#------------------------------------------------------------------------------ #$Date: 2020-04-28 01:09:58 +0300 (Tue, 28 Apr 2020) $ #$Revision: 251196 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557928.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_1557928 loop_ _publ_author_name 'Curbet, Idriss' 'Colombel-Rouen, Sophie' 'Manguin, Romane' 'Clermont, Anthony' 'Quelhas, Alexandre' 'M\"uller, Daniel S.' 'Roisnel, Thierry' 'Basle, Olivier' 'Trolez, Yann' 'Mauduit, Marc' _publ_section_title ; Expedient Synthesis of Conjugated Triynes via Alkyne Metathesis ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01124J _journal_year 2020 _chemical_absolute_configuration unk _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C16 H12' _chemical_formula_sum 'C16 H12' _chemical_formula_weight 204.26 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_update_record ; 2019-04-04 deposited with the CCDC. 2020-04-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 6 _cell_length_a 9.3055(16) _cell_length_b 10.3538(15) _cell_length_c 18.151(3) _cell_measurement_reflns_used 7576 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.26 _cell_measurement_wavelength 0.71073 _cell_volume 1748.8(5) _computing_cell_refinement 'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)' _computing_data_collection 'SAINT (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2017)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector '(CMOS) PHOTON 100' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _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 0.0274 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 10436 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.470 _diffrn_reflns_theta_min 2.943 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.164 _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.580 _exptl_crystal_size_min 0.450 _refine_diff_density_max 0.190 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.025(3) _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 3996 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0359 _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^)+(0.0480P)^2^+0.2511P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.0924 _reflns_Friedel_coverage 0.747 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 3603 _reflns_number_total 3996 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d0sc01124j2.cif _cod_data_source_block RMA43 _cod_database_code 1557928 _shelx_res_file ; TITL import_a.res in P2(1)2(1)2(1) job.res created by SHELXL-2016/6 at 15:39:46 on 07-Jul-2017 CELL 0.71073 9.3055 10.3538 18.1511 90.000 90.000 90.000 ZERR 6.00 0.0016 0.0015 0.0029 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H UNIT 96 72 MERG 2 FMAP 2 PLAN 20 SIZE 0.45 0.58 0.80 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.048000 0.251100 EXTI 0.024865 FVAR 0.81872 C1 1 1.020863 0.086901 0.759342 11.00000 0.03731 0.03433 = 0.04033 0.00013 -0.01163 0.01167 AFIX 137 H1A 2 1.110662 0.072165 0.732417 11.00000 -1.50000 H1B 2 0.970751 0.004518 0.766175 11.00000 -1.50000 H1C 2 1.042404 