#------------------------------------------------------------------------------ #$Date: 2022-04-03 21:11:37 +0100 (Sun, 03 Apr 2022) $ #$Revision: 274259 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519402.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_4519402 loop_ _publ_author_name 'Zhang, Tingting' 'Yang, Shiying' 'Zhang, Baoxi' 'Yang, Dezhi' 'Lu, Yang' 'Du, Guanhua' _publ_section_title ; Insights Into the Properties of Amygdalin Solvatomorphs: X-ray Structures, Intermolecular Interactions, and Transformations. ; _journal_issue 10 _journal_name_full 'ACS omega' _journal_page_first 8906 _journal_page_last 8918 _journal_paper_doi 10.1021/acsomega.1c07314 _journal_volume 7 _journal_year 2022 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H27 N O11, C6 H14 O, 2(H2 O)' _chemical_formula_sum 'C26 H45 N O14' _chemical_formula_weight 595.63 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2021-11-28 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133) ; _cell_angle_alpha 90.00 _cell_angle_beta 100.2992(17) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.41164(19) _cell_length_b 7.95651(14) _cell_length_c 20.6510(4) _cell_measurement_reflns_used 15207 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.1620 _cell_measurement_theta_min 4.3510 _cell_volume 1521.51(5) _computing_cell_refinement 'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)' _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 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _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 -71.00 46.00 1.00 5.00 -- -44.00 70.00 225.00 117 2 \w -71.00 46.00 1.00 5.00 -- -44.00 70.00 90.00 117 3 \w -71.00 46.00 1.00 5.00 -- -44.00 70.00 135.00 117 4 \w -71.00 2.00 1.00 5.00 -- -44.00 70.00 325.00 73 5 \w -71.00 -2.00 1.00 5.00 -- -44.00 70.00 0.00 69 6 \w -134.00 -87.00 1.00 5.00 -- -44.00 0.00 180.00 47 7 \w -24.00 6.00 1.00 5.00 -- -44.00 0.00 225.00 30 8 \w -71.00 -43.00 1.00 5.00 -- -44.00 70.00 270.00 28 9 \w -127.00 -10.00 1.00 5.00 -- -100.00 70.00 0.00 117 10 \w -127.00 -10.00 1.00 5.00 -- -100.00 70.00 325.00 117 11 \w -127.00 -10.00 1.00 5.00 -- -100.00 70.00 90.00 117 12 \w -127.00 -10.00 1.00 5.00 -- -100.00 70.00 180.00 117 13 \w -127.00 -13.00 1.00 5.00 -- -100.00 70.00 225.00 114 14 \w -119.00 -10.00 1.00 5.00 -- -100.00 45.00 225.00 109 15 \w -119.00 -10.00 1.00 5.00 -- -100.00 45.00 135.00 109 16 \w -127.00 -18.00 1.00 5.00 -- -100.00 70.00 135.00 109 17 \w -119.00 -10.00 1.00 5.00 -- -100.00 45.00 0.00 109 18 \w -119.00 -10.00 1.00 5.00 -- -100.00 45.00 325.00 109 19 \w -117.00 -10.00 1.00 5.00 -- -100.00 30.00 90.00 107 20 \w -117.00 -10.00 1.00 5.00 -- -100.00 30.00 325.00 107 21 \w -119.00 -25.00 1.00 5.00 -- -100.00 45.00 90.00 94 22 \w -145.00 -55.00 1.00 5.00 -- -100.00 0.00 90.00 90 23 \w -145.00 -55.00 1.00 5.00 -- -100.00 0.00 0.00 90 24 \w -127.00 -70.00 1.00 5.00 -- -100.00 70.00 270.00 57 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0384581000 _diffrn_orient_matrix_UB_12 0.0275973000 _diffrn_orient_matrix_UB_13 -0.0749361000 _diffrn_orient_matrix_UB_21 0.0127488000 _diffrn_orient_matrix_UB_22 -0.1904410000 _diffrn_orient_matrix_UB_23 -0.0112050000 _diffrn_orient_matrix_UB_31 -0.1613197000 _diffrn_orient_matrix_UB_32 -0.0216828000 _diffrn_orient_matrix_UB_33 0.0030019000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_unetI/netI 0.0465 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 24749 _diffrn_reflns_theta_full 72.28 _diffrn_reflns_theta_max 72.28 _diffrn_reflns_theta_min 4.35 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.893 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 640 _refine_diff_density_max 0.221 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.21(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 524 _refine_ls_number_reflns 5725 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.131 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0541 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0971P)^2^+0.1374P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1541 _refine_ls_wR_factor_ref 0.1574 _reflns_number_gt 5437 _reflns_number_total 5725 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ao1c07314_si_004.cif _cod_data_source_block 6354-20210918 _cod_database_code 4519402 _reflns_odcompleteness_completeness 97.59 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 72.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances O1W-H1WB 1 with sigma of 0.02 O1W-H1WA 1 with sigma of 0.02 H1H-H11 2.3 with sigma of 0.02 3. Others Sof(H1HA)=Sof(H1HB)=Sof(H5HA)=Sof(H5HB)=Sof(C4HA)=Sof(H4HA)=Sof(H4HB)= Sof(C3HA)=Sof(H3HA)=Sof(H3HB)=Sof(C2HA)=Sof(H2HA)=Sof(H2HB)=1-FVAR(1) Sof(H1HC)=Sof(H1HD)=Sof(H5HC)=Sof(H5HD)=Sof(C4HB)=Sof(H4HC)=Sof(H4HD)= Sof(C3HB)=Sof(H3HC)=Sof(H3HD)=Sof(C2HB)=Sof(H2HC)=Sof(H2HD)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C1H(H1HA,H1HB), C1H(H1HC,H1HD), C5H(H5HA,H5HB), C5H(H5HC,H5HD), C4HA(H4HA, H4HB), C3HA(H3HA,H3HB), C2HA(H2HA,H2HB), C4HB(H4HC,H4HD), C3HB(H3HC,H3HD), C2HB(H2HC,H2HD) 4.b Idealised Me refined as rotating group: C6H(H6HA,H6HB,H6HC) 4.c Idealised tetrahedral OH refined as rotating group: O1H(H1H) ; _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 8.431 _oxdiff_exptl_absorpt_empirical_full_min 0.397 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn O1 O 0.3825(2) -0.2373(2) 0.70344(8) 0.0446(4) Uani 1 d . . . O9 O 1.1646(2) 0.3458(2) 0.67660(9) 0.0447(4) Uani 1 d . . . H9 H 1.191(5) 0.407(7) 0.649(2) 0.075(13) Uiso 1 d . . . O7 O 1.05295(18) -0.1288(2) 0.53132(9) 0.0406(4) Uani 1 d . . . H7 H 0.983(5) -0.167(6) 0.502(2) 0.065(10) Uiso 1 d . . . O2 O 0.2121(2) -0.3861(3) 0.59192(10) 0.0448(4) Uani 1 d . . . H2 H 0.150(5) -0.329(6) 0.571(2) 0.070(12) Uiso 1 d . . . O11 O 0.8266(3) 0.3075(3) 0.72133(11) 0.0623(6) Uani 1 d . . . H11 H 0.781(5) 0.358(8) 0.750(3) 0.103(16) Uiso 1 d . . D O3 O 0.3550(2) -0.3320(2) 0.47949(9) 0.0431(4) Uani 1 d . . . H3 H 0.394(4) -0.379(6) 0.450(2) 0.069(11) Uiso 1 d . . . O8 O 1.15830(19) 0.2075(2) 0.55000(8) 