Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ulli Englert' _publ_contact_author_address ; Institute of Inorganic Chemistry RWTH Aachen Aachen 52074 GERMANY ; _publ_contact_author_email ULLRICH.ENGLERT@AC.RWTH-AACHEN.DE _publ_section_title ; Pyridine complexes of mercury(II)halides: Implications of a soft metal center for crystal engineering ; loop_ _publ_author_name 'Ulli Englert' 'Chunhua Hu.' 'Irmgard Kalf' data_hc118 _database_code_depnum_ccdc_archive 'CCDC 634015' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 1' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Cl6 Hg N2' _chemical_formula_weight 567.46 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' Cl Cl 0.1484 0.1585 '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 tetragonal _symmetry_space_group_name_H-M P-4b2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'y+1/2, x+1/2, -z' '-y+1/2, -x+1/2, -z' _cell_length_a 14.144(3) _cell_length_b 14.144(3) _cell_length_c 3.8148(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 763.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6317 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 28.37 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 11.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.180 _exptl_absorpt_correction_T_max 0.329 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.549121 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6317 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.37 _reflns_number_total 959 _reflns_number_gt 786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0320P)^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 SHELXL _refine_ls_extinction_coef 0.035(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 959 _refine_ls_number_parameters 47 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.5000 0.0000 0.5000 0.0367(2) Uani 1 4 d S . . Cl1 Cl 0.40753(9) 0.09247(9) 1.0000 0.0427(5) Uani 1 2 d S . . Cl2 Cl 0.63577(15) 0.38937(12) 0.7415(6) 0.0640(6) Uani 1 1 d . . . N N 0.6195(3) 0.1195(3) 0.5000 0.0417(16) Uani 1 2 d S . . C1 C 0.5989(4) 0.2079(4) 0.6034(17) 0.0389(15) Uani 1 1 d . . . H1 H 0.5343 0.2230 0.6785 0.051 Uiso 1 1 calc R . . C2 C 0.6656(5) 0.2769(5) 0.6060(17) 0.0413(15) Uani 1 1 d . . . C3 C 0.7581(4) 0.2581(4) 0.5000 0.046(2) Uani 1 2 d S . . H3 H 0.8071 0.3071 0.5000 0.060 Uiso 1 2 calc SR . . 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 0.0345(2) 0.0345(2) 0.0413(3) 0.000 0.000 -0.00769(15) Cl1 0.0414(6) 0.0414(6) 0.0452(11) 0.0042(11) 0.0042(11) 0.0078(8) Cl2 0.0728(12) 0.0383(9) 0.0810(13) -0.0079(11) 0.0058(12) -0.0063(9) N 0.033(2) 0.033(2) 0.058(4) 0.003(4) -0.003(4) -0.006(2) C1 0.033(3) 0.037(3) 0.047(4) 0.003(2) 0.003(2) 0.002(3) C2 0.047(4) 0.035(3) 0.042(4) 0.000(2) 0.000(3) -0.002(3) C3 0.047(3) 0.047(3) 0.044(5) 0.000(4) 0.000(4) -0.011(4) _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 N 2.390(6) 2_655 ? Hg N 2.390(6) . ? Hg Cl1 2.6570(13) 2_655 ? Hg Cl1 2.6570(13) 2_654 ? Hg Cl1 2.6570(13) . ? Hg Cl1 2.6570(13) 1_554 ? Cl1 Hg 2.6570(13) 1_556 ? Cl2 C2 1.724(7) . ? N C1 1.344(6) . ? N C1 1.344(6) 7_546 ? C1 C2 1.357(9) . ? C1 H1 0.9800 . ? C2 C3 1.395(7) . ? C3 C2 1.395(7) 7_546 ? C3 H3 0.9800 . ? 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 N Hg N 180.0(3) 2_655 . ? N Hg Cl1 90.0 2_655 2_655 ? N Hg Cl1 90.0 . 2_655 ? N Hg Cl1 90.0 2_655 2_654 ? N Hg Cl1 90.0 . 2_654 ? Cl1 Hg Cl1 91.76(6) 2_655 2_654 ? N Hg Cl1 90.0 2_655 . ? N Hg Cl1 90.0 . . ? Cl1 Hg Cl1 88.24(6) 2_655 . ? Cl1 Hg Cl1 180.00(5) 2_654 . ? N Hg Cl1 90.0 2_655 1_554 ? N Hg Cl1 90.0 . 1_554 ? Cl1 Hg Cl1 180.0 2_655 1_554 ? Cl1 Hg Cl1 88.24(6) 2_654 1_554 ? Cl1 Hg Cl1 91.76(6) . 1_554 ? Hg Cl1 Hg 91.76(6) 1_556 . ? C1 N C1 119.4(7) . 7_546 ? C1 N Hg 120.3(4) . . ? C1 N Hg 120.3(4) 7_546 . ? N C1 C2 121.4(6) . . ? N C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C1 C2 C3 120.8(7) . . ? C1 C2 Cl2 119.7(5) . . ? C3 C2 Cl2 119.5(5) . . ? C2 C3 C2 116.3(8) 7_546 . ? C2 C3 H3 121.9 7_546 . ? C2 C3 H3 121.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.427 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.141 # Attachment '2-hc122.cif' data_hc122 _database_code_depnum_ccdc_archive 'CCDC 634016' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Br4 Cl2 Hg N2' _chemical_formula_weight 745.30 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 tetragonal _symmetry_space_group_name_H-M P-4b2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'y+1/2, x+1/2, -z' '-y+1/2, -x+1/2, -z' _cell_length_a 14.147(2) _cell_length_b 14.147(2) _cell_length_c 3.8871(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 778.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5838 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 26.03 _exptl_crystal_description needle _exptl_crystal_colour colorles _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 20.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.197 _exptl_absorpt_correction_T_max 0.441 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.445909 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5838 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.03 _reflns_number_total 775 _reflns_number_gt 704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0270P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(2) _refine_ls_number_reflns 775 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0516 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.5000 0.0000 0.5000 0.02728(14) Uani 1 4 d S . . Cl Cl 0.40845(10) 0.09155(10) 1.0000 0.0332(5) Uani 1 2 d S . . Br Br 0.63585(5) 0.39759(5) 0.7837(2) 0.0397(2) Uani 1 1 d . . . N N 0.6195(3) 0.1195(3) 0.5000 0.0309(18) Uani 1 2 d S . . C1 C 0.6006(4) 0.2063(5) 0.6154(18) 0.0319(18) Uani 1 1 d . . . H1 H 0.5371 0.2205 0.7022 0.041 Uiso 1 1 calc R . . C2 C 0.6676(5) 0.2761(5) 0.6157(16) 0.0275(16) Uani 1 1 d . . . C3 C 0.7581(4) 0.2581(4) 0.5000 0.032(2) Uani 1 2 d S . . H3 H 0.8070 0.3070 0.5000 0.042 Uiso 1 2 calc SR . . 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 0.02661(17) 0.02661(17) 0.0286(2) 0.000 0.000 -0.0073(2) Cl 0.0309(7) 0.0309(7) 0.0379(13) 0.0034(11) 0.0034(11) 0.0063(9) Br 0.0436(4) 0.0279(4) 0.0475(4) -0.0065(4) 0.0044(4) -0.0022(3) N 0.026(2) 0.026(2) 0.040(5) 0.005(4) -0.005(4) 0.001(3) C1 0.020(3) 0.033(4) 0.043(5) -0.001(3) 0.004(3) 0.002(3) C2 0.037(4) 0.020(3) 0.025(4) -0.002(3) -0.004(3) 0.004(3) C3 0.035(3) 0.035(3) 0.027(4) 0.005(4) -0.005(4) -0.004(4) _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 N 2.390(7) 2_655 ? Hg N 2.390(7) . ? Hg Cl 2.6707(15) 2_655 ? Hg Cl 2.6707(15) 2_654 ? Hg Cl 2.6707(15) . ? Hg Cl 2.6707(15) 1_554 ? Cl Hg 2.6707(15) 1_556 ? Br C2 1.893(6) . ? N C1 1.334(7) . ? N C1 1.334(7) 7_546 ? C1 C2 1.369(9) . ? C1 H1 0.9800 . ? C2 C3 1.380(8) . ? C3 C2 1.380(8) 7_546 ? C3 H3 0.9800 . ? 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 N Hg N 180.0(3) 2_655 . ? N Hg Cl 90.0 2_655 2_655 ? N Hg Cl 90.0 . 2_655 ? N Hg Cl 90.0 2_655 2_654 ? N Hg Cl 90.0 . 