# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Marcos D. Garcia' 'Javier Marti-Rujas' 'Pierangelo Metrangolo' 'Carlos Peinador' 'Tullio Pilati' 'Giuseppe Resnati' 'Giancarlo Terraneo' _publ_contact_author_name 'Giancarlo Terraneo' _publ_contact_author_email giancarlo.terraneo@chem.polimi.it data_mg05a_lt _database_code_depnum_ccdc_archive 'CCDC 794577' #TrackingRef 'MG05A_LT.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 I2 N2, 2+, 2(I3, 1-)' _chemical_formula_sum 'C24 H20 I8 N2' _chemical_formula_weight 1351.62 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0768(6) _cell_length_b 8.1099(6) _cell_length_c 15.1128(12) _cell_angle_alpha 76.138(11) _cell_angle_beta 82.477(10) _cell_angle_gamma 70.923(10) _cell_volume 794.54(11) _cell_formula_units_Z 1 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 7320 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 30.55 _exptl_crystal_description table _exptl_crystal_colour red-orange' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 7.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2975 _exptl_absorpt_correction_T_max 0.4330 _exptl_special_details ; Pleochroic crystals. Red/orange. Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12554 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 30.55 _reflns_number_total 4799 _reflns_number_gt 4007 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. H atoms were refined imposing soft restraints on C-H distances (same distance for two kind of bond: aromatic and aliphatic). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.5826P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4799 _refine_ls_number_parameters 184 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.137 _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 I1 I 0.58035(4) 0.18780(3) -0.111624(16) 0.04000(8) Uani 1 1 d . . . C1 C 0.8739(6) 0.3319(5) 0.3462(3) 0.0386(8) Uani 1 1 d D . . H1 H 0.798(6) 0.450(4) 0.328(3) 0.046 Uiso 1 1 d D . . C2 C 0.8740(6) 0.2305(5) 0.4339(3) 0.0375(8) Uani 1 1 d D . . H2 H 0.798(6) 0.281(6) 0.480(2) 0.045 Uiso 1 1 d D . . C3 C 0.9965(5) 0.0551(4) 0.4530(2) 0.0272(6) Uani 1 1 d . . . C4 C 1.1120(8) -0.0126(6) 0.3805(3) 0.0499(11) Uani 1 1 d D . . H4 H 1.180(7) -0.131(4) 0.382(4) 0.060 Uiso 1 1 d D . . C5 C 1.1048(8) 0.0934(6) 0.2946(3) 0.0497(11) Uani 1 1 d D . . H5 H 1.174(7) 0.059(7) 0.243(2) 0.060 Uiso 1 1 d D . . N1 N 0.9884(5) 0.2625(4) 0.2788(2) 0.0315(6) Uani 1 1 d . . . C6 C 0.9930(7) 0.3771(6) 0.1851(3) 0.0402(8) Uani 1 1 d D . . H6A H 1.124(5) 0.388(6) 0.166(3) 0.048 Uiso 1 1 d D . . H6B H 0.935(7) 0.504(5) 0.183(3) 0.048 Uiso 1 1 d D . . C7 C 0.9006(6) 0.3227(5) 0.1171(2) 0.0328(7) Uani 1 1 d . . . C8 C 1.0102(6) 0.2754(5) 0.0390(3) 0.0367(8) Uani 1 1 d D . . H8 H 1.141(4) 0.275(6) 0.027(3) 0.044 Uiso 1 1 d D . . C9 C 0.9215(6) 0.2348(5) -0.0262(3) 0.0377(8) Uani 1 1 d D . . H9 H 0.995(6) 0.212(6) -0.079(2) 0.045 Uiso 1 1 d D . . C10 C 0.7239(6) 0.2402(5) -0.0131(2) 0.0335(7) Uani 1 1 d . . . C11 C 0.6126(6) 0.2848(6) 0.0657(3) 0.0410(8) Uani 1 1 d D . . H11 H 0.477(4) 0.296(6) 0.074(3) 0.049 Uiso 1 1 d D . . C12 C 0.7038(6) 0.3241(6) 0.1307(3) 0.0386(8) Uani 1 1 d D . . H12 H 0.623(6) 0.361(6) 0.179(2) 0.046 Uiso 1 1 d D . . I2 I 0.68496(4) 0.51987(4) 0.654784(17) 0.03936(7) Uani 1 1 d . . . I3 I 0.68296(4) 0.71785(3) 0.468008(16) 0.03485(7) Uani 1 1 d . . . I4 I 0.69580(5) 0.89401(4) 0.274040(19) 0.05112(9) 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 I1 0.05147(16) 0.04225(14) 0.02439(12) -0.00911(9) -0.00501(10) -0.00925(11) C1 0.042(2) 0.0329(17) 0.0356(19) -0.0061(14) 0.0028(16) -0.0069(15) C2 0.0375(19) 0.0359(18) 0.0317(18) -0.0081(14) 0.0063(15) -0.0040(15) C3 0.0301(16) 0.0311(15) 0.0235(15) -0.0095(12) -0.0047(12) -0.0097(12) C4 0.070(3) 0.038(2) 0.0254(18) -0.0124(15) -0.0046(18) 0.0096(19) C5 0.066(3) 0.045(2) 0.0256(18) -0.0136(16) 0.0011(18) 0.002(2) N1 0.0383(16) 0.0340(14) 0.0255(14) -0.0075(11) -0.0040(12) -0.0138(12) C6 0.054(2) 0.0422(19) 0.0286(18) -0.0057(15) 0.0008(16) -0.0231(18) C7 0.0417(19) 0.0310(16) 0.0243(16) -0.0017(12) -0.0019(14) -0.0122(14) C8 0.0379(19) 0.0411(19) 0.0305(18) -0.0086(14) 0.0043(15) -0.0132(16) C9 0.047(2) 0.0383(18) 0.0262(17) -0.0087(14) 0.0052(15) -0.0115(16) C10 0.0444(19) 0.0335(16) 0.0197(15) -0.0040(12) -0.0035(14) -0.0085(15) C11 0.0358(19) 0.056(2) 0.0289(18) -0.0139(16) 0.0011(15) -0.0085(17) C12 0.043(2) 0.048(2) 0.0236(16) -0.0118(15) 0.0026(14) -0.0107(17) I2 0.04584(15) 0.04597(14) 0.02981(13) -0.00993(10) -0.00032(10) -0.01813(11) I3 0.03846(13) 0.03932(13) 0.03202(13) -0.01162(10) -0.00355(10) -0.01542(10) I4 0.06026(19) 0.06294(18) 0.03273(14) 0.00017(12) -0.01082(12) -0.02651(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C10 2.101(4) . ? C1 N1 1.331(5) . ? C1 C2 1.382(5) . ? C1 H1 0.93(2) . ? C2 C3 1.386(5) . ? C2 H2 0.91(2) . ? C3 C4 1.389(5) . ? C3 C3 1.484(7) 2_756 ? C4 C5 1.371(6) . ? C4 H4 0.92(2) . ? C5 N1 1.332(5) . ? C5 H5 0.92(2) . ? N1 C6 1.499(5) . ? C6 C7 1.502(5) . ? C6 H6A 0.96(3) . ? C6 H6B 0.97(3) . ? C7 C12 1.378(6) . ? C7 C8 1.387(5) . ? C8 C9 1.388(6) . ? C8 H8 0.92(2) . ? C9 C10 1.374(6) . ? C9 H9 0.91(2) . ? C10 C11 1.393(5) . ? C11 C12 1.391(6) . ? C11 H11 0.93(2) . ? C12 H12 0.92(2) . ? I2 I3 2.8930(5) . ? I3 I4 2.9412(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.8(3) . . ? N1 C1 H1 114(3) . . ? C2 C1 H1 125(3) . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 120(3) . . ? C3 C2 H2 120(3) . . ? C2 C3 C4 117.2(3) . . ? C2 C3 C3 121.2(4) . 2_756 ? C4 C3 C3 121.7(4) . 2_756 ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 114(3) . . ? C3 C4 H4 125(3) . . ? N1 C5 C4 121.1(4) . . ? N1 C5 H5 113(3) . . ? C4 C5 H5 126(3) . . ? C1 N1 C5 120.5(3) . . ? C1 N1 C6 120.0(3) . . ? C5 N1 C6 119.5(3) . . ? N1 C6 C7 112.4(3) . . ? N1 C6 H6A 112(3) . . ? C7 C6 H6A 114(3) . . ? N1 C6 H6B 114(3) . . ? C7 C6 H6B 110(3) . . ? H6A C6 H6B 92(4) . . ? C12 C7 C8 119.3(4) . . ? C12 C7 C6 120.1(3) . . ? C8 C7 C6 120.6(4) . . ? C7 C8 C9 120.6(4) . . ? C7 C8 H8 122(3) . . ? C9 C8 H8 117(3) . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 122(3) . . ? C8 C9 H9 118(3) . . ? C9 C10 C11 120.4(4) . . ? C9 C10 I1 121.2(3) . . ? C11 C10 I1 118.4(3) . . ? C12 C11 C10 119.2(4) . . ? C12 C11 H11 119(3) . . ? C10 C11 H11 121(3) . . ? C7 C12 C11 120.8(4) . . ? C7 C12 H12 122(3) . . ? C11 C12 H12 117(3) . . ? I2 I3 I4 175.792(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.1(6) . . . . ? C1 C2 C3 C4 -1.7(6) . . . . ? C1 C2 C3 C3 178.3(4) . . . 2_756 ? C2 C3 C4 C5 1.0(7) . . . . ? C3 C3 C4 C5 -178.9(5) 2_756 . . . ? C3 C4 C5 N1 0.2(8) . . . . ? C2 C1 N1 C5 0.2(6) . . . . ? C2 C1 N1 C6 -177.3(4) . . . . ? C4 C5 N1 C1 -0.9(7) . . . . ? C4 C5 N1 C6 176.7(5) . . . . ? C1 N1 C6 C7 -112.5(4) . . . . ? C5 N1 C6 C7 70.0(5) . . . . ? N1 C6 C7 C12 59.4(5) . . . . ? N1 C6 C7 C8 -122.4(4) . . . . ? C12 C7 C8 C9 1.9(6) . . . . ? C6 C7 C8 C9 -176.4(4) . . . . ? C7 C8 C9 C10 -0.5(6) . . . . ? C8 C9 C10 C11 -0.5(6) . . . . ? C8 C9 C10 I1 178.1(3) . . . . ? C9 C10 C11 C12 0.1(6) . . . . ? I1 C10 C11 C12 -178.5(3) . . . . ? C8 C7 C12 C11 -2.3(6) . . . . ? C6 C7 C12 C11 176.0(4) . . . . ? C10 C11 C12 C7 1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.643 _refine_diff_density_min -1.195 _refine_diff_density_rms 0.170 # Attachment 'MG11.CIF' data_mg11 _database_code_depnum_ccdc_archive 'CCDC 794578' #TrackingRef 'MG11.