# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Lasheng Long' _publ_contact_author_email lslong@xmu.edu.cn _publ_author_name 'Lasheng Long' data_complex1-173k _database_code_depnum_ccdc_archive 'CCDC 832174' #TrackingRef 'complex1 at 173K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _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 P21/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 27.0203(14) _cell_length_b 9.5708(5) _cell_length_c 7.5370(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.110(5) _cell_angle_gamma 90.00 _cell_volume 1946.24(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8760 _exptl_absorpt_correction_T_max 0.9668 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 8759 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3806 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+7.6103P] 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 3806 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.093 _refine_ls_shift/su_mean 0.006 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 0.44968(3) 0.57757(10) 0.19119(12) 0.0099(2) Uani 1 1 d . . . O8 O 0.40986(10) 0.6478(3) 0.2874(4) 0.0156(6) Uani 1 1 d . . . O7 O 0.47261(10) 0.4693(3) 0.3094(4) 0.0145(6) Uani 1 1 d . . . O6 O 0.48759(10) 0.6825(3) 0.1536(4) 0.0157(6) Uani 1 1 d . . . O5 O 0.42889(11) 0.5136(3) 0.0282(4) 0.0176(7) Uani 1 1 d . . . N4 N 0.42487(12) 0.5760(4) -0.3498(4) 0.0134(7) Uani 1 1 d . . . H4B H 0.4129 0.6609 -0.3184 0.020 Uiso 1 1 calc R . . H4C H 0.4340 0.5794 -0.4642 0.020 Uiso 1 1 calc R . . H4D H 0.4516 0.5537 -0.2768 0.020 Uiso 1 1 calc R . . N3 N 0.44273(13) 0.2838(4) -0.4292(5) 0.0132(7) Uani 1 1 d . . . C12 C 0.39454(15) 0.3309(4) -0.3730(5) 0.0116(8) Uani 1 1 d . . . C11 C 0.35641(16) 0.2343(5) -0.3625(6) 0.0180(9) Uani 1 1 d . . . H11A H 0.3620 0.1387 -0.3889 0.022 Uiso 1 1 calc R . . C10 C 0.38633(15) 0.4700(4) -0.3339(5) 0.0116(8) Uani 1 1 d . . . C9 C 0.33994(16) 0.5121(5) -0.2828(6) 0.0167(9) Uani 1 1 d . . . H9A H 0.3344 0.6073 -0.2547 0.020 Uiso 1 1 calc R . . C8 C 0.30192(16) 0.4170(5) -0.2725(6) 0.0222(10) Uani 1 1 d . . . H8A H 0.2703 0.4465 -0.2376 0.027 Uiso 1 1 calc R . . C7 C 0.30999(17) 0.2783(5) -0.3132(7) 0.0234(10) Uani 1 1 d . . . H7A H 0.2837 0.2127 -0.3074 0.028 Uiso 1 1 calc R . . S2 S 0.04952(3) 1.57643(10) -0.29387(12) 0.0096(2) Uani 1 1 d . . . O4 O 0.09115(10) 1.6444(3) -0.1864(4) 0.0145(6) Uani 1 1 d . . . O3 O 0.02644(10) 1.4725(3) -0.1788(4) 0.0142(6) Uani 1 1 d . . . O2 O 0.01280(10) 1.6842(3) -0.3452(4) 0.0146(6) Uani 1 1 d . . . O1 O 0.06875(11) 1.5085(3) -0.4481(4) 0.0172(7) Uani 1 1 d . . . N2 N 0.07701(12) 0.9210(4) -0.3283(4) 0.0118(7) Uani 1 1 d . . . H2B H 0.0896 0.8356 -0.2977 0.018 Uiso 1 1 calc R . . H2C H 0.0693 0.9232 -0.4473 0.018 Uiso 1 1 calc R . . H2D H 0.0492 0.9372 -0.2685 0.018 Uiso 1 1 calc R . . N1 N 0.05692(13) 1.2149(4) -0.3997(5) 0.0116(7) Uani 1 1 d . . . C6 C 0.11387(14) 1.0286(4) -0.2825(5) 0.0104(8) Uani 1 1 d . . . C5 C 0.13941(16) 1.2685(5) -0.2643(6) 0.0160(9) Uani 1 1 d . . . H5A H 0.1329 1.3647 -0.2860 0.019 Uiso 1 1 calc R . . C4 C 0.19413(16) 1.0878(5) -0.1546(6) 0.0216(10) Uani 1 1 d . . . H4A H 0.2253 1.0599 -0.1022 0.026 Uiso 1 1 calc R . . C3 C 0.10420(14) 1.1694(4) -0.3160(5) 0.0107(8) Uani 1 1 d . . . C2 C 0.15916(16) 0.9883(5) -0.2037(6) 0.0176(9) Uani 1 1 d . . . H2A H 0.1661 0.8922 -0.1836 0.021 Uiso 1 1 calc R . . C1 C 0.18402(16) 1.2282(5) -0.1812(6) 0.0196(10) Uani 1 1 d . . . H1A H 0.2077 1.2967 -0.1425 0.024 Uiso 1 1 calc R . . O3W O 0.24950(14) 0.7586(4) 0.0122(5) 0.0345(9) Uani 1 1 d . . . H3WB H 0.2336 0.8205 0.0666 0.041 Uiso 1 1 d R . . H3WA H 0.2676 0.7981 -0.0617 0.041 Uiso 1 1 d R . . O2W O 0.30502(13) 0.6009(4) 0.2576(5) 0.0368(9) Uani 1 1 d . . . H2WA H 0.3379 0.6066 0.2724 0.044 Uiso 1 1 d R . . H2WB H 0.2929 0.6548 0.1762 0.044 Uiso 1 1 d R . . O1W O 0.19389(12) 0.8961(4) 0.2650(5) 0.0311(8) Uani 1 1 d . . . H1WA H 0.1607 0.8897 0.2808 0.037 Uiso 1 1 d R . . H1WB H 0.2079 0.8744 0.3649 0.037 Uiso 1 1 d R . . H1B H 0.0290(17) 1.203(5) -0.325(6) 0.010(11) Uiso 1 1 d . . . H1C H 0.0605(18) 1.308(6) -0.437(7) 0.025(13) Uiso 1 1 d . . . H1D H 0.0509(18) 1.172(6) -0.488(7) 0.017(13) Uiso 1 1 d . . . H3A H 0.452(2) 0.327(7) -0.524(9) 0.048(19) Uiso 1 1 d . . . H3B