1 d PR B 2 F5C F 0.3967(6) 0.3165(9) 0.3630(6) 0.061(3) Uiso 0.67 1 d PR B 2 F6C F 0.4143(6) 0.1561(13) 0.2844(5) 0.061(3) Uiso 0.67 1 d PR B 2 C10C C 1.0032(12) 0.2456(17) 0.2875(9) 0.024(4) Uiso 1 1 d . . . C11C C 1.0604(15) 0.3075(17) 0.3408(10) 0.045(6) Uiso 1 1 d D . . H11C H 1.0421 0.2723 0.3875 0.058 Uiso 1 1 d R . . C12C C 1.162(2) 0.2868(15) 0.3374(8) 0.070(8) Uiso 1 1 d D . . F1C F 0.6040(8) 0.3832(12) 0.2284(6) 0.056(3) Uani 1 1 d . . . F2C F 0.5675(10) 0.1903(14) 0.2133(8) 0.074(5) Uani 1 1 d . . . F3C F 0.5604(11) 0.387(3) 0.3585(10) 0.152(11) Uani 1 1 d . . . F7C F 1.0041(9) 0.1275(9) 0.3067(7) 0.056(3) Uani 1 1 d . . . F8C F 1.0495(8) 0.2494(11) 0.2220(6) 0.048(3) Uani 1 1 d . . . F9C F 1.0461(10) 0.4236(16) 0.3475(10) 0.105(6) Uani 1 1 d . . . F10C F 1.1808(10) 0.1683(13) 0.3332(7) 0.071(5) Uani 1 1 d D . . F11C F 1.2025(10) 0.3285(15) 0.3948(6) 0.086(5) Uani 1 1 d D . . F12C F 1.1976(9) 0.3414(15) 0.2825(7) 0.086(5) Uani 1 1 d D . . O1D O 0.3258(11) 0.3407(11) 0.1114(7) 0.046(4) Uani 1 1 d . . . H01D H 0.3209 0.3520 0.1552 0.070 Uiso 1 1 d R . . O4D O 0.1353(10) 0.6290(12) 0.0152(7) 0.041(3) Uani 1 1 d . . . H04D H 0.1348 0.6870 0.0448 0.062 Uiso 1 1 d R . . C1D C 0.3278(13) 0.4619(17) 0.0762(10) 0.032(4) Uiso 1 1 d . . . C2D C 0.2779(13) 0.5558(17) 0.1211(10) 0.032(4) Uiso 1 1 d . . . H21D H 0.2846 0.6376 0.1021 0.039 Uiso 1 1 d R . . H22D H 0.3041 0.5554 0.1680 0.039 Uiso 1 1 d R . . C3D C 0.1780(13) 0.5211(19) 0.1260(10) 0.035(5) Uiso 1 1 d . . . H31D H 0.1709 0.4430 0.1496 0.042 Uiso 1 1 d R . . H32D H 0.1479 0.5832 0.1535 0.042 Uiso 1 1 d R . . C4D C 0.1300(12) 0.5139(16) 0.0534(9) 0.027(4) Uiso 1 1 d . . . C5D C 0.1796(12) 0.4165(16) 0.0084(9) 0.024(4) Uiso 1 1 d . . . H51D H 0.1539 0.4152 -0.0387 0.029 Uiso 1 1 d R . . H52D H 0.1691 0.3370 0.0295 0.029 Uiso 1 1 d R . . C6D C 0.2815(13) 0.4442(18) 0.0045(10) 0.031(4) Uiso 1 1 d . . . H61D H 0.2919 0.5133 -0.0262 0.037 Uiso 1 1 d R . . H62D H 0.3095 0.3729 -0.0163 0.037 Uiso 1 1 d R . . C7D C 0.4241(16) 0.492(2) 0.0737(12) 0.046(6) Uiso 1 1 d . . . C8D C 0.4953(14) 0.3881(18) 0.0560(10) 0.062(7) Uiso 1 1 d D C . H8D H 0.4979 0.3315 0.0979 0.081 Uiso 1 1 d R . . C9D C 0.598(2) 0.4321(14) 0.0374(7) 0.080(8) Uiso 1 1 d D . . C10D C 0.0290(13) 0.4857(19) 0.0629(10) 0.031(5) Uiso 1 1 d . . . C11D C -0.0330(18) 0.4682(19) -0.0038(11) 0.058(7) Uiso 1 1 d D . . H11D H -0.0221 0.5434 -0.0333 0.076 Uiso 1 1 d R . . C12D C -0.1326(18) 0.4725(14) 0.0063(7) 0.052(6) Uiso 1 1 d D . . F1D F 0.4364(13) 0.5989(15) 0.0272(8) 0.094(5) Uani 1 1 d . . . F2D F 0.4548(10) 0.5364(12) 0.1340(6) 0.059(4) Uani 1 1 d . . . F3D F 0.4642(9) 0.3288(17) -0.0015(10) 0.112(8) Uani 1 1 d . . . F4D F 0.6470(10) 0.3261(13) 0.0427(8) 0.052(2) Uiso 0.70 1 d PD C 1 F5D F 0.6250(10) 0.5031(13) 0.0884(7) 0.052(2) Uiso 0.70 1 d PD C 1 F6D F 0.6010(11) 0.4729(14) -0.0235(7) 0.052(2) Uiso 0.70 1 d PD C 1 F4D' F 0.5942(19) 0.5545(16) 0.0338(16) 0.052(2) Uiso 0.30 1 d PD C 2 F5D' F 0.621(3) 0.393(3) 0.0957(11) 0.052(2) Uiso 0.30 1 d PD C 2 F6D' F 0.631(3) 0.389(3) -0.0192(12) 0.052(2) Uiso 0.30 1 d PD C 2 F7D F 0.0209(9) 0.3783(15) 0.0995(7) 0.070(4) Uani 1 1 d . . . F8D F -0.0083(7) 0.5741(12) 0.1040(5) 0.049(3) Uani 1 1 d . . . F9D F -0.0126(10) 0.388(2) -0.0433(10) 0.138(10) Uani 1 1 d . . . F10D F -0.1792(8) 0.4385(13) -0.0497(7) 0.068(4) Uani 1 1 d D . . F11D F -0.1611(10) 0.5858(14) 0.0199(8) 0.084(5) Uani 1 1 d D . . F12D F -0.1601(11) 0.4069(16) 0.0596(7) 0.105(7) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.043(8) 0.041(8) 0.040(7) -0.004(6) -0.001(6) 0.011(7) O4A 0.040(8) 0.050(9) 0.044(8) 0.010(7) 0.010(6) 0.012(7) C7A 0.026(10) 0.070(16) 0.034(10) -0.008(11) -0.005(8) 0.005(10) F1A 0.042(8) 0.107(12) 0.053(8) -0.030(8) 0.001(6) -0.040(8) F2A 0.037(8) 0.109(12) 0.108(11) 0.039(10) -0.017(8) -0.039(8) F7A 0.054(9) 0.172(17) 0.059(9) -0.081(10) -0.006(7) 0.056(10) F8A 0.078(10) 0.057(8) 0.043(7) 0.023(6) 0.020(7) -0.009(7) F9A 0.058(9) 0.056(8) 0.072(9) -0.025(7) -0.021(7) 0.009(7) F10A 0.057(10) 0.089(12) 0.108(13) -0.016(10) -0.011(9) 0.026(9) F11A 0.042(8) 0.168(16) 0.038(7) -0.010(9) -0.018(6) 0.001(10) F12A 0.065(11) 0.167(17) 0.083(12) 0.068(12) -0.018(9) -0.049(11) O1B 0.041(8) 0.049(8) 0.028(7) 0.008(6) 0.021(6) 0.002(7) O4B 0.077(11) 0.028(8) 0.054(9) 0.004(7) 0.016(8) -0.013(8) F1B 0.051(8) 0.169(16) 0.044(7) -0.051(9) -0.011(6) 0.070(10) F2B 0.046(7) 0.075(9) 0.073(8) 0.019(8) 0.001(6) 0.009(7) F3B 0.055(8) 0.159(16) 0.051(8) -0.027(9) 