# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/253 # Note CIF for structure 6 only data_global #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 1999-05-11 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _audit_update_record ? #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Coles, Simon J.' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton, SO17 1BJ England UK ; _publ_contact_author_email s.j.coles@soton.ac.uk _publ_contact_author_fax '44(1703)596723' _publ_contact_author_phone '44(1703)596722' _publ_requested_journal 'Acta Crystallographica Section C' _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; 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 'Coles, Simon J.' ; Department of Chemistry University of Southampton Southampton SO17 1BJ England 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. Beurskens, P.T., Beurskens, G., Bosman, W.P., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF96 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 (1992). CAD4Express Software. Enraf-Nonius, Delft, The Netherlands. Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565. Farrugia, L. J. (1998) WinGX - A Windows Program for Crystal Structure Analysis, University of Glasgow, Scotland. 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. Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G., and 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. and Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. and Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. Walker, N. and 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 DETAILS ----------------------------# data_s92 _audit_creation_date 1999-05-11T16:40:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C23 H28 N4 O4 S2' _chemical_formula_weight 488.61 #------------------ UNIT CELL INFORMATION -----------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9200(10) _cell_length_b 9.8450(10) _cell_length_c 26.8780(10) _cell_angle_alpha 90 _cell_angle_beta 92.23(2) _cell_angle_gamma 90 _cell_volume 2358.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.264 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_reflns_number 22873 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 23.24 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_max 0.899 _diffrn_measured_fraction_theta_full 0.899 _reflns_number_total 3233 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3233 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.1399 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.284 _refine_diff_density_max 0.161 _refine_diff_density_min -0.25 #------------------ 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' 