#------------------------------------------------------------------------------ #$Date: 2021-12-03 03:37:49 +0200 (Fri, 03 Dec 2021) $ #$Revision: 270997 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158428.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_7158428 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 'C30 H28 O2' _chemical_formula_sum 'C30 H28 O2' _chemical_formula_weight 420.52 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 73.101(2) _cell_angle_beta 82.359(2) _cell_angle_gamma 83.312(2) _cell_formula_units_Z 2 _cell_length_a 8.9341(4) _cell_length_b 10.7311(5) _cell_length_c 12.8284(5) _cell_measurement_reflns_used 3962 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.68 _cell_measurement_theta_min 2.92 _cell_volume 1162.40(9) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_unetI/netI 0.0272 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14444 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 1.668 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5(Bruker AXS.Inc)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.201 _exptl_crystal_description Block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.179 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.032 _refine_ls_extinction_coef 0.004(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 331 _refine_ls_number_reflns 4096 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0546 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0751P)^2^+0.3894P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1427 _refine_ls_wR_factor_ref 0.1833 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2402 _reflns_number_total 4096 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob02229f2.cif _cod_data_source_block 110_a _cod_database_code 7158428 _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 0.982 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; 110_a.res created by SHELXL-2014/7 TITL 110_a.res in P-1 CELL 0.71073 8.9341 10.7311 12.8284 73.101 82.359 83.312 ZERR 2.000 0.0004 0.0005 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H O UNIT 60 56 4 OMIT -3 50 L.S. 9 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.10 0.22 0.25 CONF SUMP 1.0 0.002 1. 2. 1. 3. CONF DFIX 1.52 0.002 C27A C28A C28A C29A C29A C30A DFIX 1.52 0.002 C26 C27 C27 C28 C28 C29 C29 C30 TEMP 23.000 WGHT 0.075100 0.389400 EXTI 0.004173 FVAR 0.59742 0.64225 0.35906 C1 1 0.737497 0.599626 0.422327 11.00000 0.06875 0.05594 = 0.05208 -0.01031 -0.00817 -0.01297 AFIX 43 H1 2 0.713619 0.679980 0.373037 11.00000 -1.20000 AFIX 0 C2 1 0.849612 0.518512 0.389367 11.00000 0.06273 0.06988 = 0.05305 -0.02108 -0.00119 -0.01308 C3 1 0.889489 0.394525 0.463244 11.00000 0.05044 0.07090 = 0.05915 -0.02712 -0.00645 -0.00574 C4 1 1.008308 0.308186 0.433354 11.00000 0.06263 0.09181 = 0.07750 -0.03638 0.00157 0.00153 AFIX 43 H4 2 1.062140 0.332906 0.364369 11.00000 -1.20000 AFIX 0 C5 1 1.045226 0.190415 0.503056 11.00000 0.06511 0.09646 = 0.10483 -0.04477 -0.01097 0.02164 AFIX 43 H5 2 1.123474 0.134944 0.481718 11.00000 -1.20000 AFIX 0 C6 1 0.967124 0.152814 0.605316 11.00000 0.07841 0.07700 = 0.09442 -0.02315 -0.01798 0.02186 AFIX 43 H6 2 0.992738 0.071726 0.652977 11.00000 -1.20000 AFIX 0 C7 1 0.852059 0.233552 0.637648 11.00000 0.06901 0.07504 = 0.06955 -0.01739 -0.00804 0.01006 AFIX 43 H7 2 0.800965 0.205934 0.707363 11.00000 -1.20000 AFIX 0 C8 1 0.808229 0.357581 0.568610 11.00000 0.05139 0.05491 = 0.05682 -0.01737 -0.01226 -0.00066 C9 1 0.685993 0.446276 0.601756 11.00000 0.04904 0.05089 = 0.04913 -0.01646 -0.01002 -0.00576 C10 1 0.595228 0.415225 0.706015 11.00000 0.05680 0.05056 = 0.05135 -0.01402 -0.00734 -0.00614 C11 1 0.485485 0.505174 0.732970 11.00000 0.06387 0.06041 = 0.05661 -0.02149 -0.00062 -0.00553 C12 1 0.455319 0.631634 0.659006 11.00000 0.06073 0.05274 = 0.07014 -0.02671 -0.00790 -0.00188 C13 1 0.340889 0.722598 0.686696 11.00000 0.08106 0.07285 = 0.09280 -0.03792 -0.00016 0.00761 AFIX 43 H13 2 0.284805 0.701207 0.755014 11.00000 -1.20000 AFIX 0 C14 1 0.312240 0.840787 0.614450 11.00000 0.09156 0.06728 = 0.12222 -0.04418 -0.01979 0.02036 AFIX 43 H14 2 0.237347 0.900313 0.633695 11.00000 -1.20000 AFIX 0 C15 1 0.393567 0.873076 0.512685 11.00000 0.09828 0.05454 = 0.10273 -0.02285 -0.03208 0.01120 AFIX 43 H15 2 0.372521 0.954072 0.463373 11.00000 -1.20000 AFIX 0 C16 1 0.504668 0.787405 0.483535 11.00000 0.08211 0.05777 = 0.07467 -0.01692 -0.01913 -0.00191 AFIX 43 H16 2 0.558703 0.811136 0.414560 11.00000 -1.20000 AFIX 0 C17 1 0.539164 0.663762 0.555800 11.00000 0.05765 0.04674 = 0.06135 -0.01757 -0.01592 -0.00411 C18 1 0.654512 0.569254 0.527432 11.00000 0.05318 0.04993 = 0.04923 -0.01437 -0.01236 -0.00757 C19 1 0.921250 0.570252 0.276554 11.00000 0.09644 0.09900 = 0.06730 -0.02607 0.01044 -0.02390 AFIX 43 H19 2 0.882305 0.652559 0.238154 11.00000 -1.20000 AFIX 0 C20 1 0.600301 0.283956 0.791516 11.00000 0.06419 0.06180 = 0.05524 -0.01534 -0.00256 -0.00570 C21 1 0.689617 0.268223 0.885247 11.00000 0.07980 0.07846 = 0.05824 -0.01210 -0.00964 -0.00971 AFIX 23 H21A 2 0.642168 0.326453 0.927664 11.00000 -1.20000 H21B 2 0.790273 0.295497 0.856455 11.00000 -1.20000 AFIX 0 C22 1 0.705008 0.130793 0.961335 11.00000 0.09855 0.09125 = 0.06693 -0.00202 -0.02021 -0.00668 AFIX 23 H22A 2 0.604588 0.100847 0.986028 11.00000 -1.20000 H22B 2 0.759563 0.073550 0.920369 11.00000 -1.20000 AFIX 0 C23 1 0.784167 0.118852 1.058241 11.00000 0.13706 0.12875 = 0.07891 -0.00805 -0.03548 -0.00216 AFIX 23 H23A 2 0.728333 0.174469 1.100206 11.00000 -1.20000 H23B 2 0.883766 0.150602 1.033640 11.00000 -1.20000 AFIX 0 C24 1 0.802274 -0.018819 1.132407 