0.124855 0.807554 11.00000 -1.50000 AFIX 0 C2 1 0.929765 0.174928 0.717505 11.00000 0.02981 0.02847 = 0.03002 -0.00339 -0.00573 0.00493 C3 1 0.856190 0.249646 0.684266 11.00000 0.02739 0.02867 = 0.02722 -0.00367 -0.00530 0.00327 C4 1 0.774428 0.340448 0.647532 11.00000 0.02509 0.02861 = 0.02492 -0.00246 -0.00411 0.00184 C5 1 0.704981 0.421362 0.616516 11.00000 0.02350 0.02727 = 0.02407 -0.00304 -0.00389 0.00068 C6 1 0.620961 0.525678 0.580964 11.00000 0.01969 0.02209 = 0.02183 -0.00097 -0.00223 0.00214 C7 1 0.638059 0.645274 0.631343 11.00000 0.01868 0.02820 = 0.02545 -0.00561 -0.00642 0.00378 C8 1 0.708158 0.756567 0.609245 11.00000 0.02437 0.02761 = 0.03549 -0.00562 -0.00529 0.00185 AFIX 43 H8 2 0.742450 0.763986 0.560130 11.00000 -1.20000 AFIX 0 C9 1 0.728756 0.858172 0.658882 11.00000 0.02954 0.02986 = 0.05623 -0.01295 -0.01048 0.00137 AFIX 43 H9 2 0.777875 0.933924 0.643453 11.00000 -1.20000 AFIX 0 C10 1 0.678240 0.849056 0.730015 11.00000 0.03212 0.04650 = 0.05039 -0.02800 -0.01162 0.00695 AFIX 43 H10 2 0.692972 0.918136 0.763623 11.00000 -1.20000 AFIX 0 C11 1 0.605787 0.738757 0.752478 11.00000 0.03749 0.06235 = 0.03237 -0.01987 -0.00362 0.00636 AFIX 43 H11 2 0.569461 0.732798 0.801272 11.00000 -1.20000 AFIX 0 C12 1 0.586483 0.637476 0.703777 11.00000 0.03020 0.04185 = 0.02915 -0.00826 -0.00246 0.00013 AFIX 43 H12 2 0.537727 0.561780 0.719591 11.00000 -1.20000 AFIX 0 C13 1 0.680735 0.551784 0.503121 11.00000 0.02470 0.01896 = 0.02461 -0.00345 0.00083 -0.00224 C14 1 0.824894 0.530035 0.487520 11.00000 0.02612 0.02958 = 0.04024 -0.00120 0.00457 -0.00380 AFIX 43 H14 2 0.886948 0.498910 0.525097 11.00000 -1.20000 AFIX 0 C15 1 0.879167 0.553425 0.417382 11.00000 0.03834 0.03215 = 0.05473 -0.00485 0.02163 -0.00796 AFIX 43 H15 2 0.977443 0.536347 0.407089 11.00000 -1.20000 AFIX 0 C16 1 0.791224 0.601218 0.362751 11.00000 0.06217 0.03129 = 0.03135 -0.00486 0.01663 -0.01307 AFIX 43 H16 2 0.828490 0.616997 0.314863 11.00000 -1.20000 AFIX 0 C17 1 0.648839 0.625970 0.378057 11.00000 0.05531 0.03964 = 0.02524 0.00037 -0.00027 -0.00711 AFIX 43 H17 2 0.588136 0.660369 0.340831 11.00000 -1.20000 AFIX 0 C18 1 0.593770 0.600842 0.447642 11.00000 0.03341 0.03710 = 0.02496 0.00129 -0.00091 0.00029 AFIX 43 H18 2 0.495203 0.617440 0.457447 11.00000 -1.20000 AFIX 0 C19 1 0.462714 0.481524 0.575015 11.00000 0.02313 0.02459 = 0.01740 0.00116 -0.00248 -0.00025 C20 1 0.350003 0.569046 0.581328 11.00000 0.02475 0.02196 = 0.03456 -0.00037 -0.00374 -0.00034 AFIX 43 H20 2 0.369747 0.657331 0.591366 11.00000 -1.20000 AFIX 0 C21 1 0.208633 0.528143 0.573042 11.00000 0.02298 0.02960 = 0.04650 -0.00250 -0.00432 0.00345 AFIX 43 H21 2 0.132502 0.588908 0.576857 11.00000 -1.20000 AFIX 0 C22 1 0.178033 0.400064 0.559330 11.00000 0.02456 0.03521 = 0.05194 0.00069 -0.00898 -0.00444 AFIX 43 H22 2 0.081184 0.372032 0.555046 11.00000 -1.20000 AFIX 0 C23 1 0.289506 0.312855 0.551876 11.00000 0.03514 0.02476 = 0.04988 -0.00477 -0.01242 -0.00372 AFIX 43 H23 2 0.269181 0.224731 0.541685 11.00000 -1.20000 AFIX 0 C24 1 0.431082 0.353313 0.559200 11.00000 0.02742 0.02493 = 0.03102 -0.00317 -0.00492 0.00219 AFIX 43 H24 2 0.506974 0.292807 0.553345 11.00000 -1.20000 AFIX 0 HKLF 4 REM import_a.res in P2(1)2(1)2(1) REM R1 = 0.0359 for 3603 Fo > 4sig(Fo) and 0.0433 for all 3996 data REM 219 parameters refined using 0 restraints END WGHT 0.0402 0.2907 REM Highest difference peak 0.190, deepest hole -0.176, 1-sigma level 0.034 Q1 1 0.6440 0.5568 0.5404 11.00000 0.05 0.19 Q2 1 0.6620 0.8638 0.6861 11.00000 0.05 0.19 Q3 1 0.6235 0.5880 0.6068 11.00000 0.05 0.15 Q4 1 0.6501 0.6328 0.6710 11.00000 0.05 0.14 Q5 1 0.8473 0.2282 0.7249 11.00000 0.05 0.14 Q6 1 0.8908 0.1829 0.6747 11.00000 0.05 0.14 Q7 1 0.6421 0.6087 0.4811 11.00000 0.05 0.13 Q8 1 0.5451 0.5062 0.5735 11.00000 0.05 0.13 Q9 1 0.7203 0.7928 0.6455 11.00000 0.05 0.13 Q10 1 0.2441 0.3549 0.5751 11.00000 0.05 0.13 Q11 1 0.6265 0.5610 0.4718 11.00000 0.05 0.13 Q12 1 0.6373 0.6361 0.4187 11.00000 0.05 0.12 Q13 1 0.3999 0.5265 0.5496 11.00000 0.05 0.12 Q14 1 0.6178 0.6875 0.7288 11.00000 0.05 0.12 Q15 1 0.6270 0.5777 0.4137 11.00000 0.05 0.12 Q16 1 0.2111 0.4646 0.5394 11.00000 0.05 0.12 Q17 1 0.5431 0.6844 0.5387 11.00000 0.05 0.12 Q18 1 0.8413 0.0966 0.6904 11.00000 0.05 0.12 Q19 1 0.1890 0.4591 0.5813 11.00000 0.05 0.12 Q20 1 0.8287 0.3154 0.6817 11.00000 0.05 0.12 ; _shelx_res_checksum 46841 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 C1 C 1.0209(2) 0.0869(2) 0.75934(12) 0.0373(5) Uani 1 1 d . . . . . H1A H 1.110662 0.072165 0.732417 0.056 Uiso 1 1 calc R U . . . H1B H 0.970751 0.004518 0.766175 0.056 Uiso 1 1 calc R U . . . H1C H 1.042404 0.124855 0.807554 0.056 Uiso 1 1 calc R U . . . C2 C 0.9298(2) 0.17493(19) 0.71751(11) 0.0294(4) Uani 1 1 d . . . . . C3 C 0.8562(2) 0.24965(18) 0.68427(10) 0.0278(4) Uani 1 1 d . . . . . C4 C 0.77443(19) 0.34045(17) 0.64753(10) 0.0262(4) Uani 1 1 d . . . . . C5 C 0.70498(18) 0.42136(17) 0.61652(10) 0.0249(4) Uani 1 1 d . . . . . C6 C 0.62096(17) 0.52568(16) 0.58096(9) 0.0212(3) Uani 1 1 d . . . . . C7 C 0.63806(18) 0.64527(17) 0.63134(10) 0.0241(4) Uani 1 1 d . . . . . C8 C 0.70816(19) 0.75657(18) 0.60925(11) 0.0292(4) Uani 1 1 d . . . . . H8 H 0.742450 0.763986 0.560130 0.035 Uiso 1 1 calc R U . . . C9 C 0.7288(2) 0.8582(2) 0.65888(13) 0.0385(5) Uani 1 1 d . . . . . H9 H 0.777875 0.933924 0.643453 0.046 Uiso 1 1 calc R U . . . C10 C 0.6782(2) 0.8491(2) 0.73001(13) 0.0430(5) Uani 1 1 d . . . . . H10 H 0.692972 0.918136 0.763623 0.052 Uiso 1 1 calc R U . . . C11 C 0.6058(2) 0.7388(2) 0.75248(13) 0.0441(5) Uani 1 1 d . . . . . H11 H 0.569461 0.732798 0.801272 0.053 Uiso 1 1 calc R U . . . C12 C 0.5865(2) 0.6375(2) 0.70378(11) 0.0337(4) Uani 1 1 d . . . . . H12 H 0.537727 0.561780 0.719591 0.040 Uiso 1 1 calc R U . . . C13 C 0.68073(18) 0.55178(15) 0.50312(10) 0.0228(4) Uani 1 1 d . . . . . C14 C 0.8249(2) 0.53004(19) 0.48752(12) 0.0320(4) Uani 1 1 d . . . . . H14 H 0.886948 0.498910 0.525097 0.038 Uiso 1 1 calc R U . . . C15 C 0.8792(2) 0.5534(2) 0.41738(14) 0.0417(5) Uani 1 1 d . . . . . H15 H 0.977443 0.536347 0.407089 0.050 Uiso 1 1 calc R U . . . C16 C 0.7912(3) 0.6012(2) 0.36275(12) 0.0416(5) Uani 1 1 d . . . . . H16 