# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Rademeyer, Melanie' _publ_contact_author_email Melanie.Rademeyer@up.ac.za _publ_section_title ; Robust motifs in 2-phenylethylammonium- and related tetrahalometallates ; _publ_author_name M.Rademeyer data_ZnCl(1) _database_code_depnum_ccdc_archive 'CCDC 791566' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Cl4 Zn' _chemical_formula_sum 'C16 H24 Cl4 N2 Zn' _chemical_formula_weight 451.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 7.432(14) _cell_length_b 24.68(3) _cell_length_c 11.157(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.70(14) _cell_angle_gamma 90.00 _cell_volume 2046(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 536 _cell_measurement_theta_min 2 _cell_measurement_theta_max 31 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4796 _exptl_absorpt_correction_T_max 0.7245 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Excalibur2' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 20369 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 31.83 _reflns_number_total 6577 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_cell_refinement 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_data_reduction 'CrysAlis RED 170 (Oxford Diffraction Ltd., 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.1010P)^2^+0.0248P] 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 6577 _refine_ls_number_parameters 208 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.1298 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2260 _refine_ls_wR_factor_gt 0.2000 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.110 _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 C16 C 0.3703(7) 0.6984(3) 0.6452(5) 0.0716(14) Uani 1 1 d . . . H16 H 0.3980 0.6696 0.5953 0.086 Uiso 1 1 calc R . . C11 C 0.2819(6) 0.6881(2) 0.7484(4) 0.0629(11) Uani 1 1 d DU . . C12 C 0.2411(6) 0.7314(2) 0.8202(4) 0.0674(13) Uani 1 1 d . . . H12 H 0.1799 0.7256 0.8905 0.081 Uiso 1 1 calc R . . C13 C 0.2896(7) 0.7833(2) 0.7892(5) 0.0725(14) Uani 1 1 d . . . H13 H 0.2626 0.8122 0.8391 0.087 Uiso 1 1 calc R . . C2 C 0.1173(7) 0.33914(18) 0.5440(6) 0.0775(15) Uani 1 1 d D . . H2A H 0.0739 0.3522 0.4664 0.093 Uiso 1 1 calc R . . H2B H 0.0233 0.3455 0.6008 0.093 Uiso 1 1 calc R . . N1 N 0.2404(6) 0.43003(15) 0.5789(4) 0.0708(11) Uani 1 1 d D . . H1E H 0.3432 0.4479 0.5919 0.106 Uiso 1 1 calc R . . H1C H 0.1638 0.4384 0.6359 0.106 Uiso 1 1 calc R . . H1D H 0.1929 0.4393 0.5077 0.106 Uiso 1 1 calc R . . C1 C 0.2759(7) 0.3706(2) 0.5810(6) 0.0796(15) Uani 1 1 d D . . H1A H 0.3733 0.3625 0.5279 0.096 Uiso 1 1 calc R . . H1B H 0.3140 0.3599 0.6615 0.096 Uiso 1 1 calc R . . C14 C 0.3775(7) 0.7924(3) 0.6852(5) 0.0773(14) Uani 1 1 d U . . H14 H 0.4091 0.8273 0.6630 0.093 Uiso 1 1 calc R . . C15 C 0.4186(7) 0.7486(3) 0.6135(4) 0.0778(15) Uani 1 1 d U . . H15 H 0.4800 0.7541 0.5430 0.093 Uiso 1 1 calc R . . C3 C 0.1496(5) 0.27885(16) 0.5355(4) 0.0516(8) Uani 1 1 d DU . . C4 C 0.2325(5) 0.25027(17) 0.6293(4) 0.0500(8) Uani 1 1 d U . . H4 H 0.2744 0.2687 0.6973 0.060 Uiso 1 1 calc R . . C5 C 0.2528(6) 0.19499(18) 0.6221(4) 0.0565(9) Uani 1 1 d U . . H5 H 0.3079 0.1764 0.6857 0.068 Uiso 1 1 calc R . . C6 C 0.1935(6) 0.16707(18) 0.5235(5) 0.0618(10) Uani 1 1 d U . . H6 H 0.2079 0.1297 0.5188 0.074 Uiso 1 1 calc R . . C8 C 0.0900(6) 0.2499(2) 0.4367(4) 0.0570(10) Uani 1 1 d U . . H8 H 0.0340 0.2679 0.3726 0.068 Uiso 1 1 calc R . . C7 C 0.1120(6) 0.1954(2) 0.4316(4) 0.0649(11) Uani 1 1 d U . . H7 H 0.0706 0.1768 0.3637 0.078 Uiso 1 1 calc R . . C10 C 0.2306(10) 0.6297(3) 0.7721(5) 0.0985(19) Uani 1 1 d DU . . H10B H 0.1007 0.6263 0.7655 0.118 Uiso 1 1 calc R . . H10A H 0.2815 0.6069 0.7110 0.118 Uiso 1 1 calc R . . N2 N 0.2316(9) 0.55373(19) 0.9098(5) 0.1037(19) Uani 1 1 d D . . H2C H 0.3269 0.5333 0.9287 0.156 Uiso 1 1 calc R . . H2E H 0.1768 0.5408 0.8438 0.156 Uiso 1 1 calc R . . H2D H 0.1555 0.5532 0.9699 0.156 Uiso 1 1 calc R . . C9 C 0.2911(12) 0.6106(3) 0.8881(6) 0.101(2) Uani 1 1 d DU . . H9B H 0.2440 0.6341 0.9495 0.121 Uiso 1 1 calc R . . H9A H 0.4215 0.6124 0.8938 0.121 Uiso 1 1 calc R . . Zn1 Zn 0.26006(6) 0.522021(19) 0.27343(5) 0.0538(2) Uani 1 1 d . . . Cl3 Cl 0.50527(18) 0.54676(7) 0.17006(13) 0.0826(4) Uani 1 1 d . . . Cl1 Cl 0.01286(18) 0.55304(7) 0.17090(14) 0.0859(4) Uani 1 1 d . . . Cl4 Cl 0.2403(3) 0.43173(6) 0.28190(15) 0.1146(7) Uani 1 1 d . . . Cl2 Cl 0.2705(2) 0.55544(5) 0.45973(12) 0.0810(4) 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 C16 0.058(3) 0.103(4) 0.054(3) -0.012(3) 0.002(2) 0.018(3) C11 0.050(2) 0.083(3) 0.055(3) 0.007(2) -0.0007(19) 0.004(2) C12 0.049(2) 0.111(4) 0.043(2) -0.001(2) 0.0013(18) 0.015(3) C13 0.063(3) 0.084(4) 0.070(3) -0.017(3) -0.007(2) 0.015(3) C2 0.066(3) 0.061(3) 0.104(4) 0.012(3) -0.008(3) 0.001(2) N1 0.097(3) 0.048(2) 0.068(3) 0.0054(17) 0.005(2) 0.000(2) C1 0.080(3) 0.062(3) 0.096(4) -0.007(3) -0.004(3) -0.002(3) C14 0.059(3) 0.092(4) 0.079(3) 0.026(2) -0.022(3) -0.003(2) C15 0.054(3) 0.136(5) 0.044(2) 0.017(2) 0.002(2) -0.006(3) C3 0.0435(19) 0.056(2) 0.056(2) 0.0071(16) 0.0045(16) -0.0008(16) C4 0.046(2) 0.062(2) 0.0422(18) 0.0020(16) -0.0054(15) -0.0070(17) C5 0.050(2) 0.062(2) 0.057(2) 0.0129(18) -0.0010(18) -0.0031(18) C6 0.059(2) 0.049(2) 0.077(3) -0.0021(18) 0.003(2) -0.0045(18) C8 0.050(2) 0.080(2) 0.0407(19) 0.0126(18) -0.0023(16) -0.0013(19) C7 0.065(3) 0.082(3) 0.048(2) -0.0163(19) 0.0019(19) -0.004(2) C10 0.112(5) 0.112(5) 0.070(4) -0.004(3) -0.022(3) -0.014(4) N2 0.162(6) 0.065(3) 0.086(4) -0.005(2) 0.035(3) -0.022(3) C9 0.140(6) 0.078(4) 0.082(4) 0.016(3) -0.013(4) -0.015(4) Zn1 0.0527(3) 0.0514(3) 0.0577(3) -0.0046(2) 0.0051(2) 0.0009(2) Cl3 0.0614(7) 0.1039(11) 0.0836(9) -0.0062(7) 0.0213(6) -0.0127(7) Cl1 0.0610(7) 0.1144(12) 0.0820(9) 0.0104(8) -0.0041(6) 0.0188(7) Cl4 0.215(2) 0.0440(7) 0.0848(11) -0.0131(6) 0.0147(12) -0.0132(9) Cl2 0.1283(12) 0.0562(7) 0.0588(7) -0.0151(5) 0.0087(7) 0.0027(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 C16 C15 1.340(8) . ? C16 C11 1.366(7) . ? C16 H16 0.9300 . ? C11 C12 1.375(7) . ? C11 C10 1.515(7) . ? C12 C13 1.377(8) . ? C12 H12 0.9300 . ? C13 C14 1.367(8) . ? C13 H13 0.9300 . ? C2 C1 1.461(6) . ? C2 C3 1.511(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N1 C1 1.491(7) . ? N1 H1E 0.8900 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C14 C15 1.384(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C3 C8 1.376(6) . ? C3 C4 1.391(6) . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 C6 1.360(7) . ? C5 H5 0.9300 . ? C6 C7 1.368(7) . ? C6 H6 0.9300 . ? C8 C7 1.355(7) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C10 C9 1.437(7) . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? N2 C9 1.495(8) . ? N2 H2C 0.8900 . ? N2 H2E 0.8900 . ? N2 H2D 0.8900 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? Zn1 Cl2 2.235(3) . ? Zn1 Cl4 2.236(3) . ? Zn1 Cl1 2.268(4) . ? Zn1 Cl3 2.269(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 C15 C16 C11 122.3(5) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? C16 C11 C12 117.8(5) . . ? C16 C11 C10 117.0(5) . . ? C12 C11 C10 125.2(5) . . ? C11 C12 C13 120.9(5) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C1 C2 C3 114.4(4) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C1 N1 H1E 109.5 . . ? C1 N1 H1C 109.5 . . ? H1E N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C2 C1 N1 112.2(5) . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 . . ? N1 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C13 C14 C15 118.9(5) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C16 C15 C14 120.2(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C8 C3 C4 117.6(4) . . ? C8 C3 C2 121.0(4) . . ? C4 C3 C2 121.3(4) . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 118.2(4) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C7 C8 C3 120.9(4) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C8 C7 C6 121.8(4) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C9 C10 C11 113.3(5) . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? H10B C10 H10A 107.7 . . ? C9 N2 H2C 109.5 . . ? C9 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? C9 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? H2E N2 H2D 109.5 . . ? C10 C9 N2 111.6(5) . . ? C10 C9 H9B 109.3 . . ? N2 C9 H9B 109.3 . . ? C10 C9 H9A 109.3 . . ? N2 C9 H9A 109.3 . . ? H9B C9 H9A 108.0 . . ? Cl2 Zn1 Cl4 109.21(15) . . ? Cl2 Zn1 Cl1 110.46(13) . . ? Cl4 Zn1 Cl1 107.73(9) . . ? Cl2 Zn1 Cl3 111.54(13) . . ? Cl4 Zn1 Cl3 110.15(8) . . ? Cl1 Zn1 Cl3 107.67(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 C15 C16 C11 C12 0.6(7) . . . . ? C15 C16 C11 C10 178.4(5) . . . . ? C16 C11 C12 C13 -0.6(7) . . . . ? C10 C11 C12 C13 -178.3(5) . . . . ? C11 C12 C13 C14 0.9(7) . . . . ? C3 C2 C1 N1 175.6(5) . . . . ? C12 C13 C14 C15 -1.0(7) . . . . ? C11 C16 C15 C14 -0.7(8) . . . . ? C13 C14 C15 C16 0.9(7) . . . . ? C1 C2 C3 C8 -132.5(5) . . . . ? C1 C2 C3 C4 50.7(7) . . . . ? C8 C3 C4 C5 -0.1(6) . . . . ? C2 C3 C4 C5 176.8(4) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C4 C5 C6 C7 -0.3(7) . . . . ? C4 C3 C8 C7 -0.1(6) . . . . ? C2 C3 C8 C7 -177.0(4) . . . . ? C3 C8 C7 C6 0.1(7) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? C16 C11 C10 C9 127.2(7) . . . . ? C12 C11 C10 C9 -55.2(9) . . . . ? C11 C10 C9 N2 177.7(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C Cl1 0.89 2.57 3.438(7) 166.7 3_566 N1 H1D Cl4 0.89 2.56 3.314(7) 142.8 . N1 H1E Cl3 0.89 2.86 3.381(7) 119.1 3_666 N2 H2E Cl1 0.89 2.71 3.310(6) 125.5 3_566 N2 H2D Cl1 0.89 2.51 3.378(8) 165.5 1_556 N2 H2C Cl3 0.89 2.98 3.499(9) 118.6 1_556 N2 H2C Cl3 0.89 2.60 3.298(7) 136.0 3_666 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.714 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.087 data_ZnI(3) _database_code_depnum_ccdc_archive 'CCDC 791567' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), I4 Zn' _chemical_formula_sum 'C16 H24 I4 N2 Zn' _chemical_formula_weight 817.34 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' Zn Zn 0.2839 1.4301 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _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 8.2036(4) _cell_length_b 26.8324(16) _cell_length_c 10.9880(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.202(4) _cell_angle_gamma 90.00 _cell_volume 2418.