0.0389(4) Uani 1 d . . . H8 H 1.211(4) 0.137(5) 0.5309(17) 0.049(8) Uiso 1 d . . . O4 O 0.6505(2) -0.4751(3) 0.50756(9) 0.0422(4) Uani 1 d . . . H4 H 0.645(5) -0.562(8) 0.519(2) 0.079(15) Uiso 1 d . . . O10 O 0.90863(18) 0.0018(2) 0.67644(8) 0.0399(4) Uani 1 d . . . O5 O 0.58618(18) -0.2983(2) 0.66357(8) 0.0380(4) Uani 1 d . . . O6 O 0.83206(18) -0.2054(2) 0.60410(9) 0.0406(4) Uani 1 d . . . N1 N 0.6591(4) -0.1001(8) 0.8206(2) 0.1044(14) Uani 1 d . . . C3 C 0.3004(3) -0.2286(4) 0.80564(12) 0.0482(6) Uani 1 d . . . C16 C 0.9989(2) -0.0159(3) 0.57396(11) 0.0329(4) Uani 1 d . . . H16 H 0.912(3) 0.040(4) 0.5510(13) 0.032(6) Uiso 1 d . . . C8 C 0.3003(4) -0.0981(5) 0.84935(17) 0.0637(8) Uani 1 d . . . H8A H 0.386(5) -0.042(7) 0.864(2) 0.081(13) Uiso 1 d . . . C13 C 0.6563(3) -0.4053(3) 0.62301(12) 0.0354(5) Uani 1 d . . . H13 H 0.646(4) -0.527(6) 0.6342(19) 0.062(10) Uiso 1 d . . . C17 C 1.1165(2) 0.1096(3) 0.60090(11) 0.0317(4) Uani 1 d . . . H17 H 1.205(3) 0.047(3) 0.6263(13) 0.027(6) Uiso 1 d . . . C2 C 0.4258(3) -0.2696(4) 0.77211(13) 0.0496(6) Uani 1 d . . . H2A H 0.451(3) -0.385(5) 0.7793(16) 0.046(8) Uiso 1 d . . . C20 C 0.9514(3) 0.2214(4) 0.75367(13) 0.0462(6) Uani 1 d . . . H20A H 0.925(3) 0.144(4) 0.7861(16) 0.045(8) Uiso 1 d . . . H20B H 1.028(4) 0.299(5) 0.7776(19) 0.062(10) Uiso 1 d . . . C12 C 0.5858(2) -0.3758(3) 0.55181(11) 0.0333(5) Uani 1 d . . . H12 H 0.598(3) -0.267(4) 0.5404(14) 0.032(6) Uiso 1 d . . . C5 C 0.0553(4) -0.2913(7) 0.81581(19) 0.0737(10) Uani 1 d . . . H5 H -0.036(5) -0.356(6) 0.804(2) 0.073(12) Uiso 1 d . . . C14 C 0.8147(3) -0.3598(3) 0.63634(13) 0.0398(5) Uani 1 d . . . H14A H 0.873(3) -0.448(4) 0.6187(13) 0.030(6) Uiso 1 d . . . H14B H 0.850(3) -0.356(4) 0.6830(15) 0.034(7) Uiso 1 d . . . C4 C 0.1758(4) -0.3243(5) 0.78876(16) 0.0619(8) Uani 1 d . . . H4A H 0.180(5) -0.410(7) 0.761(2) 0.079(13) Uiso 1 d . . . C1 C 0.5573(4) -0.1728(6) 0.79871(16) 0.0680(9) Uani 1 d . . . C18 C 1.0596(2) 0.2259(3) 0.64882(11) 0.0337(5) Uani 1 d . . . H18 H 0.971(3) 0.283(4) 0.6217(13) 0.028(6) Uiso 1 d . . . C19 C 1.0167(2) 0.1209(3) 0.70425(11) 0.0376(5) Uani 1 d . . . H19 H 1.111(3) 0.064(4) 0.7284(13) 0.033(6) Uiso 1 d . . . C9 C 0.4398(3) -0.3457(3) 0.66170(12) 0.0375(5) Uani 1 d . . . H9A H 0.437(3) -0.454(4) 0.6771(13) 0.030(6) Uiso 1 d . . . C6 C 0.0563(5) -0.1618(6) 0.85962(18) 0.0760(11) Uani 1 d . . . H6 H -0.036(4) -0.146(6) 0.879(2) 0.074(11) Uiso 1 d . . . C10 C 0.3532(2) -0.3205(3) 0.59348(11) 0.0350(5) Uani 1 d . . . H10 H 0.352(3) -0.210(4) 0.5838(13) 0.029(6) Uiso 1 d . . . C11 C 0.4230(2) -0.4042(3) 0.54048(11) 0.0346(5) Uani 1 d . . . H11A H 0.406(3) -0.527(5) 0.5447(16) 0.049(8) Uiso 1 d . . . C7 C 0.1774(6) -0.0681(6) 0.8765(2) 0.0809(12) Uani 1 d . . . H7A H 0.186(6) 0.033(8) 0.903(3) 0.106(17) Uiso 1 d . . . C15 C 0.9522(2) -0.1102(3) 0.63074(11) 0.0341(5) Uani 1 d . . . H15 H 1.030(3) -0.180(4) 0.6531(13) 0.030(6) Uiso 1 d . . . O1H O 0.6479(3) 0.3949(4) 0.80924(14) 0.0790(8) Uani 1 d A . . H1H H 0.5791 0.3323 0.7973 0.119 Uiso 