Electronic Supplementary Material for CrystEngComm this journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Inorg.Chem.Commun. _journal_coden_Cambridge 1295 _journal_year 2007 _journal_volume 10 _journal_page_first 166 _publ_contact_author_name 'N. Atoub' _publ_contact_author_address ; Department of Chemistry Tarbiat Modares University Tehran 14155-1838 IRAN ; _publ_contact_author_email najmeh_atoub@yahoo.com loop_ _publ_author_name N.Atoub 'Ghodrat Mahmoudi' 'Ali Morsali' data_ATob _database_code_depnum_ccdc_archive 'CCDC 618043' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 Hg N14 O2' _chemical_formula_sum 'C24 H16 Hg N14 O2' _chemical_formula_weight 733.10 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.6509(5) _cell_length_b 15.9095(8) _cell_length_c 7.2480(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.044(5) _cell_angle_gamma 90.00 _cell_volume 1226.44(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 8577 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 30.12 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.985 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 6.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.334 _exptl_absorpt_correction_T_max 0.540 _exptl_absorpt_process_details 'Apex2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(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 X8-APEX-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12413 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2654 _reflns_number_gt 2190 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement 'Apex2 (Bruker, 2005)' _computing_data_reduction 'Apex2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL, v. 5.10 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL, v. 5.10 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL, v. 5.10 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL, v. 5.10 (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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2654 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.5000 0.0000 0.0000 0.02756(10) Uani 1 2 d S . . O1 O 0.24176(19) 0.43345(14) -0.0451(3) 0.0288(4) Uani 1 1 d . . . N1 N 0.3968(3) 0.4767(2) 0.1468(4) 0.0321(6) Uani 1 1 d . . . N2 N 0.3229(3) 0.54685(17) 0.0913(4) 0.0315(6) Uani 1 1 d . . . N3 N 0.4501(2) 0.15652(16) 0.1191(4) 0.0320(5) Uani 1 1 d . . . N4 N -0.0684(2) 0.65426(17) -0.2871(4) 0.0358(6) Uani 1 1 d . . . N5 N 0.6800(2) 0.0312(2) -0.0795(4) 0.0336(6) Uani 1 1 d . . . N6 N 0.7382(2) 0.08792(16) -0.0062(4) 0.0331(6) Uani 1 1 d . . . N7 N 0.8026(3) 0.1403(2) 0.0528(5) 0.0506(8) Uani 1 1 d . . . C1 C 0.3446(3) 0.4125(2) 0.0622(4) 0.0313(7) Uani 1 1 d . . . C2 C 0.2349(4) 0.5186(2) -0.0203(5) 0.0305(7) Uani 1 1 d . . . C3 C 0.3821(3) 0.32492(18) 0.0778(4) 0.0289(6) Uani 1 1 d . . . C4 C 0.2992(3) 0.26114(19) 0.0188(4) 0.0302(6) Uani 1 1 d . . . H4A H 0.2183 0.2740 -0.0354 0.036 Uiso 1 1 calc R . . C5 C 0.3384(3) 0.17867(19) 0.0416(4) 0.0317(6) Uani 1 1 d . . . H5A H 0.2826 0.1353 -0.0002 0.038 Uiso 1 1 calc R . . C6 C 0.5289(3) 0.21811(19) 0.1773(4) 0.0305(6) Uani 1 1 d . . . H6A H 0.6084 0.2030 0.2333 0.037 Uiso 1 1 calc R . . C7 C 0.4994(3) 0.30296(19) 0.1592(4) 0.0300(6) Uani 1 1 d . . . H7A H 0.5575 0.3450 0.2012 0.036 Uiso 1 1 calc R . . C8 C 0.1309(3) 0.56493(19) -0.1134(4) 0.0282(6) Uani 1 1 d . . . C9 C 0.1192(3) 0.6511(2) -0.0866(5) 0.0345(7) Uani 1 1 d . . . H9A H 0.1785 0.6809 -0.0091 0.041 Uiso 1 1 calc R . . C10 C 0.0184(3) 0.6923(2) -0.1765(5) 0.0352(7) Uani 1 1 d . . . H10A H 0.0108 0.7511 -0.1581 0.042 Uiso 1 1 calc R . . C11 C -0.0550(3) 0.5708(2) -0.3105(4) 0.0337(6) Uani 1 1 d . . . H11A H -0.1155 0.5424 -0.3888 0.040 Uiso 1 1 calc R . . C12 C 0.0417(3) 0.5241(2) -0.2273(5) 0.0317(6) Uani 1 1 d . . . H12A H 0.0469 0.4653 -0.2478 0.038 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 0.02705(13) 0.02652(14) 0.02907(13) 0.00079(5) 0.00105(8) -0.00013(5) O1 0.0294(10) 0.0253(11) 0.0314(11) 0.0003(9) -0.0018(9) 0.0032(9) N1 0.0337(15) 0.0299(12) 0.0323(15) -0.0010(13) -0.0011(12) 0.0027(14) N2 0.0321(14) 0.0271(15) 0.0348(14) 0.0028(11) -0.0033(12) 0.0028(11) N3 0.0358(13) 0.0286(13) 0.0316(13) 0.0001(10) 0.0030(11) 0.0029(10) N4 0.0321(13) 0.0361(15) 0.0392(15) 0.0012(12) 0.0031(11) 0.0052(11) N5 0.0337(14) 0.0307(14) 0.0369(15) -0.0028(12) 0.0067(11) -0.0015(12) N6 0.0336(13) 0.0309(13) 0.0354(13) -0.0030(11) 0.0073(11) -0.0020(11) N7 0.0474(16) 0.0488(18) 0.057(2) -0.0184(15) 0.0196(15) -0.0135(14) C1 0.0311(15) 0.0353(17) 0.0274(15) 0.0003(12) 0.0004(12) 0.0024(13) C2 0.0376(18) 0.0230(13) 0.0314(17) -0.0001(14) 0.0052(14) 0.0010(15) C3 0.0308(14) 0.0296(15) 0.0264(14) -0.0023(11) 0.0022(12) 0.0003(11) C4 0.0301(14) 0.0327(16) 0.0277(14) -0.0001(12) 0.0001(12) 0.0011(12) C5 0.0339(15) 0.0308(15) 0.0306(15) 0.0002(12) 0.0030(12) 0.0001(12) C6 0.0309(14) 0.0306(15) 0.0302(15) -0.0012(11) 0.0024(12) 0.0016(11) C7 0.0313(14) 0.0305(15) 0.0283(15) 0.0008(11) 0.0013(12) -0.0010(12) C8 0.0257(14) 0.0324(15) 0.0264(14) 0.0004(12) 0.0024(11) 0.0010(11) C9 0.0356(15) 0.0314(16) 0.0362(16) -0.0023(13) -0.0018(13) -0.0018(12) C10 0.0357(15) 0.0289(15) 0.0406(18) -0.0020(13) -0.0014(14) 0.0040(12) C11 0.0335(15) 0.0352(16) 0.0326(16) -0.0014(13) 0.0042(13) -0.0010(13) C12 0.0338(16) 0.0294(14) 