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H14 F8 N2, 2+, 2(I3, 1-)' _chemical_formula_sum 'C24 H14 F8 I6 N2' _chemical_formula_weight 1243.77 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6088(5) _cell_length_b 7.6970(5) _cell_length_c 14.1513(9) _cell_angle_alpha 99.020(3) _cell_angle_beta 93.382(3) _cell_angle_gamma 105.947(3) _cell_volume 782.46(9) _cell_formula_units_Z 1 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4970 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 24.11 _exptl_crystal_description lamina _exptl_crystal_colour red _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 6.021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.5627 _exptl_absorpt_correction_T_max 0.7457 _exptl_special_details ; Very small and thin crystal, often curved. ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 17264 _diffrn_reflns_av_R_equivalents 0.0946 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3776 _reflns_number_gt 1934 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 'w=1/[\s^2^(Fo^2^)+(0.0333P)^2] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3776 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.866 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I2 I 0.31581(4) 0.69843(5) 0.02434(3) 0.05758(12) Uani 1 1 d . . . I1 I 0.41453(5) 0.91083(5) 0.21833(3) 0.07405(15) Uani 1 1 d . . . I3 I 0.21751(6) 0.47090(6) -0.16626(3) 0.07716(15) Uani 1 1 d . . . N1 N 0.1392(6) 0.2920(5) 0.2236(3) 0.0511(10) Uani 1 1 d . . . C1 C 0.2459(7) 0.3096(7) 0.1525(4) 0.0603(14) Uani 1 1 d . . . H1 H 0.3579 0.4009 0.1627 0.072 Uiso 1 1 calc R . . C2 C 0.1953(6) 0.1981(7) 0.0663(4) 0.0587(14) Uani 1 1 d . . . H2 H 0.2728 0.2141 0.0179 0.070 Uiso 1 1 calc R . . C3 C 0.0304(6) 0.0601(6) 0.0481(3) 0.0387(10) Uani 1 1 d . . . C4 C -0.0773(7) 0.0456(7) 0.1224(4) 0.0624(14) Uani 1 1 d . . . H4 H -0.1905 -0.0438 0.1132 0.075 Uiso 1 1 calc R . . C5 C -0.0217(7) 0.1608(7) 0.2106(4) 0.0669(15) Uani 1 1 d . . . H5 H -0.0956 0.1472 0.2606 0.080 Uiso 1 1 calc R . . C6 C 0.1902(7) 0.4245(6) 0.3166(4) 0.0607(14) Uani 1 1 d . . . H6A H 0.3026 0.5188 0.3124 0.073 Uiso 1 1 calc R . . H6B H 0.0941 0.4839 0.3272 0.073 Uiso 1 1 calc R . . C7 C 0.2172(7) 0.3361(6) 0.3997(3) 0.0491(12) Uani 1 1 d . . . C8 C 0.3834(7) 0.3030(6) 0.4229(4) 0.0514(12) Uani 1 1 d . . . C9 C 0.4123(7) 0.2312(6) 0.5032(4) 0.0530(13) Uani 1 1 d . . . C10 C 0.2797(7) 0.1883(7) 0.5641(4) 0.0610(14) Uani 1 1 d . . . H10 H 0.3006 0.1397 0.6184 0.073 Uiso 1 1 calc R . . C11 C 0.1139(7) 0.2205(7) 0.5414(4) 0.0600(14) Uani 1 1 d . . . C12 C 0.0842(7) 0.2907(6) 0.4610(4) 0.0555(14) Uani 1 1 d . . . F1 F 0.5209(4) 0.3494(4) 0.3684(2) 0.0717(8) Uani 1 1 d . . . F2 F 0.5771(4) 0.2063(4) 0.5244(2) 0.0821(10) Uani 1 1 d . . . F3 F -0.0200(4) 0.1824(5) 0.5992(2) 0.0913(11) Uani 1 1 d . . . F4 F -0.0798(4) 0.3175(4) 0.4408(2) 0.0837(10) 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 I2 0.0522(2) 0.0602(2) 0.0674(3) 0.01953(18) 0.00544(16) 0.02358(17) I1 0.0832(3) 0.0758(3) 0.0681(3) 0.0130(2) -0.0027(2) 0.0332(2) I3 0.0794(3) 0.0782(3) 0.0756(3) 0.0069(2) -0.0011(2) 0.0312(2) N1 0.059(3) 0.035(2) 0.054(3) 0.008(2) -0.008(2) 0.008(2) C1 0.051(3) 0.061(3) 0.054(4) 0.012(3) -0.008(3) -0.007(3) C2 0.039(3) 0.073(4) 0.051(4) 0.014(3) 0.000(2) -0.007(3) C3 0.039(3) 0.039(3) 0.043(3) 0.015(2) 0.004(2) 0.015(2) C4 0.051(3) 0.055(3) 0.065(4) 0.003(3) 0.006(3) -0.008(2) C5 0.071(4) 0.063(4) 0.054(4) 0.000(3) 0.016(3) 0.003(3) C6 0.077(4) 0.041(3) 0.054(4) 0.000(3) -0.006(3) 0.009(3) C7 0.061(3) 0.040(3) 0.041(3) -0.001(2) -0.008(3) 0.013(2) C8 0.058(3) 0.041(3) 0.047(3) 0.002(2) 0.007(3) 0.004(2) C9 0.050(3) 0.044(3) 0.057(4) -0.006(2) -0.008(3) 0.009(2) C10 0.072(4) 0.054(3) 0.046(3) 0.008(3) -0.006(3) 0.003(3) C11 0.061(4) 0.059(3) 0.051(4) -0.004(3) 0.011(3) 0.009(3) C12 0.050(3) 0.052(3) 0.059(4) -0.006(3) -0.007(3) 0.016(3) F1 0.0639(19) 0.072(2) 0.071(2) 0.0070(17) 0.0182(17) 0.0066(16) F2 0.058(2) 0.091(2) 0.096(3) 0.0163(19) -0.0115(17) 0.0242(18) F3 0.075(2) 0.111(3) 0.072(2) 0.000(2) 0.0313(19) 0.004(2) F4 0.062(2) 0.093(2) 0.097(3) -0.001(2) -0.0002(18) 0.0357(18) _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 I2 I1 2.9065(6) . ? I2 I3 2.9090(6) . ? N1 C1 1.329(6) . ? N1 C5 1.338(6) . ? N1 C6 1.492(6) . ? C1 C2 1.345(7) . ? C1 H1 0.9300 . ? C2 C3 1.383(6) . ? C2 H2 0.9300 . ? C3 C4 1.371(7) . ? C3 C3 1.489(9) 2 ? C4 C5 1.381(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.479(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.379(7) . ? C7 C8 1.388(6) . ? C8 F1 1.339(5) . ? C8 C9 1.371(7) . ? C9 F2 1.343(5) . ? C9 C10 1.371(7) . ? C10 C11 1.380(7) . ? C10 H10 0.9300 . ? C11 F3 1.343(6) . ? C11 C12 1.367(7) . ? C12 F4 1.342(5) . ? 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 I1 I2 I3 177.369(15) . . ? C1 N1 C5 120.2(4) . . ? C1 N1 C6 121.0(4) . . ? C5 N1 C6 118.7(5) . . ? N1 C1 C2 121.3(5) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C1 C2 C3 121.3(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 116.1(4) . . ? C4 C3 C3 121.9(5) . 2 ? C2 C3 C3 121.9(5) . 2 ? C3 C4 C5 121.5(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? N1 C5 C4 119.5(5) . . ? N1 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 N1 112.9(4) . . ? C7 C6 H6A 109.0 . . ? N1 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? N1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C12 C7 C8 116.3(4) . . ? C12 C7 C6 122.5(5) . . ? C8 C7 C6 121.1(5) . . ? F1 C8 C9 119.2(5) . . ? F1 C8 C7 119.5(5) . . ? C9 C8 C7 121.2(5) . . ? F2 C9 C10 118.8(5) . . ? F2 C9 C8 119.2(5) . . ? C10 C9 C8 122.0(5) . . ? C9 C10 C11 117.1(5) . . ? C9 C10 H10 121.4 . . ? C11 C10 H10 121.4 . . ? F3 C11 C12 119.5(5) . . ? F3 C11 C10 119.5(5) . . ? C12 C11 C10 120.9(5) . . ? F4 C12 C11 119.1(5) . . ? F4 C12 C7 118.5(5) . . ? C11 C12 C7 122.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.5(7) . . . . ? C6 N1 C1 C2 -175.6(4) . . . . ? N1 C1 C2 C3 -0.2(8) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C1 C2 C3 C3 177.8(5) . . . 2 ? C2 C3 C4 C5 -1.1(7) . . . . ? C3 C3 C4 C5 -178.3(5) 2 . . . ? C1 N1 C5 C4 -1.0(7) . . . . ? C6 N1 C5 C4 175.2(5) . . . . ? C3 C4 C5 N1 1.3(8) . . . . ? C1 N1 C6 C7 -118.7(5) . . . . ? C5 N1 C6 C7 65.2(6) . . . . ? N1 C6 C7 C12 -100.0(6) . . . . ? N1 C6 C7 C8 83.5(6) . . . . ? C12 C7 C8 F1 -177.8(4) . . . . ? C6 C7 C8 F1 -1.0(7) . . . . ? C12 C7 C8 C9 -0.7(7) . . . . ? C6 C7 C8 C9 176.0(4) . . . . ? F1 C8 C9 F2 -1.1(7) . . . . ? C7 C8 C9 F2 -178.1(4) . . . . ? F1 C8 C9 C10 177.2(4) . . . . ? C7 C8 C9 C10 0.1(7) . . . . ? F2 C9 C10 C11 178.3(4) . . . . ? C8 C9 C10 C11 0.0(8) . . . . ? C9 C10 C11 F3 -179.4(4) . . . . ? C9 C10 C11 C12 0.6(8) . . . . ? F3 C11 C12 F4 -0.9(7) . . . . ? C10 C11 C12 F4 179.1(4) . . . . ? F3 C11 C12 C7 178.7(4) . . . . ? C10 C11 C12 C7 -1.3(8) . . . . ? C8 C7 C12 F4 -179.0(4) . . . . ? C6 C7 C12 F4 4.2(7) . . . . ? C8 C7 C12 C11 1.3(7) . . . . ? C6 C7 C12 C11 -175.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.975 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.140 # Attachment 'MG17.CIF' data_mg17 _database_code_depnum_ccdc_archive 'CCDC 794579' #TrackingRef 'MG17.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 F8 N2 2+, I4 2-' _chemical_formula_sum 'C26 H16 F8 I4 N2' _chemical_formula_weight 1016.01 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.119(5) _cell_length_b 6.1713(8) _cell_length_c 12.324(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.106(16) _cell_angle_gamma 90.00 _cell_volume 2973.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5567 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 28.03 _exptl_crystal_description table _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 4.