data_xws10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Cl2 N4 O6 S2' _chemical_formula_weight 605.54 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' 'Cl' 'Cl' 0.1484 0.1585 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.487(9) _cell_length_b 11.047(12) _cell_length_c 15.467(17) _cell_angle_alpha 102.312(15) _cell_angle_beta 97.659(15) _cell_angle_gamma 90.560(16) _cell_volume 1403(3) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 645 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 17.89 _exptl_crystal_description ROD _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9546 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17165 _diffrn_reflns_av_R_equivalents 0.6133 _diffrn_reflns_av_sigmaI/netI 1.4898 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 31.21 _reflns_number_total 8726 _reflns_number_gt 1113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^+0.0000P] 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 8726 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.5785 _refine_ls_R_factor_gt 0.1455 _refine_ls_wR_factor_ref 0.4383 _refine_ls_wR_factor_gt 0.2807 _refine_ls_goodness_of_fit_ref 0.867 _refine_ls_restrained_S_all 0.867 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.3717(5) 1.9128(4) 0.7601(3) 0.0294(12) Uani 1 1 d . . . S2 S 0.8368(5) 1.6774(4) 0.2194(3) 0.0281(12) Uani 1 1 d . . . O1 O 0.8449(14) 1.6360(10) 0.6464(9) 0.053(4) Uani 1 1 d . . . O2 O 1.4067(12) 1.7820(9) 0.7277(7) 0.039(3) Uani 1 1 d . . . O3 O 1.4912(11) 2.0082(9) 0.7657(7) 0.033(3) Uani 1 1 d . . . O4 O 0.9591(12) 1.5913(9) 0.1913(7) 0.036(3) Uani 1 1 d . . . O5 O 0.8459(12) 1.8031(9) 0.2039(7) 0.037(3) Uani 1 1 d . . . N1 N 1.2178(14) 1.9435(12) 0.6923(8) 0.029(3) Uani 1 1 d . . . H1A H 1.2224 1.9990 0.6594 0.035 Uiso 1 1 calc R . . N2 N 1.0820(16) 1.8750(11) 0.6919(9) 0.029(3) Uani 1 1 d . . . N3 N 0.7690(14) 1.7930(11) 0.3747(10) 0.025(3) Uani 1 1 d . . . N4 N 0.8515(15) 1.6880(11) 0.3276(8) 0.028(3) Uani 1 1 d . . . H4B H 0.9042 1.6356 0.3549 0.034 Uiso 1 1 calc R . . C1 C 0.807(3) 1.6555(17) 0.7409(12) 0.073(7) Uani 1 1 d . . . H1B H 0.8676 1.5986 0.7720 0.110 Uiso 1 1 calc R . . H1C H 0.6929 1.6394 0.7397 0.110 Uiso 1 1 calc R . . H1D H 0.8359 1.7413 0.7722 0.110 Uiso 1 1 calc R . . C2 C 1.1320(18) 1.9459(15) 1.1198(11) 0.040(5) Uani 1 1 d . . . H2C H 1.1608 2.0274 1.1589 0.060 Uiso 1 1 calc R . . H2D H 1.1806 1.8812 1.1480 0.060 Uiso 1 1 calc R . . H2E H 1.0160 1.9329 1.1101 0.060 Uiso 1 1 calc R . . C3 C 1.1931(18) 1.9396(16) 