# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ? _publ_contact_author_email jon.steed@durham.ac.uk _publ_contact_author_phone ? _publ_contact_author_name 'Jonathan Steed' loop_ _publ_author_name 'Katharina Fucke' 'Michael Peach' 'Judith Howard' 'Jonathan Steed' data_try _database_code_depnum_ccdc_archive 'CCDC 897219' #TrackingRef '- DTA 1DMSO.cif' _audit_creation_date 2012-08-16 _audit_creation_method ; Olex2 1.2 (compiled May 9 2012 12:37:22, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 I3 N2 O4, C2 O S' _chemical_formula_sum 'C13 H15 I3 N2 O5 S' _chemical_formula_weight 692.03 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z+1/2' 4 '-x, y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z-1/2' 8 'x, -y-1/2, z' _cell_length_a 19.3415(5) _cell_length_b 12.5777(4) _cell_length_c 8.9696(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2182.05(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 120 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 4.415 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_correction_T_min 0.529425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.107 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1288 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_unetI/netI 0.0540 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 14117 _diffrn_reflns_theta_full 26.34 _diffrn_reflns_theta_max 26.34 _diffrn_reflns_theta_min 2.11 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_target Mo _diffrn_special_details hkl _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1954 _reflns_number_total 2325 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.452 _refine_diff_density_min -1.193 _refine_diff_density_rms 0.144 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 2325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0423 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+1.9262P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1113 _refine_ls_wR_factor_ref 0.1176 _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. ; _refinement_special_details 'The solvent is dynamically disordered, thus no hydrogen atoms have been added.' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I2 I 0.82534(3) 0.2500 0.09299(6) 0.05959(19) Uani 1 2 d S . . I1 I 0.58891(2) 0.49009(3) 0.36858(5) 0.0733(2) Uani 1 1 d . . . C3 C 0.6371(2) 0.3455(3) 0.3175(5) 0.0413(9) Uani 1 1 d . . . C5 C 0.7294(3) 0.2500 0.2003(6) 0.0374(12) Uani 1 2 d S . . C1 C 0.5432(3) 0.2500 0.4592(9) 0.0540(16) Uani 1 2 d S . . C2 C 0.6068(3) 0.2500 0.3606(6) 0.0423(13) Uani 1 2 d S . . C4 C 0.6987(2) 0.3466(3) 0.2371(4) 0.0394(9) Uani 1 1 d . . . N1 N 0.73033(19) 0.4442(3) 0.1974(4) 0.0460(8) Uani 1 1 d . . . H1N H 0.7229 0.4715 0.1085 0.055 Uiso 0.56(7) 1 calc PR A 1 O1 O 0.5581(3) 0.2500 0.5975(6) 0.0660(14) Uani 1 2 d S . . O3 O 0.7835(3) 0.4594(4) 0.4189(4) 0.0736(12) Uani 1 1 d . . . O2 O 0.4855(3) 0.2500 0.4087(7) 0.104(3) Uani 