# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Samar Das' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad Andhrapradesh 500046 INDIA ; _publ_contact_author_email SKDSC@UOHYD.ERNET.IN _publ_section_title ; Sulphate anion helices formed by the assistance of a flip-flop water chain ; loop_ _publ_author_name 'Samar Das' 'Pallepogu Raghavaiah' 'Sabbani Supriya' data_final _database_code_depnum_ccdc_archive 'CCDC 293163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H26 N4 O11 S2' _chemical_formula_weight 466.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P_21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 26.946(2) _cell_length_b 9.5581(9) _cell_length_c 7.5203(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.2080(10) _cell_angle_gamma 90.00 _cell_volume 1933.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 28.71 _exptl_crystal_description Plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8753 _exptl_absorpt_correction_T_max 0.9473 _exptl_absorpt_process_details 'SADABS (Sheldrick 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21667 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4646 _reflns_number_gt 4436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (2003)' _computing_cell_refinement 'Bruker SMART (2003)' _computing_data_reduction 'Bruker SAINT-Plus (2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1' _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 w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+1.9546P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4646 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.449686(13) 0.92244(4) 0.19048(5) 0.00844(10) Uani 1 d . . . S2 S 0.049500(13) 0.57636(4) 0.20578(5) 0.00850(10) Uani 1 d . . . O1 O 0.47292(4) 1.03089(12) 0.31011(15) 0.0122(2) Uani 1 d . . . O2 O 0.40960(4) 0.85209(12) 0.28812(15) 0.0122(2) Uani 1 d . . . O3 O 0.42883(4) 0.98656(12) 0.02669(15) 0.0138(2) Uani 1 d . . . O4 O 0.48756(4) 0.81690(12) 0.15281(15) 0.0123(2) Uani 1 d . . . O5 O 0.09141(4) 0.64460(12) 0.31410(15) 0.0123(2) Uani 1 d . . . O6 O 0.02612(4) 0.47228(12) 0.32185(15) 0.0117(2) Uani 1 d . . . O7 O 0.01276(4) 0.68523(12) 0.15358(15) 0.0122(2) Uani 1 d . . . O8 O 0.06868(4) 0.50777(12) 0.05035(15) 0.0138(2) Uani 1 d . . . O9 O 0.24949(5) 0.73790(16) 0.0123(2) 0.0237(3) Uani 1 d . . . O10 O 0.19398(5) 0.60381(15) 0.2681(2) 0.0231(3) Uani 1 d . . . O11 O 0.30476(6) 0.89911(16) 0.2558(2) 0.0268(3) Uani 1 d . . . N1 N 0.42439(5) 0.92380(14) 0.64975(19) 0.0104(3) Uani 1 d . . . N2 N 0.44265(5) 1.21628(15) 0.57033(18) 0.0109(3) Uani 1 d . . . N3 N 0.07736(5) 0.57904(14) 0.67148(19) 0.0107(3) Uani 1 d . . . N4 N 0.05704(5) 0.28544(14) 0.59995(19) 0.0109(3) Uani 1 d . . . C1 C 0.38612(5) 1.02966(16) 0.6661(2) 0.0099(3) Uani 1 d . . . C2 C 0.39425(5) 1.16946(16) 0.6263(2) 0.0104(3) Uani 1 d . . . C3 C 0.35632(6) 1.26654(17) 0.6375(2) 0.0138(3) Uani 1 d . . . H3 H 0.3620 1.3602 0.6118 0.017 Uiso 1 calc R . . C4 C 0.30974(6) 1.22335(18) 0.6872(2) 0.0171(3) Uani 1 d . . . H4 H 0.2842 1.2882 0.6940 0.020 Uiso 1 calc R . . C5 C 0.30138(6) 1.08380(18) 0.7266(2) 