0.025(6) -0.010(9) F4B 0.025(7) 0.167(18) 0.118(13) -0.071(13) -0.018(8) 0.018(9) F5B 0.070(11) 0.126(14) 0.087(11) 0.050(11) -0.001(9) -0.018(11) F6B 0.030(7) 0.100(12) 0.099(11) 0.018(10) 0.022(7) 0.006(8) F7B 0.060(8) 0.047(7) 0.064(8) 0.009(6) 0.021(7) 0.004(6) F8B 0.031(6) 0.084(9) 0.021(5) -0.024(6) -0.013(5) -0.013(6) F9B 0.054(8) 0.088(10) 0.050(7) -0.038(7) 0.002(6) 0.005(7) F10B 0.029(6) 0.166(15) 0.032(6) 0.001(8) 0.014(5) -0.027(8) F11B 0.059(9) 0.22(2) 0.069(9) 0.075(12) 0.025(8) 0.073(12) F12B 0.049(9) 0.134(15) 0.22(2) -0.114(15) 0.048(11) -0.052(10) O1C 0.046(8) 0.038(8) 0.034(7) -0.008(6) 0.000(6) 0.001(7) O4C 0.054(10) 0.042(8) 0.041(8) 0.002(6) 0.008(7) 0.007(7) F1C 0.039(7) 0.083(9) 0.045(7) 0.021(6) -0.014(6) 0.001(7) F2C 0.053(9) 0.085(11) 0.084(10) -0.051(9) 0.019(8) -0.034(8) F3C 0.043(10) 0.31(3) 0.106(13) -0.135(17) 0.038(9) -0.040(14) F7C 0.055(8) 0.016(6) 0.096(10) 0.008(6) 0.011(7) 0.002(5) F8C 0.045(7) 0.067(8) 0.034(6) 0.009(6) 0.027(5) 0.014(6) F9C 0.050(9) 0.108(13) 0.155(16) -0.063(12) -0.054(10) 0.009(9) F10C 0.078(11) 0.078(10) 0.058(8) 0.025(8) 0.007(8) 0.036(9) F11C 0.066(10) 0.151(15) 0.040(7) -0.033(9) -0.020(7) 0.038(11) F12C 0.032(8) 0.149(15) 0.078(10) 0.022(11) 0.009(7) 0.003(9) O1D 0.078(11) 0.032(8) 0.029(7) 0.000(6) -0.004(7) 0.007(8) O4D 0.053(9) 0.037(8) 0.033(7) -0.003(6) 0.007(6) -0.004(7) F1D 0.116(14) 0.084(11) 0.081(10) 0.032(9) -0.016(10) -0.014(11) F2D 0.084(10) 0.071(9) 0.023(6) -0.019(6) -0.015(6) -0.008(8) F3D 0.028(7) 0.148(16) 0.162(17) -0.112(14) 0.038(9) -0.029(9) F7D 0.044(8) 0.106(12) 0.060(8) 0.023(8) 0.002(6) 0.008(8) F8D 0.034(6) 0.084(9) 0.028(6) -0.017(6) 0.005(5) 0.012(6) F9D 0.041(9) 0.24(2) 0.131(15) -0.158(16) 0.027(9) -0.038(11) F10D 0.023(7) 0.106(12) 0.073(9) 0.002(9) -0.012(6) 0.005(8) F11D 0.047(9) 0.115(14) 0.091(12) -0.017(10) -0.006(8) 0.030(9) F12D 0.060(10) 0.177(19) 0.078(11) 0.064(12) 0.020(9) 0.008(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.47(2) . ? O4A C4A 1.48(2) . ? C1A C7A 1.46(3) . ? C1A C6A 1.51(3) . ? C1A C2A 1.55(3) . ? C2A C3A 1.52(3) . ? C3A C4A 1.51(3) . ? C4A C5A 1.42(3) . ? C4A C10A 1.58(3) . ? C5A C6A 1.48(3) . ? C7A F1A 1.34(2) . ? C7A F2A 1.38(3) . ? C7A C8A 1.38(3) . ? C8A F3A' 1.32(3) . ? C8A F3A 1.45(4) . ? C8A C9A 1.46(3) . ? C9A F5A' 1.301(18) . ? C9A F5A 1.31(2) . ? C9A F4A 1.320(19) . ? C9A F6A' 1.316(19) . ? C9A F4A' 1.33(2) . ? C9A F6A 1.33(2) . ? C10A F7A 1.29(2) . ? C10A F8A 1.44(2) . ? C10A C11A 1.44(2) . ? C11A F9A 1.40(2) . ? C11A C12A 1.51(3) . ? C12A F12A 1.297(17) . ? C12A F11A 1.309(17) . ? C12A F10A 1.325(17) . ? O1B C1B 1.52(2) . ? O4B C4B 1.48(2) . ? C1B C7B 1.37(3) . ? C1B C6B 1.49(3) . ? C1B C2B 1.57(3) . ? C2B C3B 1.47(3) . ? C3B C4B 1.54(3) . ? C4B C5B 1.50(3) . ? C4B C10B 1.50(3) . ? C5B C6B 1.44(3) . ? C7B F1B 1.33(2) . ? C7B F2B 1.45(2) . ? C7B C8B 1.60(3) . ? C8B F3B 1.28(2) . ? C8B C9B 1.43(3) . ? C9B F6B 1.309(17) . ? C9B F4B 1.315(17) . ? C9B F5B 1.315(17) . ? C10B F7B 1.38(2) . ? C10B F8B 1.36(2) . ? C10B C11B 1.54(3) . ? C11B F9B 1.37(2) . ? C11B C12B 1.50(3) . ? C12B F11B 1.250(17) . ? C12B F10B 1.282(17) . ? C12B F12B 1.285(17) . ? O1C C1C 1.49(2) . ? O4C C4C 1.45(2) . ? C1C C6C 1.49(3) . ? C1C C7C 1.53(3) . ? C1C C2C 1.56(3) . ? C2C C3C 1.50(2) . ? C3C C4C 1.56(2) . ? C4C C5C 1.47(2) . ? C4C C10C 1.55(3) . ? C5C C6C 1.57(2) . ? C7C F2C 1.37(2) . ? C7C F1C 1.41(2) . ? C7C C8C 1.47(3) . ? C8C F3C 1.46(3) . ? C8C C9C 1.53(2) . ? C9C F6C' 1.189(9) . ? C9C F5C' 1.278(9) . ? C9C F4C 1.278(9) . ? C9C F5C 1.278(9) . ? C9C F4C' 1.278(9) . ? C9C F6C 1.492(11) . ? C10C F7C 1.33(2) . ? C10C F8C 1.422(19) . ? C10C C11C 1.46(3) . ? C11C F9C 1.28(2) . ? C11C C12C 1.50(4) . ? C12C F12C 1.310(18) . ? C12C F11C 1.311(18) . ? C12C F10C 1.313(18) . ? O1D C1D 1.47(2) . ? O4D C4D 1.44(2) . ? C1D C7D 1.45(3) . ? C1D C2D 1.52(3) . ? C1D C6D 1.52(3) . ? C2D C3D 1.52(3) . ? C3D C4D 1.53(3) . ? C4D C10D 1.53(3) . ? C4D C5D 1.54(2) . ? C5D C6D 1.53(3) . ? C7D F2D 1.31(2) . ? C7D F1D 1.46(3) . ? C7D C8D 1.57(3) . ? C8D F3D 1.33(2) . ? C8D C9D 1.62(4) . ? C9D F5D' 1.224(17) . ? C9D F6D 1.234(16) . ? C9D F6D' 1.271(17) . ? C9D F5D 1.291(17) . ? C9D F4D' 1.324(16) . ? C9D F4D 1.358(17) . ? C10D F8D 1.35(2) . ? C10D F7D 1.36(2) . ? C10D C11D 1.55(3) . ? C11D F9D 1.18(2) . ? C11D C12D 1.48(4) . ? C12D F11D 1.319(17) . ? C12D F10D 1.302(17) . ? C12D F12D 1.301(17) . ? 