# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Sotiris Hadjikakou' _publ_contact_author_email shadjika@uoi.gr _publ_section_title ; Stabilization of poly-iodides: structural influences of the cationic disulfides of 2-mercapto-3,4,5, 6-tetrahydro-pyrimidine and 2-mercatpo-pyrimidine. ; loop_ _publ_author_name S.Hadjikakou A.Owczarzak M.Kubicki N.Kourkoumelis # Attachment '- 4.cif' data_shelxld _database_code_depnum_ccdc_archive 'CCDC 843961' #TrackingRef '- 4.cif' _audit_update_record ; 2011-12-18 # Formatted by publCIF ; _database_code_CSD 843961 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H5 I2 N2 S' _chemical_formula_weight 366.96 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2469(2) _cell_length_b 11.3129(2) _cell_length_c 10.3137(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.79(1) _cell_angle_gamma 90.00 _cell_volume 921.21(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19897 _cell_measurement_theta_min 3.1401 _cell_measurement_theta_max 27.9195 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 6.982 _exptl_absorpt_correction_T_min 0.33015 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 293(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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1544 _diffrn_reflns_number 26655 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.98 _reflns_number_total 2120 _reflns_number_gt 1922 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0160P)^2^+1.0236P] 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 2120 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0241 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0421 _refine_ls_wR_factor_gt 0.0412 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I2 I 0.36684(2) 0.410179(17) 0.236430(19) 0.03934(7) Uani 1 1 d . . . I1 I 0.10944(3) 0.47884(2) 0.42347(2) 0.05150(8) Uani 1 1 d . . . S2 S 0.30606(13) 0.33474(9) 0.86826(10) 0.0604(2) Uani 1 1 d . . . N1 N 0.4585(3) 0.3091(2) 0.6748(3) 0.0387(5) Uani 1 1 d . . . N3 N 0.2372(3) 0.1855(2) 0.6610(3) 0.0432(6) Uani 1 1 d . . . C4 C 0.2628(4) 0.1326(3) 0.5539(3) 0.0450(7) Uani 1 1 d . . . C2 C 0.3333(4) 0.2757(3) 0.7312(3) 0.0378(6) Uani 1 1 d . . . C6 C 0.4890(4) 0.2585(3) 0.5683(3) 0.0415(7) Uani 1 1 d . . . C5 C 0.3918(4) 0.1656(3) 0.5051(3) 0.0449(7) Uani 1 1 d . . . H6 H 0.579(4) 0.293(3) 0.543(3) 0.053(10) Uiso 1 1 d . . . H3 H 0.171(4) 0.162(3) 0.689(3) 0.041(10) Uiso 1 1 d . . . H5 H 0.406(4) 0.129(3) 0.427(4) 0.056(10) Uiso 1 1 d . . . H1 H 0.510(5) 0.369(4) 0.714(4) 0.059(11) Uiso 1 1 d . . . H4 H 0.191(5) 0.072(4) 0.517(4) 0.064(11) 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 I2 0.03966(11) 0.04060(11) 0.04323(11) 0.00097(8) 0.02063(8) -0.00122(7) I1 0.04127(12) 0.05882(14) 0.05633(14) 0.00076(10) 0.01717(10) 0.00340(9) S2 0.0691(6) 0.0651(6) 0.0577(5) -0.0212(4) 0.0353(5) -0.0152(4) N1 0.0370(12) 0.0385(13) 0.0412(14) -0.0028(11) 0.0123(10) -0.0075(10) N3 0.0404(14) 0.0464(15) 0.0464(15) -0.0035(12) 0.0184(12) -0.0134(12) C4 0.0509(18) 0.0391(16) 0.0431(17) -0.0044(14) 0.0106(14) -0.0083(14) C2 0.0377(14) 0.0374(15) 0.0393(15) -0.0012(12) 0.0127(12) -0.0030(11) C6 0.0385(15) 0.0461(17) 0.0421(17) 0.0051(13) 0.0150(13) 0.0023(13) C5 0.0516(18) 0.0441(17) 0.0406(17) -0.0033(13) 0.0159(14) 0.0008(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 I1 I1 2.7616(4) 3_566 ? S2 C2 1.637(3) . ? N1 C6 1.325(4) . ? N1 C2 1.376(4) . ? N3 C4 1.326(4) . ? N3 C2 1.364(4) . ? C4 C5 1.354(5) . ? C6 C5 1.368(5) . ? 