#------------------------------------------------------------------------------ #$Date: 2024-10-19 03:01:23 +0300 (Sat, 19 Oct 2024) $ #$Revision: 295545 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572885.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_1572885 loop_ _publ_author_name 'Cadeddu, Stefano' 'van den Bersselaar, Bart' 'de Waal, Bas FM' 'Cordier, Marie' 'Vanthuyne, Nicolas' 'Meskers, Stefan C. J.' 'Vantomme, Ghislaine' 'Crassous, Jeanne' _publ_section_title ; Engineering Circularly Polarized Light Emission in Nanostructured Oligodimethylsiloxane-Helicene Chiral Materials ; _journal_name_full Nanoscale _journal_paper_doi 10.1039/D4NR03389B _journal_year 2024 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C28 H18 Br2 O2' _chemical_formula_sum 'C28 H18 Br2 O2' _chemical_formula_weight 546.24 _space_group_crystal_system orthorhombic _space_group_IT_number 60 _space_group_name_Hall '-P 2n 2ab' _space_group_name_H-M_alt 'P b c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_update_record ; 2024-07-08 deposited with the CCDC. 2024-10-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.9838(13) _cell_length_b 9.3761(9) _cell_length_c 15.4285(15) _cell_measurement_reflns_used 8260 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4965 _cell_measurement_theta_min 2.5626 _cell_measurement_wavelength 0.710730 _cell_volume 2167.5(4) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'Bruker APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, ver. 2023)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector CMOS-PHOTON70 _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 0.0272333 _diffrn_orient_matrix_UB_12 0.0253210 _diffrn_orient_matrix_UB_13 0.0576400 _diffrn_orient_matrix_UB_21 -0.0973498 _diffrn_orient_matrix_UB_22 -0.0139317 _diffrn_orient_matrix_UB_23 0.0227589 _diffrn_orient_matrix_UB_31 0.0340082 _diffrn_orient_matrix_UB_32 -0.0601568 _diffrn_orient_matrix_UB_33 0.0189909 _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 15024 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.496 _diffrn_reflns_theta_min 2.563 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 3.764 _exptl_absorpt_correction_T_max 0.686 _exptl_absorpt_correction_T_min 0.493 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.674 _exptl_crystal_description prism _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.414 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 147 _refine_ls_number_reflns 2487 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.182 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0352 _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^)+(0.0116P)^2^+3.5438P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.0656 _reflns_number_gt 2157 _reflns_number_total 2487 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d4nr03389b2.cif _cod_data_source_block rac-4 _cod_database_code 1572885 _shelx_res_file ; TITL SC205 [Space group= Pbcn] job.res created by SHELXL-2018/3 at 11:24:22 on 03-Oct-2023 CELL 0.71073 14.9838 9.3761 15.4285 90.000 90.000 90.000 ZERR 4 0.0013 0.0009 0.0015 0.000 0.000 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 - Y , 0.50000 + Z SYMM 0.50000 + X , 0.50000 - Y , - Z SYMM - X , Y , 0.50000 - Z SFAC C H Br O UNIT 112 72 8 8 