0.0168(3) Uani 1 d . . . H5 H 0.2702 1.0551 0.7596 0.020 Uiso 1 calc R . . C6 C 0.33968(6) 0.98682(17) 0.7168(2) 0.0136(3) Uani 1 d . . . H6 H 0.3342 0.8934 0.7441 0.016 Uiso 1 calc R . . C7 C 0.11411(6) 0.47125(16) 0.7187(2) 0.0106(3) Uani 1 d . . . C8 C 0.15952(6) 0.51243(17) 0.7980(2) 0.0139(3) Uani 1 d . . . H8 H 0.1663 0.6069 0.8161 0.017 Uiso 1 calc R . . C9 C 0.19470(6) 0.41251(18) 0.8501(2) 0.0162(3) Uani 1 d . . . H9 H 0.2252 0.4399 0.9031 0.019 Uiso 1 calc R . . C10 C 0.18436(6) 0.27130(18) 0.8229(2) 0.0154(3) Uani 1 d . . . H10 H 0.2076 0.2042 0.8610 0.018 Uiso 1 calc R . . C11 C 0.13946(6) 0.23031(17) 0.7392(2) 0.0132(3) Uani 1 d . . . H11 H 0.1329 0.1360 0.7185 0.016 Uiso 1 calc R . . C12 C 0.10435(5) 0.33057(16) 0.68638(19) 0.0102(3) Uani 1 d . . . H1A H 0.4195(8) 0.852(3) 0.722(3) 0.020(5) Uiso 1 d . . . H1B H 0.4554(10) 0.948(3) 0.678(3) 0.026(6) Uiso 1 d . . . H1C H 0.4241(9) 0.894(3) 0.536(3) 0.022(6) Uiso 1 d . . . H2A H 0.4678(9) 1.209(3) 0.660(3) 0.026(6) Uiso 1 d . . . H2B H 0.4406(9) 1.305(3) 0.538(3) 0.023(6) Uiso 1 d . . . H2C H 0.4537(8) 1.165(2) 0.481(3) 0.017(5) Uiso 1 d . . . H3A H 0.0842(8) 0.659(2) 0.735(3) 0.016(5) Uiso 1 d . . . H3B H 0.0810(9) 0.604(2) 0.557(3) 0.021(6) Uiso 1 d . . . H3C H 0.0457(9) 0.557(3) 0.684(3) 0.022(6) Uiso 1 d . . . H4A H 0.0492(9) 0.338(3) 0.507(3) 0.022(6) Uiso 1 d . . . H4B H 0.0594(8) 0.193(3) 0.567(3) 0.016(5) Uiso 1 d . . . H4C H 0.0320(10) 0.287(3) 0.676(4) 0.030(6) Uiso 1 d . . . H9A H 0.2271(19) 0.788(6) -0.065(7) 0.124(18) Uiso 1 d . . . H9B H 0.2668(18) 0.791(5) 0.080(7) 0.113(17) Uiso 1 d . . . H10A H 0.2028(16) 0.639(5) 0.181(6) 0.084(14) Uiso 1 d . . . H10B H 0.1643(12) 0.612(3) 0.271(4) 0.043(8) Uiso 1 d . . . H11A H 0.3325(13) 0.893(3) 0.263(4) 0.042(8) Uiso 1 d . . . H11B H 0.2939(15) 0.863(4) 0.343(5) 0.074(12) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.00872(18) 0.00757(18) 0.00909(18) -0.00046(12) 0.00103(13) 0.00017(12) S2 0.00868(18) 0.00753(18) 0.00936(18) 0.00047(12) 0.00124(13) 0.00010(12) O1 0.0129(5) 0.0110(5) 0.0128(5) -0.0036(4) 0.0008(4) -0.0016(4) O2 0.0107(5) 0.0124(5) 0.0140(5) -0.0008(4) 0.0039(4) -0.0026(4) O3 0.0160(6) 0.0135(5) 0.0116(5) 0.0015(4) -0.0016(4) 0.0018(4) O4 0.0112(5) 0.0111(5) 0.0149(5) -0.0013(4) 0.0021(4) 0.0022(4) O5 0.0103(5) 0.0132(5) 0.0133(5) 0.0002(4) -0.0008(4) -0.0020(4) O6 0.0120(5) 0.0111(5) 0.0121(5) 0.0030(4) 0.0021(4) -0.0016(4) O7 0.0110(5) 0.0104(5) 0.0151(5) 0.0015(4) -0.0006(4) 0.0018(4) O8 0.0174(6) 0.0129(5) 0.0118(5) -0.0016(4) 0.0058(4) 0.0009(4) O9 0.0198(6) 0.0284(7) 0.0227(7) 0.0014(6) -0.0003(5) 0.0004(5) O10 0.0135(6) 0.0241(7) 0.0318(8) -0.0012(6) 0.0020(5) 0.0007(5) O11 0.0142(7) 0.0300(8) 0.0360(9) 0.0030(6) 0.0003(6) -0.0002(6) N1 0.0100(6) 0.0096(6) 0.0117(6) 0.0006(5) 0.0018(5) 0.0012(5) N2 0.0108(6) 0.0100(6) 0.0120(6) -0.0004(5) 0.0026(5) -0.0007(5) N3 0.0119(6) 0.0085(6) 0.0117(6) -0.0002(5) 0.0008(5) 0.0008(5) N4 0.0096(6) 0.0105(6) 0.0124(6) -0.0001(5) 0.0000(5) -0.0009(5) C1 0.0094(7) 0.0114(7) 0.0091(6) -0.0013(5) 0.0006(5) 0.0010(5) C2 0.0090(6) 0.0123(7) 0.0101(6) -0.0006(5) 