11.00000 0.17601 0.16024 = 0.10034 0.02515 -0.05876 -0.00536 AFIX 137 H24A 2 0.704128 -0.049141 1.161196 11.00000 -1.50000 H24B 2 0.857977 -0.019771 1.191715 11.00000 -1.50000 H24C 2 0.856223 -0.075034 1.091443 11.00000 -1.50000 AFIX 0 C25 1 0.393250 0.471521 0.836139 11.00000 0.08858 0.07464 = 0.07474 -0.02419 0.01021 -0.00120 C26 1 0.313711 0.447902 0.918493 11.00000 0.13976 0.08801 = 0.09000 -0.02145 0.04222 0.00148 PART 1 C27 1 0.181611 0.416410 1.006913 21.00000 0.12281 0.18166 = 0.06567 -0.00334 0.03450 0.03514 AFIX 23 H27A 2 0.176880 0.475730 1.051901 21.00000 -1.20000 H27B 2 0.088859 0.434144 0.971615 21.00000 -1.20000 AFIX 0 C28 1 0.185245 0.277651 1.081830 21.00000 0.13858 0.24913 = 0.08807 -0.03847 0.04300 -0.11609 AFIX 23 H28A 2 0.199925 0.214086 1.040152 21.00000 -1.20000 H28B 2 0.092854 0.263154 1.131252 21.00000 -1.20000 AFIX 0 C29 1 0.320916 0.271499 1.143605 21.00000 0.12931 0.19174 = 0.16348 -0.05696 -0.01510 -0.03784 AFIX 23 H29A 2 0.311151 0.344121 1.175405 21.00000 -1.20000 H29B 2 0.413383 0.276949 1.093980 21.00000 -1.20000 AFIX 0 C30 1 0.326881 0.142824 1.233386 21.00000 0.23468 0.19110 = 0.09022 0.01162 -0.04226 -0.08094 AFIX 137 H30A 2 0.226562 0.126191 1.268554 21.00000 -1.50000 H30B 2 0.390821 0.147694 1.286355 21.00000 -1.50000 H30C 2 0.367029 0.073323 1.201951 21.00000 -1.50000 PART 2 AFIX 0 C27A 1 0.268780 0.399191 1.047594 31.00000 0.08331 0.10139 = 0.11983 -0.02802 0.00870 -0.02119 AFIX 23 H27C 2 0.348209 0.411718 1.087400 31.00000 -1.20000 H27D 2 0.175055 0.445141 1.068975 31.00000 -1.20000 AFIX 0 C28A 1 0.249929 0.254805 1.068055 31.00000 0.20104 0.47466 = 0.12819 -0.12440 0.10120 -0.17783 AFIX 23 H28C 2 0.199965 0.244203 1.008867 31.00000 -1.20000 H28D 2 0.349662 0.208380 1.065928 31.00000 -1.20000 AFIX 0 C29A 1 0.159994 0.191965 1.176095 31.00000 0.21845 0.11104 = 0.12249 -0.00294 -0.00219 -0.01013 AFIX 23 H29C 2 0.092583 0.130398 1.169962 31.00000 -1.20000 H29D 2 0.104844 0.255313 1.210679 31.00000 -1.20000 AFIX 0 C30A 1 0.300598 0.125760 1.230640 31.00000 0.30321 0.08988 = 0.38021 -0.11106 -0.06752 0.03185 AFIX 137 H30D 2 0.330152 0.045435 1.211855 31.00000 -1.50000 H30E 2 0.278959 0.107645 1.308681 31.00000 -1.50000 H30F 2 0.381508 0.182373 1.205841 31.00000 -1.50000 PART 0 AFIX 0 O1 3 1.022662 0.520097 0.228293 11.00000 0.11294 0.14356 = 0.08360 -0.03945 0.03453 -0.01738 O2 3 0.525082 0.199955 0.785598 11.00000 0.09198 0.06749 = 0.08373 -0.01099 -0.01715 -0.01911 HKLF 4 REM 110_a.res in P-1 REM R1 = 0.0546 for 2402 Fo > 4sig(Fo) and 0.0982 for all 4096 data REM 331 parameters refined using 8 restraints END WGHT 0.0752 0.3878 REM Highest difference peak 0.179, deepest hole -0.164, 1-sigma level 0.032 Q1 1 0.2426 0.1593 1.1119 11.00000 0.05 0.18 Q2 1 0.8597 0.2013 1.0608 11.00000 0.05 0.18 Q3 1 0.1993 0.3042 1.0868 11.00000 