# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 O7 S, C2 H8 N, H2 O' _chemical_formula_sum 'C10 H15 N O8 S' _chemical_formula_weight 309.29 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 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 17.6223(8) _cell_length_b 6.7830(5) _cell_length_c 11.4011(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1362.80(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 625 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 28.50 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 1.50 _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method floatation _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9163 _exptl_absorpt_correction_T_max 0.9461 _exptl_absorpt_process_details ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18497 _diffrn_reflns_av_R_equivalents 0.0932 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 29.50 _reflns_number_total 1965 _reflns_number_gt 977 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland (2008). CrysAlis CCD, Version 171.32.6 ; _computing_cell_refinement ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _computing_data_reduction ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular Structure Visualisation, University of Bonn, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0150P)^2^+2.0500P] 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 0.0038(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1965 _refine_ls_number_parameters 140 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1686 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.004 _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 0.37648(6) 0.2500 0.75750(9) 0.0585(4) Uani 1 2 d S . . O1 O 0.41479(18) 0.2500 0.8659(3) 0.1126(19) Uani 1 2 d S . . O2 O 0.33190(16) 0.0795(6) 0.7392(2) 0.1304(14) Uani 1 1 d . . . C1 C 0.4467(2) 0.2500 0.6475(3) 0.0399(11) Uani 1 2 d S . . C2 C 0.4244(2) 0.2500 0.5308(3) 0.0356(10) Uani 1 2 d S . . H2 H 0.3730 0.2500 0.5120 0.043 Uiso 1 2 calc SR . . C3 C 0.4778(2) 0.2500 0.4425(3) 0.0350(10) Uani 1 2 d S . . C4 C 0.5544(2) 0.2500 0.4702(3) 0.0387(11) Uani 1 2 d S . . H4 H 0.5907 0.2500 0.4110 0.046 Uiso 1 2 calc SR . . C5 C 0.5769(2) 0.2500 0.5886(3) 0.0313(9) Uani 1 2 d S . . C6 C 0.5231(2) 0.2500 0.6757(3) 0.0395(11) Uani 1 2 d S . . H6 H 0.5381 0.2500 0.7539 0.047 Uiso 1 2 calc SR . . C7 C 0.4570(2) 0.2500 0.3154(3) 0.0371(11) Uani 1 2 d S . . O3 O 0.50092(15) 0.2500 0.2380(2) 0.0642(11) Uani 1 2 d S . . O4 O 0.38263(16) 0.2500 0.3014(2) 0.0697(12) Uani 1 2 d SD . . H41 H 0.376(3) 0.2500 0.2301(8) 0.105 Uiso 1 2 d SD . . C8 C 0.6589(2) 0.2500 0.6159(4) 0.0440(12) Uani 1 2 d S . . O5 O 0.70721(15) 0.2500 0.5410(3) 0.0677(11) Uani 1 2 d S . . O6 O 0.67394(16) 0.2500 0.7258(3) 0.0884(15) Uani 1 2 d SD . . H61 H 0.7187(10) 0.2500 0.745(5) 0.133 Uiso 1 2 d SD . . C9 C 0.0806(4) 0.2500 0.5044(5) 0.0780(18) Uani 1 2 d SD . . H91 H 0.0274(10) 0.2500 0.482(5) 0.117 Uiso 1 2 