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 C7A C1A O1A 104.9(18) . . ? C7A C1A C6A 119.1(18) . . ? O1A C1A C6A 104.9(16) . . ? C7A C1A C2A 113.5(18) . . ? O1A C1A C2A 102.9(16) . . ? C6A C1A C2A 109.5(17) . . ? C3A C2A C1A 118.8(18) . . ? C4A C3A C2A 111.9(17) . . ? C5A C4A C3A 117.0(19) . . ? C5A C4A O4A 103.1(17) . . ? C3A C4A O4A 106.9(16) . . ? C5A C4A C10A 116.6(18) . . ? C3A C4A C10A 108.9(17) . . ? O4A C4A C10A 102.5(16) . . ? C4A C5A C6A 115.8(18) . . ? C5A C6A C1A 119.1(16) . . ? F1A C7A F2A 102.3(19) . . ? F1A C7A C8A 111.3(19) . . ? F2A C7A C8A 95(2) . . ? F1A C7A C1A 114.9(18) . . ? F2A C7A C1A 108.0(17) . . ? C8A C7A C1A 121(2) . . ? F3A' C8A C7A 124(2) . . ? F3A' C8A F3A 64.5(18) . . ? C7A C8A F3A 112(2) . . ? F3A' C8A C9A 110(2) . . ? C7A C8A C9A 124(2) . . ? F3A C8A C9A 104.3(19) . . ? F5A' C9A F5A 51.6(15) . . ? F5A' C9A F4A 127(2) . . ? F5A C9A F4A 103.1(17) . . ? F5A' C9A F6A' 105.5(18) . . ? F5A C9A F6A' 133(3) . . ? F4A C9A F6A' 53.7(15) . . ? F5A' C9A F4A' 103.2(17) . . ? F5A C9A F4A' 56.3(16) . . ? F4A C9A F4A' 52.4(15) . . ? F6A' C9A F4A' 103.8(17) . . ? F5A' C9A F6A 54.8(16) . . ? F5A C9A F6A 103.0(17) . . ? F4A C9A F6A 102.5(18) . . ? F6A' C9A F6A 55.1(16) . . ? F4A' C9A F6A 131(3) . . ? F5A' C9A C8A 115.8(15) . . ? F5A C9A C8A 114.2(16) . . ? F4A C9A C8A 117.5(15) . . ? F6A' C9A C8A 113.2(16) . . ? F4A' C9A C8A 114.1(16) . . ? F6A C9A C8A 114.8(16) . . ? F7A C10A F8A 101.4(16) . . ? F7A C10A C11A 114.7(17) . . ? F8A C10A C11A 106.2(15) . . ? F7A C10A C4A 111.1(17) . . ? F8A C10A C4A 101.4(15) . . ? C11A C10A C4A 119.2(17) . . ? C10A C11A F9A 111.9(15) . . ? C10A C11A C12A 115.9(14) . . ? F9A C11A C12A 106.6(13) . . ? F12A C12A F11A 106.7(16) . . ? F12A C12A F10A 107.0(17) . . ? F11A C12A F10A 105.0(16) . . ? F12A C12A C11A 113.6(16) . . ? F11A C12A C11A 113.4(15) . . ? F10A C12A C11A 110.6(15) . . ? C7B C1B C6B 119.0(18) . . ? C7B C1B O1B 103.5(16) . . ? C6B C1B O1B 107.8(16) . . ? C7B C1B C2B 115.3(17) . . ? C6B C1B C2B 110.6(18) . . ? O1B C1B C2B 97.8(14) . . ? C3B C2B C1B 116.1(16) . . ? C2B C3B C4B 115.1(17) . . ? O4B C4B C5B 109.5(16) . . ? O4B C4B C3B 103.6(15) . . ? C5B C4B C3B 112.9(17) . . ? O4B C4B C10B 107.6(16) . . ? C5B C4B C10B 109.0(16) . . ? C3B C4B C10B 114.0(16) . . ? C6B C5B C4B 112.5(18) . . ? C5B C6B C1B 120.7(19) . . ? F1B C7B C1B 114.6(17) . . ? F1B C7B F2B 97.6(16) . . ? C1B C7B F2B 108.9(17) . . ? F1B C7B C8B 106.2(17) . . ? C1B C7B C8B 125.8(19) . . ? F2B C7B C8B 99.0(15) . . ? F3B C8B C9B 113.0(18) . . ? F3B C8B C7B 112.7(19) . . ? C9B C8B C7B 119.9(18) . . ? F6B C9B F4B 106.3(15) . . ? F6B C9B F5B 106.3(15) . . ? F4B C9B F5B 105.3(15) . . ? F6B C9B C8B 113.7(15) . . ? F4B C9B C8B 111.4(17) . . ? F5B C9B C8B 113.1(15) . . ? F7B C10B F8B 104.5(16) . . ? F7B C10B C4B 110.9(17) . . ? F8B C10B C4B 112.0(17) . . ? F7B C10B C11B 102.0(16) . . ? F8B C10B C11B 107.0(17) . . ? C4B C10B C11B 119.1(17) . . ? F9B C11B C10B 111.7(16) . . ? F9B C11B C12B 107.7(14) . . ? C10B C11B C12B 119.6(15) . . ? F11B C12B F10B 109.9(17) . . ? F11B C12B F12B 106.9(17) . . ? F10B C12B F12B 105.6(16) . . ? F11B C12B C11B 113.2(16) . . ? F10B C12B C11B 110.0(15) . . ? F12B C12B C11B 110.9(16) . . ? C6C C1C O1C 103.0(14) . . ? C6C C1C C7C 117.0(17) . . ? O1C C1C C7C 103.2(16) . . ? C6C C1C C2C 113.5(16) . . ? O1C C1C C2C 107.0(16) . . ? C7C C1C C2C 111.7(16) . . ? C3C C2C C1C 113.3(15) . . ? C2C C3C C4C 112.4(14) . . ? O4C C4C C5C 111.4(15) . . ? O4C C4C C3C 107.6(14) . . ? C5C C4C C3C 111.8(15) . . ? O4C C4C C10C 106.2(15) . . ? C5C C4C C10C 110.6(15) . . ? C3C C4C C10C 108.9(14) . . ? C4C C5C C6C 113.3(15) . . ? C1C C6C C5C 112.3(15) . . ? F2C C7C F1C 102.7(16) . . ? F2C C7C C8C 107.5(18) . . ? F1C C7C C8C 112.3(18) . . ? F2C C7C C1C 112.7(18) . . ? F1C C7C C1C 102.4(17) . . ? C8C C7C C1C 118.2(18) . . ? F3C C8C C7C 103.1(18) . . ? F3C C8C C9C 99.8(15) . . ? C7C C8C C9C 117.2(17) . . ? F6C' C9C F5C' 107.1 . . ? F6C' C9C F4C 77.2 . . ? F5C' C9C F4C 130.7 . . ? F6C' C9C F5C 119.2 . . ? F5C' C9C F5C 24.8 . . ? F4C C9C F5C 109.6 . . ? F6C' C9C F4C' 107.1 . . ? F5C' C9C F4C' 106.8 . . ? F4C C9C F4C' 33.3 . . ? F5C C9C F4C' 82.3 . . ? F6C' C9C F6C 35.5 . . ? F5C' C9C F6C 89.6 . . ? F4C C9C F6C 111.9 . . ? F5C C9C F6C 111.9 . . ? F4C' C9C F6C 142.6 . . ? F6C' C9C C8C 122.5(9) . . ? F5C' C9C C8C 107.1(9) . . ? F4C C9C C8C 110.9(9) . . ? F5C C9C C8C 111.1(8) . . ? F4C' C9C C8C 105.4(9) . . ? F6C C9C C8C 101.2(9) . . ? F7C C10C F8C 105.2(14) . . ? F7C C10C C11C 104.4(15) . . ? F8C C10C C11C 108.0(15) . . ? F7C C10C C4C 110.0(15) . . ? F8C C10C C4C 108.0(14) . . ? C11C