#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202583.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_2202583 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2003 _journal_volume 59 _journal_page_first o1517 _journal_page_last o1518 _publ_section_title ; 3,7,8-Trihydroxy-3-methyl-10-oxo-4,10-dihydro-1H,3H-pyrano[4,3-b]chromene- 9-carboxylic acid (fulvic acid) methanol 0.75-solvate ; loop_ _publ_author_name 'Wang, Jian-Feng' 'Fang, Mei-Juan' 'Huang, Hui-Qiong' 'Li, Gui-Ling' 'Su, Wen-Jin' 'Zhao, Yu-Fen' _chemical_name_common 'Fulvic acid' _chemical_formula_moiety 'C14 H12 O8, 0.75C H4 O' _chemical_formula_sum 'C14.75 H15 O8.75' _chemical_formula_iupac 'C14 H12 O8, 0.75C H4 O' _chemical_formula_weight 332.27 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4830(7) _cell_length_b 12.6558(8) _cell_length_c 19.0259(13) _cell_angle_alpha 94.608(3) _cell_angle_beta 100.871(3) _cell_angle_gamma 98.399(3) _cell_volume 2902.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _exptl_crystal_density_diffrn 1.521 _diffrn_ambient_temperature 298(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1A 0.2068(2) 0.7952(3) 0.2622(2) 0.0439(9) Uani d . 1 . . O O2A -0.0189(3) 0.6433(3) 0.3645(2) 0.0635(12) Uani d . 1 . . O O3A -0.1155(3) 0.8141(3) 0.1913(2) 0.0738(14) Uani d . 1 . . O O4A -0.1421(3) 0.9480(3) 0.1110(2) 0.0737(13) Uani d . 1 . . O O5A -0.0457(3) 1.0744(3) 0.0674(2) 0.0656(12) Uani d . 1 . . O O6A 0.1548(3) 1.1007(3) 0.0785(2) 0.0573(11) Uani d . 1 . . O O7A 0.3501(3) 1.0491(3) 0.1263(2) 0.0520(10) Uani d . 1 . . O O8A 0.0471(4) 0.5119(3) 0.3025(2) 0.0726(13) Uani d . 1 . . O C1A 0.0596(4) 0.9643(4) 0.1380(3) 0.0415(13) Uani d . 1 . . C C2A 0.1532(4) 1.0203(4) 0.1204(3) 0.0438(14) Uani d . 1 . . C C3A 0.2608(4) 0.9953(4) 0.1459(3) 0.0396(13) Uani d . 1 . . C C4A 0.2738(4) 0.9194(4) 0.1925(3) 0.0435(14) Uani d . 1 . . C C5A 0.1808(4) 0.8664(4) 0.2132(3) 0.0387(13) Uani d . 1 . . C C6A 0.0728(4) 0.8834(4) 0.1870(3) 0.0383(13) Uani d . 1 . . C C7A -0.0131(4) 0.8155(4) 0.2131(3) 0.0479(15) Uani d . 1 . . C C8A 0.0195(4) 0.7476(4) 0.2663(3) 0.0439(14) Uani d . 1 . . C C9A 0.1258(4) 0.7394(4) 0.2889(3) 0.0394(13) Uani d . 1 . . C C10A 0.1684(4) 0.6739(4) 0.3460(3) 0.0496(15) Uani d . 1 . . C C11A 0.0737(4) 0.5941(4) 0.3611(3) 0.0420(14) Uani d . 1 . . C C12A -0.0673(4) 0.6821(5) 0.2981(3) 0.0652(19) Uani d . 