Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _audit_creation_method 'SHELXL-97 plus manual editing' #============================================== # contact for queries related to this CIF only #============================================== _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; University of Southern Denmark Department of Physics and Chemistry Campusvej 55 5230 Odense Denmark ; _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_fax '+45 6615 8780' _publ_contact_author_phone '+45 6650 2545' #==================================== # denoted 13.DMSO.2H2O in manuscript #==================================== data_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O6, C2 H6 O S, 2(H2 O)' _chemical_formula_sum 'C16 H28 N4 O9 S' _chemical_formula_weight 452.48 _chemical_absolute_configuration ad 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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.2709(12) _cell_length_b 16.736(4) _cell_length_c 12.148(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.432(4) _cell_angle_gamma 90.00 _cell_volume 1062.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3673 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.728 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.745398 ; _exptl_special_details ; H atoms bound to O located in difference Fourier maps and refined with O---H distances restrained to 0.88(1) \%A. For water molecules, H...H distance also restrained to 1.40(1) \%A. Isotropic displacement parameters constrained to be 1.2 times U~eq~ of parent O atom for hydroxyl groups and 1.5 times U~eq~ of O for water molecules. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 9515 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 26.13 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4139 _reflns_number_gt 3634 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-8 (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.0926P)^2^+0.1656P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(10) _refine_ls_number_reflns 4139 _refine_ls_number_parameters 291 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.991 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.063 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 O1 O 0.2944(4) 0.24771(14) 0.41994(18) 0.0412(5) Uani 1 1 d . . . O2 O 0.3136(4) 0.05624(12) 0.15936(16) 0.0341(5) Uani 1 1 d . . . O3 O -0.2918(4) 0.04399(13) 0.93053(17) 0.0385(5) Uani 1 1 d . . . O4 O -0.3075(4) 0.22982(13) 1.20207(16) 0.0353(5) Uani 1 1 d . . . O5 O 0.3198(4) 0.13464(13) 0.64205(16) 0.0318(5) Uani 1 1 d D . . H5 H 0.380(7) 0.0914(13) 0.614(3) 0.038 Uiso 1 1 d D . . O6 O -0.0199(5) 0.24457(13) 0.74219(18) 0.0416(5) Uani 1 1 d D . . H6 H 0.146(2) 0.252(2) 0.761(3) 0.050 Uiso 1 1 d D . . N1 N 0.0236(4) 0.14077(14) 0.42585(17) 0.0269(5) Uani 1 1 d . . . N2 N 0.3041(4) 0.14826(14) 0.29410(18) 0.0275(5) Uani 1 1 d . . . H2A H 0.4303 0.1728 0.2672 0.033 