#------------------------------------------------------------------------------ #$Date: 2024-06-29 01:08:07 +0300 (Sat, 29 Jun 2024) $ #$Revision: 292643 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572007.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_1572007 loop_ _publ_author_name 'Guo, Jianwen' 'Du, Fangxin' 'Yu, Bo' 'Du, Pengcheng' 'Li, Haoyuan' 'Zhang, Jianhua' 'Xin, Hanshen' _publ_section_title ; Heptacyclic Aromatic Hydrocarbon Isomers with Two Azulene Units Fused ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02566K _journal_year 2024 _chemical_formula_moiety 'C46 H50' _chemical_formula_sum 'C46 H50' _chemical_formula_weight 602.86 _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 _atom_sites_solution_primary iterative _audit_creation_date 2024-01-19 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-02-29 deposited with the CCDC. 2024-06-27 downloaded from the CCDC. ; _cell_angle_alpha 101.504(3) _cell_angle_beta 95.881(2) _cell_angle_gamma 94.474(2) _cell_formula_units_Z 1 _cell_length_a 5.4401(2) _cell_length_b 9.1230(3) _cell_length_c 17.9486(6) _cell_measurement_reflns_used 2430 _cell_measurement_temperature 193.00 _cell_measurement_theta_max 68.01 _cell_measurement_theta_min 4.97 _cell_volume 863.86(5) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_temperature 193.00 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_unetI/netI 0.0397 _diffrn_reflns_Laue_measured_fraction_full 0.981 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8555 _diffrn_reflns_point_group_measured_fraction_full 0.981 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.185 _diffrn_reflns_theta_min 4.972 _diffrn_source_current 1.1 _diffrn_source_power 0.05500000000000001 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.483 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.6553 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0733 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8701. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'dull brownish brown' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier brownish _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 1.159 _exptl_crystal_description plate _exptl_crystal_F_000 326 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.233 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3101 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0479 _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^)+(0.0750P)^2^+0.1384P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1288 _refine_ls_wR_factor_ref 0.1381 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2423 _reflns_number_total 3101 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02566k2.cif _cod_data_source_block cu_azac_2_0m_a _cod_database_code 1572007 _shelx_shelxl_version_number 2018/3 _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_max 0.949 _shelx_estimated_absorpt_t_min 0.940 _olex2_refinement_description ; 1.