1 . . C C13A 0.1030(4) 0.5462(5) 0.4312(3) 0.0641(18) Uani d . 1 . . C C14A -0.0481(4) 0.9977(5) 0.1043(3) 0.0496(15) Uani d . 1 . . C H4A -0.1327 0.9059 0.1413 0.110 Uiso calc R 1 . . H H6A 0.0913 1.1063 0.0602 0.086 Uiso calc R 1 . . H H7A 0.3312 1.0960 0.1016 0.078 Uiso calc R 1 . . H H8A 0.0232 0.4551 0.3162 0.109 Uiso calc R 1 . . H H4AA 0.3436 0.9033 0.2100 0.052 Uiso calc R 1 . . H H10G 0.2037 0.7206 0.3896 0.060 Uiso calc R 1 . . H H10H 0.2232 0.6354 0.3306 0.060 Uiso calc R 1 . . H H12G -0.1216 0.7261 0.3074 0.078 Uiso calc R 1 . . H H12H -0.1051 0.6214 0.2636 0.078 Uiso calc R 1 . . H H13A 0.1100 0.6003 0.4709 0.096 Uiso calc R 1 . . H H13B 0.1718 0.5199 0.4335 0.096 Uiso calc R 1 . . H H13C 0.0458 0.4879 0.4338 0.096 Uiso calc R 1 . . H O1B 0.1174(2) 0.4003(3) 0.1734(2) 0.0398(9) Uani d . 1 . . O O2B -0.1088(3) 0.1737(3) 0.2331(2) 0.0536(10) Uani d . 1 . . O O3B -0.2086(3) 0.4250(3) 0.1225(2) 0.0662(12) Uani d . 1 . . O O4B -0.2396(3) 0.5762(4) 0.0600(2) 0.0763(14) Uani d . 1 . . O O5B -0.1547(3) 0.6957(3) 0.0054(2) 0.0651(12) Uani d . 1 . . O O6B 0.0461(3) 0.7337(3) 0.0157(2) 0.0543(10) Uani d . 1 . . O O7B 0.2469(3) 0.6897(3) 0.0599(2) 0.0602(11) Uani d . 1 . . O O8B -0.0187(3) 0.2966(3) 0.3318(2) 0.0498(10) Uani d . 1 . . O C1B -0.0402(4) 0.5867(4) 0.0716(2) 0.0363(12) Uani d . 1 . . C C2B 0.0512(4) 0.6490(4) 0.0548(2) 0.0378(13) Uani d . 1 . . C C3B 0.1610(4) 0.6281(4) 0.0773(3) 0.0428(14) Uani d . 1 . . C C4B 0.1783(4) 0.5431(4) 0.1164(2) 0.0387(13) Uani d . 1 . . C C5B 0.0873(4) 0.4808(4) 0.1328(2) 0.0341(12) Uani d . 1 . . C C6B -0.0226(4) 0.4967(4) 0.1128(2) 0.0363(13) Uani d . 1 . . C C7B -0.1061(4) 0.4200(4) 0.1346(3) 0.0428(14) Uani d . 1 . . C C8B -0.0698(4) 0.3355(4) 0.1738(2) 0.0387(13) Uani d . 1 . . C C9B 0.0389(4) 0.3312(4) 0.1934(2) 0.0343(12) Uani d . 1 . . C C10B 0.0823(4) 0.2554(4) 0.2436(3) 0.0460(14) Uani d . 1 . . C C11B -0.0071(4) 0.2093(4) 0.2829(3) 0.0445(14) Uani d . 1 . . C C12B -0.1542(4) 0.2579(4) 0.1979(3) 0.0520(15) Uani d . 1 . . C C13B 0.0200(5) 0.1148(4) 0.3234(3) 0.0647(18) Uani d . 1 . . C C14B -0.1503(4) 0.6223(5) 0.0441(3) 0.0465(14) Uani d . 