# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2011 data_New_Global_Publ_Block _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 #TrackingRef '- p21c_forpublication.cif' # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Nils Trapp' # Name of author for correspondence _publ_contact_author_address # Address of author for correspondence ; Institut fuer Anorganische und Analytische Chemie Universitaet Freiburg Albertstr. 21 79104 Freiburg Germany ; _publ_contact_author_email nils.trapp@ac.uni-freiburg.de _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_letter ; ? ; _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; '1-Pentafluorophenyl-2,2,3,3,4,4,5,5,6,6-decafluorocylohexanol' ; _publ_section_title_footnote # remove if not required ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. # NB if using publCIF, the Author database tool might prove useful # (see the Tools menu in publCIF) loop_ _publ_author_name _publ_author_address _publ_author_footnote N.Trapp ; Institut fuer Anorganische und Analytische Chemie Universitaet Freiburg Albertstr. 21 79104 Freiburg Germany ; ; ? ; H.Boehrer ; Institut fuer Anorganische und Analytische Chemie Universitaet Freiburg Albertstr. 21 79104 Freiburg Germany ; . I.Krossing ; Institut fuer Anorganische und Analytische Chemie Universitaet Freiburg Albertstr. 21 79104 Freiburg Germany ; . #============================================================================== # TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF. For related literature, see [type here to add references to related literature]. ; _publ_section_acknowledgements # remove if not required ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; #============================================================================== _publ_manuscript_text # Used for convenience to store draft or replaced versions # of the abstract, comment etc. # Its contents will not be output ; ? ; #============================================================================== # Formatted by publCIF data_p21c _database_code_depnum_ccdc_archive 'CCDC 800116' #TrackingRef '- p21c_forpublication.cif' _audit_update_record ; 2009-09-21 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Pentafluorophenyl-2,2,3,3,4,4,5,5,6,6-decafluorocylohexanol ; _chemical_name_common 1-Pentafluorophenyl-2,2,3,3,4,4,5,5,6,6-decafluorocylohexanol _chemical_melting_point 324 _chemical_formula_moiety 'C12 H F15 O' _chemical_formula_sum 'C12 H F15 O' _chemical_formula_weight 446.13 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' 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 'P 21 /c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.051(2) _cell_length_b 15.155(3) _cell_length_c 15.989(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.85(2) _cell_angle_gamma 90.00 _cell_volume 2670.