data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Edward Tiekink' 'Chian Sing Lai' _publ_contact_author_name 'Dr Edward Tiekink' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive 3 Singapore 117543 SINGAPORE ; _publ_contact_author_phone ' (65) 6874 2848 ' _publ_contact_author_fax ' (65) 6779 1691 ' _publ_contact_author_email ' chmtert@nus.edu.sg ' _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Supramolecular association in organomercury(II) 1,1-dithiolates. Complementarity between Hg¡S and hydrogen bonding interactions in organomercury(II) 2-amino-cyclopent-1-ene-1-carbodithioates ; #============================================================================== data_MeHg(S2CC5H6NH2)-polymorph_a _database_code_CSD 210494 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety MeHg(S2CC5H6NH2) _chemical_formula_sum 'C7 H11 Hg N S2' _chemical_formula_weight 373.88 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' Hg Hg -2.3894 9.2266 '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' _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 7.4810(6) _cell_length_b 12.2434(10) _cell_length_c 10.8863(9) _cell_angle_alpha 90 _cell_angle_beta 108.526(2) _cell_angle_gamma 90 _cell_volume 945.44(13) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2558 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description 'flattened octahedron' _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 16.657 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.245 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7802 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 30.0 _reflns_number_total 2753 _reflns_number_gt 2285 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'Bruker SHEXLTL (Bruker, 2000)' _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^)+(0.0324P)^2^] 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 2753 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.069 _refine_ls_wR_factor_gt 0.065 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _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 Hg Hg 0.21171(2) 0.100243(13) 0.426933(19) 0.02483(7) Uani 1 1 d . . . S1 S 0.31752(16) -0.08452(9) 0.45304(14) 0.0261(3) Uani 1 1 d . . . S2 S -0.09644(17) -0.08387(9) 0.31658(14) 0.0271(3) Uani 1 1 d . . . N1 N -0.1972(6) -0.3230(3) 0.2660(4) 0.0335(11) Uani 1 1 d . . . H1A H -0.2376 -0.2559 0.2589 0.040 Uiso 1 1 calc R . . H1B H -0.2756 -0.3762 0.2350 0.040 Uiso 1 1 calc R . . C1 C 0.1099(6) -0.1547(3) 0.3791(4) 0.0175(8) Uani 1 1 d . . . C2 C 0.1263(6) -0.2689(3) 0.3788(4) 0.0160(8) Uani 1 1 d . . . C3 C -0.0191(6) -0.3437(3) 0.3234(5) 0.0201(9) Uani 1 1 d . . . C4 C 0.0525(6) -0.4585(4) 0.3384(5) 0.0244(10) Uani 1 1 d . . . H4A H 0.0402 -0.4907 0.2537 0.029 Uiso 1 1 calc R . . H4B H -0.0176 -0.5035 0.3818 0.029 Uiso 1 1 calc R . . C5 C 0.2589(7) -0.4503(4) 0.4204(5) 0.0304(12) Uani 1 1 d . . . H5A H 0.2790 -0.4848 0.5050 0.036 Uiso 1 