# Electronic Supplementary Material for CrystEngComm # This journal is (c) The royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Edward R.T. Tiekink' _publ_contact_author_email EDWARD.TIEKINK@UTSA.EDU _publ_section_title ; The influence of cation upon the supramolecular aggregation patterns of dithiocarbamate anions functionalised with hydrogen bonding capacity - the prevalence of charge-assisted O-H...S interactions ; loop_ _publ_author_name 'Edward R.T. Tiekink' 'Geraldo de Lima' 'R A Howie' 'Daniela C. Menezes' 'James L. Wardell' ; S.M.S.V.Wardell ; 'David J. Young' # Attachment '1.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 690732' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H10 N O2 S2, H4 N' _chemical_formula_sum 'C5 H14 N2 O2 S2' _chemical_formula_weight 198.30 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.0102(15) _cell_length_b 8.0880(9) _cell_length_c 15.8727(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1798.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5687 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.549 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 39454 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.012 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 6.5 _diffrn_reflns_theta_max 26.5 _reflns_number_total 1838 _reflns_number_gt 1799 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0336P)^2^+0.9098P] 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 1838 _refine_ls_number_parameters 118 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.028 _refine_ls_R_factor_gt 0.028 _refine_ls_wR_factor_ref 0.068 _refine_ls_wR_factor_gt 0.067 _refine_ls_goodness_of_fit_ref 1.13 _refine_ls_restrained_S_all 1.12 _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 -0.05826(2) 0.65947(4) 0.43744(2) 0.01806(11) Uani 1 1 d . . . S2 S -0.16057(2) 0.73554(4) 0.27853(2) 0.01750(11) Uani 1 1 d . . . O1 O 0.25724(7) 0.78248(13) 0.41003(6) 0.0209(2) Uani 1 1 d D . . H1O H 0.2970 0.7669 0.3712 0.031 Uiso 1 1 d D . . O2 O 0.09359(7) 0.68934(13) 0.06772(6) 0.0204(2) Uani 1 1 d D . . H2O H 0.0553 0.7308 0.0329 0.031 Uiso 1 1 d D . . N1 N 0.02937(8) 0.72405(13) 0.29226(7) 0.0135(2) Uani 1 1 d . . . N2 N 0.25872(8) 0.55460(14) 0.55380(7) 0.0174(2) Uani 1 1 d D . . H1N H 0.2696 0.6149 0.5989 0.026 Uiso 1 1 d D . . H2N H 0.3047 0.4810 0.5494 0.026 Uiso 1 1 d D . . H3N H 0.2593 0.6202 0.5096 0.026 Uiso 1 1 d D . . H4N H 0.2032 0.5042 0.5576 0.026 Uiso 1 1 d D . . C1 C -0.05480(9) 0.70938(15) 0.33232(8) 0.0138(3) Uani 1 1 d . . . C2 C 0.12033(9) 0.67945(16) 0.33261(8) 0.0155(3) Uani 1 1 d . . . H2A H 0.1627 0.6270 0.2905 0.019 Uiso 1 1 calc R . . H2B H 0.1082 0.5980 0.3779 0.019 Uiso 1 1 calc R . . C3 C 0.16995(9) 0.83012(17) 0.36973(8) 0.0163(3) Uani 1 1 d . . . H3A H 0.1837 0.9108 0.3244 0.020 Uiso 1 1 calc R . . H3B H 0.1274 0.8840 0.4113 0.020 Uiso 1 1 calc R . . C4 C 0.03899(10) 0.78463(16) 0.20537(8) 0.0155(3) Uani 1 1 d . . . H4A H 0.0984 0.8502 0.2005 0.019 Uiso 1 1 calc R . . H4B H -0.0154 0.8584 0.1922 0.019 Uiso 1 1 calc R . . C5 C 0.04161(11) 0.64363(17) 0.14159(9) 0.0197(3) Uani 1 1 d . . . H5A H 0.0719 0.5456 0.1677 0.024 Uiso 1 1 calc R . . H5B H -0.0244 0.6133 0.1257 0.024 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 0.0157(2) 0.0262(2) 0.01227(18) 0.00248(12) -0.00033(11) -0.00421(13) S2 0.01284(19) 0.02425(19) 0.01541(18) -0.00264(12) -0.00286(12) 0.00180(12) O1 0.0146(5) 0.0321(6) 0.0159(5) 0.0016(4) -0.0031(4) -0.0010(4) O2 0.0205(6) 0.0279(5) 0.0129(5) 0.0031(4) 0.0017(4) 0.0072(4) N1 0.0118(5) 0.0161(5) 0.0127(5) 0.0009(4) -0.0007(4) -0.0001(4) N2 0.0146(6) 0.0181(6) 0.0193(6) -0.0006(4) -0.0004(5) -0.0003(4) C1 0.0155(7) 0.0118(6) 0.0141(6) -0.0018(5) -0.0012(5) -0.0003(5) C2 0.0122(6) 0.0180(6) 0.0163(6) 0.0003(5) -0.0011(5) 0.0012(5) C3 0.0141(7) 0.0206(7) 0.0143(6) 0.0005(5) -0.0013(5) -0.0001(5) C4 0.0182(7) 0.0158(6) 0.0124(6) 0.0016(5) 0.0013(5) -0.0012(5) C5 0.0244(7) 0.0192(7) 0.0154(6) -0.0010(5) 0.0040(5) -0.0011(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 C1 1.7174(14) . ? S2 C1 1.7232(14) . ? O1 C3 1.4330(16) . ? O1 H1O 0.84000 . ? O2 C5 1.4289(17) . ? O2 H2O 0.84000 . ? N1 C1 1.3450(17) . ? N1 C4 1.4698(17) . ? N1 C2 1.4711(17) . ? N2 H1N 0.88000 . ? N2 H2N 0.88000 . ? N2 H3N 0.88000 . ? N2 H4N 0.88000 . ? C2 C3 1.5216(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5253(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 O1 H1O 106.1 . . ? C5 O2 H2O 108.5 . . ? C1 N1 C4 123.60(11) . . ? C1 N1 C2 122.15(11) . . ? C4 N1 C2 114.25(11) . . ? H1N N2 H2N 108.3 . . ? H1N N2 H3N 108.3 . . ? H2N N2 H3N 109.7 . . ? H1N N2 H4N 110.7 . . ? H2N N2 H4N 109.8 . . ? H3N N2 H4N 110.0 . . ? N1 C1 S1 120.31(10) . . ? N1 C1 S2 120.60(10) . . ? S1 C1 S2 119.08(8) . . ? N1 C2 C3 111.59(10) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O1 C3 C2 110.33(11) . . ? O1 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O1 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C5 112.07(10) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O2 C5 C4 111.31(11) . . ? O2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? O2 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? 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 C4 N1 C1 S1 -172.74(9) . . . . ? C2 N1 C1 S1 7.46(16) . . . . ? C4 N1 C1 S2 8.78(17) . . . . ? C2 N1 C1 S2 -171.01(9) . . . . ? C1 N1 C2 C3 -96.74(14) . . . . ? C4 N1 C2 C3 83.44(13) . . . . ? N1 C2 C3 O1 178.83(10) . . . . ? C1 N1 C4 C5 -94.53(15) . . . . ? C2 N1 C4 C5 85.28(14) . . . . ? N1 C4 C5 O2 -152.59(12) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.36 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.049 # Attachment '2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 690733' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aza-1-azoniabicyclo(2.2.2)octanium bis(ethanol)dithiocarbamate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N2, C5 H10 N O2 S2' _chemical_formula_sum 'C11 H23 N3 O2 S2' _chemical_formula_weight 293.44 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 7.7299(3) _cell_length_b 9.8682(4) _cell_length_c 10.1834(4) _cell_angle_alpha 70.968(2) _cell_angle_beta 81.797(2) _cell_angle_gamma 75.6620(18) _cell_volume 709.83(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3079 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_type multi-scan # compare SADABS Tmin/max (below) with calc 0.8349/0.9707 _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_special_details ; Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000) but refined with the DENZO/COLLECT HKL package. Refs as: Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 12002 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.039 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 27.6 _reflns_number_total 3251 _reflns_number_gt 2557 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0336P)^2^+0.3389P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 3251 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.053 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.083 _refine_ls_wR_factor_gt 0.076 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 0.81602(6) 0.21037(5) 