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.46 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'FS-PROCESS, March 2001, T. Higashi' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku R-AXIS Spider area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 31176 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.46 _reflns_number_total 6035 _reflns_number_gt 4592 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2007)' _computing_cell_refinement 'CrystalClear (Rigaku, 2007)' _computing_data_reduction 'CrystalClear/FS-PROCESS (Rigaku, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+2.2107P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 6035 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 F1A F 0.48624(12) 0.58422(9) 0.04746(10) 0.0266(3) Uani 1 1 d . . . F2A F 0.43103(13) 0.70622(10) -0.07637(10) 0.0316(4) Uani 1 1 d . . . F3A F 0.60239(14) 0.81336(10) -0.09194(11) 0.0327(4) Uani 1 1 d . . . F4A F 0.83968(14) 0.78951(10) 0.02364(12) 0.0372(4) Uani 1 1 d . . . F5A F 0.90471(13) 0.66716(10) 0.14891(11) 0.0317(4) Uani 1 1 d . . . F6A F 0.88101(13) 0.63295(10) 0.29331(10) 0.0290(3) Uani 1 1 d . . . F7A F 0.69720(13) 0.63045(10) 0.28778(10) 0.0285(3) Uani 1 1 d . . . F8A F 0.88698(14) 0.55031(11) 0.43567(10) 0.0357(4) Uani 1 1 d . . . F9A F 0.72750(13) 0.47086(11) 0.36044(10) 0.0319(4) Uani 1 1 d . . . F10A F 1.01540(13) 0.47480(10) 0.35672(10) 0.0315(4) Uani 1 1 d . . . F11A F 0.92450(14) 0.37328(10) 0.40309(11) 0.0335(4) Uani 1 1 d . . . F12A F 0.94068(13) 0.34691(10) 0.23480(11) 0.0324(4) Uani 1 1 d . . . F13A F 0.76179(13) 0.34437(9) 0.23735(11) 0.0293(3) Uani 1 1 d . . . F14A F 0.91758(13) 0.50361(10) 0.16784(10) 0.0280(3) Uani 1 1 d . . . F15A F 0.75534(13) 0.42827(10) 0.08771(10) 0.0270(3) Uani 1 1 d . . . O1A O 0.62997(14) 0.49088(11) 0.17391(11) 0.0215(4) Uani 1 1 d . . . H1A H 0.5860 0.5210 0.1880 0.032 Uiso 1 1 d R . . C1A C 0.7007(2) 0.61511(15) 0.10679(16) 0.0196(5) Uani 1 1 d . . . C2A C 0.5810(2) 0.63078(16) 0.04587(16) 0.0210(5) Uani 1 1 d . . . C3A C 0.5482(2) 0.69547(16) -0.02085(16) 0.0223(5) Uani 1 1 d . . . C4A C 0.6345(2) 0.74911(16) -0.02912(17) 0.0238(5) Uani 1 1 d . . . C5A C 0.7539(2) 0.73696(16) 0.02912(18) 0.0250(5) Uani 1 1 d . . . C6A C 0.7860(2) 0.67162(17) 0.09540(17) 0.0242(5) Uani 1 1 d . . . C7A C 0.7304(2) 0.54131(15) 0.18027(16) 0.0193(5) Uani 1 1 d . . . C8A C 0.7854(2) 0.58041(16) 0.27855(17) 0.0219(5) Uani 1 1 d . . . C9A C 0.8255(2) 0.50982(18) 0.35514(16) 0.0254(5) Uani 1 1 d . . . C10A C 0.9068(2) 0.43832(17) 0.34159(17) 0.0267(5) Uani 1 1 d . . . C11A C 0.8547(2) 0.39783(16) 0.24469(17) 0.0234(5) Uani 1 1 d . . . C12A C 0.8152(2) 0.46933(16) 0.16860(16) 0.0209(5) Uani 1 1 d . . . F1B F 0.05543(13) 0.58552(10) 0.06063(10) 0.0278(3) Uani 1 1 d . . . F2B F -0.02413(13) 0.70207(10) -0.07092(11) 0.0317(4) Uani 1 1 d . . . F3B F 0.12492(14) 0.82868(10) -0.08926(11) 0.0341(4) Uani 1 1 d . . . F4B F 0.36067(13) 0.83514(10) 0.03346(11) 0.0322(4) Uani 1 1 d . . . F5B F 0.44794(13) 0.72115(9) 0.16586(10) 0.0288(3) Uani 1 1 d . . . F6B F 0.31228(13) 0.65703(9) 0.31201(10) 0.0272(3) Uani 1 1 d . . . F7B F 0.15265(12) 0.57480(10) 0.24041(10) 0.0255(3) Uani 1 1 d . . . F8B F 0.44554(13) 0.52084(10) 0.39664(10) 0.0296(3) Uani 1 1 d . . . F9B F 0.26918(14) 0.51071(10) 0.40392(10) 0.0311(4) Uani 1 1 d . . . F10B F 0.37490(15) 0.35478(10) 0.37528(11) 0.0346(4) Uani 1 1 d . . . F11B F 0.19257(13) 0.38949(10) 0.27710(11) 0.0323(4) Uani 1 1 d . . . F12B F 0.31291(14) 0.32151(9) 0.18903(11) 0.0305(3) Uani 1 1 d . . . F13B F 0.47310(13) 0.40094(10) 0.26215(10) 0.0284(3) Uani 1 1 d . . . F14B F 0.17937(13) 0.45315(9) 0.10905(10) 0.0286(3) Uani 1 1 d . . . F15B F 0.35042(14) 0.46571(9) 0.09495(10) 0.0278(3) Uani 1 1 d . . . O1B O 0.44565(14) 0.57281(11) 0.23301(11) 0.0215(4) Uani 1 1 d . . . H1B H 0.4590 0.6129 0.2609 0.032 Uiso 1 1 d R . . C1B C 0.2594(2) 0.64069(15) 0.11882(16) 0.0193(5) Uani 1 1 d . . . C2B C 0.1375(2) 0.64303(16) 0.05663(17) 0.0210(5) Uani 1 1 d . . . C3B C 0.0928(2) 0.70471(16) -0.01298(17) 0.0225(5) Uani 1 1 d . . . C4B C 0.1671(2) 0.76903(16) -0.02282(17) 0.0236(5) Uani 1 1 d . . . C5B C 0.2863(2) 0.77172(16) 0.03947(18) 0.0245(5) Uani 1 1 d . . . C6B C 0.3304(2) 0.70935(16) 0.10816(17) 0.0221(5) Uani 1 1 d . . . C7B C 0.3172(2) 0.56887(15) 0.19301(16) 0.0185(5) Uani 1 1 d . . . C8B C 0.2746(2) 0.57744(15) 0.27205(17) 0.0208(5) Uani 1 1 d . . . C9B C 0.3269(2) 0.50554(17) 0.34750(16) 0.0221(5) Uani 1 1 d . . . C10B C 0.3109(2) 0.41141(17) 0.30799(18) 0.0256(5) Uani 1 1 d . . . C11B C 0.3512(2) 0.40085(16) 0.22865(18) 0.0231(5) Uani 1 1 d . . . C12B C 0.2971(2) 0.47324(15) 0.15447(16) 0.0197(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 F1A 0.0219(7) 0.0256(8) 0.0305(8) 0.0050(6) 0.0086(6) -0.0023(6) F2A 0.0285(8) 0.0305(8) 0.0296(8) 0.0058(6) 0.0053(6) 0.0028(6) F3A 0.0462(9) 0.0232(8) 0.0347(9) 0.0117(6) 0.0226(7) 0.0066(7) F4A 0.0375(9) 0.0296(9) 0.0531(11) 0.0056(7) 0.0273(8) -0.0072(7) F5A 0.0208(7) 0.0331(9) 0.0397(9) 0.0032(7) 0.0108(7) -0.0026(6) F6A 0.0269(8) 0.0258(8) 0.0295(8) -0.0047(6) 0.0065(6) -0.0070(6) F7A 0.0301(8) 0.0290(8) 0.0283(8) -0.0034(6) 0.0136(6) 0.0075(6) F8A 