H 0.4392(19) 0.191(7) -0.462(7) 0.031(15) Uiso 1 1 d . . . H3C H 0.471(2) 0.297(6) -0.335(8) 0.038(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0115(5) 0.0075(5) 0.0106(5) 0.0006(4) 0.0007(4) -0.0007(4) O8 0.0130(15) 0.0146(15) 0.0195(15) 0.0010(13) 0.0037(11) 0.0028(12) O7 0.0154(15) 0.0105(14) 0.0176(15) 0.0057(12) 0.0015(11) 0.0023(12) O6 0.0150(15) 0.0136(15) 0.0185(15) 0.0030(13) 0.0017(12) -0.0044(12) O5 0.0244(17) 0.0152(15) 0.0131(14) -0.0032(12) -0.0018(12) -0.0019(13) N4 0.0161(18) 0.0130(17) 0.0111(16) 0.0004(15) 0.0012(13) -0.0015(15) N3 0.0123(18) 0.0126(19) 0.0150(18) 0.0006(16) 0.0029(14) 0.0011(15) C12 0.012(2) 0.012(2) 0.0109(19) 0.0022(16) 0.0031(15) 0.0001(16) C11 0.022(2) 0.010(2) 0.023(2) -0.0005(18) 0.0028(18) -0.0016(18) C10 0.012(2) 0.011(2) 0.0114(19) 0.0020(16) -0.0017(15) -0.0006(16) C9 0.017(2) 0.013(2) 0.020(2) 0.0000(18) 0.0017(17) 0.0027(18) C8 0.013(2) 0.022(2) 0.032(3) -0.001(2) 0.0040(18) 0.003(2) C7 0.015(2) 0.019(2) 0.036(3) 0.003(2) 0.0038(19) -0.0046(19) S2 0.0104(5) 0.0078(5) 0.0106(5) 0.0010(4) 0.0020(4) 0.0002(4) O4 0.0121(14) 0.0126(15) 0.0185(15) 0.0008(12) -0.0019(11) -0.0003(12) O3 0.0140(15) 0.0134(15) 0.0151(14) 0.0047(12) 0.0009(11) -0.0013(12) O2 0.0128(14) 0.0120(15) 0.0187(15) 0.0020(12) -0.0007(11) 0.0034(12) O1 0.0249(17) 0.0166(16) 0.0106(14) -0.0026(12) 0.0071(12) 0.0020(13) N2 0.0160(17) 0.0087(17) 0.0106(16) 0.0013(14) 0.0012(13) -0.0009(14) N1 0.0122(18) 0.0109(18) 0.0116(18) -0.0017(16) -0.0008(14) 0.0002(15) C6 0.0097(19) 0.010(2) 0.0115(19) -0.0015(16) 0.0036(15) -0.0021(16) C5 0.015(2) 0.011(2) 0.021(2) 0.0006(18) 0.0034(17) -0.0006(17) C4 0.011(2) 0.027(3) 0.027(2) 0.003(2) -0.0014(18) -0.0010(19) C3 0.0093(19) 0.014(2) 0.0088(18) -0.0004(16) 0.0019(15) 0.0000(16) C2 0.020(2) 0.013(2) 0.020(2) 0.0023(18) 0.0013(17) 0.0029(18) C1 0.011(2) 0.021(2) 0.026(2) -0.001(2) 0.0003(17) -0.0063(18) O3W 0.0308(19) 0.037(2) 0.036(2) -0.0009(17) 0.0082(16) -0.0004(17) O2W 0.0182(18) 0.038(2) 0.053(2) 0.0048(19) -0.0058(16) 0.0003(16) O1W 0.0192(17) 0.030(2) 0.043(2) 0.0072(17) -0.0007(15) -0.0013(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. ; 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 O5 1.458(3) . ? S1 O6 1.473(3) . ? S1 O7 1.480(3) . ? S1 O8 1.490(3) . ? N4 C10 1.463(5) . ? N3 C12 1.462(5) . ? C12 C10 1.384(6) . ? C12 C11 1.390(6) . ? C11 C7 1.393(6) . ? C10 C9 1.391(6) . ? C9 C8 1.378(6) . ? C8 C7 1.382(7) . ? S2 O1 1.453(3) . ? S2 O2 1.469(3) . ? S2 O3 1.480(3) . ? S2 O4 1.499(3) . ? N2 C6 1.461(5) . ? N1 C3 1.460(5) . ? C6 C2 1.385(6) . ? C6 C3 1.393(6) . ? C5 C1 1.383(6) . ? C5 C3 1.384(6) . ? C4 C2 1.378(6) . ? C4 C1 1.384(7) . ? 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 O5 S1 O6 111.37(18) . . ? O5 S1 O7 110.05(18) . . ? O6 S1 O7 108.67(17) . . ? O5 S1 O8 110.14(18) . . ? O6 S1 O8 108.32(17) . . ? O7 S1 O8 108.20(17) . . ? C10 C12 C11 120.0(4) . . ? C10 C12 N3 120.9(4) . . ? C11 C12 N3 119.1(4) . . ? C12 C11 C7 119.6(4) . . ? C12 C10 C9 119.6(4) . . ? C12 C10 N4 121.8(4) . . ? C9 C10 N4 118.6(4) . . ? C8 C9 C10 120.7(4) . . ? C9 C8 C7 119.6(4) . . ? C8 C7 C11 120.4(4) . . ? O1 S2 O2 111.69(18) . . ? O1 S2 O3 110.40(18) . . ? O2 S2 O3 109.06(16) . . ? O1 S2 O4 109.68(17) . . ? O2 S2 O4 108.29(17) . . ? O3 S2 O4 107.62(17) . . ? C2 C6 C3 120.0(4) . . ? C2 C6 N2 118.7(4) . . ? C3 C6 N2 121.3(3) . . ? C1 C5 C3 120.4(4) . . ? C2 C4 C1 120.3(4) . . ? C6 C3 C5 119.5(4) . . ? C6 C3 N1 121.2(4) . . ? C5 C3 N1 119.3(4) . . ? C4 C2 C6 120.0(4) . . ? C4 C1 C5 119.8(4) . . ? 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 N4 H4B O8 0.91 2.00 2.875(5) 160.6 4_575 N4 H4C O8 0.91 2.06 2.827(4) 141.7 1_554 N4 H4C O7 0.91 2.30 3.109(4) 147.4 1_554 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.598 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.096 # Attachment 'complex1 at 265K.cif' data_complex1-265k _database_code_depnum_ccdc_archive 'CCDC 832175' #TrackingRef 'complex1 at 265K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _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 P21/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 27.0843(12) _cell_length_b 9.6042(5) _cell_length_c 7.5562(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.993(4) _cell_angle_gamma 