2_654 ? Cl Hg Cl 93.39(7) 2_655 2_654 ? N Hg Cl 90.0 2_655 . ? N Hg Cl 90.0 . . ? Cl Hg Cl 86.61(7) 2_655 . ? Cl Hg Cl 180.00(6) 2_654 . ? N Hg Cl 90.0 2_655 1_554 ? N Hg Cl 90.0 . 1_554 ? Cl Hg Cl 180.0 2_655 1_554 ? Cl Hg Cl 86.61(7) 2_654 1_554 ? Cl Hg Cl 93.39(7) . 1_554 ? Hg Cl Hg 93.39(7) . 1_556 ? C1 N C1 118.7(8) . 7_546 ? C1 N Hg 120.6(4) . . ? C1 N Hg 120.6(4) 7_546 . ? N C1 C2 121.7(6) . . ? N C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C1 C2 C3 120.6(6) . . ? C1 C2 Br 119.4(5) . . ? C3 C2 Br 120.0(5) . . ? C2 C3 C2 116.7(8) 7_546 . ? C2 C3 H3 121.7 7_546 . ? C2 C3 H3 121.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.886 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.144 # Attachment '3a-hc212.cif' data_hc212 _database_code_depnum_ccdc_archive 'CCDC 634017' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 3a' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Cl2 Hg N2' _chemical_formula_weight 485.79 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' Cl Cl 0.1484 0.1585 '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 tetragonal _symmetry_space_group_name_H-M P-4b2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'y+1/2, x+1/2, -z' '-y+1/2, -x+1/2, -z' _cell_length_a 14.1357(7) _cell_length_b 14.1357(7) _cell_length_c 3.9721(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 793.70(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9498 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 28.30 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.033 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 10.021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.270 _exptl_absorpt_correction_T_max 0.670 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.402339 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9498 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.30 _reflns_number_total 998 _reflns_number_gt 886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0219P)^2^+0.4458P] 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 0.00(3) _refine_ls_number_reflns 998 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0497 _refine_ls_wR_factor_gt 0.0487 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.5000 0.0000 0.5000 0.03294(9) Uani 1 4 d S . . Cl Cl 0.40367(5) 0.09633(5) 1.0000 0.0354(2) Uani 1 2 d S . . N N 0.61420(17) 0.11420(17) 0.5000 0.0335(8) Uani 1 2 d S . . C1 C 0.5950(3) 0.2006(3) 0.6131(10) 0.0358(9) Uani 1 1 d . . . H1 H 0.5313 0.2140 0.6977 0.047 Uiso 1 1 calc R . . C2 C 0.6616(3) 0.2724(3) 0.6161(10) 0.0353(9) Uani 1 1 d . . . C3 C 0.7510(2) 0.2510(2) 0.5000 0.0422(12) Uani 1 2 d S . . H3 H 0.8000 0.3000 0.5000 0.055 Uiso 1 2 calc SR . . C4 C 0.6375(4) 0.3692(3) 0.7503(13) 0.0513(11) Uani 1 1 d . . . H4A H 0.6930 0.4104 0.7327 0.067 Uiso 1 1 calc R . . H4B H 0.6184 0.3640 0.9867 0.067 Uiso 1 1 calc R . . H4C H 0.5854 0.3960 0.6186 0.067 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 0.02938(10) 0.02938(10) 0.04005(15) 0.000 0.000 -0.00899(9) Cl 0.0343(3) 0.0343(3) 0.0377(5) 0.0047(8) 0.0047(8) 0.0052(4) N 0.0301(11) 0.0301(11) 0.040(2) 0.002(3) -0.002(3) -0.0070(14) C1 0.036(2) 0.033(2) 0.039(2) 0.0012(15) -0.0011(17) -0.0041(16) C2 0.043(2) 0.028(2) 0.034(2) 0.0005(15) -0.0015(17) -0.0078(17) C3 0.0423(18) 0.0423(18) 0.042(3) -0.008(3) 0.008(3) -0.017(2) C4 0.060(3) 0.036(2) 0.058(3) -0.009(2) 0.006(3) -0.006(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 N 2.283(3) 2_655 ? Hg N 2.283(3) . ? Hg Cl 2.7664(8) 1_554 ? Hg Cl 2.7664(8) . ? Hg Cl 2.7664(8) 2_655 ? Hg Cl 2.7664(8) 2_654 ? Cl Hg 2.7664(8) 1_556 ? N C1 1.329(4) . ? N C1 1.329(4) 7_546 ? C1 C2 1.384(5) . ? C1 H1 0.9800 . ? C2 C3 1.378(4) . ? C2 C4 1.507(6) . ? C3 C2 1.378(4) 7_546 ? C3 H3 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? 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 N Hg N 180.00(17) 2_655 . ? N Hg Cl 90.0 2_655 1_554 ? N Hg Cl 90.0 . 1_554 ? N Hg Cl 90.0 2_655 . ? N Hg Cl 90.0 . . ? Cl Hg Cl 91.77(3) 1_554 . ? N Hg Cl 90.0 2_655 2_655 ? N Hg Cl 90.0 . 2_655 ? Cl Hg Cl 180.00(3) 1_554 2_655 ? Cl Hg Cl 88.23(3) . 2_655 ? N Hg Cl 90.0 2_655 2_654 ? N Hg Cl 90.0 . 2_654 ? Cl Hg Cl 88.23(3) 1_554 2_654 ? Cl Hg Cl 180.0 . 2_654 ? Cl Hg Cl 91.77(3) 2_655 2_654 ? Hg Cl Hg 91.77(3) 1_556 . ? C1 N C1 119.3(4) . 7_546 ? C1 N Hg 120.4(2) . . ? C1 N Hg 120.4(2) 7_546 . ? N C1 C2 122.5(4) . . ? N C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 117.3(4) . . ? C3 C2 C4 121.7(4) . . ? C1 C2 C4 121.0(4) . . ? C2 C3 C2 121.0(4) 7_546 . ? C2 C3 H3 119.5 7_546 . ? C2 C3 H3 119.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.335 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.110 # Attachment '3b-hc114.cif' data_hc114 _database_code_depnum_ccdc_archive 'CCDC 634018' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 3b' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Cl8 Hg4 N2' _chemical_formula_weight 1300.26 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' Cl Cl 0.1484 0.1585 '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 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 3.9960(9) _cell_length_b 20.203(4) _cell_length_c 16.572(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.292(5) _cell_angle_gamma 90.00 _cell_volume 1332.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16682 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 28.31 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_max 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 23.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.621 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.542935 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16682 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3311 _reflns_number_gt 2325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0409P)^2^+0.8909P] 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 3311 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.0000 0.0000 0.5000 0.04165(15) Uani 1 2 d S . . Cl1 Cl 0.4465(6) 0.02662(13) 0.38188(15) 0.0441(6) Uani 1 1 d . . . N N 0.0240(19) 0.1034(3) 0.5333(5) 0.0331(17) Uani 1 1 d . . . C1 C 0.127(2) 0.1209(5) 0.6088(6) 0.041(2) Uani 1 1 d . . . H1 H 0.1832 0.0859 0.6488 0.053 Uiso 1 1 calc R . . C2 C 0.158(3) 0.1864(5) 0.6338(6) 0.044(2) Uani 1 1 d . . . C3 C 0.069(3) 0.2331(5) 0.5758(7) 0.048(3) Uani 1 1 d . . . H3 H 0.0878 0.2800 0.5909 0.063 Uiso 1 1 calc R . . C4 C -0.048(3) 0.2171(5) 0.4963(6) 0.046(2) Uani 1 1 d . . . C5 C -0.057(3) 0.1508(5) 0.4785(6) 0.046(3) Uani 1 1 d . . . H5 H -0.1271 0.1374 0.4226 0.060 Uiso 1 1 calc R . . C6 C 0.278(3) 0.2036(6) 0.7192(7) 0.061(3) Uani 1 1 d . . . H6A H 0.3255 0.1629 0.7503 0.079 Uiso 1 1 calc R . . H6B H 0.1042 0.2290 0.7435 0.079 Uiso 1 1 calc R . . H6C H 0.4834 0.2302 0.7198 0.079 Uiso 1 1 calc R . . C7 C -0.142(4) 0.2673(6) 0.4328(8) 0.070(4) Uani 1 1 d . . . H7A H -0.2225 0.2450 0.3822 0.091 Uiso 1 1 calc R . . H7B H 0.0546 0.2944 0.4239 0.091 