# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _audit_creation_method SHELXL-97 _audit_update_record ; April 11th, 2003 Checkcif ; _publ_contact_author_name 'Dr Pierangelo Metrangolo' _publ_contact_author_address ; DCMIC "G. Natta" Polytechnic of Milan Via L. Mancinelli 7 Milan 20131 ITALY ; _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT _publ_section_title ; Crystal engineering of brominated tectons: N-Methyl-3,5-dibromo-pyridinium iodide gives particularly short C−Br***I halogen bonding ; loop_ _publ_author_name 'Pierangelo Metrangolo' 'Thomas A. Logothetis' 'Tullio Pilati' 'Giuseppe Resnati' data_re84 _database_code_depnum_ccdc_archive 'CCDC 228986' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-Methyl-2,4-dibromo-piridinium iodide ; _chemical_formula_moiety '(C6 H6 Br2 N 1+) , I 1-)' _chemical_formula_sum 'C6 H6 Br2 I N' _chemical_formula_weight 378.84 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' Br Br -0.2901 2.4595 '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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.571(2) _cell_length_b 11.724(2) _cell_length_c 14.461(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1961.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6386 _cell_measurement_theta_min 2.817 _cell_measurement_theta_max 29.437 _exptl_crystal_description 'rounded rhombohedron' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 2.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 11.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.051028 _exptl_absorpt_correction_T_max 0.184954 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 47518 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 31.25 _reflns_number_total 3114 _reflns_number_gt 2496 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _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^)+(0.0430P)^2^+1.1830P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00395(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3114 _refine_ls_number_parameters 128 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0736 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.421001(17) 0.130884(17) 0.375681(13) 0.03923(8) Uani 1 d . . . Br1 Br 0.28319(3) 0.31760(2) 0.22015(2) 0.03906(10) Uani 1 d . . . Br2 Br -0.11120(3) 0.58322(3) 0.12856(2) 0.03995(10) Uani 1 d . . . N1 N 0.22640(18) 0.58690(17) 0.04892(13) 0.0291(4) Uani 1 d D . . C2 C 0.1132(2) 0.6109(2) 0.05865(15) 0.0299(5) Uani 1 d D . . H2 H 0.087(3) 0.676(3) 0.0211(19) 0.063(12) Uiso 1 d D . . C3 C 0.0460(2) 0.5467(2) 0.11627(15) 0.0288(5) Uani 1 d D . . C4 C 0.0935(2) 0.4567(2) 0.16504(16) 0.0310(5) Uani 1 d D . . H4 H 0.044(3) 0.411(2) 0.2062(16) 0.049(10) Uiso 1 d D . . C5 C 0.2096(2) 0.43485(19) 0.15326(15) 0.0294(5) Uani 1 d D . . C6 C 0.2761(2) 0.5004(2) 0.09485(15) 0.0297(5) Uani 1 d D . . H6 H 0.362(3) 0.489(2) 0.0833(15) 0.042(9) Uiso 1 d D . . C7 C 0.2976(3) 0.6555(3) -0.0143(3) 0.0444(8) Uani 1 d DU . . H7A H 0.259(5) 0.727(3) -0.018(4) 0.034(13) Uiso 0.50 d PDU . . H7B H 0.298(6) 0.618(5) -0.072(3) 0.041(14) Uiso 0.50 d PDU . . H7C H 0.374(3) 0.666(6) 0.006(5) 0.048(14) Uiso 0.50 d PDU . . H7D H 0.356(5) 0.612(5) -0.043(4) 0.042(14) Uiso 0.50 d PDU . . H7E H 0.333(6) 0.712(5) 0.023(4) 0.044(14) Uiso 0.50 d PDU . . H7F H 0.249(5) 0.691(6) -0.057(4) 0.049(15) Uiso 0.50 d PDU . . 