#------------------------------------------------------------------------------ #$Date: 2026-06-18 23:14:10 +0100 (Thu, 18 Jun 2026) $ #$Revision: 306593 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577417.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1577417 loop_ _publ_author_name 'Liu, Lichuan' 'Chen, Xingliang' 'Guan, Guiyu' 'Su, Xinyue' 'Liu, Mengqing' 'Hu, Yuefei' 'He, Wei' 'Zhang, Linxing' 'Ma, Wenpeng' 'An, Kun' _publ_section_title ; Rhodium-Catalyzed Enantioselective Intermolecular C--H Silylation of Simple Arenes: Synergistic Substituent Effects Overcome Silane Redistribution to Enable Synthesis of Si-Stereogenic Arylsilanes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC01404F _journal_year 2026 _chemical_absolute_configuration ad _chemical_formula_sum 'C17 H20 F2 O Si' _chemical_formula_weight 306.42 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-12-06 deposited with the CCDC. 2026-06-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.274(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.5297(2) _cell_length_b 8.1356(2) _cell_length_c 11.0854(3) _cell_measurement_reflns_used 10313 _cell_measurement_temperature 180.00(10) _cell_measurement_theta_max 74.7360 _cell_measurement_theta_min 4.1650 _cell_volume 816.11(4) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 18716 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 76.432 _diffrn_reflns_theta_min 4.200 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.424 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65541 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.247 _exptl_crystal_description rod-like _exptl_crystal_F_000 324 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.150 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.015(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 3298 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0289 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.1034P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.0859 _reflns_Friedel_coverage 0.833 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.940 _reflns_number_gt 3105 _reflns_number_total 3298 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc01404f2.cif _cod_data_source_block 3 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1577417 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; 3.res created by SHELXL-2014/7 TITL 3_a.res in P2(1) REM Old TITL 3 in P2(1) REM SHELXT solution in P2(1) REM R1 0.106, Rweak 0.030, Alpha 0.002, Orientation as input REM Flack x = 0.033 ( 0.028 ) from Parsons' quotients REM Formula found by SHELXT: C17 O F2 Si CELL 1.54178 9.5297 8.1356 11.0854 90 108.274 90 ZERR 2 0.0002 0.0002 0.0003 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O F Si UNIT 34 40 2 4 2 L.S. 10 PLAN 20 BOND $H LIST 6 CONF fmap 2 acta WGHT 0.049500 0.103400 FVAR 0.35532 SI1 5 0.155496 0.639369 0.682126 11.00000 0.03931 