TEMP -123 SIZE 0.1000 0.1500 0.3000 L.S. 5 FMAP 2 PLAN -20 ACTA CONF BOND $H WGHT 0.011600 3.543800 FVAR 0.27098 BR1 3 -0.184893 -0.263890 0.343762 11.00000 0.01963 0.02539 = 0.03168 -0.00204 -0.00061 -0.00606 O1 4 0.122348 -0.231316 0.506479 11.00000 0.02040 0.02074 = 0.02628 0.00565 -0.00189 0.00044 C1 1 0.061386 -0.176950 0.449612 11.00000 0.01540 0.01889 = 0.01598 -0.00186 0.00233 0.00356 C2 1 -0.016414 -0.244664 0.426964 11.00000 0.02204 0.01519 = 0.02033 0.00098 0.00368 0.00064 AFIX 43 H2 2 -0.030382 -0.336602 0.449002 11.00000 -1.20000 AFIX 0 C3 1 -0.074535 -0.173988 0.370367 11.00000 0.01466 0.02007 = 0.01956 -0.00554 0.00298 -0.00334 C4 1 -0.056413 -0.043870 0.335141 11.00000 0.01754 0.02106 = 0.01365 -0.00015 0.00156 0.00065 AFIX 43 H4 2 -0.098569 0.001061 0.298132 11.00000 -1.20000 AFIX 0 C5 1 0.025859 0.023861 0.354186 11.00000 0.01803 0.01530 = 0.01375 -0.00342 0.00394 -0.00023 C6 1 0.083857 -0.040469 0.415251 11.00000 0.01582 0.01882 = 0.01431 -0.00247 0.00457 0.00036 C7 1 0.104692 -0.369495 0.541392 11.00000 0.02657 0.02337 = 0.02311 0.00575 -0.00095 0.00222 AFIX 137 H7A 2 0.103631 -0.439723 0.494359 11.00000 -1.50000 H7B 2 0.046749 -0.368828 0.570851 11.00000 -1.50000 H7C 2 0.151577 -0.394773 0.582930 11.00000 -1.50000 AFIX 0 C8 1 0.049823 0.162122 0.318139 11.00000 0.01909 0.01608 = 0.01448 -0.00219 0.00373 -0.00011 C9 1 0.121103 0.237410 0.357160 11.00000 0.02170 0.01956 = 0.01715 -0.00365 0.00456 -0.00351 C10 1 0.178302 0.167602 0.417158 11.00000 0.01693 0.02457 = 0.02222 -0.00543 0.00127 -0.00366 AFIX 43 H10 2 0.229018 0.216665 0.438986 11.00000 -1.20000 AFIX 0 C11 1 0.161886 0.032241 0.443871 11.00000 0.01699 0.02476 = 0.01738 -0.00280 0.00064 0.00132 AFIX 43 H11 2 0.202568 -0.014130 0.481770 11.00000 -1.20000 AFIX 0 C12 1 0.000000 0.232051 0.250000 10.50000 0.02008 0.01559 = 0.01554 0.00000 0.00612 0.00000 C13 1 0.000000 0.383606 0.250000 10.50000 0.02862 0.01846 = 0.01374 0.00000 0.00903 0.00000 C14 1 0.069111 0.457510 0.294416 11.00000 0.03818 0.01589 = 0.01795 -0.00188 0.00867 -0.00514 AFIX 43 H14 2 0.071220 0.558706 0.292147 11.00000 -1.20000 AFIX 0 C15 1 0.131763 0.385844 0.339759 11.00000 0.02714 0.02309 = 0.02124 -0.00445 0.00472 -0.00839 AFIX 43 H15 2 0.183232 0.434532 0.360190 11.00000 -1.20000 AFIX 0 HKLF 4 REM SC205 [Space group= Pbcn] REM wR2 = 0.0656, GooF = S = 1.182, Restrained GooF = 1.182 for all data REM R1 = 0.0352 for 2157 Fo > 4sig(Fo) and 0.0443 for all 2487 data REM 147 parameters refined using 0 restraints END WGHT 0.0116 3.5436 REM Highest difference peak 0.414, deepest hole -0.422, 1-sigma level 0.079 Q1 1 -0.1226 -0.2308 0.3558 11.00000 0.05 0.41 Q2 1 -0.1881 -0.2041 0.3029 11.00000 0.05 0.41 Q3 1 0.1361 0.3009 0.3338 11.00000 0.05 0.40 Q4 1 -0.0408 0.4178 0.2410 11.00000 0.05 0.35 Q5 1 0.0817 0.2072 0.3511 11.00000 0.05 0.35 Q6 1 -0.1918 -0.2737 0.2829 11.00000 0.05 0.35 Q7 1 -0.1846 -0.3707 0.3304 11.00000 0.05 0.35 Q8 1 0.0145 0.3109 0.2328 11.00000 0.05 0.33 Q9 1 -0.2037 -0.1839 0.3691 11.00000 0.05 0.31 Q10 1 -0.0536 -0.1146 0.3427 11.00000 0.05 0.30 Q11 1 0.0438 0.0918 0.3320 11.00000 0.05 0.29 Q12 1 0.1421 0.2111 0.3964 11.00000 0.05 0.29 Q13 1 0.0058 -0.1877 0.4688 11.00000 0.05 0.29 Q14 1 0.0663 -0.1031 0.4421 11.00000 0.05 0.28 Q15 1 0.1589 0.1173 0.4519 11.00000 