#------------------------------------------------------------------------------ #$Date: 2023-12-14 02:39:30 +0200 (Thu, 14 Dec 2023) $ #$Revision: 288295 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247858.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_7247858 loop_ _publ_author_name 'Chen, Shipeng' 'Liu, Luke' 'Wang, Jinpin' 'Li, Feng' 'song, zebin' 'Wang, Xiaoji' 'Ke, Yubin' 'Lin, Hua' 'Fan, Yange' 'li, zheng' 'Hou, Yimin' 'Xue, Bao Yu' _publ_section_title ; Preparation, Characterization and Application of D-Gluconic Acetal-Based Self-Healing Supramolecular Ionogels for Desulphurization of Fuels ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC04359B _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C14 H17 N O9, H2 O' _chemical_formula_sum 'C14 H19 N O10' _chemical_formula_weight 361.30 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-11-22 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2021-12-20 deposited with the CCDC. 2023-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.61033(12) _cell_length_b 11.7809(4) _cell_length_c 29.1594(12) _cell_measurement_reflns_used 4032 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 73.5020 _cell_measurement_theta_min 2.9980 _cell_volume 1583.76(9) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -113.00 -13.00 1.00 2.00 -- -41.11 -57.00 0.00 100 2 \w 23.00 97.00 1.00 2.00 -- 41.11-125.00 60.00 74 3 \w 1.00 82.00 1.00 2.00 -- 41.11 -99.00 -60.00 81 4 \w 23.00 97.00 1.00 2.00 -- 41.11-125.00 -60.00 74 5 \w 94.00 178.00 1.00 5.00 -- 107.58 125.00-120.00 84 6 \w 31.00 136.00 1.00 5.00 -- 107.58 -30.00 90.00 105 7 \w 34.00 122.00 1.00 5.00 -- 107.58-125.00 120.00 88 8 \w 94.00 178.00 1.00 5.00 -- 107.58 125.00-150.00 84 9 \w 26.00 151.00 1.00 5.00 -- 107.58 -15.00-180.00 125 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1126874000 _diffrn_orient_matrix_UB_12 -0.0966660000 _diffrn_orient_matrix_UB_13 0.0308104000 _diffrn_orient_matrix_UB_21 0.0944764000 _diffrn_orient_matrix_UB_22 -0.0876888000 _diffrn_orient_matrix_UB_23 -0.0362644000 _diffrn_orient_matrix_UB_31 0.2999493000 _diffrn_orient_matrix_UB_32 -0.0086718000 _diffrn_orient_matrix_UB_33 0.0229597000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_unetI/netI 0.0549 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 7571 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.649 _diffrn_reflns_theta_min 3.031 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.133 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.42635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.515 _exptl_crystal_description needle _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.290 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details ; Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.07(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3130 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0435 _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^)+(0.0522P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1022 _refine_ls_wR_factor_ref 0.1056 _reflns_Friedel_coverage 0.654 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.958 _reflns_number_gt 2904 _reflns_number_total 3130 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc04359b3.cif _cod_data_source_block z _cod_database_code 7247858 _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 0.915 _shelx_estimated_absorpt_t_min 0.858 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2.a Free rotating group: O10(H10A,H10B) 2.b Ternary CH refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C11(H11) 2.c Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 2.d Aromatic/amide H refined with riding coordinates: C6(H6A), C7(H7A), C9(H9), C10(H10) 2.e Idealised Me refined as rotating group: C14(H14A,H14B,H14C) 2.f Idealised tetrahedral OH refined as rotating group: O5(H5), O6(H6) ; _shelx_res_file ; TITL z_a.res in P2(1)2(1)2(1) z.res created by SHELXL-2018/3 at 14:17:53 on 22-Nov-2021 REM Old TITL z in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.105, Rweak 0.041, Alpha 0.002 REM 0.584 for 21 systematic absences, Orientation as input REM Flack x = 0.270 ( 0.445 ) from 928 Parsons' quotients REM Formula found by SHELXT: C15 N O9 CELL 1.54184 4.610327 11.780884 29.159432 90 90 90 ZERR 4 0.000115 0.00037 0.001249 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 56 76 4 40 EQIV $1 1+X,+Y,+Z EQIV $2 -0.5+X,1.5-Y,1-Z EQIV $3 -1+X,+Y,+Z L.S. 20 PLAN 5 SIZE 0.08 0.12 0.14 CONF HTAB O5 O6_$1 HTAB O6 O5_$2 HTAB O7 O10 HTAB O10 O2_$2 HTAB O10 O7_$3 BOND list 4 fmap 2 acta MORE -1 BOND $H OMIT -5 1 15 OMIT -5 1 14 OMIT -5 2 15 OMIT -5 3 15 OMIT -5 2 14 OMIT -5 3 14 OMIT -5 4 14 OMIT -5 2 13 OMIT -5 2 16 REM REM REM WGHT 0.052200 FVAR 6.77869 O1 4 0.407036 0.852555 0.653606 11.00000 0.02289 0.01734 = 0.03702 -0.00227 -0.00214 -0.00259 O2 4 0.048596 0.907077 0.606650 11.00000 0.04106 0.01801 = 0.03852 0.00259 -0.00395 0.00996 O3 4 0.313951 0.638357 0.640915 11.00000 0.01206 0.01346 = 0.02390 0.00099 -0.00292 0.00184 O4 4 0.207749 0.493522 0.589403 11.00000 0.00937 0.01560 = 0.02086 0.00145 -0.00338 0.00169 O5 4 0.288446 0.717161 0.544286 11.00000 0.01239 