1.0287(12) 0.034(4) Uani 1 1 d . . . C4 C 1.1647(18) 1.8297(15) 0.9610(12) 0.033(5) Uani 1 1 d . . . H4C H 1.1065 1.7610 0.9705 0.040 Uiso 1 1 calc R . . C5 C 1.2203(19) 1.8243(14) 0.8846(14) 0.040(5) Uani 1 1 d . . . H5B H 1.2035 1.7492 0.8406 0.048 Uiso 1 1 calc R . . C6 C 1.3044(17) 1.9253(14) 0.8644(11) 0.027(4) Uani 1 1 d . . . C7 C 1.3314(17) 2.0315(15) 0.9364(12) 0.034(5) Uani 1 1 d . . . H7A H 1.3914 2.1003 0.9284 0.041 Uiso 1 1 calc R . . C8 C 1.2774(19) 2.0390(15) 1.0137(11) 0.032(4) Uani 1 1 d . . . H8A H 1.2966 2.1128 1.0589 0.038 Uiso 1 1 calc R . . C9 C 0.948(2) 1.9089(15) 0.6623(12) 0.036(5) Uani 1 1 d . . . C10 C 0.8983(16) 2.0127(16) 0.6172(12) 0.038(5) Uani 1 1 d . . . H10A H 0.9492 2.0125 0.5632 0.045 Uiso 1 1 calc R . . H10B H 0.9114 2.0955 0.6581 0.045 Uiso 1 1 calc R . . C11 C 0.724(2) 1.9610(15) 0.5960(11) 0.040(5) Uani 1 1 d . . . H11A H 0.6483 2.0180 0.6271 0.048 Uiso 1 1 calc R . . C12 C 0.6577(18) 1.9008(15) 0.5008(13) 0.046(5) Uani 1 1 d . . . H12A H 0.6533 1.9653 0.4649 0.055 Uiso 1 1 calc R . . H12B H 0.5470 1.8712 0.5000 0.055 Uiso 1 1 calc R . . C13 C 0.747(2) 1.7937(14) 0.4550(12) 0.034(5) Uani 1 1 d . . . C14 C 0.8066(17) 1.6971(13) 0.5088(10) 0.022(4) Uani 1 1 d . . . H14A H 0.7652 1.6134 0.4761 0.027 Uiso 1 1 calc R . . H14B H 0.9243 1.6973 0.5158 0.027 Uiso 1 1 calc R . . C15 C 0.754(2) 1.7252(16) 0.5968(13) 0.048(5) Uani 1 1 d . . . H15A H 0.6369 1.7055 0.5903 0.057 Uiso 1 1 calc R . . C16 C 0.790(2) 1.8581(17) 0.6516(12) 0.046(5) Uani 1 1 d . . . H16A H 0.7487 1.8703 0.7102 0.055 Uiso 1 1 calc R . . C17 C 0.6514(17) 1.6078(14) 0.1711(11) 0.028(4) Uani 1 1 d . . . C18 C 0.510(2) 1.6801(14) 0.1732(10) 0.035(5) Uani 1 1 d . . . H18A H 0.5145 1.7659 0.2004 0.042 Uiso 1 1 calc R . . C19 C 0.3664(18) 1.6175(12) 0.1332(10) 0.024(4) Uani 1 1 d . . . H19A H 0.2727 1.6638 0.1323 0.028 Uiso 1 1 calc R . . C20 C 0.3524(18) 1.4950(15) 0.0956(12) 0.034(5) Uani 1 1 d . . . C21 C 0.488(2) 1.4261(14) 0.0924(11) 0.038(5) Uani 1 1 d . . . H21A H 0.4794 1.3413 0.0624 0.046 Uiso 1 1 calc R . . C22 C 0.6363(19) 1.4792(14) 0.1322(11) 0.034(4) Uani 1 1 d . . . H22A H 0.7270 1.4296 0.1333 0.040 Uiso 1 1 calc R . . C23 C 0.1898(19) 1.4296(14) 0.0507(11) 0.045(5) Uani 1 1 d . . . H23A H 0.1053 1.4892 0.0582 0.068 Uiso 1 1 calc R . . H23B H 0.1681 1.3608 0.0788 0.068 Uiso 1 1 calc R . . H23C H 0.1937 1.3976 -0.0131 0.068 Uiso 1 1 calc R . . Cl1 Cl 0.5480(7) 1.4311(6) 0.6165(5) 0.094(2) Uani 1 1 d . . . Cl2 Cl 0.7414(7) 1.2570(6) 0.5057(4) 0.079(2) Uani 1 1 d . . . O6 O 