1 calc . . DGR C1H C 0.7060(6) 0.3631(11) 0.8756(2) 0.115(2) Uani 1 d . . . H1HA H 0.8022 0.4108 0.8861 0.138 Uiso 0.69(3) calc A 1 R H1HB H 0.7139 0.2427 0.8828 0.138 Uiso 0.69(3) calc A 1 R H1HC H 0.7593 0.2584 0.8770 0.138 Uiso 0.31(3) calc A 2 R H1HD H 0.7762 0.4508 0.8899 0.138 Uiso 0.31(3) calc A 2 R C5H C 0.2278(9) 0.3960(13) 0.9563(3) 0.139(3) Uani 1 d . . . H5HA H 0.2344 0.2763 0.9654 0.167 Uiso 0.69(3) calc A 1 R H5HB H 0.1794 0.4085 0.9110 0.167 Uiso 0.69(3) calc A 1 R H5HC H 0.2057 0.4586 0.9154 0.167 Uiso 0.31(3) calc A 2 R H5HD H 0.1903 0.2837 0.9461 0.167 Uiso 0.31(3) calc A 2 R C6H C 0.1346(10) 0.4663(19) 0.9970(4) 0.178(5) Uani 1 d A . . H6HA H 0.0406 0.4164 0.9859 0.268 Uiso 1 calc . . GR H6HB H 0.1271 0.5855 0.9899 0.268 Uiso 1 calc . . GR H6HC H 0.1737 0.4443 1.0424 0.268 Uiso 1 calc . . GR C4HA C 0.3702(17) 0.4562(17) 0.9600(5) 0.098(4) Uani 0.69(3) d A 1 . H4HA H 0.4187 0.4483 1.0055 0.117 Uiso 0.69(3) calc A 1 R H4HB H 0.3648 0.5744 0.9484 0.117 Uiso 0.69(3) calc A 1 R C3HA C 0.4655(18) 0.3678(15) 0.9168(5) 0.096(4) Uani 0.69(3) d A 1 . H3HA H 0.4748 0.2502 0.9294 0.115 Uiso 0.69(3) calc A 1 R H3HB H 0.4167 0.3726 0.8713 0.115 Uiso 0.69(3) calc A 1 R C2HA C 0.610(2) 0.4392(18) 0.9212(5) 0.094(4) Uani 0.69(3) d A 1 . H2HA H 0.6607 0.4274 0.9663 0.113 Uiso 0.69(3) calc A 1 R H2HB H 0.6005 0.5586 0.9120 0.113 Uiso 0.69(3) calc A 1 R C4HB C 0.399(4) 0.374(8) 0.9688(15) 0.159(18) Uani 0.31(3) d A 2 . H4HC H 0.4360 0.4316 1.0097 0.191 Uiso 0.31(3) calc A 2 R H4HD H 0.4179 0.2551 0.9770 0.191 Uiso 0.31(3) calc A 2 R C3HB C 0.494(6) 0.429(8) 0.919(2) 0.17(2) Uani 0.31(3) d A 2 . H3HC H 0.4366 0.4159 0.8752 0.208 Uiso 0.31(3) calc A 2 R H3HD H 0.5119 0.5488 0.9253 0.208 Uiso 0.31(3) calc A 2 R C2HB C 0.626(4) 0.352(8) 0.9187(17) 0.127(15) Uani 0.31(3) d A 2 . H2HC H 0.6866 0.3863 0.9596 0.153 Uiso 0.31(3) calc A 2 R H2HD H 0.6083 0.2332 0.9230 0.153 Uiso 0.31(3) calc A 2 R O1W O 0.5983(2) 0.0758(3) 0.64606(10) 0.0546(5) Uani 1 d . . D H1WA H 0.588(5) -0.045(3) 0.652(2) 0.090(15) Uiso 1 d . . D H1WB H 0.701(4) 0.091(18) 0.668(5) 0.23(5) Uiso 1 d . . D O2W O 0.4303(4) 0.2050(5) 0.73665(18) 0.0885(9) Uani 1 d . . . H2WA H 0.344(6) 0.254(7) 0.715(2) 0.086(14) Uiso 1 d . . . H2WB H 0.465(8) 0.170(11) 0.708(4) 0.13(3) Uiso 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 O1 0.0499(10) 0.0505(10) 0.0367(8) 0.0016(7) 0.0164(7) 0.0089(8) O9 0.0493(10) 0.0406(9) 0.0451(9) -0.0056(8) 0.0111(7) -0.0115(7) O7 0.0350(9) 0.0428(9) 0.0459(9) -0.0095(8) 0.0121(7) -0.0015(7) O2 0.0323(9) 0.0465(10) 0.0586(11) 0.0070(8) 0.0167(8) -0.0013(7) O11 0.0724(14) 0.0650(14) 0.0549(11) 0.0066(10) 0.0258(10) 0.0276(11) O3 0.0431(10) 0.0489(10) 0.0375(8) -0.0027(8) 0.0081(7) 0.0059(7) O8 0.0402(9) 0.0367(8) 0.0436(8) 0.0046(7) 0.0176(7) -0.0011(7) O4 0.0437(10) 0.0376(10) 0.0505(10) -0.0045(8) 0.0229(7) 0.0000(7) O10 0.0368(9) 0.0420(9) 0.0442(8) -0.0010(7) 0.0165(7) -0.0046(7) O5 0.0381(9) 0.0375(8) 0.0404(8) -0.0038(7) 0.0127(6) -0.0033(7) O6 0.0363(9) 0.0379(9) 0.0467(9) 