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3945 _cell_measurement_theta_min 3.2813 _cell_measurement_theta_max 31.8412 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 6.122 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1498 _exptl_absorpt_correction_T_max 0.3740 _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 28909 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6006 _reflns_number_gt 4464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.0529P)^2^+15.2539P] 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 6006 _refine_ls_number_parameters 199 _refine_ls_number_restraints 88 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1603 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.097 _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 C16 C 0.3116(18) 0.7114(7) 0.6779(12) 0.106(5) Uani 1 1 d . . . H16 H 0.3477 0.6870 0.6243 0.127 Uiso 1 1 calc R . . C11 C 0.2216(12) 0.6981(3) 0.7781(10) 0.068(2) Uani 1 1 d D . . C12 C 0.1726(14) 0.7366(5) 0.8547(11) 0.080(3) Uani 1 1 d . . . H12 H 0.1141 0.7292 0.9247 0.096 Uiso 1 1 calc R . . C13 C 0.2100(18) 0.7860(5) 0.8280(16) 0.104(5) Uani 1 1 d . . . H13 H 0.1734 0.8115 0.8783 0.124 Uiso 1 1 calc R . . C1 C 0.193(2) 0.3678(4) 0.5668(13) 0.116(4) Uani 1 1 d DU . . H1A H 0.1552 0.3571 0.6463 0.139 Uiso 1 1 calc R . . H1B H 0.1041 0.3639 0.5090 0.139 Uiso 1 1 calc R . . N1 N 0.2491(15) 0.4227(3) 0.5713(8) 0.091(3) Uani 1 1 d DU . . H1E H 0.3445 0.4256 0.5337 0.136 Uiso 1 1 calc R . . H1D H 0.2598 0.4322 0.6485 0.136 Uiso 1 1 calc R . . H1C H 0.1755 0.4418 0.5344 0.136 Uiso 1 1 calc R . . C2 C 0.3346(17) 0.3382(3) 0.5291(14) 0.117(4) Uani 1 1 d DU . . H2A H 0.4203 0.3392 0.5901 0.141 Uiso 1 1 calc R . . H2B H 0.3778 0.3499 0.4522 0.141 Uiso 1 1 calc R . . C14 C 0.300(2) 0.7965(7) 0.7285(18) 0.116(5) Uani 1 1 d U . . H14 H 0.3269 0.8295 0.7114 0.140 Uiso 1 1 calc R . . C15 C 0.349(2) 0.7611(8) 0.6561(15) 0.121(5) Uani 1 1 d U . . H15 H 0.4103 0.7693 0.5881 0.145 Uiso 1 1 calc R . . C3 C 0.2630(12) 0.28507(18) 0.5166(6) 0.099(3) Uani 1 1 d GDU . . C4 C 0.3278(10) 0.2532(2) 0.6038(5) 0.087(3) Uani 1 1 d GU . . H4 H 0.3828 0.2661 0.6709 0.104 Uiso 1 1 calc R . . C5 C 0.3105(9) 0.2019(2) 0.5909(6) 0.075(2) Uani 1 1 d GU . . H5 H 0.3539 0.1806 0.6493 0.090 Uiso 1 1 calc R . . C6 C 0.2284(9) 0.18255(19) 0.4906(7) 0.080(2) Uani 1 1 d GU . . H6 H 0.2168 0.1483 0.4819 0.096 Uiso 1 1 calc R . . C7 C 0.1635(9) 0.2145(3) 0.4033(6) 0.090(3) Uani 1 1 d GU . . H7 H 0.1085 0.2015 0.3363 0.108 Uiso 1 1 calc R . . C8 C 0.1808(11) 0.2657(3) 0.4163(6) 0.102(3) Uani 1 1 d GU . . H8 H 0.1374 0.2871 0.3579 0.122 Uiso 1 1 calc R . . C10 C 0.1609(13) 0.6461(4) 0.8014(15) 0.102(4) Uani 1 1 d D . . H10B H 0.0723 0.6473 0.8596 0.122 Uiso 1 1 calc R . . H10A H 0.1187 0.6321 0.7262 0.122 Uiso 1 1 calc R . . N2 N 0.2380(14) 0.5619(3) 0.8677(10) 0.089(3) Uani 1 1 d D . . H2C H 0.2489 0.5540 0.9460 0.133 Uiso 1 1 calc R . . H2E H 0.2992 0.5416 0.8230 0.133 Uiso 1 1 calc R . . H2D H 0.1340 0.5588 0.8457 0.133 Uiso 1 1 calc R . . C9 C 0.2909(14) 0.6138(4) 0.8489(13) 0.093(4) Uani 1 1 d D . . H9B H 0.3296 0.6272 0.9257 0.111 Uiso 1 1 calc R . . H9A H 0.3814 0.6141 0.7923 0.111 Uiso 1 1 calc R . . Zn1 Zn 0.25754(11) 0.52730(4) 0.26486(9) 0.0495(2) Uani 1 1 d . . . I4 I 0.51546(7) 0.55940(3) 0.15211(6) 0.0656(2) Uani 1 1 d . . . I3 I 0.00225(7) 0.56290(3) 0.15300(7) 0.0743(2) Uani 1 1 d . . . I1 I 0.24751(10) 0.43073(2) 0.24322(6) 0.0711(2) Uani 1 1 d . . . I2 I 0.25514(10) 0.55459(2) 0.49415(6) 0.0696(2) 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 C16 0.102(10) 0.139(14) 0.077(8) -0.008(8) 0.011(7) 0.003(9) C11 0.071(6) 0.065(6) 0.068(6) 0.000(5) -0.007(5) -0.004(5) C12 0.080(7) 0.084(8) 0.076(7) -0.005(6) 0.001(5) 0.006(6) C13 0.098(10) 0.072(9) 0.140(13) -0.020(8) -0.022(9) 0.017(7) C1 0.205(13) 0.052(4) 0.091(8) 0.005(6) 0.008(9) 0.004(6) N1 0.173(10) 0.046(4) 0.054(5) 0.006(4) -0.011(6) -0.009(5) C2 0.182(11) 0.064(4) 0.106(8) 0.011(5) -0.007(8) 0.004(5) C14 0.104(10) 0.101(11) 0.144(13) 0.050(8) -0.037(10) -0.023(8) C15 0.116(11) 0.152(14) 0.094(10) 0.053(9) 0.001(8) -0.026(11) C3 0.191(10) 0.054(4) 0.052(5) 0.002(3) -0.015(5) 0.008(5) C4 0.129(8) 0.063(4) 0.067(5) 0.012(4) -0.022(5) -0.023(6) C5 0.076(6) 0.055(4) 0.093(6) 0.016(4) 0.001(5) 0.002(4) C6 0.077(6) 0.058(5) 0.104(7) -0.024(4) 0.024(5) -0.004(4) C7 0.098(7) 0.106(6) 0.067(5) -0.033(5) 0.003(5) -0.007(6) C8 0.154(9) 0.091(5) 0.061(5) -0.009(5) -0.021(5) 0.034(7) C10 0.070(7) 0.087(9) 0.148(13) 0.001(9) -0.011(8) -0.006(6) N2 0.110(8) 0.069(6) 0.087(7) -0.012(5) 0.002(6) 0.008(5) C9 0.086(8) 0.079(8) 0.114(10) 0.025(7) -0.005(7) -0.005(6) Zn1 0.0430(5) 0.0474(5) 0.0581(6) 0.0002(4) 0.0005(4) 0.0007(4) I4 0.0440(3) 0.0776(4) 0.0752(4) 0.0055(3) 0.0077(3) -0.0078(3) I3 0.0455(3) 0.0909(5) 0.0863(5) 0.0082(4) -0.0076(3) 0.0151(3) I1 0.1103(6) 0.0431(3) 0.0599(4) -0.0080(3) 0.0012(3) -0.0032(3) I2 0.0999(5) 0.0519(3) 0.0570(4) -0.0092(3) 0.0044(3) -0.0012(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 C16 C11 1.375(16) . ? C16 C15 1.39(2) . ? C16 H16 0.9300 . ? C11 C12 1.392(15) . ? C11 C10 1.504(8) . ? C12 C13 1.392(19) . ? C12 H12 0.9300 . ? C13 C14 1.35(2) . ? C13 H13 0.9300 . ? C1 C2 1.468(19) . ? C1 N1 1.544(14) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 H1E 0.8900 . ? N1 H1D 0.8900 . ? N1 H1C 0.8900 . ? C2 C3 1.547(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C14 C15 1.31(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C3 C4 1.3900 . ? C3 C8 1.3900 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C9 1.469(9) . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? N2 C9 1.474(14) . ? N2 H2C 0.8900 . ? N2 H2E 0.8900 . ? N2 H2D 0.8900 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? Zn1 I4 2.6023(11) . ? Zn1 I1 2.6032(12) . ? Zn1 I3 2.6061(11) . ? Zn1 I2 2.6239(12) . ? 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 C11 C16 C15 120.5(15) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C11 C12 116.6(11) . . ? C16 C11 C10 123.9(12) . . ? C12 C11 C10 119.2(11) . . ? C13 C12 C11 121.0(12) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 119.5(14) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C2 C1 N1 106.7(10) . . ? C2 C1 H1A 110.4 . . ? N1 C1 H1A 110.4 . . ? C2 C1 H1B 110.4 . . ? N1 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? C1 N1 H1E 109.5 . . ? C1 N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? C1 N1 H1C 109.5 . . ? H1E N1 H1C 109.5 . . ? H1D N1 H1C 109.5 . . ? C1 C2 C3 102.8(8) . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C15 C14 C13 120.7(16) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 121.8(16) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C4 C3 C8 120.0 . . ? C4 C3 C2 111.2(7) . . ? C8 C3 C2 126.7(7) . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.0 . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? C9 C10 C11 111.6(9) . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? H10B C10 H10A 108.0 . . ? C9 N2 H2C 109.5 . . ? C9 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? C9 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? H2E N2 H2D 109.5 . . ? C10 C9 N2 113.2(10) . . ? C10 C9 H9B 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9A 108.9 . . ? H9B C9 H9A 107.7 . . ? I4 Zn1 I1 108.15(4) . . ? I4 Zn1 I3 107.91(4) . . ? I1 Zn1 I3 107.26(4) . . ? I4 Zn1 I2 111.94(4) . . ? I1 Zn1 I2 111.42(4) . . ? I3 Zn1 I2 109.98(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 C15 C16 C11 C12 0(2) . . . . ? C15 C16 C11 C10 173.3(13) . . . . ? C16 C11 C12 C13 1.8(18) . . . . ? C10 C11 C12 C13 -172.3(11) . . . . ? C11 C12 C13 C14 -2(2) . . . . ? N1 C1 C2 C3 -175.3(9) . . . . ? C12 C13 C14 C15 1(2) . . . . ? C13 C14 C15 C16 0(3) . . . . ? C11 C16 C15 C14 0(3) . . . . ? C1 C2 C3 C4 -113.3(10) . . . . ? C1 C2 C3 C8 83.4(12) . . . . ? C8 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C5 -164.5(8) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C6 C7 C8 C3 0.0 . . . . ? C4 C3 C8 C7 0.0 . . . . ? C2 C3 C8 C7 161.9(10) . . . . ? C16 C11 C10 C9 78.2(17) . . . . ? C12 C11 C10 C9 -108.2(14) . . . . ? C11 C10 C9 N2 -177.4(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D I4 0.89 2.87 3.627(10) 144.3 3_666 N1 H1D I3 0.89 3.07 3.690(10) 128.5 3_566 N1 H1C I2 0.89 3.13 3.640(8) 118.8 . N2 H2C I3 0.89 3.06 3.689(11) 129.5 1_556 N2 H2C I4 0.89 3.15 3.860(11) 138.7 1_556 N2 H2E I4 0.89 3.12 3.838(9) 139.3 3_666 N2 H2D I1 0.89 3.29 4.166(11) 169.5 3_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.882 _refine_diff_density_min -1.644 _refine_diff_density_rms 0.214 data_CdBr(5) _database_code_depnum_ccdc_archive 'CCDC 791568' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Br4 Cd' _chemical_formula_sum 'C16 H24 Br4 Cd N2' _chemical_formula_weight 676.41 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' Cd Cd -0.8075 1.2024 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _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 7.8680(9) _cell_length_b 25.864(3) _cell_length_c 11.0185(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.086(2) _cell_angle_gamma 90.00 _cell_volume 2241.