# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_guanidinium 3-carboxybenzenesulfonate _database_code_CSD 145854 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Veneta Videnova-Adrabinska' 'El¿bieta Janeczko' 'Teresa Borowiak' 'Grzegorz Dutkiewicz' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H11 N3 O5 S' _chemical_formula_weight 261.26 _chemical_melting_point ? _chemical_compound_source ? 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' 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 7.701(2) _cell_length_b 30.779(6) _cell_length_c 9.425(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.98(3) _cell_angle_gamma 90.00 _cell_volume 2231.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method ? _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10958 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3914 _reflns_number_observed 3510 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+1.7148P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0172(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3914 _refine_ls_number_parameters 396 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_obs 0.0512 _refine_ls_wR_factor_all 0.1446 _refine_ls_wR_factor_obs 0.1346 _refine_ls_goodness_of_fit_all 1.226 _refine_ls_goodness_of_fit_obs 1.211 _refine_ls_restrained_S_all 1.226 _refine_ls_restrained_S_obs 1.211 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1B C 0.8698(4) 0.13021(9) 0.3954(3) 0.0340(6) Uani 1 d . . S1B S 0.86896(9) 0.18753(2) 0.38081(8) 0.0357(2) Uani 1 d . . O2B O 0.7083(3) 0.19878(8) 0.3048(3) 0.0629(7) Uani 1 d . . O1B O 1.0164(3) 0.19904(8) 0.3025(3) 0.0645(7) Uani 1 d . . O3B O 0.8783(3) 0.20457(7) 0.5244(3) 0.0543(6) Uani 1 d . . C2B C 0.8993(4) 0.10523(10) 0.2771(3) 0.0363(6) Uani 1 d . . C3B C 0.8940(4) 0.06018(10) 0.2858(3) 0.0399(7) Uani 1 d . . C7B C 0.9308(4) 0.03395(10) 0.1595(3) 0.0449(7) Uani 1 d . . O4B O 0.9568(4) 0.05100(8) 0.0440(3) 0.0637(7) Uani 1 d . . O5B O 0.9360(4) -0.00778(8) 0.1799(3) 0.0637(8) Uani 1 d . . C4B C 0.8578(5) 0.04044(11) 0.4127(4) 0.0542(9) Uani 1 d . . C5B C 0.8284(6) 0.06547(13) 0.5306(4) 0.0662(11) Uani 1 d . . C6B C 0.8342(5) 0.11052(12) 0.5220(4) 0.0519(9) Uani 1 d . . C8A C 0.9291(4) 0.18170(9) 0.9378(3) 0.0367(7) Uani 1 d . . N3A N 1.0759(4) 0.20396(11) 0.9486(3) 0.0497(7) Uani 1 d . . N2A N 0.7811(4) 0.20184(11) 0.9578(3) 0.0485(7) Uani 1 d . . N1A N 0.9305(5) 0.14033(9) 0.9038(4) 0.0503(7) Uani 1 d . . C1A C 0.4048(4) 0.08710(9) 1.0861(3) 0.0330(6) Uani 1 d . . S1A S 0.42660(9) 0.11798(2) 0.92952(7) 0.0364(2) Uani 1 d . . O1A O 0.5853(3) 0.10366(8) 0.8687(2) 0.0511(6) Uani 1 d . . O2A O 0.4289(3) 0.16336(7) 0.9717(2) 