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 0.03744(9) 0.93579(7) 0.18012(3) 0.0659(3) Uani 1 d . . . S2 S 0.00771(8) 1.74802(8) -0.04498(3) 0.0627(3) Uani 1 d . . . O1 O 0.36964(17) 1.29361(17) 0.11935(6) 0.0464(4) Uani 1 d . . . O2 O -0.08158(17) 1.42358(18) 0.18947(7) 0.0517(5) Uani 1 d . . . O3 O 0.37190(16) 1.50209(17) 0.06422(6) 0.0463(4) Uani 1 d . . . O4 O -0.09239(16) 1.62268(17) 0.12811(6) 0.0489(5) Uani 1 d . . . HA H -0.069(5) 1.518(5) 0.1643(19) 0.157(17) Uiso 1 d . . . HB H 0.370(5) 1.412(5) 0.0927(18) 0.141(14) Uiso 1 d . . . N1 N 0.2132(2) 1.13790(18) 0.15128(7) 0.0412(5) Uani 1 d . . . N2 N -0.0094(2) 1.2030(2) 0.18766(7) 0.0437(5) Uani 1 d . . . N3 N 0.19715(19) 1.61798(18) 0.01738(7) 0.0386(5) Uani 1 d . . . N4 N -0.03586(19) 1.67342(18) 0.04866(7) 0.0395(5) Uani 1 d . . . C1 C 0.1997(2) 1.5240(2) 0.15515(8) 0.0347(5) Uani 1 d . . . H1 H 0.133 1.5718 0.1774 0.042 Uiso 1 calc R . . C2 C 0.3586(2) 1.5630(2) 0.17418(8) 0.0359(5) Uani 1 d . . . C3 C 0.4241(3) 1.6824(3) 0.15875(11) 0.0534(7) Uani 1 d . . . H3 H 0.374 1.7365 0.1351 0.064 Uiso 1 calc R . . C4 C 0.5632(3) 1.7220(3) 0.17810(12) 0.0632(8) Uani 1 d . . . H4 H 0.6052 1.8029 0.1674 0.076 Uiso 1 calc R . . C5 C 0.6400(3) 1.6447(3) 0.21256(11) 0.0587(8) Uani 1 d . . . H5 H 0.7338 1.6719 0.2252 0.07 Uiso 1 calc R . . C6 C 0.5765(3) 1.5263(3) 0.22835(10) 0.0576(7) Uani 1 d . . . H6 H 0.6276 1.4727 0.2519 0.069 Uiso 1 calc R . . C7 C 0.4368(3) 1.4859(3) 0.20945(9) 0.0473(6) Uani 1 d . . . H7 H 0.3949 1.4056 0.2207 0.057 Uiso 1 calc R . . C8 C 0.1608(2) 1.3750(2) 0.16131(8) 0.0359(5) Uani 1 d . . . C9 C 0.2517(3) 1.2728(2) 0.14333(8) 0.0372(6) Uani 1 d . . . C10 C 0.3177(3) 1.0328(2) 0.13366(10) 0.0511(7) Uani 1 d . . . H10A H 0.3129 0.9537 0.155 0.061 Uiso 1 calc R . . H10B H 0.4194 1.0678 0.1362 0.061 Uiso 1 calc R . . C11 C 0.2818(4) 0.9910(3) 0.08072(11) 0.0682(8) Uani 1 d . . . H11A H 0.3548 0.9262 0.0704 0.102 Uiso 1 calc R . . H11B H 0.2839 1.0694 0.0595 0.102 Uiso 1 calc R . . H11C H 0.1838 0.9507 0.0785 0.102 Uiso 1 calc R . . C12 C 0.0821(3) 1.0983(2) 0.17326(8) 0.0440(6) Uani 1 d . . . C13 C -0.1536(3) 1.1722(3) 0.21093(11) 0.0577(7) Uani 1 d . . . H13A H -0.1747 1.2424 0.235 0.069 Uiso 1 calc R . . H13B H -0.1448 1.0865 0.2286 0.069 Uiso 1 calc R . . C14 C -0.2826(3) 1.1637(4) 0.17282(13) 0.0828(10) Uani 1 d . . . H14A H -0.3733 1.1423 0.1892 0.124 Uiso 1 calc R . . H14B H -0.2623 1.094 0.149 0.124 Uiso 1 calc R . . H14C H -0.2939 1.2494 0.156 0.124 Uiso 1 calc R . . C15 C 0.0242(2) 1.3380(2) 0.17940(8) 0.0391(6) Uani 1 d . . . C16 C 0.1543(2) 1.5752(2) 0.10359(8) 0.0337(5) Uani 1 d . . . C17 C 0.2427(2) 1.5625(2) 0.06297(8) 0.0368(5) Uani 1 d . . . C18 C 0.3068(3) 1.6203(3) -0.02267(9) 0.0465(6) Uani 1 d . . . H18A H 0.2535 1.6148 -0.0548 0.056 Uiso 1 calc R . . H18B H 0.3719 1.5416 -0.0193 0.056 Uiso 1 calc R . . C19 C 0.4004(3) 1.7475(3) -0.02058(12) 0.0641(8) Uani 1 d . . . H19A H 0.4689 1.7467 -0.0473 0.096 Uiso 1 calc R . . H19B H 0.4559 1.7515 0.0107 0.096 Uiso 1 calc R . . H19C H 0.3361 1.8255 -0.0239 0.096 Uiso 1 calc R . . C20 C 0.0583(2) 1.6780(2) 0.00951(9) 0.0407(6) Uani 1 d . . . C21 C -0.1907(2) 1.7288(2) 0.04260(10) 0.0477(6) Uani 1 d . . . H21A H -0.2565 1.6781 0.0637 0.057 Uiso 1 calc R . . H21B H -0.2265 1.7166 0.0083 0.057 Uiso 1 calc R . . C22 C -0.1984(3) 1.8758(3) 0.05566(12) 0.0636(8) Uani 1 d . . . H22A H -0.3003 1.9066 0.0518 0.095 Uiso 1 calc R . . H22B H -0.1366 1.9269 0.034 0.095 Uiso 1 calc R . . H22C H -0.1632 1.8884 0.0896 0.095 Uiso 1 calc R . . C23 C 0.0073(2) 1.6235(2) 0.09523(9) 0.0376(5) Uani 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 0.0872(6) 0.0443(5) 0.0654(5) 0.0118(3) -0.0075(4) -0.0099(3) S2 0.0672(5) 0.0786(6) 0.0412(4) 0.0116(3) -0.0107(3) 0.0133(4) O1 0.0453(10) 0.0480(10) 0.0465(10) -0.0012(8) 0.0090(8) 0.0085(7) O2 0.0477(10) 0.0556(11) 0.0529(11) 0.0073(9) 0.0165(8) 0.0112(8) O3 0.0421(9) 0.0531(10) 0.0440(10) 0.0008(8) 0.0067(7) 0.0175(7) O4 0.0407(9) 0.0563(11) 0.0505(11) 0.0080(8) 0.0101(8) 0.0126(7) N1 0.0500(12) 0.0356(11) 0.0375(11) -0.0022(9) -0.0061(9) 0.0068(8) N2 0.0493(12) 0.0461(12) 0.0355(11) 0.0063(9) -0.0003(9) -0.0027(9) N3 0.0435(11) 0.0394(11) 0.0330(11) 0.0006(8) 0.0012(8) 0.0055(8) N4 0.0346(10) 0.0383(11) 0.0451(12) 0.0031(9) -0.0053(9) 0.0052(8) C1 0.0375(12) 0.0358(13) 0.0308(12) -0.0035(10) 0.0019(9) 0.0074(9) C2 0.0391(12) 0.0355(12) 0.0331(12) -0.0060(10) 0.0027(10) 0.0059(10) C3 0.0567(16) 0.0405(14) 0.0617(17) 0.0026(12) -0.0129(13) 0.0011(12) C4 0.0617(17) 0.0555(17) 0.072(2) -0.0073(15) -0.0020(15) -0.0154(13) C5 0.0444(15) 0.071(2) 0.0597(18) -0.0198(15) -0.0058(13) 0.0023(13) C6 0.0535(16) 0.0692(19) 0.0489(16) -0.0064(14) -0.0148(13) 0.0149(14) C7 0.0528(14) 0.0510(15) 0.0376(14) 0.0021(11) -0.0069(11) 0.0033(11) C8 0.0389(12) 0.0390(13) 0.0295(12) 0.0014(10) 0.0004(10) 0.0039(9) C9 0.0419(13) 0.0387(14) 0.0307(12) -0.0004(10) -0.0045(10) 0.0055(10) C10 0.0630(16) 0.0393(14) 0.0506(16) 0.0010(12) -0.0055(12) 0.0137(11) C11 0.100(2) 0.0537(17) 0.0506(17) -0.0097(14) -0.0007(15) 0.0206(15) C12 0.0521(14) 0.0465(15) 0.0326(13) 0.0043(11) -0.0090(11) 0.0002(11) C13 0.0572(16) 0.0654(17) 0.0512(16) 0.0086(14) 0.0106(13) -0.0113(13) C14 0.0537(18) 0.114(3) 0.081(2) -0.0019(19) 0.0002(16) -0.0202(17) C15 0.0445(13) 0.0437(14) 0.0293(13) 0.0027(10) 0.0016(10) 0.0023(10) C16 0.0346(11) 0.0299(11) 