# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/408 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.' 'Fuss, Robert W.' 'Spink, Robert C.H.' 'Greenhall, Martin P.' 'Kenwright, Alan M.' 'Batsanov, Andrei S.' 'Howard, Judith A. K.' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2000' _ccdc_journal_depnumber '?' _publ_section_title ; Free radical reactions. Part 10. Addition of acyclic and cyclic alkanes to hexafluoropropene. ; #====================================================================== data_20a _audit_creation_method SHELXL _chemical_name_systematic ; 2R,2'S-trans-1,4-bis(2H-hexafluoropropyl)cyclohexane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H12 F12' _chemical_formula_weight 384.22 _chemical_melting_point '80-81 deg.C' _chemical_compound_source ? _ccdc_compound_id '20a' _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' '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 6.365(4) _cell_length_b 6.829(3) _cell_length_c 8.949(5) _cell_angle_alpha 71.54(4) _cell_angle_beta 82.58(6) _cell_angle_gamma 89.22(5) _cell_volume 365.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method ? _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rihaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\w/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15.9 _diffrn_reflns_number 655 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 19.99 _reflns_number_total 578 _reflns_number_observed 335 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'AFC (MSC, 1989)' _computing_cell_refinement 'AFC (MSC, 1989)' _computing_data_reduction TEXSAN _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. 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^)+(0.0550P)^2^+0.0828P] 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 578 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_obs 0.0373 _refine_ls_wR_factor_all 0.1181 _refine_ls_wR_factor_obs 0.0938 _refine_ls_goodness_of_fit_all 1.071 _refine_ls_goodness_of_fit_obs 1.184 _refine_ls_restrained_S_all 1.071 _refine_ls_restrained_S_obs 1.184 _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 C1 C 0.4209(8) 0.3648(8) 0.4156(5) 0.041(2) Uiso 1 d . . H1 H 0.5532(8) 0.3111(8) 0.3836(5) 0.050 Uiso 1 d R . C2 C 0.4370(8) 0.5998(9) 0.3428(6) 0.049(2) Uiso 1 d . . H2A H 0.3030(8) 0.6547(9) 0.3698(6) 0.058 Uiso 1 d R . H2B H 0.4633(8) 0.6350(9) 0.2292(6) 0.058 Uiso 1 d R . C3 C 0.3897(8) 0.3056(9) 0.5970(6) 0.051(2) Uiso 1 d . . H3A H 0.3900(8) 0.1580(9) 0.6423(6) 0.061 Uiso 1 d R . H3B H 0.2543(8) 0.3519(9) 0.6310(6) 0.061 Uiso 1 d R . C4 C 0.2488(9) 0.2691(10) 0.3578(7) 0.051(2) Uiso 1 d . . C5 C 0.2666(8) 0.3171(10) 0.1778(6) 0.048(2) Uiso 1 d . . H5 H 0.2460(8) 0.4620(10) 0.1303(6) 0.058 Uiso 1 d R . C6 C 0.1158(10) 0.1989(12) 0.1189(8) 0.063(2) Uiso 1 d . . F1 F 0.0545(4) 0.3335(5) 0.4039(4) 0.0695(12) Uani 1 d . . F2 F 0.2436(5) 0.0602(5) 0.4268(4) 0.0679(12) Uani 1 d . . F3 F 0.4680(5) 0.2765(6) 0.1225(4) 0.0843(14) Uani 1 d . . F4 F 0.1306(6) 0.2707(6) -0.0388(4) 0.099(2) Uani 1 d . . F5 F -0.0804(5) 0.2186(8) 0.1712(5) 0.115(2) Uani 1 d . . F6 F 0.1528(8) 0.0039(7) 0.1555(6) 0.133(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 F1 0.037(2) 0.088(3) 0.089(3) -0.040(2) 0.002(2) -0.001(2) F2 0.085(2) 0.043(3) 0.071(2) -0.009(2) -0.015(2) -0.010(2) F3 0.051(2) 0.144(4) 0.069(2) -0.052(2) 0.000(2) 0.003(2) F4 0.111(3) 0.125(4) 0.066(3) -0.032(3) -0.020(2) -0.029(3) F5 0.057(2) 0.188(5) 0.120(4) -0.074(3) -0.013(2) -0.023(3) F6 0.197(5) 0.063(4) 0.173(5) -0.051(3) -0.113(4) 0.018(3) _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.508(7) . ? C1 C2 1.528(7) . ? C1 C3 1.530(7) . ? C2 C3' 1.522(7) . ? C4 F2 1.362(7) . ? C4 F1 1.364(6) . ? C4 C5 1.528(7) . ? C5 F3 1.371(6) . ? C5 C6 1.507(8) . ? C6 F6 1.293(7) . ? C6 F5 1.297(7) . ? C6 F4 1.330(7) . ? 