0.0464(5) Uani 1 d . . O3A O 0.2745(3) 0.10739(8) 0.8371(2) 0.0464(5) Uani 1 d . . O5A O 0.3326(5) 0.07542(9) 1.5789(3) 0.0720(9) Uani 1 d . . C3A C 0.3822(4) 0.08153(10) 1.3375(3) 0.0386(7) Uani 1 d . . O4A O 0.3807(4) 0.14183(8) 1.4934(2) 0.0611(7) Uani 1 d . . C2A C 0.3990(4) 0.10694(10) 1.2169(3) 0.0360(6) Uani 1 d . . C8B C 0.3795(4) 0.23708(9) 1.6969(3) 0.0343(6) Uani 1 d . . C7A C 0.3661(5) 0.10318(11) 1.4770(3) 0.0467(8) Uani 1 d . . C4A C 0.3750(5) 0.03663(11) 1.3252(3) 0.0468(8) Uani 1 d . . C6A C 0.3924(5) 0.04223(10) 1.0738(3) 0.0450(8) Uani 1 d . . C5A C 0.3793(5) 0.01705(11) 1.1936(4) 0.0544(9) Uani 1 d . . N2B N 0.5341(4) 0.22450(13) 1.6608(4) 0.0530(8) Uani 1 d . . N1B N 0.3621(5) 0.27042(10) 1.7804(3) 0.0488(7) Uani 1 d . . N3B N 0.2400(4) 0.21620(12) 1.6453(4) 0.0519(7) Uani 1 d . . H23B H 0.2514(50) 0.1942(13) 1.6064(42) 0.052(12) Uiso 1 d . . H13B H 0.1476(59) 0.2229(15) 1.6848(46) 0.068(13) Uiso 1 d . . H2B H 0.9230(44) 0.1167(11) 0.1932(38) 0.047(9) Uiso 1 d . . H2O5 H 0.9567(78) -0.0183(20) 0.1071(62) 0.110(21) Uiso 1 d . . H4B H 0.8584(49) 0.0107(13) 0.4183(39) 0.057(10) Uiso 1 d . . H5B H 0.8080(54) 0.0497(14) 0.6197(46) 0.072(12) Uiso 1 d . . H6B H 0.8188(61) 0.1260(16) 0.5935(52) 0.083(15) Uiso 1 d . . H23A H 1.0742(56) 0.2294(16) 0.9768(46) 0.067(13) Uiso 1 d . . H13A H 1.1667(49) 0.1909(12) 0.9481(37) 0.043(10) Uiso 1 d . . H22A H 0.6932(47) 0.1877(11) 0.9541(34) 0.036(9) Uiso 1 d . . H12A H 0.7838(57) 0.2260(16) 0.9856(47) 0.068(14) Uiso 1 d . . H21A H 0.8340(52) 0.1263(12) 0.8959(39) 0.052(10) Uiso 1 d . . H11A H 1.0228(56) 0.1289(13) 0.8884(43) 0.060(12) Uiso 1 d . . H2A H 0.4071(47) 0.1346(13) 1.2271(38) 0.052(10) Uiso 1 d . . H21B H 0.2496(58) 0.2804(13) 1.7952(41) 0.063(11) Uiso 1 d . . H11B H 0.4439(53) 0.2831(13) 1.8036(40) 0.049(12) Uiso 1 d . . H4A H 0.3619(52) 0.0195(13) 1.4056(43) 0.066(11) Uiso 1 d . . H6A H 0.3937(46) 0.0284(12) 0.9824(40) 0.053(10) Uiso 1 d . . H5A H 0.3742(53) -0.0135(15) 1.1841(43) 0.072(12) Uiso 1 d . . H22B H 0.5417(61) 0.2010(17) 1.6181(52) 0.082(16) Uiso 1 d . . H12B H 0.6263(50) 0.2373(12) 1.6962(37) 0.046(10) Uiso 1 d . . H1O5 H 0.3242(63) 0.0872(16) 1.6535(55) 0.086(16) 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 C1B 0.0289(14) 0.0325(14) 0.040(2) 0.0006(12) 0.0002(11) -0.0006(11) S1B 0.0309(4) 0.0300(4) 0.0464(4) -0.0010(3) 0.0025(3) 0.0002(3) O2B 0.0481(14) 0.0480(14) 0.090(2) 0.0055(13) -0.0227(13) 0.0070(11) O1B 0.059(2) 0.0475(14) 0.090(2) -0.0016(13) 0.0327(14) -0.0115(12) O3B 0.070(2) 0.0398(12) 0.0532(14) -0.0094(10) 0.0026(12) 0.0015(11) C2B 0.037(2) 0.0345(15) 0.038(2) 0.0030(12) 0.0054(12) 0.0031(12) C3B 0.043(2) 0.033(2) 