#------------------------------------------------------------------------------ #$Date: 2021-12-03 03:37:49 +0200 (Fri, 03 Dec 2021) $ #$Revision: 270997 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158430.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_7158430 loop_ _publ_author_name 'Baire, Beeraiah' 'Jampani, Santhi' _publ_section_title ; Ag(I)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes via a [4+2] cycloaddition of benzopyrylium ions: Access to structurally unique naphthalenes ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB02229F _journal_year 2021 _chemical_formula_moiety 'C34 H20 O2' _chemical_formula_sum 'C34 H20 O2' _chemical_formula_weight 460.50 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-11-14 deposited with the CCDC. 2021-12-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.472(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 31.9258(15) _cell_length_b 18.7977(9) _cell_length_c 8.2450(4) _cell_measurement_reflns_used 9993 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.63 _cell_measurement_theta_min 3.16 _cell_volume 4916.6(4) _computing_cell_refinement 'APEX3/SAINT (Bruker, 2016)' _computing_data_collection 'APEX3(Bruker, 2016)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2016)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker axs kappa apex3 CMOS Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 38103 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 3.314 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.7446 _exptl_absorpt_correction_T_min 0.7140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2016)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.244 _exptl_crystal_description block _exptl_crystal_F_000 1920 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.322 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 325 _refine_ls_number_reflns 4306 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0644 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0832P)^2^+3.8362P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1611 _refine_ls_wR_factor_ref 0.1763 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3169 _reflns_number_total 4306 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob02229f2.cif _cod_data_source_block SA8 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7158430 _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_estimated_absorpt_t_min 0.970 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; SA8.res created by SHELXL-2014/7 TITL sa8_a.res in C2/c CELL 0.71073 31.9258 18.7977 8.2450 90.000 96.472 90.000 ZERR 8.00 0.0015 0.0009 0.0004 0.000 0.002 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H O UNIT 272 160 16 MERG 2 OMIT -3.00 50.00 OMIT -3 1 1 DELU 0.005 C18 C34 FMAP 2 PLAN 20 SIZE 0.10 0.20 0.40 ACTA BOND $H CONF L.S. 10 TEMP 23.00 WGHT 0.083200 3.836200 FVAR 0.33896 C1 1 0.793060 