#------------------------------------------------------------------------------ #$Date: 2017-12-23 07:14:26 +0200 (Sat, 23 Dec 2017) $ #$Revision: 204512 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156043.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_7156043 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 H19 I O4' _chemical_formula_sum 'C24 H19 I O4' _chemical_formula_weight 498.29 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 90 _cell_angle_beta 103.877(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5028(6) _cell_length_b 9.0127(3) _cell_length_c 17.7036(10) _cell_measurement_reflns_used 12728 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.87 _cell_measurement_theta_min 2.35 _cell_volume 1936.69(16) _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 1.000 _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 0.1044 _diffrn_reflns_av_unetI/netI 0.0666 _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 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 32058 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.000 _diffrn_reflns_theta_min 2.370 _diffrn_source 'Varimax 50 kV 24 mA Rotating anode' _exptl_absorpt_coefficient_mu 1.683 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_correction_T_min 0.825 _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 red _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.030 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.811 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.138 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 4672 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0452 _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^)+(0.0240P)^2^+2.3963P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.0828 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3597 _reflns_number_total 4672 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02861j2.cif _cod_data_source_block shelxl_CCDC3 _cod_database_code 7156043 _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 0.951 _shelx_estimated_absorpt_t_max 0.967 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2016/6 at 23:04:34 on 04-Apr-2017 CELL 0.71075 12.50280 9.01270 17.70360 90.00000 103.87700 90.00000 ZERR 4 0.00060 0.00030 0.00100 0.00000 0.00500 0.00000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H I O UNIT 96 76 4 16 SHEL 99999.000000 0.756965 OMIT 1 0 0 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.030 0.020 0.020 WGHT 0.024000 2.396300 FVAR 0.25050 I1 3 0.149119 0.155340 0.573007 11.00000 0.01608 0.00713 = 0.02552 0.00057 