# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1326 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Batsanov, Andrei S.' 'Brooke, Gerald M.' 'Holling, Darren' 'Kenwright, Alan M.' _journal_name_full 'Chemical Communications' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '1999' _ccdc_journal_depnumber '?' _publ_section_title ; Pyrolysis reactions of 4-nonafluorobiphenyl prop-2-enyl ether: a remarkable rearrangement reaction. ; #====================================================================== data_(12) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H5 F9 O' _chemical_formula_weight 372.19 _ccdc_compound_id '12' _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' 0.0181 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.242(3) _cell_length_b 6.219(2) _cell_length_c 20.254(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.05(1) _cell_angle_gamma 90.00 _cell_volume 2671.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 34 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.838 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '\y-curves of 3 reflections (108 scans) measured' 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 0.030 1.00 0.00 0.00 0.030 0.00 1.00 0.00 0.300 0.00 -1.00 0.00 0.300 0.00 0.00 1.00 0.030 0.00 0.00 -1.00 0.030 _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_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.5 _diffrn_reflns_number 3080 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 74.92 _reflns_number_total 2394 _reflns_number_gt 1926 _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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+2.5305P] 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 0.00042(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2394 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F2 F 0.44755(6) 0.3006(2) 0.15782(6) 0.0320(3) Uani 1 1 d . . . F4 F 0.24241(6) 0.2564(2) 0.23720(6) 0.0325(3) Uani 1 1 d . . . F5 F 0.20409(6) 0.1326(2) 0.11680(7) 0.0341(3) Uani 1 1 d . . . F7 F 0.37933(6) 0.5653(2) 0.06426(6) 0.0339(3) Uani 1 1 d . . . F32 F 0.40694(7) 0.6938(2) 0.21971(6) 0.0378(4) Uani 1 1 d . . . F33 F 0.46869(7) 0.8264(2) 0.33293(7) 0.0417(4) Uani 1 1 d . . . F34 F 0.47146(7) 0.5707(3) 0.44127(7) 0.0460(4) Uani 1 1 d . . . F35 F 0.41176(8) 0.1843(3) 0.43740(7) 0.0519(5) Uani 1 1 d . . . F36 F 0.34903(7) 0.0527(2) 0.32518(7) 0.0398(4) Uani 1 1 d . . . O O 0.25228(8) 0.4664(3) 0.04757(8) 0.0357(4) Uani 1 1 d . . . C1 C 0.37534(10) 0.0401(4) 0.10632(10) 0.0255(5) Uani 1 1 d . . . H1 H 0.4061(11) -0.066(4) 0.1180(11) 0.020(6) Uiso 1 1 d . . . C2 C 0.38456(9) 0.2576(4) 0.14486(10) 0.0250(5) Uani 1 1 d . . . C3 C 0.34721(10) 0.2937(4) 