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 C4 C1 C2 112.8(4) . . ? C4 C1 C3 111.3(4) . . ? C2 C1 C3 109.6(5) . . ? C3' C2 C1 112.2(4) . . ? C2' C3 C1 111.9(4) . . ? F2 C4 F1 105.9(5) . . ? F2 C4 C1 109.7(5) . . ? F1 C4 C1 110.6(5) . . ? F2 C4 C5 108.5(5) . . ? F1 C4 C5 106.3(4) . . ? C1 C4 C5 115.4(5) . . ? F3 C5 C6 107.2(5) . . ? F3 C5 C4 108.7(4) . . ? C6 C5 C4 116.3(5) . . ? F6 C6 F5 108.0(7) . . ? F6 C6 F4 106.4(6) . . ? F5 C6 F4 106.0(6) . . ? F6 C6 C5 113.4(6) . . ? F5 C6 C5 112.2(6) . . ? F4 C6 C5 110.4(6) . . ? 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 C4 C1 C2 C3' 179.6(5) . . . . ? C3 C1 C2 C3' 55.1(6) . . . . ? C4 C1 C3 C2' 179.7(5) . . . . ? C2 C1 C3 C2' -54.9(6) . . . . ? C2 C1 C4 F2 179.8(4) . . . . ? C3 C1 C4 F2 -56.5(6) . . . . ? C2 C1 C4 F1 -63.7(6) . . . . ? C3 C1 C4 F1 59.9(6) . . . . ? C2 C1 C4 C5 56.9(7) . . . . ? C3 C1 C4 C5 -179.4(5) . . . . ? F2 C4 C5 F3 -73.1(6) . . . . ? F1 C4 C5 F3 173.4(5) . . . . ? C1 C4 C5 F3 50.4(7) . . . . ? F2 C4 C5 C6 47.9(7) . . . . ? F1 C4 C5 C6 -65.6(7) . . . . ? C1 C4 C5 C6 171.4(6) . . . . ? F3 C5 C6 F6 54.1(7) . . . . ? C4 C5 C6 F6 -67.7(8) . . . . ? F3 C5 C6 F5 176.9(5) . . . . ? C4 C5 C6 F5 55.0(8) . . . . ? F3 C5 C6 F4 -65.2(7) . . . . ? C4 C5 C6 F4 173.0(5) . . . . ? _refine_diff_density_max 0.145 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.046 #=================================================END data_34 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5,7-tetrakis(2H-hexafluoropropyl)adamantane ; _chemical_name_common ? _chemical_melting_point '110-112 deg. C' _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 F24' _chemical_formula_weight 736.35 _ccdc_compound_id '34' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; Atoms C8 to C13, H9, F2 to F8, F10, F11, F12 are disordered each between two positions, related via mirror plane. F9 is disordeered over four positions, A (occupancy 15%), B (35%) and their mirror equivalents. Atoms C15, C16, F13 are disordered over two positions: A (70%) and B (30%). F15, F16, F17, F18 are disordered over three positions: A (50%), B (30%) and C (20%), which are symmetrically unrelated. ; _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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.442(8) _cell_length_b 14.992(14) _cell_length_c 15.011(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2575(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 510 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 18.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8503 _exptl_absorpt_correction_T_max 0.9771 _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 1.00 0.00 0.00 0.3600 -1.00 0.00 0.00 0.3600 0.00 -1.00 -1.00 0.0550 0.00 1.00 1.00 0.0550 0.00 -1.00 1.00 0.0500 0.00 1.00 -1.00 0.0500 _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 (20 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 111 duplicate reflections. Crystal to detector distance 4.51 cm. Five sets of data (besides the present one) were collected on different crystals: three at room temperature with 4-circle diffractometers, one room temperature and one low temperature with a CCD area detector. All displayed the same complicated disorder and gave poorer refinements. ; _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_% 0.1 _diffrn_reflns_number 10933 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.44 _reflns_number_total 2348 _reflns_number_gt 1558 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.1576P)^2^+14.1603P] 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 2348 _refine_ls_number_parameters 250 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1636 _refine_ls_R_factor_gt 0.1190 _refine_ls_wR_factor_ref 0.3570 _refine_ls_wR_factor_gt 0.3075 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.065 _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 C1 C 0.5789(7) 0.2500 0.4405(6) 0.049(2) Uani 1 2 d S . . C2 C 0.5888(8) 0.2500 0.5437(6) 0.055(3) Uani 1 2 d S . . H22 H 0.6361 0.3022 0.5659 0.071 Uiso 0.50 1 d PR . . C3 C 0.4625(8) 0.2500 0.5821(6) 0.057(3) Uani 1 2 d S . . C4 C 0.3979(5) 0.3336(5) 0.5494(4) 0.0516(18) Uani 1 1 d . . . H41 H 0.4388 0.3882 0.5698 0.067 Uiso 1 1 d R . . H42 H 0.3182 0.3341 0.5753 0.067 Uiso 1 1 d R . . C5 C 0.3893(5) 0.3338(4) 0.4469(4) 0.0430(16) Uani 1 1 d . A . C6 C 0.3240(7) 0.2500 0.4159(6) 0.039(2) Uani 1 2 d S . . H61 H 0.3180 0.2500 0.3501 0.051 Uiso 1 2 d SR . . H62 H 0.2438 0.2500 0.4409 0.051 Uiso 1 2 d SR . . C7 C 0.5139(6) 0.3332(5) 0.4080(4) 0.0484(17) Uani 1 1 d . . . H71 H 0.5564 0.3876 0.4269 0.063 Uiso 1 1 d R . . H72 H 0.5104 0.3327 0.3420 0.063 Uiso 1 1 d R . . C8 C 0.7043(9) 0.2302(7) 0.4005(7) 0.040(3) Uiso 0.50 1 d P . . C9 C 0.7957(14) 0.2977(12) 0.4287(11) 0.060(4) Uiso 0.50 1 d P . . H9 H 0.7965 0.2985 0.4954 0.078 Uiso 0.50 1 d PR . . C10 C 0.9201(16) 0.2764(10) 0.3952(12) 0.069(5) Uiso 0.50 1 d P . . C11 C 0.4656(9) 0.2259(6) 0.6835(7) 0.036(3) Uiso 0.50 1 d P . . C12 C 0.5392(14) 0.2897(10) 0.7384(10) 0.061(4) Uiso 0.50 1 d P . . C13 C 0.5377(14) 0.2761(9) 0.8392(11) 0.057(5) Uiso 0.50 1 d P . . F1 F 0.6945(5) 0.2500 0.3089(3) 0.078(2) Uani 1 2 d S . . F2 F 0.7550(9) 0.1514(8) 0.4222(7) 0.068(3) Uiso 0.50 1 d P . . F3 F 0.7606(11) 0.3823(9) 0.3937(9) 0.091(4) Uiso 0.50 1 d P . . F4 F 0.9636(14) 0.2047(16) 0.4356(11) 0.119(10) Uani 0.50 1 d P . . F5 F 0.9927(17) 0.3424(18) 0.4163(15) 0.140(9) Uani 0.50 1 d P . . F6 F 0.9279(6) 0.265(5) 0.3108(5) 0.112(17) Uani 0.50 1 d P . . F7 F 0.3544(5) 0.2275(4) 0.7155(4) 0.0435(18) Uiso 0.50 1 d P . . F8 F 0.5171(13) 0.1450(10) 0.7113(10) 0.069(5) Uiso 0.50 1 d P . . F9A F 0.639(2) 0.3106(18) 0.7135(17) 0.056(6) Uiso 0.15 1 d P . 1 F9B F 0.4987(17) 0.3723(13) 0.7141(13) 0.062(6) Uiso 0.35 1 d P . 2 F10 F 0.4322(7) 0.272(3) 0.8726(5) 0.096(13) Uani 0.50 1 d P . . F11 F 0.592(3) 0.200(2) 0.8587(14) 0.116(9) Uani 0.50 1 d P . . F12 F 0.599(3) 0.339(2) 0.8787(14) 0.113(8) Uani 0.50 1 d P . . C14 C 0.3221(6) 0.4180(5) 0.4173(5) 0.0593(19) Uani 1 1 d D . . C15A C 0.2935(18) 0.4319(15) 0.3204(12) 0.093(7) Uiso 0.70 1 d P A 1 H15A H 0.2623 0.3749 0.2949 0.121 Uiso 0.70 1 d PR A 1 C16A C 0.2133(11) 0.5115(8) 0.2976(7) 0.079(4) Uiso 0.70 1 d PD A 1 F13A F 0.2131(6) 0.4161(5) 0.4607(5) 0.0659(19) Uiso 0.70 1 d PD A 1 F15A F 0.4048(10) 0.4622(8) 0.2869(7) 0.088(3) Uiso 0.50 1 d P A 1 F15C F 0.355(3) 0.409(2) 0.277(2) 0.093(8) Uiso 0.20 1 d P A 1 F16A F 0.2258(12) 0.5798(7) 0.3486(8) 0.076(3) Uiso 0.50 1 d PD A 1 F17A F 0.1198(15) 0.4718(12) 0.2952(11) 0.117(7) Uiso 0.50 1 d PD A 1 F18A F 0.2392(13) 0.5338(9) 0.2149(7) 0.110(4) Uiso 0.50 1 d PD A 1 F16C F 0.1113(19) 0.5127(19) 0.3423(16) 0.089(8) Uiso 0.20 1 d PD A 1 F17C F 0.2604(19) 0.5886(12) 0.3169(15) 0.070(7) Uiso 0.20 1 d PD A 1 F18C F 0.1844(18) 0.5136(13) 0.2149(9) 0.054(5) Uiso 0.20 1 d PD A 1 C15B C 0.1995(16) 0.434(2) 0.426(2) 0.062(8) Uiso 0.30 1 d PD A 2 H15B H 0.1559 0.3776 0.4134 0.081 Uiso 0.30 1 d PR A 2 C16B C 0.125(2) 0.5064(19) 0.386(2) 0.16(2) Uiso 0.30 1 d PD A 2 F13B F 0.333(2) 0.4257(15) 0.3255(8) 