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3087 _cell_measurement_theta_min 3.8320 _cell_measurement_theta_max 31.0487 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.004 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 8.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1948 _exptl_absorpt_correction_T_max 0.2941 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 26788 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5590 _reflns_number_gt 2941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.0757P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5590 _refine_ls_number_parameters 208 _refine_ls_number_restraints 76 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 1.040 _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 C16 C 0.3651(9) 0.7008(4) 0.6591(7) 0.087(3) Uani 1 1 d D . . H16 H 0.3908 0.6720 0.6122 0.105 Uiso 1 1 calc R . . C11 C 0.2652(8) 0.6949(3) 0.7749(6) 0.0740(19) Uani 1 1 d DU . . C12 C 0.2368(8) 0.7406(4) 0.8309(7) 0.073(2) Uani 1 1 d . . . H12 H 0.1783 0.7402 0.9034 0.088 Uiso 1 1 calc R . . C13 C 0.2884(10) 0.7868(4) 0.7878(9) 0.089(3) Uani 1 1 d . . . H13 H 0.2623 0.8169 0.8295 0.107 Uiso 1 1 calc R . . C2 C 0.1248(8) 0.3384(2) 0.5516(7) 0.076(2) Uani 1 1 d D . . H2A H 0.0658 0.3516 0.4799 0.091 Uiso 1 1 calc R . . H2B H 0.0519 0.3435 0.6206 0.091 Uiso 1 1 calc R . . N1 N 0.2464(9) 0.4251(2) 0.5778(6) 0.093(2) Uani 1 1 d D . . H1E H 0.3426 0.4426 0.5901 0.140 Uiso 1 1 calc R . . H1C H 0.1765 0.4310 0.6388 0.140 Uiso 1 1 calc R . . H1D H 0.1973 0.4353 0.5084 0.140 Uiso 1 1 calc R . . C1 C 0.2853(9) 0.3674(2) 0.5710(8) 0.080(2) Uani 1 1 d D . . H1A H 0.3615 0.3608 0.5047 0.096 Uiso 1 1 calc R . . H1B H 0.3407 0.3562 0.6459 0.096 Uiso 1 1 calc R . . C14 C 0.3770(10) 0.7894(4) 0.6851(9) 0.090(2) Uani 1 1 d U . . H14 H 0.4121 0.8213 0.6556 0.108 Uiso 1 1 calc R . . C15 C 0.4140(11) 0.7468(4) 0.6265(8) 0.090(2) Uani 1 1 d U . . H15 H 0.4794 0.7496 0.5574 0.108 Uiso 1 1 calc R . . C3 C 0.1588(7) 0.2816(2) 0.5359(6) 0.0538(13) Uani 1 1 d DU . . C4 C 0.2471(7) 0.2528(2) 0.6225(6) 0.0557(14) Uani 1 1 d U . . H4 H 0.2931 0.2692 0.6906 0.067 Uiso 1 1 calc R . . C5 C 0.2679(8) 0.2000(3) 0.6096(6) 0.0628(15) Uani 1 1 d U . . H5 H 0.3256 0.1809 0.6690 0.075 Uiso 1 1 calc R . . C6 C 0.2027(9) 0.1761(3) 0.5087(6) 0.0664(16) Uani 1 1 d U . . H6 H 0.2165 0.1407 0.4995 0.080 Uiso 1 1 calc R . . C7 C 0.1195(9) 0.2030(3) 0.4228(6) 0.0678(16) Uani 1 1 d U . . H7 H 0.0761 0.1859 0.3546 0.081 Uiso 1 1 calc R . . C8 C 0.0970(8) 0.2558(3) 0.4341(6) 0.0617(15) Uani 1 1 d U . . H8 H 0.0401 0.2741 0.3731 0.074 Uiso 1 1 calc R . . C10 C 0.1866(10) 0.6451(3) 0.8106(12) 0.136(4) Uani 1 1 d DU . . H10A H 0.1078 0.6516 0.8755 0.163 Uiso 1 1 calc R . . H10B H 0.1215 0.6317 0.7419 0.163 Uiso 1 1 calc R . . N2 N 0.2199(10) 0.5578(2) 0.8894(7) 0.100(2) Uani 1 1 d D . . H2C H 0.2976 0.5342 0.9098 0.151 Uiso 1 1 calc R . . H2E H 0.1550 0.5458 0.8286 0.151 Uiso 1 1 calc R . . H2D H 0.1554 0.5645 0.9530 0.151 Uiso 1 1 calc R . . C9 C 0.3066(10) 0.6063(3) 0.8502(9) 0.108(3) Uani 1 1 d DU . . H9B H 0.3746 0.6198 0.9174 0.129 Uiso 1 1 calc R . . H9A H 0.3826 0.5984 0.7844 0.129 Uiso 1 1 calc R . . Cd1 Cd 0.26240(6) 0.524228(18) 0.27496(5) 0.06177(19) Uani 1 1 d . . . Br3 Br 0.52303(10) 0.55180(3) 0.15356(8) 0.0822(3) Uani 1 1 d . . . Br1 Br 0.00093(10) 0.56250(3) 0.16196(8) 0.0862(3) Uani 1 1 d . . . Br4 Br 0.21555(12) 0.42651(3) 0.26800(8) 0.0851(3) Uani 1 1 d . . . Br2 Br 0.28028(14) 0.55426(3) 0.49612(9) 0.0981(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 C16 0.064(5) 0.114(8) 0.083(6) -0.031(5) -0.001(4) 0.013(5) C11 0.058(4) 0.083(5) 0.081(5) 0.007(4) -0.002(4) 0.001(4) C12 0.059(4) 0.094(6) 0.066(5) -0.010(4) 0.007(3) 0.014(4) C13 0.079(5) 0.074(6) 0.113(7) -0.021(5) -0.026(5) 0.017(4) C2 0.063(4) 0.067(5) 0.097(6) 0.010(4) 0.004(4) 0.005(4) N1 0.157(7) 0.050(4) 0.072(4) -0.005(3) -0.006(4) -0.019(4) C1 0.091(5) 0.051(5) 0.097(6) 0.002(4) -0.012(4) 0.000(4) C14 0.080(5) 0.096(6) 0.093(6) 0.031(4) -0.018(5) -0.014(5) C15 0.087(5) 0.108(7) 0.076(5) 0.024(5) -0.002(4) -0.023(5) C3 0.060(3) 0.047(3) 0.054(3) 0.005(2) 0.003(3) -0.004(3) C4 0.065(4) 0.054(3) 0.048(3) 0.002(3) -0.005(3) -0.012(3) C5 0.066(4) 0.055(3) 0.067(4) 0.016(3) -0.002(3) -0.007(3) C6 0.073(4) 0.050(3) 0.077(4) -0.004(3) 0.011(3) -0.010(3) C7 0.075(4) 0.074(4) 0.055(3) -0.013(3) 0.003(3) -0.013(3) C8 0.066(4) 0.073(3) 0.046(3) 0.008(3) -0.004(3) -0.002(3) C10 0.100(7) 0.088(7) 0.219(13) 0.028(7) 0.001(7) -0.006(4) N2 0.127(6) 0.067(5) 0.107(6) -0.003(4) 0.000(5) -0.009(4) C9 0.093(6) 0.099(6) 0.132(8) 0.038(6) 0.009(5) -0.010(5) Cd1 0.0563(3) 0.0486(3) 0.0804(4) -0.0006(2) 0.0001(2) 0.0004(2) Br3 0.0657(5) 0.0852(6) 0.0960(6) 0.0023(5) 0.0109(4) -0.0132(4) Br1 0.0665(5) 0.0856(6) 0.1062(7) 0.0117(5) -0.0066(4) 0.0217(4) Br4 0.1299(7) 0.0457(4) 0.0794(5) -0.0110(4) -0.0021(5) -0.0103(4) Br2 0.1514(9) 0.0587(5) 0.0842(6) -0.0197(4) 0.0047(6) -0.0024(5) _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 C16 C15 1.302(11) . ? C16 C11 1.519(8) . ? C16 H16 0.9300 . ? C11 C12 1.354(10) . ? C11 C10 1.486(7) . ? C12 C13 1.350(11) . ? C12 H12 0.9300 . ? C13 C14 1.342(12) . ? C13 H13 0.9300 . ? C2 C1 1.481(6) . ? C2 C3 1.504(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N1 C1 1.524(8) . ? N1 H1E 0.8900 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C14 C15 1.313(12) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C3 C8 1.384(8) . ? C3 C4 1.388(8) . ? C4 C5 1.383(9) . ? C4 H4 0.9300 . ? C5 C6 1.363(9) . ? C5 H5 0.9300 . ? C6 C7 1.336(10) . ? C6 H6 0.9300 . ? C7 C8 1.384(9) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C9 1.440(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N2 C9 1.496(10) . ? N2 H2C 0.8900 . ? N2 H2E 0.8900 . ? N2 H2D 0.8900 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? Cd1 Br4 2.5551(10) . ? Cd1 Br2 2.5590(11) . ? Cd1 Br3 2.5704(9) . ? Cd1 Br1 2.5816(9) . ? 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 C15 C16 C11 118.9(8) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? C12 C11 C10 124.3(8) . . ? C12 C11 C16 112.9(7) . . ? C10 C11 C16 122.3(8) . . ? C13 C12 C11 123.9(7) . . ? C13 C12 H12 118.0 . . ? C11 C12 H12 118.0 . . ? C14 C13 C12 120.4(9) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C1 C2 C3 111.0(5) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C1 N1 H1E 109.5 . . ? C1 N1 H1C 109.5 . . ? H1E N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C2 C1 N1 109.3(6) . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1B 109.8 . . ? N1 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? C15 C14 C13 119.7(9) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 124.1(9) . . ? C16 C15 H15 117.9 . . ? C14 C15 H15 117.9 . . ? C8 C3 C4 117.4(5) . . ? C8 C3 C2 120.3(6) . . ? C4 C3 C2 122.3(6) . . ? C5 C4 C3 121.3(6) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 119.1(7) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C7 C6 C5 121.1(7) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.7(7) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 120.4(6) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C9 C10 C11 114.2(7) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C9 N2 H2C 109.5 . . ? C9 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? C9 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? H2E N2 H2D 109.5 . . ? C10 C9 N2 111.8(7) . . ? C10 C9 H9B 109.3 . . ? N2 C9 H9B 109.3 . . ? C10 C9 H9A 109.3 . . ? N2 C9 H9A 109.3 . . ? H9B C9 H9A 107.9 . . ? Br4 Cd1 Br2 109.52(3) . . ? Br4 Cd1 Br3 112.02(3) . . ? Br2 Cd1 Br3 112.42(4) . . ? Br4 Cd1 Br1 104.57(3) . . ? Br2 Cd1 Br1 111.83(4) . . ? Br3 Cd1 Br1 106.20(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C16 C11 C12 0.9(10) . . . . ? C15 C16 C11 C10 172.3(8) . . . . ? C10 C11 C12 C13 -170.0(8) . . . . ? C16 C11 C12 C13 1.2(10) . . . . ? C11 C12 C13 C14 -1.7(12) . . . . ? C3 C2 C1 N1 176.1(6) . . . . ? C12 C13 C14 C15 -0.2(12) . . . . ? C11 C16 C15 C14 -2.8(13) . . . . ? C13 C14 C15 C16 2.5(14) . . . . ? C1 C2 C3 C8 -125.3(7) . . . . ? C1 C2 C3 C4 56.8(9) . . . . ? C8 C3 C4 C5 -2.0(9) . . . . ? C2 C3 C4 C5 176.0(6) . . . . ? C3 C4 C5 C6 1.1(10) . . . . ? C4 C5 C6 C7 -0.1(10) . . . . ? C5 C6 C7 C8 -0.1(11) . . . . ? C6 C7 C8 C3 -0.9(10) . . . . ? C4 C3 C8 C7 1.9(9) . . . . ? C2 C3 C8 C7 -176.2(6) . . . . ? C12 C11 C10 C9 -117.8(11) . . . . ? C16 C11 C10 C9 71.8(13) . . . . ? C11 C10 C9 N2 177.8(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C Br1 0.89 2.63 3.510(7) 170.8 3_566 N1 H1D Br4 0.89 2.67 3.418(7) 142.9 . N1 H1E Br3 0.89 3.00 3.494(6) 116.9 3_666 N2 H2E Br1 0.89 3.06 3.603(6) 121.2 3_566 N2 H2D Br1 0.89 2.62 3.493(8) 165.3 1_556 N2 H2C Br3 0.89 3.22 3.732(8) 118.6 1_556 N2 H2C Br3 0.89 2.73 3.520(7) 148.1 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.389 _refine_diff_density_min -1.054 _refine_diff_density_rms 0.229 data_CdI(6) _database_code_depnum_ccdc_archive 'CCDC 791569' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Cd I4' _chemical_formula_sum 'C16 H24 Cd I4 N2' _chemical_formula_weight 864.