0.20555(10) 0.0244(5) Uani 1 1 d . . . C4 C 0.28703(10) 0.2450(4) 0.19313(10) 0.0254(5) Uani 1 1 d . . . C5 C 0.26777(10) 0.1674(4) 0.12424(10) 0.0267(5) Uani 1 1 d . . . C6 C 0.28781(10) 0.3506(4) 0.07856(10) 0.0259(5) Uani 1 1 d . . . C7 C 0.35957(10) 0.3631(4) 0.07960(10) 0.0255(5) Uani 1 1 d . . . C8 C 0.38386(11) 0.1686(4) 0.04163(11) 0.0291(5) Uani 1 1 d . . . H81 H 0.3608(11) 0.125(4) 0.0007(12) 0.026(6) Uiso 1 1 d . . . H82 H 0.4275(12) 0.187(4) 0.0335(12) 0.032(7) Uiso 1 1 d . . . C9 C 0.30685(11) -0.0353(4) 0.11066(11) 0.0277(5) Uani 1 1 d . . . H91 H 0.3021(11) -0.143(4) 0.1460(11) 0.022(6) Uiso 1 1 d . . . H92 H 0.2916(11) -0.100(4) 0.0688(13) 0.029(6) Uiso 1 1 d . . . C31 C 0.37729(10) 0.3683(4) 0.26887(10) 0.0248(5) Uani 1 1 d . . . C32 C 0.40795(10) 0.5649(4) 0.27322(10) 0.0279(5) Uani 1 1 d . . . C33 C 0.43918(10) 0.6350(4) 0.33055(11) 0.0294(5) Uani 1 1 d . . . C34 C 0.43987(10) 0.5066(4) 0.38588(11) 0.0319(5) Uani 1 1 d . . . C35 C 0.40962(11) 0.3106(4) 0.38383(11) 0.0328(6) Uani 1 1 d . . . C36 C 0.37840(10) 0.2441(4) 0.32593(11) 0.0286(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.0208(6) 0.0443(9) 0.0311(7) -0.0049(6) 0.0023(5) -0.0058(6) F4 0.0258(6) 0.0433(8) 0.0295(7) -0.0011(6) 0.0099(5) -0.0003(6) F5 0.0211(6) 0.0430(8) 0.0380(7) -0.0040(6) -0.0006(5) -0.0063(6) F7 0.0416(7) 0.0261(7) 0.0349(7) 0.0027(6) 0.0087(6) -0.0056(6) F32 0.0454(8) 0.0375(8) 0.0300(7) 0.0087(6) -0.0023(6) -0.0082(7) F33 0.0375(7) 0.0406(9) 0.0465(8) -0.0088(7) -0.0031(6) -0.0068(7) F34 0.0416(8) 0.0697(11) 0.0255(7) -0.0132(7) -0.0094(6) 0.0087(8) F35 0.0665(10) 0.0628(11) 0.0261(7) 0.0151(7) 0.0008(7) 0.0057(9) F36 0.0470(8) 0.0336(8) 0.0392(8) 0.0072(6) 0.0062(6) -0.0054(7) O 0.0384(9) 0.0354(10) 0.0324(9) 0.0027(8) -0.0048(7) 0.0058(8) C1 0.0251(10) 0.0269(12) 0.0248(10) -0.0003(9) 0.0032(8) 0.0022(9) C2 0.0209(9) 0.0308(12) 0.0234(10) -0.0022(9) 0.0029(8) -0.0028(9) C3 0.0262(10) 0.0273(11) 0.0198(10) 0.0002(9) 0.0026(8) -0.0005(9) C4 0.0243(9) 0.0289(11) 0.0236(10) 0.0001(9) 0.0063(8) -0.0009(9) C5 0.0204(9) 0.0326(12) 0.0269(11) -0.0013(10) 0.0006(8) -0.0041(9) C6 0.0299(11) 0.0269(11) 0.0207(10) -0.0043(9) -0.0008(8) -0.0011(10) C7 0.0305(11) 0.0237(11) 0.0226(10) 0.0003(9) 0.0035(8) -0.0038(9) C8 0.0318(11) 0.0328(12) 0.0232(11) -0.0008(10) 0.0058(9) -0.0009(10) C9 0.0298(11) 0.0272(12) 0.0263(11) 0.0004(10) 0.0028(9) -0.0027(10) C31 0.0228(9) 0.0312(12) 0.0205(10) -0.0003(9) 0.0018(8) 0.0026(9) C32 0.0261(10) 0.0347(13) 0.0229(10) 0.0047(9) 0.0018(8) 0.0037(10) C33 0.0239(10) 0.0317(12) 0.0328(12) -0.0055(10) 0.0013(9) 0.0029(10) C34 0.0262(10) 0.0478(15) 0.0215(10) -0.0062(10) -0.0022(8) 0.0095(11) C35 0.0350(12) 0.0422(14) 0.0215(11) 0.0052(10) 