Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2011 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_HgI2(PTU)2.MeOH _database_code_depnum_ccdc_archive 'CCDC 773676' #TrackingRef '- Complex-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 Hg I2 N4 O3 S2' _chemical_formula_weight 822.86 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' Hg Hg -2.3894 9.2266 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5811(15) _cell_length_b 11.1302(19) _cell_length_c 13.3986(23) _cell_angle_alpha 72.850(10) _cell_angle_beta 81.900(10) _cell_angle_gamma 79.700(10) _cell_volume 1197.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 5209 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 25.96 _exptl_crystal_description platelet _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 9.198 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.173 _exptl_absorpt_correction_T_max 0.479 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17309 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 33.20 _reflns_number_total 8918 _reflns_number_gt 4049 _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^)+(0.0837P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8918 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1321 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1836 _refine_ls_wR_factor_gt 0.1567 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.035 _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 Hg Hg 0.49406(4) 0.08826(3) 0.79882(3) 0.06288(15) Uani 1 1 d . . . I1 I 0.21930(6) 0.25008(6) 0.78271(5) 0.05984(18) Uani 1 1 d . . . I2 I 0.56216(11) -0.15144(6) 0.90958(6) 0.0837(3) Uani 1 1 d . . . S1 S 0.5888(3) 0.05773(18) 0.59772(15) 0.0454(4) Uani 1 1 d . . . S2 S 0.7084(2) 0.23709(19) 0.78724(16) 0.0454(4) Uani 1 1 d . . . O1 O 0.3044(7) 0.4926(6) 0.4840(5) 0.0626(17) Uani 1 1 d . . . O2 O 1.1314(7) -0.0690(5) 0.6738(5) 0.0581(15) Uani 1 1 d . . . N1 N 0.4416(7) 0.2945(6) 0.5272(5) 0.0411(14) Uani 1 1 d . . . H1 H 0.3940 0.2821 0.5895 0.049 Uiso 1 1 calc R . . N2 N 0.6179(7) 0.2190(6) 0.4078(5) 0.0392(13) Uani 1 1 d . . . H2 H 0.6852 0.1592 0.3913 0.047 Uiso 1 1 calc R . . N3 N 0.9379(7) 0.0781(6) 0.7153(5) 0.0391(13) Uani 1 1 d . . . H3N H 0.9229 0.0262 0.7764 0.047 Uiso 1 1 calc R . . N4 N 0.8706(7) 0.2726(6) 0.5989(5) 0.0366(13) Uani 1 1 d . . . H4 H 0.8126 0.3458 0.5843 0.044 Uiso 1 1 calc R . . C1 C 0.5482(8) 0.1977(6) 0.5058(5) 0.0352(15) Uani 1 1 d . . . C2 C 0.4025(9) 0.4142(7) 0.4547(7) 0.0482(19) Uani 1 1 d . . . C3 C 0.4802(9) 0.4272(7) 0.3525(6) 0.0452(18) Uani 1 1 d . . . H3 H 0.4570 0.5019 0.2998 0.054 Uiso 1 1 calc R . . C4 C 0.5865(8) 0.3330(7) 0.3316(5) 0.0400(16) Uani 1 1 d . . . C5 C 0.6760(10) 