d SD . . H92 H 0.085(2) 0.117(2) 0.534(3) 0.117 Uiso 1 1 d D . . N1 N 0.1335(2) 0.2500 0.4070(3) 0.0707(14) Uani 1 2 d SD . . H1N H 0.130(2) 0.130(3) 0.367(3) 0.106 Uiso 1 1 d D . . C10 C 0.2153(3) 0.2500 0.4417(6) 0.088(2) Uani 1 2 d SD . . H101 H 0.243(3) 0.2500 0.368(3) 0.132 Uiso 1 2 d SD . . H102 H 0.220(2) 0.134(4) 0.491(3) 0.132 Uiso 1 1 d D . . O1W O 0.3417(2) 0.2500 0.0819(3) 0.0933(15) Uani 1 2 d SD . . H1W H 0.2957(7) 0.2500 0.093(6) 0.140 Uiso 1 2 d SD . . H2W H 0.359(4) 0.2500 0.015(2) 0.140 Uiso 1 2 d SD . . 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 0.0373(5) 0.1021(13) 0.0361(5) 0.000 0.0062(4) 0.000 O1 0.0635(19) 0.228(6) 0.0465(17) 0.000 0.0063(14) 0.000 O2 0.100(2) 0.198(4) 0.093(2) -0.045(2) 0.0570(17) -0.090(2) C1 0.0250(19) 0.066(3) 0.029(2) 0.000 0.0052(16) 0.000 C2 0.0231(18) 0.055(3) 0.0284(19) 0.000 -0.0011(16) 0.000 C3 0.0268(19) 0.049(3) 0.029(2) 0.000 -0.0013(15) 0.000 C4 0.028(2) 0.063(3) 0.0251(19) 0.000 0.0057(16) 0.000 C5 0.0236(18) 0.040(3) 0.0299(19) 0.000 0.0002(15) 0.000 C6 0.028(2) 0.064(3) 0.027(2) 0.000 -0.0032(16) 0.000 C7 0.029(2) 0.053(3) 0.028(2) 0.000 -0.0021(17) 0.000 O3 0.0392(16) 0.126(3) 0.0277(15) 0.000 0.0037(13) 0.000 O4 0.0313(16) 0.147(4) 0.0305(15) 0.000 -0.0048(14) 0.000 C8 0.0227(19) 0.067(4) 0.043(2) 0.000 -0.0029(18) 0.000 O5 0.0240(15) 0.129(3) 0.0501(18) 0.000 0.0105(14) 0.000 O6 0.0269(16) 0.203(5) 0.0359(18) 0.000 -0.0070(14) 0.000 C9 0.067(3) 0.127(6) 0.040(3) 0.000 0.009(3) 0.000 N1 0.039(2) 0.128(5) 0.045(2) 0.000 0.0007(19) 0.000 C10 0.051(3) 0.114(6) 0.099(5) 0.000 -0.016(3) 0.000 O1W 0.052(2) 0.192(5) 0.0358(18) 0.000 -0.0085(17) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.408(3) . ? S1 O2 1.413(3) . ? S1 O2 1.413(3) 7_565 ? S1 C1 1.762(4) . ? C1 C6 1.384(5) . ? C1 C2 1.388(5) . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.385(5) . ? C3 C7 1.494(5) . ? C4 C5 1.407(5) . ? C4 H4 0.9300 . ? C5 C6 1.372(5) . ? C5 C8 1.478(5) . ? C6 H6 0.9300 . ? C7 O3 1.174(4) . ? C7 O4 1.321(4) . ? O4 H41 0.821(5) . ? C8 O5 1.206(4) . ? C8 O6 1.281(5) . ? O6 H61 0.820(5) . ? C9 N1 1.451(7) . ? C9 H91 0.970(5) . ? C9 H92 0.969(5) . ? N1 C10 1.494(7) . ? N1 H1N 0.940(5) . ? C10 H101 0.970(5) . ? C10 H102 0.969(5) . ? O1W H1W 0.820(5) . ? O1W H2W 0.820(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 113.33(16) . . ? O1 S1 O2 113.33(16) . 7_565 ? O2 S1 O2 109.8(3) . 7_565 ? O1 S1 C1 106.71(18) . . ? O2 S1 C1 106.59(13) . . ? O2 S1 C1 106.59(13) 7_565 . ? C6 C1 C2 119.9(3) . . ? C6 C1 S1 121.2(3) . . ? C2 C1 S1 118.9(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 C7 122.7(3) . . ? C4 C3 C7 117.4(3) . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 C8 121.5(3) . . ? C4 C5 C8 118.5(3) . . ? C5 C6 C1 120.2(4) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O3 C7 O4 124.3(4) . . ? O3 C7 C3 124.5(3) . . ? O4 C7 C3 111.2(3) . . ? C7 O4 H41 105(4) . . ? O5 C8 O6 123.1(4) . . ? O5 C8 C5 122.8(4) . . ? O6 C8 C5 114.1(3) . . ? C8 O6 H61 118(5) . . ? N1 C9 H91 115(4) . . ? N1 C9 H92 102(3) . . ? H91 C9 H92 100(3) . . ? C9 N1 C10 114.7(4) . . ? C9 N1 H1N 109(3) . . ? C10 N1 H1N 101(3) . . ? N1 C10 H101 105(4) . . ? N1 C10 H102 104(3) . . ? H101 C10 H102 117(3) . . ? H1W O1W H2W 121(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H41 O1W 0.82(1) 1.80(1) 2.604(4) 168(6) . O6 H61 O2 0.82(1) 2.31(1) 3.041(4) 148(2) 4_556 O6 H61 O2 0.82(1) 2.31(1) 3.041(4) 148(2) 6_657 N1 H1N O2 0.94(1) 2.14(2) 3.004(5) 153(3) 2_554 O1W H1W O5 0.82(1) 2.19(2 2.753(4) 126(6) 6_556 O1W H2W O1 0.82(1) 1.97(1) 2.779(4) 171(7) 1_554 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.246 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 952224' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 O7 S, C4 H12 N' _chemical_formula_sum 'C12 H17 N O7 S' _chemical_formula_weight 319.33 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' _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 12.235(2) _cell_length_b 8.0730(10) _cell_length_c 15.736(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.620(10) _cell_angle_gamma 90.00 _cell_volume 1496.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 765 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 28.39 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 1.41 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method floatation _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9163 _exptl_absorpt_correction_T_max 0.9461 _exptl_absorpt_process_details ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19422 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3722 _reflns_number_gt 2864 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland (2008). CrysAlis CCD, Version 171.32.6 ; _computing_cell_refinement ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _computing_data_reduction ; Oxford Diffraction Poland (2008). CrysAlis Red, Version 171.32.6 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular Structure Visualisation, University of Bonn, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0880P)^2^] 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 3722 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.65534(3) 0.69616(4) 0.22109(2) 0.02711(13) Uani 1 1 d . . . O1 O 0.59138(9) 0.84878(13) 0.21095(8) 0.0427(3) Uani 1 1 d . . . O2 O 0.69238(8) 0.65344(16) 0.14379(7) 0.0438(3) Uani 1 1 d . . . O3 O 0.59706(9) 0.56093(13) 0.25127(7) 0.0407(3) Uani 1 1 d . . . C1 C 0.78123(10) 0.73283(16) 0.30737(8) 0.0263(3) Uani 1 1 d . . . C2 C 0.86758(11) 0.82593(16) 0.28919(8) 0.0261(3) Uani 1 1 d . . . H2 H 0.8598 0.8669 0.2326 0.031 Uiso 1 1 calc R . . C3 C 0.96615(11) 0.85777(17) 0.35619(8) 0.0273(3) Uani 1 1 d . . . C4 C 0.97779(12) 0.79621(17) 0.44026(9) 0.0311(3) Uani 1 1 d . . . H4 H 1.0431 0.8188 0.4850 0.037 Uiso 1 1 calc R . . C5 C 0.89182(12) 0.70054(17) 0.45788(9) 0.0307(3) Uani 1 1 d . . . C6 C 0.79332(12) 0.66871(17) 0.39124(9) 0.0298(3) Uani 1 