#============================================================================= data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 16 _journal_issue 2 _journal_year 2025 _journal_page_first 117 _journal_page_last 128 #============================================================================= #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-02-10 at 01:15:20 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\cifdoc.dat # CIF files read : fatma12(fa-09) #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_global #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2006-02-10 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Farrugia, Louis J.' _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ Scotland UK ; _publ_contact_author_email louis@chem.gla.ac.uk _publ_contact_author_fax '44(141)3304888' _publ_contact_author_phone '44(141)3305137' _publ_requested_journal 'Acta Crystallographica Section C' _publ_requested_coeditor_name ? # Include date of submission _publ_contact_letter ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Acta Crystallographica C. ; _publ_requested_category ? #------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------# _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #------------------ TITLE AND AUTHOR LIST------------------------------------# _publ_section_title ; ? ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address 'Farrugia, Louis J.' ; Department of Chemistry University of Glasgow Glasgow G12 8QQ Scotland UK ; #------------------ TEXT ----------------------------------------------------# _publ_section_synopsis ; # Insert blank lines between paragraphs ? ; _publ_section_abstract ; # Insert blank lines between paragraphs ? ; _publ_section_comment ; # Insert blank lines between paragraphs ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H., Kennard, O. & Taylor, R. (1983). Acc. Chem. Res. 16, 146-153. Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350. Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Beurskens, P.T., Beurskens, G., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft, The Netherlands. Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4 Diffractometer Data. University of Marburg, Germany. Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA. Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst, A24, 351-359 Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G., & Taylor, R. (1992). International Tables for Crystallography, Volume C. Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3, edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189. Oxford University Press. Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Spek, A.L. (1990). Acta Cryst. A46, C34 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; Figure 1. View of (I) (50% probability displacement ellipsoids) ; _publ_section_acknowledgements ; ? ; _publ_section_table_legends ; Table 1. Fractional atomic coordinates and equivalent isotropic displacement parameters (\%A^2^) Table 2. Selected geometric parameters (\%A ,\% ) ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_fatma12(fa-09) _audit_creation_date 2025-03-29 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_contact_author_address ? _audit_contact_author_email ? _audit_contact_author_name '' _audit_contact_author_phone ? _publ_contact_author_id_orcid ? #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H2 N3 O7, C10 H9 N2 S' _chemical_formula_sum 'C16 H11 N5 O7 S' _chemical_formula_weight 417.36 