Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Mr Andreas Lemmerer' _publ_contact_author_email ANDREAS.LEMMERER@GMAIL.COM _publ_section_title ; Disruption of a robust supramolecular heterosynthon in achiral benzylammonium and (pyridylmethyl)ammonium m-iodobenzoate salts ; _publ_requested_category FO loop_ _publ_author_name 'Andreas Lemmerer' 'Susan Bourne' 'Manuel A. Fernandes' # Attachment 'B808909D CIF.cif' data_1_CSD_DEP_689520 _database_code_depnum_ccdc_archive 'CCDC 689520' _audit_creation_date 2008-06-29T12:14:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _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 ; (benzylammonium)(m-iodobenzoate) ; _chemical_formula_moiety 'C7 H10 N, C7 H4 I O2' _chemical_formula_sum 'C14 H14 I N O2' _chemical_formula_weight 355.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.689(3) _cell_length_b 10.544(2) _cell_length_c 8.6613(17) _cell_angle_alpha 90 _cell_angle_beta 91.03(3) _cell_angle_gamma 90 _cell_volume 1341.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 47228 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.68 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.69 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.0\%\p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0194 _diffrn_reflns_number 34678 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2499 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+3.0823P] 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_number_reflns 2499 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.055 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.102 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.7243(3) 0.3919(3) 0.8018(4) 0.0253(8) Uani 1 1 d . . . C2 C 0.7854(3) 0.4748(4) 0.7362(4) 0.0292(8) Uani 1 1 d . . . H2 H 0.7659 0.5312 0.6568 0.035 Uiso 1 1 calc R . . C3 C 0.8758(3) 0.4751(4) 0.7875(5) 0.0311(8) Uani 1 1 d . . . C4 C 0.9056(3) 0.3939(4) 0.9028(5) 0.0343(9) Uani 1 1 d . . . H4 H 0.9677 0.3939 0.9356 0.041 Uiso 1 1 calc R . . C5 C 0.8441(3) 0.3125(4) 0.9699(5) 0.0394(10) Uani 1 1 d . . . H5 H 0.8637 0.2571 1.0504 0.047 Uiso 1 1 calc R . . C6 C 0.7541(3) 0.3114(4) 0.9201(4) 0.0307(8) Uani 1 1 d . . . H6 H 0.7122 0.2553 0.9669 0.037 Uiso 1 1 calc R . . C7 C 0.6257(3) 0.3895(3) 0.7466(4) 0.0272(8) Uani 1 1 d . . . I1 I 0.968240(19) 0.60521(3) 0.69294(4) 0.04521(14) Uani 1 1 d . . . O1 O 0.6004(2) 0.4708(3) 0.6490(3) 0.0389(7) Uani 1 1 d . . . O2 O 0.57540(19) 0.3040(3) 0.7963(3) 0.0362(7) Uani 1 1 d . . . C8 C 0.3423(3) 0.1444(4) 0.4497(4) 0.0279(8) Uani 1 1 d . . . C9 C 0.3829(3) 0.0481(4) 0.3639(5) 0.0297(8) Uani 1 1 d . . . H9 H 0.4447 0.0261 0.3838 0.036 Uiso 1 1 calc R . . C10 C 0.3338(3) -0.0153(4) 0.2505(5) 0.0344(9) Uani 1 1 d . . . H10 H 0.362 -0.08 0.1919 0.041 Uiso 1 1 calc R . . C11 C 0.2433(3) 0.0156(4) 0.2224(5) 0.0389(10) Uani 1 1 d . . . H11 H 0.2094 -0.0281 0.1445 0.047 Uiso 1 1 calc R . . C12 C 0.2027(3) 0.1094(4) 0.3070(6) 0.0406(10) Uani 1 1 d . . . H12 H 0.1406 0.1303 0.2876 0.049 Uiso 1 1 calc R . . C13 C 0.2516(3) 0.1739(4) 0.4204(5) 0.0348(9) Uani 1 1 d . . . H13 H 0.2229 0.2385 0.4784 0.042 Uiso 1 1 calc R . . C14 C 0.3965(3) 0.2144(4) 0.5724(5) 0.0343(9) Uani 1 1 d . . . H14A H 0.3542 0.2578 0.6428 0.041 Uiso 1 1 calc R . . H14B H 0.4328 0.1529 0.634 0.041 Uiso 1 1 calc R . . N1 N 0.4587(2) 0.3099(4) 0.5037(4) 0.0294(7) Uani 1 1 d . . . H1A H 0.491(4) 0.350(5) 0.567(6) 0.044 Uiso 1 1 d . . . H1B H 0.430(4) 0.373(5) 0.459(6) 0.044 Uiso 1 1 d . . . H1C H 0.494(4) 0.278(5) 0.449(6) 0.044 Uiso 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 C1 0.027(2) 0.0239(19) 0.0246(18) -0.0056(15) -0.0013(15) 0.0009(15) C2 0.030(2) 0.0268(19) 0.031(2) -0.0010(16) -0.0029(16) 0.0030(16) C3 0.030(2) 0.028(2) 0.036(2) -0.0052(16) 0.0024(16) 0.0002(16) C4 0.029(2) 0.033(2) 0.041(2) -0.0061(18) -0.0091(18) 0.0031(17) C5 0.044(2) 0.032(2) 0.041(2) 0.0031(19) -0.0121(19) 0.0021(19) C6 0.032(2) 0.0269(19) 0.033(2) 0.0000(16) -0.0040(16) -0.0020(16) C7 0.026(2) 0.0257(19) 0.030(2) -0.0077(16) -0.0026(16) 0.0025(16) I1 0.03087(19) 0.0492(2) 0.0556(2) 0.00840(14) 0.00242(13) -0.00517(13) O1 0.0372(17) 0.0344(16) 0.0446(17) 0.0071(13) -0.0138(13) 0.0018(13) O2 0.0266(14) 0.0348(16) 0.0471(17) 0.0006(13) 0.0009(12) -0.0035(12) C8 0.037(2) 0.0207(17) 0.0257(19) 0.0047(15) 0.0029(16) -0.0022(16) C9 0.032(2) 0.0226(19) 0.034(2) 0.0028(16) 0.0032(16) -0.0002(16) C10 0.038(2) 0.026(2) 0.039(2) -0.0061(17) 0.0058(18) -0.0031(17) C11 0.038(2) 0.035(2) 0.044(2) -0.0058(19) -0.0017(19) -0.0113(19) C12 0.029(2) 0.037(2) 0.056(3) 0.000(2) 0.002(2) 0.0001(18) C13 0.034(2) 0.031(2) 0.040(2) -0.0025(18) 0.0104(17) 0.0000(17) C14 0.046(2) 0.031(2) 0.0267(19) -0.0005(16) -0.0003(17) 0.0020(18) N1 0.0286(18) 0.0280(18) 0.0313(18) -0.0060(15) -0.0068(14) 0.0018(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.382(6) . ? C1 C6 1.395(5) . ? C1 C7 1.517(5) . ? C2 C3 1.393(6) . ? C2 H2 0.95 . ? C3 C4 1.381(6) . ? C3 I1 2.106(4) . ? C4 C5 1.382(6) . ? C4 H4 0.95 . ? C5 C6 1.383(6) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.247(5) . ? C7 O1 1.255(5) . ? C8 C13 1.388(6) . ? C8 C9 1.398(6) . ? C8 C14 1.509(6) . ? C9 C10 1.380(6) . ? C9 H9 0.95 . ? C10 C11 1.386(6) . ? C10 H10 0.95 . ? C11 C12 1.374(6) . ? C11 H11 0.95 . ? C12 C13 1.385(6) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 N1 1.490(5) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? N1 H1A 0.83(6) . ? N1 H1B 0.88(6) . ? N1 H1C 0.79(6) . ? 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 C2 C1 C6 119.3(4) . . ? C2 C1 C7 120.3(3) . . ? C6 C1 C7 120.4(3) . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 I1 119.2(3) . . ? C2 C3 I1 119.7(3) . