#------------------------------------------------------------------------------ #$Date: 2017-12-23 07:14:26 +0200 (Sat, 23 Dec 2017) $ #$Revision: 204512 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156041.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_7156041 loop_ _publ_author_name 'Shoji, Taku' 'Tanaka, Miwa' 'Takagaki, Sho' 'Miura, Kota' 'Ohta, Akira' 'Sekiguchi, Ryuta' 'Ito, Shunji' 'Mori, Shigeki' 'Okujima, Tetsuo' _publ_section_title ; Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C7OB02861J _journal_year 2018 _chemical_formula_moiety 'C24 H20 O4' _chemical_formula_sum 'C24 H20 O4' _chemical_formula_weight 372.40 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2017-04-18 deposited with the CCDC. 2017-12-21 downloaded from the CCDC. ; _cell_angle_alpha 67.033(5) _cell_angle_beta 83.287(5) _cell_angle_gamma 88.921(5) _cell_formula_units_Z 2 _cell_length_a 6.7449(4) _cell_length_b 11.3462(7) _cell_length_c 12.9292(7) _cell_measurement_reflns_used 6168 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.28 _cell_measurement_theta_min 1.76 _cell_volume 904.39(10) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2.4 (Rigaku, 2016)' _computing_publication_material 'CrystalStructure 4.2.4' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.0478 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 15396 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.988 _diffrn_reflns_theta_min 1.950 _diffrn_source 'Varimax 50 kV 24 mA Rotating anode' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.269 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 4353 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0514 _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^)+(0.0546P)^2^+0.3520P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1121 _refine_ls_wR_factor_ref 0.1253 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3179 _reflns_number_total 4353 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02861j2.cif _cod_data_source_block shelxl_CCDC1 _cod_database_code 7156041 _shelx_shelxl_version_number 2016/6 _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 0.977 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2016/6 at 23:17:30 on 04-Apr-2017 CELL 0.71075 6.74490 11.34620 12.92920 67.03300 83.28700 88.92100 ZERR 2 0.00040 0.00070 0.00070 0.00500 0.00500 0.00500 LATT 1 SFAC C H O UNIT 48 40 8 SHEL 99999.000000 0.756965 OMIT 0 0 1 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.250 0.040 0.040 WGHT 0.054600 0.352000 FVAR 0.55615 O1 3 0.329232 0.764223 -0.006919 11.00000 0.04695 0.01846 = 0.01315 -0.00289 -0.00104 -0.00456 O2 3 0.272361 0.552464 0.081543 11.00000 0.03881 0.01662 = 0.01420 -0.00772 -0.00212 -0.00361 O3 3 0.235755 0.539216 0.585722 11.00000 0.02531 0.01071 = 0.01254 -0.00352 -0.00234 -0.00029 O4 3 0.207943 0.522052 0.762164 11.00000 0.04028 0.01867 = 0.01672 -0.00850 -0.00370 0.00060 C1 1 0.302652 0.665656 0.194990 11.00000 0.01424 0.01120 = 0.01467 -0.00382 -0.00028 -0.00039 C2 1 0.280812 0.555212 0.293690 11.00000 0.01546 0.00984 = 0.01597 -0.00443 -0.00144 0.00086 AFIX 43 H2 2 0.273462 0.470687 0.295968 11.00000 -1.20000 AFIX 0 C3 1 0.271104 0.585665 0.389512 11.00000 0.01254 0.00996 = 0.01391 -0.00301 -0.00179 0.00103 C4 1 0.284151 0.721571 0.350758 11.00000 0.01275 0.01165 = 0.01375 -0.00343 -0.00243 0.00132 C5 1 0.270526 0.795446 0.415985 11.00000 0.01955 0.01374 = 0.01356 -0.00415 -0.00245 0.00129 AFIX 43 H5 2 0.253775 0.748201 0.495520 11.00000 -1.20000 AFIX 0 C6 1 0.277839 0.927754 0.381790 11.00000 0.02262 0.01369 = 0.01851 -0.00872 -0.00377 0.00145 AFIX 43 H6 2 0.261282 0.956337 0.442151 11.00000 -1.20000 AFIX 0 C7 1 0.305382 1.026385 0.273782 11.00000 0.01535 0.01098 = 0.02195 -0.00571 -0.00409 0.00058 C8 1 0.332217 1.010701 0.171926 11.00000 0.01830 0.01106 = 0.01827 -0.00171 -0.00320 -0.00014 AFIX 43 H8 2 0.354167 1.087794 0.106361 11.00000 -1.20000 AFIX 0 C9 1 0.331877 0.899198 0.151166 11.00000 0.01441 0.01455 = 0.01444 -0.00231 -0.00216 0.00035 AFIX 43 H9 2 0.351998 0.912051 0.073505 11.00000 -1.20000 AFIX 0 C10 1 0.306813 0.772565 0.225967 11.00000 0.01034 0.01234 = 0.01578 -0.00420 -0.00218 0.00124 C11 1 0.304516 0.669531 0.080249 11.00000 0.01878 0.01545 = 0.01600 -0.00583 -0.00070 -0.00003 C12 1 0.262330 0.548441 -0.028075 11.00000 0.04271 0.02481 = 0.01582 -0.01102 -0.00355 -0.00439 AFIX 137 H12A 2 0.388289 0.582273 -0.076386 11.00000 -1.20000 H12B 2 0.152148 0.600600 -0.063080 11.00000 -1.20000 H12C 2 0.239750 0.459723 -0.019097 11.00000 -1.20000 AFIX 0 C13 1 0.249211 0.488515 0.503922 11.00000 0.01444 0.01411 = 0.01188 -0.00537 -0.00275 0.00185 C14 1 0.215301 0.465595 0.700094 11.00000 0.01712 0.01503 = 0.01355 -0.00313 -0.00250 0.00107 C15 1 0.204137 0.327139 0.733673 11.00000 0.01302 0.01325 = 0.01573 -0.00182 -0.00211 -0.00007 C16 1 0.178733 0.247493 0.849015 11.00000 0.01695 0.02014 = 0.01531 -0.00359 -0.00336 -0.00099 AFIX 43 H16 2 0.168930 0.283569 0.904451 11.00000 -1.20000 AFIX 0 C17 1 0.168084 0.116844 0.881459 11.00000 0.01688 0.01733 = 0.01557 0.00421 -0.00272 -0.00153 AFIX 43 H17 2 0.149665 0.062484 0.959533 11.00000 -1.20000 AFIX 0 C18 1 0.184262 0.063921 0.799998 11.00000 0.01718 0.01240 = 0.02588 