0.45911(4) 0.02267(12) Uani 1 1 d . . . S2 S 0.55152(5) 0.40285(5) 0.25289(4) 0.01912(11) Uani 1 1 d . . . O1 O 1.36194(15) 0.16581(12) 0.22330(13) 0.0236(3) Uani 1 1 d . . . H1O H 1.4362 0.2117 0.2309 0.035 Uiso 1 1 calc R . . O2 O 0.85040(16) 0.12687(12) -0.03340(12) 0.0219(3) Uani 1 1 d . . . H2O H 0.9481 0.1345 -0.0803 0.033 Uiso 1 1 calc R . . N1 N 0.87721(17) 0.26504(14) 0.18500(13) 0.0143(3) Uani 1 1 d . . . N2 N 0.41867(18) 0.24538(14) 0.60033(14) 0.0169(3) Uani 1 1 d . . . H2N H 0.5127 0.2597 0.5329 0.020 Uiso 1 1 calc R . . N3 N 0.16333(18) 0.20607(15) 0.78461(14) 0.0191(3) Uani 1 1 d . . . C1 C 0.7594(2) 0.28970(16) 0.29024(16) 0.0150(3) Uani 1 1 d . . . C2 C 1.0571(2) 0.17022(17) 0.20985(16) 0.0157(3) Uani 1 1 d . . . H2A H 1.0946 0.1201 0.1373 0.019 Uiso 1 1 calc R . . H2B H 1.0540 0.0942 0.3015 0.019 Uiso 1 1 calc R . . C3 C 1.1900(2) 0.26067(18) 0.20682(18) 0.0184(3) Uani 1 1 d . . . H3A H 1.1896 0.3400 0.1172 0.022 Uiso 1 1 calc R . . H3B H 1.1579 0.3059 0.2831 0.022 Uiso 1 1 calc R . . C4 C 0.8422(2) 0.34385(17) 0.03841(16) 0.0176(3) Uani 1 1 d . . . H4A H 0.9574 0.3585 -0.0145 0.021 Uiso 1 1 calc R . . H4B H 0.7662 0.4421 0.0327 0.021 Uiso 1 1 calc R . . C5 C 0.7517(2) 0.26799(18) -0.03128(17) 0.0201(4) Uani 1 1 d . . . H5A H 0.6332 0.2585 0.0180 0.024 Uiso 1 1 calc R . . H5B H 0.7314 0.3306 -0.1283 0.024 Uiso 1 1 calc R . . C6 C 0.4873(2) 0.20858(19) 0.74106(17) 0.0207(4) Uani 1 1 d . . . H6A H 0.5352 0.2905 0.7469 0.025 Uiso 1 1 calc R . . H6B H 0.5847 0.1194 0.7576 0.025 Uiso 1 1 calc R . . C7 C 0.3301(2) 0.1822(2) 0.85030(18) 0.0273(4) Uani 1 1 d . . . H7A H 0.3581 0.0802 0.9132 0.033 Uiso 1 1 calc R . . H7B H 0.3137 0.2495 0.9071 0.033 Uiso 1 1 calc R . . C8 C 0.1256(3) 0.35645(19) 0.6883(2) 0.0300(4) Uani 1 1 d . . . H8A H 0.1114 0.4273 0.7411 0.036 Uiso 1 1 calc R . . H8B H 0.0116 0.3741 0.6456 0.036 Uiso 1 1 calc R . . C9 C 0.2761(2) 0.38226(17) 0.57288(17) 0.0202(4) Uani 1 1 d . . . H9A H 0.2296 0.4051 0.4807 0.024 Uiso 1 1 calc R . . H9B H 0.3249 0.4658 0.5735 0.024 Uiso 1 1 calc R . . C10 C 0.3466(2) 0.12062(18) 0.59321(17) 0.0199(4) Uani 1 1 d . . . H10A H 0.4407 0.0293 0.6124 0.024 Uiso 1 1 calc R . . H10B H 0.3058 0.1419 0.4993 0.024 Uiso 1 1 calc R . . C11 C 0.1884(2) 0.10269(18) 0.70367(17) 0.0217(4) Uani 1 1 d . . . H11A H 0.0776 0.1195 0.6570 0.026 Uiso 1 1 calc R . . H11B H 0.2105 0.0010 0.7675 0.026 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 0.0186(2) 0.0302(2) 0.0152(2) -0.00509(17) -0.00116(16) -0.00032(18) S2 0.0149(2) 0.0188(2) 0.0243(2) -0.00884(17) -0.00320(16) -0.00046(16) O1 0.0130(6) 0.0206(6) 0.0376(7) -0.0085(5) -0.0035(5) -0.0037(5) O2 0.0224(7) 0.0214(6) 0.0228(6) -0.0089(5) 0.0012(5) -0.0050(5) N1 0.0134(7) 0.0145(6) 0.0145(6) -0.0035(5) -0.0019(5) -0.0029(5) N2 0.0168(7) 0.0179(7) 0.0159(7) -0.0060(5) 0.0021(5) -0.0041(6) N3 0.0188(7) 0.0190(7) 0.0197(7) -0.0066(6) 0.0010(6) -0.0050(6) C1 0.0145(8) 0.0140(7) 0.0194(8) -0.0065(6) -0.0011(6) -0.0063(6) C2 0.0141(8) 0.0148(8) 0.0175(8) -0.0048(6) -0.0005(6) -0.0024(6) C3 0.0152(8) 0.0164(8) 0.0230(9) -0.0043(7) -0.0033(6) -0.0036(7) C4 0.0201(9) 0.0159(8) 0.0142(8) -0.0010(6) -0.0010(6) -0.0040(7) C5 0.0187(8) 0.0239(9) 0.0163(8) -0.0054(7) -0.0029(7) -0.0023(7) C6 0.0197(9) 0.0257(9) 0.0193(8) -0.0087(7) -0.0034(7) -0.0055(7) C7 0.0275(10) 0.0421(11) 0.0180(9) -0.0133(8) 0.0010(7) -0.0136(9) C8 0.0259(10) 0.0192(9) 0.0361(11) -0.0044(8) 0.0092(8) -0.0011(8) C9 0.0227(9) 0.0152(8) 0.0202(8) -0.0049(7) -0.0003(7) -0.0012(7) C10 0.0261(9) 0.0152(8) 0.0204(8) -0.0085(7) -0.0026(7) -0.0034(7) C11 0.0254(9) 0.0208(9) 0.0214(9) -0.0062(7) -0.0020(7) -0.0094(7) _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 C1 1.7113(16) . ? S2 C1 1.7269(16) . ? O1 C3 1.4197(19) . ? O1 H1O 0.8400 . ? O2 C5 1.418(2) . ? O2 H2O 0.8400 . ? N1 C1 1.349(2) . ? N1 C4 1.4698(19) . ? N1 C2 1.474(2) . ? N2 C9 1.490(2) . ? N2 C10 1.497(2) . ? N2 C6 1.500(2) . ? N2 H2N 0.9300 . ? N3 C7 1.469(2) . ? N3 C11 1.471(2) . ? N3 C8 1.472(2) . ? C2 C3 1.510(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.517(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.538(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.537(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.542(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 O1 H1O 109.5 . . ? C5 O2 H2O 109.5 . . ? C1 N1 C4 121.99(13) . . ? C1 N1 C2 122.04(13) . . ? C4 N1 C2 115.62(12) . . ? C9 N2 C10 110.07(12) . . ? C9 N2 C6 110.46(12) . . ? C10 N2 C6 109.53(12) . . ? C9 N2 H2N 108.9 . . ? C10 N2 H2N 108.9 . . ? C6 N2 H2N 108.9 . . ? C7 N3 C11 108.63(13) . . ? C7 N3 C8 108.91(14) . . ? C11 N3 C8 108.38(13) . . ? N1 C1 S1 120.26(12) . . ? N1 C1 S2 119.38(12) . . ? S1 C1 S2 120.36(9) . . ? N1 C2 C3 110.20(12) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O1 C3 C2 107.86(13) . . ? O1 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N1 C4 C5 115.01(13) . . ? N1 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? N1 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? O2 C5 C4 114.04(13) . . ? O2 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? O2 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N2 C6 C7 107.70(13) . . ? N2 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? N2 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? N3 C7 C6 111.48(13) . . ? N3 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N3 C8 C9 111.69(14) . . ? N3 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N3 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N2 C9 C8 107.60(13) . . ? N2 C9 H9A 110.2 . . ? C8 C9 H9A 110.2 . . ? N2 C9 H9B 110.2 . . ? C8 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? N2 C10 C11 107.41(12) . . ? N2 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? N2 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N3 C11 C10 111.61(13) . . ? N3 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? N3 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? 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 C4 N1 C1 S1 -172.87(11) . . . . ? C2 N1 C1 S1 0.06(19) . . . . ? C4 N1 C1 S2 6.76(19) . . . . ? C2 N1 C1 S2 179.68(10) . . . . ? C1 N1 C2 C3 -91.67(17) . . . . ? C4 N1 C2 C3 81.68(16) . . . . ? N1 C2 C3 O1 -176.74(12) . . . . ? C1 N1 C4 C5 -91.94(17) . . . . ? C2 N1 C4 C5 94.71(16) . . . . ? N1 C4 C5 O2 -59.91(19) . . . . ? C9 N2 C6 C7 61.65(17) . . . . ? C10 N2 C6 C7 -59.74(17) . . . . ? C11 N3 C7 C6 60.47(18) . . . . ? C8 N3 C7 C6 -57.38(18) . . . . ? N2 C6 C7 N3 -2.2(2) . . . . ? C7 N3 C8 C9 60.46(19) . . . . ? C11 N3 C8 C9 -57.55(19) . . . . ? C10 N2 C9 C8 62.29(17) . . . . ? C6 N2 C9 C8 -58.78(17) . . . . ? N3 C8 C9 N2 -2.5(2) . . . . ? C9 N2 C10 C11 -59.26(16) . . . . ? C6 N2 C10 C11 62.37(16) . . . . ? C7 N3 C11 C10 -57.61(17) . . . . ? C8 N3 C11 C10 60.58(18) . . . . ? N2 C10 C11 N3 -2.77(18) . . . . ? 