#------------------------------------------------------------------------------ #$Date: 2023-03-23 11:30:11 +0200 (Thu, 23 Mar 2023) $ #$Revision: 282004 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106953.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_8106953 loop_ _publ_author_name '\H-1-benzopyran-3-carboxylate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 98.4600(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.3751(2) _cell_length_b 17.3340(3) _cell_length_c 13.3828(2) _cell_measurement_reflns_used 8043 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.49 _cell_volume 2151.15(7) _computing_cell_refinement 'SAINT [15]' _computing_data_collection 'APEX2 [14]' _computing_data_reduction 'SAINT [15]' _computing_molecular_graphics 'PLATON [3]' _computing_publication_material 'PLATON [3]' _computing_structure_refinement 'SHELXL-97 [2]' _computing_structure_solution 'SHELXS-97 [2]' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 20004 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.94 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9729 _exptl_absorpt_correction_T_min 0.9419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS [13]' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.368 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 _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 307 _refine_ls_number_reflns 4940 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0381 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.5243P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.1065 _reflns_number_gt 4116 _reflns_number_total 4940 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL ks315, 150 K, P2(1)/n CELL 0.71073 9.3751 17.3340 13.3828 90.000 98.460 90.000 ZERR 8 0.0002 0.0003 0.0002 0.000 0.001 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H O UNIT 104 80 32 OMIT -2 55 L.S. 9 ACTA BOND $H FMAP 2 PLAN -10 HTAB SIZE 0.26 0.44 0.57 TEMP -133.000 REM molecule 1 WGHT 0.055500 0.524300 FVAR 0.13832 O1 3 0.272239 0.510735 0.865338 11.00000 0.01826 0.01494 = 0.03103 -0.00295 0.00381 -0.00114 O2 3 0.046583 0.539758 0.875859 11.00000 0.01963 0.02350 = 0.04976 -0.00123 0.00820 -0.00458 O3 3 -0.028818 0.698971 0.854533 11.00000 0.01803 0.02562 = 0.04142 -0.00058 0.00313 0.00212 O4 3 0.163898 0.776928 0.889547 11.00000 0.02148 0.01666 = 0.04228 -0.00174 -0.00033 0.00324 C2 1 0.165583 0.564853 0.873795 11.00000 0.01802 0.01791 = 0.02370 -0.00165 0.00397 0.00030 C3 1 0.211502 0.645849 0.879086 11.00000 0.01853 0.01593 = 0.01934 -0.00114 0.00269 0.00051 C4 1 0.352963 0.663726 0.886998 11.00000 0.02039 0.01558 = 0.02300 -0.00101 0.00308 -0.00157 AFIX 43 H4 2 0.381259 0.716352 0.892828 11.00000 -1.20000 