0.00001 -0.00591 -0.00113 AFIX 43 H18 2 0.178629 -0.026485 0.823125 11.00000 -1.20000 AFIX 0 C19 1 0.208272 0.141140 0.686604 11.00000 0.01858 0.01304 = 0.02207 -0.00498 -0.00355 0.00093 AFIX 43 H19 2 0.218569 0.103900 0.631977 11.00000 -1.20000 AFIX 0 C20 1 0.217623 0.275043 0.651291 11.00000 0.01187 0.01214 = 0.01649 -0.00275 -0.00233 0.00102 C21 1 0.241669 0.361021 0.534145 11.00000 0.01797 0.01142 = 0.01427 -0.00405 -0.00115 0.00092 AFIX 43 H21 2 0.252394 0.327129 0.477206 11.00000 -1.20000 AFIX 0 C22 1 0.306031 1.163613 0.267270 11.00000 0.02915 0.00923 = 0.02416 -0.00509 -0.00658 0.00010 AFIX 13 H22 2 0.331462 1.221647 0.185465 11.00000 -1.20000 AFIX 0 C23 1 0.474530 1.188888 0.326173 11.00000 0.02757 0.01801 = 0.04409 -0.01626 -0.00726 0.00046 AFIX 137 H23A 2 0.601607 1.163642 0.296807 11.00000 -1.20000 H23B 2 0.448054 1.138950 0.407827 11.00000 -1.20000 H23C 2 0.481902 1.280267 0.311628 11.00000 -1.20000 AFIX 0 C24 1 0.103199 1.195831 0.312918 11.00000 0.02871 0.01940 = 0.07111 -0.02523 -0.00989 0.00480 AFIX 137 H24A 2 0.078616 1.145938 0.394652 11.00000 -1.20000 H24B 2 -0.001119 1.174906 0.275535 11.00000 -1.20000 H24C 2 0.101439 1.287404 0.297972 11.00000 -1.20000 AFIX 0 HKLF 4 REM xcalibur REM R1 = 0.0514 for 3179 Fo > 4sig(Fo) and 0.0792 for all 4353 data REM 256 parameters refined using 0 restraints END WGHT 0.0544 0.3549 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.269, deepest hole -0.241, 1-sigma level 0.057 Q1 1 0.3177 1.1035 0.2672 11.00000 0.05 0.27 Q2 1 0.2305 0.6484 0.3800 11.00000 0.05 0.26 Q3 1 0.2800 0.5458 0.4466 11.00000 0.05 0.25 ; _shelx_res_checksum 91076 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 O1 O 0.3292(2) 0.76422(11) -0.00692(10) 0.0273(3) Uani 1 1 d . . O2 O 0.27236(19) 0.55246(11) 0.08154(9) 0.0227(3) Uani 1 1 d . . O3 O 0.23575(17) 0.53922(10) 0.58572(9) 0.0165(3) Uani 1 1 d . . O4 O 0.2079(2) 0.52205(11) 0.76216(10) 0.0247(3) Uani 1 1 d . . C1 C 0.3027(2) 0.66566(14) 0.19499(13) 0.0139(3) Uani 1 1 d . . C2 C 0.2808(2) 0.55521(15) 0.29369(13) 0.0140(3) Uani 1 1 d . . H2 H 0.273462 0.470687 0.295968 0.017 Uiso 1 1 calc R U C3 C 0.2711(2) 0.58566(14) 0.38951(13) 0.0126(3) Uani 1 1 d . . C4 C 0.2842(2) 0.72157(14) 0.35076(13) 0.0131(3) Uani 1 1 d . . C5 C 0.2705(2) 0.79545(15) 0.41598(13) 0.0160(3) Uani 1 1 d . . H5 H 0.253775 0.748201 0.495520 0.019 Uiso 1 1 calc R U C6 C 0.2778(2) 0.92775(15) 0.38179(14) 0.0174(3) Uani 1 1 d . . H6 H 0.261282 0.956337 0.442151 0.021 Uiso 1 1 calc R U C7 C 0.3054(2) 1.02639(15) 0.27378(14) 0.0162(3) Uani 1 1 d . . C8 C 0.3322(2) 1.01070(15) 0.17193(14) 0.0170(3) Uani 1 1 