1 2 d S . . C6 C 0.7720(3) 0.4959(4) 0.2954(6) 0.0535(12) Uani 1 1 d . . . C7 C 0.8003(4) 0.5993(5) 0.2415(8) 0.087(2) Uani 1 1 d . . . H7A H 0.8501 0.6020 0.2609 0.131 Uiso 1 1 calc R . . H7B H 0.7774 0.6579 0.2940 0.131 Uiso 1 1 calc R . . H7C H 0.7920 0.6061 0.1341 0.131 Uiso 1 1 calc R . . O1S O 0.5440(4) 0.7500 0.2260(8) 0.103(2) Uani 1 2 d S . . C1S C 0.5456(17) 0.6490(16) -0.032(2) 0.312(15) Uani 1 1 d . . . S1S S 0.5411(5) 0.7500 0.0694(6) 0.225(4) Uani 1 2 d S . . H1A H 0.517(6) 0.2500 0.669(12) 0.08(3) Uiso 0.89(13) 2 d SP A 2 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 I2 0.0535(3) 0.0518(3) 0.0735(4) 0.000 0.0293(2) 0.000 I1 0.0625(3) 0.0538(3) 0.1036(4) -0.00935(18) 0.01375(19) 0.01950(16) C3 0.039(2) 0.040(2) 0.044(2) -0.0034(16) -0.0001(16) 0.0059(17) C5 0.038(3) 0.041(3) 0.033(3) 0.000 0.006(2) 0.000 C1 0.034(3) 0.064(4) 0.063(5) 0.000 0.007(3) 0.000 C2 0.033(3) 0.052(4) 0.041(3) 0.000 0.000(2) 0.000 C4 0.044(2) 0.039(2) 0.036(2) 0.0000(16) 0.0015(16) 0.0007(17) N1 0.056(2) 0.0347(18) 0.047(2) -0.0019(14) 0.0081(16) -0.0040(16) O1 0.050(3) 0.094(4) 0.054(3) 0.000 0.010(2) 0.000 O3 0.096(3) 0.071(3) 0.054(2) -0.0110(18) -0.004(2) -0.020(2) O2 0.028(3) 0.207(10) 0.078(4) 0.000 -0.002(2) 0.000 C6 0.059(3) 0.044(3) 0.057(3) -0.012(2) 0.013(2) -0.0066(19) C7 0.112(5) 0.060(4) 0.091(4) -0.013(3) 0.015(4) -0.038(4) O1S 0.094(5) 0.126(6) 0.090(5) 0.000 0.039(4) 0.000 C1S 0.60(5) 0.21(2) 0.122(11) -0.035(11) 0.000(18) 0.10(2) S1S 0.399(12) 0.177(5) 0.100(3) 0.000 0.100(5) 0.000 _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 I2 C5 2.090(5) . ? I1 C3 2.094(4) . ? C3 C2 1.392(5) . ? C3 C4 1.393(6) . ? C5 C4 1.392(5) . ? C5 C4 1.392(5) 8_565 ? C1 C2 1.515(9) . ? C1 O1 1.274(9) . ? C1 O2 1.204(9) . ? C2 C3 1.392(5) 8_565 ? C4 N1 1.416(5) . ? N1 C6 1.358(6) . ? O3 C6 1.220(7) . ? C6 C7 1.492(7) . ? O1S S1S 1.405(9) . ? C1S S1S 1.566(17) . ? S1S C1S 1.566(17) 8_575 ? 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 C2 C3 I1 120.1(3) . . ? C2 C3 C4 120.9(4) . . ? C4 C3 I1 119.1(3) . . ? C4 C5 I2 119.2(3) 8_565 . ? C4 C5 I2 119.2(3) . . ? C4 C5 C4 121.6(5) . 8_565 ? O1 C1 C2 112.6(6) . . ? O2 C1 C2 122.2(7) . . ? O2 C1 O1 125.2(7) . . ? C3 C2 C3 119.3(5) . 8_565 ? C3 C2 C1 120.3(3) . . ? C3 C2 C1 120.3(3) 8_565 . ? C3 C4 N1 120.5(4) . . ? C5 C4 C3 118.6(4) . . ? C5 C4 N1 120.8(4) . . ? C6 N1 C4 120.5(4) . . ? N1 C6 C7 115.2(5) . . ? O3 C6 N1 121.1(4) . . ? O3 C6 C7 123.7(5) . . ? O1S S1S C1S 125.4(8) . . ? O1S S1S C1S 125.4(8) . 8_575 ? C1S S1S C1S 108.5(16) . 8_575 ? # Attachment '- DTA 2DMSO.cif' data_try2 _database_code_depnum_ccdc_archive 'CCDC 897220' #TrackingRef '- DTA 2DMSO.cif' _audit_creation_date 2012-06-08 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H9 I3 N2 O4, 2(C2 H6 O S)' _chemical_formula_sum 'C15 H21 I3 N2 O6 S2' _chemical_formula_weight 770.16 _chemical_melting_point ? 