0.05 0.14 Q4 1 1.0223 0.3776 0.3126 11.00000 0.05 0.14 Q5 1 0.0937 0.2969 1.0006 11.00000 0.05 0.14 ; _shelx_res_checksum 10995 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.7375(3) 0.5996(2) 0.42233(18) 0.0591(6) Uani 1 1 d . . . . . H1 H 0.7136 0.6800 0.3730 0.071 Uiso 1 1 calc R U . . . C2 C 0.8496(3) 0.5185(2) 0.38937(18) 0.0609(6) Uani 1 1 d . . . . . C3 C 0.8895(2) 0.3945(2) 0.46324(19) 0.0581(6) Uani 1 1 d . . . . . C4 C 1.0083(3) 0.3082(3) 0.4334(2) 0.0761(8) Uani 1 1 d . . . . . H4 H 1.0621 0.3329 0.3644 0.091 Uiso 1 1 calc R U . . . C5 C 1.0452(3) 0.1904(3) 0.5031(3) 0.0874(9) Uani 1 1 d . . . . . H5 H 1.1235 0.1349 0.4817 0.105 Uiso 1 1 calc R U . . . C6 C 0.9671(3) 0.1528(3) 0.6053(3) 0.0849(8) Uani 1 1 d . . . . . H6 H 0.9927 0.0717 0.6530 0.102 Uiso 1 1 calc R U . . . C7 C 0.8521(3) 0.2336(3) 0.6376(2) 0.0730(7) Uani 1 1 d . . . . . H7 H 0.8010 0.2059 0.7074 0.088 Uiso 1 1 calc R U . . . C8 C 0.8082(2) 0.3576(2) 0.56861(18) 0.0537(6) Uani 1 1 d . . . . . C9 C 0.6860(2) 0.4463(2) 0.60176(16) 0.0486(5) Uani 1 1 d . . . . . C10 C 0.5952(2) 0.4152(2) 0.70602(17) 0.0526(5) Uani 1 1 d . . . . . C11 C 0.4855(3) 0.5052(2) 0.73297(18) 0.0597(6) Uani 1 1 d . . . . . C12 C 0.4553(3) 0.6316(2) 0.6590(2) 0.0593(6) Uani 1 1 d . . . . . C13 C 0.3409(3) 0.7226(3) 0.6867(3) 0.0811(8) Uani 1 1 d . . . . . H13 H 0.2848 0.7012 0.7550 0.097 Uiso 1 1 calc R U . . . C14 C 0.3122(4) 0.8408(3) 0.6144(3) 0.0913(9) Uani 1 1 d . . . . . H14 H 0.2373 0.9003 0.6337 0.110 Uiso 1 1 calc R U . . . C15 C 0.3936(4) 0.8731(3) 0.5127(3) 0.0844(8) Uani 1 1 d . . . . . H15 H 0.3725 0.9541 0.4634 0.101 Uiso 1 1 calc R U . . . C16 C 0.5047(3) 0.7874(2) 0.4835(2) 0.0711(7) Uani 1 1 d . . . . . H16 H 0.5587 0.8111 0.4146 0.085 Uiso 1 1 calc R U . . . C17 C 0.5392(2) 0.6638(2) 0.55580(18) 0.0538(6) Uani 1 1 d . . . . . C18 C 0.6545(2) 0.5693(2) 0.52743(17) 0.0497(5) Uani 1 1 d . . . . . C19 C 0.9213(4) 0.5703(3) 0.2766(2) 0.0875(8) Uani 1 1 d . . . . . H19 H 0.8823 0.6526 0.2382 0.105 Uiso 1 1 calc R U . . . C20 C 0.6003(3) 0.2840(2) 0.79152(19) 0.0609(6) Uani 1 1 d . . . . . C21 C 0.6896(3) 0.2682(3) 0.88525(19) 0.0732(7) Uani 1 1 d . . . . . H21A H 0.6422 0.3265 0.9277 0.088 Uiso 1 1 calc R U . . . H21B H 0.7903 0.2955 0.8565 0.088 Uiso 1 1 calc R U . . . C22 C 0.7050(3) 0.1308(3) 0.9613(2) 0.0889(9) Uani 1 1 d . . . . . H22A H 0.6046 0.1008 0.9860 0.107 Uiso 1 1 calc R U . . . H22B H 0.7596 0.0735 0.9204 0.107 Uiso 1 1 calc R U . . . C23 C 0.7842(5) 0.1189(4) 1.0582(3) 0.1178(12) Uani 1 1 d . . . . . H23A H 0.7283 0.1745 1.1002 0.141 Uiso 1 1 calc R U . . . H23B H 0.8838 0.1506 1.0336 0.141 Uiso 1 1 calc R U . . . C24 C 0.8023(5) -0.0188(4) 1.1324(3) 0.1552(17) Uani 1 1 d . . . . . H24A H 0.7041 -0.0491 1.1612 0.233 Uiso 1 1 calc R U . . . H24B H 0.8580 -0.0198 1.1917 0.233 Uiso 1 