0.075(6) Uiso 0.30 1 d PD A 2 F15B F 0.209(3) 0.464(2) 0.516(2) 0.154(10) Uiso 0.30 1 d P A 2 F16B F 0.183(2) 0.5680(18) 0.3747(18) 0.128(10) Uiso 0.30 1 d PD A 2 F17B F 0.039(3) 0.526(2) 0.421(2) 0.193(14) Uiso 0.30 1 d PD A 2 F18B F 0.102(2) 0.470(2) 0.3207(19) 0.102(9) Uiso 0.30 1 d PD A 2 F14 F 0.3797(5) 0.4921(3) 0.4499(4) 0.0941(19) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(4) 0.091(7) 0.032(4) 0.000 -0.003(3) 0.000 C2 0.026(4) 0.104(8) 0.035(5) 0.000 0.002(4) 0.000 C3 0.030(5) 0.111(9) 0.029(4) 0.000 0.000(4) 0.000 C4 0.034(3) 0.082(5) 0.038(3) -0.015(3) 0.000(3) -0.004(3) C5 0.039(3) 0.050(4) 0.040(3) -0.008(3) -0.002(3) -0.006(3) C6 0.034(4) 0.047(5) 0.037(4) 0.000 -0.004(4) 0.000 C7 0.044(4) 0.064(4) 0.037(3) -0.001(3) -0.009(3) -0.010(3) F1 0.043(3) 0.162(7) 0.028(3) 0.000 0.004(2) 0.000 F4 0.043(7) 0.24(3) 0.077(8) 0.059(12) 0.014(6) 0.022(9) F5 0.054(10) 0.22(2) 0.144(16) -0.029(14) 0.013(8) -0.051(10) F6 0.047(4) 0.25(5) 0.038(4) 0.045(19) 0.014(3) 0.008(12) F10 0.058(4) 0.19(4) 0.040(4) 0.001(7) 0.005(3) 0.012(8) F11 0.102(10) 0.20(3) 0.046(10) 0.009(9) -0.016(9) 0.063(14) F12 0.105(11) 0.20(3) 0.036(8) -0.022(9) -0.019(7) -0.039(15) C14 0.058(4) 0.052(4) 0.068(5) -0.019(4) -0.014(4) -0.007(4) F14 0.096(4) 0.055(3) 0.132(5) -0.024(3) -0.037(3) -0.012(3) _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7 1.532(8) 7_565 ? C1 C7 1.532(8) . ? C1 C2 1.553(12) . ? C1 C8 1.583(13) 7_565 ? C1 C8 1.583(13) . ? C2 C3 1.555(12) . ? C3 C4 1.535(9) 7_565 ? C3 C4 1.535(9) . ? C3 C11 1.565(13) 7_565 ? C3 C11 1.565(13) . ? C4 C5 1.543(8) . ? C5 C6 1.534(8) . ? C5 C7 1.540(9) . ? C5 C14 1.543(10) . ? C6 C5 1.534(8) 7_565 ? C8 C8 0.59(2) 7_565 ? C8 C9 1.203(18) 7_565 ? C8 F2 1.355(15) . ? C8 F1 1.412(12) . ? C8 C9 1.515(19) . ? C8 F3 1.808(18) 7_565 ? C8 F2 1.895(16) 7_565 ? C9 F2 0.899(16) 7_565 ? C9 C8 1.203(18) 7_565 ? C9 F3 1.43(2) . ? C9 C9 1.43(3) 7_565 ? C9 C10 1.54(2) . ? C9 C10 1.87(2) 7_565 ? C10 C10 0.79(3) 7_565 ? C10 F4 0.83(2) 7_565 ? C10 F6 1.28(2) . ? C10 F5 1.33(3) . ? C10 F4 1.33(2) . ? C10 F6 1.42(4) 7_565 ? C10 C9 1.87(2) 7_565 ? C11 C11 0.721(19) 7_565 ? C11 C12 1.201(18) 7_565 ? C11 F7 1.361(12) . ? C11 F8 1.412(17) . ? C11 C12 1.517(18) . ? C11 F7 1.529(12) 7_565 ? C11 F9B 1.59(2) 7_565 ? C12 F8 1.090(17) 7_565 ? C12 C12 1.19(3) 7_565 ? C12 C11 1.201(18) 7_565 ? C12 F9A 1.24(3) . ? C12 F9B 1.37(3) . ? C12 C13 1.53(2) . ? C12 C13 1.81(2) 7_565 ? C13 C13 0.78(3) 7_565 ? C13 F11 0.78(2) 7_565 ? C13 F10 1.310(17) . ? C13 F12 1.32(2) . ? C13 F11 1.33(3) . ? C13 F10 1.49(3) 7_565 ? C13 C12 1.81(2) 7_565 ? F1 C8 1.412(12) 7_565 ? F2 F3 0.666(14) 7_565 ? F2 C9 0.899(16) 7_565 ? F2 C8 1.895(16) 7_565 ? F3 F2 0.666(14) 7_565 ? F3 C8 1.808(18) 7_565 ? F4 F5 0.83(3) 7_565 ? F4 C10 0.83(2) 7_565 ? F4 F4 1.36(5) 7_565 ? F5 F4 0.83(3) 7_565 ? F6 F6 0.46(15) 7_565 ? F6 C10 1.42(4) 7_565 ? F7 F7 0.673(11) 7_565 ? F7 C11 1.529(12) 7_565 ? F8 F9B 0.34(3) 7_565 ? F8 C12 1.090(17) 7_565 ? F8 F9A 1.54(3) 7_565 ? F9A F8 1.54(3) 7_565 ? F9B F8 0.34(3) 7_565 ? F9B C11 1.59(2) 7_565 ? F10 F10 0.65(8) 7_565 ? F10 C13 1.49(3) 7_565 ? F11 F12 0.67(4) 7_565 ? F11 C13 0.78(2) 7_565 ? F11 F11 1.50(7) 7_565 ? F12 F11 0.67(4) 7_565 ? C14 F14 1.381(8) . ? C14 F13B 1.389(10) . ? C14 F13A 1.407(8) . ? C14 C15B 1.429(18) . ? C14 C15A 1.51(2) . ? C15A F15C 1.02(3) . ? C15A F15A 1.44(2) . ? C15A C16A 1.54(2) . ? C16A F17A 1.225(13) . ? C16A F16A 1.286(12) . ? C16A F18C 1.286(14) . ? C16A F17C 1.309(15) . ? C16A F18A 1.319(12) . ? C16A F16C 1.345(15) . ? F15A F15C 0.98(3) . ? F16A F17C 0.63(2) . ? F16A F16C 1.65(2) . ? F17A F16C 0.94(3) . ? F17A F18C 1.55(2) . ? F18A F18C 0.70(2) . ? F18A F17C 1.75(2) . ? C15B F15B 1.42(4) . ? C15B C16B 1.51(2) . ? C16B F16B 1.15(2) . ? C16B F18B 1.15(3) . ? C16B F17B 1.15(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 C7 C1 C7 109.0(7) 7_565 . ? C7 C1 C2 110.7(5) 7_565 . ? C7 C1 C2 110.7(5) . . ? C7 C1 C8 118.2(6) 7_565 7_565 ? C7 C1 C8 99.6(6) . 