# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_smm065d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl4 Hg2 N2 O4' _chemical_formula_weight 793.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/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 11.6344(5) _cell_length_b 11.0503(5) _cell_length_c 15.0011(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.075(6) _cell_angle_gamma 90.00 _cell_volume 1917.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2850 _cell_measurement_theta_min 2.9739 _cell_measurement_theta_max 32.1682 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 16.567 _exptl_absorpt_correction_T_min 0.1150 _exptl_absorpt_correction_T_max 0.2220 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5737 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0242 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1687 _reflns_number_gt 1459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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. DFIX is applied to hydrogen atoms over water molecule (O111). ; _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^)+(0.0352P)^2^+45.3969P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1687 _refine_ls_number_parameters 117 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _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 0.94245(4) 0.06419(4) 0.12065(4) 0.0710(2) Uani 1 1 d . . . Cl1 Cl 0.8950(3) -0.1210(3) 0.04895(19) 0.0714(8) Uani 1 1 d . . . Cl2 Cl 1.1468(2) 0.0292(3) 0.21776(18) 0.0628(7) Uani 1 1 d . . . O1 O 0.7283(7) 0.1698(8) 0.0989(5) 0.071(2) Uani 1 1 d . . . N1 N 0.9530(6) 0.2634(7) 0.1154(5) 0.0422(18) Uani 1 1 d . . . C1 C 1.0548(9) 0.3154(10) 0.1412(7) 0.055(3) Uani 1 1 d . . . H1 H 1.1191 0.2657 0.1610 0.066 Uiso 1 1 calc R . . C2 C 1.0688(10) 0.4377(11) 0.1398(8) 0.061(3) Uani 1 1 d . . . H2 H 1.1419 0.4730 0.1582 0.074 Uiso 1 1 calc R . . C3 C 0.9754(10) 0.5092(11) 0.1113(7) 0.059(3) Uani 1 1 d . . . H3 H 0.9829 0.5948 0.1107 0.070 Uiso 1 1 calc R . . C4 C 0.8715(10) 0.4558(10) 0.0840(7) 0.056(3) Uani 1 1 d . . . H4 H 0.8064 0.5042 0.0638 0.068 Uiso 1 1 calc R . . C5 C 0.8616(8) 0.3325(9) 0.0857(6) 0.043(2) Uani 1 1 d . . . C6 C 0.7486(9) 0.2698(10) 0.0503(6) 0.052(2) Uani 1 1 d . . . H6 H 0.6833 0.3279 0.0536 0.062 Uiso 1 1 calc R . . O101 O 0.6301(13) 0.2382(13) 0.2438(9) 0.117(4) Uani 1 1 d D . . H111 H 0.68(4) 0.24(6) 0.20(3) 0.6(5) Uiso 1 1 d D . . H222 H 0.63(4) 0.23(4) 0.298(6) 0.4(3) Uiso 1 1 d 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 0.0704(4) 0.0537(3) 0.0844(4) -0.0043(2) -0.0117(3) -0.0100(2) Cl1 0.099(2) 0.0550(16) 0.0590(16) -0.0106(13) 0.0034(15) -0.0087(16) Cl2 0.0500(15) 0.085(2) 