# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name P.Metrangolo A.Abate M.Brischetto M.Lahtinen T.Pilati ; S.Radice ; G.Resnati K.Rissanene G.Terraneo _publ_contact_author_name 'Pierangelo Metrangolo' _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT data_re285 _database_code_depnum_ccdc_archive 'CCDC 743342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2, 2+, I4, 2-' _chemical_formula_sum 'C12 H30 I4 N2' _chemical_formula_weight 709.98 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 25.963(5) _cell_length_b 7.5588(16) _cell_length_c 5.8260(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.17(2) _cell_angle_gamma 90.00 _cell_volume 1125.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3582 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 29.52 _exptl_crystal_description table _exptl_crystal_colour red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.095 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 5.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.5056 _exptl_absorpt_correction_T_max 0.7461 _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 SMART 2000 CCD diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 6319 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 30.56 _reflns_number_total 1737 _reflns_number_gt 1514 _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 ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) and Mercury 1.4.2, CCDC ; _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^)+(0.0717P)^2^+2.5285P] 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 1737 _refine_ls_number_parameters 75 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.177031(16) 0.0000 0.33715(6) 0.05019(16) Uani 1 2 d S . . I2 I 0.05128(3) 0.0000 0.44910(15) 0.0952(3) Uani 1 2 d S . . N1 N 0.33282(17) 0.0000 0.0687(8) 0.0401(8) Uani 1 2 d S . . C1 C 0.3781(2) 0.0000 -0.0629(9) 0.0455(11) Uani 1 2 d SD . . H1 H 0.3765(19) 0.1063(18) -0.160(4) 0.055 Uiso 1 1 d D . . C2 C 0.4311(3) 0.0000 0.0859(13) 0.0656(18) Uani 1 2 d SD . . H2 H 0.436(2) 0.1048(19) 0.187(4) 0.079 Uiso 1 1 d D . . C3 C 0.4718(2) 0.0000 -0.0733(13) 0.0645(17) Uani 1 2 d SD . . H3 H 0.468(2) 0.1028(19) -0.181(4) 0.077 Uiso 1 1 d D . . C4 C 0.33266(18) 0.1616(6) 0.2161(7) 0.0520(9) Uani 1 1 d D . . H4A H 0.3656(10) 0.165(7) 0.328(7) 0.078 Uiso 1 1 d D . . H4B H 0.3305(19) 0.267(5) 0.117(8) 0.078 Uiso 1 1 d D . . H4C H 0.3025(11) 0.151(8) 0.294(7) 0.078 Uiso 1 1 d D . . C5 C 0.2836(2) 0.0000 -0.1148(10) 0.0509(12) Uani 1 2 d SD . . H5A H 0.2520(17) 0.0000 -0.044(12) 0.076 Uiso 1 2 d SD . . H5B H 0.2844(18) 0.1056(18) -0.212(4) 0.076 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0615(3) 0.0400(2) 0.0514(2) 0.000 0.01670(16) 0.000 I2 0.0838(4) 0.0563(3) 0.1347(6) 0.000 -0.0105(4) 0.000 N1 0.039(2) 0.0374(19) 0.045(2) 0.000 0.0108(16) 0.000 C1 0.045(3) 0.048(3) 0.047(2) 0.000 0.017(2) 0.000 C2 0.044(3) 0.085(5) 0.070(4) 0.000 0.018(3) 0.000 C3 0.040(3) 0.079(5) 0.076(4) 0.000 0.014(3) 0.000 C4 0.058(2) 0.045(2) 0.0544(19) -0.0099(16) 0.0138(16) 0.0005(17) C5 0.044(3) 0.060(3) 0.047(3) 0.000 0.004(2) 0.000 _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. C-H distances were restraint to similar values; the same was done for H-C-H angles. ; 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 I2 2.8285(18) 5_556 ? N1 C4 1.494(5) . ? N1 C4 1.494(5) 6 ? N1 C1 1.513(6) . ? N1 C5 1.515(7) . ? C1 C2 1.492(9) . ? C1 H1 0.978(10) . ? C2 C3 1.524(9) . ? C2 H2 0.982(10) . ? C3 C3 1.558(13) 5_655 ? C3 H3 0.991(10) . ? C4 H4A 0.979(10) . ? C4 H4B 0.978(10) . ? C4 H4C 0.977(10) . ? C5 H5A 0.981(10) . ? C5 H5B 0.980(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C4 109.7(4) . 