90.00 _cell_volume 1962.86(17) _cell_formula_units_Z 4 _cell_measurement_temperature 265(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8770 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 265(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 9745 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3847 _reflns_number_gt 2797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+8.1402P] 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 3847 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.2139 _refine_ls_wR_factor_gt 0.1858 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 0.44949(4) 0.57824(13) 0.19258(16) 0.0138(3) Uani 1 1 d . . . O8 O 0.40997(13) 0.6497(4) 0.2865(5) 0.0240(9) Uani 1 1 d . . . O7 O 0.47183(14) 0.4709(4) 0.3115(5) 0.0252(9) Uani 1 1 d . . . O6 O 0.48764(13) 0.6811(4) 0.1551(5) 0.0221(8) Uani 1 1 d . . . O5 O 0.42933(15) 0.5138(4) 0.0303(5) 0.0256(9) Uani 1 1 d . . . N4 N 0.42562(16) 0.5751(5) -0.3472(6) 0.0190(9) Uani 1 1 d . . . H4B H 0.4141 0.6580 -0.3166 0.029 Uiso 1 1 calc R . . H4C H 0.4349 0.5785 -0.4584 0.029 Uiso 1 1 calc R . . H4D H 0.4515 0.5528 -0.2754 0.029 Uiso 1 1 calc R . . N3 N 0.44287(15) 0.2842(5) -0.4290(6) 0.0166(9) Uani 1 1 d . . . H3A H 0.4523 0.3382 -0.5168 0.025 Uiso 1 1 calc R . . H3B H 0.4405 0.1965 -0.4665 0.025 Uiso 1 1 calc R . . H3C H 0.4651 0.2894 -0.3382 0.025 Uiso 1 1 calc R . . C12 C 0.39501(18) 0.3310(5) -0.3725(6) 0.0156(10) Uani 1 1 d . . . C11 C 0.3569(2) 0.2361(6) -0.3646(8) 0.0254(13) Uani 1 1 d . . . H11A H 0.3619 0.1432 -0.3932 0.030 Uiso 1 1 calc R . . C10 C 0.38679(18) 0.4701(5) -0.3327(7) 0.0160(10) Uani 1 1 d . . . C9 C 0.3407(2) 0.5121(6) -0.2820(8) 0.0244(12) Uani 1 1 d . . . H9A H 0.3354 0.6046 -0.2520 0.029 Uiso 1 1 calc R . . C8 C 0.3028(2) 0.4174(7) -0.2760(9) 0.0334(15) Uani 1 1 d . . . H8A H 0.2716 0.4468 -0.2461 0.040 Uiso 1 1 calc R . . C7 C 0.3106(2) 0.2806(7) -0.3135(10) 0.0363(16) Uani 1 1 d . . . H7A H 0.2851 0.2166 -0.3051 0.044 Uiso 1 1 calc R . . S2 S 0.04960(4) 1.57641(13) -0.29355(16) 0.0133(3) Uani 1 1 d . . . O4 O 0.09085(13) 1.6455(4) -0.1876(5) 0.0213(8) Uani 1 1 d . . . O3 O 0.02704(13) 1.4722(4) -0.1785(5) 0.0215(8) Uani 1 1 d . . . O2 O 0.01264(13) 1.6840(4) -0.3441(5) 0.0200(8) Uani 1 1 d . . . O1 O 0.06846(15) 1.5098(4) -0.4474(5) 0.0261(9) Uani 1 1 d . . . N2 N 0.07657(16) 0.9216(4) -0.3281(6) 0.0172(9) Uani 1 1 d . . . H2B H 0.0891 0.8388 -0.2977 0.026 Uiso 1 1 calc R . . H2C H 0.0688 0.9228 -0.4440 0.026 Uiso 1 1 calc R . . H2D H 0.0495 0.9371 -0.2689 0.026 Uiso 1 1 calc R . . N1 N 0.05660(15) 1.2149(4) -0.4013(6) 0.0161(9) Uani 1 1 d . . . H1B H 0.0333 1.2092 -0.3228 0.024 Uiso 1 1 calc R . . H1C H 0.0483 1.1614 -0.4944 0.024 Uiso 1 1 calc R . . H1D H 0.0594 1.3029 -0.4366 0.024 Uiso 1 1 calc R . . C6 C 0.11321(18) 1.0304(5) -0.2848(6) 0.0148(10) Uani 1 1 d . . . C5 C 0.1389(2) 1.2682(6) -0.2718(8) 0.0240(12) Uani 1 1 d . . . H5A H 0.1326 1.3619 -0.2942 0.029 Uiso 1 1 calc R . . C4 C 0.1935(2) 1.0874(7) -0.1620(9) 0.0329(15) Uani 1 1 d . . . H4A H 0.2239 1.0603 -0.1108 0.040 Uiso 1 1 calc R . . C3 C 0.10387(18) 1.1677(5) -0.3193(6) 0.0150(10) Uani 1 1 d . . . C2 C 0.1585(2) 0.9884(6) -0.2093(7) 0.0249(12) Uani 1 1 d . . . H2A H 0.1651 0.8944 -0.1908 0.030 Uiso 1 1 calc R . . C1 C 0.1835(2) 1.2268(6) -0.1905(8) 0.0281(13) Uani 1 1 d . . . H1A H 0.2069 1.2933 -0.1548 0.034 Uiso 1 1 calc R . . O3W O 0.24959(19) 0.7564(6) 0.0084(7) 0.0513(13) Uani 1 1 d . . . H3WB H 0.2337 0.8183 0.0628 0.062 Uiso 1 1 d R . . H3WA H 0.2677 0.7959 -0.0656 0.062 Uiso 1 1 d R . . O2W O 0.30550(17) 0.6011(6) 0.2581(7) 0.0525(14) Uani 1 1 d . . . H2WA H 0.3384 0.6068 0.2730 0.063 Uiso 1 1 d R . . H2WB H 0.2934 0.6550 0.1768 0.063 Uiso 1 1 d R . . O1W O 0.19339(17) 0.8971(5) 0.2610(7) 0.0484(13) Uani 1 1 d . . . H1WA H 0.1602 0.8907 0.2768 0.058 Uiso 1 1 d R . . H1WB H 0.2074 0.8754 0.3609 0.058 Uiso 1 1 d 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 0.0164(6) 0.0101(6) 0.0150(6) 0.0016(5) 0.0006(4) -0.0007(5) O8 0.0187(19) 0.024(2) 0.030(2) -0.0010(18) 0.0073(16) 0.0022(16) O7 0.026(2) 0.020(2) 0.029(2) 0.0116(17) -0.0001(16) 0.0035(17) O6 0.0214(19) 0.019(2) 0.027(2) 0.0048(17) 0.0029(15) -0.0058(16) O5 0.035(2) 0.023(2) 0.0183(19) -0.0037(17) -0.0043(16) -0.0051(18) N4 