0.00684 -0.00048 O1 4 0.494665 0.412288 0.307882 11.00000 0.02510 0.01879 = 0.02048 0.00172 0.01274 0.00251 O2 4 0.339900 0.547638 0.292257 11.00000 0.02300 0.02020 = 0.01391 0.00534 0.00505 0.00170 O3 4 0.220933 0.617347 0.545343 11.00000 0.01659 0.00830 = 0.02290 0.00087 0.00936 -0.00004 O4 4 0.145503 0.831253 0.559754 11.00000 0.02491 0.00621 = 0.04590 -0.00067 0.00919 -0.00213 C1 1 0.395283 0.415485 0.407132 11.00000 0.01517 0.01248 = 0.01330 -0.00390 0.00397 -0.00534 C2 1 0.309578 0.476442 0.435352 11.00000 0.01241 0.01048 = 0.01368 -0.00143 -0.00005 -0.00340 AFIX 43 H2 2 0.259557 0.549633 0.409130 11.00000 -1.20000 AFIX 0 C3 1 0.307708 0.414813 0.507425 11.00000 0.01028 0.01061 = 0.01694 -0.00255 0.00337 -0.00263 C4 1 0.398652 0.316117 0.528697 11.00000 0.01289 0.00838 = 0.01445 -0.00477 0.00457 -0.00500 C5 1 0.434976 0.244459 0.600051 11.00000 0.01138 0.01161 = 0.01380 -0.00392 0.00314 -0.00325 AFIX 43 H5 2 0.391335 0.261398 0.636362 11.00000 -1.20000 AFIX 0 C6 1 0.525452 0.151843 0.626239 11.00000 0.01894 0.01266 = 0.01267 0.00017 0.00447 0.00028 AFIX 43 H6 2 0.535113 0.117499 0.678174 11.00000 -1.20000 AFIX 0 C7 1 0.604667 0.101282 0.587824 11.00000 0.00941 0.00895 = 0.01745 -0.00573 -0.00167 -0.00357 C8 1 0.609903 0.137355 0.512277 11.00000 0.01241 0.01094 = 0.01939 -0.00365 0.00565 0.00063 AFIX 43 H8 2 0.667090 0.088972 0.494842 11.00000 -1.20000 AFIX 0 C9 1 0.545508 0.232134 0.458337 11.00000 0.01288 0.01449 = 0.01106 -0.00530 0.00447 -0.00326 AFIX 43 H9 2 0.567353 0.242022 0.410755 11.00000 -1.20000 AFIX 0 C10 1 0.453466 0.315090 0.463532 11.00000 0.01695 0.00707 = 0.01181 -0.00237 0.00309 -0.00404 C11 1 0.417984 0.454959 0.332544 11.00000 0.01528 0.01123 = 0.01438 -0.00351 0.00007 -0.00490 C12 1 0.359308 0.603719 0.220768 11.00000 0.02889 0.02005 = 0.01964 0.00464 0.00784 0.00154 AFIX 137 H12A 2 0.356589 0.521702 0.184011 11.00000 -1.20000 H12B 2 0.432025 0.650809 0.231087 11.00000 -1.20000 H12C 2 0.302552 0.676907 0.198433 11.00000 -1.20000 AFIX 0 C13 1 0.226875 0.463042 0.549382 11.00000 0.01000 0.00613 = 0.01851 -0.00003 -0.00177 0.00602 C14 1 0.144419 0.699655 0.571279 11.00000 0.01530 0.00994 = 0.01955 -0.00386 0.00283 0.00019 C15 1 0.072842 0.620202 0.610863 11.00000 0.00964 0.01102 = 0.01807 0.00052 -0.00167 0.00164 C16 1 -0.001390 0.701949 0.642371 11.00000 0.01280 0.01444 = 0.02880 -0.00960 -0.00203 0.00085 AFIX 43 H16 2 -0.005215 0.806762 0.636680 11.00000 -1.20000 AFIX 0 C17 1 -0.068730 0.629817 0.681589 11.00000 0.00992 0.02737 = 0.02129 -0.00979 0.00226 0.00475 AFIX 43 H17 2 -0.119477 0.684472 0.702908 