1 calc R . . H5B H 0.3387 -0.4872 0.3772 0.036 Uiso 1 1 calc R . . C6 C 0.3071(6) -0.3296(4) 0.4370(5) 0.0249(10) Uani 1 1 d . . . H6A H 0.3981 -0.3105 0.3926 0.030 Uiso 1 1 calc R . . H6B H 0.3619 -0.3114 0.5291 0.030 Uiso 1 1 calc R . . C7 C 0.1500(8) 0.2648(4) 0.3917(6) 0.0341(12) Uani 1 1 d . . . H7A H 0.2590 0.3081 0.4383 0.051 Uiso 1 1 calc R . . H7B H 0.0442 0.2841 0.4208 0.051 Uiso 1 1 calc R . . H7C H 0.1178 0.2790 0.2996 0.051 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 Hg 0.02056(11) 0.01202(10) 0.03855(13) -0.00042(7) 0.00464(8) -0.00011(7) S1 0.0142(5) 0.0121(5) 0.0459(8) -0.0013(5) 0.0008(5) -0.0010(4) S2 0.0173(5) 0.0143(5) 0.0422(8) 0.0003(5) -0.0010(5) 0.0040(4) N1 0.0182(19) 0.0145(18) 0.055(3) -0.0093(18) -0.0065(19) -0.0021(16) C1 0.018(2) 0.016(2) 0.017(2) -0.0001(16) 0.0036(17) -0.0008(17) C2 0.0139(19) 0.0107(18) 0.022(2) -0.0002(16) 0.0040(17) 0.0011(15) C3 0.016(2) 0.015(2) 0.026(2) -0.0032(18) 0.0020(18) 0.0000(17) C4 0.022(2) 0.012(2) 0.035(3) -0.0005(18) 0.004(2) -0.0008(18) C5 0.021(2) 0.017(2) 0.045(3) -0.001(2) 0.000(2) 0.0044(19) C6 0.017(2) 0.017(2) 0.038(3) 0.0023(19) 0.004(2) 0.0028(18) C7 0.034(3) 0.013(2) 0.052(3) 0.003(2) 0.010(3) 0.004(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 Hg C7 2.075(5) . ? Hg S1 2.3836(11) . ? S1 C1 1.734(4) . ? S2 C1 1.712(4) . ? N1 C3 1.304(6) . ? C1 C2 1.404(6) . ? C2 C3 1.403(6) . ? C2 C6 1.495(6) . ? C3 C4 1.494(6) . ? C4 C5 1.521(6) . ? C5 C6 1.519(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 Hg S1 171.62(16) . . ? C1 S1 Hg 101.57(15) . . ? C2 C1 S2 124.9(3) . . ? C2 C1 S1 115.4(3) . . ? S2 C1 S1 119.7(3) . . ? C1 C2 C3 126.5(4) . . ? C1 C2 C6 124.2(4) . . ? C3 C2 C6 109.4(4) . . ? N1 C3 C2 127.8(4) . . ? N1 C3 C4 120.8(4) . . ? C2 C3 C4 111.4(4) . . ? C3 C4 C5 105.3(4) . . ? C6 C5 C4 107.0(4) . . ? C5 C6 C2 106.5(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.04 _refine_diff_density_min -1.70 _refine_diff_density_rms 0.219 #==END data_MeHg(S2CC5H6NH2)-polymorph_b _database_code_CSD 210495 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety MeHg(S2CC5H6NH2) _chemical_formula_sum 'C7 H11 Hg N S2' _chemical_formula_weight 373.88 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' Hg Hg -2.3894 9.2266 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3186(14) _cell_length_b 12.7707(15) _cell_length_c 12.3438(13) _cell_angle_alpha 90 _cell_angle_beta 91.394(2) _cell_angle_gamma 90 _cell_volume 1941.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2581 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 30.1 _exptl_crystal_description needle _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 16.