Uiso 1 1 calc R . . H7C H -0.3206 0.2957 0.4503 0.091 Uiso 1 1 calc R . . Hg2 Hg 0.43881(10) 0.04972(2) 0.22348(3) 0.04655(14) Uani 1 1 d . . . Cl2 Cl 0.0774(7) -0.03822(13) 0.17933(17) 0.0552(7) Uani 1 1 d . . . Cl3 Cl -0.1677(7) 0.13577(13) 0.23021(17) 0.0519(6) Uani 1 1 d . . . Hg3 Hg 0.0000 0.0000 0.0000 0.04686(16) Uani 1 2 d S . . Cl4 Cl 0.3784(6) 0.08539(13) 0.02848(17) 0.0494(6) 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 Hg1 0.0538(3) 0.0274(3) 0.0438(3) -0.0074(2) 0.0047(3) -0.0045(2) Cl1 0.0455(14) 0.0512(14) 0.0356(13) 0.0036(10) 0.0040(11) -0.0045(11) N 0.045(4) 0.022(4) 0.033(4) -0.008(3) 0.006(3) -0.008(3) C1 0.038(5) 0.039(5) 0.046(6) 0.000(4) 0.013(4) 0.000(4) C2 0.048(6) 0.045(6) 0.040(6) -0.011(5) 0.012(5) 0.001(5) C3 0.052(6) 0.025(5) 0.069(8) -0.012(5) 0.017(6) -0.001(4) C4 0.060(7) 0.035(6) 0.044(6) -0.003(5) 0.012(5) -0.004(5) C5 0.052(6) 0.052(7) 0.035(6) -0.009(5) 0.003(5) 0.000(5) C6 0.073(8) 0.058(7) 0.050(7) -0.025(5) -0.009(6) 0.007(6) C7 0.090(10) 0.045(7) 0.070(9) 0.013(6) -0.012(7) 0.006(6) Hg2 0.0447(2) 0.0501(2) 0.0442(2) 0.00253(19) 0.00041(17) -0.01127(19) Cl2 0.0621(17) 0.0540(17) 0.0487(16) -0.0014(12) 0.0001(13) -0.0173(13) Cl3 0.0441(14) 0.0444(14) 0.0669(18) 0.0052(12) 0.0029(13) -0.0079(11) Hg3 0.0404(3) 0.0485(3) 0.0512(4) -0.0040(3) 0.0017(3) -0.0075(3) Cl4 0.0466(14) 0.0435(14) 0.0575(16) -0.0009(11) 0.0010(12) -0.0093(11) _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 N 2.162(7) 3_556 ? Hg1 N 2.162(7) . ? Hg1 Cl1 2.819(2) . ? Hg1 Cl1 2.819(2) 3_556 ? Hg1 Cl1 2.866(3) 3_656 ? Hg1 Cl1 2.866(3) 1_455 ? Cl1 Hg2 2.664(2) . ? Cl1 Hg1 2.866(3) 1_655 ? N C1 1.328(12) . ? N C5 1.339(13) . ? C1 C2 1.390(13) . ? C1 H1 0.9800 . ? C2 C3 1.371(15) . ? C2 C6 1.492(14) . ? C3 C4 1.394(15) . ? C3 H3 0.9800 . ? C4 C5 1.372(14) . ? C4 C7 1.486(15) . ? C5 H5 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? Hg2 Cl3 2.340(3) 1_655 ? Hg2 Cl2 2.363(3) . ? Hg2 Cl3 2.993(3) . ? Hg2 Cl2 3.248(3) 1_655 ? Hg2 Cl4 3.298(3) . ? Cl2 Hg3 3.058(3) . ? Cl3 Hg2 2.340(3) 1_455 ? Hg3 Cl4 2.314(2) . ? Hg3 Cl4 2.314(2) 3 ? Hg3 Cl2 3.058(3) 3 ? Hg3 Cl4 3.096(3) 3_655 ? Hg3 Cl4 3.096(3) 1_455 ? 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 N Hg1 N 180.0(4) 3_556 . ? N Hg1 Cl1 91.3(2) 3_556 . ? N Hg1 Cl1 88.7(2) . . ? N Hg1 Cl1 88.7(2) 3_556 3_556 ? N Hg1 Cl1 91.3(2) . 3_556 ? Cl1 Hg1 Cl1 180.0 . 3_556 ? N Hg1 Cl1 90.4(2) 3_556 3_656 ? N Hg1 Cl1 89.6(2) . 3_656 ? Cl1 Hg1 Cl1 90.69(7) . 3_656 ? Cl1 Hg1 Cl1 89.31(7) 3_556 3_656 ? N Hg1 Cl1 89.6(2) 3_556 1_455 ? N Hg1 Cl1 90.4(2) . 1_455 ? Cl1 Hg1 Cl1 89.31(7) . 1_455 ? Cl1 Hg1 Cl1 90.69(7) 3_556 1_455 ? Cl1 Hg1 Cl1 180.0 3_656 1_455 ? Hg2 Cl1 Hg1 140.10(10) . . ? Hg2 Cl1 Hg1 130.09(9) . 1_655 ? Hg1 Cl1 Hg1 89.31(7) . 1_655 ? C1 N C5 119.0(8) . . ? C1 N Hg1 120.0(6) . . ? C5 N Hg1 121.0(6) . . ? N C1 C2 123.0(9) . . ? N C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 115.9(9) . . ? C3 C2 C6 123.0(10) . . ? C1 C2 C6 121.1(10) . . ? C2 C3 C4 123.1(9) . . ? C2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? C5 C4 C3 115.5(10) . . ? C5 C4 C7 120.9(10) . . ? C3 C4 C7 123.5(10) . . ? N C5 C4 123.4(9) . . ? N C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Cl3 Hg2 Cl2 164.22(10) 1_655 . ? Cl3 Hg2 Cl1 97.85(9) 1_655 . ? Cl2 Hg2 Cl1 97.16(9) . . ? Cl3 Hg2 Cl3 96.29(9) 1_655 . ? Cl2 Hg2 Cl3 88.53(9) . . ? Cl1 Hg2 Cl3 90.05(8) . . ? Cl3 Hg2 Cl2 83.03(8) 1_655 1_655 ? Cl2 Hg2 Cl2 89.39(9) . 1_655 ? Cl1 Hg2 Cl2 100.85(8) . 1_655 ? Cl3 Hg2 Cl2 169.08(8) . 1_655 ? Cl3 Hg2 Cl4 82.67(8) 1_655 . ? Cl2 Hg2 Cl4 82.73(8) . . ? Cl1 Hg2 Cl4 175.64(7) . . ? Cl3 Hg2 Cl4 85.59(7) . . ? Cl2 Hg2 Cl4 83.50(7) 1_655 . ? Hg2 Cl2 Hg3 96.61(9) . . ? Hg2 Cl3 Hg2 96.29(9) 1_455 . ? Cl4 Hg3 Cl4 180.00(16) . 3 ? Cl4 Hg3 Cl2 90.89(8) . 3 ? Cl4 Hg3 Cl2 89.11(8) 3 3 ? Cl4 Hg3 Cl2 89.11(8) . . ? Cl4 Hg3 Cl2 90.89(8) 3 . ? Cl2 Hg3 Cl2 180.00(14) 3 . ? Cl4 Hg3 Cl4 85.88(9) . 3_655 ? Cl4 Hg3 Cl4 94.12(9) 3 3_655 ? Cl2 Hg3 Cl4 90.18(8) 3 3_655 ? Cl2 Hg3 Cl4 89.82(8) . 3_655 ? Cl4 Hg3 Cl4 94.12(9) . 1_455 ? Cl4 Hg3 Cl4 85.88(9) 3 1_455 ? Cl2 Hg3 Cl4 89.82(8) 3 1_455 ? Cl2 Hg3 Cl4 90.18(8) . 1_455 ? Cl4 Hg3 Cl4 180.00(14) 3_655 1_455 ? Hg3 Cl4 Hg2 91.40(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.367 _refine_diff_density_min -1.035 _refine_diff_density_rms 0.220 # Attachment '4-hc130.cif' data_hc130 _database_code_depnum_ccdc_archive 'CCDC 634019' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 4' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H3 Br2 Cl2 Hg N' _chemical_formula_weight 508.39 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 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 4.0533(9) _cell_length_b 17.987(4) _cell_length_c 13.770(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.315(5) _cell_angle_gamma 90.00 _cell_volume 1003.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10162 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 28.29 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 23.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.092 _exptl_absorpt_correction_T_max 0.240 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.384463 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10162 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2492 _reflns_number_gt 1735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0302P)^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 2492 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg -0.11048(9) 0.26432(2) 0.43855(3) 0.04530(14) Uani 1 1 d . . . Br1 Br 0.2435(2) 0.22568(6) 0.57436(7) 0.0486(3) Uani 1 1 d . . . Br2 Br -0.4930(2) 0.33149(6) 0.33125(7) 0.0514(3) Uani 1 1 d . . . Cl1 Cl -0.3010(7) 0.07178(17) 0.07934(19) 0.0662(8) Uani 1 1 d . . . Cl2 Cl 0.3163(7) -0.05204(15) 0.3865(2) 0.0583(7) Uani 1 1 d . . . N N -0.0657(17) 0.1473(4) 0.3397(5) 0.0428(18) Uani 1 1 d . . . C1 C -0.179(2) 0.1411(5) 0.2481(7) 0.043(2) Uani 1 1 d . . . H1 H -0.2890 0.1837 0.2177 0.056 Uiso 1 1 calc R . . C2 C -0.143(2) 0.0767(6) 0.1963(6) 0.044(2) Uani 1 1 d . . . C3 C 0.004(2) 0.0153(6) 0.2341(7) 0.049(3) Uani 1 1 d . . . H3 H 0.0253 -0.0308 0.1968 0.063 Uiso 1 1 calc R . . C4 C 0.125(2) 0.0215(5) 0.3297(7) 0.042(2) Uani 1 1 d . . . C5 C 0.082(2) 0.0878(6) 0.3794(7) 0.045(2) Uani 1 1 d . . . H5 H 0.1640 0.0914 0.4464 0.058 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 0.0413(2) 0.0466(2) 0.0479(2) 0.00032(18) -0.01264(15) 0.00481(16) Br1 0.0441(5) 0.0559(6) 0.0457(5) 0.0058(5) -0.0128(4) -0.0005(4) Br2 0.0407(5) 0.0628(7) 0.0506(6) 0.0164(5) -0.0080(4) 0.0032(4) Cl1 0.0847(19) 0.0696(19) 0.0440(14) -0.0065(13) -0.0188(13) 0.0002(15) Cl2 0.0736(17) 0.0448(14) 0.0564(15) 0.0072(12) -0.0037(13) 0.0096(12) N 0.045(4) 0.042(5) 0.041(4) -0.005(4) -0.010(3) 0.002(3) C1 0.048(5) 0.036(5) 0.046(6) -0.001(4) -0.004(4) 0.000(4) C2 0.041(5) 0.052(6) 0.038(5) 0.000(5) -0.003(4) 0.002(4) C3 0.063(6) 0.044(6) 0.039(6) -0.009(5) 0.007(5) -0.012(5) C4 0.040(5) 0.037(5) 0.048(6) 0.005(4) 0.004(4) -0.007(4) C5 0.039(5) 0.058(6) 0.038(5) 0.009(5) -0.008(4) -0.002(4) _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 Br1 2.4515(11) . ? Hg Br2 2.4538(10) . ? Hg N 2.515(7) . ? Hg Br2 3.1541(11) 1_655 ? Hg Br1 3.3000(12) 1_455 ? Hg Cl1 3.614(3) 4_566 ? Cl1 C2 1.733(9) . ? Cl2 C4 1.720(10) . ? N C5 1.341(11) . ? N C1 1.344(11) . ? C1 C2 1.368(13) . ? C1 H1 0.9800 . ? C2 C3 1.357(13) . ? C3 C4 1.405(12) . ? C3 H3 0.9800 . ? C4 C5 1.386(13) . ? C5 H5 0.9800 . ? 