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 120.2(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.6(4) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 123.8(4) . . ? O2 C7 C1 118.1(3) . . ? O1 C7 C1 118.0(3) . . ? C13 C8 C9 118.9(4) . . ? C13 C8 C14 120.8(4) . . ? C9 C8 C14 120.4(4) . . ? C10 C9 C8 120.5(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.0(4) . . ? C12 C11 H11 120 . . ? C10 C11 H11 120 . . ? C11 C12 C13 120.4(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.3(4) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? N1 C14 C8 111.7(3) . . ? N1 C14 H14A 109.3 . . ? C8 C14 H14A 109.3 . . ? N1 C14 H14B 109.3 . . ? C8 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 N1 H1A 115(4) . . ? C14 N1 H1B 113(3) . . ? H1A N1 H1B 100(5) . . ? C14 N1 H1C 112(4) . . ? H1A N1 H1C 104(5) . . ? H1B N1 H1C 112(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 C6 C1 C2 C3 1.1(6) . . . . ? C7 C1 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C1 C2 C3 I1 -178.0(3) . . . . ? C2 C3 C4 C5 -1.1(6) . . . . ? I1 C3 C4 C5 177.0(3) . . . . ? C3 C4 C5 C6 1.0(6) . . . . ? C4 C5 C6 C1 0.1(6) . . . . ? C2 C1 C6 C5 -1.1(6) . . . . ? C7 C1 C6 C5 179.4(4) . . . . ? C2 C1 C7 O2 172.1(3) . . . . ? C6 C1 C7 O2 -8.5(5) . . . . ? C2 C1 C7 O1 -5.2(5) . . . . ? C6 C1 C7 O1 174.2(4) . . . . ? C13 C8 C9 C10 0.9(6) . . . . ? C14 C8 C9 C10 -179.3(4) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? C9 C10 C11 C12 0.2(7) . . . . ? C10 C11 C12 C13 0.1(7) . . . . ? C11 C12 C13 C8 0.1(7) . . . . ? C9 C8 C13 C12 -0.6(6) . . . . ? C14 C8 C13 C12 179.6(4) . . . . ? C13 C8 C14 N1 -103.1(4) . . . . ? C9 C8 C14 N1 77.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.83(6) 2.16(6) 2.950(5) 158(5) . N1 H1A O2 0.83(6) 2.37(6) 3.034(5) 137(5) . N1 H1B O1 0.88(6) 1.94(6) 2.795(5) 164(5) 3_666 N1 H1C O2 0.79(6) 1.99(6) 2.778(5) 175(5) 4_565 _chemical_name_common (benzylammonium)(m-iodobenzoate) ### END data_2_CSD_DEP_689521 _database_code_depnum_ccdc_archive 'CCDC 689521' _audit_creation_date 2008-06-29T12:21:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _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 ; ((2-pyridylmethyl)ammonium) (m-iodobenzoate) ; _chemical_formula_moiety 'C6 H9 N2, C7 H4 I O2' _chemical_formula_sum 'C13 H13 I N2 O2' _chemical_formula_weight 356.15 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 16.4778(7) _cell_length_b 6.0706(2) _cell_length_c 14.3327(5) _cell_angle_alpha 90 _cell_angle_beta 108.452(2) _cell_angle_gamma 90 _cell_volume 1359.99(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 49947 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.785 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_number 41513 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2532 _reflns_number_gt 2273 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0147P)^2^+1.6907P] 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_number_reflns 2532 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0489 _refine_ls_wR_factor_gt 0.0465 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.339 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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 C1 C 0.26671(13) 0.8389(3) 0.55956(14) 0.0169(4) Uani 1 1 d . . . C2 C 0.20299(13) 0.7169(3) 0.49289(15) 0.0191(4) Uani 1 1 d . . . H2 H 0.2149 0.5728 0.4748 0.023 Uiso 1 1 calc R . . C3 C 0.12211(13) 0.8057(4) 0.45292(16) 0.0228(5) Uani 1 1 d . . . C4 C 0.10261(14) 1.0149(4) 0.47857(18) 0.0267(5) Uani 1 1 d . . . H4 H 0.0468 1.0744 0.4506 0.032 Uiso 1 1 calc R . . C5 C 0.16593(15) 1.1346(4) 0.54554(18) 0.0272(5) Uani 1 1 d . . . H5 H 0.1533 1.2772 0.5644 0.033 Uiso 1 1 calc R . . C6 C 0.24812(14) 1.0495(4) 0.58587(16) 0.0226(5) Uani 1 1 d . . . H6 H 0.2913 1.1347 0.6311 0.027 Uiso 1 1 calc R . . C7 C 0.35464(13) 0.7374(3) 0.60299(15) 0.0181(4) Uani 1 1 d . . . O1 O 0.36319(10) 0.5428(3) 0.57883(12) 0.0284(4) Uani 1 1 d . . . O2 O 0.41254(9) 0.8534(3) 0.66072(11) 0.0239(3) Uani 1 1 d . . . I1 I 0.029848(10) 0.61647(3) 0.348552(13) 0.03996(7) Uani 1 1 d . . . C8 C 0.63053(13) 0.1372(3) 0.62569(15) 0.0186(4) Uani 1 1 d . . . N2 N 0.62456(11) -0.0627(3) 0.58458(14) 0.0230(4) Uani 1 1 d . . . C10 C 0.69349(14) -0.1939(4) 0.61527(17) 0.0263(5) Uani 1 1 d . . . H10 H 0.6905 -0.3351 0.5858 0.032 Uiso 1 1 calc R . . C11 C 0.76845(15) -0.1356(4) 0.68720(17) 0.0276(5) Uani 1 1 d . . . H11 H 0.8153 -0.2349 0.7071 0.033 Uiso 1 1 calc R . . C12 C 0.77372(14) 0.0706(4) 0.72963(17) 0.0280(5) Uani 1 1 d . . . H12 H 0.8241 0.1155 0.7797 0.034 Uiso 1 1 calc R . . C13 C 0.70381(14) 0.2104(4) 0.69747(16) 0.0228(5) Uani 1 1 d . . . H13 H 0.706 0.3543 0.7242 0.027 Uiso 1 1 calc R . . C14 C 0.55270(13) 0.2825(4) 0.58928(16) 0.0216(4) Uani 1 1 d . . . H14A H 0.5709 0.4386 0.5939 0.026 Uiso 1 1 calc R . . H14B H 0.5226 0.2491 0.5192 0.026 Uiso 1 1 calc R . . N1 N 0.49304(12) 0.2503(3) 0.64698(14) 0.0181(4) Uani 1 1 d . . . H1A H 0.4530(18) 0.347(5) 0.6284(19) 0.027 Uiso 1 1 d . . . H1B H 0.5194(17) 0.270(4) 0.710(2) 0.027 Uiso 1 1 d . . . H1C H 0.4671(16) 0.116(5) 0.6375(18) 0.027 Uiso 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 C1 0.0164(10) 0.0187(10) 0.0165(10) 0.0034(8) 0.0068(8) 0.0014(8) C2 0.0189(10) 0.0183(10) 0.0198(10) 0.0011(9) 0.0058(8) 0.0014(8) C3 0.0167(10) 0.0258(11) 0.0246(11) 0.0047(9) 0.0045(9) 0.0005(9) C4 0.0191(11) 0.0265(12) 0.0365(13) 0.0105(10) 0.0115(10) 0.0092(9) C5 0.0305(12) 0.0190(11) 0.0367(13) 0.0022(10) 0.0173(11) 0.0072(9) C6 0.0249(11) 0.0190(10) 0.0248(11) -0.0011(9) 0.0094(9) -0.0010(9) C7 0.0163(10) 0.0217(11) 0.0164(10) 0.0043(9) 0.0052(8) -0.0004(8) O1 0.0189(8) 0.0248(8) 0.0345(9) -0.0056(7) -0.0015(7) 0.0081(6) O2 0.0190(7) 0.0267(8) 0.0217(8) 0.0031(6) 0.0001(6) -0.0052(6) I1 0.02261(10) 0.04041(11) 0.04226(12) 0.00202(8) -0.01047(7) -0.00168(7) C8 0.0172(10) 0.0234(11) 0.0166(10) 0.0050(9) 0.0074(8) 0.0029(8) N2 0.0188(9) 0.0232(10) 0.0265(10) -0.0003(8) 0.0062(8) 0.0012(7) C10 0.0251(12) 0.0224(11) 0.0337(13) 0.0011(10) 0.0124(10) 0.0042(9) C11 0.0204(11) 0.0333(13) 0.0302(12) 0.0089(10) 0.0094(10) 0.0118(10) C12 0.0182(11) 0.0406(14) 0.0216(11) 0.0029(10) 0.0011(9) 0.0030(10) C13 0.0230(11) 0.0250(11) 0.0206(11) -0.0006(9) 0.0072(9) 0.0017(9) C14 0.0186(10) 0.0242(11) 0.0226(11) 0.0057(9) 0.0074(9) 0.0045(9) N1 0.0135(8) 0.0164(9) 0.0217(10) 0.0003(8) 0.0018(7) 0.0030(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.389(3) . ? C1 C6 1.394(3) . ? C1 C7 1.515(3) . ? C2 C3 1.383(3) . ? C2 H2 0.95 . ? C3 C4 1.388(3) . ? C3 I1 2.105(2) . ? C4 C5 1.380(3) . ? C4 H4 0.95 . ? C5 C6 1.393(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O1 1.252(3) . ? C7 O2 1.261(3) . ? C8 N2 1.339(3) . ? C8 C13 1.388(3) . ? C8 C14 1.507(3) . ? N2 C10 1.342(3) . ? C10 C11 1.381(3) . ? C10 H10 0.95 . ? C11 C12 1.382(3) . ? C11 H11 0.95 . ? C12 C13 1.387(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 N1 1.484(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? N1 H1A 0.86(3) . ? N1 H1B 0.88(3) . ? N1 H1C 0.91(3) . ? 