1.1672(13) 1.5706(9) 0.6590(7) 0.040(3) Uani 1 1 d . . . C24 C 0.725(3) 1.3474(16) 0.6190(16) 0.114(11) Uani 1 1 d . . . H24A H 0.7235 1.2909 0.6606 0.136 Uiso 1 1 calc R . . H24B H 0.8183 1.4057 0.6404 0.136 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.026(3) 0.022(2) 0.036(3) -0.001(2) 0.003(2) 0.0021(19) S2 0.034(3) 0.017(2) 0.030(3) -0.002(2) 0.003(2) 0.0016(19) O1 0.074(10) 0.042(8) 0.053(10) 0.032(7) 0.008(8) 0.026(7) O2 0.044(7) 0.026(6) 0.040(8) 0.000(6) -0.008(6) 0.013(5) O3 0.026(6) 0.028(6) 0.035(7) -0.007(6) -0.012(6) -0.011(5) O4 0.045(7) 0.029(7) 0.034(8) 0.000(6) 0.020(6) 0.012(6) O5 0.045(7) 0.026(6) 0.040(8) 0.005(6) 0.005(6) -0.007(5) N1 0.026(8) 0.033(8) 0.030(9) 0.012(7) -0.002(7) 0.001(6) N2 0.031(9) 0.020(7) 0.028(9) -0.003(7) -0.005(7) 0.007(7) N3 0.016(7) 0.021(7) 0.037(10) 0.002(7) 0.005(7) 0.002(6) N4 0.058(10) 0.015(7) 0.015(8) 0.005(6) 0.013(7) 0.011(6) C1 0.13(2) 0.046(13) 0.041(15) 0.028(12) -0.032(14) 0.012(13) C2 0.036(11) 0.030(10) 0.045(13) -0.004(9) -0.011(10) 0.003(8) C3 0.030(10) 0.033(10) 0.036(12) 0.007(9) -0.002(9) 0.017(8) C4 0.029(10) 0.025(10) 0.045(13) 0.018(10) -0.007(10) -0.014(8) C5 0.044(12) 0.006(8) 0.065(15) -0.001(9) 0.001(11) 0.003(8) C6 0.022(9) 0.020(9) 0.041(12) 0.011(9) 0.004(8) 0.011(7) C7 0.018(10) 0.028(10) 0.055(14) 0.014(10) -0.013(10) 0.011(7) C8 0.050(12) 0.034(11) 0.018(11) 0.011(9) 0.017(9) -0.001(9) C9 0.029(11) 0.026(9) 0.047(13) 0.003(9) -0.010(10) 0.005(8) C10 0.014(9) 0.049(11) 0.056(13) 0.020(10) 0.013(9) 0.014(8) C11 0.054(13) 0.030(10) 0.027(12) -0.003(9) -0.006(10) 0.015(9) C12 0.018(10) 0.030(10) 0.089(17) 0.014(11) 0.001(11) 0.006(8) C13 0.050(12) 0.019(9) 0.025(12) 0.000(8) -0.011(10) -0.009(8) C14 0.024(9) 0.026(9) 0.018(10) 0.007(8) 0.001(8) 0.005(7) C15 0.047(12) 0.033(11) 0.073(16) 0.028(11) 0.017(12) -0.004(9) C16 0.039(12) 0.073(15) 0.036(13) 0.041(12) -0.004(10) 0.011(10) C17 0.022(9) 0.035(10) 0.030(11) 0.005(9) 0.012(8) 0.023(8) C18 0.062(13) 0.021(9) 0.015(10) -0.009(8) -0.001(9) -0.007(9) C19 0.040(11) 0.009(8) 0.021(10) 0.009(7) -0.007(8) 0.001(7) C20 0.030(10) 0.032(10) 0.052(14) 0.025(10) 0.022(10) 0.013(8) C21 0.047(12) 0.014(8) 0.041(13) -0.011(8) -0.009(10) -0.002(8) C22 0.036(11) 0.022(9) 0.042(12) 0.006(9) 0.007(10) 0.006(8) C23 0.053(12) 0.027(10) 0.045(13) -0.004(9) -0.008(11) -0.014(9) Cl1 0.073(4) 0.085(5) 0.133(6) 0.040(5) 0.015(4) 0.000(4) Cl2 0.069(4) 0.084(4) 0.087(5) 0.029(4) 0.004(4) -0.006(3) O6 0.067(8) 0.010(5) 0.046(8) 0.014(6) 0.002(7) 0.010(5) C24 0.17(2) 0.016(10) 