0.020(2) 0.018(2) 0.019(2) -0.0037(19) 0.0023(17) -0.0025(19) N3 0.019(2) 0.014(2) 0.017(2) 0.0004(18) 0.0015(17) 0.0010(18) C12 0.017(2) 0.017(3) 0.013(2) 0.002(2) 0.0025(19) 0.001(2) C11 0.023(3) 0.016(3) 0.038(3) -0.003(3) 0.002(2) -0.002(2) C10 0.019(3) 0.013(3) 0.015(2) 0.003(2) -0.0003(19) 0.000(2) C9 0.022(3) 0.019(3) 0.033(3) 0.001(2) 0.003(2) 0.002(2) C8 0.020(3) 0.033(4) 0.048(4) -0.002(3) 0.008(3) 0.002(3) C7 0.020(3) 0.026(3) 0.064(5) 0.004(3) 0.007(3) -0.005(3) S2 0.0151(6) 0.0105(6) 0.0144(6) 0.0017(5) 0.0011(4) 0.0001(5) O4 0.0190(18) 0.020(2) 0.024(2) -0.0008(16) -0.0062(15) -0.0030(16) O3 0.0219(19) 0.022(2) 0.0206(19) 0.0080(16) -0.0002(15) -0.0006(16) O2 0.0202(18) 0.0159(19) 0.024(2) 0.0021(16) -0.0012(15) 0.0080(15) O1 0.035(2) 0.029(2) 0.0147(18) -0.0044(17) 0.0074(16) 0.0046(18) N2 0.021(2) 0.013(2) 0.018(2) 0.0064(18) -0.0009(17) -0.0055(18) N1 0.016(2) 0.012(2) 0.020(2) 0.0010(18) -0.0009(17) -0.0018(17) C6 0.016(2) 0.015(3) 0.013(2) -0.003(2) 0.0023(19) -0.002(2) C5 0.021(3) 0.019(3) 0.032(3) -0.005(2) 0.001(2) -0.004(2) C4 0.018(3) 0.040(4) 0.040(4) 0.007(3) -0.005(2) -0.006(3) C3 0.015(2) 0.017(3) 0.013(2) 0.003(2) 0.0035(18) -0.002(2) C2 0.026(3) 0.018(3) 0.030(3) 0.005(2) -0.002(2) 0.005(2) C1 0.017(3) 0.028(3) 0.040(3) -0.001(3) -0.001(2) -0.010(2) O3W 0.042(3) 0.060(3) 0.053(3) -0.003(3) 0.004(2) 0.001(2) O2W 0.026(2) 0.060(4) 0.071(4) 0.006(3) -0.005(2) 0.000(2) O1W 0.028(2) 0.050(3) 0.066(3) 0.012(3) 0.000(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.454(4) . ? S1 O6 1.468(4) . ? S1 O7 1.476(4) . ? S1 O8 1.483(4) . ? N4 C10 1.466(7) . ? N3 C12 1.457(6) . ? C12 C11 1.381(8) . ? C12 C10 1.389(7) . ? C11 C7 1.396(8) . ? C10 C9 1.385(7) . ? C9 C8 1.373(8) . ? C8 C7 1.363(9) . ? S2 O1 1.443(4) . ? S2 O2 1.475(4) . ? S2 O3 1.478(4) . ? S2 O4 1.495(4) . ? N2 C6 1.466(6) . ? N1 C3 1.465(6) . ? C6 C3 1.365(7) . ? C6 C2 1.384(7) . ? C5 C1 1.384(8) . ? C5 C3 1.388(7) . ? C4 C2 1.377(8) . ? C4 C1 1.380(9) . ? 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 O5 S1 O6 111.2(2) . . ? O5 S1 O7 109.9(2) . . ? O6 S1 O7 108.5(2) . . ? O5 S1 O8 110.6(2) . . ? O6 S1 O8 108.3(2) . . ? O7 S1 O8 108.4(2) . . ? C11 C12 C10 119.7(5) . . ? C11 C12 N3 119.2(5) . . ? C10 C12 N3 121.0(4) . . ? C12 C11 C7 119.6(5) . . ? C9 C10 C12 119.8(5) . . ? C9 C10 N4 118.7(5) . . ? C12 C10 N4 121.5(4) . . ? C8 C9 C10 120.1(5) . . ? C7 C8 C9 120.5(6) . . ? C8 C7 C11 120.2(6) . . ? O1 S2 O2 111.5(2) . . ? O1 S2 O3 110.4(2) . . ? O2 S2 O3 109.3(2) . . ? O1 S2 O4 110.0(2) . . ? O2 S2 O4 107.8(2) . . ? O3 S2 O4 107.8(2) . . ? C3 C6 C2 120.8(5) . . ? C3 C6 N2 122.0(4) . . ? C2 C6 N2 117.3(5) . . ? C1 C5 C3 118.9(5) . . ? C2 C4 C1 120.2(5) . . ? C6 C3 C5 120.3(5) . . ? C6 C3 N1 121.9(4) . . ? C5 C3 N1 117.7(5) . . ? C4 C2 C6 119.2(5) . . ? C4 C1 C5 120.5(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O8 0.89 2.01 2.869(6) 161.8 4_575 N4 H4B S1 0.89 2.71 3.401(5) 135.6 4_575 O3W H3WA O2W 0.85 1.99 2.835(8) 175.4 4_575 N4 H4C O8 0.89 2.12 2.869(6) 141.0 1_554 N4 H4C O7 0.89 2.30 3.092(6) 148.7 1_554 N3 H3A O7 0.89 1.91 2.799(6) 173.8 1_554 N4 H4D O7 0.89 2.12 2.812(6) 133.8 3_665 N3 H3C O6 0.89 1.86 2.744(6) 174.2 3_665 N4 H4D O5 0.89 2.45 2.909(6) 112.9 . N3 H3B O5 0.89 2.04 2.900(6) 161.5 4_565 N2 H2B O4 0.89 2.03 2.875(6) 157.0 1_545 N2 H2C O4 0.89 2.07 2.838(6) 143.7 4_585 N2 H2C O3 0.89 2.29 3.079(6) 148.3 4_585 N1 H1C O3 0.89 1.96 2.843(6) 173.0 4_585 N2 H2D O3 0.89 2.12 2.851(6) 139.0 2_544 N1 H1B O2 0.89 1.83 2.721(6) 175.5 2_544 N2 H2D O1 0.89 2.51 2.971(6) 112.9 4_586 O1W H1WA O4 0.91 1.94 2.854(6) 173.5 4_586 O3W H3WB O1W 0.85 2.04 2.845(8) 156.2 . O2W H2WA O8 0.89 1.98 2.864(6) 170.5 . O2W H2WB O3W 0.86 1.95 2.789(7) 165.0 . O1W H1WB O3W 0.85 2.00 2.773(7) 149.4 4_576 N1 H1D O1 0.89 2.01 2.874(6) 164.