1 calc R U . . . H24C H 0.8562 -0.0750 1.0914 0.233 Uiso 1 1 calc R U . . . C25 C 0.3932(3) 0.4715(3) 0.8361(2) 0.0808(8) Uani 1 1 d . . . . . C26 C 0.3137(4) 0.4479(3) 0.9185(3) 0.1127(12) Uani 1 1 d D . . . . C27 C 0.1816(8) 0.4164(8) 1.0069(5) 0.138(3) Uani 0.642(9) 1 d D . P A 1 H27A H 0.1769 0.4757 1.0519 0.166 Uiso 0.642(9) 1 calc R U P A 1 H27B H 0.0889 0.4341 0.9716 0.166 Uiso 0.642(9) 1 calc R U P A 1 C28 C 0.1852(10) 0.2777(8) 1.0818(7) 0.157(5) Uani 0.642(9) 1 d D . P A 1 H28A H 0.1999 0.2141 1.0402 0.189 Uiso 0.642(9) 1 calc R U P A 1 H28B H 0.0929 0.2632 1.1313 0.189 Uiso 0.642(9) 1 calc R U P A 1 C29 C 0.3209(8) 0.2715(8) 1.1436(8) 0.158(4) Uani 0.642(9) 1 d D . P A 1 H29A H 0.3112 0.3441 1.1754 0.190 Uiso 0.642(9) 1 calc R U P A 1 H29B H 0.4134 0.2769 1.0940 0.190 Uiso 0.642(9) 1 calc R U P A 1 C30 C 0.3269(16) 0.1428(10) 1.2334(7) 0.175(6) Uani 0.642(9) 1 d D . P A 1 H30A H 0.2266 0.1262 1.2686 0.263 Uiso 0.642(9) 1 calc R U P A 1 H30B H 0.3908 0.1477 1.2864 0.263 Uiso 0.642(9) 1 calc R U P A 1 H30C H 0.3670 0.0733 1.2020 0.263 Uiso 0.642(9) 1 calc R U P A 1 C27A C 0.2688(14) 0.3992(12) 1.0476(10) 0.103(4) Uani 0.359(9) 1 d D . P A 2 H27C H 0.3482 0.4117 1.0874 0.123 Uiso 0.359(9) 1 calc R U P A 2 H27D H 0.1751 0.4451 1.0690 0.123 Uiso 0.359(9) 1 calc R U P A 2 C28A C 0.250(3) 0.2548(13) 1.0681(17) 0.258(19) Uani 0.359(9) 1 d D . P A 2 H28C H 0.2000 0.2442 1.0089 0.310 Uiso 0.359(9) 1 calc R U P A 2 H28D H 0.3497 0.2084 1.0659 0.310 Uiso 0.359(9) 1 calc R U P A 2 C29A C 0.1600(18) 0.1920(14) 1.1761(11) 0.159(7) Uani 0.359(9) 1 d D . P A 2 H29C H 0.0926 0.1304 1.1700 0.191 Uiso 0.359(9) 1 calc R U P A 2 H29D H 0.1048 0.2553 1.2107 0.191 Uiso 0.359(9) 1 calc R U P A 2 C30A C 0.301(3) 0.1258(17) 1.231(2) 0.25(2) Uani 0.359(9) 1 d D . P A 2 H30D H 0.3302 0.0454 1.2119 0.374 Uiso 0.359(9) 1 calc R U P A 2 H30E H 0.2790 0.1076 1.3087 0.374 Uiso 0.359(9) 1 calc R U P A 2 H30F H 0.3815 0.1824 1.2058 0.374 Uiso 0.359(9) 1 calc R U P A 2 O1 O 1.0227(3) 0.5201(2) 0.22829(18) 0.1154(8) Uani 1 1 d . . . . . O2 O 0.5251(2) 0.19995(17) 0.78560(15) 0.0814(6) 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 0.0688(15) 0.0559(14) 0.0521(13) -0.0103(11) -0.0082(11) -0.0130(12) C2 0.0627(14) 0.0699(16) 0.0530(13) -0.0211(12) -0.0012(11) -0.0131(12) C3 0.0504(12) 0.0709(16) 0.0591(14) -0.0271(13) -0.0065(11) -0.0057(11) C4 0.0626(15) 0.092(2) 0.0775(18) -0.0364(16) 0.0016(13) 0.0015(14) C5 0.0651(17) 0.096(2) 0.105(2) -0.045(2) -0.0110(16) 0.0216(15) C6 0.0784(18) 0.0770(19) 0.094(2) -0.0232(16) -0.0180(17) 0.0219(15) C7 0.0690(16) 0.0750(18) 0.0695(16) -0.0174(14) -0.0080(13) 0.0101(13) C8 0.0514(12) 0.0549(14) 0.0568(13) -0.0174(11) -0.0123(10) -0.0007(10) C9 0.0490(12) 0.0509(13) 0.0491(12) -0.0165(10) -0.0100(10) -0.0058(10) C10 0.0568(13) 0.0506(13) 