0.05 0.27 Q16 1 0.1866 0.0824 0.4139 11.00000 0.05 0.27 Q17 1 0.0240 -0.2185 0.4215 11.00000 0.05 0.27 Q18 1 -0.0568 -0.1827 0.4205 11.00000 0.05 0.26 Q19 1 0.1021 0.3995 0.3082 11.00000 0.05 0.26 Q20 1 -0.1795 -0.2658 0.4112 11.00000 0.05 0.25 ; _shelx_res_checksum 71711 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' 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 Br1 Br -0.18489(2) -0.26389(3) 0.34376(2) 0.02557(9) Uani 1 1 d . . . . . O1 O 0.12235(11) -0.23132(18) 0.50648(11) 0.0225(4) Uani 1 1 d . . . . . C1 C 0.06139(16) -0.1769(3) 0.44961(15) 0.0168(5) Uani 1 1 d . . . . . C2 C -0.01641(16) -0.2447(3) 0.42696(15) 0.0192(5) Uani 1 1 d . . . . . H2 H -0.030382 -0.336602 0.449002 0.023 Uiso 1 1 calc R U . . . C3 C -0.07453(16) -0.1740(3) 0.37037(15) 0.0181(5) Uani 1 1 d . . . . . C4 C -0.05641(16) -0.0439(3) 0.33514(14) 0.0174(5) Uani 1 1 d . . . . . H4 H -0.098569 0.001061 0.298132 0.021 Uiso 1 1 calc R U . . . C5 C 0.02586(15) 0.0239(2) 0.35419(14) 0.0157(5) Uani 1 1 d . . . . . C6 C 0.08386(15) -0.0405(3) 0.41525(14) 0.0163(5) Uani 1 1 d . . . . . C7 C 0.10469(18) -0.3695(3) 0.54139(17) 0.0243(5) Uani 1 1 d . . . . . H7A H 0.103631 -0.439723 0.494359 0.037 Uiso 1 1 calc R U . . . H7B H 0.046749 -0.368828 0.570851 0.037 Uiso 1 1 calc R U . . . H7C H 0.151577 -0.394773 0.582930 0.037 Uiso 1 1 calc R U . . . C8 C 0.04982(16) 0.1621(3) 0.31814(14) 0.0165(5) Uani 1 1 d . . . . . C9 C 0.12110(16) 0.2374(3) 0.35716(15) 0.0195(5) Uani 1 1 d . . . . . C10 C 0.17830(17) 0.1676(3) 0.41716(16) 0.0212(5) Uani 1 1 d . . . . . H10 H 0.229018 0.216665 0.438986 0.025 Uiso 1 1 calc R U . . . C11 C 0.16189(16) 0.0322(3) 0.44387(15) 0.0197(5) Uani 1 1 d . . . . . H11 H 0.202568 -0.014130 0.481770 0.024 Uiso 1 1 calc R U . . . C12 C 0.000000 0.2321(4) 0.250000 0.0171(7) Uani 1 2 d S T P . . C13 C 0.000000 0.3836(4) 0.250000 0.0203(7) Uani 1 2 d S T P . . C14 C 0.06911(18) 0.4575(3) 0.29442(16) 0.0240(6) Uani 1 1 d . . . . . H14 H 0.071220 0.558706 0.292147 0.029 Uiso 1 1 calc R U . . . C15 C 0.13176(18) 0.3858(3) 0.33976(16) 0.0238(5) Uani 1 1 d . . . . . H15 H 0.183232 0.434532 0.360190 0.029 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 Br1 0.01963(13) 0.02539(14) 0.03168(14) -0.00204(11) -0.00061(11) -0.00606(10) O1 0.0204(8) 0.0207(9) 0.0263(9) 0.0056(7) -0.0019(7) 0.0004(7) C1 0.0154(11) 0.0189(11) 0.0160(11) -0.0019(9) 0.0023(9) 0.0036(9) C2 0.0220(12) 0.0152(12) 0.0203(11) 0.0010(10) 0.0037(9) 0.0006(10) C3 0.0147(11) 0.0201(12) 0.0196(11) -0.0055(9) 0.0030(9) -0.0033(9) C4 0.0175(11) 0.0211(12) 0.0136(11) -0.0001(9) 0.0016(9) 0.0006(10) C5 0.0180(11) 0.0153(11) 0.0138(11) -0.0034(9) 0.0039(9) -0.0002(9) C6 0.0158(11) 0.0188(12) 0.0143(11) -0.0025(9) 0.0046(9) 0.0004(9) C7 0.0266(14) 0.0234(13) 0.0231(12) 0.0058(10) -0.0009(11) 0.0022(11) C8 0.0191(12) 0.0161(11) 0.0145(10) -0.0022(9) 0.0037(9) -0.0001(10) C9 0.0217(11) 0.0196(12) 0.0172(11) -0.0037(10) 0.0046(9) -0.0035(10) C10 0.0169(12) 0.0246(13) 0.0222(12) -0.0054(10) 0.0013(10) -0.0037(11) C11 0.0170(12) 0.0248(13) 0.0174(12) -0.0028(10) 0.0006(9) 0.0013(10) C12 0.0201(16) 0.0156(16) 0.0155(15) 0.000 0.0061(13) 0.000 C13 0.0286(19) 0.0185(17) 0.0137(15) 0.000 0.0090(14) 0.000 C14 0.0382(15) 0.0159(12) 0.0180(12) -0.0019(10) 0.0087(11) -0.0051(11) C15 0.0271(13) 0.0231(13) 0.0212(12) -0.0045(11) 0.0047(11) -0.0084(10) 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' Br Br -0.2901 2.4595 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 117.21(19) . . ? O1 C1 C2 124.0(2) . . ? O1 C1 C6 114.6(2) . . ? C2 C1 C6 121.4(2) . . ? C1 C2 C3 117.9(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 123.3(2) . . ? C4 C3 Br1 118.96(18) . . ? C2 C3 Br1 117.77(18) . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 118.7(2) . . ? C6 C5 C8 118.8(2) . . ? C4 C5 C8 122.3(2) . . ? C5 C6 C11 120.4(2) . . ? C5 C6 C1 119.0(2) . . ? C11 C6 C1 120.6(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C12 118.2(2) . . ? C9 C8 C5 117.9(2) . . ? C12 C8 C5 123.6(2) . . ? C8 C9 C10 120.2(2) . . ? C8 C9 C15 119.4(2) . . ? C10 C9 C15 120.3(2) . . ? C11 C10 C9 121.3(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 120.2(2) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C13 C12 C8 116.95(15) . 4 ? C13 C12 C8 116.95(15) . . ? C8 C12 C8 126.1(3) 4 . ? C12 C13 C14 119.16(16) . 4 ? C12 C13 C14 119.16(16) . . ? C14 C13 C14 121.7(3) 4 . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C9 120.4(2) . . ? C14 C15 H15 119.8 . . ? C9 C15 H15 119.8 . . ? 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 Br1 C3 1.901(2) . ? O1 C1 1.365(3) . ? O1 C7 1.428(3) . ? C1 C2 1.373(3) . ? C1 C6 1.425(3) . ? C2 C3 1.400(3) . ? C2 H2 0.9500 . ? C3 C4 1.363(3) . ? C4 C5 1.417(3) . ? C4 H4 0.9500 . ? C5 C6 1.417(3) . ? C5 C8 1.456(3) . ? C6 C11 1.424(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.415(3) . ? C8 C12 1.447(3) . ? C9 C10 1.421(3) . ? C9 C15 1.426(3) . ? C10 C11 1.357(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.421(5) . ? C13 C14 1.422(3) 4 ? C13 C14 1.422(3) . ? C14 C15 1.350(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 C7 O1 C1 C2 2.5(3) . . . . ? C7 O1 C1 C6 -178.4(2) . . . . ? O1 C1 C2 C3 177.6(2) . . . . ? C6 C1 C2 C3 -1.5(3) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? C1 C2 C3 Br1 -176.91(17) . . . . ? C2 C3 C4 C5 1.5(4) . . . . ? Br1 C3 C4 C5 -179.69(16) . . . . ? C3 C4 C5 C6 -5.2(3) . . . . ? C3 C4 C5 C8 179.4(2) . . . . ? C4 C5 C6 C11 -172.5(2) . . . . ? C8 C5 C6 C11 3.0(3) . . . . ? C4 C5 C6 C1 5.5(3) . . . . ? C8 C5 C6 C1 -179.0(2) . . . . ? O1 C1 C6 C5 178.64(19) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? O1 C1 C6 C11 -3.3(3) . . . . ? C2 C1 C6 C11 175.8(2) . . . . ? C6 C5 C8 C9 -11.3(3) . . . . ? C4 C5 C8 C9 164.0(2) . . . . ? C6 C5 C8 C12 174.41(19) . . . . ? C4 C5 C8 C12 -10.2(3) . . . . ? C12 C8 C9 C10 -172.77(19) . . . . ? C5 C8 C9 C10 12.6(3) . . . . ? C12 C8 C9 C15 11.0(3) . . . . ? C5 C8 C9 C15 -163.6(2) . . . . ? C8 C9 C10 C11 -5.6(4) . . . . ? C15 C9 C10 C11 170.7(2) . . . . ? C9 C10 C11 C6 -3.1(4) . . . . ? C5 C6 C11 C10 4.3(3) . . . . ? C1 C6 C11 C10 -173.7(2) . . . . ? C9 C8 C12 C13 -24.8(2) . . . . ? C5 C8 C12 C13 149.51(17) . . . . ? C9 C8 C12 C8 155.2(2) . . . 4 ? C5 C8 C12 C8 -30.49(17) . . . 4 ? C8 C12 C13 C14 21.12(15) 4 . . 4 ? C8 C12 C13 C14 -158.88(15) . . . 4 ? C8 C12 C13 C14 -158.87(15) 4 . . . ? C8 C12 C13 C14 21.13(15) . . . . ? C12 C13 C14 C15 -3.2(3) . . . . ? C14 C13 C14 C15 176.8(3) 4 . . . ? C13 C14 C15 C9 -11.4(4) . . . . ? C8 C9 C15 C14 7.3(4) . . . . ? C10 C9 C15 C14 -168.9(2) . . . . ?