#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/18/2101873.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2101873 loop_ _publ_author_name 'Gjerl\/ov, A.' 'Larsen, S.' _publ_section_title ; A Study of Diastereomeric Mandelate Salts of Cinchonidine and the Relation to Their Quasidiastereomeric Analogues ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 708 _journal_page_last 718 _journal_paper_doi 10.1107/S0108768197003480 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety ; 'C~19H~23~N~2~O^+^C~8~H~7~O~3~^-^ ; _chemical_formula_sum 'C27 H30 N2 O4' _chemical_formula_weight 446.53 _chemical_name_systematic ; cinchonidinium (R)-mandelate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 100.67(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.410(3) _cell_length_b 32.808(11) _cell_length_c 11.222(2) _cell_measurement_reflns_used 18 _cell_measurement_temperature 122.0(10) _cell_measurement_theta_max 30.18 _cell_measurement_theta_min 16.23 _cell_volume 2319.2(14) _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'DREADD (Blessing, 1987)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-93 (Sheldrick, 1995) and local programs' ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 122.0(10) _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 10960 _diffrn_reflns_theta_max 75.03 _diffrn_reflns_theta_min 2.69 _diffrn_standards_decay_% 7.7 _diffrn_standards_interval_time 166.7 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_type 'integration by crystal shape' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method none _exptl_crystal_description needle _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.156 _refine_diff_density_min -0.243 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.029 _refine_ls_goodness_of_fit_obs 1.027 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 775 _refine_ls_number_reflns 9153 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_obs 1.027 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_obs 0.0380 _refine_ls_shift/esd_max 0.005 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1007 _refine_ls_wR_factor_obs 0.0991 _reflns_number_observed 8951 _reflns_number_total 9154 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ab0369.cif _cod_data_source_block R _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2319.2(13) _cod_original_sg_symbol_Hall 'P 2y1' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2101873 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O4A 0.0185(5) 0.0223(5) 0.0293(6) -0.0037(4) 0.0031(4) 0.0018(4) N1A 0.0361(8) 0.0205(6) 0.0259(6) -0.0003(6) 0.0114(6) -0.0008(5) N2A 0.0223(6) 0.0183(6) 0.0229(6) 0.0028(5) 0.0043(5) -0.0006(5) C9A 0.0239(7) 0.0180(7) 0.0200(6) -0.0011(6) 0.0084(5) 0.0007(5) C10A 0.0240(7) 0.0203(7) 0.0197(7) -0.0029(6) 0.0072(6) 0.0000(5) C11A 0.0240(8) 0.0241(8) 0.0219(7) -0.0011(6) 0.0052(6) 0.0004(6) C12A 0.0251(8) 0.0318(9) 0.0276(8) -0.0028(7) 0.0051(6) -0.0008(7) C13A 0.0276(8) 0.0330(9) 0.0265(8) -0.0113(7) 0.0059(6) -0.0041(7) C14A 0.0360(9) 0.0245(7) 0.0242(7) -0.0098(7) 0.0096(6) -0.0034(6) C15A 0.0299(8) 0.0202(7) 0.0227(7) -0.0042(6) 0.0096(6) 0.0002(6) C16A 0.0322(9) 0.0212(7) 0.0275(8) 0.0038(7) 0.0103(6) 0.0008(6) C17A 0.0257(8) 0.0226(7) 0.0237(7) 0.0006(6) 0.0078(6) 0.0023(6) C18A 0.0180(7) 0.0179(7) 0.0212(7) -0.0011(5) 0.0042(5) -0.0009(5) C19A 0.0206(7) 0.0168(6) 0.0199(7) 0.0002(6) 0.0045(5) -0.0013(5) C20A 0.0275(8) 0.0191(7) 0.0226(7) 0.0047(6) 0.0050(6) 