0.0055(7) 0.0045(6) -0.0080(6) N1 0.066(2) 0.148(4) 0.095(3) -0.021(3) 0.0040(19) -0.009(2) C3 0.0559(16) 0.0561(16) 0.0345(11) 0.0012(11) 0.0129(10) 0.0071(12) C16 0.0281(11) 0.0350(11) 0.0369(10) -0.0009(9) 0.0089(8) 0.0012(8) C8 0.076(2) 0.062(2) 0.0555(17) -0.0127(15) 0.0179(15) 0.0007(16) C13 0.0375(12) 0.0270(11) 0.0440(12) 0.0017(9) 0.0134(9) -0.0003(8) C17 0.0280(10) 0.0316(10) 0.0366(10) 0.0038(9) 0.0088(8) -0.0016(8) C2 0.0533(16) 0.0594(18) 0.0372(12) -0.0005(11) 0.0113(10) 0.0072(12) C20 0.0533(16) 0.0483(14) 0.0397(12) -0.0017(11) 0.0155(10) 0.0031(11) C12 0.0327(11) 0.0290(11) 0.0418(12) -0.0025(9) 0.0165(8) -0.0027(8) C5 0.060(2) 0.105(3) 0.0616(19) 0.002(2) 0.0246(15) -0.009(2) C14 0.0336(12) 0.0337(12) 0.0530(14) 0.0070(10) 0.0104(9) -0.0007(9) C4 0.067(2) 0.071(2) 0.0508(15) -0.0115(15) 0.0207(13) -0.0065(15) C1 0.0555(19) 0.092(3) 0.0552(16) -0.0087(17) 0.0073(13) 0.0039(17) C18 0.0317(11) 0.0324(11) 0.0376(11) -0.0018(9) 0.0082(8) -0.0019(8) C19 0.0362(12) 0.0390(12) 0.0379(11) -0.0002(9) 0.0074(9) -0.0006(9) C9 0.0375(12) 0.0342(12) 0.0448(12) 0.0032(9) 0.0182(9) -0.0004(8) C6 0.075(2) 0.100(3) 0.0611(18) 0.007(2) 0.0333(17) 0.022(2) C10 0.0359(12) 0.0289(11) 0.0440(12) 0.0001(9) 0.0175(9) 0.0000(8) C11 0.0326(12) 0.0302(11) 0.0419(11) -0.0028(9) 0.0091(8) -0.0024(8) C7 0.104(3) 0.081(3) 0.064(2) -0.021(2) 0.033(2) 0.019(2) C15 0.0276(11) 0.0341(11) 0.0414(11) 0.0013(9) 0.0083(8) -0.0017(8) O1H 0.0815(19) 0.090(2) 0.0687(15) -0.0101(14) 0.0222(12) 0.0124(14) C1H 0.101(4) 0.163(6) 0.074(3) -0.014(4) 0.003(2) 0.034(4) C5H 0.167(7) 0.158(7) 0.096(4) -0.010(5) 0.036(4) 0.002(6) C6H 0.170(8) 0.270(14) 0.107(5) -0.017(7) 0.056(5) -0.062(9) C4HA 0.138(10) 0.098(7) 0.060(4) 0.001(4) 0.025(5) -0.017(6) C3HA 0.141(9) 0.083(6) 0.062(5) -0.011(5) 0.015(5) -0.014(6) C2HA 0.124(10) 0.100(7) 0.058(4) -0.014(5) 0.015(5) 0.015(7) C4HB 0.15(2) 0.24(5) 0.105(17) 0.07(2) 0.064(15) 0.08(3) C3HB 0.19(4) 0.19(4) 0.17(3) 0.11(3) 0.11(3) 0.12(4) C2HB 0.102(16) 0.19(4) 0.092(15) 0.03(2) 0.022(12) 0.07(3) O1W 0.0563(12) 0.0522(12) 0.0557(11) 0.0036(9) 0.0108(9) 0.0022(9) O2W 0.0712(18) 0.105(2) 0.089(2) -0.0061(18) 0.0124(15) 0.0242(17) 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 C9 O1 C2 115.5(2) . . ? C18 O9 H9 113(3) . . ? C16 O7 H7 110(3) . . ? C10 O2 H2 113(3) . . ? C20 O11 H11 111(4) . . ? C11 O3 H3 106(3) . . ? C17 O8 H8 104(2) . . ? C12 O4 H4 104(4) . . ? C15 O10 C19 114.55(16) . . ? C9 O5 C13 111.79(18) . . ? C15 O6 C14 116.04(18) . . ? C8 C3 C2 123.8(3) . . ? C8 C3 C4 118.6(3) . . ? C4 C3 C2 117.5(3) . . ? O7 C16 H16 110.5(16) . . ? O7 C16 C17 108.99(17) . . ? O7 C16 C15 110.60(18) . . ? C17 C16 H16 111.8(17) . . ? C17 C16 C15 109.49(18) . . ? C15 C16 H16 105.4(16) . . ? C3 C8 H8A 118(3) . . ? C3 C8 C7 119.4(4) . . ? C7 C8 H8A 122(3) . . ? O5 C13 H13 111(2) . . ? O5 C13 C12 107.83(18) . . ? O5 C13 C14 107.06(19) . . ? C12 C13 H13 109(2) . . ? C14 C13 H13 109(2) . . ? C14 C13 C12 112.68(19) . . ? O8 C17 C16 111.69(18) . . ? O8 C17 H17 109.8(15) . . ? O8 