0.0044(9) 0.0119(11) C36 0.0290(10) 0.0297(12) 0.0274(11) 0.0027(10) 0.0057(9) 0.0020(10) _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 F2 C2 1.376(2) . ? F4 C4 1.338(2) . ? F5 C5 1.370(2) . ? F7 C7 1.367(2) . ? F32 C32 1.347(3) . ? F33 C33 1.345(3) . ? F34 C34 1.337(3) . ? F35 C35 1.338(3) . ? F36 C36 1.343(3) . ? O C6 1.197(3) . ? C1 C9 1.535(3) . ? C1 C8 1.553(3) . ? C1 C2 1.569(3) . ? C1 H1 0.95(2) . ? C2 C3 1.515(3) . ? C2 C7 1.544(3) . ? C3 C4 1.325(3) . ? C3 C31 1.477(3) . ? C4 C5 1.512(3) . ? C5 C6 1.542(3) . ? C5 C9 1.542(3) . ? C6 C7 1.525(3) . ? C7 C8 1.537(3) . ? C8 H81 0.98(2) . ? C8 H82 0.96(3) . ? C9 H91 0.99(2) . ? C9 H92 0.98(3) . ? C31 C32 1.386(3) . ? C31 C36 1.389(3) . ? C32 C33 1.377(3) . ? C33 C34 1.375(3) . ? C34 C35 1.378(4) . ? C35 C36 1.380(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 C9 C1 C8 111.02(19) . . ? C9 C1 C2 109.19(17) . . ? C8 C1 C2 87.65(17) . . ? C9 C1 H1 114.5(14) . . ? C8 C1 H1 117.2(14) . . ? C2 C1 H1 114.2(14) . . ? F2 C2 C3 111.25(17) . . ? F2 C2 C7 111.55(17) . . ? C3 C2 C7 117.43(18) . . ? F2 C2 C1 110.90(17) . . ? C3 C2 C1 118.32(18) . . ? C7 C2 C1 84.97(16) . . ? C4 C3 C31 127.24(19) . . ? C4 C3 C2 110.73(18) . . ? C31 C3 C2 122.01(18) . . ? C3 C4 F4 124.89(19) . . ? C3 C4 C5 117.32(18) . . ? F4 C4 C5 117.78(18) . . ? F5 C5 C4 111.65(17) . . ? F5 C5 C6 110.69(18) . . ? C4 C5 C6 104.38(17) . . ? F5 C5 C9 112.87(18) . . ? C4 C5 C9 107.68(18) . . ? C6 C5 C9 109.18(17) . . ? O C6 C7 125.3(2) . . ? O C6 C5 125.0(2) . . ? C7 C6 C5 109.70(18) . . ? F7 C7 C6 111.26(18) . . ? F7 C7 C8 119.67(17) . . ? C6 C7 C8 108.35(18) . . ? F7 C7 C2 119.33(18) . . ? C6 C7 C2 106.73(16) . . ? C8 C7 C2 89.12(17) . . ? C7 C8 C1 85.73(16) . . ? C7 C8 H81 118.3(14) . . ? C1 C8 H81 119.9(15) . . ? C7 C8 H82 110.3(16) . . ? C1 C8 H82 111.3(15) . . ? H81 C8 H82 109(2) . . ? C1 C9 C5 106.32(18) . . ? C1 C9 H91 112.5(13) . . ? C5 C9 H91 110.3(13) . . ? C1 C9 H92 110.4(14) . . ? C5 C9 H92 109.4(15) . . ? H91 C9 H92 108(2) . . ? C32 C31 C36 116.8(2) . . ? C32 C31 C3 120.82(19) . . ? C36 C31 C3 122.4(2) . . ? F32 C32 C33 118.4(2) . . ? F32 C32 C31 119.11(19) . . ? C33 C32 C31 122.5(2) . . ? F33 C33 C34 120.0(2) . . ? F33 C33 C32 120.9(2) . . ? C34 C33 C32 119.1(2) . . ? F34 C34 C33 119.6(2) . . ? F34 C34 C35 120.1(2) . . ? C33 C34 C35 120.3(2) . . ? F35 C35 C34 120.0(2) . . ? F35 C35 C36 120.5(2) . . ? C34 C35 C36 119.5(2) . . ? F36 C36 C35 118.5(2) . . ? F36 C36 C31 119.7(2) . . ? C35 C36 C31 121.8(2) . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 74.92 _diffrn_measured_fraction_theta_full 0.869 _refine_diff_density_max 0.249 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.050 #=================================================================END data_(16) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H5 F9 O' _chemical_formula_weight 372.19 _ccdc_compound_id '16' _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' 0.0181 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.4461(15) _cell_length_b 11.0332(14) _cell_length_c 19.2485(13) _cell_angle_alpha 90.00 _cell_angle_beta 108.413(6) _cell_angle_gamma 90.00 _cell_volume 2709.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 27 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.812 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8667 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'T_max,min from psi-scans' 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 0.075 1.00 0.00 0.00 0.075 0.00 1.00 0.00 0.175 0.00 -1.00 0.00 0.175 0.00 0.00 1.00 0.040 0.00 0.00 -1.00 0.040 _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_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 5009 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 67.50 _reflns_number_total 4172 _reflns_number_gt 3238 _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. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+3.5829P] 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 0.00048(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4172 _refine_ls_number_parameters 492 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.56889(19) 0.9383(2) 0.19298(13) 0.0375(6) Uani 1 1 d . . . F2 F 0.39724(16) 1.1097(2) 0.15325(13) 0.0537(6) Uani 1 1 d . . . F5 F 0.72666(18) 1.32607(19) 0.01231(11) 0.0468(6) Uani 1 1 d . . . F6 F 0.70319(17) 1.09215(18) -0.00818(10) 0.0392(5) Uani 1 1 d . . . F7A F 0.75950(14) 1.07567(18) 0.24019(9) 0.0337(5) Uani 1 1 d . . . F12 F 0.90406(14) 0.95964(17) 0.18066(11) 0.0357(5) Uani 1 1 d . . . F13 F 0.94627(15) 0.72182(19) 0.17417(11) 0.0393(5) Uani 1 1 d . . . F14 F 0.79598(16) 0.56809(17) 0.09540(11) 0.0361(5) Uani 1 1 d . . . F15 F 0.59998(15) 0.65171(18) 0.02456(11) 0.0410(5) Uani 1 1 d . . . F16 F 0.55589(14) 0.88929(18) 0.03093(11) 0.0390(5) Uani 1 1 d . . . C1 C 0.5772(3) 1.0444(3) 0.17954(17) 0.0292(8) Uani 1 1 d . . . C2 C 0.4978(3) 1.1382(3) 0.16157(19) 0.0330(8) Uani 1 1 d . . . C3 C 0.5367(3) 1.2484(4) 0.15993(19) 0.0354(9) Uani 1 1 d . . . H3 H 0.494(3) 1.325(4) 0.147(2) 0.046(11) Uiso 1 1 d . . . C3A C 0.6539(3) 1.2445(3) 0.17740(19) 0.0287(7) Uani 1 1 d . . . H3A H 0.686(2) 1.277(3) 0.2288(18) 0.027(9) Uiso 1 1 d . . . C4 C 0.6957(3) 1.3215(3) 0.1272(2) 0.0337(8) Uani 1 1 d . . . H41 H 0.669(3) 1.405(4) 0.1252(19) 0.039(10) Uiso 1 1 d . . . H42 H 0.772(3) 1.321(4) 0.148(2) 0.051(12) Uiso 1 1 d . . . C5 C 0.6679(3) 1.2693(3) 0.05117(19) 0.0318(8) Uani 1 1 d . . . H5 H 