0.0012(5) C21A 0.0238(8) 0.0247(7) 0.0206(7) 0.0011(6) 0.0021(5) 0.0003(6) C22A 0.0232(8) 0.0297(8) 0.0288(8) -0.0042(7) 0.0019(6) -0.0043(6) C23A 0.0291(8) 0.0208(7) 0.0289(8) -0.0040(7) 0.0048(6) -0.0042(6) C24A 0.0212(7) 0.0267(8) 0.0260(7) 0.0038(7) 0.0072(6) -0.0032(6) C25A 0.0262(8) 0.0266(8) 0.0215(7) -0.0012(6) 0.0062(6) -0.0036(6) C26A 0.0336(9) 0.0315(9) 0.0310(9) -0.0057(7) 0.0076(7) -0.0025(7) C27A 0.085(2) 0.064(2) 0.0357(11) -0.038(2) 0.0178(12) 0.0009(11) O4B 0.0196(5) 0.0244(5) 0.0258(5) 0.0040(4) 0.0039(4) -0.0012(4) N1B 0.0324(7) 0.0244(6) 0.0259(7) -0.0004(6) -0.0001(5) -0.0046(5) N2B 0.0183(6) 0.0179(6) 0.0244(6) -0.0022(5) 0.0028(5) -0.0003(5) C9B 0.0201(7) 0.0204(7) 0.0190(6) 0.0016(6) 0.0007(5) 0.0000(5) C10B 0.0230(7) 0.0219(7) 0.0202(7) 0.0041(6) 0.0023(5) 0.0017(5) C11B 0.0265(8) 0.0265(8) 0.0263(8) 0.0023(7) 0.0051(6) 0.0041(6) C12B 0.0292(9) 0.0409(10) 0.0322(9) 0.0044(8) 0.0100(7) 0.0093(7) C13B 0.0364(10) 0.0459(11) 0.0256(8) 0.0120(8) 0.0098(7) 0.0020(7) C14B 0.0397(10) 0.0345(9) 0.0233(8) 0.0107(8) 0.0039(7) -0.0040(7) C15B 0.0271(8) 0.0254(8) 0.0213(7) 0.0050(6) 0.0001(6) 0.0005(6) C16B 0.0274(8) 0.0242(8) 0.0294(8) -0.0038(7) 0.0011(6) -0.0008(6) C17B 0.0225(8) 0.0244(8) 0.0229(7) -0.0003(6) 0.0022(6) 0.0002(6) C18B 0.0191(7) 0.0179(7) 0.0227(7) 0.0021(6) 0.0035(5) -0.0003(5) C19B 0.0195(7) 0.0173(7) 0.0226(7) -0.0011(6) 0.0024(5) -0.0022(5) C20B 0.0219(8) 0.0194(7) 0.0242(7) -0.0029(6) 0.0008(6) 0.0017(6) C21B 0.0204(7) 0.0248(8) 0.0225(7) 0.0002(6) 0.0042(5) -0.0001(6) C22B 0.0211(8) 0.0292(8) 0.0318(8) 0.0026(7) 0.0080(6) -0.0034(7) C23B 0.0220(7) 0.0177(7) 0.0305(8) 0.0008(6) 0.0023(6) -0.0044(6) C24B 0.0163(7) 0.0242(7) 0.0282(8) -0.0038(6) 0.0005(6) -0.0013(6) C25B 0.0194(7) 0.0245(7) 0.0224(7) -0.0006(6) 0.0017(5) -0.0029(6) C26B 0.0242(8) 0.0288(8) 0.0294(8) 0.0018(7) 0.0042(6) 0.0009(7) C27B 0.0306(9) 0.0489(12) 0.0351(10) 0.0094(9) 0.0028(8) 0.0103(9) O1A 0.0212(5) 0.0255(6) 0.0447(7) -0.0002(5) 0.0030(5) 0.0086(5) O2A 0.0239(6) 0.0201(5) 0.0292(6) 0.0043(5) 0.0007(4) -0.0010(4) O3A 0.0220(6) 0.0261(6) 0.0404(7) 0.0010(5) -0.0029(5) 0.0119(5) C1A 0.0210(7) 0.0194(7) 0.0202(6) 0.0001(6) -0.0014(5) 0.0005(5) C2A 0.0209(7) 0.0214(7) 0.0235(7) 0.0004(6) 0.0005(6) 0.0035(6) C3A 0.0220(7) 0.0192(7) 0.0234(7) -0.0015(6) 0.0037(6) 0.0040(5) C4A 0.0228(8) 0.0226(7) 0.0324(8) -0.0023(6) 0.0044(6) 0.0013(6) C5A 0.0230(8) 0.0284(8) 0.0395(10) -0.0042(7) -0.0003(7) 0.0041(7) C6A 0.0392(10) 0.0281(9) 0.0328(9) -0.0092(8) -0.0045(7) 0.0008(7) C7A 0.0448(10) 0.0241(8) 0.0303(9) -0.0018(8) 0.0054(7) -0.0035(7) C8A 0.0288(9) 0.0234(8) 0.0280(8) 0.0031(7) 0.0054(6) 0.0042(6) O1B 0.0326(6) 0.0221(5) 0.0311(6) -0.0040(5) 0.0047(5) -0.0003(4) O2B 0.0320(6) 0.0270(6) 0.0392(7) 0.0020(5) 0.0142(5) -0.0032(5) O3B 0.0425(7) 0.0273(6) 0.0226(5) 0.0058(6) 0.0067(5) -0.0019(5) C1B 0.0211(7) 0.0212(7) 0.0247(7) 0.0003(6) 0.0002(5) -0.0029(6) C2B 0.0245(8) 0.0201(7) 0.0231(7) -0.0013(6) 0.0020(6) -0.0029(6) C3B 0.0239(8) 0.0191(7) 0.0230(7) 0.0027(6) 0.0037(6) -0.0053(5) C4B 0.0258(8) 0.0268(8) 0.0245(7) -0.0024(7) 0.0062(6) -0.0036(6) C5B 0.0428(10) 0.0309(9) 0.0241(8) 0.0020(8) 0.0062(7) 0.0008(7) C6B 0.0376(9) 0.0331(9) 0.0275(8) 0.0086(8) -0.0048(7) -0.0044(7) C7B 0.0243(8) 0.0306(8) 0.0382(9) 0.0022(7) 0.0003(7) -0.0088(7) C8B 0.0240(8) 0.0237(7) 0.0310(8) 0.0007(6) 0.0048(6) -0.0029(6) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_occupancy _atom_site_type_symbol O4A 0.4411(2) 