0.3368(8) 0.2251(6) 0.0492(19) Uani 1 1 d . . . H5A H 0.7890 0.3269 0.2317 0.059 Uiso 1 1 calc R . . H5B H 0.6568 0.2650 0.2039 0.059 Uiso 1 1 calc R . . C6 C 0.6325(14) 0.4545(9) 0.1414(7) 0.068(3) Uani 1 1 d . . . H6A H 0.6461 0.5270 0.1638 0.082 Uiso 1 1 calc R . . H6B H 0.5210 0.4621 0.1314 0.082 Uiso 1 1 calc R . . C7 C 0.7320(17) 0.4583(13) 0.0365(8) 0.098(4) Uani 1 1 d . . . H7A H 0.8330 0.4832 0.0379 0.117 Uiso 1 1 calc R . . H7B H 0.6769 0.5186 -0.0192 0.117 Uiso 1 1 calc R . . H7C H 0.7484 0.3756 0.0251 0.117 Uiso 1 1 calc R . . C8 C 0.8474(8) 0.1922(7) 0.6951(6) 0.0359(15) Uani 1 1 d . . . C9 C 1.0539(9) 0.0377(7) 0.6445(6) 0.0408(16) Uani 1 1 d . . . C10 C 1.0710(9) 0.1265(7) 0.5453(6) 0.0439(18) Uani 1 1 d . . . H10 H 1.1451 0.1044 0.4937 0.053 Uiso 1 1 calc R . . C11 C 0.9833(8) 0.2422(7) 0.5233(6) 0.0395(16) Uani 1 1 d . . . C12 C 0.9969(9) 0.3446(8) 0.4224(6) 0.0464(18) Uani 1 1 d . . . H12A H 0.8917 0.3735 0.3981 0.056 Uiso 1 1 calc R . . H12B H 1.0313 0.4158 0.4366 0.056 Uiso 1 1 calc R . . C13 C 1.1061(11) 0.3102(9) 0.3363(7) 0.055(2) Uani 1 1 d . . . H13A H 1.0693 0.2418 0.3191 0.065 Uiso 1 1 calc R . . H13B H 1.2109 0.2785 0.3606 0.065 Uiso 1 1 calc R . . C14 C 1.1199(13) 0.4206(11) 0.2367(8) 0.075(3) Uani 1 1 d . . . H14A H 1.0154 0.4611 0.2181 0.090 Uiso 1 1 calc R . . H14B H 1.1764 0.3888 0.1805 0.090 Uiso 1 1 calc R . . H14C H 1.1764 0.4810 0.2492 0.090 Uiso 1 1 calc R . . C C 1.057(3) -0.156(2) 0.9519(14) 0.173(10) Uani 1 1 d . . . O O 0.9404(11) -0.0628(11) 0.9262(7) 0.112(3) Uani 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 Hg 0.0512(2) 0.0513(2) 0.0742(3) -0.00294(17) 0.00049(17) -0.00582(15) I1 0.0381(3) 0.0765(4) 0.0634(4) -0.0209(3) -0.0029(2) -0.0030(3) I2 0.1176(6) 0.0500(4) 0.0799(5) 0.0011(3) -0.0350(4) -0.0155(4) S1 0.0596(12) 0.0346(9) 0.0348(10) -0.0022(7) -0.0056(8) -0.0002(8) S2 0.0419(10) 0.0440(10) 0.0471(11) -0.0119(8) 0.0066(8) -0.0074(8) O1 0.059(4) 0.054(4) 0.058(4) -0.011(3) 0.001(3) 0.021(3) O2 0.064(4) 0.038(3) 0.057(4) -0.002(3) -0.003(3) 0.010(3) N1 0.043(3) 0.037(3) 0.034(3) -0.001(3) 0.004(3) -0.001(3) N2 0.044(3) 0.037(3) 0.032(3) -0.006(3) -0.003(2) -0.003(3) N3 0.041(3) 0.033(3) 0.038(3) -0.002(3) -0.003(3) -0.005(2) N4 0.033(3) 0.034(3) 0.040(3) -0.007(3) -0.002(2) -0.003(2) C1 0.042(4) 0.029(3) 0.032(4) -0.003(3) -0.011(3) -0.002(3) C2 0.044(4) 0.038(4) 0.057(5) -0.010(4) -0.009(4) 0.006(3) C3 0.046(4) 0.039(4) 0.039(4) 0.004(3) -0.011(3) 0.003(3) C4 0.041(4) 0.046(4) 0.026(3) 0.001(3) -0.007(3) -0.003(3) C5 0.051(4) 0.058(5) 0.033(4) -0.004(4) -0.001(3) -0.010(4) C6 0.092(7) 0.052(5) 0.048(5) 0.005(4) -0.004(5) -0.011(5) C7 0.124(10) 0.092(9) 0.051(6) 0.018(6) 0.011(6) -0.028(8) C8 