H 0.828490 0.616997 0.314863 0.050 Uiso 1 1 calc R U . . . C17 C 0.6488(3) 0.6260(2) 0.37806(11) 0.0401(5) Uani 1 1 d . . . . . H17 H 0.588136 0.660369 0.340831 0.048 Uiso 1 1 calc R U . . . C18 C 0.5938(2) 0.60084(19) 0.44764(10) 0.0318(4) Uani 1 1 d . . . . . H18 H 0.495203 0.617440 0.457447 0.038 Uiso 1 1 calc R U . . . C19 C 0.46271(18) 0.48152(16) 0.57502(9) 0.0217(3) Uani 1 1 d . . . . . C20 C 0.35000(19) 0.56905(18) 0.58133(11) 0.0271(4) Uani 1 1 d . . . . . H20 H 0.369747 0.657331 0.591366 0.033 Uiso 1 1 calc R U . . . C21 C 0.2086(2) 0.52814(18) 0.57304(12) 0.0330(4) Uani 1 1 d . . . . . H21 H 0.132502 0.588908 0.576857 0.040 Uiso 1 1 calc R U . . . C22 C 0.1780(2) 0.4001(2) 0.55933(13) 0.0372(5) Uani 1 1 d . . . . . H22 H 0.081184 0.372032 0.555046 0.045 Uiso 1 1 calc R U . . . C23 C 0.2895(2) 0.31286(18) 0.55188(12) 0.0366(5) Uani 1 1 d . . . . . H23 H 0.269181 0.224731 0.541685 0.044 Uiso 1 1 calc R U . . . C24 C 0.4311(2) 0.35331(18) 0.55920(10) 0.0278(4) Uani 1 1 d . . . . . H24 H 0.506974 0.292807 0.553345 0.033 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 C1 0.0373(10) 0.0343(10) 0.0403(11) 0.0001(9) -0.0116(9) 0.0117(9) C2 0.0298(9) 0.0285(9) 0.0300(10) -0.0034(8) -0.0057(7) 0.0049(7) C3 0.0274(8) 0.0287(9) 0.0272(9) -0.0037(8) -0.0053(7) 0.0033(7) C4 0.0251(8) 0.0286(8) 0.0249(8) -0.0025(7) -0.0041(7) 0.0018(7) C5 0.0235(8) 0.0273(8) 0.0241(8) -0.0030(7) -0.0039(7) 0.0007(7) C6 0.0197(7) 0.0221(7) 0.0218(8) -0.0010(7) -0.0022(6) 0.0021(6) C7 0.0187(7) 0.0282(8) 0.0255(8) -0.0056(7) -0.0064(6) 0.0038(7) C8 0.0244(8) 0.0276(9) 0.0355(10) -0.0056(8) -0.0053(7) 0.0018(7) C9 0.0295(9) 0.0299(9) 0.0562(13) -0.0130(9) -0.0105(9) 0.0014(8) C10 0.0321(10) 0.0465(12) 0.0504(13) -0.0280(11) -0.0116(9) 0.0069(9) C11 0.0375(11) 0.0624(14) 0.0324(11) -0.0199(11) -0.0036(9) 0.0064(11) C12 0.0302(9) 0.0418(11) 0.0291(10) -0.0083(9) -0.0025(7) 0.0001(8) C13 0.0247(8) 0.0190(8) 0.0246(8) -0.0035(7) 0.0008(7) -0.0022(6) C14 0.0261(9) 0.0296(9) 0.0402(11) -0.0012(8) 0.0046(8) -0.0038(7) C15 0.0383(11) 0.0322(10) 0.0547(13) -0.0048(10) 0.0216(10) -0.0080(9) C16 0.0622(14) 0.0313(10) 0.0314(10) -0.0049(8) 0.0166(10) -0.0131(10) C17 0.0553(13) 0.0396(11) 0.0252(9) 0.0004(9) -0.0003(9) -0.0071(10) C18 0.0334(10) 0.0371(10) 0.0250(9) 0.0013(8) -0.0009(7) 0.0003(8) C19 0.0231(8) 0.0246(8) 0.0174(7) 0.0012(7) -0.0025(6) -0.0002(6) C20 0.0247(8) 0.0220(8) 0.0346(10) -0.0004(7) -0.0037(7) -0.0003(7) C21 0.0230(9) 0.0296(9) 0.0465(11) -0.0025(9) -0.0043(8) 0.0035(7) C22 0.0246(9) 0.0352(10) 0.0519(13) 0.0007(10) -0.0090(8) -0.0044(8) C23 0.0351(11) 0.0248(9) 0.0499(12) -0.0048(9) -0.0124(9) -0.0037(8) C24 0.0274(9) 0.0249(8) 0.0310(9) -0.0032(8) -0.0049(7) 0.0022(7) 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' 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 178.4(2) . . ? C2 C3 C4 177.4(2) . . ? C5 C4 C3 178.5(2) . . ? C4 C5 C6 177.31(19) . . ? C5 C6 C13 109.67(14) . . ? C5 C6 C19 108.52(14) . . ? C13 C6 C19 109.36(14) . . ? C5 C6 C7 105.77(14) . . ? C13 C6 C7 111.35(14) . . ? C19 C6 C7 112.08(14) . . ? C8 C7 C12 118.77(17) . . ? C8 C7 C6 122.93(16) . . ? C12 C7 C6 118.22(17) . . ? C7 C8 C9 120.29(19) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.4(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 120.7(2) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C18 C13 C14 118.32(18) . . ? C18 C13 C6 121.23(15) . . ? C14 C13 C6 120.43(16) . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 120.3(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.90(19) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C24 C19 C20 118.66(16) . . ? C24 C19 C6 119.92(15) . . ? C20 C19 C6 121.33(15) . . ? C21 C20 C19 120.41(17) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 120.52(18) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.41(18) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 120.37(17) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 120.59(17) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? 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 C2 1.458(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.196(3) . ? C3 C4 1.381(2) . ? C4 C5 1.199(2) . ? C5 C6 1.481(2) . ? C6 C13 1.542(2) . ? C6 C19 1.546(2) . ? C6 C7 1.548(2) . ? C7 C8 1.384(3) . ? C7 C12 1.402(3) . ? C8 C9 1.398(3) . ? C8 H8 0.9500 . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.388(3) . ? C13 C14 1.389(2) . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C15 C16 1.378(4) . ? C15 H15 0.9500 . ? C16 C17 1.378(3) . ? C16 H16 0.9500 . ? C17 C18 1.388(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.390(2) . ? C19 C20 1.391(2) . ? C20 C21 1.390(3) . ? C20 H20 0.9500 . ? C21 C22 1.379(3) . ? C21 H21 0.9500 . ? C22 C23 1.382(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? C24 H24 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 C5 C6 C7 C8 114.66(18) . . . . ? C13 C6 C7 C8 -4.4(2) . . . . ? C19 C6 C7 C8 -127.26(17) . . . . ? C5 C6 C7 C12 -61.98(19) . . . . ? C13 C6 C7 C12 178.95(15) . . . . ? C19 C6 C7 C12 56.1(2) . . . . ? C12 C7 C8 C9 1.0(3) . . . . ? C6 C7 C8 C9 -175.64(16) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C7 -0.7(3) . . . . ? C8 C7 C12 C11 -0.3(3) . . . . ? C6 C7 C12 C11 176.47(17) . . . . ? C5 C6 C13 C18 152.78(16) . . . . ? C19 C6 C13 C18 33.9(2) . . . . ? C7 C6 C13 C18 -90.51(18) . . . . ? C5 C6 C13 C14 -29.1(2) . . . . ? C19 C6 C13 C14 -147.99(16) . . . . ? C7 C6 C13 C14 87.61(19) . . . . ? C18 C13 C14 C15 -1.9(3) . . . . ? C6 C13 C14 C15 179.98(16) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 -1.1(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C14 C13 C18 C17 0.8(3) . . . . ? C6 C13 C18 C17 178.99(18) . . . . ? C5 C6 C19 C24 -37.4(2) . . . . ? C13 C6 C19 C24 82.22(19) . . . . ? C7 C6 C19 C24 -153.81(16) . . . . ? C5 C6 C19 C20 146.07(16) . . . . ? C13 C6 C19 C20 -94.34(19) . . . . ? C7 C6 C19 C20 29.6(2) . . . . ? C24 C19 C20 C21 1.0(3) . . . . ? C6 C19 C20 C21 177.56(18) . . . . ? C19 C20 C21 C22 0.8(3) . . . . ? C20 C21 C22 C23 -1.7(3) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? C22 C23 C24 C19 0.8(3) . . . . ? C20 C19 C24 C23 -1.8(3) . . . . ? C6 C19 C24 C23 -178.40(18) . . . . ?