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 C2 C1 C6 119.49(19) . . ? C2 C1 C7 118.82(18) . . ? C6 C1 C7 121.69(19) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 I1 117.79(16) . . ? C4 C3 I1 120.81(16) . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.7(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 O2 125.49(19) . . ? O1 C7 C1 116.55(18) . . ? O2 C7 C1 117.95(18) . . ? N2 C8 C13 122.79(19) . . ? N2 C8 C14 116.23(19) . . ? C13 C8 C14 121.0(2) . . ? C8 N2 C10 117.18(19) . . ? N2 C10 C11 123.8(2) . . ? N2 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? C10 C11 C12 118.5(2) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C11 C12 C13 118.6(2) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C8 119.1(2) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? N1 C14 C8 111.78(17) . . ? N1 C14 H14A 109.3 . . ? C8 C14 H14A 109.3 . . ? N1 C14 H14B 109.3 . . ? C8 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 N1 H1A 108.3(17) . . ? C14 N1 H1B 111.0(16) . . ? H1A N1 H1B 108(2) . . ? C14 N1 H1C 113.4(15) . . ? H1A N1 H1C 107(2) . . ? H1B N1 H1C 109(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 C6 C1 C2 C3 0.4(3) . . . . ? C7 C1 C2 C3 179.53(18) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C1 C2 C3 I1 177.84(15) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? I1 C3 C4 C5 -178.41(17) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C7 C1 C6 C5 -178.74(19) . . . . ? C2 C1 C7 O1 -3.2(3) . . . . ? C6 C1 C7 O1 175.95(19) . . . . ? C2 C1 C7 O2 177.54(18) . . . . ? C6 C1 C7 O2 -3.4(3) . . . . ? C13 C8 N2 C10 -0.3(3) . . . . ? C14 C8 N2 C10 179.35(19) . . . . ? C8 N2 C10 C11 1.2(3) . . . . ? N2 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C8 1.4(3) . . . . ? N2 C8 C13 C12 -1.0(3) . . . . ? C14 C8 C13 C12 179.34(19) . . . . ? N2 C8 C14 N1 89.5(2) . . . . ? C13 C8 C14 N1 -90.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.86(3) 1.85(3) 2.713(2) 175(3) . N1 H1B O2 0.88(3) 1.90(3) 2.774(2) 169(2) 2_646 N1 H1C O2 0.91(3) 1.91(3) 2.787(2) 161(2) 1_545 _chemical_name_common '((2-pyridylmethyl)ammonium) (m-iodobenzoate)' ### END data_3_CSD_DEP_689522 _database_code_depnum_ccdc_archive 'CCDC 689522' _audit_creation_date 2008-06-29T12:27:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _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 ; ((3-pyridylmethyl)ammonium)(m-iodobenzoate) ; _chemical_formula_moiety 'C6 H9 N2, C7 H4 I O2' _chemical_formula_sum 'C13 H13 I N2 O2' _chemical_formula_weight 356.15 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.451(3) _cell_length_b 6.1494(12) _cell_length_c 17.582(4) _cell_angle_alpha 90 _cell_angle_beta 96.47(3) _cell_angle_gamma 90 _cell_volume 1337.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 29835 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.39 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; absorption corrections were made using the program SADABS (Sheldrick, 1996). ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '2.0\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_unetI/netI 0.0179 _diffrn_reflns_number 24053 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.7 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2476 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+0.7698P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0200(6) _refine_ls_number_reflns 2476 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0453 _refine_ls_wR_factor_gt 0.0437 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.313 _refine_diff_density_min -0.55 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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 C1 C 0.58336(12) 0.8980(3) 0.30112(10) 0.0175(3) Uani 1 1 d . . . C2 C 0.56875(13) 0.7846(3) 0.23226(10) 0.0187(3) Uani 1 1 d . . . H2 H 0.5397 0.6416 0.2305 0.022 Uiso 1 1 calc R . . C3 C 0.59690(14) 0.8820(3) 0.16657(10) 0.0216(4) Uani 1 1 d . . . C4 C 0.63986(15) 1.0904(3) 0.16736(11) 0.0252(4) Uani 1 1 d . . . H4 H 0.6587 1.1551 0.1216 0.03 Uiso 1 1 calc R . . C5 C 0.65470(15) 1.2022(3) 0.23624(12) 0.0240(4) Uani 1 1 d . . . H5 H 0.6845 1.3446 0.2379 0.029 Uiso 1 1 calc R . . C6 C 0.62638(13) 1.1076(3) 0.30287(10) 0.0204(4) Uani 1 1 d . . . H6 H 0.6363 1.1857 0.3497 0.024 Uiso 1 1 calc R . . C7 C 0.55313(15) 0.7912(3) 0.37347(11) 0.0228(4) Uani 1 1 d . . . O1 O 0.52542(12) 0.5950(2) 0.36874(8) 0.0321(3) Uani 1 1 d . . . O2 O 0.55861(12) 0.9064(2) 0.43264(7) 0.0308(3) Uani 1 1 d . . . I1 I 0.574356(12) 0.70865(3) 0.062788(7) 0.03845(9) Uani 1 1 d . . . C8 C 0.74455(15) 0.3734(3) 0.59006(11) 0.0250(4) Uani 1 1 d . . . C9 C 0.70464(16) 0.1629(3) 0.58671(12) 0.0283(4) Uani 1 1 d . . . H9 H 0.6506 0.1273 0.5461 0.034 Uiso 1 1 calc R . . N3 N 0.73731(13) 0.0068(3) 0.63690(10) 0.0298(4) Uani 1 1 d . . . C11 C 0.81485(15) 0.0594(3) 0.69342(11) 0.0292(4) Uani 1 1 d . . . H11 H 0.8391 -0.0489 0.7299 0.035 Uiso 1 1 calc R . . C12 C 0.86072(16) 0.2633(4) 0.70077(13) 0.0327(5) Uani 1 1 d . . . H12 H 0.9161 0.294 0.741 0.039 Uiso 1 1 calc R . . C13 C 0.82457(15) 0.4227(3) 0.64838(12) 0.0311(4) Uani 1 1 d . . . H13 H 