0.01458 = 0.02625 0.00308 0.00529 0.00132 AFIX 147 H5 2 0.391473 0.661856 0.539167 11.00000 -1.50000 AFIX 0 O6 4 -0.301598 0.571802 0.499300 11.00000 0.00991 0.02071 = 0.02592 0.00561 -0.00384 0.00148 AFIX 147 H6 2 -0.247136 0.621347 0.481524 11.00000 -1.50000 AFIX 0 O7 4 -0.077991 0.343729 0.471104 11.00000 0.01542 0.02519 = 0.03173 -0.00680 -0.00397 0.00337 H7 2 -0.243580 0.349324 0.456991 11.00000 0.04119 O8 4 1.116165 0.272473 0.769629 11.00000 0.03587 0.03939 = 0.03684 0.00412 -0.02008 0.00804 O9 4 1.030409 0.137595 0.721488 11.00000 0.07058 0.02741 = 0.04937 -0.00373 -0.02254 0.02648 N1 3 0.997830 0.235022 0.735288 11.00000 0.01856 0.02639 = 0.02734 0.00504 -0.00352 0.00547 C1 1 0.097544 0.710970 0.621777 11.00000 0.01016 0.01790 = 0.02187 0.00255 0.00083 0.00369 AFIX 13 H1 2 -0.084175 0.699369 0.638572 11.00000 -1.20000 AFIX 0 C2 1 0.045696 0.683343 0.571243 11.00000 0.00730 0.01514 = 0.02180 0.00464 0.00195 0.00182 AFIX 13 H2 2 -0.124680 0.725873 0.560820 11.00000 -1.20000 AFIX 0 C3 1 -0.021355 0.556359 0.567513 11.00000 0.00472 0.01839 = 0.02289 0.00463 -0.00003 0.00043 AFIX 13 H3 2 -0.202794 0.541162 0.583910 11.00000 -1.20000 AFIX 0 C4 1 0.223957 0.524291 0.636159 11.00000 0.00858 0.01620 = 0.02195 0.00091 0.00055 -0.00157 AFIX 13 H4 2 0.031878 0.515463 0.650106 11.00000 -1.20000 AFIX 0 C5 1 0.435701 0.448847 0.660826 11.00000 0.00685 0.01662 = 0.01952 0.00347 0.00099 -0.00049 C6 1 0.515369 0.343810 0.642983 11.00000 0.02307 0.01898 = 0.02264 -0.00092 -0.00819 0.00053 AFIX 43 H6A 2 0.442217 0.320622 0.614775 11.00000 -1.20000 AFIX 0 C7 1 0.702764 0.273541 0.666910 11.00000 0.02643 0.01627 = 0.02612 -0.00160 -0.00448 0.00540 AFIX 43 H7A 2 0.758328 0.203618 0.654995 11.00000 -1.20000 AFIX 0 C8 1 0.804958 0.310023 0.708925 11.00000 0.01259 0.02011 = 0.02147 0.00452 -0.00219 0.00133 C9 1 0.732844 0.413939 0.727300 11.00000 0.01475 0.02472 = 0.01684 -0.00186 -0.00354 0.00125 AFIX 43 H9 2 0.807277 0.436677 0.755483 11.00000 -1.20000 AFIX 0 C10 1 0.547122 0.483842 0.702908 11.00000 0.01648 0.01833 = 0.02270 -0.00226 0.00070 0.00266 AFIX 43 H10 2 0.496550 0.554489 0.714681 11.00000 -1.20000 AFIX 0 C11 1 -0.054190 0.514706 0.518214 11.00000 0.00678 0.01745 = 0.02308 0.00143 -0.00285 0.00105 AFIX 13 H11 2 0.119739 0.534004 0.500536 11.00000 -1.20000 AFIX 0 C12 1 -0.106255 0.387288 0.516384 11.00000 0.01939 0.01675 = 0.02663 0.00285 -0.00575 -0.00034 AFIX 23 H12A 2 0.031847 0.349432 0.536282 11.00000 -1.20000 H12B 2 -0.299549 0.370921 0.527736 11.00000 -1.20000 AFIX 0 C13 1 0.185573 0.834132 0.626409 11.00000 0.01912 0.01856 = 0.02229 -0.00046 0.00492 0.00253 C14 1 0.488019 0.971189 0.658609 11.00000 0.03039 0.01942 = 0.05125 -0.00818 0.00935 -0.00761 AFIX 137 H14A 2 0.549301 1.000568 0.629469 11.00000 -1.50000 H14B 2 0.644061 0.977542 0.680256 11.00000 -1.50000 H14C 2 0.324164 1.013788 0.669404 11.00000 -1.50000 AFIX 6 O10 4 -0.570874 0.370484 0.423064 11.00000 0.02251 0.02037 = 0.03217 0.00172 -0.00402 -0.00450 H10A 2 -0.720703 0.364329 0.439887 11.00000 -1.50000 H10B 2 -0.543173 0.439925 0.416535 11.00000 -1.50000 AFIX 0 HKLF 4 REM z_a.res in P2(1)2(1)2(1) REM wR2 = 0.1056, GooF = S = 1.105, Restrained GooF = 1.105 for all data REM R1 = 0.0435 for 2904 Fo > 4sig(Fo) and 0.0515 for all 3130 data REM 236 parameters refined using 0 restraints END WGHT 0.0522 0.0000 REM Highest difference peak 0.290, deepest hole -0.244, 1-sigma level 0.052 Q1 1 0.4014 0.4861 0.5876 11.00000 0.05 0.29 Q2 1 -0.2054 0.5511 0.5699 11.00000 0.05 0.24 Q3 1 0.6175 0.2936 0.7073 11.00000 0.05 0.24 Q4 1 0.0071 0.4921 0.5892 11.00000 0.05 0.23 Q5 1 0.5090 0.6393 0.6412 11.00000 0.05 0.23 ; _shelx_res_checksum 90201 _olex2_date_sample_data_collection 2021-11-20 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.707 _oxdiff_exptl_absorpt_empirical_full_min 0.208 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' '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 0.4070(4) 0.85256(18) 0.65361(8) 0.0257(5) Uani 1 1 d . . . . . O2 O 0.0486(6) 0.90708(18) 0.60665(8) 0.0325(5) Uani 1 1 d . . . . . O3 O 0.3140(4) 0.63836(16) 0.64091(7) 0.0165(4) Uani 1 1 d . . . . . O4 O 0.2077(4) 0.49352(15) 0.58940(6) 0.0153(4) Uani 1 1 d . . . . . O5 O 0.2884(4) 0.71716(16) 0.54429(7) 0.0177(4) Uani 1 1 d . . . . . H5 H 0.391473 0.661856 0.539167 0.027 Uiso 1 1 calc R U . . . O6 O -0.3016(4) 0.57180(16) 0.49930(7) 0.0188(4) Uani 1 1 d . . . . . H6 H -0.247136 0.621347 0.481524 0.028 Uiso 1 1 calc R U . . . O7 O -0.0780(4) 0.34373(18) 0.47110(8) 0.0241(5) Uani 1 1 d . . . . . H7 H -0.244(11) 0.349(4) 0.4570(13) 0.041(12) Uiso 1 1 d . . . . . O8 O 1.1162(5) 0.2725(2) 0.76963(9) 0.0374(6) Uani 1 1 d . . . . . O9 O 1.0304(7) 0.1376(2) 0.72149(9) 0.0491(8) Uani 1 1 d . . . . . N1 N 0.9978(5) 0.2350(2) 0.73529(9) 0.0241(5) Uani 1 1 d . . . . . C1 C 0.0975(5) 0.7110(2) 0.62178(10) 0.0166(5) Uani 1 1 d . . . . . H1 H -0.084175 0.699369 0.638572 0.020 Uiso 1 1 calc R U . . . C2 C 0.0457(5) 0.6833(2) 0.57124(9) 0.0147(5) Uani 1 1 d . . . . . H2 H -0.124680 0.725873 0.560820 0.018 Uiso 1 1 calc R U . . . C3 C -0.0214(5) 0.5564(2) 0.56751(9) 0.0153(5) Uani 1 1 d . . . . . H3 H -0.202794 0.541162 0.583910 0.018 Uiso 