0.22863(4) 0.15799(10) 0.0236(2) Uani d 1 O H4O_1 0.412(4) 0.2052(7) 0.193(2) 0.030 Uiso d 1 H N1A 0.7113(2) 0.35760(4) 0.37576(13) 0.0268(3) Uani d 1 N N2A 0.8311(2) 0.20179(4) 0.04372(12) 0.0211(3) Uani d 1 N H2_1 0.899(4) 0.1866(7) 0.111(2) 0.030 Uiso d 1 H C9A 0.6785(3) 0.27997(5) 0.26234(13) 0.0201(3) Uani d 1 C C10A 0.8700(3) 0.29134(5) 0.34190(14) 0.0209(3) Uani d 1 C C11A 1.0524(3) 0.26607(5) 0.36922(14) 0.0232(3) Uani d 1 C H11_1 1.045(4) 0.2378(7) 0.337(2) 0.030 Uiso d 1 H C12A 1.2322(3) 0.27922(6) 0.4445(2) 0.0281(3) Uani d 1 C H12_1 1.361(4) 0.2600(7) 0.461(2) 0.030 Uiso d 1 H C13A 1.2394(3) 0.31850(6) 0.4976(2) 0.0289(4) Uani d 1 C H13_1 1.360(4) 0.3280(7) 0.556(2) 0.030 Uiso d 1 H C14A 1.0656(3) 0.34326(5) 0.47463(15) 0.0277(3) Uani d 1 C H14_1 1.065(4) 0.3696(7) 0.514(2) 0.030 Uiso d 1 H C15A 0.8778(3) 0.33075(5) 0.39679(14) 0.0237(3) Uani d 1 C C16A 0.5388(3) 0.34555(5) 0.30125(15) 0.0263(3) Uani d 1 C H16_1 0.422(4) 0.3665(7) 0.286(2) 0.030 Uiso d 1 H C17A 0.5149(3) 0.30733(5) 0.24239(14) 0.0236(3) Uani d 1 C H17_1 0.378(4) 0.3003(7) 0.189(2) 0.030 Uiso d 1 H C18A 0.6576(2) 0.23905(5) 0.19738(13) 0.0190(3) Uani d 1 C H18_1 0.724(4) 0.2179(7) 0.251(2) 0.030 Uiso d 1 H C19A 0.7714(2) 0.24291(4) 0.08804(13) 0.0190(3) Uani d 1 C H19_1 0.909(4) 0.2559(7) 0.117(2) 0.030 Uiso d 1 H C20A 0.6454(3) 0.26658(5) -0.02063(14) 0.0230(3) Uani d 1 C H201_1 0.709(4) 0.2943(7) -0.017(2) 0.030 Uiso d 1 H H202_1 0.501(4) 0.2699(7) -0.007(2) 0.030 Uiso d 1 H C21A 0.6542(3) 0.24302(5) -0.13755(14) 0.0233(3) Uani d 1 C H21_1 0.579(4) 0.2588(7) -0.211(2) 0.030 Uiso d 1 H C22A 0.5400(3) 0.20213(6) -0.1336(2) 0.0276(3) Uani d 1 C H221_1 0.546(4) 0.1883(7) -0.209(2) 0.030 Uiso d 1 H H222_1 0.395(4) 0.2067(7) -0.131(2) 0.030 Uiso d 1 H C23A 0.6450(3) 0.17779(5) -0.0214(2) 0.0263(3) Uani d 1 C H231_1 0.704(4) 0.1521(7) -0.041(2) 0.030 Uiso d 1 H H232_1 0.545(4) 0.1725(7) 0.036(2) 0.030 Uiso d 1 H C24A 0.9872(3) 0.20801(5) -0.03895(15) 0.0243(3) Uani d 1 C H241_1 1.025(4) 0.1817(7) -0.062(2) 0.030 Uiso d 1 H H242_1 1.105(4) 0.2198(7) 0.007(2) 0.030 Uiso d 1 H C25A 0.8854(3) 0.23419(5) -0.14937(15) 0.0245(3) Uani d 1 C H25_1 0.877(4) 0.2169(7) -0.225(2) 0.030 Uiso d 1 H C26A 1.0085(3) 0.27244(6) -0.1591(2) 0.0318(4) Uani d 1 C H26_1 1.040(4) 0.2898(7) -0.090(2) 0.030 Uiso d 1 H C27A 1.0744(5) 0.28351(9) -0.2582(2) 0.0607(8) Uani d 1 C H271_1 1.148(4) 0.3088(7) -0.266(2) 0.030 Uiso d 1 H H272_1 1.044(4) 0.2694(7) -0.325(2) 0.030 Uiso d 1 H O4B 0.0289(2) 0.48126(4) 0.30277(10) 0.0233(2) Uani d 1 O H4O_2 -0.045(4) 0.4990(7) 0.244(2) 0.030 Uiso d 1 H N1B 0.1093(2) 0.35899(4) 0.04548(13) 0.0283(3) Uani d 1 N N2B 0.4908(2) 0.50434(4) 0.41613(12) 0.0204(3) Uani d 1 N H2_2 0.522(4) 0.5210(7) 0.355(2) 0.030 Uiso d 1 H C9B 0.1794(2) 0.43246(5) 0.18060(13) 0.0202(3) Uani d 1 C C10B 0.3098(3) 0.42263(5) 0.09425(14) 0.0219(3) Uani d 1 C C11B 0.4781(3) 0.44751(5) 0.0705(2) 0.0264(3) Uani d 1 C H11_2 0.507(4) 0.4725(7) 0.114(2) 0.030 Uiso d 1 H C12B 0.5943(3) 0.43641(6) -0.0156(2) 0.0335(4) Uani d 1 C H12_2 0.702(4) 0.4543(7) -0.031(2) 0.030 Uiso d 1 H C13B 0.5507(3) 0.39971(7) -0.0807(2) 0.0355(4) Uani d 1 C H13_2 0.634(4) 0.3921(7) -0.139(2) 0.030 Uiso d 1 H C14B 0.3910(3) 0.37469(6) -0.0584(2) 0.0327(4) Uani d 1 C H14_2 0.354(4) 0.3481(7) -0.101(2) 0.030 Uiso d 1 H C15B 0.2665(3) 0.38554(5) 0.02851(14) 0.0252(3) Uani d 1 C C16B -0.0066(3) 0.36954(5) 0.1259(2) 0.0275(3) Uani d 1 C H16_2 -0.118(4) 0.3523(7) 0.133(2) 0.030 Uiso d 1 H C17B 