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 Br1 Hg Br2 164.61(4) . . ? Br1 Hg N 97.58(17) . . ? Br2 Hg N 97.68(17) . . ? Br1 Hg Br2 90.19(3) . 1_655 ? Br2 Hg Br2 91.70(3) . 1_655 ? N Hg Br2 90.42(17) . 1_655 ? Br1 Hg Br1 88.33(3) . 1_455 ? Br2 Hg Br1 86.81(3) . 1_455 ? N Hg Br1 100.97(17) . 1_455 ? Br2 Hg Br1 168.61(3) 1_655 1_455 ? Br1 Hg Cl1 87.02(5) . 4_566 ? Br2 Hg Cl1 77.60(5) . 4_566 ? N Hg Cl1 171.79(17) . 4_566 ? Br2 Hg Cl1 96.39(5) 1_655 4_566 ? Br1 Hg Cl1 72.26(5) 1_455 4_566 ? C5 N C1 117.8(8) . . ? C5 N Hg 118.7(6) . . ? C1 N Hg 123.5(6) . . ? N C1 C2 121.5(9) . . ? N C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 122.4(9) . . ? C3 C2 Cl1 118.3(7) . . ? C1 C2 Cl1 119.2(8) . . ? C2 C3 C4 116.4(9) . . ? C2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? C5 C4 C3 119.1(9) . . ? C5 C4 Cl2 119.6(7) . . ? C3 C4 Cl2 121.2(8) . . ? N C5 C4 122.8(9) . . ? N C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Hg N C1 -170.2(6) . . . . ? Br1 Hg N C2 -168.7(8) . . . . ? Br2 Hg N C1 11.8(7) . . . . ? Br2 Hg N C2 13.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.257 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.209 # Attachment '5-hc187.cif' data_hc187 _database_code_depnum_ccdc_archive 'CCDC 634020' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 5' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Br6 Hg N2' _chemical_formula_weight 834.22 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' Br Br -0.2901 2.4595 '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 4.0004(11) _cell_length_b 14.637(4) _cell_length_c 14.682(4) _cell_angle_alpha 86.845(5) _cell_angle_beta 84.250(5) _cell_angle_gamma 82.925(5) _cell_volume 848.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9630 _cell_measurement_theta_min 1.40 _cell_measurement_theta_max 26.10 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 23.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.185 _exptl_absorpt_correction_T_max 0.499 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.370643 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9630 _diffrn_reflns_av_R_equivalents 0.1139 _diffrn_reflns_av_sigmaI/netI 0.1414 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 26.10 _reflns_number_total 3324 _reflns_number_gt 1824 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0235P)^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 3324 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.0000 0.0000 0.0000 0.0423(3) Uani 1 2 d S . . Br1 Br -0.4111(4) 0.09368(12) -0.09830(11) 0.0446(4) Uani 1 1 d . . . Br2 Br -0.5042(5) 0.39833(13) 0.12573(13) 0.0631(6) Uani 1 1 d . . . Br3 Br 0.0466(5) 0.14186(14) 0.39128(12) 0.0599(5) Uani 1 1 d . . . N11 N -0.105(4) 0.1277(9) 0.1205(9) 0.048(4) Uani 1 1 d . . . C12 C -0.249(4) 0.2136(11) 0.1002(11) 0.048(5) Uani 1 1 d . . . H12 H -0.3170 0.2286 0.0383 0.063 Uiso 1 1 calc R . . C13 C -0.303(4) 0.2791(11) 0.1618(11) 0.039(4) Uani 1 1 d . . . C14 C -0.218(4) 0.2595(12) 0.2536(11) 0.047(4) Uani 1 1 d . . . H14 H -0.2592 0.3060 0.3002 0.061 Uiso 1 1 calc R . . C15 C -0.075(4) 0.1717(12) 0.2721(10) 0.043(4) Uani 1 1 d . . . C16 C -0.017(4) 0.1068(11) 0.2078(11) 0.043(4) Uani 1 1 d . . . H16 H 0.0876 0.0447 0.2239 0.055 Uiso 1 1 calc R . . Hg2 Hg 0.5000 0.5000 0.5000 0.0433(3) Uani 1 2 d S . . Br4 Br 0.1785(4) 0.41579(12) 0.40063(11) 0.0478(5) Uani 1 1 d . . . Br5 Br 0.7276(6) 0.90430(14) 0.37559(14) 0.0720(6) Uani 1 1 d . . . Br6 Br 0.9746(6) 0.63285(15) 0.10924(13) 0.0683(6) Uani 1 1 d . . . N21 N 0.554(3) 0.6360(10) 0.3737(8) 0.047(4) Uani 1 1 d . . . C22 C 0.672(5) 0.6091(13) 0.2896(10) 0.061(6) Uani 1 1 d . . . H22 H 0.6573 0.5464 0.2712 0.080 Uiso 1 1 calc R . . C23 C 0.811(4) 0.6716(12) 0.2308(11) 0.051(5) Uani 1 1 d . . . C24 C 0.831(4) 0.7608(11) 0.2503(11) 0.042(4) Uani 1 1 d . . . H24 H 0.9232 0.8055 0.2055 0.055 Uiso 1 1 calc R . . C25 C 0.711(4) 0.7823(10) 0.3390(11) 0.037(4) Uani 1 1 d . . . C26 C 0.570(4) 0.7220(12) 0.3983(11) 0.051(5) Uani 1 1 d . . . H26 H 0.4778 0.7409 0.4597 0.067 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 0.0476(6) 0.0460(6) 0.0335(5) 0.0061(4) -0.0116(4) -0.0033(5) Br1 0.0476(10) 0.0492(11) 0.0369(9) 0.0127(8) -0.0106(8) -0.0070(8) Br2 0.0794(14) 0.0499(12) 0.0593(12) 0.0013(9) -0.0159(11) 0.0012(10) Br3 0.0743(13) 0.0706(14) 0.0366(10) 0.0006(9) -0.0162(9) -0.0076(11) N11 0.076(10) 0.039(9) 0.031(8) -0.002(6) -0.009(7) -0.014(8) C12 0.087(14) 0.033(10) 0.026(9) 0.009(7) -0.016(9) -0.006(10) C13 0.030(9) 0.048(11) 0.040(10) -0.007(8) -0.001(7) -0.003(8) C14 0.046(10) 0.048(12) 0.046(10) -0.009(8) 0.006(8) -0.003(9) C15 0.043(10) 0.063(13) 0.024(8) -0.015(8) -0.005(7) 0.000(9) C16 0.039(9) 0.038(10) 0.050(11) -0.011(8) 0.011(8) -0.008(8) Hg2 0.0502(6) 0.0495(6) 0.0330(5) 0.0057(4) -0.0073(4) -0.0177(5) Br4 0.0473(10) 0.0536(11) 0.0448(10) -0.0083(8) -0.0089(8) -0.0083(9) Br5 0.1071(17) 0.0514(13) 0.0604(13) 0.0073(10) -0.0132(12) -0.0213(12) Br6 0.0884(15) 0.0730(15) 0.0398(11) 0.0085(10) 0.0069(10) -0.0103(12) N21 0.068(10) 0.054(10) 0.023(7) 0.010(6) -0.013(7) -0.018(8) C22 0.104(16) 0.062(13) 0.022(9) 0.018(8) -0.009(10) -0.030(12) C23 0.064(12) 0.050(12) 0.035(10) 0.010(8) -0.006(9) 0.006(9) C24 0.035(10) 0.047(12) 0.045(10) 0.002(8) -0.009(8) 0.001(8) C25 0.039(9) 0.023(9) 0.046(10) -0.004(7) 0.001(8) 0.005(7) C26 0.069(12) 0.060(13) 0.029(9) -0.001(8) -0.001(9) -0.026(10) _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 Br1 2.5239(17) 2 ? Hg1 Br1 2.5239(17) . ? Hg1 N11 2.612(13) 2 ? Hg1 N11 2.612(13) . ? Hg1 Br1 3.0675(16) 1_655 ? Hg1 Br1 3.0675(16) 2_455 ? Br1 Hg1 3.0675(16) 1_455 ? Br2 C13 1.901(16) . ? Br3 C15 1.876(15) . ? N11 C12 1.347(19) . ? N11 C16 1.37(2) . ? C12 C13 1.34(2) . ? C12 H12 0.9800 . ? C13 C14 1.43(2) . ? C14 C15 1.36(2) . ? C14 H14 0.9800 . ? C15 C16 1.36(2) . ? C16 H16 0.9800 . ? Hg2 Br4 2.5033(16) . ? Hg2 Br4 2.5033(16) 2_666 ? Hg2 N21 2.658(12) 2_666 ? Hg2 N21 2.658(12) . ? Hg2 Br4 3.0977(18) 2_566 ? Hg2 Br4 3.0977(19) 1_655 ? Br4 Hg2 3.0977(18) 1_455 ? Br5 C25 1.904(15) . ? Br6 C23 1.929(17) . ? N21 C22 1.34(2) . ? N21 C26 1.34(2) . ? C22 C23 1.36(2) . ? C22 H22 0.9800 . ? C23 C24 1.37(2) . ? C24 C25 1.38(2) . ? C24 H24 0.9800 . ? C25 C26 1.34(2) . ? C26 H26 0.9800 . ? 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 Br1 Hg1 Br1 180.00(9) 2 . ? Br1 Hg1 N11 89.9(3) 2 2 ? Br1 Hg1 N11 90.1(3) . 2 ? Br1 Hg1 N11 90.1(3) 2 . ? Br1 Hg1 N11 89.9(3) . . ? N11 Hg1 N11 180.0(9) 2 . ? Br1 Hg1 Br1 89.17(5) 2 1_655 ? Br1 Hg1 Br1 90.83(5) . 