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #------------------ UNIT CELL INFORMATION -----------------------------------# _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.876(4) _cell_length_b 7.6675(18) _cell_length_c 13.846(3) _cell_angle_alpha 90 _cell_angle_beta 99.543(7) _cell_angle_gamma 90 _cell_volume 1766.9(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9389 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 23.36 _cell_measurement_theta_min 2.45 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details 'North et al., 1968' _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 30487 _diffrn_reflns_theta_full 26.74 _diffrn_reflns_theta_max 26.74 _diffrn_reflns_theta_min 1.2 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _reflns_number_gt 2600 _reflns_number_total 3741 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT (Bruker, 2007)' #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _refine_diff_density_max 0.3250 _refine_diff_density_min -0.2750 _refine_diff_density_rms 0.0400 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.0180 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 306 _refine_ls_number_reflns 3741 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0469 _refine_ls_restrained_S_all 1.0180 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #------------------ REFINEMENT INFORMATION ----------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+1.0050P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.1221 _olex2_refinement_description ; ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly S1 S 0.35884(4) 0.81768(11) 0.52046(5) 0.0699(3) Uani 1 d . . . O2 O 1.02559(10) 0.5317(3) 0.65054(13) 0.0659(5) Uani 1 d . . . O3 O 0.96094(11) 0.4156(3) 0.75738(12) 0.0658(5) Uani 1 d . . . O4 O 0.87592(12) 0.7957(2) 0.35546(13) 0.0674(5) Uani 1 d . . . N5 N 0.96278(12) 0.4944(3) 0.68034(13) 0.0477(5) Uani 1 d . . . O6 O 0.67398(10) 0.6730(3) 0.44581(12) 0.0670(5) Uani 1 d . . . N7 N 0.36272(12) 0.9419(3) 0.33781(15) 0.0489(5) Uani 1 d . . . N8 N 0.82060(12) 0.7004(3) 0.36927(13) 0.0504(5) Uani 1 d . . . N9 N 0.67355(12) 0.5575(3) 0.64573(15) 0.0522(5) Uani 1 d . . . O10 O 0.67367(11) 0.4520(3) 0.71259(15) 0.0756(6) Uani 1 d . . . O11 O 0.77168(12) 0.6419(3) 0.30252(13) 0.0839(7) Uani 1 d . . . N12 N 0.22472(11) 0.9335(3) 0.40230(14) 0.0508(5) Uani 1 d . . . O13 O 0.61619(12) 0.6516(3) 0.61716(16) 0.0872(7) Uani 1 d . . . C14 C 0.88737(12) 0.5437(3) 0.62081(14) 0.0379(5) Uani 1 d . . . C15 C 0.81626(13) 0.5232(3) 0.65667(16) 0.0390(5) Uani 1 d . . . C16 C 0.88750(14) 0.6095(3) 0.52740(15) 0.0389(5) Uani 1 d . . . C17 C 0.81612(13) 0.6458(3) 0.46950(14) 0.0391(5) Uani 1 d . . . C18 C 0.74518(12) 0.5721(3) 0.60035(15) 0.0402(5) Uani 1 d . . . C19 C 0.73772(13) 0.6348(3) 0.49949(16) 0.0425(5) Uani 1 d . . . C20 C 0.14469(15) 0.9580(4) 0.3812(2) 0.0528(6) Uani 1 d . . . C21 C 0.40335(14) 0.8651(3) 0.41810(18) 0.0508(6) Uani 1 d . . . C22 C 0.48438(16) 0.8249(4) 0.4194(2) 0.0621(8) Uani 1 d . . . C23 C 0.09334(18) 0.9122(4) 0.4434(2) 0.0592(7) Uani 1 d . . . C24 C 0.25425(15) 0.8620(3) 0.48886(17) 0.0492(6) Uani 1 d . . . C25 C 0.39700(15) 0.9787(4) 0.2591(2) 0.0563(6) Uani 1 d . . . C26 C 0.51976(17) 0.8638(4) 0.3405(2) 0.0657(8) Uani 1 d . . . C27 C 0.47572(16) 0.9406(4) 0.2593(2) 0.0643(7) Uani 1 d . . . C28 C 0.20682(19) 0.8143(4) 0.5567(2) 0.0612(7) Uani 1 d . . . C29 C 0.1252(2) 0.8407(4) 0.5333(2) 0.0668(8) Uani 1 d . . . H30 H 0.9370(13) 0.619(3) 0.5029(15) 0.040(6) Uiso 1 d . . . H31 H 0.8150(13) 0.478(3) 0.7187(18) 0.046(6) Uiso 