#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:33 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306474 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064340.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_7064340 loop_ _publ_author_name 'Borth, Ketlyn Wolfart' 'Leal, Let\'icia dos Santos' 'Teixeira, Ver\^onica de Carvalho' 'da Rocha, Grazielli' 'Sim\~oes, Tatiana Renata Gomes' _publ_section_title ; Hybrid azine--oxamic acid molecular design: synthesis, structure, and supramolecular implications ; _journal_issue 18 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7619 _journal_page_last 7634 _journal_paper_doi 10.1039/D5NJ04656D _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C18 H14 N4 O6, 4(C2 H6 O S)' _chemical_formula_structural (C18H14N4O6)(C2H6OS4) _chemical_formula_sum 'C26 H38 N4 O10 S4' _chemical_formula_weight 694.8607 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary intrinsic-phasing _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2025-08-08 deposited with the CCDC. 2026-03-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.583(15) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.269(4) _cell_length_b 5.3039(6) _cell_length_c 24.374(4) _cell_measurement_reflns_used 9554 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 74.1966 _cell_measurement_theta_min 3.7594 _cell_volume 1652.3(6) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX4 (2022)' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Mercury (Cambridge Crystallographic Data Centre, 2019)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT-2015 (Sheldrick 2015a)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker D8 Venture/Photon 100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 73279 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.952 _diffrn_reflns_theta_min 3.458 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 3.144 _exptl_absorpt_correction_T_max 0.7538 _exptl_absorpt_correction_T_min 0.3634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.397 _exptl_crystal_description parallelepiped _exptl_crystal_F_000 732 _exptl_crystal_size_max 0.798 _exptl_crystal_size_mid 0.163 _exptl_crystal_size_min 0.152 _refine_diff_density_max 0.432 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 3183 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0328 _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^)+(0.0516P)^2^+0.9103P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.0886 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3106 _reflns_number_total 3183 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04656d2.cif _cod_data_source_block NN-H4oba _cod_depositor_comments 'Adding full bibliography for 7064339--7064340.