# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Sitaram Velaga' _publ_contact_author_email sitvel@ltu.se _publ_section_title ; Polymorphism in acesulfame sweetener: Structure-property and stability relationships of bending and brittle crystals ; loop_ _publ_author_name 'Sitaram Velaga' 'Venu Vangala' 'Srininvas Basavoju' 'Dan Bostrom' # Attachment 'Acesulfame-Form-I.cif' # Supplementary Material (ESI) for Chemical Communications data_Form-I _database_code_depnum_ccdc_archive 'CCDC 766997' #TrackingRef '- Acesulfame_Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Acesulfame Form I' _chemical_melting_point 395 _chemical_formula_moiety 'C4 H5 N O4 S' _chemical_formula_sum 'C4 H5 N O4 S' _chemical_formula_weight 163.15 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 'P 21/c' 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 7.4940(15) _cell_length_b 11.784(2) _cell_length_c 15.238(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.36(3) _cell_angle_gamma 90.00 _cell_volume 1319.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5251 _cell_measurement_theta_min 2.546 _cell_measurement_theta_max 33.142 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _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 9845 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 33.13 _reflns_number_total 5031 _reflns_number_gt 4024 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0758P)^2^+0.4884P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5031 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.68613(5) 0.09678(3) 0.12052(3) 0.02432(10) Uani 1 1 d . . . O16 O 0.54045(16) 0.06818(11) 0.16315(9) 0.0322(3) Uani 1 1 d . . . O18 O 0.65746(19) 0.10147(13) 0.02600(9) 0.0369(3) Uani 1 1 d . . . O19 O 0.84424(16) 0.00854(10) 0.15490(9) 0.0282(2) Uani 1 1 d . . . O20 O 1.01740(16) 0.33436(10) 0.18613(8) 0.0292(2) Uani 1 1 d . . . N17 N 0.78144(17) 0.21295(11) 0.16540(9) 0.0247(3) Uani 1 1 d . . . H17 H 0.7041 0.2787 0.1667 0.030 Uiso 1 1 d R . . C12 C 1.1271(3) -0.06738(16) 0.13460(14) 0.0351(4) Uani 1 1 d . . . H12A H 1.2501 -0.0467 0.1324 0.053 Uiso 1 1 calc R . . H12B H 1.0730 -0.1052 0.0801 0.053 Uiso 1 1 calc R . . H12C H 1.1270 -0.1173 0.1844 0.053 Uiso 1 1 calc R . . C13 C 0.9623(2) 0.23777(14) 0.16663(10) 0.0239(3) Uani 1 1 d . . . C14 C 1.0213(2) 0.03597(14) 0.14527(11) 0.0262(3) Uani 1 1 d . . . C15 C 1.0770(2) 0.14418(14) 0.14897(11) 0.0266(3) Uani 1 1 d . . . H15A H 1.1935 0.1601 0.1399 0.032 Uiso 1 1 calc R . . S2 S 0.82145(5) 0.09924(3) 0.40693(3) 0.02543(10) Uani 1 1 d . . . O7 O 0.97333(17) 0.12599(11) 0.36830(11) 0.0360(3) Uani 1 1 d . . . O8 O 0.50752(18) -0.14612(11) 0.33995(11) 0.0410(3) Uani 1 1 d . . . O10 O 0.8365(2) 0.10367(13) 0.50102(9) 0.0388(3) Uani 1 1 d . . . O11 O 0.66270(15) 0.18286(10) 0.36313(8) 0.0266(2) Uani 1 1 d . . . N9 N 0.73779(18) -0.02147(11) 0.36663(10) 0.0276(3) Uani 1 1 d . . . H9 H 0.8183 -0.0701 0.3568 0.033 Uiso 1 1 d R . . C3 C 0.3690(2) 