Uiso 1 1 calc R . . N3 N -0.0044(4) 0.14677(16) 0.93805(18) 0.0293(5) Uani 1 1 d . . . N4 N -0.2929(4) 0.13853(14) 1.06564(18) 0.0281(5) Uani 1 1 d . . . H4B H -0.4184 0.1129 1.0916 0.034 Uiso 1 1 calc R . . C1 C 0.2127(5) 0.18363(18) 0.3835(2) 0.0285(6) Uani 1 1 d . . . C2 C 0.2179(5) 0.07859(17) 0.2428(2) 0.0277(6) Uani 1 1 d . . . C3 C 0.0170(5) 0.03764(17) 0.2889(2) 0.0297(6) Uani 1 1 d . . . C4 C -0.0676(5) 0.07049(17) 0.3781(2) 0.0275(6) Uani 1 1 d . . . H4A H -0.1985 0.0434 0.4101 0.033 Uiso 1 1 calc R . . C5 C -0.0858(6) -0.0379(2) 0.2353(3) 0.0401(7) Uani 1 1 d . . . H5A H -0.2268 -0.0575 0.2732 0.060 Uiso 1 1 calc R . . H5B H 0.0503 -0.0782 0.2404 0.060 Uiso 1 1 calc R . . H5C H -0.1483 -0.0277 0.1570 0.060 Uiso 1 1 calc R . . C6 C -0.0717(5) 0.17076(18) 0.5271(2) 0.0293(6) Uani 1 1 d . . . H6A H -0.2597 0.1640 0.5198 0.035 Uiso 1 1 calc R . . H6B H -0.0335 0.2285 0.5355 0.035 Uiso 1 1 calc R . . C7 C 0.0514(5) 0.12634(17) 0.6302(2) 0.0267(6) Uani 1 1 d . . . H7A H 0.0068 0.0684 0.6225 0.032 Uiso 1 1 calc R . . C8 C -0.0459(5) 0.15917(17) 0.7347(2) 0.0284(6) Uani 1 1 d . . . H8A H -0.2318 0.1459 0.7305 0.034 Uiso 1 1 calc R . . C9 C 0.0934(6) 0.11890(19) 0.8372(2) 0.0314(6) Uani 1 1 d . . . H9A H 0.0710 0.0603 0.8305 0.038 Uiso 1 1 calc R . . H9B H 0.2786 0.1307 0.8425 0.038 Uiso 1 1 calc R . . C10 C -0.2027(5) 0.10494(18) 0.9745(2) 0.0279(6) Uani 1 1 d . . . C11 C -0.2091(5) 0.20761(17) 1.1207(2) 0.0271(6) Uani 1 1 d . . . C12 C -0.0007(5) 0.24863(18) 1.0780(2) 0.0296(6) Uani 1 1 d . . . C13 C 0.0918(5) 0.21573(18) 0.9901(2) 0.0301(6) Uani 1 1 d . . . H13A H 0.2313 0.2414 0.9624 0.036 Uiso 1 1 calc R . . C14 C 0.1027(7) 0.32284(19) 1.1333(3) 0.0368(7) Uani 1 1 d . . . H14A H 0.2541 0.3401 1.1005 0.055 Uiso 1 1 calc R . . H14B H 0.1501 0.3127 1.2127 0.055 Uiso 1 1 calc R . . H14C H -0.0278 0.3648 1.1231 0.055 Uiso 1 1 calc R . . S1 S 0.54592(15) -0.07164(5) 0.56876(8) 0.0487(3) Uani 1 1 d . . . O1S O 0.5067(5) 0.01409(14) 0.5328(2) 0.0479(6) Uani 1 1 d . . . C1S C 0.3754(10) -0.0841(4) 0.6806(6) 0.111(3) Uani 1 1 d . . . H1SA H 0.4634 -0.0561 0.7455 0.166 Uiso 1 1 calc R . . H1SB H 0.3637 -0.1411 0.6975 0.166 Uiso 1 1 calc R . . H1SC H 0.2030 -0.0620 0.6621 0.166 Uiso 1 1 calc R . . C2S C 0.3519(14) -0.1266(3) 0.4637(7) 0.144(4) Uani 1 1 d . . . H2SA H 0.4289 -0.1246 0.3945 0.215 Uiso 1 1 calc R . . H2SB H 0.1803 -0.1031 0.4515 0.215 Uiso 1 1 calc R . . H2SC H 0.3400 -0.1823 0.4873 0.215 Uiso 1 1 calc R . . O1W O 0.5118(6) 0.29325(18) 0.8301(3) 0.0630(8) Uani 1 1 d D . . H1W H 0.608(7) 0.321(3) 0.881(3) 0.094 Uiso 1 1 d D . . H2W H 0.610(8) 0.282(3) 0.779(3) 0.094 Uiso 1 1 d D . . O2W O 0.6118(5) 0.42537(16) 0.9782(2) 0.0477(6) Uani 1 1 d D . . H3W H 0.670(8) 0.4608(18) 0.933(3) 0.071 Uiso 1 1 d D . . H4W H 0.507(7) 0.453(2) 1.014(3) 0.071 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0489(13) 0.0428(13) 0.0347(11) -0.0116(10) 0.0158(9) -0.0128(10) O2 