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 O1 H1O S2 0.84 2.36 3.1613(12) 160 1_655 ? O2 H2O N3 0.84 2.11 2.9341(18) 166 1_654 ? N2 H2N S1 0.93 2.34 3.1874(14) 152 . ? N2 H2N S2 0.93 2.75 3.4865(14) 137 . ? C10 H10A O1 0.99 2.45 3.341(2) 149 2_756 ? C11 H11A S1 0.99 2.84 3.7976(18) 164 1_455 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.25 # 0.69 A from N3 _refine_diff_density_min -0.32 # 0.80 A from S2 _refine_diff_density_rms 0.058 # Attachment '3.CIF' data_3 _database_code_depnum_ccdc_archive 'CCDC 690734' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N2, C4 H8 N O S2 ' _chemical_formula_sum 'C10 H21 N3 O S2' _chemical_formula_weight 263.42 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/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 11.8425(4) _cell_length_b 9.3648(3) _cell_length_c 12.1634(4) _cell_angle_alpha 90 _cell_angle_beta 106.823(2) _cell_angle_gamma 90 _cell_volume 1291.22(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3106 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.398 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.844 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17781 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.053 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2957 _reflns_number_gt 2155 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0653P)^2^+0.0615P] 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 2957 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.074 _refine_ls_R_factor_gt 0.040 _refine_ls_wR_factor_ref 0.118 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_restrained_S_all 1.10 _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 0.54638(5) 0.32495(6) 0.11555(5) 0.02136(17) Uani 1 1 d . . . S2 S 0.61748(5) 0.27612(6) 0.36879(5) 0.02094(17) Uani 1 1 d . . . O1 O 0.31762(15) 0.42714(16) 0.49690(13) 0.0265(4) Uani 1 1 d . . . H1 H 0.3321 0.5024 0.5360 0.040 Uiso 1 1 calc R . . N1 N 0.39527(16) 0.31226(19) 0.23885(15) 0.0189(4) Uani 1 1 d . . . N2 N 0.83539(16) 0.32986(18) 0.25274(15) 0.0195(4) Uani 1 1 d . . . H2 H 0.7554 0.3294 0.2474 0.023 Uiso 1 1 calc R . . N3 N 1.05292(16) 0.33140(19) 0.26726(15) 0.0195(4) Uani 1 1 d . . . C1 C 0.50906(19) 0.3065(2) 0.23989(18) 0.0160(5) Uani 1 1 d . . . C2 C 0.35734(19) 0.3001(2) 0.34302(18) 0.0199(5) Uani 1 1 d . . . H2A H 0.4145 0.2408 0.4004 0.024 Uiso 1 1 calc R . . H2B H 0.2795 0.2524 0.3243 0.024 Uiso 1 1 calc R . . C3 C 0.3489(2) 0.4462(2) 0.39318(18) 0.0212(5) Uani 1 1 d . . . H3A H 0.4256 0.4963 0.4092 0.025 Uiso 1 1 calc R . . H3B H 0.2883 0.5043 0.3382 0.025 Uiso 1 1 calc R . . C4 C 0.3014(2) 0.3365(3) 0.13197(19) 0.0254(5) Uani 1 1 d . . . H4A H 0.3191 0.4225 0.0941 0.038 Uiso 1 1 calc R . . H4B H 0.2261 0.3491 0.1492 0.038 Uiso 1 1 calc R . . H4C H 0.2960 0.2541 0.0810 0.038 Uiso 1 1 calc R . . C5 C 0.8846(2) 0.1831(2) 0.2848(2) 0.0215(5) Uani 1 1 d . . . H5A H 0.8438 0.1131 0.2256 0.026 Uiso 1 1 calc R . . H5B H 0.8736 0.1540 0.3593 0.026 Uiso 1 1 calc R . . C6 C 1.0169(2) 0.1886(2) 0.2937(2) 0.0239(5) Uani 1 1 d . . . H6A H 1.0634 0.1614 0.3724 0.029 Uiso 1 1 calc R . . H6B H 1.0339 0.1185 0.2396 0.029 Uiso 1 1 calc R . . C7 C 0.8974(2) 0.4336(2) 0.3444(2) 0.0241(5) Uani 1 1 d . . . H7A H 0.8876 0.4049 0.4194 0.029 Uiso 1 1 calc R . . H7B H 0.8642 0.5306 0.3256 0.029 Uiso 1 1 calc R . . C8 C 1.02882(19) 0.4324(2) 0.3497(2) 0.0244(5) Uani 1 1 d . . . H8A H 1.0527 0.5295 0.3332 0.029 Uiso 1 1 calc R . . H8B H 1.0765 0.4060 0.4283 0.029 Uiso 1 1 calc R . . C9 C 0.8502(2) 0.3738(3) 0.13954(19) 0.0239(5) Uani 1 1 d . . . H9A H 0.8178 0.4708 0.1190 0.029 Uiso 1 1 calc R . . H9B H 0.8077 0.3068 0.0786 0.029 Uiso 1 1 calc R . . C10 C 0.9826(2) 0.3719(3) 0.1508(2) 0.0276(5) Uani 1 1 d . . . H10A H 0.9977 0.3033 0.0948 0.033 Uiso 1 1 calc R . . H10B H 1.0072 0.4678 0.1323 0.033 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 0.0219(3) 0.0245(3) 0.0185(3) -0.0003(2) 0.0072(2) -0.0009(2) S2 0.0169(3) 0.0244(3) 0.0192(3) -0.0012(2) 0.0016(2) 0.0021(2) O1 0.0361(10) 0.0268(9) 0.0208(8) -0.0049(7) 0.0149(7) -0.0050(7) N1 0.0154(10) 0.0250(11) 0.0150(9) -0.0018(7) 0.0020(7) 0.0007(7) N2 0.0144(10) 0.0187(10) 0.0259(10) -0.0026(8) 0.0064(8) 0.0004(7) N3 0.0185(10) 0.0196(10) 0.0209(10) -0.0017(8) 0.0065(8) -0.0011(7) C1 0.0170(11) 0.0121(11) 0.0178(11) -0.0027(8) 0.0030(8) 0.0006(8) C2 0.0164(11) 0.0243(13) 0.0191(11) 0.0005(9) 0.0053(9) -0.0015(9) C3 0.0232(13) 0.0226(12) 0.0193(11) 0.0009(9) 0.0087(9) -0.0004(9) C4 0.0167(12) 0.0346(14) 0.0218(12) -0.0018(10) 0.0004(9) 0.0010(10) C5 0.0220(12) 0.0160(11) 0.0276(13) -0.0011(9) 0.0087(10) -0.0001(9) C6 0.0229(13) 0.0200(13) 0.0304(13) -0.0028(9) 0.0105(10) 0.0024(9) C7 0.0229(13) 0.0210(12) 0.0298(13) -0.0085(10) 0.0097(10) -0.0024(9) C8 0.0191(12) 0.0196(12) 0.0324(13) -0.0067(10) 0.0044(10) -0.0007(9) C9 0.0230(12) 0.0236(12) 0.0234(12) 0.0037(10) 0.0040(9) 0.0009(10) C10 0.0206(12) 0.0375(15) 0.0250(12) 0.0041(11) 0.0069(10) -0.0009(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 S1 C1 1.703(2) . ? S2 C1 1.738(2) . ? O1 C3 1.425(2) . ? O1 H1 0.8400 . ? N1 C1 1.345(3) . ? N1 C4 1.463(3) . ? N1 C2 1.466(3) . ? N2 C9 1.495(3) . ? N2 C5 1.500(3) . ? N2 C7 1.501(3) . ? N2 H2 0.9300 . ? N3 C8 1.466(3) . ? N3 C6 1.468(3) . ? N3 C10 1.471(3) . ? C2 C3 1.513(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.539(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.539(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.533(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 O1 H1 109.5 . . ? C1 N1 C4 121.08(18) . . ? C1 N1 C2 123.05(18) . . ? C4 N1 C2 115.83(18) . . ? C9 N2 C5 110.55(16) . . ? C9 N2 C7 110.06(17) . . ? C5 N2 C7 109.29(17) . . ? C9 N2 H2 109.0 . . ? C5 N2 H2 109.0 . . ? C7 N2 H2 109.0 . . ? C8 N3 C6 108.15(17) . . ? C8 N3 C10 108.95(18) . . ? C6 N3 C10 109.05(18) . . ? N1 C1 S1 120.30(16) . . ? N1 C1 S2 119.44(16) . . ? S1 C1 S2 120.25(13) . . ? N1 C2 C3 110.54(17) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O1 C3 C2 107.95(17) . . ? O1 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 107.37(17) . . ? N2 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? N2 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? N3 C6 C5 111.70(17) . . ? N3 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 107.36(17) . . ? N2 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? N2 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? N3 C8 C7 111.76(17) . . ? N3 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N3 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N2 C9 C10 107.72(17) . . ? N2 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? N2 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? N3 C10 C9 111.61(18) . . ? N3 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N3 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? 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 C4 N1 C1 S1 -0.9(3) . . . . ? C2 N1 C1 S1 -178.72(15) . . . . ? C4 N1 C1 S2 -179.50(16) . . . . ? C2 N1 C1 S2 2.7(3) . . . . ? C1 N1 C2 C3 91.8(2) . . . . ? C4 N1 C2 C3 -86.1(2) . . . . ? N1 C2 C3 O1 -177.12(16) . . . . ? C9 N2 C5 C6 60.7(2) . . . . ? C7 N2 C5 C6 -60.6(2) . . . . ? C8 N3 C6 C5 60.0(2) . . . . ? C10 N3 C6 C5 -58.3(2) . . . . ? N2 C5 C6 N3 -0.7(2) . . . . ? C9 N2 C7 C8 -60.0(2) . . . . ? C5 N2 C7 C8 61.6(2) . . . . ? C6 N3 C8 C7 -59.0(2) . . . . ? C10 N3 C8 C7 59.4(2) . . . . ? N2 C7 C8 N3 -0.9(3) . . . . ? C5 N2 C9 C10 -59.6(2) . . . . ? C7 N2 C9 C10 61.2(2) . . . . ? C8 N3 C10 C9 -58.3(2) . . . . ? C6 N3 C10 C9 59.6(2) . . . . ? N2 C9 C10 N3 -1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.31 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.078 # Attachment '4.