1 . . C H4B -0.2254 0.5297 0.0863 0.114 Uiso calc R 1 . . H H6B -0.0177 0.7454 0.0068 0.082 Uiso calc R 1 . . H H7B 0.2242 0.7335 0.0338 0.090 Uiso calc R 1 . . H H8B -0.0674 0.2768 0.3536 0.075 Uiso calc R 1 . . H H4BA 0.2491 0.5278 0.1314 0.046 Uiso calc R 1 . . H H10A 0.1463 0.2930 0.2784 0.055 Uiso calc R 1 . . H H10B 0.1054 0.1974 0.2167 0.055 Uiso calc R 1 . . H H12A -0.1893 0.2969 0.2307 0.062 Uiso calc R 1 . . H H12B -0.2108 0.2262 0.1564 0.062 Uiso calc R 1 . . H H13D -0.0388 0.0915 0.3476 0.097 Uiso calc R 1 . . H H13E 0.0878 0.1364 0.3582 0.097 Uiso calc R 1 . . H H13F 0.0280 0.0569 0.2901 0.097 Uiso calc R 1 . . H O1C 0.5987(2) 0.1707(3) 0.23126(17) 0.0411(9) Uani d . 1 . . O O2C 0.3992(3) 0.3881(3) 0.16508(17) 0.0469(10) Uani d . 1 . . O O3C 0.3252(3) 0.1831(3) 0.31545(19) 0.0621(12) Uani d . 1 . . O O4C 0.2952(3) 0.0411(4) 0.3898(2) 0.0824(15) Uani d . 1 . . O O5C 0.3778(3) -0.0807(3) 0.4392(2) 0.0722(13) Uani d . 1 . . O O6C 0.5583(3) -0.1213(3) 0.4222(2) 0.0637(12) Uani d . 1 . . O O7C 0.7318(3) -0.0939(3) 0.3612(2) 0.0644(12) Uani d . 1 . . O O8C 0.3696(3) 0.2467(3) 0.07298(19) 0.0492(10) Uani d . 1 . . O C1C 0.4761(4) 0.0191(4) 0.3643(2) 0.0405(13) Uani d . 1 . . C C2C 0.5593(4) -0.0426(4) 0.3787(3) 0.0486(15) Uani d . 1 . . C C3C 0.6536(4) -0.0317(4) 0.3470(3) 0.0470(14) Uani d . 1 . . C C4C 0.6644(4) 0.0427(4) 0.2993(3) 0.0464(14) Uani d . 1 . . C C5C 0.5807(4) 0.1038(4) 0.2830(2) 0.0387(13) Uani d . 1 . . C C6C 0.4866(4) 0.0985(4) 0.3139(2) 0.0372(13) Uani d . 1 . . C C7C 0.4129(4) 0.1753(4) 0.2923(2) 0.0389(13) Uani d . 1 . . C C8C 0.4385(4) 0.2434(4) 0.2398(3) 0.0395(13) Uani d . 1 . . C C9C 0.5253(4) 0.2369(4) 0.2096(3) 0.0385(13) Uani d . 1 . . C C10C 0.5485(4) 0.2942(4) 0.1475(3) 0.0441(14) Uani d . 1 . . C C11C 0.4468(4) 0.3384(4) 0.1115(3) 0.0404(13) Uani d . 1 . . C C12C 0.3577(4) 0.3153(4) 0.2119(3) 0.0443(14) Uani d . 1 . . C C13C 0.4743(4) 0.4210(4) 0.0619(3) 0.0526(16) Uani d . 1 . . C C14C 0.3793(4) -0.0079(5) 0.3998(3) 0.0528(16) Uani d . 1 . . C H4C 0.3074 0.0912 0.3661 0.124 Uiso calc R 1 . . H H6C 0.5012 -0.1271 0.4380 0.096 Uiso calc R 1 . . H H7C 0.7184 -0.1314 0.3927 0.097 Uiso calc R 1 . . H H8C 0.3182 0.2674 0.0472 0.074 Uiso calc R 1 . . H H4CA 0.7261 0.0522 0.2782 0.056 Uiso calc R 1 . . H H10E 0.5697 0.2451 0.1127 0.053 Uiso calc R 1 . . H H10F 0.6097 0.3529 0.1641 0.053 Uiso calc R 1 . . H H12E 0.2895 0.2711 0.1858 0.053 Uiso calc R 1 . . H H12F 0.3407 0.3566 0.2524 0.053 Uiso calc R 1 . . H H13G 0.4081 0.4458 0.0402 0.079 Uiso calc R 1 . . H H13H 0.5064 0.3892 0.0250 0.079 Uiso calc R 1 . . H H13I 0.5261 0.4805 0.0891 0.079 Uiso calc R 1 . . H O1D 0.6749(2) 0.5578(3) 0.27929(17) 0.0448(9) Uani d . 