1 d . . . H6 H 0.7358 0.6047 0.4029 0.036 Uiso 1 1 calc R . . C7 C 1.05972(12) 0.95101(18) 0.33391(9) 0.0297(3) Uani 1 1 d . . . O4 O 1.06022(11) 0.98373(16) 0.25891(7) 0.0506(3) Uani 1 1 d . . . O5 O 1.14333(9) 0.99417(14) 0.40227(7) 0.0397(3) Uani 1 1 d . . . H5 H 1.1981(19) 1.046(2) 0.3841(13) 0.060 Uiso 1 1 d . . . C8 C 0.90459(13) 0.6240(2) 0.54627(10) 0.0379(3) Uani 1 1 d . . . O6 O 0.83539(11) 0.53378(17) 0.56364(8) 0.0581(4) Uani 1 1 d . . . O7 O 1.00245(11) 0.66389(16) 0.60340(8) 0.0510(3) Uani 1 1 d . . . H7 H 1.0097(19) 0.609(3) 0.6527(15) 0.077 Uiso 1 1 d . . . N1 N 0.39265(12) 0.71160(18) 0.28423(11) 0.0460(4) Uani 1 1 d . . . H1N H 0.423(2) 0.800(3) 0.2733(15) 0.069 Uiso 1 1 d . . . H2N H 0.442(2) 0.623(3) 0.2761(14) 0.069 Uiso 1 1 d . . . C9 C 0.28379(16) 0.7064(2) 0.21424(19) 0.0675(6) Uani 1 1 d . . . H9A H 0.2384 0.6146 0.2253 0.101 Uiso 1 1 calc R . . H9B H 0.2420 0.8079 0.2159 0.101 Uiso 1 1 calc R . . C10 C 0.3027(3) 0.6872(4) 0.1257(2) 0.0966(9) Uani 1 1 d . . . H10A H 0.3458 0.7796 0.1139 0.145 Uiso 1 1 calc R . . H10B H 0.2309 0.6830 0.0820 0.145 Uiso 1 1 calc R . . H10C H 0.3437 0.5865 0.1238 0.145 Uiso 1 1 calc R . . C11 C 0.3835(2) 0.7174(3) 0.37671(17) 0.0689(6) Uani 1 1 d . . . H11A H 0.3394 0.8137 0.3840 0.103 Uiso 1 1 calc R . . H11B H 0.3438 0.6195 0.3883 0.103 Uiso 1 1 calc R . . C12 C 0.4969(3) 0.7257(4) 0.44104(18) 0.1045(10) Uani 1 1 d . . . H12A H 0.5421 0.6337 0.4318 0.157 Uiso 1 1 calc R . . H12B H 0.4885 0.7213 0.4999 0.157 Uiso 1 1 calc R . . H12C H 0.5336 0.8274 0.4330 0.157 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 0.01962(18) 0.0249(2) 0.0360(2) -0.00140(12) 0.00613(13) 0.00199(11) O1 0.0302(5) 0.0280(5) 0.0643(7) -0.0019(5) 0.0031(5) 0.0078(4) O2 0.0276(5) 0.0688(8) 0.0327(6) -0.0099(5) 0.0042(4) 0.0070(5) O3 0.0332(5) 0.0329(6) 0.0537(6) 0.0016(5) 0.0077(5) -0.0080(4) C1 0.0224(6) 0.0252(7) 0.0308(7) -0.0020(5) 0.0067(5) 0.0027(5) C2 0.0271(6) 0.0265(7) 0.0255(6) 0.0003(5) 0.0082(5) 0.0011(5) C3 0.0266(6) 0.0271(6) 0.0284(6) -0.0020(5) 0.0077(5) -0.0018(5) C4 0.0275(7) 0.0372(8) 0.0268(7) -0.0013(5) 0.0039(5) -0.0001(5) C5 0.0317(7) 0.0333(7) 0.0288(7) 0.0027(5) 0.0112(6) 0.0036(5) C6 0.0274(6) 0.0314(7) 0.0334(7) 0.0026(5) 0.0128(5) -0.0001(5) C7 0.0308(7) 0.0299(7) 0.0287(7) -0.0040(5) 0.0083(5) -0.0050(5) O4 0.0548(7) 0.0681(8) 0.0288(6) -0.0041(5) 0.0112(5) -0.0324(6) O5 0.0300(5) 0.0551(7) 0.0325(5) -0.0008(4) 0.0060(4) -0.0128(5) C8 0.0398(8) 0.0449(9) 0.0310(7) 0.0057(6) 0.0128(6) 0.0057(7) O6 0.0542(7) 0.0788(10) 0.0436(7) 0.0196(6) 0.0173(6) -0.0129(7) O7 0.0430(7) 0.0740(9) 0.0325(6) 0.0166(6) 0.0040(5) -0.0019(6) N1 0.0366(8) 0.0331(8) 0.0725(10) 0.0050(7) 0.0220(7) 0.0016(6) C9 0.0323(9) 0.0408(11) 0.121(2) -0.0002(11) 0.0054(11) -0.0029(7) C10 0.0751(17) 0.098(2) 0.0903(19) -0.0156(15) -0.0235(15) 0.0095(14) C11 0.0831(16) 0.0528(12) 0.0887(16) 0.0054(10) 0.0540(14) 0.0120(11) C12 0.116(2) 0.138(3) 0.0638(16) 0.0026(15) 