#------------------------------------------------------------------------------ #$Date: 2017-07-25 07:12:37 +0300 (Tue, 25 Jul 2017) $ #$Revision: 199012 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/87/7228730.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_7228730 loop_ _publ_author_name 'De Rosa, Margherita' 'La Manna, Pellegrino' 'Soriente, Annunziata' 'Gaeta, Carmine' 'Talotta, Carmen' 'Hickey, Neal' 'Geremia, Silvano' 'Neri, Placido' _publ_section_title ; Supramolecular Synthons in the Gamma-Hydroxybutenolides ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE00953D _journal_year 2017 _chemical_formula_moiety 'C15 H16 O5' _chemical_formula_sum 'C15 H16 O5' _chemical_formula_weight 276.28 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.3 _audit_creation_date 2017-05-17T10:47:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2017-05-17 deposited with the CCDC. 2017-07-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.186(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.6550(10) _cell_length_b 11.401(3) _cell_length_c 20.9880(19) _cell_measurement_reflns_used 29834 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.218 _cell_measurement_theta_min 1.807 _cell_measurement_wavelength 0.7 _cell_volume 2703.8(8) _computing_cell_refinement 'XDS (Kabasch, 2010)' _computing_data_collection 'ELETTRA XRD1 Data Collection SW' _computing_data_reduction XDS _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SIR-2014 (Burla et al., 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device 'Area detector' _diffrn_measurement_device_type 'Dectris Pilatus 2M' _diffrn_measurement_method 'Rotating Crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.7 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0175 _diffrn_reflns_Laue_measured_fraction_full 0.973 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 44172 _diffrn_reflns_point_group_measured_fraction_full 0.973 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 24.835 _diffrn_reflns_theta_max 28.218 _diffrn_reflns_theta_min 1.807 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.471 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.057 _refine_ls_extinction_coef 0.096(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 368 _refine_ls_number_reflns 6718 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0384 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+1.2020P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1015 _reflns_Friedel_coverage 0 _reflns_number_gt 6477 _reflns_number_total 6718 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce00953d2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7228730 _shelx_estimated_absorpt_t_min 0.976 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR2014 run in space group P 21/n CELL 0.70000 11.6550 11.4010 20.9880 90.000 104.186 90.000 ZERR 8.00 0.0010 0.0029 0.0019 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H O DISP C 0.00299 0.00157 10.98 DISP H 