7_565 ? C2 C1 C8 108.2(7) . 7_565 ? C7 C1 C8 99.6(5) 7_565 . ? C7 C1 C8 118.2(6) . . ? C2 C1 C8 108.2(7) . . ? C8 C1 C8 21.6(8) 7_565 . ? C1 C2 C3 107.6(7) . . ? C4 C3 C4 109.5(7) 7_565 . ? C4 C3 C2 109.2(5) 7_565 . ? C4 C3 C2 109.2(5) . . ? C4 C3 C11 120.6(6) 7_565 7_565 ? C4 C3 C11 97.7(5) . 7_565 ? C2 C3 C11 109.8(7) . 7_565 ? C4 C3 C11 97.7(5) 7_565 . ? C4 C3 C11 120.6(6) . . ? C2 C3 C11 109.8(7) . . ? C11 C3 C11 26.6(7) 7_565 . ? C3 C4 C5 110.5(6) . . ? C6 C5 C7 109.3(6) . . ? C6 C5 C4 109.4(6) . . ? C7 C5 C4 108.6(5) . . ? C6 C5 C14 109.8(5) . . ? C7 C5 C14 111.0(5) . . ? C4 C5 C14 108.7(5) . . ? C5 C6 C5 110.0(7) 7_565 . ? C1 C7 C5 109.5(6) . . ? C8 C8 C9 110.3(10) 7_565 7_565 ? C8 C8 F2 150.6(7) 7_565 . ? C9 C8 F2 40.6(8) 7_565 . ? C8 C8 F1 77.9(4) 7_565 . ? C9 C8 F1 119.0(11) 7_565 . ? F2 C8 F1 116.8(9) . . ? C8 C8 C9 48.1(8) 7_565 . ? C9 C8 C9 62.2(16) 7_565 . ? F2 C8 C9 102.7(12) . . ? F1 C8 C9 100.7(9) . . ? C8 C8 C1 79.2(4) 7_565 . ? C9 C8 C1 136.0(12) 7_565 . ? F2 C8 C1 117.4(9) . . ? F1 C8 C1 105.0(7) . . ? C9 C8 C1 113.2(9) . . ? C8 C8 F3 158.9(5) 7_565 7_565 ? C9 C8 F3 52.1(10) 7_565 7_565 ? F2 C8 F3 17.9(6) . 7_565 ? F1 C8 F3 99.7(7) . 7_565 ? C9 C8 F3 113.1(10) . 7_565 ? C1 C8 F3 121.3(7) . 7_565 ? C8 C8 F2 20.5(5) 7_565 7_565 ? C9 C8 F2 89.9(12) 7_565 7_565 ? F2 C8 F2 130.1(11) . 7_565 ? F1 C8 F2 89.7(6) . 7_565 ? C9 C8 F2 27.8(7) . 7_565 ? C1 C8 F2 92.1(6) . 7_565 ? F3 C8 F2 140.7(8) 7_565 7_565 ? F2 C9 C8 78.8(15) 7_565 7_565 ? F2 C9 F3 20.4(11) 7_565 . ? C8 C9 F3 86.3(13) 7_565 . ? F2 C9 C9 148.0(13) 7_565 7_565 ? C8 C9 C9 69.7(10) 7_565 7_565 ? F3 C9 C9 152.5(8) . 7_565 ? F2 C9 C8 100.3(16) 7_565 . ? C8 C9 C8 21.6(8) 7_565 . ? F3 C9 C8 107.2(12) . . ? C9 C9 C8 48.1(8) 7_565 . ? F2 C9 C10 128.1(18) 7_565 . ? C8 C9 C10 128.0(15) 7_565 . ? F3 C9 C10 108.8(13) . . ? C9 C9 C10 78.1(9) 7_565 . ? C8 C9 C10 114.1(13) . . ? F2 C9 C10 150.1(18) 7_565 7_565 ? C8 C9 C10 111.1(13) 7_565 7_565 ? F3 C9 C10 129.8(13) . 7_565 ? C9 C9 C10 53.6(7) 7_565 7_565 ? C8 C9 C10 93.0(11) . 7_565 ? C10 C9 C10 24.4(10) . 7_565 ? C10 C10 F4 110(2) 7_565 7_565 ? C10 C10 F6 82(3) 7_565 . ? F4 C10 F6 136(3) 7_565 . ? C10 C10 F5 138.0(15) 7_565 . ? F4 C10 F5 37(2) 7_565 . ? F6 C10 F5 107(3) . . ? C10 C10 F4 36.1(13) 7_565 . ? F4 C10 F4 74(3) 7_565 . ? F6 C10 F4 109(3) . . ? F5 C10 F4 105.0(17) . . ? C10 C10 F6 64(3) 7_565 7_565 ? F4 C10 F6 140(2) 7_565 7_565 ? F6 C10 F6 19(6) . 7_565 ? F5 C10 F6 120(2) . 7_565 ? F4 C10 F6 92(3) . 7_565 ? C10 C10 C9 101.9(9) 7_565 . ? F4 C10 C9 104.1(19) 7_565 . ? F6 C10 C9 114.5(16) . . ? F5 C10 C9 110.2(17) . . ? F4 C10 C9 111.3(15) . . ? F6 C10 C9 116.2(15) 7_565 . ? C10 C10 C9 53.6(7) 7_565 7_565 ? F4 C10 C9 117(2) 7_565 7_565 ? F6 C10 C9 104(2) . 7_565 ? F5 C10 C9 148.3(17) . 7_565 ? F4 C10 C9 71.5(11) . 7_565 ? F6 C10 C9 92(2) 7_565 7_565 ? C9 C10 C9 48.3(12) . 7_565 ? C11 C11 C12 101.3(9) 7_565 7_565 ? C11 C11 F7 89.0(5) 7_565 . ? C12 C11 F7 114.7(11) 7_565 . ? C11 C11 F8 149.3(8) 7_565 . ? C12 C11 F8 48.5(9) 7_565 . ? F7 C11 F8 107.5(9) . . ? C11 C11 C12 50.9(7) 7_565 . ? C12 C11 C12 50.3(14) 7_565 . ? F7 C11 C12 108.5(9) . . ? F8 C11 C12 98.6(12) . . ? C11 C11 F7 62.9(4) 7_565 7_565 ? C12 C11 F7 117.2(11) 7_565 7_565 ? F7 C11 F7 26.1(5) . 7_565 ? F8 C11 F7 130.3(10) . 7_565 ? C12 C11 F7 90.2(8) . 