AFIX 0 C4A 1 0.461258 0.605728 0.886846 11.00000 0.01792 0.01763 = 0.02059 0.00006 0.00235 0.00101 C5 1 0.609555 0.621822 0.896285 11.00000 0.01978 0.02161 = 0.03152 0.00017 0.00251 -0.00262 AFIX 43 H5 2 0.642165 0.673620 0.904869 11.00000 -1.20000 AFIX 0 C6 1 0.707892 0.563366 0.893220 11.00000 0.01664 0.03125 = 0.02997 0.00122 0.00305 0.00165 AFIX 43 H6 2 0.807990 0.574546 0.899202 11.00000 -1.20000 AFIX 0 C7 1 0.658925 0.487256 0.881199 11.00000 0.02372 0.02718 = 0.02350 -0.00114 0.00410 0.00955 AFIX 43 H7 2 0.727080 0.446886 0.879580 11.00000 -1.20000 AFIX 0 C8 1 0.513946 0.469243 0.871611 11.00000 0.02610 0.01895 = 0.02168 -0.00309 0.00370 0.00228 AFIX 43 H8 2 0.481982 0.417309 0.863443 11.00000 -1.20000 AFIX 0 C8A 1 0.416344 0.529166 0.874250 11.00000 0.01699 0.01892 = 0.01758 0.00001 0.00229 -0.00021 C9 1 0.099348 0.707671 0.872868 11.00000 0.01955 0.01975 = 0.01962 -0.00049 0.00317 0.00028 C10 1 0.072832 0.844635 0.870718 11.00000 0.02437 0.02036 = 0.03172 0.00119 0.00123 0.00669 AFIX 23 H10A 2 0.017540 0.853293 0.927300 11.00000 -1.20000 H10B 2 0.004069 0.838276 0.807646 11.00000 -1.20000 AFIX 0 C11 1 0.172187 0.910685 0.861454 11.00000 0.02948 0.02237 = 0.03162 0.00477 0.00332 0.00353 AFIX 43 H11 2 0.235321 0.906620 0.812304 11.00000 -1.20000 AFIX 0 C12 1 0.179189 0.973830 0.915769 11.00000 0.03892 0.02324 = 0.04458 0.00174 -0.00087 0.00233 AFIX 93 H12A 2 0.117846 0.980112 0.965716 11.00000 -1.20000 H12B 2 0.245608 1.013333 0.905204 11.00000 -1.20000 AFIX 0 REM molecule 2 O21 3 0.771382 0.298013 0.880729 11.00000 0.01612 0.01427 = 0.03378 -0.00097 0.00538 -0.00020 O22 3 0.545449 0.267206 0.885840 11.00000 0.01701 0.02280 = 0.05513 -0.00665 0.00736 0.00238 O23 3 0.468782 0.108794 0.863409 11.00000 0.01877 0.02337 = 0.05346 -0.00247 0.01245 -0.00349 O24 3 0.657964 0.031975 0.850720 11.00000 0.01871 0.01426 = 0.04075 -0.00037 0.00366 -0.00356 C22 1 0.663209 0.243136 0.876348 11.00000 0.01626 0.01646 = 0.02566 -0.00142 0.00258 -0.00154 C23 1 0.705232 0.163094 0.860716 11.00000 0.01542 0.01516 = 0.02014 0.00055 0.00191 -0.00126 C24 1 0.842990 0.146362 0.850258 11.00000 0.01856 0.01432 = 0.01972 0.00001 0.00225 0.00045 AFIX 43 H24 2 0.867924 0.094444 0.838048 11.00000 -1.20000 AFIX 0 C24A 1 0.952506 0.204389 0.856996 11.00000 0.01529 0.01676 = 0.01762 0.00109 0.00117 -0.00075 C25 1 1.097700 0.188951 0.849507 11.00000 0.01736 0.02187 = 0.02523 0.00097 0.00320 0.00105 AFIX 43 H25 2 1.127076 0.137663 0.837985 11.00000 -1.20000 AFIX 0 C26 1 1.197800 0.247760 0.858772 11.00000 0.01470 0.03096 = 0.02660 0.00321 0.00201 -0.00210 AFIX 43 H26 2 1.295670 0.237307 0.852831 11.00000 -1.20000 AFIX 0 C27 1 1.154031 0.322842 0.876970 11.00000 0.02108 0.02550 = 0.02533 0.00268 