0.00000 0.00000 0.67 DISP O 0.01046 0.00590 30.82 UNIT 120 128 40 MERG 2 OMIT -1 2 4 OMIT 0 1 4 OMIT 0 2 2 OMIT 0 6 1 OMIT 8 0 2 OMIT -2 0 4 FMAP 2 PLAN 25 SIZE 0.080 0.080 0.250 ACTA BOND $H CONF LIST 4 L.S. 10 TEMP -173.00 WGHT 0.054000 1.202000 EXTI 0.096061 FVAR 8.14293 C1A 1 -0.526886 0.103123 0.933498 11.00000 0.02067 0.02426 = 0.01902 -0.00022 0.00935 0.00029 AFIX 137 H1A 2 -0.576866 0.039256 0.910804 11.00000 -1.50000 H1B 2 -0.566918 0.142563 0.963501 11.00000 -1.50000 H1C 2 -0.451240 0.071072 0.958574 11.00000 -1.50000 AFIX 0 C2A 1 -0.504791 0.189993 0.883687 11.00000 0.02113 0.01968 = 0.02224 -0.00034 0.01221 0.00364 AFIX 23 H2A 2 -0.580434 0.223311 0.857935 11.00000 -1.20000 H2B 2 -0.453923 0.254907 0.905826 11.00000 -1.20000 AFIX 0 C3A 1 -0.414966 0.185540 0.793497 11.00000 0.01008 0.01556 = 0.01550 0.00074 0.00285 0.00056 C4A 1 -0.347664 0.106394 0.755363 11.00000 0.01088 0.01241 = 0.01302 0.00147 0.00322 0.00005 C5A 1 -0.372134 0.149889 0.683302 11.00000 0.01019 0.01789 = 0.01369 0.00212 0.00190 -0.00103 AFIX 13 H5A 2 -0.347337 0.233655 0.682047 11.00000 -1.20000 AFIX 0 C6A 1 -0.312920 0.075881 0.641891 11.00000 0.01310 0.02465 = 0.01472 0.00280 0.00533 0.00018 AFIX 43 H6A 2 -0.229816 0.066844 0.648415 11.00000 -1.20000 AFIX 0 C7A 1 -0.394480 0.024662 0.594528 11.00000 0.01535 0.02577 = 0.01577 -0.00095 0.00547 0.00077 AFIX 43 H7A 2 -0.379627 -0.026932 0.561917 11.00000 -1.20000 AFIX 0 C8A 1 -0.511618 0.061821 0.601449 11.00000 0.01422 0.02131 = 0.01451 0.00061 0.00331 -0.00082 C9A 1 -0.214889 0.118645 0.786053 11.00000 0.01068 0.01507 = 0.01125 0.00054 0.00316 0.00018 C10A 1 -0.161679 0.228799 0.797425 11.00000 0.01348 0.01461 = 0.01832 0.00136 0.00298 0.00031 AFIX 43 H10A 2 -0.208981 0.297574 0.788858 11.00000 -1.20000 AFIX 0 C11A 1 -0.039703 0.238410 0.821246 11.00000 0.01427 0.01744 = 0.01846 -0.00022 0.00277 -0.00289 AFIX 43 H11A 2 -0.004739 0.313986 0.829015 11.00000 -1.20000 AFIX 0 C12A 1 0.032239 0.139111 0.833941 11.00000 0.01155 0.02267 = 0.01215 -0.00045 0.00225 0.00012 C13A 1 -0.021822 0.029405 0.823071 11.00000 0.01348 0.01845 = 0.01524 0.00010 0.00258 0.00347 AFIX 43 H13A 2 0.025467 -0.039360 0.831811 11.00000 -1.20000 AFIX 0 C14A 1 -0.144008 0.018847 0.799612 11.00000 0.01346 0.01463 = 0.01481 -0.00010 0.00316 0.00060 AFIX 43 H14A 2 -0.179183 -0.056746 0.792824 11.00000 -1.20000 AFIX 0 C15A 1 0.164887 0.151450 0.856654 11.00000 0.01130 0.02887 = 0.01982 -0.00154 0.00118 -0.00072 AFIX 137 H15A 2 0.192094 0.210550 0.829778 11.00000 -1.50000 H15B 2 0.202301 0.075959 0.852108 11.00000 -1.50000 H15C 2 0.186432 0.175856 0.902829 11.00000 -1.50000 AFIX 0 O1A 3 -0.445822 0.124998 0.840971 11.00000 0.01783 0.01677 = 0.01656 0.00127 0.00856 0.00247 O2A 3 -0.432807 0.288531 0.782793 11.00000 0.02201 0.01607 = 0.02777 0.00414 0.01156 0.00491 O3A 3 -0.379882 -0.011654 0.756658 11.00000 0.01173 0.01289 = 0.01850 0.00081 0.00448 -0.00177 AFIX 147 H1O3 2 -0.453510 -0.016667 0.751442 11.00000 -1.50000 AFIX 0 