#------------------------------------------------------------------------------ #$Date: 2019-12-21 03:46:13 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245466 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125685.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_7125685 loop_ _publ_author_name 'Shoji, Taku' 'Sugiyama, Shuhei' 'Kobayashi, Yoshiaki' 'Yamazaki, Akari' 'Ariga, Yukino' 'Katoh, Ryuzi' 'Wakui, Hiroki' 'Yasunami, Masafumi' 'Ito, Shunji' _publ_section_title ; Direct synthesis of 2-arylazulenes by [8 + 2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC09376A _journal_year 2020 _chemical_formula_moiety 'C22 H22 O2' _chemical_formula_sum 'C22 H22 O2' _chemical_formula_weight 318.39 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2018-12-07 deposited with the CCDC. 2019-12-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.424(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.8804(4) _cell_length_b 9.8767(3) _cell_length_c 13.8827(5) _cell_measurement_reflns_used 13048 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.29 _cell_measurement_theta_min 2.58 _cell_volume 1731.11(10) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_publication_material 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku Varimax with Saturn' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_unetI/netI 0.0292 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14120 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.998 _diffrn_reflns_theta_min 2.618 _diffrn_source 'rotating anode X-ray generator' _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.159 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 1814 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.5(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 4153 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0348 _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^)+(0.0437P)^2^+0.4665P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.0826 _reflns_Friedel_coverage 0.986 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.988 _reflns_number_gt 3954 _reflns_number_total 4153 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09376a2.cif _cod_data_source_block shelxl_CCDC3 _cod_original_sg_symbol_H-M 'C c' _cod_database_code 7125685 _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_min 0.983 _shelx_estimated_absorpt_t_max 0.989 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2018/3 at 18:10:49 on 04-Dec-2018 CELL 0.71073 12.88040 9.87670 13.88270 90.00000 101.42400 90.00000 ZERR 4 0.00040 0.00030 0.00050 0.00000 0.00300 0.00000 LATT -7 SYMM +X, -Y, .50+Z SFAC C H O UNIT 88 88 8 SHEL 99999.000000 0.756947 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.220 0.160 0.140 WGHT 0.043700 0.466500 FVAR 0.57590 O1 3 0.354282 0.367110 0.503647 11.00000 0.01302 0.01886 = 0.03014 0.00581 0.00078 -0.00341 O2 3 0.512764 0.267058 0.549021 11.00000 0.01365 0.01341 = 0.02394 0.00114 0.00238 -0.00244 C1 1 0.512574 0.497516 0.514596 