#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:29:28 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252915 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157496.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_7157496 loop_ _publ_author_name 'St-Gelais, Jacob' 'Denavit, Vincent' 'Gigu\`ere, Denis' _publ_section_title ; Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3903 _journal_page_last 3907 _journal_paper_doi 10.1039/d0ob00910e _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C12 H16 O8), 1.25(H2 O)' _chemical_formula_sum 'C24 H34.5 O17.25' _chemical_formula_weight 599.01 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-12-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-30 deposited with the CCDC. 2020-05-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.2710(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 19.2032(9) _cell_length_b 6.1100(3) _cell_length_c 10.9617(5) _cell_measurement_reflns_used 9836 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.725 _cell_measurement_theta_min 3.606 _cell_volume 1251.81(10) _computing_cell_refinement 'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction 'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 19903 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.695 _diffrn_reflns_theta_min 4.116 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 0.755 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.6587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0970 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8760. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.589 _exptl_crystal_description block _exptl_crystal_F_000 633 _exptl_crystal_recrystallization_method 'crystallized in Acetone/Heptane' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.407 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.135 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_extinction_coef 0.161(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2861 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.145 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0507 _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^)+(0.0879P)^2^+0.3397P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1175 _refine_ls_wR_factor_ref 0.1176 _reflns_Friedel_coverage 0.823 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 2859 _reflns_number_total 2861 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00910e2.cif _cod_data_source_block dgige8 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7157496.cif. ; _cod_original_formula_sum 'C24 H34.50 O17.25' _cod_database_code 