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B) 1.b Aromatic/amide H refined with riding coordinates: C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22) 1.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL cu_AzAc_2_0m_a.res in P-1 cu_azac_2_0m_a.res created by SHELXL-2018/3 at 17:16:29 on 16-Jan-2024 REM Old TITL cu_AzAc_2_0m in P-1 REM SHELXT solution in P-1: R1 0.138, Rweak 0.005, Alpha 0.043 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C23 CELL 1.54178 5.4401 9.123 17.9486 101.504 95.881 94.474 ZERR 1 0.0002 0.0003 0.0006 0.003 0.002 0.002 LATT 1 SFAC C H UNIT 46 50 L.S. 5 PLAN 2 SIZE 0.11 0.12 0.13 TEMP -80.15 CONF LIST 4 MORE -1 BOND $H fmap 2 acta OMIT -3 -2 6 REM REM REM WGHT 0.075000 0.138400 FVAR 0.77157 C1 1 1.463158 0.811465 0.605278 11.00000 0.05622 0.23319 = 0.05224 0.03314 -0.00718 0.01155 AFIX 137 H1A 2 1.612347 0.791639 0.580139 11.00000 -1.50000 H1B 2 1.469306 0.768201 0.651137 11.00000 -1.50000 H1C 2 1.455559 0.920253 0.619931 11.00000 -1.50000 AFIX 0 C2 1 1.239776 0.742367 0.551794 11.00000 0.08206 0.14285 = 0.04899 0.03034 -0.01264 0.00668 AFIX 23 H2A 2 1.092178 0.757175 0.579393 11.00000 -1.20000 H2B 2 1.251115 0.632746 0.537590 11.00000 -1.20000 AFIX 0 C3 1 1.197814 0.800816 0.479334 11.00000 0.05206 0.09220 = 0.03702 0.00812 -0.00239 0.00949 AFIX 23 H3A 2 1.345380 0.786883 0.451643 11.00000 -1.20000 H3B 2 1.183420 0.910148 0.493190 11.00000 -1.20000 AFIX 0 C4 1 0.969820 0.726460 0.425796 11.00000 0.05748 0.07325 = 0.03920 0.01454 -0.00155 0.00020 AFIX 23 H4A 2 0.982029 0.616764 0.413310 11.00000 -1.20000 H4B 2 0.821993 0.742959 0.453117 11.00000 -1.20000 AFIX 0 C5 1 0.929734 0.780946 0.351978 11.00000 0.04455 0.04470 = 0.03281 0.00301 0.00003 0.00217 AFIX 23 H5A 2 1.078319 0.766355 0.324833 11.00000 -1.20000 H5B 2 0.912596 0.890111 0.364101 11.00000 -1.20000 AFIX 0 C6 1 0.701514 0.701039 0.298752 11.00000 0.03696 0.04106 = 0.03217 0.00495 0.00460 0.00156 AFIX 23 H6A 2 0.707583 0.591076 0.292156 11.00000 -1.20000 H6B 2 0.550916 0.726852 0.323102 11.00000 -1.20000 AFIX 0 C7 1 0.680210 0.741424 0.220386 11.00000 0.03452 0.02732 = 0.03287 0.00346 0.00400 0.00081 AFIX 23 H7A 2 0.836860 0.723560 0.197991 11.00000 -1.20000 H7B 2 0.660731 0.850063 0.226827 11.00000 -1.20000 AFIX 0 C8 1 0.462683 0.652593 0.163895 11.00000 0.02786 0.02855 = 0.03066 0.00545 0.00350 0.00487 AFIX 23 H8A 2 0.305902 0.670375 0.186225 11.00000 -1.20000 H8B 2 0.454399 0.691477 0.116089 11.00000 -1.20000 AFIX 0 C9 1 0.481757 0.485973 0.144402 11.00000 0.02494 0.02828 = 0.02697 0.00504 -0.00108 0.00120 C10 1 0.347202 0.379149 0.174119 11.00000 0.02563 0.03102 = 0.02666 0.00409 -0.00192 0.00127 C11 1 0.166978 0.407583 0.224483 11.00000 0.03227 0.03371 = 0.03413 0.00547 0.00415 0.00390 AFIX 43 H11 2 0.138259 0.510129 0.239324 11.00000 -1.20000 AFIX 0 C12 1 0.025288 0.308034 0.255603 11.00000 0.03571 0.04347 = 0.03764 0.00819 0.01007 0.00321 AFIX 43 H12 2 -0.088824 0.351990 0.287921 11.00000 -1.20000 AFIX 0 C13 1 0.025255 0.151759 0.246478 11.00000 0.03933 0.04207 = 0.03931 0.01236 0.00888 -0.00330 AFIX 43 H13 2 -0.089323 0.105030 0.273237 11.00000 -1.20000 AFIX 0 C14 1 0.167665 0.056609 0.204263 11.00000 0.04133 0.03346 = 0.04501 0.01158 0.00637 -0.00218 AFIX 43 H14 2 0.141512 -0.046339 0.206864 11.00000 -1.20000 AFIX 0 C15 1 0.346741 0.091823 0.157806 11.00000 0.03433 0.02925 = 0.03528 0.00513 0.00162 0.00132 AFIX 43 H15 2 0.425680 0.009302 0.133234 11.00000 -1.20000 AFIX 0 C16 1 0.423411 0.228682 0.142999 11.00000 0.02639 0.03147 = 0.02706 0.00486 -0.00204 0.00067 C17 1 0.603902 0.252679 0.093226 11.00000 0.02689 0.02795 = 0.02644 0.00365 -0.00063 0.00167 C18 1 0.641130 0.408207 0.093711 11.00000 0.02521 0.02792 = 0.02381 0.00375 -0.00280 0.00185 C19 1 0.735241 0.146054 0.049309 11.00000 0.03523 0.02592 = 0.03195 0.00613 0.00177 0.00167 AFIX 43 H19 2 0.704718 0.042266 0.049696 11.00000 -1.20000 AFIX 0 C20 1 0.905069 0.192852 0.006627 11.00000 0.03569 0.02672 = 0.03127 0.00235 0.00460 0.00640 AFIX 43 H20 2 0.994563 0.120943 -0.022285 11.00000 -1.20000 AFIX 0 C21 1 0.952558 0.348262 0.004152 11.00000 0.02641 0.02929 = 0.02353 0.00420 -0.00214 0.00257 C22 1 1.127988 0.392221 -0.040664 11.00000 0.02729 0.02859 = 0.02477 0.00255 0.00061 0.00505 AFIX 43 H22 2 1.215681 0.317245 -0.068090 11.00000 -1.20000 AFIX 0 C23 1 1.180889 0.540604 -0.047175 11.00000 0.02552 0.02918 = 0.02271 0.00279 -0.00299 0.00366 HKLF 4 REM cu_AzAc_2_0m_a.res in P-1 REM wR2 = 0.1381, GooF = S = 1.051, Restrained GooF = 1.051 for all data REM R1 = 0.0479 for 2423 Fo > 4sig(Fo) and 0.0631 for all 3101 data REM 209 parameters refined using 0 restraints END WGHT 0.0750 0.1384 REM Highest difference peak 0.233, deepest hole -0.194, 1-sigma level 0.039 Q1 1 1.4600 0.6708 0.5686 11.00000 0.05 0.23 Q2 1 1.4116 0.6169 0.5417 11.00000 0.05 0.23 ; _shelx_res_checksum 45960 _olex2_submission_special_instructions 'No special instructions were received' 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 1.4632(5) 0.8115(5) 0.60528(16) 0.1146(14) Uani 1 1 d . . . . . H1A H 1.612347 0.791639 0.580139 0.172 Uiso 1 1 calc R U . . . H1B H 1.469306 0.768201 0.651137 0.172 Uiso 1 1 calc R U . . . H1C H 1.455559 0.920253 0.619931 0.172 Uiso 1 1 calc R U . . . C2 C 1.2398(6) 0.7424(4) 0.55179(15) 0.0916(10) Uani 1 1 d . . . . . H2A H 1.092178 0.757175 0.579393 0.110 Uiso 1 1 calc R U . . . H2B H 1.251115 0.632746 0.537590 0.110 Uiso 1 1 calc R U . . . C3 C 1.1978(4) 0.8008(3) 0.47933(12) 0.0616(6) Uani 1 1 d . . . . . H3A H 1.345380 0.786883 0.451643 0.074 Uiso 1 1 calc R U . . . H3B H 1.183420 0.910148 0.493190 0.074 Uiso 1 1 calc R U . . . C4 C 0.9698(4) 0.7265(3) 0.42580(12) 0.0571(6) Uani 1 1 d . . . . . H4A H 0.982029 0.616764 0.413310 0.069 Uiso 1 1 calc R U . . . H4B H 0.821993 0.742959 0.453117 0.069 Uiso 1 1 calc R U . . . C5 C 0.9297(4) 0.7809(2) 0.35198(10) 0.0419(4) Uani 1 1 d . . . . . H5A H 1.078319 0.766355 0.324833 