1 . . O O2D 0.4875(3) 0.7893(3) 0.22805(18) 0.0484(10) Uani d . 1 . . O O3D 0.3919(3) 0.5564(3) 0.3543(2) 0.0613(11) Uani d . 1 . . O O4D 0.3713(3) 0.4281(4) 0.4381(2) 0.0741(13) Uani d . 1 . . O O5D 0.4550(3) 0.3076(3) 0.4887(2) 0.0758(13) Uani d . 1 . . O O6D 0.6302(3) 0.2618(3) 0.4683(2) 0.0563(11) Uani d . 1 . . O O7D 0.8000(3) 0.2826(3) 0.40396(19) 0.0492(10) Uani d . 1 . . O O8D 0.4676(3) 0.6673(3) 0.1261(2) 0.0612(11) Uani d . 1 . . O C1D 0.5466(4) 0.3996(4) 0.4075(2) 0.0382(13) Uani d . 1 . . C C2D 0.6306(4) 0.3358(4) 0.4227(3) 0.0418(13) Uani d . 1 . . C C3D 0.7226(4) 0.3468(4) 0.3895(2) 0.0371(13) Uani d . 1 . . C C4D 0.7348(4) 0.4233(4) 0.3434(2) 0.0413(13) Uani d . 1 . . C C5D 0.6537(4) 0.4883(4) 0.3287(3) 0.0386(13) Uani d . 1 . . C C6D 0.5585(4) 0.4797(4) 0.3579(3) 0.0382(13) Uani d . 1 . . C C7D 0.4844(4) 0.5542(4) 0.3354(3) 0.0412(13) Uani d . 1 . . C C8D 0.5129(4) 0.6287(4) 0.2867(3) 0.0388(13) Uani d . 1 . . C C9D 0.6045(4) 0.6274(4) 0.2608(3) 0.0396(13) Uani d . 1 . . C C10D 0.6385(4) 0.6989(4) 0.2076(3) 0.0473(15) Uani d . 1 . . C C11D 0.5407(4) 0.7504(5) 0.1732(3) 0.0483(15) Uani d . 1 . . C C12D 0.4381(4) 0.7077(4) 0.2648(3) 0.0517(15) Uani d . 1 . . C C13D 0.5742(5) 0.8453(4) 0.1340(3) 0.0691(19) Uani d . 1 . . C C14D 0.4533(4) 0.3770(5) 0.4468(3) 0.0526(16) Uani d . 1 . . C H4D 0.3837 0.4776 0.4139 0.111 Uiso calc R 1 . . H H6D 0.5739 0.2584 0.4848 0.084 Uiso calc R 1 . . H H7D 0.7797 0.2376 0.4294 0.074 Uiso calc R 1 . . H H8D 0.4147 0.6917 0.1049 0.092 Uiso calc R 1 . . H H4DA 0.7963 0.4318 0.3221 0.050 Uiso calc R 1 . . H H10C 0.6636 0.6574 0.1706 0.057 Uiso calc R 1 . . H H10D 0.6992 0.7545 0.2315 0.057 Uiso calc R 1 . . H H12C 0.3704 0.6698 0.2337 0.062 Uiso calc R 1 . . H H12D 0.4187 0.7409 0.3074 0.062 Uiso calc R 1 . . H H13J 0.6058 0.8217 0.0945 0.104 Uiso calc R 1 . . H H13K 0.6277 0.8980 0.1666 0.104 Uiso calc R 1 . . H H13L 0.5102 0.8766 0.1161 0.104 Uiso calc R 1 . . H O1 0.7551(3) 0.1438(3) 0.0163(2) 0.0734(13) Uani d . 1 . . O O2 0.7988(3) 0.1351(4) 0.4928(2) 0.0732(13) Uani d . 1 . . O O3 0.7243(4) 0.7420(5) 0.4397(3) 0.1075(19) Uani d . 1 . . O C1 0.6625(4) 0.0780(5) 0.0314(3) 0.0675(18) Uani d . 1 . . C C2 0.8893(5) 0.0816(5) 0.5165(3) 0.080(2) Uani d . 1 . . C C3 0.8148(5) 0.7136(6) 0.4787(4) 0.096(3) Uani d . 