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 C6 N1 C2 125.2(3) . . ? C4 N3 C2 124.9(3) . . ? N3 C4 C5 121.1(3) . . ? N3 C2 N1 111.9(3) . . ? N3 C2 S2 124.0(2) . . ? N1 C2 S2 124.1(2) . . ? N1 C6 C5 120.0(3) . . ? C4 C5 C6 116.8(3) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.577 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.079 # Attachment '- 3.CIF' data_shelxlc _database_code_depnum_ccdc_archive 'CCDC 843962' #TrackingRef '- 3.CIF' _database_code_CSD 843962 _diffrn_ambient_temperature 100(2) #Added by publCIF _audit_update_record ; 2011-12-16 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C96 H192 Cl6 I38 N48 S24' _chemical_formula_weight 7823.32 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' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnnm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 20.982(2) _cell_length_b 42.307(4) _cell_length_c 12.4442(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 11046.5(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 34508 _cell_measurement_theta_min 2.8833 _cell_measurement_theta_max 27.7179 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7208 _exptl_absorpt_coefficient_mu 5.662 _exptl_absorpt_correction_T_min 0.20525 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method '/w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50417 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 55 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.79 _reflns_number_total 12664 _reflns_number_gt 10382 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0203P)^2^+153.8940P] 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 12664 _refine_ls_number_parameters 525 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.91494(4) 0.15676(2) 0.0000 0.0445(2) Uani 1 2 d S . . I2 I 0.78336(4) 0.142024(18) 0.0000 0.02898(17) Uani 1 2 d S . . I3 I 0.64284(3) 0.125842(17) 0.0000 0.02379(15) Uani 1 2 d S . . I4 I 0.44329(3) 0.276337(16) 0.0000 0.02314(15) Uani 1 2 d S . . I5 I 0.41284(3) 0.209785(15) 0.0000 0.01640(13) Uani 1 2 d S . . I6 I 0.38031(3) 0.142425(15) 0.0000 0.01932(14) Uani 1 2 d S . . I7 I 0.90317(4) 0.134807(17) -0.5000 0.02874(17) Uani 1 2 d S . . I8 I 0.77335(4) 0.149543(15) -0.5000 0.02214(15) Uani 1 2 d S . . I9 I 0.62660(3) 0.165350(16) -0.5000 0.02305(15) Uani 1 2 d S . . I10 I 0.55660(3) 0.406680(16) 0.0000 0.02350(15) Uani 1 2 d S . . I11 I 0.69392(3) 0.392299(15) 0.0000 0.01752(14) Uani 1 2 d S . . I12 I 0.82798(3) 0.377941(16) 0.0000 0.02350(15) Uani 1 2 d S . . I13 I 1.02082(3) 0.068293(18) 0.0000 0.02728(16) Uani 1 2 d S . . I14 I 1.0000 0.0000 0.0000 0.0204(2) Uani 1 4 d S . . I15 I 0.48510(3) 0.068651(16) -0.5000 0.02340(15) Uani 1 2 d S . . I16 I 0.5000 0.0000 -0.5000 0.01985(19) Uani 1 4 d S . . I17 I 1.26867(3) 0.002887(17) 0.0000 0.02456(15) Uani 1 2 d S . . I18 I 0.63272(3) 0.284537(15) -0.5000 0.01582(13) Uani 1 2 d S . . I19 I 0.69842(3) 0.261272(14) 0.0000 0.01404(12) Uani 1 2 d S . . I20 I 1.22233(3) -0.028708(14) -0.5000 0.01394(13) Uani 1 2 d S . . Cl1 Cl 1.4719(3) 0.03844(13) 0.0000 0.0302(13) Uani 0.50 2 d SP . . Cl2 Cl 0.90441(11) 0.29174(6) 0.0000 0.0198(5) Uani 1 2 d S . . Cl3 Cl 1.0000 0.0000 -0.5000 0.0150(6) Uani 1 4 d S . . Cl4 Cl 1.19833(11) 0.10585(5) 0.0000 0.0141(4) Uani 1 2 d S . . N1A N 0.6292(3) 0.35727(13) 0.3148(5) 0.0160(12) Uani 1 1 d . . . H1A H 0.6448 0.3701 0.3637 0.019 Uiso 1 1 calc R . . N3A N 0.6499(3) 0.32011(13) 0.1859(5) 0.0147(12) Uani 1 1 d . . . H3A H 0.6780 0.3077 0.1544 0.018 Uiso 1 1 calc R . . N1B N 0.7613(3) 0.26497(13) 0.3252(5) 0.0154(12) Uani 1 1 d . . . H1B H 0.7367 0.2782 0.3608 0.018 Uiso 1 1 calc R . . N3B N 0.8353(3) 0.25695(13) 0.1912(5) 0.0166(12) Uani 1 1 d . . . H3B H 0.8626 0.2657 0.1464 0.020 Uiso 1 1 calc R . . N1C N 0.5550(3) 0.17736(13) -0.1791(5) 0.0153(12) Uani 1 1 d . . . H1C H 0.5629 0.1596 -0.1444 0.018 Uiso 1 1 calc R . . N3C N 0.4976(3) 0.20299(13) -0.3101(5) 0.0178(12) Uani 1 1 d . . . H3C H 0.4668 0.2019 -0.3578 0.021 Uiso 1 1 calc R . . N1D N 0.5713(3) 0.06308(14) -0.1886(5) 0.0259(15) Uani 1 1 d . . . H1D H 0.5428 0.0563 -0.1421 0.031 Uiso 1 1 calc R . . N3D N 