#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:21:09 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301810 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500092.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_3500092 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. ; _publ_section_title ; benzoic acid 3,5-dicarboxylate N-N'-bis(2-Ammonioethyl)oxamide dimethylsulfoxide' ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C9 H4 O6, C6 H16 N4 O2, C2 H6 O S' _chemical_formula_sum 'C17 H26 N4 O9 S' _chemical_formula_weight 462.48 _chemical_name_common ; benzoic acid 3,5-dicarboxylate N-N'-bis(2-Ammonioethyl)oxamide dimethylsulfoxide' ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2017-09-27 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _cell_angle_alpha 90 _cell_angle_beta 97.7760(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7597(3) _cell_length_b 16.5287(4) _cell_length_c 13.0405(3) _cell_measurement_reflns_used 9993 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.655 _cell_measurement_theta_min 2.326 _cell_volume 2084.29(9) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0277 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 28323 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.646 _diffrn_reflns_theta_min 3.778 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 1.244 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.6780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1152 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.9017. 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 1.474 _exptl_crystal_description Block _exptl_crystal_F_000 976 _exptl_crystal_recrystallization_method 'crystallized from DMSO' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.331 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.104 _refine_ls_extinction_coef 0.0443(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 385 _refine_ls_number_reflns 4784 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0373 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.7550P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.0961 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 4647 _reflns_number_total 4784 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file tma2cb.cif _cod_data_source_block tma2cb _cod_database_code 3500092 _cod_database_fobs_code 3500092 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.76418(9) 0.31345(5) 1.16332(6) 0.02119(19) Uani 1 1 d . . . . . H1 H 0.810(2) 0.3375(12) 1.2226(16) 0.042(5) Uiso 1 1 d . . . . . C1 C 0.66599(11) 0.33722(7) 0.99122(8) 0.0155(2) Uani 1 1 d . . . . . C2 C 0.64114(11) 0.38863(7) 0.90597(8) 0.0161(2) Uani 1 1 d . . . . . H2A H 0.6743(16) 0.4414(10) 0.9110(12) 0.022(4) Uiso 