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.3493 _exptl_absorpt_correction_T_max 0.4682 _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 18758 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -55 _diffrn_reflns_limit_h_max 55 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 30.57 _reflns_number_total 4542 _reflns_number_gt 3139 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The 1,2-dipiridylethylene group is disordered by rotation of 180 \% around the N1...N1(1-x,1-y,1-z) axis. Escluding N1 all the other atoms of this mojety were split with population factor 0.5 and refined with soft restraints both on geometric parameters (distances and angles) and on ADPs. Only H13A and H13B were refined with restraints; all the others were in calculated position. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+6.6793P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4542 _refine_ls_number_parameters 223 _refine_ls_number_restraints 100 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.003 _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 I1 I 0.535728(7) 0.14179(4) 0.268135(19) 0.05933(9) Uani 1 1 d . . . I2 I 0.618384(6) 0.13435(4) 0.308315(19) 0.05254(8) Uani 1 1 d . . . F1 F 0.67724(7) 0.6368(4) 0.3791(2) 0.0779(7) Uani 1 1 d . . . F2 F 0.71835(7) 0.3881(5) 0.2641(2) 0.0946(10) Uani 1 1 d . . . F3 F 0.72241(7) -0.1235(4) 0.5466(3) 0.0875(8) Uani 1 1 d . . . F4 F 0.68217(7) 0.1258(4) 0.6617(2) 0.0839(8) Uani 1 1 d . . . C1 C 0.68830(9) 0.4496(6) 0.4219(3) 0.0516(8) Uani 1 1 d . . . C2 C 0.70933(9) 0.3195(8) 0.3630(3) 0.0592(10) Uani 1 1 d . . . C3 C 0.72091(9) 0.1259(7) 0.4025(3) 0.0620(11) Uani 1 1 d . . . H3 H 0.7350 0.0384 0.3621 0.074 Uiso 1 1 calc R . . C4 C 0.71124(9) 0.0641(6) 0.5027(3) 0.0570(9) Uani 1 1 d . . . C5 C 0.69041(8) 0.1931(6) 0.5625(3) 0.0510(8) Uani 1 1 d . . . C6 C 0.67792(8) 0.3880(6) 0.5231(3) 0.0455(7) Uani 1 1 d . . . C7 C 0.65528(9) 0.5286(8) 0.5899(3) 0.0633(11) Uani 1 1 d . A . H7A H 0.6586 0.4891 0.6657 0.076 Uiso 1 1 calc R . . H7B H 0.6623 0.6784 0.5824 0.076 Uiso 1 1 calc R . . N1 N 0.61838(6) 0.5111(4) 0.55902(18) 0.0420(6) Uani 1 1 d DU . . C8A C 0.5972(2) 0.3532(11) 0.5916(5) 0.0503(15) Uani 0.50 1 d PDU A -1 H8A H 0.6063 0.2379 0.6317 0.060 Uiso 0.50 1 calc PR A -1 C9A C 0.5629(2) 0.3565(13) 0.5681(5) 0.051(2) Uani 0.50 1 d PDU A -1 H9A H 0.5489 0.2466 0.5924 0.061 Uiso 0.50 1 calc PR A -1 C10A C 0.54953(18) 0.5246(11) 0.5079(4) 0.045(2) Uani 0.50 1 d PDU A -1 C11A C 0.5718(2) 0.6788(15) 0.4745(8) 0.056(2) Uani 0.50 1 d PDU A -1 H11A H 0.5630 0.7929 0.4327 0.067 Uiso 0.50 1 calc PR A -1 C12A C 0.6060(2) 0.6760(12) 0.4985(6) 0.0531(17) Uani 0.50 1 d PDU A -1 H12A H 0.6203 0.7845 0.4739 0.064 Uiso 0.50 1 calc PR A -1 C13A C 0.51292(13) 0.5518(11) 0.4773(5) 0.0547(17) Uani 0.50 1 d PDU A -1 H13A H 0.5062(6) 0.674(2) 0.4336(10) 0.066 Uiso 0.50 1 d PD B -1 C8B C 0.3977(2) 0.6424(11) 0.3839(6) 0.0503(15) Uani 0.50 1 d PDU . -1 H8B H 0.3855 0.7329 0.3361 0.060 Uiso 0.50 1 calc PR . -1 C9B C 0.4322(2) 0.6611(13) 0.3981(6) 0.056(2) Uani 0.50 1 d PDU A -1 H9B H 0.4433 0.7656 0.3578 0.067 Uiso 0.50 1 calc PR A -1 C10B C 0.45172(19) 0.5360(12) 0.4677(5) 0.048(2) Uani 0.50 1 d PDU A -1 C11B C 0.4346(3) 0.3828(16) 0.5267(9) 0.0531(17) Uani 0.50 1 d PDU A -1 H11B H 0.4468 0.2946 0.5756 0.064 Uiso 0.50 1 calc PR A -1 C12B C 0.39999(12) 0.3601(7) 0.5137(4) 0.052(3) Uani 0.50 1 d PD . -1 H12B H 0.3887 0.2569 0.5541 0.062 Uiso 0.50 1 calc PR . -1 C13B C 0.48917(12) 0.5702(7) 0.4747(4) 0.0500(16) Uani 0.50 1 d PRD A -1 H13B H 0.4985 0.6832 0.4313 0.060 Uiso 0.50 1 d PRD . -1 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 I1 0.07216(18) 0.05554(16) 0.05037(14) -0.00104(11) 0.00343(12) 0.00097(12) I2 0.04679(13) 0.05756(15) 0.05336(13) 0.00052(10) 0.00322(9) -0.00650(10) F1 0.0795(17) 0.0719(17) 0.0816(17) 0.0158(13) -0.0081(13) 0.0031(13) F2 0.0761(18) 0.156(3) 0.0526(13) 0.0052(15) 0.0193(12) -0.0125(17) F3 0.0690(16) 0.0599(16) 0.133(2) 0.0070(15) 0.0020(16) 0.0126(12) F4 0.0758(17) 0.105(2) 0.0724(16) 0.0254(14) 0.0231(13) 0.0024(14) C1 0.0407(17) 0.062(2) 0.0519(18) -0.0019(17) -0.0034(14) -0.0049(16) C2 0.0423(19) 0.090(3) 0.0459(18) -0.0086(19) 0.0071(15) -0.0132(19) C3 0.0352(17) 0.079(3) 0.072(2) -0.029(2) 0.0058(16) -0.0031(18) C4 0.0372(17) 0.053(2) 0.081(3) -0.0071(19) 0.0029(17) -0.0025(16) C5 0.0360(16) 0.063(2) 0.0546(19) 0.0006(17) 0.0061(14) -0.0074(15) C6 0.0328(14) 0.058(2) 0.0459(16) -0.0139(15) 0.0013(12) -0.0041(14) C7 0.0395(18) 0.081(3) 0.069(2) -0.032(2) -0.0008(16) 0.0028(18) N1 0.0371(13) 0.0470(15) 0.0423(13) -0.0041(11) 0.0063(10) 0.0042(11) C8A 0.054(3) 0.060(2) 0.037(3) 0.014(2) 0.001(3) 0.0090(19) C9A 0.042(4) 0.070(5) 0.041(4) 0.011(4) 0.007(3) -0.007(4) C10A 0.035(3) 0.058(4) 0.044(3) 0.002(3) 0.009(3) 0.005(3) C11A 0.042(4) 0.060(5) 0.065(4) 0.014(4) 0.001(3) 0.001(4) C12A 0.043(3) 0.055(4) 0.061(3) 0.009(3) -0.004(3) 0.005(3) C13A 0.038(4) 0.065(5) 0.061(4) 0.004(4) 0.005(3) 0.014(3) C8B 0.054(3) 0.060(2) 0.037(3) 0.014(2) 0.001(3) 0.0090(19) C9B 0.050(4) 0.064(4) 0.053(5) 0.023(4) 0.007(4) -0.003(3) C10B 0.043(4) 0.051(4) 0.050(4) 0.001(4) 0.011(3) 0.001(3) C11B 0.043(3) 0.055(4) 0.061(3) 0.009(3) -0.004(3) 0.005(3) C12B 0.054(6) 0.034(4) 0.068(5) 0.010(4) 0.020(4) -0.010(3) C13B 0.043(4) 0.048(4) 0.060(4) 0.008(3) 0.015(3) 0.000(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 I1 I1 2.8145(7) 2_655 ? F1 C1 1.336(4) . ? F2 C2 1.349(4) . ? F3 C4 1.344(5) . ? F4 C5 1.341(4) . ? C1 C2 1.375(5) . ? C1 C6 1.379(5) . ? C2 C3 1.361(6) . ? C3 C4 1.359(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C5 C6 1.380(5) . ? C6 C7 1.507(5) . ? C7 N1 1.483(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 C12A 1.342(4) . ? N1 C8B 1.350(4) 5_666 ? N1 C8A 1.351(4) . ? N1 C12B 1.379(3) 5_666 ? C8A C9A 1.360(5) . ? C8A H8A 0.9300 . ? C9A C10A 1.368(5) . ? C9A H9A 0.9300 . ? C10A C11A 1.364(5) . ? C10A C13A 1.477(7) . ? C11A C12A 1.359(5) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C13A C13B 0.935(6) . ? C13A H13A 0.958(14) . ? C13A H13B 1.1284 . ? C8B N1 1.350(4) 5_666 ? C8B C9B 1.360(5) . ? C8B H8B 0.9300 . ? C9B C10B 1.365(5) . ? C9B H9B 0.9300 . ? C10B C11B 1.380(12) . ? C10B C13B 1.480(7) . ? C11B C12B 1.366(12) . ? C11B H11B 0.9300 . ? C12B N1 1.379(3) 5_666 ? C12B H12B 0.9300 . ? C13B H13A 1.07(2) . ? C13B H13B 0.9587 . ? 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 F1 C1 C2 119.2(4) . . ? F1 C1 C6 119.6(3) . . ? C2 C1 C6 121.2(4) . . ? F2 C2 C3 120.3(4) . . ? F2 C2 C1 118.3(4) . . ? C3 C2 C1 121.4(4) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? F3 C4 C3 120.7(4) . . ? F3 C4 C5 118.3(4) . . ? C3 C4 C5 121.0(4) . . ? F4 C5 C4 118.5(4) . . ? F4 C5 C6 119.8(3) . . ? C4 C5 C6 121.7(3) . . ? C1 C6 C5 116.5(3) . . ? C1 C6 C7 122.3(4) . . ? C5 C6 C7 121.1(3) . . ? N1 C7 C6 113.8(3) . . ? N1 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N1 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C12A N1 C8B 131.0(7) . 5_666 ? C12A N1 C8A 119.9(7) . . ? C8B N1 C8A 15.2(6) 5_666 . ? C12A N1 C12B 14.8(6) . 5_666 ? C8B N1 C12B 120.1(5) 5_666 5_666 ? C8A N1 C12B 107.3(5) . 