1 d . . . H32 H 0.5771(18) 0.840(3) 0.343(2) 0.073(8) Uiso 1 d . . . H33 H 0.5058(16) 0.777(3) 0.470(2) 0.059(8) Uiso 1 d . . . H34 H 0.3631(16) 1.031(3) 0.205(2) 0.063(8) Uiso 1 d . . . H35 H 0.1270(17) 1.008(4) 0.322(2) 0.073(9) Uiso 1 d . . . H36 H 0.0369(17) 0.927(3) 0.4251(18) 0.063(8) Uiso 1 d . . . H37 H 0.2326(16) 0.764(3) 0.616(2) 0.064(8) Uiso 1 d . . . H38 H 0.0915(17) 0.808(4) 0.574(2) 0.071(9) Uiso 1 d . . . H39 H 0.4985(18) 0.963(4) 0.207(2) 0.078(10) Uiso 1 d . . . H40 H 0.3131(19) 0.960(4) 0.340(2) 0.078(10) 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 S1 0.0594(4) 0.0887(5) 0.0540(4) 0.0204(4) -0.0127(3) -0.0080(4) O2 0.0377(9) 0.1041(15) 0.0554(10) 0.0053(10) 0.0063(8) 0.0091(9) O3 0.0604(11) 0.0937(14) 0.0408(10) 0.0150(9) 0.0012(8) 0.0186(10) O4 0.0744(13) 0.0709(12) 0.0551(11) 0.0173(9) 0.0055(9) -0.0182(10) N5 0.0463(12) 0.0620(13) 0.0331(10) -0.0040(9) 0.0015(8) 0.0111(9) O6 0.0438(10) 0.0998(15) 0.0528(10) 0.0068(10) -0.0053(8) 0.0148(9) N7 0.0349(11) 0.0534(12) 0.0557(13) 0.0060(9) -0.0009(9) 0.0034(9) N8 0.0532(12) 0.0570(12) 0.0379(11) 0.0049(9) -0.0012(9) -0.0036(10) N9 0.0434(12) 0.0653(13) 0.0482(12) -0.0081(11) 0.0083(9) -0.0028(10) O10 0.0604(12) 0.0993(16) 0.0709(13) 0.0160(12) 0.0220(10) -0.0085(11) O11 0.0745(13) 0.1359(19) 0.0364(9) -0.0013(11) -0.0053(9) -0.0336(13) N12 0.0439(11) 0.0587(12) 0.0475(11) 0.0033(9) 0.0010(9) -0.0031(9) O13 0.0561(12) 0.1247(19) 0.0850(15) 0.0129(13) 0.0240(11) 0.0324(12) C14 0.0384(12) 0.0442(12) 0.0295(10) -0.0049(9) 0.0008(9) 0.0049(9) C15 0.0452(13) 0.0421(12) 0.0291(11) -0.0052(9) 0.0042(9) 0.0020(10) C16 0.0382(12) 0.0437(12) 0.0348(11) -0.0053(9) 0.0059(9) -0.0003(10) C17 0.0461(12) 0.0406(12) 0.0291(10) -0.0010(9) 0.0020(9) 0.0001(10) C18 0.0372(11) 0.0461(12) 0.0379(11) -0.0096(9) 0.0083(9) -0.0014(10) C19 0.0420(12) 0.0449(12) 0.0380(12) -0.0041(9) -0.0013(10) 0.0020(10) C20 0.0452(14) 0.0638(16) 0.0488(15) -0.0033(12) 0.0061(12) -0.0004(12) C21 0.0456(14) 0.0472(13) 0.0532(14) 0.0010(11) -0.0104(11) -0.0035(11) C22 0.0513(16) 0.0546(16) 0.0696(19) -0.0008(14) -0.0217(15) 0.0088(12) C23 0.0530(16) 0.0642(17) 0.0629(17) -0.0131(13) 0.0169(14) -0.0034(13) C24 0.0564(15) 0.0467(13) 0.0416(13) -0.0036(10) -0.0007(11) -0.0098(11) C25 0.0420(14) 0.0643(17) 0.0611(16) 0.0087(13) 0.0043(12) 0.0037(12) C26 0.0409(15) 0.0678(18) 0.085(2) -0.0132(16) 0.0015(15) 0.0064(13) C27 0.0444(15) 0.0744(19) 0.075(2) 0.0002(16) 0.0124(14) 0.0048(13) C28 0.081(2) 0.0586(16) 0.0431(15) -0.0023(12) 0.0066(14) -0.0064(14) C29 0.083(2) 0.0642(18) 0.0603(18) -0.0089(14) 0.0327(17) -0.0115(16) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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. ; 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 C21 1.749(3) . ? S1 C24 1.779(3) . ? O2 N5 1.233(2) . ? O3 N5 1.231(2) . ? O4 N8 1.225(3) . ? N5 C14 1.447(3) . ? O6 C19 1.237(3) . ? N7 C21 1.342(3) . ? N7 C25 1.346(3) . ? N7 H40 0.86(3) . ? N8 O11 1.218(2) . ? N8 C17 1.463(3) . ? N9 O10 1.229(3) . ? N9 O13 1.220(3) . ? N9 C18 1.456(3) . ? N12 C20 1.347(3) . ? N12 C24 1.337(3) . ? C14 C15 1.382(3) . ? C14 C16 1.389(3) . ? C15 C18 1.370(3) . ? C15 H31 0.93(2) . ? C16 C17 1.361(3) . ? C16 H30 0.96(2) . ? C17 C19 1.453(3) . ? C18 C19 1.462(3) . ? C20 C23 1.365(4) . ? C20 H35 0.91(3) . ? C21 C22 1.399(4) . ? C22 C26 1.362(4) . ? C22 H33 0.82(3) . ? C23 C29 1.384(4) . ? C23 H36 0.95(3) . ? C24 C28 1.381(4) . ? C25 C27 1.360(4) . ? C25 H34 0.95(3) . ? C26 C27 1.373(4) . ? C26 H32 0.98(3) . ? C27 H39 0.89(3) . ? C28 C29 1.376(4) . ? C28 H37 0.94(3) . ? C29 H38 0.90(3) . ? 