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15443 _diffrn_reflns_av_R_equivalents 0.123 _diffrn_reflns_av_sigmaI/netI 0.135 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_theta_max 30.1 _reflns_number_total 5650 _reflns_number_gt 3400 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'Bruker SHEXLTL (Bruker, 2000)' _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^)+(0.0437P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00150(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5650 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.116 _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_ref 0.131 _refine_ls_wR_factor_gt 0.109 _refine_ls_goodness_of_fit_ref 0.96 _refine_ls_restrained_S_all 0.96 _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 Hg1 Hg 0.15320(3) 0.11302(4) 0.36742(3) 0.03226(14) Uani 1 1 d . . . Hg2 Hg -0.34432(3) -0.33065(4) 0.41021(3) 0.03361(15) Uani 1 1 d . . . S1 S 0.34107(19) 0.15497(19) 0.38689(19) 0.0232(5) Uani 1 1 d . . . S1A S -0.1650(2) -0.2747(3) 0.3672(2) 0.0423(8) Uani 1 1 d . . . S2 S 0.3197(2) -0.0516(2) 0.2762(2) 0.0369(7) Uani 1 1 d . . . S2A S -0.1655(2) -0.3807(2) 0.58108(19) 0.0305(6) Uani 1 1 d . . . N1 N 0.5487(8) -0.1246(7) 0.2435(7) 0.043(2) Uani 1 1 d . . . H1A H 0.4799 -0.1360 0.2309 0.051 Uiso 1 1 calc R . . H1B H 0.5968 -0.1682 0.2198 0.051 Uiso 1 1 calc R . . N1A N 0.0732(7) -0.4141(7) 0.6397(6) 0.039(2) Uani 1 1 d . . . H1A1 H 0.0065 -0.4219 0.6597 0.047 Uiso 1 1 calc R . . H1A2 H 0.1263 -0.4387 0.6799 0.047 Uiso 1 1 calc R . . C1 C 0.4008(7) 0.0421(7) 0.3346(6) 0.0172(18) Uani 1 1 d . . . C1A C -0.0940(8) -0.3282(7) 0.4791(7) 0.023(2) Uani 1 1 d . . . C2 C 0.5128(7) 0.0358(7) 0.3417(6) 0.020(2) Uani 1 1 d . . . C2A C 0.0177(7) -0.3211(8) 0.4759(7) 0.025(2) Uani 1 1 d . . . C3 C 0.5805(7) -0.0396(8) 0.2995(7) 0.023(2) Uani 1 1 d . . . C3A C 0.0937(8) -0.3655(7) 0.5499(7) 0.023(2) Uani 1 1 d . . . C4 C 0.6983(8) -0.0154(10) 0.3192(9) 0.045(3) Uani 1 1 d . . . H4A H 0.7356 -0.0742 0.3550 0.054 Uiso 1 1 calc R . . H4B H 0.7341 -0.0002 0.2509 0.054 Uiso 1 1 calc R . . C4A C 0.2081(8) -0.3497(9) 0.5148(8) 0.036(3) Uani 1 1 d . . . H4A1 H 0.2473 -0.4165 0.5138 0.043 Uiso 1 1 calc R . . H4A2 H 0.2468 -0.3014 0.5637 0.043 Uiso 1 1 calc R . . C5 C 0.5843(7) 0.1184(8) 0.3964(8) 0.026(2) Uani 1 1 d . . . H5A H 0.5639 0.1280 0.4720 0.032 Uiso 1 1 calc R . . H5B H 0.5770 0.1856 0.3586 0.032 Uiso 1 1 calc R . . C5A C 0.1976(9) -0.3039(12) 0.4014(10) 0.056(4) Uani 1 1 d . . . H5A1 H 0.2489 -0.2460 0.3928 0.067 Uiso 1 1 calc R . . H5A2 H 0.2126 -0.3575 0.3469 0.067 Uiso 1 1 calc R . . C6 C 0.6984(8) 0.0786(9) 0.3907(9) 0.039(3) Uani 1 1 d . . . H6A H 0.7456 0.1329 0.3613 0.047 Uiso 1 1 calc R . . H6B H 0.7259 0.0600 0.4633 0.047 Uiso 1 1 calc R . . C6A C 0.0803(8) -0.2645(10) 0.3882(9) 0.042(3) Uani 1 1 d . . . H6A1 H 0.0505 -0.2816 0.3160 0.050 Uiso 1 1 calc R . . H6A2 H 0.0770 -0.1884 0.3984 0.050 Uiso 1 1 calc R . . C7 C -0.0116(7) 0.0717(10) 0.3613(10) 0.053(4) Uani 1 1 d . . . H7A H -0.0208 0.0034 0.3941 0.079 Uiso 1 1 calc R . . H7B H -0.0372 0.0694 0.2864 0.079 Uiso 1 1 calc R . . H7C H -0.0532 0.1232 0.4005 0.079 Uiso 1 1 calc R . . C7A C -0.5060(8) -0.3650(9) 