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.672 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.160 # Attachment 'complex1 at 280K.cif' data_complex1-280k _database_code_depnum_ccdc_archive 'CCDC 832176' #TrackingRef 'complex1 at 280K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _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 P21/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 27.1493(13) _cell_length_b 9.5940(5) _cell_length_c 7.5415(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.860(4) _cell_angle_gamma 90.00 _cell_volume 1961.89(17) _cell_formula_units_Z 4 _cell_measurement_temperature 280(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8769 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 280(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 8556 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3842 _reflns_number_gt 2765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+12.4236P] 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 0.0034(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3842 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.1991 _refine_ls_wR_factor_gt 0.1916 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.006 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 0.44941(5) 0.57845(14) 0.19317(17) 0.0162(3) Uani 1 1 d . . . O8 O 0.40977(14) 0.6502(4) 0.2852(6) 0.0275(10) Uani 1 1 d . . . O7 O 0.47152(15) 0.4712(4) 0.3127(5) 0.0287(10) Uani 1 1 d . . . O6 O 0.48755(14) 0.6804(4) 0.1557(5) 0.0251(9) Uani 1 1 d . . . O5 O 0.42958(16) 0.5130(4) 0.0301(5) 0.0297(10) Uani 1 1 d . . . N4 N 0.42576(17) 0.5738(5) -0.3456(6) 0.0216(10) Uani 1 1 d . . . H4B H 0.4144 0.6570 -0.3151 0.032 Uiso 1 1 calc R . . H4C H 0.4353 0.5771 -0.4567 0.032 Uiso 1 1 calc R . . H4D H 0.4513 0.5508 -0.2730 0.032 Uiso 1 1 calc R . . N3 N 0.44265(16) 0.2843(5) -0.4290(6) 0.0198(10) Uani 1 1 d . . . H3A H 0.4538 0.3445 -0.5074 0.030 Uiso 1 1 calc R . . H3B H 0.4395 0.2005 -0.4789 0.030 Uiso 1 1 calc R . . H3C H 0.4639 0.2794 -0.3353 0.030 Uiso 1 1 calc R . . C12 C 0.3950(2) 0.3309(6) -0.3725(7) 0.0184(11) Uani 1 1 d . . . C11 C 0.3569(2) 0.2356(7) -0.3633(8) 0.0293(14) Uani 1 1 d . . . H11A H 0.3621 0.1421 -0.3889 0.035 Uiso 1 1 calc R . . C10 C 0.3869(2) 0.4699(6) -0.3326(7) 0.0188(12) Uani 1 1 d . . . C9 C 0.3410(2) 0.5127(6) -0.2822(8) 0.0260(13) Uani 1 1 d . . . H9A H 0.3357 0.6055 -0.2528 0.031 Uiso 1 1 calc R . . C8 C 0.3030(2) 0.4174(7) -0.2755(10) 0.0364(16) Uani 1 1 d . . . H8A H 0.2720 0.4465 -0.2436 0.044 Uiso 1 1 calc R . . C7 C 0.3108(2) 0.2811(7) -0.3156(10) 0.0392(17) Uani 1 1 d . . . H7A H 0.2849 0.2177 -0.3110 0.047 Uiso 1 1 calc R . . S2 S 0.04970(5) 1.57690(14) -0.29339(17) 0.0154(3) Uani 1 1 d . . . O4 O 0.09066(14) 1.6453(4) -0.1874(5) 0.0236(9) Uani 1 1 d . . . O3 O 0.02735(14) 1.4730(4) -0.1780(5) 0.0234(9) Uani 1 1 d . . . O2 O 0.01262(14) 1.6830(4) -0.3440(5) 0.0224(9) Uani 1 1 d . . . O1 O 0.06862(15) 1.5096(4) -0.4474(5) 0.0279(10) Uani 1 1 d . . . N2 N 0.07626(17) 0.9219(5) -0.3276(6) 0.0198(10) Uani 1 1 d . . . H2B H 0.0884 0.8385 -0.2978 0.030 Uiso 1 1 calc R . . H2C H 0.0682 0.9234 -0.4435 0.030 Uiso 1 1 calc R . . H2D H 0.0495 0.9385 -0.2672 0.030 Uiso 1 1 calc R . . N1 N 0.05661(16) 1.2144(5) -0.4022(6) 0.0188(10) Uani 1 1 d . . . H1B H 0.0343 1.2199 -0.3198 0.028 Uiso 1 1 calc R . . H1C H 0.0464 1.1536 -0.4854 0.028 Uiso 1 1 calc R . . H1D H 0.0604 1.2978 -0.4513 0.028 Uiso 1 1 calc R . . C6 C 0.11330(19) 1.0288(6) -0.2857(7) 0.0174(11) Uani 1 1 d . . . C5 C 0.1388(2) 1.2675(6) -0.2733(8) 0.0255(13) Uani 1 1 d . . . H5A H 0.1325 1.3613 -0.2959 0.031 Uiso 1 1 calc R . . C4 C 0.1933(2) 1.0872(8) -0.1650(9) 0.0359(16) Uani 1 1 d . . . H4A H 0.2239 1.0598 -0.1161 0.043 Uiso 1 1 calc R . . C3 C 0.10372(19) 1.1681(6) -0.3202(7) 0.0177(11) Uani 1 1 d . . . C2 C 0.1582(2) 0.9884(6) -0.2097(8) 0.0271(13) Uani 1 1 d . . . H2A H 0.1648 0.8945 -0.1887 0.033 Uiso 1 1 calc R . . C1 C 0.1834(2) 1.2267(7) -0.1923(9) 0.0325(15) Uani 1 1 d . . . H1A H 0.2067 1.2934 -0.1564 0.039 Uiso 1 1 calc R . . O3W O 0.2494(2) 0.7555(6) 0.0095(8) 0.0580(15) Uani 1 1 d . . . H3WB H 0.2336 0.8173 0.0639 0.070 Uiso 1 1 d R . . H3WA H 0.2676 0.7950 -0.0645 0.070 Uiso 1 1 d R . . O2W O 0.30542(18) 0.6016(6) 0.2554(8) 0.0581(16) Uani 1 1 d . . . H2WA H 0.3383 0.6072 0.2702 0.070 Uiso 1 1 d R . . H2WB H 0.2933 0.6554 0.1740 0.070 Uiso 1 1 d R . . O1W O 0.19331(18) 0.8975(6) 0.2590(8) 0.0520(15) Uani 1 1 d . . . H1WA H 0.1602 0.8911 0.2748 0.062 Uiso 1 1 d R . . H1WB H 0.2073 0.8758 0.3588 0.062 Uiso 1 1 d 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 0.0190(7) 0.0129(7) 0.0167(6) 0.0011(5) 0.0005(5) -0.0007(5) O8 0.022(2) 0.028(2) 0.034(2) -0.0010(19) 0.0088(17) 0.0027(18) O7 