1 1 calc R U . . . C4 C 0.2240(5) 0.5243(2) 0.63616(9) 0.0156(5) Uani 1 1 d . . . . . H4 H 0.031878 0.515463 0.650106 0.019 Uiso 1 1 calc R U . . . C5 C 0.4357(5) 0.4488(2) 0.66083(9) 0.0143(5) Uani 1 1 d . . . . . C6 C 0.5154(6) 0.3438(2) 0.64298(10) 0.0216(6) Uani 1 1 d . . . . . H6A H 0.442217 0.320622 0.614775 0.026 Uiso 1 1 calc R U . . . C7 C 0.7028(7) 0.2735(2) 0.66691(11) 0.0229(6) Uani 1 1 d . . . . . H7A H 0.758328 0.203618 0.654995 0.028 Uiso 1 1 calc R U . . . C8 C 0.8050(6) 0.3100(2) 0.70893(10) 0.0181(5) Uani 1 1 d . . . . . C9 C 0.7328(6) 0.4139(2) 0.72730(10) 0.0188(6) Uani 1 1 d . . . . . H9 H 0.807277 0.436677 0.755483 0.023 Uiso 1 1 calc R U . . . C10 C 0.5471(6) 0.4838(2) 0.70291(10) 0.0192(5) Uani 1 1 d . . . . . H10 H 0.496550 0.554489 0.714681 0.023 Uiso 1 1 calc R U . . . C11 C -0.0542(5) 0.5147(2) 0.51821(9) 0.0158(5) Uani 1 1 d . . . . . H11 H 0.119739 0.534004 0.500536 0.019 Uiso 1 1 calc R U . . . C12 C -0.1063(6) 0.3873(2) 0.51638(10) 0.0209(6) Uani 1 1 d . . . . . H12A H 0.031847 0.349432 0.536282 0.025 Uiso 1 1 calc R U . . . H12B H -0.299549 0.370921 0.527736 0.025 Uiso 1 1 calc R U . . . C13 C 0.1856(6) 0.8341(2) 0.62641(10) 0.0200(6) Uani 1 1 d . . . . . C14 C 0.4880(7) 0.9712(3) 0.65861(13) 0.0337(8) Uani 1 1 d . . . . . H14A H 0.549301 1.000568 0.629469 0.051 Uiso 1 1 calc R U . . . H14B H 0.644061 0.977542 0.680256 0.051 Uiso 1 1 calc R U . . . H14C H 0.324164 1.013788 0.669404 0.051 Uiso 1 1 calc R U . . . O10 O -0.5709(4) 0.37048(18) 0.42306(8) 0.0250(5) Uani 1 1 d G . . . . H10A H -0.720703 0.364329 0.439887 0.038 Uiso 1 1 d G U . . . H10B H -0.543173 0.439925 0.416535 0.038 Uiso 1 1 d G 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 O1 0.0229(10) 0.0173(10) 0.0370(12) -0.0023(9) -0.0021(9) -0.0026(8) O2 0.0411(12) 0.0180(10) 0.0385(13) 0.0026(10) -0.0039(12) 0.0100(9) O3 0.0121(8) 0.0135(9) 0.0239(10) 0.0010(8) -0.0029(8) 0.0018(7) O4 0.0094(8) 0.0156(9) 0.0209(9) 0.0015(8) -0.0034(7) 0.0017(7) O5 0.0124(8) 0.0146(9) 0.0262(10) 0.0031(8) 0.0053(8) 0.0013(7) O6 0.0099(8) 0.0207(10) 0.0259(10) 0.0056(8) -0.0038(9) 0.0015(7) O7 0.0154(9) 0.0252(10) 0.0317(11) -0.0068(9) -0.0040(9) 0.0034(8) O8 0.0359(13) 0.0394(14) 0.0368(14) 0.0041(11) -0.0201(11) 0.0080(10) O9 0.0706(19) 0.0274(12) 0.0494(15) -0.0037(12) -0.0225(15) 0.0265(13) N1 0.0186(11) 0.0264(13) 0.0273(13) 0.0050(11) -0.0035(12) 0.0055(10) C1 0.0102(10) 0.0179(13) 0.0219(13) 0.0026(10) 0.0008(10) 0.0037(10) C2 0.0073(11) 0.0151(12) 0.0218(13) 0.0046(10) 0.0019(11) 0.0018(9) C3 0.0047(10) 0.0184(12) 0.0229(13) 0.0046(11) 0.0000(11) 