0.0314(17) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4452(10) . ? S1 O2 1.4494(11) . ? S1 O3 1.4521(10) . ? S1 C1 1.7825(13) . ? C1 C2 1.3877(18) . ? C1 C6 1.3879(19) . ? C2 C3 1.3956(18) . ? C2 H2 0.9300 . ? C3 C4 1.3842(19) . ? C3 C7 1.4887(18) . ? C4 C5 1.3916(19) . ? C4 H4 0.9300 . ? C5 C6 1.392(2) . ? C5 C8 1.4913(19) . ? C6 H6 0.9300 . ? C7 O4 1.2111(17) . ? C7 O5 1.3162(17) . ? O5 H5 0.90(2) . ? C8 O6 1.2027(18) . ? C8 O7 1.329(2) . ? O7 H7 0.88(2) . ? N1 C9 1.483(3) . ? N1 C11 1.490(3) . ? N1 H1N 0.84(2) . ? N1 H2N 0.96(2) . ? C9 C10 1.480(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.483(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 O1 S1 O2 113.12(7) . . ? O1 S1 O3 112.21(7) . . ? O2 S1 O3 112.81(7) . . ? O1 S1 C1 105.88(6) . . ? O2 S1 C1 106.11(6) . . ? O3 S1 C1 105.99(6) . . ? C2 C1 C6 120.39(12) . . ? C2 C1 S1 118.85(10) . . ? C6 C1 S1 120.76(10) . . ? C1 C2 C3 119.68(12) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.10(12) . . ? C4 C3 C7 121.26(12) . . ? C2 C3 C7 118.57(12) . . ? C3 C4 C5 120.06(13) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.99(12) . . ? C4 C5 C8 121.39(13) . . ? C6 C5 C8 118.56(13) . . ? C1 C6 C5 119.77(13) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O4 C7 O5 122.14(13) . . ? O4 C7 C3 123.08(12) . . ? O5 C7 C3 114.78(11) . . ? C7 O5 H5 110.2(13) . . ? O6 C8 O7 123.65(14) . . ? O6 C8 C5 124.02(14) . . ? O7 C8 C5 112.31(13) . . ? C8 O7 H7 109.5(15) . . ? C9 N1 C11 115.93(18) . . ? C9 N1 H1N 103.1(16) . . ? C11 N1 H1N 108.9(16) . . ? C9 N1 H2N 110.3(13) . . ? C11 N1 H2N 111.5(12) . . ? H1N N1 H2N 106.3(19) . . ? C10 C9 N1 111.42(18) . . ? C10 C9 H9A 109.3 . . ? N1 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? N1 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N1 111.41(18) . . ? C12 C11 H11A 109.3 . . ? N1 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? N1 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O5 H5 O2 0.90(2) 1.75(2) 2.646(2) 176(2) 2_755 y O7 H7 O4 0.88(2) 1.78(2) 2.641(2) 166(2) 4_576 y N1 H1N O3 0.84(2) 2.14(2) 2.884(2) 147(2) 2_655 y N1 H1N O1 0.84(2) 2.54(2) 3.159(2) 131(2) . y N1 H2N O3 0.96(2) 2.10(2) 2.950(2) 146(2) . y N1 H2N O1 0.96(2) 2.27(2) 2.935(2) 125(2) 2_645 y _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.279 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 952225' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 O7 S, C6 H16 N, H2 O' _chemical_formula_sum 'C14 H23 N O8 S' _chemical_formula_weight 365.39 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' _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 13.1122(3) _cell_length_b 9.5655(2) _cell_length_c 14.8057(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.892(3) _cell_angle_gamma 90.00 _cell_volume 1786.03(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1282 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.34 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 1.355 