0.033(2) 0.022(2) 0.031(2) 0.0149(18) -0.0008(18) 0.0004(18) O6 0.023(2) 0.024(2) 0.028(2) 0.0037(18) 0.0025(16) -0.0071(17) O5 0.042(3) 0.028(2) 0.018(2) -0.0072(18) -0.0054(18) -0.005(2) N4 0.024(2) 0.020(2) 0.021(2) -0.005(2) 0.0030(19) -0.003(2) N3 0.020(2) 0.018(2) 0.021(2) 0.0007(19) 0.0009(19) 0.0017(19) C12 0.020(3) 0.021(3) 0.015(3) 0.003(2) 0.001(2) -0.002(2) C11 0.028(3) 0.021(3) 0.039(4) 0.000(3) 0.003(3) -0.006(3) C10 0.020(3) 0.018(3) 0.018(3) 0.002(2) -0.001(2) 0.001(2) C9 0.026(3) 0.020(3) 0.032(3) 0.000(3) 0.003(2) 0.004(3) C8 0.022(3) 0.032(4) 0.057(4) -0.003(3) 0.009(3) 0.001(3) C7 0.021(3) 0.033(4) 0.064(5) 0.000(3) 0.008(3) -0.009(3) S2 0.0178(7) 0.0132(7) 0.0154(6) 0.0013(5) 0.0014(5) 0.0004(5) O4 0.023(2) 0.020(2) 0.027(2) -0.0013(17) -0.0053(16) -0.0025(17) O3 0.025(2) 0.023(2) 0.023(2) 0.0102(17) 0.0022(16) -0.0019(17) O2 0.022(2) 0.020(2) 0.025(2) 0.0036(17) -0.0021(16) 0.0051(16) O1 0.038(2) 0.030(2) 0.017(2) -0.0041(18) 0.0111(17) 0.004(2) N2 0.025(2) 0.018(2) 0.016(2) 0.0037(19) -0.0007(18) -0.001(2) N1 0.018(2) 0.019(2) 0.019(2) -0.0026(19) -0.0004(18) 0.0011(19) C6 0.019(3) 0.019(3) 0.014(3) -0.001(2) 0.004(2) -0.003(2) C5 0.025(3) 0.017(3) 0.035(3) -0.002(3) 0.002(2) -0.004(2) C4 0.018(3) 0.048(4) 0.040(4) 0.006(3) -0.006(3) -0.004(3) C3 0.016(3) 0.021(3) 0.016(3) -0.002(2) 0.003(2) -0.001(2) C2 0.031(3) 0.021(3) 0.030(3) 0.006(3) 0.002(3) 0.006(3) C1 0.018(3) 0.037(4) 0.042(4) 0.002(3) -0.003(3) -0.012(3) O3W 0.046(3) 0.067(4) 0.061(4) 0.000(3) 0.007(3) 0.002(3) O2W 0.029(3) 0.068(4) 0.076(4) 0.009(3) -0.008(3) 0.001(3) O1W 0.032(3) 0.053(3) 0.071(4) 0.012(3) 0.000(3) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.459(4) . ? S1 O6 1.462(4) . ? S1 O7 1.476(4) . ? S1 O8 1.479(4) . ? N4 C10 1.459(7) . ? N3 C12 1.452(7) . ? C12 C11 1.385(8) . ? C12 C10 1.386(8) . ? C11 C7 1.391(9) . ? C10 C9 1.384(8) . ? C9 C8 1.381(9) . ? C8 C7 1.362(10) . ? S2 O1 1.445(4) . ? S2 O2 1.469(4) . ? S2 O3 1.474(4) . ? S2 O4 1.489(4) . ? N2 C6 1.460(7) . ? N1 C3 1.462(7) . ? C6 C2 1.378(8) . ? C6 C3 1.383(8) . ? C5 C1 1.386(9) . ? C5 C3 1.381(8) . ? C4 C1 1.379(10) . ? C4 C2 1.374(9) . ? 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 O5 S1 O6 111.1(2) . . ? O5 S1 O7 109.7(3) . . ? O6 S1 O7 108.3(2) . . ? O5 S1 O8 110.4(3) . . ? O6 S1 O8 108.6(2) . . ? O7 S1 O8 108.7(2) . . ? C11 C12 C10 119.8(5) . . ? C11 C12 N3 119.3(5) . . ? C10 C12 N3 120.9(5) . . ? C12 C11 C7 119.4(6) . . ? C9 C10 C12 120.0(5) . . ? C9 C10 N4 118.7(5) . . ? C12 C10 N4 121.3(5) . . ? C10 C9 C8 119.9(6) . . ? C7 C8 C9 120.2(6) . . ? C8 C7 C11 120.7(6) . . ? O1 S2 O2 111.5(2) . . ? O1 S2 O3 110.2(2) . . ? O2 S2 O3 109.0(2) . . ? O1 S2 O4 110.0(2) . . ? O2 S2 O4 108.5(2) . . ? O3 S2 O4 107.4(2) . . ? C2 C6 C3 120.3(5) . . ? C2 C6 N2 118.6(5) . . ? C3 C6 N2 121.1(5) . . ? C1 C5 C3 119.6(6) . . ? C1 C4 C2 120.3(6) . . ? C6 C3 C5 119.9(5) . . ? C6 C3 N1 121.7(5) . . ? C5 C3 N1 118.4(5) . . ? C6 C2 C4 119.8(6) . . ? C4 C1 C5 120.0(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O8 0.89 2.01 2.866(6) 162.5 4_575 O3W H3WA O2W 0.85 2.01 2.855(8) 175.2 4_575 N4 H4C O8 0.89 2.15 2.890(6) 140.1 1_554 N4 H4C O7 0.89 2.28 3.077(6) 149.3 1_554 N3 H3A O7 0.89 1.90 2.788(6) 174.3 1_554 N4 H4D O7 0.89 2.14 2.821(6) 132.6 3_665 N3 H3C O6 0.89 1.88 2.750(6) 164.3 3_665 N4 H4D O5 0.89 2.42 2.890(6) 113.6 . N3 H3B O5 0.89 2.07 2.890(6) 153.0 4_565 N2 H2B O4 0.89 2.03 2.876(6) 157.9 1_545 N2 H2C O4 0.89 2.07 2.835(6) 142.8 4_585 N2 H2C O3 0.89 2.27 3.068(6) 149.2 4_585 N1 H1C O3 0.89 1.94 2.832(6) 176.1 4_585 N2 H2D O3 0.89 2.13 2.858(6) 138.0 2_544 N1 H1B O2 0.89 1.85 2.724(6) 165.5 2_544 N2 H2D O1 0.89 2.49 2.959(6) 113.3 4_586 O1W H1WA O4 0.92 1.95 2.865(6) 173.5 4_586 O3W H3WB O1W 0.85 2.03 2.830(8) 156.8 . O2W H2WA O8 0.90 1.98 2.869(6) 170.6 . O2W H2WB O3W 0.85 1.93 2.765(8) 164.4 . O1W H1WB O3W 0.85 2.01 2.785(8) 150.1 4_576 N1 H1D O1 0.89 2.04 2.873(6) 154.5 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.496 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.103 # Attachment 'complex1 at 286K.cif' data_complex1-286k _database_code_depnum_ccdc_archive 'CCDC 832177' #TrackingRef 'complex1 at 286K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _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 