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' I I -0.4742 1.8119 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 15.845(2) _cell_length_b 9.1061(13) _cell_length_c 32.832(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4737.3(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1281 _cell_measurement_temperature 120 _cell_measurement_theta_max 23.12 _cell_measurement_theta_min 2.57 _exptl_absorpt_coefficient_mu 4.167 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.4781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0996 before and 0.0764 after correction. The Ratio of minimum to maximum transmission is 0.6414. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.160 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 2912 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (25 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 5.85 cm. ; _diffrn_reflns_av_R_equivalents 0.2330 _diffrn_reflns_av_unetI/netI 0.2073 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 26730 _diffrn_reflns_theta_full 26.32 _diffrn_reflns_theta_max 26.32 _diffrn_reflns_theta_min 1.24 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2017 _reflns_number_total 4808 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.109 _refine_diff_density_min -1.384 _refine_diff_density_rms 0.267 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 4808 _refine_ls_number_restraints 168 _refine_ls_R_factor_all 0.1695 _refine_ls_R_factor_gt 0.0522 _refine_ls_restrained_S_all 0.846 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1036 _refine_ls_wR_factor_ref 0.1369 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I2 I 0.45682(6) 0.31818(11) 0.27012(3) 0.0218(2) Uani 1 1 d U . . I1 I 0.54218(6) 0.51319(11) 0.44114(3) 0.0230(2) Uani 1 1 d U . . I3 I 0.24513(6) 0.11146(10) 0.41178(3) 0.0246(2) Uani 1 1 d U . . S2S S 0.3811(2) 0.9045(5) 0.54914(13) 0.0310(10) Uani 1 1 d U . . C2 C 0.3982(8) 0.3105(15) 0.4156(4) 0.015(3) Uani 1 1 d U . . C7 C 0.3449(8) 0.2351(14) 0.3885(4) 0.014(3) Uani 1 1 d U . . C6 C 0.3581(8) 0.2461(15) 0.3474(4) 0.015(3) Uani 1 1 d U . . C3 C 0.4639(8) 0.3978(15) 0.3996(4) 0.019(3) Uani 1 1 d U . . C4 C 0.4787(8) 0.4081(16) 0.3584(4) 0.019(3) Uani 1 1 d U . . C5 C 0.4246(8) 0.3252(16) 0.3321(4) 0.018(3) Uani 1 1 d U . . S1S S 0.4812(2) 0.9294(4) 0.33458(12) 0.0237(9) Uani 1 1 d U . . N1 N 0.5430(7) 0.4990(13) 0.3423(3) 0.021(3) Uani 1 1 d U . . H1N H 0.5290 0.5866 0.3333 0.025 Uiso 1 1 calc R . . O1 O 0.4199(6) 0.1685(11) 0.4745(3) 0.027(3) Uani 1 1 d U . . H1 H 0.4133 0.1645 0.4998 0.041 Uiso 1 1 calc R . . O2 O 0.3505(6) 0.3842(11) 0.4823(3) 0.025(2) Uani 1 1 d U . . N2 N 0.3019(7) 0.1755(14) 0.3191(3) 0.023(3) Uani 1 1 d U . . H2N H 0.3093 0.0823 0.3131 0.028 Uiso 1 1 calc R . . C11 C 0.1859(8) 0.1670(17) 0.2717(4) 0.026(4) Uani 1 1 d U . . H11A H 0.2060 0.0653 0.2703 0.039 Uiso 1 1 calc R . . H11B H 0.1911 0.2127 0.2447 0.039 Uiso 1 1 calc R . . H11C H 0.1266 0.1681 0.2802 0.039 Uiso 1 1 calc R . . O4 O 0.2224(6) 0.3794(13) 0.3105(4) 0.042(3) Uani 1 1 d U . . O3 O 0.6486(6) 0.3369(13) 0.3547(3) 0.039(3) Uani 1 1 d U . . C10 C 0.2377(9) 0.2506(16) 0.3017(4) 0.021(3) Uani 1 1 d U . . C1 C 0.3872(8) 0.2901(15) 0.4606(4) 0.014(3) Uani 1 1 d U . . C8 C 0.6232(10) 0.4586(19) 0.3402(5) 0.033(4) Uani 1 1 d U . . C9 C 0.6816(10) 0.5577(18) 0.3185(5) 0.035(4) Uani 1 1 d U . . H9A H 0.6492 0.6319 0.3036 0.053 Uiso 1 1 calc R . . H9B H 0.7158 0.5007 0.2992 0.053 Uiso 1 1 calc R . . H9C H 0.7188 0.6063 0.3382 0.053 Uiso 1 1 calc R . . C3S C 0.2770(9) 0.864(2) 0.5659(5) 0.046(5) Uani 1 1 d U . . H3SA H 0.2363 0.9021 0.5460 0.069 Uiso 1 1 calc R . . H3SB H 0.2672 0.9105 0.5924 0.069 Uiso 1 1 calc R . . H3SC H 0.2702 0.7576 0.5684 0.069 Uiso 1 1 calc R . . C4S C 0.3709(10) 0.8336(19) 0.4999(5) 0.037(4) Uani 1 1 d U . . H4SA H 0.3265 0.8872 0.4854 0.056 Uiso 1 1 calc R . . H4SB H 0.3560 0.7293 0.5014 0.056 Uiso 1 1 calc R . . H4SC H 0.4245 0.8447 0.4853 0.056 Uiso 1 1 calc R . . O1S O 0.4943(6) 0.7824(11) 0.3145(3) 0.028(3) Uani 1 1 d U . . C2S C 0.4568(9) 0.8890(17) 0.3850(4) 0.030(4) Uani 1 1 d U . . H2SA H 0.3956 0.8953 0.3889 0.045 Uiso 1 1 calc R . . H2SB H 0.4850 0.9596 0.4029 0.045 Uiso 1 1 calc R . . H2SC H 0.4761 0.7895 0.3915 0.045 Uiso 1 1 calc R . . C1S C 0.5822(9) 1.005(2) 0.3413(5) 0.040(4) Uani 1 1 d U . . H1SA H 0.6220 0.9275 0.3489 0.060 Uiso 1 1 calc R . . H1SB H 0.5803 1.0794 0.3629 0.060 Uiso 1 1 calc R . . H1SC H 0.6008 1.0511 0.3158 0.060 Uiso 1 1 calc R . . O2S O 0.3863(8) 1.0673(12) 0.5438(3) 0.043(3) Uani 1 1 d U . . 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 I2 0.0227(5) 0.0219(5) 0.0208(5) -0.0006(4) 0.0009(5) -0.0006(5) I1 0.0209(4) 0.0242(6) 0.0239(5) -0.0014(5) -0.0022(5) -0.0046(5) I3 0.0197(4) 0.0222(5) 0.0320(6) 0.0005(5) 0.0036(5) -0.0043(5) S2S 0.0258(19) 0.037(2) 0.030(2) 0.0020(19) -0.0011(18) -0.0021(18) C2 0.015(4) 0.013(5) 0.018(5) 0.002(4) 0.001(4) 0.002(4) C7 0.015(5) 0.015(5) 0.013(5) 0.003(4) 0.003(4) 0.000(4) C6 0.014(5) 0.015(5) 0.015(5) -0.002(4) -0.004(4) 0.005(4) C3 0.018(5) 0.020(5) 0.020(5) 0.004(4) -0.001(4) -0.003(4) C4 0.016(5) 0.024(5) 0.017(5) -0.003(4) 0.001(4) -0.001(4) C5 0.018(5) 0.016(5) 0.022(5) -0.006(4) -0.001(4) 0.001(4) S1S 0.026(2) 0.020(2) 0.025(2) 0.0004(16) -0.0013(16) 0.0002(15) N1 0.025(4) 0.017(4) 0.021(4) 0.006(4) -0.003(4) -0.005(4) O1 0.033(5) 0.029(6) 0.020(5) 0.008(5) 0.003(5) 0.001(5) O2 0.027(5) 0.028(5) 0.019(5) -0.008(5) 0.006(4) -0.002(5) N2 0.028(4) 0.020(5) 0.023(5) -0.004(4) -0.010(4) 0.000(4) C11 0.031(7) 0.030(7) 0.016(6) 0.005(6) -0.005(6) 0.002(6) O4 0.038(6) 0.024(5) 0.065(7) -0.010(5) -0.020(5) 0.013(5) O3 0.028(5) 0.038(6) 0.050(6) 0.006(5) 0.007(5) -0.001(5) C10 0.019(5) 0.018(5) 0.025(5) -0.004(4) -0.001(4) -0.002(4) C1 0.009(4) 0.017(5) 0.016(5) 0.002(4) -0.003(4) -0.002(4) C8 0.031(6) 0.033(6) 0.034(6) -0.001(4) 0.002(4) -0.002(4) C9 0.037(7) 0.035(8) 0.033(8) 0.010(6) 