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7064340 _shelx_shelxl_version_number 2017/1 _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_min 0.188 _shelx_estimated_absorpt_t_max 0.646 _shelx_res_file ; TITL shelxt_a.res in P2(1)/c shelx.res created by SHELXL-2017/1 at 08:54:40 on 08-Aug-2025 CELL 1.54178 13.2690 5.3039 24.3736 90.000 105.583 90.000 ZERR 4.00 0.0037 0.0006 0.0040 0.000 0.015 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 52 76 8 20 8 MERG 2 OMIT 0.00 142.00 OMIT 1 0 2 OMIT -2 0 10 OMIT 1 0 8 OMIT -1 0 12 OMIT -6 1 4 OMIT 0 0 2 OMIT -7 0 2 EQIV $2 x, -y+3/2, z+1/2 EQIV $3 -x+2, y+1/2, -z+3/2 HTAB C12 O5_$3 HTAB N1 N2 EQIV $4 -x+2, -y+1, -z+1 EQIV $5 x, y+1, z HTAB C11 O1_$5 HTAB C11 O1 HTAB C12 O2_$2 HTAB C13 O3_$2 HTAB O2 O4 HTAB C10 O3_$4 HTAB C10 O5 HTAB C11 O5 FMAP 2 PLAN 20 SIZE 0.152 0.163 0.798 ACTA BOND CONF LIST 4 L.S. 10 TEMP -173.05 WGHT 0.051600 0.910300 FVAR 0.20907 S1 5 0.894769 0.754527 0.553428 11.00000 0.02119 0.01624 = 0.01971 0.00008 0.00773 -0.00306 S2 5 0.819060 1.001670 0.741349 11.00000 0.03299 0.02703 = 0.02361 -0.00347 0.00980 -0.00510 O1 4 0.731069 0.332740 0.478060 11.00000 0.02707 0.02369 = 0.02477 -0.00346 0.01474 -0.00512 O2 4 0.848100 0.413351 0.428808 11.00000 0.02298 0.02388 = 0.02355 -0.00438 0.01184 -0.00728 O3 4 0.770906 0.025612 0.358569 11.00000 0.02290 0.02756 = 0.02183 -0.00370 0.01206 -0.00539 O4 4 0.885892 0.797985 0.490439 11.00000 0.02575 0.02219 = 0.01946 -0.00185 0.01087 -0.00620 O5 4 0.872232 0.899950 0.699057 11.00000 0.07485 0.03499 = 0.02719 -0.00598 0.02519 0.00331 N1 3 0.648613 -0.042376 0.408572 11.00000 0.01753 0.02210 = 0.01828 -0.00265 0.00831 -0.00317 N2 3 0.521184 -0.032845 0.477600 11.00000 0.01812 0.02703 = 0.02037 -0.00068 0.01035 -0.00081 C1 1 0.771065 0.289502 0.439594 11.00000 0.01842 0.01977 = 0.01875 0.00137 0.00631 -0.00075 C2 1 0.731155 0.073567 0.396904 11.00000 0.01700 0.02043 = 0.01825 0.00160 0.00600 -0.00055 C3 1 0.589076 -0.242529 0.380098 11.00000 0.01650 0.01883 = 0.01816 0.00169 0.00436 0.00022 C4 1 0.609917 -0.360595 0.333022 11.00000 0.01891 0.02342 = 0.02001 0.00094 0.00725 -0.00071 C5 1 0.548487 -0.559577 0.306202 11.00000 0.02563 0.02352 = 0.02141 -0.00206 0.00719 0.00079 C6 1 0.465494 -0.646858 0.325633 11.00000 0.02511 0.02435 = 0.02948 -0.00497 0.00669 -0.00635 C7 1 0.445182 -0.532540 0.372478 11.00000 0.02143 0.02698 = 0.03059 -0.00115 0.01047 -0.00608 C8 1 0.504881 -0.330186 0.400543 11.00000 0.01727 0.02201 = 0.02103 0.00125 0.00625 0.00013 C9 1 0.475403 -0.224297 0.449256 11.00000 0.01550 0.02537 = 0.02447 0.00195 0.00922 -0.00192 C10 1 0.962058 1.023165 0.588519 11.00000 0.02406 0.02348 = 0.02471 -0.00486 0.00903 -0.00631 C11 1 0.769071 0.823799 0.562806 11.00000 0.02196 0.03366 = 0.02375 -0.00264 0.01100 -0.00592 C12 1 0.911492 0.999744 0.807996 11.00000 0.05352 0.06756 = 0.02123 -0.00268 0.00362 0.02767 AFIX 33 H15 2 0.879399 1.065367 0.836911 11.00000 -1.50000 H14 2 0.935630 0.826773 0.817824 11.00000 -1.50000 H16 2 0.971121 1.106014 0.806515 11.00000 -1.50000 AFIX 0 C13 1 0.813176 1.334013 0.732139 11.00000 0.10777 0.03681 = 0.04372 0.01097 0.03294 0.02900 AFIX 33 H17 2 