5_666 ? C12A N1 C7 114.6(5) . . ? C8B N1 C7 112.7(5) 5_666 . ? C8A N1 C7 125.4(5) . . ? C12B N1 C7 127.1(4) 5_666 . ? N1 C8A C9A 122.5(8) . . ? N1 C8A H8A 118.8 . . ? C9A C8A H8A 118.8 . . ? C8A C9A C10A 118.8(9) . . ? C8A C9A H9A 120.6 . . ? C10A C9A H9A 120.6 . . ? C11A C10A C9A 117.2(8) . . ? C11A C10A C13A 117.9(6) . . ? C9A C10A C13A 124.9(7) . . ? C12A C11A C10A 124.0(10) . . ? C12A C11A H11A 118.0 . . ? C10A C11A H11A 118.0 . . ? N1 C12A C11A 117.6(9) . . ? N1 C12A H12A 121.2 . . ? C11A C12A H12A 121.2 . . ? C13B C13A C10A 167.2(6) . . ? C13B C13A H13A 68.5(14) . . ? C10A C13A H13A 118.4(15) . . ? C13B C13A H13B 54.4 . . ? C10A C13A H13B 132.2 . . ? H13A C13A H13B 14.1 . . ? N1 C8B C9B 118.2(8) 5_666 . ? N1 C8B H8B 120.9 5_666 . ? C9B C8B H8B 120.9 . . ? C8B C9B C10B 124.1(9) . . ? C8B C9B H9B 117.9 . . ? C10B C9B H9B 117.9 . . ? C9B C10B C11B 116.7(8) . . ? C9B C10B C13B 119.0(7) . . ? C11B C10B C13B 124.4(8) . . ? C12B C11B C10B 120.4(9) . . ? C12B C11B H11B 119.8 . . ? C10B C11B H11B 119.8 . . ? C11B C12B N1 120.5(6) . 5_666 ? C11B C12B H12B 119.7 . . ? N1 C12B H12B 119.7 5_666 . ? C13A C13B C10B 164.7(6) . . ? C13A C13B H13A 56.7(10) . . ? C10B C13B H13A 133.9(11) . . ? C13A C13B H13B 73.1 . . ? C10B C13B H13B 117.9 . . ? H13A C13B H13B 16.4 . . ? 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 F1 C1 C2 F2 0.8(5) . . . . ? C6 C1 C2 F2 179.4(3) . . . . ? F1 C1 C2 C3 -179.1(3) . . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? F2 C2 C3 C4 179.7(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 F3 -178.8(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? F3 C4 C5 F4 -0.1(5) . . . . ? C3 C4 C5 F4 -178.8(3) . . . . ? F3 C4 C5 C6 180.0(3) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? F1 C1 C6 C5 -179.8(3) . . . . ? C2 C1 C6 C5 1.6(5) . . . . ? F1 C1 C6 C7 -2.2(5) . . . . ? C2 C1 C6 C7 179.2(3) . . . . ? F4 C5 C6 C1 178.1(3) . . . . ? C4 C5 C6 C1 -2.0(5) . . . . ? F4 C5 C6 C7 0.5(5) . . . . ? C4 C5 C6 C7 -179.6(3) . . . . ? C1 C6 C7 N1 81.7(4) . . . . ? C5 C6 C7 N1 -100.8(4) . . . . ? C6 C7 N1 C12A -102.0(5) . . . . ? C6 C7 N1 C8B 91.3(5) . . . 5_666 ? C6 C7 N1 C8A 81.8(5) . . . . ? C6 C7 N1 C12B -92.8(5) . . . 5_666 ? C12A N1 C8A C9A -1.9(6) . . . . ? C8B N1 C8A C9A 138(3) 5_666 . . . ? C12B N1 C8A C9A -10.4(5) 5_666 . . . ? C7 N1 C8A C9A 174.2(3) . . . . ? N1 C8A C9A C10A 0.9(3) . . . . ? C8A C9A C10A C11A 0.5(3) . . . . ? C8A C9A C10A C13A -179.1(3) . . . . ? C9A C10A C11A C12A -0.8(6) . . . . ? C13A C10A C11A C12A 178.8(5) . . . . ? C8B N1 C12A C11A -11.4(9) 5_666 . . . ? C8A N1 C12A C11A 1.5(7) . . . . ? C12B N1 C12A C11A 34.9(19) 5_666 . . . ? C7 N1 C12A C11A -175.0(5) . . . . ? C10A C11A C12A N1 -0.2(8) . . . . ? C11A C10A C13A C13B -118(3) . . . . ? C9A C10A C13A C13B 61(3) . . . . ? N1 C8B C9B C10B -0.9(3) 5_666 . . . ? C8B C9B C10B C11B -0.3(2) . . . . ? C8B C9B C10B C13B 179.2(2) . . . . ? C9B C10B C11B C12B 0.6(6) . . . . ? C13B C10B C11B C12B -178.9(6) . . . . ? C10B C11B C12B N1 0.3(9) . . . 5_666 ? C10A C13A C13B C10B -96(4) . . . . ? C9B C10B C13B C13A -132(2) . . . . ? C11B C10B C13B C13A 48(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.57 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.091 _refine_diff_density_min -1.007 _refine_diff_density_rms 0.093 # Attachment 'MG47.CIF' data_mg47 _database_code_depnum_ccdc_archive 'CCDC 794580' #TrackingRef 'MG47.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 N2 2+, 2(I3 1-)' _chemical_formula_sum 'C24 H22 I6 N2' _chemical_formula_weight 1099.84 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' _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 13.980(2) _cell_length_b 7.1080(9) _cell_length_c 15.520(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.51(2) _cell_angle_gamma 90.00 _cell_volume 1511.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5550 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.54 _exptl_crystal_description table _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 6.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.5082 _exptl_absorpt_correction_T_max 0.7456 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12361 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.83 _reflns_number_total 3415 _reflns_number_gt 2268 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0156P)^2^+4.9839P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3415 _refine_ls_number_parameters 199 _refine_ls_number_restraints 164 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.219 _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 I1 I 0.52753(3) 0.04536(7) 0.86258(3) 0.06847(16) Uani 1 1 d . . . I2 I 0.32750(4) 0.04152(9) 0.76375(4) 0.0859(2) Uani 1 1 d . . . I3 I 0.73343(4) 0.05171(10) 0.94835(4) 0.0971(2) Uani 1 1 d . . . N1 N 0.2703(4) 0.5013(8) 0.8620(3) 0.0641(15) Uani 1 1 d . . . C1 C 0.3482(5) 0.5450(11) 0.8302(4) 0.0690(18) Uani 1 1 d . A . H1 H 0.3410 0.5767 0.7711 0.083 Uiso 1 1 calc R . . C2 C 0.4392(5) 0.5445(10) 0.8825(4) 0.0622(16) Uani 1 1 d . . . H2 H 0.4933 0.5742 0.8587 0.075 Uiso 1 1 calc R A . C3 C 0.4510(4) 0.4999(8) 0.9710(4) 0.0464(13) Uani 1 1 d . . . C4 C 0.3684(5) 0.4538(13) 1.0011(4) 0.084(3) Uani 1 1 d . . . H4 H 0.3731 0.4195 1.0596 0.101 Uiso 1 1 calc R A . C5 C 0.2798(5) 0.4577(14) 0.9463(4) 0.092(3) Uani 1 1 d . A . H5 H 0.2245 0.4292 0.9684 0.111 Uiso 1 1 calc R . . C7 C 0.0879(4) 0.5384(10) 0.8395(3) 0.0679(19) Uani 1 1 d D . . C6A C 0.174(3) 0.524(4) 0.795(4) 0.092(9) Uani 0.50 1 d PDU A 1 H6A1 H 0.1772 0.6369 0.7599 0.111 Uiso 0.50 1 calc PR A 1 H6A2 H 0.1649 0.4175 0.7548 0.111 Uiso 0.50 1 calc PR A 1 C8A C 0.0602(11) 0.7151(17) 0.8594(11) 0.095(5) Uani 0.50 1 d PDU A 1 H8A H 0.0991 0.8182 0.8528 0.114 Uiso 0.50 1 calc PR A 1 C9A C -0.0251(12) 0.740(2) 0.8891(14) 0.103(6) Uani 0.50 1 d PDU A 1 H9A H -0.0442 0.8599 0.9027 0.124 Uiso 0.50 1 calc PR A 1 C10A C -0.0820(9) 0.587(3) 0.8985(12) 0.092(6) Uani 0.50 1 d PDU A 1 H10A H -0.1401 0.6005 0.9185 0.111 Uiso 0.50 1 calc PR A 1 C11A C -0.0501(12) 0.410(2) 0.8773(14) 0.109(6) Uani 0.50 1 d PDU A 1 H11A H -0.0889 0.3073 0.8839 0.131 Uiso 0.50 1 calc PR A 1 C12A C 0.0368(11) 0.3763(18) 0.8466(12) 0.116(7) Uani 0.50 1 d PDU A 1 H12A H 0.0570 0.2575 0.8328 0.139 Uiso 0.50 1 calc PR A 1 C6B C 0.173(3) 0.462(4) 0.805(4) 0.084(9) Uani 0.50 1 d PDU A 2 H6B1 H 0.1653 0.3266 0.7980 0.101 Uiso 0.50 1 calc PR A 2 H6B2 H 0.1719 0.5149 0.7471 0.101 Uiso 0.50 1 calc PR A 2 C8B C 0.0870(10) 0.7234(16) 0.8620(11) 0.084(5) Uani 0.50 1 d PDU A 2 H8B H 0.1389 0.8003 0.8554 0.100 Uiso 0.50 1 calc PR A 2 C9B C 0.0106(11) 0.799(2) 0.8942(14) 0.090(5) Uani 0.50 1 d PDU A 2 H9B H 0.0110 0.9252 0.9092 0.109 Uiso 0.50 1 calc PR A 2 C10B C -0.0665(10) 0.686(2) 0.9041(12) 0.088(5) Uani 0.50 1 d PDU A 2 H10B H -0.1188 0.7349 0.9257 0.106 Uiso 0.50 1 calc PR A 2 C11B C -0.0641(10) 0.498(2) 0.8809(13) 0.085(5) Uani 0.50 1 d PDU A 2 H11B H -0.1161 0.4212 0.8878 0.101 Uiso 0.50 1 calc PR A 2 C12B C 0.0133(9) 0.4156(17) 0.8476(11) 0.087(5) Uani 0.50 1 d PDU A 2 H12B H 0.0139 0.2893 0.8322 0.105 Uiso 0.50 1 calc PR A 2 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 I1 0.0693(3) 0.0731(3) 0.0657(3) -0.0098(2) 0.0199(2) -0.0003(2) I2 0.0689(3) 0.1037(4) 0.0836(3) -0.0112(3) 0.0114(3) 0.0041(3) I3 0.0756(4) 0.1106(5) 0.0986(4) -0.0099(4) 0.0015(3) -0.0050(3) N1 0.043(3) 0.097(5) 0.049(3) -0.006(3) 0.003(2) 0.013(3) C1 0.060(4) 0.102(6) 0.044(3) 0.004(3) 0.006(3) 0.005(4) C2 0.050(3) 0.084(5) 0.053(3) 0.005(3) 0.012(3) -0.003(3) C3 0.045(3) 0.048(4) 0.047(3) -0.003(2) 0.011(2) 0.007(2) C4 0.047(4) 0.156(8) 0.049(3) 0.024(4) 0.010(3) 0.003(4) C5 0.042(3) 0.176(9) 0.059(4) 0.019(5) 0.011(3) 0.003(5) C7 0.042(3) 0.107(6) 0.049(3) -0.006(4) -0.003(3) 0.008(4) C6A 0.045(9) 0.17(2) 0.050(13) -0.004(19) -0.014(7) 0.025(14) C8A 0.077(11) 0.130(11) 0.075(9) 0.001(9) 0.010(9) 0.038(9) C9A 0.073(11) 0.148(13) 0.084(9) 0.006(10) 0.006(10) 0.035(10) C10A 0.046(8) 0.160(15) 