d . . H8 H 0.354167 1.087794 0.106361 0.020 Uiso 1 1 calc R U C9 C 0.3319(2) 0.89920(15) 0.15117(14) 0.0155(3) Uani 1 1 d . . H9 H 0.351998 0.912051 0.073505 0.019 Uiso 1 1 calc R U C10 C 0.3068(2) 0.77257(14) 0.22597(13) 0.0132(3) Uani 1 1 d . . C11 C 0.3045(2) 0.66953(15) 0.08025(14) 0.0170(3) Uani 1 1 d . . C12 C 0.2623(3) 0.54844(18) -0.02808(14) 0.0267(4) Uani 1 1 d . . H12A H 0.388289 0.582273 -0.076386 0.032 Uiso 1 1 calc R U H12B H 0.152148 0.600600 -0.063080 0.032 Uiso 1 1 calc R U H12C H 0.239750 0.459723 -0.019097 0.032 Uiso 1 1 calc R U C13 C 0.2492(2) 0.48851(15) 0.50392(13) 0.0133(3) Uani 1 1 d . . C14 C 0.2153(2) 0.46560(15) 0.70009(13) 0.0159(3) Uani 1 1 d . . C15 C 0.2041(2) 0.32714(15) 0.73367(13) 0.0151(3) Uani 1 1 d . . C16 C 0.1787(2) 0.24749(16) 0.84902(14) 0.0184(4) Uani 1 1 d . . H16 H 0.168930 0.283569 0.904451 0.022 Uiso 1 1 calc R U C17 C 0.1681(2) 0.11684(16) 0.88146(14) 0.0198(4) Uani 1 1 d . . H17 H 0.149665 0.062484 0.959533 0.024 Uiso 1 1 calc R U C18 C 0.1843(2) 0.06392(16) 0.80000(15) 0.0205(4) Uani 1 1 d . . H18 H 0.178629 -0.026485 0.823125 0.025 Uiso 1 1 calc R U C19 C 0.2083(2) 0.14114(15) 0.68660(14) 0.0184(4) Uani 1 1 d . . H19 H 0.218569 0.103900 0.631977 0.022 Uiso 1 1 calc R U C20 C 0.2176(2) 0.27504(15) 0.65129(13) 0.0143(3) Uani 1 1 d . . C21 C 0.2417(2) 0.36102(14) 0.53415(13) 0.0149(3) Uani 1 1 d . . H21 H 0.252394 0.327129 0.477206 0.018 Uiso 1 1 calc R U C22 C 0.3060(3) 1.16361(15) 0.26727(15) 0.0210(4) Uani 1 1 d . . H22 H 0.331462 1.221647 0.185465 0.025 Uiso 1 1 calc R U C23 C 0.4745(3) 1.18889(17) 0.32617(17) 0.0284(4) Uani 1 1 d . . H23A H 0.601607 1.163642 0.296807 0.034 Uiso 1 1 calc R U H23B H 0.448054 1.138950 0.407827 0.034 Uiso 1 1 calc R U H23C H 0.481902 1.280267 0.311628 0.034 Uiso 1 1 calc R U C24 C 0.1032(3) 1.19583(18) 0.3129(2) 0.0371(5) Uani 1 1 d . . H24A H 0.078616 1.145938 0.394652 0.045 Uiso 1 1 calc R U H24B H -0.001119 1.174906 0.275535 0.045 Uiso 1 1 calc R U H24C H 0.101439 1.287404 0.297972 0.045 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 0.0469(9) 0.0185(6) 0.0132(6) -0.0029(5) -0.0010(6) -0.0046(6) O2 0.0388(8) 0.0166(6) 0.0142(6) -0.0077(5) -0.0021(5) -0.0036(5) O3 0.0253(6) 0.0107(5) 0.0125(6) -0.0035(4) -0.0023(5) -0.0003(5) O4 0.0403(8) 0.0187(6) 0.0167(6) -0.0085(5) -0.0037(5) 0.0006(5) C1 0.0142(8) 0.0112(7) 0.0147(8) -0.0038(6) -0.0003(6) -0.0004(6) C2 0.0155(8) 0.0098(7) 0.0160(8) -0.0044(6) -0.0014(6) 0.0009(6) C3 0.0125(8) 0.0100(7) 0.0139(8) -0.0030(6) -0.0018(6) 0.0010(6) C4 0.0128(8) 0.0117(7) 0.0137(8) -0.0034(6) -0.0024(6) 0.0013(6) C5 0.0196(9) 0.0137(8) 