0.050 Uiso 1 1 calc R U . . . H5B H 0.912596 0.890111 0.364101 0.050 Uiso 1 1 calc R U . . . C6 C 0.7015(3) 0.7010(2) 0.29875(9) 0.0372(4) Uani 1 1 d . . . . . H6A H 0.707583 0.591076 0.292156 0.045 Uiso 1 1 calc R U . . . H6B H 0.550916 0.726852 0.323102 0.045 Uiso 1 1 calc R U . . . C7 C 0.6802(3) 0.74142(17) 0.22039(9) 0.0321(4) Uani 1 1 d . . . . . H7A H 0.836860 0.723560 0.197991 0.039 Uiso 1 1 calc R U . . . H7B H 0.660731 0.850063 0.226827 0.039 Uiso 1 1 calc R U . . . C8 C 0.4627(3) 0.65259(17) 0.16389(9) 0.0290(4) Uani 1 1 d . . . . . H8A H 0.305902 0.670375 0.186225 0.035 Uiso 1 1 calc R U . . . H8B H 0.454399 0.691477 0.116089 0.035 Uiso 1 1 calc R U . . . C9 C 0.4818(3) 0.48597(17) 0.14440(9) 0.0272(4) Uani 1 1 d . . . . . C10 C 0.3472(3) 0.37915(17) 0.17412(9) 0.0285(4) Uani 1 1 d . . . . . C11 C 0.1670(3) 0.40758(19) 0.22448(9) 0.0336(4) Uani 1 1 d . . . . . H11 H 0.138259 0.510129 0.239324 0.040 Uiso 1 1 calc R U . . . C12 C 0.0253(3) 0.3080(2) 0.25560(10) 0.0386(4) Uani 1 1 d . . . . . H12 H -0.088824 0.351990 0.287921 0.046 Uiso 1 1 calc R U . . . C13 C 0.0253(3) 0.1518(2) 0.24648(10) 0.0398(4) Uani 1 1 d . . . . . H13 H -0.089323 0.105030 0.273237 0.048 Uiso 1 1 calc R U . . . C14 C 0.1677(3) 0.0566(2) 0.20426(10) 0.0397(4) Uani 1 1 d . . . . . H14 H 0.141512 -0.046339 0.206864 0.048 Uiso 1 1 calc R U . . . C15 C 0.3467(3) 0.09182(18) 0.15781(9) 0.0335(4) Uani 1 1 d . . . . . H15 H 0.425680 0.009302 0.133234 0.040 Uiso 1 1 calc R U . . . C16 C 0.4234(3) 0.22868(17) 0.14300(9) 0.0290(4) Uani 1 1 d . . . . . C17 C 0.6039(3) 0.25268(17) 0.09323(9) 0.0277(4) Uani 1 1 d . . . . . C18 C 0.6411(3) 0.40821(17) 0.09371(8) 0.0263(3) Uani 1 1 d . . . . . C19 C 0.7352(3) 0.14605(17) 0.04931(9) 0.0313(4) Uani 1 1 d . . . . . H19 H 0.704718 0.042266 0.049696 0.038 Uiso 1 1 calc R U . . . C20 C 0.9051(3) 0.19285(17) 0.00663(9) 0.0315(4) Uani 1 1 d . . . . . H20 H 0.994563 0.120943 -0.022285 0.038 Uiso 1 1 calc R U . . . C21 C 0.9526(3) 0.34826(17) 0.00415(8) 0.0270(4) Uani 1 1 d . . . . . C22 C 1.1280(3) 0.39222(17) -0.04066(8) 0.0274(3) Uani 1 1 d . . . . . H22 H 1.215681 0.317245 -0.068090 0.033 Uiso 1 1 calc R U . . . C23 C 1.1809(3) 0.54060(17) -0.04718(8) 0.0265(3) 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 0.0562(17) 0.233(5) 0.0522(16) 0.033(2) -0.0072(13) 0.012(2) C2 0.082(2) 0.143(3) 0.0490(14) 0.0303(16) -0.0126(13) 0.0067(18) C3 0.0521(13) 0.0922(18) 0.0370(11) 0.0081(11) -0.0024(9) 0.0095(12) C4 0.0575(13) 0.0733(15) 0.0392(11) 0.0145(10) -0.0016(9) 0.0002(11) C5 0.0446(10) 0.0447(10) 0.0328(9) 0.0030(7) 0.0000(8) 0.0022(8) C6 0.0370(9) 0.0411(10) 0.0322(9) 0.0049(7) 0.0046(7) 0.0016(7) C7 0.0345(9) 0.0273(8) 0.0329(9) 0.0035(6) 0.0040(7) 0.0008(6) C8 0.0279(8) 0.0286(8) 0.0307(8) 0.0054(6) 0.0035(6) 0.0049(6) C9 0.0249(8) 0.0283(8) 0.0270(7) 0.0050(6) -0.0011(6) 0.0012(6) C10 0.0256(8) 0.0310(8) 0.0267(8) 0.0041(6) -0.0019(6) 0.0013(6) C11 0.0323(9) 0.0337(9) 0.0341(8) 0.0055(7) 