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 690735' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N2, C5 H10 N O S2 ' _chemical_formula_sum 'C11 H23 N3 O S2' _chemical_formula_weight 277.44 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 7.7319(2) _cell_length_b 9.5151(2) _cell_length_c 9.5940(2) _cell_angle_alpha 84.292(1) _cell_angle_beta 77.195(1) _cell_angle_gamma 85.278(1) _cell_volume 683.54(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3160 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.751 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16659 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.9 _diffrn_reflns_theta_max 27.5 _reflns_number_total 3141 _reflns_number_gt 2780 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 and PLATON (Spek, 2003)' _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^)+(0.0600P)^2^+0.2276P] 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 3141 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.111 _refine_ls_wR_factor_gt 0.106 _refine_ls_goodness_of_fit_ref 1.18 _refine_ls_restrained_S_all 1.18 _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 0.81519(5) 0.41919(4) 0.22507(4) 0.01881(13) Uani 1 1 d . . . S2 S 0.52145(5) 0.23312(4) 0.23615(4) 0.01719(13) Uani 1 1 d . . . O1 O 0.69048(19) -0.19688(13) 0.43566(14) 0.0279(3) Uani 1 1 d . . . H1 H 0.6326 -0.2173 0.5193 0.042 Uiso 1 1 calc R . . N1 N 0.85085(17) 0.13860(14) 0.25068(13) 0.0129(3) Uani 1 1 d . . . N2 N 0.40050(18) 0.56798(14) 0.23804(14) 0.0155(3) Uani 1 1 d . . . H2 H 0.4785 0.4879 0.2308 0.019 Uiso 1 1 calc R . . N3 N 0.18865(17) 0.78495(14) 0.25759(15) 0.0167(3) Uani 1 1 d . . . C1 C 0.7407(2) 0.25409(16) 0.23938(16) 0.0136(3) Uani 1 1 d . . . C2 C 0.7929(2) -0.00552(16) 0.26740(16) 0.0141(3) Uani 1 1 d . . . H2A H 0.8892 -0.0689 0.2164 0.017 Uiso 1 1 calc R . . H2B H 0.6880 -0.0077 0.2246 0.017 Uiso 1 1 calc R . . C3 C 0.7461(2) -0.05701(17) 0.42456(17) 0.0182(3) Uani 1 1 d . . . H3A H 0.8508 -0.0559 0.4679 0.022 Uiso 1 1 calc R . . H3B H 0.6494 0.0056 0.4762 0.022 Uiso 1 1 calc R . . C4 C 1.0416(2) 0.14807(17) 0.24343(17) 0.0150(3) Uani 1 1 d . . . H4A H 1.0858 0.0650 0.2991 0.018 Uiso 1 1 calc R . . H4B H 1.0594 0.2341 0.2874 0.018 Uiso 1 1 calc R . . C5 C 1.1473(2) 0.1535(2) 0.09030(18) 0.0217(4) Uani 1 1 d . . . H5A H 1.2735 0.1597 0.0893 0.033 Uiso 1 1 calc R . . H5B H 1.1053 0.2367 0.0354 0.033 Uiso 1 1 calc R . . H5C H 1.1315 0.0677 0.0470 0.033 Uiso 1 1 calc R . . C6 C 0.2667(2) 0.55572(19) 0.1512(2) 0.0263(4) Uani 1 1 d . . . H6A H 0.1964 0.4725 0.1889 0.032 Uiso 1 1 calc R . . H6B H 0.3265 0.5436 0.0502 0.032 Uiso 1 1 calc R . . C7 C 0.1446(2) 0.69189(18) 0.1599(2) 0.0228(4) Uani 1 1 d . . . H7A H 0.1569 0.7422 0.0632 0.027 Uiso 1 1 calc R . . H7B H 0.0194 0.6672 0.1938 0.027 Uiso 1 1 calc R . . C8 C 0.3140(3) 0.5801(2) 0.39140(19) 0.0319(5) Uani 1 1 d . . . H8A H 0.4039 0.5941 0.4471 0.038 Uiso 1 1 calc R . . H8B H 0.2538 0.4927 0.4324 0.038 Uiso 1 1 calc R . . C9 C 0.1776(3) 0.7080(2) 0.39828(19) 0.0266(4) Uani 1 1 d . . . H9A H 0.0564 0.6748 0.4341 0.032 Uiso 1 1 calc R . . H9B H 0.1997 0.7724 0.4665 0.032 Uiso 1 1 calc R . . C10 C 0.5022(2) 0.69511(18) 0.1820(2) 0.0255(4) Uani 1 1 d . . . H10A H 0.5582 0.6896 0.0792 0.031 Uiso 1 1 calc R . . H10B H 0.5970 0.7012 0.2353 0.031 Uiso 1 1 calc R . . C11 C 0.3712(2) 0.82538(18) 0.2017(2) 0.0243(4) Uani 1 1 d . . . H11A H 0.4047 0.8855 0.2688 0.029 Uiso 1 1 calc R . . H11B H 0.3783 0.8817 0.1083 0.029 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 0.0183(2) 0.0122(2) 0.0260(2) 0.00058(16) -0.00589(16) -0.00081(15) S2 0.0119(2) 0.0167(2) 0.0226(2) 0.00077(15) -0.00472(15) 0.00096(15) O1 0.0415(8) 0.0164(6) 0.0233(6) 0.0009(5) 0.0011(6) -0.0121(5) N1 0.0119(6) 0.0128(6) 0.0138(6) 0.0005(5) -0.0032(5) 0.0001(5) N2 0.0159(7) 0.0136(6) 0.0164(6) -0.0019(5) -0.0035(5) 0.0044(5) N3 0.0148(7) 0.0146(6) 0.0209(7) -0.0026(5) -0.0049(5) 0.0018(5) C1 0.0137(7) 0.0155(7) 0.0103(7) 0.0001(5) -0.0013(5) 0.0006(6) C2 0.0150(7) 0.0115(7) 0.0157(7) -0.0012(6) -0.0038(6) 0.0001(6) C3 0.0225(8) 0.0145(8) 0.0173(8) -0.0002(6) -0.0028(6) -0.0047(6) C4 0.0123(7) 0.0165(7) 0.0170(7) -0.0003(6) -0.0055(6) 0.0003(6) C5 0.0129(8) 0.0325(10) 0.0189(8) 0.0013(7) -0.0035(6) -0.0011(6) C6 0.0245(9) 0.0206(9) 0.0396(10) -0.0130(8) -0.0173(8) 0.0056(7) C7 0.0214(9) 0.0195(8) 0.0315(9) -0.0064(7) -0.0141(7) 0.0045(7) C8 0.0426(12) 0.0284(10) 0.0169(8) 0.0030(7) 0.0022(8) 0.0140(8) C9 0.0305(10) 0.0255(9) 0.0192(8) -0.0019(7) 0.0007(7) 0.0091(7) C10 0.0163(8) 0.0179(8) 0.0408(11) -0.0020(7) -0.0036(7) -0.0006(6) C11 0.0170(8) 0.0141(8) 0.0408(10) -0.0006(7) -0.0051(7) -0.0004(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 C1 1.6998(16) . ? S2 C1 1.7305(16) . ? O1 C3 1.4188(19) . ? O1 H1 0.8400 . ? N1 C1 1.344(2) . ? N1 C2 1.4602(19) . ? N1 C4 1.4711(19) . ? N2 C6 1.483(2) . ? N2 C8 1.487(2) . ? N2 C10 1.487(2) . ? N2 H2 0.9300 . ? N3 C9 1.459(2) . ? N3 C7 1.461(2) . ? N3 C11 1.463(2) . ? C2 C3 1.512(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.513(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.537(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.540(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.534(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 O1 H1 109.5 . . ? C1 N1 C2 123.18(13) . . ? C1 N1 C4 122.18(13) . . ? C2 N1 C4 114.61(12) . . ? C6 N2 C8 111.03(15) . . ? C6 N2 C10 109.42(14) . . ? C8 N2 C10 109.30(14) . . ? C6 N2 H2 109.0 . . ? C8 N2 H2 109.0 . . ? C10 N2 H2 109.0 . . ? C9 N3 C7 109.02(14) . . ? C9 N3 C11 108.91(14) . . ? C7 N3 C11 108.37(13) . . ? N1 C1 S1 120.88(12) . . ? N1 C1 S2 119.16(12) . . ? S1 C1 S2 119.95(9) . . ? N1 C2 C3 110.11(12) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C2 108.16(12) . . ? O1 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N1 C4 C5 111.56(12) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 107.91(13) . . ? N2 C6 H6A 110.1 . . ? C7 C6 H6A 110.1 . . ? N2 C6 H6B 110.1 . . ? C7 C6 H6B 110.1 . . ? H6A C6 H6B 108.4 . . ? N3 C7 C6 111.16(14) . . ? N3 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? N3 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N2 C8 C9 107.56(14) . . ? N2 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? N2 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N3 C9 C8 111.28(13) . . ? N3 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? N3 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C11 107.61(14) . . ? N2 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? N2 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N3 C11 C10 111.49(14) . . ? N3 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? N3 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? 