0.563879 0.303557 11.00000 0.05646 0.05530 = 0.10250 -0.01278 0.01903 0.00368 AFIX 43 H1 2 0.801866 0.609013 0.275993 11.00000 -1.20000 AFIX 0 C2 1 0.816593 0.505718 0.271848 11.00000 0.06478 0.08190 = 0.12507 -0.02758 0.01714 0.01989 AFIX 43 H2 2 0.841154 0.511855 0.222588 11.00000 -1.20000 AFIX 0 C3 1 0.804809 0.440194 0.310616 11.00000 0.09254 0.07099 = 0.10760 -0.03428 -0.01088 0.03225 AFIX 43 H3 2 0.821211 0.401207 0.288794 11.00000 -1.20000 AFIX 0 C4 1 0.768824 0.430550 0.381991 11.00000 0.11945 0.03654 = 0.12631 -0.00436 -0.01341 -0.00090 AFIX 43 H4 2 0.760657 0.384937 0.408772 11.00000 -1.20000 AFIX 0 C5 1 0.744180 0.488795 0.415070 11.00000 0.07283 0.05956 = 0.11351 0.00490 0.01510 -0.00412 AFIX 43 H5 2 0.719524 0.482160 0.463433 11.00000 -1.20000 AFIX 0 C6 1 0.756524 0.556314 0.375752 11.00000 0.04449 0.04549 = 0.06130 -0.00830 -0.00123 0.00512 C7 1 0.732208 0.617809 0.406458 11.00000 0.04405 0.05392 = 0.06089 -0.00329 0.00439 0.00849 C8 1 0.712326 0.670217 0.426904 11.00000 0.04709 0.05614 = 0.06170 -0.00031 0.00891 0.01106 C9 1 0.687686 0.734286 0.441368 11.00000 0.03794 0.04393 = 0.05476 0.00504 0.00409 0.00779 C10 1 0.671629 0.747892 0.600921 11.00000 0.04450 0.03427 = 0.04699 0.00309 0.00172 0.00342 C11 1 0.695621 0.726789 0.743069 11.00000 0.05335 0.05307 = 0.05849 0.00751 -0.00497 0.01057 AFIX 43 H11 2 0.720118 0.700670 0.736621 11.00000 -1.20000 AFIX 0 C12 1 0.683854 0.743781 0.893565 11.00000 0.07250 0.06460 = 0.05019 0.00894 -0.00839 -0.00101 AFIX 43 H12 2 0.700515 0.729796 0.987998 11.00000 -1.20000 AFIX 0 C13 1 0.647461 0.781428 0.904094 11.00000 0.07206 0.06720 = 0.04443 -0.00230 0.00911 -0.00674 AFIX 43 H13 2 0.639371 0.793014 1.005712 11.00000 -1.20000 AFIX 0 C14 1 0.622883 0.802071 0.763606 11.00000 0.05370 0.05164 = 0.05538 -0.00294 0.01104 0.00360 AFIX 43 H14 2 0.598142 0.827250 0.771946 11.00000 -1.20000 AFIX 0 C15 1 0.634218 0.786143 0.610284 11.00000 0.04411 0.03423 = 0.04782 0.00266 0.00598 0.00078 C16 1 0.606359 0.809286 0.462647 11.00000 0.03610 0.04277 = 0.04935 0.00413 0.00848 0.01093 C17 1 0.599838 0.882205 0.434664 11.00000 0.04378 0.04430 = 0.06117 0.00452 0.01382 0.00925 AFIX 43 H17 2 0.613752 0.914445 0.507476 11.00000 -1.20000 AFIX 0 C18 1 0.573782 0.907925 0.304322 11.00000 0.04514 0.05367 = 0.05964 0.01814 0.02330 0.01732 C19 1 0.552058 0.860046 0.190689 11.00000 0.04215 0.07194 = 0.04792 0.02055 0.02180 0.02223 C20 1 0.523478 0.881340 0.055445 11.00000 0.05366 0.10161 = 0.04971 0.02903 0.02173 0.03003 AFIX 43 H20 2 0.519119 0.929598 0.035197 11.00000 -1.20000 AFIX 0 C21 1 0.502463 0.833540 -0.044529 11.00000 0.05828 0.13517 = 0.03819 0.02059 0.01200 0.03085 AFIX 43 H21 2 0.483615 0.849281 -0.131343 11.00000 -1.20000 AFIX 0 C22 1 0.508563 0.761055 -0.019721 11.00000 0.05871 0.12702 = 0.04067 -0.00913 0.00611 0.01074 AFIX 43 H22 2 0.494056 0.728664 -0.090505 11.00000 -1.20000 AFIX 0 C23 1 0.535975 