0.4337(9) 0.042(3) Uani 1 1 d . . . H7A1 H -0.5512 -0.3136 0.3964 0.063 Uiso 1 1 calc R . . H7A2 H -0.5205 -0.3633 0.5106 0.063 Uiso 1 1 calc R . . H7A3 H -0.5223 -0.4342 0.4053 0.063 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 0.0177(2) 0.0422(3) 0.0371(3) -0.00653(19) 0.00617(15) -0.00238(19) Hg2 0.0307(2) 0.0455(3) 0.0245(2) -0.00533(18) -0.00179(15) 0.0092(2) S1 0.0182(12) 0.0244(14) 0.0272(12) -0.0080(10) 0.0030(9) 0.0017(10) S1A 0.0300(15) 0.072(2) 0.0253(14) 0.0202(14) 0.0031(11) 0.0148(15) S2 0.0314(14) 0.0331(17) 0.0456(17) -0.0168(13) -0.0103(12) -0.0054(13) S2A 0.0287(14) 0.0377(16) 0.0252(13) 0.0089(11) 0.0064(10) 0.0071(12) N1 0.060(7) 0.025(5) 0.044(6) -0.009(4) 0.011(5) 0.018(5) N1A 0.032(5) 0.056(7) 0.029(5) 0.018(4) -0.006(4) 0.001(5) C1 0.020(4) 0.018(5) 0.014(4) 0.001(4) 0.004(3) 0.001(4) C1A 0.033(5) 0.018(5) 0.018(4) -0.005(4) -0.002(4) -0.001(4) C2 0.026(5) 0.024(5) 0.009(4) 0.002(4) -0.001(3) -0.002(4) C2A 0.020(5) 0.034(6) 0.021(5) -0.003(4) -0.002(4) -0.007(4) C3 0.028(5) 0.023(5) 0.018(4) 0.005(4) 0.004(4) 0.013(4) C3A 0.035(6) 0.014(5) 0.021(5) -0.004(4) -0.004(4) 0.006(4) C4 0.030(6) 0.049(8) 0.056(8) -0.004(6) 0.015(5) 0.010(6) C4A 0.031(6) 0.032(7) 0.044(7) -0.008(5) -0.001(5) -0.005(5) C5 0.019(5) 0.019(5) 0.042(6) -0.004(4) 0.001(4) -0.008(4) C5A 0.029(6) 0.085(11) 0.055(8) 0.019(7) 0.011(5) -0.001(7) C6 0.022(5) 0.053(8) 0.041(6) -0.017(6) 0.007(4) -0.002(6) C6A 0.037(7) 0.048(8) 0.042(6) 0.020(6) 0.012(5) -0.014(6) C7 0.006(5) 0.069(10) 0.085(10) -0.006(7) 0.006(5) -0.014(6) C7A 0.034(6) 0.047(8) 0.045(7) -0.009(6) -0.006(5) -0.002(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 Hg1 C7 2.098(9) . ? Hg1 S1 2.382(2) . ? Hg2 C7A 2.067(10) . ? Hg2 S1A 2.393(3) . ? S1 C1 1.750(9) . ? S1A C1A 1.756(9) . ? S2 C1 1.707(9) . ? S2A C1A 1.692(10) . ? N1 C3 1.339(12) . ? N1A C3A 1.301(12) . ? C1 C2 1.383(11) . ? C1A C2A 1.381(12) . ? C2 C3 1.383(12) . ? C2 C5 1.522(12) . ? C2A C3A 1.410(12) . ? C2A C6A 1.527(13) . ? C3 C4 1.498(13) . ? C3A C4A 1.498(14) . ? C4 C6 1.489(15) . ? C4A C5A 1.520(15) . ? C5 C6 1.497(14) . ? C5A C6A 1.534(15) . ? 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 C7 Hg1 S1 176.0(3) . . ? C7A Hg2 S1A 172.8(3) . . ? C1 S1 Hg1 101.2(3) . . ? C1A S1A Hg2 98.9(3) . . ? C2 C1 S1 116.9(7) . . ? C2 C1 S2 124.0(7) . . ? S1 C1 S2 119.1(5) . . ? C2A C1A S2A 125.8(7) . . ? C2A C1A S1A 115.5(7) . . ? S2A C1A S1A 118.8(6) . . ? C1 C2 C3 128.7(9) . . ? C1 C2 C5 123.7(8) . . ? C3 C2 C5 107.6(8) . . ? C1A C2A C3A 127.0(9) . . ? C1A C2A C6A 124.9(9) . . ? C3A C2A C6A 108.1(8) . . ? N1 C3 C2 125.9(9) . . ? N1 C3 C4 121.4(9) . . ? C2 C3 C4 112.6(9) . . ? N1A C3A C2A 127.2(9) . . ? N1A C3A C4A 120.9(9) . . ? C2A C3A C4A 111.9(9) . . ? C6 C4 C3 104.5(8) . . ? C3A C4A C5A 105.0(8) . . ? C2 C5 C6 106.1(8) . . ? C6A C5A C4A 106.4(9) . . ? C4 C6 C5 108.3(9) . . ? C5A C6A C2A 105.0(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.07 _refine_diff_density_min -3.22 _refine_diff_density_rms 0.312 #==END data_shelxl _database_code_CSD 210496 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Hg N S2' _chemical_formula_weight 435.94 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' Hg Hg -2.3894 9.2266 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 11.1294(7) _cell_length_b 8.9365(6) _cell_length_c 25.7799(16) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2564.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 5101 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.0 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 12.302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.272 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19879 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.046 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.4 _diffrn_reflns_theta_max 30.0 _reflns_number_total 3738 _reflns_number_gt 2964 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'Bruker SHEXLTL (Bruker, 2000)' _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^)+(0.0360P)^2^] 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 3738 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.047 _refine_ls_R_factor_gt 0.032 _refine_ls_wR_factor_ref 0.073 _refine_ls_wR_factor_gt 0.068 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 Hg Hg 0.153610(13) 0.232757(18) 0.225855(7) 0.01913(7) Uani 1 1 d . . . S1 S 0.18696(9) 0.29537(13) 0.31423(5) 0.0239(2) Uani 1 1 d . . . S2 S 0.39831(9) 0.38974(12) 0.25050(4) 0.0201(2) Uani 1 1 d . . . N1 N 0.5536(3) 0.5668(4) 0.32631(14) 0.0224(8) Uani 1 1 d . . . H1A H 0.5429 0.5410 0.2937 0.027 Uiso 1 1 calc R . . H1B H 0.6156 0.6223 0.3351 0.027 Uiso 1 1 calc R . . C1 C 0.3276(3) 0.3786(4) 0.30958(15) 0.0134(7) Uani 1 1 d . . . C2 C 0.3739(3) 0.4349(4) 0.35621(16) 0.0140(8) Uani 1 1 d . . . C3 C 0.4762(3) 0.5220(4) 0.36219(16) 0.0165(8) Uani 1 1 d . . . C4 C 0.4894(4) 0.5735(5) 0.41688(18) 0.0270(10) Uani 1 1 d . . . H4A H 0.4657 0.6798 0.4205 0.032 Uiso 1 1 calc R . . H4B H 0.5732 0.5614 0.4290 0.032 Uiso 1 1 calc R . . C5 C 0.4038(4) 0.4711(5) 0.44722(19) 0.0315(11) Uani 1 1 d . . . H5A H 0.4475 0.3839 0.4616 0.038 Uiso 1 1 calc R . . H5B H 0.3654 0.5262 0.4761 0.038 Uiso 1 1 calc R . . C6 C 0.3107(3) 0.4214(5) 0.40769(17) 0.0222(9) Uani 1 1 d . . . H6A H 0.2855 0.3168 0.4142 0.027 Uiso 1 1 calc R . . H6B H 0.2390 0.4868 0.4089 0.027 Uiso 1 1 calc R . . C7 C 0.1401(3) 0.1924(5) 0.14690(17) 0.0180(8) Uani 1 1 d . . . C8 C 0.2140(4) 0.2701(5) 0.11237(18) 0.0239(9) Uani 1 1 d . . . H8 H 0.2686 0.3428 0.1253 0.029 Uiso 1 1 calc R . . C9 C 0.2089(4) 0.2427(5) 0.0595(2) 0.0304(11) Uani 1 1 d . . . H9 H 0.2607 0.2960 0.0367 0.036 Uiso 1 1 calc R . . C10 C 0.1301(4) 0.1397(6) 0.0396(2) 0.0399(13) Uani 1 1 d . . . H10 H 0.1270 0.1208 0.0034 0.048 Uiso 1 1 calc R . . C11 C 0.0549(4) 0.0635(6) 0.0735(2) 0.0410(13) Uani 1 1 d . . . H11 H -0.0002 -0.0079 0.0601 