0.0216(3) 0.40577(5) 0.19479(14) 0.0235(3) Uani d 1 C H17_2 -0.074(4) 0.4119(7) 0.248(2) 0.030 Uiso d 1 H C18B 0.2129(2) 0.47126(5) 0.25676(13) 0.0199(3) Uani d 1 C H18_2 0.254(4) 0.4946(7) 0.207(2) 0.030 Uiso d 1 H C19B 0.4006(2) 0.46453(5) 0.36328(13) 0.0200(3) Uani d 1 C H19_2 0.516(4) 0.4512(7) 0.330(2) 0.030 Uiso d 1 H C20B 0.3461(3) 0.43816(5) 0.46719(14) 0.0223(3) Uani d 1 C H201_2 0.419(4) 0.4117(7) 0.468(2) 0.030 Uiso d 1 H H202_2 0.200(4) 0.4340(7) 0.457(2) 0.030 Uiso d 1 H C21B 0.4198(2) 0.45965(5) 0.58882(14) 0.0225(3) Uani d 1 C H21_2 0.393(4) 0.4421(7) 0.659(2) 0.030 Uiso d 1 H C22B 0.3003(3) 0.49997(5) 0.5890(2) 0.0269(3) Uani d 1 C H221_2 0.347(4) 0.5157(7) 0.668(2) 0.030 Uiso d 1 H H222_2 0.148(4) 0.4936(7) 0.577(2) 0.030 Uiso d 1 H C23B 0.3430(3) 0.52675(5) 0.4835(2) 0.0237(3) Uani d 1 C H231_2 0.410(4) 0.5513(7) 0.511(2) 0.030 Uiso d 1 H H232_2 0.209(4) 0.5346(7) 0.427(2) 0.030 Uiso d 1 H C24B 0.6975(2) 0.49602(5) 0.50102(15) 0.0233(3) Uani d 1 C H241_2 0.757(4) 0.5231(7) 0.530(2) 0.030 Uiso d 1 H H242_2 0.793(4) 0.4826(7) 0.449(2) 0.030 Uiso d 1 H C25B 0.6593(2) 0.46938(5) 0.60854(14) 0.0224(3) Uani d 1 C H25_2 0.695(4) 0.4849(7) 0.685(2) 0.030 Uiso d 1 H C26B 0.7959(3) 0.43158(6) 0.6219(2) 0.0276(3) Uani d 1 C H26_2 0.774(4) 0.4135(7) 0.553(2) 0.030 Uiso d 1 H C27B 0.9434(3) 0.42382(7) 0.7185(2) 0.0386(4) Uani d 1 C H271_2 0.968(4) 0.4419(7) 0.784(2) 0.030 Uiso d 1 H H272_2 1.025(4) 0.3989(8) 0.728(2) 0.030 Uiso d 1 H O1A 0.3819(2) 0.15654(4) 0.26121(12) 0.0309(3) Uani d 1 O O2A 0.0433(2) 0.17436(4) 0.25104(10) 0.0249(2) Uani d 1 O O3A 0.3388(2) 0.08458(4) 0.34974(13) 0.0306(3) Uani d 1 O H3O_3 0.429(4) 0.0981(7) 0.323(2) 0.030 Uiso d 1 H C1A 0.1958(2) 0.14980(5) 0.27276(13) 0.0209(3) Uani d 1 C C2A 0.1489(3) 0.10713(5) 0.32049(14) 0.0224(3) Uani d 1 C H2_3 0.096(4) 0.1128(7) 0.395(2) 0.030 Uiso d 1 H C3A -0.0173(3) 0.08477(5) 0.22980(14) 0.0216(3) Uani d 1 C C4A -0.2266(3) 0.09872(5) 0.2072(2) 0.0261(3) Uani d 1 C H4_3 -0.263(4) 0.1232(7) 0.251(2) 0.030 Uiso d 1 H C5A -0.3791(3) 0.07947(6) 0.1213(2) 0.0311(4) Uani d 1 C H5_3 -0.528(4) 0.0892(7) 0.106(2) 0.030 Uiso d 1 H C6A -0.3259(3) 0.04579(6) 0.0590(2) 0.0348(4) Uani d 1 C H6_3 -0.442(4) 0.0325(7) -0.001(2) 0.030 Uiso d 1 H C7A -0.1184(3) 0.03143(5) 0.0821(2) 0.0333(4) Uani d 1 C H7_3 -0.088(4) 0.0092(7) 0.030(2) 0.030 Uiso d 1 H C8A 0.0356(3) 0.05103(5) 0.1664(2) 0.0267(3) Uani d 1 C H8_3 0.171(4) 0.0413(7) 0.180(2) 0.030 Uiso d 1 H O1B 0.1782(2) 0.03520(4) 0.85158(11) 0.0288(3) Uani d 1 O O2B 0.3772(2) 0.06011(4) 0.72375(12) 0.0318(3) Uani d 1 O O3B 0.1203(2) 0.10775(4) 0.94186(11) 0.0307(3) Uani d 1 O H3O_4 0.101(4) 0.0842(8) 0.954(2) 0.030 Uiso d 1 H C1B 0.2571(2) 0.06338(5) 0.79960(14) 0.0229(3) Uani d 1 C C2B 0.1997(3) 0.10715(5) 0.83200(14) 0.0229(3) Uani d 1 C H2_4 0.328(4) 0.1236(7) 0.842(2) 0.030 Uiso d 1 H C3B 0.0377(3) 0.12522(5) 0.72889(14) 0.0221(3) Uani d 1 C C4B 0.0988(3) 0.15309(5) 0.64803(15) 0.0255(3) Uani d 1 C H4_4 0.239(4) 0.1618(7) 0.658(2) 0.030 Uiso d 1 H C5B -0.0501(3) 0.16901(6) 0.5533(2) 0.0326(4) Uani d 1 C H5_4 -0.004(4) 0.1892(7) 0.496(2) 0.030 Uiso d 1 H C6B -0.2606(3) 0.15683(6) 0.5374(2) 0.0341(4) Uani d 1 C H6_4 -0.365(4) 0.1678(7) 0.468(2) 0.030 Uiso d 1 H C7B -0.3223(3) 0.12901(6) 0.6177(2) 0.0317(4) Uani d 1 C H7_4 -0.467(4) 0.1206(7) 0.611(2) 0.030 Uiso d 1 H C8B -0.1739(3) 0.11337(5) 0.7131(2) 0.0263(3) Uani d 1 C H8_4 -0.214(4) 0.0942(7) 0.771(2) 0.030 Uiso d 1 H 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' O O 0.0492 0.0322 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H4O_1 O4A C18A . . 