0.044(2) -0.0019(13) 0.0043(13) 0.0022(13) C7B 0.055(2) 0.030(2) 0.050(2) -0.0006(14) 0.0065(15) 0.0040(14) O4B 0.103(2) 0.0409(13) 0.0491(14) 0.0002(11) 0.0183(14) 0.0153(13) O5B 0.100(2) 0.0330(13) 0.059(2) -0.0041(11) 0.015(2) 0.0031(13) C4B 0.076(2) 0.033(2) 0.054(2) 0.0041(15) 0.009(2) 0.000(2) C5B 0.108(3) 0.047(2) 0.045(2) 0.009(2) 0.016(2) -0.005(2) C6B 0.075(2) 0.043(2) 0.038(2) -0.0022(14) 0.008(2) -0.002(2) C8A 0.044(2) 0.0344(15) 0.0318(14) 0.0057(11) 0.0054(12) -0.0010(13) N3A 0.046(2) 0.039(2) 0.065(2) -0.0036(14) 0.0070(14) -0.0045(14) N2A 0.044(2) 0.038(2) 0.065(2) -0.0006(14) 0.0112(14) -0.0029(14) N1A 0.044(2) 0.036(2) 0.071(2) -0.0006(13) 0.0071(15) -0.0010(14) C1A 0.0339(14) 0.0370(15) 0.0284(14) -0.0002(11) 0.0036(11) 0.0007(11) S1A 0.0389(4) 0.0410(4) 0.0298(4) 0.0003(3) 0.0056(3) -0.0015(3) O1A 0.0434(12) 0.0629(15) 0.0487(13) -0.0013(11) 0.0178(10) -0.0010(11) O2A 0.0571(13) 0.0391(12) 0.0434(12) 0.0030(9) 0.0059(10) -0.0030(10) O3A 0.0435(12) 0.0639(15) 0.0316(11) -0.0011(10) -0.0007(9) 0.0006(10) O5A 0.126(3) 0.059(2) 0.0325(13) -0.0043(12) 0.0180(15) -0.012(2) C3A 0.044(2) 0.041(2) 0.0310(14) -0.0037(12) 0.0040(12) -0.0014(13) O4A 0.099(2) 0.0452(14) 0.0396(13) -0.0112(10) 0.0110(13) -0.0037(13) C2A 0.045(2) 0.0307(15) 0.0324(15) -0.0033(12) 0.0037(12) -0.0025(13) C8B 0.0331(14) 0.038(2) 0.0313(14) 0.0057(12) 0.0017(11) 0.0006(12) C7A 0.059(2) 0.049(2) 0.032(2) -0.0030(14) 0.0036(14) -0.003(2) C4A 0.064(2) 0.039(2) 0.038(2) 0.0046(14) 0.0106(15) -0.0016(15) C6A 0.060(2) 0.038(2) 0.037(2) -0.0079(13) 0.0105(14) -0.0003(14) C5A 0.086(3) 0.031(2) 0.048(2) -0.0033(14) 0.015(2) -0.004(2) N2B 0.041(2) 0.064(2) 0.054(2) -0.006(2) 0.0061(14) 0.008(2) N1B 0.046(2) 0.046(2) 0.055(2) -0.0093(13) 0.0094(14) -0.0012(14) N3B 0.050(2) 0.055(2) 0.051(2) -0.0056(15) 0.0034(14) -0.009(2) _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 C1B C6B 1.378(4) . ? C1B C2B 1.383(4) . ? C1B S1B 1.770(3) . ? S1B O1B 1.431(2) . ? S1B O2B 1.439(2) . ? S1B O3B 1.449(2) . ? C2B C3B 1.390(4) . ? C2B H2B 0.89(4) . ? C3B C4B 1.383(5) . ? C3B C7B 1.478(4) . ? C7B O4B 1.234(4) . ? C7B O5B 1.299(4) . ? O5B H2O5 0.78(6) . ? C4B C5B 1.380(5) . ? C4B H4B 0.92(4) . ? C5B C6B 1.390(5) . ? C5B H5B 0.99(4) . ? C6B H6B 0.84(5) . ? C8A N1A 1.313(4) . ? C8A N2A 1.320(4) . ? C8A N3A 1.321(4) . ? N3A H23A 0.83(5) . ? N3A H13A 0.81(4) . ? N2A H22A 0.80(4) . ? N2A H12A 0.79(5) . ? N1A H21A 0.86(4) . ? N1A H11A 0.81(4) . ? C1A C2A 1.379(4) . ? C1A C6A 1.389(4) . ? C1A S1A 1.770(3) . ? S1A O1A 1.445(2) . ? S1A O2A 1.452(2) . ? S1A O3A 1.460(2) . ? O5A C7A 1.320(4) . ? O5A H1O5 0.80(5) . ? C3A C4A 1.388(4) . ? C3A C2A 1.391(4) . ? C3A C7A 1.485(4) . ? O4A C7A 1.204(4) . ? C2A H2A 0.86(4) . ? C8B N1B 1.305(4) . ? C8B N2B 1.313(4) . ? C8B N3B 1.322(4) . ? C4A C5A 1.381(5) . ? C4A H4A 0.93(4) . ? C6A C5A 1.377(5) . ? C6A H6A 0.96(4) . ? C5A H5A 0.95(4) . ? N2B H22B 0.83(5) . ? N2B H12B 0.86(4) . ? N1B H21B 0.94(4) . ? N1B H11B 0.76(4) . ? N3B H23B 0.78(4) . ? N3B H13B 0.85(5) . ? 