O4A 3 -0.496960 0.137708 0.652723 11.00000 0.01052 0.02105 = 0.01432 -0.00018 0.00123 0.00102 O5A 3 -0.608941 0.035202 0.568883 11.00000 0.01362 0.03650 = 0.02104 -0.00606 0.00091 -0.00265 C1B 1 0.327740 0.345677 0.460894 11.00000 0.01936 0.04027 = 0.01889 0.00429 0.00693 -0.00278 AFIX 137 H1D 2 0.361197 0.267305 0.458861 11.00000 -1.50000 H1E 2 0.382174 0.404784 0.451258 11.00000 -1.50000 H1F 2 0.251512 0.351417 0.428468 11.00000 -1.50000 AFIX 0 C2B 1 0.309859 0.366409 0.528492 11.00000 0.02064 0.02564 = 0.02178 0.00034 0.00911 -0.00661 AFIX 23 H2C 2 0.386777 0.365597 0.561541 11.00000 -1.20000 H2D 2 0.271467 0.443310 0.530526 11.00000 -1.20000 AFIX 0 C3B 1 0.208909 0.274683 0.599605 11.00000 0.01144 0.01899 = 0.01360 -0.00025 0.00252 -0.00025 C4B 1 0.131525 0.169044 0.607947 11.00000 0.01161 0.01569 = 0.01166 -0.00242 0.00232 -0.00084 C5B 1 0.158764 0.136414 0.681792 11.00000 0.01010 0.02183 = 0.01262 -0.00051 0.00195 0.00021 AFIX 13 H5B 2 0.141263 0.204153 0.708174 11.00000 -1.20000 AFIX 0 C6B 1 0.093046 0.029674 0.694271 11.00000 0.01134 0.02657 = 0.01433 0.00144 0.00310 -0.00299 AFIX 43 H6B 2 0.009391 0.023430 0.685863 11.00000 -1.20000 AFIX 0 C7B 1 0.169258 -0.055221 0.718908 11.00000 0.01206 0.02370 = 0.01555 0.00116 0.00275 -0.00416 AFIX 43 H7B 2 0.149638 -0.131310 0.731366 11.00000 -1.20000 AFIX 0 C8B 1 0.289174 -0.010461 0.723440 11.00000 0.01267 0.02105 = 0.01227 0.00029 0.00259 -0.00193 C9B 1 0.001892 0.206849 0.586082 11.00000 0.01132 0.01639 = 0.01227 -0.00006 0.00239 -0.00082 C10B 1 -0.039143 0.301837 0.616290 11.00000 0.01539 0.01880 = 0.01480 -0.00346 0.00286 -0.00098 AFIX 43 H10B 2 0.013998 0.343762 0.650198 11.00000 -1.20000 AFIX 0 C11B 1 -0.157451 0.335403 0.596990 11.00000 0.01693 0.01873 = 0.01806 -0.00153 0.00569 0.00148 AFIX 43 H11B 2 -0.184184 0.400370 0.617769 11.00000 -1.20000 AFIX 0 C12B 1 -0.237323 0.274788 0.547477 11.00000 0.01282 0.01955 = 0.01682 0.00359 0.00398 0.00009 C13B 1 -0.195372 0.180137 0.517740 11.00000 0.01420 0.01868 = 0.01617 -0.00055 0.00065 -0.00263 AFIX 43 H13B 2 -0.248583 0.138004 0.483959 11.00000 -1.20000 AFIX 0 C14B 1 -0.077064 0.145967 0.536487 11.00000 0.01484 0.01610 = 0.01494 -0.00200 0.00228 -0.00100 AFIX 43 H14B 2 -0.050277 0.081295 0.515502 11.00000 -1.20000 AFIX 0 C15B 1 -0.365915 0.309715 0.527378 11.00000 0.01324 0.02707 = 0.02570 0.00475 0.00337 0.00284 AFIX 137 H15D 2 -0.375386 0.376673 0.497257 11.00000 -1.50000 H15E 2 -0.392841 0.331595 0.566479 11.00000 -1.50000 H15F 2 -0.413108 0.243579 0.505334 11.00000 -1.50000 AFIX 0 O1B 3 0.234671 0.272076 0.541089 11.00000 0.01924 0.02179 = 0.01477 -0.00178 0.00688 -0.00516 O2B 3 0.239102 0.350673 0.639930 11.00000 0.02220 0.02328 = 0.01877 -0.00646 0.00634 -0.00749 O3B 3 0.151093 0.071978 0.570832 11.00000 0.01329 0.01740 = 0.01676 -0.00485 0.00423 -0.00003 AFIX 147 H2O3 2 0.223686 0.066419 0.572633 11.00000 -1.50000 AFIX 0 O4B 3 0.282155 0.103234 0.703520 11.00000 0.00976 0.02086 = 0.01572 0.00116 0.00115 -0.00174 