C17 C18 108.94(18) . . ? C16 C17 H17 109.6(15) . . ? C16 C17 C18 108.65(17) . . ? C18 C17 H17 108.1(15) . . ? O1 C2 C3 108.0(2) . . ? O1 C2 H2A 110(2) . . ? O1 C2 C1 110.3(3) . . ? C3 C2 H2A 109(2) . . ? C1 C2 C3 112.9(3) . . ? C1 C2 H2A 106(2) . . ? O11 C20 H20A 109.9(19) . . ? O11 C20 H20B 113(2) . . ? O11 C20 C19 109.9(2) . . ? H20A C20 H20B 107(3) . . ? C19 C20 H20A 108(2) . . ? C19 C20 H20B 108(2) . . ? O4 C12 C13 111.83(19) . . ? O4 C12 H12 105.8(18) . . ? O4 C12 C11 110.65(19) . . ? C13 C12 H12 110.1(18) . . ? C13 C12 C11 112.26(18) . . ? C11 C12 H12 105.7(18) . . ? C4 C5 H5 123(3) . . ? C6 C5 H5 117(3) . . ? C6 C5 C4 120.2(4) . . ? O6 C14 C13 108.31(19) . . ? O6 C14 H14A 108.8(16) . . ? O6 C14 H14B 113.2(18) . . ? C13 C14 H14A 110.5(16) . . ? C13 C14 H14B 110.1(17) . . ? H14A C14 H14B 106(2) . . ? C3 C4 H4A 117(3) . . ? C5 C4 C3 120.9(4) . . ? C5 C4 H4A 122(3) . . ? N1 C1 C2 178.4(5) . . ? O9 C18 C17 111.80(18) . . ? O9 C18 H18 111.2(16) . . ? O9 C18 C19 108.82(18) . . ? C17 C18 H18 105.2(15) . . ? C17 C18 C19 109.01(18) . . ? C19 C18 H18 110.9(15) . . ? O10 C19 C20 105.97(19) . . ? O10 C19 C18 108.94(18) . . ? O10 C19 H19 113.1(17) . . ? C20 C19 C18 114.2(2) . . ? C20 C19 H19 108.7(15) . . ? C18 C19 H19 106.1(16) . . ? O1 C9 O5 107.4(2) . . ? O1 C9 H9A 109.0(17) . . ? O1 C9 C10 106.91(19) . . ? O5 C9 H9A 109.2(17) . . ? O5 C9 C10 110.43(18) . . ? C10 C9 H9A 113.6(17) . . ? C5 C6 H6 117(3) . . ? C7 C6 C5 119.3(3) . . ? C7 C6 H6 124(3) . . ? O2 C10 C9 108.60(19) . . ? O2 C10 H10 112.0(17) . . ? O2 C10 C11 110.09(19) . . ? C9 C10 H10 108.7(17) . . ? C9 C10 C11 112.42(19) . . ? C11 C10 H10 105.0(17) . . ? O3 C11 C12 110.80(18) . . ? O3 C11 C10 105.93(18) . . ? O3 C11 H11A 114.7(19) . . ? C12 C11 C10 112.00(19) . . ? C12 C11 H11A 107.9(18) . . ? C10 C11 H11A 105.5(19) . . ? C8 C7 H7A 112(4) . . ? C6 C7 C8 121.6(4) . . ? C6 C7 H7A 126(3) . . ? O10 C15 C16 111.22(18) . . ? O10 C15 H15 109.2(16) . . ? O6 C15 O10 107.21(17) . . ? O6 C15 C16 106.87(18) . . ? O6 C15 H15 111.6(17) . . ? C16 C15 H15 110.7(16) . . ? C1H O1H H1H 109.5 . . ? O1H C1H H1HA 109.4 . . ? O1H C1H H1HB 109.4 . . ? O1H C1H H1HC 107.0 . . ? O1H C1H H1HD 107.0 . . ? O1H C1H C2HA 111.0(7) . . ? H1HA C1H H1HB 108.0 . . ? H1HA C1H H1HC 82.7 . . ? H1HA C1H H1HD 24.8 . . ? H1HB C1H H1HC 28.7 . . ? H1HB C1H H1HD 129.4 . . ? H1HC C1H H1HD 106.7 . . ? C2HA C1H H1HA 109.4 . . ? C2HA C1H H1HB 109.4 . . ? C2HA C1H H1HC 132.6 . . ? C2HA C1H H1HD 88.3 . . ? C2HB C1H O1H 121.4(15) . . ? C2HB C1H H1HA 121.1 . . ? C2HB C1H H1HB 82.3 . . ? C2HB C1H H1HC 107.0 . . ? C2HB C1H H1HD 107.0 . . ? C2HB C1H C2HA 27(3) . . ? H5HA C5H H5HB 106.8 . . ? H5HA C5H H5HC 131.9 . . ? H5HA C5H H5HD 31.4 . . ? H5HB C5H H5HC 28.0 . . ? H5HB C5H H5HD 78.1 . . ? H5HC C5H H5HD 105.7 . . ? C6H C5H H5HA 107.2 . . ? C6H C5H H5HB 107.2 . . ? C6H C5H H5HC 104.5 . . ? C6H C5H H5HD 104.5 . . ? C6H C5H C4HB 130.9(17) . . ? C4HA C5H H5HA 107.2 . . ? C4HA C5H H5HB 107.2 . . ? C4HA C5H H5HC 85.8 . . ? C4HA C5H H5HD 129.0 . . ? C4HA C5H C6H 