7157496 _shelx_shelxl_version_number 2018/3 _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_max 0.889 _shelx_estimated_absorpt_t_min 0.834 _olex2_refinement_description ; 1. Twinned data refinement Scales: 1.0(2) -0.0(2) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups, All O(H,H,H) groups 3. Restrained distances O2-H2 = O7-H7 = O9-H9A 0.85 with sigma of 0.002 O2-H2 \\sim O7-H7 \\sim O9-H9A with sigma of 0.002 4. Others Fixed Sof: O10(0.125) H10A(0.125) H10B(0.125) 5.a Riding coordinates: O10(H10A,H10B) 5.b Ternary CH refined with riding coordinates: C1(H1), C2(H2A), C3(H3), C4(H4), C6(H6), C7(H7A), C8(H8), C9(H9), C10(H10), C12(H12) 5.c Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C11(H11A,H11B) ; _shelx_res_file ; TITL dgige8_a.res in C2 dgige8.res created by SHELXL-2018/3 at 09:32:00 on 17-Dec-2018 REM Old TITL dgige8 in C2 REM SHELXT solution in C2 REM R1 0.148, Rweak 0.055, Alpha 0.010, Orientation as input REM Flack x = 0.195 ( 0.115 ) from Parsons' quotients REM Formula found by SHELXT: C24 O17 CELL 1.34139 19.2032 6.11 10.9617 90 103.271 90 ZERR 2 0.0009 0.0003 0.0005 0 0.001 0 LATT -7 SYMM -X,+Y,-Z SFAC C H O DISP C 0.0137 0.0057 57.1 DISP H -0 0 0.6 DISP O 0.0389 0.0241 193.4 UNIT 48 69 34.5 EQIV $1 1-X,+Y,2-Z EQIV $2 0.5+X,0.5+Y,+Z EQIV $3 0.5-X,0.5+Y,1-Z DFIX 0.85 0.002 O2 H2 O7 H7 O9 H9a SADI 0.002 O2 H2 O7 H7 O9 H9a L.S. 15 PLAN 8 SIZE 0.16 0.2 0.25 TEMP -123 HTAB O2 O9_$2 HTAB O7 O2_$3 HTAB O10 O3_$1 HTAB O10 O3 HTAB O9 O7 HTAB O9 O8 MORE -1 HTAB CONF WPDB BOND $H list 4 fmap 2 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 OMIT 1 1 1 OMIT 1 -1 1 REM REM REM WGHT 0.087900 0.339700 EXTI 0.160668 BASF -0.03838 FVAR 1.55956 O1 3 0.284582 0.309424 0.683279 11.00000 0.01769 0.01662 = 0.03022 -0.00060 0.01113 0.00004 O2 3 0.409082 0.479006 0.512708 11.00000 0.02410 0.02542 = 0.02177 -0.00519 0.01214 -0.00538 H2 2 0.438345 0.585289 0.521346 11.00000 -1.50000 O3 3 0.444381 0.404581 0.851562 11.00000 0.03262 0.06524 = 0.02290 -0.00196 0.00773 0.01305 O4 3 0.441499 0.731760 0.752646 11.00000 0.01863 0.04555 = 0.04053 -0.02217 0.01554 -0.01307 O5 3 0.257309 0.676648 0.778813 11.00000 0.01325 0.02151 = 0.02327 -0.00581 0.00785 -0.00328 O6 3 0.168074 0.394447 0.927847 11.00000 0.02297 0.03291 = 0.01982 0.00390 0.00411 -0.00029 O7 3 0.066957 0.655688 0.647342 11.00000 0.01579 0.02124 = 0.02799 0.00634 0.00348 0.00141 H7 2 0.075612 0.765598 0.605677 11.00000 -1.50000 O8 3 0.109155 0.236261 0.745896 11.00000 0.01650 0.01981 = 0.02873 -0.00076 0.00803 -0.00477 C1 1 0.318379 0.487193 0.635400 11.00000 0.01585 0.01884 = 0.01944 -0.00269 0.00653 -0.00198 