0.737012 0.109127 11.00000 0.05759 0.08470 = 0.04593 -0.00445 0.00606 0.01219 AFIX 43 H23 2 0.540056 0.688404 0.124872 11.00000 -1.20000 AFIX 0 C24 1 0.557873 0.785600 0.217226 11.00000 0.03998 0.06610 = 0.04102 0.00474 0.01246 0.01354 C25 1 0.585340 0.761217 0.356527 11.00000 0.04208 0.04557 = 0.04413 0.00388 0.01031 0.01023 C26 1 0.589696 0.686366 0.385986 11.00000 0.04769 0.05250 = 0.04922 -0.00193 0.00066 0.00459 C27 1 0.592722 0.623848 0.408238 11.00000 0.06764 0.04788 = 0.06683 -0.00244 0.00665 0.00277 C28 1 0.596480 0.548562 0.430446 11.00000 0.09258 0.04652 = 0.09771 0.00333 0.03858 -0.00030 C29 1 0.630180 0.520581 0.532961 11.00000 0.09376 0.07821 = 0.16009 0.04850 0.05084 0.02872 AFIX 43 H29 2 0.649643 0.550846 0.589974 11.00000 -1.20000 AFIX 0 C30 1 0.634581 0.447479 0.549635 11.00000 0.13538 0.09755 = 0.26892 0.09279 0.12214 0.04792 AFIX 43 H30 2 0.657162 0.428170 0.616380 11.00000 -1.20000 AFIX 0 C31 1 0.604936 0.403956 0.465653 11.00000 0.23638 0.06237 = 0.29475 0.02684 0.19233 0.01519 AFIX 43 H31 2 0.608183 0.354911 0.475049 11.00000 -1.20000 AFIX 0 C32 1 0.571316 0.430102 0.370128 11.00000 0.23476 0.07481 = 0.21322 -0.02878 0.09401 -0.05649 AFIX 43 H32 2 0.551305 0.399610 0.317094 11.00000 -1.20000 AFIX 0 C33 1 0.567116 0.503703 0.352362 11.00000 0.15997 0.06793 = 0.14220 -0.01361 0.02827 -0.03607 AFIX 43 H33 2 0.544125 0.522383 0.286788 11.00000 -1.20000 AFIX 0 C34 1 0.570607 0.986734 0.298103 11.00000 0.07483 0.07070 = 0.07942 0.03431 0.03716 0.03873 AFIX 43 H34 2 0.584989 1.010964 0.385677 11.00000 -1.20000 AFIX 0 O1 3 0.681781 0.774184 0.325864 11.00000 0.06738 0.06739 = 0.06001 0.01892 0.01880 0.01895 O2 3 0.552304 1.022295 0.197004 11.00000 0.14494 0.08374 = 0.10577 0.03791 0.02712 0.04808 HKLF 4 REM sa8_a.res in C2/c REM R1 = 0.0644 for 3169 Fo > 4sig(Fo) and 0.0894 for all 4306 data REM 325 parameters refined using 1 restraints END WGHT 0.0826 3.9064 REM Highest difference peak 0.322, deepest hole -0.224, 1-sigma level 0.049 Q1 1 0.5885 1.0325 0.3224 11.00000 0.05 0.32 Q2 1 0.6100 0.6587 0.3559 11.00000 0.05 0.20 Q3 1 0.7053 0.6290 0.4607 11.00000 0.05 0.19 Q4 1 0.5269 0.6900 0.1626 11.00000 0.05 0.18 Q5 1 0.7106 0.6360 0.3308 11.00000 0.05 0.17 Q6 1 0.8868 0.5232 0.3142 11.00000 0.05 0.17 Q7 1 0.6715 0.7127 0.6693 11.00000 0.05 0.16 Q8 1 0.5692 0.6656 0.3449 11.00000 0.05 0.15 Q9 1 0.6212 0.5161 0.3930 11.00000 0.05 0.15 Q10 1 0.6470 0.7519 0.5903 11.00000 0.05 0.15 Q11 1 0.5186 0.6977 0.3187 11.00000 0.05 0.15 Q12 1 0.4900 0.6403 0.1159 11.00000 0.05 0.14 Q13 1 0.5156 0.6454 0.2576 11.00000 0.05 0.14 Q14 1 0.5609 0.9878 0.1271 11.00000 0.05 0.14 Q15 1 0.4705 0.6582 -0.0003 11.00000 0.05 0.14 Q16 1 0.5707 0.9909 0.1737 11.00000 0.05 0.14 Q17 1 0.4871 0.6883 -0.0627 11.00000 0.05 0.14 Q18 1 0.5817 0.9978 0.2056 11.00000 0.05 0.13 Q19 1 0.5853 1.0271 0.0866 11.00000 0.05 0.13 Q20 1 0.5594 0.7754 0.3143 11.00000 0.05 0.13 ; _shelx_res_checksum 92527 loop_ _space_group_symop_operation_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' 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 0.79306(9) 0.56388(15) 0.3036(4) 0.0707(8) Uani 1 1 d . . . . . H1 H 0.8019 0.6090 0.2760 0.085 Uiso 1 1 calc R U . . . C2 C 0.81659(11) 0.5057(2) 0.2718(5) 0.0901(11) Uani 1 1 d . . . . . H2 H 0.8412 0.5119 0.2226 0.108 Uiso 1 1 calc R U . . . C3 C 0.80481(13) 0.4402(2) 0.3106(5) 0.0921(11) Uani 1 1 d . . . . . H3 H 0.8212 0.4012 0.2888 0.110 Uiso 1 1 calc R U . . . C4 C 0.76882(14) 0.43055(16) 0.3820(5) 0.0962(12) Uani 1 1 d . . . . . H4 H 0.7607 0.3849 0.4088 0.115 Uiso 1 1 calc R U . . . C5 C 0.74418(11) 0.48880(16) 0.4151(4) 0.0816(9) Uani 1 1 d . . . . . H5 H 0.7195 0.4822 0.4634 0.098 Uiso 1 1 calc R U . . . C6 C 0.75652(7) 0.55631(12) 0.3758(3) 0.0510(6) Uani 1 1 d . . . . . C7 C 0.73221(8) 0.61781(13) 0.4065(3) 0.0531(6) Uani 1 1 d . . . . . C8 C 0.71233(8) 0.67022(14) 0.4269(3) 0.0548(6) Uani 1 1 d . . . . . C9 C 0.68769(7) 0.73429(12) 0.4414(3) 0.0456(6) Uani 1 1 d . . . . . C10 C 0.67163(7) 0.74789(11) 0.6009(3) 0.0422(5) Uani 1 1 d . . . . . C11 C 0.69562(8) 0.72679(13) 0.7431(3) 0.0558(7) Uani 1 1 d . . . . . H11 H 0.7201 0.7007 0.7366 0.067 Uiso 1 1 calc R U . . . C12 C 0.68385(9) 0.74378(15) 0.8936(3) 0.0636(7) Uani 1 1 d . . . . . H12 H 0.7005 0.7298 0.9880 0.076 Uiso 1 1 calc R U . . . C13 C 0.64746(9) 0.78143(14) 0.9041(3) 0.0610(7) Uani 1 1 d . . . . . H13 H 0.6394 0.7930 1.0057 0.073 Uiso 1 1 calc R U . . . C14 C 0.62288(8) 0.80207(13) 0.7636(3) 0.0532(6) Uani 1 1 d . . . . . H14 H 0.5981 0.8273 0.7719 0.064 Uiso 1 1 calc R U . . . C15 C 0.63422(7) 0.78614(11) 0.6103(3) 0.0420(5) Uani 1 1 d . . . . . C16 C 0.60636(7) 0.80929(12) 0.4626(3) 0.0425(5) Uani 1 1 d . . . . . C17 C 0.59984(7) 0.88221(12) 0.4347(3) 0.0491(6) Uani 1 1 d . . . . . H17 H 0.6138 0.9144 0.5075 0.059 Uiso 1 1 calc R U . . . C18 C 0.57378(7) 0.90792(13) 0.3043(3) 0.0515(6) Uani 1 1 d . U . . . C19 C 0.55206(7) 0.86005(14) 0.1907(3) 0.0527(7) Uani 1 1 d . . . . . C20 C 0.52348(9) 0.88134(18) 0.0554(3) 0.0671(8) Uani 1 1 d . . . . . H20 H 0.5191 0.9296 0.0352 0.081 Uiso 1 1 calc R U . . . C21 C 0.50246(9) 0.8335(2) -0.0445(3) 0.0767(10) Uani 1 1 d . . . . . H21 H 0.4836 0.8493 -0.1313 0.092 Uiso 1 1 calc R U . . . C22 C 0.50856(9) 0.7611(2) -0.0197(3) 0.0754(9) Uani 1 1 d . . . . . H22 H 0.4941 0.7287 -0.0905 0.091 Uiso 1 1 calc R U . . . C23 C 0.53598(8) 0.73701(17) 0.1091(3) 0.0627(7) Uani 1 1 d . . . . . H23 H 0.5401 0.6884 0.1249 0.075 Uiso 1 1 calc R U . . . C24 C 0.55787(7) 0.78560(13) 0.2172(3) 0.0484(6) Uani 1 1 d . . . . . C25 C 0.58534(7) 0.76122(12) 0.3565(3) 0.0435(5) Uani 1 1 d . . . . . C26 C 0.58970(7) 0.68637(13) 0.3860(3) 0.0502(6) Uani 1 1 d . . . . . C27 C 0.59272(9) 0.62385(14) 0.4082(3) 0.0609(7) Uani 1 1 d . . . . . C28 C 0.59648(11) 0.54856(15) 0.4304(4) 