11.00000 0.01228 0.01518 = 0.01352 -0.00020 0.00290 -0.00132 C2 1 0.621624 0.518576 0.557803 11.00000 0.01305 0.01707 = 0.01132 -0.00096 0.00388 -0.00128 C3 1 0.651478 0.647221 0.531082 11.00000 0.01401 0.01749 = 0.01453 -0.00116 0.00206 -0.00394 AFIX 43 H3 2 0.719971 0.685819 0.550654 11.00000 -1.20000 AFIX 0 C4 1 0.564667 0.710451 0.470920 11.00000 0.01426 0.01591 = 0.01383 -0.00248 0.00416 -0.00210 C5 1 0.566047 0.838178 0.429910 11.00000 0.01602 0.01560 = 0.01880 -0.00261 0.00428 -0.00481 AFIX 43 H5 2 0.630513 0.887004 0.448004 11.00000 -1.20000 AFIX 0 C6 1 0.485430 0.904050 0.365803 11.00000 0.02176 0.01216 = 0.02344 0.00262 0.00548 -0.00255 AFIX 43 H6 2 0.502294 0.991940 0.345714 11.00000 -1.20000 AFIX 0 C7 1 0.382580 0.858787 0.326620 11.00000 0.01814 0.01531 = 0.01757 0.00200 0.00363 0.00254 AFIX 43 H7 2 0.340940 0.920391 0.282528 11.00000 -1.20000 AFIX 0 C8 1 0.331180 0.738979 0.341361 11.00000 0.01361 0.01617 = 0.01312 -0.00019 0.00244 0.00091 C9 1 0.373756 0.630900 0.402368 11.00000 0.01337 0.01500 = 0.01402 -0.00084 0.00257 -0.00087 AFIX 43 H9 2 0.326482 0.557766 0.404961 11.00000 -1.20000 AFIX 0 C10 1 0.474559 0.614700 0.459523 11.00000 0.01322 0.01478 = 0.01285 -0.00218 0.00367 -0.00141 C11 1 0.450297 0.374955 0.521139 11.00000 0.01422 0.01475 = 0.01249 -0.00012 0.00204 -0.00207 C12 1 0.458359 0.143385 0.562474 11.00000 0.01999 0.01430 = 0.02985 0.00355 0.00244 -0.00291 AFIX 137 H12A 2 0.408295 0.121099 0.501710 11.00000 -1.20000 H12B 2 0.419755 0.154916 0.616070 11.00000 -1.20000 H12C 2 0.509969 0.069898 0.578806 11.00000 -1.20000 AFIX 0 C13 1 0.694406 0.427222 0.624489 11.00000 0.01067 0.01535 = 0.01434 -0.00094 -0.00048 -0.00434 C14 1 0.673803 0.389693 0.716576 11.00000 0.01442 0.01536 = 0.01623 -0.00066 0.00163 -0.00340 C15 1 0.746445 0.306194 0.777159 11.00000 0.01755 0.01968 = 0.01761 0.00379 0.00136 -0.00476 AFIX 43 H15 2 0.733676 0.280848 0.839795 11.00000 -1.20000 AFIX 0 C16 1 0.837043 0.259440 0.747641 11.00000 0.01366 0.02102 = 0.02534 0.00491 -0.00315 -0.00114 AFIX 43 H16 2 0.884819 0.201430 0.789461 11.00000 -1.20000 AFIX 0 C17 1 0.857623 0.297443 0.657282 11.00000 0.01160 0.02347 = 0.02507 -0.00026 0.00182 0.00009 AFIX 43 H17 2 0.919617 0.266133 0.636924 11.00000 -1.20000 AFIX 0 C18 1 0.786745 0.381861 0.596570 11.00000 0.01404 0.01964 = 0.01590 -0.00080 0.00188 -0.00413 AFIX 43 H18 2 0.801436 0.409128 0.535021 11.00000 -1.20000 AFIX 0 C19 1 0.576702 0.438039 0.752171 11.00000 0.01834 0.02216 = 0.01693 0.00189 0.00535 -0.00042 AFIX 137 H19A 2 0.595296 0.456908 0.822797 11.00000 -1.20000 H19B 2 0.521949 0.367774 0.739908 11.00000 -1.20000 H19C 2 0.549858 0.520803 0.716905 11.00000 -1.20000 AFIX 0 C20 1 0.216371 0.722907 0.287616 11.00000 0.01567 0.01493 = 0.01751 0.00225 -0.00108 -0.00007 AFIX 13 H20 2 0.198799 0.802751 0.243077 11.00000 -1.20000 AFIX 0 C21 1 0.198398 0.595948 0.223738 11.00000 0.02669 0.02023 = 0.02457 -0.00298 -0.00651 0.00094 AFIX 137 H21A 2 0.247554 0.595807 0.178139 11.00000 -1.20000 H21B 2 