0.8546 0.5648 0.6525 0.037 Uiso 1 1 calc R . . C14 C 0.69899(17) 0.5377(3) 0.53194(11) 0.0307(4) Uani 1 1 d . . . H14A H 0.7572 0.6379 0.5202 0.037 Uiso 1 1 calc R . . H14B H 0.6713 0.4619 0.484 0.037 Uiso 1 1 calc R . . N1 N 0.60998(14) 0.6653(3) 0.56029(10) 0.0244(3) Uani 1 1 d . . . H1A H 0.583(2) 0.743(4) 0.5238(17) 0.037 Uiso 1 1 d . . . H1B H 0.638(2) 0.753(4) 0.5979(16) 0.037 Uiso 1 1 d . . . H1C H 0.5622(19) 0.580(4) 0.5802(13) 0.037 Uiso 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 C1 0.0145(8) 0.0173(9) 0.0208(9) 0.0014(7) 0.0029(6) 0.0016(6) C2 0.0165(8) 0.0174(8) 0.0224(9) -0.0003(7) 0.0025(7) -0.0015(6) C3 0.0222(8) 0.0246(9) 0.0177(8) -0.0021(7) 0.0013(7) 0.0009(7) C4 0.0253(9) 0.0254(10) 0.0258(9) 0.0081(8) 0.0072(8) 0.0008(8) C5 0.0214(9) 0.0167(9) 0.0340(11) 0.0028(7) 0.0042(8) -0.0018(7) C6 0.0177(8) 0.0186(9) 0.0246(9) -0.0024(7) 0.0009(7) 0.0011(7) C7 0.0224(9) 0.0253(10) 0.0216(10) 0.0026(7) 0.0062(7) 0.0019(7) O1 0.0459(8) 0.0217(7) 0.0314(7) 0.0030(6) 0.0163(6) -0.0079(6) O2 0.0447(8) 0.0299(8) 0.0188(7) -0.0005(6) 0.0081(6) -0.0016(6) I1 0.05413(12) 0.04199(12) 0.01988(10) -0.00673(5) 0.00698(6) -0.00576(6) C8 0.0248(9) 0.0252(10) 0.0269(10) -0.0044(8) 0.0109(8) -0.0037(8) C9 0.0292(10) 0.0267(10) 0.0279(10) -0.0036(8) -0.0014(8) -0.0056(8) N3 0.0297(8) 0.0254(9) 0.0332(9) -0.0001(7) -0.0008(7) -0.0035(7) C11 0.0234(9) 0.0348(11) 0.0297(10) -0.0006(8) 0.0037(8) 0.0037(8) C12 0.0202(9) 0.0415(12) 0.0355(12) -0.0098(9) -0.0014(8) -0.0030(8) C13 0.0250(9) 0.0281(10) 0.0408(12) -0.0084(9) 0.0064(8) -0.0087(8) C14 0.0395(11) 0.0274(11) 0.0273(10) 0.0009(8) 0.0127(9) -0.0039(9) N1 0.0318(9) 0.0200(8) 0.0218(8) 0.0010(7) 0.0045(7) -0.0068(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.391(2) . ? C1 C6 1.394(2) . ? C1 C7 1.516(2) . ? C2 C3 1.381(3) . ? C2 H2 0.95 . ? C3 C4 1.388(3) . ? C3 I1 2.1046(18) . ? C4 C5 1.387(3) . ? C4 H4 0.95 . ? C5 C6 1.389(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O2 1.254(2) . ? C7 O1 1.255(2) . ? C8 C13 1.381(3) . ? C8 C9 1.385(3) . ? C8 C14 1.502(3) . ? C9 N3 1.336(3) . ? C9 H9 0.95 . ? N3 C11 1.345(3) . ? C11 C12 1.378(3) . ? C11 H11 0.95 . ? C12 C13 1.385(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 N1 1.489(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? N1 H1A 0.84(3) . ? N1 H1B 0.89(3) . ? N1 H1C 0.89(3) . ? 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 C2 C1 C6 119.66(16) . . ? C2 C1 C7 119.49(15) . . ? C6 C1 C7 120.85(16) . . ? C3 C2 C1 119.32(16) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.73(17) . . ? C2 C3 I1 118.94(13) . . ? C4 C3 I1 119.33(13) . . ? C5 C4 C3 118.68(17) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 120.48(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 120.13(17) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 O1 125.93(17) . . ? O2 C7 C1 117.11(16) . . ? O1 C7 C1 116.95(16) . . ? C13 C8 C9 117.54(19) . . ? C13 C8 C14 122.89(18) . . ? C9 C8 C14 119.56(17) . . ? N3 C9 C8 124.21(18) . . ? N3 C9 H9 117.9 . . ? C8 C9 H9 117.9 . . ? C9 N3 C11 117.06(18) . . ? N3 C11 C12 122.9(2) . . ? N3 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 118.78(19) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C8 C13 C12 119.45(19) . . ? C8 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? N1 C14 C8 111.41(15) . . ? N1 C14 H14A 109.3 . . ? C8 C14 H14A 109.3 . . ? N1 C14 H14B 109.3 . . ? C8 C14 H14B 109.3 . . ? H14A C14 H14B 108 . . ? C14 N1 H1A 107.1(18) . . ? C14 N1 H1B 109.1(16) . . ? H1A N1 H1B 108(2) . . ? C14 N1 H1C 112.0(16) . . ? H1A N1 H1C 114(2) . . ? H1B N1 H1C 106(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 C6 C1 C2 C3 -0.2(2) . . . . ? C7 C1 C2 C3 -179.66(15) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 I1 -179.99(12) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? I1 C3 C4 C5 -179.71(13) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C7 C1 C6 C5 179.32(16) . . . . ? C2 C1 C7 O2 -173.79(16) . . . . ? C6 C1 C7 O2 6.7(2) . . . . ? C2 C1 C7 O1 6.6(2) . . . . ? C6 C1 C7 O1 -172.91(16) . . . . ? C13 C8 C9 N3 1.2(3) . . . . ? C14 C8 C9 N3 -177.92(18) . . . . ? C8 C9 N3 C11 -0.8(3) . . . . ? C9 N3 C11 C12 -0.3(3) . . . . ? N3 C11 C12 C13 0.9(3) . . . . ? C9 C8 C13 C12 -0.5(3) . . . . ? C14 C8 C13 C12 178.59(17) . . . . ? C11 C12 C13 C8 -0.5(3) . . . . ? C13 C8 C14 N1 -85.6(2) . . . . ? C9 C8 C14 N1 93.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.84(3) 1.89(3) 2.706(2) 165(3) . N1 H1B N3 0.89(3) 2.06(3) 2.874(3) 151(2) 1_565 N1 H1C O1 0.89(3) 1.84(3) 2.727(2) 173(2) 3_666 _chemical_name_common ((3-pyridylmethyl)ammonium)(m-iodobenzoate) ### END data_4_CSD_DEP_689523 _database_code_depnum_ccdc_archive 'CCDC 689523' _audit_creation_date 2008-06-29T12:32:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _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 ; ((4-pyridylamethyl)ammonium)(m-iodobenzoate) ; _chemical_formula_moiety 'C6 H9 N2, C7 H4 I O2' _chemical_formula_sum 'C13 H13 I N2 O2' _chemical_formula_weight 356.15 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.56520(10) _cell_length_b 17.7228(4) _cell_length_c 11.8193(2) _cell_angle_alpha 90 _cell_angle_beta 91.0100(10) _cell_angle_gamma 90 _cell_volume 1375.01(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6851 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.72 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 2 0.061 0 1 -2 0.077 1 0 0 0.155 -1 0 0 0.264 0 -1 0 0.075 0 1 0 0.053 0 -1 -2 0.05 1 2 -1 0.114 0 2 1 0.074 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.325 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.4144 _exptl_absorpt_correction_T_max 0.7367 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '0.5\% \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0278 _diffrn_reflns_number 19418 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 5095 _reflns_number_gt 4953 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5095 