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.940(2) _cell_length_b 8.214(2) _cell_length_c 13.556(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.132(17) _cell_angle_gamma 90.00 _cell_volume 1202.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 634 _cell_measurement_theta_min 2 _cell_measurement_theta_max 31 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 6.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2644 _exptl_absorpt_correction_T_max 0.3778 _exptl_absorpt_process_details 'Blessing, 1995 ' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Excalibur2' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 11900 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 31.87 _reflns_number_total 6415 _reflns_number_gt 3852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_cell_refinement 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_data_reduction 'CrysAlis RED 170 (Oxford Diffraction Ltd., 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.1358P)^2^+3.1667P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(10) _refine_ls_number_reflns 6415 _refine_ls_number_parameters 253 _refine_ls_number_restraints 341 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.2383 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.024 _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 C3 C 0.0785(9) 0.2351(16) 0.4340(6) 0.061(3) Uani 1 1 d DU . . C8 C 0.0117(12) 0.196(2) 0.5094(8) 0.077(3) Uani 1 1 d DU . . H8 H -0.0658 0.1477 0.4941 0.093 Uiso 1 1 calc R . . C7 C 0.0609(15) 0.230(2) 0.6081(8) 0.094(4) Uani 1 1 d DU . . H7 H 0.0201 0.1960 0.6595 0.113 Uiso 1 1 calc R . . C6 C 0.1712(14) 0.316(2) 0.6294(8) 0.095(4) Uani 1 1 d DU . . H6 H 0.2022 0.3424 0.6953 0.114 Uiso 1 1 calc R . . C5 C 0.2359(14) 0.362(3) 0.5539(9) 0.098(4) Uani 1 1 d DU . . H5 H 0.3087 0.4215 0.5684 0.117 Uiso 1 1 calc R . . C4 C 0.1901(10) 0.317(2) 0.4559(8) 0.076(4) Uani 1 1 d DU . . H4 H 0.2348 0.3416 0.4050 0.091 Uiso 1 1 calc R . . C2 C 0.0238(16) 0.188(2) 0.3252(10) 0.077(3) Uani 1 1 d DU . . H2A H 0.0872 0.1342 0.2945 0.093 Uiso 1 1 calc R . . H2B H -0.0436 0.1115 0.3262 0.093 Uiso 1 1 calc R . . C1 C -0.0212(14) 0.3277(17) 0.2663(8) 0.066(3) Uani 1 1 d DU . . H1A H 0.0412 0.4126 0.2752 0.079 Uiso 1 1 calc R . . H1B H -0.0947 0.3695 0.2893 0.079 Uiso 1 1 calc R . . N1 N -0.0513(11) 0.286(3) 0.1594(7) 0.083(3) Uani 1 1 d DU . . H1C H -0.0809 0.3740 0.1251 0.124 Uiso 1 1 calc R . . H1E H -0.1080 0.2077 0.1512 0.124 Uiso 1 1 calc R . . H1D H 0.0168 0.2523 0.1374 0.124 Uiso 1 1 calc R . . C11B C -0.3688(10) 0.2556(17) 0.5981(6) 0.076(3) Uani 0.864(13) 1 d PGDU A 1 C12B C -0.2831(10) 0.3538(17) 0.5611(9) 0.080(4) Uani 0.864(13) 1 d PGDU A 1 H12B H -0.2196 0.4030 0.6047 0.096 Uiso 0.864(13) 1 calc PR A 1 C13B C -0.2922(11) 0.3786(17) 0.4587(9) 0.086(4) Uani 0.864(13) 1 d PGDU A 1 H13B H -0.2349 0.4443 0.4339 0.103 Uiso 0.864(13) 1 calc PR A 1 C14B C -0.3871(12) 0.3051(18) 0.3935(7) 0.080(4) Uani 0.864(13) 1 d PGDU A 1 H14B H -0.3932 0.3216 0.3250 0.096 Uiso 0.864(13) 1 calc PR A 1 C15B C -0.4728(11) 0.2069(16) 0.4306(8) 0.080(4) Uani 0.864(13) 1 d PGDU A 1 H15B H -0.5363 0.1577 0.3869 0.097 Uiso 0.864(13) 1 calc PR A 1 C16B C -0.4636(9) 0.1822(16) 0.5329(9) 0.079(4) Uani 0.864(13) 1 d PGDU A 1 H16B H -0.5210 0.1165 0.5577 0.095 Uiso 0.864(13) 1 calc PR A 1 C10B C -0.348(2) 0.222(3) 0.7117(11) 0.107(5) Uani 0.864(13) 1 d PDU A 1 H1B1 H -0.3690 0.1096 0.7229 0.128 Uiso 0.864(13) 1 calc PR A 1 H1B2 H -0.2603 0.2359 0.7377 0.128 Uiso 0.864(13) 1 calc PR A 1 C9B C -0.418(2) 0.326(3) 0.7662(11) 0.102(5) Uani 0.864(13) 1 d PDU A 1 H9B1 H -0.5057 0.3123 0.7404 0.123 Uiso 0.864(13) 1 calc PR A 1 H9B2 H -0.3970 0.4387 0.7552 0.123 Uiso 0.864(13) 1 calc PR A 1 N2B N -0.3978(17) 0.294(5) 0.8737(9) 0.105(6) Uani 0.864(13) 1 d PDU A 1 H2CB H -0.4361 0.3691 0.9047 0.157 Uiso 0.864(13) 1 calc PR A 1 H2EB H -0.3170 0.2962 0.8968 0.157 Uiso 0.864(13) 1 calc PR A 1 H2DB H -0.4278 0.1959 0.8849 0.157 Uiso 0.864(13) 1 calc PR A 1 C11A C -0.309(7) 0.406(10) 0.584(4) 0.082(6) Uani 0.136(13) 1 d PGDU A 2 C12A C -0.297(7) 0.291(8) 0.511(5) 0.081(5) Uani 0.136(13) 1 d PGDU A 2 H12A H -0.2616 0.1907 0.5287 0.098 Uiso 0.136(13) 1 calc PR A 2 C13A C -0.339(8) 0.327(9) 0.411(5) 0.079(6) Uani 0.136(13) 1 d PGDU A 2 H13A H -0.3311 0.2507 0.3620 0.094 Uiso 0.136(13) 1 calc PR A 2 C14A C -0.392(8) 0.478(10) 0.385(4) 0.084(7) Uiso 0.136(13) 1 d PGDU A 2 H14A H -0.4202 0.5019 0.3177 0.101 Uiso 0.136(13) 1 calc PR A 2 C15A C -0.404(8) 0.592(8) 0.458(6) 0.072(14) Uiso 0.136(13) 1 d PGDU A 2 H15A H -0.4398 0.6932 0.4402 0.086 Uiso 0.136(13) 1 calc PR A 2 C16A C -0.362(8) 0.557(8) 0.558(5) 0.085(11) Uiso 0.136(13) 1 d PGDU A 2 H16A H -0.3704 0.6332 0.6069 0.102 Uiso 0.136(13) 1 calc PR A 2 C10A C -0.276(7) 0.352(15) 0.695(4) 0.100(7) Uani 0.136(13) 1 d PDU A 2 H1A1 H -0.2224 0.2581 0.6987 0.120 Uiso 0.136(13) 1 calc PR A 2 H1A2 H -0.2310 0.4394 0.7328 0.120 Uiso 0.136(13) 1 calc PR A 2 C9A C -0.384(10) 0.31(3) 0.739(6) 0.103(7) Uani 0.136(13) 1 d PDU A 2 H9A1 H -0.4122 0.2048 0.7177 0.123 Uiso 0.136(13) 1 calc PR A 2 H9A2 H -0.4494 0.3893 0.7154 0.123 Uiso 0.136(13) 1 calc PR A 2 N2A N -0.358(13) 0.32(2) 0.849(5) 0.105(11) Uani 0.136(13) 1 d PDU A 2 H2DA H -0.4282 0.3037 0.8729 0.158 Uiso 0.136(13) 1 calc PR A 2 H2CA H -0.3255 0.4143 0.8684 0.158 Uiso 0.136(13) 1 calc PR A 2 H2EA H -0.3048 0.2394 0.8710 0.158 Uiso 0.136(13) 1 calc PR A 2 I4 I 0.28867(8) 0.2694(3) 0.16233(6) 0.0856(4) Uani 1 1 d . . . I1 I 0.33199(16) 0.55054(16) -0.11224(11) 0.0923(5) Uani 1 1 d . . . I3 I 0.33339(16) 0.02025(15) -0.12249(12) 0.0879(4) Uani 1 1 d . . . I2 I -0.02897(7) 0.2774(3) -0.10233(6) 0.0864(3) Uani 1 1 d . . . Cd1 Cd 0.22491(7) 0.2799(2) -0.04182(6) 0.0596(2) 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 C3 0.067(5) 0.074(8) 0.042(3) -0.002(4) 0.009(3) 0.001(4) C8 0.083(7) 0.093(9) 0.060(5) 0.005(6) 0.022(5) -0.004(6) C7 0.130(9) 0.109(11) 0.047(4) 0.014(6) 0.024(6) 0.020(7) C6 0.120(9) 0.104(11) 0.051(5) -0.004(6) -0.019(5) 0.034(7) C5 0.088(8) 0.112(11) 0.083(7) -0.016(8) -0.017(6) -0.001(7) C4 0.062(5) 0.100(11) 0.063(5) 0.006(6) 0.004(4) -0.001(5) C2 0.093(8) 0.089(8) 0.045(4) -0.004(5) -0.005(5) 0.011(7) C1 0.071(7) 0.083(9) 0.043(4) -0.004(4) 0.008(5) 0.001(6) N1 0.076(6) 0.125(10) 0.043(4) 0.001(7) -0.003(4) 0.018(11) C11B 0.066(6) 0.091(9) 0.071(5) 0.000(6) 0.012(4) 0.010(6) C12B 0.062(7) 0.089(9) 0.089(6) -0.009(7) 0.012(6) -0.003(6) C13B 0.076(7) 0.087(8) 0.100(7) 0.005(7) 0.032(6) 0.000(6) C14B 0.089(7) 0.080(9) 0.073(6) 0.003(6) 0.018(5) 0.022(6) C15B 0.078(8) 0.073(9) 0.085(6) -0.007(7) -0.004(7) 0.007(6) C16B 0.072(8) 0.071(9) 0.092(6) 0.012(7) 0.007(6) -0.004(6) C10B 0.119(11) 0.124(12) 0.076(5) 0.013(7) 0.011(6) 0.020(9) C9B 0.113(12) 0.134(14) 0.063(6) 0.013(8) 0.024(7) 0.004(10) N2B 0.096(11) 0.152(16) 0.059(6) 0.009(11) -0.009(6) -0.002(15) C11A 0.075(10) 0.093(11) 0.081(8) 0.000(8) 0.017(9) 0.004(10) C12A 0.071(10) 0.090(11) 0.085(8) 0.001(8) 0.018(9) 0.007(10) C13A 0.073(11) 0.084(11) 0.082(8) 0.001(9) 0.023(10) 0.010(11) C10A 0.104(14) 0.114(15) 0.081(8) 0.005(11) 0.014(11) 0.010(13) C9A 0.113(14) 0.124(15) 0.072(10) 0.009(12) 0.018(10) 0.010(13) N2A 0.11(2) 0.13(2) 0.073(11) 0.01(2) 0.006(15) 0.01(2) I4 0.0678(5) 0.1371(10) 0.0492(4) -0.0014(8) 0.0011(3) 0.0085(9) I1 0.0986(11) 0.0794(9) 0.0952(11) 0.0032(7) 0.0041(8) -0.0011(7) I3 0.0904(10) 0.0798(9) 0.0933(10) -0.0178(7) 0.0135(7) -0.0017(6) I2 0.0561(4) 0.1531(10) 0.0476(4) -0.0024(9) 0.0009(3) -0.0020(10) Cd1 0.0629(4) 0.0653(5) 0.0496(4) -0.0010(6) 0.0057(3) -0.0010(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 C3 C4 1.384(17) . ? C3 C8 1.385(15) . ? C3 C2 1.549(14) . ? C8 C7 1.389(8) . ? C8 H8 0.9300 . ? C7 C6 1.39(2) . ? C7 H7 0.9300 . ? C6 C5 1.39(2) . ? C6 H6 0.9300 . ? C5 C4 1.393(18) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C2 C1 1.441(19) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 N1 1.473(14) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 H1C 0.8900 . ? N1 H1E 0.8900 . ? N1 H1D 0.8900 . ? C11B C12B 1.3900 . ? C11B C16B 1.3900 . ? C11B C10B 1.545(14) . ? C12B C13B 1.3900 . ? C12B H12B 0.9300 . ? C13B C14B 1.3900 . ? C13B H13B 0.9300 . ? C14B C15B 1.3900 . ? C14B H14B 0.9300 . ? C15B C16B 1.3900 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C10B C9B 1.44(2) . ? C10B H1B1 0.9700 . ? C10B H1B2 0.9700 . ? C9B N2B 1.463(15) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? N2B H2CB 0.8900 . ? N2B H2EB 0.8900 . ? N2B H2DB 0.8900 . ? C11A C12A 1.3900 . ? C11A C16A 1.3900 . ? C11A C10A 1.547(15) . ? C12A C13A 1.3900 . ? C12A H12A 0.9300 . ? C13A C14A 1.3900 . ? C13A H13A 0.9300 . ? C14A C15A 1.3900 . ? C14A H14A 0.9300 . ? C15A C16A 1.3900 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C10A C9A 1.44(2) . ? C10A H1A1 0.9700 . ? C10A H1A2 0.9700 . ? C9A N2A 1.468(16) . ? C9A H9A1 0.9500 . ? C9A H9A2 0.9700 . ? N2A H2DA 0.8900 . ? N2A H2CA 0.8900 . ? N2A H2EA 0.8900 . ? I4 Cd1 2.7460(13) . ? I1 Cd1 2.754(2) . ? I3 Cd1 2.750(2) . ? I2 Cd1 2.7684(12) . ? 