11.00000 -1.20000 AFIX 0 C18 1 -0.062013 0.476289 0.689819 11.00000 0.01520 0.02734 = 0.01580 0.00124 0.00299 0.00018 AFIX 43 H18 2 -0.107505 0.426852 0.717797 11.00000 -1.20000 AFIX 0 C19 1 0.010023 0.394395 0.657829 11.00000 0.01420 0.01621 = 0.02131 0.00162 0.00321 0.00318 AFIX 43 H19 2 0.012005 0.289469 0.663102 11.00000 -1.20000 AFIX 0 C20 1 0.079720 0.464302 0.617939 11.00000 0.01048 0.01156 = 0.01335 -0.00029 -0.00314 0.00070 C21 1 0.157725 0.387199 0.582202 11.00000 0.01356 0.00461 = 0.01561 -0.00270 -0.00008 -0.00075 C22 1 0.698219 0.003281 0.632335 11.00000 0.01198 0.01704 = 0.01868 -0.00259 0.00128 0.00084 AFIX 13 H22 2 0.708374 -0.077982 0.596231 11.00000 -1.20000 AFIX 0 C23 1 0.805528 0.093670 0.651703 11.00000 0.01374 0.02368 = 0.03325 0.00638 0.00000 0.00066 AFIX 137 H23A 2 0.798325 0.175709 0.686477 11.00000 -1.20000 H23B 2 0.819971 0.133501 0.603602 11.00000 -1.20000 H23C 2 0.866736 0.029454 0.677384 11.00000 -1.20000 AFIX 0 C24 1 0.679406 -0.070464 0.705494 11.00000 0.01783 0.02206 = 0.01922 0.00347 0.00370 0.00557 AFIX 137 H24A 2 0.609794 -0.125510 0.692657 11.00000 -1.20000 H24B 2 0.676179 0.005639 0.744424 11.00000 -1.20000 H24C 2 0.740143 -0.138963 0.726466 11.00000 -1.20000 AFIX 0 HKLF 4 REM xcalibur REM R1 = 0.0452 for 3597 Fo > 4sig(Fo) and 0.0669 for all 4672 data REM 265 parameters refined using 0 restraints END WGHT 0.0239 2.4077 REM Instructions for potential hydrogen bonds EQIV $1 x, -y+1/2, z-1/2 HTAB C12 I1_$1 REM Highest difference peak 0.811, deepest hole -0.619, 1-sigma level 0.138 Q1 1 0.1091 0.1493 0.6081 11.00000 0.05 0.81 Q2 1 0.1756 0.7643 0.5259 11.00000 0.05 0.78 Q3 1 0.1255 0.6559 0.6089 11.00000 0.05 0.63 ; _shelx_res_checksum 68155 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 I1 I 0.14912(2) 0.15534(3) 0.57301(2) 0.01593(8) Uani 1 1 d . . O1 O 0.4947(2) 0.4123(3) 0.30788(16) 0.0202(7) Uani 1 1 d . . O2 O 0.3399(2) 0.5476(3) 0.29226(15) 0.0189(6) Uani 1 1 d . . O3 O 0.2209(2) 0.6173(3) 0.54534(16) 0.0151(6) Uani 1 1 d . . O4 O 0.1455(2) 0.8313(3) 0.55975(18) 0.0256(7) Uani 1 1 d . . C1 C 0.3953(3) 0.4155(4) 0.4071(2) 0.0136(8) Uani 1 1 d . . C2 C 0.3096(3) 0.4764(4) 0.4354(2) 0.0127(8) Uani 1 1 d . . H2 H 0.259557 0.549633 0.409130 0.015 Uiso 1 1 calc R U C3 C 0.3077(3) 0.4148(4) 0.5074(2) 0.0126(8) Uani 1 1 d . . C4 C 0.3987(3) 0.3161(4) 0.5287(2) 0.0117(8) Uani 1 1 d . . C5 C 0.4350(3) 0.2445(4) 0.6001(2) 0.0122(8) Uani 1 1 d . . H5 H 0.391335 0.261398 0.636362 0.015 Uiso 1 1 calc R U C6 C 0.5255(3) 0.1518(4) 0.6262(2) 0.0146(8) Uani 1 1 d . . H6 H 0.535113 0.117499 0.678174 0.018 