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0523 _refine_ls_wR_factor_gt 0.0519 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 2459 Friedel Pairs' _refine_ls_abs_structure_Flack -0.030(13) _refine_diff_density_max 0.495 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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 C1A C -0.1273(5) 0.32619(18) 0.6845(3) 0.0251(7) Uani 1 1 d . . . C2A C -0.0080(5) 0.27900(17) 0.7520(3) 0.0260(6) Uani 1 1 d . . . H2D H 0.1263 0.2663 0.7301 0.031 Uiso 1 1 calc R . . C3A C -0.0856(5) 0.25067(18) 0.8511(3) 0.0296(7) Uani 1 1 d . . . C4A C -0.2820(5) 0.26788(19) 0.8838(3) 0.0340(8) Uani 1 1 d . . . H4A H -0.335 0.2479 0.9519 0.041 Uiso 1 1 calc R . . C5A C -0.3997(5) 0.3149(2) 0.8153(3) 0.0319(8) Uani 1 1 d . . . H5A H -0.5346 0.3271 0.8366 0.038 Uiso 1 1 calc R . . C6A C -0.3231(5) 0.34413(18) 0.7166(3) 0.0279(7) Uani 1 1 d . . . H6A H -0.4048 0.3766 0.6706 0.033 Uiso 1 1 calc R . . C7A C -0.0376(5) 0.35735(18) 0.5767(3) 0.0256(6) Uani 1 1 d . . . O1A O 0.1489(3) 0.34989(15) 0.5643(2) 0.0371(6) Uani 1 1 d . . . O2A O -0.1572(3) 0.38866(13) 0.50709(18) 0.0302(5) Uani 1 1 d . . . I1A I 0.09728(4) 0.180706(13) 0.954007(17) 0.04109(7) Uani 1 1 d . . . C1B C 0.3600(4) 0.41938(17) 0.0473(2) 0.0217(6) Uani 1 1 d . . . C2B C 0.4813(4) 0.46858(17) -0.0150(2) 0.0227(6) Uani 1 1 d . . . H2E H 0.6185 0.4778 0.0079 0.027 Uiso 1 1 calc R . . C3B C 0.4011(5) 0.50353(18) -0.1096(3) 0.0280(7) Uani 1 1 d . . . C4B C 0.2023(5) 0.49149(19) -0.1450(3) 0.0307(7) Uani 1 1 d . . . H4B H 0.1489 0.5164 -0.2102 0.037 Uiso 1 1 calc R . . C5B C 0.0823(5) 0.4427(2) -0.0841(3) 0.0311(7) Uani 1 1 d . . . H5B H -0.0546 0.4338 -0.1078 0.037 Uiso 1 1 calc R . . C6B C 0.1606(4) 0.40621(17) 0.0123(3) 0.0240(6) Uani 1 1 d . . . H6B H 0.0773 0.3726 0.0536 0.029 Uiso 1 1 calc R . . C7B C 0.4513(5) 0.38228(17) 0.1511(2) 0.0251(6) Uani 1 1 d . . . O1B O 0.6401(4) 0.38504(15) 0.1627(2) 0.0399(6) Uani 1 1 d . . . O2B O 0.3334(3) 0.34986(13) 0.21825(18) 0.0276(5) Uani 1 1 d . . . I1B I 0.59382(3) 0.573716(11) -0.204737(17) 0.03422(6) Uani 1 1 d . . . C8A C 0.7193(5) 0.21583(16) 0.4171(3) 0.0239(6) Uani 1 1 d . . . C9A C 0.8465(5) 0.17329(18) 0.4868(3) 0.0301(7) Uani 1 1 d . . . H9A H 0.8094 0.1618 0.5622 0.036 Uiso 1 1 calc R . . C10A C 1.0280(6) 0.1480(2) 0.4443(3) 0.0364(8) Uani 1 1 d . . . H10A H 1.1127 0.1176 0.4916 0.044 Uiso 1 1 calc R . . N4A N 1.0918(5) 0.16372(17) 0.3407(3) 0.0398(7) Uani 1 1 d . . . C12A C 0.9708(6) 0.2058(2) 0.2763(3) 0.0383(8) Uani 1 1 d . . . H12A H 1.016 0.219 0.203 0.046 Uiso 1 1 calc R . . C13A C 0.7839(5) 0.23147(19) 0.3089(3) 0.0314(7) Uani 1 1 d . . . H13A H 0.7 0.2596 0.258 0.038 Uiso 1 1 calc R . . C14A C 0.5161(5) 0.24102(19) 0.4595(3) 0.0321(7) Uani 1 1 d . . . H14A H 0.4076 0.2098 0.4239 0.039 Uiso 1 1 calc R . . H14B H 0.5118 0.233 0.5423 0.039 Uiso 1 1 calc R . . N1 N 0.4758(4) 0.32130(16) 0.4344(2) 0.0247(6) Uani 1 1 d . . . H1A H 0.365(7) 0.336(2) 0.471(3) 0.037 Uiso 1 1 d . . . H1B H 0.448(6) 0.330(2) 0.353(3) 0.037 Uiso 1 1 d . . . H1C H 0.571(7) 0.348(3) 0.453(3) 0.037 Uiso 1 1 d . . . C8B C 0.2096(5) 0.52194(18) 0.3089(3) 0.0254(7) Uani 1 1 d . . . C9B C 0.3204(5) 0.5706(2) 0.2436(3) 0.0326(7) Uani 1 1 d . . . H9B H 0.2705 0.586 0.1713 0.039 Uiso 1 1 calc R . . C10B C 0.5058(6) 0.5966(2) 0.2850(3) 0.0382(8) Uani 1 1 d . . . H10B H 0.5788 0.6311 0.2394 0.046 Uiso 1 1 calc R . . N4B N 0.5887(4) 0.57696(19) 0.3833(3) 0.0384(6) Uani 1 1 d . . . C12B C 0.4786(5) 0.52930(19) 0.4458(3) 0.0343(8) Uani 1 1 d . . . H12B H 0.5343 0.5137 0.5167 0.041 Uiso 1 1 calc R . . C13B C 0.2912(5) 0.50165(18) 0.4142(3) 0.0286(7) Uani 1 1 d . . . H13B H 0.2183 0.4693 0.4631 0.034 Uiso 1 1 calc R . . C14B C 0.0047(5) 0.49516(19) 0.2686(3) 0.0290(7) Uani 1 1 d . . . H14C H -0.1022 0.5245 0.307 0.035 Uiso 1 1 calc R . . H14D H -0.0095 0.5046 0.1863 0.035 Uiso 1 1 calc R . . N2 N -0.0269(5) 0.41366(17) 0.2909(2) 0.0261(6) Uani 1 1 d . . . H2A H -0.134(7) 0.402(2) 0.262(3) 0.039 Uiso 1 1 d . . . H2B H -0.048(6) 0.406(2) 0.366(4) 0.039 Uiso 1 1 d . . . H2C H 0.087(7) 0.388(2) 0.270(3) 0.039 Uiso 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 C1A 0.0261(16) 0.0302(16) 0.0189(15) -0.0041(12) 0.0022(12) -0.0057(13) C2A 0.0261(16) 0.0298(16) 0.0222(15) -0.0036(12) 0.0019(12) -0.0010(13) C3A 0.0377(18) 0.0281(15) 0.0229(15) -0.0033(13) 0.0003(13) 0.0007(14) C4A 0.041(2) 0.0381(18) 0.0236(16) -0.0033(14) 0.0098(15) -0.0043(15) C5A 0.0237(18) 0.040(2) 0.0326(18) -0.0073(15) 0.0121(14) -0.0017(14) C6A 0.0285(17) 0.0298(16) 0.0253(16) -0.0035(13) 0.0002(13) 0.0014(13) C7A 0.0262(16) 0.0271(15) 0.0234(15) -0.0021(13) 0.0029(12) -0.0010(13) O1A 0.0228(12) 0.0504(15) 0.0386(13) 0.0090(12) 0.0124(10) 0.0040(11) O2A 0.0276(12) 0.0365(12) 0.0265(11) 0.0025(10) 0.0016(9) -0.0023(10) I1A 0.05660(16) 0.04146(13) 0.02519(11) 0.00329(10) 0.00016(10) 0.00900(11) C1B 0.0227(14) 0.0233(14) 0.0190(14) -0.0018(11) -0.0007(11) 0.0017(12) C2B 0.0188(14) 0.0271(14) 0.0221(14) -0.0005(12) -0.0023(11) -0.0006(12) C3B 0.0291(17) 0.0295(16) 0.0254(16) 0.0012(13) 0.0003(13) -0.0027(13) C4B 0.0333(18) 0.0361(17) 0.0223(15) 0.0077(13) -0.0061(13) 0.0009(14) C5B 0.0212(16) 0.0419(19) 0.0300(17) -0.0007(15) -0.0068(13) -0.0021(14) C6B 0.0210(15) 0.0276(15) 0.0234(15) -0.0013(12) 0.0010(12) -0.0024(12) C7B 0.0269(17) 0.0282(16) 0.0202(15) -0.0010(12) -0.0019(12) 0.0032(13) O1B 0.0230(12) 0.0577(16) 0.0386(14) 0.0198(12) -0.0121(10) -0.0051(11) O2B 0.0247(12) 0.0333(12) 0.0249(11) 0.0047(9) 0.0027(9) 0.0045(10) I1B 0.03622(12) 0.03439(11) 0.03197(11) 0.01050(9) -0.00167(8) -0.00620(10) C8A 0.0248(16) 0.0159(13) 0.0310(16) -0.0015(12) -0.0011(13) -0.0031(12) C9A 0.0276(16) 0.0303(16) 0.0324(16) 0.0089(14) -0.0011(13) -0.0050(14) C10A 0.0273(18) 0.0343(18) 0.047(2) 0.0049(15) -0.0062(15) 0.0050(14) N4A 0.0329(16) 0.0389(17) 0.0477(17) -0.0008(14) 0.0052(13) 0.0074(13) C12A 0.047(2) 0.042(2) 0.0262(16) -0.0026(14) 