0.778786 1.409490 0.759073 11.00000 -1.50000 H18 2 0.884247 1.401579 0.739146 11.00000 -1.50000 H19 2 0.773247 1.374358 0.693116 11.00000 -1.50000 AFIX 0 H1 2 0.863000 0.562500 0.452151 11.00000 0.05775 H2 2 0.628808 0.020516 0.436704 11.00000 0.02920 H3 2 0.665837 -0.306222 0.320568 11.00000 0.02373 H4 2 0.563372 -0.636775 0.274398 11.00000 0.03234 H5 2 0.424139 -0.783061 0.307190 11.00000 0.03694 H6 2 0.390604 -0.592379 0.389943 11.00000 0.03369 H7 2 0.420673 -0.302950 0.458910 11.00000 0.01665 H8 2 1.031456 0.999525 0.589090 11.00000 0.03652 H9 2 0.928967 1.174268 0.568544 11.00000 0.02981 H10 2 0.954051 1.021829 0.625229 11.00000 0.02798 H11 2 0.748201 0.991640 0.547415 11.00000 0.04084 H12 2 0.772047 0.823807 0.600961 11.00000 0.03404 H13 2 0.722482 0.694505 0.543468 11.00000 0.03515 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0328 for 3106 Fo > 4sig(Fo) and 0.0334 for all 3183 data REM 251 parameters refined using 0 restraints END WGHT 0.0514 0.9210 REM Highest difference peak 0.432, deepest hole -0.376, 1-sigma level 0.061 Q1 1 0.7709 1.2185 0.7249 11.00000 0.05 0.43 Q2 1 0.7926 1.1746 0.7358 11.00000 0.05 0.42 Q3 1 0.9247 0.9151 0.5664 11.00000 0.05 0.38 Q4 1 0.9191 0.5939 0.5600 11.00000 0.05 0.34 Q5 1 0.7509 0.1792 0.4167 11.00000 0.05 0.29 Q6 1 0.8358 1.3350 0.7416 11.00000 0.05 0.28 Q7 1 0.7864 0.8530 0.7480 11.00000 0.05 0.26 Q8 1 0.5445 -0.2853 0.3904 11.00000 0.05 0.24 Q9 1 0.8303 0.8173 0.5586 11.00000 0.05 0.23 Q10 1 0.8673 0.7324 0.7072 11.00000 0.05 0.23 Q11 1 0.8840 1.1400 0.8299 11.00000 0.05 0.22 Q12 1 0.8204 1.3830 0.7131 11.00000 0.05 0.21 Q13 1 0.8699 1.0018 0.7769 11.00000 0.05 0.21 Q14 1 0.6089 -0.3296 0.3625 11.00000 0.05 0.21 Q15 1 0.4706 -0.3924 0.3786 11.00000 0.05 0.20 Q16 1 0.4871 -0.4409 0.3904 11.00000 0.05 0.18 Q17 1 0.5175 -0.6162 0.3240 11.00000 0.05 0.18 Q18 1 0.5908 -0.2697 0.3530 11.00000 0.05 0.18 Q19 1 0.8128 0.8240 0.6962 11.00000 0.05 0.18 Q20 1 0.5731 -0.4435 0.3195 11.00000 0.05 0.17 ; _shelx_res_checksum 27587 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S1 S 0.89477(2) 0.75453(6) 0.55343(2) 0.01861(12) Uani 1 1 d . . . . . S2 S 0.81906(3) 1.00167(7) 0.74135(2) 0.02745(13) Uani 1 1 d . . . . . O1 O 0.73107(8) 0.3327(2) 0.47806(4) 0.0237(2) Uani 1 1 d . . . . . O2 O 0.84810(8) 0.4134(2) 0.42881(4) 0.0224(2) Uani 1 1 d . . . . . O3 O 0.77091(8) 0.02561(19) 0.35857(4) 0.0229(2) Uani 1 1 d . . . . . O4 O 0.88589(8) 0.79799(19) 0.49044(4) 0.0215(2) Uani 1 1 d . . . . . O5 O 0.87223(12) 0.8999(2) 0.69906(5) 0.0435(3) Uani 1 1 d . . . . . N1 N 0.64861(9) -0.0424(2) 0.40857(5) 0.0186(2) Uani 1 1 d . . . . . N2 N 0.52118(9) -0.0328(2) 0.47760(5) 0.0208(3) Uani 1 1 d . . . . . C1 C 0.77107(10) 0.2895(3) 0.43959(6) 0.0187(3) Uani 1 1 d . . . . . C2 C 0.73115(10) 0.0736(3) 0.39690(6) 0.0183(3) Uani 1 1 d . . . . . C3 C 0.58908(10) -0.2425(2) 0.38010(6) 0.0179(3) Uani 1 1 d . . . . . C4 C 0.60992(11) -0.3606(3) 0.33302(6) 0.0204(3) Uani 1 1 d . . . . . C5 C 0.54849(11) -0.5596(3) 0.30620(6) 0.0234(3) Uani 1 1 d . . . . . C6 C 0.46549(12) -0.6469(3) 0.32563(7) 0.0264(3) Uani 1 1 d . . . . . C7 C 0.44518(11) -0.5325(3) 0.37248(7) 0.0257(3) Uani 1 1 d . . . . . C8 C 0.50488(10) -0.3302(3) 0.40054(6) 0.0199(3) Uani 1 1 d . . . . . C9 C 0.47540(11) -0.2243(3) 0.44926(6) 0.0210(3) Uani 1 1 d . . . . . C10 C 0.96206(12) 1.0232(3) 0.58852(7) 0.0236(3) Uani 1 1 d . . . . . C11 C 0.76907(11) 0.8238(3) 0.56281(7) 0.0255(3) Uani 1 1 d . . . . . C12 C 0.91149(17) 0.9997(4) 0.80800(7) 0.0487(5) Uani 1 1 d . . . . . H15 H 0.879399 1.065367 0.836911 0.073 Uiso 1 1 calc R U . . . H14 H 0.935630 0.826773 0.817824 0.073 Uiso 1 1 calc R U . . . H16 H 0.971121 1.106014 0.806515 0.073 Uiso 1 1 calc R U . . . C13 C 0.8132(2) 1.3340(4) 0.73214(9) 0.0603(7) Uani 1 1 d . . . . . H17 H 0.778786 1.409490 0.759073 0.091 Uiso 1 1 calc R U . . . H18 H 0.884247 1.401579 0.739146 0.091 Uiso 1 1 calc R U . . . H19 H 0.773247 1.374358 0.693116 0.091 Uiso 1 1 calc R U . . . H1 H 0.8630(19) 0.563(5) 0.4522(11) 0.058(7) Uiso 1 1 d . . . . . H2 H 0.6288(15) 0.021(4) 0.4367(9) 0.029(5) Uiso 1 1 d . . . . . H3 H 0.6658(14) -0.306(3) 0.3206(7) 0.024(4) Uiso 1 1 d . . . . . H4 H 0.5634(15) -0.637(4) 0.2744(8) 0.032(5) Uiso 1 1 d . . . . . H5 H 0.4241(17) -0.783(4) 0.3072(9) 0.037(5) Uiso 1 1 d . . . . . H6 H 0.3906(15) -0.592(4) 0.3899(8) 0.034(5) Uiso 1 1 d . . . . . H7 H 0.4207(13) -0.303(3) 0.4589(7) 0.017(4) Uiso 1 1 d . . . . . H8 H 1.0315(17) 1.000(4) 0.5891(9) 0.037(5) Uiso 1 1 d . . . . . H9 H 0.9290(15) 1.174(4) 0.5685(8) 0.030(5) Uiso 1 1 d . . . . . H10 H 0.9541(14) 1.022(3) 0.6252(9) 0.028(5) Uiso 1 1 d . . . . . H11 H 0.7482(17) 0.992(4) 0.5474(10) 0.041(6) Uiso 1 1 d . . . . . H12 H 0.7720(15) 0.824(4) 0.6010(9) 0.034(5) Uiso 1 1 d . . . . . H13 H 0.7225(16) 0.695(4) 0.5435(9) 0.035(5) Uiso 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 S1 0.02119(19) 0.01624(19) 0.01971(19) 0.00008(11) 0.00773(14) -0.00306(11) S2 0.0330(2) 0.0270(2) 0.0236(2) -0.00347(13) 0.00980(16) -0.00510(14) O1 0.0271(5) 0.0237(5) 0.0248(5) -0.0035(4) 0.0147(4) -0.0051(4) O2 0.0230(5) 0.0239(5) 0.0236(5) -0.0044(4) 0.0118(4) -0.0073(4) O3 0.0229(5) 0.0276(5) 0.0218(5) -0.0037(4) 0.0121(4) -0.0054(4) O4 0.0258(5) 0.0222(5) 0.0195(5) -0.0019(4) 0.0109(4) -0.0062(4) O5 0.0748(9) 0.0350(7) 0.0272(6) -0.0060(5) 0.0252(6) 0.0033(6) N1 0.0175(5) 0.0221(6) 0.0183(5) -0.0027(5) 0.0083(4) -0.0032(4) N2 0.0181(5) 0.0270(6) 0.0204(6) -0.0007(5) 0.0103(5) -0.0008(5) C1 0.0184(6) 0.0198(6) 0.0187(6) 0.0014(5) 0.0063(5) -0.0008(5) C2 0.0170(6) 0.0204(6) 0.0183(6) 0.0016(5) 0.0060(5) -0.0005(5) C3 0.0165(6) 0.0188(7) 0.0182(6) 0.0017(5) 0.0044(5) 0.0002(5) C4 0.0189(6) 0.0234(7) 0.0200(6) 0.0009(5) 0.0072(5) -0.0007(5) C5 0.0256(7) 0.0235(7) 0.0214(7) -0.0021(6) 0.0072(6) 0.0008(6) C6 0.0251(7) 0.0243(7) 0.0295(8) -0.0050(6) 0.0067(6) -0.0063(6) C7 0.0214(7) 0.0270(7) 0.0306(8) -0.0011(6) 0.0105(6) -0.0061(6) C8 