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 C4 C3 C8 120.2(7) . . ? C4 C3 C2 121.3(10) . . ? C8 C3 C2 118.4(10) . . ? C3 C8 C7 119.7(8) . . ? C3 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C6 C7 C8 119.7(9) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C6 C5 120.9(8) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C5 C4 118.9(9) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C3 C4 C5 120.4(8) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C1 C2 C3 112.0(12) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C1 N1 111.4(13) . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? N1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C1 N1 H1C 109.5 . . ? C1 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? C1 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? C12B C11B C16B 120.0 . . ? C12B C11B C10B 117.5(10) . . ? C16B C11B C10B 122.4(10) . . ? C13B C12B C11B 120.0 . . ? C13B C12B H12B 120.0 . . ? C11B C12B H12B 120.0 . . ? C12B C13B C14B 120.0 . . ? C12B C13B H13B 120.0 . . ? C14B C13B H13B 120.0 . . ? C13B C14B C15B 120.0 . . ? C13B C14B H14B 120.0 . . ? C15B C14B H14B 120.0 . . ? C16B C15B C14B 120.0 . . ? C16B C15B H15B 120.0 . . ? C14B C15B H15B 120.0 . . ? C15B C16B C11B 120.0 . . ? C15B C16B H16B 120.0 . . ? C11B C16B H16B 120.0 . . ? C9B C10B C11B 113.4(14) . . ? C9B C10B H1B1 108.9 . . ? C11B C10B H1B1 108.9 . . ? C9B C10B H1B2 108.9 . . ? C11B C10B H1B2 108.9 . . ? H1B1 C10B H1B2 107.7 . . ? C10B C9B N2B 113.1(17) . . ? C10B C9B H9B1 109.0 . . ? N2B C9B H9B1 109.0 . . ? C10B C9B H9B2 109.0 . . ? N2B C9B H9B2 109.0 . . ? H9B1 C9B H9B2 107.8 . . ? C9B N2B H2CB 109.5 . . ? C9B N2B H2EB 109.5 . . ? H2CB N2B H2EB 109.5 . . ? C9B N2B H2DB 109.5 . . ? H2CB N2B H2DB 109.5 . . ? H2EB N2B H2DB 109.5 . . ? C12A C11A C16A 120.0 . . ? C12A C11A C10A 117.8(13) . . ? C16A C11A C10A 121.8(13) . . ? C11A C12A C13A 120.0 . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? C13A C14A C15A 120.0 . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C16A C15A C14A 120.0 . . ? C16A C15A H15A 120.0 . . ? C14A C15A H15A 120.0 . . ? C15A C16A C11A 120.0 . . ? C15A C16A H16A 120.0 . . ? C11A C16A H16A 120.0 . . ? C9A C10A C11A 112.8(18) . . ? C9A C10A H1A1 109.0 . . ? C11A C10A H1A1 109.0 . . ? C9A C10A H1A2 109.0 . . ? C11A C10A H1A2 109.0 . . ? H1A1 C10A H1A2 107.8 . . ? C10A C9A N2A 112(2) . . ? C10A C9A H9A1 108.0 . . ? N2A C9A H9A1 110.00 . . ? C10A C9A H9A2 108.0 . . ? N2A C9A H9A2 108.0 . . ? H9A1 C9A H9A2 109.0 . . ? C9A N2A H2DA 109.5 . . ? C9A N2A H2CA 111.0 . . ? H2DA N2A H2CA 111.0 . . ? C9A N2A H2EA 108.0 . . ? H2DA N2A H2EA 109.5 . . ? H2CA N2A H2EA 109.5 . . ? I4 Cd1 I3 108.66(7) . . ? I4 Cd1 I1 108.70(7) . . ? I3 Cd1 I1 104.71(5) . . ? I4 Cd1 I2 112.39(4) . . ? I3 Cd1 I2 110.63(6) . . ? I1 Cd1 I2 111.42(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 C4 C3 C8 C7 -4(3) . . . . ? C2 C3 C8 C7 177.0(15) . . . . ? C3 C8 C7 C6 6(3) . . . . ? C8 C7 C6 C5 -3(3) . . . . ? C7 C6 C5 C4 -2(3) . . . . ? C8 C3 C4 C5 -1(3) . . . . ? C2 C3 C4 C5 178.3(16) . . . . ? C6 C5 C4 C3 3(3) . . . . ? C4 C3 C2 C1 -71.7(19) . . . . ? C8 C3 C2 C1 107.2(18) . . . . ? C3 C2 C1 N1 169.4(12) . . . . ? C16B C11B C12B C13B 0.0 . . . . ? C10B C11B C12B C13B 175.3(13) . . . . ? C11B C12B C13B C14B 0.0 . . . . ? C12B C13B C14B C15B 0.0 . . . . ? C13B C14B C15B C16B 0.0 . . . . ? C14B C15B C16B C11B 0.0 . . . . ? C12B C11B C16B C15B 0.0 . . . . ? C10B C11B C16B C15B -175.0(14) . . . . ? C12B C11B C10B C9B 98(2) . . . . ? C16B C11B C10B C9B -87(2) . . . . ? C11B C10B C9B N2B 180.0(19) . . . . ? C16A C11A C12A C13A 0.0 . . . . ? C10A C11A C12A C13A 173(6) . . . . ? C11A C12A C13A C14A 0.0 . . . . ? C12A C13A C14A C15A 0.0 . . . . ? C13A C14A C15A C16A 0.0 . . . . ? C14A C15A C16A C11A 0.0 . . . . ? C12A C11A C16A C15A 0.0 . . . . ? C10A C11A C16A C15A -172(6) . . . . ? C12A C11A C10A C9A -100(11) . . . . ? C16A C11A C10A C9A 73(13) . . . . ? C11A C10A C9A N2A -160(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C I3 0.89 3.01 3.602(15) 125.9 2 N1 H1E I1 0.89 2.75 3.601(17) 161.5 2_545 N1 H1D I4 0.89 2.94 3.716(12) 146.2 . N1 H1D I2 0.89 3.22 3.596(9) 108.3 . N2B H2CB I1 0.89 2.92 3.66(3) 141.9 1_456 N2B H2CB I3 0.89 3.24 3.82(2) 125.2 2_556 N2B H2EB I2 0.89 3.15 3.999(18) 159.5 1_556 N2B H2DB I3 0.89 2.97 3.71(3) 141.1 1_456 N2B H2DB I1 0.89 3.32 3.77(2) 114.4 2_546 _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.516 _refine_diff_density_min -2.642 _refine_diff_density_rms 0.230 data_HgBr(8) _database_code_depnum_ccdc_archive 'CCDC 791570' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Br4 Hg' _chemical_formula_sum 'C16 H24 Br4 Hg N2' _chemical_formula_weight 764.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 monoclinic _symmetry_space_group_name_H-M P21/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 7.8392(16) _cell_length_b 25.756(5) _cell_length_c 11.016(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.03(3) _cell_angle_gamma 90.00 _cell_volume 2223.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2865 _cell_measurement_theta_min 3.5403 _cell_measurement_theta_max 30.5846 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 14.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0536 _exptl_absorpt_correction_T_max 0.1647 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 26516 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5548 _reflns_number_gt 2746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5548 _refine_ls_number_parameters 208 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.908 _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 C16 C 0.3623(10) 0.6989(4) 0.6641(7) 0.075(2) Uani 1 1 d D . . H16 H 0.3871 0.6692 0.6195 0.090 Uiso 1 1 calc R . . C11 C 0.2697(9) 0.6950(3) 0.7739(7) 0.071(2) Uani 1 1 d D . . C12 C 0.2381(9) 0.7405(4) 0.8337(7) 0.070(2) Uani 1 1 d . . . H12 H 0.1797 0.7397 0.9064 0.084 Uiso 1 1 calc R . . C13 C 0.2914(12) 0.7874(4) 0.7877(10) 0.088(3) Uani 1 1 d . . . H13 H 0.2690 0.8181 0.8289 0.106 Uiso 1 1 calc R . . C2 C 0.1278(9) 0.3400(2) 0.5507(8) 0.075(2) Uani 1 1 d D . . H2A H 0.0682 0.3538 0.4798 0.089 Uiso 1 1 calc R . . H2B H 0.0563 0.3449 0.6206 0.089 Uiso 1 1 calc R . . N1 N 0.2514(10) 0.4263(2) 0.5769(6) 0.091(2) Uani 1 1 d D . . H1E H 0.3473 0.4442 0.5893 0.136 Uiso 1 1 calc R . . H1C H 0.1811 0.4319 0.6381 0.136 Uiso 1 1 calc R . . H1D H 0.2017 0.4366 0.5077 0.136 Uiso 1 1 calc R . . C1 C 0.2932(10) 0.3678(3) 0.5694(8) 0.077(3) Uani 1 1 d D . . H1A H 0.3684 0.3611 0.5022 0.092 Uiso 1 1 calc R . . H1B H 0.3492 0.3563 0.6438 0.092 Uiso 1 1 calc R . . C14 C 0.3750(12) 0.7884(4) 0.6839(9) 0.083(2) Uani 1 1 d U . . H14 H 0.4078 0.8200 0.6510 0.100 Uiso 1 1 calc R . . C15 C 0.4120(12) 0.7444(4) 0.6267(8) 0.084(2) Uani 1 1 d U . . H15 H 0.4764 0.7462 0.5568 0.100 Uiso 1 1 calc R . . C3 C 0.1627(9) 0.2824(2) 0.5329(6) 0.0512(13) Uani 1 1 d DU . . C4 C 0.2497(9) 0.2535(3) 0.6213(6) 0.0519(13) Uani 1 1 d U . . H4 H 0.2945 0.2699 0.6900 0.062 Uiso 1 1 calc R . . C5 C 0.2699(9) 0.1998(3) 0.6071(7) 0.0548(14) Uani 1 1 d U . . H5 H 0.3280 0.1806 0.6661 0.066 Uiso 1 1 calc R . . C6 C 0.2043(9) 0.1761(3) 0.5069(7) 0.0576(14) Uani 1 1 d U . . H6 H 0.2161 0.1404 0.4980 0.069 Uiso 1 1 calc R . . C8 C 0.1004(9) 0.2566(3) 0.4318(6) 0.0565(14) Uani 1 1 d U . . H8 H 0.0433 0.2750 0.3707 0.068 Uiso 1 1 calc R . . C7 C 0.1228(10) 0.2035(3) 0.4209(7) 0.0587(14) Uani 1 1 d U . . H7 H 0.0802 0.1865 0.3522 0.070 Uiso 1 1 calc R . . C10 C 0.1938(13) 0.6444(4) 0.8092(13) 0.148(5) Uani 1 1 d D . . H10B H 0.1102 0.6509 0.8712 0.177 Uiso 1 1 calc R . . H10A H 0.1330 0.6304 0.7390 0.177 Uiso 1 1 calc R . . N2 N 0.2245(10) 0.5576(2) 0.8928(7) 0.092(2) Uani 1 1 d D . . H2C H 0.3036 0.5343 0.9131 0.138 Uiso 1 1 calc R . . H2E H 0.1592 0.5452 0.8326 0.138 Uiso 1 1 calc R . . H2D H 0.1602 0.5643 0.9568 0.138 Uiso 1 1 calc R . . C9 C 0.3076(12) 0.6057(4) 0.8533(11) 0.114(4) Uani 1 1 d D . . H9B H 0.3729 0.6199 0.9212 0.136 Uiso 1 1 calc R . . H9A H 0.3872 0.5972 0.7899 0.136 Uiso 1 1 calc R . . Hg1 Hg 0.26486(4) 0.524695(12) 0.27592(3) 0.06464(14) Uani 1 1 d . . . Br3 Br 0.52506(11) 0.55320(4) 0.15214(9) 0.0774(3) Uani 1 1 d . . . Br1 Br -0.00204(11) 0.56272(4) 0.16202(9) 0.0801(3) Uani 1 1 d . . . Br4 Br 0.21803(14) 0.42611(3) 0.26534(8) 0.0835(3) Uani 1 1 d . . . Br2 Br 0.28007(16) 0.55465(3) 0.49806(9) 0.0921(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 C16 0.055(5) 0.106(7) 0.064(6) -0.014(5) 0.006(4) 0.005(5) C11 0.047(4) 0.081(6) 0.085(6) 0.018(5) -0.005(4) -0.012(4) C12 0.051(5) 0.105(8) 0.053(5) -0.020(5) 0.010(4) 0.018(5) C13 0.075(6) 0.064(6) 0.125(9) -0.025(6) -0.035(7) 0.019(5) C2 0.064(5) 0.065(5) 0.095(7) 0.018(5) 0.015(5) 0.010(4) N1 0.162(8) 0.037(4) 0.071(5) -0.007(3) -0.012(5) -0.010(4) C1 0.097(7) 0.040(4) 0.093(7) 0.000(4) -0.017(5) -0.007(4) C14 0.073(5) 0.105(7) 0.072(6) 0.030(5) -0.013(4) -0.009(5) C15 0.071(5) 0.116(7) 0.064(5) 0.020(5) -0.005(4) -0.012(5) C3 0.061(3) 0.045(3) 0.047(3) 0.004(2) 0.001(3) -0.006(3) C4 0.061(3) 0.047(3) 0.047(3) 0.005(2) -0.004(3) -0.009(3) C5 0.061(3) 0.048(3) 0.055(3) 0.009(3) 0.002(3) -0.005(3) C6 0.065(3) 0.050(3) 0.059(3) -0.002(2) 0.009(3) -0.008(3) C8 0.062(3) 0.062(3) 0.045(3) 0.003(3) 0.000(3) -0.002(3) C7 0.065(3) 0.061(3) 0.050(3) -0.009(3) 0.003(3) -0.010(3) C10 0.098(9) 0.103(10) 0.243(16) 0.007(10) 0.013(10) -0.007(8) N2 0.112(6) 0.059(4) 0.105(6) 0.002(4) 0.005(5) -0.013(4) C9 0.074(6) 0.114(9) 0.153(10) 0.042(8) 0.019(7) -0.002(6) Hg1 0.0568(2) 0.0545(2) 0.0826(3) 0.00198(17) -0.00053(16) -0.00036(15) Br3 0.0582(5) 0.0824(6) 0.0919(7) 0.0012(5) 0.0122(5) -0.0126(4) Br1 0.0578(5) 0.0818(6) 0.1003(7) 0.0100(5) -0.0072(5) 0.0208(4) Br4 0.1295(8) 0.0469(5) 0.0739(6) -0.0116(4) -0.0025(6) -0.0104(5) Br2 0.1458(9) 0.0545(5) 0.0760(6) -0.0168(5) 0.0041(6) -0.0024(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 C16 C15 1.304(11) . ? C16 C11 1.425(8) . ? C16 H16 0.9300 . ? C11 C12 1.369(11) . ? C11 C10 1.488(8) . ? C12 C13 1.377(12) . ? C12 H12 0.9300 . ? C13 C14 1.328(13) . ? C13 H13 0.9300 . ? C2 C1 1.493(7) . ? C2 C3 1.522(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N1 C1 1.544(9) . ? N1 H1E 0.8900 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C14 C15 1.332(12) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C3 C8 1.378(9) . ? C3 C4 1.394(9) . ? C4 C5 1.400(9) . ? C4 H4 0.9300 . ? C5 C6 1.356(10) . ? C5 H5 0.9300 . ? C6 C7 1.335(10) . ? C6 H6 0.9300 . ? C8 C7 1.385(9) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C10 C9 1.417(8) . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? N2 C9 1.468(10) . ? N2 H2C 0.8900 . ? N2 H2E 0.8900 . ? N2 H2D 0.8900 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? Hg1 Br2 2.5665(11) . ? Hg1 Br4 2.5679(10) . ? Hg1 Br3 2.5805(11) . ? Hg1 Br1 2.6109(11) . ? 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 C15 C16 C11 119.4(9) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C12 C11 C16 116.6(7) . . ? C12 C11 C10 123.2(9) . . ? C16 C11 C10 119.7(9) . . ? C11 C12 C13 121.0(8) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 119.5(9) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C1 C2 C3 109.2(6) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C1 N1 H1E 109.5 . . ? C1 N1 H1C 109.5 . . ? H1E N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C2 C1 N1 107.0(6) . . ? C2 C1 H1A 110.3 . . ? N1 C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? N1 C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? C13 C14 C15 120.3(10) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 123.2(10) . . ? C16 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C8 C3 C4 118.1(6) . . ? C8 C3 C2 120.7(7) . . ? C4 C3 C2 121.1(6) . . ? C3 C4 C5 120.2(7) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.6(7) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 120.6(7) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C3 C8 C7 120.1(7) . . ? C3 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C6 C7 C8 121.4(7) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C10 C11 117.0(9) . . ? C9 C10 H10B 108.0 . . ? C11 C10 H10B 108.0 . . ? C9 C10 H10A 108.0 . . ? C11 C10 H10A 108.0 . . ? H10B C10 H10A 107.3 . . ? C9 N2 H2C 109.5 . . ? C9 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? C9 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? H2E N2 H2D 109.5 . . ? C10 C9 N2 114.5(8) . . ? C10 C9 H9B 108.6 . . ? N2 C9 H9B 108.6 . . ? C10 C9 H9A 108.6 . . ? N2 C9 H9A 108.6 . . ? H9B C9 H9A 107.6 . . ? Br2 Hg1 Br4 110.16(3) . . ? Br2 Hg1 Br3 113.25(4) . . ? Br4 Hg1 Br3 111.78(3) . . ? Br2 Hg1 Br1 111.63(4) . . ? Br4 Hg1 Br1 103.67(3) . . ? Br3 Hg1 Br1 105.88(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C16 C11 C12 0.2(12) . . . . ? C15 C16 C11 C10 172.4(9) . . . . ? C16 C11 C12 C13 1.1(12) . . . . ? C10 C11 C12 C13 -170.7(9) . . . . ? C11 C12 C13 C14 -0.1(13) . . . . ? C3 C2 C1 N1 175.7(6) . . . . ? C12 C13 C14 C15 -2.2(14) . . . . ? C11 C16 C15 C14 -2.6(14) . . . . ? C13 C14 C15 C16 3.7(15) . . . . ? C1 C2 C3 C8 -125.3(8) . . . . ? C1 C2 C3 C4 58.5(9) . . . . ? C8 C3 C4 C5 -0.9(10) . . . . ? C2 C3 C4 C5 175.5(6) . . . . ? C3 C4 C5 C6 0.0(10) . . . . ? C4 C5 C6 C7 1.0(11) . . . . ? C4 C3 C8 C7 0.9(10) . . . . ? C2 C3 C8 C7 -175.4(6) . . . . ? C5 C6 C7 C8 -1.0(11) . . . . ? C3 C8 C7 C6 0.0(11) . . . . ? C12 C11 C10 C9 -114.2(13) . . . . ? C16 C11 C10 C9 74.1(15) . . . . ? C11 C10 C9 N2 176.8(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C Br1 0.89 2.64 3.517(8) 170.9 3_566 N1 H1D Br4 0.89 2.69 3.438(7) 142.4 . N1 H1E Br3 0.89 3.00 3.474(7) 115.0 3_666 N2 H2E Br1 0.89 3.04 3.602(7) 122.8 3_566 N2 H2D Br1 0.89 2.61 3.486(8) 166.6 1_556 N2 H2C Br3 0.89 2.73 3.505(7) 146.8 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.502 _refine_diff_density_min -1.551 _refine_diff_density_rms 0.169 data_HgI(9) _database_code_depnum_ccdc_archive 'CCDC 791571' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Hg I4' _chemical_formula_sum 'C16 H24 Hg I4 N2' _chemical_formula_weight 952.56 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 P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8319(16) _cell_length_b 8.3960(12) _cell_length_c 13.5792(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.660(3) _cell_angle_gamma 90.00 _cell_volume 1220.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2684 _cell_measurement_theta_min 2.3154 _cell_measurement_theta_max 31.5806 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 11.362 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1076 _exptl_absorpt_correction_T_max 0.5103 _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _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 '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 10815 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5583 _reflns_number_gt 4125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0111(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.396(9) _refine_ls_number_reflns 5583 _refine_ls_number_parameters 268 _refine_ls_number_restraints 385 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.002 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 C3 C 0.0767(8) 0.2260(11) 0.4350(5) 0.060(2) Uani 1 1 d DU . . C8 C 0.0077(10) 0.1858(14) 0.5094(6) 0.073(3) Uani 1 1 d DU . . H8 H -0.0688 0.1345 0.4935 0.088 Uiso 1 1 calc R . . C7 C 0.0533(11) 0.2223(15) 0.6078(6) 0.093(3) Uani 1 1 d DU . . H7 H 0.0097 0.1897 0.6582 0.111 Uiso 1 1 calc R . . C6 C 0.1632(11) 0.3071(17) 0.6312(6) 0.093(3) Uani 1 1 d DU . . H6 H 0.1901 0.3396 0.6964 0.112 Uiso 1 1 calc R . . C5 C 0.2327(10) 0.3430(15) 0.5569(7) 0.096(3) Uani 1 1 d DU . . H5 H 0.3098 0.3925 0.5733 0.115 Uiso 1 1 calc R . . C4 C 0.1892(8) 0.3065(17) 0.4578(6) 0.076(3) Uani 1 1 d DU . . H4 H 0.2347 0.3356 0.4077 0.092 Uiso 1 1 calc R . . C2 C 0.0294(11) 0.1831(12) 0.3258(6) 0.068(3) Uani 1 1 d DU . . H2A H 0.0965 0.1353 0.2960 0.081 Uiso 1 1 calc R . . H2B H -0.0379 0.1061 0.3227 0.081 Uiso 1 1 calc R . . C1 C -0.0154(11) 0.3267(12) 0.2704(6) 0.073(3) Uani 1 1 d DU . . H1A H 0.0464 0.4104 0.2844 0.088 Uiso 1 1 calc R . . H1B H -0.0918 0.3628 0.2924 0.088 Uiso 1 1 calc R . . N1 N -0.0395(8) 0.2963(19) 0.1605(5) 0.086(3) Uani 1 1 d DU . . H1C H -0.0682 0.3848 0.1290 0.128 Uiso 1 1 calc R . . H1E H -0.0960 0.2191 0.1475 0.128 Uiso 1 1 calc R . . H1D H 0.0312 0.2669 0.1398 0.128 Uiso 1 1 calc R . . C11B C -0.3672(7) 0.2477(10) 0.5976(4) 0.060(2) Uani 0.877(9) 1 d PGDU A 1 C12B C -0.2837(7) 0.3491(11) 0.5606(5) 0.077(3) Uani 0.877(9) 1 d PGDU A 1 H12B H -0.2211 0.3993 0.6040 0.093 Uiso 0.877(9) 1 calc PR A 1 C13B C -0.2939(8) 0.3755(11) 0.4586(6) 0.083(3) Uani 0.877(9) 1 d PGDU A 1 H13B H -0.2380 0.4433 0.4338 0.099 Uiso 0.877(9) 1 calc PR A 1 C14B C -0.3875(9) 0.3005(12) 0.3937(4) 0.075(3) Uani 0.877(9) 1 d PGDU A 1 H14B H -0.3942 0.3182 0.3255 0.090 Uiso 0.877(9) 1 calc PR A 1 C15B C -0.4709(8) 0.1991(11) 0.4308(5) 0.078(3) Uani 0.877(9) 1 d PGDU A 1 H15B H -0.5336 0.1490 0.3873 0.094 Uiso 0.877(9) 1 calc PR A 1 C16B C -0.4608(7) 0.1727(10) 0.5327(5) 0.068(3) Uani 0.877(9) 1 d PGDU A 1 H16B H -0.5166 0.1049 0.5575 0.082 Uiso 0.877(9) 1 calc PR A 1 C10B C -0.3515(14) 0.2064(16) 0.7088(7) 0.087(3) Uani 0.877(9) 1 d PDU A 1 H1B1 H -0.3864 0.1017 0.7169 0.104 Uiso 0.877(9) 1 calc PR A 1 H1B2 H -0.2632 0.2027 0.7353 0.104 Uiso 0.877(9) 1 calc PR A 1 C9B C -0.4125(14) 0.3216(17) 0.7648(7) 0.077(4) Uani 0.877(9) 1 d PDU A 1 H9B1 H -0.5017 0.3173 0.7419 0.093 Uiso 0.877(9) 1 calc PR A 1 H9B2 H -0.3840 0.4273 0.7500 0.093 Uiso 0.877(9) 1 calc PR A 1 N2B N -0.3903(12) 0.299(2) 0.8750(6) 0.072(3) Uani 0.877(9) 1 d PDU A 1 H2CB H -0.4292 0.3750 0.9039 0.108 Uiso 0.877(9) 1 calc PR A 1 H2EB H -0.3088 0.3031 0.8970 0.108 Uiso 0.877(9) 1 calc PR A 1 H2DB H -0.4198 0.2040 0.8898 0.108 Uiso 0.877(9) 1 calc PR A 1 C11A C -0.313(6) 0.344(7) 0.600(3) 0.074(5) Uani 0.123(9) 1 d PGDU A 2 C12A C -0.290(6) 0.233(6) 0.529(4) 0.074(5) Uani 0.123(9) 1 d PGDU A 2 H12A H -0.2473 0.1398 0.5478 0.089 Uiso 0.123(9) 1 calc PR A 2 C13A C -0.332(6) 0.263(7) 0.428(3) 0.077(5) Uani 0.123(9) 1 d PGDU A 2 H13A H -0.3169 0.1889 0.3805 0.093 Uiso 0.123(9) 1 calc PR A 2 C14A C -0.396(7) 0.403(8) 0.400(3) 0.081(6) Uani 0.123(9) 1 d PGDU A 2 H14A H -0.4241 0.4222 0.3325 0.097 Uiso 0.123(9) 1 calc PR A 2 C15A C -0.419(6) 0.513(7) 0.471(4) 0.079(8) Uani 0.123(9) 1 d PGDU A 2 H15A H -0.4618 0.6064 0.4518 0.095 Uiso 0.123(9) 1 calc PR A 2 C16A C -0.377(6) 0.483(6) 0.571(4) 0.079(6) Uani 0.123(9) 1 d PGDU A 2 H16A H -0.3922 0.5573 0.6191 0.095 Uiso 0.123(9) 1 calc PR A 2 C10A C -0.287(5) 0.302(11) 0.711(3) 0.082(5) Uani 0.123(9) 1 d PDU A 2 H1A1 H -0.2356 0.2076 0.7209 0.099 Uiso 0.123(9) 1 calc PR A 2 H1A2 H -0.2423 0.3889 0.7477 0.099 Uiso 0.123(9) 1 calc PR A 2 C9A C -0.403(7) 0.27(2) 0.751(5) 0.080(6) Uani 0.123(9) 1 d PDU A 2 H9A1 H -0.4511 0.1928 0.7110 0.096 Uiso 0.123(9) 1 calc PR A 2 H9A2 H -0.4525 0.3711 0.7448 0.096 Uiso 0.123(9) 1 calc PR A 2 N2A N -0.383(10) 0.222(14) 0.857(4) 0.083(11) Uani 0.123(9) 1 d PDU A 2 H2DA H -0.4563 0.2060 0.8776 0.125 Uiso 0.123(9) 1 calc PR A 2 H2CA H -0.3414 0.2979 0.8948 0.125 Uiso 0.123(9) 1 calc PR A 2 H2EA H -0.3387 0.1326 0.8634 0.125 Uiso 0.123(9) 1 calc PR A 2 I4 I 0.29447(5) 0.26897(18) 0.16107(4) 0.0745(2) Uani 1 1 d . . . I1 I 0.32905(9) 0.55473(7) -0.11529(7) 0.0642(3) Uani 1 1 d . . . I3 I 0.33577(10) 0.02141(7) -0.12453(8) 0.0663(3) Uani 1 1 d . . . I2 I -0.02965(6) 0.2694(2) -0.10046(5) 0.0949(3) Uani 1 1 d . . . Hg1 Hg 0.22959(3) 0.28215(9) -0.04403(2) 0.05856(12) 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 C3 0.068(5) 0.066(5) 0.044(3) -0.001(3) 0.001(3) 0.001(4) C8 0.096(6) 0.078(7) 0.048(4) 0.000(4) 0.017(4) -0.004(5) C7 0.129(8) 0.100(8) 0.048(4) 0.002(5) 0.012(5) 0.021(6) C6 0.139(8) 0.076(9) 0.052(4) -0.006(6) -0.028(4) 0.028(6) C5 0.093(7) 0.095(8) 0.086(5) -0.011(6) -0.033(5) 0.002(6) C4 0.062(4) 0.094(8) 0.069(4) -0.002(6) -0.002(4) 0.000(5) C2 0.086(7) 0.073(6) 0.043(3) -0.002(4) 0.004(4) -0.006(5) C1 0.078(6) 0.093(9) 0.046(4) 0.005(4) 0.001(5) 0.015(6) N1 0.075(5) 0.136(8) 0.043(3) 0.006(6) 0.003(4) 0.044(8) C11B 0.057(5) 0.070(7) 0.052(3) -0.001(4) 0.002(3) 0.017(4) C12B 0.063(6) 0.091(7) 0.078(5) -0.018(5) 0.010(5) -0.010(4) C13B 0.079(6) 0.084(7) 0.091(6) 0.005(5) 0.031(5) -0.006(5) C14B 0.100(7) 0.068(7) 0.057(5) 0.015(6) 0.010(4) 0.018(6) C15B 0.091(7) 0.076(7) 0.063(4) -0.012(5) -0.007(5) -0.007(5) C16B 0.069(6) 0.068(7) 0.066(5) 0.000(5) 0.008(5) -0.008(5) C10B 0.103(8) 0.101(8) 0.055(4) 0.004(4) 0.006(5) 0.042(6) C9B 0.101(7) 0.084(10) 0.047(4) 0.005(5) 0.012(5) 0.020(6) N2B 0.074(5) 0.095(10) 0.045(4) 0.012(6) 0.005(4) 0.011(8) C11A 0.070(10) 0.086(10) 0.067(7) 0.001(7) 0.011(8) 0.005(9) C12A 0.070(10) 0.085(9) 0.067(7) -0.002(8) 0.011(9) -0.001(9) C13A 0.084(10) 0.080(10) 0.068(7) 0.000(9) 0.011(9) 0.002(9) C14A 0.087(12) 0.082(11) 0.075(9) 0.003(9) 0.015(11) 0.004(10) C15A 0.077(16) 0.087(14) 0.074(12) 0.003(11) 0.010(15) 0.010(13) C16A 0.073(13) 0.088(11) 0.075(10) 0.002(9) 0.006(12) 0.007(11) C10A 0.092(11) 0.090(12) 0.066(7) 0.000(9) 0.017(9) 0.023(11) C9A 0.094(11) 0.091(13) 0.057(10) 0.001(11) 0.017(9) 0.028(12) N2A 0.09(2) 0.09(2) 0.062(14) 0.01(2) 0.004(14) 0.00(2) I4 0.0560(3) 0.1172(7) 0.0482(3) -0.0026(6) 0.0008(2) 0.0101(6) I1 0.0777(6) 0.0429(5) 0.0700(6) 0.0029(4) 0.0041(5) -0.0060(4) I3 0.0759(7) 0.0435(5) 0.0781(7) -0.0096(4) 0.0069(5) 0.0013(4) I2 0.0487(3) 0.1829(9) 0.0515(3) -0.0177(9) 0.0024(3) -0.0010(8) Hg1 0.0639(2) 0.0546(2) 0.05655(19) 0.0000(3) 0.00690(14) -0.0014(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 C3 C8 1.387(7) . ? C3 C4 1.387(7) . ? C3 C2 1.537(10) . ? C8 C7 1.387(7) . ? C8 H8 0.9300 . ? C7 C6 1.382(17) . ? C7 H7 0.9300 . ? C6 C5 1.380(7) . ? C6 H6 0.9300 . ? C5 C4 1.391(7) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C2 C1 1.465(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C1 N1 1.497(10) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 H1C 0.8900 . ? N1 H1E 0.8900 . ? N1 H1D 0.8900 . ? C11B C12B 1.3900 . ? C11B C16B 1.3900 . ? C11B C10B 1.533(10) . ? C12B C13B 1.3900 . ? C12B H12B 0.9300 . ? C13B C14B 1.3900 . ? C13B H13B 0.9300 . ? C14B C15B 1.3900 . ? C14B H14B 0.9300 . ? C15B C16B 1.3900 . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C10B C9B 1.449(12) . ? C10B H1B1 0.9700 . ? C10B H1B2 0.9700 . ? C9B N2B 1.492(10) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? N2B H2CB 0.8900 . ? N2B H2EB 0.8900 . ? N2B H2DB 0.8900 . ? C11A C12A 1.3900 . ? C11A C16A 1.3900 . ? C11A C10A 1.535(11) . ? C12A C13A 1.4013 . ? C12A H12A 0.9300 . ? C13A C14A 1.3900 . ? C13A H13A 0.9300 . ? C14A C15A 1.3900 . ? C14A H14A 0.9300 . ? C15A C16A 1.3900 . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C10A C9A 1.457(14) . ? C10A H1A1 0.9700 . ? C10A H1A2 0.9700 . ? C9A N2A 1.495(12) . ? C9A H9A1 0.9500 . ? C9A H9A2 1.000 . ? N2A H2DA 0.8900 . ? N2A H2CA 0.8900 . ? N2A H2EA 0.8900 . ? I4 Hg1 2.7701(7) . ? I1 Hg1 2.7656(10) . ? I3 Hg1 2.7729(10) . ? I2 Hg1 2.7992(8) . ? 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 C8 C3 C4 120.5(6) . . ? C8 C3 C2 120.5(7) . . ? C4 C3 C2 118.9(7) . . ? C7 C8 C3 119.7(7) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? C6 C7 C8 120.3(8) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C5 C6 C7 119.3(8) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C5 C4 121.1(8) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C3 C4 C5 118.8(7) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C1 C2 C3 109.8(8) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C1 N1 111.5(9) . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? N1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C1 N1 H1C 109.5 . . ? C1 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? C1 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? C12B C11B C16B 120.0 . . ? C12B C11B C10B 120.9(7) . . ? C16B C11B C10B 119.0(7) . . ? C11B C12B C13B 120.0 . . ? C11B C12B H12B 120.0 . . ? C13B C12B H12B 120.0 . . ? C14B C13B C12B 120.0 . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? C15B C14B C13B 120.0 . . ? C15B C14B H14B 120.0 . . ? C13B C14B H14B 120.0 . . ? C14B C15B C16B 120.0 . . ? C14B C15B H15B 120.0 . . ? C16B C15B H15B 120.0 . . ? C15B C16B C11B 120.0 . . ? C15B C16B H16B 120.0 . . ? C11B C16B H16B 120.0 . . ? C9B C10B C11B 111.9(8) . . ? C9B C10B H1B1 109.2 . . ? C11B C10B H1B1 109.2 . . ? C9B C10B H1B2 109.2 . . ? C11B C10B H1B2 109.2 . . ? H1B1 C10B H1B2 107.9 . . ? C10B C9B N2B 115.0(10) . . ? C10B C9B H9B1 108.5 . . ? N2B C9B H9B1 108.5 . . ? C10B C9B H9B2 108.5 . . ? N2B C9B H9B2 108.5 . . ? H9B1 C9B H9B2 107.5 . . ? C9B N2B H2CB 109.5 . . ? C9B N2B H2EB 109.5 . . ? H2CB N2B H2EB 109.5 . . ? C9B N2B H2DB 109.5 . . ? H2CB N2B H2DB 109.5 . . ? H2EB N2B H2DB 109.5 . . ? C12A C11A C16A 120.0 . . ? C12A C11A C10A 120.8(11) . . ? C16A C11A C10A 118.4(11) . . ? C13A C12A C11A 120.0 . . ? C13A C12A H12A 120.0 . . ? C11A C12A H12A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? C15A C14A C13A 120.0 . . ? C15A C14A H14A 120.0 . . ? C13A C14A H14A 120.0 . . ? C14A C15A C16A 120.0 . . ? C14A C15A H15A 120.0 . . ? C16A C15A H15A 120.0 . . ? C15A C16A C11A 120.0 . . ? C15A C16A H16A 120.0 . . ? C11A C16A H16A 120.0 . . ? C9A C10A C11A 111.3(14) . . ? C9A C10A H1A1 108.0 . . ? C11A C10A H1A1 109.4 . . ? C9A C10A H1A2 109.4 . . ? C11A C10A H1A2 109.4 . . ? H1A1 C10A H1A2 108.0 . . ? C10A C9A N2A 113.1(16) . . ? C10A C9A H9A1 110.0 . . ? N2A C9A H9A1 111.0 . . ? C10A C9A H9A2 107.0 . . ? N2A C9A H9A2 108.0 . . ? H9A1 C9A H9A2 107.8 . . ? C9A N2A H2DA 109.4 . . ? C9A N2A H2CA 111.0 . . ? H2DA N2A H2CA 109.5 . . ? C9A N2A H2EA 109.6 . . ? H2DA N2A H2EA 109.5 . . ? H2CA N2A H2EA 109.5 . . ? I1 Hg1 I4 109.37(4) . . ? I1 Hg1 I3 107.99(2) . . ? I4 Hg1 I3 107.90(4) . . ? I1 Hg1 I2 111.31(4) . . ? I4 Hg1 I2 111.46(2) . . ? I3 Hg1 I2 108.69(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 C4 C3 C8 C7 -1.8(18) . . . . ? C2 C3 C8 C7 178.5(10) . . . . ? C3 C8 C7 C6 4.0(19) . . . . ? C8 C7 C6 C5 -6(2) . . . . ? C7 C6 C5 C4 5(2) . . . . ? C8 C3 C4 C5 1.4(19) . . . . ? C2 C3 C4 C5 -179.0(11) . . . . ? C6 C5 C4 C3 -3(2) . . . . ? C8 C3 C2 C1 106.5(12) . . . . ? C4 C3 C2 C1 -73.2(13) . . . . ? C3 C2 C1 N1 169.2(8) . . . . ? C16B C11B C12B C13B 0.0 . . . . ? C10B C11B C12B C13B 175.1(8) . . . . ? C11B C12B C13B C14B 0.0 . . . . ? C12B C13B C14B C15B 0.0 . . . . ? C13B C14B C15B C16B 0.0 . . . . ? C14B C15B C16B C11B 0.0 . . . . ? C12B C11B C16B C15B 0.0 . . . . ? C10B C11B C16B C15B -175.2(8) . . . . ? C12B C11B C10B C9B 87.3(14) . . . . ? C16B C11B C10B C9B -97.6(13) . . . . ? C11B C10B C9B N2B -174.1(11) . . . . ? C16A C11A C12A C13A 0.0 . . . . ? C10A C11A C12A C13A 170(4) . . . . ? C11A C12A C13A C14A 0.0 . . . . ? C12A C13A C14A C15A 0.0 . . . . ? C13A C14A C15A C16A 0.0 . . . . ? C14A C15A C16A C11A 0.0 . . . . ? C12A C11A C16A C15A 0.0 . . . . ? C10A C11A C16A C15A -170(4) . . . . ? C12A C11A C10A C9A -106(9) . . . . ? C16A C11A C10A C9A 64(9) . . . . ? C11A C10A C9A N2A 176(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.858 _refine_diff_density_min -1.289 _refine_diff_density_rms 0.138 data_znclbri(10) _database_code_depnum_ccdc_archive 'CCDC 791572' #TrackingRef '2294_web_deposit_cif_file_0_MelanieRademeyer_1283335000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N), Br Cl2 I Zn' _chemical_formula_sum 'C16 H24 Br Cl2 I N2 Zn' _chemical_formula_weight 587.45 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' Cd Cd -0.8075 1.2024 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 7.6962(17) _cell_length_b 25.541(4) _cell_length_c 11.1314(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.782(16) _cell_angle_gamma 90.00 _cell_volume 2187.