0.0513(12) -0.0140(10) -0.0073(10) -0.0061(10) C11 0.0639(14) 0.0604(15) 0.0566(14) -0.0215(12) -0.0006(11) -0.0055(11) C12 0.0607(14) 0.0527(14) 0.0701(15) -0.0267(12) -0.0079(12) -0.0019(11) C13 0.0811(18) 0.0729(19) 0.093(2) -0.0379(16) -0.0002(15) 0.0076(14) C14 0.092(2) 0.067(2) 0.122(3) -0.0442(19) -0.020(2) 0.0204(15) C15 0.098(2) 0.0545(16) 0.103(2) -0.0229(16) -0.0321(19) 0.0112(15) C16 0.0821(17) 0.0578(16) 0.0747(17) -0.0169(13) -0.0191(14) -0.0019(13) C17 0.0576(13) 0.0467(13) 0.0613(14) -0.0176(11) -0.0159(11) -0.0041(10) C18 0.0532(12) 0.0499(13) 0.0492(12) -0.0144(10) -0.0124(10) -0.0076(10) C19 0.096(2) 0.099(2) 0.0673(17) -0.0261(16) 0.0104(16) -0.0239(17) C20 0.0642(14) 0.0618(15) 0.0552(14) -0.0153(12) -0.0026(11) -0.0057(12) C21 0.0798(17) 0.0785(18) 0.0582(15) -0.0121(13) -0.0096(13) -0.0097(13) C22 0.099(2) 0.091(2) 0.0669(17) -0.0020(15) -0.0202(15) -0.0067(16) C23 0.137(3) 0.129(3) 0.079(2) -0.008(2) -0.035(2) -0.002(2) C24 0.176(4) 0.160(4) 0.100(3) 0.025(3) -0.059(3) -0.005(3) C25 0.0886(19) 0.0746(18) 0.0747(18) -0.0242(15) 0.0102(16) -0.0012(14) C26 0.140(3) 0.088(2) 0.090(2) -0.0215(18) 0.042(2) 0.001(2) C27 0.123(6) 0.182(7) 0.066(4) -0.003(4) 0.034(4) 0.035(6) C28 0.139(7) 0.249(11) 0.088(7) -0.038(7) 0.043(5) -0.116(7) C29 0.129(6) 0.192(10) 0.163(8) -0.057(8) -0.015(5) -0.038(6) C30 0.235(13) 0.191(13) 0.090(5) 0.012(6) -0.042(6) -0.081(10) C27A 0.083(7) 0.101(9) 0.120(10) -0.028(7) 0.009(6) -0.021(7) C28A 0.20(2) 0.47(5) 0.128(17) -0.12(3) 0.101(18) -0.18(3) C29A 0.218(17) 0.111(10) 0.122(11) -0.003(8) -0.002(11) -0.010(10) C30A 0.30(4) 0.090(13) 0.38(4) -0.11(2) -0.07(3) 0.032(16) O1 0.1129(17) 0.144(2) 0.0836(14) -0.0394(14) 0.0345(13) -0.0174(14) O2 0.0920(13) 0.0675(12) 0.0837(13) -0.0110(10) -0.0172(10) -0.0191(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' 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 C18 123.9(2) . . ? C2 C1 H1 118.0 . . ? C18 C1 H1 118.0 . . ? C1 C2 C3 119.5(2) . . ? C1 C2 C19 114.8(2) . . ? C3 C2 C19 125.8(2) . . ? C4 C3 C8 119.4(2) . . ? C4 C3 C2 121.4(2) . . ? C8 C3 C2 119.2(2) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 122.1(3) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C7 C8 C3 116.6(2) . . ? C7 C8 C9 123.1(2) . . ? C3 C8 C9 120.3(2) . . ? C18 C9 C10 117.70(19) . . ? C18 C9 C8 118.36(19) . . ? C10 C9 C8 123.94(19) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 C20 113.59(19) . . ? C9 C10 C20 125.56(19) . . ? C10 C11 C12 121.9(2) . . ? C10 C11 C25 120.0(2) . . ? C12 C11 C25 118.0(2) . . ? C17 C12 C13 119.7(2) . . ? C17 C12 C11 118.77(19) . . ? C13 C12 C11 121.5(2) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 121.3(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 117.7(2) . . ? C12 C17 C18 119.3(2) . . ? C16 C17 C18 123.0(2) . . ? C9 C18 C1 118.73(19) . . ? C9 C18 C17 121.51(19) . . ? C1 C18 C17 119.8(2) . . ? O1 C19 C2 128.4(3) . . ? O1 C19 H19 115.8 . . ? C2 C19 H19 115.8 . . ? O2 C20 C21 122.7(2) . . ? O2 C20 C10 119.7(2) . . ? C21 C20 C10 117.4(2) . . ? C20 C21 C22 115.0(2) . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C23 C22 C21 114.3(3) . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C21 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C24 114.0(3) . . ? C22 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? C22 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C11 177.3(3) . . ? C25 C26 C27 165.8(5) . . ? C25 C26 C27A 157.5(6) . . ? C28 C27 C26 116.4(5) . . ? C28 C27 H27A 108.2 . . ? C26 C27 H27A 108.2 . . ? C28 C27 H27B 108.2 . . ? C26 C27 H27B 108.2 . . ? H27A C27 H27B 107.3 . . ? C27 C28 C29 102.2(6) . . ? C27 C28 H28A 111.3 . . ? C29 C28 H28A 111.3 . . ? C27 C28 H28B 111.3 . . ? C29 C28 H28B 111.3 . . ? H28A C28 H28B 109.2 . . ? C28 C29 C30 108.3(6) . . ? C28 C29 H29A 110.0 . . ? C30 C29 H29A 110.0 . . ? C28 C29 H29B 110.0 . . ? C30 C29 H29B 110.0 . . ? H29A C29 H29B 108.4 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28A C27A C26 103.3(9) . . ? C28A C27A H27C 111.1 . . ? C26 C27A H27C 111.1 . . ? C28A C27A H27D 111.1 . . ? C26 C27A H27D 111.1 . . ? H27C C27A H27D 109.1 . . ? C29A C28A C27A 114.8(12) . . ? C29A C28A H28C 108.6 . . ? C27A C28A H28C 108.6 . . ? C29A C28A H28D 108.6 . . ? C27A C28A H28D 108.6 . . ? H28C C28A H28D 107.6 . . ? C28A C29A C30A 93.5(18) . . ? C28A C29A H29C 113.0 . . ? C30A C29A H29C 113.0 . . ? C28A C29A H29D 113.0 . . ? C30A C29A H29D 113.0 . . ? H29C C29A H29D 110.4 . . ? C29A C30A H30D 109.5 . . ? C29A C30A H30E 109.5 . . ? H30D C30A H30E 109.5 . . ? C29A C30A H30F 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 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 C1 C2 1.356(3) . ? C1 C18 1.417(3) . ? C1 H1 0.9300 . ? C2 C3 1.429(3) . ? C2 C19 1.477(4) . ? C3 C4 1.415(3) . ? C3 C8 1.416(3) . ? C4 C5 1.353(4) . ? C4 H4 0.9300 . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 C7 1.367(3) . ? C6 H6 0.9300 . ? C7 C8 1.412(3) . ? C7 H7 0.9300 . ? C8 C9 1.466(3) . ? C9 C18 1.408(3) . ? C9 C10 1.440(3) . ? C10 C11 1.377(3) . ? C10 C20 1.513(3) . ? C11 C12 1.431(3) . ? C11 C25 1.436(3) . ? C12 C17 1.401(3) . ? C12 C13 1.413(3) . ? C13 C14 1.355(4) . ? C13 H13 0.9300 . ? C14 C15 1.377(4) . ? C14 H14 0.9300 . ? C15 C16 1.363(4) . ? C15 H15 0.9300 . ? C16 C17 1.407(3) . ? C16 H16 0.9300 . ? C17 C18 1.447(3) . ? C19 O1 1.194(3) . ? C19 H19 0.9300 . ? C20 O2 1.210(3) . ? C20 C21 1.489(3) . ? C21 C22 1.516(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.477(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.511(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.171(4) . ? C26 C27 1.519(2) . ? C26 C27A 1.596(12) . ? C27 C28 