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method floatation _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9577 _exptl_absorpt_process_details ; Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6, Wroc\/law, Poland ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method '1024x1024 with blocks 2x2' _diffrn_detector_area_resol_mean \w-scan _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24104 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4427 _reflns_number_gt 2848 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_cell_refinement ; Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6, Wroc\/law, Poland ; _computing_data_reduction ; Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6, Wroc\/law, Poland ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular Structure Visualisation, University of Bonn, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0310P)^2^+0.9582P] 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 4427 _refine_ls_number_parameters 239 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.34321(3) 0.29202(5) 0.10823(3) 0.03864(13) Uani 1 1 d . . . O1 O 0.33921(12) 0.2411(2) 0.01683(11) 0.0790(6) Uani 1 1 d . . . O2 O 0.38971(10) 0.42861(14) 0.12873(12) 0.0598(4) Uani 1 1 d . . . O3 O 0.39288(11) 0.19313(14) 0.18113(11) 0.0587(4) Uani 1 1 d . . . C1 C 0.21017(12) 0.30633(17) 0.11393(12) 0.0321(4) Uani 1 1 d . . . C2 C 0.15230(13) 0.18630(17) 0.11521(13) 0.0357(4) Uani 1 1 d . . . H2 H 0.1826 0.0995 0.1109 0.043 Uiso 1 1 calc R . . C3 C 0.04933(13) 0.19383(16) 0.12289(13) 0.0341(4) Uani 1 1 d . . . C4 C 0.00436(13) 0.32347(17) 0.12913(13) 0.0353(4) Uani 1 1 d . . . H4 H -0.0642 0.3294 0.1353 0.042 Uiso 1 1 calc R . . C5 C 0.06180(13) 0.44394(16) 0.12613(12) 0.0337(4) Uani 1 1 d . . . C6 C 0.16494(13) 0.43527(17) 0.11808(12) 0.0336(4) Uani 1 1 d . . . H6 H 0.2032 0.5163 0.1155 0.040 Uiso 1 1 calc R . . C7 C -0.00811(14) 0.06080(18) 0.12653(14) 0.0397(4) Uani 1 1 d . . . O4 O 0.03541(12) -0.05071(13) 0.12322(13) 0.0687(5) Uani 1 1 d . . . O5 O -0.10331(10) 0.07320(13) 0.13401(12) 0.0536(4) Uani 1 1 d D . . H5O H -0.1318(18) -0.0034(13) 0.1336(18) 0.080 Uiso 1 1 d D . . C8 C 0.01269(15) 0.58236(18) 0.13291(13) 0.0399(4) Uani 1 1 d . . . O6 O -0.07278(11) 0.59551(14) 0.14746(12) 0.0592(4) Uani 1 1 d . . . O7 O 0.07268(13) 0.68676(13) 0.12233(14) 0.0651(5) Uani 1 1 d D . . H7O H 0.041(2) 0.7609(16) 0.122(2) 0.098 Uiso 1 1 d D . . C11 C 0.67655(14) 0.3761(2) 0.22476(14) 0.0459(5) Uani 1 1 d . . . H11 H 0.7461 0.3882 0.2702 0.069 Uiso 1 1 calc R . . C12 C 0.66793(18) 0.2274(2) 0.19010(16) 0.0618(6) Uani 1 1 d . . . H121 H 0.6005 0.2139 0.1449 0.093 Uiso 1 1 calc R . . H122 H 0.6740 0.1649 0.2420 0.093 Uiso 1 1 calc R . . H123 H 0.7237 0.2086 0.1612 0.093 Uiso 1 1 calc R . . C13 C 0.6666(2) 0.4813(3) 0.14737(18) 0.0714(7) Uani 1 1 d . . . H131 H 0.6000 0.4686 0.1009 0.107 Uiso 1 1 calc R . . H132 H 0.7235 0.4685 0.1189 0.107 Uiso 1 1 calc R . . H133 H 0.6699 