O5B 3 0.383607 -0.060396 0.741158 11.00000 0.01161 0.02662 = 0.02158 0.00448 0.00330 0.00095 HKLF 4 REM SIR2014 run in space group P 21/n REM R1 = 0.0384 for 6477 Fo > 4sig(Fo) and 0.0391 for all 6718 data REM 368 parameters refined using 0 restraints END WGHT 0.0540 1.2020 REM Highest difference peak 0.471, deepest hole -0.244, 1-sigma level 0.057 Q1 1 0.0642 0.1857 0.5972 11.00000 0.05 0.47 Q2 1 -0.3828 0.1459 0.7742 11.00000 0.05 0.41 Q3 1 -0.1816 0.0683 0.7940 11.00000 0.05 0.41 Q4 1 -0.2801 0.1097 0.7724 11.00000 0.05 0.40 Q5 1 -0.1015 0.2238 0.8097 11.00000 0.05 0.40 Q6 1 0.2260 -0.0396 0.7205 11.00000 0.05 0.39 Q7 1 0.1437 0.1539 0.6435 11.00000 0.05 0.39 Q8 1 -0.4572 0.0432 0.5947 11.00000 0.05 0.39 Q9 1 0.1650 0.2222 0.6018 11.00000 0.05 0.38 Q10 1 -0.0154 0.2526 0.5969 11.00000 0.05 0.37 Q11 1 -0.1915 0.1723 0.7967 11.00000 0.05 0.36 Q12 1 -0.0821 0.0276 0.8106 11.00000 0.05 0.35 Q13 1 -0.0058 0.1829 0.8302 11.00000 0.05 0.35 Q14 1 0.1231 0.0834 0.6871 11.00000 0.05 0.35 Q15 1 -0.0366 0.1781 0.5623 11.00000 0.05 0.34 Q16 1 -0.2137 0.2316 0.5289 11.00000 0.05 0.34 Q17 1 0.0992 0.1457 0.8465 11.00000 0.05 0.32 Q18 1 -0.3424 0.1106 0.6624 11.00000 0.05 0.32 Q19 1 -0.1366 0.1601 0.5309 11.00000 0.05 0.31 Q20 1 0.1247 -0.0137 0.7076 11.00000 0.05 0.31 Q21 1 -0.3585 0.1254 0.7198 11.00000 0.05 0.30 Q22 1 -0.5124 0.1466 0.9061 11.00000 0.05 0.29 Q23 1 0.0055 0.0835 0.8313 11.00000 0.05 0.29 Q24 1 0.3236 0.3574 0.4960 11.00000 0.05 0.29 Q25 1 -0.3023 0.2879 0.5398 11.00000 0.05 0.28 ; _shelx_res_checksum 43728 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1A C -0.52689(9) 0.10312(10) 0.93350(5) 0.0205(2) Uani 1 1 d . . H1A H -0.5769 0.0393 0.9108 0.031 Uiso 1 1 calc R U H1B H -0.5669 0.1426 0.9635 0.031 Uiso 1 1 calc R U H1C H -0.4512 0.0711 0.9586 0.031 Uiso 1 1 calc R U C2A C -0.50479(9) 0.18999(10) 0.88369(5) 0.0198(2) Uani 1 1 d . . H2A H -0.5804 0.2233 0.8579 0.024 Uiso 1 1 calc R U H2B H -0.4539 0.2549 0.9058 0.024 Uiso 1 1 calc R U C3A C -0.41497(8) 0.18554(9) 0.79350(5) 0.01376(18) Uani 1 1 d . . C4A C -0.34766(8) 0.10639(8) 0.75536(4) 0.01205(17) Uani 1 1 d . . C5A C -0.37213(8) 0.14989(9) 0.68330(4) 0.01410(18) Uani 1 1 d . . H5A H -0.3473 0.2337 0.682 0.017 Uiso 1 1 calc R U C6A C -0.31292(8) 0.07588(10) 0.64189(5) 0.0172(2) Uani 1 1 d . . H6A H -0.2298 0.0668 0.6484 0.021 Uiso 1 1 calc R U C7A C -0.39448(9) 0.02466(10) 0.59453(5) 0.0187(2) Uani 1 1 d . . H7A H -0.3796 -0.0269 0.5619 0.022 Uiso 1 1 calc R U C8A C -0.51162(8) 0.06182(9) 0.60145(5) 0.01672(19) Uani 1 1 d . . C9A C -0.21489(8) 0.11864(8) 0.78605(4) 0.01225(17) Uani 1 1 d . . C10A C -0.16168(8) 0.22880(9) 0.79743(5) 0.01563(19) Uani 1 1 d . . H10A H -0.209 0.2976 0.7889 0.019 Uiso 1 1 calc R U C11A C -0.03970(8) 0.23841(9) 0.82125(5) 0.01694(19) Uani 1 1 d . . H11A H -0.0047 0.314 0.829 0.02 Uiso 1 1 calc R U C12A C 0.03224(8) 0.13911(9) 0.83394(5) 0.01557(19) Uani 1 1 d . . C13A C -0.02182(8) 0.02940(9) 0.82307(5) 0.01589(19) Uani 1 1 d . . H13A H 0.0255 -0.0394 0.8318 0.019 Uiso 1 1 calc R U C14A C -0.14401(8) 0.01885(9) 0.79961(5) 0.01435(18) Uani 1 1 d . . H14A H -0.1792 -0.0567 0.7928 0.017 Uiso 1 1 calc R U C15A C 0.16489(9) 0.15145(10) 0.85665(5) 0.0205(2) Uani 1 1 d . . H15A H 0.1921 0.2105 0.8298 0.031 Uiso 1 1 calc R U H15B H 0.2023 0.076 0.8521 0.031 Uiso 1 1 calc R U H15C H 0.1864 0.1759 0.9028 0.031 Uiso 1 1 calc R U O1A O -0.44582(6) 0.12500(7) 0.84097(3) 0.01630(15) Uani 1 1 d . . O2A O -0.43281(7) 0.28853(7) 0.78279(4) 0.02100(17) Uani 1 1 d . . O3A O -0.37988(6) -0.01165(6) 0.75666(3) 0.01424(15) Uani 1 1 d . . H1O3 H -0.4535 -0.0167 0.7514 0.021 Uiso 1 1 calc R U O4A O -0.49696(6) 0.13771(7) 0.65272(3) 0.01561(15) Uani 1 1 d . . O5A O -0.60894(7) 0.03520(8) 0.56888(4) 0.02430(18) Uani 1 1 d . . C1B C 0.32774(10) 0.34568(12) 0.46089(5) 0.0258(2) Uani 1 1 d . . H1D H 0.3612 0.2673 0.4589 0.039 Uiso 1 1 calc R U H1E H 0.3822 0.4048 0.4513 0.039 Uiso 1 1 calc R U H1F H 0.2515 0.3514 0.4285 0.039 Uiso 1 1 calc R U C2B C 0.30986(10) 0.36641(10) 0.52849(5) 0.0220(2) Uani 1 1 d . . H2C H 0.3868 0.3656 0.5615 0.026 Uiso 1 1 calc R U H2D H 0.2715 0.4433 0.5305 0.026 Uiso 1 1 calc R U C3B C 0.20891(8) 0.27468(9) 0.59960(5) 0.01477(18) Uani 1 1 d . . C4B C 0.13153(8) 0.16904(9) 0.60795(4) 0.01308(18) Uani 1 1 d . . C5B C 0.15876(8) 0.13641(9) 0.68179(5) 0.01500(19) Uani 1 1 d . . H5B H 0.1413 0.2042 0.7082 0.018 Uiso 1 1 calc R U C6B C 0.09305(8) 0.02967(10) 0.69427(5) 0.0174(2) Uani 1 1 d . . H6B H 0.0094 0.0234 0.6859 0.021 Uiso 1 1 calc R U C7B C 0.16926(8) -0.05522(10) 0.71891(5) 0.0172(2) Uani 1 1 d . . H7B H 0.1496 -0.1313 0.7314 0.021 Uiso 1 1 calc R U C8B C 0.28917(8) -0.01046(9) 0.72344(4) 0.01541(19) Uani 1 1 d . . C9B C 0.00189(8) 0.20685(9) 0.58608(4) 0.01341(18) Uani 1 1 d . . C10B C -0.03914(8) 0.30184(9) 0.61629(5) 0.01647(19) Uani 1 1 d . . H10B H 0.014 0.3438 0.6502 0.02 Uiso 1 1 calc R U C11B C -0.15745(9) 0.33540(9) 0.59699(5) 0.0177(2) Uani 1 1 d . . H11B H -0.1842 0.4004 0.6178 0.021 Uiso 1 1 calc R U C12B C -0.23732(8) 0.27479(9) 0.54748(5) 0.01634(19) Uani 1 1 d . . C13B C -0.19537(8) 0.18014(9) 0.51774(5) 0.01688(19) Uani 1 1 d . . H13B H -0.2486 0.138 0.484 0.02 Uiso 1 1 calc R U C14B C -0.07706(8) 0.14597(9) 0.53649(5) 0.01553(19) Uani 1 1 d . . H14B H -0.0503 0.0813 0.5155 0.019 Uiso 1 1 calc R U C15B C -0.36592(9) 0.30971(11) 0.52738(5) 0.0222(2) Uani 1 1 d . . H15D H -0.3754 0.3767 0.4973 0.033 Uiso 1 1 calc R U H15E H -0.3928 0.3316 0.5665 0.033 Uiso 1 1 calc R U H15F H -0.4131 0.2436 0.5053 0.033 Uiso 1 1 calc R U O1B O 0.23467(6) 0.27208(7) 0.54109(3) 0.01813(16) Uani 1 1 d . . O2B O 0.23910(7) 0.35067(7) 0.63993(4) 0.02119(17) Uani 1 1 d . . O3B O 0.15109(6) 0.07198(6) 0.57083(3) 0.01572(15) Uani 1 1 d . . H2O3 H 0.2237 0.0664 0.5726 0.024 Uiso 1 1 calc R U O4B O 0.28216(6) 0.10323(7) 0.70352(3) 0.01579(15) Uani 1 1 d . . O5B O 0.38361(6) -0.06040(7) 0.74116(4) 0.02007(16) Uani 1 1 d . . 