6 ? C4 N1 C1 111.9(3) . . ? C4 N1 C1 111.9(3) 6 . ? C4 N1 C5 108.5(3) . . ? C4 N1 C5 108.5(3) 6 . ? C1 N1 C5 106.1(4) . . ? C2 C1 N1 115.2(5) . . ? C2 C1 H1 106(3) . . ? N1 C1 H1 110(3) . . ? C1 C2 C3 108.3(6) . . ? C1 C2 H2 111(3) . . ? C3 C2 H2 109(3) . . ? C2 C3 C3 110.5(8) . 5_655 ? C2 C3 H3 112(3) . . ? C3 C3 H3 109(3) 5_655 . ? N1 C4 H4A 108(3) . . ? N1 C4 H4B 109(3) . . ? H4A C4 H4B 109(3) . . ? N1 C4 H4C 107(3) . . ? H4A C4 H4C 112(3) . . ? H4B C4 H4C 112(3) . . ? N1 C5 H5A 111(4) . . ? N1 C5 H5B 108(3) . . ? H5A C5 H5B 110(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 61.8(3) . . . . ? C4 N1 C1 C2 -61.8(3) 6 . . . ? C5 N1 C1 C2 180.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C3 180.0 . . . 5_655 ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.721 _refine_diff_density_min -1.664 _refine_diff_density_rms 0.139 data_re292lt _database_code_depnum_ccdc_archive 'CCDC 755087' #TrackingRef 're292lt.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2, 2+, 2(I5, 1-)' _chemical_formula_sum 'C12 H30 I10 N2' _chemical_formula_weight 1471.38 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 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.675(4) _cell_length_b 7.736(2) _cell_length_c 12.727(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.22(2) _cell_angle_gamma 90.00 _cell_volume 1615.7(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5313 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 31.09 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1292 _exptl_absorpt_coefficient_mu 9.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.3087 _exptl_absorpt_correction_T_max 0.7462 _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 123(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 SMART 2000 CCD diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 15847 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 31.33 _reflns_number_total 2726 _reflns_number_gt 2464 _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 ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) and Mercury 1.4.2, CCDC ; _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^)+(0.0359P)^2^+29.3939P] 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 2726 _refine_ls_number_parameters 71 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.31654(3) 0.0000 0.48904(4) 0.02425(11) Uani 1 2 d S . . I2 I 0.47555(3) 0.0000 0.65456(4) 0.03402(13) Uani 1 2 d S . . I3 I 0.17993(3) 0.0000 0.32605(5) 0.03635(14) Uani 1 2 d S . . I4 I 0.40080(3) 0.0000 0.85781(5) 0.03606(14) Uani 1 2 d S . . I5 I 0.32355(5) 0.0000 1.03683(5) 0.04911(17) Uani 1 2 d S . . N1 N 0.6224(4) 0.5000 0.7167(5) 0.0282(12) Uani 1 2 d S . . C1 C 0.5505(4) 0.5000 0.7739(6) 0.0274(14) Uani 1 2 d S . . H1A H 0.5167 0.6032 0.7511 0.033 Uiso 0.50 1 calc PR . . H1B H 0.5167 0.3968 0.7511 0.033 Uiso 0.50 1 calc PR . . C2 C 0.5717(5) 0.5000 0.8942(6) 0.0334(16) Uani 1 2 d S . . H2A H 0.6044 0.6038 0.9191 0.040 Uiso 0.50 1 calc PR . . H2B H 0.6044 0.3962 0.9191 0.040 Uiso 0.50 1 calc PR . . C3 C 0.4916(5) 0.5000 0.9402(6) 0.0316(15) Uani 1 2 d S . . H3A H 0.4592 0.6035 0.9142 0.038 Uiso 0.50 1 calc PR . . H3B H 0.4592 0.3965 0.9142 0.038 Uiso 0.50 1 calc PR . . C4 C 0.6742(3) 0.6577(8) 0.7419(4) 0.0316(11) Uani 1 1 d . . . H4A H 0.6400 0.7611 0.7288 0.047 Uiso 1 