0.0375(9) 0.0426(10) 0.0207(8) -0.0047(7) 0.0052(7) 0.0022(7) F9A 0.0278(8) 0.0405(9) 0.0298(8) 0.0063(7) 0.0140(7) -0.0003(7) F10A 0.0197(7) 0.0344(9) 0.0341(9) -0.0003(7) 0.0042(6) -0.0027(6) F11A 0.0334(9) 0.0326(9) 0.0305(8) 0.0129(7) 0.0088(7) 0.0057(7) F12A 0.0292(8) 0.0268(8) 0.0407(9) -0.0003(7) 0.0137(7) 0.0102(6) F13A 0.0263(8) 0.0205(7) 0.0369(9) 0.0018(6) 0.0085(7) -0.0031(6) F14A 0.0226(7) 0.0275(8) 0.0370(9) 0.0014(6) 0.0151(6) 0.0007(6) F15A 0.0296(8) 0.0260(8) 0.0235(8) -0.0061(6) 0.0088(6) 0.0003(6) O1A 0.0179(8) 0.0195(9) 0.0277(9) -0.0001(7) 0.0098(7) -0.0011(6) C1A 0.0247(12) 0.0162(11) 0.0201(12) 0.0003(9) 0.0113(10) 0.0020(9) C2A 0.0242(12) 0.0192(12) 0.0234(12) -0.0016(9) 0.0136(10) -0.0012(9) C3A 0.0251(13) 0.0198(12) 0.0214(12) -0.0002(9) 0.0086(10) 0.0037(10) C4A 0.0355(14) 0.0164(12) 0.0239(13) 0.0025(9) 0.0167(11) 0.0026(10) C5A 0.0284(14) 0.0203(12) 0.0338(14) -0.0022(10) 0.0202(11) -0.0031(10) C6A 0.0220(13) 0.0238(13) 0.0285(13) -0.0029(10) 0.0119(10) 0.0036(10) C7A 0.0174(11) 0.0188(12) 0.0219(12) 0.0007(9) 0.0081(9) -0.0002(9) C8A 0.0196(12) 0.0208(12) 0.0239(12) -0.0028(9) 0.0074(10) 0.0021(9) C9A 0.0252(13) 0.0323(14) 0.0169(12) -0.0002(10) 0.0067(10) -0.0011(10) C10A 0.0247(13) 0.0272(14) 0.0245(13) 0.0050(10) 0.0061(10) -0.0008(10) C11A 0.0207(12) 0.0176(12) 0.0309(14) 0.0004(10) 0.0094(10) 0.0019(9) C12A 0.0185(12) 0.0240(13) 0.0202(12) -0.0028(9) 0.0079(9) -0.0013(9) F1B 0.0218(7) 0.0267(8) 0.0333(8) 0.0035(6) 0.0095(6) -0.0054(6) F2B 0.0224(8) 0.0335(9) 0.0324(9) 0.0042(7) 0.0039(6) 0.0014(6) F3B 0.0319(8) 0.0305(9) 0.0359(9) 0.0140(7) 0.0096(7) 0.0046(7) F4B 0.0304(8) 0.0237(8) 0.0418(9) 0.0099(7) 0.0138(7) -0.0046(6) F5B 0.0228(7) 0.0216(8) 0.0333(8) 0.0056(6) 0.0023(6) -0.0057(6) F6B 0.0364(8) 0.0184(7) 0.0278(8) -0.0075(6) 0.0139(7) -0.0039(6) F7B 0.0204(7) 0.0294(8) 0.0292(8) -0.0016(6) 0.0125(6) 0.0014(6) F8B 0.0274(8) 0.0330(9) 0.0234(8) 0.0035(6) 0.0052(6) -0.0032(6) F9B 0.0367(9) 0.0352(9) 0.0280(8) 0.0008(7) 0.0199(7) -0.0006(7) F10B 0.0470(10) 0.0271(8) 0.0345(9) 0.0142(7) 0.0217(8) 0.0068(7) F11B 0.0309(8) 0.0273(8) 0.0454(10) -0.0026(7) 0.0222(7) -0.0088(6) F12B 0.0431(9) 0.0141(7) 0.0383(9) -0.0029(6) 0.0206(7) -0.0020(6) F13B 0.0263(8) 0.0224(8) 0.0395(9) 0.0080(6) 0.0164(7) 0.0065(6) F14B 0.0254(8) 0.0212(8) 0.0329(8) -0.0046(6) 0.0052(6) -0.0059(6) F15B 0.0405(9) 0.0219(7) 0.0272(8) -0.0011(6) 0.0201(7) 0.0012(6) O1B 0.0185(8) 0.0177(8) 0.0269(9) -0.0003(7) 0.0077(7) -0.0009(6) C1B 0.0246(12) 0.0134(11) 0.0220(12) -0.0014(9) 0.0115(10) 0.0010(9) C2B 0.0218(12) 0.0177(12) 0.0255(13) -0.0017(9) 0.0116(10) -0.0022(9) C3B 0.0189(12) 0.0221(12) 0.0242(13) -0.0017(9) 