0.0513(14) -0.0006(13) -0.0032(11) 0.0109(14) O1 0.072(5) 0.073(5) 0.067(5) 0.008(4) 0.006(4) -0.014(4) N1 0.036(4) 0.047(4) 0.043(4) 0.000(3) 0.000(3) -0.010(3) C1 0.041(6) 0.066(7) 0.054(6) -0.001(5) -0.007(4) -0.008(5) C2 0.046(6) 0.075(8) 0.062(7) -0.001(6) -0.002(5) -0.023(6) C3 0.058(7) 0.051(6) 0.066(7) -0.008(5) 0.008(5) -0.018(5) C4 0.050(6) 0.058(7) 0.060(6) -0.011(5) 0.001(5) -0.007(5) C5 0.038(5) 0.049(6) 0.043(5) -0.010(4) 0.006(4) -0.008(4) C6 0.045(6) 0.060(6) 0.049(5) 0.001(5) 0.001(4) -0.015(5) O101 0.149(11) 0.115(9) 0.093(8) -0.010(7) 0.044(8) 0.005(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 Hg1 N1 2.206(8) . ? Hg1 Cl1 2.351(3) . ? Hg1 Cl2 2.682(3) . ? Hg1 Cl2 2.764(3) 2_755 ? Cl2 Hg1 2.764(3) 2_755 ? O1 C6 1.358(13) . ? N1 C1 1.335(12) . ? N1 C5 1.346(12) . ? C1 C2 1.361(15) . ? C1 H1 0.9500 . ? C2 C3 1.374(16) . ? C2 H2 0.9500 . ? C3 C4 1.369(15) . ? C3 H3 0.9500 . ? C4 C5 1.367(14) . ? C4 H4 0.9500 . ? C5 C6 1.532(13) . ? C6 C6 1.574(19) 7_655 ? C6 H6 1.0000 . ? O101 H111 0.880(11) . ? O101 H222 0.820(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Hg1 Cl1 149.7(2) . . ? N1 Hg1 Cl2 96.5(2) . . ? Cl1 Hg1 Cl2 105.94(11) . . ? N1 Hg1 Cl2 101.5(2) . 2_755 ? Cl1 Hg1 Cl2 100.81(10) . 2_755 ? Cl2 Hg1 Cl2 84.10(9) . 2_755 ? Hg1 Cl2 Hg1 93.57(9) . 2_755 ? C1 N1 C5 119.7(9) . . ? C1 N1 Hg1 118.0(7) . . ? C5 N1 Hg1 122.2(6) . . ? N1 C1 C2 121.8(10) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C1 C2 C3 118.9(10) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 119.3(11) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 119.8(11) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 120.5(9) . . ? N1 C5 C6 118.5(9) . . ? C4 C5 C6 121.0(9) . . ? O1 C6 C5 111.9(9) . . ? O1 C6 C6 108.2(11) . 7_655 ? C5 C6 C6 110.7(10) . 7_655 ? O1 C6 H6 108.7 . . ? C5 C6 H6 108.7 . . ? C6 C6 H6 108.7 7_655 . ? H111 O101 H222 142(10) . . ? 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 N1 Hg1 Cl2 Hg1 84.9(2) . . . 2_755 ? Cl1 Hg1 Cl2 Hg1 -115.58(10) . . . 2_755 ? Cl2 Hg1 Cl2 Hg1 -15.99(13) 2_755 . . 2_755 ? Cl1 Hg1 N1 C1 -125.6(7) . . . . ? Cl2 Hg1 N1 C1 12.5(7) . . . . ? Cl2 Hg1 N1 C1 97.7(7) 2_755 . . . ? Cl1 Hg1 N1 C5 53.1(9) . . . . ? Cl2 Hg1 N1 C5 -168.8(7) . . . . ? Cl2 Hg1 N1 C5 -83.5(7) 2_755 . . . ? C5 N1 C1 C2 1.1(15) . . . . ? Hg1 N1 C1 C2 179.9(8) . . . . ? N1 C1 C2 C3 0.2(18) . . . . ? C1 C2 C3 C4 -0.9(18) . . . . ? C2 C3 C4 C5 0.4(17) . . . . ? C1 N1 C5 C4 -1.7(14) . . . . ? Hg1 N1 C5 C4 179.6(7) . . . . ? C1 N1 C5 C6 175.7(9) . . . . ? Hg1 N1 C5 C6 -3.1(11) . . . . ? C3 C4 C5 N1 0.9(16) . . . . ? C3 C4 C5 C6 -176.3(9) . . . . ? N1 C5 C6 O1 38.1(12) . . . . ? C4 C5 C6 O1 -144.6(10) . . . . ? N1 C5 C6 C6 -82.6(13) . . . 