# Electronic Supplementary Material (ESI) for CrystEngComm # 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_p-1 _database_code_depnum_ccdc_archive 'CCDC 898294' #TrackingRef '24.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Br2 Hg N2' _chemical_formula_sum 'C9 H8 Br2 Hg N2' _chemical_formula_weight 504.58 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' 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' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6554(4) _cell_length_b 8.3794(4) _cell_length_c 9.4395(4) _cell_angle_alpha 78.6490(10) _cell_angle_beta 69.6310(10) _cell_angle_gamma 73.8840(10) _cell_volume 541.97(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2130 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour grey _exptl_crystal_size_max 0.330 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.120 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 21.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1614 _exptl_absorpt_correction_T_max 0.4356 _exptl_absorpt_process_details SADABS _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 APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6008 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2592 _reflns_number_gt 2435 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0282P)^2^+1.4458P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2592 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 -0.11995(2) -0.25504(2) 0.100744(18) 0.01846(7) Uani 1 1 d . . . Br1 Br -0.20691(6) 0.00406(5) -0.07436(5) 0.01703(10) Uani 1 1 d . . . Br2 Br 0.17839(6) -0.47562(5) 0.10738(5) 0.01756(10) Uani 1 1 d . . . N1 N -0.2529(5) -0.1987(5) 0.3585(4) 0.0148(7) Uani 1 1 d . . . N2 N -0.4381(6) -0.3078(5) 0.2025(5) 0.0199(8) Uani 1 1 d . . . H1N H -0.5056 -0.2130 0.1655 0.024 Uiso 1 1 d R . . H2N H -0.4283 -0.3784 0.1382 0.024 Uiso 1 1 d R . . C1 C -0.1624(6) -0.1451(6) 0.4301(5) 0.0178(9) Uani 1 1 d . . . H1A H -0.0433 -0.1172 0.3730 0.021 Uiso 1 1 calc R . . C2 C -0.2343(7) -0.1275(6) 0.5867(6) 0.0216(9) Uani 1 1 d . . . H2A H -0.1638 -0.0902 0.6339 0.026 Uiso 1 1 calc R . . C3 C -0.4052(7) -0.1646(6) 0.6692(5) 0.0199(9) Uani 1 1 d . . . H3A H -0.4570 -0.1510 0.7744 0.024 Uiso 1 1 calc R . . C4 C -0.5069(6) -0.2241(5) 0.5974(5) 0.0161(8) Uani 1 1 d . . . C5 C -0.6846(7) -0.2676(6) 0.6772(6) 0.0228(10) Uani 1 1 d . . . H5A H -0.7416 -0.2561 0.7827 0.027 Uiso 1 1 calc R . . C6 C -0.7742(7) -0.3262(6) 0.6021(6) 0.0234(10) Uani 1 1 d . . . H6A H -0.8919 -0.3577 0.6565 0.028 Uiso 1 1 calc R . . C7 C -0.6932(6) -0.3404(6) 0.4445(6) 0.0192(9) Uani 1 1 d . . . H7A H -0.7575 -0.3813 0.3944 0.023 Uiso 1 1 calc R . . C8 C -0.5227(6) -0.2958(5) 0.3624(5) 0.0157(8) Uani 1 1 d . . . C9 C -0.4246(6) -0.2386(5) 0.4398(5) 0.0124(8) 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 0.01567(10) 0.02191(10) 0.01034(10) -0.00031(6) -0.00098(7) 0.00244(7) Br1 0.0165(2) 0.0194(2) 0.0157(2) 0.00194(16) -0.00779(17) -0.00420(16) Br2 0.0157(2) 0.0172(2) 0.0171(2) -0.00300(16) -0.00466(17) 0.00068(16) N1 0.0128(17) 0.0155(17) 0.0124(17) -0.0004(14) -0.0023(14) -0.0003(14) N2 0.021(2) 0.0213(19) 0.018(2) -0.0046(16) -0.0084(16) -0.0011(16) C1 0.013(2) 0.018(2) 0.020(2) -0.0026(17) -0.0053(18) -0.0003(16) C2 0.027(2) 0.020(2) 0.019(2) -0.0036(18) -0.012(2) -0.0008(19) C3 0.026(2) 0.018(2) 0.013(2) -0.0031(17) -0.0095(19) 0.0047(18) C4 0.017(2) 0.0136(19) 0.009(2) 0.0012(15) -0.0006(17) 0.0025(16) C5 0.020(2) 0.021(2) 0.017(2) -0.0015(18) 0.0014(19) 0.0026(18) C6 0.014(2) 0.019(2) 0.029(3) 0.0036(19) -0.003(2) -0.0008(18) C7 0.013(2) 0.017(2) 0.027(2) 0.0014(18) -0.0072(19) -0.0031(17) C8 0.016(2) 0.0153(19) 0.016(2) -0.0015(16) -0.0074(17) 0.0002(16) C9 0.0114(18) 0.0108(18) 0.0109(19) 0.0023(15) -0.0048(16) 0.0031(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 N1 2.375(4) . ? Hg1 N2 2.419(4) . ? Hg1 Br2 2.5193(5) . ? Hg1 Br1 2.5377(5) . ? N1 C1 1.325(6) . ? N1 C9 1.367(6) . ? N2 C8 1.433(6) . ? N2 H1N 0.9000 . ? N2 H2N 0.8999 . ? C1 C2 1.409(7) . ? C1 H1A 0.9500 . ? C2 C3 1.355(7) . ? C2 H2A 0.9500 . ? C3 C4 1.424(7) . ? C3 H3A 0.9500 . ? C4 C9 1.415(6) . ? C4 C5 1.416(7) . ? C5 C6 1.371(8) . ? C5 H5A 0.9500 . ? C6 C7 1.414(7) . ? C6 H6A 0.9500 . ? C7 C8 1.377(6) . ? C7 H7A 0.9500 . ? C8 C9 1.431(6) . ? 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 N2 70.82(13) . . ? N1 Hg1 Br2 101.48(9) . . ? N2 Hg1 Br2 123.46(10) . . ? N1 Hg1 Br1 110.51(9) . . ? N2 Hg1 Br1 95.41(10) . . ? Br2 Hg1 Br1 136.264(16) . . ? C1 N1 C9 118.8(4) . . ? C1 N1 Hg1 123.5(3) . . ? C9 N1 Hg1 117.4(3) . . ? C8 N2 Hg1 113.6(3) . . ? C8 N2 H1N 100.4 . . ? Hg1 N2 H1N 100.7 . . ? C8 N2 H2N 136.0 . . ? Hg1 N2 H2N 99.8 . . ? H1N N2 H2N 100.7 . . ? N1 C1 C2 123.2(4) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C3 C2 C1 119.1(4) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C9 C4 C5 119.7(4) . . ? C9 C4 C3 117.6(4) . . ? C5 C4 C3 122.7(4) . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 120.7(5) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C8 C7 C6 121.0(4) . . ? C8 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? C7 C8 C9 119.0(4) . . ? C7 C8 N2 122.2(4) . . ? C9 C8 N2 118.7(4) . . ? N1 C9 C4 121.6(4) . . ? N1 C9 C8 118.8(4) . . ? C4 C9 C8 119.6(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 N2 Hg1 N1 C1 -179.3(4) . . . . ? Br2 Hg1 N1 C1 59.0(3) . . . . ? Br1 Hg1 N1 C1 -90.7(3) . . . . ? N2 Hg1 N1 C9 6.8(3) . . . . ? Br2 Hg1 N1 C9 -114.9(3) . . . . ? Br1 Hg1 N1 C9 95.5(3) . . . . ? N1 Hg1 N2 C8 -6.7(3) . . . . ? Br2 Hg1 N2 C8 84.6(3) . . . . ? Br1 Hg1 N2 C8 -116.6(3) . . . . ? C9 N1 C1 C2 0.2(7) . . . . ? Hg1 N1 C1 C2 -173.6(3) . . . . ? N1 C1 C2 C3 -0.9(7) . . . . ? C1 C2 C3 C4 1.5(7) . . . . ? C2 C3 C4 C9 -1.3(6) . . . . ? C2 C3 C4 C5 179.0(4) . . . . ? C9 C4 C5 C6 1.2(7) . . . . ? C3 C4 C5 C6 -179.1(4) . . . . ? C4 C5 C6 C7 -1.4(7) . . . . ? C5 C6 C7 C8 0.0(7) . . . . ? C6 C7 C8 C9 1.6(7) . . . . ? C6 C7 C8 N2 -179.6(4) . . . . ? Hg1 N2 C8 C7 -172.3(3) . . . . ? Hg1 N2 C8 C9 6.5(5) . . . . ? C1 N1 C9 C4 -0.1(6) . . . . ? Hg1 N1 C9 C4 174.1(3) . . . . ? C1 N1 C9 C8 179.8(4) . . . . ? Hg1 N1 C9 C8 -6.0(5) . . . . ? C5 C4 C9 N1 -179.7(4) . . . . ? C3 C4 C9 N1 0.6(6) . . . . ? C5 C4 C9 C8 0.5(6) . . . . ? C3 C4 C9 C8 -179.2(4) . . . . ? C7 C8 C9 N1 178.3(4) . . . . ? N2 C8 C9 N1 -0.5(6) . . . . ? C7 C8 C9 C4 -1.9(6) . . . . ? N2 C8 C9 C4 179.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H1N Br1 2_455 0.900 2.690 3.544(2) 159 ? N2 H2N Br2 2_545 0.900 2.694 3.441(2) 141 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.828 _refine_diff_density_min -1.555 _refine_diff_density_rms 0.191 data_m _database_code_depnum_ccdc_archive 'CCDC 898295' #TrackingRef '41.cif' _vrf_PLAT232_m ; PROBLEM: Hirshfeld Test Diff for Hg2-I2, Hg2-I1a and Hg3-I2 RESPONSE: This is related to the impossibility to correctly take into account the thermal motion. This can also be due to the following reasons: the first one is the disorder of C9N2 cycle that cannot be correctly resolved. The second one is a very high absorption that cannot be correctly taken into account. Moreover, the single crystalline samples can be obtained only as very thin plates, additionally complicating our efforts to correct for the absorption effects. ; _vrf_PLAT342_m ; PROBLEM: Low Bond Precision on C-C Bonds RESPONSE: High termal parameters of some carbon atoms are probably due to the following reasons: the first one is the disorder of C9N2 cycle that cannot be correctly resolved. The second one is a very high absorption that cannot be correctly taken into account. Moreover, the single crystalline samples can be obtained only as very thin plates, additionally complicating our efforts to correct for the absorption effects. ; _vrf_PLAT971_m ; PROBLEM: Large Calcd. Non-Metal Positive Residual Density 2.95 eA-3 RESPONSE: This is related to a very high absorption that cannot be correctly taken into account. Moreover, the single crystalline samples can be obtained only as very thin plates, additionally complicating our efforts to correct for the absorption effects. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Hg5 I10 N4' _chemical_formula_sum 'C9 H8 Hg2.50 I5 N2' _chemical_formula_weight 1280.15 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6657(6) _cell_length_b 14.5794(12) _cell_length_c 17.3760(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.3150(10) _cell_angle_gamma 90.00 _cell_volume 1933.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3083 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 4.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2164 _exptl_absorpt_coefficient_mu 27.782 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.032 _exptl_absorpt_correction_T_max 0.103 _exptl_absorpt_process_details SADABS _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 APEX II CCD area detector'" _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16790 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3760 _reflns_number_gt 3276 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0538P)^2^+36.6668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3760 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.51250(7) 0.11511(5) 0.24170(3) 0.02995(18) Uani 1 1 d . . . Hg2 Hg -0.00865(8) 0.03440(5) 0.36075(3) 0.03182(18) Uani 1 1 d . . . Hg3 Hg 0.5000 0.0000 0.5000 0.0285(2) Uani 1 2 d S . . I1 I 0.83919(11) 0.18068(6) 0.23368(5) 0.0219(2) Uani 1 1 d . . . I2 I 0.33572(10) 0.16116(6) 0.36275(4) 0.0186(2) Uani 1 1 d . . . I3 I 0.05484(12) -0.09721(7) 0.26414(5) 0.0255(2) Uani 1 1 d . . . I4 I -0.12329(11) 0.12397(6) 0.47777(5) 0.0185(2) Uani 1 1 d . . . I5 I 0.40799(11) 0.11652(6) 0.60252(5) 0.0201(2) Uani 1 1 d . . . N1 N 0.3331(16) 0.1031(8) 0.1294(7) 0.026(3) Uani 1 1 d . . . N2 N 0.5125(19) -0.0440(10) 0.2021(8) 0.038(3) Uani 1 1 d . . . H1N H 0.6236 -0.0646 0.2042 0.046 Uiso 1 1 d R . . H2N H 0.4547 -0.0779 0.2348 0.046 Uiso 1 1 d R . . C1 C 0.243(2) 0.1705(15) 0.0978(12) 0.051(5) Uani 1 1 d . . . H1A H 0.2383 0.2266 0.1252 0.061 Uiso 1 1 calc R . . C2 C 0.1496(19) 0.1627(11) 0.0212(9) 0.0302(17) Uani 1 1 d . . . H2A H 0.0821 0.2133 0.0009 0.036 Uiso 1 1 calc R . . C3 C 0.1556(19) 0.0870(11) -0.0209(9) 0.0302(17) Uani 1 1 d . . . H3A H 0.0981 0.0836 -0.0717 0.036 Uiso 1 1 calc R . . C4 C 0.2564(19) 0.0070(12) 0.0146(8) 0.032(4) Uani 1 1 d . . . C5 C 0.263(2) -0.0711(14) -0.0257(10) 0.044(4) Uani 1 1 d . . . H5A H 0.2042 -0.0777 -0.0759 0.052 Uiso 1 1 