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 C2 N1 C1 S1 178.17(11) . . . . ? C4 N1 C1 S1 -3.4(2) . . . . ? C2 N1 C1 S2 -3.0(2) . . . . ? C4 N1 C1 S2 175.41(11) . . . . ? C1 N1 C2 C3 -94.12(17) . . . . ? C4 N1 C2 C3 87.34(15) . . . . ? N1 C2 C3 O1 179.92(13) . . . . ? C1 N1 C4 C5 -86.93(18) . . . . ? C2 N1 C4 C5 91.62(16) . . . . ? C8 N2 C6 C7 62.19(19) . . . . ? C10 N2 C6 C7 -58.54(18) . . . . ? C9 N3 C7 C6 -56.65(19) . . . . ? C11 N3 C7 C6 61.75(19) . . . . ? N2 C6 C7 N3 -4.1(2) . . . . ? C6 N2 C8 C9 -56.4(2) . . . . ? C10 N2 C8 C9 64.42(19) . . . . ? C7 N3 C9 C8 62.69(19) . . . . ? C11 N3 C9 C8 -55.37(19) . . . . ? N2 C8 C9 N3 -6.0(2) . . . . ? C6 N2 C10 C11 63.32(18) . . . . ? C8 N2 C10 C11 -58.45(19) . . . . ? C9 N3 C11 C10 61.71(19) . . . . ? C7 N3 C11 C10 -56.77(19) . . . . ? N2 C10 C11 N3 -4.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.56 _refine_diff_density_min -0.66 _refine_diff_density_rms 0.235 # Attachment '5.CIF' data_5 _database_code_depnum_ccdc_archive 'CCDC 690736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H16 N Na O5 S2 ' _chemical_formula_sum 'C5 H16 N Na O5 S2' _chemical_formula_weight 257.30 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' Na Na 0.0362 0.0249 '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 b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.4181(4) _cell_length_b 8.1107(2) _cell_length_c 19.0611(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2229.02(10) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2891 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19691 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.027 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2557 _reflns_number_gt 2150 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 and PLATON (Spek, 2003)' _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^)+(0.0292P)^2^+1.1201P] 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 2557 _refine_ls_number_parameters 151 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.039 _refine_ls_R_factor_gt 0.029 _refine_ls_wR_factor_ref 0.068 _refine_ls_wR_factor_gt 0.064 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_restrained_S_all 1.11 _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 Na Na 0.31374(4) 0.05872(7) 0.96776(3) 0.01483(15) Uani 1 1 d . . . S1 S 0.48899(3) 0.04716(5) 0.588145(19) 0.01442(10) Uani 1 1 d . . . S2 S 0.35080(2) 0.13177(5) 0.697627(19) 0.01348(10) Uani 1 1 d . . . O1 O 0.77199(7) 0.14017(14) 0.64742(6) 0.0157(2) Uani 1 1 d D . . H1O H 0.8087 0.1306 0.6814 0.024 Uiso 1 1 d D . . O2 O 0.46447(7) 0.07988(15) 0.90893(5) 0.0170(2) Uani 1 1 d D . . H2O H 0.5095 0.1134 0.9330 0.025 Uiso 1 1 d D . . O3 O 0.24904(8) 0.12366(13) 1.08396(5) 0.0183(2) Uani 1 1 d D . . H3O H 0.2198 0.0552 1.1085 0.027 Uiso 1 1 d D . . H4O H 0.2781 0.1903 1.1096 0.027 Uiso 1 1 d D . . O4 O 0.17593(8) -0.13415(14) 0.97706(6) 0.0176(2) Uani 1 1 d D . . H5O H 0.1455 -0.1159 1.0138 0.026 Uiso 1 1 d D . . H6O H 0.1403 -0.1183 0.9428 0.026 Uiso 1 1 d D . . O5 O 0.38647(7) -0.18637(13) 1.01113(6) 0.0165(2) Uani 1 1 d D . . H7O H 0.3492 -0.2448 1.0342 0.025 Uiso 1 1 d D . . H8O H 0.4175 -0.2469 0.9841 0.025 Uiso 1 1 d D . . N1 N 0.53311(8) 0.10946(15) 0.72106(6) 0.0105(2) Uani 1 1 d . . . C1 C 0.46486(10) 0.09812(17) 0.67304(8) 0.0110(3) Uani 1 1 d . . . C2 C 0.62923(10) 0.06124(18) 0.70433(8) 0.0117(3) Uani 1 1 d . . . H2A H 0.6281 -0.0325 0.6711 0.014 Uiso 1 1 calc R . . H2B H 0.6603 0.0236 0.7478 0.014 Uiso 1 1 calc R . . C3 C 0.68517(10) 0.20169(18) 0.67226(8) 0.0130(3) Uani 1 1 d . . . H3A H 0.6501 0.2513 0.6329 0.016 Uiso 1 1 calc R . . H3B H 0.6960 0.2883 0.7079 0.016 Uiso 1 1 calc R . . C4 C 0.51727(10) 0.16709(18) 0.79321(7) 0.0116(3) Uani 1 1 d . . . H4A H 0.4647 0.2455 0.7937 0.014 Uiso 1 1 calc R . . H4B H 0.5731 0.2262 0.8101 0.014 Uiso 1 1 calc R . . C5 C 0.49614(10) 0.02365(19) 0.84256(8) 0.0138(3) Uani 1 1 d . . . H5A H 0.4482 -0.0477 0.8211 0.017 Uiso 1 1 calc R . . H5B H 0.5529 -0.0434 0.8491 0.017 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 Na 0.0148(3) 0.0167(3) 0.0130(3) -0.0001(2) -0.0001(2) 0.0018(2) S1 0.01312(18) 0.0201(2) 0.01004(18) -0.00227(14) 0.00100(14) -0.00074(15) S2 0.00883(17) 0.01876(19) 0.01284(19) -0.00012(14) 0.00072(13) 0.00116(14) O1 0.0078(5) 0.0260(6) 0.0131(5) -0.0004(5) 0.0010(4) 0.0026(4) O2 0.0129(5) 0.0285(6) 0.0095(5) -0.0007(4) 0.0011(4) -0.0026(5) O3 0.0211(6) 0.0186(6) 0.0151(6) 0.0001(5) 0.0005(5) -0.0066(5) O4 0.0169(6) 0.0227(6) 0.0133(5) -0.0009(5) -0.0031(4) 0.0023(5) O5 0.0149(5) 0.0182(5) 0.0163(6) 0.0013(4) 0.0015(4) 0.0010(5) N1 0.0084(6) 0.0126(6) 0.0105(6) -0.0005(5) 0.0009(5) 0.0005(5) C1 0.0123(7) 0.0081(6) 0.0124(7) 0.0004(5) 0.0007(5) -0.0014(6) C2 0.0084(6) 0.0143(7) 0.0126(7) 0.0005(5) 0.0002(5) 0.0012(6) C3 0.0094(7) 0.0158(7) 0.0137(7) 0.0005(6) 0.0011(5) 0.0013(6) C4 0.0109(7) 0.0135(7) 0.0103(7) -0.0024(5) -0.0002(5) -0.0010(6) C5 0.0146(7) 0.0145(7) 0.0121(7) -0.0001(6) 0.0011(6) 0.0000(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 Na O1 2.3704(12) 8_557 ? Na O5 2.3947(12) . ? Na O2 2.4515(12) . ? Na O3 2.4604(12) . ? Na O4 2.5018(13) 6_665 ? Na O4 2.5350(13) . ? S1 C1 1.7060(15) . ? S2 C1 1.7316(15) . ? O1 C3 1.4284(17) . ? O1 H1O 0.8398 . ? O2 C5 1.4202(18) . ? O2 H2O 0.8399 . ? O3 H3O 0.8400 . ? O3 H4O 0.8401 . ? O4 H5O 0.8402 . ? O4 H6O 0.8402 . ? O5 H7O 0.8400 . ? O5 H8O 0.8401 . ? N1 C1 1.3470(19) . ? N1 C4 1.4704(18) . ? N1 C2 1.4748(18) . ? C2 C3 1.524(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C4 1.527(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? 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 Na O5 131.48(4) 8_557 . ? O1 Na O2 77.40(4) 8_557 . ? O5 Na O2 80.09(4) . . ? O1 Na O3 132.68(4) 8_557 . ? O5 Na O3 91.89(4) . . ? O2 Na O3 137.13(4) . . ? O1 Na O4 78.65(4) 8_557 6_665 ? O5 Na O4 140.90(5) . 6_665 ? O2 Na O4 84.83(4) . 6_665 ? O3 Na O4 75.26(4) . 6_665 ? O1 Na O4 92.16(4) 8_557 . ? O5 Na O4 78.86(4) . . ? O2 Na O4 140.35(4) . . ? O3 Na O4 76.82(4) . . ? O4 Na O4 131.01(4) 6_665 . ? C3 O1 Na 128.82(9) . 8_657 ? C3 O1 H1O 109.2 . . ? Na O1 H1O 121.9 8_657 . ? C5 O2 Na 132.06(9) . . ? C5 O2 H2O 110.0 . . ? Na O2 H2O 117.3 . . ? Na O3 H3O 123.5 . . ? Na O3 H4O 118.2 . . ? H3O O3 H4O 110.5 . . ? Na O4 Na 124.25(5) 6_655 . ? Na O4 H5O 105.4 6_655 . ? Na O4 H5O 111.1 . . ? Na O4 H6O 97.7 6_655 . ? Na O4 H6O 109.3 . . ? H5O O4 H6O 107.5 . . ? Na O5 H7O 111.7 . . ? Na O5 H8O 120.4 . . ? H7O O5 H8O 109.3 . . ? C1 N1 C4 122.94(12) . . ? C1 N1 C2 121.43(12) . . ? C4 N1 C2 115.62(11) . . ? N1 C1 S1 120.80(11) . . ? N1 C1 S2 119.94(11) . . ? S1 C1 S2 119.25(9) . . ? N1 C2 C3 112.70(12) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? O1 C3 C2 109.61(12) . . ? O1 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? O1 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? O2 C5 C4 111.61(12) . . ? O2 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? O2 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N1 C4 C5 111.41(12) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.41 _refine_diff_density_min -0.50 _refine_diff_density_rms 0.139 # Attachment '6.CIF' data_6 _database_code_depnum_ccdc_archive 'CCDC 690737' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H16 N Na O3 S2 ' _chemical_formula_sum 'C6 H16 N Na O3 S2 ' _chemical_formula_weight 237.33 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' Na Na 0.0362 0.0249 