0.25559(15) 0.36618(14) 0.0330(4) Uani 1 1 d . . . H3A H 0.2464 0.2333 0.3676 0.049 Uiso 1 1 calc R . . H3B H 0.3705 0.2974 0.3123 0.049 Uiso 1 1 calc R . . H3C H 0.4151 0.3025 0.4171 0.049 Uiso 1 1 calc R . . C4 C 0.5565(2) -0.04808(14) 0.35933(12) 0.0286(3) Uani 1 1 d . . . C5 C 0.4841(2) 0.15345(14) 0.36856(11) 0.0251(3) Uani 1 1 d . . . C6 C 0.4348(2) 0.04435(14) 0.37049(12) 0.0281(3) Uani 1 1 d . . . H6A H 0.3185 0.0272 0.3793 0.034 Uiso 1 1 calc R . . 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 0.01902(17) 0.02425(18) 0.0299(2) -0.00079(13) 0.00535(13) -0.00181(13) O16 0.0214(5) 0.0311(6) 0.0463(7) -0.0015(5) 0.0118(5) -0.0042(5) O18 0.0330(6) 0.0465(8) 0.0294(6) -0.0034(5) 0.0016(5) -0.0033(6) O19 0.0227(5) 0.0220(5) 0.0414(6) 0.0027(5) 0.0103(4) 0.0012(4) O20 0.0272(5) 0.0253(5) 0.0355(6) -0.0021(5) 0.0071(5) -0.0057(4) N17 0.0186(5) 0.0216(6) 0.0343(7) -0.0009(5) 0.0060(5) 0.0003(4) C12 0.0317(8) 0.0302(8) 0.0471(10) 0.0029(7) 0.0169(7) 0.0077(7) C13 0.0206(6) 0.0257(7) 0.0256(7) 0.0015(5) 0.0048(5) -0.0020(5) C14 0.0215(6) 0.0286(7) 0.0299(7) 0.0009(6) 0.0085(5) 0.0024(6) C15 0.0201(6) 0.0299(7) 0.0310(7) 0.0005(6) 0.0078(5) -0.0002(5) S2 0.01920(17) 0.02321(18) 0.0329(2) -0.00038(14) 0.00283(13) -0.00225(12) O7 0.0196(5) 0.0309(6) 0.0580(9) 0.0031(6) 0.0091(5) -0.0042(5) O8 0.0285(6) 0.0241(6) 0.0729(10) -0.0070(6) 0.0163(6) -0.0069(5) O10 0.0391(7) 0.0420(8) 0.0319(7) -0.0027(5) -0.0014(5) 0.0031(6) O11 0.0206(5) 0.0217(5) 0.0375(6) 0.0022(4) 0.0057(4) -0.0014(4) N9 0.0212(6) 0.0209(6) 0.0421(8) -0.0023(5) 0.0094(5) -0.0011(5) C3 0.0230(7) 0.0263(7) 0.0485(10) -0.0019(7) 0.0043(6) 0.0019(6) C4 0.0230(7) 0.0239(7) 0.0406(9) -0.0013(6) 0.0101(6) -0.0037(6) C5 0.0201(6) 0.0256(7) 0.0295(7) -0.0010(6) 0.0049(5) -0.0009(5) C6 0.0218(6) 0.0253(7) 0.0391(8) -0.0014(6) 0.0105(6) -0.0024(5) _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 O18 1.4149(14) . ? S1 O16 1.4166(13) . ? S1 O19 1.5859(12) . ? S1 N17 1.6308(14) . ? O19 C14 1.4011(19) . ? O20 C13 1.2272(19) . ? N17 C13 1.3832(19) . ? N17 H17 0.9699 . ? C12 C14 1.480(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C15 1.455(2) . ? C14 C15 1.340(2) . ? C15 H15A 0.9300 . ? S2 O7 1.4161(14) . ? S2 O10 1.4168(15) . ? S2 O11 1.5872(12) . ? S2 N9 1.6253(14) . ? O8 C4 1.231(2) . ? O11 C5 1.4007(19) . ? N9 C4 1.377(2) . ? N9 H9 0.8662 . ? C3 C5 1.477(2) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C6 1.452(2) . ? C5 C6 1.340(2) . ? C6 H6A 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 O18 S1 O16 119.99(9) . . ? O18 S1 O19 108.40(8) . . ? O16 S1 O19 106.60(7) . . ? O18 S1 N17 111.11(8) . . ? O16 S1 N17 108.71(8) . . ? O19 S1 N17 100.07(7) . . ? C14 O19 S1 118.39(10) . . ? C13 N17 S1 122.02(11) . . ? C13 N17 H17 114.8 . . ? S1 N17 H17 117.7 . . ? C14 C12 H12A 109.5 . . ? C14 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C14 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O20 C13 N17 118.78(14) . . ? O20 