0.0136(8) -0.0042(6) -0.0024(6) 0.0013(6) C6 0.0226(9) 0.0137(8) 0.0185(8) -0.0087(7) -0.0038(7) 0.0014(6) C7 0.0153(8) 0.0110(7) 0.0220(9) -0.0057(7) -0.0041(7) 0.0006(6) C8 0.0183(8) 0.0111(7) 0.0183(8) -0.0017(6) -0.0032(7) -0.0001(6) C9 0.0144(8) 0.0146(8) 0.0144(8) -0.0023(6) -0.0022(6) 0.0004(6) C10 0.0103(7) 0.0123(7) 0.0158(8) -0.0042(6) -0.0022(6) 0.0012(6) C11 0.0188(9) 0.0154(8) 0.0160(8) -0.0058(7) -0.0007(7) 0.0000(6) C12 0.0427(12) 0.0248(9) 0.0158(9) -0.0110(8) -0.0036(8) -0.0044(8) C13 0.0144(8) 0.0141(8) 0.0119(7) -0.0054(6) -0.0027(6) 0.0018(6) C14 0.0171(8) 0.0150(8) 0.0136(8) -0.0031(6) -0.0025(6) 0.0011(6) C15 0.0130(8) 0.0133(8) 0.0157(8) -0.0018(6) -0.0021(6) -0.0001(6) C16 0.0169(8) 0.0201(8) 0.0153(8) -0.0036(7) -0.0034(7) -0.0010(7) C17 0.0169(8) 0.0173(8) 0.0156(8) 0.0042(7) -0.0027(7) -0.0015(6) C18 0.0172(9) 0.0124(8) 0.0259(9) 0.0000(7) -0.0059(7) -0.0011(6) C19 0.0186(9) 0.0130(8) 0.0221(9) -0.0050(7) -0.0036(7) 0.0009(6) C20 0.0119(8) 0.0121(7) 0.0165(8) -0.0028(6) -0.0023(6) 0.0010(6) C21 0.0180(8) 0.0114(7) 0.0143(8) -0.0041(6) -0.0012(6) 0.0009(6) C22 0.0292(10) 0.0092(7) 0.0242(9) -0.0051(7) -0.0066(8) 0.0001(7) C23 0.0276(10) 0.0180(9) 0.0441(12) -0.0163(8) -0.0073(9) 0.0005(7) C24 0.0287(11) 0.0194(10) 0.0711(16) -0.0252(10) -0.0099(10) 0.0048(8) 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 115.10(13) C14 O3 C13 123.52(12) C2 C1 C10 108.04(14) C2 C1 C11 125.22(14) C10 C1 C11 126.57(14) C1 C2 C3 110.78(14) C1 C2 H2 124.6 C3 C2 H2 124.6 C2 C3 C4 107.44(13) C2 C3 C13 122.50(13) C4 C3 C13 130.06(14) C5 C4 C3 127.74(14) C5 C4 C10 125.35(14) C3 C4 C10 106.87(13) C6 C5 C4 129.61(15) C6 C5 H5 115.2 C4 C5 H5 115.2 C5 C6 C7 131.24(15) C5 C6 H6 114.4 C7 C6 H6 114.4 C8 C7 C6 125.91(15) C8 C7 C22 116.87(14) C6 C7 C22 117.23(14) C7 C8 C9 129.84(15) C7 C8 H8 115.1 C9 C8 H8 115.1 C10 C9 C8 130.10(16) C10 C9 H9 115.0 C8 C9 H9 115.0 C9 C10 C1 125.34(15) C9 C10 C4 127.79(14) C1 C10 C4 106.86(13) O1 C11 O2 122.31(15) O1 C11 C1 126.22(15) O2 C11 C1 111.47(13) 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 C21 C13 O3 120.15(14) C21 C13 C3 126.74(14) O3 C13 C3 113.11(13) O4 C14 O3 116.69(14) O4 C14 C15 126.62(15) O3 C14 C15 116.69(13) C20 C15 C16 120.67(14) C20 C15 C14 120.12(14) C16 C15 C14 119.21(15) C17 C16 C15 119.61(15) C17 C16 H16 120.2 C15 C16 H16 120.2 C16 C17 C18 120.15(15) C16 C17 H17 119.9 C18 C17 H17 119.9 C19 C18 C17 120.74(15) C19 C18 H18 119.6 C17 C18 H18 119.6 C18 C19 C20 120.18(16) C18 C19 H19 119.9 C20 C19 H19 119.9 C15 C20 C19 118.64(15) C15 C20 C21 118.45(14) C19 C20 C21 122.91(15) C13 C21 C20 121.06(15) C13 