0.599(3) 1.283(4) 0.028(2) 0.039(11) Uiso 1 1 d . . . C6 C 0.6929(3) 1.1358(3) 0.05485(17) 0.0282(8) Uani 1 1 d . . . C7 C 0.7033(2) 1.0635(3) 0.11016(17) 0.0238(7) Uani 1 1 d . . . C7A C 0.6784(2) 1.1074(3) 0.17710(16) 0.0251(7) Uani 1 1 d . . . C11 C 0.7278(2) 0.9316(3) 0.10663(16) 0.0240(7) Uani 1 1 d . . . C12 C 0.8276(2) 0.8855(3) 0.14209(17) 0.0259(7) Uani 1 1 d . . . C13 C 0.8502(2) 0.7643(3) 0.13895(17) 0.0273(7) Uani 1 1 d . . . C14 C 0.7741(3) 0.6855(3) 0.09949(17) 0.0271(7) Uani 1 1 d . . . C15 C 0.6748(3) 0.7284(3) 0.06366(17) 0.0283(7) Uani 1 1 d . . . C16 C 0.6534(2) 0.8500(3) 0.06743(17) 0.0268(7) Uani 1 1 d . . . O1' O 0.38493(18) 0.4422(2) 0.20451(13) 0.0381(6) Uani 1 1 d . . . F2' F 0.49403(16) 0.6243(2) 0.14586(12) 0.0525(6) Uani 1 1 d . . . F5' F 0.03037(16) 0.83354(18) 0.06292(11) 0.0411(5) Uani 1 1 d . . . F6' F 0.03451(16) 0.60909(18) 0.02749(11) 0.0452(6) Uani 1 1 d . . . F7A' F 0.24148(15) 0.55865(18) 0.26266(9) 0.0334(5) Uani 1 1 d . . . F12' F 0.00977(16) 0.46256(19) 0.18381(12) 0.0441(5) Uani 1 1 d . . . F13' F -0.04680(18) 0.2274(2) 0.16878(14) 0.0567(7) Uani 1 1 d . . . F14' F 0.04940(18) 0.07242(19) 0.10104(14) 0.0544(6) Uani 1 1 d . . . F15' F 0.19847(17) 0.15466(19) 0.04541(11) 0.0466(6) Uani 1 1 d . . . F16' F 0.25529(15) 0.39014(19) 0.06039(10) 0.0373(5) Uani 1 1 d . . . C1' C 0.3578(2) 0.5467(3) 0.19166(16) 0.0290(8) Uani 1 1 d . . . C2' C 0.4096(3) 0.6463(4) 0.16700(18) 0.0339(9) Uani 1 1 d . . . C3' C 0.3684(3) 0.7523(4) 0.17334(18) 0.0319(8) Uani 1 1 d . . . H3' H 0.392(2) 0.830(3) 0.1637(17) 0.025(9) Uiso 1 1 d . . . C3A' C 0.2783(3) 0.7402(3) 0.20316(17) 0.0279(7) Uani 1 1 d . . . H3A' H 0.307(2) 0.759(3) 0.2572(17) 0.022(8) Uiso 1 1 d . . . C4' C 0.1835(3) 0.8191(3) 0.16666(19) 0.0316(8) Uani 1 1 d . . . H41' H 0.132(3) 0.813(3) 0.1943(18) 0.027(9) Uiso 1 1 d . . . H42' H 0.203(2) 0.902(3) 0.1655(17) 0.024(9) Uiso 1 1 d . . . C5' C 0.1287(3) 0.7791(3) 0.08902(18) 0.0290(8) Uani 1 1 d . . . H5' H 0.166(3) 0.802(3) 0.0577(18) 0.025(9) Uiso 1 1 d . . . C6' C 0.1128(2) 0.6450(3) 0.08623(17) 0.0270(7) Uani 1 1 d . . . C7' C 0.1655(2) 0.5640(3) 0.13404(16) 0.0218(7) Uani 1 1 d . . . C7A' C 0.2571(2) 0.6023(3) 0.19869(15) 0.0240(7) Uani 1 1 d . . . C11' C 0.1378(2) 0.4325(3) 0.12569(16) 0.0238(7) Uani 1 1 d . . . C12' C 0.0595(3) 0.3871(3) 0.15179(18) 0.0305(8) Uani 1 1 d . . . C13' C 0.0304(3) 0.2672(3) 0.1441(2) 0.0365(9) Uani 1 1 d . . . C14' C 0.0779(3) 0.1895(3) 0.1091(2) 0.0369(9) Uani 1 1 d . . . C15' C 0.1548(3) 0.2305(3) 0.08159(18) 0.0317(8) Uani 1 1 d . . . C16' C 0.1827(2) 0.3510(3) 0.08984(16) 0.0271(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0403(14) 0.0279(15) 0.0489(14) 0.0065(12) 0.0209(12) -0.0002(12) F2 