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.8102(15) _cell_length_b 5.8617(2) _cell_length_c 14.8147(5) _cell_angle_alpha 90 _cell_angle_beta 106.278(2) _cell_angle_gamma 90 _cell_volume 2234.85(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 24718 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.493 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.586 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 10254 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 25.0 _reflns_number_total 1948 _reflns_number_gt 1651 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0356P)^2^+42.6193P] 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 1948 _refine_ls_number_parameters 133 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.070 _refine_ls_R_factor_gt 0.059 _refine_ls_wR_factor_ref 0.170 _refine_ls_wR_factor_gt 0.165 _refine_ls_goodness_of_fit_ref 1.14 _refine_ls_restrained_S_all 1.14 _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 0.68585(5) 1.2466(2) 0.26623(9) 0.0148(3) Uani 1 1 d . . . S2 S 0.59583(5) 1.0909(2) 0.33253(9) 0.0150(3) Uani 1 1 d . . . Na Na 0.78079(8) 1.0073(3) 0.04792(14) 0.0152(5) Uani 1 1 d . . . O1 O 0.69461(14) 0.8577(7) 0.0166(2) 0.0153(8) Uani 1 1 d D . . H1O H 0.6703 0.8749 -0.0330 0.023 Uiso 1 1 d D . . O2 O 0.86763(15) 1.0872(7) 0.0742(3) 0.0207(9) Uani 1 1 d D . . H2O H 0.8783 1.2165 0.0955 0.031 Uiso 1 1 d D . . H3O H 0.8883 0.9833 0.0999 0.031 Uiso 1 1 d D . . O3 O 0.74956(14) 1.3343(7) 0.1082(3) 0.0178(9) Uani 1 1 d D . . H4O H 0.7667 1.4554 0.1223 0.027 Uiso 1 1 d D . . H5O H 0.7234 1.3347 0.1287 0.027 Uiso 1 1 d D . . N1 N 0.60464(17) 1.0125(7) 0.1605(3) 0.0119(9) Uani 1 1 d . . . C1 C 0.62730(19) 1.1065(9) 0.2448(3) 0.0122(11) Uani 1 1 d . . . C2 C 0.6295(2) 1.0216(10) 0.0840(3) 0.0143(11) Uani 1 1 d . . . H2A H 0.6469 1.1713 0.0855 0.017 Uiso 1 1 calc R . . H2B H 0.6025 1.0089 0.0230 0.017 Uiso 1 1 calc R . . C3 C 0.6697(2) 0.8317(10) 0.0907(4) 0.0159(11) Uani 1 1 d . . . H3A H 0.6961 0.8387 0.1526 0.019 Uiso 1 1 calc R . . H3B H 0.6523 0.6812 0.0851 0.019 Uiso 1 1 calc R . . C4 C 0.5531(2) 0.9007(10) 0.1376(4) 0.0171(12) Uani 1 1 d . . . H4A H 0.5334 0.9429 0.0727 0.021 Uiso 1 1 calc R . . H4B H 0.5337 0.9601 0.1806 0.021 Uiso 1 1 calc R . . C5 C 0.5554(2) 0.6432(11) 0.1453(5) 0.0255(14) Uani 1 1 d . . . H5A H 0.5758 0.5986 0.2094 0.031 Uiso 1 1 calc R . . H5B H 0.5730 0.5809 0.1002 0.031 Uiso 1 1 calc R . . C6 C 0.5012(2) 0.5447(12) 0.1245(5) 0.0332(16) Uani 1 1 d . . . H6A H 0.5033 0.3781 0.1293 0.050 Uiso 1 1 calc R . . H6B H 0.4811 0.5880 0.0607 0.050 Uiso 1 1 calc R . . H6C H 0.4840 0.6043 0.1699 0.050 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 0.0153(6) 0.0175(7) 0.0119(6) -0.0011(5) 0.0044(5) -0.0021(5) S2 0.0178(7) 0.0172(7) 0.0117(6) -0.0008(5) 0.0070(5) -0.0009(5) Na 0.0150(10) 0.0151(11) 0.0158(10) -0.0006(9) 0.0049(8) -0.0008(8) O1 0.0156(19) 0.021(2) 0.0106(17) -0.0003(16) 0.0061(14) 0.0002(16) O2 0.020(2) 0.018(2) 0.021(2) 0.0008(18) 0.0021(16) -0.0020(17) O3 0.019(2) 0.020(2) 0.0169(19) -0.0033(17) 0.0090(16) -0.0037(16) N1 0.016(2) 0.012(2) 0.009(2) -0.0008(17) 0.0055(17) 0.0023(17) C1 0.013(3) 0.012(3) 0.011(2) 0.004(2) 0.004(2) 0.005(2) C2 0.017(3) 0.021(3) 0.006(2) -0.002(2) 0.004(2) 0.002(2) C3 0.019(3) 0.019(3) 0.012(2) 0.000(2) 0.010(2) 0.001(2) C4 0.012(3) 0.029(3) 0.010(2) -0.004(2) 0.002(2) 0.001(2) C5 0.020(3) 0.024(3) 0.033(3) -0.004(3) 0.008(3) -0.005(2) C6 0.026(3) 0.035(4) 0.040(4) -0.008(3) 0.011(3) -0.014(3) _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 C1 1.720(5) . ? S1 Na 3.055(2) 4_655 ? S2 C1 1.739(5) . ? Na O2 2.299(4) . ? Na O3 2.365(4) . ? Na O1 2.392(4) . ? Na O3 2.412(4) 7_675 ? Na O1 2.506(4) 7_665 ? Na S1 3.055(2) 4_645 ? Na Na 3.394(4) 7_675 ? Na Na 3.540(4) 7_665 ? O1 C3 1.444(6) . ? O1 H1O 0.8400 . ? O2 H2O 0.8400 . ? O2 H3O 0.8400 . ? O3 H4O 0.8400 . ? O3 H5O 0.8400 . ? N1 C1 1.344(7) . ? N1 C2 1.469(6) . ? N1 C4 1.481(7) . ? C2 C3 1.532(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.513(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.513(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 C1 S1 Na 115.25(18) . 4_655 ? O2 Na O3 102.71(16) . . ? O2 Na O1 170.06(17) . . ? O3 Na O1 86.87(15) . . ? O2 Na O3 97.90(15) . 7_675 ? O3 Na O3 89.45(14) . 7_675 ? O1 Na O3 84.68(14) . 7_675 ? O2 Na O1 82.89(15) . 7_665 ? O3 Na O1 174.28(15) . 7_665 ? O1 Na O1 87.49(14) . 7_665 ? O3 Na O1 90.96(14) 7_675 7_665 ? O2 Na S1 85.56(12) . 4_645 ? O3 Na S1 96.33(12) . 4_645 ? O1 Na S1 90.81(11) . 4_645 ? O3 Na S1 172.47(13) 7_675 4_645 ? O1 Na S1 82.81(10) 7_665 4_645 ? O2 Na Na 104.53(14) . 7_675 ? O3 Na Na 45.29(10) . 7_675 ? O1 Na Na 84.03(12) . 7_675 ? O3 Na Na 44.16(10) 7_675 7_675 ? O1 Na Na 134.84(13) 7_665 7_675 ? S1 Na Na 141.39(10) 4_645 7_675 ? O2 Na Na 125.31(15) . 7_665 ? O3 Na Na 131.88(14) . 7_665 ? O1 Na Na 45.02(10) . 7_665 ? O3 Na Na 87.08(12) 7_675 7_665 ? O1 Na Na 42.47(9) 7_665 7_665 ? S1 Na Na 85.47(8) 4_645 7_665 ? Na Na Na 115.40(11) 7_675 7_665 ? C3 O1 Na 121.3(3) . . ? C3 O1 Na 115.3(3) . 7_665 ? Na O1 Na 92.51(14) . 7_665 ? C3 O1 H1O 105.5 . . ? Na O1 H1O 126.6 . . ? Na O1 H1O 89.5 7_665 . ? Na O2 H2O 118.1 . . ? Na O2 H3O 116.0 . . ? H2O O2 H3O 111.8 . . ? Na O3 Na 90.55(14) . 7_675 ? Na O3 H4O 123.5 . . ? Na O3 H4O 85.8 7_675 . ? Na O3 H5O 124.0 . . ? Na O3 H5O 104.7 7_675 . ? H4O O3 H5O 111.3 . . ? C1 N1 C2 121.1(4) . . ? C1 N1 C4 123.0(4) . . ? C2 N1 C4 115.9(4) . . ? N1 C1 S1 121.2(4) . . ? N1 C1 S2 119.0(4) . . ? S1 C1 S2 119.7(3) . . ? N1 C2 C3 112.7(4) . . ? N1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O1 C3 C2 109.9(4) . . ? O1 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? O1 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N1 C4 C5 114.1(4) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 110.4(5) . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 Na O1 C3 107.5(10) . . . . ? O3 Na O1 C3 -57.3(4) . . . . ? O3 Na O1 C3 -147.0(4) 7_675 . . . ? O1 Na O1 C3 121.8(4) 7_665 . . . ? S1 Na O1 C3 39.0(4) 4_645 . . . ? Na Na O1 C3 -102.6(4) 7_675 . . . ? Na Na O1 C3 121.8(4) 7_665 . . . ? O2 Na O1 Na -14.3(10) . . . 7_665 ? O3 Na O1 Na -179.06(16) . . . 7_665 ? O3 Na O1 Na 91.20(14) 7_675 . . 7_665 ? O1 Na O1 Na 0.0 7_665 . . 7_665 ? S1 Na O1 Na -82.77(10) 4_645 . . 7_665 ? Na Na O1 Na 135.58(13) 7_675 . . 7_665 ? O2 Na O3 Na 97.97(16) . . . 7_675 ? O1 Na O3 Na -84.70(14) . . . 7_675 ? O3 Na O3 Na 0.000(1) 7_675 . . 7_675 ? O1 Na O3 Na -94.1(16) 7_665 . . 7_675 ? S1 Na O3 Na -175.17(12) 4_645 . . 7_675 ? Na Na O3 Na -85.59(19) 7_665 . . 7_675 ? C2 N1 C1 S1 1.3(7) . . . . ? C4 N1 C1 S1 -176.8(4) . . . . ? C2 N1 C1 S2 179.8(4) . . . . ? C4 N1 C1 S2 1.7(7) . . . . ? Na S1 C1 N1 170.5(4) 4_655 . . . ? Na S1 C1 S2 -7.9(4) 4_655 . . . ? C1 N1 C2 C3 83.5(6) . . . . ? C4 N1 C2 C3 -98.2(5) . . . . ? Na O1 C3 C2 103.8(4) . . . . ? Na O1 C3 C2 -146.1(3) 7_665 . . . ? N1 C2 C3 O1 -176.9(4) . . . . ? C1 N1 C4 C5 -98.9(6) . . . . ? C2 N1 C4 C5 82.8(6) . . . . ? N1 C4 C5 C6 177.