7_565 ? C11 C11 C3 76.7(4) 7_565 . ? C12 C11 C3 136.7(12) 7_565 . ? F7 C11 C3 108.5(8) . . ? F8 C11 C3 119.7(9) . . ? C12 C11 C3 113.3(9) . . ? F7 C11 C3 100.4(7) 7_565 . ? C11 C11 F9B 158.0(8) 7_565 7_565 ? C12 C11 F9B 56.9(11) 7_565 7_565 ? F7 C11 F9B 97.9(10) . 7_565 ? F8 C11 F9B 11.0(10) . 7_565 ? C12 C11 F9B 107.2(11) . 7_565 ? F7 C11 F9B 122.0(10) 7_565 7_565 ? C3 C11 F9B 120.0(9) . 7_565 ? F8 C12 C12 154.0(11) 7_565 7_565 ? F8 C12 C11 76.0(14) 7_565 7_565 ? C12 C12 C11 78.7(9) 7_565 7_565 ? F8 C12 F9A 82.8(18) 7_565 . ? C12 C12 F9A 104.6(14) 7_565 . ? C11 C12 F9A 119.2(18) 7_565 . ? F8 C12 F9B 8.7(14) 7_565 . ? C12 C12 F9B 154.5(10) 7_565 . ? C11 C12 F9B 76.0(12) 7_565 . ? F9A C12 F9B 90.2(18) . . ? F8 C12 C11 103.6(15) 7_565 . ? C12 C12 C11 50.9(7) 7_565 . ? C11 C12 C11 27.8(8) 7_565 . ? F9A C12 C11 120.4(17) . . ? F9B C12 C11 103.7(13) . . ? F8 C12 C13 119.1(15) 7_565 . ? C12 C12 C13 82.3(8) 7_565 . ? C11 C12 C13 130.2(15) 7_565 . ? F9A C12 C13 110.0(17) . . ? F9B C12 C13 112.3(13) . . ? C11 C12 C13 116.6(12) . . ? F8 C12 C13 143.2(16) 7_565 7_565 ? C12 C12 C13 56.9(7) 7_565 7_565 ? C11 C12 C13 117.5(13) 7_565 7_565 ? F9A C12 C13 113.5(17) . 7_565 ? F9B C12 C13 135.4(14) . 7_565 ? C11 C12 C13 96.1(10) . 7_565 ? C13 C12 C13 25.4(10) . 7_565 ? C13 C13 F11 117(3) 7_565 7_565 ? C13 C13 F10 87.2(19) 7_565 . ? F11 C13 F10 128(3) 7_565 . ? C13 C13 F12 136.0(18) 7_565 . ? F11 C13 F12 22(4) 7_565 . ? F10 C13 F12 111(2) . . ? C13 C13 F11 31.3(18) 7_565 . ? F11 C13 F11 86(5) 7_565 . ? F10 C13 F11 108(2) . . ? F12 C13 F11 105.5(14) . . ? C13 C13 F10 61.3(14) 7_565 7_565 ? F11 C13 F10 138(2) 7_565 7_565 ? F10 C13 F10 26(3) . 7_565 ? F12 C13 F10 128.6(19) . 7_565 ? F11 C13 F10 84(2) . 7_565 ? C13 C13 C12 97.7(8) 7_565 . ? F11 C13 C12 108(2) 7_565 . ? F10 C13 C12 113.3(14) . . ? F12 C13 C12 110.1(18) . . ? F11 C13 C12 109.1(15) . . ? F10 C13 C12 114.0(13) 7_565 . ? C13 C13 C12 56.9(7) 7_565 7_565 ? F11 C13 C12 124(3) 7_565 7_565 ? F10 C13 C12 107.6(15) . 7_565 ? F12 C13 C12 139.9(17) . 7_565 ? F11 C13 C12 73.3(14) . 7_565 ? F10 C13 C12 91.5(13) 7_565 7_565 ? C12 C13 C12 40.8(11) . 7_565 ? C8 F1 C8 24.3(9) 7_565 . ? F3 F2 C9 132(2) 7_565 7_565 ? F3 F2 C8 123.3(19) 7_565 . ? C9 F2 C8 60.5(13) 7_565 . ? F3 F2 C8 129.1(18) 7_565 7_565 ? C9 F2 C8 51.9(12) 7_565 7_565 ? C8 F2 C8 8.8(4) . 7_565 ? F2 F3 C9 28.0(14) 7_565 . ? F2 F3 C8 38.8(14) 7_565 7_565 ? C9 F3 C8 41.6(8) . 7_565 ? F5 F4 C10 106(4) 7_565 7_565 ? F5 F4 C10 133(3) 7_565 . ? C10 F4 C10 34.1(16) 7_565 . ? F5 F4 F4 148(3) 7_565 7_565 ? C10 F4 F4 70(2) 7_565 7_565 ? C10 F4 F4 36.1(13) . 7_565 ? F4 F5 C10 37.1(19) 7_565 . ? F6 F6 C10 98(3) 7_565 . ? F6 F6 C10 64(3) 7_565 7_565 ? C10 F6 C10 33.7(14) . 7_565 ? F7 F7 C11 91.0(5) 7_565 . ? F7 F7 C11 62.9(4) 7_565 7_565 ? C11 F7 C11 28.2(8) . 7_565 ? F9B F8 C12 142(6) 7_565 7_565 ? F9B F8 C11 116(6) 7_565 . ? C12 F8 C11 55.6(11) 7_565 . ? F9B F8 F9A 153(6) 7_565 7_565 ? C12 F8 F9A 52.8(14) 7_565 7_565 ? C11 F8 F9A 90.7(14) . 7_565 ? C12 F9A F8 44.4(11) . 7_565 ? F8 F9B C12 29(5) 7_565 . ? F8 F9B C11 53(5) 7_565 7_565 ? C12 F9B C11 47.2(9) . 7_565 ? F10 F10 C13 92.8(18) 7_565 . ? F10 F10 C13 61.3(14) 7_565 7_565 ? C13 F10 C13 31.6(12) . 7_565 ? F12 F11 C13 132(8) 7_565 7_565 ? F12 F11 C13 155(6) 7_565 . ? C13 F11 C13 31.4(17) 7_565 . ? F12 F11 F11 152(5) 7_565 7_565 ? C13 F11 F11 63(3) 7_565 7_565 ? C13 F11 F11 31.3(18) . 