0.0323(16) -0.0004(15) 0.0049(13) -0.0021(15) _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 N5 2.091(3) 3_655 ? Hg1 N5 2.091(3) . ? Hg1 N3 2.698(3) 3_655 ? Hg1 N3 2.698(3) . ? Hg1 N1 2.757(3) 2_645 ? Hg1 N1 2.757(3) 4_565 ? O1 C1 1.351(4) . ? O1 C2 1.369(4) . ? N1 C1 1.301(5) . ? N1 N2 1.412(4) . ? N1 Hg1 2.757(3) 2_655 ? N2 C2 1.285(5) . ? N3 C5 1.335(4) . ? N3 C6 1.344(4) . ? N4 C10 1.336(4) . ? N4 C11 1.347(4) . ? N5 N6 1.202(4) . ? N6 N7 1.148(4) . ? C1 C3 1.451(5) . ? C2 C8 1.466(5) . ? C3 C4 1.397(4) . ? C3 C7 1.397(4) . ? C4 C5 1.384(4) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.391(4) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C12 1.387(5) . ? C8 C9 1.391(4) . ? C9 C10 1.391(5) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.382(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Hg1 N5 180.00(18) 3_655 . ? N5 Hg1 N3 93.91(10) 3_655 3_655 ? N5 Hg1 N3 86.09(10) . 3_655 ? N5 Hg1 N3 86.09(10) 3_655 . ? N5 Hg1 N3 93.91(10) . . ? N3 Hg1 N3 180.00(11) 3_655 . ? N5 Hg1 N1 92.20(10) 3_655 2_645 ? N5 Hg1 N1 87.80(10) . 2_645 ? N3 Hg1 N1 95.57(9) 3_655 2_645 ? N3 Hg1 N1 84.43(9) . 2_645 ? N5 Hg1 N1 87.80(10) 3_655 4_565 ? N5 Hg1 N1 92.20(10) . 4_565 ? N3 Hg1 N1 84.43(9) 3_655 4_565 ? N3 Hg1 N1 95.57(9) . 4_565 ? N1 Hg1 N1 180.00(15) 2_645 4_565 ? C1 O1 C2 102.5(3) . . ? C1 N1 N2 105.6(3) . . ? C1 N1 Hg1 133.0(2) . 2_655 ? N2 N1 Hg1 110.3(2) . 2_655 ? C2 N2 N1 106.2(3) . . ? C5 N3 C6 117.9(3) . . ? C5 N3 Hg1 107.20(19) . . ? C6 N3 Hg1 130.0(2) . . ? C10 N4 C11 116.5(3) . . ? N6 N5 Hg1 121.0(2) . . ? N7 N6 N5 173.5(3) . . ? N1 C1 O1 113.0(3) . . ? N1 C1 C3 127.4(3) . . ? O1 C1 C3 119.6(3) . . ? N2 C2 O1 112.7(3) . . ? N2 C2 C8 128.5(3) . . ? O1 C2 C8 118.8(3) . . ? C4 C3 C7 118.9(3) . . ? C4 C3 C1 120.4(3) . . ? C7 C3 C1 120.6(3) . . ? C5 C4 C3 118.0(3) . . ? C5 C4 H4A 121.0 . . ? C3 C4 H4A 121.0 . . ? N3 C5 C4 123.8(3) . . ? N3 C5 H5A 118.1 . . ? C4 C5 H5A 118.1 . . ? N3 C6 C7 122.9(3) . . ? N3 C6 H6A 118.5 . . ? C7 C6 H6A 118.5 . . ? C6 C7 C3 118.4(3) . . ? C6 C7 H7A 120.8 . . ? C3 C7 H7A 120.8 . . ? C12 C8 C9 118.8(3) . . ? C12 C8 C2 121.1(3) . . ? C9 C8 C2 120.1(3) . . ? C8 C9 C10 118.1(3) . . ? C8 C9 H9A 120.9 . . ? C10 C9 H9A 120.9 . . ? N4 C10 C9 124.1(3) . . ? N4 C10 H10A 118.0 . . ? C9 C10 H10A 118.0 . . ? N4 C11 C12 123.8(3) . . ? N4 C11 H11A 118.1 . . ? C12 C11 H11A 118.1 . . ? C11 C12 C8 118.6(3) . . ? C11 C12 H12A 120.7 . . ? C8 C12 H12A 120.7 . . ? 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 C1 N1 N2 C2 -0.3(4) . . . . ? Hg1 N1 N2 C2 -149.5(2) 2_655 . . . ? N5 Hg1 N3 C5 -50.2(2) 3_655 . . . ? N5 Hg1 N3 C5 129.8(2) . . . . ? N3 Hg1 N3 C5 127(100) 3_655 . . . ? N1 Hg1 N3 C5 -142.8(2) 2_645 . . . ? N1 Hg1 N3 C5 37.2(2) 4_565 . . . ? N5 Hg1 N3 C6 155.9(3) 3_655 . . . ? N5 Hg1 N3 C6 -24.1(3) . . . . ? N3 Hg1 N3 C6 -27(100) 3_655 . . . ? N1 Hg1 N3 C6 63.3(3) 2_645 . . . ? N1 Hg1 N3 C6 -116.7(3) 4_565 . . . ? N5 Hg1 N5 N6 0(100) 3_655 . . . ? N3 Hg1 N5 N6 -153.2(3) 3_655 . . . ? N3 Hg1 N5 N6 26.8(3) . . . . ? N1 Hg1 N5 N6 -57.5(3) 2_645 . . . ? N1 Hg1 N5 N6 122.5(3) 4_565 . . . ? Hg1 N5 N6 N7 -180(100) . . . . ? N2 N1 C1 O1 -0.1(4) . . . . ? Hg1 N1 C1 O1 138.8(2) 2_655 . . . ? N2 N1 C1 C3 -177.6(3) . . . . ? Hg1 N1 C1 C3 -38.7(5) 2_655 . . . ? C2 O1 C1 N1 0.4(4) . . . . ? C2 O1 C1 C3 178.2(3) . . . . ? N1 N2 C2 O1 0.6(4) . . . . ? N1 N2 C2 C8 178.1(3) . . . . ? C1 O1 C2 N2 -0.6(4) . . . . ? C1 O1 C2 C8 -178.4(3) . . . . ? N1 C1 C3 C4 162.8(3) . . . . ? O1 C1 C3 C4 -14.6(4) . . . . ? N1 C1 C3 C7 -14.4(5) . . . . ? O1 C1 C3 C7 168.2(3) . . . . ? C7 C3 C4 C5 -0.9(4) . . . . ? C1 C3 C4 C5 -178.2(3) . . . . ? C6 N3 C5 C4 -0.3(5) . . . . ? Hg1 N3 C5 C4 -158.0(3) . . . . ? C3 C4 C5 N3 1.0(5) . . . . ? C5 N3 C6 C7 -0.4(4) . . . . ? Hg1 N3 C6 C7 151.3(2) . . . . ? N3 C6 C7 C3 0.4(4) . . . . ? C4 C3 C7 C6 0.3(4) . . . . ? C1 C3 C7 C6 177.6(3) . . . . ? N2 C2 C8 C12 -178.5(4) . . . . ? O1 C2 C8 C12 -1.1(5) . . . . ? N2 C2 C8 C9 0.7(5) . . . . ? O1 C2 C8 C9 178.1(3) . . . . ? C12 C8 C9 C10 -0.2(5) . . . . ? C2 C8 C9 C10 -179.4(3) . . . . ? C11 N4 C10 C9 -0.1(5) . . . . ? C8 C9 C10 N4 0.1(5) . . . . ? C10 N4 C11 C12 0.2(5) . . . . ? N4 C11 C12 C8 -0.3(5) . . . . ? C9 C8 C12 C11 0.3(5) . . . . ? C2 C8 C12 C11 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 2.043 _refine_diff_density_min -0.718 _refine_diff_density_rms 0.152 _publ_section_references ; Bruker (2005). APEX2 software package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL, v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The hydrogen atoms were placed in calculated positions and refined in riding model with fixed thermal parameters (Uiso(H) = 1.2Ueq(Ci), where Ueq(Ci) are the equivalent thermal parameters of the carbon atoms to which corresponding H atoms are bonded. ; # Attachment 'g-100.cif' data_g-100 _database_code_depnum_ccdc_archive 'CCDC 621194' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 Hg N6 O S2' _chemical_formula_weight 540.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 34.493(4) _cell_length_b 5.9210(7) _cell_length_c 18.570(2) _cell_angle_alpha 90.00 _cell_angle_beta 121.5660(10) _cell_angle_gamma 90.00 _cell_volume 3231.