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 C1A 0.0207(5) 0.0243(6) 0.0190(5) -0.0002(4) 0.0093(4) 0.0003(4) C2A 0.0211(5) 0.0197(5) 0.0222(5) -0.0003(4) 0.0122(4) 0.0036(4) C3A 0.0101(4) 0.0156(5) 0.0155(4) 0.0007(3) 0.0029(3) 0.0006(3) C4A 0.0109(4) 0.0124(4) 0.0130(4) 0.0015(3) 0.0032(3) 0.0000(3) C5A 0.0102(4) 0.0179(5) 0.0137(4) 0.0021(3) 0.0019(3) -0.0010(3) C6A 0.0131(4) 0.0247(5) 0.0147(4) 0.0028(4) 0.0053(3) 0.0002(3) C7A 0.0153(4) 0.0258(5) 0.0158(4) -0.0009(4) 0.0055(3) 0.0008(4) C8A 0.0142(4) 0.0213(5) 0.0145(4) 0.0006(3) 0.0033(3) -0.0008(3) C9A 0.0107(4) 0.0151(4) 0.0112(4) 0.0005(3) 0.0032(3) 0.0002(3) C10A 0.0135(4) 0.0146(5) 0.0183(4) 0.0014(3) 0.0030(3) 0.0003(3) C11A 0.0143(4) 0.0174(5) 0.0185(4) -0.0002(3) 0.0028(3) -0.0029(3) C12A 0.0115(4) 0.0227(5) 0.0122(4) -0.0004(3) 0.0023(3) 0.0001(3) C13A 0.0135(4) 0.0184(5) 0.0152(4) 0.0001(3) 0.0026(3) 0.0035(3) C14A 0.0135(4) 0.0146(5) 0.0148(4) -0.0001(3) 0.0032(3) 0.0006(3) C15A 0.0113(4) 0.0289(6) 0.0198(5) -0.0015(4) 0.0012(3) -0.0007(4) O1A 0.0178(3) 0.0168(4) 0.0166(3) 0.0013(3) 0.0086(3) 0.0025(3) O2A 0.0220(4) 0.0161(4) 0.0278(4) 0.0041(3) 0.0116(3) 0.0049(3) O3A 0.0117(3) 0.0129(3) 0.0185(3) 0.0008(2) 0.0045(2) -0.0018(2) O4A 0.0105(3) 0.0210(4) 0.0143(3) -0.0002(3) 0.0012(2) 0.0010(2) O5A 0.0136(3) 0.0365(5) 0.0210(4) -0.0061(3) 0.0009(3) -0.0026(3) C1B 0.0194(5) 0.0403(7) 0.0189(5) 0.0043(4) 0.0069(4) -0.0028(4) C2B 0.0206(5) 0.0256(6) 0.0218(5) 0.0003(4) 0.0091(4) -0.0066(4) C3B 0.0114(4) 0.0190(5) 0.0136(4) -0.0002(3) 0.0025(3) -0.0003(3) C4B 0.0116(4) 0.0157(5) 0.0117(4) -0.0024(3) 0.0023(3) -0.0008(3) C5B 0.0101(4) 0.0218(5) 0.0126(4) -0.0005(3) 0.0020(3) 0.0002(3) C6B 0.0113(4) 0.0266(5) 0.0143(4) 0.0014(4) 0.0031(3) -0.0030(3) C7B 0.0121(4) 0.0237(5) 0.0156(4) 0.0012(3) 0.0028(3) -0.0042(3) C8B 0.0127(4) 0.0211(5) 0.0123(4) 0.0003(3) 0.0026(3) -0.0019(3) C9B 0.0113(4) 0.0164(5) 0.0123(4) -0.0001(3) 0.0024(3) -0.0008(3) C10B 0.0154(4) 0.0188(5) 0.0148(4) -0.0035(3) 0.0029(3) -0.0010(3) C11B 0.0169(4) 0.0187(5) 0.0181(4) -0.0015(3) 0.0057(3) 0.0015(3) C12B 0.0128(4) 0.0195(5) 0.0168(4) 0.0036(3) 0.0040(3) 0.0001(3) C13B 0.0142(4) 0.0187(5) 0.0162(4) -0.0006(3) 0.0006(3) -0.0026(3) C14B 0.0148(4) 0.0161(5) 0.0149(4) -0.0020(3) 0.0023(3) -0.0010(3) C15B 0.0132(4) 0.0271(6) 0.0257(5) 0.0047(4) 0.0034(4) 0.0028(4) O1B 0.0192(3) 0.0218(4) 0.0148(3) -0.0018(3) 0.0069(3) -0.0052(3) O2B 0.0222(4) 0.0233(4) 0.0188(3) -0.0065(3) 0.0063(3) -0.0075(3) O3B 0.0133(3) 0.0174(4) 0.0168(3) -0.0049(3) 0.0042(2) 0.0000(2) O4B 0.0098(3) 0.0209(4) 0.0157(3) 0.0012(3) 0.0011(2) -0.0017(2) O5B 0.0116(3) 0.0266(4) 0.0216(3) 0.0045(3) 0.0033(3) 0.0010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0105 0.0059 '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 C2A C1A H1A 109.5 C2A C1A H1B 109.5 H1A C1A H1B 109.5 C2A C1A H1C 109.5 H1A C1A H1C 109.5 H1B C1A H1C 109.5 O1A C2A C1A 106.19(8) O1A C2A H2A 110.5 C1A C2A H2A 110.5 O1A C2A H2B 110.5 C1A C2A H2B 110.5 H2A C2A H2B 108.7 O2A