7_655 ? C4 C5 C6 C6 94.7(14) . . . 7_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.044 _refine_diff_density_min -1.526 _refine_diff_density_rms 0.164 _database_code_depnum_ccdc_archive 'CCDC 926951' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl4 Hg2 N2 O2' _chemical_formula_weight 759.22 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' O O 0.0106 0.0060 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2128(4) _cell_length_b 7.3831(4) _cell_length_c 9.4670(4) _cell_angle_alpha 107.164(4) _cell_angle_beta 92.654(4) _cell_angle_gamma 112.675(5) _cell_volume 437.07(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3619 _cell_measurement_theta_min 3.1728 _cell_measurement_theta_max 32.4853 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.884 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 18.158 _exptl_absorpt_correction_T_min 0.2192 _exptl_absorpt_correction_T_max 0.3630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2875 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1538 _reflns_number_gt 1519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0374P)^2^+0.0226P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1538 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.79657(3) 0.22240(2) 0.489957(17) 0.01814(10) Uani 1 1 d . . . Cl1 Cl 0.7886(2) 0.0177(2) 0.24477(14) 0.0246(3) Uani 1 1 d . . . Cl2 Cl 0.77828(19) 0.55676(18) 0.42540(13) 0.0183(3) Uani 1 1 d . . . O1 O 0.6320(6) -0.0971(6) 0.5810(4) 0.0251(8) Uani 1 1 d . . . N1 N 0.7582(6) 0.3226(6) 0.7233(5) 0.0171(9) Uani 1 1 d . . . C1 C 0.7805(9) 0.5204(8) 0.7867(6) 0.0217(11) Uani 1 1 d . . . H1 H 0.8037 0.6063 0.7259 0.026 Uiso 1 1 calc R . . C2 C 0.7713(9) 0.6037(9) 0.9346(6) 0.0268(12) Uani 1 1 d . . . H2 H 0.7862 0.7435 0.9755 0.032 Uiso 1 1 calc R . . C3 C 0.7400(9) 0.4791(9) 1.0227(6) 0.0259(12) Uani 1 1 d . . . H3 H 0.7350 0.5329 1.1261 0.031 Uiso 1 1 calc R . . C4 C 0.7162(8) 0.2773(9) 0.9600(6) 0.0259(12) Uani 1 1 d . . . H4 H 0.6937 0.1903 1.0197 0.031 Uiso 1 1 calc R . . C5 C 0.7249(7) 0.2001(8) 0.8092(5) 0.0181(10) Uani 1 1 d . . . C6 C 0.7003(9) -0.0214(8) 0.7398(6) 0.0239(11) Uani 1 1 d . . . H6A H 0.8328 -0.0279 0.7612 0.029 Uiso 1 1 calc R . . H6B H 0.6004 -0.1117 0.7855 0.029 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 0.02155(15) 0.01710(14) 0.01277(14) 0.00147(9) 0.00815(9) 0.00710(10) Cl1 0.0243(7) 0.0268(7) 0.0156(6) -0.0025(5) 0.0079(5) 0.0100(5) Cl2 0.0207(6) 0.0199(6) 0.0158(6) 0.0057(5) 0.0059(5) 0.0099(5) O1 0.029(2) 0.0208(19) 0.028(2) 0.0075(16) 0.0088(17) 0.0132(16) N1 0.016(2) 0.019(2) 0.016(2) 0.0066(18) 0.0072(17) 0.0070(18) C1 0.030(3) 0.020(3) 0.014(2) 0.004(2) 0.007(2) 