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3656 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 24.57 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 9.798 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1701 _exptl_absorpt_correction_T_max 0.2328 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11502 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3017 _reflns_number_gt 2565 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0318P)^2^+12.8307P] 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 3017 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0780 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.035764(9) 0.19728(4) 0.380819(15) 0.03908(11) Uani 1 1 d . . . S1 S 0.07217(6) 0.0340(3) 0.31260(11) 0.0416(4) Uani 1 1 d . . . S2 S -0.02700(6) 0.4049(3) 0.37152(13) 0.0485(4) Uani 1 1 d . . . N1 N 0.09075(18) 0.2493(8) 0.5306(3) 0.0356(12) Uani 1 1 d . . . N2 N 0.1749(2) 0.6437(9) 0.8155(3) 0.0476(15) Uani 1 1 d . . . N3 N 0.1928(2) 0.6337(10) 0.9028(3) 0.0489(15) Uani 1 1 d . . . N4 N 0.2271(2) 0.1679(12) 1.1610(4) 0.0575(17) Uani 1 1 d . . . N5 N 0.0762(2) -0.4225(10) 0.3559(4) 0.0593(17) Uani 1 1 d . . . N6 N 0.0129(2) 0.8327(10) 0.4219(4) 0.0542(16) Uani 1 1 d . . . O1 O 0.16803(14) 0.2938(7) 0.8499(2) 0.0329(9) Uani 1 1 d . . . C1 C 0.0933(2) 0.1092(11) 0.5889(4) 0.0386(15) Uani 1 1 d . . . H1 H 0.0780 -0.0279 0.5710 0.046 Uiso 1 1 calc R . . C2 C 0.1180(2) 0.1560(11) 0.6761(4) 0.0399(16) Uani 1 1 d . . . H2 H 0.1201 0.0520 0.7155 0.048 Uiso 1 1 calc R . . C3 C 0.13886(19) 0.3657(10) 0.7000(4) 0.0311(13) Uani 1 1 d . . . C4 C 0.1373(2) 0.5099(11) 0.6406(4) 0.0390(15) Uani 1 1 d . . . H4 H 0.1523 0.6482 0.6564 0.047 Uiso 1 1 calc R . . C5 C 0.1129(2) 0.4445(11) 0.5564(4) 0.0399(15) Uani 1 1 d . . . H5 H 0.1120 0.5418 0.5162 0.048 Uiso 1 1 calc R . . C6 C 0.1614(2) 0.4428(11) 0.7883(4) 0.0335(14) Uani 1 1 d . . . C7 C 0.18851(19) 0.4287(11) 0.9195(4) 0.0336(14) Uani 1 1 d . . . C8 C 0.20169(19) 0.3327(11) 1.0018(4) 0.0338(14) Uani 1 1 d . . . C9 C 0.1884(2) 0.1220(12) 1.0106(4) 0.0432(16) Uani 1 1 d . . . H9 H 0.1707 0.0304 0.9638 0.052 Uiso 1 1 calc R . . C10 C 0.2021(3) 0.0504(13) 1.0910(5) 0.0545(19) Uani 1 1 d . . . H10 H 0.1930 -0.0930 1.0966 0.065 Uiso 1 1 calc R . . C11 C 0.2285(2) 0.4600(12) 1.0728(4) 0.0438(16) Uani 1 1 d . . . H11 H 0.2387 0.6022 1.0689 0.053 Uiso 1 1 calc R . . C12 C 0.2399(2) 0.3706(15) 1.1503(4) 0.054(2) Uani 1 1 d . . . H12 H 0.2576 0.4583 1.1982 0.065 Uiso 1 1 calc R . . C13 C 0.0732(2) -0.2371(10) 0.3371(4) 0.0319(14) Uani 1 1 d . . . C14 C -0.0028(2) 0.6561(10) 0.4007(4) 0.0319(14) 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 0.05602(18) 0.02454(15) 0.04258(17) -0.00360(11) 0.02989(13) 0.00494(12) S1 0.0656(11) 0.0271(8) 0.0510(10) 0.0118(7) 0.0437(9) 0.0119(8) S2 0.0443(9) 0.0318(9) 0.0758(12) -0.0137(9) 0.0359(9) -0.0041(7) N1 0.042(3) 0.034(3) 0.028(3) -0.001(2) 0.017(2) 0.000(2) N2 0.068(4) 0.033(3) 0.036(3) -0.007(2) 0.024(3) -0.015(3) N3 0.061(4) 0.041(3) 0.036(3) -0.007(3) 0.019(3) -0.016(3) N4 0.069(4) 0.066(5) 0.045(4) 0.006(3) 0.035(3) 0.018(4) N5 0.090(5) 0.030(3) 0.090(5) 0.004(3) 0.069(4) 0.003(3) N6 0.085(5) 0.031(4) 0.072(4) -0.001(3) 0.059(4) -0.004(3) O1 0.039(2) 0.033(2) 0.028(2) -0.0061(18) 0.0175(19) -0.0044(19) C1 0.051(4) 0.029(3) 0.037(3) -0.003(3) 0.024(3) -0.006(3) C2 0.054(4) 0.035(4) 0.023(3) 0.007(3) 0.014(3) 0.000(3) C3 0.032(3) 0.034(3) 0.030(3) 0.000(3) 0.018(3) 0.000(3) C4 0.042(3) 0.036(4) 0.038(4) -0.001(3) 0.020(3) -0.011(3) C5 0.050(4) 0.036(4) 0.037(3) 0.010(3) 0.025(3) -0.001(3) C6 0.034(3) 0.037(4) 0.031(3) -0.003(3) 0.017(3) -0.003(3) C7 0.033(3) 0.033(4) 0.032(3) -0.006(3) 0.015(3) -0.003(3) C8 0.031(3) 0.041(4) 0.026(3) -0.007(3) 0.012(3) 0.001(3) C9 0.047(4) 0.038(4) 0.038(4) -0.006(3) 0.017(3) 0.001(3) C10 0.080(5) 0.042(4) 0.052(4) 0.006(3) 0.042(4) 0.014(4) C11 0.042(4) 0.048(4) 0.041(4) -0.012(3) 0.021(3) -0.010(3) C12 0.042(4) 0.081(6) 0.028(4) -0.015(4) 0.011(3) 0.010(4) C13 0.046(4) 0.023(3) 0.040(3) -0.003(3) 0.032(3) 0.002(3) C14 0.044(3) 0.023(3) 0.036(3) 0.004(3) 0.027(3) 0.009(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 Hg1 S1 2.4046(15) . ? Hg1 S2 2.4158(17) . ? Hg1 N1 2.430(5) . ? Hg1 N6 2.548(6) 1_545 ? S1 C13 1.664(6) . ? S2 C14 1.652(6) . ? N1 C1 1.329(8) . ? N1 C5 1.329(8) . ? N2 C6 1.280(8) . ? N2 N3 1.402(7) . ? N3 C7 1.279(8) . ? N4 C10 1.320(10) . ? N4 C12 1.328(11) . ? N5 C13 1.140(8) . ? N6 C14 1.148(8) . ? N6 Hg1 2.548(6) 1_565 ? O1 C7 1.361(7) . ? O1 C6 1.366(7) . ? C1 C2 1.408(8) . ? C1 H1 0.9300 . ? C2 C3 1.387(9) . ? C2 H2 0.9300 . ? C3 C4 1.374(8) . ? C3 C6 1.472(8) . ? C4 C5 1.387(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.462(8) . ? C8 C9 1.368(9) . ? C8 C11 1.373(8) . ? C9 C10 1.378(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.385(10) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 S1 Hg1 S2 149.60(6) . . ? S1 Hg1 N1 110.12(13) . . ? S2 Hg1 N1 98.66(13) . . ? S1 Hg1 N6 98.38(14) . 1_545 ? S2 Hg1 N6 92.67(15) . 1_545 ? N1 Hg1 N6 86.7(2) . 1_545 ? C13 S1 Hg1 100.7(2) . . ? C14 S2 Hg1 98.9(2) . . ? C1 N1 C5 117.9(5) . . ? C1 N1 Hg1 122.2(4) . . ? C5 N1 Hg1 118.7(4) . . ? C6 N2 N3 105.5(5) . . ? C7 N3 N2 106.4(5) . . ? C10 N4 C12 115.2(6) . . ? C14 N6 Hg1 146.5(5) . 