1.519(2) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.519(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.520(2) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C27A C28A 1.520(2) . ? C27A H27C 0.9700 . ? C27A H27D 0.9700 . ? C28A C29A 1.519(2) . ? C28A H28C 0.9700 . ? C28A H28D 0.9700 . ? C29A C30A 1.520(2) . ? C29A H29C 0.9700 . ? C29A H29D 0.9700 . ? C30A H30D 0.9600 . ? C30A H30E 0.9600 . ? C30A H30F 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 C18 C1 C2 C3 -0.2(3) . . . . ? C18 C1 C2 C19 -179.8(2) . . . . ? C1 C2 C3 C4 -178.4(2) . . . . ? C19 C2 C3 C4 1.1(4) . . . . ? C1 C2 C3 C8 1.6(3) . . . . ? C19 C2 C3 C8 -178.9(2) . . . . ? C8 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 C5 -179.5(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C3 0.2(4) . . . . ? C6 C7 C8 C9 -179.5(2) . . . . ? C4 C3 C8 C7 -0.5(3) . . . . ? C2 C3 C8 C7 179.5(2) . . . . ? C4 C3 C8 C9 179.21(19) . . . . ? C2 C3 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C18 178.3(2) . . . . ? C3 C8 C9 C18 -1.5(3) . . . . ? C7 C8 C9 C10 -2.0(3) . . . . ? C3 C8 C9 C10 178.34(19) . . . . ? C18 C9 C10 C11 -2.4(3) . . . . ? C8 C9 C10 C11 177.84(19) . . . . ? C18 C9 C10 C20 173.20(19) . . . . ? C8 C9 C10 C20 -6.6(3) . . . . ? C9 C10 C11 C12 0.9(3) . . . . ? C20 C10 C11 C12 -175.2(2) . . . . ? C9 C10 C11 C25 178.4(2) . . . . ? C20 C10 C11 C25 2.3(3) . . . . ? C10 C11 C12 C17 0.7(3) . . . . ? C25 C11 C12 C17 -176.9(2) . . . . ? C10 C11 C12 C13 179.0(2) . . . . ? C25 C11 C12 C13 1.4(3) . . . . ? C17 C12 C13 C14 -0.3(4) . . . . ? C11 C12 C13 C14 -178.6(2) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C13 C14 C15 C16 -0.6(5) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? C13 C12 C17 C16 0.1(3) . . . . ? C11 C12 C17 C16 178.4(2) . . . . ? C13 C12 C17 C18 -179.0(2) . . . . ? C11 C12 C17 C18 -0.7(3) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? C15 C16 C17 C18 179.0(2) . . . . ? C10 C9 C18 C1 -177.05(18) . . . . ? C8 C9 C18 C1 2.8(3) . . . . ? C10 C9 C18 C17 2.4(3) . . . . ? C8 C9 C18 C17 -177.80(17) . . . . ? C2 C1 C18 C9 -2.0(3) . . . . ? C2 C1 C18 C17 178.5(2) . . . . ? C12 C17 C18 C9 -0.9(3) . . . . ? C16 C17 C18 C9 -179.9(2) . . . . ? C12 C17 C18 C1 178.53(19) . . . . ? C16 C17 C18 C1 -0.5(3) . . . . ? C1 C2 C19 O1 179.0(3) . . . . ? C3 C2 C19 O1 -0.5(5) . . . . ? C11 C10 C20 O2 90.6(3) . . . . ? C9 C10 C20 O2 -85.3(3) . . . . ? C11 C10 C20 C21 -84.6(3) . . . . ? C9 C10 C20 C21 99.6(3) . . . . ? O2 C20 C21 C22 11.5(4) . . . . ? C10 C20 C21 C22 -173.5(2) . . . . ? C20 C21 C22 C23 -175.7(3) . . . . ? C21 C22 C23 C24 -178.7(3) . . . . ? C25 C26 C27 C28 106.3(17) . . . . ? C26 C27 C28 C29 66.5(11) . . . . ? C27 C28 C29 C30 172.6(8) . . . . ? C25 C26 C27A C28A -90.1(18) . . . . ? C26 C27A C28A C29A -161(2) . . . . ? C27A C28A C29A C30A -103(2) . . . . ?