0.002(7) -0.007(6) C3S 0.033(7) 0.054(9) 0.051(8) 0.004(7) -0.007(7) -0.003(7) C4S 0.039(7) 0.033(8) 0.039(8) -0.005(7) -0.005(7) 0.002(7) O1S 0.030(5) 0.021(6) 0.032(6) -0.009(4) 0.000(5) -0.007(4) C2S 0.027(6) 0.031(7) 0.033(7) -0.009(6) 0.002(6) -0.002(7) C1S 0.032(7) 0.046(8) 0.042(8) -0.009(7) 0.001(6) 0.002(7) O2S 0.061(6) 0.031(6) 0.037(6) 0.008(5) 0.010(5) -0.007(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 I2 C5 2.099(14) . ? I1 C3 2.122(14) . ? I3 C7 2.085(13) . ? S2S C3S 1.777(15) . ? S2S C4S 1.747(16) . ? S2S O2S 1.496(11) . ? C2 C7 1.404(18) . ? C2 C3 1.411(18) . ? C2 C1 1.500(19) . ? C7 C6 1.371(19) . ? C6 C5 1.371(18) . ? C6 N2 1.438(16) . ? C3 C4 1.376(18) . ? C4 C5 1.433(18) . ? C4 N1 1.415(17) . ? S1S O1S 1.507(10) . ? S1S C2S 1.738(14) . ? S1S C1S 1.758(15) . ? N1 C8 1.325(18) . ? O1 C1 1.304(16) . ? O2 C1 1.257(16) . ? N2 C10 1.353(17) . ? C11 C10 1.492(19) . ? O4 C10 1.232(16) . ? O3 C8 1.272(18) . ? C8 C9 1.48(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 C4S S2S C3S 97.1(8) . . ? O2S S2S C3S 107.0(8) . . ? O2S S2S C4S 105.2(8) . . ? C7 C2 C3 119.0(12) . . ? C7 C2 C1 119.5(12) . . ? C3 C2 C1 121.5(12) . . ? C2 C7 I3 119.3(10) . . ? C6 C7 I3 121.1(10) . . ? C6 C7 C2 119.7(12) . . ? C7 C6 C5 121.1(13) . . ? C7 C6 N2 120.6(12) . . ? C5 C6 N2 118.3(12) . . ? C2 C3 I1 118.1(10) . . ? C4 C3 I1 119.9(10) . . ? C4 C3 C2 122.0(13) . . ? C3 C4 C5 117.0(13) . . ? C3 C4 N1 122.0(12) . . ? N1 C4 C5 121.0(12) . . ? C6 C5 I2 121.8(10) . . ? C6 C5 C4 121.1(13) . . ? C4 C5 I2 117.0(10) . . ? O1S S1S C2S 105.1(7) . . ? O1S S1S C1S 106.1(7) . . ? C2S S1S C1S 99.6(8) . . ? C8 N1 C4 123.2(13) . . ? C10 N2 C6 120.9(12) . . ? N2 C10 C11 115.8(13) . . ? O4 C10 N2 122.1(13) . . ? O4 C10 C11 122.1(13) . . ? O1 C1 C2 113.8(12) . . ? O2 C1 C2 121.8(13) . . ? O2 C1 O1 124.4(13) . . ? N1 C8 C9 117.2(15) . . ? O3 C8 N1 121.7(15) . . ? O3 C8 C9 121.0(15) . . ? # Attachment '- DTA 4DMSO.cif' data_09srv382 _database_code_depnum_ccdc_archive 'CCDC 897221' #TrackingRef '- DTA 4DMSO.cif' _audit_creation_date 2012-06-07 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H9 I3 N2 O4, 4(C2 H6 O S)' _chemical_formula_sum 'C19 H33 I3 N2 O8 S4' _chemical_formula_weight 926.41 _chemical_melting_point ? 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' I I -0.4742 1.8119 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 20.5386(5) _cell_length_b 9.6418(2) _cell_length_c 16.3885(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.7640(10) _cell_angle_gamma 90.00 _cell_volume 3222.81(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 120 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 3.209 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1792 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_unetI/netI 0.0487 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 20916 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 1.00 _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_target Mo _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5307 _reflns_number_total 6584 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 1.402 _refine_diff_density_min -1.096 _refine_diff_density_rms 0.149 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 6584 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0336 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0833 _refine_ls_wR_factor_ref 0.0885 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I 0.435263(13) 0.02491(3) 0.603739(17) 0.02235(8) Uani 1 1 d . . . I2 I 0.227457(14) 0.33388(3) 0.384222(17) 0.02376(9) Uani 1 1 d . . . I3 I 0.150754(13) 0.00716(3) 0.672130(17) 0.02097(8) Uani 1 1 d . . . S3S S 0.31460(6) 0.86229(12) 0.39697(7) 0.0277(3) Uani 1 1 d . . . S4S S 0.07664(5) 0.70324(12) 0.31815(7) 0.0233(2) Uani 1 1 d . . . S1S S 0.42612(5) 0.41136(12) 0.75203(7) 0.0268(2) Uani 1 1 d . . . S2S S 0.89183(7) 0.46256(13) 0.35379(8) 0.0364(3) Uani 1 1 d . . . O3 O 0.38064(17) 0.4270(3) 0.5237(2) 0.0347(8) Uani 1 1 d . . . O2 O 0.33059(18) -0.0026(3) 0.7630(2) 0.0354(8) Uani 1 1 d . . . O4 O 0.11568(16) 0.0077(3) 0.4380(2) 0.0321(8) Uani 1 1 d . . . O1 O 0.29455(17) -0.1813(3) 0.6840(2) 0.0353(8) Uani 1 1 d . . . H1 H 0.3089 -0.2291 0.7251 0.053 Uiso 1 1 calc R . . C5 C 0.2543(2) 0.2102(4) 0.4880(2) 0.0184(8) Uani 1 1 d . . . C6 C 0.2058(2) 0.1637(4) 0.5344(2) 0.0180(8) Uani 1 1 d . . . C8 C 0.3967(2) 0.3456(4) 0.4718(3) 0.0225(9) Uani 1 1 d . . . C3 C 0.33706(19) 0.0852(4) 0.5749(2) 0.0180(8) Uani 1 1 d . . . C4 C 0.3198(2) 0.1726(4) 0.5073(2) 0.0166(8) Uani 1 1 d . . . N1 N 0.36849(16) 0.2196(4) 0.4597(2) 0.0199(7) Uani 1 1 d . . . H1A H 0.3807 0.1653 0.4211 0.024 Uiso 1 1 calc R . . C10 C 0.0981(2) 0.1200(5) 0.4634(3) 0.0240(9) Uani 1 1 d . . . C7 C 0.22407(19) 0.0763(4) 0.6015(2) 0.0184(8) Uani 1 1 d . . . C2 C 0.2891(2) 0.0375(4) 0.6216(3) 0.0198(9) Uani 1 1 d . . . C9 C 0.4473(2) 0.3799(5) 0.4157(3) 0.0281(10) Uani 1 1 d . . . H9A H 0.4256 0.3958 0.3599 0.042 Uiso 1 1 calc R . . H9B H 0.4782 0.3026 0.4151 0.042 Uiso 1 1 calc R . . H9C H 0.4711 0.4638 0.4354 0.042 Uiso 1 1 calc R . . N2 N 0.13908(16) 0.2020(4) 0.5121(2) 0.0200(7) Uani 1 1 d . . . H2 H 0.1244 0.2805 0.5304 0.024 Uiso 1 1 calc R . . C1 C 0.3078(2) -0.0508(5) 0.6989(3) 0.0280(10) Uani 1 1 d . . . C11 C 0.0298(2) 0.1759(5) 0.4420(3) 0.0303(11) Uani 1 1 d . . . H11A H 0.0172 0.1676 0.3826 0.046 Uiso 1 1 calc R . . H11B H 0.0287 0.2737 0.4581 0.046 Uiso 1 1 calc R . . H11C H -0.0008 0.1228 0.4713 0.046 Uiso 1 1 calc R . . O1S O 0.42865(15) 0.4455(3) 0.84302(18) 0.0267(7) Uani 1 1 d . . . O2S O 0.91755(15) 0.5652(3) 0.41804(18) 0.0265(7) Uani 1 1 d . . . O4S O 0.05173(15) 0.5820(3) 0.26510(19) 0.0301(7) Uani 1 1 d . . . O3S O 0.29123(17) 0.8468(3) 0.3062(2) 0.0349(8) Uani 1 1 d . . . C8S C 0.0081(2) 0.8142(5) 0.3241(3) 0.0291(10) Uani 1 1 d . . . H8SA H -0.0088 0.8459 0.2688 0.044 Uiso 1 1 calc R . . H8SB