1_565 ? C7 O1 C6 101.1(5) . . ? N1 C1 C2 123.8(6) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C3 C2 C1 116.4(6) . . ? C3 C2 H2 121.8 . . ? C1 C2 H2 121.8 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 C6 118.5(6) . . ? C2 C3 C6 121.2(5) . . ? C3 C4 C5 118.5(6) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 123.0(6) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N2 C6 O1 113.7(5) . . ? N2 C6 C3 126.8(6) . . ? O1 C6 C3 119.4(5) . . ? N3 C7 O1 113.3(5) . . ? N3 C7 C8 127.5(6) . . ? O1 C7 C8 119.2(5) . . ? C9 C8 C11 119.0(6) . . ? C9 C8 C7 122.6(5) . . ? C11 C8 C7 118.4(6) . . ? C8 C9 C10 117.6(6) . . ? C8 C9 H9 121.2 . . ? C10 C9 H9 121.2 . . ? N4 C10 C9 125.6(7) . . ? N4 C10 H10 117.2 . . ? C9 C10 H10 117.2 . . ? C8 C11 C12 118.1(7) . . ? C8 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? N4 C12 C11 124.4(7) . . ? N4 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? N5 C13 S1 176.6(6) . . ? N6 C14 S2 177.5(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 S2 Hg1 S1 C13 -118.9(3) . . . . ? N1 Hg1 S1 C13 80.8(3) . . . . ? N6 Hg1 S1 C13 -8.7(3) 1_545 . . . ? S1 Hg1 S2 C14 -100.1(2) . . . . ? N1 Hg1 S2 C14 61.2(3) . . . . ? N6 Hg1 S2 C14 148.3(3) 1_545 . . . ? S1 Hg1 N1 C1 -101.9(5) . . . . ? S2 Hg1 N1 C1 88.0(5) . . . . ? N6 Hg1 N1 C1 -4.2(5) 1_545 . . . ? S1 Hg1 N1 C5 91.0(5) . . . . ? S2 Hg1 N1 C5 -79.1(5) . . . . ? N6 Hg1 N1 C5 -171.3(5) 1_545 . . . ? C6 N2 N3 C7 0.2(8) . . . . ? C5 N1 C1 C2 0.3(10) . . . . ? Hg1 N1 C1 C2 -166.9(5) . . . . ? N1 C1 C2 C3 2.5(10) . . . . ? C1 C2 C3 C4 -4.0(9) . . . . ? C1 C2 C3 C6 173.5(6) . . . . ? C2 C3 C4 C5 2.7(9) . . . . ? C6 C3 C4 C5 -174.9(6) . . . . ? C1 N1 C5 C4 -1.8(10) . . . . ? Hg1 N1 C5 C4 165.8(5) . . . . ? C3 C4 C5 N1 0.4(10) . . . . ? N3 N2 C6 O1 0.8(8) . . . . ? N3 N2 C6 C3 178.2(6) . . . . ? C7 O1 C6 N2 -1.5(7) . . . . ? C7 O1 C6 C3 -179.1(5) . . . . ? C4 C3 C6 N2 10.3(10) . . . . ? C2 C3 C6 N2 -167.1(7) . . . . ? C4 C3 C6 O1 -172.4(5) . . . . ? C2 C3 C6 O1 10.1(9) . . . . ? N2 N3 C7 O1 -1.2(8) . . . . ? N2 N3 C7 C8 -179.3(6) . . . . ? C6 O1 C7 N3 1.7(7) . . . . ? C6 O1 C7 C8 179.9(5) . . . . ? N3 C7 C8 C9 168.0(7) . . . . ? O1 C7 C8 C9 -10.0(9) . . . . ? N3 C7 C8 C11 -12.0(10) . . . . ? O1 C7 C8 C11 170.0(6) . . . . ? C11 C8 C9 C10 1.2(10) . . . . ? C7 C8 C9 C10 -178.8(6) . . . . ? C12 N4 C10 C9 -0.7(11) . . . . ? C8 C9 C10 N4 0.0(11) . . . . ? C9 C8 C11 C12 -1.7(9) . . . . ? C7 C8 C11 C12 178.3(6) . . . . ? C10 N4 C12 C11 0.2(11) . . . . ? C8 C11 C12 N4 1.0(11) . . . . ? Hg1 S1 C13 N5 -120(10) . . . . ? Hg1 N6 C14 S2 -125(15) 1_565 . . . ? Hg1 S2 C14 N6 -158(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.569 _refine_diff_density_min -1.405 _refine_diff_density_rms 0.188 # Attachment 'x-new_rev1.cif' data_x _database_code_depnum_ccdc_archive 'CCDC 621195' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Hg2 I4 N4 O' _chemical_formula_weight 1133.00 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' 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4448(10) _cell_length_b 22.0985(19) _cell_length_c 8.4069(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.226(2) _cell_angle_gamma 90.00 _cell_volume 2092.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 20.564 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.029 _exptl_absorpt_correction_T_max 0.128 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11121 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.30 _reflns_number_total 3799 _reflns_number_gt 3179 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0445P)^2^+11.5514P] 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 3799 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.28484(5) 0.84993(2) 1.20923(7) 0.05019(18) Uani 1 1 d . . . Hg2 Hg 0.63008(5) 0.79403(3) 1.24334(7) 0.0617(2) Uani 1 1 d . . . I1 I 0.09315(10) 0.79532(5) 1.25928(15) 0.0670(3) Uani 1 1 d . . . I2 I 0.46715(8) 0.92025(4) 1.33775(11) 0.0490(2) Uani 1 1 d . . . I3 I 0.43032(8) 0.74730(4) 1.08456(10) 0.0461(2) Uani 1 1 d . . . I4 I 0.79468(8) 0.79576(5) 1.50434(11) 0.0534(3) Uani 1 1 d . . . O1 O 0.2232(7) 1.0116(4) 0.4197(9) 0.038(2) Uani 1 1 d . . . N1 N 0.2366(10) 0.8963(5) 0.9415(13) 0.048(3) Uani 1 1 d . . . N2 N 0.0592(12) 0.9581(5) 0.3681(14) 0.062(4) Uani 1 1 d . . . N3 N 0.0709(12) 0.9923(5) 0.2280(13) 0.058(3) Uani 1 1 d . . . N4 N 0.3071(10) 1.1358(4) -0.0596(13) 0.040(2) Uani 1 1 d . . . C1 C 0.3043(14) 0.9389(6) 0.8931(15) 0.056(4) Uani 1 1 d . . . H1 H 0.3715 0.9516 0.9645 0.067 Uiso 1 1 calc R . . C2 C 0.2797(13) 0.9654(6) 0.7412(17) 0.054(4) Uani 1 1 d . . . H2 H 0.3277 0.9960 0.7124 0.064 Uiso 1 1 calc R . . C3 C 0.1821(12) 0.9452(5) 0.6343(14) 0.039(3) Uani 1 1 d . . . C4 C 0.1146(15) 0.9005(7) 0.6807(17) 0.060(4) Uani 1 1 d . . . H4 H 0.0493 0.8856 0.6097 0.072 Uiso 1 1 calc R . . C5 C 0.1440(15) 0.8775(6) 0.8350(17) 0.058(4) Uani 1 1 d . . . H5 H 0.0965 0.8472 0.8661 0.070 Uiso 1 1 calc R . . C6 C 0.1505(12) 0.9708(5) 0.4720(16) 0.041(3) Uani 1 1 d . . . C7 C 0.1660(13) 1.0229(5) 0.2663(14) 0.041(3) Uani 1 1 d . . . C8 C 0.2190(11) 1.0627(5) 0.1572(14) 0.039(3) Uani 1 1 d . . . C9 C 0.3279(13) 1.0890(6) 0.1998(15) 0.048(3) Uani 1 1 d . . . H9 H 0.3732 1.0827 0.3018 0.057 Uiso 1 1 calc R . . C10 C 0.3690(13) 1.1249(6) 0.0885(15) 0.048(3) Uani 1 1 d . . . H10 H 0.4435 1.1425 0.1173 0.058 Uiso 1 1 calc R . . C11 C 0.1990(12) 1.1105(6) -0.0947(15) 0.046(3) Uani 1 1 d . . . H11 H 0.1543 1.1183 -0.1962 0.056 Uiso 1 1 calc R . . C12 C 0.1505(12) 1.0751(6) 0.0048(16) 0.048(3) Uani 1 1 d . . . H12 H 0.0745 1.0593 -0.0256 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 Hg1 0.0413(3) 0.0574(3) 0.0525(3) 0.0128(3) 0.0100(3) -0.0036(3) Hg2 0.0438(4) 0.0899(5) 0.0471(3) 0.0224(3) -0.0034(3) -0.0142(3) I1 0.0435(6) 0.0695(7) 0.0928(8) 0.0105(6) 0.0255(5) -0.0059(5) I2 0.0456(6) 0.0461(5) 0.0530(5) -0.0011(4) 0.0026(4) -0.0040(4) I3 0.0411(5) 0.0585(5) 0.0393(5) -0.0152(4) 0.0083(4) -0.0011(4) I4 0.0368(5) 0.0797(7) 0.0415(5) 0.0127(4) 0.0005(4) -0.0095(5) O1 0.038(5) 0.048(5) 0.026(4) 0.005(4) 0.001(4) -0.005(4) N1 0.057(8) 0.047(6) 0.039(6) 0.016(5) 0.004(6) -0.001(6) N2 0.073(9) 0.063(8) 0.043(7) 0.012(6) -0.006(6) -0.018(7) N3 0.071(9) 0.065(7) 0.033(6) 0.015(5) 0.000(6) -0.025(7) N4 0.036(6) 0.043(6) 0.043(6) 0.001(5) 0.009(5) -0.002(5) C1 0.062(10) 0.076(10) 0.026(7) 0.015(7) 0.000(6) -0.025(8) C2 0.061(10) 0.047(8) 0.051(9) 0.008(6) 0.006(7) -0.017(7) C3 0.059(9) 0.029(6) 0.030(6) 0.001(5) 0.010(6) -0.007(6) C4 0.076(11) 0.062(9) 0.040(8) -0.003(7) 0.005(7) -0.028(8) C5 0.075(11) 0.049(8) 0.047(9) 0.018(7) 0.000(8) -0.020(8) C6 0.048(8) 0.034(6) 0.043(8) 0.001(6) 0.012(6) -0.007(6) C7 0.056(9) 0.036(7) 0.032(7) 0.009(5) 0.008(6) -0.004(6) C8 0.042(8) 0.045(7) 0.028(6) 0.001(5) 0.002(5) -0.001(6) C9 0.055(9) 0.053(8) 0.030(7) 0.004(6) -0.006(6) -0.002(7) C10 0.044(8) 0.068(9) 0.034(7) -0.003(6) 0.013(6) -0.010(7) C11 0.046(9) 0.063(8) 0.028(7) 0.010(6) 0.000(6) -0.007(7) C12 0.037(8) 0.064(9) 0.041(7) 0.011(6) 0.001(6) -0.019(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 Hg1 N1 2.445(10) . ? Hg1 I1 2.6027(12) . ? Hg1 I2 2.6712(10) . ? Hg1 I3 3.1038(11) . ? Hg2 N4 2.388(10) 3_676 ? Hg2 I4 2.6262(10) . ? Hg2 I3 2.6442(11) . ? O1 C6 1.352(14) . ? O1 C7 1.362(14) . ? N1 C5 1.327(17) . ? N1 C1 1.328(17) . ? N2 C6 1.269(17) . ? N2 N3 1.425(15) . ? N3 C7 1.273(17) . ? N4 C10 1.341(16) . ? N4 C11 1.342(16) . ? N4 Hg2 2.388(10) 3_676 ? C1 C2 1.388(18) . ? C1 H1 0.9300 . ? C2 C3 1.379(18) . ? C2 H2 0.9300 . ? C3 C4 1.353(18) . ? C3 C6 1.462(17) . ? C4 C5 1.378(19) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.477(17) . ? C8 C9 1.364(18) . ? C8 C12 1.406(16) . ? C9 C10 1.372(18) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.337(17) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 I1 106.5(3) . . ? N1 Hg1 I2 99.3(3) . . ? I1 Hg1 I2 145.55(4) . . ? N1 Hg1 I3 92.4(3) . . ? I1 Hg1 I3 103.53(3) . . ? I2 Hg1 I3 97.72(3) . . ? N4 Hg2 I4 106.1(3) 3_676 . ? N4 Hg2 I3 105.1(3) 3_676 . ? I4 Hg2 I3 148.77(4) . . ? Hg2 I3 Hg1 90.67(3) . . ? C6 O1 C7 102.1(10) . . ? C5 N1 C1 117.0(11) . . ? C5 N1 Hg1 120.8(9) . . ? C1 N1 Hg1 122.0(9) . . ? C6 N2 N3 105.3(11) . . ? C7 N3 N2 106.0(11) . . ? C10 N4 C11 116.3(11) . . ? C10 N4 Hg2 123.2(9) . 3_676 ? C11 N4 Hg2 120.0(8) . 3_676 ? N1 C1 C2 123.1(13) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.2(13) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C4 C3 C2 119.1(12) . . ? C4 C3 C6 119.5(12) . . ? C2 C3 C6 121.4(11) . . ? C3 C4 C5 119.0(14) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 123.5(13) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? N2 C6 O1 113.8(11) . . ? N2 C6 C3 126.4(12) . . ? O1 C6 C3 119.8(11) . . ? N3 C7 O1 112.8(10) . . ? N3 C7 C8 125.9(11) . . ? O1 C7 C8 121.0(11) . . ? C9 C8 C12 119.5(12) . . ? C9 C8 C7 123.2(11) . . ? C12 C8 C7 117.2(11) . . ? C8 C9 C10 118.3(12) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N4 C10 C9 123.3(13) . . ? N4 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C12 C11 N4 125.2(12) . . ? C12 C11 H11 117.4 . . ? N4 C11 H11 117.4 . . ? C11 C12 C8 117.3(12) . . ? C11 C12 H12 121.4 . . ? C8 C12 H12 121.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.250 _refine_diff_density_min -2.149 _refine_diff_density_rms 0.286 # Attachment '136-G_06mz252m_new.cif' data_06mz252m _database_code_depnum_ccdc_archive 'CCDC 621196' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Br2 Hg N4 O' _chemical_formula_weight 584.63 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 5.2468(6) _cell_length_b 21.221(2) _cell_length_c 13.2169(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.837(2) _cell_angle_gamma 90.00 _cell_volume 1461.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5192 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 30.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 16.002 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.040 _exptl_absorpt_correction_T_max 0.326 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14537 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3609 _reflns_number_gt 3257 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3609 _refine_ls_number_parameters 181 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.054 _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 Br1 Br -0.52831(13) 0.12693(3) -0.07481(4) 0.02545(16) Uani 1 1 d . . . Br2 Br -0.65381(11) 0.20141(2) 0.25882(4) 0.01513(13) Uani 1 1 d . . . C1 C -0.1492(11) 0.2987(2) 0.1726(4) 0.0107(10) Uani 1 1 d U . . H1 H -0.2439 0.2942 0.2291 0.013 Uiso 1 1 calc R . . C2 C 0.0413(11) 0.3450(2) 0.1771(4) 0.0106(10) Uani 1 1 d U . . H2 H 0.0767 0.3714 0.2352 0.013 Uiso 1 1 calc R . . C3 C 0.1765(10) 0.3509(2) 