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 981 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 4.606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2066 _exptl_absorpt_correction_T_max 0.4594 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Excalibur2' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 18209 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5263 _reflns_number_gt 3764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_cell_refinement 'CrysAlis CCD 170 (Oxford Diffraction Ltd., 2003)' _computing_data_reduction 'CrysAlis RED 170 (Oxford Diffraction Ltd., 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al, 2002)' _computing_publication_material 'PLATON (Spek, 2000) and 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^)+(0.1520P)^2^+7.9293P] 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 5263 _refine_ls_number_parameters 208 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.1198 _refine_ls_R_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.3010 _refine_ls_wR_factor_gt 0.2772 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.141 _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 C16 C 0.3624(18) 0.7019(7) 0.6748(13) 0.091(4) Uani 1 1 d . . . H16 H 0.3940 0.6730 0.6297 0.109 Uiso 1 1 calc R . . C11 C 0.2700(16) 0.6951(4) 0.7807(11) 0.075(3) Uani 1 1 d DU . . C12 C 0.2264(16) 0.7385(6) 0.8440(11) 0.080(3) Uani 1 1 d . . . H12 H 0.1634 0.7351 0.9135 0.096 Uiso 1 1 calc R . . C13 C 0.274(2) 0.7862(6) 0.8068(16) 0.094(5) Uani 1 1 d . . . H13 H 0.2455 0.8154 0.8522 0.113 Uiso 1 1 calc R . . C2 C 0.1340(19) 0.3337(4) 0.528(2) 0.131(8) Uani 1 1 d D . . H2A H 0.0992 0.3468 0.4487 0.158 Uiso 1 1 calc R . . H2B H 0.0375 0.3390 0.5804 0.158 Uiso 1 1 calc R . . N1 N 0.2332(14) 0.4223(3) 0.5740(10) 0.075(3) Uani 1 1 d D . . H1E H 0.3274 0.4420 0.5869 0.113 Uiso 1 1 calc R . . H1C H 0.1583 0.4280 0.6319 0.113 Uiso 1 1 calc R . . H1D H 0.1836 0.4306 0.5032 0.113 Uiso 1 1 calc R . . C1 C 0.2854(18) 0.3642(5) 0.5738(17) 0.098(4) Uani 1 1 d D . . H1A H 0.3839 0.3589 0.5229 0.117 Uiso 1 1 calc R . . H1B H 0.3179 0.3529 0.6547 0.117 Uiso 1 1 calc R . . C14 C 0.3613(19) 0.7928(6) 0.7040(16) 0.094(4) Uani 1 1 d U . . H14 H 0.3911 0.8262 0.6788 0.113 Uiso 1 1 calc R . . C15 C 0.4052(17) 0.7508(7) 0.6389(12) 0.087(3) Uani 1 1 d U . . H15 H 0.4656 0.7553 0.5686 0.105 Uiso 1 1 calc R . . C3 C 0.1710(15) 0.2763(4) 0.5188(10) 0.068(2) Uani 1 1 d DU . . C4 C 0.2549(14) 0.2472(5) 0.6083(10) 0.065(2) Uani 1 1 d U . . H4 H 0.2995 0.2639 0.6767 0.078 Uiso 1 1 calc R . . C5 C 0.2732(15) 0.1936(5) 0.5973(11) 0.070(2) Uani 1 1 d U . . H5 H 0.3333 0.1749 0.6570 0.084 Uiso 1 1 calc R . . C6 C 0.2040(17) 0.1682(5) 0.5001(13) 0.080(3) Uani 1 1 d U . . H6 H 0.2132 0.1319 0.4951 0.096 Uiso 1 1 calc R . . C8 C 0.1075(15) 0.2494(5) 0.4197(10) 0.074(2) Uani 1 1 d U . . H8 H 0.0534 0.2678 0.3569 0.089 Uiso 1 1 calc R . . C7 C 0.1227(18) 0.1948(6) 0.4115(12) 0.081(3) Uani 1 1 d U . . H7 H 0.0764 0.1772 0.3448 0.098 Uiso 1 1 calc R . . C10 C 0.181(2) 0.6438(6) 0.802(2) 0.139(8) Uani 1 1 d DU . . H10B H 0.0764 0.6496 0.8461 0.167 Uiso 1 1 calc R . . H10A H 0.1483 0.6279 0.7253 0.167 Uiso 1 1 calc R . . N2 N 0.201(2) 0.5581(4) 0.8949(14) 0.117(5) Uani 1 1 d D . . H2C H 0.2763 0.5331 0.9162 0.176 Uiso 1 1 calc R . . H2E H 0.1412 0.5483 0.8289 0.176 Uiso 1 1 calc R . . H2D H 0.1279 0.5634 0.9542 0.176 Uiso 1 1 calc R . . C9 C 0.299(3) 0.6085(7) 0.870(2) 0.151(9) Uani 1 1 d DU . . H9B H 0.3361 0.6248 0.9453 0.181 Uiso 1 1 calc R . . H9A H 0.4009 0.6010 0.8242 0.181 Uiso 1 1 calc R . . Zn Zn 0.25832(16) 0.52180(5) 0.27071(12) 0.0617(4) Uani 1 1 d . . . Br1 Br 0.52036(19) 0.54864(7) 0.15974(14) 0.0907(5) Uani 1 1 d . . . Cl1 Cl 0.0168(4) 0.55640(12) 0.1674(3) 0.0770(8) Uani 1 1 d . . . Cl2 Cl 0.2288(4) 0.43063(9) 0.2680(2) 0.0660(7) Uani 1 1 d . . . I1 I 0.26748(11) 0.55772(3) 0.48904(7) 0.0723(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 C16 0.078(8) 0.110(11) 0.084(9) -0.033(8) 0.006(7) 0.010(7) C11 0.070(7) 0.085(7) 0.070(7) 0.010(6) 0.003(5) 0.000(5) C12 0.073(7) 0.115(11) 0.053(6) -0.012(6) 0.011(5) 0.010(7) C13 0.096(10) 0.074(9) 0.111(11) -0.019(8) -0.031(9) 0.023(7) C2 0.107(11) 0.051(7) 0.23(2) 0.012(10) -0.082(13) -0.012(7) N1 0.097(7) 0.048(5) 0.081(6) -0.008(4) 0.003(5) -0.005(4) C1 0.095(9) 0.061(7) 0.136(13) -0.010(8) -0.006(9) -0.008(7) C14 0.084(8) 0.085(8) 0.111(10) 0.025(6) -0.028(8) -0.007(6) C15 0.076(7) 0.123(10) 0.063(7) 0.014(6) -0.004(5) -0.023(7) C3 0.074(6) 0.065(5) 0.064(5) 0.006(4) 0.000(4) -0.003(4) C4 0.071(6) 0.066(4) 0.059(5) 0.004(4) 0.000(4) -0.008(4) C5 0.065(5) 0.066(4) 0.078(5) 0.012(4) 0.007(4) 0.000(4) C6 0.079(7) 0.066(5) 0.095(7) -0.007(4) 0.014(5) -0.009(5) C8 0.074(6) 0.090(5) 0.059(5) 0.004(4) 0.000(4) -0.004(5) C7 0.080(7) 0.091(5) 0.073(6) -0.017(5) 0.005(5) -0.018(6) C10 0.128(14) 0.124(14) 0.162(19) 0.049(13) -0.022(13) -0.040(11) N2 0.173(15) 0.068(7) 0.111(10) -0.005(6) 0.008(10) -0.036(8) C9 0.147(17) 0.114(14) 0.19(2) 0.062(15) 0.007(15) -0.007(13) Zn 0.0625(7) 0.0546(7) 0.0680(7) -0.0045(5) 0.0012(5) 0.0000(5) Br1 0.0807(9) 0.1038(11) 0.0882(10) -0.0049(7) 0.0114(7) -0.0064(7) Cl1 0.0633(15) 0.0826(19) 0.0841(19) 0.0077(14) -0.0149(13) 0.0148(13) Cl2 0.1002(19) 0.0331(10) 0.0643(14) -0.0082(9) -0.0036(13) -0.0119(10) I1 0.0869(6) 0.0552(5) 0.0751(5) -0.0141(3) 0.0065(4) 0.0004(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 C16 C15 1.36(2) . ? C16 C11 1.406(19) . ? C16 H16 0.9300 . ? C11 C12 1.362(18) . ? C11 C10 1.501(19) . ? C12 C13 1.34(2) . ? C12 H12 0.9300 . ? C13 C14 1.36(2) . ? C13 H13 0.9300 . ? C2 C1 1.48(2) . ? C2 C3 1.497(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? N1 C1 1.538(16) . ? N1 H1E 0.8900 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C14 C15 1.34(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C3 C8 1.376(16) . ? C3 C4 1.388(15) . ? C4 C5 1.381(17) . ? C4 H4 0.9300 . ? C5 C6 1.357(18) . ? C5 H5 0.9300 . ? C6 C7 1.34(2) . ? C6 H6 0.9300 . ? C8 C7 1.403(19) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C10 C9 1.47(3) . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? N2 C9 1.52(2) . ? N2 H2C 0.8900 . ? N2 H2E 0.8900 . ? N2 H2D 0.8900 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? Zn Cl1 2.329(3) . ? Zn Cl2 2.340(2) . ? Zn Br1 2.494(2) . ? Zn I1 2.5967(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 C16 C11 119.7(13) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C12 C11 C16 118.2(12) . . ? C12 C11 C10 120.7(15) . . ? C16 C11 C10 118.9(15) . . ? C13 C12 C11 120.5(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.2(14) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C1 C2 C3 112.8(10) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C1 N1 H1E 109.5 . . ? C1 N1 H1C 109.5 . . ? H1E N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1E N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C2 C1 N1 107.7(10) . . ? C2 C1 H1A 110.2 . . ? N1 C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? N1 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C15 C14 C13 119.8(14) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.6(13) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C8 C3 C4 117.0(10) . . ? C8 C3 C2 118.6(12) . . ? C4 C3 C2 124.3(11) . . ? C5 C4 C3 120.9(11) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 120.4(12) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.5(13) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C3 C8 C7 121.4(11) . . ? C3 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C6 C7 C8 119.7(12) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C10 C11 109.9(11) . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? H10B C10 H10A 108.2 . . ? C9 N2 H2C 109.5 . . ? C9 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? C9 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? H2E N2 H2D 109.5 . . ? C10 C9 N2 108.2(14) . . ? C10 C9 H9B 110.1 . . ? N2 C9 H9B 110.1 . . ? C10 C9 H9A 110.1 . . ? N2 C9 H9A 110.1 . . ? H9B C9 H9A 108.4 . . ? Cl1 Zn Cl2 107.19(12) . . ? Cl1 Zn Br1 107.23(11) . . ? Cl2 Zn Br1 110.31(10) . . ? Cl1 Zn I1 109.03(10) . . ? Cl2 Zn I1 111.32(8) . . ? Br1 Zn I1 111.57(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 C15 C16 C11 C12 0(2) . . . . ? C15 C16 C11 C10 163.2(13) . . . . ? C16 C11 C12 C13 -1.1(19) . . . . ? C10 C11 C12 C13 -164.1(13) . . . . ? C11 C12 C13 C14 2(2) . . . . ? C3 C2 C1 N1 177.9(15) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C13 C14 C15 C16 0(2) . . . . ? C11 C16 C15 C14 1(2) . . . . ? C1 C2 C3 C8 -139.1(16) . . . . ? C1 C2 C3 C4 46(2) . . . . ? C8 C3 C4 C5 0.0(17) . . . . ? C2 C3 C4 C5 175.2(13) . . . . ? C3 C4 C5 C6 -2.2(18) . . . . ? C4 C5 C6 C7 2.4(19) . . . . ? C4 C3 C8 C7 1.8(18) . . . . ? C2 C3 C8 C7 -173.6(14) . . . . ? C5 C6 C7 C8 -1(2) . . . . ? C3 C8 C7 C6 -2(2) . . . . ? C12 C11 C10 C9 -105(2) . . . . ? C16 C11 C10 C9 92(2) . . . . ? C11 C10 C9 N2 177.2(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1D I1 0.89 3.49 3.928(11) 113.4 3_566 N1 H1C Cl1 0.89 2.67 3.554(11) 169.7 3_566 N1 H1D Cl2 0.89 2.65 3.412(11) 143.9 . N1 H1E Br1 0.89 3.03 3.547(10) 119.0 3_666 N1 H1E I1 0.89 3.18 3.598(9) 111.1 . N2 H2E Cl1 0.89 2.94 3.430(12) 116.5 3_566 N2 H2D Cl1 0.89 2.55 3.387(17) 156.3 1_556 N2 H2C Br1 0.89 3.27 3.787(17) 119.0 1_556 N2 H2C Br1 0.89 2.76 3.533(16) 146.5 3_666 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.265 _refine_diff_density_min -0.927 _refine_diff_density_rms 0.179