0.028(3) 0.036(3) 0.043(4) -0.009(3) -0.005(3) -0.005(3) C9 0.039(4) 0.030(3) 0.050(5) -0.010(3) -0.002(3) -0.001(3) C10 0.038(4) 0.041(4) 0.045(4) -0.010(3) 0.009(3) 0.004(3) C11 0.031(3) 0.040(4) 0.045(4) -0.010(3) -0.001(3) -0.004(3) C12 0.045(4) 0.045(4) 0.044(4) -0.007(3) -0.002(3) -0.005(3) C13 0.057(5) 0.052(5) 0.047(5) -0.009(4) 0.010(4) -0.009(4) C14 0.074(6) 0.090(8) 0.043(5) 0.002(5) 0.009(5) -0.012(6) C 0.189(19) 0.170(18) 0.093(12) -0.005(12) -0.017(12) 0.095(16) O 0.098(6) 0.131(8) 0.078(6) 0.018(6) -0.004(5) -0.024(6) _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 Hg S2 2.647(2) . ? Hg I2 2.6483(9) . ? Hg I1 2.6916(8) . ? Hg S1 2.804(2) . ? S1 C1 1.691(7) . ? S2 C8 1.712(7) . ? O1 C2 1.213(9) . ? O2 C9 1.233(9) . ? N1 C1 1.355(9) . ? N1 C2 1.414(10) . ? N2 C1 1.335(9) . ? N2 C4 1.385(9) . ? N3 C8 1.339(9) . ? N3 C9 1.385(10) . ? N4 C8 1.346(9) . ? N4 C11 1.373(9) . ? C2 C3 1.415(12) . ? C3 C4 1.330(11) . ? C4 C5 1.515(10) . ? C5 C6 1.480(12) . ? C6 C7 1.532(15) . ? C9 C10 1.409(11) . ? C10 C11 1.343(10) . ? C11 C12 1.495(11) . ? C12 C13 1.478(11) . ? C13 C14 1.531(13) . ? C O 1.307(19) . ? 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 S2 Hg I2 115.89(5) . . ? S2 Hg I1 103.12(5) . . ? I2 Hg I1 131.71(3) . . ? S2 Hg S1 94.15(6) . . ? I2 Hg S1 98.68(5) . . ? I1 Hg S1 106.01(5) . . ? C1 S1 Hg 110.1(3) . . ? C8 S2 Hg 100.5(2) . . ? C1 N1 C2 124.9(6) . . ? C1 N2 C4 123.0(6) . . ? C8 N3 C9 124.6(6) . . ? C8 N4 C11 122.6(6) . . ? N2 C1 N1 116.1(6) . . ? N2 C1 S1 122.2(5) . . ? N1 C1 S1 121.8(5) . . ? O1 C2 N1 118.3(8) . . ? O1 C2 C3 126.8(7) . . ? N1 C2 C3 114.9(7) . . ? C4 C3 C2 120.2(7) . . ? C3 C4 N2 120.8(7) . . ? C3 C4 C5 124.6(7) . . ? N2 C4 C5 114.6(7) . . ? C6 C5 C4 114.6(8) . . ? C5 C6 C7 113.2(9) . . ? N3 C8 N4 117.4(6) . . ? N3 C8 S2 122.2(6) . . ? N4 C8 S2 120.4(5) . . ? O2 C9 N3 118.1(7) . . ? O2 C9 C10 127.1(7) . . ? N3 C9 C10 114.8(6) . . ? C11 C10 C9 121.9(7) . . ? C10 C11 N4 118.6(7) . . ? C10 C11 C12 126.0(7) . . ? N4 C11 C12 115.4(6) . . ? C13 C12 C11 116.4(7) . . ? C12 C13 C14 113.8(8) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 33.20 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 3.378 _refine_diff_density_min -2.707 _refine_diff_density_rms 0.183 data_HgI2(PTU)2.HgI2 _database_code_depnum_ccdc_archive 'CCDC 773945' #TrackingRef '- Complex-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Hg2 I4 N4 O2 S2' _chemical_formula_weight 1249.24 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' Hg Hg -2.3894 9.2266 '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 8.5338(6) _cell_length_b 12.8631(9) _cell_length_c 13.8786(10) _cell_angle_alpha 67.41(1) _cell_angle_beta 88.16(1) _cell_angle_gamma 75.56(1) _cell_volume 1358.