110.0(15) ? H4O_1 O4A O1A . . 4.3(15) ? C18A O4A O1A . . 106.59(9) ? H4O_1 O4A H4O_1 . . 0.(5) ? C18A O4A H4O_1 . . 110.0(15) ? O1A O4A H4O_1 . . 4.3(15) ? C16A N1A C15A . . 116.87(14) ? H2_1 N2A C24A . . 107.8(14) ? H2_1 N2A C23A . . 108.9(14) ? C24A N2A C23A . . 109.36(12) yes H2_1 N2A C19A . . 108.3(14) ? C24A N2A C19A . . 108.71(12) yes C23A N2A C19A . . 113.68(12) yes H2_1 N2A O2A . 1_655 11.7(14) ? C24A N2A O2A . 1_655 107.41(10) ? C23A N2A O2A . 1_655 119.06(10) ? C19A N2A O2A . 1_655 97.78(9) ? H2_1 N2A H2_1 . . 0.(4) ? C24A N2A H2_1 . . 107.8(14) ? C23A N2A H2_1 . . 108.9(14) ? C19A N2A H2_1 . . 108.3(14) ? O2A N2A H2_1 1_655 . 11.7(14) ? C17A C9A C10A . . 118.40(14) ? C17A C9A C18A . . 120.25(14) yes C10A C9A C18A . . 121.32(14) yes C11A C10A C9A . . 124.12(14) ? C11A C10A C15A . . 118.25(15) ? C9A C10A C15A . . 117.63(15) ? C12A C11A C10A . . 121.1(2) ? C12A C11A H11_1 . . 119.8(14) ? C10A C11A H11_1 . . 119.0(14) ? C11A C12A C13A . . 120.3(2) ? C11A C12A H12_1 . . 118.4(13) ? C13A C12A H12_1 . . 121.3(13) ? C14A C13A C12A . . 120.0(2) ? C14A C13A H13_1 . . 117.5(14) ? C12A C13A H13_1 . . 122.3(14) ? C13A C14A C15A . . 121.1(2) ? C13A C14A H14_1 . . 121.2(14) ? C15A C14A H14_1 . . 117.6(14) ? N1A C15A C14A . . 117.9(2) ? N1A C15A C10A . . 122.9(2) ? C14A C15A C10A . . 119.2(2) ? N1A C16A C17A . . 124.6(2) ? N1A C16A H16_1 . . 114.4(13) ? C17A C16A H16_1 . . 121.0(13) ? C9A C17A C16A . . 119.5(2) ? C9A C17A H17_1 . . 120.7(13) ? C16A C17A H17_1 . . 119.8(13) ? O4A C18A C9A . . 110.90(12) yes O4A C18A C19A . . 110.54(12) yes C9A C18A C19A . . 107.18(12) yes O4A C18A H18_1 . . 108.5(14) ? C9A C18A H18_1 . . 110.1(13) ? C19A C18A H18_1 . . 109.7(13) ? N2A C19A C20A . . 108.46(12) yes N2A C19A C18A . . 111.96(12) yes C20A C19A C18A . . 114.48(13) yes N2A C19A H19_1 . . 103.2(14) ? C20A C19A H19_1 . . 110.7(14) ? C18A C19A H19_1 . . 107.4(13) ? C21A C20A C19A . . 109.03(12) ? C21A C20A H201_1 . . 115.0(13) ? C19A C20A H201_1 . . 105.9(13) ? C21A C20A H202_1 . . 112.5(14) ? C19A C20A H202_1 . . 107.6(14) ? H201_1 C20A H202_1 . . 106.3(19) ? C20A C21A C22A . . 108.86(14) ? C20A C21A C25A . . 110.93(13) ? C22A C21A C25A . . 108.07(14) ? C20A C21A H21_1 . . 110.7(13) ? C22A C21A H21_1 . . 108.1(13) ? C25A C21A H21_1 . . 110.1(13) ? C21A C22A C23A . . 109.84(13) ? C21A C22A H221_1 . . 106.8(14) ? C23A C22A H221_1 . . 113.1(14) ? C21A C22A H222_1 . . 109.9(14) ? C23A C22A H222_1 . . 109.9(13) ? H221_1 C22A H222_1 . . 107.2(19) ? N2A C23A C22A . . 108.30(13) ? N2A C23A H231_1 . . 105.1(13) ? C22A C23A H231_1 . . 113.3(13) ? N2A C23A H232_1 . . 108.9(13) ? C22A C23A H232_1 . . 112.3(13) ? H231_1 C23A H232_1 . . 108.6(18) ? N2A C24A C25A . . 109.86(13) ? N2A C24A H241_1 . . 106.4(14) ? C25A C24A H241_1 . . 112.1(14) ? N2A C24A H242_1 . . 106.4(14) ? C25A C24A H242_1 . . 113.5(14) ? H241_1 C24A H242_1 . . 108.(2) ? C26A C25A C21A . . 112.17(14) ? C26A C25A C24A . . 111.93(14) ? C21A C25A C24A . . 107.77(13) ? C26A C25A H25_1 . . 110.8(13) ? C21A C25A H25_1 . . 106.0(13) ? C24A C25A H25_1 . . 107.8(13) ? C27A C26A C25A . . 123.4(2) yes C27A C26A H26_1 . . 118.3(14) ? C25A C26A H26_1 . . 118.3(14) ? C26A C27A H271_1 . . 123.6(14) ? C26A C27A H272_1 . . 121.9(16) ? H271_1 C27A H272_1 . . 114.(2) ? H4O_2 O4B C18B . . 103.3(14) ? H4O_2 O4B O1B . 2_556 4.0(14) ? C18B O4B O1B . 2_556 105.49(9) ? H4O_2 O4B H4O_2 . . 