0.0389(11) 0.0349(11) 0.0310(10) -0.0080(9) 0.0143(8) -0.0045(9) O3 0.0458(12) 0.0384(12) 0.0331(11) -0.0049(9) 0.0118(9) -0.0043(10) O4 0.0376(11) 0.0385(12) 0.0329(11) -0.0045(9) 0.0163(9) -0.0026(9) O5 0.0245(10) 0.0433(12) 0.0283(10) -0.0067(9) 0.0060(7) 0.0029(8) O6 0.0582(14) 0.0344(12) 0.0350(11) -0.0042(10) 0.0161(10) 0.0083(11) N1 0.0293(12) 0.0317(13) 0.0206(11) 0.0003(10) 0.0068(9) -0.0030(10) N2 0.0276(12) 0.0309(12) 0.0253(11) -0.0012(10) 0.0084(9) -0.0046(9) N3 0.0281(12) 0.0376(14) 0.0231(11) 0.0022(10) 0.0069(9) 0.0032(10) N4 0.0286(12) 0.0331(12) 0.0246(11) 0.0002(10) 0.0107(9) -0.0043(10) C1 0.0307(15) 0.0303(14) 0.0249(14) -0.0024(11) 0.0054(11) -0.0041(12) C2 0.0271(14) 0.0306(14) 0.0247(14) 0.0026(11) 0.0009(11) 0.0022(11) C3 0.0295(14) 0.0297(15) 0.0292(14) 0.0036(12) 0.0017(11) 0.0001(11) C4 0.0247(13) 0.0296(14) 0.0283(14) 0.0047(11) 0.0037(10) -0.0015(10) C5 0.0399(17) 0.0335(16) 0.0477(19) -0.0049(14) 0.0089(14) -0.0085(13) C6 0.0273(14) 0.0348(16) 0.0277(14) 0.0001(11) 0.0110(11) 0.0067(11) C7 0.0261(13) 0.0307(14) 0.0238(13) -0.0008(11) 0.0056(10) 0.0008(11) C8 0.0271(14) 0.0322(15) 0.0274(14) -0.0003(11) 0.0090(11) 0.0045(11) C9 0.0282(14) 0.0407(16) 0.0267(14) 0.0004(12) 0.0089(11) 0.0050(12) C10 0.0302(14) 0.0337(15) 0.0202(13) 0.0010(12) 0.0042(10) 0.0019(12) C11 0.0250(14) 0.0331(15) 0.0236(13) 0.0014(12) 0.0045(10) 0.0001(11) C12 0.0273(14) 0.0363(16) 0.0256(14) 0.0049(12) 0.0052(11) 0.0001(11) C13 0.0256(14) 0.0405(16) 0.0250(13) 0.0033(12) 0.0062(10) -0.0035(12) C14 0.0381(17) 0.0387(18) 0.0344(16) 0.0001(13) 0.0078(13) -0.0096(13) S1 0.0309(4) 0.0308(4) 0.0824(7) 0.0008(4) -0.0008(4) 0.0004(3) O1S 0.0572(15) 0.0291(12) 0.0636(15) -0.0016(11) 0.0319(12) -0.0017(10) C1S 0.076(3) 0.106(5) 0.164(6) 0.099(5) 0.066(4) 0.043(3) C2S 0.131(5) 0.031(2) 0.231(9) 0.010(3) -0.116(6) -0.002(3) O1W 0.074(2) 0.0492(17) 0.073(2) -0.0153(14) 0.0371(16) -0.0033(14) O2W 0.0552(14) 0.0412(13) 0.0492(14) 0.0104(12) 0.0167(10) 0.0112(12) _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 O1 C1 1.217(4) . ? O2 C2 1.246(3) . ? O3 C10 1.217(4) . ? O4 C11 1.231(3) . ? O5 C7 1.411(3) . ? O5 H5 0.88(1) . ? O6 C8 1.437(4) . ? O6 H6 0.88(1) . ? N1 C4 1.371(4) . ? N1 C1 1.380(4) . ? N1 C6 1.475(3) . ? N2 C2 1.372(4) . ? N2 C1 1.378(4) . ? N2 H2A 0.880 . ? N3 C10 1.378(4) . ? N3 C13 1.381(4) . ? N3 C9 1.465(3) . ? N4 C11 1.379(4) . ? N4 C10 1.380(3) . ? N4 H4B 0.880 . ? C2 C3 1.435(4) . ? C3 C4 1.342(4) . ? C3 C5 1.492(4) . ? C4 H4A 0.950 . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C5 H5C 0.980 . ? C6 C7 1.528(4) . ? C6 H6A 0.990 . ? C6 H6B 0.990 . ? C7 C8 1.531(3) . ? C7 H7A 1.000 . ? C8 C9 1.519(4) . ? C8 H8A 1.000 . ? C9 H9A 0.990 . ? C9 H9B 0.990 . ? C11 C12 1.448(4) . ? C12 C13 1.347(4) . ? C12 C14 1.482(4) . ? C13 H13A 0.950 . ? C14 H14A 0.980 . ? C14 H14B 0.980 . ? C14 H14C 0.980 . ? S1 O1S 1.506(2) . ? S1 C1S 1.736(5) . ? S1 C2S 1.784(6) . ? C1S H1SA 0.980 . ? C1S H1SB 0.980 . ? C1S H1SC 0.980 . ? C2S H2SA 0.980 . ? C2S H2SB 0.980 . ? C2S H2SC 0.980 . ? O1W H1W 0.88(1) . ? O1W H2W 0.88(1) . ? O2W H3W 0.89(1) . ? O2W H4W 0.88(1) . ? 