C10C C4C 120.2(16) . . ? F9C C11C C10C 115.1(17) . . ? F9C C11C C12C 108.3(16) . . ? C10C C11C C12C 117.3(15) . . ? F12C C12C F11C 108.2(18) . . ? F12C C12C F10C 107.6(18) . . ? F11C C12C F10C 106.8(17) . . ? F12C C12C C11C 112.2(17) . . ? F11C C12C C11C 110.7(17) . . ? F10C C12C C11C 111.1(17) . . ? O1D C1D C7D 103.9(16) . . ? O1D C1D C2D 109.3(15) . . ? C7D C1D C2D 110.3(16) . . ? O1D C1D C6D 106.2(15) . . ? C7D C1D C6D 114.9(17) . . ? C2D C1D C6D 111.7(16) . . ? C1D C2D C3D 110.1(15) . . ? C4D C3D C2D 112.9(16) . . ? O4D C4D C10D 106.9(15) . . ? O4D C4D C5D 106.5(14) . . ? C10D C4D C5D 113.3(15) . . ? O4D C4D C3D 112.1(15) . . ? C10D C4D C3D 109.8(15) . . ? C5D C4D C3D 108.2(15) . . ? C6D C5D C4D 111.3(14) . . ? C1D C6D C5D 114.0(15) . . ? F2D C7D F1D 100.8(17) . . ? F2D C7D C1D 112.0(19) . . ? F1D C7D C1D 109.0(18) . . ? F2D C7D C8D 103.0(18) . . ? F1D C7D C8D 110.3(18) . . ? C1D C7D C8D 119.9(18) . . ? F3D C8D C7D 107.2(17) . . ? F3D C8D C9D 105.7(14) . . ? C7D C8D C9D 117.3(15) . . ? F5D' C9D F6D 161(4) . . ? F5D' C9D F6D' 121(2) . . ? F6D C9D F6D' 47.5(15) . . ? F5D' C9D F5D 56.9(16) . . ? F6D C9D F5D 117.9(18) . . ? F6D' C9D F5D 136(3) . . ? F5D' C9D F4D' 113.6(16) . . ? F6D C9D F4D' 66.3(14) . . ? F6D' C9D F4D' 109.7(16) . . ? F5D C9D F4D' 57.0(15) . . ? F5D' C9D F4D 60.0(15) . . ? F6D C9D F4D 109.9(15) . . ? F6D' C9D F4D 62.6(16) . . ? F5D C9D F4D 106.7(16) . . ? F4D' C9D F4D 150(3) . . ? F5D' C9D C8D 87(2) . . ? F6D C9D C8D 111.0(18) . . ? F6D' C9D C8D 117(2) . . ? F5D C9D C8D 106.9(16) . . ? F4D' C9D C8D 105.6(18) . . ? F4D C9D C8D 103.4(15) . . ? F8D C10D F7D 105.8(15) . . ? F8D C10D C4D 109.2(15) . . ? F7D C10D C4D 108.9(15) . . ? F8D C10D C11D 108.3(16) . . ? F7D C10D C11D 104.7(16) . . ? C4D C10D C11D 119.1(17) . . ? F9D C11D C12D 111.4(18) . . ? F9D C11D C10D 117(2) . . ? C12D C11D C10D 117.4(16) . . ? F11D C12D F10D 104.9(16) . . ? F11D C12D F12D 104.6(16) . . ? F10D C12D F12D 108.0(16) . . ? F11D C12D C11D 111.8(15) . . ? F10D C12D C11D 113.2(15) . . ? F12D C12D C11D 113.6(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H01A F11B 0.84 2.31 3.15(2) 174.4 . O4A H04A O4C 0.84 2.05 2.831(18) 153.7 . O1B H01B F8A 0.84 2.38 3.207(16) 170.5 1_455 O4B H04B O1D 0.84 1.98 2.810(18) 168.8 1_565 O1C H01C O1A 0.84 2.10 2.846(18) 147.1 1_545 O4C H04C F7D 0.84 2.32 3.161(18) 175.7 1_655 O1D H01D F4C 0.84 2.48 3.135(16) 136.1 . O4D H04D O1B 0.84 1.97 2.780(18) 163.0 . _refine_diff_density_max 1.578 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.189 #================================================END data_25/aldol _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-1,4-di-(1,1,2,3,3,3-hexafluoropropyl)-cyclohexane-1,4-diol aldol (3:2) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C12 H12 F12 O2)3,(C6 H12 O2)2' _chemical_formula_sum 'C48 H60 F36 O10' _chemical_formula_weight 1480.96 _ccdc_compound_id '25/aldol' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Atoms C15, C16, H15, F13 and F14 are disordered between two positions: A (occupancy 82.5(7)%) and B (occupancy 17.5(7)%). Atoms C35, C36, H35, F33 and F35 are disordered between two positions, A (occupancy 79.6(7)%) and B (occupancy 20.4(7)%). ; _ccdc_comments '?' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 10.709(4) _cell_length_b 10.853(3) _cell_length_c 13.926(4) _cell_angle_alpha 106.98(1) _cell_angle_beta 99.83(2) _cell_angle_gamma 91.33(1) _cell_volume 1520.7(8) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 308 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 20.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9307 _exptl_absorpt_correction_T_max 0.9820 _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (30 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing duplicate reflections. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 150(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9023 _diffrn_reflns_av_R_equivalents 0.1134 _diffrn_reflns_av_sigmaI/netI 0.0977 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.0 _reflns_number_total 5331 _reflns_number_gt 3702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0387P)^2^+5.6326P] 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 5331 _refine_ls_number_parameters 461 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.2403 _refine_ls_wR_factor_gt 0.1996 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.182 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5318(3) 0.4070(3) 0.1290(3) 0.0304(8) Uani 