0.11(2) -0.020(13) -0.08(2) 0.029(13) _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 1.437(10) . ? S1 O2 1.472(11) . ? S1 N1 1.648(12) . ? S1 C6 1.761(17) . ? S2 O4 1.461(10) . ? S2 O5 1.461(10) . ? S2 N4 1.639(12) . ? S2 C17 1.745(16) . ? O1 C1 1.51(2) . ? O1 C15 1.530(19) . ? N1 N2 1.372(16) . ? N2 C9 1.261(18) . ? N3 C13 1.279(19) . ? N3 N4 1.469(16) . ? C2 C3 1.55(2) . ? C3 C8 1.38(2) . ? C3 C4 1.42(2) . ? C4 C5 1.32(2) . ? C5 C6 1.43(2) . ? C6 C7 1.43(2) . ? C7 C8 1.32(2) . ? C9 C16 1.42(2) . ? C9 C10 1.50(2) . ? C10 C11 1.55(2) . ? C11 C12 1.51(2) . ? C11 C16 1.63(2) . ? C12 C13 1.51(2) . ? C13 C14 1.54(2) . ? C14 C15 1.46(2) . ? C15 C16 1.54(2) . ? C17 C22 1.42(2) . ? C17 C18 1.45(2) . ? C18 C19 1.393(19) . ? C19 C20 1.35(2) . ? C20 C21 1.39(2) . ? C20 C23 1.56(2) . ? C21 C22 1.39(2) . ? Cl1 C24 1.77(2) . ? Cl2 C24 1.85(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 O2 119.7(7) . . ? O3 S1 N1 106.2(7) . . ? O2 S1 N1 106.9(6) . . ? O3 S1 C6 110.0(7) . . ? O2 S1 C6 107.5(7) . . ? N1 S1 C6 105.6(7) . . ? O4 S2 O5 118.9(7) . . ? O4 S2 N4 104.1(7) . . ? O5 S2 N4 107.9(6) . . ? O4 S2 C17 108.1(7) . . ? O5 S2 C17 109.4(7) . . ? N4 S2 C17 107.9(7) . . ? C1 O1 C15 110.5(13) . . ? N2 N1 S1 114.0(10) . . ? C9 N2 N1 120.7(14) . . ? C13 N3 N4 117.8(14) . . ? N3 N4 S2 114.0(10) . . ? C8 C3 C4 119.8(17) . . ? C8 C3 C2 120.6(16) . . ? C4 C3 C2 119.6(16) . . ? C5 C4 C3 119.1(16) . . ? C4 C5 C6 123.5(16) . . ? C7 C6 C5 114.1(16) . . ? C7 C6 S1 124.8(13) . . ? C5 C6 S1 121.1(14) . . ? C8 C7 C6 123.5(17) . . ? C7 C8 C3 119.9(18) . . ? N2 C9 C16 133.7(17) . . ? N2 C9 C10 132.5(16) . . ? C16 C9 C10 93.5(13) . . ? C9 C10 C11 91.2(12) . . ? C12 C11 C10 119.2(15) . . ? C12 C11 C16 111.2(14) . . ? C10 C11 C16 84.0(11) . . ? C11 C12 C13 116.8(14) . . ? N3 C13 C12 116.6(16) . . ? N3 C13 C14 125.5(16) . . ? C12 C13 C14 117.9(16) . . ? C15 C14 C13 110.2(14) . . ? C14 C15 O1 103.6(14) . . ? C14 C15 C16 116.1(14) . . ? O1 C15 C16 108.5(14) . . ? C9 C16 C15 118.8(16) . . ? C9 C16 C11 91.0(13) . . ? C15 C16 C11 111.8(14) . . ? C22 C17 C18 119.1(14) . . ? C22 C17 S2 120.6(11) . . ? C18 C17 S2 120.3(12) . . ? C19 C18 C17 116.7(14) . . ? C20 C19 C18 124.1(15) . . ? C19 C20 C21 119.3(15) . . ? C19 C20 C23 122.2(14) . . ? C21 C20 C23 118.5(15) . . ? C20 C21 C22 121.0(15) . . ? C21 C22 C17 119.6(14) . . ? Cl1 C24 Cl2 109.5(11) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 31.21 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.597 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.137