# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Yoo, Jung' 'Feketeova, Linda' 'Khairallah, George' 'White, Jonathan M.' "O'Hair, Richard" _publ_contact_author_name "O'Hair, Richard" _publ_contact_author_email rohair@unimelb.edu.au _publ_section_title ; Structure and Unimolecular Chemistry of Protonated Sulfur Betaines, (CH3)2S+(CH2)nCO2H (n = 1 and 2) ; # Attachment '- DMSA.cif' data_jmwroh1 _database_code_depnum_ccdc_archive 'CCDC 794852' #TrackingRef '- DMSA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H9 Cl O2 S' _chemical_formula_weight 156.62 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 ' 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 7.0225(8) _cell_length_b 7.3868(8) _cell_length_c 13.8536(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.912(2) _cell_angle_gamma 90.00 _cell_volume 705.65(13) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2209 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.52 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.752 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 3359 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1608 _reflns_number_gt 1493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _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^)+(0.0435P)^2^+0.1888P] 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 1608 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.006 _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 Cl1 Cl 0.14406(5) 0.84952(4) 0.41684(2) 0.02118(12) Uani 1 1 d . . . S1 S 0.34054(5) 0.14303(4) 0.68574(2) 0.01795(12) Uani 1 1 d . . . O2 O 0.25801(15) 0.47217(15) 0.46178(7) 0.0241(2) Uani 1 1 d . . . O1 O 0.22890(15) 0.50513(14) 0.61953(7) 0.0250(2) Uani 1 1 d . . . C2 C 0.34047(19) 0.22367(18) 0.56358(9) 0.0176(3) Uani 1 1 d . . . H2A H 0.4736 0.2175 0.5498 0.021 Uiso 1 1 calc R . . H2B H 0.2558 0.1457 0.5154 0.021 Uiso 1 1 calc R . . C3 C 0.4376(2) -0.07847(19) 0.67488(10) 0.0236(3) Uani 1 1 d . . . H3A H 0.5562 -0.0692 0.6476 0.035 Uiso 1 1 calc R . . H3B H 0.3420 -0.1523 0.6312 0.035 Uiso 1 1 calc R . . H3C H 0.4678 -0.1352 0.7399 0.035 Uiso 1 1 calc R . . C4 C 0.5447(2) 0.2559(2) 0.75760(10) 0.0242(3) Uani 1 1 d . . . H4A H 0.5712 0.2049 0.8241 0.036 Uiso 1 1 calc R . . H4B H 0.5163 0.3854 0.7611 0.036 Uiso 1 1 calc R . . H4C H 0.6584 0.2393 0.7270 0.036 Uiso 1 1 calc R . . C1 C 0.26856(18) 0.41621(19) 0.55288(9) 0.0184(3) Uani 1 1 d . . . H1 H 0.224(3) 0.579(4) 0.4551(17) 0.053(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 Cl1 0.01998(19) 0.01897(19) 0.0238(2) 0.00059(12) 0.00215(14) 0.00059(11) S1 0.01842(19) 0.0197(2) 0.01558(19) 0.00089(11) 0.00267(13) -0.00051(11) O2 0.0339(6) 0.0200(5) 0.0177(5) 0.0022(4) 0.0035(4) 0.0047(4) O1 0.0335(6) 0.0214(5) 0.0210(5) -0.0016(4) 0.0075(4) 0.0020(4) C2 0.0209(7) 0.0182(6) 0.0134(6) -0.0002(5) 0.0029(5) -0.0006(5) C3 0.0298(7) 0.0168(6) 0.0243(7) 0.0029(5) 0.0054(6) 0.0012(6) C4 0.0247(7) 0.0271(7) 0.0185(6) -0.0023(5) -0.0019(5) -0.0048(6) C1 0.0163(6) 0.0203(7) 0.0177(6) 0.0005(5) 0.0006(5) -0.0019(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 C3 1.7899(14) . ? S1 C4 1.7892(14) . ? S1 C2 1.7941(13) . ? O2 C1 1.3166(16) . ? O1 C1 1.2079(17) . ? C2 C1 1.5072(19) . ? 