0.00032 -0.00863 AFIX 43 H27 2 1.223492 0.363126 0.884029 11.00000 -1.20000 AFIX 0 C28 1 1.012122 0.339992 0.884967 11.00000 0.02359 0.01706 = 0.02684 0.00040 0.00205 -0.00344 AFIX 43 H28 2 0.983499 0.391233 0.897532 11.00000 -1.20000 AFIX 0 C28A 1 0.912732 0.280134 0.874094 11.00000 0.01552 0.01754 = 0.01933 0.00130 0.00153 -0.00042 C29 1 0.594774 0.100600 0.857963 11.00000 0.01807 0.01595 = 0.02393 -0.00022 0.00367 -0.00143 C30 1 0.567769 -0.036105 0.851825 11.00000 0.02342 0.01721 = 0.03496 0.00132 0.00281 -0.00776 AFIX 23 H30A 2 0.490379 -0.036103 0.792891 11.00000 -1.20000 H30B 2 0.522976 -0.037709 0.914326 11.00000 -1.20000 AFIX 0 C31 1 0.665068 -0.103133 0.847427 11.00000 0.03039 0.01866 = 0.02905 -0.00398 0.00375 -0.00484 AFIX 43 H31 2 0.721758 -0.104658 0.794175 11.00000 -1.20000 AFIX 0 C32 1 0.678084 -0.160636 0.912393 11.00000 0.03690 0.02255 = 0.04225 0.00325 0.00431 -0.00111 AFIX 93 H32A 2 0.622980 -0.160930 0.966556 11.00000 -1.20000 H32B 2 0.742583 -0.201836 0.905112 11.00000 -1.20000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM ks315, 150 K, P2(1)/n REM R1 = 0.0381 for 4116 Fo > 4sig(Fo) and 0.0477 for all 4940 data REM 307 parameters refined using 0 restraints END WGHT 0.0555 0.5244 REM Highest difference peak 0.368, deepest hole -0.210, 1-sigma level 0.042 Q1 1 0.6798 0.1991 0.8681 11.00000 0.05 0.37 Q2 1 0.6554 0.1336 0.8616 11.00000 0.05 0.36 Q3 1 0.9047 0.1726 0.8596 11.00000 0.05 0.35 Q4 1 0.4374 0.5685 0.8702 11.00000 0.05 0.34 Q5 1 0.9379 0.2385 0.8752 11.00000 0.05 0.33 Q6 1 0.1547 0.6734 0.8819 11.00000 0.05 0.32 Q7 1 0.9651 0.3086 0.8792 11.00000 0.05 0.30 Q8 1 1.0259 0.1967 0.8549 11.00000 0.05 0.27 Q9 1 0.6746 0.5265 0.8871 11.00000 0.05 0.26 Q10 1 0.4658 0.4999 0.8753 11.00000 0.05 0.26 ; _cod_data_source_file suppl_ncrs-2015-0209_suppl.cif _cod_data_source_block ks315 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 8106953 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.27224(8) 0.51074(5) 0.86534(6) 0.02139(19) Uani 1 1 d . . . O2 O 0.04658(9) 0.53976(5) 0.87586(7) 0.0307(2) Uani 1 1 d . . . O3 O -0.02882(9) 0.69897(5) 0.85453(7) 0.0285(2) Uani 1 1 d . . . O4 O 0.16390(9) 0.77693(5) 0.88955(7) 0.0273(2) Uani 1 1 d . . . C2 C 0.16558(12) 0.56485(7) 0.87380(9) 0.0198(2) Uani 1 1 d . . . C3 C 0.21150(12) 0.64585(6) 0.87909(8) 0.0179(2) Uani 1 1 d . . . C4 C 0.35296(12) 0.66373(7) 0.88700(9) 0.0197(2) Uani 1 1 d . . . H4 H 0.3813 0.7164 0.8928 0.024 Uiso 1 1 calc R . . C4A C 0.46126(12) 0.60573(6) 0.88685(8) 0.0188(2) Uani 1 1 d . . . C5 C 0.60955(13) 0.62182(7) 0.89628(9) 0.0244(3) Uani 1 1 d . . . H5 H 0.6422 0.6736 0.9049 0.029 Uiso 1 1 calc R . . C6 C 0.70789(13) 0.56337(8) 0.89322(10) 0.0260(3) Uani 1 1 d . . . H6 H 0.8080 0.5745 0.8992 0.031 Uiso 1 1 calc R . . C7 C 0.65892(13) 0.48726(7) 0.88120(9) 0.0247(3) Uani 1 1 d . . . H7 H 0.7271 0.4469 0.8796 0.030 Uiso 1 1 calc R . . C8 C 0.51395(13) 0.46924(7) 0.87161(9) 0.0222(2) Uani 1 1 d . . . H8 H 0.4820 0.4173 0.8634 0.027 Uiso 1 1 calc R . . C8A C 0.41634(12) 0.52917(7) 0.87425(8) 0.0179(2) Uani 1 1 d . . . C9 C 0.09935(12) 0.70767(7) 0.87287(8) 0.0196(2) Uani 1 1 d . . . C10 C 0.07283(13) 0.84463(7) 0.87072(10) 0.0258(3) Uani 1 1 d . . . H10A H 0.0175 0.8533 0.9273 0.031 Uiso 1 1 calc R . . H10B H 0.0041 0.8383 0.8076 0.031 Uiso 1 1 calc R . . C11 C 0.17219(14) 0.91068(7) 0.86145(10) 0.0279(3) Uani 1 1 d . . . H11 H 0.2353 0.9066 0.8123 0.034 Uiso 1 1 calc R . . C12 C 0.17919(16) 0.97383(8) 0.91577(12) 0.0363(3) Uani 1 1 d . . . H12A H 0.1178 0.9801 0.9657 0.044 Uiso 1 1 calc R . . H12B H 0.2456 1.0133 0.9052 0.044 Uiso 1 1 calc R . . O21 O 0.77138(8) 0.29801(4) 0.88073(6) 0.02122(19) Uani 1 1 d . . . O22 O 0.54545(9) 0.26721(5) 0.88584(8) 0.0314(2) Uani 1 1 d . . . O23 O 0.46878(9) 0.10879(5) 0.86341(8) 0.0312(2) Uani 1 1 d . . . O24 O 0.65796(9) 0.03197(5) 0.85072(7) 0.0246(2) Uani 1 1 d . . . C22 C 0.66321(12) 0.24314(7) 0.87635(9) 0.0195(2) Uani 1 1 d . . . C23 C 0.70523(11) 0.16309(6) 0.86072(8) 0.0170(2) Uani 1 1 d . . . C24 C 0.84299(12) 0.14636(6) 0.85026(8) 0.0176(2) Uani 1 1 d . . . H24 H 0.8679 0.0944 0.8380 0.021 Uiso 1 1 calc R . . C24A C 0.95251(11) 0.20439(6) 0.85700(8) 0.0167(2) Uani 1 1 d . . . C25 C 1.09770(12) 0.18895(7) 0.84951(9) 0.0215(2) Uani 1 1 d . . . H25 H 1.1271 0.1377 0.8380 0.026 Uiso 1 1 calc R . . C26 C 1.19780(12) 0.24776(7) 0.85877(9) 0.0242(3) Uani 1 1 d . . . H26 H 1.2957 0.2373 0.8528 0.029 Uiso 1 1 calc R . . C27 C 1.15403(13) 0.32284(7) 0.87697(9) 0.0243(3) Uani 1 1 d . . . H27 H 1.2235 0.3631 0.8840 0.029 Uiso 1 1 calc R . . C28 C 1.01212(13) 0.33999(7) 0.88497(9) 0.0227(2) Uani 1 1 d . . . H28 H 0.9835 0.3912 0.8975 0.027 Uiso 1 1 calc R . . C28A C 0.91273(11) 0.28013(7) 0.87409(8) 0.0176(2) Uani 1 1 d . . . C29 C 0.59477(12) 0.10060(6) 0.85796(9) 0.0193(2) Uani 1 1 d . . . C30 C 0.56777(13) -0.03611(7) 0.85183(10) 0.0253(3) Uani 1 1 d . . . H30A H 0.4904 -0.0361 0.7929 0.030 Uiso 1 1 calc R . . H30B H 0.5230 -0.0377 0.9143 0.030 Uiso 1 1 calc R . . C31 C 0.66507(14) -0.10313(7) 0.84743(10) 0.0261(3) Uani 1 1 d . . . H31 H 0.7218 -0.1047 0.7942 0.031 Uiso 1 1 calc R . . C32 C 0.67808(16) -0.16064(8) 0.91239(11) 0.0341(3) Uani 1 1 d . . . H32A H 0.6230 -0.1609 0.9666 0.041 Uiso 1 1 calc R . . H32B H 0.7426 -0.2018 0.9051 0.041 Uiso 1 1 calc R . . 