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 5128 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.86 _exptl_crystal_description platelet _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 16.001 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.058 _exptl_absorpt_correction_T_max 0.326 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11385 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 29.38 _reflns_number_total 6673 _reflns_number_gt 4812 _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^)+(0.0414P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6673 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.65341(3) 0.27441(2) 0.20955(2) 0.05404(9) Uani 1 1 d . . . Hg2 Hg 1.24580(4) 0.00836(3) -0.49676(3) 0.07331(11) Uani 1 1 d . . . I1 I 0.48425(5) 0.11339(4) 0.27319(3) 0.05727(12) Uani 1 1 d . . . I2 I 0.65176(5) 0.47963(3) 0.21168(3) 0.05259(11) Uani 1 1 d . . . I3 I 1.33738(5) -0.18024(4) -0.53115(4) 0.05529(12) Uani 1 1 d . . . I4 I 1.15289(5) 0.19801(3) -0.46301(4) 0.05433(12) Uani 1 1 d . . . S1 S 0.97071(17) 0.14661(11) 0.30298(11) 0.0371(3) Uani 1 1 d . . . S2 S 0.7074(2) 0.26169(13) 0.02436(11) 0.0492(4) Uani 1 1 d . . . O1 O 1.1161(7) -0.1889(4) 0.2030(4) 0.0721(15) Uani 1 1 d . . . O2 O 0.8550(6) 0.6336(3) -0.0676(3) 0.0545(11) Uani 1 1 d . . . N1 N 1.0473(6) -0.0258(4) 0.2345(4) 0.0423(11) Uani 1 1 d . . . H1 H 1.0006 -0.0620 0.2883 0.051 Uiso 1 1 calc R . . N2 N 1.1151(5) 0.1404(3) 0.1306(3) 0.0343(10) Uani 1 1 d . . . H2 H 1.1161 0.2113 0.1169 0.041 Uiso 1 1 calc R . . N3 N 0.7814(6) 0.4682(4) -0.0366(3) 0.0403(11) Uani 1 1 d . . . H3N H 0.7520 0.4682 0.0232 0.048 Uiso 1 1 calc R . . N4 N 0.8100(5) 0.3820(3) -0.1540(3) 0.0351(10) Uani 1 1 d . . . H4 H 0.8091 0.3236 -0.1697 0.042 Uiso 1 1 calc R . . C1 C 1.0468(6) 0.0857(4) 0.2168(4) 0.0340(11) Uani 1 1 d . . . C2 C 1.1162(8) -0.0859(5) 0.1736(5) 0.0468(14) Uani 1 1 d . . . C3 C 1.1843(7) -0.0197(5) 0.0821(5) 0.0466(14) Uani 1 1 d . . . H3 H 1.2292 -0.0540 0.0361 0.056 Uiso 1 1 calc R . . C4 C 1.1842(7) 0.0910(4) 0.0617(4) 0.0371(12) Uani 1 1 d . . . C5 C 1.2510(8) 0.1687(5) -0.0304(5) 0.0480(14) Uani 1 1 d . . . H5A H 1.3366 0.1913 -0.0051 0.058 Uiso 1 1 calc R . . H5B H 1.1658 0.2390 -0.0656 0.058 Uiso 1 1 calc R . . C6 C 1.3182(9) 0.1195(6) -0.1101(5) 0.0557(16) Uani 1 1 d . . . H6A H 1.2327 0.0992 -0.1379 0.067 Uiso 1 1 calc R . . H6B H 1.4030 0.0486 -0.0758 0.067 Uiso 1 1 calc R . . C7 C 1.3868(11) 0.2040(7) -0.1997(6) 0.074(2) Uani 1 1 d . . . H7A H 1.3025 0.2732 -0.2355 0.088 Uiso 1 1 calc R . . H7B H 1.4292 0.1682 -0.2477 0.088 Uiso 1 1 calc R . . H7C H 1.4722 0.2239 -0.1727 0.088 Uiso 1 1 calc R . . C8 C 0.7692(6) 