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 C6B C1B C2B 120.1(3) . . ? C6B C1B S1B 120.4(2) . . ? C2B C1B S1B 119.4(2) . . ? O1B S1B O2B 111.6(2) . . ? O1B S1B O3B 112.9(2) . . ? O2B S1B O3B 112.2(2) . . ? O1B S1B C1B 106.70(14) . . ? O2B S1B C1B 106.15(14) . . ? O3B S1B C1B 106.74(14) . . ? C1B C2B C3B 120.0(3) . . ? C1B C2B H2B 123.0(22) . . ? C3B C2B H2B 117.0(22) . . ? C4B C3B C2B 119.8(3) . . ? C4B C3B C7B 120.8(3) . . ? C2B C3B C7B 119.3(3) . . ? O4B C7B O5B 123.1(3) . . ? O4B C7B C3B 121.7(3) . . ? O5B C7B C3B 115.2(3) . . ? C7B O5B H2O5 106.7(44) . . ? C5B C4B C3B 120.0(3) . . ? C5B C4B H4B 120.8(24) . . ? C3B C4B H4B 119.2(24) . . ? C4B C5B C6B 120.2(3) . . ? C4B C5B H5B 116.8(25) . . ? C6B C5B H5B 123.0(25) . . ? C1B C6B C5B 119.8(3) . . ? C1B C6B H6B 119.2(33) . . ? C5B C6B H6B 121.0(33) . . ? N1A C8A N2A 120.5(3) . . ? N1A C8A N3A 120.3(3) . . ? N2A C8A N3A 119.2(3) . . ? C8A N3A H23A 119.2(31) . . ? C8A N3A H13A 118.6(26) . . ? H23A N3A H13A 120.1(40) . . ? C8A N2A H22A 118.1(24) . . ? C8A N2A H12A 118.8(33) . . ? H22A N2A H12A 122.2(41) . . ? C8A N1A H21A 119.4(25) . . ? C8A N1A H11A 118.8(30) . . ? H21A N1A H11A 121.8(40) . . ? C2A C1A C6A 120.6(3) . . ? C2A C1A S1A 121.1(2) . . ? C6A C1A S1A 118.3(2) . . ? O1A S1A O2A 113.77(14) . . ? O1A S1A O3A 111.37(14) . . ? O2A S1A O3A 112.10(14) . . ? O1A S1A C1A 106.58(14) . . ? O2A S1A C1A 106.77(13) . . ? O3A S1A C1A 105.63(13) . . ? C7A O5A H1O5 112.0(36) . . ? C4A C3A C2A 119.8(3) . . ? C4A C3A C7A 121.1(3) . . ? C2A C3A C7A 119.1(3) . . ? C1A C2A C3A 119.4(3) . . ? C1A C2A H2A 122.3(24) . . ? C3A C2A H2A 118.3(24) . . ? N1B C8B N2B 120.7(3) . . ? N1B C8B N3B 119.8(3) . . ? N2B C8B N3B 119.5(3) . . ? O4A C7A O5A 124.5(3) . . ? O4A C7A C3A 123.0(3) . . ? O5A C7A C3A 112.5(3) . . ? C5A C4A C3A 120.5(3) . . ? C5A C4A H4A 119.5(25) . . ? C3A C4A H4A 120.0(25) . . ? C5A C6A C1A 119.9(3) . . ? C5A C6A H6A 119.3(22) . . ? C1A C6A H6A 120.7(22) . . ? C6A C5A C4A 119.8(3) . . ? C6A C5A H5A 119.1(25) . . ? C4A C5A H5A 121.1(25) . . ? C8B N2B H22B 118.0(34) . . ? C8B N2B H12B 120.2(24) . . ? H22B N2B H12B 120.4(40) . . ? C8B N1B H21B 118.3(25) . . ? C8B N1B H11B 117.7(29) . . ? H21B N1B H11B 123.1(39) . . ? C8B N3B H23B 119.2(30) . . ? C8B N3B H13B 114.0(30) . . ? H23B N3B H13B 122.4(43) . . ? _refine_diff_density_max 0.424 