0.0768(9) Uani 1 1 d . . . . . C29 C 0.63018(13) 0.52058(19) 0.5330(6) 0.1079(14) Uani 1 1 d . . . . . H29 H 0.6496 0.5508 0.5900 0.129 Uiso 1 1 calc R U . . . C30 C 0.63458(19) 0.4475(3) 0.5496(9) 0.160(3) Uani 1 1 d . . . . . H30 H 0.6572 0.4282 0.6164 0.192 Uiso 1 1 calc R U . . . C31 C 0.6049(3) 0.4040(3) 0.4657(12) 0.185(4) Uani 1 1 d . . . . . H31 H 0.6082 0.3549 0.4750 0.223 Uiso 1 1 calc R U . . . C32 C 0.5713(3) 0.4301(3) 0.3701(9) 0.169(3) Uani 1 1 d . . . . . H32 H 0.5513 0.3996 0.3171 0.203 Uiso 1 1 calc R U . . . C33 C 0.56712(17) 0.5037(2) 0.3524(6) 0.1225(16) Uani 1 1 d . . . . . H33 H 0.5441 0.5224 0.2868 0.147 Uiso 1 1 calc R U . . . C34 C 0.57061(10) 0.98673(16) 0.2981(4) 0.0728(9) Uani 1 1 d . U . . . H34 H 0.5850 1.0110 0.3857 0.087 Uiso 1 1 calc R U . . . O1 O 0.68178(6) 0.77418(10) 0.3259(2) 0.0640(5) Uani 1 1 d . . . . . O2 O 0.55230(9) 1.02229(13) 0.1970(3) 0.1105(9) 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 C1 0.0565(17) 0.0553(16) 0.102(2) -0.0128(15) 0.0190(16) 0.0037(13) C2 0.065(2) 0.082(2) 0.125(3) -0.028(2) 0.0171(19) 0.0199(17) C3 0.093(3) 0.071(2) 0.108(3) -0.034(2) -0.011(2) 0.032(2) C4 0.119(3) 0.0365(16) 0.126(3) -0.0044(17) -0.013(3) -0.0009(18) C5 0.073(2) 0.0596(19) 0.114(3) 0.0049(17) 0.0151(18) -0.0041(15) C6 0.0445(13) 0.0455(14) 0.0613(15) -0.0083(11) -0.0012(11) 0.0051(11) C7 0.0440(13) 0.0539(15) 0.0609(16) -0.0033(12) 0.0044(11) 0.0085(12) C8 0.0471(14) 0.0561(15) 0.0617(16) -0.0003(12) 0.0089(12) 0.0111(12) C9 0.0379(12) 0.0439(13) 0.0548(14) 0.0050(11) 0.0041(10) 0.0078(10) C10 0.0445(12) 0.0343(11) 0.0470(13) 0.0031(9) 0.0017(10) 0.0034(9) C11 0.0534(15) 0.0531(15) 0.0585(16) 0.0075(12) -0.0050(12) 0.0106(12) C12 0.0725(19) 0.0646(17) 0.0502(16) 0.0089(13) -0.0084(13) -0.0010(14) C13 0.0721(18) 0.0672(17) 0.0444(15) -0.0023(12) 0.0091(13) -0.0067(14) C14 0.0537(14) 0.0516(14) 0.0554(15) -0.0029(12) 0.0110(12) 0.0036(11) C15 0.0441(12) 0.0342(11) 0.0478(13) 0.0027(9) 0.0060(10) 0.0008(10) C16 0.0361(12) 0.0428(12) 0.0494(13) 0.0041(10) 0.0085(10) 0.0109(10) C17 0.0438(13) 0.0443(13) 0.0612(15) 0.0045(11) 0.0138(11) 0.0092(10) C18 0.0451(13) 0.0537(14) 0.0596(15) 0.0181(12) 0.0233(12) 0.0173(11) C19 0.0422(13) 0.0719(17) 0.0479(14) 0.0206(13) 0.0218(11) 0.0222(12) C20 0.0537(16) 0.102(2) 0.0497(16) 0.0290(16) 0.0217(14) 0.0300(16) C21 0.0583(18) 0.135(3) 0.0382(15) 0.0206(18) 0.0120(13) 0.0308(19) C22 0.0587(17) 0.127(3) 0.0407(15) -0.0091(17) 0.0061(13) 0.0107(18) C23 0.0576(16) 0.085(2) 0.0459(14) -0.0045(14) 0.0061(13) 0.0122(14) C24 0.0400(12) 0.0661(16) 0.0410(13) 0.0047(11) 0.0125(10) 0.0135(11) C25 0.0421(12) 0.0456(13) 0.0441(13) 0.0039(10) 0.0103(10) 0.0102(10) C26 0.0477(14) 0.0525(16) 0.0492(14) -0.0019(11) 0.0007(11) 0.0046(11) C27 0.0676(17) 0.0479(16) 0.0668(17) -0.0024(13) 0.0066(14) 0.0028(13) C28 0.093(2) 0.0465(16) 0.098(2) 0.0033(16) 0.0386(19) -0.0003(16) C29 0.094(3) 