Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_grd511_m _database_code_depnum_ccdc_archive 'CCDC 611646' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Saccharin, pyridine ; _chemical_name_common 'Saccharin, pyridine' _chemical_melting_point 221 _chemical_formula_moiety 'C7 H4 N O3 S, C5 H6 N' _chemical_formula_sum 'C12 H10 N2 O3 S' _chemical_formula_weight 262.28 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4613(15) _cell_length_b 12.954(3) _cell_length_c 14.179(3) _cell_angle_alpha 65.251(2) _cell_angle_beta 74.747(3) _cell_angle_gamma 78.160(3) _cell_volume 1193.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2614 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9100 _exptl_absorpt_correction_T_max 0.9699 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14741 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4725 _reflns_number_gt 3042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4725 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.97899(9) 0.82389(5) 0.38904(5) 0.0482(2) Uani 1 1 d . . . O4 O 0.7346(3) 1.08312(15) 0.42450(14) 0.0606(5) Uani 1 1 d . . . O5 O 0.8732(3) 0.74387(15) 0.38794(15) 0.0634(5) Uani 1 1 d . . . O6 O 1.1547(3) 0.77562(16) 0.42173(15) 0.0665(6) Uani 1 1 d . . . N2 N 0.8539(3) 0.89654(18) 0.45633(16) 0.0517(6) Uani 1 1 d . . . C10 C 0.9128(3) 1.1390(2) 0.19531(19) 0.0477(6) Uani 1 1 d . . . H10 H 0.8493 1.2047 0.2049 0.057 Uiso 1 1 calc R . . N3 N 0.3935(3) -0.0125(2) 0.36791(18) 0.0500(6) Uani 1 1 d . . . C14 C 1.0109(3) 0.9390(2) 0.26424(18) 0.0412(6) Uani 1 1 d . . . C9 C 0.9172(3) 1.0355(2) 0.27978(18) 0.0403(6) Uani 1 1 d . . . C13 C 1.1029(4) 0.9410(2) 0.1654(2) 0.0548(7) Uani 1 1 d . . . H13 H 1.1644 0.8751 0.1555 0.066 Uiso 1 1 calc R . . C20 C 0.3657(4) 0.0971(3) 0.3061(2) 0.0596(7) Uani 1 1 d . . . H20 H 0.3007 0.1495 0.3356 0.072 Uiso 1 1 calc R . . C24 C 0.4870(4) -0.0890(2) 0.3293(2) 0.0546(7) Uani 1 1 d . . . H24 H 0.5054 -0.1651 0.3747 0.065 Uiso 1 1 calc R . . C11 C 1.0049(4) 1.1429(2) 0.0964(2) 0.0565(7) Uani 1 1 d . . . H11 H 1.0034 1.2121 0.0383 0.068 Uiso 1 1 calc R . . C8 C 0.8273(3) 1.0076(2) 0.39377(19) 0.0445(6) Uani 1 1 d . . . C21 C 0.4318(4) 0.1329(3) 0.2000(2) 0.0656(8) Uani 1 1 d . . . H21 H 0.4125 0.2097 0.1564 0.079 Uiso 1 1 calc R . . C23 C 0.5568(4) -0.0573(3) 0.2234(2) 0.0588(7) Uani 1 1 d . . . H23 H 0.6233 -0.1110 0.1960 0.071 Uiso 1 1 calc R . . C22 C 0.5272(4) 0.0550(3) 0.1580(2) 0.0629(8) Uani 1 1 d . . . H22 H 0.5719 0.0782 0.0853 0.076 Uiso 1 1 calc R . . C12 C 1.0989(4) 1.0461(3) 0.0821(2) 0.0614(8) Uani 1 1 d . . . H12 H 1.1616 1.0514 0.0144 0.074 Uiso 1 1 calc R . . S2 S 0.58129(10) 0.68322(6) 0.11864(5) 0.0525(2) Uani 1 1 d . . . O1 O 0.7221(3) 0.42448(15) 0.06432(15) 0.0645(5) Uani 1 1 d . . . O3 O 0.4174(3) 0.75475(16) 0.08425(15) 0.0751(6) Uani 1 1 d . . . O2 O 0.7169(3) 0.73946(16) 0.12937(15) 0.0719(6) Uani 1 1 d . . . C7 C 0.5139(3) 0.5667(2) 0.23714(18) 0.0430(6) Uani 1 1 d . . . N4 N 0.1177(3) 0.4992(2) 0.13791(19) 0.0518(6) Uani 1 1 d . . . N1 N 0.6762(3) 0.61200(18) 0.04539(16) 0.0522(6) Uani 1 1 d . . . C3 C 0.5240(3) 0.3651(2) 0.2910(2) 0.0544(7) Uani 1 1 d . . . H3 H 0.5565 0.2996 0.2758 0.065 Uiso 1 1 calc R . . C2 C 0.5630(3) 0.4707(2) 0.21393(18) 0.0433(6) Uani 1 1 d . . . C6 C 0.4274(4) 0.5623(2) 0.3373(2) 0.0567(7) Uani 1 1 d . . . H6 H 0.3960 0.6277 0.3525 0.068 Uiso 1 1 calc R . . C15 C 0.0809(4) 0.5717(2) 0.1855(2) 0.0595(8) Uani 1 1 d . . . H15 H 0.1142 0.6457 0.1478 0.071 Uiso 1 1 calc R . . C4 C 0.4355(4) 0.3592(3) 0.3912(2) 0.0633(8) Uani 1 1 d . . . H4 H 0.4063 0.2889 0.4443 0.076 Uiso 1 1 calc R . . C1 C 0.6600(3) 0.5001(2) 0.10045(19) 0.0470(6) Uani 1 1 d . . . C16 C -0.0060(4) 0.5389(3) 0.2900(2) 0.0650(8) Uani 1 1 d . . . H16 H -0.0341 0.5903 0.3234 0.078 Uiso 1 1 calc R . . C18 C -0.0098(4) 0.3552(2) 0.2936(2) 0.0611(8) Uani 1 1 d . . . H18 H -0.0392 0.2803 0.3299 0.073 Uiso 1 1 calc R . . C19 C 0.0740(4) 0.3927(2) 0.1892(2) 0.0571(7) Uani 1 1 d . . . H19 H 0.1007 0.3434 0.1537 0.069 Uiso 1 1 calc R . . C17 C -0.0504(4) 0.4293(3) 0.3442(2) 0.0636(8) Uani 1 1 d . . . H17 H -0.1081 0.4050 0.4155 0.076 Uiso 1 1 calc R . . C5 C 0.3898(4) 0.4557(3) 0.4140(2) 0.0655(8) Uani 1 1 d . . . H5 H 0.3321 0.4491 0.4826 0.079 Uiso 1 1 calc R . . H3A H 0.351(4) -0.033(3) 0.435(2) 0.075(10) Uiso 1 1 d . . . H4B H 0.179(4) 0.527(3) 0.069(2) 0.082(10) 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 0.0515(4) 0.0365(4) 0.0459(4) -0.0132(3) 0.0023(3) -0.0034(3) O4 0.0786(13) 0.0474(11) 0.0523(11) -0.0274(9) 0.0001(9) 0.0017(10) O5 0.0713(13) 0.0444(11) 0.0713(13) -0.0262(10) 0.0063(10) -0.0178(10) O6 0.0564(12) 0.0537(12) 0.0661(13) -0.0074(10) -0.0123(10) 0.0085(10) N2 0.0597(14) 0.0459(13) 0.0422(12) -0.0178(10) 0.0012(10) -0.0035(11) C10 0.0481(15) 0.0371(14) 0.0525(16) -0.0132(12) -0.0076(12) -0.0054(12) N3 0.0535(14) 0.0554(15) 0.0419(13) -0.0209(12) -0.0071(11) -0.0061(11) C14 0.0406(14) 0.0387(14) 0.0401(13) -0.0137(11) -0.0022(11) -0.0062(11) C9 0.0384(14) 0.0391(14) 0.0441(14) -0.0182(11) -0.0034(11) -0.0072(11) C13 0.0555(17) 0.0519(17) 0.0520(16) -0.0262(14) 0.0060(13) -0.0035(13) C20 0.0600(18) 0.0551(18) 0.0635(19) -0.0295(15) -0.0103(14) 0.0063(14) C24 0.0563(17) 0.0498(17) 0.0579(18) -0.0215(14) -0.0117(14) -0.0045(14) C11 0.0624(18) 0.0480(16) 0.0436(15) -0.0062(13) -0.0032(13) -0.0081(14) C8 0.0489(16) 0.0450(15) 0.0410(14) -0.0211(12) -0.0015(11) -0.0077(12) C21 0.074(2) 0.0534(18) 0.0573(19) -0.0140(15) -0.0138(16) 0.0045(15) C23 0.0631(19) 0.0619(19) 0.0578(18) -0.0339(16) -0.0072(14) -0.0027(15) C22 0.065(2) 0.077(2) 0.0435(16) -0.0229(16) -0.0083(14) -0.0053(17) C12 0.0614(18) 0.071(2) 0.0424(16) -0.0203(15) 0.0056(13) -0.0120(16) S2 0.0633(5) 0.0373(4) 0.0435(4) -0.0138(3) 0.0038(3) 0.0001(3) O1 0.0830(14) 0.0493(11) 0.0579(12) -0.0294(10) 0.0029(10) -0.0030(10) O3 0.0782(15) 0.0561(13) 0.0604(13) -0.0113(10) -0.0055(10) 0.0218(11) O2 0.0878(16) 0.0535(12) 0.0746(14) -0.0312(11) 0.0099(11) -0.0277(11) C7 0.0404(14) 0.0423(14) 0.0403(14) -0.0144(11) -0.0037(11) -0.0007(11) N4 0.0538(14) 0.0539(15) 0.0475(14) -0.0213(12) -0.0097(11) -0.0017(11) N1 0.0626(15) 0.0425(13) 0.0421(12) -0.0162(10) 0.0019(10) -0.0020(11) C3 0.0517(17) 0.0431(15) 0.0598(17) -0.0162(13) -0.0020(13) -0.0069(13) C2 0.0388(14) 0.0437(15) 0.0412(14) -0.0144(11) -0.0032(11) -0.0021(11) C6 0.0623(18) 0.0564(18) 0.0463(16) -0.0235(14) 0.0014(13) -0.0034(14) C15 0.0656(19) 0.0507(17) 0.0631(19) -0.0253(15) -0.0119(15) -0.0020(15) C4 0.0599(19) 0.0554(19) 0.0510(17) -0.0037(14) -0.0003(14) -0.0077(15) C1 0.0481(16) 0.0471(15) 0.0444(15) -0.0205(13) -0.0059(12) -0.0004(12) C16 0.081(2) 0.062(2) 0.0591(19) -0.0354(16) -0.0163(16) 0.0065(16) C18 0.0642(19) 0.0441(16) 0.0659(19) -0.0152(15) -0.0111(15) -0.0026(14) C19 0.0623(18) 0.0531(18) 0.0642(19) -0.0321(15) -0.0157(15) 0.0012(14) C17 0.068(2) 0.069(2) 0.0444(16) -0.0199(15) -0.0079(14) 0.0019(16) C5 0.0644(19) 0.077(2) 0.0395(15) -0.0156(15) 0.0050(13) -0.0095(17) _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 O5 1.4330(18) . ? S1 O6 1.4370(18) . ? S1 N2 1.610(2) . ? S1 C14 1.768(2) . ? O4 C8 1.243(3) . ? N2 C8 1.343(3) . ? C10 C9 1.375(3) . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? N3 C24 1.319(3) . ? N3 C20 1.327(3) . ? N3 H3A 0.86(3) . ? C14 C9 1.375(3) . ? C14 C13 1.381(3) . ? C9 C8 1.494(3) . ? C13 C12 1.380(4) . ? C13 H13 0.9300 . ? C20 C21 1.357(4) . ? C20 H20 0.9300 . ? C24 C23 1.362(4) . ? C24 H24 0.9300 . ? C11 C12 1.372(4) . ? C11 H11 0.9300 . ? C21 C22 1.367(4) . ? C21 H21 0.9300 . ? C23 C22 1.368(4) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? C12 H12 0.9300 . ? S2 O2 1.433(2) . ? S2 O3 1.4360(19) . ? S2 N1 1.606(2) . ? S2 C7 1.760(2) . ? O1 C1 1.244(3) . ? C7 C2 1.372(3) . ? C7 C6 1.379(3) . ? N4 C15 1.320(3) . ? N4 C19 1.326(3) . ? N4 H4B 0.91(3) . ? N1 C1 1.341(3) . ? C3 C2 1.376(3) . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C2 C1 1.499(3) . ? C6 C5 1.381(4) . ? C6 H6 0.9300 . ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C16 C17 1.365(4) . ? C16 H16 0.9300 . ? C18 C19 1.361(4) . ? C18 C17 1.368(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C17 H17 0.9300 . ? C5 H5 0.9300 . ? 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 O5 S1 O6 115.00(12) . . ? O5 S1 N2 110.88(12) . . ? O6 S1 N2 111.53(12) . . ? O5 S1 C14 110.16(11) . . ? O6 S1 C14 110.72(11) . . ? N2 S1 C14 97.15(11) . . ? C8 N2 S1 110.94(17) . . ? C9 C10 C11 118.3(2) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C24 N3 C20 121.7(2) . . ? C24 N3 H3A 120(2) . . ? C20 N3 H3A 118(2) . . ? C9 C14 C13 122.4(2) . . ? C9 C14 S1 106.87(17) . . ? C13 C14 S1 130.7(2) . . ? C10 C9 C14 120.1(2) . . ? C10 C9 C8 129.1(2) . . ? C14 C9 C8 110.8(2) . . ? C12 C13 C14 116.5(2) . . ? C12 C13 H13 121.8 . . ? C14 C13 H13 121.8 . . ? N3 C20 C21 120.1(3) . . ? N3 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? N3 C24 C23 120.4(3) . . ? N3 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? O4 C8 N2 124.8(2) . . ? O4 C8 C9 121.0(2) . . ? N2 C8 C9 114.2(2) . . ? C20 C21 C22 119.3(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C24 C23 C22 118.9(3) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? O2 S2 O3 115.79(13) . . ? O2 S2 N1 110.96(12) . . ? O3 S2 N1 110.81(12) . . ? O2 S2 C7 110.86(12) . . ? O3 S2 C7 109.31(12) . . ? N1 S2 C7 97.63(11) . . ? C2 C7 C6 122.3(2) . . ? C2 C7 S2 106.68(18) . . ? C6 C7 S2 131.0(2) . . ? C15 N4 C19 121.5(3) . . ? C15 N4 H4B 115(2) . . ? C19 N4 H4B 123(2) . . ? C1 N1 S2 110.66(17) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C7 C2 C3 120.4(2) . . ? C7 C2 C1 110.9(2) . . ? C3 C2 C1 128.7(2) . . ? C7 C6 C5 116.7(3) . . ? C7 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? N4 C15 C16 120.5(3) . . ? N4 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? O1 C1 N1 124.8(2) . . ? O1 C1 C2 121.1(2) . . ? N1 C1 C2 114.1(2) . . ? C17 C16 C15 118.7(3) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? N4 C19 C18 120.3(3) . . ? N4 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C4 C5 C6 121.5(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.255 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.050 data_4abks2_a _database_code_depnum_ccdc_archive 'CCDC 611647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Saccharin, 4,4'-bipyridine ; _chemical_name_common "Saccharin, 4,4'-bipyridine" _chemical_melting_point 194 _chemical_formula_moiety 'C10 H10 N2, 2(C7 H4 N O3 S)' _chemical_formula_sum 'C24 H18 N4 O6 S2' _chemical_formula_weight 522.54 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 monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.705(11) _cell_length_b 11.706(13) _cell_length_c 10.411(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.089(19) _cell_angle_gamma 90.00 _cell_volume 1142(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9217 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7265 _diffrn_reflns_av_R_equivalents 0.0803 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2744 _reflns_number_gt 1460 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2744 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.7758(2) 0.3312(2) 0.1811(2) 0.0416(6) Uani 1 1 d . . . C7 C 0.8754(2) 0.2539(2) 0.2503(2) 0.0418(6) Uani 1 1 d . . . C6 C 0.8726(2) 0.2114(2) 0.3738(2) 0.0475(6) Uani 1 1 d . . . H6 H 0.9403 0.1595 0.4196 0.057 Uiso 1 1 calc R . . C5 C 0.7632(3) 0.2508(2) 0.4253(2) 0.0559(7) Uani 1 1 d . . . H5 H 0.7568 0.2238 0.5075 0.067 Uiso 1 1 calc R . . C4 C 0.6636(3) 0.3288(2) 0.3579(2) 0.0553(7) Uani 1 1 d . . . H4 H 0.5923 0.3539 0.3960 0.066 Uiso 1 1 calc R . . C3 C 0.6683(2) 0.3701(2) 0.2345(2) 0.0498(6) Uani 1 1 d . . . H3 H 0.6012 0.4225 0.1890 0.060 Uiso 1 1 calc R . . C1 C 0.8058(3) 0.3624(2) 0.0497(2) 0.0479(6) Uani 1 1 d . . . C8 C 0.9616(3) 0.4202(2) 0.7689(2) 0.0621(8) Uani 1 1 d . . . H8 H 1.0058 0.3795 0.8452 0.074 Uiso 1 1 calc R . . C10 C 0.9655(2) 0.49326(19) 0.5558(2) 0.0347(5) Uani 1 1 d . . . C11 C 0.8336(2) 0.5406(2) 0.5492(2) 0.0448(6) Uani 1 1 d . . . H11 H 0.7878 0.5831 0.4749 0.054 Uiso 1 1 calc R . . C12 C 0.7693(2) 0.5256(2) 0.6509(2) 0.0493(6) Uani 1 1 d . . . H12 H 0.6803 0.5579 0.6450 0.059 Uiso 1 1 calc R . . C9 C 1.0289(3) 0.4329(2) 0.6691(2) 0.0571(7) Uani 1 1 d . . . H9 H 1.1184 0.4004 0.6782 0.069 Uiso 1 1 calc R . . N2 N 0.8334(2) 0.46563(18) 0.7570(2) 0.0466(5) Uani 1 1 d . . . O1 O 0.97945(16) 0.10683(14) 0.10943(15) 0.0532(5) Uani 1 1 d . . . O2 O 1.13720(16) 0.25992(15) 0.21410(16) 0.0573(5) Uani 1 1 d . . . O3 O 0.73099(18) 0.43301(15) -0.02748(16) 0.0610(5) Uani 1 1 d . . . S1 S 0.99369(6) 0.22431(6) 0.15054(6) 0.04273(19) Uani 1 1 d . . . N1 N 0.9199(2) 0.30756(18) 0.02895(18) 0.0503(5) Uani 1 1 d . . . H2A H 0.793(3) 0.458(2) 0.828(3) 0.075 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 C2 0.0481(14) 0.0440(14) 0.0374(12) -0.0069(12) 0.0193(11) -0.0099(11) C7 0.0450(13) 0.0440(16) 0.0404(12) -0.0093(11) 0.0185(10) -0.0095(11) C6 0.0543(15) 0.0519(16) 0.0387(13) -0.0014(12) 0.0166(11) -0.0073(11) C5 0.0696(18) 0.066(2) 0.0403(14) -0.0074(14) 0.0298(13) -0.0174(14) C4 0.0612(17) 0.0626(18) 0.0539(15) -0.0128(15) 0.0359(13) -0.0060(14) C3 0.0569(15) 0.0471(16) 0.0523(14) -0.0068(13) 0.0265(12) 0.0009(12) C1 0.0555(16) 0.0499(17) 0.0440(13) -0.0007(13) 0.0231(12) -0.0035(12) C8 0.0661(18) 0.074(2) 0.0541(15) 0.0276(15) 0.0293(13) 0.0241(14) C10 0.0349(12) 0.0334(13) 0.0362(12) 0.0004(10) 0.0098(9) -0.0032(9) C11 0.0410(14) 0.0544(17) 0.0389(12) 0.0088(12) 0.0103(10) 0.0071(11) C12 0.0385(14) 