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.67 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.109 # Attachment '7.CIF' data_7 _database_code_depnum_ccdc_archive 'CCDC 690738' # _audit_creation_method SHELXL-97 _chemical_name_systematic ; Potassium bis(ethanol)dithiocarbamate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H10 K N O2 S2 ' _chemical_formula_sum 'C5 H10 K N O2 S2' _chemical_formula_weight 219.36 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' K K 0.2009 0.2494 '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 b c m' _symmetry_space_group_name_Hall '-P 2c 2b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y+1/2, z+1/2' '-x, y+1/2, z' '-x, -y, -z' 'x, y, -z-1/2' '-x, y-1/2, -z-1/2' 'x, -y-1/2, -z' _cell_length_a 7.6968(2) _cell_length_b 14.1288(3) _cell_length_c 8.0270(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 872.92(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1168 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 1.037 _exptl_absorpt_correction_type multi-scan # compare SADABS Tmin/max (below) with calc. 0.5994/0.9034 _exptl_absorpt_correction_T_min 0.615 _exptl_absorpt_correction_T_max 0.901 _exptl_absorpt_process_details 'SADAB (Sheldrick, 2003)' _exptl_special_details ; Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000) but refined with the DENZO/COLLECT HKL package. Refs as: Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6688 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.016 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.8 _diffrn_reflns_theta_max 27.5 _reflns_number_total 1065 _reflns_number_gt 1029 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL-97 _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. Final refinement in the space group Pbcm after initial structure solution and expansion in the space group Pca21. ; _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^)+(0.0059P)^2^+1.4274P] 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 1065 _refine_ls_number_parameters 84 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.029 _refine_ls_R_factor_gt 0.027 _refine_ls_wR_factor_ref 0.068 _refine_ls_wR_factor_gt 0.067 _refine_ls_goodness_of_fit_ref 1.31 _refine_ls_restrained_S_all 1.31 _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 K1 K 0.88524(7) 0.2500 0.0000 0.01424(15) Uani 1 2 d S . . S1 S 0.89754(8) 0.43149(4) 0.2500 0.01120(16) Uani 1 2 d S . . S2 S 0.55859(8) 0.33318(4) 0.2500 0.01191(16) Uani 1 2 d S . . O1 O 0.8352(3) 0.74370(17) 0.2905(3) 0.0143(8) Uani 0.50 1 d P . . H1 H 0.7734 0.7775 0.2280 0.021 Uiso 0.50 1 d PR . . O2 O 0.1492(2) 0.60918(13) 0.2500 0.0124(4) Uani 1 2 d S . . H2 H 0.0790 0.5663 0.2232 0.019 Uiso 0.50 1 d PR . . N1 N 0.5973(4) 0.5195(2) 0.1906(4) 0.0083(6) Uani 0.50 1 d P . . C1 C 0.6761(4) 0.4363(2) 0.2500 0.0243(7) Uani 1 2 d S . . C2 C 0.6965(5) 0.6078(3) 0.1673(5) 0.0108(7) Uani 0.50 1 d P . . H2A H 0.6269 0.6517 0.0981 0.013 Uiso 0.50 1 calc PR . . H2B H 0.8044 0.5931 0.1054 0.013 Uiso 0.50 1 calc PR . . C3 C 0.7443(5) 0.6573(3) 0.3287(5) 0.0121(7) Uani 0.50 1 d P . . H3A H 0.6379 0.6717 0.3932 0.014 Uiso 0.50 1 calc PR . . H3B H 0.8192 0.6157 0.3971 0.014 Uiso 0.50 1 calc PR . . C4 C 0.4102(4) 0.5279(2) 0.1537(5) 0.0106(7) Uani 0.50 1 d P . . H4A H 0.3633 0.4647 0.1247 0.013 Uiso 0.50 1 calc PR . . H4B H 0.3939 0.5699 0.0562 0.013 Uiso 0.50 1 calc PR . . C5 C 0.3098(5) 0.5676(3) 0.3013(5) 0.0141(8) Uani 0.50 1 d P . . H5A H 0.2862 0.5162 0.3818 0.017 Uiso 0.50 1 calc PR . . H5B H 0.3814 0.6160 0.3581 0.017 Uiso 0.50 1 calc PR . . 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 K1 0.0170(3) 0.0101(3) 0.0155(3) -0.0009(2) 0.000 0.000 S1 0.0058(3) 0.0065(3) 0.0213(3) 0.000 0.000 0.0008(2) S2 0.0092(3) 0.0069(3) 0.0197(3) 0.000 0.000 -0.0031(2) O1 0.0094(10) 0.0069(10) 0.027(2) 0.0016(9) -0.0022(10) -0.0014(9) O2 0.0056(8) 0.0083(9) 0.0232(10) 0.000 0.000 -0.0001(7) N1 0.0050(13) 0.0047(12) 0.0152(13) -0.0004(10) -0.0005(10) -0.0004(10) C1 0.0091(13) 0.0063(12) 0.057(2) 0.000 0.000 0.0013(10) C2 0.0117(17) 0.0057(17) 0.0151(19) 0.0027(15) -0.0006(15) -0.0010(15) C3 0.0109(17) 0.0077(18) 0.0176(19) 0.0008(15) 0.0017(15) -0.0014(15) C4 0.0069(16) 0.0094(15) 0.0155(18) -0.0010(14) -0.0021(14) 0.0027(13) C5 0.0084(16) 0.0191(18) 0.0146(18) -0.0027(13) -0.0020(12) 0.0015(15) _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. Data below corresponds to an ordered structure, effectively in the space group Pbc21, with no trace of the disorder over two mirror plane related orientations of the bis(ethanol)amino substituent of the dithiocarbamate. ; 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 K1 O1 2.732(2) 2_764 ? K1 O2 2.8382(13) 5_665 ? K1 O2 2.8382(13) 7_656 ? K1 O1 3.174(2) 4_745 ? K1 S1 3.2575(5) . ? K1 S1 3.2575(5) 3_554 ? K1 S2 3.4248(7) 3_554 ? K1 S2 3.4248(7) . ? S1 C1 1.706(3) . ? S1 K1 3.2575(5) 6_556 ? S2 C1 1.715(3) . ? S2 K1 3.4248(7) 6_556 ? O1 C3 1.440(5) . ? O1 H1 0.8400 . ? O2 C5 1.429(4) . ? O2 H2 0.8400 . ? N1 C1 1.406(4) . ? N1 C2 1.475(5) . ? N1 C4 1.475(4) . ? C2 C3 1.518(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.522(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 K1 O2 67.38(6) 2_764 5_665 ? O1 K1 O2 122.11(6) 2_764 7_656 ? O2 K1 O2 169.29(8) 5_665 7_656 ? O1 K1 O1 85.37(6) 2_764 4_745 ? O2 K1 O1 127.04(6) 5_665 4_745 ? O2 K1 O1 61.59(5) 7_656 4_745 ? O1 K1 S1 109.31(5) 2_764 . ? O2 K1 S1 83.48(3) 5_665 . ? O2 K1 S1 96.83(3) 7_656 . ? O1 K1 S1 63.24(4) 4_745 . ? O1 K1 S1 67.89(5) 2_764 3_554 ? O2 K1 S1 96.83(3) 5_665 3_554 ? O2 K1 S1 83.48(3) 7_656 3_554 ? O1 K1 S1 114.26(5) 4_745 3_554 ? S1 K1 S1 176.67(3) . 3_554 ? O1 K1 S2 103.21(5) 2_764 3_554 ? O2 K1 S2 75.98(3) 5_665 3_554 ? O2 K1 S2 96.04(3) 7_656 3_554 ? O1 K1 S2 156.70(5) 4_745 3_554 ? S1 K1 S2 130.72(2) . 3_554 ? S1 K1 S2 52.428(15) 3_554 3_554 ? O1 K1 S2 158.06(5) 2_764 . ? O2 K1 S2 96.04(3) 5_665 . ? O2 K1 S2 75.98(3) 7_656 . ? O1 K1 S2 94.40(4) 4_745 . ? S1 K1 S2 52.429(15) . . ? S1 K1 S2 130.72(2) 3_554 . ? S2 K1 S2 85.54(2) 3_554 . ? C1 S1 K1 90.14(8) . . ? C1 S1 K1 90.14(8) . 6_556 ? K1 S1 K1 76.056(14) . 6_556 ? C1 S2 K1 84.51(8) . 6_556 ? C1 S2 K1 84.51(8) . . ? K1 S2 K1 71.740(16) 6_556 . ? C3 O1 K1 106.2(2) . 2_765 ? C3 O1 K1 120.7(2) . 5_765 ? K1 O1 K1 85.27(6) 2_765 5_765 ? C3 O1 H1 109.5 . . ? K1 O1 H1 142.7 2_765 . ? K1 O1 H1 85.9 5_765 . ? C5 O2 K1 99.50(16) . 2_665 ? C5 O2 K1 124.91(18) . 5_665 ? K1 O2 K1 89.99(5) 2_665 5_665 ? C5 O2 H2 109.5 . . ? K1 O2 H2 128.8 2_665 . ? K1 O2 H2 105.4 5_665 . ? C1 N1 C2 121.8(3) . . ? C1 N1 C4 123.8(3) . . ? C2 N1 C4 114.3(3) . . ? N1 C1 S1 117.7(2) . . ? N1 C1 S2 118.9(2) . . ? S1 C1 S2 119.54(17) . . ? N1 C2 C3 114.1(3) . . ? N1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? O1 C3 C2 109.1(3) . . ? O1 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? O1 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N1 C4 C5 111.7(3) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? O2 C5 C4 111.5(3) . . ? O2 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? O2 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? 