1 1 d . . . H01 H 0.5693 0.3231 0.1121 0.046 Uiso 1 1 d R . . C11 C 0.5971(5) 0.4920(4) 0.0883(4) 0.0267(11) Uani 1 1 d . . . C12 C 0.5170(5) 0.6095(5) 0.0946(4) 0.0284(11) Uani 1 1 d . . . H121 H 0.5037 0.6474 0.1656 0.034 Uiso 1 1 d R . . H122 H 0.5644 0.6759 0.0760 0.034 Uiso 1 1 d R . . C13 C 0.3884(5) 0.5732(5) 0.0220(4) 0.0290(11) Uani 1 1 d . . . H131 H 0.3378 0.5133 0.0448 0.035 Uiso 1 1 d R . . H132 H 0.3416 0.6516 0.0254 0.035 Uiso 1 1 d R . . C14 C 0.7273(5) 0.5328(5) 0.1569(4) 0.0313(12) Uani 1 1 d D . . C15A C 0.7261(7) 0.6038(8) 0.2698(5) 0.0316(16) Uani 0.825(7) 1 d P A 1 H15A H 0.6418 0.5866 0.2938 0.041 Uiso 0.825(7) 1 d PR A 1 C16A C 0.8470(7) 0.6029(8) 0.3446(6) 0.0387(18) Uani 0.825(7) 1 d P A 1 C15B C 0.736(4) 0.556(2) 0.2723(15) 0.055(18) Uiso 0.175(7) 1 d PD A 2 C16B C 0.835(2) 0.664(2) 0.3385(15) 0.044(11) Uiso 0.175(7) 1 d PD A 2 F11 F 0.7954(3) 0.4256(3) 0.1501(3) 0.0442(8) Uani 1 1 d . A . F12 F 0.7966(3) 0.6137(3) 0.1233(3) 0.0409(8) Uani 1 1 d . A . F13A F 0.7101(4) 0.7344(4) 0.2804(3) 0.0449(13) Uani 0.825(7) 1 d P A 1 F14A F 0.8578(5) 0.4836(4) 0.3552(4) 0.0544(14) Uani 0.825(7) 1 d P A 1 F13B F 0.7591(18) 0.4510(16) 0.3038(14) 0.035(5) Uiso 0.175(7) 1 d PD A 2 F14B F 0.805(2) 0.7763(17) 0.3247(15) 0.042(6) Uiso 0.175(7) 1 d PD A 2 F15 F 0.9522(3) 0.6367(4) 0.3174(3) 0.0540(10) Uani 1 1 d D . . F16 F 0.8411(4) 0.6821(4) 0.4371(3) 0.0589(10) Uani 1 1 d D . . O2 O 0.3525(4) 0.8255(3) 0.4618(3) 0.0348(9) Uani 1 1 d . . . H02 H 0.3332 0.8417 0.5206 0.052 Uiso 1 1 d R . . C21 C 0.3723(6) 0.9434(5) 0.4365(4) 0.0337(13) Uani 1 1 d . . . C22 C 0.4938(6) 0.9344(5) 0.3899(4) 0.0350(13) Uani 1 1 d . . . H221 H 0.4869 0.8534 0.3327 0.042 Uiso 1 1 d R . . H222 H 0.5014 1.0080 0.3622 0.042 Uiso 1 1 d R . . C23 C 0.6131(6) 0.9379(5) 0.4688(4) 0.0368(13) Uani 1 1 d . . . H231 H 0.6891 0.9363 0.4368 0.044 Uiso 1 1 d R . . H232 H 0.6088 0.8594 0.4910 0.044 Uiso 1 1 d R . . C24 C 0.2517(6) 0.9502(5) 0.3589(5) 0.0426(15) Uani 1 1 d . . . C25 C 0.2088(7) 0.8329(7) 0.2684(5) 0.0568(18) Uani 1 1 d . . . H25 H 0.2306 0.7240 0.2618 0.074 Uiso 1 1 d R . . C26 C 0.0884(7) 0.8416(7) 0.1939(6) 0.0585(19) Uani 1 1 d . . . F21 F 0.2676(4) 1.0573(3) 0.3291(3) 0.0623(11) Uani 1 1 d . . . F22 F 0.1493(4) 0.9702(4) 0.4101(3) 0.0620(11) Uani 1 1 d . . . F23 F 0.3037(5) 0.8123(5) 0.2100(4) 0.0880(16) Uani 1 1 d . . . F24 F 0.0946(4) 0.9431(4) 0.1596(3) 0.0704(12) Uani 1 1 d . . . F25 F 0.0673(5) 0.7365(5) 0.1152(4) 0.1010(19) Uani 1 1 d . . . F26 F -0.0137(4) 0.8548(5) 0.2396(4) 0.0789(14) Uani 1 1 d . . . O3 O 0.4512(4) 0.5922(3) 0.3717(3) 0.0350(9) Uani 1 1 d . . . H03 H 0.4154 0.6607 0.3923 0.052 Uiso 1 1 d R . . C31 C 0.4018(5) 0.4927(5) 0.4072(4) 0.0313(12) Uani 1 1 d . . . C32 C 0.3768(5) 0.5453(5) 0.5162(4) 0.0329(13) Uani 1 1 d . . . H321 H 0.3136 0.6108 0.5183 0.040 Uiso 1 1 d R . . H322 H 0.3394 0.4733 0.5350 0.040 Uiso 1 1 d R . . C33 C 0.4962(5) 0.6054(5) 0.5957(4) 0.0317(12) Uani 1 1 d . . . H331 H 0.4746 0.6346 0.6648 0.038 Uiso 1 1 d R . . H332 H 0.5305 0.6819 0.5806 0.038 Uiso 1 1 d R . . C34 C 0.2780(6) 0.4330(5) 0.3348(5) 0.0369(13) Uani 1 1 d D . . C35A C 0.2894(7) 0.3685(8) 0.2209(6) 0.0364(18) Uani 0.796(7) 1 d P B 1 H35A H 0.3728 0.4353 0.2087 0.047 Uiso 0.796(7) 1 d PR B 1 C36A C 0.1646(9) 0.3458(11) 0.1433(7) 0.044(2) Uani 0.796(7) 1 d P B 1 C35B C 0.277(2) 0.4205(18) 0.2227(12) 0.015(6) Uiso 0.204(7) 1 d PD B 2 C36B C 0.1869(18) 0.309(2) 0.1530(14) 0.036(12) Uiso 0.204(7) 1 d PD B 2 F31 F 0.2258(3) 0.3368(3) 0.3636(3) 0.0444(9) Uani 1 1 d . B . F32 F 0.1917(3) 0.5246(3) 0.3404(3) 0.0574(10) Uani 1 1 d . B . F33A F 0.3353(4) 0.2464(4) 0.2092(3) 0.0465(13) Uani 0.796(7) 1 d P B 1 F33B F 0.2413(16) 0.5290(15) 0.2010(13) 0.046(5) Uiso 0.204(7) 1 d PD B 2 F34 F 0.0704(4) 0.2922(5) 0.1704(3) 0.0819(15) Uani 1 1 d D . . F35A F 0.1257(5) 0.4577(5) 0.1318(4) 0.0678(17) Uani 0.796(7) 1 d P B 1 F35B F 0.222(2) 0.198(2) 0.1640(17) 0.074(7) Uiso 0.204(7) 1 d PD B 2 F36 F 0.1815(4) 0.2780(4) 0.0528(3) 0.0703(12) Uani 1 1 d D . . O41 O 0.3067(4) 0.8534(4) 0.6592(3) 0.0411(10) Uani 1 1 d . . . O42 O 0.4014(4) 0.8384(3) 0.8632(3) 0.0400(10) Uani 1 1 d . . . H042 H 0.4233 0.8166 0.8057 0.060 Uiso 1 1 d R . . C41 C 0.0840(7) 0.8085(8) 0.6006(6) 0.065(2) Uani 1 1 d . . . H411 H 0.0432 0.8871 0.5962 0.097 Uiso 1 1 d R . . H412 H 0.0247 0.7512 0.6175 0.097 Uiso 1 1 d R . . H413 H 0.1073 0.7640 0.5348 0.097 Uiso 1 1 d R . . C42 C 0.2014(6) 0.8436(5) 0.6818(5) 0.0402(14) Uani 1 1 d . . . C43 