1 . . C H1 0.8120 0.1262 0.0377 0.110 Uiso calc R 1 . . H H2 0.7490 0.1166 0.5141 0.110 Uiso calc R 1 . . H H3 0.6728 0.7313 0.4608 0.161 Uiso calc R 1 . . H H1A 0.6755 0.0688 0.0818 0.101 Uiso calc R 1 . . H H1B 0.6509 0.0092 0.0036 0.101 Uiso calc R 1 . . H H1C 0.5981 0.1114 0.0193 0.101 Uiso calc R 1 . . H H2A 0.9548 0.1338 0.5343 0.119 Uiso calc R 1 . . H H2B 0.9005 0.0354 0.4769 0.119 Uiso calc R 1 . . H H2C 0.8737 0.0395 0.5542 0.119 Uiso calc R 1 . . H H3A 0.8387 0.7608 0.5228 0.144 Uiso calc R 1 . . H H3B 0.8727 0.7188 0.4518 0.144 Uiso calc R 1 . . H H3C 0.7978 0.6410 0.4895 0.144 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1A 0.035(2) 0.041(2) 0.061(2) 0.011(2) 0.011(2) 0.026(2) O2A 0.056(2) 0.077(3) 0.077(3) 0.026(2) 0.035(2) 0.043(2) O3A 0.034(2) 0.091(3) 0.099(3) 0.002(2) 0.005(2) 0.057(3) O4A 0.045(2) 0.075(3) 0.100(4) 0.008(2) -0.002(2) 0.050(3) O5A 0.058(2) 0.063(3) 0.079(3) 0.011(2) 0.005(2) 0.042(2) O6A 0.059(2) 0.046(3) 0.065(3) 0.001(2) 0.005(2) 0.030(2) O7A 0.051(2) 0.041(3) 0.068(3) 0.002(2) 0.022(2) 0.019(2) O8A 0.115(4) 0.050(3) 0.053(3) -0.004(3) 0.029(2) 0.009(2) C1A 0.042(3) 0.036(4) 0.046(3) 0.004(3) 0.005(3) 0.014(3) C2A 0.062(4) 0.031(3) 0.037(3) 0.006(3) 0.006(3) 0.008(3) C3A 0.048(3) 0.028(3) 0.043(3) 0.004(3) 0.012(3) 0.002(3) C4A 0.036(3) 0.043(4) 0.053(3) 0.009(3) 0.007(3) 0.014(3) C5A 0.040(3) 0.032(3) 0.047(3) 0.007(3) 0.016(3) 0.010(3) C6A 0.034(3) 0.037(3) 0.043(3) 0.008(3) 0.005(2) 0.005(3) C7A 0.037(3) 0.043(4) 0.064(4) 0.004(3) 0.009(3) 0.020(3) C8A 0.034(3) 0.049(4) 0.049(3) 0.006(3) 0.006(3) 0.015(3) C9A 0.039(3) 0.035(3) 0.051(3) 0.010(3) 0.017(3) 0.014(3) C10A 0.043(3) 0.052(4) 0.058(4) 0.010(3) 0.013(3) 0.026(3) C11A 0.051(3) 0.040(4) 0.038(3) 0.005(3) 0.016(3) 0.008(3) C12A 0.046(3) 0.076(5) 0.082(4) 0.011(3) 0.015(3) 0.055(4) C13A 0.073(4) 0.068(5) 0.059(4) 0.011(3) 0.020(3) 0.032(3) C14A 0.047(4) 0.040(4) 0.062(4) 0.008(3) 0.006(3) 0.016(3) O1B 0.035(2) 0.042(2) 0.050(2) 0.014(2) 0.016(2) 0.025(2) O2B 0.054(2) 0.043(3) 0.062(3) -0.002(2) 0.013(2) 0.018(2) O3B 0.031(2) 0.080(3) 0.094(3) 0.010(2) 0.015(2) 0.044(3) O4B 0.042(2) 0.098(4) 0.099(4) 0.025(2) 0.012(2) 0.058(3) O5B 0.058(2) 0.065(3) 0.078(3) 0.024(2) 0.008(2) 0.035(2) O6B 0.056(2) 0.050(3) 0.062(2) 0.014(2) 0.011(2) 0.028(2) O7B 0.045(2) 0.065(3) 0.076(3) 0.008(2) 0.010(2) 0.043(2) O8B 0.058(2) 0.046(2) 0.053(2) 0.006(2) 0.028(2) 0.011(2) C1B 0.041(3) 0.037(3) 0.032(3) 0.012(3) 0.006(2) 0.005(3) C2B 0.048(3) 