0.0084(15) 0.0080(16) C13A 0.0352(18) 0.0331(17) 0.0258(16) 0.0008(13) -0.0016(14) 0.0073(14) C14A 0.0244(16) 0.0319(17) 0.0402(19) 0.0074(15) 0.0056(14) -0.0004(14) N1 0.0164(13) 0.0327(15) 0.0250(14) 0.0036(11) 0.0012(11) 0.0039(11) C8B 0.0205(16) 0.0235(15) 0.0323(17) -0.0045(13) 0.0032(13) 0.0059(12) C9B 0.0326(16) 0.0341(16) 0.0312(16) 0.0004(16) 0.0057(13) 0.0058(17) C10B 0.0326(19) 0.0352(19) 0.047(2) -0.0021(15) 0.0144(16) -0.0036(14) N4B 0.0257(13) 0.0356(14) 0.0537(18) -0.0081(16) -0.0013(12) -0.0012(14) C12B 0.0327(18) 0.0286(17) 0.0412(19) -0.0046(15) -0.0095(15) 0.0061(14) C13B 0.0294(17) 0.0258(14) 0.0306(17) -0.0021(13) -0.0015(13) 0.0012(13) C14B 0.0237(16) 0.0321(16) 0.0311(16) 0.0006(13) -0.0038(13) 0.0047(13) N2 0.0183(13) 0.0381(15) 0.0218(14) 0.0004(12) -0.0007(11) -0.0029(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C6A 1.384(4) . ? C1A C2A 1.388(5) . ? C1A C7A 1.517(4) . ? C2A C3A 1.380(4) . ? C2A H2D 0.95 . ? C3A C4A 1.387(5) . ? C3A I1A 2.099(3) . ? C4A C5A 1.387(5) . ? C4A H4A 0.95 . ? C5A C6A 1.380(5) . ? C5A H5A 0.95 . ? C6A H6A 0.95 . ? C7A O1A 1.243(4) . ? C7A O2A 1.257(4) . ? C1B C6B 1.385(4) . ? C1B C2B 1.399(4) . ? C1B C7B 1.508(4) . ? C2B C3B 1.375(4) . ? C2B H2E 0.95 . ? C3B C4B 1.380(5) . ? C3B I1B 2.112(3) . ? C4B C5B 1.382(5) . ? C4B H4B 0.95 . ? C5B C6B 1.399(5) . ? C5B H5B 0.95 . ? C6B H6B 0.95 . ? C7B O1B 1.246(4) . ? C7B O2B 1.257(4) . ? C8A C13A 1.382(4) . ? C8A C9A 1.386(4) . ? C8A C14A 1.501(5) . ? C9A C10A 1.377(5) . ? C9A H9A 0.95 . ? C10A N4A 1.330(5) . ? C10A H10A 0.95 . ? N4A C12A 1.321(5) . ? C12A C13A 1.371(5) . ? C12A H12A 0.95 . ? C13A H13A 0.95 . ? C14A N1 1.476(4) . ? C14A H14A 0.99 . ? C14A H14B 0.99 . ? N1 H1A 0.90(4) . ? N1 H1B 0.99(4) . ? N1 H1C 0.81(5) . ? C8B C9B 1.373(5) . ? C8B C13B 1.393(5) . ? C8B C14B 1.496(5) . ? C9B C10B 1.383(5) . ? C9B H9B 0.95 . ? C10B N4B 1.322(5) . ? C10B H10B 0.95 . ? N4B C12B 1.341(5) . ? C12B C13B 1.370(5) . ? C12B H12B 0.95 . ? C13B H13B 0.95 . ? C14B N2 1.483(4) . ? C14B H14C 0.99 . ? C14B H14D 0.99 . ? N2 H2A 0.81(5) . ? N2 H2B 0.91(4) . ? N2 H2C 0.92(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 C6A C1A C2A 119.9(3) . . ? C6A C1A C7A 121.5(3) . . ? C2A C1A C7A 118.6(3) . . ? C3A C2A C1A 119.6(3) . . ? C3A C2A H2D 120.2 . . ? C1A C2A H2D 120.2 . . ? C2A C3A C4A 121.1(3) . . ? C2A C3A I1A 119.4(2) . . ? C4A C3A I1A 119.6(2) . . ? C3A C4A C5A 118.7(3) . . ? C3A C4A H4A 120.6 . . ? C5A C4A H4A 120.6 . . ? C6A C5A C4A 120.8(3) . . ? C6A C5A H5A 119.6 . . ? C4A C5A H5A 119.6 . . ? C5A C6A C1A 120.0(3) . . ? C5A C6A H6A 120 . . ? C1A C6A H6A 120 . . ? O1A C7A O2A 125.1(3) . . ? O1A C7A C1A 117.3(3) . . ? O2A C7A C1A 117.6(3) . . ? C6B C1B C2B 119.5(3) . . ? C6B C1B C7B 122.0(3) . . ? C2B C1B C7B 118.6(3) . . ? C3B C2B C1B 119.7(3) . . ? C3B C2B H2E 120.2 . . ? C1B C2B H2E 120.2 . . ? C2B C3B C4B 121.6(3) . . ? C2B C3B I1B 118.3(2) . . ? C4B C3B I1B 120.1(2) . . ? C3B C4B C5B 119.0(3) . . ? C3B C4B H4B 120.5 . . ? C5B C4B H4B 120.5 . . ? C4B C5B C6B 120.6(3) . . ? C4B C5B H5B 119.7 . . ? C6B C5B H5B 119.7 . . ? C1B C6B C5B 119.8(3) . . ? C1B C6B H6B 120.1 . . ? C5B C6B H6B 120.1 . . ? O1B C7B O2B 124.8(3) . . ? O1B C7B C1B 117.0(3) . . ? O2B C7B C1B 118.2(3) . . ? C13A C8A C9A 117.9(3) . . ? C13A C8A C14A 122.6(3) . . ? C9A C8A C14A 119.5(3) . . ? C10A C9A C8A 118.4(3) . . ? C10A C9A H9A 120.8 . . ? C8A C9A H9A 120.8 . . ? N4A C10A C9A 123.8(3) . . ? N4A C10A H10A 118.1 . . ? C9A C10A H10A 118.1 . . ? C12A N4A C10A 116.9(3) . . ? N4A C12A C13A 123.9(3) . . ? N4A C12A H12A 118.1 . . ? C13A C12A H12A 118.1 . . ? C12A C13A C8A 119.0(3) . . ? C12A C13A H13A 120.5 . . ? C8A C13A H13A 120.5 . . ? N1 C14A C8A 112.1(3) . . ? N1 C14A H14A 109.2 . . ? C8A C14A H14A 109.2 . . ? N1 C14A H14B 109.2 . . ? C8A C14A H14B 109.2 . . ? H14A C14A H14B 107.9 . . ? C14A N1 H1A 110(2) . . ? C14A N1 H1B 112(2) . . ? H1A N1 H1B 107(3) . . ? C14A N1 H1C 112(3) . . ? H1A N1 H1C 109(4) . . ? H1B N1 H1C 108(3) . . ? C9B C8B C13B 117.7(3) . . ? C9B C8B C14B 120.2(3) . . ? C13B C8B C14B 122.1(3) . . ? C8B C9B C10B 118.9(3) . . ? C8B C9B H9B 120.6 . . ? C10B C9B H9B 120.6 . . ? N4B C10B C9B 124.7(3) . . ? N4B C10B H10B 117.7 . . ? C9B C10B H10B 117.7 . . ? C10B N4B C12B 115.6(3) . . ? N4B C12B C13B 124.4(3) . . ? N4B C12B H12B 117.8 . . ? C13B C12B H12B 117.8 . . ? C12B C13B C8B 118.7(3) . . ? C12B C13B H13B 120.6 . . ? C8B C13B H13B 120.6 . . ? N2 C14B C8B 112.3(3) . . ? N2 C14B H14C 109.1 . . ? C8B C14B H14C 109.1 . . ? N2 C14B H14D 109.1 . . ? C8B C14B H14D 109.1 . . ? H14C C14B H14D 107.9 . . ? C14B N2 H2A 108(3) . . ? C14B N2 H2B 110(3) . . ? H2A N2 H2B 103(4) . . ? C14B N2 H2C 109(3) . . ? H2A N2 H2C 117(4) . . ? H2B N2 H2C 109(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 C6A C1A C2A C3A -0.4(5) . . . . ? C7A C1A C2A C3A 179.3(3) . . . . ? C1A C2A C3A C4A 0.7(5) . . . . ? C1A C2A C3A I1A -179.1(2) . . . . ? C2A C3A C4A C5A -0.5(5) . . . . ? I1A C3A C4A C5A 179.3(3) . . . . ? C3A C4A C5A C6A -0.1(5) . . . . ? C4A C5A C6A C1A 0.5(5) . . . . ? C2A C1A C6A C5A -0.2(5) . . . . ? C7A C1A C6A C5A -179.9(3) . . . . ? C6A C1A C7A O1A 167.3(3) . . . . ? C2A C1A C7A O1A -12.3(4) . . . . ? C6A C1A C7A O2A -12.6(4) . . . . ? C2A C1A C7A O2A 167.7(3) . . . . ? C6B C1B C2B C3B 0.4(4) . . . . ? C7B C1B C2B C3B -179.5(3) . . . . ? C1B C2B C3B C4B 0.2(5) . . . . ? C1B C2B C3B I1B -177.5(2) . . . . ? C2B C3B C4B C5B -0.5(5) . . . . ? I1B C3B C4B C5B 177.1(3) . . . . ? C3B C4B C5B C6B 0.3(5) . . . . ? C2B C1B C6B C5B -0.6(5) . . . . ? C7B C1B C6B C5B 179.3(3) . . . . ? C4B C5B C6B C1B 0.3(5) . . . . ? C6B C1B C7B O1B 165.6(3) . . . . ? C2B C1B C7B O1B -14.5(4) . . . . ? C6B C1B C7B O2B -13.1(4) . . . . ? C2B C1B C7B O2B 166.8(3) . . . . ? C13A C8A C9A C10A -1.0(5) . . . . ? C14A C8A C9A C10A 177.1(3) . . . . ? C8A C9A C10A N4A 1.9(5) . . . . ? C9A C10A N4A C12A -0.4(5) . . . . ? C10A N4A C12A C13A -2.1(6) . . . . ? N4A C12A C13A C8A 3.0(6) . . . . ? C9A C8A C13A C12A -1.2(5) . . . . ? C14A C8A C13A C12A -179.3(3) . . . . ? C13A C8A C14A N1 -47.7(4) . . . . ? C9A C8A C14A N1 134.2(3) . . . . ? C13B C8B C9B C10B 0.1(5) . . . . ? C14B C8B C9B C10B 177.6(3) . . . . ? C8B C9B C10B N4B 1.4(5) . . . . ? C9B C10B N4B C12B -1.2(5) . . . . ? C10B N4B C12B C13B -0.5(5) . . . . ? N4B C12B C13B C8B 2.0(5) . . . . ? C9B C8B C13B C12B -1.7(4) . . . . ? C14B C8B C13B C12B -179.1(3) . . . . ? C9B C8B C14B N2 138.2(3) . . . . ? C13B C8B C14B N2 -44.