0.0594(17) 0.0522(15) 0.0079(14) 0.0156(11) 0.0036(11) C9 0.0507(15) 0.0710(19) 0.0556(15) 0.0271(14) 0.0246(12) 0.0226(13) N2 0.0518(13) 0.0480(13) 0.0460(12) 0.0036(11) 0.0236(10) -0.0001(10) O1 0.0528(11) 0.0498(12) 0.0599(10) -0.0182(9) 0.0196(8) -0.0033(8) O2 0.0433(10) 0.0692(14) 0.0599(11) -0.0101(10) 0.0146(8) -0.0158(8) O3 0.0696(12) 0.0670(13) 0.0541(11) 0.0141(10) 0.0300(9) 0.0148(10) S1 0.0423(4) 0.0498(4) 0.0402(3) -0.0064(3) 0.0180(2) -0.0054(3) N1 0.0526(13) 0.0659(15) 0.0387(11) 0.0062(10) 0.0234(9) 0.0055(10) _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 C2 C3 1.381(3) . ? C2 C7 1.382(3) . ? C2 C1 1.516(3) . ? C7 C6 1.385(3) . ? C7 S1 1.772(3) . ? C6 C5 1.386(3) . ? C6 H6 0.9300 . ? C5 C4 1.381(4) . ? C5 H5 0.9300 . ? C4 C3 1.385(3) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C1 O3 1.246(3) . ? C1 N1 1.345(3) . ? C8 N2 1.328(3) . ? C8 C9 1.372(3) . ? C8 H8 0.9300 . ? C10 C9 1.375(3) . ? C10 C11 1.380(3) . ? C10 C10 1.493(4) 3_766 ? C11 C12 1.373(3) . ? C11 H11 0.9300 . ? C12 N2 1.320(3) . ? C12 H12 0.9300 . ? C9 H9 0.9300 . ? N2 H2A 0.93(3) . ? O1 S1 1.436(2) . ? O2 S1 1.439(2) . ? S1 N1 1.610(2) . ? 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 C3 C2 C7 120.3(2) . . ? C3 C2 C1 128.8(2) . . ? C7 C2 C1 110.8(2) . . ? C2 C7 C6 122.7(2) . . ? C2 C7 S1 107.10(17) . . ? C6 C7 S1 130.2(2) . . ? C7 C6 C5 116.2(2) . . ? C7 C6 H6 121.9 . . ? C5 C6 H6 121.9 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? O3 C1 N1 125.4(2) . . ? O3 C1 C2 121.6(2) . . ? N1 C1 C2 113.0(2) . . ? N2 C8 C9 120.3(2) . . ? N2 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C9 C10 C11 116.84(19) . . ? C9 C10 C10 122.1(2) . 3_766 ? C11 C10 C10 121.1(2) . 3_766 ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? N2 C12 C11 120.2(2) . . ? N2 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C8 C9 C10 120.7(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C12 N2 C8 121.1(2) . . ? C12 N2 H2A 120.7(17) . . ? C8 N2 H2A 118.0(16) . . ? O1 S1 O2 114.89(10) . . ? O1 S1 N1 110.89(12) . . ? O2 S1 N1 111.41(11) . . ? O1 S1 C7 109.60(10) . . ? O2 S1 C7 111.78(12) . . ? N1 S1 C7 96.85(12) . . ? C1 N1 S1 112.25(16) . . ? 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 C2 C7 C6 0.5(4) . . . . ? C1 C2 C7 C6 179.9(2) . . . . ? C3 C2 C7 S1 179.73(19) . . . . ? C1 C2 C7 S1 -0.9(2) . . . . ? C2 C7 C6 C5 0.0(3) . . . . ? S1 C7 C6 C5 -178.94(18) . . . . ? C7 C6 C5 C4 -0.7(4) . . . . ? C6 C5 C4 C3 0.7(4) . . . . ? C7 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C4 -179.7(2) . . . . ? C5 C4 C3 C2 -0.1(4) . . . . ? C3 C2 C1 O3 1.0(4) . . . . ? C7 C2 C1 O3 -178.3(2) . . . . ? C3 C2 C1 N1 -179.8(2) . . . . ? C7 C2 C1 N1 0.9(3) . . . . ? C9 C10 C11 C12 -1.1(4) . . . . ? C10 C10 C11 C12 178.5(3) 3_766 . . . ? C10 C11 C12 N2 0.1(4) . . . . ? N2 C8 C9 C10 0.3(4) . . . . ? C11 C10 C9 C8 0.8(4) . . . . ? C10 C10 C9 C8 -178.7(3) 3_766 . . . ? C11 C12 N2 C8 1.1(4) . . . . ? C9 C8 N2 C12 -1.3(4) . . . . ? C2 C7 S1 O1 -114.43(18) . . . . ? C6 C7 S1 O1 64.7(2) . . . . ? C2 C7 S1 O2 117.01(18) . . . . ? C6 C7 S1 O2 -63.9(3) . . . . ? C2 C7 S1 N1 0.66(18) . . . . ? C6 C7 S1 N1 179.8(2) . . . . ? O3 C1 N1 S1 178.7(2) . . . . ? C2 C1 N1 S1 -0.4(3) . . . . ? O1 S1 N1 C1 113.89(19) . . . . ? O2 S1 N1 C1 -116.8(2) . . . . ? C7 S1 N1 C1 -0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.196 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.053 data_an50_m _database_code_depnum_ccdc_archive 'CCDC 611648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; saccharin, 4-picoline ; _chemical_name_common 'saccharin, 4-picoline' _chemical_melting_point 202 _chemical_formula_moiety 'C7 H4 N O3 S, C6 H8 N' _chemical_formula_sum 'C13 H12 N2 O3 S' _chemical_formula_weight 276.31 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4299(5) _cell_length_b 11.1506(7) _cell_length_c 15.3450(9) _cell_angle_alpha 88.0950(10) _cell_angle_beta 76.7170(10) _cell_angle_gamma 81.4900(10) _cell_volume 1223.67(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7111 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10008 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4770 _reflns_number_gt 4486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+1.4391P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4770 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.82198(7) 0.79408(4) 0.45934(3) 0.01678(13) Uani 1 1 d . . . O1 O 0.6931(2) 0.52590(12) 0.58893(9) 0.0224(3) Uani 1 1 d . . . O3 O 0.6852(2) 0.85964(13) 0.41531(9) 0.0218(3) Uani 1 1 d . . . O2 O 1.0131(2) 0.80690(13) 0.41848(10) 0.0228(3) Uani 1 1 d . . . N1 N 0.7925(2) 0.65283(15) 0.47210(11) 0.0189(4) Uani 1 1 d . . . C7 C 0.7667(3) 0.83355(18) 0.57450(13) 0.0164(4) Uani 1 1 d . . . C1 C 0.7318(3) 0.62716(18) 0.55923(13) 0.0175(4) Uani 1 1 d . . . C3 C 0.6530(3) 0.73412(19) 0.71376(13) 0.0194(4) Uani 1 1 d . . . H3 H 0.6138 0.6650 0.7463 0.023 Uiso 1 1 calc R . . C6 C 0.7681(3) 0.94083(18) 0.61664(14) 0.0197(4) Uani 1 1 d . . . H6 H 0.8069 1.0098 0.5838 0.024 Uiso 1 1 calc R . . C4 C 0.6517(3) 0.8422(2) 0.75712(14) 0.0222(4) Uani 1 1 d . . . H4 H 0.6102 0.8470 0.8204 0.027 Uiso 1 1 calc R . . C2 C 0.7136(3) 0.73128(17) 0.62144(13) 0.0166(4) Uani 1 1 d . . . C5 C 0.7099(3) 0.94297(19) 0.70954(14) 0.0223(4) Uani 1 1 d . . . H5 H 0.7100 1.0149 0.7411 0.027 Uiso 1 1 calc R . . S2 S 0.78494(7) 0.28750(4) 1.05339(3) 0.01838(14) Uani 1 1 d . . . O4 O 0.7712(2) 0.03214(12) 0.91262(9) 0.0219(3) Uani 1 1 d . . . O6 O 0.9400(2) 0.29180(14) 1.09432(10) 0.0255(3) Uani 1 1 d . . . O5 O 0.6089(2) 0.35473(13) 1.09997(10) 0.0251(3) Uani 1 1 d . . . N3 N 0.3000(2) 0.14142(15) 0.96253(12) 0.0187(4) Uani 1 1 d . . . N2 N 0.7608(2) 0.14978(15) 1.03406(11) 0.0207(4) Uani 1 1 d . . . C10 C 0.8627(3) 0.25046(18) 0.79636(13) 0.0185(4) Uani 1 1 d . . . H10 H 0.8615 0.1839 0.7595 0.022 Uiso 1 1 calc R . . C14 C 0.8385(3) 0.33543(18) 0.94056(13) 0.0169(4) Uani 1 1 d . . . C13 C 0.8729(3) 0.44760(18) 0.90526(14) 0.0196(4) Uani 1 1 d . . . H13 H 0.8785 0.5130 0.9422 0.024 Uiso 1 1 calc R . . C9 C 0.8327(3) 0.23795(17) 0.88808(13) 0.0166(4) Uani 1 1 d . . . C12 C 0.8990(3) 0.46003(18) 0.81303(14) 0.0211(4) Uani 1 1 d . . . H12 H 0.9203 0.5362 0.7862 0.025 Uiso 1 1 calc R . . C8 C 0.7859(3) 0.12960(18) 0.94590(13) 0.0174(4) Uani 1 1 d . . . C15 C 0.3410(3) 0.25026(18) 0.97915(14) 0.0196(4) Uani 1 1 d . . . H15 H 0.3465 0.2700 1.0381 0.024 Uiso 1 1 calc R . . C11 C 0.8946(3) 0.36319(19) 0.75906(14) 0.0210(4) Uani 1 1 d . . . H11 H 0.9136 0.3740 0.6961 0.025 Uiso 1 1 calc R . . C17 C 0.3658(3) 0.30512(18) 0.82458(14) 0.0192(4) Uani 1 1 d . . . C18 C 0.3244(3) 0.19071(19) 0.80987(14) 0.0206(4) Uani 1 1 d . . . H18 H 0.3187 0.1680 0.7515 0.025 Uiso 1 1 calc R . . C26 C 0.4015(3) 0.3945(2) 0.74991(15) 