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 C21 S1 C24 107.63(11) . . ? O2 N5 C14 118.20(19) . . ? O3 N5 O2 123.39(19) . . ? O3 N5 C14 118.40(19) . . ? C21 N7 C25 122.3(2) . . ? C21 N7 H40 114(2) . . ? C25 N7 H40 124(2) . . ? O4 N8 C17 118.64(19) . . ? O11 N8 O4 122.6(2) . . ? O11 N8 C17 118.6(2) . . ? O10 N9 C18 118.6(2) . . ? O13 N9 O10 122.4(2) . . ? O13 N9 C18 119.0(2) . . ? C24 N12 C20 117.6(2) . . ? C15 C14 N5 120.00(19) . . ? C15 C14 C16 120.77(19) . . ? C16 C14 N5 119.23(19) . . ? C14 C15 H31 121.9(14) . . ? C18 C15 C14 119.7(2) . . ? C18 C15 H31 118.5(14) . . ? C14 C16 H30 119.7(13) . . ? C17 C16 C14 119.0(2) . . ? C17 C16 H30 121.1(13) . . ? C16 C17 N8 115.9(2) . . ? C16 C17 C19 125.4(2) . . ? C19 C17 N8 118.70(18) . . ? N9 C18 C19 119.42(19) . . ? C15 C18 N9 116.4(2) . . ? C15 C18 C19 124.2(2) . . ? O6 C19 C17 123.8(2) . . ? O6 C19 C18 125.5(2) . . ? C17 C19 C18 110.70(18) . . ? N12 C20 C23 123.1(3) . . ? N12 C20 H35 115.0(18) . . ? C23 C20 H35 121.9(18) . . ? N7 C21 S1 122.25(19) . . ? N7 C21 C22 118.1(3) . . ? C22 C21 S1 119.6(2) . . ? C21 C22 H33 113.6(19) . . ? C26 C22 C21 120.0(3) . . ? C26 C22 H33 126.5(19) . . ? C20 C23 C29 118.4(3) . . ? C20 C23 H36 121.0(16) . . ? C29 C23 H36 120.6(16) . . ? N12 C24 S1 120.39(19) . . ? N12 C24 C28 123.1(2) . . ? C28 C24 S1 116.5(2) . . ? N7 C25 C27 120.3(3) . . ? N7 C25 H34 116.2(15) . . ? C27 C25 H34 123.4(15) . . ? C22 C26 C27 120.1(3) . . ? C22 C26 H32 119.6(16) . . ? C27 C26 H32 120.3(16) . . ? C25 C27 C26 119.3(3) . . ? C25 C27 H39 121(2) . . ? C26 C27 H39 120(2) . . ? C24 C28 H37 117.5(16) . . ? C29 C28 C24 118.1(3) . . ? C29 C28 H37 124.5(16) . . ? C23 C29 H38 118.7(18) . . ? C28 C29 C23 119.7(3) . . ? C28 C29 H38 121.5(18) . . ? 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 S1 C21 C22 C26 -179.0(2) . . . . ? S1 C24 C28 C29 -177.7(2) . . . . ? O2 N5 C14 C15 -172.3(2) . . . . ? O2 N5 C14 C16 8.4(3) . . . . ? O3 N5 C14 C15 8.6(3) . . . . ? O3 N5 C14 C16 -170.7(2) . . . . ? O4 N8 C17 C16 -38.4(3) . . . . ? O4 N8 C17 C19 141.5(2) . . . . ? N5 C14 C15 C18 179.22(19) . . . . ? N5 C14 C16 C17 176.07(19) . . . . ? N7 C21 C22 C26 0.0(4) . . . . ? N7 C25 C27 C26 0.2(4) . . . . ? N8 C17 C19 O6 -1.8(3) . . . . ? N8 C17 C19 C18 177.91(18) . . . . ? N9 C18 C19 O6 -2.4(3) . . . . ? N9 C18 C19 C17 177.88(19) . . . . ? O10 N9 C18 C15 -25.0(3) . . . . ? O10 N9 C18 C19 154.4(2) . . . . ? O11 N8 C17 C16 137.8(2) . . . . ? O11 N8 C17 C19 -42.4(3) . . . . ? N12 C20 C23 C29 1.5(4) . . . . ? N12 C24 C28 C29 0.6(4) . . . . ? O13 N9 C18 C15 154.0(2) . . . . ? O13 N9 C18 C19 -26.6(3) . . . . ? C14 C15 C18 N9 -175.99(19) . . . . ? C14 C15 C18 C19 4.7(3) . . . . ? C14 C16 C17 N8 -174.94(19) . . . . ? C14 C16 C17 C19 5.2(3) . . . . ? C15 C14 C16 C17 -3.2(3) . . . . ? C15 C18 C19 O6 176.9(2) . . . . ? C15 C18 C19 C17 -2.8(3) . . . . ? C16 C14 C15 C18 -1.5(3) . . . . ? C16 C17 C19 O6 178.0(2) . . . . ? C16 C17 C19 C18 -2.3(3) . . . . ? C20 N12 C24 S1 177.64(18) . . . . ? C20 N12 C24 C28 -0.5(4) . . . . ? C20 C23 C29 C28 -1.4(4) . . . . ? C21 S1 C24 N12 -5.2(2) . . . . ? C21 S1 C24 C28 173.05(19) . . . . ? C21 N7 C25 C27 -1.0(4) . . . . ? C21 C22 C26 C27 -0.8(4) . . . . ? C22 C26 C27 C25 0.7(4) . . . . ? C24 S1 C21 N7 7.6(2) . . . . ? C24 S1 C21 C22 -173.5(2) . . . . ? C24 N12 C20 C23 -0.5(4) . . . . ? C24 C28 C29 C23 0.4(4) . . . . ? C25 N7 C21 S1 179.9(2) . . . . ? C25 N7 C21 C22 0.9(4) . . . . ? _olex2_submission_special_instructions 'No special instructions were received'