0.0274(11) 0.0624(16) 0.0746(16) 0.0163(13) 0.0208(11) 0.0061(11) F5 0.0731(16) 0.0282(12) 0.0497(12) 0.0060(10) 0.0346(12) -0.0061(11) F6 0.0632(14) 0.0289(11) 0.0321(10) -0.0015(9) 0.0245(10) 0.0011(10) F7A 0.0326(10) 0.0391(12) 0.0250(9) 0.0015(9) 0.0030(8) 0.0040(9) F12 0.0267(10) 0.0288(11) 0.0465(11) -0.0045(10) 0.0044(9) -0.0035(9) F13 0.0298(10) 0.0363(12) 0.0470(12) 0.0021(10) 0.0053(9) 0.0111(10) F14 0.0474(12) 0.0197(11) 0.0439(11) -0.0005(9) 0.0183(9) 0.0052(9) F15 0.0359(11) 0.0307(12) 0.0531(12) -0.0149(10) 0.0094(10) -0.0088(10) F16 0.0259(10) 0.0334(12) 0.0492(12) -0.0063(10) -0.0005(9) 0.0036(9) C1 0.0293(18) 0.033(2) 0.0258(16) 0.0010(15) 0.0100(14) 0.0005(16) C2 0.0220(17) 0.039(2) 0.0404(19) 0.0054(17) 0.0130(14) 0.0068(17) C3 0.038(2) 0.033(2) 0.0390(19) 0.0057(17) 0.0175(16) 0.0115(19) C3A 0.0332(18) 0.0208(18) 0.0329(17) -0.0038(15) 0.0119(15) 0.0011(16) C4 0.041(2) 0.022(2) 0.0389(19) -0.0009(16) 0.0141(17) -0.0008(18) C5 0.039(2) 0.026(2) 0.0337(18) 0.0038(16) 0.0154(16) 0.0001(18) C6 0.0299(17) 0.0286(19) 0.0275(16) -0.0049(15) 0.0112(14) -0.0019(16) C7 0.0212(15) 0.0209(17) 0.0299(16) -0.0023(14) 0.0091(13) 0.0004(15) C7A 0.0224(16) 0.0289(19) 0.0221(15) 0.0009(14) 0.0044(12) 0.0016(15) C11 0.0251(16) 0.0224(18) 0.0255(15) 0.0007(14) 0.0096(13) 0.0009(15) C12 0.0231(16) 0.0234(19) 0.0306(16) -0.0002(15) 0.0076(13) -0.0044(15) C13 0.0246(17) 0.030(2) 0.0277(16) 0.0016(15) 0.0082(13) 0.0072(16) C14 0.0374(19) 0.0183(17) 0.0296(16) 0.0006(14) 0.0161(15) 0.0014(16) C15 0.0286(17) 0.0247(18) 0.0305(16) -0.0040(15) 0.0078(14) -0.0054(16) C16 0.0219(16) 0.028(2) 0.0303(16) 0.0021(15) 0.0072(13) 0.0043(16) O1' 0.0326(13) 0.0364(16) 0.0394(13) -0.0016(12) 0.0032(11) 0.0074(13) F2' 0.0327(11) 0.0720(17) 0.0600(14) 0.0034(13) 0.0249(10) 0.0022(12) F5' 0.0397(12) 0.0237(11) 0.0452(11) -0.0028(9) -0.0077(9) 0.0057(10) F6' 0.0487(13) 0.0276(11) 0.0367(11) -0.0036(9) -0.0188(9) -0.0003(10) F7A' 0.0404(11) 0.0373(12) 0.0220(9) 0.0030(8) 0.0093(8) -0.0018(10) F12' 0.0429(12) 0.0349(12) 0.0656(14) -0.0033(11) 0.0327(11) 0.0006(10) F13' 0.0479(13) 0.0402(14) 0.0916(18) 0.0080(13) 0.0355(13) -0.0133(12) F14' 0.0586(15) 0.0190(11) 0.0763(16) 0.0000(11) 0.0082(12) -0.0084(11) F15' 0.0547(14) 0.0334(12) 0.0483(12) -0.0126(10) 0.0115(10) 0.0102(11) F16' 0.0407(11) 0.0402(12) 0.0356(10) -0.0080(9) 0.0188(9) -0.0012(10) C1' 0.0235(16) 0.035(2) 0.0215(15) -0.0035(15) -0.0024(12) 0.0028(16) C2' 0.0218(17) 0.046(2) 0.0346(18) -0.0013(17) 0.0100(14) -0.0029(18) C3' 0.0265(17) 0.033(2) 0.0310(17) 0.0029(16) 0.0017(14) -0.0104(18) C3A' 0.0262(16) 0.0269(19) 0.0268(16) -0.0051(15) 0.0030(13) -0.0051(16) C4' 0.036(2) 0.022(2) 0.0331(18) -0.0065(16) 0.0051(16) -0.0027(17) C5' 