0.03710 = 0.03321 0.00176 0.00331 0.00616 H1 2 0.053104 0.761179 0.691743 11.00000 -1.20000 F1 4 0.266752 0.747988 0.958537 11.00000 0.05875 0.06968 = 0.04117 -0.00492 0.01796 -0.00074 F2 4 0.686303 0.864217 0.735019 11.00000 0.05611 0.06167 = 0.08375 -0.00347 0.03041 -0.00612 O1 3 0.316337 0.342484 0.702577 11.00000 0.03743 0.03807 = 0.04123 0.00046 0.01545 0.00494 C1 1 0.147392 0.616852 0.512694 11.00000 0.06010 0.05585 = 0.03295 0.00567 0.00093 -0.00418 AFIX 137 H1A 2 0.149369 0.723622 0.476391 11.00000 -1.50000 H1B 2 0.057813 0.561273 0.466440 11.00000 -1.50000 H1C 2 0.230822 0.554066 0.508012 11.00000 -1.50000 AFIX 0 C2 1 0.341982 0.724894 0.776821 11.00000 0.04482 0.03056 = 0.03620 0.00032 0.00700 0.00577 C3 1 0.373019 0.771680 0.902366 11.00000 0.04667 0.04293 = 0.03514 0.00248 0.00760 0.00535 C4 1 0.504003 0.843433 0.974187 11.00000 0.05424 0.05400 = 0.03471 -0.00160 -0.00083 0.00526 AFIX 43 H4 2 0.519064 0.871396 1.058658 11.00000 -1.20000 AFIX 0 C5 1 0.612026 0.872784 0.918115 11.00000 0.04364 0.04591 = 0.05286 -0.00130 -0.00250 -0.00064 AFIX 43 H5 2 0.701532 0.920768 0.963683 11.00000 -1.20000 AFIX 0 C6 1 0.583530 0.829134 0.793260 11.00000 0.04511 0.03983 = 0.05382 0.00227 0.01380 0.00317 C7 1 0.453292 0.756081 0.722566 11.00000 0.04962 0.03614 = 0.04060 -0.00041 0.01169 0.00356 AFIX 43 H7 2 0.439422 0.727420 0.638406 11.00000 -1.20000 AFIX 0 C8 1 0.112473 0.443082 0.752245 11.00000 0.03271 0.04322 = 0.02608 -0.00338 0.00398 0.00228 C9 1 -0.002588 0.420113 0.805260 11.00000 0.03589 0.06202 = 0.02869 -0.00269 0.00682 0.00488 C10 1 -0.026080 0.264229 0.847844 11.00000 0.04307 0.07669 = 0.03605 0.00539 0.01441 -0.00442 AFIX 43 H10 2 -0.101713 0.249334 0.883197 11.00000 -1.20000 AFIX 0 C11 1 0.059251 0.133409 0.838802 11.00000 0.05934 0.05439 = 0.04003 0.00712 0.01458 -0.01028 AFIX 43 H11 2 0.039799 0.030300 0.866114 11.00000 -1.20000 AFIX 0 C12 1 0.175083 0.152857 0.789099 11.00000 0.04990 0.04069 = 0.03638 0.00307 0.00964 0.00199 AFIX 43 H12 2 0.234361 0.064064 0.783861 11.00000 -1.20000 AFIX 0 C13 1 0.200356 0.306192 0.747761 11.00000 0.03341 0.03915 = 0.02715 -0.00054 0.00624 0.00180 C14 1 -0.101339 0.560078 0.817510 11.00000 0.04715 0.08300 = 0.04587 -0.00190 0.01641 0.01739 AFIX 137 H14A 2 -0.041712 0.649471 0.862328 11.00000 -1.50000 H14B 2 -0.165675 0.523408 0.863550 11.00000 -1.50000 H14C 2 -0.159403 0.596323 0.734438 11.00000 -1.50000 AFIX 0 C15 1 0.400203 0.211540 0.671646 11.00000 0.04994 0.04808 = 0.04131 0.00314 0.01768 0.01607 AFIX 13 H15 2 0.426420 0.130890 0.740794 11.00000 -1.20000 AFIX 0 C16 1 0.310936 0.128380 0.549484 11.00000 0.08833 0.05711 = 0.04625 -0.00885 0.02442 0.01100 AFIX 137 H16A 2 0.225180 0.077761 0.561284 11.00000 -1.50000 H16B 2 0.370372 0.046023 0.526875 11.00000 -1.50000 H16C 2 0.280661 0.208634 0.482844 11.00000 -1.50000 AFIX 0 C17 1 0.539040 0.292171 0.661468 11.00000 0.05194 0.08944 = 0.08579 -0.00115 0.03666 0.01205 