C3A O1A 125.38(9) O2A C3A C4A 124.08(9) O1A C3A C4A 110.48(8) O3A C4A C9A 109.16(7) O3A C4A C3A 112.31(7) C9A C4A C3A 108.59(7) O3A C4A C5A 109.91(8) C9A C4A C5A 107.87(7) C3A C4A C5A 108.89(7) O4A C5A C6A 104.20(7) O4A C5A C4A 109.08(7) C6A C5A C4A 112.68(8) O4A C5A H5A 110.2 C6A C5A H5A 110.2 C4A C5A H5A 110.2 C7A C6A C5A 109.56(8) C7A C6A H6A 125.2 C5A C6A H6A 125.2 C6A C7A C8A 108.09(9) C6A C7A H7A 126 C8A C7A H7A 126 O5A C8A O4A 121.69(9) O5A C8A C7A 129.51(10) O4A C8A C7A 108.80(8) C14A C9A C10A 118.92(8) C14A C9A C4A 119.95(8) C10A C9A C4A 121.04(8) C11A C10A C9A 120.32(9) C11A C10A H10A 119.8 C9A C10A H10A 119.8 C10A C11A C12A 121.21(9) C10A C11A H11A 119.4 C12A C11A H11A 119.4 C13A C12A C11A 118.07(9) C13A C12A C15A 121.50(9) C11A C12A C15A 120.40(9) C14A C13A C12A 121.15(9) C14A C13A H13A 119.4 C12A C13A H13A 119.4 C13A C14A C9A 120.33(9) C13A C14A H14A 119.8 C9A C14A H14A 119.8 C12A C15A H15A 109.5 C12A C15A H15B 109.5 H15A C15A H15B 109.5 C12A C15A H15C 109.5 H15A C15A H15C 109.5 H15B C15A H15C 109.5 C3A O1A C2A 116.80(8) C4A O3A H1O3 109.5 C8A O4A C5A 109.29(7) C2B C1B H1D 109.5 C2B C1B H1E 109.5 H1D C1B H1E 109.5 C2B C1B H1F 109.5 H1D C1B H1F 109.5 H1E C1B H1F 109.5 O1B C2B C1B 106.56(9) O1B C2B H2C 110.4 C1B C2B H2C 110.4 O1B C2B H2D 110.4 C1B C2B H2D 110.4 H2C C2B H2D 108.6 O2B C3B O1B 124.83(9) O2B C3B C4B 124.20(9) O1B C3B C4B 110.94(8) O3B C4B C9B 109.79(7) O3B C4B C3B 111.97(8) C9B C4B C3B 107.97(8) O3B C4B C5B 110.15(8) C9B C4B C5B 108.24(7) C3B C4B C5B 108.62(7) O4B C5B C6B 104.13(8) O4B C5B C4B 108.78(7) C6B C5B C4B 112.49(8) O4B C5B H5B 110.4 C6B C5B H5B 110.4 C4B C5B H5B 110.4 C7B C6B C5B 109.79(8) C7B C6B H6B 125.1 C5B C6B H6B 125.1 C6B C7B C8B 107.86(9) C6B C7B H7B 126.1 C8B C7B H7B 126.1 O5B C8B O4B 121.58(9) O5B C8B C7B 129.34(10) O4B C8B C7B 109.09(8) C14B C9B C10B 119.22(9) C14B C9B C4B 120.44(9) C10B C9B C4B 120.34(8) C11B C10B C9B 120.39(9) C11B C10B H10B 119.8 C9B C10B H10B 119.8 C10B C11B C12B 120.84(9) C10B C11B H11B 119.6 C12B C11B H11B 119.6 C13B C12B C11B 118.25(9) C13B C12B C15B 120.86(9) C11B C12B C15B 120.88(10) C14B C13B C12B 121.43(9) C14B C13B H13B 119.3 C12B C13B H13B 119.3 C13B C14B C9B 119.88(9) C13B C14B H14B 120.1 C9B C14B H14B 120.1 C12B C15B H15D 109.5 C12B C15B H15E 109.5 H15D C15B H15E 109.5 C12B C15B H15F 109.5 H15D C15B H15F 109.5 H15E C15B H15F 109.5 C3B O1B C2B 115.67(8) C4B O3B H2O3 109.5 C8B O4B C5B 109.05(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1A C2A 1.5074(15) C1A H1A 0.98 C1A H1B 0.98 C1A H1C 0.98 C2A O1A 1.4585(12) C2A H2A 0.99 C2A H2B 0.99 C3A O2A 1.2040(13) C3A O1A 1.3320(11) C3A C4A 1.5420(13) C4A O3A 1.3993(12) C4A C9A 1.5299(12) C4A C5A 1.5502(13) C5A O4A 1.4457(11) C5A C6A 1.4959(14) C5A H5A 1 C6A C7A 1.3303(14) C6A H6A 0.95 C7A C8A 1.4703(13) C7A H7A 0.95 C8A O5A 1.2107(12) C8A O4A 1.3586(12) C9A C14A 1.3938(13) C9A C10A 1.3951(14) C10A C11A 1.3909(13) C10A H10A 0.95 C11A C12A 1.3951(14) C11A H11A 0.95 C12A C13A 1.3939(15) C12A C15A 