0.0014(5) -0.0007(5) C3 0.0135(7) 0.0106(7) 0.0174(8) 0.0012(6) 0.0016(6) 0.0009(6) C4 0.0121(7) 0.0166(8) 0.0228(8) 0.0000(6) 0.0029(6) 0.0034(6) C5 0.0105(7) 0.0179(8) 0.0223(8) -0.0005(6) 0.0037(6) -0.0009(6) C6 0.0122(7) 0.0124(7) 0.0163(7) 0.0005(6) 0.0017(6) -0.0019(6) C7 0.0111(7) 0.0107(7) 0.0101(6) 0.0009(5) 0.0023(5) 0.0021(5) C8 0.0128(7) 0.0133(7) 0.0157(7) -0.0018(6) 0.0006(6) -0.0011(6) C9 0.0099(7) 0.0191(8) 0.0193(8) -0.0014(6) -0.0009(6) 0.0004(6) C10 0.0111(7) 0.0169(8) 0.0182(8) 0.0012(6) 0.0014(6) 0.0042(6) C11 0.0133(7) 0.0114(7) 0.0153(7) 0.0003(6) 0.0030(6) 0.0017(6) C12 0.0094(6) 0.0122(7) 0.0091(6) 0.0002(5) 0.0016(5) -0.0007(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 O3 1.4598(12) . ? S1 O4 1.4736(11) . ? S1 O1 1.4876(11) . ? S1 O2 1.4989(11) . ? S2 O8 1.4597(11) . ? S2 O7 1.4742(11) . ? S2 O6 1.4866(11) . ? S2 O5 1.5037(11) . ? N1 C1 1.4548(19) . ? N2 C2 1.4626(19) . ? N3 C7 1.4591(19) . ? N4 C12 1.4633(19) . ? C1 C2 1.389(2) . ? C1 C6 1.390(2) . ? C2 C3 1.387(2) . ? C3 C4 1.392(2) . ? C4 C5 1.388(2) . ? C5 C6 1.392(2) . ? C7 C8 1.388(2) . ? C7 C12 1.389(2) . ? C8 C9 1.387(2) . ? C9 C10 1.391(2) . ? C10 C11 1.389(2) . ? C11 C12 1.389(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O4 111.29(7) . . ? O3 S1 O1 110.29(7) . . ? O4 S1 O1 108.70(7) . . ? O3 S1 O2 110.35(7) . . ? O4 S1 O2 108.23(7) . . ? O1 S1 O2 107.87(6) . . ? O8 S2 O7 111.49(7) . . ? O8 S2 O6 110.50(7) . . ? O7 S2 O6 109.17(7) . . ? O8 S2 O5 109.86(7) . . ? O7 S2 O5 108.11(7) . . ? O6 S2 O5 107.60(7) . . ? C2 C1 C6 119.84(14) . . ? C2 C1 N1 121.98(13) . . ? C6 C1 N1 118.13(14) . . ? C3 C2 C1 120.32(14) . . ? C3 C2 N2 119.00(14) . . ? C1 C2 N2 120.67(13) . . ? C2 C3 C4 119.78(15) . . ? C5 C4 C3 120.13(15) . . ? C4 C5 C6 119.94(15) . . ? C1 C6 C5 119.99(15) . . ? C8 C7 C12 120.24(14) . . ? C8 C7 N3 118.32(14) . . ? C12 C7 N3 121.45(14) . . ? C9 C8 C7 119.89(15) . . ? C8 C9 C10 119.92(15) . . ? C11 C10 C9 120.16(15) . . ? C10 C11 C12 119.82(15) . . ? C11 C12 C7 119.91(14) . . ? C11 C12 N4 119.09(14) . . ? C7 C12 N4 120.99(14) . . ? 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 N1 H1C O2 0.90(3) 1.92(3) 2.8113(18) 167(2) . N2 H2C O1 0.90(2) 1.91(2) 2.7953(18) 171(2) . N3 H3B O5 0.91(3) 1.90(3) 2.8059(18) 176(2) . N4 H4A O6 0.88(3) 1.97(3) 2.8394(18) 171(2) . O10 H10B O5 0.80(3) 2.03(3) 2.8317(18) 172(3) . O10 H10A O9 0.79(5) 2.06(5) 2.811(2) 159(4) . O9 H9B O11 0.84(5) 1.93(5) 2.764(2) 174(5) . O11 H11A O2 0.75(3) 2.11(3) 2.8575(19) 174(3) . N1 H1B O1 0.88(3) 1.94(3) 2.8001(18) 165(2) 3_676 N2 H2A O4 0.93(3) 1.81(3) 2.7449(18) 174(2) 3_676 N1 H1A O2 0.89(2) 2.03(2) 2.8709(18) 156(2) 4_576 N3 H3A O5 0.91(2) 1.98(2) 2.8680(18) 164(2) 4_576 O11 H11B O9 0.81(4) 2.04(4) 2.824(2) 164(4) 4_576 N2 H2B O3 0.88(3) 2.02(3) 2.8809(19) 165(2) 4_586 N3 H3C O6 0.89(3) 1.95(3) 2.8344(18) 171(2) 3_566 N4 H4C O7 0.91(3) 1.83(3) 2.7280(18) 170(2) 3_566 N4 H4B O8 0.92(2) 1.94(2) 2.8469(18) 168(2) 4_566 O9 H9A O10 0.95(6) 1.82(6) 2.755(2) 170(5) 4_575 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.409 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.093