0.6004(3) 0.10157(14) -0.3092(5) 0.0195(13) Uani 1 1 d . . . H3D H 0.5920 0.1201 -0.3379 0.023 Uiso 1 1 calc R . . N1E N 1.2555(3) 0.03468(13) -0.3210(5) 0.0162(12) Uani 1 1 d . . . N3E N 1.2701(3) 0.07266(13) -0.1906(5) 0.0191(13) Uani 1 1 d . . . H3E H 1.2522 0.0856 -0.1442 0.023 Uiso 1 1 calc R . . N1F N 1.0737(3) -0.03313(15) -0.3113(5) 0.0176(13) Uani 1 1 d . . . N3F N 1.1497(3) -0.02220(13) -0.1832(5) 0.0157(12) Uani 1 1 d . . . H3F H 1.1744 -0.0081 -0.1520 0.019 Uiso 1 1 calc R . . C2A C 0.6683(3) 0.33838(15) 0.2655(5) 0.0137(13) Uani 1 1 d . . . C4A C 0.5835(3) 0.31993(16) 0.1484(6) 0.0176(14) Uani 1 1 d . . . H4A2 H 0.5728 0.2989 0.1184 0.021 Uiso 1 1 calc R . . H4A1 H 0.5778 0.3359 0.0912 0.021 Uiso 1 1 calc R . . C5A C 0.5401(3) 0.32736(17) 0.2423(6) 0.0211(15) Uani 1 1 d . . . H5A2 H 0.5424 0.3102 0.2961 0.025 Uiso 1 1 calc R . . H5A1 H 0.4955 0.3290 0.2170 0.025 Uiso 1 1 calc R . . C6A C 0.5602(3) 0.35832(18) 0.2934(6) 0.0231(16) Uani 1 1 d . . . H6A2 H 0.5503 0.3761 0.2445 0.028 Uiso 1 1 calc R . . H6A1 H 0.5366 0.3616 0.3615 0.028 Uiso 1 1 calc R . . C2B C 0.7969(3) 0.27527(16) 0.2457(5) 0.0141(13) Uani 1 1 d . . . C4B C 0.8350(4) 0.22243(17) 0.2016(6) 0.0233(16) Uani 1 1 d . . . H4B2 H 0.8721 0.2156 0.2449 0.028 Uiso 1 1 calc R . . H4B1 H 0.8386 0.2126 0.1296 0.028 Uiso 1 1 calc R . . C5B C 0.7739(4) 0.21168(17) 0.2553(6) 0.0227(16) Uani 1 1 d . . . H5B1 H 0.7377 0.2142 0.2051 0.027 Uiso 1 1 calc R . . H5B2 H 0.7772 0.1890 0.2747 0.027 Uiso 1 1 calc R . . C6B C 0.7626(3) 0.23104(15) 0.3546(6) 0.0168(14) Uani 1 1 d . . . H6B1 H 0.7215 0.2249 0.3879 0.020 Uiso 1 1 calc R . . H6B2 H 0.7970 0.2271 0.4074 0.020 Uiso 1 1 calc R . . C2C C 0.5137(3) 0.17748(16) -0.2575(5) 0.0147(14) Uani 1 1 d . . . C4C C 0.5292(3) 0.23347(16) -0.2923(6) 0.0205(15) Uani 1 1 d . . . H4C2 H 0.5034 0.2466 -0.2429 0.025 Uiso 1 1 calc R . . H4C1 H 0.5334 0.2449 -0.3613 0.025 Uiso 1 1 calc R . . C5C C 0.5945(3) 0.22793(17) -0.2444(6) 0.0192(15) Uani 1 1 d . . . H5C2 H 0.6227 0.2181 -0.2986 0.023 Uiso 1 1 calc R . . H5C1 H 0.6135 0.2484 -0.2227 0.023 Uiso 1 1 calc R . . C6C C 0.5887(3) 0.20656(16) -0.1478(6) 0.0193(15) Uani 1 1 d . . . H6C2 H 0.6316 0.2013 -0.1201 0.023 Uiso 1 1 calc R . . H6C1 H 0.5648 0.2175 -0.0901 0.023 Uiso 1 1 calc R . . C2D C 0.5622(3) 0.09006(16) -0.2365(6) 0.0189(15) Uani 1 1 d . . . C4D C 0.6575(4) 0.08413(19) -0.3441(7) 0.0277(18) Uani 1 1 d . . . H4D1 H 0.6912 0.0992 -0.3661 0.033 Uiso 1 1 calc R . . H4D2 H 0.6469 0.0706 -0.4065 0.033 Uiso 1 1 calc R . . C5D C 0.6810(4) 0.0639(2) -0.2517(7) 0.034(2) Uani 1 1 d . . . H5D2 H 0.7168 0.0504 -0.2765 0.041 Uiso 1 1 calc R . . H5D1 H 0.6969 0.0776 -0.1932 0.041 Uiso 1 1 calc R . . C6D C 0.6285(5) 0.0434(2) -0.2104(7) 0.043(2) Uani 1 1 d . . . H6D2 H 0.6180 0.0270 -0.2642 0.051 Uiso 1 1 calc R . . H6D1 H 0.6423 0.0328 -0.1436 0.051 Uiso 1 1 calc R . . C2E C 1.2338(3) 0.05259(15) -0.2422(6) 0.0153(14) Uani 1 1 d . . . C4E C 1.3394(3) 0.07457(16) -0.2064(6) 0.0215(16) Uani 1 1 d . . . H4E2 H 1.3607 0.0782 -0.1365 0.026 Uiso 1 1 calc R . . H4E1 H 1.3496 0.0925 -0.2544 0.026 Uiso 1 1 calc R . . C5E C 1.3633(3) 0.04416(16) -0.2556(6) 0.0212(16) Uani 1 1 d . . . H5E1 H 1.3610 0.0269 -0.2019 0.025 Uiso 1 1 calc R . . H5E2 H 1.4083 0.0467 -0.2777 0.025 Uiso 1 1 calc R . . C6E C 1.3229(3) 0.03572(16) -0.3527(6) 0.0196(15) Uani 1 1 d . . . H6E2 H 1.3291 0.0517 -0.4099 0.023 Uiso 1 1 calc R . . H6E1 H 1.3361 0.0149 -0.3813 0.023 Uiso 1 1 calc R . . C2F C 1.1118(3) -0.01339(15) -0.2619(5) 0.0142(14) Uani 1 1 d . . . C4F C 1.1516(4) -0.05511(17) -0.1468(6) 0.0213(16) Uani 1 1 d . . . H4F2 H 1.1199 -0.0584 -0.0889 0.026 Uiso 1 1 calc R . . H4F1 H 1.1944 -0.0601 -0.1179 0.026 Uiso 1 1 calc R . . C5F C 1.1366(4) -0.07673(17) -0.2411(6) 0.0245(17) Uani 1 1 d . . . H5F1 H 1.1708 -0.0752 -0.2957 0.029 