C 0.1837(6) 0.8645(5) 0.7893(5) 0.0370(13) Uani 1 1 d . . . H431 H 0.1558 0.7827 0.7951 0.044 Uiso 1 1 d R . . H432 H 0.1159 0.9203 0.8011 0.044 Uiso 1 1 d R . . C44 C 0.2980(6) 0.9213(5) 0.8755(4) 0.0373(13) Uani 1 1 d . . . C45 C 0.3434(7) 1.0583(5) 0.8779(5) 0.0514(17) Uani 1 1 d . . . H451 H 0.4148 1.0904 0.9327 0.077 Uiso 1 1 d R . . H452 H 0.3686 1.0544 0.8142 0.077 Uiso 1 1 d R . . H453 H 0.2762 1.1151 0.8883 0.077 Uiso 1 1 d R . . C46 C 0.2634(7) 0.9239(7) 0.9774(5) 0.0532(17) Uani 1 1 d . . . H461 H 0.2340 0.8388 0.9756 0.080 Uiso 1 1 d R . . H462 H 0.3376 0.9538 1.0299 0.080 Uiso 1 1 d R . . H463 H 0.1978 0.9816 0.9917 0.080 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.031(2) 0.0267(18) 0.040(2) 0.0167(16) 0.0121(17) 0.0001(15) C11 0.032(3) 0.020(2) 0.032(3) 0.013(2) 0.007(2) 0.000(2) C12 0.035(3) 0.021(2) 0.028(3) 0.005(2) 0.004(2) -0.004(2) C13 0.032(3) 0.023(2) 0.034(3) 0.011(2) 0.009(2) 0.002(2) C14 0.027(3) 0.031(3) 0.042(3) 0.019(2) 0.010(2) 0.000(2) C15A 0.030(4) 0.031(4) 0.035(4) 0.010(3) 0.010(3) 0.004(3) C16A 0.032(4) 0.050(5) 0.039(4) 0.021(4) 0.007(3) -0.002(3) F11 0.0384(19) 0.0343(17) 0.056(2) 0.0128(16) -0.0018(16) 0.0097(14) F12 0.0374(19) 0.0416(18) 0.046(2) 0.0201(15) 0.0044(15) -0.0130(14) F13A 0.054(3) 0.033(2) 0.040(2) 0.0036(18) -0.001(2) 0.0081(19) F14A 0.054(3) 0.061(3) 0.058(3) 0.036(2) 0.005(2) 0.007(2) F15 0.0298(19) 0.075(3) 0.060(2) 0.030(2) 0.0031(17) -0.0077(17) F16 0.057(2) 0.074(3) 0.037(2) 0.0076(19) 0.0016(18) -0.009(2) O2 0.050(2) 0.0189(17) 0.038(2) 0.0096(16) 0.0118(19) -0.0005(16) C21 0.049(4) 0.018(2) 0.037(3) 0.012(2) 0.009(3) 0.002(2) C22 0.050(4) 0.019(2) 0.034(3) 0.003(2) 0.010(3) -0.002(2) C23 0.042(3) 0.022(3) 0.044(3) 0.006(2) 0.009(3) 0.001(2) C24 0.052(4) 0.027(3) 0.052(4) 0.015(3) 0.013(3) 0.007(3) C25 0.059(4) 0.050(4) 0.049(4) 0.006(3) -0.006(4) 0.010(3) C26 0.052(4) 0.056(4) 0.065(5) 0.024(4) -0.004(4) 0.000(3) F21 0.077(3) 0.0350(19) 0.075(3) 0.0317(19) -0.010(2) 0.0013(18) F22 0.043(2) 0.067(3) 0.069(3) 0.009(2) 0.011(2) 0.0051(18) F23 0.072(3) 0.106(4) 0.062(3) -0.010(3) 0.006(3) 0.023(3) F24 0.062(3) 0.082(3) 0.078(3) 0.050(3) -0.002(2) 0.001(2) F25 0.100(4) 0.075(3) 0.092(4) 0.002(3) -0.038(3) 0.014(3) F26 0.059(3) 0.097(3) 0.084(3) 0.043(3) -0.001(2) -0.022(2) O3 0.041(2) 0.0239(18) 0.049(2) 0.0191(18) 0.0167(19) 0.0051(16) C31 0.035(3) 0.026(3) 0.041(3) 0.019(2) 0.011(3) 0.002(2) C32 0.032(3) 0.029(3) 0.050(3) 0.026(3) 0.017(3) 0.013(2) C33 0.037(3) 0.023(2) 0.042(3) 0.014(2) 0.017(3) 0.007(2) C34 0.039(3) 0.032(3) 0.046(3) 0.019(3) 0.012(3) -0.001(2) C35A 0.044(5) 0.022(4) 0.049(5) 0.017(3) 0.010(4) 0.004(3) C36A 0.040(5) 0.048(5) 0.045(6) 0.016(5) 0.012(4) 0.001(5) F31 0.051(2) 0.0380(18) 0.048(2) 0.0180(16) 0.0127(17) -0.0142(15) F32 0.039(2) 0.046(2) 0.082(3) 0.0170(19) -0.0019(19) 0.0093(16) F33A 0.059(3) 0.035(2) 0.047(3) 0.010(2) 0.016(2) 0.009(2) F34 0.052(3) 0.120(4) 0.072(3) 0.032(3) 0.004(2) -0.039(3) F35A 0.065(4) 0.067(3) 0.073(4) 0.028(3) 0.002(3) 0.018(3) F36 0.072(3) 0.088(3) 0.044(2) 0.011(2) 0.009(2) -0.010(2) O41 0.044(3) 0.037(2) 0.043(2) 0.0103(18) 0.015(2) 0.0028(18) O42 0.049(3) 0.030(2) 0.042(2) 0.0122(18) 0.010(2) 0.0043(18) C41 0.044(4) 0.084(5) 0.061(5) 0.023(4) -0.002(4) 0.003(4) C42 0.043(4) 0.026(3) 0.051(4) 0.010(3) 0.011(3) 0.005(2) C43 0.039(3) 0.027(3) 0.047(3) 0.012(3) 0.013(3) 0.003(2) C44 0.046(4) 0.025(3) 0.041(3) 0.011(2) 0.007(3) 0.005(2) C45 0.067(5) 0.027(3) 0.058(4) 0.011(3) 0.010(4) -0.001(3) C46 0.069(5) 0.053(4) 0.043(4) 0.017(3) 0.019(3) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.440(6) . ? C11 C14 1.524(7) . ? C11 C13 1.527(7) 2_665 ? C11 C12 1.543(7) . ? C12 C13 1.531(7) . ? C13 C11 1.527(7) 2_665 ? C14 F12 1.366(6) . ? C14 F11 1.376(6) . ? C14 C15B 1.538(19) . ? C14 C15A 1.539(9) . ? C15A F13A 1.400(10) . ? C15A C16A 1.519(10) . ? C16A F15 1.324(8) . ? C16A F16 1.336(8) . ? C16A F14A 1.351(9) . ? C15B F13B 1.355(19) . ? C15B C16B 1.53(2) . ? C16B F16 1.319(18) . ? C16B F14B 1.329(19) . ? C16B F15 1.352(18) . ? O2 C21 1.443(6) . ? C21 C23 1.533(7) 2_676 ? C21 C22 1.543(8) . ? C21 C24 1.555(9) . ? C22 C23 1.527(8) . ? C23 C21 1.533(7) 2_676 ? C24 F21 1.360(6) . ? C24 F22 1.395(7) . ? C24 C25 1.502(9) . ? C25 F23 1.390(9) . ? C25 C26 1.534(10) . ? C26 F25 1.314(9) . ? C26 F24 1.327(8) . ? C26 F26 1.346(9) . ? O3 C31 1.437(6) . ? C31 C34 1.522(8) . ? C31 C32 1.530(8) . ? C31 C33 1.540(7) 2_666 ? C32 C33 1.531(8) . ? C33 C31 1.540(7) 2_666 ? C34 F31 1.362(6) . ? C34 F32 1.368(7) . ? C34 C35B 1.527(16) . ? C34 C35A 1.564(10) . ? C35A F33A 1.399(9) . ? C35A C36A 1.533(12) . ? C36A F36 1.306(9) . ? C36A F34 1.314(9) . ? C36A F35A 1.337(13) . ? C35B F33B 1.348(17) . ? C35B C36B 1.512(18) . ? C36B F35B 1.319(18) . ? C36B F36 1.327(18) . ? C36B F34 1.329(18) . ? O41 C42 1.232(7) . ? O42 C44 1.445(7) . ? C41 C42 1.499(9) . ? C42 C43 1.492(8) . ? C43 C44 1.534(9) . ? C44 C46 1.520(8) . ? C44 C45 1.542(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C11 C14 107.0(4) . . ? O1 C11 C13 112.1(4) . 