0.0363(13) -0.0020(10) -0.0003(10) 0.0050(9) C17 0.0382(12) 0.0316(12) 0.0403(14) -0.0027(10) -0.0007(10) 0.0024(9) C18 0.0531(14) 0.0504(15) 0.0364(14) -0.0037(11) 0.0084(11) 0.0081(11) C19 0.0704(19) 0.0563(17) 0.068(2) -0.0050(14) 0.0313(16) -0.0022(14) C20 0.0421(13) 0.0389(13) 0.0407(14) -0.0012(11) -0.0042(11) 0.0000(10) C21 0.0348(13) 0.0516(15) 0.0557(16) 0.0022(12) -0.0097(11) 0.0090(10) C22 0.0607(17) 0.0563(17) 0.073(2) -0.0057(15) -0.0150(14) 0.0181(13) C23 0.0389(12) 0.0331(12) 0.0407(14) -0.0004(10) 0.0014(11) 0.0046(9) #------------------ 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 C12 1.661(3) . ? S2 C20 1.665(2) . ? O1 C9 1.272(3) . ? O2 C15 1.301(3) . ? O3 C17 1.296(3) . ? O4 C23 1.278(3) . ? N1 C12 1.386(3) . ? N1 C9 1.390(3) . ? N1 C10 1.482(3) . ? N2 C12 1.379(3) . ? N2 C15 1.383(3) . ? N2 C13 1.483(3) . ? N3 C20 1.381(3) . ? N3 C17 1.388(3) . ? N3 C18 1.482(3) . ? N4 C20 1.372(3) . ? N4 C23 1.385(3) . ? N4 C21 1.488(3) . ? C1 C16 1.515(3) . ? C1 C8 1.518(3) . ? C1 C2 1.537(3) . ? C2 C3 1.383(3) . ? C2 C7 1.381(3) . ? C3 C4 1.383(4) . ? C4 C5 1.362(4) . ? C5 C6 1.370(4) . ? C6 C7 1.386(3) . ? C8 C15 1.378(3) . ? C8 C9 1.391(3) . ? C10 C11 1.504(4) . ? C13 C14 1.512(4) . ? C16 C17 1.378(3) . ? C16 C23 1.405(3) . ? C18 C19 1.506(4) . ? C21 C22 1.491(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 C12 N1 C9 123.44(19) . . ? C12 N1 C10 119.4(2) . . ? C9 N1 C10 117.1(2) . . ? C12 N2 C15 122.6(2) . . ? C12 N2 C13 119.9(2) . . ? C15 N2 C13 117.5(2) . . ? C20 N3 C17 122.26(19) . . ? C20 N3 C18 119.69(19) . . ? C17 N3 C18 117.91(18) . . ? C20 N4 C23 123.22(18) . . ? C20 N4 C21 119.80(19) . . ? C23 N4 C21 116.93(19) . . ? C16 C1 C8 111.54(17) . . ? C16 C1 C2 115.58(18) . . ? C8 C1 C2 114.63(16) . . ? C3 C2 C7 117.7(2) . . ? C3 C2 C1 120.45(19) . . ? C7 C2 C1 121.72(19) . . ? C2 C3 C4 120.7(2) . . ? C5 C4 C3 121.2(3) . . ? C4 C5 C6 118.9(2) . . ? C5 C6 C7 120.5(2) . . ? C2 C7 C6 121.1(2) . . ? C15 C8 C9 117.8(2) . . ? C15 C8 C1 120.19(19) . . ? C9 C8 C1 121.5(2) . . ? O1 C9 C8 124.4(2) . . ? O1 C9 N1 116.46(19) . . ? C8 C9 N1 119.2(2) . . ? N1 C10 C11 112.3(2) . . ? N1 C12 N2 115.4(2) . . ? N1 C12 S1 121.87(18) . . ? N2 C12 S1 122.76(19) . . ? N2 C13 C14 112.0(2) . . ? O2 C15 C8 124.1(2) . . ? O2 C15 N2 115.2(2) . . ? C8 C15 N2 120.7(2) . . ? C17 C16 C23 117.6(2) . . ? C17 C16 C1 123.63(18) . . ? C23 C16 C1 118.27(19) . . ? O3 C17 C16 123.9(2) . . ? O3 C17 N3 115.7(2) . . ? C16 C17 N3 120.46(19) . . ? N3 C18 C19 111.5(2) . . ? N4 C20 N3 116.12(19) . . ? N4 C20 S2 122.36(16) . . ? N3 C20 S2 121.50(18) . . ? N4 C21 C22 112.4(2) . . ? O4 C23 N4 116.81(19) . . ? O4 C23 C16 123.9(2) . . ? N4 C23 C16 119.3(2) . . ?