1 1 d . . . . . O2 O 0.75324(13) 0.44184(6) 1.10874(7) 0.0360(3) Uani 1 1 d . . . . . O3 O 0.59468(10) 0.48688(5) 0.72845(7) 0.0247(2) Uani 1 1 d . . . . . C3 C 0.56711(11) 0.36165(6) 0.81343(8) 0.0137(2) Uani 1 1 d . . . . . O4 O 0.45194(8) 0.39461(5) 0.64633(6) 0.01830(18) Uani 1 1 d . . . . . C4 C 0.51853(10) 0.28205(6) 0.80671(8) 0.0136(2) Uani 1 1 d . . . . . H4 H 0.4689(16) 0.2644(10) 0.7450(12) 0.020(4) Uiso 1 1 d . . . . . O5 O 0.40133(8) 0.11980(5) 0.82399(6) 0.01663(18) Uani 1 1 d . . . . . C5 C 0.55009(10) 0.22864(6) 0.88980(8) 0.0131(2) Uani 1 1 d . . . . . C6 C 0.62424(11) 0.25670(7) 0.98189(8) 0.0145(2) Uani 1 1 d . . . . . H6 H 0.6440(15) 0.2207(10) 1.0382(12) 0.019(4) Uiso 1 1 d . . . . . O6 O 0.58648(8) 0.09090(5) 0.93726(6) 0.01701(18) Uani 1 1 d . . . . . C7 C 0.73284(12) 0.37040(7) 1.09259(9) 0.0183(2) Uani 1 1 d . . . . . C8 C 0.53632(11) 0.41923(6) 0.72191(8) 0.0147(2) Uani 1 1 d . . . . . C9 C 0.50872(11) 0.14041(6) 0.88314(8) 0.0127(2) Uani 1 1 d . . . . . N1 N 0.61547(10) 0.59848(6) 0.56991(7) 0.0157(2) Uani 1 1 d . . . . . H1A H 0.7100(19) 0.5984(10) 0.5657(14) 0.028(4) Uiso 1 1 d . . . . . H1B H 0.5712(19) 0.5923(10) 0.5072(15) 0.028(4) Uiso 1 1 d . . . . . H1C H 0.5959(18) 0.5564(12) 0.6085(14) 0.031(4) Uiso 1 1 d . . . . . N2 N 0.33366(10) 0.68258(6) 0.53239(8) 0.0181(2) Uani 1 1 d . . . . . H2 H 0.3196(18) 0.7341(12) 0.5069(14) 0.031(4) Uiso 1 1 d . . . . . N3 N 0.10455(10) 0.57529(6) 0.34519(8) 0.0184(2) Uani 1 1 d . . . . . H3 H 0.1159(17) 0.5295(11) 0.3778(14) 0.027(4) Uiso 1 1 d . . . . . N4 N -0.18371(10) 0.54552(6) 0.34789(7) 0.0167(2) Uani 1 1 d . . . . . H4A H -0.2739(18) 0.5534(10) 0.3533(13) 0.026(4) Uiso 1 1 d . . . . . H4B H -0.1707(17) 0.4945(12) 0.3342(14) 0.028(4) Uiso 1 1 d . . . . . H4C H -0.1369(17) 0.5556(11) 0.4118(14) 0.027(4) Uiso 1 1 d . . . . . H10A H 0.6336(17) 0.6822(10) 0.6798(13) 0.024(4) Uiso 1 1 d . . . . . H10B H 0.5951(17) 0.7208(11) 0.5695(13) 0.028(4) Uiso 1 1 d . . . . . H11A H 0.4016(15) 0.6261(10) 0.6658(12) 0.019(3) Uiso 1 1 d . . . . . H11B H 0.4079(17) 0.7228(11) 0.6731(13) 0.027(4) Uiso 1 1 d . . . . . O7 O 0.29458(8) 0.54774(5) 0.51094(6) 0.01980(18) Uani 1 1 d . . . . . O8 O 0.16833(10) 0.70793(5) 0.34771(7) 0.0281(2) Uani 1 1 d . . . . . H14A H 0.0089(16) 0.5260(10) 0.2171(13) 0.023(4) Uiso 1 1 d . . . . . H14B H 0.0425(16) 0.6197(10) 0.2066(13) 0.021(4) Uiso 1 1 d . . . . . H15A H -0.1412(16) 0.6561(10) 0.2970(13) 0.022(4) Uiso 1 1 d . . . . . H15B H -0.2008(16) 0.5957(10) 0.2071(13) 0.021(4) Uiso 1 1 d . . . . . C10 C 0.57614(12) 0.67646(7) 0.61543(9) 0.0184(2) Uani 1 1 d . . . . . C11 C 0.42452(12) 0.67636(7) 0.63012(9) 0.0189(2) Uani 1 1 d . . . . . C12 C 0.27580(11) 0.61851(7) 0.48295(8) 0.0160(2) Uani 1 1 d . . . . . C13 C 