0.5740 0.1729 0.107 Uiso 1 1 calc R . . N1 N 0.59244(12) 0.40740(17) 0.27351(11) 0.0367(3) Uani 1 1 d . . . H1N H 0.6004(16) 0.498(2) 0.2934(14) 0.055 Uiso 1 1 d . . . H2N H 0.5304(18) 0.401(2) 0.2317(15) 0.055 Uiso 1 1 d . . . C14 C 0.58750(16) 0.3190(2) 0.35572(14) 0.0472(5) Uani 1 1 d . . . H14 H 0.5741 0.2218 0.3348 0.071 Uiso 1 1 calc R . . C15 C 0.6911(2) 0.3256(3) 0.43159(16) 0.0712(7) Uani 1 1 d . . . H151 H 0.7475 0.2943 0.4068 0.107 Uiso 1 1 calc R . . H152 H 0.6872 0.2664 0.4829 0.107 Uiso 1 1 calc R . . H153 H 0.7044 0.4201 0.4534 0.107 Uiso 1 1 calc R . . C16 C 0.49507(19) 0.3704(3) 0.38912(17) 0.0714(7) Uani 1 1 d . . . H161 H 0.4857 0.3104 0.4382 0.107 Uiso 1 1 calc R . . H162 H 0.4318 0.3695 0.3377 0.107 Uiso 1 1 calc R . . H163 H 0.5089 0.4640 0.4127 0.107 Uiso 1 1 calc R . . O1W O 0.80589(11) 0.83913(15) 0.14242(11) 0.0517(4) Uani 1 1 d D . . H1W H 0.7576(14) 0.825(3) 0.0947(11) 0.078 Uiso 1 1 d D . . H2W H 0.8390(18) 0.7656(15) 0.1482(18) 0.078 Uiso 1 1 d 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 0.0289(2) 0.0386(2) 0.0476(3) -0.0018(2) 0.00912(18) 0.00046(19) O1 0.0449(8) 0.1378(16) 0.0576(10) -0.0329(10) 0.0199(7) -0.0033(10) O2 0.0367(7) 0.0423(8) 0.0975(12) 0.0040(8) 0.0133(7) -0.0078(6) O3 0.0395(7) 0.0491(8) 0.0817(11) 0.0149(8) 0.0069(7) 0.0105(6) C1 0.0296(8) 0.0299(8) 0.0359(9) 0.0008(7) 0.0074(7) 0.0006(7) C2 0.0345(9) 0.0234(8) 0.0488(11) 0.0011(8) 0.0107(8) 0.0055(7) C3 0.0334(8) 0.0220(8) 0.0460(10) 0.0002(7) 0.0092(7) -0.0009(7) C4 0.0313(8) 0.0254(8) 0.0482(11) -0.0009(7) 0.0094(8) 0.0032(7) C5 0.0377(9) 0.0213(8) 0.0396(10) -0.0009(7) 0.0064(7) 0.0034(7) C6 0.0348(9) 0.0233(8) 0.0418(10) 0.0010(7) 0.0088(7) -0.0023(7) C7 0.0367(9) 0.0249(9) 0.0572(12) -0.0006(8) 0.0126(8) 0.0004(7) O4 0.0591(9) 0.0223(7) 0.1316(15) -0.0016(8) 0.0378(9) 0.0011(6) O5 0.0384(7) 0.0316(7) 0.0923(11) -0.0009(7) 0.0203(7) -0.0053(6) C8 0.0420(10) 0.0250(9) 0.0505(12) -0.0001(8) 0.0091(8) 0.0055(8) O6 0.0469(8) 0.0350(7) 0.0986(12) -0.0049(7) 0.0249(8) 0.0119(6) O7 0.0682(10) 0.0208(7) 0.1150(14) 0.0012(8) 0.0397(9) 0.0038(7) C11 0.0340(9) 0.0603(13) 0.0460(11) -0.0024(10) 0.0152(8) -0.0014(9) C12 0.0654(14) 0.0663(15) 0.0611(14) -0.0097(12) 0.0299(11) 0.0128(12) C13 0.0789(16) 0.0804(17) 0.0676(16) 0.0092(14) 0.0414(13) -0.0082(14) N1 0.0340(8) 0.0386(8) 0.0380(9) -0.0048(7) 0.0109(6) -0.0040(7) C14 0.0586(12) 0.0428(11) 0.0443(12) -0.0010(9) 0.0214(9) -0.0102(9) C15 0.0749(16) 0.0870(19) 0.0478(13) 0.0150(13) 0.0101(12) 0.0003(14) C16 0.0729(16) 0.0898(19) 0.0656(16) -0.0089(14) 0.0425(13) -0.0169(14) O1W 0.0399(8) 0.0439(8) 0.0685(10) -0.0044(8) 0.0100(7) -0.0049(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 O1 1.4257(16) . ? S1 O2 1.4387(14) . ? S1 O3 1.4488(14) . ? S1 C1 1.7746(16) . ? C1 C6 1.377(2) . ? C1 C2 1.379(2) . ? C2 C3 1.388(2) . ? C2 H2 0.9300 . ? C3 C4 1.387(2) . ? C3 C7 1.487(2) . ? C4 C5 1.384(2) . ? C4 H4 0.9300 . ? C5 C6 1.392(2) . ? C5 C8 1.488(2) . ? C6 