0.125376 0.595129 0.186386 11.00000 -1.20000 H21C 2 0.210729 0.515416 0.265689 11.00000 -1.20000 AFIX 0 C22 1 0.142081 0.726586 0.361214 11.00000 0.01297 0.02193 = 0.02851 0.00164 0.00113 -0.00026 AFIX 137 H22A 2 0.151861 0.811978 0.397844 11.00000 -1.20000 H22B 2 0.158378 0.650556 0.407077 11.00000 -1.20000 H22C 2 0.068493 0.719578 0.325788 11.00000 -1.20000 AFIX 0 HKLF 4 REM xcalibur REM wR2 = 0.0826, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0348 for 3954 Fo > 4sig(Fo) and 0.0371 for all 4153 data REM 221 parameters refined using 2 restraints END WGHT 0.0437 0.4665 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.159, deepest hole -0.210, 1-sigma level 0.042 Q1 1 0.2756 0.7285 0.3144 11.00000 0.05 0.16 Q2 1 0.7010 0.4390 0.6797 11.00000 0.05 0.16 Q3 1 0.6569 0.4755 0.6001 11.00000 0.05 0.14 ; _shelx_res_checksum 51142 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' 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 O1 O 0.35428(11) 0.36711(14) 0.50365(11) 0.0212(3) Uani 1 1 d . . O2 O 0.51276(10) 0.26706(13) 0.54902(10) 0.0172(3) Uani 1 1 d . . C1 C 0.51257(14) 0.49752(19) 0.51460(13) 0.0136(4) Uani 1 1 d . . C2 C 0.62162(14) 0.51858(19) 0.55780(13) 0.0136(3) Uani 1 1 d . . C3 C 0.65148(14) 0.64722(19) 0.53108(14) 0.0154(4) Uani 1 1 d . . H3 H 0.719971 0.685819 0.550654 0.019 Uiso 1 1 calc R U C4 C 0.56467(14) 0.71045(19) 0.47092(13) 0.0145(4) Uani 1 1 d . . C5 C 0.56605(15) 0.83818(19) 0.42991(14) 0.0167(4) Uani 1 1 d . . H5 H 0.630513 0.887004 0.448004 0.020 Uiso 1 1 calc R U C6 C 0.48543(16) 0.90405(19) 0.36580(14) 0.0190(4) Uani 1 1 d . . H6 H 0.502294 0.991940 0.345714 0.023 Uiso 1 1 calc R U C7 C 0.38258(15) 0.85879(19) 0.32662(14) 0.0170(4) Uani 1 1 d . . H7 H 0.340940 0.920391 0.282528 0.020 Uiso 1 1 calc R U C8 C 0.33118(15) 0.73898(18) 0.34136(14) 0.0143(3) Uani 1 1 d . . C9 C 0.37376(14) 0.63090(19) 0.40237(13) 0.0141(4) Uani 1 1 d . . H9 H 0.326482 0.557766 0.404961 0.017 Uiso 1 1 calc R U C10 C 0.47456(14) 0.61470(19) 0.45952(13) 0.0135(4) Uani 1 1 d . . C11 C 0.45030(14) 0.37495(18) 0.52114(13) 0.0139(3) Uani 1 1 d . . C12 C 0.45836(16) 0.1434(2) 0.56247(17) 0.0217(4) Uani 1 1 d . . H12A H 0.408295 0.121099 0.501710 0.026 Uiso 1 1 calc R U H12B H 0.419755 0.154916 0.616070 0.026 Uiso 1 1 calc R U H12C H 0.509969 0.069898 0.578806 0.026 Uiso 1 1 calc R U C13 C 0.69441(14) 0.42722(19) 0.62449(13) 0.0139(4) Uani 1 1 d . . C14 C 0.67380(14) 0.38969(19) 0.71658(14) 0.0155(4) Uani 1 1 d . . C15 C 0.74645(15) 0.3062(2) 0.77716(14) 0.0186(4) Uani 1 1 d . . H15 H 0.733676 0.280848 0.839795 0.022 Uiso 1 1 calc R U C16 C 0.83704(15) 0.2594(2) 0.74764(15) 0.0210(4) Uani 1 1 d . . H16 H 0.884819 0.201430 0.789461 0.025 Uiso 1 1 calc R U C17 C 0.85762(15) 0.2974(2) 0.65728(15) 0.0203(4) Uani 1 1 d . . H17 H 0.919617 0.266133 0.636924 0.024 Uiso 1 1 calc R U C18 C 0.78675(15) 0.38186(19) 0.59657(14) 0.0167(4) Uani 1 1 d . . H18 H 0.801436 0.409128 0.535021 0.020 Uiso 1 1 calc R U C19 C 0.57670(15) 0.4380(2) 0.75217(15) 