# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Lyssenko, Konstantin' _publ_contact_author_email kostya@xray.ineos.ac.ru _publ_section_title ; Unexpected amphoteric character of the halogen bond: the charge density study of the co-crystal of N-methylpyrazine iodide with I2 ; loop_ _publ_author_name Yu.Nelyubina M.Antipin D.Dunin V.Kotov K.Lyssenko # Attachment '- a_xd.cif' data_A _database_code_depnum_ccdc_archive 'CCDC 764429' #TrackingRef '- a_xd.cif' _audit_creation_date '26-May-05 T15:34:47-00:00' _audit_creation_method 'XD routine XDCIF' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H7 N2, 0.5(I2), I' _chemical_formula_sum 'C5 H7 I2 N2' _chemical_formula_weight 348.93 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 5.3648(5) _cell_length_b 7.1380(7) _cell_length_c 12.2613(12) _cell_angle_alpha 96.671(3) _cell_angle_beta 93.576(3) _cell_angle_gamma 104.256(3) _cell_volume 449.97(8) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.916 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.177 _exptl_absorpt_correction_T_max 0.350 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 71539 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 47.49 _reflns_number_total 8329 _reflns_number_gt 7705 _reflns_threshold_expression I>2/s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'Volkov et al, (2006)' _computing_molecular_graphics 'Volkov et al, (2006)' _computing_publication_material 'Volkov et al, (2006)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w1 = [Fo*sqrt(w2) + sqrt(Fo^2^w2^2^ + sqrt(w2^2^))]^2^ where calc w2 = q/[s^2^(Fo^2^) + (0.01 P)^2^ + 0.20 P + 0.00 + 0.00 sin(th)] where P = (0.3333 Fo^2^ + 0.6667 Fc^2^) q = 1.0 ; _refine_ls_extinction_method none _refine_ls_number_reflns 8238 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.016 _refine_ls_R_factor_gt 0.012 _refine_ls_wR_factor_ref 0.015 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.464 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity I(1) 0.598985 0.267664 0.137224 0.016 1 2 I(2) 1.124974 -0.425158 0.604881 0.017 1 2 N(1) 1.094342 -0.171552 0.189526 0.013 1 2 N(4) 1.444006 -0.128313 0.371532 0.02 1 2 C(5) 1.279647 -0.015438 0.366712 0.019 1 2 C(7) 0.912919 -0.193699 0.090168 0.017 1 2 C(6) 1.102673 -0.033749 0.275113 0.017 1 2 C(2) 1.254966 -0.289413 0.192229 0.016 1 2 C(3) 1.429411 -0.264227 0.284852 0.019 1 2 H(2) 1.251719 -0.38785 0.132815 0.021 1 2 H(3) 1.540031 -0.341004 0.284499 0.033 1 2 H(5) 1.288234 0.08558 0.425795 0.034 1 2 H(6) 1.005191 0.049506 0.264592 0.028 1 2 H(7A) 0.840034 -0.092178 0.097231 0.025 1 2 H(7B) 1.01328 -0.186306 0.025896 0.031 1 2 H(7C) 0.796525 -0.32313 0.083146 0.024 1 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 I(1) 0.018034 0.014601 0.013982 0.001371 -0.000668 0.004281 I(2) 0.018338 0.014463 0.019537 0.002545 -0.001223 0.004849 N(1) 0.013552 0.012084 0.013409 0.001919 0.001049 0.003598 N(4) 0.019169 0.021232 0.018414 0.00182 -0.003132 0.004515 C(5) 0.020509 0.019023 0.016348 -0.002412 -0.001426 0.004553 C(7) 0.018025 0.016916 0.015336 0.003545 -0.000541 0.004938 C(6) 0.017338 0.015084 0.017212 -0.001152 0.00045 0.00573 C(2) 0.017531 0.016078 0.015853 0.000229 -0.0001 0.007668 C(3) 0.018492 0.020525 