H6 0.9300 . ? C7 O4 1.217(2) . ? C7 O5 1.289(2) . ? O5 H5O 0.822(5) . ? C8 O6 1.204(2) . ? C8 O7 1.307(2) . ? O7 H7O 0.820(5) . ? C11 C13 1.504(3) . ? C11 N1 1.504(2) . ? C11 C12 1.506(3) . ? C11 H11 0.9800 . ? C12 H121 0.9600 . ? C12 H122 0.9600 . ? C12 H123 0.9600 . ? C13 H131 0.9600 . ? C13 H132 0.9600 . ? C13 H133 0.9600 . ? N1 C14 1.498(2) . ? N1 H1N 0.91(2) . ? N1 H2N 0.88(2) . ? C14 C15 1.508(3) . ? C14 C16 1.511(3) . ? C14 H14 0.9800 . ? C15 H151 0.9600 . ? C15 H152 0.9600 . ? C15 H153 0.9600 . ? C16 H161 0.9600 . ? C16 H162 0.9600 . ? C16 H163 0.9600 . ? O1W H1W 0.82(2) . ? O1W H2W 0.82(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 O1 S1 O2 114.43(11) . . ? O1 S1 O3 112.11(11) . . ? O2 S1 O3 110.96(9) . . ? O1 S1 C1 106.88(8) . . ? O2 S1 C1 106.58(8) . . ? O3 S1 C1 105.20(8) . . ? C6 C1 C2 119.98(15) . . ? C6 C1 S1 120.80(12) . . ? C2 C1 S1 119.21(12) . . ? C1 C2 C3 120.62(15) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 119.52(15) . . ? C2 C3 C7 118.19(14) . . ? C4 C3 C7 122.27(15) . . ? C5 C4 C3 119.82(15) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.20(15) . . ? C4 C5 C8 119.31(15) . . ? C6 C5 C8 120.49(15) . . ? C1 C6 C5 119.83(15) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O4 C7 O5 124.06(16) . . ? O4 C7 C3 120.06(16) . . ? O5 C7 C3 115.88(15) . . ? C7 O5 H5O 111.5(18) . . ? O6 C8 O7 124.18(17) . . ? O6 C8 C5 123.10(17) . . ? O7 C8 C5 112.71(16) . . ? C8 O7 H7O 110(2) . . ? C13 C11 N1 108.09(17) . . ? C13 C11 C12 112.94(19) . . ? N1 C11 C12 110.79(16) . . ? C13 C11 H11 108.3 . . ? N1 C11 H11 108.3 . . ? C12 C11 H11 108.3 . . ? C11 C12 H121 109.5 . . ? C11 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C11 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C11 C13 H131 109.5 . . ? C11 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C11 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? C14 N1 C11 118.55(15) . . ? C14 N1 H1N 107.4(13) . . ? C11 N1 H1N 108.1(13) . . ? C14 N1 H2N 107.3(14) . . ? C11 N1 H2N 107.9(14) . . ? H1N N1 H2N 107.1(19) . . ? N1 C14 C15 110.56(17) . . ? N1 C14 C16 107.39(18) . . ? C15 C14 C16 112.45(19) . . ? N1 C14 H14 108.8 . . ? C15 C14 H14 108.8 . . ? C16 C14 H14 108.8 . . ? C14 C15 H151 109.5 . . ? C14 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C14 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? C14 C16 H161 109.5 . . ? C14 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C14 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? H1W O1W H2W 102(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5O O1W 0.82(1) 1.74(1) 2.555(2) 175(3) 1_445 O7 H7O O4 0.82(2) 1.80(1) 2.559(2) 153(3) 1_565 N1 H1N O3 0.91(2) 1.90(2) 2.808(2) 173(2) 2_655 N1 H2N O2 0.88(2) 2.06(2) 2.929(2) 168(2) . O1W H1W O1 0.82(1) 1.90(1) 2.704(2) 169(3) 3_665 O1W H2W O6 0.82(1) 2.00(1) 2.811(2) 172(3) 1_655 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.275 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 952226'