0.(5) ? C18B O4B H4O_2 . . 103.3(14) ? O1B O4B H4O_2 2_556 . 4.0(14) ? C16B N1B C15B . . 116.78(14) ? H2_2 N2B C19B . . 109.9(14) ? H2_2 N2B C24B . . 106.9(14) ? C19B N2B C24B . . 108.70(12) yes H2_2 N2B C23B . . 108.8(14) ? C19B N2B C23B . . 112.91(12) yes C24B N2B C23B . . 109.39(12) yes H2_2 N2B O2B . 2_656 11.0(14) ? C19B N2B O2B . 2_656 120.49(10) ? C24B N2B O2B . 2_656 99.21(9) ? C23B N2B O2B . 2_656 105.03(10) ? H2_2 N2B H2_2 . . 0.(4) ? C19B N2B H2_2 . . 109.9(14) ? C24B N2B H2_2 . . 106.9(14) ? C23B N2B H2_2 . . 108.8(14) ? O2B N2B H2_2 2_656 . 11.0(14) ? C17B C9B C10B . . 118.16(14) ? C17B C9B C18B . . 119.93(14) yes C10B C9B C18B . . 121.91(14) yes C11B C10B C15B . . 118.51(15) ? C11B C10B C9B . . 123.98(15) ? C15B C10B C9B . . 117.51(14) ? C12B C11B C10B . . 120.7(2) ? C12B C11B H11_2 . . 120.4(14) ? C10B C11B H11_2 . . 118.9(14) ? C11B C12B C13B . . 120.7(2) ? C11B C12B H12_2 . . 118.3(14) ? C13B C12B H12_2 . . 121.0(14) ? C14B C13B C12B . . 120.0(2) ? C14B C13B H13_2 . . 120.0(14) ? C12B C13B H13_2 . . 120.0(14) ? C13B C14B C15B . . 120.7(2) ? C13B C14B H14_2 . . 123.6(13) ? C15B C14B H14_2 . . 115.7(13) ? N1B C15B C14B . . 117.3(2) ? N1B C15B C10B . . 123.28(15) ? C14B C15B C10B . . 119.4(2) ? N1B C16B C17B . . 124.4(2) ? N1B C16B H16_2 . . 115.8(14) ? C17B C16B H16_2 . . 119.7(14) ? C9B C17B C16B . . 119.9(2) ? C9B C17B H17_2 . . 120.8(14) ? C16B C17B H17_2 . . 119.3(14) ? O4B C18B C9B . . 110.99(12) yes O4B C18B C19B . . 109.50(12) yes C9B C18B C19B . . 108.81(12) yes O4B C18B H18_2 . . 110.2(13) ? C9B C18B H18_2 . . 110.4(13) ? C19B C18B H18_2 . . 106.8(13) ? N2B C19B C20B . . 108.24(12) yes N2B C19B C18B . . 111.58(12) yes C20B C19B C18B . . 114.27(12) yes N2B C19B H19_2 . . 105.8(14) ? C20B C19B H19_2 . . 108.9(14) ? C18B C19B H19_2 . . 107.7(13) ? C21B C20B C19B . . 109.86(13) ? C21B C20B H201_2 . . 109.1(13) ? C19B C20B H201_2 . . 109.1(13) ? C21B C20B H202_2 . . 108.4(14) ? C19B C20B H202_2 . . 110.6(14) ? H201_2 C20B H202_2 . . 110.(2) ? C22B C21B C20B . . 109.10(13) ? C22B C21B C25B . . 107.82(13) ? C20B C21B C25B . . 110.96(13) ? C22B C21B H21_2 . . 109.6(13) ? C20B C21B H21_2 . . 111.1(13) ? C25B C21B H21_2 . . 108.3(13) ? C21B C22B C23B . . 109.44(13) ? C21B C22B H221_2 . . 111.9(13) ? C23B C22B H221_2 . . 108.4(13) ? C21B C22B H222_2 . . 107.4(14) ? C23B C22B H222_2 . . 109.1(13) ? H221_2 C22B H222_2 . . 110.5(18) ? N2B C23B C22B . . 108.96(13) ? N2B C23B H231_2 . . 106.9(14) ? C22B C23B H231_2 . . 111.9(14) ? N2B C23B H232_2 . . 110.4(13) ? C22B C23B H232_2 . . 112.5(13) ? H231_2 C23B H232_2 . . 106.1(19) ? N2B C24B C25B . . 110.39(12) ? N2B C24B H241_2 . . 106.6(13) ? C25B C24B H241_2 . . 110.7(13) ? N2B C24B H242_2 . . 105.6(13) ? C25B C24B H242_2 . . 113.5(13) ? H241_2 C24B H242_2 . . 109.7(18) ? C26B C25B C21B . . 112.79(13) ? C26B C25B C24B . . 111.67(13) ? C21B C25B C24B . . 107.59(12) ? C26B C25B H25_2 . . 107.5(13) ? C21B C25B H25_2 . . 107.1(14) ? C24B C25B H25_2 . . 110.0(13) ? C27B C26B C25B . . 123.5(2) yes C27B C26B H26_2 . . 121.1(14) ? C25B C26B H26_2 . . 115.3(14) ? C26B C27B H271_2 . . 121.0(14) ? C26B C27B H272_2 . . 122.9(14) ? H271_2 C27B H272_2 . . 116.(2) ? C1A O1A H4O_1 . . 112.4(7) ? C1A O1A H3O_3 . . 83.2(7) ? H4O_1 O1A H3O_3 . . 163.6(10) ? C1A O1A O3A . . 68.05(9) ? H4O_1 O1A O3A . . 177.3(7) ? H3O_3 O1A O3A . . 15.3(7) ? C1A O1A O4A . . 114.56(10) ? H4O_1 O1A O4A . . 2.2(7) ? H3O_3 O1A O4A . . 161.4(7) ? O3A O1A O4A . . 175.94(7) ? H3O_3 O3A C2A . . 