0.078(2) 0.160(4) 0.048(2) 0.051(3) 0.029(2) C30 0.135(4) 0.098(3) 0.269(7) 0.093(4) 0.122(5) 0.048(3) C31 0.236(9) 0.062(3) 0.295(10) 0.027(4) 0.192(8) 0.015(4) C32 0.235(8) 0.075(4) 0.213(7) -0.029(4) 0.094(6) -0.056(4) C33 0.160(4) 0.068(2) 0.142(4) -0.014(2) 0.028(3) -0.036(3) C34 0.0748(19) 0.0707(18) 0.079(2) 0.0343(16) 0.0372(16) 0.0387(16) O1 0.0674(12) 0.0674(12) 0.0600(11) 0.0189(10) 0.0188(9) 0.0189(9) O2 0.145(2) 0.0837(16) 0.1058(19) 0.0379(14) 0.0271(17) 0.0481(16) 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' 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 C2 C1 C6 120.7(3) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C7 119.8(2) . . ? C5 C6 C7 121.8(2) . . ? C8 C7 C6 177.6(3) . . ? C7 C8 C9 176.6(3) . . ? O1 C9 C8 119.2(2) . . ? O1 C9 C10 123.4(2) . . ? C8 C9 C10 117.4(2) . . ? C11 C10 C15 119.6(2) . . ? C11 C10 C9 119.1(2) . . ? C15 C10 C9 121.14(19) . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.8(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 121.5(2) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C14 C15 C10 118.2(2) . . ? C14 C15 C16 119.3(2) . . ? C10 C15 C16 122.6(2) . . ? C25 C16 C17 118.9(2) . . ? C25 C16 C15 122.0(2) . . ? C17 C16 C15 119.0(2) . . ? C18 C17 C16 122.7(2) . . ? C18 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 C34 114.3(3) . . ? C19 C18 C34 125.6(2) . . ? C20 C19 C18 124.2(3) . . ? C20 C19 C24 117.4(3) . . ? C18 C19 C24 118.3(2) . . ? C21 C20 C19 121.7(3) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C20 C21 C22 120.9(3) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.3(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 119.6(2) . . ? C23 C24 C25 120.9(2) . . ? C19 C24 C25 119.5(2) . . ? C16 C25 C26 120.4(2) . . ? C16 C25 C24 120.5(2) . . ? C26 C25 C24 119.2(2) . . ? C27 C26 C25 178.8(3) . . ? C26 C27 C28 178.5(3) . . ? C33 C28 C29 119.6(4) . . ? C33 C28 C27 120.5(4) . . ? C29 C28 C27 119.9(3) . . ? C30 C29 C28 119.8(5) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 118.9(6) . . ? C31 C30 H30 120.6 . . ? C29 C30 H30 120.6 . . ? C32 C31 C30 122.2(5) . . ? C32 C31 H31 118.9 . . ? C30 C31 H31 118.9 . . ? C31 C32 C33 118.8(6) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C28 C33 C32 120.6(6) . . ? C28 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? O2 C34 C18 128.3(4) . . ? O2 C34 H34 115.8 . . ? C18 C34 H34 115.8 . . ? 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 C1 C2 1.368(4) . ? C1 C6 1.375(4) . ? C1 H1 0.9300 . ? C2 C3 1.337(5) . ? C2 H2 0.9300 . ? C3 C4 1.361(5) . ? C3 H3 0.9300 . ? C4 C5 1.393(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 H5 0.9300 . ? C6 C7 1.431(3) . ? C7 C8 1.194(3) . ? C8 C9 1.451(3) . ? C9 O1 1.210(3) . ? C9 C10 1.487(3) . ? C10 C11 1.384(3) . ? C10 C15 1.404(3) . ? C11 C12 1.374(4) . ? C11 H11 0.9300 . ? C12 C13 1.372(4) . ? C12 H12 0.9300 . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 C15 1.386(3) . ? C14 H14 0.9300 . ? C15 C16 1.489(3) . ? C16 C25 1.378(3) . ? C16 C17 1.402(3) . ? C17 C18 1.371(3) . ? C17 H17 0.9300 . ? C18 C19 1.422(4) . ? C18 C34 1.485(4) . ? C19 C20 1.417(4) . ? C19 C24 1.425(4) . ? C20 C21 1.346(5) . ? C20 H20 0.9300 . ? C21 C22 1.388(5) . ? C21 H21 0.9300 . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 C24 1.406(4) . ? C23 H23 0.9300 . ? C24 C25 1.439(3) . ? C25 C26 1.432(3) . ? C26 C27 1.192(3) . ? C27 C28 1.430(4) . ? C28 C33 1.367(5) . ? C28 C29 1.394(5) . ? C29 C30 1.387(6) . ? C29 H29 0.9300 . ? C30 C31 1.377(10) . ? C30 H30 0.9300 . ? C31 C32 1.350(10) . ? C31 H31 0.9300 . ? C32 C33 1.396(7) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 O2 1.172(3) . ? C34 H34 0.9300 . ? 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 C6 C1 C2 C3 -0.2(5) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C2 C1 C6 C5 -0.1(5) . . . . ? C2 C1 C6 C7 -179.4(3) . . . . ? C4 C5 C6 C1 0.4(5) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? O1 C9 C10 C11 -145.1(2) . . . . ? C8 C9 C10 C11 33.7(3) . . . . ? O1 C9 C10 C15 30.2(4) . . . . ? C8 C9 C10 C15 -151.0(2) . . . . ? C15 C10 C11 C12 -1.2(4) . . . . ? C9 C10 C11 C12 174.2(2) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? C13 C14 C15 C10 0.2(3) . . . . ? C13 C14 C15 C16 179.6(2) . . . . ? C11 C10 C15 C14 0.6(3) . . . . ? C9 C10 C15 C14 -174.7(2) . . . . ? C11 C10 C15 C16 -178.7(2) . . . . ? C9 C10 C15 C16 6.0(3) . . . . ? C14 C15 C16 C25 -114.2(2) . . . . ? C10 C15 C16 C25 65.2(3) . . . . ? C14 C15 C16 C17 63.0(3) . . . . ? C10 C15 C16 C17 -117.7(2) . . . . ? C25 C16 C17 C18 -1.0(3) . . . . ? C15 C16 C17 C18 -178.2(2) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C16 C17 C18 C34 179.0(2) . . . . ? C17 C18 C19 C20 177.9(2) . . . . ? C34 C18 C19 C20 -1.1(4) . . . . ? C17 C18 C19 C24 0.6(3) . . . . ? C34 C18 C19 C24 -178.4(2) . . . . ? C18 C19 C20 C21 -177.2(2) . . . . ? C24 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 -0.9(4) . . . . ? C20 C21 C22 C23 0.7(4) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C19 -1.1(3) . . . . ? C22 C23 C24 C25 177.4(2) . . . . ? C20 C19 C24 C23 0.9(3) . . . . ? C18 C19 C24 C23 178.4(2) . . . . ? C20 C19 C24 C25 -177.64(19) . . . . ? C18 C19 C24 C25 -0.1(3) . . . . ? C17 C16 C25 C26 -177.0(2) . . . . ? C15 C16 C25 C26 0.2(3) . . . . ? C17 C16 C25 C24 1.4(3) . . . . ? C15 C16 C25 C24 178.5(2) . . . . ? C23 C24 C25 C16 -179.4(2) . . . . ? C19 C24 C25 C16 -0.8(3) . . . . ? C23 C24 C25 C26 -1.0(3) . . . . ? C19 C24 C25 C26 177.5(2) . . . . ? C33 C28 C29 C30 2.6(6) . . . . ? C27 C28 C29 C30 -177.7(3) . . . . ? C28 C29 C30 C31 -1.0(7) . . . . ? C29 C30 C31 C32 -1.3(9) . . . . ? C30 C31 C32 C33 1.8(10) . . . . ? C29 C28 C33 C32 -2.1(6) . . . . ? C27 C28 C33 C32 178.2(4) . . . . ? C31 C32 C33 C28 -0.1(9) . . . . ? C17 C18 C34 O2 176.2(3) . . . . ? C19 C18 C34 O2 -4.8(4) . . . . ?