AFIX 137 H17A 2 0.513545 0.368371 0.591833 11.00000 -1.50000 H17B 2 0.604033 0.209568 0.647208 11.00000 -1.50000 H17C 2 0.587674 0.349756 0.738901 11.00000 -1.50000 AFIX 0 HKLF 4 REM 3_a.res in P2(1) REM R1 = 0.0289 for 3105 Fo > 4sig(Fo) and 0.0319 for all 3298 data REM 197 parameters refined using 1 restraints END WGHT 0.0420 0.1267 REM Highest difference peak 0.150, deepest hole -0.203, 1-sigma level 0.032 Q1 1 0.1270 0.6351 0.5832 11.00000 0.05 0.15 Q2 1 0.4170 0.1336 0.5150 11.00000 0.05 0.11 Q3 1 -0.0417 0.7879 0.8084 11.00000 0.05 0.10 Q4 1 0.1020 0.4913 0.6826 11.00000 0.05 0.10 Q5 1 0.5145 0.5444 0.6174 11.00000 0.05 0.10 Q6 1 0.4346 0.3342 0.4682 11.00000 0.05 0.10 Q7 1 0.4735 0.9477 1.0643 11.00000 0.05 0.10 Q8 1 0.1862 0.0344 0.9507 11.00000 0.05 0.10 Q9 1 -0.0591 0.6313 0.9053 11.00000 0.05 0.10 Q10 1 0.5217 0.4166 0.6051 11.00000 0.05 0.10 Q11 1 0.5264 0.9491 1.0734 11.00000 0.05 0.09 Q12 1 -0.0158 -0.0580 0.8418 11.00000 0.05 0.09 Q13 1 0.1704 0.5193 0.7618 11.00000 0.05 0.09 Q14 1 0.2966 -0.0264 0.7266 11.00000 0.05 0.09 Q15 1 0.1799 0.0789 0.5740 11.00000 0.05 0.09 Q16 1 0.0442 0.5603 1.0114 11.00000 0.05 0.09 Q17 1 0.1552 0.8938 0.7621 11.00000 0.05 0.09 Q18 1 0.4295 0.7249 0.5534 11.00000 0.05 0.09 Q19 1 0.1220 0.4743 0.4799 11.00000 0.05 0.08 Q20 1 -0.1202 0.3435 0.9723 11.00000 0.05 0.08 ; _shelx_res_checksum 23974 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.15550(7) 0.63937(8) 0.68213(5) 0.03841(17) Uani 1 1 d . . . . . H1 H 0.053(3) 0.761(4) 0.692(3) 0.046 Uiso 1 1 d . U . . . F1 F 0.26675(19) 0.7480(2) 0.95854(15) 0.0560(4) Uani 1 1 d . . . . . F2 F 0.6863(2) 0.8642(2) 0.7350(2) 0.0652(5) Uani 1 1 d . . . . . O1 O 0.31634(18) 0.3425(2) 0.70258(16) 0.0382(4) Uani 1 1 d . . . . . C1 C 0.1474(3) 0.6169(4) 0.5127(2) 0.0528(7) Uani 1 1 d . . . . . H1A H 0.1494 0.7236 0.4764 0.079 Uiso 1 1 calc R U . . . H1B H 0.0578 0.5613 0.4664 0.079 Uiso 1 1 calc R U . . . H1C H 0.2308 0.5541 0.5080 0.079 Uiso 1 1 calc R U . . . C2 C 0.3420(3) 0.7249(3) 0.7768(2) 0.0385(5) Uani 1 1 d . . . . . C3 C 0.3730(3) 0.7717(3) 0.9024(2) 0.0428(6) Uani 1 1 d . . . . . C4 C 0.5040(3) 0.8434(4) 0.9742(2) 0.0511(7) Uani 1 1 d . . . . . H4 H 0.5191 0.8714 1.0587 0.061 Uiso 1 1 calc R U . . . C5 C 0.6120(3) 0.8728(4) 0.9181(3) 0.0516(7) Uani 1 1 d . . . . . H5 H 0.7015 0.9208 0.9637 0.062 Uiso 1 1 calc R U . . . C6 C 0.5835(3) 0.8291(3) 0.7933(3) 0.0466(6) Uani 1 1 d . . . . . C7 C 0.4533(3) 0.7561(3) 0.7226(2) 0.0427(6) Uani 1 1 d . . . . . H7 H 0.4394 0.7274 0.6384 0.051 Uiso 1 1 calc R U . . . C8 C 0.1125(2) 0.4431(3) 0.7522(2) 0.0352(5) Uani 1 1 d . . . . . C9 C -0.0026(3) 0.4201(4) 0.8053(2) 0.0430(6) Uani 1 1 d . . . . . C10 C -0.0261(3) 0.2642(4) 0.8478(3) 0.0515(7) Uani 1 1 d . . . . . H10 H -0.1017 0.2493 0.8832 0.062 Uiso 1 1 calc R U . . . C11 C 0.0593(3) 0.1334(4) 0.8388(2) 0.0515(6) Uani 1 1 d . . . . . H11 H 0.0398 0.0303 0.8661 0.062 Uiso 1 1 