7_565 ? F11 F12 C13 26(4) 7_565 . ? F14 C14 F13B 103.9(11) . . ? F14 C14 F13A 106.0(6) . . ? F13B C14 F13A 122.9(12) . . ? F14 C14 C15B 107.4(13) . . ? F13B C14 C15B 99.7(17) . . ? F13A C14 C15B 24.6(12) . . ? F14 C14 C15A 109.5(10) . . ? F13B C14 C15A 18.2(12) . . ? F13A C14 C15A 104.9(9) . . ? C15B C14 C15A 81.6(15) . . ? F14 C14 C5 108.5(5) . . ? F13B C14 C5 107.9(11) . . ? F13A C14 C5 107.1(6) . . ? C15B C14 C5 126.9(14) . . ? C15A C14 C5 120.0(10) . . ? F15C C15A F15A 43.0(19) . . ? F15C C15A C14 115(3) . . ? F15A C15A C14 100.9(13) . . ? F15C C15A C16A 122(2) . . ? F15A C15A C16A 101.8(14) . . ? C14 C15A C16A 116.8(14) . . ? F17A C16A F16A 120.1(13) . . ? F17A C16A F18C 76.1(12) . . ? F16A C16A F18C 125.7(15) . . ? F17A C16A F17C 142.7(17) . . ? F16A C16A F17C 28.2(10) . . ? F18C C16A F17C 107.3(13) . . ? F17A C16A F18A 107.0(11) . . ? F16A C16A F18A 109.4(11) . . ? F18C C16A F18A 31.0(9) . . ? F17C C16A F18A 83.8(12) . . ? F17A C16A F16C 42.6(13) . . ? F16A C16A F16C 77.8(13) . . ? F18C C16A F16C 104.9(13) . . ? F17C C16A F16C 103.6(13) . . ? F18A C16A F16C 131.3(17) . . ? F17A C16A C15A 98.6(15) . . ? F16A C16A C15A 114.6(12) . . ? F18C C16A C15A 112.7(14) . . ? F17C C16A C15A 112.9(15) . . ? F18A C16A C15A 105.7(12) . . ? F16C C16A C15A 114.6(17) . . ? F15C F15A C15A 45(2) . . ? F15A F15C C15A 92(3) . . ? F17C F16A C16A 77.9(15) . . ? F17C F16A F16C 125.4(19) . . ? C16A F16A F16C 52.7(9) . . ? F16C F17A C16A 75.5(13) . . ? F16C F17A F18C 111.7(17) . . ? C16A F17A F18C 53.8(8) . . ? F18C F18A C16A 71.9(13) . . ? F18C F18A F17C 109.2(16) . . ? C16A F18A F17C 47.9(7) . . ? F17A F16C C16A 61.8(10) . . ? F17A F16C F16A 111.0(12) . . ? C16A F16C F16A 49.5(7) . . ? F16A F17C C16A 73.9(15) . . ? F16A F17C F18A 118.1(17) . . ? C16A F17C F18A 48.4(7) . . ? F18A F18C C16A 77.2(14) . . ? F18A F18C F17A 127.2(17) . . ? C16A F18C F17A 50.2(8) . . ? C14 C15B F15B 94(2) . . ? C14 C15B C16B 130(2) . . ? F15B C15B C16B 101(2) . . ? F16B C16B F18B 112(3) . . ? F16B C16B F17B 111(2) . . ? F18B C16B F17B 108(2) . . ? F16B C16B C15B 108(3) . . ? F18B C16B C15B 98(3) . . ? F17B C16B C15B 119(3) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.44 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.615 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.098 #=================================================END data_41a _audit_creation_method SHELXL _chemical_name_systematic ; trans-1,4-bis(Z-pentafluoroprop-2-enyl)cyclohexane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H10 F10' _chemical_formula_weight 344.20 _chemical_melting_point '101-102 deg.C' _chemical_compound_source ? _ccdc_compound_id '41a' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder ; CF3 group is severely disordered. It was refined in two orientations (A and B) opposite with respect to the rotation arownd C(4)-C(5) bond, with a 2:1 occupancy ratio. For both orientations, the F(3) is situated on the mirror plane, and two other fluorine atoms, F(4) and F(4'), are related via this plane. However, very large displacement parameters of all F atoms suggest further 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' '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 'C2/m ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 15.006(13) _cell_length_b 7.217(4) _cell_length_c 6.223(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.74(7) _cell_angle_gamma 90.00 _cell_volume 657.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 11.9 _cell_measurement_theta_max 13.6 _exptl_crystal_description Bulk _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method ? _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _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 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method 'Lehmann-Larsen \w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 1042 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 27.49 _reflns_number_total 816 _reflns_number_observed 672 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'AFC (MSC, 1989)' _computing_cell_refinement 'AFC (MSC, 1989)' _computing_data_reduction 'TEXSAN' _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. 