0.068(8) -0.002(11) 0.005(7) 0.007(10) C11A 0.080(10) 0.152(13) 0.084(9) 0.005(11) -0.011(9) -0.017(11) C12A 0.093(12) 0.151(14) 0.087(11) -0.003(11) -0.020(10) -0.038(12) C6B 0.051(9) 0.148(18) 0.050(15) -0.01(2) -0.001(9) 0.025(13) C8B 0.059(9) 0.114(11) 0.074(9) 0.005(9) 0.003(8) 0.019(8) C9B 0.069(10) 0.122(11) 0.076(8) 0.000(9) 0.003(9) 0.017(9) C10B 0.052(8) 0.139(13) 0.076(8) 0.021(10) 0.016(7) 0.004(9) C11B 0.041(6) 0.134(13) 0.077(8) -0.006(10) 0.008(6) 0.027(8) C12B 0.052(8) 0.125(11) 0.080(9) -0.008(9) 0.002(7) 0.006(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9089(9) . ? I1 I3 2.9208(9) . ? N1 C1 1.319(8) . ? N1 C5 1.325(8) . ? N1 C6B 1.49(5) . ? N1 C6A 1.54(6) . ? C1 C2 1.366(9) . ? C1 H1 0.9300 . ? C2 C3 1.387(8) . ? C2 H2 0.9300 . ? C3 C4 1.369(8) . ? C3 C3 1.482(11) 3_667 ? C4 C5 1.355(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8B 1.361(10) . ? C7 C8A 1.368(10) . ? C7 C12A 1.372(10) . ? C7 C12B 1.385(10) . ? C7 C6B 1.502(12) . ? C7 C6A 1.509(13) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C8A C9A 1.373(10) . ? C8A H8A 0.9300 . ? C9A C10A 1.373(10) . ? C9A H9A 0.9300 . ? C10A C11A 1.392(10) . ? C10A H10A 0.9300 . ? C11A C12A 1.411(10) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C8B C9B 1.375(10) . ? C8B H8B 0.9300 . ? C9B C10B 1.374(10) . ? C9B H9B 0.9300 . ? C10B C11B 1.390(10) . ? C10B H10B 0.9300 . ? C11B C12B 1.415(10) . ? C11B H11B 0.9300 . ? C12B H12B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 I1 I3 175.41(2) . . ? C1 N1 C5 119.7(5) . . ? C1 N1 C6B 123.0(15) . . ? C5 N1 C6B 116.3(16) . . ? C1 N1 C6A 113.3(12) . . ? C5 N1 C6A 126.7(13) . . ? C6B N1 C6A 18(2) . . ? N1 C1 C2 121.2(6) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C1 C2 C3 120.1(6) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.8(5) . . ? C4 C3 C3 122.3(6) . 3_667 ? C2 C3 C3 120.9(6) . 3_667 ? C5 C4 C3 120.6(6) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 121.6(6) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C8B C7 C8A 15.7(9) . . ? C8B C7 C12A 139.3(9) . . ? C8A C7 C12A 125.2(9) . . ? C8B C7 C12B 122.6(8) . . ? C8A C7 C12B 107.8(8) . . ? C12A C7 C12B 18.1(8) . . ? C8B C7 C6B 119.4(10) . . ? C8A C7 C6B 134.0(12) . . ? C12A C7 C6B 100.8(12) . . ? C12B C7 C6B 118.0(10) . . ? C8B C7 C6A 103.4(12) . . ? C8A C7 C6A 116.9(10) . . ? C12A C7 C6A 117.3(10) . . ? C12B C7 C6A 133.2(13) . . ? C6B C7 C6A 18(2) . . ? C7 C6A N1 111(3) . . ? C7 C6A H6A1 109.4 . . ? N1 C6A H6A1 109.4 . . ? C7 C6A H6A2 109.4 . . ? N1 C6A H6A2 109.4 . . ? H6A1 C6A H6A2 108.0 . . ? C7 C8A C9A 119.9(10) . . ? C7 C8A H8A 120.1 . . ? C9A C8A H8A 120.1 . . ? C8A C9A C10A 119.6(10) . . ? C8A C9A H9A 120.2 . . ? C10A C9A H9A 120.2 . . ? C9A C10A C11A 118.0(9) . . ? C9A C10A H10A 121.0 . . ? C11A C10A H10A 121.0 . . ? C10A C11A C12A 124.9(10) . . ? C10A C11A H11A 117.5 . . ? C12A C11A H11A 117.5 . . ? C7 C12A C11A 112.4(9) . . ? C7 C12A H12A 123.8 . . ? C11A C12A H12A 123.8 . . ? N1 C6B C7 114(3) . . ? N1 C6B H6B1 108.7 . . ? C7 C6B H6B1 108.7 . . ? N1 C6B H6B2 108.7 . . ? C7 C6B H6B2 108.7 . . ? H6B1 C6B H6B2 107.6 . . ? C7 C8B C9B 121.1(10) . . ? C7 C8B H8B 119.5 . . ? C9B C8B H8B 119.5 . . ? C10B C9B C8B 119.9(10) . . ? C10B C9B H9B 120.1 . . ? C8B C9B H9B 120.1 . . ? C9B C10B C11B 118.1(9) . . ? C9B C10B H10B 120.9 . . ? C11B C10B H10B 120.9 . . ? C10B C11B C12B 123.5(9) . . ? C10B C11B H11B 118.3 . . ? C12B C11B H11B 118.3 . . ? C7 C12B C11B 114.7(9) . . ? C7 C12B H12B 122.6 . . ? C11B C12B H12B 122.6 . . ? 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 C5 N1 C1 C2 0.7(12) . . . . ? C6B N1 C1 C2 -167.1(14) . . . . ? C6A N1 C1 C2 175.7(11) . . . . ? N1 C1 C2 C3 -0.8(11) . . . . ? C1 C2 C3 C4 1.3(10) . . . . ? C1 C2 C3 C3 -179.5(7) . . . 3_667 ? C2 C3 C4 C5 -1.8(12) . . . . ? C3 C3 C4 C5 179.1(8) 3_667 . . . ? C1 N1 C5 C4 -1.1(13) . . . . ? C6B N1 C5 C4 167.5(12) . . . . ? C6A N1 C5 C4 -175.4(13) . . . . ? C3 C4 C5 N1 1.7(15) . . . . ? C8B C7 C6A N1 83.5(18) . . . . ? C8A C7 C6A N1 92(2) . . . . ? C12A C7 C6A N1 -96.2(18) . . . . ? C12B C7 C6A N1 -107(3) . . . . ? C6B C7 C6A N1 -70(14) . . . . ? C1 N1 C6A C7 -160.6(11) . . . . ? C5 N1 C6A C7 14(2) . . . . ? C6B N1 C6A C7 73(6) . . . . ? C8B C7 C8A C9A -157(5) . . . . ? C12A C7 C8A C9A -0.02(19) . . . . ? C12B C7 C8A C9A 5.3(13) . . . . ? C6B C7 C8A C9A 179(3) . . . . ? C6A C7 C8A C9A 171(3) . . . . ? C7 C8A C9A C10A -0.03(18) . . . . ? C8A C9A C10A C11A 0.1(4) . . . . ? C9A C10A C11A C12A -0.1(5) . . . . ? C8B C7 C12A C11A 9(2) . . . . ? C8A C7 C12A C11A 0.0(4) . . . . ? C12B C7 C12A C11A -17(4) . . . . ? C6B C7 C12A C11A -179(3) . . . . ? C6A C7 C12A C11A -171(3) . . . . ? C10A C11A C12A C7 0.0(5) . . . . ? C1 N1 C6B C7 -141.2(19) . . . . ? C5 N1 C6B C7 51(3) . . . . ? C6A N1 C6B C7 -79(4) . . . . ? C8B C7 C6B N1 53(4) . . . . ? C8A C7 C6B N1 60(5) . . . . ? C12A C7 C6B N1 -121(2) . . . . ? C12B C7 C6B N1 -127.1(16) . . . . ? C6A C7 C6B N1 83(12) . . . . ? C8A C7 C8B C9B 20(5) . . . . ? C12A C7 C8B C9B -9(2) . . . . ? C12B C7 C8B C9B 0.01(18) . . . . ? C6B C7 C8B C9B -180(3) . . . . ? C6A C7 C8B C9B 171(3) . . . . ? C7 C8B C9B C10B -0.04(18) . . . . ? C8B C9B C10B C11B 0.1(4) . . . . ? C9B C10B C11B C12B -0.2(5) . . . . ? C8B C7 C12B C11B -0.1(4) . . . . ? C8A C7 C12B C11B -5.7(14) . . . . ? C12A C7 C12B C11B 160(5) . . . . ? C6B C7 C12B C11B 180(3) . . . . ? C6A C7 C12B C11B -168(3) . . . . ? C10B C11B C12B C7 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.751 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.088 # Attachment 'MG53.CIF' data_mg53 _database_code_depnum_ccdc_archive 'CCDC 794581' #TrackingRef 'MG53.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 2+, I3 1-, I 1-' _chemical_formula_sum 'C12 H14 I4 N2' _chemical_formula_weight 693.85 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 9.5397(10) _cell_length_b 11.3337(11) _cell_length_c 17.3668(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1877.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9938 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 34.95 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 6.626 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.3549 _exptl_absorpt_correction_T_max 0.4216 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 29311 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 35.68 _reflns_number_total 3866 _reflns_number_gt 3443 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0138P)^2^+1.1578P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3866 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0217 _refine_ls_R_factor_gt 0.0169 _refine_ls_wR_factor_ref 0.0370 _refine_ls_wR_factor_gt 0.0360 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.017 _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 I3 I 0.860517(16) 0.2500 0.388738(9) 0.01930(4) Uani 1 2 d S . . I1 I 0.280835(16) 0.2500 0.667472(8) 0.01673(3) Uani 1 2 d S . . I4 I 1.101223(17) 0.2500 0.287774(9) 0.02164(4) Uani 1 2 d S . . I2 I 0.616405(16) 0.2500 0.494090(10) 0.02144(4) Uani 1 2 d S . . N1 N 0.71640(14) 0.00934(12) 0.62825(8) 0.0174(2) Uani 1 1 d . . . C1 C 0.83376(19) 0.06955(15) 0.64461(10) 0.0213(3) Uani 1 1 d . . . H1 H 0.8389 0.1135 0.6898 0.026 Uiso 1 1 calc R . . C2 C 0.94665(18) 0.06700(15) 0.59526(9) 0.0201(3) Uani 1 1 d . . . H2 H 1.0276 0.1087 0.6074 0.024 Uiso 1 1 calc R . . C3 C 0.93998(16) 0.00212(13) 0.52720(9) 0.0143(3) Uani 1 1 d . . . C4 C 0.81656(18) -0.05911(16) 0.51233(10) 0.0217(3) Uani 1 1 d . . . H4 H 0.8082 -0.1038 0.4677 0.026 Uiso 1 1 calc R . . C5 C 