0.0041(7) 0.0039(6) C12 0.0357(9) 0.0435(10) 0.0376(9) 0.0082(7) 0.0101(7) 0.0032(7) C13 0.0393(10) 0.0421(10) 0.0393(9) 0.0124(8) 0.0089(8) -0.0033(7) C14 0.0413(10) 0.0335(9) 0.0450(10) 0.0116(7) 0.0064(8) -0.0022(7) C15 0.0343(9) 0.0292(8) 0.0353(9) 0.0051(7) 0.0016(7) 0.0013(6) C16 0.0264(8) 0.0315(8) 0.0271(8) 0.0049(6) -0.0020(6) 0.0007(6) C17 0.0269(8) 0.0280(8) 0.0264(7) 0.0037(6) -0.0006(6) 0.0017(6) C18 0.0252(8) 0.0279(8) 0.0238(7) 0.0038(6) -0.0028(6) 0.0019(6) C19 0.0352(9) 0.0259(8) 0.0319(8) 0.0061(6) 0.0018(7) 0.0017(6) C20 0.0357(9) 0.0267(8) 0.0313(8) 0.0023(6) 0.0046(7) 0.0064(6) C21 0.0264(8) 0.0293(8) 0.0235(7) 0.0042(6) -0.0021(6) 0.0026(6) C22 0.0273(8) 0.0286(8) 0.0248(7) 0.0025(6) 0.0006(6) 0.0051(6) C23 0.0255(8) 0.0292(8) 0.0227(7) 0.0028(6) -0.0030(6) 0.0037(6) 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' 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 H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C1 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C1 C2 C3 116.2(3) . . ? H2A C2 H2B 107.4 . . ? C3 C2 H2A 108.2 . . ? C3 C2 H2B 108.2 . . ? C2 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C2 C3 C4 114.7(2) . . ? H3A C3 H3B 107.6 . . ? C4 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? C3 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C5 C4 C3 115.17(19) . . ? C5 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C4 C5 C6 113.67(17) . . ? H5A C5 H5B 107.7 . . ? C6 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C5 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C7 C6 C5 113.51(15) . . ? C7 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C6 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C6 C7 C8 114.17(13) . . ? H7A C7 H7B 107.6 . . ? C8 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C7 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C9 C8 C7 113.84(12) . . ? C9 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C10 C9 C8 124.93(15) . . ? C10 C9 C18 107.94(13) . . ? C18 C9 C8 127.13(14) . . ? C9 C10 C11 126.18(15) . . ? C9 C10 C16 108.68(14) . . ? C11 C10 C16 125.14(15) . . ? C10 C11 H11 115.3 . . ? C12 C11 C10 129.42(16) . . ? C12 C11 H11 115.3 . . ? C11 C12 H12 115.2 . . ? C11 C12 C13 129.52(17) . . ? C13 C12 H12 115.2 . . ? C12 C13 H13 115.4 . . ? C14 C13 C12 129.13(17) . . ? C14 C13 H13 115.4 . . ? C13 C14 H14 115.8 . . ? C13 C14 C15 128.43(16) . . ? C15 C14 H14 115.8 . . ? C14 C15 H15 115.5 . . ? C16 C15 C14 128.99(17) . . ? C16 C15 H15 115.5 . . ? C15 C16 C10 129.30(15) . . ? C15 C16 C17 124.84(15) . . ? C17 C16 C10 105.85(13) . . ? C18 C17 C16 109.07(14) . . ? C19 C17 C16 128.74(15) . . ? C19 C17 C18 122.19(15) . . ? C9 C18 C23 132.75(14) . 2_765 ? C17 C18 C9 108.46(14) . . ? C17 C18 C23 118.79(14) . 2_765 ? C17 C19 H19 120.2 . . ? C20 C19 C17 119.55(15) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 119.3 . . ? C19 C20 C21 121.45(15) . . ? C21 C20 H20 119.3 . . ? C20 C21 C23 120.41(15) . 