P21/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 27.1531(13) _cell_length_b 9.5952(4) _cell_length_c 7.5456(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.837(4) _cell_angle_gamma 90.00 _cell_volume 1963.52(15) _cell_formula_units_Z 4 _cell_measurement_temperature 286(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8770 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details 'CrysAlis RED' _exptl_special_details ; ? ; _diffrn_ambient_temperature 286(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 'CrysAlis CCD, Oxford Diffraction Ltd.' _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 8788 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3847 _reflns_number_gt 2763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+14.2742P] 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 3847 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2069 _refine_ls_wR_factor_gt 0.1995 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.007 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 0.44937(5) 0.57851(15) 0.19312(18) 0.0159(3) Uani 1 1 d . . . O8 O 0.40975(15) 0.6508(5) 0.2852(6) 0.0283(10) Uani 1 1 d . . . O7 O 0.47132(17) 0.4719(5) 0.3134(6) 0.0292(11) Uani 1 1 d . . . O6 O 0.48756(15) 0.6805(4) 0.1555(6) 0.0249(10) Uani 1 1 d . . . O5 O 0.42982(17) 0.5129(5) 0.0301(6) 0.0298(11) Uani 1 1 d . . . N4 N 0.42586(18) 0.5729(5) -0.3449(6) 0.0216(11) Uani 1 1 d . . . H4B H 0.4145 0.6561 -0.3144 0.032 Uiso 1 1 calc R . . H4C H 0.4356 0.5762 -0.4558 0.032 Uiso 1 1 calc R . . H4D H 0.4513 0.5496 -0.2720 0.032 Uiso 1 1 calc R . . N3 N 0.44287(17) 0.2840(5) -0.4285(6) 0.0199(11) Uani 1 1 d . . . H3A H 0.4552 0.3470 -0.5007 0.030 Uiso 1 1 calc R . . H3B H 0.4394 0.2030 -0.4851 0.030 Uiso 1 1 calc R . . H3C H 0.4633 0.2733 -0.3335 0.030 Uiso 1 1 calc R . . C12 C 0.3949(2) 0.3309(6) -0.3729(7) 0.0176(12) Uani 1 1 d . . . C11 C 0.3568(2) 0.2364(7) -0.3645(9) 0.0303(15) Uani 1 1 d . . . H11A H 0.3619 0.1431 -0.3916 0.036 Uiso 1 1 calc R . . C10 C 0.3871(2) 0.4700(6) -0.3328(7) 0.0173(12) Uani 1 1 d . . . C9 C 0.3411(2) 0.5122(7) -0.2821(8) 0.0257(14) Uani 1 1 d . . . H9A H 0.3359 0.6047 -0.2515 0.031 Uiso 1 1 calc R . . C8 C 0.3028(3) 0.4176(8) -0.2769(11) 0.0379(17) Uani 1 1 d . . . H8A H 0.2717 0.4470 -0.2469 0.045 Uiso 1 1 calc R . . C7 C 0.3109(3) 0.2814(8) -0.3156(11) 0.0391(18) Uani 1 1 d . . . H7A H 0.2852 0.2176 -0.3092 0.047 Uiso 1 1 calc R . . S2 S 0.04968(5) 1.57691(15) -0.29333(18) 0.0150(3) Uani 1 1 d . . . O4 O 0.09066(15) 1.6453(4) -0.1873(6) 0.0227(9) Uani 1 1 d . . . O3 O 0.02729(15) 1.4730(4) -0.1782(5) 0.0232(10) Uani 1 1 d . . . O2 O 0.01260(15) 1.6830(4) -0.3442(5) 0.0220(9) Uani 1 1 d . . . O1 O 0.06854(16) 1.5093(5) -0.4478(5) 0.0276(10) Uani 1 1 d . . . N2 N 0.07620(18) 0.9218(5) -0.3276(6) 0.0194(10) Uani 1 1 d . . . H2B H 0.0884 0.8385 -0.2977 0.029 Uiso 1 1 calc R . . H2C H 0.0682 0.9233 -0.4434 0.029 Uiso 1 1 calc R . . H2D H 0.0495 0.9384 -0.2672 0.029 Uiso 1 1 calc R . . N1 N 0.05661(17) 1.2143(5) -0.4023(6) 0.0189(10) Uani 1 1 d . . . H1B H 0.0345 1.2202 -0.3196 0.028 Uiso 1 1 calc R . . H1C H 0.0463 1.1531 -0.4848 0.028 Uiso 1 1 calc R . . H1D H 0.0603 1.2974 -0.4522 0.028 Uiso 1 1 calc R . . C6 C 0.1133(2) 1.0291(6) -0.2856(7) 0.0175(12) Uani 1 1 d . . . C5 C 0.1388(2) 1.2675(7) -0.2740(8) 0.0250(14) Uani 1 1 d . . . H5A H 0.1325 1.3613 -0.2965 0.030 Uiso 1 1 calc R . . C4 C 0.1934(2) 1.0868(8) -0.1659(9) 0.0357(17) Uani 1 1 d . . . H4A H 0.2240 1.0592 -0.1176 0.043 Uiso 1 1 calc R . . C3 C 0.1037(2) 1.1685(6) -0.3211(7) 0.0169(12) Uani 1 1 d . . . C2 C 0.1580(2) 0.9888(7) -0.2105(8) 0.0264(14) Uani 1 1 d . . . H2A H 0.1644 0.8949 -0.1896 0.032 Uiso 1 1 calc R . . C1 C 0.1833(2) 1.2264(8) -0.1930(9) 0.0327(16) Uani 1 1 d . . . H1A H 0.2065 1.2931 -0.1567 0.039 Uiso 1 1 calc R . . O3W O 0.2493(2) 0.7550(7) 0.0093(8) 0.0588(16) Uani 1 1 d . . . H3WB H 0.2334 0.8168 0.0637 0.071 Uiso 1 1 d R . . H3WA H 0.2674 0.7944 -0.0647 0.071 Uiso 1 1 d R . . O2W O 0.3054(2) 0.6011(7) 0.2555(8) 0.0586(17) Uani 1 1 d . . . H2WA H 0.3383 0.6067 0.2704 0.070 Uiso 1 1 d R . . H2WB H 0.2933 0.6549 0.1742 0.070 Uiso 1 1 d R . . O1W O 0.19336(19) 0.8979(6) 0.2585(8) 0.0525(15) Uani 1 1 d . . . H1WA H 0.1602 0.8914 0.2743 0.063 Uiso 1 