0.049 Uiso 1 1 calc R . . C12 C 0.0589(4) 0.0897(5) 0.1262(2) 0.0289(10) Uani 1 1 d . . . H12 H 0.0059 0.0372 0.1486 0.035 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 Hg 0.01618(9) 0.02630(10) 0.01491(11) -0.00449(6) -0.00270(6) -0.00184(5) S1 0.0177(5) 0.0384(6) 0.0157(6) -0.0064(5) 0.0027(4) -0.0132(4) S2 0.0178(5) 0.0291(5) 0.0132(6) -0.0025(4) 0.0038(4) -0.0036(4) N1 0.0160(16) 0.0263(17) 0.025(2) -0.0012(15) -0.0006(15) -0.0102(13) C1 0.0135(17) 0.0145(17) 0.012(2) 0.0012(14) -0.0008(14) 0.0000(13) C2 0.0115(17) 0.0196(18) 0.011(2) -0.0010(15) 0.0019(14) -0.0015(13) C3 0.0125(18) 0.0204(18) 0.017(2) -0.0002(15) -0.0035(15) 0.0026(13) C4 0.021(2) 0.036(2) 0.024(3) -0.0095(19) -0.0078(18) -0.0036(17) C5 0.027(2) 0.048(3) 0.019(3) -0.005(2) -0.0026(19) -0.007(2) C6 0.0182(19) 0.035(2) 0.014(2) -0.0014(18) 0.0026(16) -0.0076(16) C7 0.0161(19) 0.0233(19) 0.014(2) -0.0039(16) -0.0042(15) 0.0061(14) C8 0.019(2) 0.031(2) 0.022(3) 0.0006(18) -0.0032(18) 0.0039(16) C9 0.030(3) 0.043(3) 0.018(3) 0.005(2) 0.002(2) 0.0083(19) C10 0.045(3) 0.056(3) 0.019(3) -0.007(2) -0.009(2) 0.012(2) C11 0.040(3) 0.048(3) 0.035(3) -0.012(2) -0.020(2) -0.002(2) C12 0.022(2) 0.030(2) 0.034(3) 0.000(2) -0.0045(19) -0.0026(17) _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 C7 2.073(4) . ? Hg S1 2.3752(12) . ? S1 C1 1.737(4) . ? S2 C1 1.717(4) . ? N1 C3 1.326(5) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? C1 C2 1.401(5) . ? C2 C3 1.388(5) . ? C2 C6 1.507(6) . ? C3 C4 1.490(6) . ? C4 C5 1.535(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.520(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.397(6) . ? C7 C12 1.394(6) . ? C8 C9 1.387(7) . ? C8 H8 0.9500 . ? C9 C10 1.371(7) . ? C9 H9 0.9500 . ? C10 C11 1.387(8) . ? C10 H10 0.9500 . ? C11 C12 1.379(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 C7 Hg S1 173.90(11) . . ? C1 S1 Hg 100.11(14) . . ? C3 N1 H1A 120.0 . . ? C3 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C2 C1 S2 124.8(3) . . ? C2 C1 S1 115.2(3) . . ? S2 C1 S1 119.9(2) . . ? C1 C2 C3 126.8(4) . . ? C1 C2 C6 123.7(3) . . ? C3 C2 C6 109.3(3) . . ? N1 C3 C2 128.7(4) . . ? N1 C3 C4 120.2(3) . . ? C2 C3 C4 111.1(3) . . ? C3 C4 C5 103.7(3) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C4 104.8(4) . . ? C6 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? C6 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C2 C6 C5 104.4(3) . . ? C2 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? C2 C6 H6B 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? C8 C7 C12 117.7(4) . . ? C8 C7 Hg 119.8(3) . . ? C12 C7 Hg 122.5(3) . . ? C7 C8 C9 121.0(4) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 120.7(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 118.8(5) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C7 120.6(4) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.00 _refine_diff_density_min -2.33 _refine_diff_density_rms 0.211