0.0254(5) Uani 1 1 d . . . H26A H 0.3475 0.4763 0.7723 0.038 Uiso 1 1 calc R . . H26B H 0.3439 0.3746 0.7019 0.038 Uiso 1 1 calc R . . H26C H 0.5365 0.3913 0.7267 0.038 Uiso 1 1 calc R . . C16 C 0.3752(3) 0.33337(18) 0.91157(14) 0.0203(4) Uani 1 1 d . . . H16 H 0.4052 0.4101 0.9238 0.024 Uiso 1 1 calc R . . C19 C 0.2917(3) 0.11048(19) 0.88001(14) 0.0210(4) Uani 1 1 d . . . H19 H 0.2631 0.0326 0.8698 0.025 Uiso 1 1 calc R . . N4 N 0.7368(2) 0.35850(15) 0.46607(12) 0.0187(4) Uani 1 1 d . . . C24 C 0.6766(3) 0.25211(18) 0.49019(14) 0.0194(4) Uani 1 1 d . . . H24 H 0.6153 0.2394 0.5506 0.023 Uiso 1 1 calc R . . C20 C 0.8222(3) 0.38009(19) 0.38133(14) 0.0207(4) Uani 1 1 d . . . H20 H 0.8626 0.4565 0.3658 0.025 Uiso 1 1 calc R . . C22 C 0.7936(3) 0.17991(18) 0.33967(13) 0.0182(4) Uani 1 1 d . . . C23 C 0.7027(3) 0.16147(18) 0.42827(14) 0.0196(4) Uani 1 1 d . . . H23 H 0.6591 0.0864 0.4457 0.024 Uiso 1 1 calc R . . C25 C 0.8246(3) 0.08270(19) 0.27052(14) 0.0226(4) Uani 1 1 d . . . H25A H 0.8600 0.0038 0.2967 0.034 Uiso 1 1 calc R . . H25B H 0.9248 0.0989 0.2196 0.034 Uiso 1 1 calc R . . H25C H 0.7092 0.0818 0.2500 0.034 Uiso 1 1 calc R . . C21 C 0.8513(3) 0.29254(19) 0.31701(14) 0.0208(4) Uani 1 1 d . . . H21 H 0.9109 0.3086 0.2569 0.025 Uiso 1 1 calc R . . H2 H 0.273(4) 0.088(3) 1.0096(19) 0.036(7) Uiso 1 1 d . . . H1 H 0.721(4) 0.418(3) 0.5089(19) 0.035(7) 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 0.0222(3) 0.0157(2) 0.0133(2) 0.00141(17) -0.00404(18) -0.00554(18) O1 0.0350(8) 0.0142(7) 0.0170(7) 0.0016(5) -0.0025(6) -0.0066(6) O3 0.0290(8) 0.0209(7) 0.0174(7) 0.0050(6) -0.0083(6) -0.0064(6) O2 0.0256(8) 0.0250(8) 0.0184(7) 0.0012(6) -0.0030(6) -0.0086(6) N1 0.0264(9) 0.0156(8) 0.0144(8) -0.0001(6) -0.0032(7) -0.0046(7) C7 0.0184(9) 0.0177(9) 0.0133(9) 0.0011(7) -0.0045(7) -0.0020(7) C1 0.0188(9) 0.0173(10) 0.0161(10) 0.0006(8) -0.0039(7) -0.0021(7) C3 0.0192(10) 0.0206(10) 0.0175(10) 0.0024(8) -0.0035(8) -0.0013(8) C6 0.0221(10) 0.0170(10) 0.0214(10) -0.0003(8) -0.0069(8) -0.0039(8) C4 0.0231(10) 0.0278(11) 0.0151(10) -0.0019(8) -0.0047(8) -0.0007(8) C2 0.0166(9) 0.0163(9) 0.0175(10) 0.0003(7) -0.0054(7) -0.0013(7) C5 0.0233(10) 0.0211(10) 0.0235(11) -0.0064(8) -0.0071(8) -0.0026(8) S2 0.0255(3) 0.0164(2) 0.0131(2) 0.00040(18) -0.00160(19) -0.00674(19) O4 0.0344(8) 0.0146(7) 0.0167(7) 0.0005(5) -0.0043(6) -0.0056(6) O6 0.0337(8) 0.0271(8) 0.0181(7) 0.0014(6) -0.0070(6) -0.0107(7) O5 0.0299(8) 0.0219(8) 0.0199(8) -0.0031(6) 0.0033(6) -0.0061(6) N3 0.0217(9) 0.0161(8) 0.0175(9) 0.0028(7) -0.0038(7) -0.0021(7) N2 0.0291(9) 0.0176(9) 0.0152(8) 0.0008(7) -0.0028(7) -0.0067(7) C10 0.0195(10) 0.0186(10) 0.0166(10) -0.0010(8) -0.0034(8) -0.0016(8) C14 0.0178(9) 0.0177(10) 0.0141(9) 0.0017(7) -0.0019(7) -0.0027(7) C13 0.0214(10) 0.0169(10) 0.0196(10) -0.0003(8) -0.0013(8) -0.0048(8) C9 0.0165(9) 0.0160(9) 0.0163(9) 0.0007(7) -0.0020(7) -0.0017(7) C12 0.0220(10) 0.0174(10) 0.0222(10) 0.0060(8) -0.0014(8) -0.0045(8) C8 0.0202(10) 0.0152(9) 0.0164(10) 0.0014(7) -0.0034(8) -0.0028(7) C15 0.0216(10) 0.0193(10) 0.0174(10) -0.0028(8) -0.0036(8) -0.0015(8) C11 0.0203(10) 0.0248(11) 0.0167(10) 0.0050(8) -0.0025(8) -0.0032(8) C17 0.0158(9) 0.0196(10) 0.0209(10) 0.0027(8) -0.0030(8) -0.0007(7) C18 0.0239(10) 0.0210(10) 0.0173(10) -0.0005(8) -0.0053(8) -0.0033(8) C26 0.0284(11) 0.0248(11) 0.0241(11) 0.0082(9) -0.0070(9) -0.0076(9) C16 0.0211(10) 0.0169(10) 0.0226(11) 0.0001(8) -0.0040(8) -0.0035(8) C19 0.0261(11) 0.0181(10) 0.0188(10) -0.0006(8) -0.0050(8) -0.0033(8) N4 0.0216(9) 0.0162(8) 0.0187(9) -0.0016(7) -0.0061(7) -0.0012(7) C24 0.0198(10) 0.0190(10) 0.0191(10) 0.0044(8) -0.0045(8) -0.0032(8) C20 0.0246(10) 0.0179(10) 0.0199(10) 0.0032(8) -0.0054(8) -0.0047(8) C22 0.0183(9) 0.0182(10) 0.0191(10) 0.0010(8) -0.0079(8) -0.0005(7) C23 0.0198(10) 0.0168(10) 0.0228(10) 0.0025(8) -0.0060(8) -0.0034(8) C25 0.0258(11) 0.0201(10) 0.0223(11) -0.0036(8) -0.0046(8) -0.0048(8) C21 0.0243(10) 0.0208(10) 0.0170(10) 0.0031(8) -0.0039(8) -0.0047(8) _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 O2 1.4408(15) . ? S1 O3 1.4445(15) . ? S1 N1 1.6214(17) . ? S1 C7 1.775(2) . ? O1 C1 1.252(2) . ? N1 C1 1.345(3) . ? C7 C6 1.381(3) . ? C7 C2 1.387(3) . ? C1 C2 1.498(3) . ? C3 C2 1.384(3) . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C6 C5 1.391(3) . ? C6 H6 0.9500 . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? S2 O6 1.4406(16) . ? S2 O5 1.4489(16) . ? S2 N2 1.6169(17) . ? S2 C14 1.768(2) . ? O4 C8 1.246(2) . ? N3 C15 1.340(3) . ? N3 C19 1.341(3) . ? N3 H2 0.93(3) . ? N2 C8 1.344(3) . ? C10 C9 1.379(3) . ? C10 C11 1.394(3) . ? C10 H10 0.9500 . ? C14 C13 1.382(3) . ? C14 C9 1.386(3) . ? C13 C12 1.389(3) . ? C13 H13 0.9500 . ? C9 C8 1.510(3) . ? C12 C11 1.391(3) . ? C12 H12 0.9500 . ? C15 C16 1.372(3) . ? C15 H15 0.9500 . ? C11 H11 0.9500 . ? C17 C18 1.393(3) . ? C17 C16 1.401(3) . ? C17 C26 1.497(3) . ? C18 C19 1.378(3) . ? C18 H18 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C16 H16 0.9500 . ? C19 H19 0.9500 . ? N4 C20 1.340(3) . ? N4 C24 1.340(3) . ? N4 H1 0.92(3) . ? C24 C23 1.372(3) . ? C24 H24 0.9500 . ? C20 C21 1.370(3) . ? C20 H20 0.9500 . ? C22 C21 1.394(3) . ? C22 C23 1.396(3) . ? C22 C25 1.498(3) . ? C23 H23 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C21 H21 0.9500 . ? 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 O2 S1 O3 114.88(9) . . ? O2 S1 N1 111.76(9) . . ? O3 S1 N1 110.47(9) . . ? O2 S1 C7 110.85(9) . . ? O3 S1 C7 110.10(9) . . ? N1 S1 C7 97.44(9) . . ? C1 N1 S1 110.57(14) . . ? C6 C7 C2 122.43(18) . . ? C6 C7 S1 131.23(16) . . ? C2 C7 S1 106.33(14) . . ? O1 C1 N1 124.75(18) . . ? O1 C1 C2 120.75(18) . . ? N1 C1 C2 114.50(17) . . ? C2 C3 C4 117.48(19) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? C7 C6 C5 116.77(19) . . ? C7 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? C5 C4 C3 121.24(19) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C3 C2 C7 120.70(18) . . ? C3 C2 C1 128.28(18) . . ? C7 C2 C1 111.01(17) . . ? C4 C5 C6 121.34(19) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? O6 S2 O5 115.12(9) . . ? O6 S2 N2 111.83(9) . . ? O5 S2 N2 110.91(9) . . ? O6 S2 C14 110.73(9) . . ? O5 S2 C14 109.66(9) . . ? N2 S2 C14 97.15(9) . . ? C15 N3 C19 121.29(18) . . ? C15 N3 H2 118.9(17) . . ? C19 N3 H2 119.8(17) . . ? C8 N2 S2 111.35(14) . . ? C9 C10 C11 118.34(19) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C13 C14 C9 122.88(18) . . ? C13 C14 S2 129.96(16) . . ? C9 C14 S2 107.10(14) . . ? C14 C13 C12 116.69(19) . . ? C14 C13 H13 121.7 . . ? C12 C13 H13 121.7 . . ? C10 C9 C14 120.00(18) . . ? C10 C9 C8 129.46(18) . . ? C14 C9 C8 110.52(17) . . ? C13 C12 C11 121.36(19) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? O4 C8 N2 124.71(18) . . ? O4 C8 C9 