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 C7 O5 H5 107(2) . . ? C8 O6 H6 103(3) . . ? C4 N1 C1 121.3(2) . . ? C4 N1 C6 120.4(2) . . ? C1 N1 C6 118.3(2) . . ? C2 N2 C1 126.5(2) . . ? C2 N2 H2A 116.7 . . ? C1 N2 H2A 116.7 . . ? C10 N3 C13 121.8(2) . . ? C10 N3 C9 118.1(3) . . ? C13 N3 C9 120.1(2) . . ? C11 N4 C10 127.5(2) . . ? C11 N4 H4B 116.3 . . ? C10 N4 H4B 116.3 . . ? O1 C1 N2 121.4(2) . . ? O1 C1 N1 124.1(2) . . ? N2 C1 N1 114.4(2) . . ? O2 C2 N2 118.7(2) . . ? O2 C2 C3 124.8(3) . . ? N2 C2 C3 116.5(2) . . ? C4 C3 C2 117.3(3) . . ? C4 C3 C5 124.1(3) . . ? C2 C3 C5 118.6(3) . . ? C3 C4 N1 124.0(2) . . ? C3 C4 H4A 118.0 . . ? N1 C4 H4A 118.0 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 111.3(2) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O5 C7 C6 110.5(2) . . ? O5 C7 C8 108.6(2) . . ? C6 C7 C8 110.7(2) . . ? O5 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? O6 C8 C9 110.9(3) . . ? O6 C8 C7 111.7(2) . . ? C9 C8 C7 110.0(2) . . ? O6 C8 H8A 108.0 . . ? C9 C8 H8A 108.0 . . ? C7 C8 H8A 108.0 . . ? N3 C9 C8 111.1(2) . . ? 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 . . ? O3 C10 N3 123.4(2) . . ? O3 C10 N4 122.7(3) . . ? N3 C10 N4 113.9(3) . . ? O4 C11 N4 120.0(3) . . ? O4 C11 C12 124.2(3) . . ? N4 C11 C12 115.7(2) . . ? C13 C12 C11 117.4(3) . . ? C13 C12 C14 123.5(3) . . ? C11 C12 C14 119.1(3) . . ? C12 C13 N3 123.8(3) . . ? C12 C13 H13A 118.1 . . ? N3 C13 H13A 118.1 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1S S1 C1S 106.0(2) . . ? O1S S1 C2S 103.8(2) . . ? C1S S1 C2S 101.0(5) . . ? S1 C1S H1SA 109.5 . . ? S1 C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? S1 C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? S1 C2S H2SA 109.5 . . ? S1 C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? S1 C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? H1W O1W H2W 106(2) . . ? H3W O2W H4W 104(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N2 C1 O1 -176.5(3) . . . . ? C2 N2 C1 N1 3.0(4) . . . . ? C4 N1 C1 O1 177.2(3) . . . . ? C6 N1 C1 O1 -5.2(4) . . . . ? C4 N1 C1 N2 -2.3(4) . . . . ? C6 N1 C1 N2 175.3(2) . . . . ? C1 N2 C2 O2 176.9(3) . . . . ? C1 N2 C2 C3 -1.7(4) . . . . ? O2 C2 C3 C4 -178.9(3) . . . . ? N2 C2 C3 C4 -0.4(4) . . . . ? O2 C2 C3 C5 0.8(4) . . . . ? N2 C2 C3 C5 179.3(3) . . . . ? C2 C3 C4 N1 1.1(4) . . . . ? C5 C3 C4 N1 -178.6(3) . . . . ? C1 N1 C4 C3 0.4(4) . . . . ? C6 N1 C4 C3 -177.1(3) . . . . ? C4 N1 C6 C7 78.1(3) . . . . ? C1 N1 C6 C7 -99.5(3) . . . . ? N1 C6 C7 O5 58.6(3) . . . . ? N1 C6 C7 C8 179.0(2) . . . . ? O5 C7 C8 O6 69.5(3) . . . . ? C6 C7 C8 O6 -51.9(3) . . . . ? O5 C7 C8 C9 -54.2(3) . . . . ? C6 C7 C8 C9 -175.6(3) . . . . ? C10 N3 C9 C8 91.0(3) . . . . ? C13 N3 C9 C8 -85.4(3) . . . . ? O6 C8 C9 