1.5086(13) C13A C14A 1.3933(13) C13A H13A 0.95 C14A H14A 0.95 C15A H15A 0.98 C15A H15B 0.98 C15A H15C 0.98 O3A H1O3 0.84 C1B C2B 1.5024(15) C1B H1D 0.98 C1B H1E 0.98 C1B H1F 0.98 C2B O1B 1.4519(13) C2B H2C 0.99 C2B H2D 0.99 C3B O2B 1.2020(12) C3B O1B 1.3342(11) C3B C4B 1.5402(14) C4B O3B 1.4038(11) C4B C9B 1.5295(12) C4B C5B 1.5492(13) C5B O4B 1.4484(11) C5B C6B 1.4948(14) C5B H5B 1 C6B C7B 1.3297(15) C6B H6B 0.95 C7B C8B 1.4689(13) C7B H7B 0.95 C8B O5B 1.2137(12) C8B O4B 1.3583(13) C9B C14B 1.3938(13) C9B C10B 1.3972(14) C10B C11B 1.3921(13) C10B H10B 0.95 C11B C12B 1.3964(14) C11B H11B 0.95 C12B C13B 1.3938(14) C12B C15B 1.5076(13) C13B C14B 1.3935(13) C13B H13B 0.95 C14B H14B 0.95 C15B H15D 0.98 C15B H15E 0.98 C15B H15F 0.98 O3B H2O3 0.84 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 O2A C3A C4A O3A -154.92(9) O1A C3A C4A O3A 27.49(10) O2A C3A C4A C9A 84.26(11) O1A C3A C4A C9A -93.32(9) O2A C3A C4A C5A -32.95(12) O1A C3A C4A C5A 149.47(8) O3A C4A C5A O4A 60.27(10) C9A C4A C5A O4A 179.18(7) C3A C4A C5A O4A -63.15(10) O3A C4A C5A C6A -54.94(10) C9A C4A C5A C6A 63.97(10) C3A C4A C5A C6A -178.36(8) O4A C5A C6A C7A -1.72(11) C4A C5A C6A C7A 116.39(9) C5A C6A C7A C8A 0.28(12) C6A C7A C8A O5A -179.52(11) C6A C7A C8A O4A 1.39(12) O3A C4A C9A C14A 10.63(11) C3A C4A C9A C14A 133.37(9) C5A C4A C9A C14A -108.76(10) O3A C4A C9A C10A -173.06(8) C3A C4A C9A C10A -50.32(11) C5A C4A C9A C10A 67.55(11) C14A C9A C10A C11A 0.68(14) C4A C9A C10A C11A -175.67(8) C9A C10A C11A C12A 0.38(15) C10A C11A C12A C13A -1.02(14) C10A C11A C12A C15A 177.04(9) C11A C12A C13A C14A 0.61(14) C15A C12A C13A C14A -177.43(9) C12A C13A C14A C9A 0.44(14) C10A C9A C14A C13A -1.08(14) C4A C9A C14A C13A 175.31(8) O2A C3A O1A C2A -0.76(14) C4A C3A O1A C2A 176.79(8) C1A C2A O1A C3A -178.54(8) O5A C8A O4A C5A 178.31(10) C7A C8A O4A C5A -2.51(11) C6A C5A O4A C8A 2.58(10) C4A C5A O4A C8A -117.98(9) O2B C3B C4B O3B -153.99(9) O1B C3B C4B O3B 27.84(11) O2B C3B C4B C9B 85.04(11) O1B C3B C4B C9B -93.13(9) O2B C3B C4B C5B -32.12(13) O1B C3B C4B C5B 149.71(8) O3B C4B C5B O4B 61.37(10) C9B C4B C5B O4B -178.59(8) C3B C4B C5B O4B -61.60(10) O3B C4B C5B C6B -53.46(10) C9B C4B C5B C6B 66.59(10) C3B C4B C5B C6B -176.43(8) O4B C5B C6B C7B -1.12(11) C4B C5B C6B C7B 116.50(9) C5B C6B C7B C8B -0.66(11) C6B C7B C8B O5B -177.34(10) C6B C7B C8B O4B 2.36(11) O3B C4B C9B C14B 0.64(12) C3B C4B C9B C14B 122.95(10) C5B C4B C9B C14B -119.63(10) O3B C4B C9B C10B 179.70(9) C3B C4B C9B C10B -57.98(11) C5B C4B C9B C10B 59.43(12) C14B C9B C10B C11B -0.12(15) C4B C9B C10B C11B -179.19(9) C9B C10B C11B C12B 0.29(15) C10B C11B C12B C13B -0.24(15) C10B C11B C12B C15B 178.90(10) C11B C12B C13B C14B 0.03(15) C15B C12B C13B C14B -179.12(9) C12B C13B C14B C9B 0.14(15) C10B C9B C14B C13B -0.10(15) C4B C9B C14B C13B 178.98(9) O2B C3B O1B C2B 3.25(14) C4B C3B O1B C2B -178.60(8) C1B C2B O1B C3B 179.62(9) O5B C8B O4B C5B 176.65(9) C7B C8B O4B C5B -3.08(10) C6B C5B O4B C8B 2.59(10) C4B C5B O4B C8B -117.56(8)