105.3(16) ? H3O_3 O3A O1A . . 40.7(16) ? C2A O3A O1A . . 65.31(9) ? H3O_3 O3A H3O_3 . . 0.(5) ? C2A O3A H3O_3 . . 105.3(16) ? O1A O3A H3O_3 . . 40.7(16) ? O1A C1A O2A . . 126.38(15) yes O1A C1A C2A . . 116.65(14) yes O2A C1A C2A . . 116.97(14) yes O3A C2A C3A . . 111.75(14) yes O3A C2A C1A . . 109.89(13) yes C3A C2A C1A . . 111.22(12) yes O3A C2A H2_3 . . 108.8(14) ? C3A C2A H2_3 . . 110.7(14) ? C1A C2A H2_3 . . 104.2(13) ? C8A C3A C4A . . 119.0(2) yes C8A C3A C2A . . 121.31(15) yes C4A C3A C2A . . 119.65(15) yes C5A C4A C3A . . 120.4(2) yes C5A C4A H4_3 . . 120.9(13) ? C3A C4A H4_3 . . 118.7(13) ? C6A C5A C4A . . 120.4(2) yes C6A C5A H5_3 . . 119.5(14) ? C4A C5A H5_3 . . 120.1(14) ? C5A C6A C7A . . 119.5(2) yes C5A C6A H6_3 . . 117.6(13) ? C7A C6A H6_3 . . 122.9(13) ? C6A C7A C8A . . 120.3(2) yes C6A C7A H7_3 . . 115.5(14) ? C8A C7A H7_3 . . 123.9(14) ? C3A C8A C7A . . 120.4(2) yes C3A C8A H8_3 . . 120.4(15) ? C7A C8A H8_3 . . 119.2(15) ? C1B O1B H3O_4 . . 81.1(7) ? C1B O1B O3B . . 67.03(10) ? H3O_4 O1B O3B . . 14.2(7) ? H3O_4 O3B C2B . . 103.3(17) ? H3O_4 O3B O1B . . 39.8(17) ? C2B O3B O1B . . 63.60(8) ? H3O_4 O3B H3O_4 . . 0.(5) ? C2B O3B H3O_4 . . 103.3(17) ? O1B O3B H3O_4 . . 39.8(17) ? O1B C1B O2B . . 127.4(2) yes O1B C1B C2B . . 116.37(14) yes O2B C1B C2B . . 116.28(14) yes O3B C2B C3B . . 110.51(13) yes O3B C2B C1B . . 110.94(13) yes C3B C2B C1B . . 109.99(12) yes O3B C2B H2_4 . . 108.8(14) ? C3B C2B H2_4 . . 108.3(14) ? C1B C2B H2_4 . . 108.2(14) ? C8B C3B C4B . . 119.0(2) yes C8B C3B C2B . . 119.95(15) yes C4B C3B C2B . . 120.99(15) yes C5B C4B C3B . . 120.5(2) yes C5B C4B H4_4 . . 119.3(14) ? C3B C4B H4_4 . . 120.2(14) ? C6B C5B C4B . . 120.2(2) yes C6B C5B H5_4 . . 120.1(14) ? C4B C5B H5_4 . . 119.7(14) ? C5B C6B C7B . . 119.5(2) yes C5B C6B H6_4 . . 119.4(14) ? C7B C6B H6_4 . . 121.1(14) ? C6B C7B C8B . . 120.3(2) yes C6B C7B H7_4 . . 121.8(14) ? C8B C7B H7_4 . . 117.9(14) ? C3B C8B C7B . . 120.4(2) yes C3B C8B H8_4 . . 117.9(14) ? C7B C8B H8_4 . . 121.6(14) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O4A H4O_1 . 0.90(2) ? O4A C18A . 1.418(2) yes O4A O1A . 2.691(2) ? O4A H4O_1 . 0.90(2) ? N1A C16A . 1.318(2) ? N1A C15A . 1.370(2) ? N2A H2_1 . 0.94(2) ? N2A C24A . 1.499(2) yes N2A C23A . 1.501(2) yes N2A C19A . 1.511(2) yes N2A O2A 1_655 2.627(2) ? N2A H2_1 . 0.94(2) ? C9A C17A . 1.367(2) ? C9A C10A . 1.427(2) ? C9A C18A . 1.522(2) yes C10A C11A . 1.420(2) ? C10A C15A . 1.429(2) ? C11A C12A . 1.367(2) ? C11A H11_1 . 0.99(2) ? C12A C13A . 1.417(3) ? C12A H12_1 . 1.03(2) ? C13A C14A . 1.364(3) ? C13A H13_1 . 0.97(2) ? C14A C15A . 1.411(2) ? C14A H14_1 . 0.97(2) ? C16A C17A . 1.412(2) ? C16A H16_1 . 1.01(2) ? C17A H17_1 . 0.99(2) ? C18A C19A . 1.544(2) yes C18A H18_1 . 0.97(2) ? C19A C20A . 1.542(2) ? C19A H19_1 . 0.98(2) ? C20A C21A . 1.533(2) ? C20A H201_1 . 0.99(2) ? C20A H202_1 . 0.97(3) ? C21A C22A . 1.533(2) ? C21A C25A . 1.539(2) ? C21A H21_1 . 1.02(2) ? C22A C23A . 1.537(2) ? C22A H221_1 . 0.97(2) ? C22A H222_1 . 0.95(2) ? C23A H231_1 . 0.97(2) ? C23A H232_1 . 1.00(2) ? C24A C25A . 1.549(2) ? C24A H241_1 . 0.95(2) ? C24A H242_1 . 0.92(2) ? C25A C26A . 1.497(2) yes C25A H25_1 . 1.01(2) ? C26A C27A . 1.311(3) yes C26A H26_1 . 0.96(2) ? C27A H271_1 . 0.97(2) ? C27A H272_1 . 0.87(2) ? O4B H4O_2 . 0.94(2) ? O4B C18B . 1.411(2) yes O4B O1B 2_556 2.654(2) ? O4B H4O_2 . 0.94(2) ? N1B C16B . 1.317(2) ? N1B C15B . 1.372(2) ? N2B H2_2 . 0.93(2) ? N2B C19B . 1.505(2) yes N2B C24B . 1.507(2) yes N2B C23B . 