1 calc R . . H4B H 0.7159 0.6604 0.6965 0.047 Uiso 1 1 calc R . . H4C H 0.7006 0.6547 0.8171 0.047 Uiso 1 1 calc R . . C5 C 0.5891(6) 0.5000 0.5980(7) 0.046(2) Uani 1 2 d S . . H5A H 0.6344 0.5000 0.5584 0.069 Uiso 1 2 calc SR . . H5B H 0.5556 0.6034 0.5795 0.069 Uiso 0.50 1 calc PR . . H5C H 0.5556 0.3966 0.5795 0.069 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 0.02117(19) 0.0267(2) 0.0244(2) 0.000 0.00293(15) 0.000 I2 0.0242(2) 0.0390(3) 0.0355(3) 0.000 -0.00396(18) 0.000 I3 0.0276(2) 0.0412(3) 0.0356(3) 0.000 -0.00703(19) 0.000 I4 0.0338(3) 0.0333(3) 0.0353(3) 0.000 -0.0098(2) 0.000 I5 0.0607(4) 0.0507(4) 0.0328(3) 0.000 -0.0003(3) 0.000 N1 0.025(3) 0.038(3) 0.022(3) 0.000 0.005(2) 0.000 C1 0.019(3) 0.039(4) 0.025(3) 0.000 0.005(2) 0.000 C2 0.029(4) 0.046(5) 0.026(3) 0.000 0.008(3) 0.000 C3 0.024(3) 0.039(4) 0.032(4) 0.000 0.007(3) 0.000 C4 0.027(2) 0.036(3) 0.031(2) 0.002(2) 0.0047(19) -0.004(2) C5 0.044(5) 0.071(7) 0.020(3) 0.000 -0.004(3) 0.000 _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 I3 2.7955(10) . ? I1 I2 3.0800(11) . ? I2 I4 3.0642(11) . ? I4 I5 2.8093(11) . ? N1 C4 1.496(7) . ? N1 C4 1.496(7) 6_565 ? N1 C1 1.511(9) . ? N1 C5 1.513(10) . ? C1 C2 1.509(11) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.549(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C3 1.499(16) 5_667 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 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 I3 I1 I2 175.40(2) . . ? I4 I2 I1 98.49(3) . . ? I5 I4 I2 176.77(3) . . ? C4 N1 C4 109.3(6) . 6_565 ? C4 N1 C1 111.9(4) . . ? C4 N1 C1 111.9(4) 6_565 . ? C4 N1 C5 108.1(4) . . ? C4 N1 C5 108.1(4) 6_565 . ? C1 N1 C5 107.4(6) . . ? C2 C1 N1 115.2(6) . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? N1 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C1 C2 C3 108.7(7) . . ? C1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? C3 C3 C2 111.5(8) 5_667 . ? C3 C3 H3A 109.3 5_667 . ? C2 C3 H3A 109.3 . . ? C3 C3 H3B 109.3 5_667 . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 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 C4 N1 C1 C2 -61.5(4) . . . . ? C4 N1 C1 C2 61.5(4) 6_565 . . . ? C5 N1 C1 C2 180.000(2) . . . . ? N1 C1 C2 C3 180.000(2) . . . . ? C1 C2 C3 C3 180.000(2) . . . 5_667 ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 4.355 _refine_diff_density_min -2.081 _refine_diff_density_rms 0.227 # Attachment '2.cif' data_re293 _database_code_depnum_ccdc_archive 'CCDC 755088' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2, 2+ , 2(I3, 1-)' _chemical_formula_sum 'C12 H30 I6 N2' _chemical_formula_weight 963.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.891(4) _cell_length_b 7.6086(14) _cell_length_c 7.8147(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.79(2) _cell_angle_gamma 90.00 _cell_volume 1300.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3095 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.92 _exptl_crystal_description table _exptl_crystal_colour 'intense red' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 7.