0.0309(18) 0.0224(18) 0.0290(17) 0.0003(15) 0.0026(15) 0.0035(16) C6' 0.0257(17) 0.0254(19) 0.0248(15) -0.0032(14) 0.0007(13) -0.0012(15) C7' 0.0199(15) 0.0208(17) 0.0244(15) -0.0041(14) 0.0067(12) -0.0025(14) C7A' 0.0270(16) 0.0270(19) 0.0166(14) 0.0006(13) 0.0050(12) -0.0031(15) C11' 0.0251(16) 0.0206(18) 0.0220(14) 0.0010(13) 0.0021(12) 0.0005(15) C12' 0.0301(18) 0.029(2) 0.0327(17) 0.0002(15) 0.0097(14) 0.0036(16) C13' 0.0309(18) 0.029(2) 0.048(2) 0.0030(18) 0.0100(16) -0.0053(17) C14' 0.037(2) 0.020(2) 0.044(2) 0.0039(17) -0.0003(17) -0.0038(17) C15' 0.0351(19) 0.0256(19) 0.0291(17) -0.0060(15) 0.0029(14) 0.0074(17) C16' 0.0254(16) 0.030(2) 0.0237(15) -0.0019(14) 0.0040(13) -0.0019(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.212(4) . ? F2 C2 1.347(4) . ? F5 C5 1.396(4) . ? F6 C6 1.353(4) . ? F7A C7A 1.396(3) . ? F12 C12 1.339(4) . ? F13 C13 1.340(4) . ? F14 C14 1.336(4) . ? F15 C15 1.348(4) . ? F16 C16 1.348(4) . ? C1 C2 1.449(5) . ? C1 C7A 1.542(5) . ? C2 C3 1.328(5) . ? C3 C3A 1.505(5) . ? C3 H3 1.00(4) . ? C3A C4 1.522(5) . ? C3A C7A 1.548(5) . ? C3A H3A 1.01(3) . ? C4 C5 1.505(5) . ? C4 H41 0.99(4) . ? C4 H42 0.97(4) . ? C5 C6 1.507(5) . ? C5 H5 0.91(4) . ? C6 C7 1.303(4) . ? C7 C11 1.498(5) . ? C7 C7A 1.510(4) . ? C11 C16 1.380(5) . ? C11 C12 1.395(4) . ? C12 C13 1.377(5) . ? C13 C14 1.375(5) . ? C14 C15 1.378(5) . ? C15 C16 1.379(5) . ? O1' C1' 1.211(4) . ? F2' C2' 1.343(4) . ? F5' C5' 1.393(4) . ? F6' C6' 1.339(3) . ? F7A' C7A' 1.399(3) . ? F12' C12' 1.335(4) . ? F13' C13' 1.344(4) . ? F14' C14' 1.343(4) . ? F15' C15' 1.338(4) . ? F16' C16' 1.346(4) . ? C1' C2' 1.459(5) . ? C1' C7A' 1.531(5) . ? C2' C3' 1.316(5) . ? C3' C3A' 1.503(5) . ? C3' H3' 0.95(3) . ? C3A' C4' 1.519(5) . ? C3A' C7A' 1.545(5) . ? C3A' H3A' 1.01(3) . ? C4' C5' 1.508(4) . ? C4' H41' 1.00(3) . ? C4' H42' 0.95(4) . ? C5' C6' 1.493(5) . ? C5' H5' 0.93(3) . ? C6' C7' 1.318(4) . ? C7' C11' 1.494(4) . ? C7' C7A' 1.508(4) . ? C11' C16' 1.382(5) . ? C11' C12' 1.395(5) . ? C12' C13' 1.374(5) . ? C13' C14' 1.367(5) . ? C14' C15' 1.378(5) . ? C15' C16' 1.377(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 129.1(3) . . ? O1 C1 C7A 125.7(3) . . ? C2 C1 C7A 105.2(3) . . ? C3 C2 F2 126.8(3) . . ? C3 C2 C1 113.1(3) . . ? F2 C2 C1 119.9(3) . . ? C2 C3 C3A 111.2(3) . . ? C2 C3 H3 125(2) . . ? C3A C3 H3 123(2) . . ? C3 C3A C4 114.4(3) . . ? C3 C3A C7A 103.7(3) . . ? C4 C3A C7A 114.9(3) . . ? C3 C3A H3A 107.8(18) . . ? C4 C3A H3A 106.7(19) . . ? C7A C3A H3A 109.1(19) . . ? C5 C4 C3A 112.0(3) . . ? C5 C4 H41 110(2) . . ? C3A C4 H41 110(2) . . ? C5 C4 H42 107(2) . . ? C3A C4 H42 107(2) . . ? H41 C4 H42 110(3) . . ? F5 C5 C4 109.9(3) . . ? F5 C5 C6 108.0(3) . . ? C4 C5 C6 