Uiso 1 1 calc R U C7 C 0.6047(3) 0.1013(4) 0.5878(2) 0.0128(8) Uani 1 1 d . . C8 C 0.6099(3) 0.1374(4) 0.5123(2) 0.0139(8) Uani 1 1 d . . H8 H 0.667090 0.088972 0.494842 0.017 Uiso 1 1 calc R U C9 C 0.5455(3) 0.2321(4) 0.4583(2) 0.0125(8) Uani 1 1 d . . H9 H 0.567353 0.242022 0.410755 0.015 Uiso 1 1 calc R U C10 C 0.4535(3) 0.3151(4) 0.4635(2) 0.0120(8) Uani 1 1 d . . C11 C 0.4180(3) 0.4550(4) 0.3325(2) 0.0142(8) Uani 1 1 d . . C12 C 0.3593(4) 0.6037(5) 0.2208(2) 0.0225(10) Uani 1 1 d . . H12A H 0.356589 0.521702 0.184011 0.027 Uiso 1 1 calc R U H12B H 0.432025 0.650809 0.231087 0.027 Uiso 1 1 calc R U H12C H 0.302552 0.676907 0.198433 0.027 Uiso 1 1 calc R U C13 C 0.2269(3) 0.4630(4) 0.5494(2) 0.0124(8) Uani 1 1 d . . C14 C 0.1444(3) 0.6997(4) 0.5713(2) 0.0152(8) Uani 1 1 d . . C15 C 0.0728(3) 0.6202(4) 0.6109(2) 0.0138(9) Uani 1 1 d . . C16 C -0.0014(3) 0.7019(5) 0.6424(2) 0.0199(10) Uani 1 1 d . . H16 H -0.005215 0.806762 0.636680 0.024 Uiso 1 1 calc R U C17 C -0.0687(3) 0.6298(5) 0.6816(2) 0.0198(10) Uani 1 1 d . . H17 H -0.119477 0.684472 0.702908 0.024 Uiso 1 1 calc R U C18 C -0.0620(3) 0.4763(5) 0.6898(2) 0.0196(9) Uani 1 1 d . . H18 H -0.107505 0.426852 0.717797 0.023 Uiso 1 1 calc R U C19 C 0.0100(3) 0.3944(5) 0.6578(2) 0.0174(9) Uani 1 1 d . . H19 H 0.012005 0.289469 0.663102 0.021 Uiso 1 1 calc R U C20 C 0.0797(3) 0.4643(4) 0.6179(2) 0.0128(8) Uani 1 1 d . . C21 C 0.1577(3) 0.3872(4) 0.5822(2) 0.0119(8) Uani 1 1 d . . C22 C 0.6982(3) 0.0033(4) 0.6323(2) 0.0163(9) Uani 1 1 d . . H22 H 0.708374 -0.077982 0.596231 0.020 Uiso 1 1 calc R U C23 C 0.8055(3) 0.0937(5) 0.6517(3) 0.0245(10) Uani 1 1 d . . H23A H 0.798325 0.175709 0.686477 0.029 Uiso 1 1 calc R U H23B H 0.819971 0.133501 0.603602 0.029 Uiso 1 1 calc R U H23C H 0.866736 0.029454 0.677384 0.029 Uiso 1 1 calc R U C24 C 0.6794(3) -0.0705(5) 0.7055(2) 0.0198(9) Uani 1 1 d . . H24A H 0.609794 -0.125510 0.692657 0.024 Uiso 1 1 calc R U H24B H 0.676179 0.005639 0.744424 0.024 Uiso 1 1 calc R U H24C H 0.740143 -0.138963 0.726466 0.024 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 I1 0.01608(14) 0.00713(12) 0.02552(16) 0.00057(12) 0.00684(10) -0.00048(11) O1 0.0251(17) 0.0188(15) 0.0205(16) 0.0017(13) 0.0127(14) 0.0025(13) O2 0.0230(16) 0.0202(15) 0.0139(15) 0.0053(12) 0.0050(12) 0.0017(13) O3 0.0166(15) 0.0083(14) 0.0229(16) 0.0009(11) 0.0094(12) 0.0000(11) O4 0.0249(17) 0.0062(14) 0.046(2) -0.0007(14) 0.0092(15) -0.0021(13) C1 0.015(2) 0.012(2) 0.013(2) -0.0039(16) 0.0040(17) -0.0053(16) C2 0.012(2) 0.0105(18) 0.014(2) -0.0014(16) -0.0001(16) -0.0034(16) C3 0.010(2) 