C13 C15 124.39(14) . . ? N17 C13 C15 116.75(14) . . ? C15 C14 O19 120.59(14) . . ? C15 C14 C12 128.23(15) . . ? O19 C14 C12 111.15(14) . . ? C14 C15 C13 122.59(14) . . ? C14 C15 H15A 118.7 . . ? C13 C15 H15A 118.7 . . ? O7 S2 O10 120.14(9) . . ? O7 S2 O11 106.51(8) . . ? O10 S2 O11 107.84(8) . . ? O7 S2 N9 108.63(8) . . ? O10 S2 N9 111.26(9) . . ? O11 S2 N9 100.55(7) . . ? C5 O11 S2 117.86(10) . . ? C4 N9 S2 122.05(12) . . ? C4 N9 H9 123.0 . . ? S2 N9 H9 114.4 . . ? C5 C3 H3A 109.5 . . ? C5 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C5 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O8 C4 N9 118.44(15) . . ? O8 C4 C6 124.58(15) . . ? N9 C4 C6 116.89(14) . . ? C6 C5 O11 120.65(14) . . ? C6 C5 C3 128.32(15) . . ? O11 C5 C3 110.93(13) . . ? C5 C6 C4 122.33(14) . . ? C5 C6 H6A 118.8 . . ? C4 C6 H6A 118.8 . . ? 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 O18 S1 O19 C14 68.30(14) . . . . ? O16 S1 O19 C14 -161.24(12) . . . . ? N17 S1 O19 C14 -48.10(13) . . . . ? O18 S1 N17 C13 -72.82(15) . . . . ? O16 S1 N17 C13 153.02(13) . . . . ? O19 S1 N17 C13 41.52(14) . . . . ? S1 N17 C13 O20 166.82(12) . . . . ? S1 N17 C13 C15 -16.4(2) . . . . ? S1 O19 C14 C15 31.5(2) . . . . ? S1 O19 C14 C12 -150.43(13) . . . . ? O19 C14 C15 C13 2.6(3) . . . . ? C12 C14 C15 C13 -175.12(18) . . . . ? O20 C13 C15 C14 166.51(16) . . . . ? N17 C13 C15 C14 -10.1(2) . . . . ? O7 S2 O11 C5 161.20(12) . . . . ? O10 S2 O11 C5 -68.59(13) . . . . ? N9 S2 O11 C5 47.99(13) . . . . ? O7 S2 N9 C4 -151.89(14) . . . . ? O10 S2 N9 C4 73.70(16) . . . . ? O11 S2 N9 C4 -40.30(16) . . . . ? S2 N9 C4 O8 -170.15(14) . . . . ? S2 N9 C4 C6 13.1(2) . . . . ? S2 O11 C5 C6 -30.4(2) . . . . ? S2 O11 C5 C3 152.90(12) . . . . ? O11 C5 C6 C4 -5.5(3) . . . . ? C3 C5 C6 C4 170.61(18) . . . . ? O8 C4 C6 C5 -162.32(18) . . . . ? N9 C4 C6 C5 14.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.437 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.103 #= = = END # Attachment 'Acesulfame-Form-II.cif' # Supplementary Material (ESI) for Chemical Communications data_Form-II _database_code_depnum_ccdc_archive 'CCDC 766998' #TrackingRef '- Acesulfame_Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Acesulfame Form II' _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N O4 S' _chemical_formula_sum 'C4 H5 N O4 S' _chemical_formula_weight 163.15 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' O O 0.0106 0.0060 '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' 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 6.3310(2) _cell_length_b 7.4720(3) _cell_length_c 7.7150(3) _cell_angle_alpha 62.5460(15) _cell_angle_beta 73.1710(18) _cell_angle_gamma 77.874(2) _cell_volume 308.73(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1278 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.103 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _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 1307 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 