0.0063(10) 0.0013(9) C4B 0.0278(13) 0.0198(12) 0.0241(13) 0.0047(10) 0.0114(10) 0.0062(10) C5B 0.0280(13) 0.0195(12) 0.0289(13) 0.0031(10) 0.0147(11) -0.0004(10) C6B 0.0211(12) 0.0196(12) 0.0242(13) -0.0021(9) 0.0076(10) -0.0003(9) C7B 0.0200(12) 0.0151(11) 0.0200(12) -0.0004(9) 0.0076(9) -0.0009(9) C8B 0.0207(12) 0.0175(12) 0.0239(12) -0.0049(9) 0.0087(10) -0.0026(9) C9B 0.0207(12) 0.0267(13) 0.0204(12) 0.0013(10) 0.0100(10) -0.0024(10) C10B 0.0259(13) 0.0230(13) 0.0296(14) 0.0067(10) 0.0130(11) -0.0005(10) C11B 0.0257(13) 0.0145(11) 0.0314(14) 0.0005(9) 0.0141(11) -0.0003(9) C12B 0.0231(12) 0.0176(11) 0.0210(12) -0.0022(9) 0.0118(10) -0.0018(9) _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 F1A C2A 1.351(3) . ? F2A C3A 1.340(3) . ? F3A C4A 1.339(3) . ? F4A C5A 1.336(3) . ? F5A C6A 1.339(3) . ? F6A C8A 1.341(3) . ? F7A C8A 1.361(3) . ? F8A C9A 1.346(3) . ? F9A C9A 1.353(3) . ? F10A C10A 1.350(3) . ? F11A C10A 1.347(3) . ? F12A C11A 1.351(3) . ? F13A C11A 1.348(3) . ? F14A C12A 1.343(3) . ? F15A C12A 1.351(3) . ? O1A C7A 1.400(3) . ? O1A H1A 0.7979 . ? C1A C2A 1.397(3) . ? C1A C6A 1.405(3) . ? C1A C7A 1.556(3) . ? C2A C3A 1.384(3) . ? C3A C4A 1.368(3) . ? C4A C5A 1.374(4) . ? C5A C6A 1.386(4) . ? C7A C8A 1.555(3) . ? C7A C12A 1.557(3) . ? C8A C9A 1.549(3) . ? C9A C10A 1.534(4) . ? C10A C11A 1.544(4) . ? C11A C12A 1.553(3) . ? F1B C2B 1.339(3) . ? F2B C3B 1.337(3) . ? F3B C4B 1.329(3) . ? F4B C5B 1.344(3) . ? F5B C6B 1.354(3) . ? F6B C8B 1.355(3) . ? F7B C8B 1.347(3) . ? F8B C9B 1.344(3) . ? F9B C9B 1.346(3) . ? F10B C10B 1.348(3) . ? F11B C10B 1.349(3) . ? F12B C11B 1.350(3) . ? F13B C11B 1.345(3) . ? F14B C12B 1.342(3) . ? F15B C12B 1.351(3) . ? O1B C7B 1.417(3) . ? O1B H1B 0.7326 . ? C1B C6B 1.401(3) . ? C1B C2B 1.403(3) . ? C1B C7B 1.552(3) . ? C2B C3B 1.385(3) . ? C3B C4B 1.375(3) . ? C4B C5B 1.379(4) . ? C5B C6B 1.382(3) . ? C7B C8B 1.550(3) . ? C7B C12B 1.555(3) . ? C8B C9B 1.557(3) . ? C9B C10B 1.540(4) . ? C10B C11B 1.539(4) . ? C11B C12B 1.552(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 C7A O1A H1A 108.7 . . ? C2A C1A C6A 114.2(2) . . ? C2A C1A C7A 120.4(2) . . ? C6A C1A C7A 125.4(2) . . ? F1A C2A C3A 113.9(2) . . ? F1A C2A C1A 122.7(2) . . ? C3A C2A C1A 123.4(2) . . ? F2A C3A C4A 120.2(2) . . ? F2A C3A C2A 119.5(2) . . ? C4A C3A C2A 120.3(2) . . ? F3A C4A C3A 120.3(2) . . ? F3A C4A C5A 120.8(2) . . ? C3A C4A C5A 118.9(2) . . ? F4A C5A C4A 120.1(2) . . ? F4A C5A C6A 119.5(2) . . ? C4A C5A C6A 120.4(2) . . ? F5A C6A C5A 114.9(2) . . ? F5A C6A C1A 122.3(2) . . ? C5A C6A C1A 122.8(2) . . ? O1A C7A C8A 106.52(18) . . ? O1A C7A C1A 114.21(19) . . ? C8A C7A C1A 111.30(19) . . ? O1A C7A