AFIX 13 H1 2 0.290881 0.518067 0.548001 11.00000 -1.20000 AFIX 0 C2 1 0.394834 0.414650 0.629563 11.00000 0.01781 0.02469 = 0.02082 -0.00405 0.00902 -0.00018 AFIX 13 H2A 2 0.396813 0.251245 0.634251 11.00000 -1.20000 AFIX 0 C3 1 0.451568 0.504986 0.738988 11.00000 0.01573 0.04590 = 0.02713 -0.01075 0.00689 0.00023 AFIX 13 H3 2 0.500427 0.476673 0.724973 11.00000 -1.20000 AFIX 0 C4 1 0.383544 0.736075 0.816748 11.00000 0.01662 0.04253 = 0.03225 -0.02015 0.01086 -0.00916 AFIX 13 H4 2 0.381500 0.879720 0.859508 11.00000 -1.20000 AFIX 0 C5 1 0.404267 0.552765 0.911169 11.00000 0.01889 0.07050 = 0.02288 -0.01167 0.00528 0.00113 AFIX 23 H5A 2 0.433995 0.608477 0.991117 11.00000 -1.20000 H5B 2 0.361310 0.480243 0.927921 11.00000 -1.20000 AFIX 0 C6 1 0.315029 0.694902 0.716639 11.00000 0.01556 0.02050 = 0.02723 -0.00563 0.01010 -0.00433 AFIX 13 H6 2 0.305943 0.824943 0.659803 11.00000 -1.20000 AFIX 0 C7 1 0.195843 0.592427 0.693711 11.00000 0.01306 0.01487 = 0.01905 0.00032 0.00571 -0.00136 AFIX 13 H7A 2 0.189158 0.675473 0.613243 11.00000 -1.20000 AFIX 0 C8 1 0.128621 0.626312 0.746684 11.00000 0.01437 0.01782 = 0.02108 0.00012 0.00586 -0.00044 AFIX 13 H8 2 0.135408 0.758230 0.802155 11.00000 -1.20000 AFIX 0 C9 1 0.111918 0.427931 0.820086 11.00000 0.01690 0.02104 = 0.02010 0.00053 0.00659 -0.00232 AFIX 13 H9 2 0.065450 0.449561 0.844981 11.00000 -1.20000 AFIX 0 C10 1 0.183664 0.193221 0.755334 11.00000 0.01838 0.01485 = 0.03189 0.00293 0.01013 -0.00073 AFIX 13 H10 2 0.191199 0.037764 0.732890 11.00000 -1.20000 AFIX 0 C11 1 0.215416 0.234250 0.893928 11.00000 0.02133 0.03067 = 0.02879 0.01068 0.00710 0.00321 AFIX 23 H11A 2 0.216046 0.098225 0.943242 11.00000 -1.20000 H11B 2 0.264779 0.291906 0.907467 11.00000 -1.20000 AFIX 0 C12 1 0.209665 0.349995 0.667290 11.00000 0.01577 0.01608 = 0.02277 -0.00218 0.00748 -0.00244 AFIX 13 H12 2 0.184797 0.314627 0.578959 11.00000 -1.20000 AFIX 0 O9 3 0.000000 0.308504 0.500000 10.50000 0.02392 0.02440 = 0.02221 0.00000 0.00238 0.00000 O10 3 0.500000 0.063692 1.000000 10.12500 0.04397 0.02523 = 0.03559 0.00000 0.01049 0.00000 AFIX 3 H10A 2 0.544530 0.096932 1.031710 10.12500 -1.50000 H10B 2 0.489040 0.136192 0.929890 10.12500 -1.50000 AFIX 0 H9A 2 0.020000 0.402642 0.553815 11.00000 -1.50000 HKLF 4 REM dgige8_a.res in C2 REM wR2 = 0.1176, GooF = S = 1.147, Restrained GooF = 1.145 for all data REM R1 = 0.0507 for 2859 Fo > 4sig(Fo) and 0.0507 for all 2861 data REM 202 parameters refined using 7 restraints END WGHT 0.0879 0.3397 REM Instructions for potential hydrogen bonds HTAB O2 O9_$2 HTAB O7 O2_$3 EQIV $5 x+1/2, y-1/2, z HTAB C3 O7_$5 HTAB C3 O8_$2 EQIV $6 x-1/2, y+1/2, z HTAB C9 O10_$6 EQIV $7 x, y-1, z HTAB C10 O5_$7 EQIV $8 -x+1/2, y-1/2, -z+2 HTAB C11 O6_$8 HTAB O10 O3_$1 HTAB O10 O3 HTAB O9 O7 HTAB O9 O8 REM Highest difference peak 0.407, deepest hole -0.652, 1-sigma level 0.135 Q1 1 0.1187 0.7071 0.9383 11.00000 0.05 0.41 Q2 1 0.5475 0.1063 0.9166 11.00000 0.05 0.36 Q3 1 0.0247 0.7631 0.4812 11.00000 0.05 0.35 Q4 1 0.5759 0.1746 0.9692 11.00000 0.05 0.34 Q5 1 0.4931 0.0589 0.8200 11.00000 0.05 0.32 Q6 1 0.0039 0.5158 0.7998 11.00000 0.05 0.32 Q7 1 0.1516 0.7161 0.5248 11.00000 0.05 0.31 Q8 1 0.3624 1.0733 0.7954 11.00000 0.05 0.31 ; _shelx_res_checksum 87840 _olex2_exptl_crystal_mounting_method 'mounted on a cryoloop' _olex2_submission_original_sample_id JSTG020334 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.28458(9) 0.3094(3) 0.68328(16) 0.0206(4) Uani 1 1 d . . . . . O2 O 0.40908(9) 0.4790(3) 0.51271(15) 0.0226(4) Uani 1 1 d D . . . . H2 H 0.4383(16) 0.585(4) 0.521(3) 0.034 Uiso 1 1 d DR . . . . O3 O 0.44438(11) 0.4046(5) 0.85156(17) 0.0400(6) Uani 1 1 d . . . . . O4 O 0.44150(9) 0.7318(4) 0.75265(19) 0.0335(5) Uani 1 1 d . . . . . O5 O 0.25731(8) 0.6766(3) 0.77881(14) 0.0188(4) Uani 1 1 d . . . . . O6 O 0.16807(9) 0.3944(3) 0.92785(15) 0.0254(4) Uani 1 1 d . . . . . O7 O 0.06696(8) 0.6557(3) 0.64734(16) 0.0219(4) Uani 1 1 d D . . . . H7 H 0.076(2) 0.766(4) 0.606(3) 0.033 Uiso 1 1 d DR . . . . O8 O 0.10915(8) 0.2363(3) 0.74590(15) 0.0212(4) Uani 1 1 d . . . . . C1 C 0.31838(10) 0.4872(4) 0.63540(19) 0.0176(5) Uani 1 1 d . . . . . H1 H 0.290881 0.518067 0.548001 0.021 Uiso 1 1 calc R . . . . C2 C 0.39483(11) 0.4146(4) 0.6296(2) 0.0204(5) Uani 1 1 d . . . . . H2A H 0.396813 0.251245 0.634251 0.024 Uiso 1 1 calc R . . . . C3 C 0.45157(12) 0.5050(6) 0.7390(2) 0.0293(6) Uani 1 1 d . . . . . H3 H 0.500427 0.476673 0.724973 0.035 Uiso 1 1 calc R . . . . C4 C 0.38354(12) 0.7361(5) 0.8167(2) 0.0296(6) Uani 1 1 d . . . . . H4 H 0.381500 0.879720 0.859508 0.036 Uiso 1 1 calc R . . . . C5 C 0.40427(13) 0.5528(7) 0.9112(2) 0.0373(8) Uani 1 1 d . . . . . H5A H 0.433995 0.608477 0.991117 0.045 Uiso 1 1 calc R . . . . H5B H 0.361310 0.480243 0.927921 0.045 Uiso 1 1 calc R . . . . C6 C 0.31503(11) 0.6949(4) 0.7166(2) 0.0203(5) Uani 1 1 d . . . . . H6 H 0.305943 0.824943 0.659803 0.024 Uiso 1 1 calc R . . . . C7 C 0.19584(11) 0.5924(4) 0.69371(19) 0.0153(4) Uani 1 1 d . . . . . H7A H 0.189158 0.675473 0.613243 0.018 Uiso 1 1 calc R . . . . C8 C 0.12862(11) 0.6263(4) 0.7467(2) 0.0175(4) Uani 1 1 d . . . . . H8 H 0.135408 0.758230 0.802155 0.021 Uiso 1 1 calc R . . . . C9 C 0.11192(11) 0.4279(4) 0.82009(19) 0.0190(5) Uani 1 1 d . . . . . H9 H 0.065450 0.449561 0.844981 0.023 Uiso 1 1 calc R . . . . C10 C 0.18366(11) 0.1932(4) 0.7553(2) 0.0210(5) Uani 1 1 d . . . . . H10 H 0.191199 0.037764 0.732890 0.025 Uiso 1 1 calc R . . . . C11 C 0.21542(12) 0.2342(5) 0.8939(2) 0.0267(5) Uani 1 1 d . . . . . H11A H 0.216046 0.098225 0.943242 0.032 Uiso 1 1 calc R . . . . H11B H 0.264779 0.291906 0.907467 0.032 Uiso 1 1 calc R . . . . C12 C 0.20967(11) 0.3500(4) 0.6673(2) 0.0177(4) Uani 1 1 d . . . . . H12 H 0.184797 0.314627 0.578959 0.021 Uiso 1 1 calc R . . . . O9 O 0.000000 0.3085(4) 0.500000 0.0240(5) Uani 1 2 d DS T P . . O10 O 0.500000 0.064(2) 1.000000 0.035(2) Uani 0.25 2 d S T P . . H10A H 0.544530 0.096932 1.031710 0.052 Uiso 0.125 1 d R . . . . H10B H 0.489040 0.136192 0.929890 0.052 Uiso 0.125 1 d R . . . . H9A H 0.020(2) 0.403(5) 0.554(3) 0.052 Uiso 1 1 d DR . . . . 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 0.0177(8) 0.0166(7) 0.0302(8) -0.0006(6) 0.0111(6) 0.0000(6) O2 0.0241(8) 0.0254(8) 0.0218(8) -0.0052(6) 0.0121(6) -0.0054(6) O3 0.0326(9) 0.0652(16) 0.0229(8) -0.0020(10) 0.0077(7) 0.0131(11) O4 0.0186(8) 0.0456(12) 0.0405(10) -0.0222(9) 0.0155(7) -0.0131(8) O5 0.0133(7) 0.0215(8) 0.0233(7) -0.0058(6) 0.0079(5) -0.0033(6) O6 0.0230(8) 0.0329(10) 0.0198(7) 0.0039(6) 0.0041(6) -0.0003(7) O7 0.0158(7) 0.0212(8) 0.0280(8) 0.0063(6) 0.0035(6) 0.0014(6) O8 0.0165(7) 0.0198(8) 0.0287(8) -0.0008(6) 0.0080(6) -0.0048(6) C1 0.0159(9) 0.0188(10) 0.0194(9) -0.0027(8) 0.0065(7) -0.0020(7) C2 0.0178(9) 0.0247(10) 0.0208(9) -0.0041(8) 0.0090(7) -0.0002(8) C3 0.0157(9) 0.0459(15) 0.0271(11) -0.0107(11) 0.0069(8) 0.0002(10) C4 0.0166(10) 0.0425(15) 0.0322(12) -0.0202(11) 0.0109(9) -0.0092(10) C5 0.0189(10) 0.070(2) 0.0229(11) -0.0117(12) 0.0053(8) 0.0011(12) C6 0.0156(9) 0.0205(10) 0.0272(10) -0.0056(8) 0.0101(8) -0.0043(8) C7 0.0131(9) 0.0149(9) 0.0190(9) 0.0003(7) 0.0057(7) -0.0014(7) C8 0.0144(9) 0.0178(10) 0.0211(9) 0.0001(8) 0.0059(7) -0.0004(7) C9 0.0169(9) 0.0210(10) 0.0201(9) 0.0005(8) 0.0066(7) -0.0023(8) C10 0.0184(9) 0.0148(9) 0.0319(11) 0.0029(8) 0.0101(8) -0.0007(8) C11 0.0213(10) 0.0307(13) 0.0288(11) 0.0107(10) 0.0071(8) 0.0032(9) C12 0.0158(9) 0.0161(9) 0.0228(9) -0.0022(7) 0.0075(7) -0.0024(7) O9 0.0239(11) 0.0244(12) 0.0222(10) 0.000 0.0024(8) 0.000 O10 0.044(6) 0.025(5) 0.036(5) 0.000 0.010(5) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0057 '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 0.0389 0.0241 '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 _geom_angle_publ_flag C1 O1 C12 110.66(17) . . ? C2 O2 H2 112(2) . . ? C3 O3 C5 107.0(2) . . ? C3 O4 C4 102.1(2) . . ? C7 