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 S1 C4 101.24(7) . . ? C3 S1 C2 98.99(6) . . ? C4 S1 C2 103.13(7) . . ? C1 C2 S1 110.26(9) . . ? O1 C1 O2 125.65(13) . . ? O1 C1 C2 124.02(12) . . ? O2 C1 C2 110.34(11) . . ? 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 S1 C2 C1 -178.27(9) . . . . ? C4 S1 C2 C1 -74.41(10) . . . . ? S1 C2 C1 O1 4.27(17) . . . . ? S1 C2 C1 O2 -176.46(9) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.369 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.064 # Attachment '- DMSP.cif' data_jmwelle2 _database_code_depnum_ccdc_archive 'CCDC 794853' #TrackingRef '- DMSP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N3 O9 S' _chemical_formula_weight 363.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3627(9) _cell_length_b 9.5890(9) _cell_length_c 11.7822(19) _cell_angle_alpha 69.895(12) _cell_angle_beta 73.702(12) _cell_angle_gamma 79.988(9) _cell_volume 746.99(17) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 799 _cell_measurement_theta_min 4.1113 _cell_measurement_theta_max 72.8126 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 2.469 _exptl_absorpt_correction_T_min 0.82263 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5047 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.1425 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 73.07 _reflns_number_total 2860 _reflns_number_gt 1396 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution ? _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^)+(0.0438P)^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 2860 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.777 _refine_ls_restrained_S_all 0.777 _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 C1 C 0.6223(6) 0.7224(4) 0.5758(4) 0.0339(11) Uani 1 1 d . . . C2 C 0.5357(6) 0.8075(4) 0.4682(4) 0.0348(11) Uani 1 1 d . . . H2A H 0.6305 0.8644 0.4006 0.042 Uiso 1 1 calc R . . H2B H 0.4329 0.8772 0.4932 0.042 Uiso 1 1 calc R . . C3 C 0.4597(6) 0.7041(4) 0.4229(4) 0.0354(11) Uani 1 1 d . . . H3A H 0.3846 0.6348 0.4946 0.042 Uiso 1 1 calc R . . H3B H 0.5667 0.6463 0.3857 0.042 Uiso 1 1 calc R . . C4 C 0.4278(7) 0.9558(4) 0.2097(4) 0.0434(12) Uani 1 1 d . . . H4A H 0.5406 0.9282 0.1544 0.065 Uiso 1 1 calc R . . H4B H 0.4609 1.0065 0.2576 0.065 Uiso 1 1 calc R . . H4C H 0.3422 1.0206 0.1620 0.065 Uiso 1 1 calc R . . C5 C 0.1146(6) 0.8694(5) 0.4022(4) 0.0464(12) Uani 1 1 d . . . H5A H 0.0418 0.7904 0.4621 0.070 Uiso 1 1 calc R . . H5B H 0.0375 0.9360 0.3490 0.070 Uiso 1 1 calc R . . H5C H 0.1555 0.9231 0.4447 0.070 Uiso 1 1 calc R . . C6 C 0.8099(6) 0.5695(4) 0.8867(4) 0.0267(9) Uani 1 1 d . . . C7 C 0.7264(5) 0.5346(4) 1.0179(4) 0.0241(9) Uani 1 1 d . . . C8 C 0.7410(6) 0.3996(4) 1.1060(4) 0.0262(9) Uani 1 1 d . . . H8 H 0.6873 0.3874 1.1899 0.031 Uiso 1 1 calc R . . C9 C 0.8392(6) 