1_655 ? N11 Hg1 Br1 89.7(3) 2 1_655 ? N11 Hg1 Br1 90.3(3) . 1_655 ? Br1 Hg1 Br1 90.83(5) 2 2_455 ? Br1 Hg1 Br1 89.17(5) . 2_455 ? N11 Hg1 Br1 90.3(3) 2 2_455 ? N11 Hg1 Br1 89.7(3) . 2_455 ? Br1 Hg1 Br1 180.00(5) 1_655 2_455 ? Hg1 Br1 Hg1 90.83(5) . 1_455 ? C12 N11 C16 118.5(13) . . ? C12 N11 Hg1 122.1(10) . . ? C16 N11 Hg1 119.4(10) . . ? C13 C12 N11 122.2(15) . . ? C13 C12 H12 118.9 . . ? N11 C12 H12 118.9 . . ? C12 C13 C14 120.7(16) . . ? C12 C13 Br2 118.8(13) . . ? C14 C13 Br2 120.5(12) . . ? C15 C14 C13 115.7(15) . . ? C15 C14 H14 122.2 . . ? C13 C14 H14 122.2 . . ? C16 C15 C14 122.5(16) . . ? C16 C15 Br3 119.8(14) . . ? C14 C15 Br3 117.7(12) . . ? C15 C16 N11 120.4(16) . . ? C15 C16 H16 119.8 . . ? N11 C16 H16 119.8 . . ? Br4 Hg2 Br4 180.00(7) . 2_666 ? Br4 Hg2 N21 88.3(3) . 2_666 ? Br4 Hg2 N21 91.7(3) 2_666 2_666 ? Br4 Hg2 N21 91.7(3) . . ? Br4 Hg2 N21 88.3(3) 2_666 . ? N21 Hg2 N21 180.000(3) 2_666 . ? Br4 Hg2 Br4 89.48(5) . 2_566 ? Br4 Hg2 Br4 90.52(5) 2_666 2_566 ? N21 Hg2 Br4 83.7(3) 2_666 2_566 ? N21 Hg2 Br4 96.3(3) . 2_566 ? Br4 Hg2 Br4 90.52(5) . 1_655 ? Br4 Hg2 Br4 89.48(5) 2_666 1_655 ? N21 Hg2 Br4 96.3(3) 2_666 1_655 ? N21 Hg2 Br4 83.7(3) . 1_655 ? Br4 Hg2 Br4 180.0 2_566 1_655 ? Hg2 Br4 Hg2 90.52(5) . 1_455 ? C22 N21 C26 121.1(14) . . ? C22 N21 Hg2 115.0(11) . . ? C26 N21 Hg2 120.4(10) . . ? N21 C22 C23 117.6(17) . . ? N21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? C22 C23 C24 124.7(17) . . ? C22 C23 Br6 117.4(14) . . ? C24 C23 Br6 117.9(12) . . ? C23 C24 C25 114.0(15) . . ? C23 C24 H24 123.0 . . ? C25 C24 H24 123.0 . . ? C26 C25 C24 122.5(15) . . ? C26 C25 Br5 119.1(13) . . ? C24 C25 Br5 118.3(12) . . ? C25 C26 N21 120.0(15) . . ? C25 C26 H26 120.0 . . ? N21 C26 H26 120.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.323 _refine_diff_density_min -1.478 _refine_diff_density_rms 0.247 # Attachment '6-HC115.CIF' data_hc115 _database_code_depnum_ccdc_archive 'CCDC 634021' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 6' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Br2 Hg N2' _chemical_formula_weight 574.71 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 8.0661(8) _cell_length_b 8.8122(8) _cell_length_c 12.9850(12) _cell_angle_alpha 79.354(2) _cell_angle_beta 86.643(2) _cell_angle_gamma 74.281(3) _cell_volume 873.13(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8130 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 25.99 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 13.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.284 _exptl_absorpt_correction_T_max 0.448 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.634237 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8130 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.1025 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3423 _reflns_number_gt 2175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0224P)^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 3423 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.09180(6) 0.32565(6) 0.24683(4) 0.0626(2) Uani 1 1 d . . . Br1 Br -0.18362(18) 0.49781(17) 0.29949(12) 0.0878(4) Uani 1 1 d . . . Br2 Br 0.41008(16) 0.27630(19) 0.24320(11) 0.0823(4) Uani 1 1 d . . . N11 N 0.0616(11) 0.0641(11) 0.3289(6) 0.058(2) Uani 1 1 d . . . C12 C 0.1988(12) -0.0627(14) 0.3421(8) 0.052(3) Uani 1 1 d . . . H12 H 0.3115 -0.0482 0.3173 0.068 Uiso 1 1 calc R . . C13 C 0.1879(14) -0.2142(15) 0.3897(8) 0.059(3) Uani 1 1 d . . . C14 C 0.0303(13) -0.2323(13) 0.4218(8) 0.055(3) Uani 1 1 d . . . H14 H 0.0181 -0.3380 0.4551 0.071 Uiso 1 1 calc R . . C15 C -0.1152(13) -0.1010(15) 0.4075(7) 0.053(3) Uani 1 1 d . . . C16 C -0.0896(12) 0.0425(14) 0.3605(7) 0.051(3) Uani 1 1 d . . . H16 H -0.1902 0.1355 0.3494 0.066 Uiso 1 1 calc R . . C17 C 0.3460(15) -0.3538(17) 0.4063(12) 0.090(4) Uani 1 1 d . . . H17A H 0.3855 -0.3711 0.4786 0.117 Uiso 1 1 calc R . . H17B H 0.4373 -0.3308 0.3577 0.117 Uiso 1 1 calc R . . H17C H 0.3181 -0.4502 0.3935 0.117 Uiso 1 1 calc R . . C18 C -0.2923(13) -0.1169(16) 0.4398(9) 0.069(3) Uani 1 1 d . . . H18A H -0.3401 -0.1558 0.3853 0.090 Uiso 1 1 calc R . . H18B H -0.3667 -0.0123 0.4495 0.090 Uiso 1 1 calc R . . H18C H -0.2856 -0.1931 0.5058 0.090 Uiso 1 1 calc R . . N21 N 0.0310(12) 0.2805(12) 0.0783(7) 0.063(3) Uani 1 1 d . . . C22 C 0.1604(16) 0.2114(14) 0.0202(8) 0.064(3) Uani 1 1 d . . . H22 H 0.2787 0.1923 0.0438 0.083 Uiso 1 1 calc R . . C23 C 0.1343(18) 0.1654(15) -0.0723(9) 0.074(4) Uani 1 1 d . . . C24 C -0.035(2) 0.1965(17) -0.1010(9) 0.078(4) Uani 1 1 d . . . H24 H -0.0597 0.1655 -0.1661 0.101 Uiso 1 1 calc R . . C25 C -0.1709(17) 0.2680(18) -0.0434(11) 0.080(4) Uani 1 1 d . . . C26 C -0.1308(15) 0.3082(16) 0.0480(10) 0.073(4) Uani 1 1 d . . . H26 H -0.2245 0.3588 0.0921 0.095 Uiso 1 1 calc R . . C27 C 0.2869(18) 0.0853(18) -0.1345(10) 0.090(4) Uani 1 1 d . . . H27A H 0.2660 -0.0099 -0.1544 0.117 Uiso 1 1 calc R . . H27B H 0.3908 0.0537 -0.0916 0.117 Uiso 1 1 calc R . . H27C H 0.3028 0.1602 -0.1978 0.117 Uiso 1 1 calc R . . C28 C -0.3540(18) 0.295(2) -0.0761(12) 0.106(5) Uani 1 1 d . . . H28A H -0.3693 0.3533 -0.1483 0.138 Uiso 1 1 calc R . . H28B H -0.4323 0.3576 -0.0294 0.138 Uiso 1 1 calc R . . H28C H -0.3796 0.1914 -0.0718 0.138 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 0.0620(3) 0.0601(3) 0.0660(3) -0.0162(2) 0.0048(2) -0.0145(2) Br1 0.0826(9) 0.0644(9) 0.1065(11) -0.0226(8) 0.0192(8) -0.0019(7) Br2 0.0615(8) 0.0904(11) 0.0964(10) -0.0146(8) 0.0049(7) -0.0248(7) N11 0.057(6) 0.055(6) 0.060(5) -0.011(4) -0.006(4) -0.013(5) C12 0.038(6) 0.061(8) 0.061(7) -0.022(6) -0.001(5) -0.011(6) C13 0.053(7) 0.058(8) 0.059(7) -0.008(6) -0.012(5) 0.000(6) C14 0.048(6) 0.044(7) 0.070(7) -0.002(5) -0.011(5) -0.011(5) C15 0.049(6) 0.079(9) 0.040(6) -0.016(6) 0.000(4) -0.028(6) C16 0.042(6) 0.062(8) 0.044(6) -0.009(5) 0.005(4) -0.006(5) C17 0.061(8) 0.068(10) 0.132(12) -0.014(8) 0.004(8) -0.003(7) C18 0.052(7) 0.088(10) 0.073(8) -0.018(7) 0.009(5) -0.029(7) N21 0.062(6) 0.067(7) 0.059(6) -0.019(5) 0.004(5) -0.013(5) C22 0.077(8) 0.063(8) 0.054(7) -0.020(6) 0.008(6) -0.017(7) C23 0.102(10) 0.064(9) 0.055(7) -0.001(6) -0.002(7) -0.028(8) C24 0.111(11) 0.083(10) 0.046(7) -0.001(6) -0.019(7) -0.039(9) C25 0.070(8) 0.089(11) 0.080(9) 0.015(8) -0.012(7) -0.038(8) C26 0.058(8) 0.089(11) 0.078(8) -0.025(7) -0.001(6) -0.021(7) C27 0.112(11) 0.079(11) 0.080(9) -0.033(8) 0.006(8) -0.016(9) C28 0.098(11) 0.111(14) 0.107(11) 0.006(9) -0.035(9) -0.034(10) _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 N21 2.397(9) . ? Hg N11 2.423(9) . ? Hg Br1 2.4665(14) . ? Hg Br2 2.4841(13) . ? N11 C16 1.316(13) . ? N11 C12 1.336(12) . ? C12 C13 1.387(16) . ? C12 H12 0.9800 . ? C13 C14 1.356(15) . ? C13 C17 1.507(15) . ? C14 C15 1.401(14) . ? C14 H14 0.9800 . ? C15 C16 1.362(15) . ? C15 C18 1.501(14) . ? C16 H16 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.328(13) . ? N21 C26 1.330(13) . ? C22 C23 1.380(15) . ? C22 