121.42(18) . . ? N2 C8 C9 113.87(17) . . ? N3 C15 C16 120.48(19) . . ? N3 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C12 C11 C10 120.71(19) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C18 C17 C16 117.75(18) . . ? C18 C17 C26 121.27(19) . . ? C16 C17 C26 120.97(19) . . ? C19 C18 C17 119.93(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C17 C26 H26A 109.5 . . ? C17 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C17 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C15 C16 C17 120.02(19) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? N3 C19 C18 120.52(19) . . ? N3 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C20 N4 C24 121.40(18) . . ? C20 N4 H1 119.3(17) . . ? C24 N4 H1 119.3(17) . . ? N4 C24 C23 120.47(19) . . ? N4 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? N4 C20 C21 120.35(19) . . ? N4 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C21 C22 C23 117.95(19) . . ? C21 C22 C25 120.96(18) . . ? C23 C22 C25 121.07(18) . . ? C24 C23 C22 119.78(19) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 C21 C22 120.03(19) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.433 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.058 data_an25_m _database_code_depnum_ccdc_archive 'CCDC 611649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; saccharine, isonicotinamide ; _chemical_name_common 'saccharine, isonicotinamide' _chemical_melting_point 185 _chemical_formula_moiety 'C7 H4 N O3 S, C6 H7 N2 O' _chemical_formula_sum 'C13 H11 N3 O4 S' _chemical_formula_weight 305.31 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.9157(12) _cell_length_b 17.351(3) _cell_length_c 10.6553(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.421(2) _cell_angle_gamma 90.00 _cell_volume 1248.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2051 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.95 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7458 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2447 _reflns_number_gt 2041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.9620P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2447 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.34750(8) 0.25490(3) 0.26723(5) 0.01579(16) Uani 1 1 d . . . O1 O 0.2544(2) 0.07427(8) 0.41809(14) 0.0186(3) Uani 1 1 d . . . N3 N 0.8817(3) 0.05902(10) 0.28047(17) 0.0167(4) Uani 1 1 d . . . O4 O 0.1957(2) -0.03069(9) 0.13408(15) 0.0237(4) Uani 1 1 d . . . N1 N 0.2180(3) 0.18182(10) 0.29267(16) 0.0160(4) Uani 1 1 d . . . O2 O 0.2728(2) 0.32529(9) 0.31156(15) 0.0239(4) Uani 1 1 d . . . N2 N 0.1941(3) 0.07094(11) 0.00209(18) 0.0197(4) Uani 1 1 d . . . C1 C 0.3233(3) 0.13501(12) 0.38207(19) 0.0156(4) Uani 1 1 d . . . O3 O 0.3695(2) 0.25682(9) 0.13644(14) 0.0224(4) Uani 1 1 d . . . C2 C 0.5331(3) 0.16080(12) 0.43186(19) 0.0149(4) Uani 1 1 d . . . C9 C 0.6060(3) 0.09982(12) 0.1244(2) 0.0179(5) Uani 1 1 d . . . H9 H 0.5480 0.1349 0.0585 0.021 Uiso 1 1 calc R . . C7 C 0.5697(3) 0.22860(12) 0.37270(19) 0.0158(4) Uani 1 1 d . . . C11 C 0.5846(3) -0.01087(12) 0.2542(2) 0.0174(5) Uani 1 1 d . . . H11 H 0.5120 -0.0528 0.2783 0.021 Uiso 1 1 calc R . . C13 C 0.2802(3) 0.02433(12) 0.0962(2) 0.0175(5) Uani 1 1 d . . . C8 C 0.8007(3) 0.10840(12) 0.1875(2) 0.0180(5) Uani 1 1 d . . . H8 H 0.8776 0.1494 0.1649 0.022 Uiso 1 1 calc R . . C6 C 0.7508(3) 0.26551(13) 0.3990(2) 0.0196(5) Uani 1 1 d . . . H6 H 0.7728 0.3116 0.3561 0.024 Uiso 1 1 calc R . . C10 C 0.4950(3) 0.03932(12) 0.1581(2) 0.0155(4) Uani 1 1 d . . . C4 C 0.8637(3) 0.16483(13) 0.5535(2) 0.0206(5) Uani 1 1 d . . . H4 H 0.9664 0.1439 0.6183 0.025 Uiso 1 1 calc R . . C5 C 0.8989(3) 0.23189(13) 0.4913(2) 0.0211(5) Uani 1 1 d . . . H5 H 1.0262 0.2551 0.5122 0.025 Uiso 1 1 calc R . . C12 C 0.7792(3) 0.00036(12) 0.3145(2) 0.0183(5) Uani 1 1 d . . . H12 H 0.8409 -0.0338 0.3808 0.022 Uiso 1 1 calc R . . C3 C 0.6820(3) 0.12742(13) 0.5236(2) 0.0179(5) Uani 1 1 d . . . H3 H 0.6606 0.0805 0.5647 0.021 Uiso 1 1 calc R . . H2 H 0.257(4) 0.1108(15) -0.028(2) 0.025(7) Uiso 1 1 d . . . H7 H 0.071(4) 0.0599(15) -0.034(2) 0.030(7) Uiso 1 1 d . . . H1 H 1.020(5) 0.0656(17) 0.326(3) 0.050(9) 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 0.0131(3) 0.0166(3) 0.0164(3) 0.0013(2) 0.0003(2) -0.0010(2) O1 0.0167(8) 0.0174(8) 0.0217(8) 0.0025(6) 0.0041(6) -0.0024(6) N3 0.0145(9) 0.0191(9) 0.0167(9) -0.0019(7) 0.0037(7) -0.0011(8) O4 0.0181(8) 0.0271(9) 0.0244(9) 0.0027(7) 0.0015(7) -0.0072(7) N1 0.0123(9) 0.0181(9) 0.0168(9) 0.0009(7) 0.0017(7) -0.0008(7) O2 0.0223(9) 0.0178(8) 0.0288(9) 0.0003(7) -0.0009(7) 0.0031(7) N2 0.0127(10) 0.0210(10) 0.0240(11) 0.0001(8) 0.0011(8) -0.0037(8) C1 0.0166(11) 0.0187(11) 0.0127(10) -0.0045(8) 0.0059(8) 0.0002(9) O3 0.0169(8) 0.0320(9) 0.0173(8) 0.0059(7) 0.0014(6) -0.0029(7) C2 0.0128(10) 0.0190(11) 0.0137(10) -0.0033(8) 0.0044(8) 0.0018(9) C9 0.0182(11) 0.0172(11) 0.0180(11) 0.0000(9) 0.0031(9) 0.0007(9) C7 0.0146(10) 0.0189(11) 0.0136(10) -0.0033(8) 0.0021(8) 0.0023(9) C11 0.0175(11) 0.0160(11) 0.0201(11) -0.0016(9) 0.0073(9) -0.0016(9) C13 0.0177(11) 0.0195(11) 0.0162(11) -0.0054(9) 0.0062(9) -0.0019(9) C8 0.0189(11) 0.0173(11) 0.0188(11) -0.0001(9) 0.0061(9) -0.0028(9) C6 0.0173(11) 0.0198(11) 0.0222(12) -0.0021(9) 0.0049(9) -0.0037(9) C10 0.0137(10) 0.0184(11) 0.0157(10) -0.0061(8) 0.0056(8) -0.0006(9) C4 0.0159(11) 0.0253(12) 0.0182(11) -0.0048(9) -0.0013(9) 0.0062(9) C5 0.0129(11) 0.0259(12) 0.0232(12) -0.0092(9) 0.0009(9) -0.0026(9) C12 0.0187(11) 0.0187(11) 0.0178(11) -0.0002(9) 0.0048(9) 0.0011(9) C3 0.0189(11) 0.0197(11) 0.0152(10) -0.0005(9) 0.0039(9) 0.0040(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 O3 1.4344(16) . ? S1 O2 1.4445(16) . ? S1 N1 1.6086(18) . ? S1 C7 1.758(2) . ? O1 C1 1.251(2) . ? N3 C12 1.335(3) . ? N3 C8 1.338(3) . ? N3 H1 0.98(3) . ? O4 C13 1.232(3) . ? N1 C1 1.341(3) . ? N2 C13 1.326(3) . ? N2 H2 0.91(3) . ? N2 H7 0.88(3) . ? C1 C2 1.502(3) . ? C2 C7 1.384(3) . ? C2 C3 1.385(3) . ? C9 C8 1.377(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C7 C6 1.381(3) . ? C11 C12 1.375(3) . ? C11 C10 1.385(3) . ? C11 H11 0.9500 . ? C13 C10 1.512(3) . ? C8 H8 0.9500 . ? C6 C5 1.387(3) . ? C6 H6 0.9500 . ? C4 C5 1.386(3) . ? C4 C3 1.389(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C12 H12 0.9500 . ? C3 H3 0.9500 . ? 