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 O1 H1 S2 0.84 2.68 3.300(2) 131.9 4_655 Y O2 H2 S1 0.84 2.37 3.1708(19) 159.2 1_455 y _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.0 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.27 _refine_diff_density_min -0.37 _refine_diff_density_rms 0.065 # Attachment '8.CIF' data_8 _database_code_depnum_ccdc_archive 'CCDC 690739' # 06src1138 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cesium bis(ethanol)dithiocarbamate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H10 Cs N O2 S2' _chemical_formula_sum 'C5 H10 Cs N O2 S2' _chemical_formula_weight 313.17 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' Cs Cs -0.3680 2.1192 '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 b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 16.0465(4) _cell_length_b 14.2446(3) _cell_length_c 8.4274(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1926.30(8) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2506 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 4.233 _exptl_absorpt_correction_type multi-scan # compare SADABS Tmin/max (below) with calc 0.2823/0.6769 _exptl_absorpt_correction_T_min 0.454 _exptl_absorpt_correction_T_max 0.677 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_special_details ; Unit cell determined with DirAx (Duisenberg, 1992; Duisenberg et al. 2000) but refined with the DENZO/COLLECT HKL package. Refs as: Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 17609 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.019 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 2207 _reflns_number_gt 1918 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL-97 _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^)+(0.0184P)^2^+1.856P] 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 SHELXL _refine_ls_extinction_coef 0.00301(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2207 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.023 _refine_ls_R_factor_gt 0.018 _refine_ls_wR_factor_ref 0.044 _refine_ls_wR_factor_gt 0.042 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 Cs1 Cs 0.450582(8) 0.252704(8) 0.559747(14) 0.01380(7) Uani 1 1 d . . . S1 S 0.43510(3) 0.44892(4) 0.83367(7) 0.01638(12) Uani 1 1 d . . . S2 S 0.27909(3) 0.34358(3) 0.77000(6) 0.01561(12) Uani 1 1 d . . . O1 O 0.40177(10) 0.75563(9) 0.69431(17) 0.0164(3) Uani 1 1 d . . . H1O H 0.3644 0.7956 0.7118 0.025 Uiso 1 1 calc R . . O2 O 0.06752(9) 0.58955(11) 0.81341(17) 0.0164(3) Uani 1 1 d . . . H2O H 0.0304 0.5510 0.7875 0.025 Uiso 1 1 calc R . . N1 N 0.28964(10) 0.53074(11) 0.77010(19) 0.0112(3) Uani 1 1 d . . . C1 C 0.33086(13) 0.44889(14) 0.7878(2) 0.0120(4) Uani 1 1 d . . . C2 C 0.32823(13) 0.62188(13) 0.8063(2) 0.0134(4) Uani 1 1 d . . . H2A H 0.3732 0.6128 0.8853 0.016 Uiso 1 1 calc R . . H2B H 0.2859 0.6641 0.8534 0.016 Uiso 1 1 calc R . . C3 C 0.36425(13) 0.66729(13) 0.6578(2) 0.0147(4) Uani 1 1 d . . . H3A H 0.4065 0.6251 0.6105 0.018 Uiso 1 1 calc R . . H3B H 0.3193 0.6766 0.5788 0.018 Uiso 1 1 calc R . . C4 C 0.20272(12) 0.53702(14) 0.7166(2) 0.0132(4) Uani 1 1 d . . . H4A H 0.1897 0.4821 0.6490 0.016 Uiso 1 1 calc R . . H4B H 0.1957 0.5942 0.6512 0.016 Uiso 1 1 calc R . . C5 C 0.14156(13) 0.54020(15) 0.8550(2) 0.0177(4) Uani 1 1 d . . . H5A H 0.1271 0.4754 0.8870 0.021 Uiso 1 1 calc R . . H5B H 0.1683 0.5715 0.9467 0.021 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 Cs1 0.01516(10) 0.01375(9) 0.01250(9) 0.00010(4) 0.00173(4) 0.00033(4) S1 0.0101(2) 0.0143(2) 0.0248(3) 0.0051(2) -0.0025(2) -0.00068(19) S2 0.0127(2) 0.0107(2) 0.0235(3) -0.0011(2) 0.0022(2) -0.00259(19) O1 0.0111(8) 0.0117(7) 0.0262(9) -0.0004(6) 0.0015(6) -0.0014(5) O2 0.0088(7) 0.0170(7) 0.0236(8) -0.0039(6) -0.0017(6) 0.0004(6) N1 0.0097(8) 0.0097(7) 0.0143(8) 0.0001(6) -0.0013(7) -0.0007(6) C1 0.0123(10) 0.0131(9) 0.0106(9) 0.0001(7) 0.0024(8) -0.0013(8) C2 0.0150(11) 0.0101(9) 0.0153(10) -0.0015(7) 0.0001(8) -0.0001(8) C3 0.0139(11) 0.0121(9) 0.0182(10) 0.0000(8) -0.0005(8) -0.0012(8) C4 0.0108(10) 0.0152(10) 0.0134(9) 0.0026(8) -0.0011(8) 0.0010(8) C5 0.0147(11) 0.0214(10) 0.0171(10) 0.0026(8) 0.0010(9) 0.0038(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 # v. -x+1/2, 1-y, z-1/2 # ii. 1-x, y-1/2, -z+3/2 # iv. -x+1/2, y-1/2, z # iii. 1-x, 1-y, 1-z # i. x, -y+1/2, z-1/2 # i. x, -y+1/2, z-1/2 Cs1 O2 3.0730(14) 4_564 ? Cs1 O1 3.1482(16) 3_646 ? Cs1 O2 3.1711(15) 6_655 ? Cs1 O1 3.1956(15) 5_666 ? Cs1 S1 3.4555(5) 7_565 ? Cs1 S2 3.5196(5) . ? Cs1 S1 3.6335(6) . ? Cs1 S2 3.9263(6) 7_565 ? S1 C1 1.717(2) . ? S2 C1 1.721(2) . ? O1 C3 1.429(2) . ? O1 H1O 0.8400 . ? O2 C5 1.424(2) . ? O2 H2O 0.8400 . ? N1 C1 1.349(3) . ? N1 C4 1.469(2) . ? N1 C2 1.470(2) . ? C2 C3 1.522(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.525(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? 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 # v. -x+1/2, 1-y, z-1/2; iv. -x+1/2, y-1/2, z # iii. 1-x, 1-y, 1-z # i. x, -y+1/2, z-1/2 # ii.1-x, y-1/2, -z+3/2; i. x, -y+1/2, z-1/2 O2 Cs1 O1 120.41(4) 4_564 3_646 ? O2 Cs1 O2 169.32(6) 4_564 6_655 ? O1 Cs1 O2 68.58(4) 3_646 6_655 ? O2 Cs1 O1 69.18(4) 4_564 5_666 ? O1 Cs1 O1 83.32(4) 3_646 5_666 ? O2 Cs1 O1 119.50(4) 6_655 5_666 ? O2 Cs1 S1 103.21(3) 4_564 7_565 ? O1 Cs1 S1 115.35(3) 3_646 7_565 ? O2 Cs1 S1 75.87(3) 6_655 7_565 ? O1 Cs1 S1 69.70(3) 5_666 7_565 ? O2 Cs1 S2 89.84(3) 4_564 . ? O1 Cs1 S2 104.60(3) 3_646 . ? O2 Cs1 S2 81.87(3) 6_655 . ? O1 Cs1 S2 158.54(3) 5_666 . ? S1 Cs1 S2 121.807(13) 7_565 . ? O2 Cs1 S1 81.97(3) 4_564 . ? O1 Cs1 S1 67.85(3) 3_646 . ? O2 Cs1 S1 97.42(3) 6_655 . ? O1 Cs1 S1 120.33(3) 5_666 . ? S1 Cs1 S1 169.973(17) 7_565 . ? S2 Cs1 S1 48.990(12) . . ? O2 Cs1 S2 76.65(3) 4_564 7_565 ? O1 Cs1 S2 160.31(2) 3_646 7_565 ? O2 Cs1 S2 95.68(3) 6_655 7_565 ? O1 Cs1 S2 95.16(3) 5_666 7_565 ? S1 Cs1 S2 46.874(11) 7_565 7_565 ? S2 Cs1 S2 83.891(13) . 7_565 ? S1 Cs1 S2 128.017(12) . 7_565 ? C1 S1 Cs1 101.18(7) . 7_566 ? C1 S1 Cs1 85.61(7) . . ? Cs1 S1 Cs1 72.905(10) 7_566 . ? C1 S2 Cs1 89.26(7) . . ? C1 S2 Cs1 84.95(7) . 7_566 ? Cs1 S2 Cs1 68.694(10) . 7_566 ? C3 O1 Cs1 116.57(11) . 3_656 ? C3 O1 Cs1 97.78(11) . 5_666 ? Cs1 O1 Cs1 83.26(4) 3_656 5_666 ? C3 O1 H1O 109.5 . . ? C5 O2 H2O 109.5 . . ? C1 N1 C4 123.53(16) . . ? C1 N1 C2 122.27(16) . . ? C4 N1 C2 114.20(16) . . ? N1 C1 S1 120.17(15) . . ? N1 C1 S2 120.47(15) . . ? S1 C1 S2 119.34(12) . . ? N1 C2 C3 111.39(15) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O1 C3 C2 110.93(16) . . ? O1 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? N1 C4 C5 112.21(16) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O2 C5 C4 111.30(16) . . ? O2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? O2 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? 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 C4 N1 C1 S1 174.10(14) . . . . ? C2 N1 C1 S1 -7.1(2) . . . . ? C4 N1 C1 S2 -7.6(2) . . . . ? C2 N1 C1 S2 171.16(14) . . . . ? C1 N1 C2 C3 95.6(2) . . . . ? C4 N1 C2 C3 -85.5(2) . . . . ? N1 C2 C3 O1 -179.84(16) . . . . ? C1 N1 C4 C5 93.6(2) . . . . ? C2 N1 C4 C5 -85.3(2) . . . . ? N1 C4 C5 O2 151.85(16) . . . . ? 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 # '1/2-x, 1/2+y, z' O1 H1O S2 0.84 2.45 3.2247(17) 154 6_665 ? O2 H2O S1 0.84 2.34 3.1724(16) 169 8_557 ? # 'x-1/2, y, 3/2-z' _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.92 # 1.60 A from H3B _refine_diff_density_min -0.61 # 0.80 A from CS1 _refine_diff_density_rms 0.096