0.0173(6) 0.0220(7) 0.0210(6) 0.0013(5) 0.0063(5) 0.0001(5) C9 0.0155(6) 0.0254(7) 0.0245(7) 0.0019(6) 0.0092(5) -0.0019(5) C10 0.0241(7) 0.0235(7) 0.0247(8) -0.0049(6) 0.0090(6) -0.0063(6) C11 0.0220(7) 0.0337(8) 0.0237(7) -0.0026(6) 0.0110(6) -0.0059(6) C12 0.0535(11) 0.0676(14) 0.0212(8) -0.0027(8) 0.0036(8) 0.0277(10) C13 0.108(2) 0.0368(11) 0.0437(11) 0.0110(9) 0.0329(12) 0.0290(12) 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' S S 0.3331 0.5567 '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 O4 S1 C10 104.87(7) . . ? O4 S1 C11 106.03(7) . . ? C10 S1 C11 98.03(8) . . ? O5 S2 C12 107.10(9) . . ? O5 S2 C13 106.47(9) . . ? C12 S2 C13 96.83(12) . . ? C2 N1 C3 128.73(12) . . ? C9 N2 N2 112.65(14) . 3_656 ? O1 C1 O2 126.16(13) . . ? O1 C1 C2 121.20(12) . . ? O2 C1 C2 112.64(11) . . ? O3 C2 N1 127.55(13) . . ? O3 C2 C1 122.15(12) . . ? N1 C2 C1 110.29(11) . . ? N1 C3 C4 122.66(12) . . ? N1 C3 C8 118.02(12) . . ? C4 C3 C8 119.31(13) . . ? C5 C4 C3 120.48(13) . . ? C4 C5 C6 120.84(14) . . ? C7 C6 C5 118.93(14) . . ? C6 C7 C8 122.03(13) . . ? C7 C8 C3 118.41(13) . . ? C7 C8 C9 116.94(12) . . ? C3 C8 C9 124.65(13) . . ? N2 C9 C8 123.39(13) . . ? 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 S1 O4 1.5254(10) . ? S1 C10 1.7744(15) . ? S1 C11 1.7815(15) . ? S2 O5 1.4974(12) . ? S2 C12 1.7529(19) . ? S2 C13 1.776(2) . ? O1 C1 1.2168(17) . ? O2 C1 1.2999(17) . ? O3 C2 1.2169(17) . ? N1 C2 1.3513(18) . ? N1 C3 1.3922(18) . ? N2 C9 1.2853(19) . ? N2 N2 1.400(2) 3_656 ? C1 C2 1.5423(19) . ? C3 C4 1.3984(19) . ? C3 C8 1.4183(19) . ? C4 C5 1.385(2) . ? C5 C6 1.390(2) . ? C6 C7 1.382(2) . ? C7 C8 1.399(2) . ? C8 C9 1.4586(19) . ? 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 C12 H16 O5 0.98 2.63 3.611(3) 178.5 2_756 yes N1 H2 N2 0.86(2) 1.97(2) 2.6871(17) 139.7(17) . yes C11 H11 O1 0.98(2) 2.44(2) 3.354(2) 154.7(17) 1_565 yes C11 H13 O1 0.96(2) 2.52(2) 3.2779(19) 136.4(15) . yes C12 H15 O2 0.98 2.39 3.305(2) 155.5 4_576 yes C13 H17 O3 0.98 2.48 3.361(2) 149.5 4_576 yes O2 H1 O4 0.96(3) 1.54(3) 2.5030(14) 179(2) . yes C10 H8 O3 0.93(2) 2.59(2) 3.439(2) 152.2(17) 3_766 yes C10 H10 O5 0.93(2) 2.43(2) 3.291(2) 155.0(16) . yes C11 H12 O5 0.92(2) 2.44(2) 3.259(2) 148.8(16) . 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 C3 N1 C2 O3 -0.1(2) . . . . ? C3 N1 C2 C1 179.02(12) . . . . ? O1 C1 C2 O3 -179.14(13) . . . . ? O2 C1 C2 O3 1.63(19) . . . . ? O1 C1 C2 N1 1.69(19) . . . . ? O2 C1 C2 N1 -177.54(11) . . . . ? C2 N1 C3 C4 1.3(2) . . . . ? C2 N1 C3 C8 -179.43(13) . . . . ? N1 C3 C4 C5 179.85(13) . . . . ? C8 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C5 C6 C7 C8 0.7(2) . . . . ? C6 C7 C8 C3 -0.4(2) . . . . ? C6 C7 C8 C9 179.61(14) . . . . ? N1 C3 C8 C7 -179.49(13) . . . . ? C4 C3 C8 C7 -0.2(2) . . . . ? N1 C3 C8 C9 0.5(2) . . . . ? C4 C3 C8 C9 179.73(13) . . . . ? N2 N2 C9 C8 -179.97(14) 3_656 . . . ? C7 C8 C9 N2 -177.49(14) . . . . ? C3 C8 C9 N2 2.6(2) . . . . ?