2_665 ? C14 C11 C13 110.3(4) . 2_665 ? O1 C11 C12 106.1(4) . . ? C14 C11 C12 110.6(4) . . ? C13 C11 C12 110.6(4) 2_665 . ? C13 C12 C11 112.0(4) . . ? C11 C13 C12 112.0(4) 2_665 . ? F12 C14 F11 105.3(4) . . ? F12 C14 C11 111.0(4) . . ? F11 C14 C11 109.0(4) . . ? F12 C14 C15B 119.6(12) . . ? F11 C14 C15B 90.9(12) . . ? C11 C14 C15B 117.7(15) . . ? F12 C14 C15A 106.1(5) . . ? F11 C14 C15A 109.5(5) . . ? C11 C14 C15A 115.5(5) . . ? C15B C14 C15A 20.0(10) . . ? F13A C15A C16A 105.2(6) . . ? F13A C15A C14 108.7(6) . . ? C16A C15A C14 115.7(6) . . ? F15 C16A F16 108.4(6) . . ? F15 C16A F14A 107.9(6) . . ? F16 C16A F14A 106.4(6) . . ? F15 C16A C15A 114.1(6) . . ? F16 C16A C15A 110.0(6) . . ? F14A C16A C15A 109.8(6) . . ? F13B C15B C16B 107(2) . . ? F13B C15B C14 114.5(19) . . ? C16B C15B C14 114(2) . . ? F16 C16B F14B 104.6(17) . . ? F16 C16B F15 107.8(14) . . ? F14B C16B F15 110.8(18) . . ? F16 C16B C15B 112.6(16) . . ? F14B C16B C15B 110.1(19) . . ? F15 C16B C15B 111(2) . . ? C16A F15 C16B 30.5(10) . . ? C16B F16 C16A 30.7(10) . . ? O2 C21 C23 111.4(4) . 2_676 ? O2 C21 C22 107.6(4) . . ? C23 C21 C22 110.1(5) 2_676 . ? O2 C21 C24 105.8(4) . . ? C23 C21 C24 109.5(4) 2_676 . ? C22 C21 C24 112.3(5) . . ? C23 C22 C21 112.0(5) . . ? C22 C23 C21 113.0(5) . 2_676 ? F21 C24 F22 105.8(5) . . ? F21 C24 C25 111.2(5) . . ? F22 C24 C25 104.8(5) . . ? F21 C24 C21 108.3(5) . . ? F22 C24 C21 108.2(5) . . ? C25 C24 C21 117.8(5) . . ? F23 C25 C24 107.9(6) . . ? F23 C25 C26 104.7(6) . . ? C24 C25 C26 116.7(6) . . ? F25 C26 F24 108.5(6) . . ? F25 C26 F26 108.6(6) . . ? F24 C26 F26 105.3(6) . . ? F25 C26 C25 110.0(6) . . ? F24 C26 C25 113.2(6) . . ? F26 C26 C25 111.0(6) . . ? O3 C31 C34 107.5(4) . . ? O3 C31 C32 112.2(4) . . ? C34 C31 C32 109.5(4) . . ? O3 C31 C33 106.1(4) . 2_666 ? C34 C31 C33 111.9(4) . 2_666 ? C32 C31 C33 109.6(4) . 2_666 ? C31 C32 C33 113.7(4) . . ? C32 C33 C31 110.5(4) . 2_666 ? F31 C34 F32 106.3(4) . . ? F31 C34 C31 110.8(4) . . ? F32 C34 C31 109.2(4) . . ? F31 C34 C35B 121.6(9) . . ? F32 C34 C35B 91.2(9) . . ? C31 C34 C35B 114.9(9) . . ? F31 C34 C35A 104.7(5) . . ? F32 C34 C35A 109.8(5) . . ? C31 C34 C35A 115.6(5) . . ? C35B C34 C35A 21.4(6) . . ? F33A C35A C36A 105.4(7) . . ? F33A C35A C34 109.9(6) . . ? C36A C35A C34 115.4(6) . . ? F36 C36A F34 110.8(7) . . ? F36 C36A F35A 105.0(8) . . ? F34 C36A F35A 106.0(8) . . ? F36 C36A C35A 110.5(8) . . ? F34 C36A C35A 113.5(8) . . ? F35A C36A C35A 110.6(7) . . ? F33B C35B C36B 108.1(18) . . ? F33B C35B C34 111.0(15) . . ? C36B C35B C34 111.2(14) . . ? F35B C36B F36 97.1(17) . . ? F35B C36B F34 94.6(17) . . ? F36 C36B F34 108.6(14) . . ? F35B C36B C35B 111.5(19) . . ? F36 C36B C35B 119.2(15) . . ? F34 C36B C35B 120.5(16) . . ? C36A F34 C36B 22.2(10) . . ? C36A F36 C36B 22.3(10) . . ? O41 C42 C43 122.6(6) . . ? O41 C42 C41 120.5(6) . . ? C43 C42 C41 116.8(6) . . ? C42 C43 C44 118.1(5) . . ? O42 C44 C46 105.6(5) . . ? O42 C44 C43 110.1(4) . . ? C46 C44 C43 109.7(5) . . ? O42 C44 C45 109.5(5) . . ? C46 C44 C45 110.2(5) . . ? C43 C44 C45 111.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C11 C12 C13 -67.5(5) . . . . ? C14 C11 C12 C13 176.8(4) . . . . ? C13 C11 C12 C13 54.3(6) 2_665 . . . ? C11 C12 C13 C11 -55.1(6) . . . 2_665 ? O1 C11 C14 F12 179.7(4) . . . . ? C13 C11 C14 F12 57.5(5) 2_665 . . . ? C12 C11 C14 F12 -65.2(5) . . . . ? O1 C11 C14 F11 64.2(5) . . . . ? C13 C11 C14 F11 -58.0(5) 2_665 . . . ? C12 C11 C14 F11 179.3(4) . . . . ? O1 C11 C14 C15B -37.3(12) . . . . ? C13 C11 C14 C15B -159.5(11) 2_665 . . . ? C12 C11 C14 C15B 77.9(12) . . . . ? O1 C11 C14 C15A -59.6(6) . . . . ? C13 C11 C14 C15A 178.2(5) 2_665 . . . ? C12 C11 C14 C15A 55.6(6) . . . . ? F12 C14 C15A F13A 40.6(6) . . . . ? F11 C14 C15A F13A 153.8(5) . . . . ? C11 C14 C15A F13A -82.7(6) . . . . ? C15B C14 C15A F13A 176(5) . . . . ? F12 C14 C15A C16A -77.4(8) . . . . ? F11 C14 C15A C16A 35.8(8) . . . . ? C11 C14 C15A C16A 159.2(6) . . . . ? C15B