C21 H21 119.5 C20 C21 H21 119.5 C24 C22 C7 111.04(14) C24 C22 C23 111.93(15) C7 C22 C23 111.70(14) C24 C22 H22 107.3 C7 C22 H22 107.3 C23 C22 H22 107.3 C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C22 C24 H24A 109.5 C22 C24 H24B 109.5 H24A C24 H24B 109.5 C22 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.2125(19) O2 C11 1.3432(19) O2 C12 1.445(2) O3 C14 1.3770(18) O3 C13 1.3813(18) O4 C14 1.2031(19) C1 C2 1.391(2) C1 C10 1.420(2) C1 C11 1.465(2) C2 C3 1.405(2) C2 H2 0.9500 C3 C4 1.424(2) C3 C13 1.452(2) C4 C5 1.397(2) C4 C10 1.476(2) C5 C6 1.390(2) C5 H5 0.9500 C6 C7 1.402(2) C6 H6 0.9500 C7 C8 1.387(2) C7 C22 1.526(2) C8 C9 1.392(2) C8 H8 0.9500 C9 C10 1.384(2) C9 H9 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C21 1.343(2) C14 C15 1.458(2) C15 C20 1.400(2) C15 C16 1.402(2) C16 C17 1.375(2) C16 H16 0.9500 C17 C18 1.395(3) C17 H17 0.9500 C18 C19 1.375(2) C18 H18 0.9500 C19 C20 1.406(2) C19 H19 0.9500 C20 C21 1.438(2) C21 H21 0.9500 C22 C24 1.521(3) C22 C23 1.529(2) C22 H22 1.0000 C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 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 -0.23(18) C11 C1 C2 C3 -175.77(15) C1 C2 C3 C4 0.92(18) C1 C2 C3 C13 -179.73(14) C2 C3 C4 C5 176.41(16) C13 C3 C4 C5 -2.9(3) C2 C3 C4 C10 -1.21(17) C13 C3 C4 C10 179.51(15) C3 C4 C5 C6 -178.36(16) C10 C4 C5 C6 -1.2(3) C4 C5 C6 C7 -1.7(3) C5 C6 C7 C8 0.2(3) C5 C6 C7 C22 -179.77(17) C6 C7 C8 C9 2.4(3) C22 C7 C8 C9 -177.60(16) C7 C8 C9 C10 -0.7(3) C8 C9 C10 C1 177.80(16) C8 C9 C10 C4 -3.7(3) C2 C1 C10 C9 178.23(15) C11 C1 C10 C9 -6.3(3) C2 C1 C10 C4 -0.53(17) C11 C1 C10 C4 174.93(15) C5 C4 C10 C9 4.7(3) C3 C4 C10 C9 -177.64(15) C5 C4 C10 C1 -176.61(15) C3 C4 C10 C1 1.08(17) C12 O2 C11 O1 -2.1(2) C12 O2 C11 C1 177.19(14) C2 C1 C11 O1 -177.67(17) C10 C1 C11 O1 7.6(3) C2 C1 C11 O2 3.1(2) C10 C1 C11 O2 -171.65(15) C14 O3 C13 C21 0.3(2) C14 O3 C13 C3 -179.66(13) C2 C3 C13 C21 2.2(3) C4 C3 C13 C21 -178.64(17) C2 C3 C13 O3 -177.85(14) C4 C3 C13 O3 1.3(2) C13 O3 C14 O4 179.05(14) C13 O3 C14 C15 -1.1(2) O4 C14 C15 C20 -179.12(16) O3 C14 C15 C20 1.1(2) O4 C14 C15 C16 1.2(3) O3 C14 C15 C16 -178.57(14) C20 C15 C16 C17 0.4(2) C14 C15 C16 C17 -179.99(15) C15 C16 C17 C18 0.6(2) C16 C17 C18 C19 -0.9(3) C17 C18 C19 C20 0.3(3) C16 C15 C20 C19 -1.0(2) C14 C15 C20 C19 179.38(15) C16 C15 C20 C21 179.40(14) C14 C15 C20 C21 -0.2(2) C18 C19 C20 C15 0.7(2) C18 C19 C20 C21 -179.72(15) O3 C13 C21 C20 0.6(2) C3 C13 C21 C20 -179.42(15) C15 C20 C21 C13 -0.6(2) C19 C20 C21 C13 179.76(16) C8 C7 C22 C24 115.17(18) C6 C7 C22 C24 -64.8(2) C8 C7 C22 C23 -119.11(17) C6 C7 C22 C23 60.9(2)