0.70658(18) -0.05369(16) 0.56373(10) 0.0229(3) Uani 1 1 d . . . H5 H 0.6243 -0.0947 0.5532 0.027 Uiso 1 1 calc R . . C6 C 0.59673(19) 0.01314(18) 0.68221(11) 0.0267(4) Uani 1 1 d . . . H6A H 0.5344 0.0758 0.6677 0.040 Uiso 1 1 calc R . . H6B H 0.6306 0.0267 0.7335 0.040 Uiso 1 1 calc R . . H6C H 0.5474 -0.0606 0.6805 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I3 0.01939(7) 0.01687(6) 0.02163(7) 0.000 -0.00542(5) 0.000 I1 0.01917(7) 0.01743(6) 0.01359(6) 0.000 -0.00484(5) 0.000 I4 0.02439(8) 0.01878(7) 0.02177(7) 0.000 0.00063(6) 0.000 I2 0.01518(7) 0.01942(7) 0.02971(8) 0.000 -0.00244(5) 0.000 N1 0.0164(6) 0.0173(6) 0.0185(6) 0.0006(5) 0.0028(5) 0.0015(5) C1 0.0216(8) 0.0239(7) 0.0184(7) -0.0057(6) 0.0019(6) -0.0020(6) C2 0.0181(7) 0.0246(7) 0.0178(7) -0.0070(6) 0.0007(6) -0.0042(6) C3 0.0146(7) 0.0139(6) 0.0144(6) -0.0009(5) -0.0014(5) 0.0003(5) C4 0.0187(8) 0.0273(8) 0.0191(8) -0.0093(6) 0.0017(6) -0.0057(6) C5 0.0175(7) 0.0259(8) 0.0252(8) -0.0060(7) 0.0013(6) -0.0055(6) C6 0.0203(8) 0.0322(9) 0.0277(9) -0.0021(7) 0.0100(7) -0.0013(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 I3 I4 2.8892(3) . ? I3 I2 2.9615(3) . ? N1 C5 1.332(2) . ? N1 C1 1.342(2) . ? N1 C6 1.478(2) . ? C1 C2 1.377(2) . ? C1 H1 0.9300 . ? C2 C3 1.394(2) . ? C2 H2 0.9300 . ? C3 C4 1.391(2) . ? C3 C3 1.485(3) 5_756 ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 I4 I3 I2 179.210(7) . . ? C5 N1 C1 120.63(15) . . ? C5 N1 C6 119.65(15) . . ? C1 N1 C6 119.71(14) . . ? N1 C1 C2 120.68(15) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 120.23(15) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 117.35(14) . . ? C4 C3 C3 121.23(17) . 5_756 ? C2 C3 C3 121.42(17) . 5_756 ? C5 C4 C3 120.12(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N1 C5 C4 120.99(15) . . ? N1 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.3(3) . . . . ? C6 N1 C1 C2 179.83(17) . . . . ? N1 C1 C2 C3 0.4(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C3 179.90(18) . . . 5_756 ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C3 C4 C5 -179.96(19) 5_756 . . . ? C1 N1 C5 C4 0.2(3) . . . . ? C6 N1 C5 C4 -179.88(17) . . . . ? C3 C4 C5 N1 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.689 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.131 # Attachment 'MG62.CIF' data_mg62 _database_code_depnum_ccdc_archive 'CCDC 794582' #TrackingRef 'MG62.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 2+, 2(I3 1-), 0.5(I2)' _chemical_formula_sum 'C12 H14 I7 N2' _chemical_formula_weight 1074.55 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2715(8) _cell_length_b 12.4980(16) _cell_length_c 14.3479(18) _cell_angle_alpha 104.800(16) _cell_angle_beta 99.824(17) _cell_angle_gamma 102.526(17) _cell_volume 1194.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7608 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 29.29 _exptl_crystal_description table _exptl_crystal_colour black _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 942 _exptl_absorpt_coefficient_mu 9.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.1894 _exptl_absorpt_correction_T_max 0.2674 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 16861 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 29.50 _reflns_number_total 6586 _reflns_number_gt 4744 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+2.9349P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6586 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 I1 I 0.23863(5) 0.91060(3) 0.07118(3) 0.05653(9) Uani 1 1 d . . . I2 I 0.35515(6) 1.15923(3) 0.13341(4) 0.07784(13) Uani 1 1 d . . . I3 I 0.11420(6) 0.65723(3) -0.00510(3) 0.07386(12) Uani 1 1 d . . . I4 I 0.29280(6) 1.14237(4) 0.44320(3) 0.07572(12) Uani 1 1 d . . . I5 I 0.15464(5) 0.90251(3) 0.39427(3) 0.06196(10) Uani 1 1 d . . . I6 I 0.01697(6) 0.63844(4) 0.35700(4) 0.07841(13) Uani 1 1 d . . . I7A I 0.35484(12) 0.46189(6) 0.54579(5) 0.0920(3) Uani 0.6655(12) 1 d P . . I7B I 0.3592(2) 0.54676(10) 0.46053(10) 0.0790(5) Uani 0.3345(12) 1 d P . . N1 N 0.5419(6) 0.5872(4) 0.1723(3) 0.0558(10) Uani 1 1 d . . . N2 N 0.8461(6) 1.1849(4) 0.2839(3) 0.0558(10) Uani 1 1 d . . . C1 C 0.4598(8) 0.6532(5) 0.2299(4) 0.0682(15) Uani 1 1 d . . . H1 H 0.3634 0.6190 0.2565 0.082 Uiso 1 1 calc R . . C2 C 0.5129(8) 0.7701(5) 0.2512(4) 0.0630(13) Uani 1 1 d . . . H2 H 0.4523 0.8143 0.2916 0.076 Uiso 1 1 calc R . . C3 C 0.6574(6) 0.8233(4) 0.2127(3) 0.0465(10) Uani 1 1 d . . . C4 C 0.7396(8) 0.7525(4) 0.1521(4) 0.0582(12) Uani 1 1 d . . . H4 H 0.8348 0.7844 0.1237 0.070 Uiso 1 1 calc R . . C5 C 0.6819(8) 0.6356(5) 0.1336(4) 0.0625(13) Uani 1 1 d . . . H5 H 0.7403 0.5892 0.0938 0.075 Uiso 1 1 calc R . . C6 C 0.7210(6) 0.9494(4) 0.2367(3) 0.0465(10) Uani 1 1 d . . . C7 C 0.7011(8) 1.0195(5) 0.3239(4) 0.0617(13) Uani 1 1 d . . . H7 H 0.6440 0.9871 0.3672 0.074 Uiso 1 1 calc R . . C8 C 0.7656(9) 1.1365(5) 0.3465(4) 0.0702(15) Uani 1 1 d . . . H8 H 0.7537 1.1832 0.4057 0.084 Uiso 1 1 calc R . . C9 C 0.8631(8) 1.1197(5) 0.1990(4) 0.0625(13) Uani 1 1 d . . . H9 H 0.9162 1.1543 0.1558 0.075 Uiso 1 1 calc R . . C10 C 0.8041(8) 1.0023(4) 0.1737(4) 0.0576(12) Uani 1 1 d . . . H10 H 0.8194 0.9577 0.1143 0.069 Uiso 1 1 calc R . . C11 C 0.9121(11) 1.3107(5) 0.3090(5) 0.087(2) Uani 1 1 d . . . H11A H 0.8801 1.3453 0.3697 0.130 Uiso 0.50 1 calc PR . . H11B H 0.8493 1.3346 0.2565 0.130 Uiso 0.50 1 calc PR . . H11C H 1.0501 1.3343 0.3170 0.130 Uiso 0.50 1 calc PR . . H11D H 0.9729 1.3308 0.2591 0.130 Uiso 0.50 1 calc PR . . H11E H 1.0037 1.3415 0.3723 0.130 Uiso 0.50 1 calc PR . . H11F H 0.8029 1.3419 0.3118 0.130 Uiso 0.50 1 calc PR . . C12 C 0.4849(9) 0.4616(5) 0.1543(5) 0.0781(17) Uani 1 1 d . . . H12A H 0.5517 0.4261 0.1083 0.117 Uiso 0.50 1 calc PR . . H12B H 0.3474 0.4318 0.1270 0.117 Uiso 0.50 1 calc PR . . H12C H 0.5184 0.4450 0.2157 0.117 Uiso 0.50 1 calc PR . . H12D H 0.3933 0.4425 0.1924 0.117 Uiso 0.50 1 calc PR . . H12E H 0.5976 0.4368 0.1737 0.117 Uiso 0.50 1 calc PR . . H12F H 0.4266 0.4236 0.0849 0.117 Uiso 0.50 1 calc PR . . 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 I1 0.04548(17) 0.0610(2) 0.0641(2) 0.02497(16) 0.00904(14) 0.01249(14) I2 0.0646(2) 0.0574(2) 0.1037(3) 0.0257(2) 0.0047(2) 0.01113(18) I3 0.0654(2) 0.0580(2) 0.0948(3) 0.0165(2) 0.0223(2) 0.01567(17) I4 0.0656(2) 0.0804(3) 0.0872(3) 0.0317(2) 0.0193(2) 0.0242(2) I5 0.05385(19) 0.0859(3) 0.05478(19) 0.02386(18) 0.01520(15) 0.03208(18) I6 0.0791(3) 0.0693(2) 0.0927(3) 0.0319(2) 0.0221(2) 0.0224(2) I7A 0.1309(7) 0.0719(4) 0.0688(4) 0.0193(3) 0.0028(4) 0.0376(4) I7B 0.0853(9) 0.0608(7) 0.0801(8) 0.0233(6) 0.0106(6) 0.0031(6) N1 0.058(2) 0.054(2) 0.058(2) 0.020(2) 0.013(2) 0.018(2) N2 0.053(2) 0.051(2) 0.055(2) 0.0132(19) -0.0007(19) 0.0113(19) C1 0.068(3) 0.071(4) 0.079(4) 0.034(3) 0.035(3) 0.019(3) C2 0.068(3) 0.066(3) 0.072(3) 0.026(3) 0.039(3) 0.029(3) C3 0.048(2) 0.054(3) 0.042(2) 0.019(2) 0.0095(19) 0.020(2) C4 0.061(3) 0.057(3) 0.063(3) 0.017(2) 0.028(2) 0.019(2) C5 0.066(3) 0.059(3) 0.064(3) 0.012(3) 0.023(3) 0.021(3) C6 0.045(2) 0.055(3) 0.046(2) 0.018(2) 0.0116(19) 0.022(2) C7 0.079(4) 0.062(3) 0.049(3) 0.016(2) 0.024(3) 0.023(3) C8 0.085(4) 0.072(4) 0.052(3) 0.011(3) 0.018(3) 0.024(3) C9 0.064(3) 0.065(3) 0.064(3) 0.027(3) 0.022(3) 0.015(3) C10 0.071(3) 0.060(3) 0.054(3) 0.022(2) 0.029(2) 0.027(3) C11 0.100(5) 0.056(3) 0.091(5) 0.018(3) 0.004(4) 0.012(3) C12 0.080(4) 0.060(3) 0.092(5) 0.025(3) 0.019(3) 0.014(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 I1 I2 2.8902(7) . ? I1 I3 2.9483(8) . ? I4 I5 2.8048(8) . ? I5 I6 3.1084(8) . ? I7A I7A 2.7936(18) 2_666 ? I7B I7B 2.787(3) 2_666 ? N1 C1 1.323(7) . ? N1 C5 1.345(7) . ? N1 C12 1.476(7) . ? N2 C9 1.324(7) . ? N2 C8 1.348(7) . ? N2 C11 1.468(7) . ? C1 C2 1.366(8) . ? C1 H1 0.9300 . ? C2 C3 1.391(7) . ? C2 H2 0.9300 . ? C3 C4 1.382(6) . ? C3 C6 1.473(7) . ? C4 C5 1.370(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.382(6) . ? C6 C10 1.392(6) . ? C7 C8 1.369(8) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.368(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11D 0.9600 . ? C11 H11E 0.9600 . ? C11 H11F 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12E 0.9600 . ? C12 H12F 0.9600 . ? 