calc R . . C6 C 0.3616(19) -0.1420(11) 0.0103(9) 0.0302(17) Uani 1 1 d . . . H6A H 0.3748 -0.1971 -0.0177 0.036 Uiso 1 1 calc R . . C7 C 0.4432(19) -0.1354(11) 0.0870(9) 0.0302(17) Uani 1 1 d . . . H7A H 0.5045 -0.1861 0.1108 0.036 Uiso 1 1 calc R . . C8 C 0.431(2) -0.0547(12) 0.1254(10) 0.035(4) Uani 1 1 d . . . C9 C 0.3375(17) 0.0248(10) 0.0881(7) 0.021(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Hg1 0.0258(3) 0.0458(4) 0.0180(3) -0.0078(2) 0.0011(2) -0.0083(2) Hg2 0.0302(3) 0.0384(4) 0.0263(3) -0.0131(2) -0.0002(2) 0.0087(3) Hg3 0.0292(4) 0.0302(5) 0.0261(4) -0.0137(3) 0.0024(3) 0.0024(3) I1 0.0223(4) 0.0220(5) 0.0208(4) 0.0047(3) -0.0013(3) -0.0028(3) I2 0.0176(4) 0.0191(5) 0.0188(4) -0.0023(3) 0.0006(3) -0.0006(3) I3 0.0297(5) 0.0220(5) 0.0255(4) -0.0069(4) 0.0062(3) -0.0025(4) I4 0.0219(4) 0.0134(4) 0.0205(4) -0.0012(3) 0.0035(3) -0.0010(3) I5 0.0233(4) 0.0176(5) 0.0195(4) -0.0063(3) 0.0033(3) -0.0018(3) N1 0.037(7) 0.012(6) 0.030(6) 0.000(5) 0.004(5) 0.004(5) N2 0.040(8) 0.036(9) 0.039(8) 0.013(6) 0.005(6) 0.009(6) C1 0.015(8) 0.062(14) 0.076(13) 0.043(11) 0.006(7) 0.003(8) C2 0.025(4) 0.021(4) 0.046(4) 0.010(3) 0.009(3) -0.001(3) C3 0.025(4) 0.021(4) 0.046(4) 0.010(3) 0.009(3) -0.001(3) C4 0.025(8) 0.043(10) 0.029(7) -0.015(7) 0.014(6) -0.024(7) C5 0.033(9) 0.063(14) 0.036(9) -0.005(8) 0.008(7) -0.018(9) C6 0.025(4) 0.021(4) 0.046(4) 0.010(3) 0.009(3) -0.001(3) C7 0.025(4) 0.021(4) 0.046(4) 0.010(3) 0.009(3) -0.001(3) C8 0.031(8) 0.026(9) 0.051(10) 0.006(7) 0.017(7) -0.001(7) C9 0.016(6) 0.029(8) 0.018(6) -0.001(5) 0.009(5) -0.005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Hg1 N1 2.287(12) . ? Hg1 N2 2.420(15) . ? Hg1 I2 2.6907(10) . ? Hg1 I1 2.6962(10) . ? Hg2 I3 2.6244(10) . ? Hg2 I4 2.6350(10) . ? Hg2 I1 3.2105(11) 1_455 ? Hg2 I2 3.2200(11) . ? Hg3 I5 2.6057(8) . ? Hg3 I5 2.6057(8) 3_656 ? I1 Hg2 3.2105(11) 1_655 ? N1 C1 1.29(2) . ? N1 C9 1.351(18) . ? N2 C8 1.43(2) . ? N2 H1N 0.9000 . ? N2 H2N 0.8999 . ? C1 C2 1.46(3) . ? C1 H1A 0.9500 . ? C2 C3 1.33(2) . ? C2 H2A 0.9500 . ? C3 C4 1.50(2) . ? C3 H3A 0.9500 . ? C4 C5 1.34(2) . ? C4 C9 1.391(19) . ? C5 C6 1.39(3) . ? C5 H5A 0.9500 . ? C6 C7 1.42(2) . ? C6 H6A 0.9500 . ? C7 C8 1.36(2) . ? C7 H7A 0.9500 . ? C8 C9 1.48(2) . ? 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 N2 72.5(4) . . ? N1 Hg1 I2 112.3(3) . . ? N2 Hg1 I2 118.4(3) . . ? N1 Hg1 I1 118.1(3) . . ? N2 Hg1 I1 107.5(3) . . ? I2 Hg1 I1 119.30(3) . . ? I3 Hg2 I4 161.95(4) . . ? I3 Hg2 I1 97.06(3) . 1_455 ? I4 Hg2 I1 94.34(3) . 1_455 ? I3 Hg2 I2 103.07(3) . . ? I4 Hg2 I2 92.23(3) . . ? I1 Hg2 I2 82.62(3) 1_455 . ? I5 Hg3 I5 180.0 . 