0.0004(9) C4 0.0086(11) 0.0162(13) 0.0219(13) 0.0009(11) 0.0006(11) -0.0016(9) C5 0.0069(10) 0.0166(12) 0.0195(12) 0.0035(10) 0.0010(11) -0.0005(10) C6 0.0231(13) 0.0190(13) 0.0226(14) -0.0009(11) -0.0082(12) 0.0005(11) C7 0.0264(13) 0.0163(13) 0.0261(15) -0.0016(12) -0.0045(13) 0.0054(12) C8 0.0126(11) 0.0201(13) 0.0215(14) 0.0045(11) -0.0022(11) 0.0013(10) C9 0.0148(12) 0.0247(14) 0.0168(13) -0.0019(11) -0.0035(11) 0.0012(10) C10 0.0165(12) 0.0183(13) 0.0227(13) -0.0023(11) 0.0007(12) 0.0027(10) C11 0.0068(10) 0.0175(12) 0.0231(13) 0.0014(10) -0.0029(10) 0.0011(9) C12 0.0194(13) 0.0167(13) 0.0266(15) 0.0028(11) -0.0058(12) -0.0003(10) C13 0.0191(12) 0.0186(14) 0.0223(14) -0.0005(11) 0.0049(12) 0.0025(11) C14 0.0304(16) 0.0194(15) 0.051(2) -0.0082(14) 0.0093(16) -0.0076(12) O10 0.0225(10) 0.0204(10) 0.0322(12) 0.0017(9) -0.0040(9) -0.0045(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C13 O1 C14 114.8(2) . . ? C4 O3 C1 109.0(2) . . ? C4 O4 C3 109.57(19) . . ? C2 O5 H5 109.5 . . ? C11 O6 H6 109.5 . . ? C12 O7 H7 109(3) . . ? O8 N1 O9 123.5(3) . . ? O8 N1 C8 118.8(3) . . ? O9 N1 C8 117.7(3) . . ? O3 C1 H1 108.6 . . ? O3 C1 C2 111.0(2) . . ? O3 C1 C13 110.6(2) . . ? C2 C1 H1 108.6 . . ? C13 C1 H1 108.6 . . ? C13 C1 C2 109.4(2) . . ? O5 C2 C1 110.5(2) . . ? O5 C2 H2 108.4 . . ? O5 C2 C3 113.1(2) . . ? C1 C2 H2 108.4 . . ? C1 C2 C3 107.9(2) . . ? C3 C2 H2 108.4 . . ? O4 C3 C2 108.8(2) . . ? O4 C3 H3 108.4 . . ? O4 C3 C11 109.0(2) . . ? C2 C3 H3 108.4 . . ? C11 C3 C2 113.6(2) . . ? C11 C3 H3 108.4 . . ? O3 C4 H4 109.0 . . ? O3 C4 C5 108.9(2) . . ? O4 C4 O3 110.7(2) . . ? O4 C4 H4 109.0 . . ? O4 C4 C5 110.1(2) . . ? C5 C4 H4 109.0 . . ? C6 C5 C4 121.2(2) . . ? C6 C5 C10 119.7(2) . . ? C10 C5 C4 119.1(2) . . ? C5 C6 H6A 119.7 . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6A 119.7 . . ? C6 C7 H7A 120.9 . . ? C8 C7 C6 118.3(3) . . ? C8 C7 H7A 120.9 . . ? C7 C8 N1 118.9(3) . . ? C9 C8 N1 118.5(3) . . ? C9 C8 C7 122.6(3) . . ? C8 C9 H9 120.7 . . ? C8 C9 C10 118.6(3) . . ? C10 C9 H9 120.7 . . ? C5 C10 H10 119.8 . . ? C9 C10 C5 120.3(3) . . ? C9 C10 H10 119.8 . . ? O6 C11 C3 106.9(2) . . ? O6 C11 H11 109.9 . . ? O6 C11 C12 108.9(2) . . ? C3 C11 H11 109.9 . . ? C12 C11 C3 111.5(2) . . ? C12 C11 H11 109.9 . . ? O7 C12 C11 112.0(2) . . ? O7 C12 H12A 109.2 . . ? O7 C12 H12B 109.2 . . ? C11 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O1 C13 C1 114.9(2) . . ? O2 C13 O1 125.2(3) . . ? O2 C13 C1 119.9(3) . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H10A O10 H10B 109.5 . . ? 