0.010(2) C2 0.032(3) 0.027(3) 0.016(3) 0.000(2) 0.005(2) 0.012(2) C3 0.019(3) 0.044(3) 0.012(2) 0.005(2) 0.007(2) 0.013(2) C4 0.020(3) 0.039(3) 0.019(3) 0.016(2) 0.003(2) 0.009(2) C5 0.011(2) 0.028(3) 0.018(2) 0.011(2) 0.006(2) 0.007(2) C6 0.024(3) 0.027(3) 0.028(3) 0.015(2) 0.010(2) 0.014(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 Hg1 N1 2.180(4) . ? Hg1 Cl1 2.3506(12) . ? Hg1 O1 2.618(4) . ? Hg1 Cl2 2.7603(12) . ? Hg1 Cl2 2.8018(13) 2_766 ? Cl2 Hg1 2.8018(13) 2_766 ? O1 C6 1.427(6) . ? N1 C1 1.346(7) . ? N1 C5 1.350(6) . ? C1 C2 1.370(7) . ? C1 H1 0.9500 . ? C2 C3 1.379(8) . ? C2 H2 0.9500 . ? C3 C4 1.368(8) . ? C3 H3 0.9500 . ? C4 C5 1.386(7) . ? C4 H4 0.9500 . ? C5 C6 1.506(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Hg1 Cl1 163.21(12) . . ? N1 Hg1 O1 68.88(13) . . ? Cl1 Hg1 O1 94.36(9) . . ? N1 Hg1 Cl2 96.26(11) . . ? Cl1 Hg1 Cl2 98.19(4) . . ? O1 Hg1 Cl2 150.13(9) . . ? N1 Hg1 Cl2 91.08(11) . 2_766 ? Cl1 Hg1 Cl2 97.60(4) . 2_766 ? O1 Hg1 Cl2 115.83(9) . 2_766 ? Cl2 Hg1 Cl2 89.28(4) . 2_766 ? Hg1 Cl2 Hg1 90.72(4) . 2_766 ? C6 O1 Hg1 106.5(3) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Hg1 118.0(3) . . ? C5 N1 Hg1 123.2(3) . . ? N1 C1 C2 123.0(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.2(5) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 119.5(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 120.6(5) . . ? N1 C5 C6 119.1(4) . . ? C4 C5 C6 120.3(5) . . ? O1 C6 C5 111.3(4) . . ? O1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? 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 N1 Hg1 Cl2 Hg1 91.00(11) . . . 2_766 ? Cl1 Hg1 Cl2 Hg1 -97.57(4) . . . 2_766 ? O1 Hg1 Cl2 Hg1 148.54(17) . . . 2_766 ? Cl2 Hg1 Cl2 Hg1 0.0 2_766 . . 2_766 ? N1 Hg1 O1 C6 -27.3(3) . . . . ? Cl1 Hg1 O1 C6 153.9(3) . . . . ? Cl2 Hg1 O1 C6 -91.3(3) . . . . ? Cl2 Hg1 O1 C6 53.3(3) 2_766 . . . ? Cl1 Hg1 N1 C1 -163.2(3) . . . . ? O1 Hg1 N1 C1 -167.2(4) . . . . ? Cl2 Hg1 N1 C1 -13.9(4) . . . . ? Cl2 Hg1 N1 C1 75.4(4) 2_766 . . . ? Cl1 Hg1 N1 C5 20.7(7) . . . . ? O1 Hg1 N1 C5 16.7(4) . . . . ? Cl2 Hg1 N1 C5 170.0(4) . . . . ? Cl2 Hg1 N1 C5 -100.6(4) 2_766 . . . ? C5 N1 C1 C2 0.1(8) . . . . ? Hg1 N1 C1 C2 -176.2(5) . . . . ? N1 C1 C2 C3 0.7(9) . . . . ? C1 C2 C3 C4 -1.0(9) . . . . ? C2 C3 C4 C5 0.4(8) . . . . ? C1 N1 C5 C4 -0.7(8) . . . . ? Hg1 N1 C5 C4 175.4(4) . . . . ? C1 N1 C5 C6 -179.8(5) . . . . ? Hg1 N1 C5 C6 -3.8(6) . . . . ? C3 C4 C5 N1 0.4(8) . . . . ? C3 C4 C5 C6 179.6(5) . . . . ? Hg1 O1 C6 C5 33.8(5) . . . . ? N1 C5 C6 O1 -24.5(7) . . . . ? C4 C5 C6 O1 156.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.514 _refine_diff_density_min -2.270 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 926952'