Uiso 1 1 calc R . . H5F2 H 1.1343 -0.0989 -0.2162 0.029 Uiso 1 1 calc R . . C6F C 1.0735(4) -0.06705(16) -0.2902(6) 0.0246(17) Uani 1 1 d . . . H6F1 H 1.0666 -0.0787 -0.3581 0.030 Uiso 1 1 calc R . . H6F2 H 1.0384 -0.0724 -0.2403 0.030 Uiso 1 1 calc R . . S2A S 0.74747(8) 0.33854(4) 0.31674(14) 0.0169(3) Uani 1 1 d . . . S2B S 0.79743(8) 0.31522(4) 0.20130(14) 0.0172(3) Uani 1 1 d . . . S2C S 0.47487(8) 0.14250(4) -0.30386(16) 0.0206(4) Uani 1 1 d . . . S2D S 0.49419(8) 0.11074(4) -0.18636(16) 0.0201(4) Uani 1 1 d . . . S2E S 1.15348(8) 0.05151(4) -0.19611(15) 0.0198(4) Uani 1 1 d . . . S2F S 1.10818(8) 0.02621(4) -0.31194(15) 0.0193(4) Uani 1 1 d . . . H1E H 1.232(3) 0.0254(16) -0.358(6) 0.009(19) Uiso 1 1 d . . . H1F H 1.054(4) -0.0268(17) -0.358(6) 0.02(2) 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 I1 0.0297(4) 0.0550(6) 0.0489(5) 0.000 0.000 0.0199(4) I2 0.0359(4) 0.0274(4) 0.0237(4) 0.000 0.000 0.0145(3) I3 0.0300(4) 0.0251(4) 0.0163(3) 0.000 0.000 0.0064(3) I4 0.0190(3) 0.0208(3) 0.0296(4) 0.000 0.000 -0.0058(3) I5 0.0111(3) 0.0203(3) 0.0177(3) 0.000 0.000 -0.0006(2) I6 0.0171(3) 0.0176(3) 0.0232(3) 0.000 0.000 -0.0001(2) I7 0.0297(4) 0.0191(3) 0.0374(4) 0.000 0.000 -0.0027(3) I8 0.0342(4) 0.0127(3) 0.0195(3) 0.000 0.000 0.0021(3) I9 0.0287(4) 0.0208(3) 0.0197(3) 0.000 0.000 0.0090(3) I10 0.0220(3) 0.0175(3) 0.0309(4) 0.000 0.000 0.0049(3) I11 0.0212(3) 0.0132(3) 0.0181(3) 0.000 0.000 -0.0018(2) I12 0.0210(3) 0.0178(3) 0.0317(4) 0.000 0.000 -0.0005(3) I13 0.0185(3) 0.0326(4) 0.0308(4) 0.000 0.000 -0.0040(3) I14 0.0121(4) 0.0313(5) 0.0178(5) 0.000 0.000 0.0018(4) I15 0.0243(4) 0.0215(3) 0.0245(4) 0.000 0.000 -0.0014(3) I16 0.0153(4) 0.0222(5) 0.0221(5) 0.000 0.000 -0.0018(4) I17 0.0264(4) 0.0290(4) 0.0183(3) 0.000 0.000 0.0021(3) I18 0.0159(3) 0.0193(3) 0.0123(3) 0.000 0.000 -0.0011(2) I19 0.0158(3) 0.0147(3) 0.0117(3) 0.000 0.000 -0.0013(2) I20 0.0165(3) 0.0132(3) 0.0121(3) 0.000 0.000 -0.0003(2) Cl1 0.064(4) 0.023(3) 0.003(2) 0.000 0.000 0.003(3) Cl2 0.0128(11) 0.0346(14) 0.0120(11) 0.000 0.000 -0.0042(10) Cl3 0.0128(15) 0.0187(16) 0.0136(15) 0.000 0.000 0.0012(12) Cl4 0.0172(11) 0.0132(10) 0.0118(10) 0.000 0.000 0.0020(8) N1A 0.021(3) 0.013(3) 0.014(3) -0.004(2) -0.001(2) 0.001(2) N3A 0.015(3) 0.015(3) 0.015(3) -0.004(2) 0.001(2) 0.003(2) N1B 0.015(3) 0.019(3) 0.013(3) 0.003(2) 0.001(2) 0.000(2) N3B 0.013(3) 0.021(3) 0.016(3) 0.001(2) 0.003(2) 0.000(2) N1C 0.020(3) 0.011(3) 0.015(3) 0.001(2) -0.002(2) -0.001(2) N3C 0.013(3) 0.020(3) 0.021(3) -0.001(3) -0.005(2) 0.004(2) N1D 0.037(4) 0.018(3) 0.022(3) 0.003(3) 0.004(3) 0.011(3) N3D 0.020(3) 0.017(3) 0.022(3) -0.001(3) -0.002(3) 0.006(2) N1E 0.021(3) 0.013(3) 0.015(3) -0.006(2) 0.000(3) -0.005(2) N3E 0.028(3) 0.013(3) 0.017(3) -0.008(2) 0.007(3) -0.006(2) N1F 0.015(3) 0.023(3) 0.015(3) 0.001(3) -0.005(3) -0.002(2) N3F 0.012(3) 0.021(3) 0.014(3) -0.002(2) -0.001(2) -0.003(2) C2A 0.018(3) 0.014(3) 0.009(3) 0.005(3) -0.001(3) -0.006(3) C4A 0.019(3) 0.017(3) 0.017(3) -0.006(3) -0.004(3) 0.001(3) C5A 0.016(3) 0.024(4) 0.023(4) -0.003(3) -0.006(3) -0.001(3) C6A 0.018(4) 0.031(4) 0.021(4) -0.008(3) -0.001(3) 0.006(3) C2B 0.010(3) 0.018(3) 0.014(3) -0.001(3) -0.004(3) -0.003(3) C4B 0.032(4) 0.021(4) 0.016(4) 0.000(3) 0.005(3) 0.006(3) C5B 0.031(4) 0.021(4) 0.016(4) 0.002(3) -0.001(3) -0.001(3) C6B 0.016(3) 0.017(3) 0.017(4) 0.006(3) 0.001(3) 0.003(3) C2C 0.009(3) 0.020(3) 0.015(3) -0.003(3) 0.001(3) 0.004(3) C4C 0.027(4) 0.013(3) 0.022(4) 0.002(3) -0.004(3) 0.002(3) C5C 0.022(4) 0.020(3) 0.015(3) 0.000(3) -0.002(3) -0.004(3) C6C 0.021(3) 0.021(4) 0.017(4) 0.000(3) -0.006(3) -0.005(3) C2D 0.021(3) 0.017(3) 0.019(4) -0.005(3) -0.003(3) 0.004(3) C4D 0.024(4) 0.031(4) 0.028(4) 0.003(4) 0.006(3) 0.017(3) C5D 0.034(5) 0.048(5) 0.022(4) -0.006(4) -0.002(4) 0.022(4) C6D 0.064(6) 0.037(5) 