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1A 0.90(4) 1.83(4) 2.708(3) 168(4) . N1 H1B O2B 0.99(4) 1.78(4) 2.752(3) 165(3) . N1 H1C O2A 0.81(5) 2.02(5) 2.809(4) 165(4) 1_655 N2 H2A O1B 0.81(5) 1.90(5) 2.686(4) 167(4) 1_455 N2 H2B O2A 0.91(4) 1.86(4) 2.745(4) 166(4) . N2 H2C O2B 0.92(5) 1.86(5) 2.772(4) 171(4) . _chemical_name_common ((4-pyridylamethyl)ammonium)(m-iodobenzoate) ### END data_5_CSD_DEP_689524 _database_code_depnum_ccdc_archive 'CCDC 689524' _audit_creation_date 2008-06-29T12:41:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _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 ; (m-iodobenzoic)(((4-pyridylamethl)ammonium)(m-iodobenzoate) ; _chemical_formula_moiety 'C6 H9 N2, C7 H5 I O2, C7 H4 I O2' _chemical_formula_sum 'C20 H18 I2 N2 O4' _chemical_formula_weight 604.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 34.329(7) _cell_length_b 6.2971(13) _cell_length_c 21.548(4) _cell_angle_alpha 90 _cell_angle_beta 114.77(3) _cell_angle_gamma 90 _cell_volume 4229.6(18) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 27872 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.064 1 0 0 0.043 1 0 -3 0.075 -1 0 3 0.074 0 1 0 0.285 0 -1 0 0.249 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999). ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.002 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_absorpt_correction_T_min 0.3094 _exptl_absorpt_correction_T_max 0.7414 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '1.7\% \p and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_number 22957 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3932 _reflns_number_gt 3357 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+4.9643P] 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_number_reflns 3932 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.505 _refine_diff_density_min -0.991 _refine_diff_density_rms 0.102 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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 C1A C 0.36207(9) 0.0562(5) 0.23231(15) 0.0237(6) Uani 1 1 d . . . C2A C 0.38212(10) 0.1910(5) 0.20341(18) 0.0267(7) Uani 1 1 d . . . H2A H 0.3715 0.3307 0.1901 0.032 Uiso 1 1 calc R . . C3A C 0.41742(10) 0.1220(5) 0.19412(17) 0.0260(7) Uani 1 1 d . . . C4A C 0.43341(10) -0.0817(5) 0.21337(17) 0.0306(7) Uani 1 1 d . . . H6A H 0.4575 -0.1297 0.2063 0.037 Uiso 1 1 calc R . . C5A C 0.41390(11) -0.2133(5) 0.24288(19) 0.0324(8) Uani 1 1 d . . . H5A H 0.425 -0.352 0.2569 0.039 Uiso 1 1 calc R . . C6A C 0.37853(11) -0.1469(5) 0.25244(17) 0.0275(7) Uani 1 1 d . . . H4A H 0.3654 -0.2398 0.2728 0.033 Uiso 1 1 calc R . . C7A C 0.32367(10) 0.1356(5) 0.24159(17) 0.0271(7) Uani 1 1 d . . . O1A O 0.31151(9) 0.3208(4) 0.22346(16) 0.0459(7) Uani 1 1 d . . . O2A O 0.30528(7) 0.0106(4) 0.26666(13) 0.0344(5) Uani 1 1 d . . . I1A I 0.445605(8) 0.32909(4) 0.147958(14) 0.03837(9) Uani 1 1 d . . . C1B C 0.10805(10) 0.8542(5) 0.56509(17) 0.0267(7) Uani 1 1 d . . . C2B C 0.07083(10) 0.7526(5) 0.56057(16) 0.0241(6) Uani 1 1 d . . . H2B H 0.0642 0.6128 0.5427 0.029 Uiso 1 1 calc R . . C3B C 0.04384(10) 0.8599(5) 0.58269(17) 0.0260(7) Uani 1 1 d . . . C4B C 0.05260(10) 1.0653(5) 0.60804(16) 0.0295(7) Uani 1 1 d . . . H4B H 0.0335 1.1373 0.6225 0.035 Uiso 1 1 calc R . . C5B C 0.08955(11) 1.1637(5) 0.61188(19) 0.0333(8) Uani 1 1 d . . . H5B H 0.096 1.3043 0.6291 0.04 Uiso 1 1 calc R . . C6B C 0.11722(10) 1.0578(5) 0.59069(17) 0.0317(7) Uani 1 1 d . . . H6B H 0.1427 1.1259 0.5938 0.038 Uiso 1 1 calc R . . C7B C 0.13848(11) 0.7435(6) 0.54235(19) 0.0325(8) Uani 1 1 d . . . O1B O 0.12562(7) 0.5539(4) 0.51596(13) 0.0358(6) Uani 1 1 d . . . O2B O 0.17157(9) 0.8250(4) 0.54677(17) 0.0521(8) Uani 1 1 d . . . I1B I -0.011131(7) 0.70284(4) 0.578696(13) 0.03688(9) Uani 1 1 d . . . H1 H 0.1429(13) 0.496(7) 0.497(2) 0.055 Uiso 1 1 d . . . C8 C 0.23030(10) 0.2760(5) 0.40042(17) 0.0281(7) Uani 1 1 d . . . C9 C 0.19951(11) 0.1390(5) 0.40309(19) 0.0328(8) Uani 1 1 d . . . H9 H 0.197 -0.0016 0.3858 0.039 Uiso 1 1 calc R . . C10 C 0.17239(11) 0.2110(6) 0.43143(19) 0.0328(8) Uani 1 1 d . . . H10 H 0.1512 0.1167 0.4328 0.039 Uiso 1 1 calc R . . N4 N 0.17459(8) 0.4052(4) 0.45674(14) 0.0291(6) Uani 1 1 d . . . C12 C 0.20409(10) 0.5374(5) 0.45277(17) 0.0318(7) Uani 1 1 d . . . H12 H 0.2056 0.6781 0.4695 0.038 Uiso 1 1 calc R . . C13 C 0.23249(11) 0.4783(5) 0.42536(17) 0.0328(8) Uani 1 1 d . . . H13 H 0.2531 0.5761 0.4239 0.039 Uiso 1 1 calc R . . C14 C 0.26226(11) 0.2045(6) 0.3726(2) 0.0391(9) Uani 1 1 d . . . H14A H 0.2838 0.3179 0.3805 0.047 Uiso 1 1 calc R . . H14B H 0.2775 0.0765 0.3978 0.047 Uiso 1 1 calc R . . N1 N 0.24117(10) 0.1555(5) 0.29866(15) 0.0273(6) Uani 1 1 d . . . H1A H 0.2587(13) 0.122(6) 0.284(2) 0.041 Uiso 1 1 d . . . H1B H 0.2232(12) 0.266(7) 0.273(2) 0.041 Uiso 1 1 d . . . H1C H 0.2221(12) 0.029(6) 0.2893(18) 0.041 Uiso 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 C1A 0.0210(15) 0.0309(16) 0.0221(16) -0.0030(13) 0.0120(14) -0.0006(13) C2A 0.0244(17) 0.0283(16) 0.0316(19) 0.0001(13) 0.0159(15) 0.0017(12) C3A 0.0215(16) 0.0325(16) 0.0278(18) -0.0013(14) 0.0139(15) -0.0028(13) C4A 0.0245(17) 0.0418(19) 0.0319(19) -0.0001(15) 0.0180(16) 0.0069(14) C5A 0.0313(19) 0.0333(17) 0.036(2) 0.0034(15) 0.0175(17) 0.0095(14) C6A 0.0301(17) 0.0295(16) 0.0273(18) 0.0003(13) 0.0165(16) -0.0016(13) C7A 0.0241(16) 0.0320(17) 0.0293(19) -0.0045(14) 0.0153(15) -0.0020(14) O1A 0.0453(16) 