0.3762(4) -0.0580(4) 0.0344(11) Uani 1 1 d . . . C9 C 0.8372(7) 0.5632(4) -0.1024(5) 0.0406(13) Uani 1 1 d . . . C10 C 0.8671(7) 0.5656(4) -0.2054(4) 0.0418(13) Uani 1 1 d . . . H10 H 0.8960 0.6290 -0.2556 0.050 Uiso 1 1 calc R . . C11 C 0.8533(6) 0.4765(4) -0.2296(4) 0.0350(11) Uani 1 1 d . . . C12 C 0.8800(7) 0.4701(5) -0.3347(4) 0.0421(13) Uani 1 1 d . . . H12A H 0.9483 0.3940 -0.3258 0.050 Uiso 1 1 calc R . . H12B H 0.9358 0.5281 -0.3757 0.050 Uiso 1 1 calc R . . C13 C 0.7200(9) 0.4909(7) -0.3931(5) 0.0615(18) Uani 1 1 d . . . H13A H 0.6686 0.4292 -0.3545 0.074 Uiso 1 1 calc R . . H13B H 0.6485 0.5641 -0.3966 0.074 Uiso 1 1 calc R . . C14 C 0.7426(9) 0.4947(7) -0.5029(5) 0.070(2) Uani 1 1 d . . . H14A H 0.7807 0.5616 -0.5439 0.084 Uiso 1 1 calc R . . H14B H 0.6409 0.4996 -0.5341 0.084 Uiso 1 1 calc R . . H14C H 0.8206 0.4252 -0.5002 0.084 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 Hg1 0.06938(18) 0.04053(13) 0.05265(16) -0.01541(11) 0.00444(12) -0.01920(11) Hg2 0.0759(2) 0.05767(18) 0.0957(3) -0.04143(18) 0.00847(18) -0.01485(15) I1 0.0566(3) 0.0624(3) 0.0489(3) -0.0070(2) -0.00283(19) -0.0313(2) I2 0.0667(3) 0.0393(2) 0.0538(3) -0.02330(19) 0.0129(2) -0.00975(18) I3 0.0565(3) 0.0462(2) 0.0611(3) -0.0208(2) 0.0039(2) -0.00961(19) I4 0.0629(3) 0.0421(2) 0.0581(3) -0.01790(19) 0.0074(2) -0.01672(19) S1 0.0417(7) 0.0341(7) 0.0370(8) -0.0179(6) 0.0008(6) -0.0053(5) S2 0.0860(11) 0.0384(7) 0.0303(7) -0.0104(6) 0.0068(7) -0.0330(8) O1 0.127(5) 0.036(2) 0.071(3) -0.031(2) 0.041(3) -0.039(3) O2 0.090(3) 0.035(2) 0.050(3) -0.0211(19) 0.006(2) -0.027(2) N1 0.059(3) 0.032(2) 0.043(3) -0.018(2) 0.015(2) -0.021(2) N2 0.044(3) 0.026(2) 0.036(3) -0.0155(19) 0.004(2) -0.0083(18) N3 0.065(3) 0.035(2) 0.029(2) -0.018(2) 0.008(2) -0.020(2) N4 0.049(3) 0.026(2) 0.033(2) -0.0132(18) 0.007(2) -0.0121(19) C1 0.032(3) 0.031(3) 0.043(3) -0.018(2) -0.003(2) -0.007(2) C2 0.064(4) 0.037(3) 0.049(4) -0.024(3) 0.009(3) -0.017(3) C3 0.059(4) 0.041(3) 0.049(4) -0.029(3) 0.010(3) -0.012(3) C4 0.044(3) 0.035(3) 0.037(3) -0.018(2) 0.003(2) -0.011(2) C5 0.064(4) 0.040(3) 0.045(4) -0.022(3) 0.013(3) -0.016(3) C6 0.074(4) 0.051(4) 0.047(4) -0.024(3) 0.012(3) -0.019(3) C7 0.108(6) 0.067(5) 0.055(5) -0.031(4) 0.036(4) -0.030(4) C8 0.042(3) 0.029(3) 0.031(3) -0.009(2) -0.003(2) -0.010(2) C9 0.051(3) 0.028(3) 0.043(3) -0.012(2) 0.001(3) -0.013(2) C10 0.054(3) 0.027(3) 0.043(3) -0.008(2) 0.009(3) -0.017(2) C11 0.041(3) 0.031(3) 0.032(3) -0.010(2) 0.007(2) -0.011(2) C12 0.056(4) 0.037(3) 0.033(3) -0.015(2) 0.011(3) -0.012(3) C13 0.067(4) 0.081(5) 0.040(4) -0.025(4) 0.017(3) -0.025(4) C14 0.089(6) 0.085(6) 0.045(4) -0.033(4) 0.010(4) -0.028(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 