120.6(9) . . ? C4HA C5H C4HB 26.8(19) . . ? C4HB C5H H5HA 80.4 . . ? C4HB C5H H5HB 117.0 . . ? C4HB C5H H5HC 104.5 . . ? C4HB C5H H5HD 104.5 . . ? C5H C6H H6HA 109.5 . . ? C5H C6H H6HB 109.5 . . ? C5H C6H H6HC 109.5 . . ? H6HA C6H H6HB 109.5 . . ? H6HA C6H H6HC 109.5 . . ? H6HB C6H H6HC 109.5 . . ? C5H C4HA H4HA 108.0 . . ? C5H C4HA H4HB 108.0 . . ? C5H C4HA C3HA 117.2(9) . . ? H4HA C4HA H4HB 107.2 . . ? C3HA C4HA H4HA 108.0 . . ? C3HA C4HA H4HB 108.0 . . ? C4HA C3HA H3HA 108.6 . . ? C4HA C3HA H3HB 108.6 . . ? H3HA C3HA H3HB 107.6 . . ? C2HA C3HA C4HA 114.7(9) . . ? C2HA C3HA H3HA 108.6 . . ? C2HA C3HA H3HB 108.6 . . ? C1H C2HA H2HA 108.1 . . ? C1H C2HA H2HB 108.1 . . ? C3HA C2HA C1H 116.6(9) . . ? C3HA C2HA H2HA 108.1 . . ? C3HA C2HA H2HB 108.1 . . ? H2HA C2HA H2HB 107.3 . . ? C5H C4HB H4HC 106.5 . . ? C5H C4HB H4HD 106.5 . . ? H4HC C4HB H4HD 106.5 . . ? C3HB C4HB C5H 123(3) . . ? C3HB C4HB H4HC 106.5 . . ? C3HB C4HB H4HD 106.5 . . ? C4HB C3HB H3HC 107.3 . . ? C4HB C3HB H3HD 107.3 . . ? H3HC C3HB H3HD 106.9 . . ? C2HB C3HB C4HB 120(4) . . ? C2HB C3HB H3HC 107.3 . . ? C2HB C3HB H3HD 107.3 . . ? C1H C2HB C3HB 128(3) . . ? C1H C2HB H2HC 105.2 . . ? C1H C2HB H2HD 105.2 . . ? C3HB C2HB H2HC 105.2 . . ? C3HB C2HB H2HD 105.2 . . ? H2HC C2HB H2HD 106.0 . . ? H1WA O1W H1WB 100(8) . . ? H2WA O2W H2WB 104(6) . . ? 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 C2 1.427(3) . ? O1 C9 1.394(3) . ? O9 H9 0.82(5) . ? O9 C18 1.419(3) . ? O7 H7 0.86(5) . ? O7 C16 1.415(3) . ? O2 H2 0.80(5) . ? O2 C10 1.422(3) . ? O11 H11 0.89(5) . ? O11 C20 1.420(4) . ? O3 H3 0.86(5) . ? O3 C11 1.428(3) . ? O8 H8 0.89(4) . ? O8 C17 1.419(3) . ? O4 H4 0.73(6) . ? O4 C12 1.425(3) . ? O10 C19 1.433(3) . ? O10 C15 1.411(3) . ? O5 C13 1.435(3) . ? O5 C9 1.422(3) . ? O6 C14 1.420(3) . ? O6 C15 1.390(3) . ? N1 C1 1.141(6) . ? C3 C8 1.376(5) . ? C3 C2 1.507(4) . ? C3 C4 1.389(5) . ? C16 H16 0.98(3) . ? C16 C17 1.520(3) . ? C16 C15 1.522(3) . ? C8 H8A 0.92(5) . ? C8 C7 1.394(6) . ? C13 H13 1.00(4) . ? C13 C12 1.520(3) . ? C13 C14 1.511(3) . ? C17 H17 1.03(3) . ? C17 C18 1.520(3) . ? C2 H2A 0.95(4) . ? C2 C1 1.478(5) . ? C20 H20A 0.98(3) . ? C20 H20B 1.01(4) . ? C20 C19 1.511(3) . ? C12 H12 0.91(3) . ? C12 C11 1.525(3) . ? C5 H5 0.99(5) . ? C5 C4 1.376(5) . ? C5 C6 1.370(7) . ? C14 H14A 1.00(3) . ? C14 H14B 0.96(3) . ? C4 H4A 0.90(5) . ? C18 H18 1.02(3) . ? C18 C19 1.528(3) . ? C19 H19 1.04(3) . ? C9 H9A 0.92(3) . ? C9 C10 1.509(3) . ? C6 H6 1.03(4) . ? C6 C7 1.354(7) . ? C10 H10 0.90(3) . ? C10 C11 1.526(3) . ? C11 H11A 0.99(4) . ? C7 H7A 0.97(6) . ? C15 H15 0.97(3) . ? O1H H1H 0.8200 . ? O1H C1H 1.405(6) . ? C1H H1HA 0.9700 . ? C1H H1HB 0.9700 . ? C1H H1HC 0.9700 . ? C1H H1HD 0.9700 . ? C1H C2HA 1.539(15) . ? C1H C2HB 1.27(3) . ? C5H H5HA 0.9700 . ? C5H H5HB 0.9700 . ? C5H H5HC 0.9700 . ? C5H H5HD 0.9700 . ? C5H C6H 1.432(11) . ? C5H C4HA 1.412(15) . ? C5H C4HB 1.60(3) . ? C6H H6HA 0.9600 . ? C6H H6HB 0.9600 . ? C6H H6HC 0.9600 . ? C4HA H4HA 0.9700 . ? C4HA H4HB 0.9700 . ? C4HA C3HA 1.54(2) . ? C3HA H3HA 0.9700 . ? C3HA H3HB 0.9700 . ? C3HA C2HA 1.47(2) . ? C2HA H2HA 0.9700 . ? C2HA H2HB 0.9700 . ? C4HB H4HC 0.9700 . ? C4HB H4HD 0.9700 . ? C4HB C3HB 1.54(6) . ? C3HB H3HC 0.9700 . ? C3HB H3HD 0.9700 . ? C3HB C2HB 1.39(5) . ? C2HB H2HC 0.9700 . ? C2HB H2HD 0.9700 . ? O1W H1WA 0.97(2) . ? O1W H1WB 1.00(2) . ? O2W H2WA 0.93(6) . ? O2W H2WB 0.78(8) . ? 