0.020218 0.001933 -0.002052 0.008741 loop_ _atom_site_anharm_GC_C_label _atom_site_anharm_GC_C_111 _atom_site_anharm_GC_C_222 _atom_site_anharm_GC_C_333 _atom_site_anharm_GC_C_112 _atom_site_anharm_GC_C_122 _atom_site_anharm_GC_C_113 _atom_site_anharm_GC_C_133 _atom_site_anharm_GC_C_223 _atom_site_anharm_GC_C_233 _atom_site_anharm_GC_C_123 I(1) 0.000435 0.000097 0.000018 0.000395 0.000172 0.000112 0.000005 -0.000019 0.000022 0.000003 I(2) 0.000013 -0.000155 -0.000013 0.00001 0.000057 -0.000186 0.00011 -0.000133 0.000008 0.000042 loop_ _atom_site_anharm_GC_D_label _atom_site_anharm_GC_D_1111 _atom_site_anharm_GC_D_2222 _atom_site_anharm_GC_D_3333 _atom_site_anharm_GC_D_1112 _atom_site_anharm_GC_D_1222 _atom_site_anharm_GC_D_1113 _atom_site_anharm_GC_D_1333 _atom_site_anharm_GC_D_2223 _atom_site_anharm_GC_D_2333 _atom_site_anharm_GC_D_1122 _atom_site_anharm_GC_D_1133 _atom_site_anharm_GC_D_2233 _atom_site_anharm_GC_D_1123 _atom_site_anharm_GC_D_1223 _atom_site_anharm_GC_D_1233 I(1) 0.000513 0.000335 0.000034 0.000196 0.000204 -0.000058 0.000002 0.000089 0.000004 0.00023 0.00005 0.000044 0.000056 0.000067 0.000041 I(2) 0.000792 0.000505 0.000059 0.000295 0.000294 -0.000035 0.000004 0.000123 0.000014 0.00032 0.000083 0.000085 0.000075 0.000083 0.000047 #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 I(1) 7.9484 0 0.08(2) 0.04(2) 0.01(2) -0.05(3) 0.07(3) -0.21(3) -0.19(3) 0.07(3) -0.02(2) -0.02(2) -0.08(2) -0.02(2) -0.01(2) 0.05(2) -0.05(2) 0.00(3) 0.03(3) 0.20(3) -0.09(3) 0.09(3) 0.23(3) 0.04(3) -0.07(3) -0.10(3) 1.038283 1.293658 1.293658 1.293658 1.293658 1.293658 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 I(2) 7.0268 0 -0.01(2) 0.09(2) -0.05(2) -0.21(3) -0.09(3) -0.14(3) 0.03(3) -0.14(3) -0.02(2) 0.02(2) -0.01(2) 0.04(2) 0.03(2) 0.04(2) 0.01(2) 0.10(3) 0.07(3) -0.10(3) -0.12(3) 0.08(3) -0.08(3) -0.05(3) 0.20(3) -0.13(3) 0.98755 1.311485 1.311485 1.311485 1.311485 1.311485 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 8 4.8152571428571 N(1) 5.1767 0 0.016(19) 0.04(2) 0.02(2) 0.10(2) 0.011(19) -0.01(2) -0.108(19) 0.008(19) 0.22(3) 0.02(3) -0.02(3) 0.17(3) 0.00(3) 0.03(2) 0.02(2) 0 0 0 0 0 0 0 0 0 0.988514 0.923307 0.923307 0.923307 0.923307 0.923307 2 3.81056 2 3.81056 2 3.81056 3 3.81056 4 3.81056 N(4) 5.1383 0 0.039(17) -0.090(17) -0.031(18) 0.06(2) 0.011(19) 0.012(19) -0.093(18) -0.010(18) 0.09(3) -0.01(2) 0.02(3) 0.07(2) 0.02(2) 0.01(2) -0.04(2) 0 0 0 0 0 0 0 0 0 0.987802 1.103873 1.103873 1.103873 1.103873 1.103873 2 3.81056 2 3.81056 2 3.81056 3 3.81056 4 3.81056 C(5) 4.0853 0 -0.10(3) 0.10(3) 0.10(3) 0.14(3) -0.01(2) -0.01(3) -0.10(3) 0.06(3) 0.23(3) 0.05(3) 0.08(4) 0.15(3) -0.04(3) 0.04(3) 0.01(3) 0 0 0 0 0 0 0 0 0 1.004367 0.992846 0.992846 0.992846 0.992846 0.992846 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(7) 4.0605 0 0.06(3) 0.10(2) -0.02(3) 0.03(2) -0.08(2) -0.02(2) -0.11(2) -0.11(2) 0.21(3) 0.06(3) 0.05(3) -0.01(3) 0.00(3) 0.00(3) -0.18(3) 0 0 0 0 0 0 0 0 0 1.009052 0.984729 0.984729 0.984729 0.984729 0.984729 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(6) 4.0915 0 -0.04(2) -0.17(3) -0.05(3) 0.15(3) -0.10(2) 0.01(3) -0.14(2) -0.04(3) 0.23(3) -0.02(3) -0.03(3) 0.18(3) -0.05(3) -0.02(3) 0.00(3) 0 0 0 0 