3_656 ? Hg1 I1 Hg2 90.51(3) . 1_655 ? Hg1 I2 Hg2 108.67(3) . . ? C1 N1 C9 117.0(16) . . ? C1 N1 Hg1 124.0(13) . . ? C9 N1 Hg1 118.4(9) . . ? C8 N2 Hg1 111.0(10) . . ? C8 N2 H1N 109.3 . . ? Hg1 N2 H1N 109.5 . . ? C8 N2 H2N 109.4 . . ? Hg1 N2 H2N 109.5 . . ? H1N N2 H2N 108.1 . . ? N1 C1 C2 122(2) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 121.9(16) . . ? C3 C2 H2A 119.0 . . ? C1 C2 H2A 119.0 . . ? C2 C3 C4 117.5(15) . . ? C2 C3 H3A 121.2 . . ? C4 C3 H3A 121.2 . . ? C5 C4 C9 127.0(18) . . ? C5 C4 C3 119.3(15) . . ? C9 C4 C3 113.7(14) . . ? C4 C5 C6 116.2(16) . . ? C4 C5 H5A 121.9 . . ? C6 C5 H5A 121.9 . . ? C5 C6 C7 122.9(16) . . ? C5 C6 H6A 118.5 . . ? C7 C6 H6A 118.5 . . ? C8 C7 C6 118.4(15) . . ? C8 C7 H7A 120.8 . . ? C6 C7 H7A 120.8 . . ? C7 C8 N2 120.7(15) . . ? C7 C8 C9 120.9(15) . . ? N2 C8 C9 118.4(14) . . ? N1 C9 C4 127.9(14) . . ? N1 C9 C8 117.6(13) . . ? C4 C9 C8 114.4(14) . . ? 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 I1 Hg2 -140.7(3) . . . 1_655 ? N2 Hg1 I1 Hg2 -61.6(3) . . . 1_655 ? I2 Hg1 I1 Hg2 76.80(4) . . . 1_655 ? N1 Hg1 I2 Hg2 46.6(3) . . . . ? N2 Hg1 I2 Hg2 -34.9(4) . . . . ? I1 Hg1 I2 Hg2 -168.91(3) . . . . ? I3 Hg2 I2 Hg1 14.98(4) . . . . ? I4 Hg2 I2 Hg1 -174.68(3) . . . . ? I1 Hg2 I2 Hg1 -80.59(3) 1_455 . . . ? N2 Hg1 N1 C1 176.5(13) . . . . ? I2 Hg1 N1 C1 62.4(13) . . . . ? I1 Hg1 N1 C1 -82.6(13) . . . . ? N2 Hg1 N1 C9 -12.5(10) . . . . ? I2 Hg1 N1 C9 -126.6(9) . . . . ? I1 Hg1 N1 C9 88.4(10) . . . . ? N1 Hg1 N2 C8 11.1(10) . . . . ? I2 Hg1 N2 C8 117.5(9) . . . . ? I1 Hg1 N2 C8 -103.6(10) . . . . ? C9 N1 C1 C2 0(2) . . . . ? Hg1 N1 C1 C2 171.6(10) . . . . ? N1 C1 C2 C3 -2(2) . . . . ? C1 C2 C3 C4 3(2) . . . . ? C2 C3 C4 C5 178.9(14) . . . . ? C2 C3 C4 C9 -2.2(18) . . . . ? C9 C4 C5 C6 0(2) . . . . ? C3 C4 C5 C6 178.9(13) . . . . ? C4 C5 C6 C7 3(2) . . . . ? C5 C6 C7 C8 -3(2) . . . . ? C6 C7 C8 N2 -179.2(13) . . . . ? C6 C7 C8 C9 -1(2) . . . . ? Hg1 N2 C8 C7 168.9(11) . . . . ? Hg1 N2 C8 C9 -9.8(16) . . . . ? C1 N1 C9 C4 0(2) . . . . ? Hg1 N1 C9 C4 -171.7(10) . . . . ? C1 N1 C9 C8 -176.6(13) . . . . ? Hg1 N1 C9 C8 11.8(16) . . . . ? C5 C4 C9 N1 179.6(15) . . . . ? C3 C4 C9 N1 0.9(19) . . . . ? C5 C4 C9 C8 -4(2) . . . . ? C3 C4 C9 C8 177.5(12) . . . . ? C7 C8 C9 N1 -179.1(13) . . . . ? N2 C8 C9 N1 -1(2) . . . . ? C7 C8 C9 C4 4(2) . . . . ? N2 C8 C9 C4 -177.5(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2N I5 3_656 0.900 2.978 3.55(1) 123 ? N2 H2N I3 1_555 0.900 3.166 3.84(1) 134 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 4.375 _refine_diff_density_min -2.855 _refine_diff_density_rms 0.481