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.083 data_guanidinium 4-carboxybenzenesulfonate _database_code_CSD 145855 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Veneta Videnova-Adrabinska' 'El¿bieta Janeczko' 'Teresa Borowiak' 'Grzegorz Dutkiewicz' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H11 N3 O5 S' _chemical_formula_weight 261.26 _chemical_melting_point ? _chemical_compound_source ? 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' 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 10.626(2) _cell_length_b 15.597(3) _cell_length_c 7.1820(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.38(2) _cell_angle_gamma 90.00 _cell_volume 1158.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method ? _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6766 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2264 _reflns_number_observed 2152 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.3627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0152(33) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2264 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_obs 0.0428 _refine_ls_wR_factor_all 0.1203 _refine_ls_wR_factor_obs 0.1180 _refine_ls_goodness_of_fit_all 1.115 _refine_ls_goodness_of_fit_obs 1.124 _refine_ls_restrained_S_all 1.115 _refine_ls_restrained_S_obs 1.124 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.28822(4) 0.56160(3) 0.04236(6) 0.0403(2) Uani 1 d . . C1 C 0.1629(2) 0.63522(11) -0.0554(2) 0.0370(4) Uani 1 d . . C2 C 0.1853(2) 0.72260(12) -0.0422(3) 0.0418(4) Uani 1 d . . C3 C 0.0847(2) 0.77875(11) -0.1127(3) 0.0425(4) Uani 1 d . . C4 C -0.0374(2) 0.74716(11) -0.1957(2) 0.0379(4) Uani 1 d . . C5 C -0.0586(2) 0.65942(12) -0.2093(3) 0.0449(4) Uani 1 d . . C6 C 0.0409(2) 0.60302(11) -0.1394(3) 0.0439(4) Uani 1 d . . C7 C -0.1476(2) 0.80588(12) -0.2712(3) 0.0441(4) Uani 1 d . . C8 C 0.5013(2) 0.62268(11) 0.6197(3) 0.0447(4) Uani 1 d . . O1 O 0.25084(14) 0.52031(9) 0.2011(2) 0.0545(4) Uani 1 d . . O2 O 0.40701(13) 0.61128(9) 0.0974(2) 0.0519(4) Uani 1 d . . O3 O 0.29420(13) 0.50217(8) -0.1130(2) 0.0482(3) Uani 1 d . . O4 O -0.25472(14) 0.78157(10) -0.3513(3) 0.0694(5) Uani 1 d . . O5 O -0.1176(2) 0.88685(10) -0.2432(3) 0.0581(4) Uani 1 d . . N1 N 0.3964(2) 0.57488(13) 0.5812(3) 0.0564(5) Uani 1 d . . N2 N 0.5556(2) 0.64777(14) 0.4817(3) 0.0628(5) Uani 1 d . . N3 N 0.5511(2) 0.64637(13) 0.7977(3) 0.0573(5) Uani 1 d . . H2 H 0.2644(24) 0.7431(17) 0.0119(35) 0.060(7) Uiso 1 d . . H3 H 0.0999(21) 0.8405(15) -0.1067(30) 0.049(5) Uiso 1 d . . H5 H -0.1370(24) 0.6386(16) -0.2634(35) 0.061(7) Uiso 1 d . . H6 H 0.0227(20) 0.5409(14) -0.1572(29) 0.045(5) Uiso 1 d . . HO5 