0.0383(14) 0.074(2) 0.0148(13) 0.0450(16) 0.0154(11) O2A 0.0358(13) 0.0356(12) 0.0475(15) -0.0046(11) 0.0328(13) -0.0027(10) I1A 0.03481(15) 0.04303(15) 0.05267(18) 0.00296(10) 0.03347(13) -0.00072(9) C1B 0.0218(16) 0.0332(17) 0.0287(18) 0.0005(14) 0.0140(15) -0.0017(13) C2B 0.0221(15) 0.0258(15) 0.0253(17) -0.0023(13) 0.0109(14) -0.0024(12) C3B 0.0229(16) 0.0316(16) 0.0280(18) 0.0001(14) 0.0153(15) -0.0025(13) C4B 0.0292(17) 0.0378(18) 0.0228(17) -0.0057(14) 0.0121(15) 0.0031(14) C5B 0.0327(19) 0.0305(17) 0.036(2) -0.0072(15) 0.0142(17) -0.0036(14) C6B 0.0242(16) 0.0365(18) 0.036(2) -0.0038(15) 0.0144(16) -0.0090(14) C7B 0.0270(18) 0.0393(19) 0.037(2) -0.0012(16) 0.0195(17) -0.0031(15) O1B 0.0329(13) 0.0342(13) 0.0548(16) -0.0090(12) 0.0325(13) -0.0041(10) O2B 0.0350(15) 0.0586(17) 0.081(2) -0.0211(15) 0.0429(16) -0.0174(12) I1B 0.02804(14) 0.04956(16) 0.04314(16) -0.01163(11) 0.02484(12) -0.01133(10) C8 0.0191(16) 0.0457(19) 0.0210(17) -0.0014(14) 0.0100(14) 0.0019(14) C9 0.0289(18) 0.0379(18) 0.036(2) -0.0048(15) 0.0184(17) -0.0012(15) C10 0.0271(18) 0.0408(19) 0.037(2) -0.0032(16) 0.0193(17) -0.0053(14) N4 0.0226(14) 0.0403(16) 0.0285(15) -0.0004(13) 0.0148(13) 0.0001(12) C12 0.0313(18) 0.0366(17) 0.0328(19) -0.0047(15) 0.0185(16) -0.0002(15) C13 0.0276(17) 0.0414(19) 0.036(2) -0.0045(16) 0.0201(17) -0.0081(15) C14 0.0249(18) 0.061(2) 0.040(2) -0.0109(18) 0.0219(17) -0.0016(16) N1 0.0266(14) 0.0324(15) 0.0333(17) -0.0039(13) 0.0228(14) -0.0018(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1A C6A 1.392(4) . ? C1A C2A 1.393(4) . ? C1A C7A 1.500(4) . ? C2A C3A 1.378(4) . ? C2A H2A 0.95 . ? C3A C4A 1.389(5) . ? C3A I1A 2.105(3) . ? C4A C5A 1.377(5) . ? C4A H6A 0.95 . ? C5A C6A 1.379(5) . ? C5A H5A 0.95 . ? C6A H4A 0.95 . ? C7A O1A 1.245(4) . ? C7A O2A 1.263(4) . ? C1B C6B 1.379(5) . ? C1B C2B 1.395(4) . ? C1B C7B 1.498(5) . ? C2B C3B 1.383(4) . ? C2B H2B 0.95 . ? C3B C4B 1.387(5) . ? C3B I1B 2.100(3) . ? C4B C5B 1.382(5) . ? C4B H4B 0.95 . ? C5B C6B 1.385(5) . ? C5B H5B 0.95 . ? C6B H6B 0.95 . ? C7B O2B 1.213(4) . ? C7B O1B 1.317(4) . ? O1B H1 0.92(4) . ? C8 C13 1.372(5) . ? C8 C9 1.384(5) . ? C8 C14 1.521(4) . ? C9 C10 1.386(5) . ? C9 H9 0.95 . ? C10 N4 1.328(4) . ? C10 H10 0.95 . ? N4 C12 1.341(4) . ? C12 C13 1.386(4) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 N1 1.481(5) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? N1 H1A 0.81(4) . ? N1 H1B 0.94(4) . ? N1 H1C 1.00(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6A C1A C2A 119.2(3) . . ? C6A C1A C7A 122.0(3) . . ? C2A C1A C7A 118.9(3) . . ? C3A C2A C1A 120.1(3) . . ? C3A C2A H2A 119.9 . . ? C1A C2A H2A 119.9 . . ? C2A C3A C4A 120.6(3) . . ? C2A C3A I1A 118.6(2) . . ? C4A C3A I1A 120.7(2) . . ? C5A C4A C3A 119.1(3) . . ? C5A C4A H6A 120.5 . . ? C3A C4A H6A 120.5 . . ? C4A C5A C6A 121.1(3) . . ? C4A C5A H5A 119.5 . . ? C6A C5A H5A 119.5 . . ? C5A C6A C1A 120.0(3) . . ? C5A C6A H4A 120 . . ? C1A C6A H4A 120 . . ? O1A C7A O2A 123.8(3) . . ? O1A C7A C1A 117.9(3) . . ? O2A C7A C1A 118.3(3) . . ? C6B C1B C2B 120.2(3) . . ? C6B C1B C7B 119.3(3) . . ? C2B C1B C7B 120.5(3) . . ? C3B C2B C1B 118.6(3) . . ? C3B C2B H2B 120.7 . . ? C1B C2B H2B 120.7 . . ? C2B C3B C4B 121.7(3) . . ? C2B C3B I1B 118.4(2) . . ? C4B C3B I1B 119.9(2) . . ? C5B C4B C3B 118.9(3) . . ? C5B C4B H4B 120.5 . . ? C3B C4B H4B 120.5 . . ? C4B C5B C6B 120.2(3) . . ? C4B C5B H5B 119.9 . . ? C6B C5B H5B 119.9 . . ? C1B C6B C5B 120.4(3) . . ? C1B C6B H6B 119.8 . . ? C5B C6B H6B 119.8 . . ? O2B C7B O1B 123.4(3) . . ? O2B C7B C1B 122.4(3) . . ? O1B C7B C1B 114.2(3) . . ? C7B O1B H1 113(3) . . ? C13 C8 C9 118.7(3) . . ? C13 C8 C14 119.9(3) . . ? C9 C8 C14 121.4(3) . . ? C8 C9 C10 118.7(3) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N4 C10 C9 123.3(3) . . ? N4 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 N4 C12 117.4(3) . . ? N4 C12 C13 123.0(3) . . ? N4 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C8 C13 C12 118.9(3) . . ? C8 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N1 C14 C8 112.2(3) . . ? N1 C14 H14A 109.2 . . ? C8 C14 H14A 109.2 . . ? N1 C14 H14B 109.2 . . ? C8 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C14 N1 H1A 111(3) . . ? C14 N1 H1B 113(2) . . ? H1A N1 H1B 112(3) . . ? C14 N1 H1C 112(2) . . ? H1A N1 H1C 104(3) . . ? H1B N1 H1C 105(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A 0.9(5) . . . . ? C7A C1A C2A C3A -179.8(3) . . . . ? C1A C2A C3A C4A 0.0(5) . . . . ? C1A C2A C3A I1A 178.5(2) . . . . ? C2A C3A C4A C5A -1.0(5) . . . . ? I1A C3A C4A C5A -179.4(3) . . . . ? C3A C4A C5A C6A 1.1(5) . . . . ? C4A C5A C6A C1A -0.2(5) . . . . ? C2A C1A C6A C5A -0.8(5) . . . . ? C7A C1A C6A C5A 180.0(3) . . . . ? C6A C1A C7A O1A 178.6(3) . . . . ? C2A C1A C7A O1A -0.6(5) . . . . ? C6A C1A C7A O2A -2.1(5) . . . . ? C2A C1A C7A O2A 178.7(3) . . . . ? C6B C1B C2B C3B -0.5(5) . . . . ? C7B C1B C2B C3B 179.4(3) . . . . ? C1B C2B C3B C4B 1.0(5) . . . . ? C1B C2B C3B I1B -178.1(2) . . . . ? C2B C3B C4B C5B -0.7(5) . . . . ? I1B C3B C4B C5B 178.3(3) . . . . ? C3B C4B C5B C6B 0.0(5) . . . . ? C2B C1B C6B C5B -0.2(5) . . . . ? C7B C1B C6B C5B 179.8(3) . . . . ? C4B C5B C6B C1B 0.5(5) . . . . ? C6B C1B C7B O2B 1.5(6) . . . . ? C2B C1B C7B O2B -178.5(4) . . . . ? C6B C1B C7B O1B -177.1(3) . . . . ? C2B C1B C7B O1B 3.0(5) . . . . ? C13 C8 C9 C10 -0.6(5) . . . . ? C14 C8 C9 C10 177.5(3) . . . . ? C8 C9 C10 N4 -0.5(6) . . . . ? C9 C10 N4 C12 1.6(5) . . . . ? C10 N4 C12 C13 -1.7(5) . . . . ? C9 C8 C13 C12 0.5(5) . . . . ? C14 C8 C13 C12 -177.6(3) . . . . ? N4 C12 C13 C8 0.6(5) . . . . ? C13 C8 C14 N1 -115.8(4) . . . . ? C9 C8 C14 N1 66.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 N4 0.92(4) 1.76(4) 2.670(3) 175(4) . N1 H1A O2A 0.81(4) 1.93(4) 2.725(3) 169(4) . N1 H1B O2A 0.94(4) 1.83(4) 2.765(4) 170(4) 4 N1 H1C O1A 1.00(4) 1.69(4) 2.686(4) 177(3) 4_545 ###END _chemical_name_common (m-iodobenzoic)(((4-pyridylamethl)ammonium)(m-iodobenzoate)