0.0939(4) 0.0098(10) Uani 1 1 d U . . C4 C 0.1169(11) 0.3125(3) 0.0088(4) 0.0128(11) Uani 1 1 d U . . H4 H 0.2053 0.3168 -0.0496 0.015 Uiso 1 1 calc R . . C5 C -0.0749(11) 0.2679(2) 0.0117(4) 0.0141(11) Uani 1 1 d U . . H5 H -0.1167 0.2414 -0.0458 0.017 Uiso 1 1 calc R . . C6 C 0.3851(11) 0.3966(2) 0.0902(4) 0.0110(10) Uani 1 1 d U . . C7 C 0.6652(11) 0.4657(2) 0.1397(4) 0.0114(10) Uani 1 1 d . . . C8 C 0.8290(10) 0.5095(2) 0.2059(4) 0.0099(10) Uani 1 1 d . . . C9 C 0.8214(12) 0.5161(2) 0.3090(4) 0.0139(11) Uani 1 1 d . . . H9 H 0.7003 0.4934 0.3428 0.017 Uiso 1 1 calc R . . C10 C 0.9949(11) 0.5567(3) 0.3621(4) 0.0159(11) Uani 1 1 d . . . H10 H 0.9939 0.5606 0.4336 0.019 Uiso 1 1 calc R . . C11 C 1.1678(11) 0.5846(2) 0.2166(4) 0.0151(11) Uani 1 1 d . . . H11 H 1.2878 0.6087 0.1843 0.018 Uiso 1 1 calc R . . C12 C 1.0037(11) 0.5446(2) 0.1578(4) 0.0121(10) Uani 1 1 d . . . H12 H 1.0097 0.5411 0.0864 0.015 Uiso 1 1 calc R . . Hg1 Hg -0.47254(4) 0.168318(8) 0.101550(13) 0.01130(9) Uani 1 1 d . . . N1 N -0.2042(9) 0.2607(2) 0.0927(3) 0.0118(9) Uani 1 1 d . . . N2 N 0.5107(9) 0.40717(19) 0.0140(3) 0.0121(9) Uani 1 1 d . . . N3 N 0.6955(9) 0.4523(2) 0.0466(3) 0.0124(9) Uani 1 1 d . . . N4 N 1.1649(9) 0.5909(2) 0.3169(3) 0.0125(9) Uani 1 1 d . . . O1 O 0.4716(7) 0.43243(16) 0.1747(3) 0.0107(7) 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 Br1 0.0442(4) 0.0247(3) 0.0050(2) -0.0053(2) -0.0072(2) 0.0043(3) Br2 0.0220(3) 0.0161(3) 0.0082(2) 0.00390(18) 0.0056(2) 0.0045(2) C1 0.017(3) 0.010(2) 0.004(2) 0.0016(16) -0.0014(18) 0.0028(19) C2 0.016(3) 0.012(2) 0.004(2) 0.0002(16) -0.0015(18) 0.0025(19) C3 0.013(2) 0.012(2) 0.004(2) 0.0014(17) 0.0001(18) 0.0015(19) C4 0.020(3) 0.015(2) 0.004(2) -0.0009(18) 0.0028(19) -0.002(2) C5 0.020(3) 0.016(2) 0.006(2) -0.0031(17) 0.0000(19) -0.004(2) C6 0.019(3) 0.010(2) 0.004(2) -0.0017(16) 0.0008(18) 0.0026(19) C7 0.015(3) 0.013(2) 0.006(2) 0.0009(18) -0.0011(19) 0.001(2) C8 0.011(3) 0.008(2) 0.010(2) 0.0002(17) -0.0014(19) 0.0018(19) C9 0.021(3) 0.015(2) 0.006(2) -0.0003(18) 0.002(2) -0.002(2) C10 0.026(3) 0.018(2) 0.004(2) 0.0005(19) 0.004(2) -0.001(2) C11 0.020(3) 0.017(2) 0.009(2) 0.0005(19) 0.002(2) 0.002(2) C12 0.019(3) 0.011(2) 0.006(2) -0.0007(17) 0.000(2) 0.000(2) Hg1 0.01941(15) 0.01099(12) 0.00302(12) 0.00052(6) -0.00062(8) -0.00075(7) N1 0.016(2) 0.014(2) 0.0046(19) -0.0010(15) -0.0001(17) -0.0022(17) N2 0.019(3) 0.0119(19) 0.006(2) -0.0003(15) 0.0015(18) -0.0034(18) N3 0.017(3) 0.012(2) 0.008(2) -0.0003(16) 0.0006(18) -0.0042(18) N4 0.019(3) 0.014(2) 0.0040(19) -0.0008(15) -0.0014(17) -0.0017(18) O1 0.016(2) 0.0111(16) 0.0044(16) -0.0006(13) 0.0005(14) -0.0023(14) _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 Br1 Hg1 2.4754(6) . ? Br2 Hg1 2.4878(6) . ? C1 N1 1.332(6) . ? C1 C2 1.397(8) . ? C1 H1 0.9500 . ? C2 C3 1.384(7) . ? C2 H2 0.9500 . ? C3 C4 1.395(7) . ? C3 C6 1.467(7) . ? C4 C5 1.386(8) . ? C4 H4 0.9500 . ? C5 N1 1.343(7) . ? C5 H5 0.9500 . ? C6 N2 1.287(6) . ? C6 O1 1.382(6) . ? C7 N3 1.292(6) . ? C7 O1 1.362(6) . ? C7 C8 1.480(7) . ? C8 C9 1.375(7) . ? C8 C12 1.393(7) . ? C9 C10 1.383(8) . ? C9 H9 0.9500 . ? C10 N4 1.344(7) . ? C10 H10 0.9500 . ? C11 N4 1.334(7) . ? C11 C12 1.381(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? Hg1 N1 2.425(4) . ? Hg1 N4 2.460(4) 2_645 ? N2 N3 1.394(6) . ? N4 Hg1 2.460(4) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.1(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 117.5(5) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 120.1(5) . . ? C2 C3 C6 122.8(5) . . ? C4 C3 C6 117.1(4) . . ? C5 C4 C3 118.1(5) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 122.5(5) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? N2 C6 O1 112.8(4) . . ? N2 C6 C3 126.5(4) . . ? O1 C6 C3 120.7(4) . . ? N3 C7 O1 113.0(5) . . ? N3 C7 C8 125.0(5) . . ? O1 C7 C8 121.9(4) . . ? C9 C8 C12 119.8(5) . . ? C9 C8 C7 124.5(5) . . ? C12 C8 C7 115.7(5) . . ? C8 C9 C10 118.1(5) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? N4 C10 C9 122.9(5) . . ? N4 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N4 C11 C12 122.7(5) . . ? N4 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C11 C12 C8 118.2(5) . . ? C11 C12 H12 120.9 . . ? C8 C12 H12 120.9 . . ? N1 Hg1 N4 101.92(15) . 2_645 ? N1 Hg1 Br1 104.24(10) . . ? N4 Hg1 Br1 100.00(10) 2_645 . ? N1 Hg1 Br2 95.38(10) . . ? N4 Hg1 Br2 96.80(10) 2_645 . ? Br1 Hg1 Br2 150.79(2) . . ? C1 N1 C5 118.7(5) . . ? C1 N1 Hg1 121.6(3) . . ? C5 N1 Hg1 118.8(3) . . ? C6 N2 N3 106.3(4) . . ? C7 N3 N2 106.6(4) . . ? C11 N4 C10 118.3(5) . . ? C11 N4 Hg1 114.7(4) . 2_655 ? C10 N4 Hg1 127.0(3) . 2_655 ? C7 O1 C6 101.4(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 N1 C1 C2 C3 0.2(8) . . . . ? C1 C2 C3 C4 1.4(8) . . . . ? C1 C2 C3 C6 -178.5(5) . . . . ? C2 C3 C4 C5 -1.6(8) . . . . ? C6 C3 C4 C5 178.3(5) . . . . ? C3 C4 C5 N1 0.2(9) . . . . ? C2 C3 C6 N2 -176.2(5) . . . . ? C4 C3 C6 N2 3.9(8) . . . . ? C2 C3 C6 O1 5.8(8) . . . . ? C4 C3 C6 O1 -174.1(5) . . . . ? N3 C7 C8 C9 -169.3(5) . . . . ? O1 C7 C8 C9 6.9(8) . . . . ? N3 C7 C8 C12 9.4(8) . . . . ? O1 C7 C8 C12 -174.3(5) . . . . ? C12 C8 C9 C10 -1.8(8) . . . . ? C7 C8 C9 C10 176.9(5) . . . . ? C8 C9 C10 N4 1.7(9) . . . . ? N4 C11 C12 C8 -0.2(8) . . . . ? C9 C8 C12 C11 1.0(8) . . . . ? C7 C8 C12 C11 -177.8(5) . . . . ? C2 C1 N1 C5 -1.5(8) . . . . ? C2 C1 N1 Hg1 167.5(4) . . . . ? C4 C5 N1 C1 1.3(8) . . . . ? C4 C5 N1 Hg1 -168.0(4) . . . . ? N4 Hg1 N1 C1 -81.7(4) 2_645 . . . ? Br1 Hg1 N1 C1 174.6(4) . . . . ? Br2 Hg1 N1 C1 16.4(4) . . . . ? N4 Hg1 N1 C5 87.3(4) 2_645 . . . ? Br1 Hg1 N1 C5 -16.4(4) . . . . ? Br2 Hg1 N1 C5 -174.6(4) . . . . ? O1 C6 N2 N3 0.4(6) . . . . ? C3 C6 N2 N3 -177.8(5) . . . . ? O1 C7 N3 N2 0.4(6) . . . . ? C8 C7 N3 N2 177.0(5) . . . . ? C6 N2 N3 C7 -0.5(6) . . . . ? C12 C11 N4 C10 0.1(8) . . . . ? C12 C11 N4 Hg1 -178.2(4) . . . 