0.027(5) 0.001(4) -0.001(5) 0.033(5) C2E 0.017(3) 0.014(3) 0.015(3) 0.001(3) 0.001(3) 0.000(3) C4E 0.026(4) 0.014(3) 0.024(4) -0.009(3) 0.008(3) -0.011(3) C5E 0.019(3) 0.020(4) 0.025(4) -0.006(3) 0.007(3) -0.008(3) C6E 0.024(4) 0.015(3) 0.020(4) -0.006(3) 0.008(3) -0.005(3) C2F 0.013(3) 0.016(3) 0.014(3) 0.000(3) 0.002(3) 0.002(3) C4F 0.022(4) 0.025(4) 0.017(4) 0.009(3) -0.003(3) -0.002(3) C5F 0.031(4) 0.018(4) 0.025(4) 0.002(3) -0.007(4) -0.001(3) C6F 0.034(4) 0.017(4) 0.023(4) 0.002(3) -0.006(3) -0.009(3) S2A 0.0161(8) 0.0171(8) 0.0176(9) -0.0041(7) -0.0014(7) -0.0035(6) S2B 0.0173(8) 0.0165(8) 0.0179(9) 0.0000(7) 0.0037(7) -0.0042(6) S2C 0.0153(8) 0.0197(9) 0.0268(10) -0.0060(8) -0.0080(8) 0.0015(7) S2D 0.0158(8) 0.0163(8) 0.0284(10) -0.0015(7) 0.0029(8) -0.0006(6) S2E 0.0176(8) 0.0195(9) 0.0222(9) -0.0088(8) 0.0012(7) 0.0013(7) S2F 0.0203(9) 0.0167(9) 0.0209(9) -0.0024(7) -0.0053(7) 0.0023(7) _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 I2 2.8305(12) . ? I2 I3 3.0269(11) . ? I4 I5 2.8872(9) . ? I5 I6 2.9304(9) . ? I7 I8 2.7945(11) . ? I8 I9 3.1509(10) . ? I10 I11 2.9449(9) . ? I11 I12 2.8777(10) . ? I13 I14 2.9221(8) . ? I14 I13 2.9221(8) 5_755 ? I15 I16 2.9212(7) . ? I16 I15 2.9212(7) 5_654 ? N1A C2A 1.300(8) . ? N1A C6A 1.473(9) . ? N3A C2A 1.314(8) . ? N3A C4A 1.469(8) . ? N1B C2B 1.314(8) . ? N1B C6B 1.482(8) . ? N3B C2B 1.309(8) . ? N3B C4B 1.466(9) . ? N1C C2C 1.306(8) . ? N1C C6C 1.476(8) . ? N3C C2C 1.306(9) . ? N3C C4C 1.467(9) . ? N1D C2D 1.302(9) . ? N1D C6D 1.485(10) . ? N3D C2D 1.303(9) . ? N3D C4D 1.471(8) . ? N1E C2E 1.320(9) . ? N1E C6E 1.470(9) . ? N3E C2E 1.310(8) . ? N3E C4E 1.470(9) . ? N1F C2F 1.309(9) . ? N1F C6F 1.459(9) . ? N3F C2F 1.316(8) . ? N3F C4F 1.465(9) . ? C2A S2A 1.779(7) . ? C4A C5A 1.515(10) . ? C5A C6A 1.516(10) . ? C2B S2B 1.778(7) . ? C4B C5B 1.517(10) . ? C5B C6B 1.502(10) . ? C2C S2C 1.785(7) . ? C4C C5C 1.511(9) . ? C5C C6C 1.509(10) . ? C2D S2D 1.787(7) . ? C4D C5D 1.517(11) . ? C5D C6D 1.492(13) . ? C2E S2E 1.780(7) . ? C4E C5E 1.510(9) . ? C5E C6E 1.518(10) . ? C2F S2F 1.789(7) . ? C4F C5F 1.521(10) . ? C5F C6F 1.514(10) . ? S2A S2B 2.034(2) . ? S2C S2D 2.027(3) . ? S2E S2F 2.032(3) . ? 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 I1 I2 I3 179.66(4) . . ? I4 I5 I6 179.32(3) . . ? I7 I8 I9 179.36(3) . . ? I12 I11 I10 179.74(3) . . ? I13 I14 I13 180.000(4) . 5_755 ? I15 I16 I15 180.0 5_654 . ? C2A N1A C6A 123.6(6) . . ? C2A N3A C4A 121.3(6) . . ? C2B N1B C6B 119.8(6) . . ? C2B N3B C4B 122.8(6) . . ? C2C N1C C6C 120.8(6) . . ? C2C N3C C4C 122.3(6) . . ? C2D N1D C6D 121.7(7) . . ? C2D N3D C4D 121.2(6) . . ? C2E N1E C6E 121.0(6) . . ? C2E N3E C4E 123.1(6) . . ? C2F N1F C6F 123.0(6) . . ? C2F N3F C4F 121.0(6) . . ? N1A C2A N3A 122.2(6) . . ? N1A C2A S2A 114.7(5) . . ? N3A C2A S2A 123.1(5) . . ? N3A C4A C5A 109.0(5) . . ? C4A C5A C6A 109.6(6) . . ? N1A C6A C5A 108.9(6) . . ? N3B C2B N1B 123.0(6) . . ? N3B C2B S2B 113.5(5) . . ? N1B C2B S2B 123.6(5) . . ? N3B C4B C5B 109.9(6) . . ? C6B C5B C4B 109.5(6) . . ? N1B C6B C5B 109.2(6) . . ? N3C C2C N1C 123.3(6) . . ? N3C C2C S2C 113.9(5) . . ? N1C C2C S2C 122.8(5) . . ? N3C C4C C5C 109.4(5) . . ? C6C C5C C4C 109.5(6) . . ? N1C C6C C5C 109.2(6) . . ? N1D C2D N3D 123.7(7) . . ? N1D C2D S2D 112.7(6) . . ? N3D C2D S2D 123.5(5) . . ? N3D C4D C5D 109.0(6) . . ? C6D C5D C4D 110.3(7) . . ? N1D C6D C5D 109.7(7) . . ? N3E C2E N1E 122.4(6) . . ? N3E C2E S2E 114.2(5) . . ? N1E C2E S2E 123.4(5) . . ? N3E C4E C5E 109.6(5) . . ? C4E C5E C6E 109.8(6) . . ? N1E C6E C5E 109.3(6) . . ? N1F C2F N3F 122.6(6) . . ? N1F C2F S2F 114.1(5) . . ? N3F C2F S2F 123.3(5) . . ? N3F C4F C5F 109.1(6) . . ? C6F C5F C4F 109.2(6) . . ? N1F C6F C5F 109.7(6) . . ? C2A S2A S2B 103.1(2) . . ? C2B S2B S2A 103.8(2) . . ? C2C S2C S2D 103.0(2) . . ? C2D S2D S2C 103.4(3) . . ? C2E