calc R U . . . C12 C 0.1751(3) 0.1529(4) 0.7891(2) 0.0432(5) Uani 1 1 d . . . . . H12 H 0.2344 0.0641 0.7839 0.052 Uiso 1 1 calc R U . . . C13 C 0.2004(2) 0.3062(3) 0.7478(2) 0.0340(5) Uani 1 1 d . . . . . C14 C -0.1013(3) 0.5601(5) 0.8175(3) 0.0582(8) Uani 1 1 d . . . . . H14A H -0.0417 0.6495 0.8623 0.087 Uiso 1 1 calc R U . . . H14B H -0.1657 0.5234 0.8635 0.087 Uiso 1 1 calc R U . . . H14C H -0.1594 0.5963 0.7344 0.087 Uiso 1 1 calc R U . . . C15 C 0.4002(3) 0.2115(4) 0.6716(3) 0.0457(6) Uani 1 1 d . . . . . H15 H 0.4264 0.1309 0.7408 0.055 Uiso 1 1 calc R U . . . C16 C 0.3109(4) 0.1284(5) 0.5495(3) 0.0631(8) Uani 1 1 d . . . . . H16A H 0.2252 0.0778 0.5613 0.095 Uiso 1 1 calc R U . . . H16B H 0.3704 0.0460 0.5269 0.095 Uiso 1 1 calc R U . . . H16C H 0.2807 0.2086 0.4828 0.095 Uiso 1 1 calc R U . . . C17 C 0.5390(4) 0.2922(5) 0.6615(4) 0.0722(10) Uani 1 1 d . . . . . H17A H 0.5135 0.3684 0.5918 0.108 Uiso 1 1 calc R U . . . H17B H 0.6040 0.2096 0.6472 0.108 Uiso 1 1 calc R U . . . H17C H 0.5877 0.3498 0.7389 0.108 Uiso 1 1 calc R U . . . 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 Si1 0.0393(3) 0.0371(3) 0.0332(3) 0.0018(3) 0.0033(2) 0.0062(3) F1 0.0587(9) 0.0697(10) 0.0412(8) -0.0049(8) 0.0180(7) -0.0007(8) F2 0.0561(10) 0.0617(10) 0.0838(13) -0.0035(10) 0.0304(9) -0.0061(8) O1 0.0374(8) 0.0381(9) 0.0412(9) 0.0005(7) 0.0154(7) 0.0049(7) C1 0.0601(15) 0.0558(18) 0.0329(11) 0.0057(12) 0.0009(10) -0.0042(14) C2 0.0448(12) 0.0306(11) 0.0362(11) 0.0003(9) 0.0070(9) 0.0058(10) C3 0.0467(13) 0.0429(13) 0.0351(12) 0.0025(10) 0.0076(10) 0.0054(10) C4 0.0542(15) 0.0540(16) 0.0347(13) -0.0016(11) -0.0008(11) 0.0053(13) C5 0.0436(14) 0.0459(14) 0.0529(15) -0.0013(12) -0.0025(12) -0.0006(11) C6 0.0451(13) 0.0398(13) 0.0538(15) 0.0023(12) 0.0138(11) 0.0032(11) C7 0.0496(14) 0.0361(12) 0.0406(13) -0.0004(10) 0.0117(11) 0.0036(10) C8 0.0327(11) 0.0432(12) 0.0261(10) -0.0034(9) 0.0040(8) 0.0023(9) C9 0.0359(11) 0.0620(16) 0.0287(11) -0.0027(11) 0.0068(9) 0.0049(11) C10 0.0431(13) 0.077(2) 0.0360(13) 0.0054(13) 0.0144(10) -0.0044(13) C11 0.0593(14) 0.0544(15) 0.0400(12) 0.0071(14) 0.0146(11) -0.0103(16) C12 0.0499(12) 0.0407(12) 0.0364(11) 0.0031(11) 0.0096(9) 0.0020(12) C13 0.0334(10) 0.0391(11) 0.0272(10) -0.0005(9) 0.0062(8) 0.0018(9) C14 0.0472(14) 0.083(2) 0.0459(15) -0.0019(15) 0.0164(12) 0.0174(15) C15 0.0499(14) 0.0481(13) 0.0413(13) 0.0031(11) 0.0177(11) 0.0161(11) C16 0.088(2) 0.0571(17) 0.0462(14) -0.0089(15) 0.0244(14) 0.0110(18) C17 0.0519(18) 0.089(3) 0.086(2) -0.001(2) 0.0367(17) 0.0120(17) 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' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Si1 C8 112.84(12) . . ? C1 Si1 C2 109.29(13) . . ? C8 Si1 C2 111.87(10) . . ? C1 Si1 H1 109.4(12) . . ? C8 Si1 H1 108.6(12) . . ? C2 Si1 H1 104.5(13) . . ? C13 O1 C15 119.77(19) . . ? Si1 C1 H1A 109.5 . . ? Si1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Si1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 115.6(2) . . ? C3 C2 Si1 121.8(2) . . ? C7 C2 Si1 122.43(19) . . ? F1 C3 C4 117.7(2) . . ? F1 C3 C2 117.9(2) . . ? C4 C3 C2 124.5(3) . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? F2 C6 C5 118.7(3) . . ? F2 C6 C7 118.3(3) . . ? C5 C6 C7 123.0(3) . . ? C6 C7 C2 120.2(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C13 C8 C9 117.4(2) . . ? C13 C8 Si1 116.76(17) . . ? C9 C8 Si1 125.80(19) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 C14 119.0(2) . . ? C8 C9 C14 121.7(3) . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 118.6(3) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 O1 123.9(2) . . ? C12 C13 C8 122.6(2) . . ? O1 C13 C8 113.4(2) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C17 105.2(2) . . ? O1 C15 C16 110.3(2) . . ? C17 C15 C16 112.7(3) . . ? O1 C15 H15 109.5 . . ? C17 C15 H15 109.5 . . ? C16 C15 H15 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 Si1 C1 1.864(3) . ? Si1 C8 1.877(3) . ? Si1 C2 1.891(3) . ? Si1 H1 1.42(3) . ? F1 C3 1.359(3) . ? F2 C6 1.362(3) . ? O1 C13 1.381(3) . ? O1 C15 1.436(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.382(3) . ? C2 C7 1.397(4) . ? C3 C4 1.382(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.371(4) . ? C5 H5 0.9300 . ? C6 C7 1.378(4) . ? C7 H7 0.9300 . ? C8 C13 1.404(3) . ? C8 C9 1.410(4) . ? C9 C10 1.396(4) . ? C9 C14 1.510(4) . ? C10 C11 1.362(5) . ? C10 H10 0.9300 . ? C11 C12 1.389(4) . ? C11 H11 0.9300 . ? C12 C13 1.376(4) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C17 1.512(5) . ? C15 C16 1.514(4) . ? C15 H15 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 C1 Si1 C2 C3 172.6(2) . . . . ? C8 Si1 C2 C3 -61.7(2) . . . . ? C1 Si1 C2 C7 -2.7(2) . . . . ? C8 Si1 C2 C7 123.0(2) . . . . ? C7 C2 C3 F1 178.3(2) . . . . ? Si1 C2 C3 F1 2.7(3) . . . . ? C7 C2 C3 C4 -0.6(4) . . . . ? Si1 C2 C3 C4 -176.2(2) . . . . ? F1 C3 C4 C5 -178.3(2) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 F2 177.0(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? F2 C6 C7 C2 -177.0(2) . . . . ? C5 C6 C7 C2 0.8(4) . . . . ? C3 C2 C7 C6 -0.1(3) . . . . ? Si1 C2 C7 C6 175.44(19) . . . . ? C1 Si1 C8 C13 56.7(2) . . . . ? C2 Si1 C8 C13 -67.02(19) . . . . ? C1 Si1 C8 C9 -121.3(2) . . . . ? C2 Si1 C8 C9 115.0(2) . . . . ? C13 C8 C9 C10 -1.4(3) . . . . ? Si1 C8 C9 C10 176.61(19) . . . . ? C13 C8 C9 C14 178.5(2) . . . . ? Si1 C8 C9 C14 -3.5(3) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C14 C9 C10 C11 179.8(3) . . . . ? C9 C10 C11 C12 1.5(4) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 O1 176.6(2) . . . . ? C11 C12 C13 C8 -0.9(3) . . . . ? C15 O1 C13 C12 13.1(3) . . . . ? C15 O1 C13 C8 -169.2(2) . . . . ? C9 C8 C13 C12 2.0(3) . . . . ? Si1 C8 C13 C12 -176.16(18) . . . . ? C9 C8 C13 O1 -175.77(19) . . . . ? Si1 C8 C13 O1 6.1(2) . . . . ? C13 O1 C15 C17 -164.8(2) . . . . ? C13 O1 C15 C16 73.4(3) . . . . ?