0.032(3) 0.035(3) 0.012(3) 0.006(3) 0.012(3) C3B 0.036(3) 0.048(4) 0.044(3) -0.003(3) 0.009(3) 0.015(3) C4B 0.033(3) 0.045(4) 0.041(3) 0.007(3) 0.008(2) 0.017(3) C5B 0.036(3) 0.037(3) 0.035(3) 0.012(3) 0.014(2) 0.009(3) C6B 0.039(3) 0.037(3) 0.034(3) 0.008(3) 0.007(2) 0.008(3) C7B 0.040(3) 0.046(4) 0.044(3) 0.007(3) 0.010(3) 0.010(3) C8B 0.039(3) 0.040(4) 0.038(3) 0.004(3) 0.011(2) 0.006(3) C9B 0.040(3) 0.035(3) 0.031(3) 0.003(3) 0.016(2) 0.008(2) C10B 0.047(3) 0.047(4) 0.052(3) 0.012(3) 0.021(3) 0.019(3) C11B 0.054(4) 0.039(4) 0.047(3) 0.014(3) 0.018(3) 0.011(3) C12B 0.048(3) 0.045(4) 0.062(4) 0.001(3) 0.010(3) 0.016(3) C13B 0.077(4) 0.053(4) 0.078(4) 0.024(3) 0.031(3) 0.033(4) C14B 0.047(3) 0.048(4) 0.045(3) 0.013(3) 0.005(3) 0.009(3) O1C 0.032(2) 0.048(2) 0.050(2) 0.009(2) 0.012(2) 0.027(2) O2C 0.052(2) 0.043(2) 0.054(2) 0.014(2) 0.019(2) 0.023(2) O3C 0.054(2) 0.078(3) 0.073(3) 0.028(2) 0.034(2) 0.045(2) O4C 0.070(3) 0.102(4) 0.107(4) 0.038(3) 0.053(3) 0.073(3) O5C 0.078(3) 0.078(3) 0.080(3) 0.019(2) 0.039(2) 0.056(3) O6C 0.068(3) 0.068(3) 0.068(3) 0.021(2) 0.023(2) 0.046(2) O7C 0.062(2) 0.068(3) 0.076(3) 0.026(2) 0.021(2) 0.041(2) O8C 0.044(2) 0.046(3) 0.057(2) 0.001(2) 0.0065(19) 0.024(2) C1C 0.046(3) 0.038(3) 0.038(3) 0.006(3) 0.006(2) 0.013(3) C2C 0.056(4) 0.046(4) 0.047(3) 0.013(3) 0.006(3) 0.027(3) C3C 0.046(3) 0.053(4) 0.047(3) 0.019(3) 0.006(3) 0.021(3) C4C 0.040(3) 0.047(4) 0.057(4) 0.010(3) 0.014(3) 0.018(3) C5C 0.042(3) 0.035(3) 0.040(3) 0.002(3) 0.008(2) 0.020(3) C6C 0.039(3) 0.035(3) 0.038(3) 0.002(3) 0.007(2) 0.009(3) C7C 0.040(3) 0.042(4) 0.034(3) 0.002(3) 0.011(2) 0.007(3) C8C 0.034(3) 0.041(4) 0.044(3) 0.004(3) 0.008(2) 0.013(3) C9C 0.040(3) 0.035(3) 0.041(3) 0.002(3) 0.007(3) 0.016(3) C10C 0.040(3) 0.050(4) 0.047(3) 0.010(3) 0.012(3) 0.023(3) C11C 0.037(3) 0.038(4) 0.048(3) 0.003(3) 0.008(3) 0.018(3) C12C 0.049(3) 0.049(4) 0.046(3) 0.017(3) 0.022(3) 0.025(3) C13C 0.053(3) 0.054(4) 0.055(3) 0.005(3) 0.012(3) 0.033(3) C14C 0.054(4) 0.056(4) 0.053(4) 0.002(3) 0.019(3) 0.024(3) O1D 0.037(2) 0.054(2) 0.052(2) 0.0140(2) 0.018(2) 0.028(2) O2D 0.049(2) 0.039(2) 0.063(2) 0.014(2) 0.014(2) 0.019(2) O3D 0.048(2) 0.074(3) 0.083(3) 0.031(2) 0.036(2) 0.039(2) O4D 0.064(3) 0.083(4) 0.103(3) 0.033(3) 0.052(2) 0.054(3) O5D 0.072(3) 0.092(3) 0.092(3) 0.038(2) 0.047(2) 0.066(3) O6D 0.053(2) 0.066(3) 0.064(3) 0.022(2) 0.025(2) 0.038(2) O7D 0.050(2) 