S2E S2F 103.2(2) . . ? C2F S2F S2E 103.1(2) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 4.825 _refine_diff_density_min -2.754 _refine_diff_density_rms 0.213 # Attachment '- 2.cif' data_shelxlb _database_code_depnum_ccdc_archive 'CCDC 843963' #TrackingRef '- 2.cif' _audit_update_record ; 2011-12-18 # Formatted by publCIF ; _database_code_CSD 843963 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Cl I9 N8 S4' _chemical_formula_weight 1642.29 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' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.502(2) _cell_length_b 12.310(2) _cell_length_c 12.354(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.59(1) _cell_angle_gamma 90.00 _cell_volume 2050.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3487 _cell_measurement_theta_min 2.4827 _cell_measurement_theta_max 28.9555 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 7.094 _exptl_absorpt_correction_T_min 0.66470 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1544 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14097 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.1860 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 29.04 _reflns_number_total 4792 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0014P)^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 4792 _refine_ls_number_parameters 175 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0452 _refine_ls_wR_factor_gt 0.0430 _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_restrained_S_all 0.880 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.004 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 1.09180(5) 0.23090(5) 0.88230(5) 0.02539(18) Uani 1 1 d . . . I2 I 0.95808(5) 0.20376(4) 0.99801(5) 0.01559(15) Uani 1 1 d . . . I3 I 0.80974(4) 0.17319(4) 1.11621(5) 0.01678(16) Uani 1 1 d . . . I4 I 0.38086(4) 0.19442(4) 0.48237(5) 0.02115(16) Uani 1 1 d . . . I5 I 0.5000 0.0000 0.5000 0.0165(2) Uani 1 2 d S . . Cl1 Cl 0.5000 0.5000 0.5000 0.0172(8) Uani 1 2 d S . . S2A S 0.57398(17) 0.21653(15) 0.84339(18) 0.0152(5) Uani 1 1 d . . . S2B S 0.57189(17) 0.33287(16) 0.72619(18) 0.0163(6) Uani 1 1 d . . . C4B C 0.8145(6) 0.4746(6) 0.9717(6) 0.018(2) Uani 1 1 d U . . H4B H 0.8699 0.4339 1.0249 0.022 Uiso 1 1 calc R . . H4B' H 0.7938 0.5276 1.0161 0.022 Uiso 1 1 calc R . . C6A C 0.6960(6) -0.0781(6) 0.8448(7) 0.015(2) Uani 1 1 d U . . H6A H 0.6572 -0.1208 0.7774 0.019 Uiso 1 1 calc R . . H6A' H 0.7115 -0.1235 0.9134 0.019 Uiso 1 1 calc R . . N3A N 0.7081(5) 0.1312(5) 0.7599(5) 0.0120(17) Uani 1 1 d U . . H3A H 0.7125 0.1963 0.7369 0.014 Uiso 1 1 calc R . . N3B N 0.7323(5) 0.4010(5) 0.9108(6) 0.0152(18) Uani 1 1 d U . . H3B H 0.7249 0.3425 0.9447 0.018 Uiso 1 1 calc R . . N1A N 0.6387(5) 0.0166(5) 0.8552(5) 0.0145(18) Uani 1 1 d . . . H1A H 0.5971 0.0092 0.8896 0.017 Uiso 1 1 calc R . . N1B N 0.6752(5) 0.5099(5) 0.7501(6) 0.0171(17) Uani 1 1 d . . . H1B H 0.6285 0.5230 0.6843 0.020 Uiso 1 1 calc R . . C2B C 0.6696(7) 0.4229(6) 0.8050(7) 0.008(2) Uani 1 1 d . . . C5A C 0.7902(7) -0.0409(6) 0.8321(7) 0.021(2) Uani 1 1 d . . . H5A H 0.8347 -0.0112 0.9055 0.025 Uiso 1 1 calc R . . H5A' H 0.8229 -0.1023 0.8124 0.025 Uiso 1 1 calc R . . C2A C 0.6485(7) 0.1125(6) 0.8141(7) 0.014(2) Uani 1 1 d . . . C6B C 0.7584(7) 0.5893(6) 0.7946(7) 0.019(2) Uani 1 1 d . . . H6B H 0.7392 0.6499 0.8319 0.023 Uiso 1 1 calc R . . H6B' H 0.7753 0.6171 0.7308 0.023 Uiso 1 1 calc R . . C4A C 0.7678(6) 0.0462(6) 0.7365(6) 0.017(2) Uani 1 1 d . . . H4A H 0.8293 0.0766 0.7357 0.020 Uiso 1 1 calc R . . H4A' H 0.7322 0.0139 0.6610 0.020 Uiso 1 1 calc R . . C5B C 0.8452(7) 0.5318(6) 0.8801(7) 0.026(3) Uani 1 1 d . . . H5B' H 0.8705 0.4788 0.8399 0.031 Uiso 1 1 calc R . . H5B H 0.8976 0.5836 0.9178 0.031 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 