0 0 0 0 0 1.004367 0.992846 0.992846 0.992846 0.992846 0.992846 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(2) 4.0951 0 0.03(2) -0.14(3) -0.04(3) 0.16(3) 0.02(2) 0.08(2) -0.17(2) 0.07(3) 0.27(3) -0.01(3) 0.07(3) 0.17(3) -0.05(3) 0.01(3) -0.07(3) 0 0 0 0 0 0 0 0 0 1.004367 0.992846 0.992846 0.992846 0.992846 0.992846 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 C(3) 3.9312 0 -0.09(2) 0.06(3) 0.04(3) 0.13(2) 0.01(2) -0.06(3) -0.17(3) 0.03(3) 0.18(3) 0.00(3) 0.05(3) 0.16(3) -0.03(3) -0.01(3) 0.01(3) 0 0 0 0 0 0 0 0 0 1.004367 0.992846 0.992846 0.992846 0.992846 0.992846 2 3.1303 2 3.1303 2 3.1303 3 3.1303 4 3.1303 H(2) 0.7995 0 0 0 0.00(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(3) 0.7901 0 0 0 -0.06(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(5) 0.73 0 0 0 -0.02(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(6) 0.7559 0 0 0 -0.04(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(7A) 0.7699 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(7B) 0.8294 0 0 0 0.01(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 H(7C) 0.7712 0 0 0 -0.06(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2 1.2 1.2 1.2 1.2 0 1.9154 1 1.9154 2 1.9154 3 1.9154 4 1.9154 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 I(1) H(7A) Z I(1) H(6) Y I(2) N(4) Z I(2) C(5) Y N(1) C(6) Z N(1) C(2) Y N(4) C(3) Z N(4) C(5) Y C(5) H(5) Z C(5) N(4) Y C(7) H(7A) Z C(7) H(7C) Y C(6) H(6) Z C(6) N(1) Y C(2) H(2) Z C(2) N(1) Y C(3) H(3) Z C(3) N(4) Y H(2) C(2) Z H(2) N(1) Y H(3) C(3) Z H(3) N(4) Y H(5) C(5) Z H(5) N(4) Y H(6) C(6) Z H(6) N(1) Y H(7A) C(7) Z H(7A) H(7B) Y H(7B) C(7) Z H(7B) H(7A) Y H(7C) C(7) Z H(7C) H(7B) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N(1) C(6) 1.3429323627815 1_555 1_555 yes N(1) C(2) 1.3458780182292 1_555 1_555 yes N(4) C(5) 1.3358868950747 1_555 1_555 yes N(4) C(3) 1.3377368451979 1_555 1_555 yes C(5) C(6) 1.3970187938281 1_555 1_555 yes C(5) H(5) 0.9513022491474 1_555 1_555 yes C(7) H(7A) 0.90261608920402 1_555 1_555 yes C(7) H(7B) 0.98097502336664 1_555 1_555 yes C(7) H(7C) 0.97034085516665 1_555 1_555 yes C(6) H(6) 0.89764389154252 1_555 1_555 yes C(2) C(3) 1.3910568095644 1_555 1_555 yes C(2) H(2) 0.94772094061068 1_555 1_555 yes C(3) H(3) 0.90138691334035 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(6) N(1) C(2) 120.28279400158 1_555 1_555 1_555 yes C(5) N(4) C(3) 116.98338188474 1_555 1_555 1_555 yes N(4) C(5) C(6) 122.29782375404 1_555 1_555 1_555 yes N(4) C(5) H(5) 119.31007244456 1_555 1_555 1_555 yes C(6) C(5) H(5) 118.31371939928 1_555 1_555 1_555 yes H(7A) C(7) H(7B) 108.97124158877 1_555 1_555 1_555 yes H(7A) C(7) H(7C) 116.62462596847 1_555 1_555 1_555 yes H(7B) C(7) H(7C) 108.26620243787 1_555 1_555 1_555 yes N(1) C(6) C(5) 118.96854430607 1_555 1_555 1_555 yes N(1) C(6) H(6) 115.70305266941 1_555 1_555 1_555 yes C(5) C(6) H(6) 124.88117588838 1_555 1_555 1_555 yes N(1) C(2) C(3) 118.58948342993 1_555 1_555 1_555 yes N(1) C(2) H(2) 121.59017134751 1_555 1_555 1_555 yes C(3) C(2) H(2) 119.82015947591 1_555 1_555 1_555 yes N(4) C(3) C(2) 122.86697921612 1_555 1_555 1_555 yes N(4) C(3) H(3) 119.4136923721 1_555 1_555 1_555 yes C(2) C(3) H(3) 117.68610326091 1_555 1_555 1_555 yes