2_765 ? C22 C21 C20 119.86(14) . . ? C22 C21 C23 119.73(14) . 2_765 ? C21 C22 H22 118.4 . . ? C23 C22 C21 123.21(15) . . ? C23 C22 H22 118.4 . . ? C21 C23 C18 117.59(14) 2_765 2_765 ? C22 C23 C18 125.35(14) . 2_765 ? C22 C23 C21 117.06(15) . 2_765 ? 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 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.482(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.504(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.512(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.507(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.524(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.519(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.537(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.505(2) . ? C9 C10 1.395(2) . ? C9 C18 1.443(2) . ? C10 C11 1.405(2) . ? C10 C16 1.483(2) . ? C11 H11 0.9500 . ? C11 C12 1.383(2) . ? C12 H12 0.9500 . ? C12 C13 1.402(3) . ? C13 H13 0.9500 . ? C13 C14 1.375(3) . ? C14 H14 0.9500 . ? C14 C15 1.404(3) . ? C15 H15 0.9500 . ? C15 C16 1.370(2) . ? C16 C17 1.426(2) . ? C17 C18 1.416(2) . ? C17 C19 1.413(2) . ? C18 C23 1.450(2) 2_765 ? C19 H19 0.9500 . ? C19 C20 1.355(2) . ? C20 H20 0.9500 . ? C20 C21 1.432(2) . ? C21 C22 1.395(2) . ? C21 C23 1.438(2) 2_765 ? C22 H22 0.9500 . ? C22 C23 1.392(2) . ? 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 C2 C3 C4 179.3(3) . . . . ? C2 C3 C4 C5 -178.3(2) . . . . ? C3 C4 C5 C6 178.71(18) . . . . ? C4 C5 C6 C7 -172.48(17) . . . . ? C5 C6 C7 C8 175.42(14) . . . . ? C6 C7 C8 C9 -63.04(19) . . . . ? C7 C8 C9 C10 102.96(17) . . . . ? C7 C8 C9 C18 -76.01(19) . . . . ? C8 C9 C10 C11 2.4(2) . . . . ? C8 C9 C10 C16 -178.27(13) . . . . ? C8 C9 C18 C17 178.67(13) . . . . ? C8 C9 C18 C23 -1.1(3) . . . 2_765 ? C9 C10 C11 C12 179.34(16) . . . . ? C9 C10 C16 C15 177.96(15) . . . . ? C9 C10 C16 C17 -0.96(16) . . . . ? C10 C9 C18 C17 -0.45(16) . . . . ? C10 C9 C18 C23 179.74(15) . . . 2_765 ? C10 C11 C12 C13 1.2(3) . . . . ? C10 C16 C17 C18 0.67(16) . . . . ? C10 C16 C17 C19 179.93(14) . . . . ? C11 C10 C16 C15 -2.7(2) . . . . ? C11 C10 C16 C17 178.38(14) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 -1.6(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C10 2.8(3) . . . . ? C14 C15 C16 C17 -178.48(16) . . . . ? C15 C16 C17 C18 -178.30(14) . . . . ? C15 C16 C17 C19 1.0(3) . . . . ? C16 C10 C11 C12 0.1(3) . . . . ? C16 C17 C18 C9 -0.17(17) . . . . ? C16 C17 C18 C23 179.68(12) . . . 2_765 ? C16 C17 C19 C20 -178.42(15) . . . . ? C17 C19 C20 C21 -0.8(2) . . . . ? C18 C9 C10 C11 -178.47(14) . . . . ? C18 C9 C10 C16 0.86(16) . . . . ? C18 C17 C19 C20 0.8(2) . . . . ? C19 C17 C18 C9 -179.48(13) . . . . ? C19 C17 C18 C23 0.4(2) . . . 2_765 ? C19 C20 C21 C22 -179.74(14) . . . . ? C19 C20 C21 C23 -0.2(2) . . . 2_765 ? C20 C21 C22 C23 178.71(13) . . . . ? C21 C22 C23 C18 -179.14(13) . . . 2_765 ? C21 C22 C23 C21 0.8(2) . . . 2_765 ? C23 C21 C22 C23 -0.8(2) 2_765 . . . ?