C14 C15A C16A 58(4) . . . . ? F13A C15A C16A F15 -70.8(7) . . . . ? C14 C15A C16A F15 49.2(10) . . . . ? F13A C15A C16A F16 51.3(7) . . . . ? C14 C15A C16A F16 171.3(6) . . . . ? F13A C15A C16A F14A 168.0(5) . . . . ? C14 C15A C16A F14A -72.0(8) . . . . ? F12 C14 C15B F13B -130(2) . . . . ? F11 C14 C15B F13B -22(3) . . . . ? C11 C14 C15B F13B 90(3) . . . . ? C15A C14 C15B F13B 179(7) . . . . ? F12 C14 C15B C16B -6(3) . . . . ? F11 C14 C15B C16B 102(2) . . . . ? C11 C14 C15B C16B -146.0(19) . . . . ? C15A C14 C15B C16B -57(3) . . . . ? F13B C15B C16B F16 -52(3) . . . . ? C14 C15B C16B F16 -179.8(17) . . . . ? F13B C15B C16B F14B -169(2) . . . . ? C14 C15B C16B F14B 64(3) . . . . ? F13B C15B C16B F15 68(2) . . . . ? C14 C15B C16B F15 -59(3) . . . . ? F16 C16A F15 C16B -67.1(19) . . . . ? F14A C16A F15 C16B 178(2) . . . . ? C15A C16A F15 C16B 56(2) . . . . ? F16 C16B F15 C16A 68.5(16) . . . . ? F14B C16B F15 C16A -178(3) . . . . ? C15B C16B F15 C16A -55.1(19) . . . . ? F14B C16B F16 C16A 176(3) . . . . ? F15 C16B F16 C16A -66.1(15) . . . . ? C15B C16B F16 C16A 56(3) . . . . ? F15 C16A F16 C16B 69.6(19) . . . . ? F14A C16A F16 C16B -175(2) . . . . ? C15A C16A F16 C16B -56(2) . . . . ? O2 C21 C22 C23 -68.2(5) . . . . ? C23 C21 C22 C23 53.4(6) 2_676 . . . ? C24 C21 C22 C23 175.7(4) . . . . ? C21 C22 C23 C21 -55.0(6) . . . 2_676 ? O2 C21 C24 F21 -177.5(4) . . . . ? C23 C21 C24 F21 62.3(6) 2_676 . . . ? C22 C21 C24 F21 -60.3(6) . . . . ? O2 C21 C24 F22 68.3(5) . . . . ? C23 C21 C24 F22 -51.9(6) 2_676 . . . ? C22 C21 C24 F22 -174.6(4) . . . . ? O2 C21 C24 C25 -50.3(7) . . . . ? C23 C21 C24 C25 -170.5(5) 2_676 . . . ? C22 C21 C24 C25 66.9(7) . . . . ? F21 C24 C25 F23 62.3(7) . . . . ? F22 C24 C25 F23 176.2(5) . . . . ? C21 C24 C25 F23 -63.5(7) . . . . ? F21 C24 C25 C26 -55.0(8) . . . . ? F22 C24 C25 C26 58.8(7) . . . . ? C21 C24 C25 C26 179.1(6) . . . . ? F23 C25 C26 F25 56.4(8) . . . . ? C24 C25 C26 F25 175.5(6) . . . . ? F23 C25 C26 F24 -65.2(8) . . . . ? C24 C25 C26 F24 54.0(9) . . . . ? F23 C25 C26 F26 176.7(6) . . . . ? C24 C25 C26 F26 -64.2(8) . . . . ? O3 C31 C32 C33 -61.8(5) . . . . ? C34 C31 C32 C33 178.9(4) . . . . ? C33 C31 C32 C33 55.7(6) 2_666 . . . ? C31 C32 C33 C31 -56.2(6) . . . 2_666 ? O3 C31 C34 F31 179.6(4) . . . . ? C32 C31 C34 F31 -58.2(5) . . . . ? C33 C31 C34 F31 63.6(6) 2_666 . . . ? O3 C31 C34 F32 -63.6(5) . . . . ? C32 C31 C34 F32 58.5(5) . . . . ? C33 C31 C34 F32 -179.7(4) 2_666 . . . ? O3 C31 C34 C35B 37.0(10) . . . . ? C32 C31 C34 C35B 159.2(9) . . . . ? C33 C31 C34 C35B -79.0(10) 2_666 . . . ? O3 C31 C34 C35A 60.7(6) . . . . ? C32 C31 C34 C35A -177.1(5) . . . . ? C33 C31 C34 C35A -55.3(6) 2_666 . . . ? F31 C34 C35A F33A -43.4(7) . . . . ? F32 C34 C35A F33A -157.1(5) . . . . ? C31 C34 C35A F33A 78.8(7) . . . . ? C35B C34 C35A F33A 172(3) . . . . ? F31 C34 C35A C36A 75.6(8) . . . . ? F32 C34 C35A C36A -38.1(9) . . . . ? C31 C34 C35A C36A -162.2(7) . . . . ? C35B C34 C35A C36A -69(3) . . . . ? F33A C35A C36A F36 -50.9(9) . . . . ? C34 C35A C36A F36 -172.3(6) . . . . ? F33A C35A C36A F34 74.2(9) . . . . ? C34 C35A C36A F34 -47.2(11) . . . . ? F33A C35A C36A F35A -166.8(6) . . . . ? C34 C35A C36A F35A 71.8(8) . . . . ? F31 C34 C35B F33B 134.2(13) . . . . ? F32 C34 C35B F33B 24.2(16) . . . . ? C31 C34 C35B F33B -87.7(17) . . . . ? C35A C34 C35B F33B 175(4) . . . . ? F31 C34 C35B C36B 14(2) . . . . ? F32 C34 C35B C36B -96.1(16) . . . . ? C31 C34 C35B C36B 152.1(14) . . . . ? C35A C34 C35B C36B 55(2) . . . . ? F33B C35B C36B F35B 174.8(18) . . . . ? C34 C35B C36B F35B -63(2) . . . . ? F33B C35B C36B F36 63(2) . . . . ? C34 C35B C36B F36 -175.0(15) . . . . ? F33B C35B C36B F34 -76(2) . . . . ? C34 C35B C36B F34 46(3) . . . . ? F36 C36A F34 C36B 77(3) . . . . ? F35A C36A F34 C36B -170(3) . . . . ? C35A C36A F34 C36B -48(2) . . . . ? F35B C36B F34 C36A -170(3) . . . . ? F36 C36B F34 C36A -71(2) . . . . ? C35B C36B F34 C36A 72(3) . . . . ? F34 C36A F36 C36B -76(3) . . . . ? F35A C36A F36 C36B 170(3) . . . . ? C35A C36A F36 C36B 50(2) . . . . ? F35B C36B F36 C36A 169(3) . . . . ? F34 C36B F36 C36A 71(2) . . . . ? C35B C36B F36 C36A -72(3) . . . . ? O41 C42 C43 C44 10.1(8) . . . . ? C41 C42 C43 C44 -170.4(5) . . . . ? C42 C43 C44 O42 -59.3(6) . . . . ? C42 C43 C44 C46 -175.1(5) . . . . ? C42 C43 C44 C45 62.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.487 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.083 #========================================================END