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 C2 C1 N1 -169(17) . . . . ? O1 C9 C10 O2 -69.7(2) . . . . ? O1 C9 C10 C11 168.25(19) . . . . ? O9 C18 C19 O10 178.91(18) . . . . ? O9 C18 C19 C20 60.6(3) . . . . ? O7 C16 C17 O8 62.1(2) . . . . ? O7 C16 C17 C18 -177.69(18) . . . . ? O7 C16 C15 O10 175.37(17) . . . . ? O7 C16 C15 O6 -67.9(2) . . . . ? O2 C10 C11 O3 74.8(2) . . . . ? O2 C10 C11 C12 -164.2(2) . . . . ? O11 C20 C19 O10 -61.5(3) . . . . ? O11 C20 C19 C18 58.4(3) . . . . ? O8 C17 C18 O9 -58.7(2) . . . . ? O8 C17 C18 C19 -179.10(17) . . . . ? O4 C12 C11 O3 -70.5(2) . . . . ? O4 C12 C11 C10 171.47(19) . . . . ? O5 C13 C12 O4 178.94(17) . . . . ? O5 C13 C12 C11 -56.0(2) . . . . ? O5 C13 C14 O6 -75.4(2) . . . . ? O5 C9 C10 O2 173.77(19) . . . . ? O5 C9 C10 C11 51.7(3) . . . . ? C3 C8 C7 C6 -1.7(6) . . . . ? C3 C2 C1 N1 70(18) . . . . ? C16 C17 C18 O9 179.36(18) . . . . ? C16 C17 C18 C19 59.0(2) . . . . ? C8 C3 C2 O1 -113.1(3) . . . . ? C8 C3 C2 C1 9.1(4) . . . . ? C8 C3 C4 C5 -0.9(5) . . . . ? C13 O5 C9 O1 178.75(17) . . . . ? C13 O5 C9 C10 -65.0(2) . . . . ? C13 C12 C11 O3 163.80(18) . . . . ? C13 C12 C11 C10 45.8(3) . . . . ? C17 C16 C15 O10 55.3(2) . . . . ? C17 C16 C15 O6 171.96(18) . . . . ? C17 C18 C19 O10 -58.9(2) . . . . ? C17 C18 C19 C20 -177.19(19) . . . . ? C2 O1 C9 O5 -75.8(3) . . . . ? C2 O1 C9 C10 165.6(2) . . . . ? C2 C3 C8 C7 178.4(3) . . . . ? C2 C3 C4 C5 -178.1(3) . . . . ? C12 C13 C14 O6 42.9(3) . . . . ? C5 C6 C7 C8 1.3(7) . . . . ? C14 O6 C15 O10 -92.1(2) . . . . ? C14 O6 C15 C16 148.55(19) . . . . ? C14 C13 C12 O4 61.0(3) . . . . ? C14 C13 C12 C11 -173.92(19) . . . . ? C4 C3 C8 C7 1.5(5) . . . . ? C4 C3 C2 O1 63.9(4) . . . . ? C4 C3 C2 C1 -173.9(3) . . . . ? C4 C5 C6 C7 -0.8(7) . . . . ? C19 O10 C15 O6 -174.46(18) . . . . ? C19 O10 C15 C16 -58.0(2) . . . . ? C9 O1 C2 C3 -145.4(2) . . . . ? C9 O1 C2 C1 90.8(3) . . . . ? C9 O5 C13 C12 66.5(2) . . . . ? C9 O5 C13 C14 -172.03(18) . . . . ? C9 C10 C11 O3 -163.93(18) . . . . ? C9 C10 C11 C12 -43.0(3) . . . . ? C6 C5 C4 C3 0.6(6) . . . . ? C15 O10 C19 C20 -177.23(19) . . . . ? C15 O10 C19 C18 59.4(2) . . . . ? C15 O6 C14 C13 154.7(2) . . . . ? C15 C16 C17 O8 -176.79(17) . . . . ? C15 C16 C17 C18 -56.6(2) . . . . ? O1H C1H C2HA C3HA 65.4(14) . . . . ? O1H C1H C2HB C3HB -28(10) . . . . ? C5H C4HA C3HA C2HA 178.1(10) . . . . ? C5H C4HB C3HB C2HB -155(5) . . . . ? C6H C5H C4HA C3HA 177.2(11) . . . . ? C6H C5H C4HB C3HB -130(5) . . . . ? C4HA C5H C4HB C3HB -53(5) . . . . ? C4HA C3HA C2HA C1H -176.0(9) . . . . ? C2HA C1H C2HB C3HB 46(5) . . . . ? C4HB C5H C4HA C3HA 56(3) . . . . ? C4HB C3HB C2HB C1H 168(5) . . . . ? C2HB C1H C2HA C3HA -53(5) . . . . ?