H 0.0217 0.8945 0.3586 0.044 Uiso 1 1 calc R . . H8SC H -0.0263 0.7633 0.3480 0.044 Uiso 1 1 calc R . . C7S C 0.0842(2) 0.6420(5) 0.4218(3) 0.0315(11) Uani 1 1 d . . . H7SA H 0.0424 0.6016 0.4333 0.047 Uiso 1 1 calc R . . H7SB H 0.0956 0.7196 0.4595 0.047 Uiso 1 1 calc R . . H7SC H 0.1186 0.5714 0.4296 0.047 Uiso 1 1 calc R . . C2S C 0.4244(2) 0.5753(5) 0.7015(3) 0.0333(11) Uani 1 1 d . . . H2SA H 0.3878 0.6305 0.7172 0.050 Uiso 1 1 calc R . . H2SB H 0.4186 0.5611 0.6418 0.050 Uiso 1 1 calc R . . H2SC H 0.4657 0.6243 0.7175 0.050 Uiso 1 1 calc R . . C1S C 0.3438(2) 0.3593(5) 0.7200(3) 0.0310(11) Uani 1 1 d . . . H1SA H 0.3356 0.2691 0.7443 0.046 Uiso 1 1 calc R . . H1SB H 0.3371 0.3520 0.6599 0.046 Uiso 1 1 calc R . . H1SC H 0.3136 0.4283 0.7381 0.046 Uiso 1 1 calc R . . C5S C 0.3796(3) 0.7428(6) 0.4187(4) 0.0423(13) Uani 1 1 d . . . H5SA H 0.3668 0.6528 0.3941 0.063 Uiso 1 1 calc R . . H5SB H 0.3896 0.7322 0.4783 0.063 Uiso 1 1 calc R . . H5SC H 0.4185 0.7771 0.3957 0.063 Uiso 1 1 calc R . . C6S C 0.2549(3) 0.7787(6) 0.4503(4) 0.0482(15) Uani 1 1 d . . . H6SA H 0.2127 0.8262 0.4383 0.072 Uiso 1 1 calc R . . H6SB H 0.2690 0.7820 0.5096 0.072 Uiso 1 1 calc R . . H6SC H 0.2503 0.6818 0.4325 0.072 Uiso 1 1 calc R . . C4S C 0.8735(3) 0.5545(6) 0.2609(3) 0.0451(14) Uani 1 1 d . . . H4SA H 0.8445 0.6326 0.2696 0.068 Uiso 1 1 calc R . . H4SB H 0.8515 0.4926 0.2189 0.068 Uiso 1 1 calc R . . H4SC H 0.9141 0.5895 0.2426 0.068 Uiso 1 1 calc R . . C3S C 0.8093(3) 0.4292(9) 0.3718(4) 0.089(3) Uani 1 1 d . . . H3SA H 0.8092 0.3796 0.4240 0.133 Uiso 1 1 calc R . . H3SB H 0.7877 0.3724 0.3270 0.133 Uiso 1 1 calc R . . H3SC H 0.7858 0.5172 0.3743 0.133 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 I1 0.01832(14) 0.02587(16) 0.02307(16) 0.00179(11) 0.00332(11) 0.00259(11) I2 0.02939(16) 0.02451(16) 0.01766(15) 0.00565(11) 0.00399(11) 0.00305(11) I3 0.01974(15) 0.02374(16) 0.02019(16) 0.00451(10) 0.00549(11) -0.00033(10) S3S 0.0391(6) 0.0219(6) 0.0228(6) -0.0056(4) 0.0069(5) -0.0044(5) S4S 0.0229(5) 0.0254(6) 0.0220(6) -0.0026(4) 0.0046(4) -0.0005(4) S1S 0.0292(6) 0.0283(6) 0.0240(6) -0.0019(4) 0.0076(4) -0.0004(5) S2S 0.0492(8) 0.0207(6) 0.0349(7) -0.0029(5) -0.0128(6) 0.0024(5) O3 0.048(2) 0.0304(19) 0.0282(19) -0.0095(15) 0.0150(15) -0.0142(16) O2 0.047(2) 0.040(2) 0.0175(18) 0.0050(14) -0.0014(15) 0.0077(16) O4 0.0302(18) 0.0321(19) 0.033(2) -0.0130(14) -0.0002(15) 0.0043(14) O1 0.040(2) 0.0267(19) 0.037(2) 0.0055(15) -0.0045(15) 0.0011(15) C5 0.026(2) 0.013(2) 0.016(2) -0.0017(15) 0.0004(16) -0.0012(16) C6 0.021(2) 0.019(2) 0.014(2) -0.0020(15) 0.0009(15) -0.0002(16) C8 0.025(2) 0.023(2) 0.019(2) 0.0025(17) 0.0009(17) -0.0042(18) C3 0.020(2) 0.016(2) 0.018(2) -0.0026(16) 0.0020(16) 0.0000(16) C4 0.022(2) 0.0129(19) 0.015(2) -0.0038(15) 0.0033(16) -0.0030(16) N1 0.0224(18) 0.0204(19) 0.0177(18) -0.0016(14) 0.0061(14) -0.0020(14) C10 0.023(2) 0.031(2) 0.018(2) -0.0011(18) 0.0020(17) 