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 I2 I1 I3 176.457(18) . . ? I4 I5 I6 175.516(17) . . ? C1 N1 C5 119.7(5) . . ? C1 N1 C12 119.9(5) . . ? C5 N1 C12 120.4(5) . . ? C9 N2 C8 120.4(5) . . ? C9 N2 C11 119.6(5) . . ? C8 N2 C11 120.0(5) . . ? N1 C1 C2 121.8(5) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C1 C2 C3 120.2(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.9(5) . . ? C4 C3 C6 121.8(4) . . ? C2 C3 C6 121.2(4) . . ? C5 C4 C3 120.6(5) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 120.9(5) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C6 C10 117.7(5) . . ? C7 C6 C3 120.6(4) . . ? C10 C6 C3 121.7(4) . . ? C8 C7 C6 119.9(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N2 C8 C7 120.9(5) . . ? N2 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? N2 C9 C10 121.1(5) . . ? N2 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C6 120.1(5) . . ? C9 C10 H10 120.0 . . ? C6 C10 H10 120.0 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C11 H11D 109.5 . . ? H11A C11 H11D 141.1 . . ? H11B C11 H11D 56.3 . . ? H11C C11 H11D 56.3 . . ? N2 C11 H11E 109.5 . . ? H11A C11 H11E 56.3 . . ? H11B C11 H11E 141.1 . . ? H11C C11 H11E 56.3 . . ? H11D C11 H11E 109.5 . . ? N2 C11 H11F 109.5 . . ? H11A C11 H11F 56.3 . . ? H11B C11 H11F 56.3 . . ? H11C C11 H11F 141.1 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C12 H12D 109.5 . . ? H12A C12 H12D 141.1 . . ? H12B C12 H12D 56.3 . . ? H12C C12 H12D 56.3 . . ? N1 C12 H12E 109.5 . . ? H12A C12 H12E 56.3 . . ? H12B C12 H12E 141.1 . . ? H12C C12 H12E 56.3 . . ? H12D C12 H12E 109.5 . . ? N1 C12 H12F 109.5 . . ? H12A C12 H12F 56.3 . . ? H12B C12 H12F 56.3 . . ? H12C C12 H12F 141.1 . . ? H12D C12 H12F 109.5 . . ? H12E C12 H12F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.2(9) . . . . ? C12 N1 C1 C2 177.8(5) . . . . ? N1 C1 C2 C3 -0.3(9) . . . . ? C1 C2 C3 C4 0.9(8) . . . . ? C1 C2 C3 C6 -178.3(5) . . . . ? C2 C3 C4 C5 -1.3(8) . . . . ? C6 C3 C4 C5 177.8(5) . . . . ? C1 N1 C5 C4 -0.7(8) . . . . ? C12 N1 C5 C4 -178.3(5) . . . . ? C3 C4 C5 N1 1.3(8) . . . . ? C4 C3 C6 C7 -153.4(5) . . . . ? C2 C3 C6 C7 25.7(7) . . . . ? C4 C3 C6 C10 26.1(7) . . . . ? C2 C3 C6 C10 -154.8(5) . . . . ? C10 C6 C7 C8 -1.2(8) . . . . ? C3 C6 C7 C8 178.3(5) . . . . ? C9 N2 C8 C7 0.4(8) . . . . ? C11 N2 C8 C7 179.2(6) . . . . ? C6 C7 C8 N2 1.0(9) . . . . ? C8 N2 C9 C10 -1.5(8) . . . . ? C11 N2 C9 C10 179.6(5) . . . . ? N2 C9 C10 C6 1.2(8) . . . . ? C7 C6 C10 C9 0.2(8) . . . . ? C3 C6 C10 C9 -179.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.487 _refine_diff_density_min -1.352 _refine_diff_density_rms 0.103 # Attachment 'MG67.CIF' data_mg67 _database_code_depnum_ccdc_archive 'CCDC 794583' #TrackingRef 'MG67.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 2+, 2(I3 1-)' _chemical_formula_sum 'C12 H14 I6 N2' _chemical_formula_weight 947.65 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' _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 9.770(2) _cell_length_b 7.3538(14) _cell_length_c 14.749(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.324(15) _cell_angle_gamma 90.00 _cell_volume 1058.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6455 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 32.16 _exptl_crystal_description table _exptl_crystal_colour red _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 8.796 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2438 _exptl_absorpt_correction_T_max 0.3604 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 11629 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 32.52 _reflns_number_total 3365 _reflns_number_gt 2948 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0132P)^2^+0.3823P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3365 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0416 _refine_ls_wR_factor_gt 0.0400 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 I1 I 0.064244(15) 0.11170(2) 0.351135(10) 0.01846(4) Uani 1 1 d . . . I2 I -0.211431(16) 0.13093(2) 0.268011(11) 0.02234(5) Uani 1 1 d . . . I3 I 0.345890(15) 0.07966(2) 0.426712(11) 0.02288(5) Uani 1 1 d . . . C1 C 0.3025(2) 0.5922(3) 0.54378(16) 0.0223(5) Uani 1 1 d . . . H1 H 0.3737 0.6737 0.5292 0.027 Uiso 1 1 calc R . . C2 C 0.1759(2) 0.6081(3) 0.50011(16) 0.0212(5) Uani 1 1 d . . . H2 H 0.1611 0.6982 0.4546 0.025 Uiso 1 1 calc R . . C3 C 0.0697(2) 0.4930(3) 0.52231(14) 0.0151(4) Uani 1 1 d . . . C4 C 0.0976(2) 0.3621(3) 0.58938(17) 0.0234(5) Uani 1 1 d . . . H4 H 0.0274 0.2818 0.6071 0.028 Uiso 1 1 calc R . . N1 N 0.32657(18) 0.4628(3) 0.60674(13) 0.0178(4) Uani 1 1 d . . . C5 C 0.2266(2) 0.3498(4) 0.62976(17) 0.0243(5) Uani 1 1 d . . . H5 H 0.2450 0.2595 0.6747 0.029 Uiso 1 1 calc R . . C6 C 0.4630(2) 0.4457(4) 0.65363(17) 0.0254(5) Uani 1 1 d . . . H6A H 0.4530 0.4523 0.7194 0.038 Uiso 1 1 calc R . . H6B H 0.5223 0.5449 0.6344 0.038 Uiso 1 1 calc R . . H6C H 0.5040 0.3288 0.6381 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02232(8) 0.01486(8) 0.01810(8) -0.00077(5) -0.00025(6) -0.00021(5) I2 0.02394(8) 0.02001(9) 0.02260(8) -0.00008(6) -0.00500(6) 0.00025(6) I3 0.01981(8) 0.02096(9) 0.02767(9) -0.00081(6) -0.00120(6) -0.00142(6) C1 0.0232(11) 0.0246(13) 0.0191(11) 0.0029(10) 0.0013(9) -0.0075(10) C2 0.0235(11) 0.0230(13) 0.0170(11) 0.0053(9) -0.0008(9) -0.0057(9) C3 0.0184(10) 0.0142(11) 0.0127(10) -0.0014(8) 0.0024(8) -0.0007(8) C4 0.0208(11) 0.0222(13) 0.0273(13) 0.0095(10) 0.0010(9) -0.0034(9) N1 0.0171(9) 0.0199(11) 0.0163(9) -0.0018(8) 0.0005(7) 0.0026(8) C5 0.0230(12) 0.0217(13) 0.0279(13) 0.0071(10) -0.0013(10) 0.0008(10) C6 0.0225(11) 0.0296(15) 0.0236(13) 0.0040(11) -0.0053(9) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9171(6) . ? I1 I3 2.9362(6) . ? C1 N1 1.344(3) . ? C1 C2 1.376(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C3 C3 1.492(4) 3_566 ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? N1 C5 1.336(3) . ? N1 C6 1.482(3) . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 I1 I3 176.915(7) . . ? N1 C1 C2 120.9(2) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 117.4(2) . . ? C2 C3 C3 122.1(3) . 3_566 ? C4 C3 C3 120.5(2) . 3_566 ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C5 N1 C1 120.4(2) . . ? C5 N1 C6 118.8(2) . . ? C1 N1 C6 120.8(2) . . ? N1 C5 C4 121.0(2) . . ? N1 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.7(4) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C3 179.1(3) . . . 3_566 ? C2 C3 C4 C5 -0.8(4) . . . . ? C3 C3 C4 C5 179.7(3) 3_566 . . . ? C2 C1 N1 C5 -1.7(4) . . . . ? C2 C1 N1 C6 179.9(2) . . . . ? C1 N1 C5 C4 0.5(4) . . . . ? C6 N1 C5 C4 178.9(2) . . . . ? C3 C4 C5 N1 0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.690 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.142 # Attachment 'MG69.CIF' data_mg69 _database_code_depnum_ccdc_archive 'CCDC 794584' #TrackingRef 'MG69.