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 0.03244(12) 0.04622(13) 0.03902(13) -0.00334(8) -0.00484(7) 0.01195(8) Br1 0.04560(18) 0.03286(15) 0.03871(16) 0.00634(11) -0.00460(12) 0.01047(12) Br2 0.02745(15) 0.04762(19) 0.04477(18) 0.00193(12) 0.00016(10) 0.00695(12) N1 0.0257(10) 0.0297(10) 0.0319(11) 0.0026(8) -0.0056(8) -0.0017(8) C2 0.0283(12) 0.0275(11) 0.0339(13) 0.0008(10) -0.0076(10) 0.0012(9) C3 0.0246(11) 0.0322(12) 0.0296(12) -0.0044(10) -0.0044(9) 0.0047(10) C4 0.0318(12) 0.0320(13) 0.0291(13) 0.0025(10) 0.0011(10) 0.0019(10) C5 0.0341(13) 0.0258(11) 0.0283(12) -0.0007(9) -0.0073(10) 0.0035(10) C6 0.0279(12) 0.0289(12) 0.0323(12) -0.0001(10) -0.0066(10) 0.0026(10) C7 0.0317(14) 0.0480(17) 0.053(2) 0.0209(15) 0.0003(13) -0.0044(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C5 1.884(2) . NO Br2 C3 1.877(3) . NO N1 C6 1.341(3) . NO N1 C2 1.348(3) . NO N1 C7 1.470(4) . NO C2 C3 1.365(4) . NO C2 H2 0.99(4) . NO C3 C4 1.383(4) . NO C4 C5 1.379(4) . NO C4 H4 0.98(4) . NO C5 C6 1.377(4) . NO C6 H6 1.01(3) . NO C7 H7A 0.95(2) . NO C7 H7B 0.94(3) . NO C7 H7C 0.94(3) . NO C7 H7D 0.94(3) . NO C7 H7E 0.95(2) . NO C7 H7F 0.94(2) . NO 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 C6 N1 C2 121.5(2) . . NO C6 N1 C7 118.8(2) . . NO C2 N1 C7 119.7(2) . . NO N1 C2 C3 120.1(2) . . NO N1 C2 H2 114(2) . . NO C3 C2 H2 126(2) . . NO C2 C3 C4 120.4(2) . . NO C2 C3 Br2 118.92(19) . . NO C4 C3 Br2 120.7(2) . . NO C5 C4 C3 117.8(3) . . NO C5 C4 H4 123(2) . . NO C3 C4 H4 119(2) . . NO C6 C5 C4 121.1(2) . . NO C6 C5 Br1 118.03(19) . . NO C4 C5 Br1 120.8(2) . . NO N1 C6 C5 119.1(2) . . NO N1 C6 H6 116.1(19) . . NO C5 C6 H6 124.8(19) . . NO N1 C7 H7A 105(4) . . NO N1 C7 H7B 107(4) . . NO H7A C7 H7B 111(3) . . NO N1 C7 H7C 114(4) . . NO H7A C7 H7C 110(3) . . NO H7B C7 H7C 109(3) . . NO N1 C7 H7D 112(4) . . NO H7A C7 H7D 142(6) . . NO H7B C7 H7D 50(4) . . NO H7C C7 H7D 62(4) . . NO N1 C7 H7E 106(4) . . NO H7A C7 H7E 68(4) . . NO H7B C7 H7E 146(6) . . NO H7C C7 H7E 48(4) . . NO H7D C7 H7E 109(3) . . NO N1 C7 H7F 108(4) . . NO H7A C7 H7F 44(4) . . NO H7B C7 H7F 67(4) . . NO H7C C7 H7F 136(6) . . NO H7D C7 H7F 112(3) . . NO H7E C7 H7F 109(3) . . NO 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 C6 N1 C2 C3 0.00(3) . . . . NO C7 N1 C2 C3 179.1(2) . . . . NO N1 C2 C3 C4 -0.01(3) . . . . NO N1 C2 C3 Br2 179.66(13) . . . . NO C2 C3 C4 C5 0.02(6) . . . . NO Br2 C3 C4 C5 -179.64(13) . . . . NO C3 C4 C5 C6 -0.02(9) . . . . NO C3 C4 C5 Br1 177.67(13) . . . . NO C2 N1 C6 C5 0.00(7) . . . . NO C7 N1 C6 C5 -179.2(2) . . . . NO C4 C5 C6 N1 0.01(9) . . . . NO Br1 C5 C6 N1 -177.74(13) . . . . NO _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 31.25 _diffrn_measured_fraction_theta_full 0.873 _refine_diff_density_max 1.506 _refine_diff_density_min -0.977 _refine_diff_density_rms 0.132