0.0005(19) C7 0.021(2) 0.016(2) 0.018(2) -0.0002(16) 0.0047(16) -0.0024(17) C2 0.025(2) 0.017(2) 0.017(2) -0.0004(16) 0.0000(16) -0.0016(17) C9 0.027(2) 0.032(3) 0.027(3) -0.0001(19) 0.0084(18) -0.009(2) N2 0.0181(17) 0.0230(19) 0.0179(19) 0.0000(14) -0.0014(13) 0.0031(14) C1 0.021(2) 0.026(2) 0.038(3) 0.003(2) 0.0038(19) 0.0029(19) C11 0.022(2) 0.041(3) 0.027(3) -0.009(2) -0.0025(18) 0.005(2) O1S 0.0284(17) 0.0309(18) 0.0210(17) -0.0007(13) 0.0038(13) -0.0048(14) O2S 0.0300(17) 0.0275(17) 0.0217(17) -0.0046(13) 0.0013(13) -0.0012(14) O4S 0.0327(18) 0.0285(18) 0.0303(18) -0.0124(14) 0.0088(14) -0.0006(14) O3S 0.042(2) 0.037(2) 0.0250(18) -0.0103(14) 0.0013(15) 0.0028(16) C8S 0.034(3) 0.025(2) 0.028(3) -0.0021(19) 0.004(2) 0.006(2) C7S 0.035(3) 0.031(3) 0.028(3) 0.004(2) 0.003(2) 0.008(2) C2S 0.038(3) 0.033(3) 0.030(3) 0.001(2) 0.008(2) -0.010(2) C1S 0.040(3) 0.030(3) 0.023(2) -0.0021(19) 0.005(2) -0.008(2) C5S 0.046(3) 0.036(3) 0.042(3) 0.004(2) -0.005(2) 0.000(3) C6S 0.059(4) 0.042(3) 0.048(4) -0.005(3) 0.022(3) -0.018(3) C4S 0.063(4) 0.047(3) 0.025(3) -0.001(2) 0.002(2) -0.002(3) C3S 0.070(5) 0.130(7) 0.059(5) 0.034(5) -0.021(4) -0.074(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 I1 C3 2.099(4) . ? I2 C5 2.097(4) . ? I3 C7 2.112(4) . ? S3S O3S 1.516(4) . ? S3S C5S 1.768(5) . ? S3S C6S 1.780(5) . ? S4S O4S 1.510(3) . ? S4S C8S 1.779(4) . ? S4S C7S 1.788(5) . ? S1S O1S 1.522(3) . ? S1S C2S 1.783(5) . ? S1S C1S 1.782(5) . ? S2S O2S 1.495(3) . ? S2S C4S 1.764(5) . ? S2S C3S 1.783(7) . ? O3 C8 1.230(5) . ? O2 C1 1.193(6) . ? O4 C10 1.229(5) . ? O1 C1 1.304(6) . ? C5 C6 1.397(5) . ? C5 C4 1.393(6) . ? C6 C7 1.401(6) . ? C6 N2 1.425(5) . ? C8 N1 1.350(5) . ? C8 C9 1.504(6) . ? C3 C4 1.403(6) . ? C3 C2 1.395(5) . ? C4 N1 1.413(5) . ? C10 N2 1.345(6) . ? C10 C11 1.505(6) . ? C7 C2 1.388(6) . ? C2 C1 1.536(6) . ? 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 O3S S3S C5S 106.1(2) . . ? O3S S3S C6S 106.3(3) . . ? C5S S3S C6S 98.8(3) . . ? O4S S4S C8S 106.3(2) . . ? O4S S4S C7S 106.1(2) . . ? C8S S4S C7S 97.3(2) . . ? O1S S1S C2S 105.1(2) . . ? O1S S1S C1S 105.8(2) . . ? C1S S1S C2S 98.4(2) . . ? O2S S2S C4S 107.3(2) . . ? O2S S2S C3S 105.5(3) . . ? C4S S2S C3S 97.1(3) . . ? C6 C5 I2 119.2(3) . . ? C4 C5 I2 119.1(3) . . ? C4 C5 C6 121.7(4) . . ? C5 C6 C7 118.5(4) . . ? C5 C6 N2 120.2(4) . . ? C7 C6 N2 121.2(4) . . ? O3 C8 N1 122.0(4) . . ? O3 C8 C9 122.9(4) . . ? N1 C8 C9 115.1(4) . . ? C4 C3 I1 119.4(3) . . ? C2 C3 I1 120.5(3) . . ? C2 C3 C4 120.2(4) . . ? C5 C4 C3 118.8(4) . . ? C5 C4 N1 121.2(4) . . ? C3 C4 N1 120.0(4) . . ? C8 N1 C4 121.7(3) . . ? O4 C10 N2 122.1(4) . . ? O4 C10 C11 122.6(4) . . ? N2 C10 C11 115.4(4) . . ? C6 C7 I3 118.5(3) . . ? C2 C7 I3 120.8(3) . . ? C2 C7 C6 120.7(4) . . ? C3 C2 C1 120.7(4) . . ? C7 C2 C3 120.1(4) . . ? C7 C2 C1 119.1(4) . . ? C10 N2 C6 121.0(4) . . ? O2 C1 O1 126.3(5) . . ? O2 C1 C2 123.0(4) . . ? O1 C1 C2 110.7(4) . . ?