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N2 2+, I5 1-, 0.5(I8 2-)' _chemical_formula_sum 'C12 H14 I9 N2' _chemical_formula_weight 1328.35 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3666(9) _cell_length_b 7.5376(9) _cell_length_c 26.010(3) _cell_angle_alpha 89.788(6) _cell_angle_beta 86.141(7) _cell_angle_gamma 70.266(6) _cell_volume 1356.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9767 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.04 _exptl_crystal_description lamina _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1154 _exptl_absorpt_coefficient_mu 10.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.1410 _exptl_absorpt_correction_T_max 0.2464 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 91753 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 33.15 _reflns_number_total 9911 _reflns_number_gt 6018 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 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 'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+6.1607P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9911 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 I1 I 0.15330(9) 0.92033(10) 0.37198(2) 0.07898(17) Uani 1 1 d . . . I2 I 0.31060(7) 0.83171(7) 0.483100(18) 0.06341(13) Uani 1 1 d . . . I3 I 0.44638(9) 0.74368(9) 0.58093(2) 0.07703(16) Uani 1 1 d . . . I4 I 0.16547(6) 0.89967(6) 0.250478(18) 0.05649(11) Uani 1 1 d . . . I5 I 0.15327(8) 0.90141(7) 0.143724(19) 0.06608(13) Uani 1 1 d . . . I6 I 0.43680(6) 0.31741(6) 0.180344(16) 0.05053(10) Uani 1 1 d . . . I7 I 0.54226(7) 0.27435(7) 0.285353(17) 0.05994(12) Uani 1 1 d . . . I8 I 0.34893(10) 0.34389(10) 0.070082(19) 0.08331(18) Uani 1 1 d . . . I9A I 0.7679(3) 0.1178(3) 0.02303(8) 0.0732(5) Uani 0.50 1 d P . . I9B I 1.1441(3) -0.0924(4) -0.01240(10) 0.0863(6) Uani 0.50 1 d P . . N1 N 0.7622(8) 0.6270(7) 0.12127(18) 0.0490(11) Uani 1 1 d . . . N2 N 0.8812(8) 0.5783(9) 0.38575(19) 0.0553(13) Uani 1 1 d . . . C1 C 0.7128(9) 0.7773(9) 0.2026(2) 0.0502(13) Uani 1 1 d . . . H1 H 0.6606 0.8869 0.2227 0.060 Uiso 1 1 calc R . . C2 C 0.6924(9) 0.7827(9) 0.1508(2) 0.0506(13) Uani 1 1 d . . . H2 H 0.6286 0.8971 0.1358 0.061 Uiso 1 1 calc R . . C3 C 0.8597(10) 0.4587(9) 0.1420(2) 0.0547(15) Uani 1 1 d . . . H3 H 0.9086 0.3513 0.1209 0.066 Uiso 1 1 calc R . . C4 C 0.8863(9) 0.4462(9) 0.1932(2) 0.0488(13) Uani 1 1 d . . . H4 H 0.9540 0.3305 0.2070 0.059 Uiso 1 1 calc R . . C5 C 0.8117(7) 0.6076(8) 0.2256(2) 0.0386(10) Uani 1 1 d . . . C6 C 0.8360(8) 0.5973(8) 0.2813(2) 0.0412(11) Uani 1 1 d . . . C7 C 0.9907(9) 0.4644(10) 0.3011(3) 0.0581(16) Uani 1 1 d . . . H7 H 1.0832 0.3783 0.2790 0.070 Uiso 1 1 calc R . . C8 C 1.0102(11) 0.4573(11) 0.3530(3) 0.0636(18) Uani 1 1 d . . . H8 H 1.1161 0.3657 0.3657 0.076 Uiso 1 1 calc R . . C9 C 0.7272(11) 0.7092(11) 0.3679(3) 0.0632(17) Uani 1 1 d . . . H9 H 0.6361 0.7915 0.3910 0.076 Uiso 1 1 calc R . . C10 C 0.7012(9) 0.7245(10) 0.3165(2) 0.0549(15) Uani 1 1 d . . . H10 H 0.5949 0.8184 0.3047 0.066 Uiso 1 1 calc R . . C11 C 0.7381(13) 0.6363(11) 0.0654(3) 0.071(2) Uani 1 1 d . . . H11A H 0.8402 0.5353 0.0480 0.106 Uiso 1 1 calc R . . H11B H 0.7427 0.7549 0.0530 0.106 Uiso 1 1 calc R . . H11C H 0.6157 0.6249 0.0590 0.106 Uiso 1 1 calc R . . C12 C 0.9059(13) 0.5720(15) 0.4410(3) 0.081(2) Uani 1 1 d . . . H12A H 0.8165 0.6841 0.4575 0.121 Uiso 1 1 calc R . . H12B H 1.0357 0.5644 0.4467 0.121 Uiso 1 1 calc R . . H12C H 0.8819 0.4635 0.4550 0.121 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0817(4) 0.1096(5) 0.0581(3) 0.0165(3) -0.0146(2) -0.0468(3) I2 0.0631(3) 0.0745(3) 0.0588(3) -0.0005(2) -0.0014(2) -0.0317(2) I3 0.0822(4) 0.0906(4) 0.0657(3) 0.0069(3) -0.0209(3) -0.0361(3) I4 0.0546(2) 0.0551(2) 0.0631(3) 0.00908(19) -0.01070(19) -0.02178(18) I5 0.0770(3) 0.0656(3) 0.0595(3) 0.0077(2) -0.0135(2) -0.0276(2) I6 0.0525(2) 0.0485(2) 0.0520(2) 0.00184(16) -0.00489(16) -0.01873(16) I7 0.0643(3) 0.0714(3) 0.0503(2) 0.00325(19) -0.01156(19) -0.0297(2) I8 0.1015(4) 0.1132(5) 0.0429(2) 0.0044(3) -0.0095(2) -0.0455(4) I9A 0.1251(16) 0.0503(8) 0.0551(8) 0.0112(6) -0.0287(9) -0.0400(10) I9B 0.1160(16) 0.0632(9) 0.0834(13) -0.0009(8) -0.0196(11) -0.0328(11) N1 0.062(3) 0.055(3) 0.038(2) -0.001(2) -0.003(2) -0.031(2) N2 0.055(3) 0.078(4) 0.040(3) 0.010(2) -0.009(2) -0.030(3) C1 0.052(3) 0.048(3) 0.050(3) -0.004(3) -0.007(3) -0.016(3) C2 0.054(3) 0.049(3) 0.048(3) 0.004(3) -0.010(3) -0.015(3) C3 0.066(4) 0.050(3) 0.049(3) -0.011(3) 0.003(3) -0.022(3) C4 0.050(3) 0.044(3) 0.050(3) 0.000(2) -0.003(3) -0.012(2) C5 0.034(2) 0.041(3) 0.040(3) -0.002(2) -0.0008(19) -0.011(2) C6 0.045(3) 0.041(3) 0.040(3) 0.000(2) -0.009(2) -0.015(2) C7 0.047(3) 0.062(4) 0.058(4) 0.001(3) -0.014(3) -0.006(3) C8 0.062(4) 0.073(5) 0.055(4) 0.013(3) -0.023(3) -0.018(3) C9 0.063(4) 0.071(5) 0.051(4) -0.004(3) 0.004(3) -0.019(3) C10 0.048(3) 0.062(4) 0.047(3) 0.003(3) -0.004(3) -0.008(3) C11 0.106(6) 0.066(5) 0.050(4) 0.004(3) -0.018(4) -0.038(4) C12 0.085(6) 0.121(7) 0.039(4) 0.013(4) -0.012(3) -0.038(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 I1 I4 3.1585(8) . ? I2 I3 2.7923(8) . ? I4 I5 2.7839(7) . ? I6 I7 2.8770(7) . ? I6 I8 2.9735(7) . ? I8 I9A 3.143(2) . ? I9A I9B 0.653(3) 2_755 ? I9A I9B 2.783(3) . ? I9B I9A 0.653(3) 2_755 ? I9B I9B 2.165(4) 2_755 ? N1 C2 1.333(8) . ? N1 C3 1.359(8) . ? N1 C11 1.473(8) . ? N2 C8 1.332(9) . ? N2 C9 1.337(9) . ? N2 C12 1.459(8) . ? C1 C2 1.367(8) . ? C1 C5 1.395(8) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.357(9) . ? C3 H3 0.9300 . ? C4 C5 1.409(8) . ? C4 H4 0.9300 . ? C5 C6 1.471(7) . ? C6 C7 1.368(8) . ? C6 C10 1.408(8) . ? C7 C8 1.365(9) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.362(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 I5 I4 I1 176.21(2) . . ? I7 I6 I8 176.69(2) . . ? I6 I8 I9A 97.54(4) . . ? I9B I9A I8 176.30(5) . . ? C2 N1 C3 120.6(5) . . ? C2 N1 C11 120.2(6) . . ? C3 N1 C11 119.2(5) . . ? C8 N2 C9 119.7(6) . . ? C8 N2 C12 121.1(6) . . ? C9 N2 C12 119.2(6) . . ? C2 C1 C5 120.2(6) . . ? C2 C1 H1 119.9 . . ? C5 C1 H1 119.9 . . ? N1 C2 C1 121.2(6) . . ? N1 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 N1 120.5(6) . . ? C4 C3 H3 119.7 . . ? N1 C3 H3 119.7 . . ? C3 C4 C5 120.3(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C1 C5 C4 117.2(5) . . ? C1 C5 C6 121.4(5) . . ? C4 C5 C6 121.4(5) . . ? C7 C6 C10 117.3(6) . . ? C7 C6 C5 121.4(5) . . ? C10 C6 C5 121.3(5) . . ? C8 C7 C6 120.4(6) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? N2 C8 C7 121.6(6) . . ? N2 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? N2 C9 C10 121.4(6) . . ? N2 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C6 119.6(6) . . ? C9 C10 H10 120.2 . . ? C6 C10 H10 120.2 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C2 C1 -1.5(9) . . . . ? C11 N1 C2 C1 179.9(6) . . . . ? C5 C1 C2 N1 1.4(9) . . . . ? C2 N1 C3 C4 0.6(9) . . . . ? C11 N1 C3 C4 179.2(6) . . . . ? N1 C3 C4 C5 0.5(9) . . . . ? C2 C1 C5 C4 -0.4(8) . . . . ? C2 C1 C5 C6 180.0(5) . . . . ? C3 C4 C5 C1 -0.5(9) . . . . ? C3 C4 C5 C6 179.1(6) . . . . ? C1 C5 C6 C7 -152.1(6) . . . . ? C4 C5 C6 C7 28.3(8) . . . . ? C1 C5 C6 C10 27.7(8) . . . . ? C4 C5 C6 C10 -151.9(6) . . . . ? C10 C6 C7 C8 0.3(10) . . . . ? C5 C6 C7 C8 -179.9(6) . . . . ? C9 N2 C8 C7 0.8(11) . . . . ? C12 N2 C8 C7 -178.6(7) . . . . ? C6 C7 C8 N2 -0.2(11) . . . . ? C8 N2 C9 C10 -1.5(11) . . . . ? C12 N2 C9 C10 177.9(7) . . . . ? N2 C9 C10 C6 1.6(11) . . . . ? C7 C6 C10 C9 -1.0(10) . . . . ? C5 C6 C10 C9 179.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.580 _refine_diff_density_min -1.016 _refine_diff_density_rms 0.158