O5 C6 109.41(15) . . ? C9 O6 C11 106.67(17) . . ? C8 O7 H7 106(3) . . ? C9 O8 C10 101.79(16) . . ? O1 C1 H1 108.1 . . ? O1 C1 C2 108.25(18) . . ? O1 C1 C6 109.13(16) . . ? C2 C1 H1 108.1 . . ? C2 C1 C6 114.84(17) . . ? C6 C1 H1 108.1 . . ? O2 C2 C1 109.73(18) . . ? O2 C2 H2A 108.0 . . ? O2 C2 C3 110.91(18) . . ? C1 C2 H2A 108.0 . . ? C3 C2 C1 112.11(17) . . ? C3 C2 H2A 108.0 . . ? O3 C3 C2 109.5(2) . . ? O3 C3 H3 110.0 . . ? O4 C3 O3 106.9(2) . . ? O4 C3 C2 110.4(2) . . ? O4 C3 H3 110.0 . . ? C2 C3 H3 110.0 . . ? O4 C4 H4 111.2 . . ? O4 C4 C5 102.0(2) . . ? O4 C4 C6 106.25(18) . . ? C5 C4 H4 111.2 . . ? C5 C4 C6 114.6(2) . . ? C6 C4 H4 111.2 . . ? O3 C5 C4 103.8(2) . . ? O3 C5 H5A 111.0 . . ? O3 C5 H5B 111.0 . . ? C4 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? O5 C6 C1 110.24(17) . . ? O5 C6 C4 107.69(17) . . ? O5 C6 H6 108.4 . . ? C1 C6 H6 108.4 . . ? C4 C6 C1 113.72(19) . . ? C4 C6 H6 108.4 . . ? O5 C7 H7A 108.3 . . ? O5 C7 C8 110.12(16) . . ? O5 C7 C12 108.52(17) . . ? C8 C7 H7A 108.3 . . ? C12 C7 H7A 108.3 . . ? C12 C7 C8 113.16(17) . . ? O7 C8 C7 110.43(16) . . ? O7 C8 H8 109.4 . . ? O7 C8 C9 105.32(16) . . ? C7 C8 H8 109.4 . . ? C9 C8 C7 112.68(18) . . ? C9 C8 H8 109.4 . . ? O6 C9 O8 106.21(18) . . ? O6 C9 C8 109.94(18) . . ? O6 C9 H9 110.3 . . ? O8 C9 C8 109.71(16) . . ? O8 C9 H9 110.3 . . ? C8 C9 H9 110.3 . . ? O8 C10 H10 110.8 . . ? O8 C10 C11 101.89(17) . . ? O8 C10 C12 107.79(18) . . ? C11 C10 H10 110.8 . . ? C11 C10 C12 114.48(19) . . ? C12 C10 H10 110.8 . . ? O6 C11 C10 103.73(18) . . ? O6 C11 H11A 111.0 . . ? O6 C11 H11B 111.0 . . ? C10 C11 H11A 111.0 . . ? C10 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? O1 C12 C7 110.77(17) . . ? O1 C12 C10 106.27(18) . . ? O1 C12 H12 108.9 . . ? C7 C12 H12 108.9 . . ? C10 C12 C7 112.90(17) . . ? C10 C12 H12 108.9 . . ? H9A O9 H9A 95(6) . 2_556 ? H10A O10 H10A 153.0 . 2_657 ? H10A O10 H10B 104.5 2_657 2_657 ? H10A O10 H10B 104.5 . . ? H10A O10 H10B 60.8 . 2_657 ? H10B O10 H10A 60.8 . 2_657 ? H10B O10 H10B 118.8 . 2_657 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.426(3) . ? O1 C12 1.430(2) . ? O2 H2 0.850(2) . ? O2 C2 1.425(3) . ? O3 C3 1.413(4) . ? O3 C5 1.439(4) . ? O4 C3 1.412(4) . ? O4 C4 1.446(3) . ? O5 C6 1.433(2) . ? O5 C7 1.422(2) . ? O6 C9 1.420(2) . ? O6 C11 1.442(3) . ? O7 H7 0.850(2) . ? O7 C8 1.424(2) . ? O8 C9 1.420(3) . ? O8 C10 1.435(2) . ? C1 H1 1.0000 . ? C1 C2 1.549(3) . ? C1 C6 1.560(3) . ? C2 H2A 1.0000 . ? C2 C3 1.527(3) . ? C3 H3 1.0000 . ? C4 H4 1.0000 . ? C4 C5 1.515(5) . ? C4 C6 1.528(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6 1.0000 . ? C7 H7A 1.0000 . ? C7 C8 