0.0222(4) 0.0294(4) 0.0298(4) -0.0006(3) 0.0158(4) 0.0009(3) I2 0.0146(4) 0.0139(3) 0.0190(3) -0.0025(2) 0.0070(3) 0.0000(3) I3 0.0193(4) 0.0144(3) 0.0185(4) -0.0002(3) 0.0092(3) 0.0007(3) I4 0.0209(4) 0.0129(3) 0.0305(4) -0.0066(3) 0.0104(3) 0.0006(3) I5 0.0151(6) 0.0149(4) 0.0207(5) -0.0037(4) 0.0079(5) -0.0009(4) Cl1 0.022(2) 0.0154(16) 0.0164(19) 0.0025(14) 0.0093(18) 0.0044(16) S2A 0.0177(15) 0.0110(11) 0.0213(13) 0.0027(10) 0.0125(12) 0.0044(11) S2B 0.0137(15) 0.0116(11) 0.0213(14) 0.0030(10) 0.0038(12) 0.0007(11) C4B 0.018(2) 0.018(2) 0.019(2) -0.0011(10) 0.0067(12) 0.0005(10) C6A 0.016(2) 0.015(2) 0.016(2) 0.0007(10) 0.0057(12) -0.0003(10) N3A 0.0120(19) 0.0117(19) 0.0126(19) 0.0009(10) 0.0049(11) 0.0002(10) N3B 0.015(2) 0.0148(19) 0.0158(19) 0.0004(10) 0.0058(11) -0.0008(10) N1A 0.009(5) 0.018(4) 0.020(5) 0.006(3) 0.009(4) 0.008(4) N1B 0.010(5) 0.018(4) 0.019(4) 0.000(4) 0.000(4) 0.003(4) C2B 0.014(6) 0.007(4) 0.005(5) -0.004(4) 0.004(5) -0.003(4) C5A 0.019(7) 0.017(5) 0.024(6) -0.003(4) 0.004(5) 0.005(5) C2A 0.017(7) 0.013(5) 0.019(6) 0.002(4) 0.014(5) 0.005(4) C6B 0.030(8) 0.012(5) 0.010(6) 0.002(4) 0.002(5) -0.010(5) C4A 0.013(6) 0.017(5) 0.018(6) 0.002(4) 0.004(5) 0.006(4) C5B 0.041(8) 0.026(6) 0.017(6) -0.015(4) 0.019(6) -0.013(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 I2 2.8205(7) . ? I2 I3 3.0354(7) . ? I4 I5 2.9128(5) . ? I5 I4 2.9128(5) 3_656 ? S2A C2A 1.797(7) . ? S2A S2B 2.029(3) . ? S2B C2B 1.780(8) . ? C4B N3B 1.465(9) . ? C4B C5B 1.532(9) . ? C6A N1A 1.465(8) . ? C6A C5A 1.503(10) . ? N3A C2A 1.293(8) . ? N3A C4A 1.454(8) . ? N3B C2B 1.316(9) . ? N1A C2A 1.314(8) . ? N1B C2B 1.286(8) . ? N1B C6B 1.492(9) . ? C5A C4A 1.539(9) . ? C6B C5B 1.491(11) . ? 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 I1 I2 I3 178.44(3) . . ? I4 I5 I4 180.00(2) 3_656 . ? C2A S2A S2B 102.2(2) . . ? C2B S2B S2A 104.4(3) . . ? N3B C4B C5B 107.9(6) . . ? N1A C6A C5A 109.5(6) . . ? C2A N3A C4A 122.3(6) . . ? C2B N3B C4B 121.2(6) . . ? C2A N1A C6A 122.4(6) . . ? C2B N1B C6B 123.4(8) . . ? N1B C2B N3B 122.6(8) . . ? N1B C2B S2B 114.9(7) . . ? N3B C2B S2B 122.5(6) . . ? C4A C5A C6A 110.4(7) . . ? N3A C2A N1A 123.3(7) . . ? N3A C2A S2A 122.9(6) . . ? N1A C2A S2A 113.8(6) . . ? N1B C6B C5B 107.9(6) . . ? N3A C4A C5A 108.8(6) . . ? C4B C5B C6B 110.0(8) . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.346 _refine_diff_density_min -1.305 _refine_diff_density_rms 0.226 # Attachment '- 1_tHPMT_HI_I2.cif' data_thpmthi _database_code_depnum_ccdc_archive 'CCDC 843964' #TrackingRef '- 1_tHPMT_HI_I2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H16 I3 N4 S2' _chemical_formula_weight 613.07 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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 12.21180(10) _cell_length_b 25.3633(2) _cell_length_c 5.69180(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1762.93(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12527 _cell_measurement_theta_min 2.9230 _cell_measurement_theta_max 27.8990 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 5.544 _exptl_absorpt_correction_T_min 0.46184 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1544 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7941 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.60 _reflns_number_total 3330 _reflns_number_gt 3215 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1322P)^2^+7.3374P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.97(7) _refine_ls_number_reflns 3330 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.76141(7) 0.77989(3) 0.06249(13) 0.0382(2) Uani 1 1 d . . . I2 I 1.14134(7) 0.92958(3) 0.24393(16) 0.0441(3) Uani 1 1 d . . . I3 I 1.39214(9) 0.97956(3) 0.1524(2) 0.0576(3) Uani 1 1 d . . . S2B S 1.0745(2) 0.78845(11) 0.4167(6) 0.0364(6) Uani 1 1 d . . . S2A S 