H -0.1688(35) 0.9172(24) -0.2827(50) 0.094(11) Uiso 1 d . . H1N1 H 0.3708(26) 0.5618(16) 0.4836(41) 0.058(8) Uiso 1 d . . H2N1 H 0.3694(25) 0.5551(16) 0.6717(39) 0.060(7) Uiso 1 d . . H1N2 H 0.6135(29) 0.6846(20) 0.5047(41) 0.078(9) Uiso 1 d . . H2N2 H 0.5188(27) 0.6387(18) 0.3639(41) 0.072(8) Uiso 1 d . . H1N3 H 0.6182(26) 0.6722(18) 0.8173(36) 0.061(7) Uiso 1 d . . H2N3 H 0.5139(25) 0.6292(16) 0.8821(37) 0.060(7) 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 0.0372(3) 0.0392(3) 0.0407(3) -0.0002(2) 0.0009(2) -0.0005(2) C1 0.0374(9) 0.0374(8) 0.0347(8) -0.0002(6) 0.0057(6) -0.0008(7) C2 0.0366(9) 0.0401(9) 0.0453(9) -0.0026(7) 0.0027(7) -0.0064(7) C3 0.0442(10) 0.0341(9) 0.0474(9) -0.0011(7) 0.0068(7) -0.0055(7) C4 0.0376(9) 0.0378(9) 0.0369(8) 0.0025(6) 0.0058(7) -0.0007(7) C5 0.0371(9) 0.0424(10) 0.0508(10) 0.0005(8) 0.0013(7) -0.0064(7) C6 0.0416(9) 0.0339(9) 0.0520(10) 0.0000(7) 0.0022(7) -0.0048(7) C7 0.0435(10) 0.0404(9) 0.0462(9) 0.0049(7) 0.0059(7) -0.0011(7) C8 0.0467(10) 0.0354(9) 0.0468(9) 0.0005(7) 0.0004(8) 0.0026(7) O1 0.0586(8) 0.0559(8) 0.0452(7) 0.0120(6) 0.0043(6) -0.0015(7) O2 0.0380(7) 0.0541(8) 0.0571(8) -0.0052(6) -0.0024(6) -0.0045(6) O3 0.0463(7) 0.0437(7) 0.0526(8) -0.0075(6) 0.0076(6) 0.0004(5) O4 0.0437(8) 0.0492(8) 0.0994(13) 0.0087(8) -0.0155(8) -0.0018(6) O5 0.0512(8) 0.0381(7) 0.0775(10) 0.0032(7) -0.0003(7) 0.0033(6) N1 0.0607(11) 0.0634(11) 0.0420(10) -0.0043(8) 0.0053(9) -0.0176(9) N2 0.0712(13) 0.0616(12) 0.0511(11) 0.0016(9) 0.0048(9) -0.0245(10) N3 0.0563(11) 0.0600(11) 0.0496(10) -0.0097(8) 0.0002(9) -0.0065(9) _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 O1 1.4427(14) . ? S1 O2 1.4557(14) . ? S1 O3 1.4632(13) . ? S1 C1 1.775(2) . ? C1 C2 1.383(2) . ? C1 C6 1.391(2) . ? C2 C3 1.384(3) . ? C3 C4 1.387(2) . ? C4 C5 1.387(3) . ? C4 C7 1.487(2) . ? C5 C6 1.378(3) . ? C7 O4 1.211(2) . ? C7 O5 1.307(2) . ? C8 N1 1.316(3) . ? C8 N2 1.316(3) . ? C8 N3 1.318(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 O1 S1 O2 113.76(9) . . ? O1 S1 O3 112.84(9) . . ? O2 S1 O3 110.88(8) . . ? O1 S1 C1 106.42(8) . . ? O2 S1 C1 106.68(8) . . ? O3 S1 C1 105.61(8) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 S1 120.59(13) . . ? C6 C1 S1 118.45(13) . . ? C1 C2 C3 119.5(2) . . ? C2 C3 C4 119.9(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 C7 118.8(2) . . ? C3 C4 C7 121.2(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C1 119.2(2) . . ? O4 C7 O5 123.0(2) . . ? O4 C7 C4 123.7(2) . . ? O5 C7 C4 113.3(2) . . ? N1 C8 N2 120.5(2) . . ? N1 C8 N3 119.5(2) . . ? N2 C8 N3 119.9(2) . . ? _refine_diff_density_max 0.284 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.055