0.17688(12) 0.63918(7) 0.38407(9) 0.0178(2) Uani 1 1 d . . . . . C14 C 0.00837(12) 0.57917(7) 0.24979(9) 0.0187(2) Uani 1 1 d . . . . . C15 C -0.13719(12) 0.60075(7) 0.26914(8) 0.0176(2) Uani 1 1 d . . . . . S1 S 0.32852(3) 0.91224(2) 0.45934(2) 0.02068(11) Uani 1 1 d . . . . . H16A H 0.453(2) 0.8793(13) 0.3346(17) 0.049(6) Uiso 1 1 d . . . . . H16B H 0.3178(19) 0.8249(12) 0.3230(15) 0.036(5) Uiso 1 1 d . . . . . H16C H 0.308(2) 0.9185(12) 0.2822(16) 0.040(5) Uiso 1 1 d . . . . . H17A H 0.117(2) 0.9135(13) 0.5088(19) 0.053(6) Uiso 1 1 d . . . . . H17B H 0.1281(19) 0.8393(13) 0.4353(15) 0.039(5) Uiso 1 1 d . . . . . H17C H 0.098(2) 0.9251(12) 0.3891(17) 0.042(5) Uiso 1 1 d . . . . . O9 O 0.39128(11) 0.84759(6) 0.53228(7) 0.0323(2) Uani 1 1 d . . . . . C16 C 0.35435(14) 0.87928(9) 0.33326(10) 0.0259(3) Uani 1 1 d . . . . . C17 C 0.14577(15) 0.89549(9) 0.44658(13) 0.0319(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0305(4) 0.0167(4) 0.0136(4) -0.0001(3) -0.0074(3) -0.0009(3) C1 0.0188(5) 0.0144(5) 0.0123(5) -0.0003(4) -0.0015(4) -0.0002(4) C2 0.0207(5) 0.0124(5) 0.0144(5) 0.0006(4) -0.0011(4) -0.0016(4) O2 0.0640(7) 0.0166(4) 0.0218(5) 0.0002(3) -0.0148(4) -0.0080(4) O3 0.0361(5) 0.0180(4) 0.0185(4) 0.0055(3) -0.0022(3) -0.0072(4) C3 0.0158(5) 0.0135(5) 0.0115(5) 0.0018(4) 0.0009(4) 0.0008(4) O4 0.0210(4) 0.0196(4) 0.0129(4) 0.0031(3) -0.0025(3) 0.0006(3) C4 0.0154(5) 0.0139(5) 0.0108(5) 0.0000(4) -0.0005(4) 0.0006(4) O5 0.0190(4) 0.0150(4) 0.0142(4) 0.0019(3) -0.0039(3) -0.0033(3) C5 0.0149(4) 0.0119(5) 0.0120(5) 0.0000(4) 0.0006(4) 0.0000(4) C6 0.0177(5) 0.0137(5) 0.0114(5) 0.0012(4) -0.0007(4) 0.0006(4) O6 0.0214(4) 0.0127(4) 0.0151(4) 0.0019(3) -0.0038(3) 0.0010(3) C7 0.0236(5) 0.0154(5) 0.0143(5) 0.0000(4) -0.0027(4) -0.0013(4) C8 0.0174(5) 0.0148(5) 0.0120(5) 0.0025(4) 0.0022(4) 0.0023(4) C9 0.0169(5) 0.0127(5) 0.0084(4) 0.0004(3) 0.0011(3) -0.0002(4) N1 0.0178(4) 0.0154(4) 0.0133(4) 0.0006(3) -0.0003(3) 0.0008(3) N2 0.0194(4) 0.0145(5) 0.0196(5) 0.0015(4) -0.0006(4) 0.0006(3) N3 0.0200(5) 0.0155(5) 0.0184(5) 0.0035(4) -0.0018(4) 0.0002(4) N4 0.0185(5) 0.0168(5) 0.0143(4) 0.0001(3) 0.0002(3) 0.0004(3) O7 0.0239(4) 0.0147(4) 0.0200(4) 0.0025(3) 0.0000(3) 0.0015(3) O8 0.0357(5) 0.0174(4) 0.0281(5) 0.0067(3) -0.0067(4) -0.0029(4) C10 0.0204(5) 0.0148(5) 0.0191(5) -0.0026(4) -0.0007(4) -0.0006(4) C11 0.0216(5) 0.0188(5) 0.0160(5) -0.0020(4) 0.0015(4) 0.0012(4) C12 0.0157(5) 0.0154(5) 0.0173(5) 0.0015(4) 0.0035(4) 0.0010(4) C13 0.0182(5) 0.0170(5) 0.0183(5) 0.0021(4) 0.0022(4) 0.0009(4) C14 0.0206(5) 0.0201(6) 0.0148(5) 0.0002(4) 0.0006(4) 0.0006(4) C15 0.0210(5) 0.0173(5) 0.0138(5) 0.0029(4) -0.0002(4) 0.0026(4) S1 0.02941(18) 0.01457(16) 0.01840(16) -0.00094(9) 0.00443(11) -0.00081(10) O9 0.0512(6) 