0.2806(4) 1.0660(4) 0.0296(10) Uani 1 1 d . . . C10 C 0.9192(6) 0.2991(4) 0.9423(4) 0.0303(10) Uani 1 1 d . . . H10 H 0.9815 0.2179 0.9170 0.036 Uiso 1 1 calc R . . C11 C 0.9074(6) 0.4380(4) 0.8553(4) 0.0277(9) Uani 1 1 d . . . N1 N 1.0128(5) 0.4507(4) 0.7279(3) 0.0348(9) Uani 1 1 d . . . N2 N 0.8581(6) 0.1363(4) 1.1592(4) 0.0407(10) Uani 1 1 d . . . N3 N 0.6258(5) 0.6572(4) 1.0649(3) 0.0294(8) Uani 1 1 d . . . O1 O 0.7137(4) 0.8090(3) 0.6042(3) 0.0376(8) Uani 1 1 d . . . O2 O 0.6084(4) 0.5921(3) 0.6331(3) 0.0412(8) Uani 1 1 d . . . O3 O 0.8015(4) 0.6992(3) 0.8139(3) 0.0347(7) Uani 1 1 d . . . O4 O 1.0663(4) 0.5724(3) 0.6590(3) 0.0441(9) Uani 1 1 d . . . O5 O 1.0492(4) 0.3377(3) 0.6952(3) 0.0424(8) Uani 1 1 d . . . O6 O 0.9636(6) 0.0365(3) 1.1249(3) 0.0650(11) Uani 1 1 d . . . O7 O 0.7710(5) 0.1213(3) 1.2675(3) 0.0471(9) Uani 1 1 d . . . O8 O 0.6532(4) 0.6623(3) 1.1623(3) 0.0407(8) Uani 1 1 d . . . O9 O 0.5181(4) 0.7484(3) 1.0072(3) 0.0419(8) Uani 1 1 d . . . S1 S 0.31618(16) 0.79321(12) 0.31134(10) 0.0340(3) Uani 1 1 d . . . H H 0.771(10) 0.732(7) 0.716(7) 0.14(3) 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 C1 0.039(3) 0.028(2) 0.026(2) -0.0061(19) 0.003(2) -0.0018(19) C2 0.043(3) 0.025(2) 0.031(2) -0.0013(18) -0.012(2) -0.003(2) C3 0.046(3) 0.026(2) 0.029(2) -0.0060(19) -0.004(2) 0.000(2) C4 0.057(3) 0.030(2) 0.036(3) -0.005(2) -0.009(2) -0.001(2) C5 0.029(3) 0.049(3) 0.054(3) -0.014(2) -0.007(2) 0.006(2) C6 0.028(2) 0.023(2) 0.028(2) -0.0052(17) -0.0081(19) -0.0029(17) C7 0.021(2) 0.0182(19) 0.032(2) -0.0101(17) -0.0022(18) -0.0002(16) C8 0.028(2) 0.028(2) 0.023(2) -0.0099(17) -0.0019(18) -0.0063(18) C9 0.036(2) 0.0190(19) 0.030(2) -0.0030(17) -0.006(2) -0.0054(17) C10 0.029(2) 0.029(2) 0.034(2) -0.0143(19) -0.003(2) -0.0053(18) C11 0.025(2) 0.027(2) 0.026(2) -0.0070(18) 0.0035(18) -0.0056(18) N1 0.032(2) 0.035(2) 0.038(2) -0.0121(18) -0.0091(18) -0.0021(17) N2 0.057(3) 0.0233(19) 0.039(2) -0.0059(17) -0.012(2) -0.0056(18) N3 0.028(2) 0.0287(18) 0.028(2) -0.0099(16) -0.0003(16) -0.0003(15) O1 0.0440(19) 0.0304(15) 0.0377(18) -0.0064(14) -0.0125(15) -0.0052(14) O2 0.055(2) 0.0259(16) 0.0382(17) -0.0066(14) -0.0097(16) -0.0019(14) O3 0.047(2) 0.0255(15) 0.0272(16) -0.0013(13) -0.0123(15) -0.0017(14) O4 0.050(2) 0.0357(17) 0.0333(18) -0.0034(14) 0.0042(16) -0.0069(15) O5 0.047(2) 0.0419(18) 0.0429(19) -0.0250(15) -0.0031(16) -0.0035(15) O6 0.110(3) 0.0254(16) 0.057(2) -0.0160(16) -0.028(2) 0.0195(19) O7 0.061(2) 0.0301(17) 0.0355(19) 0.0024(14) -0.0020(17) -0.0071(15) O8 0.046(2) 0.0429(18) 0.0361(18) -0.0224(15) -0.0098(15) 0.0084(15) O9 0.0423(19) 0.0364(17) 0.049(2) -0.0183(15) -0.0191(16) 0.0156(15) S1 0.0319(6) 0.0317(6) 0.0364(6) -0.0118(5) -0.0039(5) -0.0019(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 C1 O2 1.205(4) . ? C1 O1 1.329(5) . ? C1 C2 1.497(6) . ? C2 C3 1.518(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 S1 1.808(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 S1 1.775(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 S1 1.775(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 O3 1.248(4) . ? C6 C7 1.436(5) . ? C6 C11 1.449(5) . ? C7 C8 1.362(5) . ? C7 N3 1.467(4) . ? C8 C9 1.393(5) . ? C8 H8 0.9300 . ? C9 C10 1.371(5) . ? C9 N2 1.454(5) . ? C10 C11 1.379(5) . ? C10 H10 0.9300 . ? C11 N1 1.457(5) . ? N1 O4 1.227(4) . ? N1 O5 1.234(4) . ? N2 O7 1.228(4) . ? N2 O6 1.231(4) . ? N3 O9 1.229(4) . ? N3 O8 1.238(4) . ? O1 H 1.41(8) . ? O3 H 1.16(8) . ? 