0.0189(4) Uani 1 1 d . . H19A H 0.595296 0.456908 0.822797 0.023 Uiso 1 1 calc R U H19B H 0.521949 0.367774 0.739908 0.023 Uiso 1 1 calc R U H19C H 0.549858 0.520803 0.716905 0.023 Uiso 1 1 calc R U C20 C 0.21637(14) 0.7229(2) 0.28762(14) 0.0166(4) Uani 1 1 d . . H20 H 0.198799 0.802751 0.243077 0.020 Uiso 1 1 calc R U C21 C 0.19840(18) 0.5959(2) 0.22374(17) 0.0254(5) Uani 1 1 d . . H21A H 0.247554 0.595807 0.178139 0.031 Uiso 1 1 calc R U H21B H 0.125376 0.595129 0.186386 0.031 Uiso 1 1 calc R U H21C H 0.210729 0.515416 0.265689 0.031 Uiso 1 1 calc R U C22 C 0.14208(15) 0.7266(2) 0.36121(16) 0.0215(4) Uani 1 1 d . . H22A H 0.151861 0.811978 0.397844 0.026 Uiso 1 1 calc R U H22B H 0.158378 0.650556 0.407077 0.026 Uiso 1 1 calc R U H22C H 0.068493 0.719578 0.325788 0.026 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 O1 0.0130(6) 0.0189(7) 0.0301(8) 0.0058(6) 0.0008(5) -0.0034(5) O2 0.0137(6) 0.0134(6) 0.0239(7) 0.0011(5) 0.0024(5) -0.0024(5) C1 0.0123(8) 0.0152(8) 0.0135(8) -0.0002(7) 0.0029(7) -0.0013(7) C2 0.0131(8) 0.0171(8) 0.0113(8) -0.0010(7) 0.0039(6) -0.0013(7) C3 0.0140(9) 0.0175(9) 0.0145(9) -0.0012(7) 0.0021(7) -0.0039(7) C4 0.0143(9) 0.0159(9) 0.0138(9) -0.0025(7) 0.0042(7) -0.0021(7) C5 0.0160(9) 0.0156(9) 0.0188(9) -0.0026(7) 0.0043(7) -0.0048(7) C6 0.0218(10) 0.0122(8) 0.0234(10) 0.0026(7) 0.0055(8) -0.0026(7) C7 0.0181(9) 0.0153(8) 0.0176(9) 0.0020(7) 0.0036(7) 0.0025(7) C8 0.0136(8) 0.0162(9) 0.0131(8) -0.0002(7) 0.0024(6) 0.0009(7) C9 0.0134(8) 0.0150(9) 0.0140(8) -0.0008(7) 0.0026(7) -0.0009(7) C10 0.0132(8) 0.0148(9) 0.0128(8) -0.0022(7) 0.0037(7) -0.0014(7) C11 0.0142(9) 0.0148(8) 0.0125(8) -0.0001(7) 0.0020(7) -0.0021(7) C12 0.0200(10) 0.0143(9) 0.0298(11) 0.0035(8) 0.0024(8) -0.0029(7) C13 0.0107(8) 0.0154(8) 0.0143(8) -0.0009(7) -0.0005(6) -0.0043(7) C14 0.0144(9) 0.0154(9) 0.0162(9) -0.0007(7) 0.0016(7) -0.0034(7) C15 0.0175(9) 0.0197(9) 0.0176(9) 0.0038(7) 0.0014(7) -0.0048(8) C16 0.0137(9) 0.0210(9) 0.0253(11) 0.0049(8) -0.0031(7) -0.0011(7) C17 0.0116(8) 0.0235(10) 0.0251(10) -0.0003(8) 0.0018(7) 0.0001(8) C18 0.0140(8) 0.0196(9) 0.0159(9) -0.0008(7) 0.0019(7) -0.0041(7) C19 0.0183(9) 0.0222(10) 0.0169(9) 0.0019(8) 0.0054(7) -0.0004(7) C20 0.0157(9) 0.0149(9) 0.0175(9) 0.0022(7) -0.0011(7) -0.0001(7) C21 0.0267(11) 0.0202(10) 0.0246(11) -0.0030(8) -0.0065(8) 0.0009(8) C22 0.0130(9) 0.0219(10) 0.0285(11) 0.0016(8) 0.0011(8) -0.0003(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' 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 C11 O2 C12 115.53(14) C10 C1 C2 108.23(16) C10 C1 C11 124.92(16) C2 C1 C11 126.80(17) C3 C2 C1 108.66(16) C3 C2 C13 122.98(16) C1 C2 C13 128.30(17) C2 C3 C4 109.49(16) C2 C3 H3 125.3 C4 C3 H3 125.3 C5 C4 C3 125.19(17) C5 C4 C10 127.66(17) C3 C4 C10 107.14(16) C4 C5 C6 128.40(18) C4 C5 H5 115.8 C6 C5 H5 115.8 C5 C6 C7 128.95(18) C5 C6 H6 115.5 C7 C6 H6 115.5 C8 C7 C6 130.92(18) C8 C7 H7 114.5 C6 C7 H7 114.5 C7 C8 C9 126.50(17) C7 C8 C20 117.37(16) C9 C8 C20 116.12(16) C10 