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 0.0183(4) 0.0149(4) 0.0310(4) -0.0029(3) 0.0038(3) -0.0011(3) O2 0.0196(4) 0.0235(5) 0.0498(6) -0.0012(4) 0.0082(4) -0.0046(4) O3 0.0180(4) 0.0256(5) 0.0414(5) -0.0006(4) 0.0031(4) 0.0021(4) O4 0.0215(4) 0.0167(4) 0.0423(5) -0.0017(4) -0.0003(4) 0.0032(3) C2 0.0180(5) 0.0179(6) 0.0237(6) -0.0016(4) 0.0040(4) 0.0003(4) C3 0.0185(5) 0.0159(5) 0.0193(5) -0.0011(4) 0.0027(4) 0.0005(4) C4 0.0204(6) 0.0156(5) 0.0230(6) -0.0010(4) 0.0031(4) -0.0016(4) C4A 0.0179(5) 0.0176(5) 0.0206(5) 0.0001(4) 0.0024(4) 0.0010(4) C5 0.0198(6) 0.0216(6) 0.0315(6) 0.0002(5) 0.0025(5) -0.0026(5) C6 0.0166(5) 0.0313(7) 0.0300(6) 0.0012(5) 0.0031(5) 0.0016(5) C7 0.0237(6) 0.0272(6) 0.0235(6) -0.0011(5) 0.0041(5) 0.0095(5) C8 0.0261(6) 0.0190(6) 0.0217(6) -0.0031(4) 0.0037(5) 0.0023(5) C8A 0.0170(5) 0.0189(5) 0.0176(5) 0.0000(4) 0.0023(4) -0.0002(4) C9 0.0196(5) 0.0198(6) 0.0196(5) -0.0005(4) 0.0032(4) 0.0003(4) C10 0.0244(6) 0.0204(6) 0.0317(7) 0.0012(5) 0.0012(5) 0.0067(5) C11 0.0295(7) 0.0224(6) 0.0316(7) 0.0048(5) 0.0033(5) 0.0035(5) C12 0.0389(8) 0.0232(7) 0.0446(8) 0.0017(6) -0.0009(6) 0.0023(6) O21 0.0161(4) 0.0143(4) 0.0338(5) -0.0010(3) 0.0054(3) -0.0002(3) O22 0.0170(4) 0.0228(4) 0.0551(6) -0.0066(4) 0.0074(4) 0.0024(3) O23 0.0188(4) 0.0234(5) 0.0535(6) -0.0025(4) 0.0125(4) -0.0035(4) O24 0.0187(4) 0.0143(4) 0.0408(5) -0.0004(3) 0.0037(4) -0.0036(3) C22 0.0163(5) 0.0165(5) 0.0257(6) -0.0014(4) 0.0026(4) -0.0015(4) C23 0.0154(5) 0.0152(5) 0.0201(5) 0.0005(4) 0.0019(4) -0.0013(4) C24 0.0186(5) 0.0143(5) 0.0197(5) 0.0000(4) 0.0023(4) 0.0005(4) C24A 0.0153(5) 0.0168(5) 0.0176(5) 0.0011(4) 0.0012(4) -0.0008(4) C25 0.0174(5) 0.0219(6) 0.0252(6) 0.0010(5) 0.0032(4) 0.0011(5) C26 0.0147(5) 0.0310(7) 0.0266(6) 0.0032(5) 0.0020(4) -0.0021(5) C27 0.0211(6) 0.0255(6) 0.0253(6) 0.0027(5) 0.0003(5) -0.0086(5) C28 0.0236(6) 0.0171(5) 0.0268(6) 0.0004(5) 0.0020(5) -0.0034(5) C28A 0.0155(5) 0.0175(5) 0.0193(5) 0.0013(4) 0.0015(4) -0.0004(4) C29 0.0181(5) 0.0159(5) 0.0239(6) -0.0002(4) 0.0037(4) -0.0014(4) C30 0.0234(6) 0.0172(6) 0.0350(7) 0.0013(5) 0.0028(5) -0.0078(5) C31 0.0304(7) 0.0187(6) 0.0291(6) -0.0040(5) 0.0037(5) -0.0048(5) C32 0.0369(8) 0.0225(6) 0.0423(8) 0.0032(6) 0.0043(6) -0.0011(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C8A O1 C2 123.09(9) . . C9 O4 C10 116.94(9) . . O2 C2 O1 116.09(10) . . O2 C2 C3 127.75(11) . . O1 C2 C3 116.17(9) . . C4 C3 C2 120.07(10) . . C4 C3 C9 120.95(10) . . C2 C3 C9 118.96(10) . . C3 C4 C4A 121.87(11) . . C3 C4 H4 119.1 . . C4A C4 H4 119.1 . . C8A C4A C5 118.47(10) . . C8A C4A C4 117.88(10) . . C5 C4A C4 123.63(11) . . C6 C5 C4A 120.66(11) . . C6 C5 H5 119.7 . . C4A C5 H5 119.7 . . C5 C6 C7 119.25(11) . . C5 C6 H6 120.4 . . C7 C6 H6 120.4 . . C8 C7 C6 121.71(11) . . C8 C7 H7 119.1 . . C6 C7 H7 119.1 . . C7 C8 C8A 