26.81 _reflns_number_total 1307 _reflns_number_gt 1256 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0499P)^2^+0.1263P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1307 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 S1 S 0.32384(6) 0.29766(5) 0.51038(5) 0.02210(17) Uani 1 1 d . . . O2 O 0.26233(18) 0.52983(15) 0.37444(16) 0.0241(3) Uani 1 1 d . . . O3 O 0.04567(19) 0.14800(17) 0.23567(16) 0.0255(3) Uani 1 1 d . . . O4 O 0.54836(19) 0.24665(18) 0.43369(19) 0.0300(3) Uani 1 1 d . . . O5 O 0.2523(2) 0.27075(18) 0.71193(17) 0.0305(3) Uani 1 1 d . . . N6 N 0.1579(2) 0.19207(18) 0.46565(19) 0.0226(3) Uani 1 1 d . . . H6 H 0.0740 0.0854 0.5739 0.027 Uiso 1 1 d R . . C7 C 0.2126(2) 0.4488(2) 0.1251(2) 0.0219(3) Uani 1 1 d . . . H7 H 0.2294 0.4813 -0.0137 0.026 Uiso 1 1 d R . . C8 C 0.2622(2) 0.5817(2) 0.1748(2) 0.0221(3) Uani 1 1 d . . . C9 C 0.1355(2) 0.2528(2) 0.2729(2) 0.0210(3) Uani 1 1 d . . . C10 C 0.3131(3) 0.7939(2) 0.0430(3) 0.0275(4) Uani 1 1 d . . . H10A H 0.3109 0.8256 -0.0920 0.033 Uiso 1 1 d R . . H10B H 0.4573 0.8107 0.0477 0.033 Uiso 1 1 d R . . H10C H 0.2043 0.8830 0.0882 0.033 Uiso 1 1 d R . . 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 0.0241(3) 0.0194(2) 0.0235(3) -0.00709(17) -0.00751(17) -0.00500(16) O2 0.0309(6) 0.0172(5) 0.0249(6) -0.0081(4) -0.0069(5) -0.0043(4) O3 0.0298(6) 0.0241(6) 0.0247(6) -0.0093(5) -0.0060(5) -0.0094(4) O4 0.0234(6) 0.0298(6) 0.0378(7) -0.0137(5) -0.0102(5) -0.0014(5) O5 0.0391(7) 0.0305(6) 0.0232(6) -0.0089(5) -0.0081(5) -0.0106(5) N6 0.0256(7) 0.0195(6) 0.0222(6) -0.0052(5) -0.0063(5) -0.0083(5) C7 0.0205(7) 0.0211(7) 0.0226(7) -0.0074(6) -0.0049(6) -0.0034(5) C8 0.0196(7) 0.0202(7) 0.0228(7) -0.0063(6) -0.0044(6) -0.0020(5) C9 0.0179(7) 0.0203(7) 0.0245(7) -0.0095(6) -0.0043(6) -0.0016(5) C10 0.0306(9) 0.0184(8) 0.0305(8) -0.0062(6) -0.0072(7) -0.0057(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 S1 O5 1.4162(12) . ? S1 O4 1.4175(12) . ? S1 O2 1.5925(11) . ? S1 N6 1.6292(13) . ? O2 C8 1.4043(18) . ? O3 C9 1.2277(18) . ? N6 C9 1.382(2) . ? N6 H6 0.9599 . ? C7 C8 1.335(2) . ? C7 C9 1.457(2) . ? C7 H7 0.9600 . ? C8 C10 1.480(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 O4 120.28(8) . . ? O5 S1 O2 106.71(7) . . ? O4 S1 O2 108.03(7) . . ? O5 S1 N6 108.80(7) . . ? O4 S1 N6 110.96(7) . . ? O2 S1 N6 100.05(6) . . ? C8 O2 S1 116.85(9) . . ? C9 N6 S1 121.10(10) . . ? C9 N6 H6 118.8 . . ? S1 N6 H6 120.1 . . ? C8 C7 C9 122.89(14) . . ? C8 C7 H7 119.5 . . ? C9 C7 H7 117.6 . . ? C7 C8 O2 120.71(13) . . ? C7 C8 C10 127.95(15) . . ? O2 C8 C10 111.30(13) . . ? O3 C9 N6 120.25(14) . . ? O3 C9 C7 123.53(14) . . ? N6 C9 C7 116.14(13) . . ? C8 C10 H10A 109.6 . . ? C8 C10 H10B 109.4 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.4 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.81 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.327 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.067