2_655 ? C9 C10 N4 C11 -0.9(8) . . . . ? C9 C10 N4 Hg1 177.2(4) . . . 2_655 ? N3 C7 O1 C6 -0.2(6) . . . . ? C8 C7 O1 C6 -176.9(5) . . . . ? N2 C6 O1 C7 -0.1(5) . . . . ? C3 C6 O1 C7 178.1(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.023 _refine_diff_density_min -2.829 _refine_diff_density_rms 0.287 data_06mz251m _database_code_depnum_ccdc_archive 'CCDC 621197' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Hg N6 O5' _chemical_formula_weight 516.83 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' 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 P2(1)/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 5.9134(8) _cell_length_b 18.776(2) _cell_length_c 13.2924(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.608(2) _cell_angle_gamma 90.00 _cell_volume 1445.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5891 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 30.59 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 10.687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.073 _exptl_absorpt_correction_T_max 0.224 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14753 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3586 _reflns_number_gt 3365 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0276P)^2^+2.2373P] 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 3586 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.002 _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 C1 C 0.3206(6) 0.42492(19) 0.2905(3) 0.0156(7) Uani 1 1 d . . . H1 H 0.2111 0.4001 0.3208 0.019 Uiso 1 1 calc R . . C2 C 0.4875(6) 0.46491(19) 0.3527(3) 0.0152(7) Uani 1 1 d . . . H2 H 0.4947 0.4668 0.4247 0.018 Uiso 1 1 calc R . . C3 C 0.6468(6) 0.50282(18) 0.3083(3) 0.0128(6) Uani 1 1 d . . . C4 C 0.6314(6) 0.49796(19) 0.2028(3) 0.0148(7) Uani 1 1 d . . . H4 H 0.7357 0.5232 0.1700 0.018 Uiso 1 1 calc R . . C5 C 0.4600(6) 0.45537(19) 0.1467(3) 0.0154(7) Uani 1 1 d . . . H5 H 0.4510 0.4513 0.0748 0.019 Uiso 1 1 calc R . . C6 C 0.8155(6) 0.54643(18) 0.3758(3) 0.0127(6) Uani 1 1 d . . . C7 C 1.1003(6) 0.61564(17) 0.4263(3) 0.0113(6) Uani 1 1 d . . . C8 C 1.2999(6) 0.65977(17) 0.4199(3) 0.0115(6) Uani 1 1 d . . . C9 C 1.3970(6) 0.70186(19) 0.5043(3) 0.0138(7) Uani 1 1 d . . . H9 H 1.3364 0.7013 0.5653 0.017 Uiso 1 1 calc R . . C10 C 1.5848(6) 0.74465(18) 0.4965(3) 0.0127(6) Uani 1 1 d . . . H10 H 1.6520 0.7735 0.5534 0.015 Uiso 1 1 calc R . . C11 C 1.5801(6) 0.70574(18) 0.3306(3) 0.0123(6) Uani 1 1 d . . . H11 H 1.6436 0.7073 0.2704 0.015 Uiso 1 1 calc R . . C12 C 1.3941(6) 0.66158(17) 0.3320(3) 0.0121(6) Uani 1 1 d . . . H12 H 1.3316 0.6330 0.2741 0.014 Uiso 1 1 calc R . . Hg1 Hg 0.05740(2) 0.331987(6) 0.103886(9) 0.01151(6) Uani 1 1 d . . . N1 N 0.3062(5) 0.41956(15) 0.1887(2) 0.0126(5) Uani 1 1 d . . . N2 N 0.8191(5) 0.56043(15) 0.4720(2) 0.0143(6) Uani 1 1 d . . . N3 N 1.0060(5) 0.60603(16) 0.5048(2) 0.0145(6) Uani 1 1 d . . . N4 N 1.6747(5) 0.74662(15) 0.4112(2) 0.0113(5) Uani 1 1 d . . . N5 N -0.1380(5) 0.29304(16) 0.2809(2) 0.0163(6) Uani 1 1 d . . . N6 N -0.1111(6) 0.39570(19) -0.0933(2) 0.0220(7) Uani 1 1 d . . . O1 O 0.9889(4) 0.57946(12) 0.34069(18) 0.0116(5) Uani 1 1 d . . . O2 O 0.0527(5) 0.26654(15) 0.2777(2) 0.0209(6) Uani 1 1 d . . . O3 O -0.2185(5) 0.33328(14) 0.2055(2) 0.0226(6) Uani 1 1 d . . . O4 O 0.1008(5) 0.39224(16) -0.0613(2) 0.0248(6) Uani 1 1 d . . . O5 O -0.2293(5) 0.36864(18) -0.0336(2) 0.0317(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0151(16) 0.0195(17) 0.0133(16) -0.0020(14) 0.0055(13) -0.0020(14) C2 0.0157(16) 0.0173(16) 0.0134(16) -0.0027(13) 0.0050(13) -0.0040(13) C3 0.0102(14) 0.0137(15) 0.0143(16) 0.0003(13) 0.0016(12) 0.0013(13) C4 0.0137(15) 0.0168(16) 0.0151(17) 0.0014(14) 0.0059(13) -0.0010(13) C5 0.0157(16) 0.0194(17) 0.0113(16) 0.0013(13) 0.0030(13) -0.0013(13) C6 0.0109(15) 0.0118(15) 0.0157(16) 0.0005(13) 0.0037(12) -0.0002(12) C7 0.0086(14) 0.0114(14) 0.0134(16) -0.0010(12) 0.0010(12) 0.0007(12) C8 0.0090(15) 0.0124(15) 0.0121(16) 0.0023(12) -0.0001(12) 0.0001(12) C9 0.0130(16) 0.0177(16) 0.0106(15) -0.0012(13) 0.0025(12) -0.0009(13) C10 0.0134(15) 0.0145(15) 0.0098(15) -0.0018(12) 0.0016(12) -0.0013(12) C11 0.0131(16) 0.0136(15) 0.0104(15) -0.0004(12) 0.0024(12) -0.0004(12) C12 0.0124(16) 0.0124(15) 0.0116(16) -0.0016(12) 0.0028(13) -0.0006(12) Hg1 0.00903(8) 0.01397(8) 0.01127(8) 0.00011(4) 0.00140(5) 0.00047(4) N1 0.0109(13) 0.0143(13) 0.0123(13) -0.0005(11) 0.0015(10) 0.0000(11) N2 0.0123(14) 0.0145(14) 0.0162(15) -0.0002(11) 0.0026(11) -0.0044(11) N3 0.0126(13) 0.0162(14) 0.0146(14) 0.0004(12) 0.0024(11) -0.0034(11) N4 0.0097(12) 0.0150(13) 0.0087(13) 0.0021(11) 0.0006(10) 0.0011(11) N5 0.0146(14) 0.0183(15) 0.0174(15) -0.0047(12) 