C9 C8 129.82(17) C10 C9 H9 115.1 C8 C9 H9 115.1 C9 C10 C1 125.78(17) C9 C10 C4 127.66(17) C1 C10 C4 106.48(15) O1 C11 O2 122.29(16) O1 C11 C1 126.06(17) O2 C11 C1 111.64(15) O2 C12 H12A 109.5 O2 C12 H12B 109.5 H12A C12 H12B 109.5 O2 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C18 C13 C14 119.51(17) C18 C13 C2 119.29(17) C14 C13 C2 121.16(17) C15 C14 C13 118.59(17) C15 C14 C19 119.27(17) C13 C14 C19 122.13(16) C16 C15 C14 121.33(18) C16 C15 H15 119.3 C14 C15 H15 119.3 C17 C16 C15 119.98(18) C17 C16 H16 120.0 C15 C16 H16 120.0 C16 C17 C18 119.42(19) C16 C17 H17 120.3 C18 C17 H17 120.3 C17 C18 C13 121.15(18) C17 C18 H18 119.4 C13 C18 H18 119.4 C14 C19 H19A 109.5 C14 C19 H19B 109.5 H19A C19 H19B 109.5 C14 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C21 C20 C8 112.95(16) C21 C20 C22 111.34(17) C8 C20 C22 110.12(15) C21 C20 H20 107.4 C8 C20 H20 107.4 C22 C20 H20 107.4 C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C20 C22 H22A 109.5 C20 C22 H22B 109.5 H22A C22 H22B 109.5 C20 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.215(2) O2 C11 1.345(2) O2 C12 1.439(2) C1 C10 1.420(3) C1 C2 1.429(2) C1 C11 1.465(2) C2 C3 1.399(3) C2 C13 1.485(2) C3 C4 1.403(3) C3 H3 0.9500 C4 C5 1.386(3) C4 C10 1.481(2) C5 C6 1.388(3) C5 H5 0.9500 C6 C7 1.402(3) C6 H6 0.9500 C7 C8 1.391(3) C7 H7 0.9500 C8 C9 1.405(3) C8 C20 1.527(2) C9 C10 1.390(2) C9 H9 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C18 1.396(3) C13 C14 1.406(3) C14 C15 1.397(3) C14 C19 1.510(3) C15 C16 1.390(3) C15 H15 0.9500 C16 C17 1.384(3) C16 H16 0.9500 C17 C18 1.391(3) C17 H17 0.9500 C18 H18 0.9500 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C20 C21 1.527(3) C20 C22 1.532(3) C20 H20 1.0000 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 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 C10 C1 C2 C3 0.5(2) C11 C1 C2 C3 177.93(17) C10 C1 C2 C13 177.61(18) C11 C1 C2 C13 -4.9(3) C1 C2 C3 C4 -0.4(2) C13 C2 C3 C4 -177.66(17) C2 C3 C4 C5 -179.14(18) C2 C3 C4 C10 0.1(2) C3 C4 C5 C6 176.21(19) C10 C4 C5 C6 -2.9(3) C4 C5 C6 C7 0.2(3) C5 C6 C7 C8 1.5(4) C6 C7 C8 C9 0.0(4) C6 C7 C8 C20 178.93(19) C7 C8 C9 C10 -1.7(3) C20 C8 C9 C10 179.40(18) C8 C9 C10 C1 -175.94(19) C8 C9 C10 C4 0.3(3) C2 C1 C10 C9 176.43(17) C11 C1 C10 C9 -1.1(3) C2 C1 C10 C4 -0.43(19) C11 C1 C10 C4 -177.93(17) C5 C4 C10 C9 2.6(3) C3 C4 C10 C9 -176.57(18) C5 C4 C10 C1 179.42(18) C3 C4 C10 C1 0.21(19) C12 O2 C11 O1 -3.6(3) C12 O2 C11 C1 176.84(16) C10 C1 C11 O1 -20.4(3) C2 C1 C11 O1 162.61(18) C10 C1 C11 O2 159.21(17) C2 C1 C11 O2 -17.8(3) C3 C2 C13 C18 -62.1(2) C1 C2 C13 C18 121.2(2) C3 C2 C13 C14 115.6(2) C1 C2 C13 C14 -61.1(3) C18 C13 C14 C15 -0.8(3) C2 C13 C14 C15 -178.44(17) C18 C13 C14 C19 178.52(17) C2 C13 C14 C19 0.8(3) C13 C14 C15 C16 -0.6(3) C19 C14 C15 C16 -179.86(18) C14 C15 C16 C17 1.1(3) C15 C16 C17 C18 -0.3(3) C16 C17 C18 C13 -1.0(3) C14 C13 C18 C17 1.6(3) C2 C13 C18 C17 179.29(17) C7 C8 C20 C21 123.9(2) C9 C8 C20 C21 -57.1(2) C7 C8 C20 C22 -110.95(19) C9 C8 C20 C22 68.1(2)