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 O3 S1 O2 114.72(10) . . ? O3 S1 N1 111.17(9) . . ? O2 S1 N1 111.11(10) . . ? O3 S1 C7 111.50(10) . . ? O2 S1 C7 109.60(9) . . ? N1 S1 C7 97.44(10) . . ? C12 N3 C8 121.81(19) . . ? C12 N3 H1 118.3(18) . . ? C8 N3 H1 119.8(18) . . ? C1 N1 S1 111.11(14) . . ? C13 N2 H2 124.2(15) . . ? C13 N2 H7 115.8(17) . . ? H2 N2 H7 120(2) . . ? O1 C1 N1 122.94(19) . . ? O1 C1 C2 123.07(19) . . ? N1 C1 C2 113.97(18) . . ? C7 C2 C3 119.75(19) . . ? C7 C2 C1 110.47(18) . . ? C3 C2 C1 129.8(2) . . ? C8 C9 C10 119.4(2) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C6 C7 C2 123.3(2) . . ? C6 C7 S1 129.76(18) . . ? C2 C7 S1 106.96(15) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? O4 C13 N2 123.6(2) . . ? O4 C13 C10 118.76(19) . . ? N2 C13 C10 117.64(19) . . ? N3 C8 C9 120.1(2) . . ? N3 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C7 C6 C5 116.6(2) . . ? C7 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? C11 C10 C9 118.72(19) . . ? C11 C10 C13 117.09(19) . . ? C9 C10 C13 124.19(19) . . ? C5 C4 C3 121.7(2) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? N3 C12 C11 120.3(2) . . ? N3 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C2 C3 C4 117.7(2) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.340 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.064 data_an71 _database_code_depnum_ccdc_archive 'CCDC 611650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Saccharin, 3-aminopyridine ; _chemical_name_common 'Saccharin, 3-aminopyridine' _chemical_melting_point 173 _chemical_formula_moiety 'C7 H4 N O3 S, C5 H7 N2' _chemical_formula_sum 'C12 H11 N3 O3 S' _chemical_formula_weight 277.30 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1321(9) _cell_length_b 8.3859(6) _cell_length_c 13.1779(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.6100(10) _cell_angle_gamma 90.00 _cell_volume 1237.66(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5536 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.26 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8360 _exptl_absorpt_correction_T_max 0.9140 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6231 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2290 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.7113P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2290 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C12 C 0.09096(13) 0.56535(17) 0.23905(12) 0.0184(3) Uani 1 1 d . . . O2 O 0.30628(9) 0.45308(13) 0.14789(9) 0.0238(3) Uani 1 1 d . . . S1 S 0.41173(3) 0.55086(4) 0.18338(3) 0.01650(15) Uani 1 1 d . . . O3 O 0.61549(9) 0.57055(13) 0.47151(8) 0.0217(3) Uani 1 1 d . . . O1 O 0.40545(10) 0.68827(13) 0.11485(8) 0.0238(3) Uani 1 1 d . . . N1 N 0.45137(11) 0.60283(15) 0.31079(10) 0.0181(3) Uani 1 1 d . . . C7 C 0.53929(13) 0.43557(17) 0.19843(12) 0.0164(3) Uani 1 1 d . . . C1 C 0.56037(13) 0.54545(17) 0.37136(12) 0.0164(3) Uani 1 1 d . . . C2 C 0.61427(13) 0.44441(16) 0.30826(12) 0.0162(3) Uani 1 1 d . . . C3 C 0.72306(13) 0.36660(18) 0.34642(13) 0.0201(3) Uani 1 1 d . . . H3 H 0.7750 0.3715 0.4217 0.024 Uiso 1 1 calc R . . C6 C 0.56838(14) 0.35157(18) 0.12189(12) 0.0211(3) Uani 1 1 d . . . H6 H 0.5159 0.3470 0.0467 0.025 Uiso 1 1 calc R . . C5 C 0.67822(15) 0.27413(19) 0.16034(13) 0.0244(4) Uani 1 1 d . . . H5 H 0.7020 0.2157 0.1104 0.029 Uiso 1 1 calc R . . C4 C 0.75383(14) 0.28085(19) 0.27081(13) 0.0238(4) Uani 1 1 d . . . H4 H 0.8279 0.2258 0.2951 0.029 Uiso 1 1 calc R . . N3 N 0.03594(11) 0.71770(15) 0.07571(10) 0.0174(3) Uani 1 1 d . . . C11 C -0.10224(13) 0.53533(18) 0.09115(13) 0.0198(3) Uani 1 1 d . . . H11 H -0.1785 0.4858 0.0614 0.024 Uiso 1 1 calc R . . C8 C -0.02207(13) 0.49363(19) 0.19468(12) 0.0202(3) Uani 1 1 d . . . H8 H -0.0437 0.4158 0.2361 0.024 Uiso 1 1 calc R . . N2 N 0.17158(14) 0.52770(18) 0.34176(12) 0.0269(3) Uani 1 1 d . . . C9 C 0.11630(13) 0.68090(18) 0.17547(12) 0.0179(3) Uani 1 1 d . . . H9 H 0.1912 0.7340 0.2031 0.022 Uiso 1 1 calc R . . C10 C -0.07150(13) 0.64891(18) 0.03104(12) 0.0190(3) Uani 1 1 d . . . H10 H -0.1255 0.6777 -0.0406 0.023 Uiso 1 1 calc R . . H2 H 0.242(2) 0.560(3) 0.3560(18) 0.039(6) Uiso 1 1 d . . . H1 H 0.1600(18) 0.439(3) 0.3685(16) 0.029(5) Uiso 1 1 d . . . H12 H 0.0570(19) 0.788(3) 0.0376(19) 0.046(6) 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 C12 0.0201(7) 0.0178(7) 0.0158(7) -0.0009(5) 0.0054(6) 0.0035(6) O2 0.0154(5) 0.0290(6) 0.0223(6) -0.0020(4) 0.0020(4) -0.0014(4) S1 0.0161(2) 0.0183(2) 0.0139(2) -0.00015(13) 0.00449(15) 0.00208(13) O3 0.0197(5) 0.0267(6) 0.0148(5) -0.0035(4) 0.0022(4) 0.0029(4) O1 0.0315(6) 0.0217(6) 0.0181(5) 0.0030(4) 0.0095(5) 0.0058(5) N1 0.0175(6) 0.0214(7) 0.0148(6) -0.0015(5) 0.0055(5) 0.0021(5) C7 0.0169(7) 0.0147(7) 0.0183(7) 0.0017(5) 0.0075(6) -0.0003(5) C1 0.0167(7) 0.0150(7) 0.0182(7) 0.0001(5) 0.0076(6) -0.0013(5) C2 0.0160(7) 0.0145(7) 0.0192(7) 0.0000(5) 0.0081(6) -0.0024(5) C3 0.0175(7) 0.0196(8) 0.0230(7) 0.0022(6) 0.0077(6) 0.0001(6) C6 0.0278(8) 0.0184(7) 0.0191(7) -0.0005(6) 0.0112(6) 0.0004(6) C5 0.0331(9) 0.0196(8) 0.0282(8) 0.0002(6) 0.0205(7) 0.0034(7) C4 0.0215(8) 0.0214(8) 0.0328(9) 0.0051(6) 0.0152(7) 0.0050(6) N3 0.0200(6) 0.0164(6) 0.0170(6) 0.0003(5) 0.0084(5) 0.0016(5) C11 0.0160(7) 0.0195(7) 0.0230(8) -0.0021(6) 0.0062(6) 0.0000(5) C8 0.0220(8) 0.0181(7) 0.0226(8) 0.0013(6) 0.0107(6) 0.0015(6) N2 0.0259(8) 0.0258(8) 0.0213(7) 0.0059(6) 0.0006(6) 0.0001(6) C9 0.0159(7) 0.0181(7) 0.0187(7) -0.0027(6) 0.0054(6) 0.0009(5) C10 0.0183(7) 0.0201(7) 0.0162(7) -0.0007(6) 0.0039(6) 0.0030(6) _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 C12 N2 1.368(2) . ? C12 C9 1.390(2) . ? C12 C8 1.403(2) . ? O2 S1 1.4380(11) . ? S1 O1 1.4479(11) . ? S1 N1 1.6184(12) . ? S1 C7 1.7700(15) . ? O3 C1 1.2469(18) . ? N1 C1 1.3438(19) . ? C7 C6 1.383(2) . ? C7 C2 1.384(2) . ? C1 C2 1.502(2) . ? C2 C3 1.382(2) . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C6 C5 1.391(2) . ? C6 H6 0.9500 . ? C5 C4 1.392(2) . ? C5 H5 0.9500 . ? C4 H4 0.9500 . ? N3 C9 1.3373(19) . ? N3 C10 1.3374(19) . ? N3 H12 0.88(2) . ? C11 C10 1.379(2) . ? C11 C8 1.382(2) . ? C11 H11 0.9500 . ? C8 H8 0.9500 . ? N2 H2 0.85(2) . ? N2 H1 0.85(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 N2 C12 C9 121.17(14) . . ? N2 C12 C8 121.75(15) . . ? C9 C12 C8 117.05(13) . . ? O2 S1 O1 115.09(7) . . ? O2 S1 N1 111.31(7) . . ? O1 S1 N1 110.86(7) . . ? O2 S1 C7 110.81(7) . . ? O1 S1 C7 109.80(7) . . ? N1 S1 C7 97.62(6) . . ? C1 N1 S1 110.60(10) . . ? C6 C7 C2 122.73(14) . . ? C6 C7 S1 130.84(12) . . ? C2 C7 S1 106.43(11) . . ? O3 C1 N1 124.97(13) . . ? O3 C1 C2 120.72(13) . . ? N1 C1 C2 114.32(13) . . ? C3 C2 C7 120.47(14) . . ? C3 C2 C1 128.54(14) . . ? C7 C2 C1 110.99(13) . . ? C2 C3 C4 117.72(14) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C7 C6 C5 116.71(14) . . ? C7 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? C6 C5 C4 121.06(14) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C3 C4 C5 121.31(14) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C9 N3 C10 123.50(13) . . ? C9 N3 H12 117.1(14) . . ? C10 N3 H12 119.3(14) . . ? C10 C11 C8 119.93(14) . . ? C10 C11 H11 120.0 . . ? C8 C11 H11 120.0 . . ? C11 C8 C12 120.49(14) . . ? C11 C8 H8 119.8 . . ? C12 C8 H8 119.8 . . ? C12 N2 H2 115.1(15) . . ? C12 N2 H1 116.1(13) . . ? H2 N2 H1 120(2) . . ? N3 C9 C12 120.44(13) . . ? N3 C9 H9 119.8 . . ? C12 C9 H9 119.8 . . ? N3 C10 C11 118.57(13) . . ? N3 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.351 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.056 data_an90 _database_code_depnum_ccdc_archive 'CCDC 611651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; saccharin, 2-aminopyridine ; _chemical_name_common 'Saccharin, 2-aminopyridine' _chemical_melting_point 152 _chemical_formula_moiety 'C7 H4 N O3 S, C5 H7 N2' _chemical_formula_sum 'C12 H11 N3 O3 S' _chemical_formula_weight 277.30 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 Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.7712(12) _cell_length_b 12.4593(11) _cell_length_c 14.3461(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2461.