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.3507 _exptl_absorpt_correction_T_max 0.7461 _exptl_special_details ; Crystals were mixed with others containing C12 H30 N2 2+, 2(I5 1-). This second material is also red, but it seems to be more dark, the thinner crystals being not transparent. ; _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 SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 7324 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.65 _reflns_number_total 2014 _reflns_number_gt 1463 _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 ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _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^)+(0.0308P)^2^+1.8082P] 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 SHELXL _refine_ls_extinction_coef 0.00301(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2014 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.133555(15) 0.0000 0.56410(4) 0.05718(13) Uani 1 2 d S . . I2 I 0.24010(2) 0.0000 0.34029(5) 0.07056(15) Uani 1 2 d S . . I3 I 0.032172(18) 0.0000 0.78132(5) 0.07193(15) Uani 1 2 d S . . N1 N 0.35233(19) 0.0000 0.8726(5) 0.0541(9) Uani 1 2 d S . . C1 C 0.3780(3) 0.0000 0.6953(6) 0.0579(12) Uani 1 2 d S . . H1A H 0.3626 -0.1028 0.6337 0.069 Uiso 0.50 1 calc PR . . H1B H 0.3626 0.1028 0.6337 0.069 Uiso 0.50 1 calc PR . . C2 C 0.4472(2) 0.0000 0.6931(7) 0.0625(13) Uani 1 2 d S . . H2A H 0.4636 -0.1034 0.7515 0.075 Uiso 0.50 1 calc PR . . H2B H 0.4636 0.1034 0.7515 0.075 Uiso 0.50 1 calc PR . . C3 C 0.4652(2) 0.0000 0.5061(8) 0.0677(14) Uani 1 2 d S . . H3A H 0.4482 -0.1031 0.4485 0.081 Uiso 0.50 1 calc PR . . H3B H 0.4482 0.1031 0.4485 0.081 Uiso 0.50 1 calc PR . . C4 C 0.37163(19) 0.1604(7) 0.9699(5) 0.0816(13) Uani 1 1 d . . . H4A H 0.3516 0.1635 1.0765 0.122 Uiso 1 1 calc R . . H4B H 0.3605 0.2629 0.9038 0.122 Uiso 1 1 calc R . . H4C H 0.4151 0.1584 0.9921 0.122 Uiso 1 1 calc R . . C5 C 0.2839(2) 0.0000 0.8472(7) 0.0649(13) Uani 1 2 d S . . H5A H 0.2658 0.0000 0.9567 0.097 Uiso 1 2 calc SR . . H5B H 0.2710 -0.1030 0.7843 0.097 Uiso 0.50 1 calc PR . . H5C H 0.2710 0.1030 0.7843 0.097 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 0.0576(2) 0.0526(2) 0.0602(2) 0.000 -0.00814(15) 0.000 I2 0.0827(3) 0.0723(3) 0.0572(2) 0.000 0.00923(18) 0.000 I3 0.0627(3) 0.0696(3) 0.0836(3) 0.000 0.00513(19) 0.000 N1 0.056(2) 0.056(2) 0.050(2) 0.000 -0.0030(17) 0.000 C1 0.062(3) 0.058(3) 0.054(3) 0.000 0.003(2) 0.000 C2 0.048(3) 0.067(3) 0.072(3) 0.000 0.002(2) 0.000 C3 0.058(3) 0.065(3) 0.081(4) 0.000 0.018(3) 0.000 C4 0.080(3) 0.084(3) 0.081(3) -0.027(2) 0.000(2) -0.010(2) C5 0.047(3) 0.083(4) 0.064(3) 0.000 0.004(2) 0.000 _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 I3 2.8590(8) . ? I1 I2 2.9827(8) . ? N1 C4 1.488(5) . ? N1 C4 1.488(5) 6 ? N1 C5 1.502(6) . ? N1 C1 1.521(6) . ? C1 C2 1.514(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.532(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C3 1.530(11) 5_656 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 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 I3 I1 I2 179.479(15) . . ? C4 N1 C4 110.2(5) . 6 ? C4 N1 C5 108.9(3) . . ? C4 N1 C5 108.9(3) 6 . ? C4 N1 C1 110.9(3) . . ? C4 N1 C1 110.9(3) 6 . ? C5 N1 C1 106.9(4) . . ? C2 C1 N1 115.1(5) . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? N1 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C1 C2 C3 108.4(5) . . ? C1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C3 C3 C2 111.3(7) 5_656 . ? C3 C3 H3A 109.4 5_656 . ? C2 C3 H3A 109.4 . . ? C3 C3 H3B 109.4 5_656 . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 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 C4 N1 C1 C2 61.4(3) . . . . ? C4 N1 C1 C2 -61.4(3) 6 . . . ? C5 N1 C1 C2 180.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C3 180.0 . . . 5_656 ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.833 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.114