C12A 101.47(18) . . ? C8A C7A C12A 110.85(19) . . ? C1A C7A C12A 112.00(19) . . ? F6A C8A F7A 107.65(19) . . ? F6A C8A C9A 107.44(19) . . ? F7A C8A C9A 107.9(2) . . ? F6A C8A C7A 112.89(19) . . ? F7A C8A C7A 106.82(18) . . ? C9A C8A C7A 113.9(2) . . ? F8A C9A F9A 107.2(2) . . ? F8A C9A C10A 108.7(2) . . ? F9A C9A C10A 108.9(2) . . ? F8A C9A C8A 108.5(2) . . ? F9A C9A C8A 110.5(2) . . ? C10A C9A C8A 112.9(2) . . ? F11A C10A F10A 108.2(2) . . ? F11A C10A C9A 109.6(2) . . ? F10A C10A C9A 108.3(2) . . ? F11A C10A C11A 108.8(2) . . ? F10A C10A C11A 108.3(2) . . ? C9A C10A C11A 113.5(2) . . ? F13A C11A F12A 107.20(19) . . ? F13A C11A C10A 108.2(2) . . ? F12A C11A C10A 109.0(2) . . ? F13A C11A C12A 111.72(19) . . ? F12A C11A C12A 108.3(2) . . ? C10A C11A C12A 112.3(2) . . ? F14A C12A F15A 107.83(19) . . ? F14A C12A C11A 106.56(19) . . ? F15A C12A C11A 107.73(19) . . ? F14A C12A C7A 112.33(19) . . ? F15A C12A C7A 108.38(18) . . ? C11A C12A C7A 113.78(19) . . ? C7B O1B H1B 103.9 . . ? C6B C1B C2B 114.3(2) . . ? C6B C1B C7B 120.4(2) . . ? C2B C1B C7B 125.3(2) . . ? F1B C2B C3B 115.0(2) . . ? F1B C2B C1B 122.1(2) . . ? C3B C2B C1B 122.8(2) . . ? F2B C3B C4B 119.6(2) . . ? F2B C3B C2B 119.7(2) . . ? C4B C3B C2B 120.7(2) . . ? F3B C4B C3B 121.2(2) . . ? F3B C4B C5B 120.5(2) . . ? C3B C4B C5B 118.4(2) . . ? F4B C5B C4B 120.0(2) . . ? F4B C5B C6B 119.5(2) . . ? C4B C5B C6B 120.5(2) . . ? F5B C6B C5B 114.3(2) . . ? F5B C6B C1B 122.5(2) . . ? C5B C6B C1B 123.2(2) . . ? O1B C7B C8B 106.88(19) . . ? O1B C7B C1B 112.74(18) . . ? C8B C7B C1B 111.70(19) . . ? O1B C7B C12B 100.65(18) . . ? C8B C7B C12B 110.57(18) . . ? C1B C7B C12B 113.63(19) . . ? F7B C8B F6B 108.08(18) . . ? F7B C8B C7B 111.24(19) . . ? F6B C8B C7B 107.49(19) . . ? F7B C8B C9B 107.97(19) . . ? F6B C8B C9B 107.70(19) . . ? C7B C8B C9B 114.15(19) . . ? F8B C9B F9B 108.30(19) . . ? F8B C9B C10B 109.0(2) . . ? F9B C9B C10B 108.44(19) . . ? F8B C9B C8B 109.50(19) . . ? F9B C9B C8B 108.76(19) . . ? C10B C9B C8B 112.7(2) . . ? F10B C10B F11B 108.31(19) . . ? F10B C10B C11B 108.8(2) . . ? F11B C10B C11B 108.2(2) . . ? F10B C10B C9B 109.0(2) . . ? F11B C10B C9B 108.4(2) . . ? C11B C10B C9B 113.9(2) . . ? F13B C11B F12B 107.37(19) . . ? F13B C11B C10B 109.2(2) . . ? F12B C11B C10B 108.52(19) . . ? F13B C11B C12B 110.90(19) . . ? F12B C11B C12B 108.2(2) . . ? C10B C11B C12B 112.44(19) . . ? F14B C12B F15B 107.43(19) . . ? F14B C12B C11B 106.15(18) . . ? F15B C12B C11B 107.85(19) . . ? F14B C12B C7B 112.77(19) . . ? F15B C12B C7B 108.41(18) . . ? C11B C12B C7B 113.94(19) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.448 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.075