0.0106(19) 0.017(2) -0.0026(16) 0.0034(16) -0.0026(16) C4 0.013(2) 0.0084(19) 0.014(2) -0.0048(15) 0.0046(16) -0.0050(15) C5 0.011(2) 0.0116(19) 0.014(2) -0.0039(16) 0.0031(16) -0.0033(15) C6 0.019(2) 0.0127(19) 0.013(2) 0.0002(17) 0.0045(16) 0.0003(18) C7 0.0094(19) 0.0089(18) 0.017(2) -0.0057(16) -0.0017(16) -0.0036(15) C8 0.012(2) 0.011(2) 0.019(2) -0.0036(16) 0.0056(16) 0.0006(16) C9 0.013(2) 0.014(2) 0.011(2) -0.0053(16) 0.0045(16) -0.0033(16) C10 0.017(2) 0.0071(19) 0.012(2) -0.0024(14) 0.0031(16) -0.0040(15) C11 0.015(2) 0.0112(19) 0.014(2) -0.0035(16) 0.0001(17) -0.0049(16) C12 0.029(3) 0.020(2) 0.020(2) 0.0046(18) 0.008(2) 0.0015(19) C13 0.010(2) 0.0061(18) 0.019(2) 0.0000(16) -0.0018(16) 0.0060(15) C14 0.015(2) 0.0099(18) 0.020(2) -0.0039(17) 0.0028(17) 0.0002(17) C15 0.010(2) 0.011(2) 0.018(2) 0.0005(16) -0.0017(17) 0.0016(15) C16 0.013(2) 0.014(2) 0.029(3) -0.0096(18) -0.0020(18) 0.0009(16) C17 0.010(2) 0.027(2) 0.021(2) -0.0098(19) 0.0023(17) 0.0048(18) C18 0.015(2) 0.027(2) 0.016(2) 0.0012(18) 0.0030(18) 0.0002(18) C19 0.014(2) 0.016(2) 0.021(2) 0.0016(17) 0.0032(18) 0.0032(17) C20 0.010(2) 0.0116(19) 0.013(2) -0.0003(16) -0.0031(16) 0.0007(16) C21 0.014(2) 0.0046(17) 0.016(2) -0.0027(15) -0.0001(16) -0.0008(15) C22 0.012(2) 0.017(2) 0.019(2) -0.0026(17) 0.0013(17) 0.0008(16) C23 0.014(2) 0.024(2) 0.033(3) 0.006(2) 0.000(2) 0.0007(19) C24 0.018(2) 0.022(2) 0.019(2) 0.0035(18) 0.0037(18) 0.0056(18) 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' I I -0.4742 1.8119 '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 115.4(3) C14 O3 C13 123.7(3) C2 C1 C10 107.9(3) C2 C1 C11 124.0(4) C10 C1 C11 128.1(4) C3 C2 C1 110.6(4) C3 C2 H2 124.7 C1 C2 H2 124.7 C2 C3 C4 107.7(3) C2 C3 C13 120.8(4) C4 C3 C13 131.3(4) C5 C4 C3 126.6(4) C5 C4 C10 126.4(3) C3 C4 C10 106.8(3) C6 C5 C4 129.9(4) C6 C5 H5 115.1 C4 C5 H5 115.1 C5 C6 C7 130.1(4) C5 C6 H6 115.0 C7 C6 H6 115.0 C8 C7 C6 126.1(4) C8 C7 C22 115.1(3) C6 C7 C22 118.7(4) C9 C8 C7 130.7(4) C9 C8 H8 114.7 C7 C8 H8 114.7 C8 C9 C10 129.6(4) C8 C9 H9 115.2 C10 C9 H9 115.2 C9 C10 C1 126.2(4) C9 C10 C4 126.9(3) C1 C10 C4 106.9(3) O1 C11 O2 122.8(4) O1 C11 C1 126.4(4) O2 C11 C1 110.8(3) 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 120.0(3) C21 C13 C3 131.9(3) O3 C13 C3 107.9(3) O4 C14 O3 116.0(4) O4 C14 C15 127.0(4) O3 C14 C15 117.0(3) C16 C15 C20 121.3(4) C16 C15 C14 118.5(3) C20 C15 C14 120.2(3) C17 C16 C15 119.7(4) C17 C16 H16 120.1 C15 C16 H16 120.1 C16 C17 C18 119.6(4) C16 C17 H17 120.2 C18 C17 H17 120.2 C19 C18 C17 121.0(4) C19 C18 H18 119.5 C17 C18 H18 119.5 C18 