0.0064(12) -0.0026(11) N6 0.0240(16) 0.0263(17) 0.0136(15) 0.0030(13) -0.0014(13) 0.0006(14) O1 0.0097(11) 0.0129(11) 0.0119(11) -0.0014(9) 0.0017(9) -0.0027(9) O2 0.0173(13) 0.0271(14) 0.0187(13) 0.0032(11) 0.0047(10) 0.0035(11) O3 0.0179(14) 0.0240(15) 0.0276(16) 0.0037(11) 0.0086(12) 0.0033(10) O4 0.0201(14) 0.0336(16) 0.0209(14) 0.0088(12) 0.0045(11) -0.0002(12) O5 0.0178(14) 0.0474(19) 0.0277(16) 0.0137(14) -0.0002(12) -0.0021(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.342(4) . ? C1 C2 1.376(5) . ? C1 H1 0.9500 . ? C2 C3 1.402(5) . ? C2 H2 0.9500 . ? C3 C4 1.390(5) . ? C3 C6 1.453(5) . ? C4 C5 1.385(5) . ? C4 H4 0.9500 . ? C5 N1 1.340(4) . ? C5 H5 0.9500 . ? C6 N2 1.300(5) . ? C6 O1 1.359(4) . ? C7 N3 1.292(4) . ? C7 O1 1.374(4) . ? C7 C8 1.458(5) . ? C8 C12 1.393(5) . ? C8 C9 1.397(5) . ? C9 C10 1.392(5) . ? C9 H9 0.9500 . ? C10 N4 1.345(4) . ? C10 H10 0.9500 . ? C11 N4 1.346(4) . ? C11 C12 1.381(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? Hg1 N4 2.291(3) 2_745 ? Hg1 O3 2.319(3) . ? Hg1 O5 2.333(3) . ? Hg1 N1 2.339(3) . ? Hg1 O4 2.529(3) . ? Hg1 O2 2.622(3) . ? N2 N3 1.397(4) . ? N4 Hg1 2.291(3) 2_755 ? N5 O2 1.241(4) . ? N5 O3 1.268(4) . ? N6 O4 1.242(4) . ? N6 O5 1.265(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.6(3) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.1(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 118.5(3) . . ? C4 C3 C6 123.9(3) . . ? C2 C3 C6 117.6(3) . . ? C5 C4 C3 118.3(3) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.3(3) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N2 C6 O1 112.4(3) . . ? N2 C6 C3 126.5(3) . . ? O1 C6 C3 121.1(3) . . ? N3 C7 O1 112.8(3) . . ? N3 C7 C8 127.7(3) . . ? O1 C7 C8 119.5(3) . . ? C12 C8 C9 119.4(3) . . ? C12 C8 C7 121.8(3) . . ? C9 C8 C7 118.8(3) . . ? C10 C9 C8 118.1(3) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N4 C10 C9 122.4(3) . . ? N4 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N4 C11 C12 122.4(3) . . ? N4 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C11 C12 C8 118.7(3) . . ? C11 C12 H12 120.6 . . ? C8 C12 H12 120.6 . . ? N4 Hg1 O3 129.70(10) 2_745 . ? N4 Hg1 O5 122.96(11) 2_745 . ? O3 Hg1 O5 88.15(11) . . ? N4 Hg1 N1 98.92(10) 2_745 . ? O3 Hg1 N1 99.20(10) . . ? O5 Hg1 N1 117.24(11) . . ? N4 Hg1 O4 92.52(10) 2_745 . ? O3 Hg1 O4 135.04(10) . . ? O5 Hg1 O4 51.13(10) . . ? N1 Hg1 O4 86.57(10) . . ? N4 Hg1 O2 83.08(9) 2_745 . ? O3 Hg1 O2 50.06(9) . . ? O5 Hg1 O2 133.94(9) . . ? N1 Hg1 O2 91.25(9) . . ? O4 Hg1 O2 174.74(8) . . ? C5 N1 C1 118.2(3) . . ? C5 N1 Hg1 124.5(2) . . ? C1 N1 Hg1 116.4(2) . . ? C6 N2 N3 106.7(3) . . ? C7 N3 N2 106.0(3) . . ? C10 N4 C11 118.9(3) . . ? C10 N4 Hg1 119.4(2) . 2_755 ? C11 N4 Hg1 120.9(2) . 2_755 ? O2 N5 O3 114.3(3) . . ? O4 N6 O5 114.3(3) . . ? C6 O1 C7 102.1(3) . . ? N5 O2 Hg1 90.7(2) . . ? N5 O3 Hg1 104.9(2) . . ? N6 O4 Hg1 92.8(2) . . ? N6 O5 Hg1 101.8(2) . . ? 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 C1 C2 C3 1.3(5) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C1 C2 C3 C6 177.9(3) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C6 C3 C4 C5 -178.9(3) . . . . ? C3 C4 C5 N1 1.1(5) . . . . ? C4 C3 C6 N2 170.3(4) . . . . ? C2 C3 C6 N2 -8.2(5) . . . . ? C4 C3 C6 O1 -7.8(5) . . . . ? C2 C3 C6 O1 173.8(3) . . . . ? N3 C7 C8 C12 175.5(3) . . . . ? O1 C7 C8 C12 -5.7(5) . . . . ? N3 C7 C8 C9 -5.2(5) . . . . ? O1 C7 C8 C9 173.6(3) . . . . ? C12 C8 C9 C10 0.4(5) . . . . ? C7 C8 C9 C10 -178.9(3) . . . . ? C8 C9 C10 N4 -0.1(5) . . . . ? N4 C11 C12 C8 0.6(5) . . . . ? C9 C8 C12 C11 -0.7(5) . . . . ? C7 C8 C12 C11 178.6(3) . . . . ? C4 C5 N1 C1 -0.5(5) . . . . ? C4 C5 N1 Hg1 -168.7(3) . . . . ? C2 C1 N1 C5 -0.7(5) . . . . ? C2 C1 N1 Hg1 168.4(3) . . . . ? N4 Hg1 N1 C5 67.4(3) 2_745 . . . ? O3 Hg1 N1 C5 -159.7(3) . . . . ? O5 Hg1 N1 C5 -67.0(3) . . . . ? O4 Hg1 N1 C5 -24.6(3) . . . . ? O2 Hg1 N1 C5 150.6(3) . . . . ? N4 Hg1 N1 C1 -100.9(3) 2_745 . . . ? O3 Hg1 N1 C1 32.0(3) . . . . ? O5 Hg1 N1 C1 124.6(2) . . . . ? O4 Hg1 N1 C1 167.1(3) . . . . ? O2 Hg1 N1 C1 -17.7(3) . . . . ? O1 C6 N2 N3 0.2(4) . . . . ? C3 C6 N2 N3 -178.0(3) . . . . ? O1 C7 N3 N2 0.2(4) . . . . ? C8 C7 N3 N2 179.1(3) . . . . ? C6 N2 N3 C7 -0.2(4) . . . . ? C9 C10 N4 C11 -0.1(5) . . . . ? C9 C10 N4 Hg1 169.8(3) . . . 2_755 ? C12 C11 N4 C10 -0.2(5) . . . . ? C12 C11 N4 Hg1 -169.9(3) . . . 2_755 ? N2 C6 O1 C7 -0.1(4) . . . . ? C3 C6 O1 C7 178.2(3) . . . . ? N3 C7 O1 C6 -0.1(4) . . . . ? C8 C7 O1 C6 -179.1(3) . . . . ? O3 N5 O2 Hg1 0.1(3) . . . . ? N4 Hg1 O2 N5 -160.2(2) 2_745 . . . ? O3 Hg1 O2 N5 -0.05(19) . . . . ? O5 Hg1 O2 N5 -30.1(3) . . . . ? N1 Hg1 O2 N5 100.9(2) . . . . ? O2 N5 O3 Hg1 -0.1(3) . . . . ? N4 Hg1 O3 N5 26.0(3) 2_745 . . . ? O5 Hg1 O3 N5 158.9(2) . . . . ? N1 Hg1 O3 N5 -83.8(2) . . . . ? O4 Hg1 O3 N5 -178.20(19) . . . . ? O2 Hg1 O3 N5 0.05(19) . . . . ? O5 N6 O4 Hg1 -1.2(3) . . . . ? N4 Hg1 O4 N6 132.4(2) 2_745 . . . ? O3 Hg1 O4 N6 -29.2(3) . . . . ? O5 Hg1 O4 N6 0.8(2) . . . . ? N1 Hg1 O4 N6 -128.8(2) . . . . ? O4 N6 O5 Hg1 1.3(4) . . . . ? N4 Hg1 O5 N6 -63.7(3) 2_745 . . . ? O3 Hg1 O5 N6 158.5(3) . . . . ? N1 Hg1 O5 N6 59.1(3) . . . . ? O4 Hg1 O5 N6 -0.8(2) . . . . ? O2 Hg1 O5 N6 -178.9(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.555 _refine_diff_density_min -1.981 _refine_diff_density_rms 0.156