110.2(3) . . ? F5 C5 H5 109(2) . . ? C4 C5 H5 108(2) . . ? C6 C5 H5 112(3) . . ? C7 C6 F6 120.0(3) . . ? C7 C6 C5 127.0(3) . . ? F6 C6 C5 113.0(3) . . ? C6 C7 C11 121.8(3) . . ? C6 C7 C7A 120.3(3) . . ? C11 C7 C7A 117.5(3) . . ? F7A C7A C7 109.8(2) . . ? F7A C7A C1 108.3(2) . . ? C7 C7A C1 108.5(3) . . ? F7A C7A C3A 110.5(3) . . ? C7 C7A C3A 114.9(3) . . ? C1 C7A C3A 104.5(3) . . ? C16 C11 C12 116.7(3) . . ? C16 C11 C7 121.8(3) . . ? C12 C11 C7 121.5(3) . . ? F12 C12 C13 118.4(3) . . ? F12 C12 C11 120.0(3) . . ? C13 C12 C11 121.6(3) . . ? F13 C13 C14 119.2(3) . . ? F13 C13 C12 120.6(3) . . ? C14 C13 C12 120.2(3) . . ? F14 C14 C13 120.4(3) . . ? F14 C14 C15 120.0(3) . . ? C13 C14 C15 119.5(3) . . ? F15 C15 C14 119.8(3) . . ? F15 C15 C16 120.6(3) . . ? C14 C15 C16 119.6(3) . . ? F16 C16 C15 118.1(3) . . ? F16 C16 C11 119.5(3) . . ? C15 C16 C11 122.4(3) . . ? O1' C1' C2' 129.8(3) . . ? O1' C1' C7A' 125.6(3) . . ? C2' C1' C7A' 104.7(3) . . ? C3' C2' F2' 127.5(3) . . ? C3' C2' C1' 112.4(3) . . ? F2' C2' C1' 119.9(3) . . ? C2' C3' C3A' 111.8(3) . . ? C2' C3' H3' 128(2) . . ? C3A' C3' H3' 120(2) . . ? C3' C3A' C4' 115.7(3) . . ? C3' C3A' C7A' 102.8(3) . . ? C4' C3A' C7A' 115.2(3) . . ? C3' C3A' H3A' 106.6(17) . . ? C4' C3A' H3A' 110.2(18) . . ? C7A' C3A' H3A' 105.5(18) . . ? C5' C4' C3A' 111.5(3) . . ? C5' C4' H41' 107.7(19) . . ? C3A' C4' H41' 109.7(19) . . ? C5' C4' H42' 108.0(19) . . ? C3A' C4' H42' 111(2) . . ? H41' C4' H42' 109(3) . . ? F5' C5' C6' 107.8(3) . . ? F5' C5' C4' 110.0(3) . . ? C6' C5' C4' 110.1(3) . . ? F5' C5' H5' 107(2) . . ? C6' C5' H5' 110(2) . . ? C4' C5' H5' 112(2) . . ? C7' C6' F6' 119.6(3) . . ? C7' C6' C5' 127.4(3) . . ? F6' C6' C5' 112.9(3) . . ? C6' C7' C11' 121.5(3) . . ? C6' C7' C7A' 120.3(3) . . ? C11' C7' C7A' 118.2(3) . . ? F7A' C7A' C7' 108.6(2) . . ? F7A' C7A' C1' 108.8(3) . . ? C7' C7A' C1' 109.2(2) . . ? F7A' C7A' C3A' 111.5(3) . . ? C7' C7A' C3A' 114.2(3) . . ? C1' C7A' C3A' 104.3(3) . . ? C16' C11' C12' 116.4(3) . . ? C16' C11' C7' 123.5(3) . . ? C12' C11' C7' 120.1(3) . . ? F12' C12' C13' 118.9(3) . . ? F12' C12' C11' 119.2(3) . . ? C13' C12' C11' 121.9(3) . . ? F13' C13' C14' 120.2(3) . . ? F13' C13' C12' 120.1(3) . . ? C14' C13' C12' 119.7(3) . . ? F14' C14' C13' 120.0(3) . . ? F14' C14' C15' 119.5(3) . . ? C13' C14' C15' 120.5(3) . . ? F15' C15' C16' 121.0(3) . . ? F15' C15' C14' 120.1(3) . . ? C16' C15' C14' 118.9(3) . . ? F16' C16' C15' 117.9(3) . . ? F16' C16' C11' 119.4(3) . . ? C15' C16' C11' 122.6(3) . . ? _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.854 _refine_diff_density_max 0.225 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.055 #==================================================================END