0.0216(5) 0.0207(4) 0.0030(3) -0.0074(4) -0.0019(4) C16 0.0291(6) 0.0301(7) 0.0193(6) -0.0014(5) 0.0060(5) -0.0019(5) C17 0.0295(7) 0.0244(7) 0.0449(8) -0.0006(6) 0.0161(6) -0.0010(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 '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 C7 O1 H1 108.4(13) . . C2 C1 C7 119.26(10) . . C6 C1 C2 119.72(10) . . C6 C1 C7 120.98(10) . . C1 C2 H2A 119.6(10) . . C3 C2 C1 120.62(10) . . C3 C2 H2A 119.7(10) . . C2 C3 C4 119.18(10) . . C2 C3 C8 120.17(10) . . C4 C3 C8 120.63(9) . . C3 C4 H4 118.9(10) . . C3 C4 C5 120.55(9) . . C5 C4 H4 120.5(10) . . C4 C5 C9 122.32(9) . . C6 C5 C4 119.41(10) . . C6 C5 C9 118.26(9) . . C1 C6 C5 120.31(10) . . C1 C6 H6 120.5(9) . . C5 C6 H6 119.1(10) . . O1 C7 C1 112.75(10) . . O2 C7 O1 123.69(10) . . O2 C7 C1 123.54(10) . . O3 C8 C3 117.67(10) . . O3 C8 O4 125.68(10) . . O4 C8 C3 116.64(9) . . O5 C9 C5 119.27(9) . . O5 C9 O6 123.57(10) . . O6 C9 C5 117.16(9) . . H1A N1 H1B 108.1(15) . . H1A N1 H1C 108.7(15) . . H1B N1 H1C 108.6(16) . . C10 N1 H1A 109.6(11) . . C10 N1 H1B 110.6(11) . . C10 N1 H1C 111.2(12) . . C11 N2 H2 115.3(11) . . C12 N2 H2 122.1(11) . . C12 N2 C11 122.60(10) . . C13 N3 H3 118.6(11) . . C13 N3 C14 122.54(10) . . C14 N3 H3 118.9(11) . . H4A N4 H4B 109.0(15) . . H4A N4 H4C 106.0(15) . . H4B N4 H4C 107.1(16) . . C15 N4 H4A 110.9(11) . . C15 N4 H4B 112.5(12) . . C15 N4 H4C 110.9(11) . . N1 C10 H10A 106.6(10) . . N1 C10 H10B 108.9(10) . . N1 C10 C11 110.94(9) . . H10A C10 H10B 109.1(14) . . C11 C10 H10A 111.0(10) . . C11 C10 H10B 110.2(10) . . N2 C11 H11A 108.7(9) . . N2 C11 H11B 108.6(10) . . N2 C11 C10 112.25(9) . . H11A C11 H11B 108.8(13) . . C10 C11 H11A 110.2(9) . . C10 C11 H11B 108.2(10) . . N2 C12 C13 114.03(10) . . O7 C12 N2 125.31(10) . . O7 C12 C13 120.66(10) . . N3 C13 C12 112.49(10) . . O8 C13 N3 125.53(11) . . O8 C13 C12 121.98(10) . . N3 C14 H14A 107.0(10) . . N3 C14 H14B 107.2(9) . . N3 C14 C15 112.21(9) . . H14A C14 H14B 110.3(14) . . C15 C14 H14A 110.2(9) . . C15 C14 H14B 109.8(9) . . N4 C15 H15A 106.5(9) . . N4 C15 H15B 107.8(10) . . N4 C15 C14 110.48(9) . . H15A C15 H15B 109.8(13) . . C14 C15 H15A 111.3(9) . . C14 C15 H15B 110.8(10) . . O9 S1 C16 105.66(6) . . O9 S1 C17 105.32(7) . . C16 S1 C17 97.49(7) . . S1 C16 H16A 104.5(13) . . S1 C16 H16B 108.4(11) . . S1 C16 H16C 108.1(12) . . H16A C16 H16B 110.6(17) . . H16A C16 H16C 112.0(17) . . H16B C16 H16C 112.8(16) . . S1 C17 H17A 106.2(14) . . S1 C17 H17B 108.8(11) . . S1 C17 H17C 111.5(12) . . H17A C17 H17B 111.9(18) . . H17A C17 H17C 109.9(18) . . H17B C17 H17C 108.5(17) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 H1 0.93(2) . O1 C7 1.3244(14) . C1 C2 1.3943(15) . C1 C6 1.3923(15) . C1 C7 1.4969(14) . C2 H2A 0.930(17) . C2 C3 1.3933(15) . O2 