N3 58.4(3) . . . . ? C7 C8 C9 N3 -177.5(2) . . . . ? C13 N3 C10 O3 -180.0(3) . . . . ? C9 N3 C10 O3 3.8(4) . . . . ? C13 N3 C10 N4 0.3(4) . . . . ? C9 N3 C10 N4 -176.0(2) . . . . ? C11 N4 C10 O3 -179.0(3) . . . . ? C11 N4 C10 N3 0.8(4) . . . . ? C10 N4 C11 O4 -179.3(3) . . . . ? C10 N4 C11 C12 -0.7(4) . . . . ? O4 C11 C12 C13 178.1(3) . . . . ? N4 C11 C12 C13 -0.4(4) . . . . ? O4 C11 C12 C14 -0.8(4) . . . . ? N4 C11 C12 C14 -179.3(2) . . . . ? C11 C12 C13 N3 1.4(4) . . . . ? C14 C12 C13 N3 -179.7(3) . . . . ? C10 N3 C13 C12 -1.4(4) . . . . ? C9 N3 C13 C12 174.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O1S 0.88(1) 1.81(1) 2.672(3) 169(3) . O6 H6 O1W 0.88(1) 2.12(1) 2.981(4) 165(3) . O1W H1W O2W 0.88(1) 2.11(3) 2.857(4) 143(5) . O1W H2W O6 0.88(1) 2.15(3) 2.929(3) 148(5) 1_655 O2W H3W O2 0.89(1) 1.96(2) 2.813(3) 160(4) 2_656 O2W H4W O3 0.88(1) 2.06(2) 2.916(3) 164(3) 2_557 #==================================== # denoted 14.2DMSO in manuscript #==================================== data_14 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O6, 2(C2 H6 O S)' _chemical_formula_sum 'C18 H30 N4 O8 S2' _chemical_formula_weight 494.58 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 5.224(2) _cell_length_b 9.313(4) _cell_length_c 12.558(6) _cell_angle_alpha 101.76(3) _cell_angle_beta 91.68(3) _cell_angle_gamma 105.00(3) _cell_volume 575.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1203 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 22.35 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 262 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.763 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'TwinSolve (Svensson, 2005)' _exptl_special_details ; Data collected on protein-based experimental station. Kappa axis of goniometer constrained so that only a 360 deg. phi scan is possible. Hence the data are ca 88% complete with low redundancy. Diffraction was relatively weak and is truncated to 1 \%A resolution. (The impressive merging R-factor results only from the fact that very few reflections are available to be merged!). A suitable weighting scheme could not be obtained, so unit weights are retained. Data corrected for beam decay during integration on the basis of the ring current values. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.7500 _diffrn_radiation_type synchrotron _diffrn_radiation_source ; Beamline I911-3 at the MAX-II storage ring: MAX-Lab, Lund, Sweden ; _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type ; MARmosaic multi-element CCD (225x225mm) on CrystalLogic Kappa goniometer ; _diffrn_measurement_method '\f scans' _diffrn_standards_number 0 _diffrn_reflns_number 1231 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 22.02 _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 22.02 _diffrn_measured_fraction_theta_full 0.873 _reflns_number_total 1047 _reflns_number_gt 918 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Local to MAXLAB' _computing_cell_refinement 'TwinSolve v.1.62 (Svensson, 2005)' _computing_data_reduction 'TwinSolve v.1.62' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1047 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1272 _refine_ls_R_factor_gt 0.1169 _refine_ls_wR_factor_ref 0.3156 _refine_ls_wR_factor_gt 0.2928 _refine_ls_goodness_of_fit_ref 3.024 _refine_ls_restrained_S_all 3.