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^)+(0.0469P)^2^+0.7858P] 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 0.068(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 816 _refine_ls_number_parameters 88 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_obs 0.0441 _refine_ls_wR_factor_all 0.1142 _refine_ls_wR_factor_obs 0.1084 _refine_ls_goodness_of_fit_all 1.069 _refine_ls_goodness_of_fit_obs 1.132 _refine_ls_restrained_S_all 1.083 _refine_ls_restrained_S_obs 1.147 _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 C1 C 0.09304(14) 0.0000 0.1452(4) 0.0292(6) Uani 1 d S . H1 H 0.1308(16) 0.0000 0.0368(39) 0.024(6) Uiso 1 d S . C2 C 0.03316(11) 0.1751(3) 0.1126(3) 0.0319(4) Uani 1 d . . H2A H 0.0720(13) 0.2856(31) 0.1309(30) 0.039(5) Uiso 1 d . . H2B H -0.0010(12) 0.1802(30) 0.2311(31) 0.038(5) Uiso 1 d . . C3 C 0.1551(2) 0.0000 0.3687(4) 0.0318(6) Uani 1 d S . C4 C 0.2451(2) 0.0000 0.4303(4) 0.0297(6) Uani 1 d S . C5 C 0.3128(2) 0.0000 0.2869(4) 0.0377(6) Uani 1 d SD . F1 F 0.11002(10) 0.0000 0.5348(2) 0.0544(6) Uani 1 d S . F2 F 0.28685(10) 0.0000 0.6461(2) 0.0448(5) Uani 1 d S . F3A F 0.3015(2) 0.1429(4) 0.1497(6) 0.0829(9) Uani 0.66 d PD . F4A F 0.3965(2) 0.0000 0.3932(7) 0.097(2) Uani 0.66 d SPD . F3B F 0.3657(4) 0.1450(8) 0.3400(12) 0.111(3) Uani 0.34 d PD . F4B F 0.2834(4) 0.0000 0.0875(9) 0.087(3) Uani 0.34 d SPD . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0215(10) 0.0408(14) 0.0262(11) 0.000 0.0073(8) 0.000 C2 0.0281(8) 0.0344(9) 0.0331(9) -0.0031(7) 0.0065(6) -0.0023(7) C3 0.0288(11) 0.0409(13) 0.0281(11) 0.000 0.0113(9) 0.000 C4 0.0273(11) 0.0329(12) 0.0273(11) 0.000 0.0024(9) 0.000 C5 0.0247(11) 0.046(2) 0.0427(14) 0.000 0.0089(10) 0.000 F1 0.0334(8) 0.104(2) 0.0285(8) 0.000 0.0131(6) 0.000 F2 0.0369(8) 0.0621(11) 0.0302(8) 0.000 -0.0040(6) 0.000 F3A 0.095(2) 0.075(2) 0.099(2) 0.038(2) 0.065(2) 0.015(2) F4A 0.0199(14) 0.205(7) 0.063(2) 0.000 -0.0001(13) 0.000 F3B 0.090(4) 0.121(6) 0.149(6) -0.068(5) 0.083(4) -0.083(4) F4B 0.025(2) 0.209(11) 0.029(3) 0.000 0.011(2) 0.000 _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.494(3) . ? C1 C2 1.538(2) 6 ? C1 C2 1.538(2) . ? C2 C2 1.530(3) 2 ? C3 C4 1.320(3) . ? C3 F1 1.354(3) . ? C4 F2 1.351(3) . ? C4 C5 1.493(3) . ? C5 F4B 1.222(6) . ? C5 F4A 1.284(4) . ? C5 F3B 1.311(5) . ? C5 F3B 1.311(5) 6 ? C5 F3A 1.325(3) 6 ? C5 F3A 1.325(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C2 110.41(13) . 6 ? C3 C1 C2 110.41(13) . . ? C2 C1 C2 110.5(2) 6 . ? C2 C2 C1 111.33(13) 2 . ? C4 C3 F1 115.5(2) . . ? C4 C3 C1 131.2(2) . . ? F1 C3 C1 113.4(2) . . ? C3 C4 F2 120.6(2) . . ? C3 C4 C5 127.9(2) . . ? F2 C4 C5 111.5(2) . . ? F4B C5 F4A 128.1(4) . . ? F4B C5 F3B 108.6(4) . . ? F4A C5 F3B 53.2(4) . . ? F4B C5 F3B 108.6(4) . 6 ? F4A C5 F3B 53.2(4) . 6 ? F3B C5 F3B 106.0(7) . 6 ? F4B C5 F3A 51.7(2) . 6 ? F4A C5 F3A 107.6(2) . 6 ? F3B C5 F3A 140.2(3) . 6 ? F3B C5 F3A 61.7(4) 6 6 ? F4B C5 F3A 51.7(2) . . ? F4A C5 F3A 107.6(2) . . ? F3B C5 F3A 61.7(4) . . ? F3B C5 F3A 140.2(3) 6 . ? F3A C5 F3A 102.2(4) 6 . ? F4B C5 C4 117.8(3) . . ? F4A C5 C4 114.2(3) . . ? F3B C5 C4 107.6(3) . . ? F3B C5 C4 107.6(3) 6 . ? F3A C5 C4 112.2(2) 6 . ? F3A C5 C4 112.2(2) . . ? _refine_diff_density_max 0.262 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.046 #=================================================END