0.050(3) 0.062(3) 0.024(2) 0.026(2) 0.028(2) O8D 0.056(3) 0.059(3) 0.067(3) 0.016(2) 0.001(2) 0.013(2) C1D 0.036(3) 0.041(3) 0.043(3) 0.010(3) 0.017(2) 0.010(3) C2D 0.047(3) 0.040(4) 0.044(3) 0.010(3) 0.019(3) 0.017(3) C3D 0.037(3) 0.039(3) 0.038(3) 0.010(3) 0.010(2) 0.008(3) C4D 0.039(3) 0.047(4) 0.045(3) 0.012(3) 0.017(3) 0.019(3) C5D 0.037(3) 0.038(3) 0.045(3) 0.006(3) 0.012(2) 0.013(3) C6D 0.031(3) 0.038(3) 0.046(3) 0.003(3) 0.009(2) 0.009(3) C7D 0.035(3) 0.048(4) 0.048(3) 0.017(3) 0.016(3) 0.016(3) C8D 0.031(3) 0.041(4) 0.046(3) 0.003(3) 0.009(2) 0.015(3) C9D 0.033(3) 0.039(3) 0.050(3) 0.010(3) 0.008(3) 0.018(3) C10D 0.036(3) 0.051(4) 0.059(4) 0.010(3) 0.011(3) 0.025(3) C11D 0.047(3) 0.039(4) 0.060(4) 0.009(3) 0.006(3) 0.017(3) C12D 0.043(3) 0.050(4) 0.069(4) 0.011(3) 0.015(3) 0.026(3) C13D 0.080(4) 0.059(4) 0.078(4) 0.020(4) 0.020(4) 0.038(4) C14D 0.049(3) 0.058(4) 0.063(4) 0.018(3) 0.027(3) 0.024(3) O1 0.048(2) 0.075(3) 0.100(3) 0.004(2) 0.008(2) 0.054(3) O2 0.067(3) 0.086(3) 0.090(3) 0.037(3) 0.036(2) 0.055(3) O3 0.081(3) 0.138(5) 0.148(4) 0.062(3) 0.064(3) 0.108(4) C1 0.067(4) 0.070(5) 0.064(4) 0.007(4) 0.013(3) 0.009(4) C2 0.076(4) 0.083(5) 0.098(5) 0.039(4) 0.034(4) 0.029(4) C3 0.053(4) 0.140(7) 0.104(6) 0.022(4) 0.018(4) 0.057(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1A C9A . 1.350(5) no O1A C5A . 1.375(5) no O2A C11A . 1.401(6) no O2A C12A . 1.450(5) no O3A C7A . 1.265(5) no O4A C14A . 1.281(6) no O5A C14A . 1.244(6) no O6A C2A . 1.342(5) no O7A C3A . 1.350(5) no O8A C11A . 1.417(6) no C1A C2A . 1.387(6) no C1A C6A . 1.445(6) no C1A C14A . 1.511(7) no C2A C3A . 1.429(7) no C3A C4A . 1.364(6) no C4A C5A . 1.394(6) no C5A C6A . 1.400(6) no C6A C7A . 1.462(6) no C7A C8A . 1.419(6) no C8A C9A . 1.337(6) no C8A C12A . 1.514(6) no C9A C10A . 1.484(6) no C10A C11A . 1.525(6) no C11A C13A . 1.514(6) no O4A H4A . 0.8200 no O6A H6A . 0.8200 no O7A H7A . 0.8200 no O8A H8A . 0.8200 no C4A H4AA . 0.9300 no C10A H10G . 0.9700 no C10A H10H . 0.9700 no C12A H12G . 0.9700 no C12A H12H . 0.9700 no C13A H13A . 0.9600 no C13A H13B . 0.9600 no C13A H13C . 0.9600 no O1B C9B . 1.346(5) no O1B C5B . 1.381(5) no O2B C11B . 1.422(6) no O2B C12B . 1.433(5) no O3B C7B . 1.268(5) no O4B C14B . 1.281(6) no O5B C14B . 1.232(6) no O6B C2B . 1.356(5) no O7B C3B . 1.342(5) no O8B C11B . 1.427(6) no C1B C2B . 1.393(6) no C1B C6B . 1.453(6) no C1B C14B . 