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.899 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.127 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 O1 O 0.8958(12) 0.6966(6) 0.7818(4) 0.0620(18) Uani 1 1 d . . . O2 O 0.7250(10) 0.3443(5) 0.4640(4) 0.0545(17) Uani 1 1 d . . . O5 O 0.4403(13) 0.3186(6) 0.9075(4) 0.0699(19) Uani 1 1 d . . . H5 H 0.5404 0.2875 0.8625 0.105 Uiso 1 1 d R . . N1 N 0.5003(13) 0.5131(6) 0.7556(4) 0.0471(18) Uani 1 1 d . . . N2 N 0.8044(12) 0.5218(6) 0.6231(4) 0.0445(18) Uani 1 1 d . . . H2A H 0.9578 0.5665 0.6016 0.053 Uiso 1 1 calc R . . C1 C 0.7375(16) 0.5828(8) 0.7240(5) 0.047(2) Uani 1 1 d . . . C2 C 0.6418(17) 0.3930(8) 0.5533(6) 0.053(2) Uani 1 1 d . . . C3 C 0.3953(15) 0.3236(8) 0.5889(5) 0.048(2) Uani 1 1 d . . . C4 C 0.3341(17) 0.3876(8) 0.6879(6) 0.050(2) Uani 1 1 d . . . H4A H 0.1670 0.3431 0.7117 0.060 Uiso 1 1 calc R . . C5 C 0.2141(17) 0.1805(8) 0.5169(6) 0.056(2) Uani 1 1 d . . . H5A H 0.0526 0.1467 0.5531 0.084 Uiso 1 1 calc R . . H5B H 0.3065 0.1002 0.5041 0.084 Uiso 1 1 calc R . . H5C H 0.1658 0.2021 0.4469 0.084 Uiso 1 1 calc R . . C6 C 0.4329(17) 0.5612(8) 0.8662(5) 0.050(2) Uani 1 1 d . . . H6A H 0.2374 0.5408 0.8668 0.060 Uiso 1 1 calc R . . H6B H 0.5127 0.6722 0.8923 0.060 Uiso 1 1 calc R . . C7 C 0.5354(17) 0.4762(7) 0.9419(5) 0.052(2) Uani 1 1 d . . . H7A H 0.7337 0.5034 0.9429 0.062 Uiso 1 1 calc R . . S1 S 0.7785(4) 0.0623(2) 0.76400(15) 0.0599(12) Uani 1 1 d . . . O1S O 0.7582(11) 0.2194(5) 0.7638(4) 0.0616(17) Uani 1 1 d . . . C1S C 0.4527(17) -0.0572(10) 0.7444(7) 0.071(3) Uani 1 1 d . . . H1SA H 0.3803 -0.0692 0.6692 0.106 Uiso 1 1 calc R . . H1SB H 0.3417 -0.0120 0.7953 0.106 Uiso 1 1 calc R . . H1SC H 0.4541 -0.1571 0.7577 0.106 Uiso 1 1 calc R . . C2S C 0.843(2) 0.0590(10) 0.9014(7) 0.080(3) Uani 1 1 d . . . H2SA H 1.0239 0.1215 0.9277 0.120 Uiso 1 1 calc R . . H2SB H 0.8254 -0.0461 0.9080 0.120 Uiso 1 1 calc R . . H2SC H 0.7152 0.0999 0.9453 0.120 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 O1 0.060(5) 0.060(4) 0.057(3) 0.006(3) 0.015(3) 0.003(3) O2 0.046(4) 0.052(3) 0.055(3) 0.007(2) 0.014(2) -0.002(2) O5 0.083(5) 0.054(4) 0.068(3) 0.014(2) 0.021(3) 0.008(3) N1 0.048(5) 0.038(4) 0.047(3) 0.007(3) 0.011(3) -0.002(3) N2 0.042(5) 0.036(3) 0.044(4) 0.003(3) 0.012(3) -0.005(3) C1 0.045(7) 0.037(4) 0.054(5) 0.012(4) 0.004(4) -0.003(4) C2 0.062(7) 0.043(5) 0.053(4) 0.017(4) 0.012(4) 0.008(4) C3 0.043(6) 0.042(4) 0.055(4) 0.013(3) 0.011(4) 0.002(4) C4 0.052(6) 0.043(5) 0.060(5) 0.022(4) 