C7 1.2111(16) . O3 C8 1.2525(14) . C3 C4 1.3973(15) . C3 C8 1.5242(14) . O4 C8 1.2632(14) . C4 H4 0.928(16) . C4 C5 1.3994(14) . O5 C9 1.2612(13) . C5 C6 1.3949(14) . C5 C9 1.5125(14) . C6 H6 0.945(16) . O6 C9 1.2644(13) . N1 H1A 0.932(18) . N1 H1B 0.877(19) . N1 H1C 0.894(19) . N1 C10 1.4908(14) . N2 H2 0.918(19) . N2 C11 1.4544(14) . N2 C12 1.3258(15) . N3 H3 0.868(18) . N3 C13 1.3319(15) . N3 C14 1.4550(14) . N4 H4A 0.902(17) . N4 H4B 0.87(2) . N4 H4C 0.910(18) . N4 C15 1.4900(14) . O7 C12 1.2317(14) . O8 C13 1.2298(15) . C10 H10A 0.949(17) . C10 H10B 0.980(18) . C10 C11 1.5176(16) . C11 H11A 0.993(16) . C11 H11B 0.977(18) . C12 C13 1.5409(15) . C14 H14A 0.977(17) . C14 H14B 0.963(17) . C14 C15 1.5185(16) . C15 H15A 0.986(17) . C15 H15B 0.954(17) . S1 O9 1.5046(10) . S1 C16 1.7820(13) . S1 C17 1.7903(15) . C16 H16A 0.96(2) . C16 H16B 0.97(2) . C16 H16C 0.99(2) . C17 H17A 0.94(2) . C17 H17B 0.95(2) . C17 H17C 0.96(2) . 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 O1 H1 O5 0.93(2) 1.65(2) 2.5767(11) 176.1(19) 4_666 yes N1 H1A O6 0.932(18) 1.996(18) 2.9257(13) 175.9(16) 2_656 yes N1 H1B O4 0.877(19) 1.996(19) 2.8099(13) 153.7(16) 3_666 yes N1 H1C O3 0.894(19) 1.94(2) 2.7985(13) 159.9(17) . yes N2 H2 O9 0.918(19) 2.014(19) 2.7848(14) 140.6(15) . yes N3 H3 O6 0.868(18) 2.169(18) 3.0125(13) 163.9(15) 4_565 yes N4 H4A O4 0.902(17) 1.938(18) 2.8092(13) 161.6(16) 3_566 yes N4 H4B O5 0.87(2) 2.03(2) 2.8849(13) 166.7(16) 4_565 yes N4 H4C O6 0.910(18) 2.048(18) 2.9315(12) 163.3(15) 2_556 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 C1 C2 C3 C4 -0.38(16) . . . . C1 C2 C3 C8 177.91(10) . . . . C2 C1 C6 C5 -4.08(16) . . . . C2 C1 C7 O1 -172.91(10) . . . . C2 C1 C7 O2 8.61(18) . . . . C2 C3 C4 C5 -3.48(15) . . . . C2 C3 C8 O3 9.20(15) . . . . C2 C3 C8 O4 -169.79(10) . . . . C3 C4 C5 C6 3.54(15) . . . . C3 C4 C5 C9 -175.39(9) . . . . C4 C3 C8 O3 -172.54(10) . . . . C4 C3 C8 O4 8.47(15) . . . . C4 C5 C6 C1 0.27(15) . . . . C4 C5 C9 O5 -29.40(15) . . . . C4 C5 C9 O6 149.69(10) . . . . C6 C1 C2 C3 4.14(17) . . . . C6 C1 C7 O1 9.28(15) . . . . C6 C1 C7 O2 -169.20(12) . . . . C6 C5 C9 O5 151.66(10) . . . . C6 C5 C9 O6 -29.25(14) . . . . C7 C1 C2 C3 -173.69(10) . . . . C7 C1 C6 C5 173.72(10) . . . . C8 C3 C4 C5 178.25(9) . . . . C9 C5 C6 C1 179.24(9) . . . . N1 C10 C11 N2 -72.23(12) . . . . N2 C12 C13 N3 -170.27(10) . . . . N2 C12 C13 O8 9.49(16) . . . . N3 C14 C15 N4 -52.57(13) . . . . O7 C12 C13 N3 8.89(15) . . . . O7 C12 C13 O8 -171.35(11) . . . . C11 N2 C12 O7 -2.39(17) . . . . C11 N2 C12 C13 176.72(9) . . . . C12 N2 C11 C10 96.92(12) . . . . C13 N3 C14 C15 -90.50(13) . . . . C14 N3 C13 O8 2.71(19) . . . . C14 N3 C13 C12 -177.54(10) . . . . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 168327391