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3441 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.96 _exptl_crystal_description Prismic _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9224 _exptl_absorpt_correction_T_max 0.9450 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7903 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2293 _reflns_number_gt 2065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+1.3471P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2293 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.10361(3) 0.10898(4) 0.23742(3) 0.02319(16) Uani 1 1 d . . . O1 O 0.12196(10) 0.05622(11) -0.01225(9) 0.0288(3) Uani 1 1 d . . . O3 O 0.01017(10) 0.11474(11) 0.28312(10) 0.0295(3) Uani 1 1 d . . . N1 N 0.09790(11) 0.03620(13) 0.14481(11) 0.0233(4) Uani 1 1 d . . . O2 O 0.18258(10) 0.07630(11) 0.29689(10) 0.0310(3) Uani 1 1 d . . . C1 C 0.11946(13) 0.09394(15) 0.06809(14) 0.0230(4) Uani 1 1 d . . . C7 C 0.13174(13) 0.23218(15) 0.18235(14) 0.0234(4) Uani 1 1 d . . . C4 C 0.18107(14) 0.39263(17) 0.06182(16) 0.0308(5) Uani 1 1 d . . . C2 C 0.14020(13) 0.21021(15) 0.08811(13) 0.0228(4) Uani 1 1 d . . . C3 C 0.16502(14) 0.29052(17) 0.02618(15) 0.0271(4) Uani 1 1 d . . . C6 C 0.14609(15) 0.33345(17) 0.21904(16) 0.0285(5) Uani 1 1 d . . . C5 C 0.17095(15) 0.41394(17) 0.15675(17) 0.0318(5) Uani 1 1 d . . . N2 N 0.10440(11) 0.65917(15) 0.46390(12) 0.0241(4) Uani 1 1 d . . . N3 N 0.05883(13) 0.69540(15) 0.61580(12) 0.0300(4) Uani 1 1 d . . . C11 C 0.13122(16) 0.79543(19) 0.35308(15) 0.0333(5) Uani 1 1 d . . . C10 C 0.10455(15) 0.87151(19) 0.41954(16) 0.0331(5) Uani 1 1 d . . . C12 C 0.13060(14) 0.69010(18) 0.37693(14) 0.0279(5) Uani 1 1 d . . . C8 C 0.08024(13) 0.73109(16) 0.53094(13) 0.0243(4) Uani 1 1 d . . . C9 C 0.07922(15) 0.84079(17) 0.50668(15) 0.0283(5) Uani 1 1 d . . . H2 H 0.1061(15) 0.592(2) 0.4717(16) 0.031(6) Uiso 1 1 d . . . H12 H 0.1473(16) 0.6355(19) 0.3391(15) 0.027(6) Uiso 1 1 d . . . H9 H 0.0618(16) 0.8908(19) 0.5554(16) 0.035(6) Uiso 1 1 d . . . H4 H 0.1974(15) 0.4489(18) 0.0241(15) 0.028(6) Uiso 1 1 d . . . H3 H 0.1701(15) 0.2765(18) -0.0380(16) 0.030(6) Uiso 1 1 d . . . H5 H 0.1813(17) 0.483(2) 0.1824(16) 0.044(7) Uiso 1 1 d . . . H10 H 0.1019(16) 0.948(2) 0.4025(17) 0.045(7) Uiso 1 1 d . . . H3B H 0.0382(18) 0.744(2) 0.6594(17) 0.048(7) Uiso 1 1 d . . . H11 H 0.1506(18) 0.814(2) 0.2929(19) 0.049(7) Uiso 1 1 d . . . H6 H 0.1410(16) 0.3459(18) 0.2821(16) 0.029(6) Uiso 1 1 d . . . H3A H 0.065(2) 0.619(2) 0.6255(19) 0.060(8) 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 0.0278(3) 0.0190(3) 0.0228(3) -0.00153(19) -0.00104(19) -0.00048(19) O1 0.0343(8) 0.0278(8) 0.0242(7) -0.0032(6) -0.0001(6) 0.0001(6) O3 0.0339(8) 0.0247(7) 0.0301(7) -0.0011(6) 0.0057(6) -0.0007(6) N1 0.0273(8) 0.0188(8) 0.0238(8) -0.0025(7) -0.0013(7) -0.0009(6) O2 0.0365(8) 0.0271(8) 0.0295(7) 0.0009(6) -0.0085(6) -0.0010(6) C1 0.0179(9) 0.0238(10) 0.0273(10) -0.0014(8) -0.0010(8) 0.0017(7) C7 0.0193(9) 0.0206(10) 0.0303(10) 0.0010(8) -0.0019(8) 0.0002(7) C4 0.0223(10) 0.0260(11) 0.0442(13) 0.0086(10) 0.0042(9) -0.0008(8) C2 0.0157(8) 0.0236(10) 0.0291(10) 0.0002(8) -0.0001(8) 0.0019(7) C3 0.0201(9) 0.0286(11) 0.0326(11) 0.0035(9) 0.0016(8) -0.0002(8) C6 0.0258(10) 0.0235(11) 0.0362(12) -0.0048(9) -0.0019(9) -0.0012(8) C5 0.0241(10) 0.0202(11) 0.0512(13) -0.0031(10) 0.0001(9) -0.0016(8) N2 0.0213(8) 0.0255(10) 0.0254(9) 0.0001(7) -0.0024(7) 0.0014(7) N3 0.0410(10) 0.0225(9) 0.0264(9) 0.0005(8) 0.0054(8) 0.0029(8) C11 0.0314(11) 0.0419(13) 0.0265(11) 0.0067(10) -0.0005(9) -0.0046(10) C10 0.0343(12) 0.0299(12) 0.0352(12) 0.0056(10) -0.0044(9) -0.0050(9) C12 0.0232(10) 0.0363(12) 0.0243(10) -0.0038(9) 0.0003(8) 0.0013(9) C8 0.0200(9) 0.0287(11) 0.0242(9) -0.0009(8) -0.0018(8) -0.0019(8) C9 0.0270(10) 0.0235(10) 0.0346(11) -0.0012(9) -0.0006(9) -0.0013(8) _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 O2 1.4410(14) . ? S1 O3 1.4460(14) . ? S1 N1 1.6105(16) . ? S1 C7 1.7693(19) . ? O1 C1 1.245(2) . ? N1 C1 1.348(2) . ? C1 C2 1.504(3) . ? C7 C6 1.381(3) . ? C7 C2 1.384(3) . ? C4 C3 1.389(3) . ? C4 C5 1.395(3) . ? C4 H4 0.91(2) . ? C2 C3 1.381(3) . ? C3 H3 0.94(2) . ? C6 C5 1.386(3) . ? C6 H6 0.92(2) . ? C5 H5 0.95(3) . ? N2 C12 1.355(3) . ? N2 C8 1.356(3) . ? N2 H2 0.85(2) . ? N3 C8 1.329(3) . ? N3 H3B 0.92(3) . ? N3 H3A 0.96(3) . ? C11 C12 1.356(3) . ? C11 C10 1.394(3) . ? C11 H11 0.93(3) . ? C10 C9 1.353(3) . ? C10 H10 0.99(3) . ? C12 H12 0.90(2) . ? C8 C9 1.410(3) . ? C9 H9 0.97(2) . ? 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 O2 S1 O3 114.66(9) . . ? O2 S1 N1 111.48(8) . . ? O3 S1 N1 111.01(8) . . ? O2 S1 C7 110.14(9) . . ? O3 S1 C7 110.75(8) . . ? N1 S1 C7 97.52(9) . . ? C1 N1 S1 111.24(13) . . ? O1 C1 N1 124.08(18) . . ? O1 C1 C2 122.34(18) . . ? N1 C1 C2 113.58(16) . . ? C6 C7 C2 122.73(19) . . ? C6 C7 S1 130.82(16) . . ? C2 C7 S1 106.44(14) . . ? C3 C4 C5 121.2(2) . . ? C3 C4 H4 121.6(13) . . ? C5 C4 H4 117.2(13) . . ? C3 C2 C7 120.39(19) . . ? C3 C2 C1 128.46(18) . . ? C7 C2 C1 111.15(17) . . ? C2 C3 C4 117.8(2) . . ? C2 C3 H3 121.0(14) . . ? C4 C3 H3 121.3(14) . . ? C7 C6 C5 116.8(2) . . ? C7 C6 H6 121.2(15) . . ? C5 C6 H6 122.0(14) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 116.5(15) . . ? C4 C5 H5 122.4(15) . . ? C12 N2 C8 122.04(19) . . ? C12 N2 H2 113.3(16) . . ? C8 N2 H2 124.6(16) . . ? C8 N3 H3B 118.2(16) . . ? C8 N3 H3A 116.3(17) . . ? H3B N3 H3A 126(2) . . ? C12 C11 C10 118.9(2) . . ? C12 C11 H11 118.3(17) . . ? C10 C11 H11 122.7(17) . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.5(14) . . ? C11 C10 H10 120.0(14) . . ? N2 C12 C11 120.6(2) . . ? N2 C12 H12 114.1(14) . . ? C11 C12 H12 125.3(14) . . ? N3 C8 N2 118.88(19) . . ? N3 C8 C9 123.23(19) . . ? N2 C8 C9 117.89(18) . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 123.4(13) . . ? C8 C9 H9 116.6(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.379 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.053 data_grd99_m _database_code_depnum_ccdc_archive 'CCDC 611652' _audit_creation_method SHELXL-97 _chemical_name_systematic ; saccharin, 2-amino-4,6-dimethylpyrimidine ; _chemical_name_common 'saccharin, 2-amino-4,6-dimethylpyrimidine' _chemical_melting_point 188 _chemical_formula_moiety 'C6 H10 N3, C7 H4 N O3 S' _chemical_formula_sum 'C13 H14 N4 O3 S' _chemical_formula_weight 306.34 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2644(15) _cell_length_b 7.3820(15) _cell_length_c 13.752(3) _cell_angle_alpha 98.667(3) _cell_angle_beta 95.025(3) _cell_angle_gamma 100.566(3) _cell_volume 711.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2134 _cell_measurement_theta_min 2.845 _cell_measurement_theta_max 27.989 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9320 _exptl_absorpt_correction_T_max 0.9509 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4992 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2894 _reflns_number_gt 2430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.1226P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2894 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.37831(7) 0.27724(6) 0.35763(3) 0.04515(19) Uani 1 1 d . . . N1 N 1.0748(2) 0.7628(2) 0.24080(12) 0.0426(4) Uani 1 1 d . . . O1 O 0.2419(2) 0.1342(2) 0.09093(10) 0.0652(5) Uani 1 1 d . . . O3 O 0.5433(2) 0.2232(2) 0.39979(11) 0.0605(4) Uani 1 1 d . . . O2 O 0.2409(2) 0.3057(2) 0.42372(11) 0.0644(4) Uani 1 1 d . . . N4 N 0.2830(2) 0.1335(2) 0.25778(12) 0.0491(4) Uani 1 1 d . . . N2 N 0.9404(2) 0.4894(2) 0.12787(14) 0.0540(4) Uani 1 1 d . . . C8 C 0.3955(3) 0.4160(2) 0.19988(14) 0.0398(4) Uani 1 1 d . . . C1 C 1.0258(3) 0.6705(3) 0.14708(15) 0.0461(5) Uani 1 1 d . . . C13 C 0.4441(3) 0.4733(3) 0.30048(14) 0.0401(4) Uani 1 1 d . . . C2 C 1.0348(3) 0.6795(3) 0.32002(15) 0.0482(5) Uani 1 1 d . . . C9 C 0.4351(3) 0.5401(3) 0.13519(15) 0.0510(5) Uani 1 1 d . . . H9 H 0.4025 0.5018 0.0657 0.061 Uiso 1 1 calc R . . N3 N 1.0648(3) 0.7582(3) 0.07310(15) 0.0663(6) Uani 1 1 d . . . C4 C 0.8989(3) 0.4057(3) 0.20421(18) 0.0529(5) Uani 1 1 d . . . C7 C 0.3003(3) 0.2148(3) 0.17627(15) 0.0462(5) Uani 1 1 d . . . C12 C 0.5315(3) 0.6549(3) 0.34118(16) 0.0497(5) Uani 1 1 d . . . H12 H 0.5639 0.6930 0.4106 0.060 Uiso 1 1 calc R . . C11 C 0.5692(3) 0.7784(3) 0.27573(17) 0.0555(5) Uani 1 1 d . . . H11 H 0.6277 0.9048 0.3009 0.067 Uiso 1 1 calc R . . C3 C 0.9419(3) 0.4978(3) 0.30140(17) 0.0552(5) Uani 1 1 d . . . H3 H 0.9069 0.4349 0.3544 0.066 Uiso 1 1 calc R . . C10 C 0.5240(3) 0.7224(3) 0.17482(18) 0.0581(6) Uani 1 1 d . . . H10 H 0.5542 0.8100 0.1318 0.070 Uiso 1 1 calc R . . C5 C 1.0964(4) 0.7944(4) 0.41980(17) 0.0696(7) Uani 1 1 d . . . H5A H 1.0284 0.7351 0.4689 0.104 Uiso 1 1 calc R . . H5B H 1.0693 0.9196 0.4199 0.104 Uiso 1 1 calc R . . H5C H 1.2323 0.8042 0.4364 0.104 Uiso 1 1 calc R . . C6 C 0.8045(4) 0.2040(3) 0.1800(2) 0.0747(7) Uani 1 1 d . . . H6A H 0.7022 0.1868 0.1260 0.112 Uiso 1 1 calc R . . H6B H 0.7527 0.1645 0.2386 0.112 Uiso 1 1 calc R . . H6C H 0.8966 0.1285 0.1596 0.112 Uiso 1 1 calc R . . H3B H 1.111(4) 0.866(4) 0.0825(19) 0.068(8) Uiso 1 1 d . . . H1 H 1.138(3) 0.875(4) 0.2482(16) 0.062(7) Uiso 1 1 d . . . H3A H 1.047(4) 0.705(4) 0.019(2) 0.065(8) 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 0.0541(3) 0.0387(3) 0.0401(3) 0.0103(2) 0.0032(2) 0.0010(2) N1 0.0426(9) 0.0357(8) 0.0467(9) 0.0090(7) 0.0039(7) -0.0004(7) O1 0.0947(12) 0.0458(8) 0.0421(8) 0.0053(6) -0.0050(8) -0.0118(8) O3 0.0686(10) 0.0522(9) 0.0582(9) 0.0135(7) -0.0096(8) 0.0104(7) O2 0.0741(10) 0.0692(10) 0.0520(9) 0.0182(7) 0.0228(8) 0.0061(8) N4 0.0602(10) 0.0369(8) 0.0444(9) 0.0109(7) -0.0007(8) -0.0056(7) N2 0.0566(10) 0.0366(9) 0.0631(11) 0.0072(8) 0.0064(8) -0.0043(7) C8 0.0395(9) 0.0336(9) 0.0457(10) 0.0078(7) 0.0081(8) 0.0036(7) C1 0.0469(10) 0.0358(10) 0.0512(11) 0.0070(8) 0.0001(9) -0.0001(8) C13 0.0394(9) 0.0364(9) 0.0447(10) 0.0085(7) 0.0076(8) 0.0055(7) C2 0.0424(10) 0.0522(11) 0.0536(12) 0.0166(9) 0.0125(9) 0.0091(9) C9 0.0598(12) 0.0459(11) 0.0478(11) 0.0142(9) 0.0131(9) 0.0035(9) N3 0.1003(17) 0.0406(11) 0.0433(11) 0.0075(8) -0.0095(10) -0.0159(10) C4 0.0434(11) 0.0383(10) 0.0786(15) 0.0152(10) 0.0168(10) 0.0032(8) C7 0.0511(11) 0.0375(10) 0.0463(11) 0.0089(8) 0.0037(9) -0.0013(8) C12 0.0521(11) 0.0386(10) 0.0535(11) 0.0017(8) 0.0030(9) 0.0032(8) C11 0.0547(12) 0.0335(10) 0.0738(15) 0.0077(9) 0.0065(11) -0.0007(9) C3 0.0511(12) 0.0522(12) 0.0696(14) 0.0272(11) 0.0203(10) 0.0091(9) C10 0.0637(13) 0.0419(11) 0.0726(15) 0.0245(10) 0.0199(11) 0.0026(10) C5 0.0805(16) 0.0770(17) 0.0480(12) 0.0126(11) 0.0172(11) 0.0010(13) C6 0.0735(16) 0.0384(12) 0.111(2) 0.0163(13) 0.0329(15) -0.0047(11) _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 O2 1.4301(16) . ? S1 O3 1.4336(15) . ? S1 N4 1.6171(16) . ? S1 C13 1.7595(19) . ? N1 C1 1.348(2) . ? N1 C2 1.357(2) . ? N1 H1 0.86(3) . ? O1 C7 1.233(2) . ? N4 C7 1.354(2) . ? N2 C4 1.326(3) . ? N2 C1 1.342(2) . ? C8 C13 1.379(3) . ? C8 C9 1.381(3) . ? C8 C7 1.493(2) . ? C1 N3 1.310(3) . ? C13 C12 1.383(3) . ? C2 C3 1.362(3) . ? C2 C5 1.485(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? N3 H3B 0.79(3) . ? N3 H3A 0.78(3) . ? C4 C3 1.386(3) . ? C4 C6 1.495(3) . ? C12 C11 1.384(3) . ? C12 H12 0.9500 . ? C11 C10 1.379(3) . ? C11 H11 0.9500 . ? C3 H3 0.9500 . ? C10 H10 0.9500 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 O2 S1 O3 115.45(10) . . ? O2 S1 N4 110.86(10) . . ? O3 S1 N4 110.98(9) . . ? O2 S1 C13 111.47(9) . . ? O3 S1 C13 109.92(9) . . ? N4 S1 C13 96.60(8) . . ? C1 N1 C2 121.80(17) . . ? C1 N1 H1 116.8(15) . . ? C2 N1 H1 121.3(15) . . ? C7 N4 S1 111.68(13) . . ? C4 N2 C1 117.75(18) . . ? C13 C8 C9 120.45(17) . . ? C13 C8 C7 111.30(16) . . ? C9 C8 C7 128.25(18) . . ? N3 C1 N2 119.18(19) . . ? N3 C1 N1 119.44(18) . . ? N2 C1 N1 121.38(18) . . ? C8 C13 C12 122.34(18) . . ? C8 C13 S1 107.32(13) . . ? C12 C13 S1 130.33(16) . . ? N1 C2 C3 117.3(2) . . ? N1 C2 C5 117.14(19) . . ? C3 C2 C5 125.5(2) . . ? C8 C9 C10 117.9(2) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C1 N3 H3B 121.0(19) . . ? C1 N3 H3A 120.7(19) . . ? H3B N3 H3A 118(3) . . ? N2 C4 C3 122.44(18) . . ? N2 C4 C6 116.3(2) . . ? C3 C4 C6 121.3(2) . . ? O1 C7 N4 124.37(17) . . ? O1 C7 C8 122.62(17) . . ? N4 C7 C8 113.01(16) . . ? C13 C12 C11 116.72(19) . . ? C13 C12 H12 121.6 . . ? C11 C12 H12 121.6 . . ? C10 C11 C12 121.57(19) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C2 C3 C4 119.22(19) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C11 C10 C9 121.01(19) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.196 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.062