1.520(6) no C2B C3B . 1.427(6) no C3B C4B . 1.375(6) no C4B C5B . 1.385(6) no C5B C6B . 1.401(6) no C6B C7B . 1.461(6) no C7B C8B . 1.431(6) no C8B C9B . 1.348(6) no C8B C12B . 1.496(6) no C9B C10B . 1.494(6) no C10B C11B . 1.531(6) no C11B C13B . 1.518(6) no O4B H4B . 0.8200 no O6B H6B . 0.8200 no O7B H7B . 0.8200 no O8B H8B . 0.8200 no C4B H4BA . 0.9300 no C10B H10A . 0.9700 no C10B H10B . 0.9700 no C12B H12A . 0.9700 no C12B H12B . 0.9700 no C13B H13D . 0.9600 no C13B H13E . 0.9600 no C13B H13F . 0.9600 no O1C C9C . 1.359(5) no O1C C5C . 1.378(5) no O2C C11C . 1.423(6) no O2C C12C . 1.441(5) no O3C C7C . 1.268(5) no O4C C14C . 1.287(6) no O5C C14C . 1.233(6) no O6C C2C . 1.344(5) no O7C C3C . 1.344(6) no O8C C11C . 1.443(6) no C1C C2C . 1.388(7) no C1C C6C . 1.453(6) no C1C C14C . 1.502(6) no C2C C3C . 1.415(7) no C3C C4C . 1.370(6) no C4C C5C . 1.392(6) no C5C C6C . 1.404(6) no C6C C7C . 1.464(6) no C7C C8C . 1.423(6) no C8C C9C . 1.328(6) no C8C C12C . 1.508(6) no C9C C10C . 1.487(6) no C10C C11C . 1.529(6) no C11C C13C . 1.508(6) no O4C H4C . 0.8200 no O6C H6C . 0.8200 no O7C H7C . 0.8200 no O8C H8C . 0.8200 no C4C H4CA . 0.9300 no C10C H10E . 0.9700 no C10C H10F . 0.9700 no C12C H12E . 0.9700 no C12C H12F . 0.9700 no C13C H13G . 0.9600 no C13C H13H . 0.9600 no C13C H13I . 0.9600 no O1D C9D . 1.353(5) no O1D C5D . 1.374(5) no O2D C12D . 1.425(5) no O2D C11D . 1.431(6) no O3D C7D . 1.276(5) no O4D C14D . 1.280(6) no O5D C14D . 1.233(6) no O6D C2D . 1.327(5) no O7D C3D . 1.354(5) no O8D C11D . 1.414(6) no C1D C2D . 1.417(6) no C1D C6D . 1.451(6) no C1D C14D . 1.504(6) no C2D C3D . 1.406(6) no C3D C4D . 1.369(6) no C4D C5D . 1.399(6) no C5D C6D . 1.397(6) no C6D C7D . 1.449(6) no C7D C8D . 1.429(6) no C8D C9D . 1.329(6) no C8D C12D . 1.495(6) no C9D C10D . 1.489(6) no C10D C11D . 1.531(6) no C11D C13D . 1.513(6) no O4D H4D . 0.8200 no O6D H6D . 0.8200 no O7D H7D . 0.8200 no O8D H8D . 0.8200 no C4D H4DA . 0.9300 no C10D H10C . 0.9700 no C10D H10D . 0.9700 no C12D H12C . 0.9700 no C12D H12D . 0.9700 no C13D H13J . 0.9600 no C13D H13K . 0.9600 no C13D H13L . 0.9600 no O1 C1 . 1.413(6) no O2 C2 . 1.420(6) no O3 C3 . 1.342(6) no O1 H1 . 0.8200 no O2 H2 . 0.8200 no O3 H3 . 0.8200 no C1 H1A . 0.9600 no C1 H1B . 0.9600 no C1 H1C . 0.9600 no C2 H2A . 0.9600 no C2 H2B . 0.9600 no C2 H2C . 0.9600 no C3 H3A . 0.9600 no C3 H3B . 0.9600 no C3 H3C . 0.9600 no