H22 0.9800 . ? C23 C24 1.381(17) . ? C23 C27 1.513(17) . ? C24 C25 1.362(18) . ? C24 H24 0.9800 . ? C25 C26 1.379(17) . ? C25 C28 1.505(17) . ? C26 H26 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 N21 Hg N11 91.1(3) . . ? N21 Hg Br1 103.4(2) . . ? N11 Hg Br1 100.4(2) . . ? N21 Hg Br2 103.1(2) . . ? N11 Hg Br2 101.0(2) . . ? Br1 Hg Br2 145.31(6) . . ? C16 N11 C12 118.2(10) . . ? C16 N11 Hg 121.2(8) . . ? C12 N11 Hg 120.6(7) . . ? N11 C12 C13 122.5(10) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C14 C13 C12 117.8(10) . . ? C14 C13 C17 121.0(12) . . ? C12 C13 C17 121.2(11) . . ? C13 C14 C15 120.4(11) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 116.9(9) . . ? C16 C15 C18 121.1(11) . . ? C14 C15 C18 122.0(11) . . ? N11 C16 C15 124.1(10) . . ? N11 C16 H16 117.9 . . ? C15 C16 H16 117.9 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 120.2(10) . . ? C22 N21 Hg 118.9(7) . . ? C26 N21 Hg 120.5(7) . . ? N21 C22 C23 122.3(12) . . ? N21 C22 H22 118.8 . . ? C23 C22 H22 118.8 . . ? C22 C23 C24 115.8(12) . . ? C22 C23 C27 119.9(12) . . ? C24 C23 C27 124.3(12) . . ? C25 C24 C23 123.3(12) . . ? C25 C24 H24 118.4 . . ? C23 C24 H24 118.4 . . ? C24 C25 C26 116.4(12) . . ? C24 C25 C28 121.4(14) . . ? C26 C25 C28 122.2(14) . . ? N21 C26 C25 122.1(11) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.836 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.152 # Attachment '7-HC188.CIF' data_hc188 _database_code_depnum_ccdc_archive 'CCDC 634022' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 7' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H3 Cl2 Hg I2 N' _chemical_formula_weight 602.37 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' 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.270(7) _cell_length_b 4.2661(10) _cell_length_c 18.671(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.470(4) _cell_angle_gamma 90.00 _cell_volume 2176.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 10928 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.33 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 20.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.246 _exptl_absorpt_correction_T_max 0.545 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.450861 ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10928 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2713 _reflns_number_gt 2301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0284P)^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 2713 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.105962(10) 0.40592(7) 0.480893(16) 0.01890(9) Uani 1 1 d . . . I1 I 0.183298(17) 0.09447(11) 0.49098(3) 0.01915(12) Uani 1 1 d . . . I2 I 0.032982(17) 0.81160(11) 0.42816(3) 0.01969(12) Uani 1 1 d . . . Cl1 Cl 0.22902(7) 0.0785(5) 0.82265(11) 0.0256(4) Uani 1 1 d . . . Cl2 Cl 0.06535(7) 0.7503(5) 0.76166(11) 0.0265(4) Uani 1 1 d . . . N N 0.1233(2) 0.3994(14) 0.6246(3) 0.0172(13) Uani 1 1 d . . . C1 C 0.1636(3) 0.2595(18) 0.6779(4) 0.0186(15) Uani 1 1 d . . . H1 H 0.1851 0.1504 0.6591 0.024 Uiso 1 1 calc R . . C2 C 0.1759(3) 0.2622(17) 0.7572(4) 0.0169(15) Uani 1 1 d . . . C3 C 0.1465(3) 0.4152(18) 0.7867(4) 0.0202(16) Uani 1 1 d . . . H3 H 0.1549 0.4225 0.8436 0.026 Uiso 1 1 calc R . . C4 C 0.1049(3) 0.5559(18) 0.7308(4) 0.0198(16) Uani 1 1 d . . . C5 C 0.0942(3) 0.5519(17) 0.6516(4) 0.0184(15) Uani 1 1 d . . . H5 H 0.0649 0.6611 0.6139 0.024 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 0.01860(16) 0.01927(16) 0.01720(14) 0.00091(11) 0.00615(12) 0.00512(12) I1 0.0167(2) 0.0185(3) 0.0212(2) -0.00153(19) 0.0072(2) 0.00153(19) I2 0.0148(2) 0.0141(2) 0.0267(3) 0.00145(19) 0.0056(2) 0.00074(19) Cl1 0.0186(9) 0.0316(11) 0.0215(9) 0.0034(8) 0.0039(8) 0.0054(8) Cl2 0.0250(10) 0.0345(12) 0.0218(9) 0.0018(8) 0.0117(8) 0.0087(9) N 0.022(3) 0.018(3) 0.015(3) -0.002(2) 0.011(3) 0.001(3) C1 0.021(4) 0.023(4) 0.013(3) -0.002(3) 0.008(3) -0.002(3) C2 0.012(3) 0.017(4) 0.018(4) 0.001(3) 0.003(3) -0.002(3) C3 0.019(4) 0.026(4) 0.015(3) 0.001(3) 0.006(3) -0.003(3) C4 0.013(4) 0.021(4) 0.026(4) -0.002(3) 0.009(3) -0.005(3) C5 0.018(4) 0.017(4) 0.017(3) 0.002(3) 0.004(3) -0.004(3) _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 N 2.502(6) . ? Hg I1 2.6271(7) . ? Hg I2 2.6408(7) . ? Hg I2 3.2260(8) 1_545 ? Hg I1 3.7101(9) 1_565 ? Hg Cl2 3.792(2) 6_565 ? I2 Hg 3.2260(8) 1_565 ? Cl1 C2 1.732(7) . ? Cl2 C4 1.746(8) . ? N C1 1.338(9) . ? N C5 1.355(9) . ? C1 C2 1.362(10) . ? C1 H1 0.9800 . ? C2 C3 1.394(10) . ? C3 C4 1.380(10) . ? C3 H3 0.9800 . ? C4 C5 1.371(10) . ? C5 H5 0.9800 . ? 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 N Hg I1 98.50(14) . . ? N Hg I2 99.39(14) . . ? I1 Hg I2 159.21(2) . . ? N Hg I2 96.83(14) . 1_545 ? I1 Hg I2 95.54(2) . 1_545 ? I2 Hg I2 92.75(2) . 1_545 ? N Hg I1 96.75(14) . 1_565 ? I1 Hg I1 82.73(2) . 1_565 ? I2 Hg I1 84.75(2) . 1_565 ? I2 Hg I1 166.421(15) 1_545 1_565 ? N Hg Cl2 167.51(14) . 6_565 ? I1 Hg Cl2 81.59(3) . 6_565 ? I2 Hg Cl2 83.21(4) . 6_565 ? I2 Hg Cl2 70.78(3) 1_545 6_565 ? I1 Hg Cl2 95.65(3) 1_565 6_565 ? Hg I2 Hg 92.75(2) . 1_565 ? C1 N C5 117.9(6) . . ? C1 N Hg 120.4(4) . . ? C5 N Hg 121.6(5) . . ? N C1 C2 122.8(7) . . ? N C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 120.7(7) . . ? C1 C2 Cl1 120.0(6) . . ? C3 C2 Cl1 119.3(6) . . ? C4 C3 C2 115.8(7) . . ? C4 C3 H3 122.1 . . ? C2 C3 H3 122.1 . . ? C5 C4 C3 121.7(7) . . ? C5 C4 Cl2 118.9(6) . . ? C3 C4 Cl2 119.3(6) . . ? N C5 C4 121.1(7) . . ? N C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 Hg N C1 0.1(6) . . . . ? I1 Hg N C2 3.2(6) . . . . ? I2 Hg N C1 -169.2(5) . . . . ? I2 Hg N C2 -166.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.651 _refine_diff_density_min -1.640 _refine_diff_density_rms 0.275 # Attachment '8-HC119.CIF' data_hc119 _database_code_depnum_ccdc_archive 'CCDC 634023' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 8' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H3 Br2 Hg I2 N' _chemical_formula_weight 691.29 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.509(4) _cell_length_b 4.3075(5) _cell_length_c 19.009(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.703(2) _cell_angle_gamma 90.00 _cell_volume 2324.