1.509(2) yes N2B O2B 2_656 2.649(2) ? N2B H2_2 . 0.93(2) ? C9B C17B . 1.369(2) ? C9B C10B . 1.429(2) ? C9B C18B . 1.526(2) yes C10B C11B . 1.416(2) ? C10B C15B . 1.423(2) ? C11B C12B . 1.374(2) ? C11B H11_2 . 0.95(2) ? C12B C13B . 1.409(3) ? C12B H12_2 . 0.94(2) ? C13B C14B . 1.371(3) ? C13B H13_2 . 0.95(2) ? C14B C15B . 1.415(2) ? C14B H14_2 . 1.00(2) ? C16B C17B . 1.411(2) ? C16B H16_2 . 0.92(2) ? C17B H17_2 . 0.95(2) ? C18B C19B . 1.547(2) yes C18B H18_2 . 1.01(2) ? C19B C20B . 1.543(2) ? C19B H19_2 . 0.99(2) ? C20B C21B . 1.531(2) ? C20B H201_2 . 0.99(2) ? C20B H202_2 . 0.93(2) ? C21B C22B . 1.529(2) ? C21B C25B . 1.543(2) ? C21B H21_2 . 1.01(2) ? C22B C23B . 1.539(2) ? C22B H221_2 . 1.02(2) ? C22B H222_2 . 0.98(2) ? C23B H231_2 . 0.94(2) ? C23B H232_2 . 1.00(2) ? C24B C25B . 1.546(2) ? C24B H241_2 . 1.00(2) ? C24B H242_2 . 1.02(2) ? C25B C26B . 1.510(2) yes C25B H25_2 . 0.99(2) ? C26B C27B . 1.325(3) yes C26B H26_2 . 0.97(2) ? C27B H271_2 . 0.94(2) ? C27B H272_2 . 0.96(3) ? O1A C1A . 1.244(2) yes O1A H3O_3 . 2.04(2) ? O1A O3A . 2.596(2) ? O2A C1A . 1.255(2) yes O3A H3O_3 . 0.83(3) ? O3A C2A . 1.410(2) yes O3A H3O_3 . 0.83(3) ? C1A C2A . 1.548(2) yes C2A C3A . 1.519(2) yes C2A H2_3 . 0.98(2) ? C3A C8A . 1.391(2) yes C3A C4A . 1.395(2) yes C4A C5A . 1.391(2) yes C4A H4_3 . 0.99(2) ? C5A C6A . 1.384(3) yes C5A H5_3 . 0.99(2) ? C6A C7A . 1.390(3) yes C6A H6_3 . 1.01(2) ? C7A C8A . 1.392(3) yes C7A H7_3 . 0.97(2) ? C8A H8_3 . 0.91(3) ? O1B C1B . 1.249(2) yes O1B H3O_4 . 2.09(3) ? O1B O3B . 2.640(2) ? O2B C1B . 1.254(2) yes O3B H3O_4 . 0.80(3) ? O3B C2B . 1.419(2) yes O3B H3O_4 . 0.80(3) ? C1B C2B . 1.543(2) yes C2B C3B . 1.524(2) yes C2B H2_4 . 0.97(2) ? C3B C8B . 1.391(2) yes C3B C4B . 1.394(2) yes C4B C5B . 1.392(2) yes C4B H4_4 . 0.93(2) ? C5B C6B . 1.387(3) yes C5B H5_4 . 1.01(2) ? C6B C7B . 1.391(3) yes C6B H6_4 . 1.00(2) ? C7B C8B . 1.392(3) yes C7B H7_4 . 0.96(2) ? C8B H8_4 . 0.98(2) ? 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_publ_flag O1A C1A C2A O3A 3.9(2) yes O1A C1A C2A C3A -120.4(2) yes C1A C2A C3A C4A -68.5(2) yes O3A C2A C3A C4A 168.25(14) yes C10A C9A C18A O4A 160.26(13) yes C17A C9A C18A O4A -21.8(2) yes C17A C9A C18A C19A 98.9(2) yes C10A C9A C18A C19A -79.0(2) yes C9A C18A C19A N2A 159.40(12) yes C9A C18A C19A C20A -76.6(2) yes O4A C18A C19A C20A 44.3(2) yes O4A C18A C19A N2A -79.63(15) yes C25A C21A N2A C24A -1.50(11) yes C25A C21A N2A C19A 116.46(12) yes C25A C21A N2A C23A -119.99(12) yes C20A C21A N2A C19A -5.21(11) yes C20A C21A N2A C23A 118.35(12) yes C20A C21A N2A C24A -123.16(13) yes C22A C21A N2A C23A -1.49(11) yes C22A C21A N2A C24A 117.00(13) yes C22A C21A N2A C19A -125.05(12) yes C24A C25A C26A C27A 127.5(3) yes O1B C1B C2B O3B 18.0(2) yes O1B C1B C2B C3B -104.6(2) yes C1B C2B C3B C4B -102.4(2) yes O3B C2B C3B C4B 134.8(2) yes C10B C9B C18B O4B 160.06(13) yes C17B C9B C18B O4B -20.5(2) yes C17B C9B C18B C19B 100.1(2) yes C10B C9B C18B C19B -79.4(2) yes C9B C18B C19B N2B 160.55(12) yes C9B C18B C19B C20B -76.3(2) yes O4B C18B C19B C20B 45.2(2) yes O4B C18B C19B N2B -77.98(15) yes C25B C21B N2B C24B 0.90(10) yes C25B C21B N2B C19B 118.91(11) yes C25B C21B N2B C23B -118.25(12) yes C20B C21B N2B C19B -3.04(10) yes C20B C21B N2B C23B 119.80(12) yes C20B C21B N2B C24B -121.06(12) yes C22B C21B N2B C23B -0.40(11) yes C22B C21B N2B C24B 118.75(12) yes C22B C21B N2B C19B -123.24(12) yes C24B C25B C26B C27B 117.0(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063359