0.019(4) 0.014(4) C5 0.052(6) 0.049(4) 0.058(4) 0.010(3) 0.011(4) -0.002(4) C6 0.050(6) 0.044(4) 0.052(4) 0.005(3) 0.014(3) 0.008(4) C7 0.070(7) 0.028(4) 0.054(4) 0.011(3) 0.021(4) 0.003(4) S1 0.056(2) 0.0522(17) 0.0699(17) 0.0147(11) 0.0156(11) 0.0103(12) O1S 0.059(4) 0.051(3) 0.075(3) 0.021(2) 0.019(3) 0.009(3) C1S 0.041(7) 0.070(6) 0.084(6) 0.005(4) 0.003(4) -0.004(4) C2S 0.076(8) 0.066(6) 0.096(6) 0.033(5) -0.009(5) 0.005(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 O1 C1 1.237(8) . ? O2 C2 1.256(8) . ? O5 C7 1.392(8) . ? O5 H5 0.840 . ? N1 C1 1.354(10) . ? N1 C4 1.367(9) . ? N1 C6 1.452(8) . ? N2 C1 1.373(8) . ? N2 C2 1.389(9) . ? N2 H2A 0.880 . ? C2 C3 1.413(11) . ? C3 C4 1.350(9) . ? C3 C5 1.515(10) . ? C4 H4A 0.950 . ? C5 H5A 0.980 . ? C5 H5B 0.980 . ? C5 H5C 0.980 . ? C6 C7 1.521(10) . ? C6 H6A 0.990 . ? C6 H6B 0.990 . ? C7 C7 1.522(13) 2_667 ? C7 H7A 1.000 . ? S1 O1S 1.495(5) . ? S1 C1S 1.755(9) . ? S1 C2S 1.756(8) . ? C1S H1SA 0.980 . ? C1S H1SB 0.980 . ? C1S H1SC 0.980 . ? C2S H2SA 0.980 . ? C2S H2SB 0.980 . ? C2S H2SC 0.980 . ? 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 C7 O5 H5 108.7 . . ? C1 N1 C4 120.4(6) . . ? C1 N1 C6 120.0(6) . . ? C4 N1 C6 119.2(6) . . ? C1 N2 C2 123.2(6) . . ? C1 N2 H2A 118.4 . . ? C2 N2 H2A 118.4 . . ? O1 C1 N1 123.2(6) . . ? O1 C1 N2 119.1(7) . . ? N1 C1 N2 117.7(6) . . ? O2 C2 N2 118.1(7) . . ? O2 C2 C3 124.3(7) . . ? N2 C2 C3 117.6(6) . . ? C4 C3 C2 117.7(7) . . ? C4 C3 C5 122.7(7) . . ? C2 C3 C5 119.5(6) . . ? C3 C4 N1 123.4(7) . . ? C3 C4 H4A 118.3 . . ? N1 C4 H4A 118.3 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 110.3(6) . . ? N1 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N1 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O5 C7 C6 112.9(7) . . ? O5 C7 C7 109.0(6) . 2_667 ? C6 C7 C7 111.2(7) . 2_667 ? O5 C7 H7A 107.9 . . ? C6 C7 H7A 107.9 . . ? C7 C7 H7A 107.9 2_667 . ? O1S S1 C1S 106.9(4) . . ? O1S S1 C2S 106.0(4) . . ? C1S S1 C2S 97.5(4) . . ? S1 C1S H1SA 109.5 . . ? S1 C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? S1 C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? S1 C2S H2SA 109.5 . . ? S1 C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? S1 C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 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 C4 N1 C1 O1 -180.0(6) . . . . ? C6 N1 C1 O1 -6.6(11) . . . . ? C4 N1 C1 N2 -0.8(10) . . . . ? C6 N1 C1 N2 172.6(6) . . . . ? C2 N2 C1 O1 178.9(7) . . . . ? C2 N2 C1 N1 -0.3(10) . . . . ? C1 N2 C2 O2 -178.2(6) . . . . ? C1 N2 C2 C3 0.5(10) . . . . ? O2 C2 C3 C4 178.9(6) . . . . ? N2 C2 C3 C4 0.3(10) . . . . ? O2 C2 C3 C5 0.2(11) . . . . ? N2 C2 C3 C5 -178.4(6) . . . . ? C2 C3 C4 N1 -1.5(10) . . . . ? C5 C3 C4 N1 177.3(7) . . . . ? C1 N1 C4 C3 1.8(11) . . . . ? C6 N1 C4 C3 -171.7(6) . . . . ? C1 N1 C6 C7 -87.4(8) . . . . ? C4 N1 C6 C7 86.1(8) . . . . ? N1 C6 C7 O5 -56.7(8) . . . . ? N1 C6 C7 C7 -179.5(8) . . . 2_667 ?