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14973 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 28.30 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 25.375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.058 _exptl_absorpt_correction_T_max 0.169 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.343992 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14973 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2882 _reflns_number_gt 2165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0170P)^2^+9.8617P] 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 2882 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.106040(13) 0.42456(9) 0.48496(2) 0.04891(13) Uani 1 1 d . . . I1 I 0.17993(2) 0.12276(13) 0.49282(4) 0.04810(17) Uani 1 1 d . . . I2 I 0.03539(2) 0.81847(13) 0.43587(4) 0.04789(17) Uani 1 1 d . . . Br1 Br 0.22935(3) 0.0720(3) 0.82877(6) 0.0582(3) Uani 1 1 d . . . Br2 Br 0.06211(4) 0.7441(3) 0.76343(6) 0.0652(3) Uani 1 1 d . . . N N 0.1229(3) 0.4033(17) 0.6278(4) 0.0486(18) Uani 1 1 d . . . C1 C 0.1622(3) 0.266(2) 0.6791(5) 0.043(2) Uani 1 1 d . . . H1 H 0.1833 0.1646 0.6606 0.056 Uiso 1 1 calc R . . C2 C 0.1735(3) 0.2663(19) 0.7578(5) 0.0399(19) Uani 1 1 d . . . C3 C 0.1444(3) 0.409(2) 0.7863(5) 0.043(2) Uani 1 1 d . . . H3 H 0.1524 0.4143 0.8422 0.056 Uiso 1 1 calc R . . C4 C 0.1039(3) 0.542(2) 0.7312(5) 0.045(2) Uani 1 1 d . . . C5 C 0.0942(3) 0.544(2) 0.6539(5) 0.043(2) Uani 1 1 d . . . H5 H 0.0658 0.6500 0.6166 0.056 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 0.0507(2) 0.0556(2) 0.0384(2) 0.00285(16) 0.01741(16) 0.01587(17) I1 0.0435(3) 0.0516(3) 0.0480(4) -0.0045(3) 0.0187(3) 0.0070(3) I2 0.0381(3) 0.0413(3) 0.0590(4) 0.0039(3) 0.0160(3) 0.0041(2) Br1 0.0431(5) 0.0781(7) 0.0444(6) 0.0089(5) 0.0105(4) 0.0126(5) Br2 0.0542(6) 0.0978(8) 0.0507(6) 0.0049(6) 0.0295(5) 0.0209(6) N 0.050(5) 0.064(5) 0.033(4) 0.003(4) 0.019(4) -0.001(4) C1 0.035(5) 0.060(5) 0.030(5) -0.007(4) 0.010(4) -0.004(4) C2 0.023(4) 0.053(5) 0.034(5) -0.001(4) 0.003(3) -0.003(4) C3 0.043(5) 0.059(5) 0.028(4) 0.000(4) 0.016(4) 0.000(4) C4 0.039(5) 0.056(5) 0.042(5) -0.009(4) 0.021(4) -0.005(4) C5 0.030(4) 0.068(6) 0.031(5) 0.004(4) 0.013(4) 0.004(4) _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 N 2.532(7) . ? Hg I1 2.6138(7) . ? Hg I2 2.6275(7) . ? Hg I2 3.2925(8) 1_545 ? Hg I1 3.7665(8) 1_565 ? Hg Br2 3.8887(12) 6_565 ? I2 Hg 3.2925(8) 1_565 ? Br1 C2 1.887(8) . ? Br2 C4 1.888(8) . ? N C1 1.336(10) . ? N C5 1.350(11) . ? C1 C2 1.379(12) . ? C1 H1 0.9800 . ? C2 C3 1.393(12) . ? C3 C4 1.378(11) . ? C3 H3 0.9800 . ? C4 C5 1.365(12) . ? C5 H5 0.9800 . ? 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 N Hg I1 98.84(17) . . ? N Hg I2 98.94(17) . . ? I1 Hg I2 159.72(3) . . ? N Hg I2 94.40(17) . 1_545 ? I1 Hg I2 95.62(2) . 1_545 ? I2 Hg I2 92.68(2) . 1_545 ? N Hg I1 98.51(17) . 1_565 ? I1 Hg I1 82.81(2) . 1_565 ? I2 Hg I1 84.97(2) . 1_565 ? I2 Hg I1 167.088(19) 1_545 1_565 ? N Hg Br2 164.81(17) . 6_565 ? I1 Hg Br2 81.88(2) . 6_565 ? I2 Hg Br2 83.52(3) . 6_565 ? I2 Hg Br2 70.46(2) 1_545 6_565 ? I1 Hg Br2 96.64(2) 1_565 6_565 ? Hg I2 Hg 92.68(2) . 1_565 ? C1 N C5 119.1(7) . . ? C1 N Hg 119.7(6) . . ? C5 N Hg 121.1(6) . . ? N C1 C2 121.0(8) . . ? N C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 121.2(8) . . ? C1 C2 Br1 119.9(7) . . ? C3 C2 Br1 118.9(6) . . ? C4 C3 C2 115.9(8) . . ? C4 C3 H3 122.1 . . ? C2 C3 H3 122.1 . . ? C5 C4 C3 121.5(8) . . ? C5 C4 Br2 118.9(7) . . ? C3 C4 Br2 119.5(7) . . ? N C5 C4 121.3(8) . . ? N C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 Hg N C1 1.4(7) . . . . ? I1 Hg N C2 4.9(8) . . . . ? I2 Hg N C1 -168.8(6) . . . . ? I2 Hg N C2 -165.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.478 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.209 # Attachment '9a-HC124.CIF' data_hc124 _database_code_depnum_ccdc_archive 'CCDC 634024' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 9a' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 Hg I2 N' _chemical_formula_weight 561.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.055(3) _cell_length_b 4.3117(4) _cell_length_c 19.1185(18) _cell_angle_alpha 90.00 _cell_angle_beta 115.520(2) _cell_angle_gamma 90.00 _cell_volume 2310.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10369 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.36 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 18.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.135 _exptl_absorpt_correction_T_max 0.272 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.497903 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10369 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2862 _reflns_number_gt 1967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0311P)^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 2862 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.109314(14) 0.43919(10) 0.49620(2) 0.05475(16) Uani 1 1 d . . . I1 I 0.18259(2) 0.14226(16) 0.49428(4) 0.0567(2) Uani 1 1 d . . . I2 I 0.03793(2) 0.83569(15) 0.43678(4) 0.0552(2) Uani 1 1 d . . . N N 0.1230(3) 0.416(2) 0.6298(4) 0.054(2) Uani 1 1 d . . . C1 C 0.1630(3) 0.277(2) 0.6816(5) 0.048(2) Uani 1 1 d . . . H1 H 0.1855 0.1905 0.6634 0.063 Uiso 1 1 calc R . . C2 C 0.1733(3) 0.253(2) 0.7583(6) 0.051(2) Uani 1 1 d . . . C3 C 0.1411(4) 0.384(2) 0.7831(6) 0.054(3) Uani 1 1 d . . . H3 H 0.1476 0.3743 0.8380 0.071 Uiso 1 1 calc R . . C4 C 0.1000(4) 0.529(2) 0.7301(6) 0.050(2) Uani 1 1 d . . . C5 C 0.0933(4) 0.535(3) 0.6536(6) 0.057(3) Uani 1 1 d . . . H5 H 0.0644 0.6345 0.6152 0.074 Uiso 1 1 calc R . . C6 C 0.2184(4) 0.103(3) 0.8132(6) 0.063(3) Uani 1 1 d . . . H6A H 0.2200 0.1055 0.8655 0.081 Uiso 1 1 calc R . . H6B H 0.2457 0.2172 0.8131 0.081 Uiso 1 1 calc R . . H6C H 0.2192 -0.1115 0.7971 0.081 Uiso 1 1 calc R . . C7 C 0.0647(4) 0.667(3) 0.7551(7) 0.077(4) Uani 1 1 d . . . H7A H 0.0759 0.6368 0.8110 0.100 Uiso 1 1 calc R . . H7B H 0.0337 0.5652 0.7274 0.100 Uiso 1 1 calc R . . H7C H 0.0614 0.8893 0.7434 0.100 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 0.0572(3) 0.0655(3) 0.0412(2) 0.00266(19) 0.02086(19) 0.0184(2) I1 0.0524(4) 0.0604(4) 0.0601(4) -0.0045(3) 0.0269(3) 0.0089(3) I2 0.0449(4) 0.0455(4) 0.0681(5) 0.0033(3) 0.0176(3) 0.0046(3) N 0.054(5) 0.080(6) 0.031(4) -0.005(4) 0.022(4) 0.001(4) C1 0.044(6) 0.067(6) 0.034(5) 0.002(5) 0.016(4) -0.001(5) C2 0.046(6) 0.048(6) 0.050(6) 0.006(5) 0.012(5) -0.010(5) C3 0.062(7) 0.070(7) 0.035(5) 0.002(5) 0.026(5) -0.005(5) C4 0.051(6) 0.066(7) 0.041(5) -0.009(5) 0.027(5) -0.008(5) C5 0.051(6) 0.075(7) 0.045(6) 0.003(5) 0.019(5) -0.004(5) C6 0.053(7) 0.082(8) 0.047(6) 0.009(5) 0.016(5) -0.004(5) C7 0.067(8) 0.116(11) 0.055(7) -0.008(7) 0.033(6) 0.013(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 Hg N 2.404(7) . ? Hg I1 2.6251(8) . ? Hg I2 2.6377(8) . ? Hg I2 3.2873(9) 1_545 ? Hg I1 3.8002(9) 1_565 ? I2 Hg 3.2873(9) 1_565 ? N C5 1.297(13) . ? N C1 1.350(12) . ? C1 C2 1.363(13) . ? C1 H1 0.9800 . ? C2 C3 1.398(15) . ? C2 C6 1.487(14) . ? C3 C4 1.391(15) . ? C3 H3 0.9800 . ? C4 C5 1.386(14) . ? C4 C7 1.494(14) . ? C5 H5 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 N Hg I1 103.7(2) . . ? N Hg I2 102.4(2) . . ? I1 Hg I2 151.99(3) . . ? N Hg I2 96.8(2) . 1_545 ? I1 Hg I2 93.94(2) . 1_545 ? I2 Hg I2 92.73(2) . 1_545 ? N Hg I1 102.2(2) . 1_565 ? I1 Hg I1 82.10(2) . 1_565 ? I2 Hg I1 82.79(2) . 1_565 ? I2 Hg I1 161.01(2) 1_545 1_565 ? Hg I2 Hg 92.73(2) . 1_565 ? C5 N C1 119.1(8) . . ? C5 N Hg 122.0(7) . . ? C1 N Hg 118.9(6) . . ? N C1 C2 122.6(9) . . ? N C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 117.6(9) . . ? C1 C2 C6 120.3(10) . . ? C3 C2 C6 122.0(9) . . ? C4 C3 C2 120.1(9) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 116.7(10) . . ? C5 C4 C7 122.3(10) . . ? C3 C4 C7 121.0(9) . . ? N C5 C4 123.9(10) . . ? N C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 Hg N C1 2.0(8) . . . . ? I1 Hg N C2 1.7(9) . . . . ? I2 Hg N C1 -168.0(7) . . . . ? I2 Hg N C2 -168.