Hg1 I2 2.6479(5) . ? Hg1 S2 2.6559(15) . ? Hg1 I1 2.6754(5) . ? Hg1 S1 2.8433(14) . ? Hg2 I3 2.5776(5) . ? Hg2 I4 2.5861(5) . ? S1 C1 1.698(5) . ? S2 C8 1.676(5) . ? O1 C2 1.227(7) . ? O2 C9 1.219(6) . ? N1 C1 1.358(6) . ? N1 C2 1.379(7) . ? N2 C1 1.334(7) . ? N2 C4 1.382(6) . ? N3 C8 1.354(6) . ? N3 C9 1.400(7) . ? N4 C8 1.345(7) . ? N4 C11 1.391(6) . ? C2 C3 1.429(9) . ? C3 C4 1.341(7) . ? C4 C5 1.488(8) . ? C5 C6 1.506(8) . ? C6 C7 1.518(9) . ? C9 C10 1.434(8) . ? C10 C11 1.345(7) . ? C11 C12 1.500(7) . ? C12 C13 1.521(9) . ? C13 C14 1.513(8) . ? 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 I2 Hg1 S2 113.61(3) . . ? I2 Hg1 I1 140.852(18) . . ? S2 Hg1 I1 95.28(3) . . ? I2 Hg1 S1 99.58(3) . . ? S2 Hg1 S1 95.92(5) . . ? I1 Hg1 S1 103.21(3) . . ? I3 Hg2 I4 179.72(2) . . ? C1 S1 Hg1 101.83(18) . . ? C8 S2 Hg1 111.70(19) . . ? C1 N1 C2 125.6(5) . . ? C1 N2 C4 124.5(4) . . ? C8 N3 C9 126.4(5) . . ? C8 N4 C11 124.2(4) . . ? N2 C1 N1 115.4(4) . . ? N2 C1 S1 123.4(4) . . ? N1 C1 S1 121.1(4) . . ? O1 C2 N1 118.2(6) . . ? O1 C2 C3 126.9(5) . . ? N1 C2 C3 114.9(5) . . ? C4 C3 C2 121.0(5) . . ? C3 C4 N2 118.5(5) . . ? C3 C4 C5 126.1(5) . . ? N2 C4 C5 115.4(4) . . ? C4 C5 C6 116.5(5) . . ? C5 C6 C7 112.7(5) . . ? N4 C8 N3 114.8(5) . . ? N4 C8 S2 120.2(4) . . ? N3 C8 S2 125.0(4) . . ? O2 C9 N3 118.1(5) . . ? O2 C9 C10 127.3(5) . . ? N3 C9 C10 114.5(5) . . ? C11 C10 C9 120.2(5) . . ? C10 C11 N4 119.5(5) . . ? C10 C11 C12 124.8(5) . . ? N4 C11 C12 115.7(4) . . ? C11 C12 C13 111.2(5) . . ? C14 C13 C12 112.2(6) . . ? _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 29.38 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 1.617 _refine_diff_density_min -2.005 _refine_diff_density_rms 0.173 data_Hg2I4(MeImSH)2 _database_code_depnum_ccdc_archive 'CCDC 773946' #TrackingRef '- Complex-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Hg2 I4 N4 S2' _chemical_formula_weight 1137.12 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' Hg Hg -2.3894 9.2266 '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 5.5676(7) _cell_length_b 9.2909(11) _cell_length_c 10.5376(13) _cell_angle_alpha 102.520(13) _cell_angle_beta 90.210(10) _cell_angle_gamma 100.330(10) _cell_volume 522.99(11) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.97 _cell_measurement_theta_max 25.96 _exptl_crystal_description pseudoprism _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 20.758 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.095 _exptl_absorpt_correction_T_max 0.288 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4606 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2034 _reflns_number_gt 1860 _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^)+(0.1025P)^2^+2.7019P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2034 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1518 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 C1 C 0.6241(18) 0.7121(12) 0.1718(10) 0.029(2) Uani 1 1 d . . . C3 C 0.525(2) 0.9385(14) 0.2117(15) 0.047(3) Uani 1 1 d . . . H3 H 0.5260 1.0391 0.2483 0.056 Uiso 1 1 calc R . . C2 C 0.369(2) 0.8477(16) 0.1131(14) 0.049(3) Uani 1 1 d . . . H2 H 0.2457 0.8749 0.0686 0.059 Uiso 1 1 calc R . . C4 C 0.869(3) 0.9019(15) 0.3496(14) 0.051(3) Uani 1 1 d . . . H4A H 0.9598 0.8236 0.3506 0.061 Uiso 1 1 calc R . . H4B H 0.7939 0.9262 0.4316 0.061 Uiso 1 1 calc R . . H4C H 0.9767 0.9892 0.3353 0.061 Uiso 1 1 calc R . . N2 N 0.6808(16) 0.8513(10) 0.2459(9) 0.0328(18) Uani 1 1 d . . . N1 N 0.4318(17) 0.7099(11) 0.0944(10) 0.039(2) Uani 1 1 d . . . H1 H 0.3576 0.6315 0.0399 0.047 Uiso 1 1 calc R . . S1 S 0.7815(5) 0.5669(3) 0.1734(3) 0.0361(6) Uani 1 1 d . . . I1 I 0.11299(14) 0.23522(9) 0.16842(8) 0.0476(3) Uani 1 1 d . . . I2 I 0.69163(15) 0.32614(8) 0.51108(8) 0.0430(3) Uani 1 1 d . . . Hg Hg 0.49482(10) 0.42797(5) 0.30989(5) 0.0502(2) Uani 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 C1 0.031(5) 0.034(5) 0.023(5) 0.004(4) 0.004(4) 0.009(4) C3 0.041(6) 0.033(6) 0.069(9) 0.007(6) -0.001(6) 0.015(5) C2 0.050(7) 0.052(7) 0.050(7) 0.016(6) -0.010(6) 0.016(6) C4 0.062(8) 0.036(6) 0.046(7) -0.003(5) -0.019(6) 0.000(5) N2 0.034(4) 0.028(4) 0.035(5) 0.002(4) -0.007(4) 0.008(3) N1 0.035(5) 0.041(5) 0.034(5) -0.008(4) -0.006(4) 0.011(4) S1 0.0410(14) 0.0289(12) 0.0392(15) 0.0040(11) 0.0025(11) 0.0128(10) I1 0.0460(5) 0.0448(5) 0.0491(5) 0.0054(4) -0.0043(4) 0.0070(3) I2 0.0583(5) 0.0380(4) 0.0384(5) 0.0070(3) 0.0021(3) 0.0256(4) Hg 0.0711(4) 0.0373(3) 0.0390(4) 0.0089(2) -0.0016(2) 0.0007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.338(14) . ? C1 N2 1.340(13) . ? C1 S1 1.738(10) . ? C3 C2 1.378(19) . ? C3 N2 1.383(14) . ? C2 N1 1.361(17) . ? C4 N2 1.450(15) . ? S1 Hg 2.523(3) . ? I1 Hg 2.7208(10) . ? I2 Hg 2.7956(10) . ? I2 Hg 2.9752(10) 2_666 ? Hg I2 2.9752(10) 2_666 ? 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 N1 C1 N2 106.7(9) . . ? N1 C1 S1 127.5(8) . . ? N2 C1 S1 125.7(8) . . ? C2 C3 N2 106.9(11) . . ? N1 C2 C3 105.7(10) . . ? C1 N2 C3 109.4(9) . . ? C1 N2 C4 125.6(9) . . ? C3 N2 C4 125.0(10) . . ? C1 N1 C2 111.2(10) . . ? C1 S1 Hg 97.9(3) . . ? Hg I2 Hg 85.96(2) . 2_666 ? S1 Hg I1 113.17(7) . . ? S1 Hg I2 118.81(7) . . ? I1 Hg I2 115.42(3) . . ? S1 Hg I2 102.82(6) . 2_666 ? I1 Hg I2 109.33(3) . 2_666 ? I2 Hg I2 94.04(2) . 2_666 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.557 _refine_diff_density_min -1.988 _refine_diff_density_rms 0.391