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 C13 1.311(4) . ? O1 C14 1.454(4) . ? O2 C13 1.212(4) . ? O3 C1 1.428(3) . ? O3 C4 1.413(3) . ? O4 C3 1.439(3) . ? O4 C4 1.413(3) . ? O5 H5 0.8200 . ? O5 C2 1.424(3) . ? O6 H6 0.8200 . ? O6 C11 1.434(3) . ? O7 H7 0.87(5) . ? O7 C12 1.423(4) . ? O8 N1 1.223(4) . ? O9 N1 1.226(4) . ? N1 C8 1.470(3) . ? C1 H1 0.9800 . ? C1 C2 1.528(4) . ? C1 C13 1.513(4) . ? C2 H2 0.9800 . ? C2 C3 1.531(4) . ? C3 H3 0.9800 . ? C3 C11 1.526(4) . ? C4 H4 0.9800 . ? C4 C5 1.503(4) . ? C5 C6 1.392(4) . ? C5 C10 1.393(4) . ? C6 H6A 0.9300 . ? C6 C7 1.385(4) . ? C7 H7A 0.9300 . ? C7 C8 1.381(4) . ? C8 C9 1.377(4) . ? C9 H9 0.9300 . ? C9 C10 1.385(4) . ? C10 H10 0.9300 . ? C11 H11 0.9800 . ? C11 C12 1.521(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O10 H10A 0.8503 . ? O10 H10B 0.8496 . ? 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 O5 H5 O6 0.82 2.12 2.868(3) 152.3 1_655 yes O6 H6 O5 0.82 2.05 2.823(3) 156.4 4_466 yes O7 H7 O10 0.87(5) 1.82(5) 2.688(3) 174(4) . yes O10 H10A O7 0.85 1.90 2.744(3) 173.1 1_455 yes O10 H10B O2 0.85 1.97 2.814(3) 171.8 4_466 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 O3 C1 C2 O5 -70.6(3) . . . . ? O3 C1 C2 C3 53.6(3) . . . . ? O3 C1 C13 O1 -12.0(3) . . . . ? O3 C1 C13 O2 169.9(3) . . . . ? O3 C4 C5 C6 -141.9(2) . . . . ? O3 C4 C5 C10 39.9(3) . . . . ? O4 C3 C11 O6 174.63(19) . . . . ? O4 C3 C11 C12 55.8(3) . . . . ? O4 C4 C5 C6 -20.2(3) . . . . ? O4 C4 C5 C10 161.6(2) . . . . ? O5 C2 C3 O4 68.8(3) . . . . ? O5 C2 C3 C11 -52.8(3) . . . . ? O6 C11 C12 O7 74.4(3) . . . . ? O8 N1 C8 C7 171.2(3) . . . . ? O8 N1 C8 C9 -9.0(4) . . . . ? O9 N1 C8 C7 -9.0(4) . . . . ? O9 N1 C8 C9 170.8(3) . . . . ? N1 C8 C9 C10 -178.9(2) . . . . ? C1 O3 C4 O4 64.8(2) . . . . ? C1 O3 C4 C5 -173.9(2) . . . . ? C1 C2 C3 O4 -53.7(3) . . . . ? C1 C2 C3 C11 -175.4(2) . . . . ? C2 C1 C13 O1 -134.6(2) . . . . ? C2 C1 C13 O2 47.3(3) . . . . ? C2 C3 C11 O6 -63.8(3) . . . . ? C2 C3 C11 C12 177.3(2) . . . . ? C3 O4 C4 O3 -66.7(2) . . . . ? C3 O4 C4 C5 172.74(19) . . . . ? C3 C11 C12 O7 -167.9(2) . . . . ? C4 O3 C1 C2 -58.6(3) . . . . ? C4 O3 C1 C13 179.8(2) . . . . ? C4 O4 C3 C2 60.6(3) . . . . ? C4 O4 C3 C11 -175.00(19) . . . . ? C4 C5 C6 C7 -177.7(3) . . . . ? C4 C5 C10 C9 177.2(2) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C5 C10 C9 -1.0(4) . . . . ? C6 C7 C8 N1 178.4(3) . . . . ? C6 C7 C8 C9 -1.4(5) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C8 C9 C10 C5 0.3(4) . . . . ? C10 C5 C6 C7 0.5(4) . . . . ? C13 C1 C2 O5 51.8(3) . . . . ? C13 C1 C2 C3 176.0(2) . . . . ? C14 O1 C13 O2 -1.0(4) . . . . ? C14 O1 C13 C1 -179.0(2) . . . . ?