1.546(3) . ? C7 C12 1.544(3) . ? C8 H8 1.0000 . ? C8 C9 1.529(3) . ? C9 H9 1.0000 . ? C10 H10 1.0000 . ? C10 C11 1.522(3) . ? C10 C12 1.523(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12 1.0000 . ? O9 H9A 0.850(2) . ? O9 H9A 0.850(2) 2_556 ? O10 H10A 0.8700 . ? O10 H10A 0.8700 2_657 ? O10 H10B 0.8700 2_657 ? O10 H10B 0.8700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O2 H2 O9 0.850(2) 1.856(9) 2.689(3) 166(4) 3 yes O7 H7 O2 0.850(2) 1.909(7) 2.750(2) 170(3) 4_556 yes O10 H10A O3 0.87 2.26 2.707(10) 112.2 2_657 yes O10 H10B O3 0.87 1.96 2.707(10) 143.9 . yes O9 H9A O7 0.850(2) 1.957(9) 2.794(3) 168(4) . yes O9 H9A O8 0.850(2) 2.60(4) 3.0430(17) 114(3) . yes 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 135.07(19) . . . . ? O1 C1 C2 C3 -101.2(2) . . . . ? O1 C1 C6 O5 -23.1(2) . . . . ? O1 C1 C6 C4 97.9(2) . . . . ? O2 C2 C3 O3 -168.5(2) . . . . ? O2 C2 C3 O4 74.1(2) . . . . ? O4 C4 C5 O3 -28.7(3) . . . . ? O4 C4 C6 O5 174.4(2) . . . . ? O4 C4 C6 C1 51.9(3) . . . . ? O5 C7 C8 O7 149.10(17) . . . . ? O5 C7 C8 C9 -93.4(2) . . . . ? O5 C7 C12 O1 -27.0(2) . . . . ? O5 C7 C12 C10 92.1(2) . . . . ? O7 C8 C9 O6 -175.43(16) . . . . ? O7 C8 C9 O8 68.1(2) . . . . ? O8 C10 C11 O6 -28.9(2) . . . . ? O8 C10 C12 O1 177.45(17) . . . . ? O8 C10 C12 C7 55.8(2) . . . . ? C1 O1 C12 C7 -39.5(2) . . . . ? C1 O1 C12 C10 -162.52(17) . . . . ? C1 C2 C3 O3 68.4(3) . . . . ? C1 C2 C3 O4 -49.0(3) . . . . ? C2 C1 C6 O5 -144.86(19) . . . . ? C2 C1 C6 C4 -23.8(3) . . . . ? C3 O3 C5 C4 5.1(3) . . . . ? C3 O4 C4 C5 41.4(2) . . . . ? C3 O4 C4 C6 -79.0(3) . . . . ? C4 O4 C3 O3 -40.0(2) . . . . ? C4 O4 C3 C2 79.0(2) . . . . ? C5 O3 C3 O4 21.5(3) . . . . ? C5 O3 C3 C2 -98.1(3) . . . . ? C5 C4 C6 O5 62.6(3) . . . . ? C5 C4 C6 C1 -59.9(3) . . . . ? C6 O5 C7 C8 -165.60(18) . . . . ? C6 O5 C7 C12 70.0(2) . . . . ? C6 C1 C2 O2 -102.7(2) . . . . ? C6 C1 C2 C3 21.0(3) . . . . ? C6 C4 C5 O3 85.7(2) . . . . ? C7 O5 C6 C1 -43.0(2) . . . . ? C7 O5 C6 C4 -167.6(2) . . . . ? C7 C8 C9 O6 64.1(2) . . . . ? C7 C8 C9 O8 -52.3(2) . . . . ? C8 C7 C12 O1 -149.49(16) . . . . ? C8 C7 C12 C10 -30.4(2) . . . . ? C9 O6 C11 C10 3.8(2) . . . . ? C9 O8 C10 C11 42.8(2) . . . . ? C9 O8 C10 C12 -78.1(2) . . . . ? C10 O8 C9 O6 -42.07(19) . . . . ? C10 O8 C9 C8 76.71(19) . . . . ? C11 O6 C9 O8 23.3(2) . . . . ? C11 O6 C9 C8 -95.3(2) . . . . ? C11 C10 C12 O1 64.9(2) . . . . ? C11 C10 C12 C7 -56.8(3) . . . . ? C12 O1 C1 C2 -168.32(16) . . . . ? C12 O1 C1 C6 66.1(2) . . . . ? C12 C7 C8 O7 -89.3(2) . . . . ? C12 C7 C8 C9 28.2(2) . . . . ? C12 C10 C11 O6 87.1(2) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 1.0(2) 2 -0.0(2)