1 d R . . H1WB H 0.2074 0.8762 0.3584 0.063 Uiso 1 1 d 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 0.0189(7) 0.0125(7) 0.0163(7) 0.0015(6) 0.0003(5) -0.0009(6) O8 0.022(2) 0.029(3) 0.034(3) -0.003(2) 0.0091(19) 0.004(2) O7 0.035(3) 0.022(2) 0.030(2) 0.0151(19) -0.0008(19) 0.000(2) O6 0.025(2) 0.022(2) 0.028(2) 0.0038(19) 0.0039(18) -0.0078(18) O5 0.041(3) 0.028(2) 0.020(2) -0.0074(19) -0.0060(19) -0.006(2) N4 0.024(3) 0.020(3) 0.020(2) -0.005(2) 0.003(2) -0.003(2) N3 0.021(3) 0.019(3) 0.020(2) -0.001(2) 0.001(2) 0.001(2) C12 0.017(3) 0.020(3) 0.016(3) 0.003(2) 0.002(2) -0.001(2) C11 0.027(4) 0.021(3) 0.043(4) -0.002(3) 0.006(3) -0.005(3) C10 0.019(3) 0.016(3) 0.016(3) 0.003(2) -0.003(2) 0.001(2) C9 0.025(3) 0.020(3) 0.032(3) 0.000(3) 0.002(3) 0.003(3) C8 0.021(3) 0.034(4) 0.058(5) -0.006(4) 0.008(3) 0.000(3) C7 0.023(4) 0.031(4) 0.064(5) 0.001(4) 0.008(3) -0.009(3) S2 0.0172(7) 0.0130(7) 0.0150(7) 0.0016(6) 0.0012(5) 0.0003(6) O4 0.021(2) 0.020(2) 0.026(2) -0.0027(18) -0.0053(17) -0.0021(18) O3 0.024(2) 0.023(2) 0.022(2) 0.0109(18) 0.0029(17) -0.0015(18) O2 0.021(2) 0.019(2) 0.025(2) 0.0041(18) -0.0029(17) 0.0064(17) O1 0.038(3) 0.029(2) 0.017(2) -0.0035(19) 0.0109(18) 0.004(2) N2 0.024(3) 0.017(2) 0.017(2) 0.002(2) -0.0003(19) -0.002(2) N1 0.018(2) 0.018(3) 0.020(3) -0.001(2) -0.001(2) 0.002(2) C6 0.017(3) 0.020(3) 0.016(3) -0.003(2) 0.003(2) -0.002(2) C5 0.024(3) 0.018(3) 0.033(3) -0.003(3) 0.003(3) -0.003(3) C4 0.016(3) 0.049(5) 0.041(4) 0.003(4) -0.005(3) -0.002(3) C3 0.015(3) 0.021(3) 0.015(3) 0.000(2) 0.002(2) -0.001(2) C2 0.029(3) 0.019(3) 0.031(3) 0.006(3) 0.000(3) 0.005(3) C1 0.018(3) 0.037(4) 0.042(4) 0.000(3) -0.004(3) -0.010(3) O3W 0.049(3) 0.065(4) 0.062(4) 0.001(3) 0.006(3) 0.000(3) O2W 0.030(3) 0.071(4) 0.074(4) 0.009(3) -0.009(3) 0.001(3) O1W 0.032(3) 0.055(4) 0.071(4) 0.009(3) -0.001(3) 0.001(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 O5 1.458(4) . ? S1 O6 1.464(4) . ? S1 O7 1.474(4) . ? S1 O8 1.481(4) . ? N4 C10 1.450(7) . ? N3 C12 1.458(7) . ? C12 C11 1.380(8) . ? C12 C10 1.387(8) . ? C11 C7 1.388(9) . ? C10 C9 1.385(8) . ? C9 C8 1.380(9) . ? C8 C7 1.359(10) . ? S2 O1 1.449(4) . ? S2 O3 1.473(4) . ? S2 O2 1.470(4) . ? S2 O4 1.490(4) . ? N2 C6 1.464(7) . ? N1 C3 1.457(7) . ? C6 C2 1.371(8) . ? C6 C3 1.386(8) . ? C5 C1 1.385(9) . ? C5 C3 1.380(8) . ? C4 C2 1.373(9) . ? C4 C1 1.380(10) . ? 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 O5 S1 O6 110.9(3) . . ? O5 S1 O7 109.8(3) . . ? O6 S1 O7 108.3(3) . . ? O5 S1 O8 110.8(3) . . ? O6 S1 O8 108.4(3) . . ? O7 S1 O8 108.5(3) . . ? C11 C12 C10 119.9(5) . . ? C11 C12 N3 119.5(5) . . ? C10 C12 N3 120.6(5) . . ? C12 C11 C7 119.6(6) . . ? C12 C10 C9 119.5(5) . . ? C12 C10 N4 121.4(5) . . ? C9 C10 N4 119.1(5) . . ? C8 C9 C10 120.4(6) . . ? C7 C8 C9 119.8(6) . . ? C8 C7 C11 120.8(6) . . ? O1 S2 O3 110.1(3) . . ? O1 S2 O2 111.4(3) . . ? O3 S2 O2 109.0(2) . . ? O1 S2 O4 110.1(3) . . ? O3 S2 O4 107.5(2) . . ? O2 S2 O4 108.6(2) . . ? C2 C6 C3 120.4(5) . . ? C2 C6 N2 118.5(5) . . ? C3 C6 N2 121.1(5) . . ? C1 C5 C3 119.6(6) . . ? C2 C4 C1 119.8(6) . . ? C6 C3 C5 119.6(5) . . ? C6 C3 N1 121.6(5) . . ? C5 C3 N1 118.7(5) . . ? C6 C2 C4 120.2(6) . . ? C4 C1 C5 120.3(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4B O8 0.89 2.01 2.868(7) 162.7 4_575 O3W H3WA O2W 0.85 2.01 2.860(9) 175.1 4_575 N4 H4C O8 0.89 2.17 2.902(7) 139.7 1_554 N4 H4C O7 0.89 2.27 3.071(7) 149.8 1_554 N3 H3A O7 0.89 1.91 2.791(6) 169.0 1_554 N4 H4D O7 0.89 2.15 2.823(7) 131.9 3_665 N3 H3C O6 0.89 1.90 2.746(7) 158.6 3_665 N4 H4D O5 0.89 2.41 2.884(6) 113.9 . N3 H3B O5 0.89 2.09 2.886(7) 148.1 4_565 N2 H2B O4 0.89 2.03 2.877(6) 157.9 1_545 N2 H2C O4 0.89 2.08 2.836(6) 142.9 4_585 N2 H2C O3 0.89 2.27 3.071(6) 149.2 4_585 N1 H1C O3 0.89 1.95 2.834(6) 175.4 4_585 N2 H2D O3 0.89 2.13 2.855(6) 138.0 2_544 N1 H1B O2 0.89 1.86 2.725(6) 165.1 2_544 N2 H2D O1 0.89 2.49 2.958(6) 113.3 4_586 O1W H1WA O4 0.92 1.96 2.868(7) 173.4 4_586 O3W H3WB O1W 0.85 2.03 2.830(9) 157.0 . O2W H2WA O8 0.90 1.98 2.872(7) 170.4 . O2W H2WB O3W 0.86 1.94 2.769(9) 164.4 . O1W H1WB O3W 0.85 2.01 2.784(8) 150.2 4_576 N1 H1D O1 0.89 2.05 2.872(7) 154.0 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.662 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.107