1.0510(2) 0.82450(11) 0.7307(5) 0.0354(6) Uani 1 1 d . . . N3B N 0.9311(8) 0.7188(4) 0.6105(19) 0.036(2) Uani 1 1 d . . . H3B H 0.9168 0.7429 0.7123 0.043 Uiso 1 1 calc R . . N1A N 0.9481(10) 0.9129(4) 0.7989(19) 0.041(2) Uani 1 1 d . . . H1A H 0.9972 0.9148 0.9071 0.050 Uiso 1 1 calc R . . N3A N 0.8775(8) 0.8658(4) 0.4920(17) 0.033(2) Uani 1 1 d . . . H3A H 0.8803 0.8376 0.4081 0.040 Uiso 1 1 calc R . . N1B N 1.0389(11) 0.6901(4) 0.312(3) 0.051(3) Uani 1 1 d . . . H1B H 1.0949 0.6961 0.2251 0.061 Uiso 1 1 calc R . . C2A C 0.9475(10) 0.8722(4) 0.659(2) 0.031(2) Uani 1 1 d . . . C6B C 0.9852(15) 0.6378(5) 0.290(3) 0.055(4) Uani 1 1 d . . . H6B' H 1.0266 0.6114 0.3755 0.066 Uiso 1 1 calc R . . H6B H 0.9819 0.6275 0.1262 0.066 Uiso 1 1 calc R . . C5A C 0.7634(14) 0.9351(6) 0.665(3) 0.057(4) Uani 1 1 d . . . H5A' H 0.7143 0.9639 0.6269 0.068 Uiso 1 1 calc R . . H5A H 0.7261 0.9116 0.7731 0.068 Uiso 1 1 calc R . . C5B C 0.8704(15) 0.6423(6) 0.390(3) 0.057(4) Uani 1 1 d . . . H5B' H 0.8245 0.6615 0.2806 0.068 Uiso 1 1 calc R . . H5B H 0.8398 0.6073 0.4092 0.068 Uiso 1 1 calc R . . C4B C 0.8690(13) 0.6694(5) 0.617(3) 0.051(3) Uani 1 1 d . . . H4B' H 0.9001 0.6464 0.7361 0.061 Uiso 1 1 calc R . . H4B H 0.7939 0.6768 0.6611 0.061 Uiso 1 1 calc R . . C6A C 0.8662(16) 0.9563(5) 0.777(3) 0.057(4) Uani 1 1 d . . . H6A' H 0.8961 0.9846 0.6818 0.069 Uiso 1 1 calc R . . H6A H 0.8493 0.9704 0.9314 0.069 Uiso 1 1 calc R . . C2B C 1.0077(9) 0.7274(4) 0.454(2) 0.034(2) Uani 1 1 d . . . C4A C 0.7934(13) 0.9053(6) 0.442(3) 0.054(4) Uani 1 1 d . . . H4A' H 0.7287 0.8881 0.3791 0.064 Uiso 1 1 calc R . . H4A H 0.8203 0.9298 0.3249 0.064 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 0.0362(4) 0.0395(4) 0.0390(4) -0.0053(3) -0.0083(3) -0.0019(3) I2 0.0357(4) 0.0397(4) 0.0569(5) 0.0136(3) -0.0143(4) -0.0091(3) I3 0.0655(6) 0.0367(4) 0.0705(6) -0.0056(4) -0.0111(5) 0.0139(4) S2B 0.0327(13) 0.0319(12) 0.0447(15) -0.0035(11) 0.0099(12) -0.0082(10) S2A 0.0349(14) 0.0358(12) 0.0356(13) -0.0024(11) -0.0047(12) 0.0014(11) N3B 0.029(4) 0.030(4) 0.047(5) 0.001(4) 0.009(4) 0.002(4) N1A 0.050(6) 0.035(4) 0.039(5) -0.016(4) -0.006(5) -0.001(4) N3A 0.034(5) 0.034(4) 0.032(5) -0.001(3) -0.008(4) 0.000(4) N1B 0.045(6) 0.038(5) 0.068(8) -0.017(5) 0.009(6) -0.008(5) C2A 0.032(5) 0.031(4) 0.030(5) -0.004(4) 0.008(5) -0.008(4) C6B 0.073(10) 0.032(5) 0.061(9) -0.013(6) 0.010(8) -0.001(6) C5A 0.051(8) 0.052(7) 0.067(9) -0.017(7) -0.013(8) 0.019(7) C5B 0.064(10) 0.046(7) 0.060(9) -0.003(6) -0.007(8) -0.016(7) C4B 0.055(8) 0.037(6) 0.062(9) -0.001(6) 0.023(7) -0.012(6) C6A 0.097(13) 0.034(6) 0.041(7) -0.015(5) 0.000(8) 0.007(7) C2B 0.024(5) 0.035(5) 0.043(5) -0.006(5) -0.004(5) 0.005(4) C4A 0.058(9) 0.055(7) 0.048(7) -0.027(6) -0.014(7) 0.025(7) _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 I3 I3 2.831(2) 2_875 ? S2B C2B 1.763(12) . ? S2B S2A 2.028(4) . ? S2A C2A 1.797(12) . ? N3B C2B 1.309(16) . ? N3B C4B 1.466(15) . ? N1A C2A 1.304(14) . ? N1A C6A 1.493(19) . ? N3A C2A 1.287(16) . ? N3A C4A 1.464(16) . ? N1B C2B 1.302(16) . ? N1B C6B 1.483(16) . ? C6B C5B 1.52(3) . ? C5A C6A 1.51(2) . ? C5A C4A 1.52(2) . ? C5B C4B 1.46(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 C2B S2B S2A 102.9(4) . . ? C2A S2A S2B 101.6(4) . . ? C2B N3B C4B 122.0(10) . . ? C2A N1A C6A 121.9(11) . . ? C2A N3A C4A 121.5(10) . . ? C2B N1B C6B 125.0(13) . . ? N3A C2A N1A 123.8(12) . . ? N3A C2A S2A 123.3(8) . . ? N1A C2A S2A 112.9(9) . . ? N1B C6B C5B 108.0(11) . . ? C6A C5A C4A 109.3(13) . . ? C4B C5B C6B 112.2(14) . . ? C5B C4B N3B 111.9(12) . . ? N1A C6A C5A 109.3(10) . . ? N1B C2B N3B 120.6(11) . . ? N1B C2B S2B 115.4(10) . . ? N3B C2B S2B 124.0(9) . . ? N3A C4A C5A 110.3(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.576 _refine_diff_density_min -1.576 _refine_diff_density_rms 0.284