C19 C20 120.8(4) C18 C19 H19 119.6 C20 C19 H19 119.6 C19 C20 C15 117.5(4) C19 C20 C21 124.6(3) C15 C20 C21 117.9(3) C13 C21 C20 120.9(3) C13 C21 I1 120.1(3) C20 C21 I1 118.7(3) C24 C22 C7 115.9(3) C24 C22 C23 110.3(3) C7 C22 C23 109.2(3) C24 C22 H22 107.0 C7 C22 H22 107.0 C23 C22 H22 107.0 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 I1 C21 2.097(3) O1 C11 1.208(5) O2 C11 1.351(5) O2 C12 1.436(5) O3 C14 1.374(4) O3 C13 1.394(4) O4 C14 1.204(4) C1 C2 1.399(5) C1 C10 1.413(5) C1 C11 1.460(5) C2 C3 1.397(5) C2 H2 0.9500 C3 C4 1.421(5) C3 C13 1.457(5) C4 C5 1.394(5) C4 C10 1.476(5) C5 C6 1.393(5) C5 H5 0.9500 C6 C7 1.405(5) C6 H6 0.9500 C7 C8 1.393(5) C7 C22 1.525(5) C8 C9 1.386(5) C8 H8 0.9500 C9 C10 1.394(5) C9 H9 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C21 1.339(5) C14 C15 1.451(5) C15 C16 1.401(5) C15 C20 1.411(5) C16 C17 1.376(6) C16 H16 0.9500 C17 C18 1.392(6) C17 H17 0.9500 C18 C19 1.386(5) C18 H18 0.9500 C19 C20 1.396(5) C19 H19 0.9500 C20 C21 1.460(5) C22 C24 1.523(5) C22 C23 1.536(5) 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 -2.1(4) C11 C1 C2 C3 178.9(3) C1 C2 C3 C4 3.0(4) C1 C2 C3 C13 178.7(3) C2 C3 C4 C5 172.0(4) C13 C3 C4 C5 -3.0(7) C2 C3 C4 C10 -2.7(4) C13 C3 C4 C10 -177.8(4) C3 C4 C5 C6 -177.0(4) C10 C4 C5 C6 -3.2(6) C4 C5 C6 C7 -1.6(7) C5 C6 C7 C8 1.1(7) C5 C6 C7 C22 178.0(4) C6 C7 C8 C9 3.0(7) C22 C7 C8 C9 -174.0(4) C7 C8 C9 C10 -2.7(7) C8 C9 C10 C1 176.6(4) C8 C9 C10 C4 -2.9(6) C2 C1 C10 C9 -179.3(4) C11 C1 C10 C9 -0.3(6) C2 C1 C10 C4 0.3(4) C11 C1 C10 C4 179.2(4) C5 C4 C10 C9 6.3(6) C3 C4 C10 C9 -178.9(4) C5 C4 C10 C1 -173.3(3) C3 C4 C10 C1 1.5(4) C12 O2 C11 O1 -5.6(5) C12 O2 C11 C1 174.9(3) C2 C1 C11 O1 175.2(4) C10 C1 C11 O1 -3.6(7) C2 C1 C11 O2 -5.2(5) C10 C1 C11 O2 176.0(4) C14 O3 C13 C21 -2.2(6) C14 O3 C13 C3 172.6(3) C2 C3 C13 C21 130.0(5) C4 C3 C13 C21 -55.5(7) C2 C3 C13 O3 -43.9(5) C4 C3 C13 O3 130.6(4) C13 O3 C14 O4 -175.8(4) C13 O3 C14 C15 5.4(5) O4 C14 C15 C16 -2.5(7) O3 C14 C15 C16 176.0(3) O4 C14 C15 C20 178.3(4) O3 C14 C15 C20 -3.2(6) C20 C15 C16 C17 0.5(6) C14 C15 C16 C17 -178.7(4) C15 C16 C17 C18 0.3(6) C16 C17 C18 C19 -1.2(6) C17 C18 C19 C20 1.5(6) C18 C19 C20 C15 -0.7(6) C18 C19 C20 C21 -179.8(4) C16 C15 C20 C19 -0.2(6) C14 C15 C20 C19 178.9(4) C16 C15 C20 C21 178.9(4) C14 C15 C20 C21 -2.0(6) O3 C13 C21 C20 -3.4(6) C3 C13 C21 C20 -176.8(4) O3 C13 C21 I1 170.4(3) C3 C13 C21 I1 -3.0(6) C19 C20 C21 C13 -175.6(4) C15 C20 C21 C13 5.4(5) C19 C20 C21 I1 10.5(5) C15 C20 C21 I1 -168.5(3) C8 C7 C22 C24 -164.5(3) C6 C7 C22 C24 18.2(5) C8 C7 C22 C23 70.3(4) C6 C7 C22 C23 -106.9(4)