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 C1 O1 123.1(4) . . ? O2 C1 C2 125.1(4) . . ? O1 C1 C2 111.8(3) . . ? C1 C2 C3 111.4(3) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 S1 115.9(3) . . ? C2 C3 H3A 108.3 . . ? S1 C3 H3A 108.3 . . ? C2 C3 H3B 108.3 . . ? S1 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? S1 C4 H4A 109.5 . . ? S1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? S1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? S1 C5 H5A 109.5 . . ? S1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? S1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 C7 122.2(4) . . ? O3 C6 C11 126.6(4) . . ? C7 C6 C11 111.1(3) . . ? C8 C7 C6 126.5(4) . . ? C8 C7 N3 115.6(3) . . ? C6 C7 N3 117.7(3) . . ? C7 C8 C9 117.7(4) . . ? C7 C8 H8 121.2 . . ? C9 C8 H8 121.2 . . ? C10 C9 C8 121.1(4) . . ? C10 C9 N2 120.7(4) . . ? C8 C9 N2 118.2(4) . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 123.4(4) . . ? C10 C11 N1 116.4(4) . . ? C6 C11 N1 120.0(3) . . ? O4 N1 O5 122.9(4) . . ? O4 N1 C11 118.6(4) . . ? O5 N1 C11 118.5(3) . . ? O7 N2 O6 123.7(4) . . ? O7 N2 C9 118.5(4) . . ? O6 N2 C9 117.7(4) . . ? O9 N3 O8 123.3(3) . . ? O9 N3 C7 119.0(3) . . ? O8 N3 C7 117.7(3) . . ? C1 O1 H 111(3) . . ? C6 O3 H 125(3) . . ? C4 S1 C5 101.8(2) . . ? C4 S1 C3 105.7(2) . . ? C5 S1 C3 101.6(2) . . ? 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 O2 C1 C2 C3 -11.2(6) . . . . ? O1 C1 C2 C3 170.7(3) . . . . ? C1 C2 C3 S1 169.9(3) . . . . ? O3 C6 C7 C8 -174.3(4) . . . . ? C11 C6 C7 C8 3.3(6) . . . . ? O3 C6 C7 N3 1.1(6) . . . . ? C11 C6 C7 N3 178.7(3) . . . . ? C6 C7 C8 C9 -3.1(6) . . . . ? N3 C7 C8 C9 -178.5(4) . . . . ? C7 C8 C9 C10 0.4(6) . . . . ? C7 C8 C9 N2 179.2(4) . . . . ? C8 C9 C10 C11 1.6(6) . . . . ? N2 C9 C10 C11 -177.2(4) . . . . ? C9 C10 C11 C6 -1.2(7) . . . . ? C9 C10 C11 N1 173.8(4) . . . . ? O3 C6 C11 C10 176.4(4) . . . . ? C7 C6 C11 C10 -1.1(6) . . . . ? O3 C6 C11 N1 1.6(7) . . . . ? C7 C6 C11 N1 -175.9(4) . . . . ? C10 C11 N1 O4 -153.3(4) . . . . ? C6 C11 N1 O4 21.9(6) . . . . ? C10 C11 N1 O5 24.6(6) . . . . ? C6 C11 N1 O5 -160.2(4) . . . . ? C10 C9 N2 O7 -173.9(4) . . . . ? C8 C9 N2 O7 7.3(6) . . . . ? C10 C9 N2 O6 7.3(6) . . . . ? C8 C9 N2 O6 -171.6(4) . . . . ? C8 C7 N3 O9 -140.3(4) . . . . ? C6 C7 N3 O9 43.8(5) . . . . ? C8 C7 N3 O8 39.1(5) . . . . ? C6 C7 N3 O8 -136.8(4) . . . . ? C2 C3 S1 C4 39.8(4) . . . . ? C2 C3 S1 C5 -66.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 73.07 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.410 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.068