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.171 _refine_diff_density_min -1.197 _refine_diff_density_rms 0.211 # Attachment '9b-HC125.CIF' data_hc125 _database_code_depnum_ccdc_archive 'CCDC 634025' _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 9b' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Hg I2 N2' _chemical_formula_weight 668.69 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' 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 8.2309(6) _cell_length_b 9.1784(7) _cell_length_c 13.0920(10) _cell_angle_alpha 79.229(3) _cell_angle_beta 88.173(3) _cell_angle_gamma 74.877(3) _cell_volume 937.83(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14350 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 28.31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 11.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.295 _exptl_absorpt_correction_T_max 0.502 _exptl_absorpt_process_details SADABS _exptl_special_details ; Ratio of minimum to maximum apparent transmission: 0.586879 ; _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14350 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4625 _reflns_number_gt 2722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 1998)' _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^)+(0.0271P)^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 4625 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.08913(4) 0.31581(4) 0.24294(3) 0.05991(14) Uani 1 1 d . . . I1 I -0.19274(8) 0.50042(7) 0.29314(6) 0.0792(2) Uani 1 1 d . . . I2 I 0.41904(7) 0.28040(8) 0.24458(5) 0.0794(2) Uani 1 1 d . . . N11 N 0.0625(8) 0.0630(7) 0.3285(5) 0.0505(16) Uani 1 1 d . . . C12 C 0.1985(10) -0.0571(10) 0.3427(6) 0.052(2) Uani 1 1 d . . . H12 H 0.3074 -0.0416 0.3179 0.068 Uiso 1 1 calc R . . C13 C 0.1899(10) -0.2027(10) 0.3914(7) 0.058(2) Uani 1 1 d . . . C14 C 0.0323(11) -0.2196(10) 0.4214(6) 0.058(2) Uani 1 1 d . . . H14 H 0.0214 -0.3214 0.4547 0.076 Uiso 1 1 calc R . . C15 C -0.1087(10) -0.0997(10) 0.4065(6) 0.052(2) Uani 1 1 d . . . C16 C -0.0874(10) 0.0449(10) 0.3601(6) 0.054(2) Uani 1 1 d . . . H16 H -0.1851 0.1344 0.3509 0.070 Uiso 1 1 calc R . . C17 C 0.3446(12) -0.3324(12) 0.4082(8) 0.086(3) Uani 1 1 d . . . H17A H 0.3845 -0.3502 0.4803 0.112 Uiso 1 1 calc R . . H17B H 0.4322 -0.3071 0.3610 0.112 Uiso 1 1 calc R . . H17C H 0.3190 -0.4254 0.3942 0.112 Uiso 1 1 calc R . . C18 C -0.2770(11) -0.1177(12) 0.4405(7) 0.076(3) Uani 1 1 d . . . H18A H -0.3271 -0.1562 0.3876 0.099 Uiso 1 1 calc R . . H18B H -0.3495 -0.0181 0.4499 0.099 Uiso 1 1 calc R . . H18C H -0.2656 -0.1908 0.5064 0.099 Uiso 1 1 calc R . . N21 N 0.0286(10) 0.2656(9) 0.0763(5) 0.0648(19) Uani 1 1 d . . . C22 C 0.1539(12) 0.1975(11) 0.0211(7) 0.069(2) Uani 1 1 d . . . H22 H 0.2691 0.1770 0.0479 0.089 Uiso 1 1 calc R . . C23 C 0.1320(14) 0.1539(11) -0.0714(7) 0.074(3) Uani 1 1 d . . . C24 C -0.0323(17) 0.1805(13) -0.1046(8) 0.086(3) Uani 1 1 d . . . H24 H -0.0544 0.1483 -0.1689 0.112 Uiso 1 1 calc R . . C25 C -0.1653(15) 0.2505(13) -0.0502(8) 0.080(3) Uani 1 1 d . . . C26 C -0.1289(12) 0.2933(11) 0.0423(7) 0.071(3) Uani 1 1 d . . . H26 H -0.2216 0.3445 0.0826 0.092 Uiso 1 1 calc R . . C27 C 0.2789(16) 0.0761(12) -0.1281(8) 0.100(4) Uani 1 1 d . . . H27A H 0.2577 -0.0157 -0.1471 0.130 Uiso 1 1 calc R . . H27B H 0.3799 0.0464 -0.0834 0.130 Uiso 1 1 calc R . . H27C H 0.2960 0.1465 -0.1913 0.130 Uiso 1 1 calc R . . C28 C -0.3512(14) 0.2866(16) -0.0823(10) 0.116(5) Uani 1 1 d . . . H28A H -0.3677 0.3442 -0.1538 0.151 Uiso 1 1 calc R . . H28B H -0.4207 0.3482 -0.0355 0.151 Uiso 1 1 calc R . . H28C H -0.3840 0.1904 -0.0781 0.151 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 0.0523(2) 0.0624(3) 0.0675(2) -0.01903(17) 0.00330(16) -0.01450(17) I1 0.0667(4) 0.0613(4) 0.1053(5) -0.0229(4) 0.0139(4) -0.0052(3) I2 0.0528(4) 0.0898(5) 0.0980(5) -0.0153(4) 0.0026(3) -0.0243(4) N11 0.051(4) 0.051(4) 0.051(4) -0.009(3) 0.000(3) -0.016(3) C12 0.039(4) 0.059(6) 0.058(5) -0.014(4) 0.003(4) -0.010(4) C13 0.050(5) 0.062(6) 0.064(5) -0.020(5) -0.002(4) -0.010(5) C14 0.070(6) 0.048(5) 0.057(5) -0.007(4) -0.012(4) -0.015(5) C15 0.044(5) 0.061(6) 0.056(5) -0.019(4) -0.009(4) -0.016(4) C16 0.049(5) 0.062(6) 0.059(5) -0.025(4) -0.005(4) -0.016(4) C17 0.073(7) 0.071(7) 0.101(8) -0.010(6) -0.001(6) 0.001(6) C18 0.071(6) 0.087(8) 0.076(6) -0.025(5) -0.003(5) -0.024(6) N21 0.064(5) 0.074(5) 0.060(5) -0.019(4) 0.008(4) -0.022(4) C22 0.071(6) 0.077(7) 0.064(6) -0.023(5) -0.001(5) -0.021(5) C23 0.097(8) 0.067(7) 0.065(6) -0.010(5) -0.001(6) -0.035(6) C24 0.120(10) 0.090(8) 0.054(6) 0.001(6) -0.004(7) -0.046(8) C25 0.104(8) 0.083(8) 0.062(6) 0.009(5) -0.028(6) -0.053(7) C26 0.069(6) 0.070(7) 0.068(6) -0.003(5) -0.008(5) -0.014(5) C27 0.156(12) 0.076(8) 0.069(7) -0.029(6) 0.016(7) -0.022(8) C28 0.095(9) 0.134(12) 0.125(10) 0.006(8) -0.047(8) -0.053(8) _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 N21 2.405(7) . ? Hg N11 2.442(6) . ? Hg I1 2.6369(7) . ? Hg I2 2.6497(7) . ? N11 C16 1.331(9) . ? N11 C12 1.339(9) . ? C12 C13 1.388(11) . ? C12 H12 0.9800 . ? C13 C14 1.382(11) . ? C13 C17 1.489(12) . ? C14 C15 1.365(11) . ? C14 H14 0.9800 . ? C15 C16 1.405(11) . ? C15 C18 1.482(11) . ? C16 H16 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N21 C22 1.327(11) . ? N21 C26 1.330(11) . ? C22 C23 1.375(12) . ? C22 H22 0.9800 . ? C23 C24 1.379(14) . ? C23 C27 1.488(14) . ? C24 C25 1.369(15) . ? C24 H24 0.9800 . ? C25 C26 1.404(13) . ? C25 C28 1.534(14) . ? C26 H26 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 N21 Hg N11 90.9(2) . . ? N21 Hg I1 104.59(19) . . ? N11 Hg I1 102.54(15) . . ? N21 Hg I2 104.47(18) . . ? N11 Hg I2 102.69(15) . . ? I1 Hg I2 140.84(3) . . ? C16 N11 C12 120.3(7) . . ? C16 N11 Hg 119.8(5) . . ? C12 N11 Hg 119.9(5) . . ? N11 C12 C13 122.1(7) . . ? N11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 116.7(8) . . ? C14 C13 C17 122.8(8) . . ? C12 C13 C17 120.5(8) . . ? C15 C14 C13 122.4(8) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C16 117.1(8) . . ? C14 C15 C18 122.3(8) . . ? C16 C15 C18 120.6(8) . . ? N11 C16 C15 121.4(8) . . ? N11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C22 N21 C26 119.2(8) . . ? C22 N21 Hg 119.4(6) . . ? C26 N21 Hg 121.2(6) . . ? N21 C22 C23 124.0(9) . . ? N21 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C22 C23 C24 116.1(10) . . ? C22 C23 C27 120.8(10) . . ? C24 C23 C27 123.0(10) . . ? C25 C24 C23 121.8(10) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C24 C25 C26 117.5(10) . . ? C24 C25 C28 125.2(11) . . ? C26 C25 C28 117.3(11) . . ? N21 C26 C25 121.3(10) . . ? N21 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.715 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.152