118.13(11) . . C7 C8 H8 120.9 . . C8A C8 H8 120.9 . . O1 C8A C8 117.80(10) . . O1 C8A C4A 120.42(10) . . C8 C8A C4A 121.77(10) . . O3 C9 O4 123.87(11) . . O3 C9 C3 126.60(11) . . O4 C9 C3 109.52(9) . . O4 C10 C11 106.04(10) . . O4 C10 H10A 110.5 . . C11 C10 H10A 110.5 . . O4 C10 H10B 110.5 . . C11 C10 H10B 110.5 . . H10A C10 H10B 108.7 . . C12 C11 C10 125.15(13) . . C12 C11 H11 117.4 . . C10 C11 H11 117.4 . . C11 C12 H12A 120.0 . . C11 C12 H12B 120.0 . . H12A C12 H12B 120.0 . . C28A O21 C22 123.26(9) . . C29 O24 C30 117.16(9) . . O22 C22 O21 115.75(10) . . O22 C22 C23 127.80(11) . . O21 C22 C23 116.46(9) . . C24 C23 C22 119.95(10) . . C24 C23 C29 120.74(10) . . C22 C23 C29 119.31(10) . . C23 C24 C24A 122.05(10) . . C23 C24 H24 119.0 . . C24A C24 H24 119.0 . . C28A C24A C25 118.47(10) . . C28A C24A C24 117.78(10) . . C25 C24A C24 123.73(10) . . C26 C25 C24A 120.43(11) . . C26 C25 H25 119.8 . . C24A C25 H25 119.8 . . C25 C26 C27 119.41(11) . . C25 C26 H26 120.3 . . C27 C26 H26 120.3 . . C28 C27 C26 121.64(11) . . C28 C27 H27 119.2 . . C26 C27 H27 119.2 . . C27 C28 C28A 118.03(11) . . C27 C28 H28 121.0 . . C28A C28 H28 121.0 . . O21 C28A C28 117.57(10) . . O21 C28A C24A 120.42(10) . . C28 C28A C24A 122.01(10) . . O23 C29 O24 123.95(10) . . O23 C29 C23 126.57(11) . . O24 C29 C23 109.47(9) . . O24 C30 C31 105.87(9) . . O24 C30 H30A 110.6 . . C31 C30 H30A 110.6 . . O24 C30 H30B 110.6 . . C31 C30 H30B 110.6 . . H30A C30 H30B 108.7 . . C32 C31 C30 124.37(13) . . C32 C31 H31 117.8 . . C30 C31 H31 117.8 . . C31 C32 H32A 120.0 . . C31 C32 H32B 120.0 . . H32A C32 H32B 120.0 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C8A 1.3763(13) . O1 C2 1.3878(13) . O2 C2 1.2015(14) . O3 C9 1.2000(14) . O4 C9 1.3482(14) . O4 C10 1.4514(14) . C2 C3 1.4671(16) . C3 C4 1.3508(15) . C3 C9 1.4950(15) . C4 C4A 1.4290(15) . C4 H4 0.9500 . C4A C8A 1.3950(16) . C4A C5 1.4054(16) . C5 C6 1.3746(17) . C5 H5 0.9500 . C6 C7 1.3984(18) . C6 H6 0.9500 . C7 C8 1.3820(17) . C7 H7 0.9500 . C8 C8A 1.3881(16) . C8 H8 0.9500 . C10 C11 1.4926(18) . C10 H10A 0.9900 . C10 H10B 0.9900 . C11 C12 1.3102(19) . C11 H11 0.9500 . C12 H12A 0.9500 . C12 H12B 0.9500 . O21 C28A 1.3765(13) . O21 C22 1.3854(13) . O22 C22 1.2043(14) . O23 C29 1.2025(14) . O24 C29 1.3387(14) . O24 C30 1.4531(13) . C22 C23 1.4657(15) . C23 C24 1.3509(15) . C23 C29 1.4953(15) . C24 C24A 1.4306(15) . C24 H24 0.9500 . C24A C28A 1.3930(15) . C24A C25 1.4052(15) . C25 C26 1.3788(17) . C25 H25 0.9500 . C26 C27 1.3967(18) . C26 H26 0.9500 . C27 C28 1.3827(17) . C27 H27 0.9500 . C28 C28A 1.3878(16) . C28 H28 0.9500 . C30 C31 1.4837(17) . C30 H30A 0.9900 . C30 H30B 0.9900 . C31 C32 1.3165(19) . C31 H31 0.9500 . C32 H32A 0.9500 . C32 H32B 0.9500 .